I went shoe shopping with my partner the past two weekends, and I’ll be the first to plead ignorance to the difference between the B and D suffix for shoe sizes. And even after two weekends, I’m still learning.
I’ve never looked much into shoes. Having spent much of my early life bathed in chlorine (so much that at one point, my hair was brown with blond tips. FYI, for those I’ve never met in person before, I sport naturally black hair.), I’ve spent more time choosing the right $300-400 swimsuit than what I’d wear on my two lower appendages the other eight hours of the day. All that to say, I’m ill-equipped to speak the language of sneakerheads and running shoe geeks.
But just as I’m still learning how shoe geeks around the world understand the finer nuances of heel to toe drop impacting ankle versus knee strain, most founders who haven’t spent the time understanding the nuances of VCs think all money is green. In fact, just last month, I spoke with a founder I randomly met at an event who said, “Money is money.”
And he’s not completely wrong. There is some truth to it. At the end of the day, as investors, we sell money. Moreover, most investors who promise to be helpful are not. As well-intentioned as they are at the time of investment, most fall short of being truly helpful. There are multiple studies that show that founders believe a huge majority of their investors are not helpful.
That said, one of my investor buddies said something quite interesting to me earlier this week. Many founders see investors as saviors not partners. A source of capital to save them when they’re near the gates of hell, but not while they’re building their stairway to heaven. All that to say, as someone who’s been an operator, now a “VC”, but also someone who invests in other VCs, here are some of the nuances I’ve really come to appreciate over the years that I overlooked when I first stepped into the world of entrepreneurship.
Consensus and conviction-driven decision making
Some firms are consensus-driven. Others are conviction-driven. The former requires majority or unanimous buy-in. The latter doesn’t. Neither is universally better than the other, but knowing how decisions are made is extremely helpful. Not only to know who else you need to convince on the team, but also to know how the firm will help you post-investment.
The former is usually a firm where carry is split equally among all partners, so all partners are theoretically incented to see every portfolio company succeed. So as a founder, if you want to rely on the expertise and network of the collective partnership, these are the firms you should pursue. The latter, the conviction-driven ones, are most helpful if you really want one specific partner’s experience. They’ll be the person who takes the board seat. Opportunistically, they may ask for 1-2 junior team members to also have board observer seats. The downside is when and if this partner leaves the firm, there may be a gaping hole in governance as well as interest in the continued success of your company. But otherwise, this will be the partner you will have on speed dial.
I shared a presentation I made recently on LinkedIn. Of which, I share that three kinds of friends in the world. When shit hits the fan at 3AM in the morning…
There’s the friend you call. They see the call. And they go back to sleep.
There’s the friend you call. They see the call. And begrudgingly pick up.
And there’s the friend you call. And as they’re picking up the phone, they’ve got their pants on already and are running out the door with their keys.
Conviction-driven firms, where the partner that pounds the table for you will likely be on you board, or even if not, they’re going to be the third friend. At consensus-driven firms, and I’m clearly being reductive here, you’re more likely — not always — to have the reluctant one or sleepers.
Then it comes down to how the team is compensated. Not something most founders can find out or ask out, but how carry is distributed for each fund matters.
Disagreeableness
I’ve realized a lot of the best investors are quite disagreeable. They have their opinions and are quite vocal about them.
A lot of them quite often score incredibly low on investor review sites. Of course, some just score low on NPS purely because their assholes. But I want to caveat. Assholes are often disagreeable, but not all disagreeable people are assholes.
But it takes a lot of courage to have a contrarian viewpoint that one can back up. You don’t have to agree with it. But it matters. More often than not, these folks will also have negative references. For an LP evaluating VCs, that’s ok. Negative is always better than neutral references. The latter means you’re easily forgettable.
Regardless of whether you agree with these investors or not (equally, if not more true, in great founders), they make you stop and think. And that pause to think makes you a more well-rounded professional, and makes your own opinions more robust when you choose to adopt or not adopt said piece of advice.
There’s a great Steve Jobs line, which I think is quite applicable here. “Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.”
Great investors are troublemakers. In a good way.
P.S. To the three verified troublemakers I know who are reading this blogpost, can’t wait for your debut.
Small talk
Small talk was definitely one of those things I was rather dismissive of earlier in my career. Who da hell cares about the weather? Or what you did over the weekend?
But over the years, I realize some of the best investors are remarkably good at this. Not in the sense that they know how to ask great weather questions, but they learn how to build rapport early and quickly. And even better, they get a founder comfortable, honest, and candid about where they are at.
No one’s perfect. Every investor gets that. Most founders often pretend that they are. But a great investor is great at helping a founder realize they don’t have to be, and also get to understand a founder from a personal level. Not jumping straight into the pitch. Or give me your metrics. Or how much are you raising at how high of a valuation?
Radical candor
Borrowing this phrase from the amazing Kim Scott, the best investors are upfront with expectations. They don’t waste your time. Some even go as far as to share what their incentives are. And the harsh reality that they may be wrong many times before they’re right. They don’t beat around the bush. They don’t delay the inevitable. They’re great at ripping bandages off quickly, so they can prioritize their focus on other matters that require more attention. They have tough conversations early and synchronously. The last thing one can ever say about them is that they aren’t thoughtful. It seems remarkably simple, but most cannot do just that.
To be fair, it’s sometimes easier said than done. Even for myself, and I would not even dare to put myself in the category of great, I’ve been berated, gaslit, and shamed (haha!) for giving and attempting to give honest feedback to founders and investors. In fact, I was introed to a fund manager recently for the purpose of giving feedback. When I realized a couple red flags about her fund (namely her raising a $100M fund with no track record), I asked if she wanted feedback. To which, she replied with something to the effect that she only takes feedback from people who invest and that I didn’t deserve to give her feedback.
So I can see why some managers are averse to giving any.
Raising junior talent
I was reminded of this in my recent episode with Rick Zullo. And I noticed Rick is really good at giving credit and lifting up his team. In a soon-to-be-released episode, Eric Bahn from Hustle Fund does the same. I’ve asked him to speak at events before and he’s often referred one of his junior team members to the event. Not as a “I don’t want to do this, so someone else should”, but as a “I believe XX person will be a great future leader of this firm, and I believe others need to hear her insights.” And he’s been right every time.
Building an institutional firm takes more than one person. It takes a village. To build a legacy also requires more than one generation. I often see great investors taking less credit and giving a lot more to their team. Those often hidden from the limelight.
Discipline
Every great investor I know does something consistently every day. They set ground rules and while it’s less so for others, they hold themselves accountable to do so. Whether it’s a cup of coffee brewed from home every morning, or going to the gym on a daily basis or quality time with family or calling their significant other at a set time every day, I have yet to meet an investor who can’t keep to a promise they made to themselves consistently.
Venture capital is a long game, and it’s very possible for these multi-decade games, to be lucky at least once. Good investors, at some point, hit a unicorn. Great investors can discover many before others do. But any more than twice requires extreme discipline and the ability to say no to things that are good to make room for the great. And it’s so much harder than one might think.
And the simplest proxy to an investor’s ability to do so is their ability to fulfill promises to themselves when no one else is looking.
In closing
At the end of the day, not all shoes are the same. Just like not all VCs are. But if all you need is to get from Point A to Point B, and you don’t care for what kind of support you get along the way, VCs, like shoes, may all be the same.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Recently I’ve been hearing a lot of power law this, power law that. And you guessed right, that’s VC and LP talk. Definitely not founder vocabulary. Simply, that 20% of inputs lead to 80% of outputs. For instance, 20% of investments yield 80% of the returns.
Along a similar vein… what about questions? What 20% of questions lead to 80% of answers you need to make a decision? Or help you get 80% of the way to conviction in a deal?
‘Cause really, every question after those delivers only marginal and diminishing returns. And too much so, then you end up just wasting the founder’s or GP’s time. As the late Don Valentineonce said, “[VC] is all about figuring out which questions are the right questions to ask, and since we don’t have a clue what the right answer is, we’re very interested in the process by which the entrepreneur get to the conclusion that he offers.”
While I can’t speak for everyone, here are the questions that help me get to 80% conviction. For emerging GPs.
I’m going to exclude “What is your fund strategy?” Because you should have either asked this at the beginning or found out before the meeting. This question informs if you should even take the meeting in the first place. Is it a fit for what you’re looking for or not? There, as one would expect, you’d be looking into fund size, vertical, portfolio size, and stage largely. Simple, but necessary. At least to not waste anyone’s time from the get go.
Where are you at as a GP by Fund III? What does Fund I and II look like by Fund III?
Discipline. In the first 4 years of a fund, you’re evaluated on nothing else except for the discipline and the prepared mind that you have going in. All the small and early DPI and TVPI mean close to nothing. And it’s far too early for a GP to fall into their respective quartile. In other words, Fund I is selling that promise. The prepared mind. Fund II is selling Fund I’s strategy and discipline. Fund III, you’re selling the returns on Fund I.
Vision. Is this GP thinking about institutionalizing a firm versus just a fund? How are they thinking about creating processes and repeatability into their model? How do they think about succession and talent? And sometimes I go a few steps further. What does Fund V look like? And what does the steady state of your fund strategy look like?
What value do you bring to your portfolio companies?
This is going to help with reference calls and for you to fact check if an investor actually brings that kind of value to their portfolio companies. So, in effect, the question to portfolio companies would be: How has X investor helped you in your journey?
On the flip side, even during those reference calls, I like asking: Would you take their check if they doubled their ownership? And for me to figure out how high can they take their ownership in a company before the check is no longer worth it. There are some investors who are phenomenal $250K pre-seed/seed checks for 2.5-5% ownership (other times less), but not worth their value for $2-3M checks for the same stages. To me, that’s indicative of where the market thinks GP-market fit is at.
I also love the line of questioning that Eric Bahn once taught me. “How would you rate this GP on a scale of 1 to 10?” Oftentimes, founders will give them a rating of 6, 7, 8, or if you’re lucky 9. And the follow up question then becomes, “What would get this investor to a 10?” And that’s where meaty parts are.
Of course, it’s important to do this exercise a few times, especially with the top performers in their portfolio to truly have a decent benchmark. And the ones that didn’t do so well. After all, our brand is made by our winners. And our reputation is made by those that didn’t.
In the trifecta of sourcing, picking, and winning, this is how GPs win deals.
How do you resolve conflict or disagreement in the partnership?
This is really prescient in a partnership. Same as a co-foundership. If someone says, we never disagree, I’m running fast in the other direction. Everyone disagrees and has conflicts. Even twins and best friends do. If you don’t, you either have been sweeping things under the rug or one (or both or all) of you doesn’t care enough to give a shit. Because if you give a damn, you’re gonna have opinions. And not all humans have the same opinions. If everyone does, realistically, we only need one of you.
Hell, Jaclyn Freeman Hester even goes a step further and asks, How would you fire your partner?
Jaclyn on firing partners and team risk
Personally I think that last question yields interesting results and thought exercises, but lower on my totem pole (or higher if you want to be culturally accurate) of questions I need answers to in the initial meetings.
How are you finding companies? How are you building your pipeline?
This is always a question I get to, but especially valuable, when I ask it to spinouts. Building a repeatable and scalable sourcing pipeline is one of the cruxes of being a great fund manager. But in the age when a lot of LPs are shifting their focus to spinouts from top-tier funds, it’s an important reminder that (a) not all spinouts are created equal, and (b) most often, I find spinouts who rely largely on their existing “brand” and “network” without being able to quantify the pillars of it and how it’s repeatable.
For (a), a GP spinning out is evaluated differently than a partner or a junior investment member. A GP is one who manages the LP relationships, and knows intimately the value of what goes in an LPA, on top of her/his investing prowess. And the further you go down the food chain, the less visibility one gets of the end to end process. In many ways, the associates and analysts spinning out need the most help, but are also most willing to hustle.
Which brings me to (b). Most spinouts rely on the infrastructure and brand of their previous firm, and once they’ve left, they lose that brand within a year’s time. Meaning if they don’t find a way or have an existing way to continue to build deal flow, oftentimes, they’ll be left with the leftovers on the venture table. This question, for me, gives me a sense of whether an investor is a lean-in investor or a lean-back investor. The devil’s in the details.
What are the top 3 reasons I shouldn’t invest?
This is a test to see how much self-awareness a founder/GP has. The most dangerous answer is saying “There are no reasons not to invest.” There are always reasons not to. The question is, are you aware of them? And can you prioritize which risks to de-risk first?
In many ways, I think pitching a Fund I as illustrating the minimum viable assumption you need to get to the minimum viable product. And Fund II is getting to the minimum lovable strategy (by founders and other investors in the ecosystem). And with anything that is minimally viable, there are a bunch of holes in it.
Another way to say the above is also, “If halfway through the fund we realize the fund isn’t working, what is the most likely reason why?”
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
At the end of last week, an LP told me something quite provocative. That right now in 2024, we’re in a low-risk environment.
And in all fairness, I thought he was completely bonkers. Fear is high. Investments have slowed their pace, especially in the private markets. Markets have really yet to recover. Some believe we’ve hit the bottom and will bounce around the bottom a few times. Others think we’ve yet to see the worst of it. Hell, just yesterday, Eric Bahn tweeted the below:
These articles were published by the same company within hours of each other… pic.twitter.com/k9TPc2Si5a
Wars are raging across the world. Currency is fluctuating on a global scale. Hell, even for the average person, prices are going up at a rate unfamiliar to most people’s memory.
But his next line really made me pause. “You’re right. There’s geopolitical risk, currency risk, market risk, and valuation/pricing risk. And we can identify every single one of them. In fact, the actual risk of investing today is really low, but the perceived risk is really high. Risk is highest when you can’t tell what the risk is. That was 2020 and 2021, when you couldn’t put a finger on what kinds of risk were out there.”
And that really stuck with me. To underscore again, risk is highest when you can’t tell what the risk is.
And so paved way for this blogpost. Albeit, that last line was the punchline.
He later told me that the concept wasn’t original, but that its origin traces its way back to Ken Moelis. Regardless of the attribution, it’s worth doing a double take on.
There’s that famous Peter Drucker line, “You can’t manage what you don’t measure.” And in many ways, it is just as true for risk as it is for tasks and KPIs and OKRs.
The family office for a well-known luxury brand once told me that they like to pay the complexity premium on esoteric alternatives. To them, venture is one of those esoteric alternatives. In addition, they’re also happy to overpay during bull markets. Access to a volatile and nascent asset class, to them, deserves a premium.
But taking a step back, there may be more wisdom to it than I initially thought. In bear markets, when the risk is real and discrete, there is no complexity premium to pay. After all, you can begin to manage what you do measure. On the flip side, in a bull market, where no one really knows who will win or what the macro risks are, a premium can be and often is paid as a bet on a company’s future and insurance against a margin of error that is hard to define.
Of course, one can say that the premium is often hype-driven instead of risk-driven. But really, hype is just long-term risk donned with a new set of clothes. A short-term luxury with a buy-now-pay-later tag that comes in quarterly installments of belt-tightening and regret.
While I personally have always believed that as an investor it’s better to be disciplined and to “dollar cost average” across vintages vis a vis time diversification, there are several great investors who believe price is a trap. At the top of my head, Peter Fenton and Keith Rabois. The latter shared his thoughts earlier this year on why. At least for seed and Series A. That in summary, there is no limit on how much you pay for a great company at the seed and Series A (likely the pre-seed as well) that won’t return you multiple-fold back. And that debates on price really are leading indicators on conviction or lack thereof.
The last part of which I agree to an extent.
All that to say, I think a useful exercise to go through whenever making a major (investment) decision is to take out a notepad and write down all the risks you can think of. If you can think of it, you can probably find a way to hedge against it. On the flip side, if you’re about to make a decision and you can’t think of any risks, that’s probably the biggest risk you’ll take.
As my mom told me since I was a kid, “There’s no such thing as a free lunch.”
But if you do come up with a good list, and the world around you is still scared, and you think there might be something special in the opportunity in front of you, sometimes it pays to be bullish when others are bearish.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
I’ve always admired the way Mike Maples has thought about backcasting. In summary, he proposes that true innovators are visitors from the future. Or as he puts it: “Breakthrough builders are visitors from the future, telling us what’s coming.” Such that they “pull the present from the current reality to the future of their design.” In other words, start from the future, then work your way backwards to figure out what you need to do today to get there.
And I find it equally as empowering to do the same exercise as an emerging manager. Hell, for any aspiring institutional investor. Be it from an angel to a GP. Or an individual LP to a fund of funds.
Start from your ideal fund model. Your ideal LP base. Your ideal pitch deck. Then work backwards to figure out what you need to do today. For the purpose of this blogpost, I’ll focus on reference checks.
For everyone in the investing world, especially in the early-stage private markets, we all know that reference checks is a key component of making investment decisions. Yet too often, founders and emerging managers alike think about them retroactively. Post-mortem. Testimonials that are often not indicative of one’s strengths. And especially not indicative of how a GP won that investment, as well as how they can win such investments in the future.
An exercise I often recommend investors do is write your ideal reference you would like to get from a founder. Be as specific as you can. What would your portfolio founders say about you? How have you helped them in a way that no one else can? What do founders who you didn’t fund say about you?
Another way to think about it is if you were to own a word — something that would live rent free in people’s minds — what would you own? Hustle Fund owns “hilariously early.” Spacecadet Ventures owns “the marketing VC” and they live up to it. Cowboy’s Aileen Lee created the idea of “unicorns.” “Software is eating the world” is attributed to Marc Andreessen.
On the flip side of the token, what are testimonials that should never be written about you?
Hell, at this point, if you’re an aspiring institutional investor, and have yet to spell things out, create the whole deck. Fill in the numbers and the facts later, but for now, make up your ideal deck. When leading indicators become lagging, then update it and fill it in.
Then be that kind of investor for every founder you help. As Warren Buffett once said, “You should write your obituary and then try and figure out how to live up to it.”
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
There was a fascinating episode on the Tim Ferriss Show recently, where we get the inside baseball on how David Maisel, founder of Marvel Studios, raised half a billion on a promise for a company who’s public market cap at the time was only a fifth of a billion. Naturally, not only was he against a lot of headwind externally, but internally as well. According to the board at the time, they would only greenlight the idea of producing their own films (as opposed to licensing their IP out) if “Marvel had no risk. Not little risk, but no risk.”
On the cusp of Captain America and Thor being licensed away, David asked the board to give him six months. The “zero risk” pitch then came in the form of external funding, huge financial upside (if things worked out), market timing, and a promise.
Financial upside for Marvel
As David puts it:
“First to my board, the argument, was if we own our own studio, it means we get the full financial upside that they understood very well.” As opposed to licensing, their traditional business model. Where Marvel only got five cents on every dollar of profit. As was the case with SONY and Spiderman.
“Number two, we decide on greenlight when the movies get made that they also understood because they only sold toys really at the time, and the toys were contingent on a movie, which they then control the timing. Now when you’re doing a public company and you’re giving guidance every year, how can you give guidance if you don’t even know what movies are going to get made? And so controlling greenlight was important, full creative control.”
Moreover, the team was able to take 5% of revenues as the producer fee AND keep all non-film revenues (i.e. toys, video games, etc.). And even if four out of the five films lost capital, they’d still make $25M in revenue each. In other words, $100M in sum. Half of Marvel’s public market cap at the time. Whose cap was only based on toy sales.
Market timing
“The bond bubble of 2004 was happening,” as David shared, “so it was a time where there was loans being made that shouldn’t have been made. And a lot of people were enamored with Hollywood as they get enamored every few years.”
Zero downside
Instead of funding the studio off balance sheet, David would go out to fundraise from others. So what was the external pitch?
“Give me four at bats, and if one of them hits, then every movie’s a sequel after that.”
On top of all the above, to me, there were some interesting terms for the investment that helped sweeten the deal:
Merrill Lynch got a 3% success fee upon the $525M closing.
David got a low interest rate loan from Merrill by getting it insured by MPAC, therefore the debt became AAA debt, which “was easy to sell to pensions and easy to sell to individual investors” in case things went awry.
Now I’m not sure if this is standard Hollywood practice. But I imagine it’s not, at least back in ’03 and ’04. I’m a venture guy after all. And as one, the above is news to me.
That said, the banks David went to fundraise from were not taking equity. It was “pure debt. So very low interest rate. And the only collateral were the film rights to ten Marvel characters of which we could make for the movies.” Which, to me, ten characters sounds like a lot for a company whose business is characters. I also imagine these were characters that had some level of historical fanbase, so they weren’t random ones from the archives.
But David clarifies. “A lot of people misunderstand that they think we pledged ten of our characters as collateral. It wasn’t that at all because in the worst case scenario, it only got collected if we lost money on those first four movies. And then those six characters, we owned all the rights besides film. And if a film was ever made by the bank, whoever collected this collateral, we got the same license fee that we get if we just license it that day to a party. So there was no opportunity cost.”
And the promise
This is history now, but at the time, was a bold claim. The idea was borne out of frustration as an entertainment investor. That:
Marvel couldn’t capture a large part of enterprise value through productions with just licensing
The first movie business was horrible. Sequels, on the other hand, were a lot more predictable. So, the focus after the first movie would not be on predicting profit, but maximizing profit margins.
So David had a thought. “What if after the first movie, every movie after that was a sequel or a quasi-sequel, which required all the characters, or a lot of the characters, to show up in multiple movies?”
The idea of sequel snowballed into what we now know as the MCU — the Marvel Cinematic Universe.
Bringing it back to venture
It’s a nice corollary to raising a Fund I, where you’re also selling a promise. A world vision. A painting of the future. Nothing’s proven yet. You’re sure as hell not selling a repeatable strategy yet, and definitely not any returns. Since there’s a good chance you haven’t returned capital to LPs before.
And this is true for not just funders, but also founders. In the words of Mike Maples, “Breakthrough builders are visitors from the future, telling us what’s coming. They seem crazy in the present but they are right about the future.
“Legendary builders, therefore, must stand in the future and pull the present from the current reality to the future of their design. People living in the present usually dislike breakthrough ideas when they first hear about them. They have no context for what will be radically different in the future. So an important additional job of the builder is to persuade early like-minded people to join a new movement.”
Dissent is a luxury
The truth is loads of people will disagree with you. You’re not looking for consensus. In fact, it’s better to be wrong and alone than right and with the crowd if you’re in the venture world. Either as a founder or an emerging GP. It’s something I recently learned from the one and only Chris Douvos. If you imagine a 2×2 matrix… On one axis, you have right and wrong. On the other, you have with the crowd and alone. You want to be in the right and alone quadrant for sure. That’s where “fortune and glory” exists. It’s where alpha exists. It is how you become an outlier and achieved outsized returns.
But the prerequisite to be there is to have the guts to start in the wrong and alone quadrant. If you start from being right and in the crowd, you’re one among many. And that doesn’t give you the liberty to have independent thinking. You’re constantly trapped in noise.
It’s as Abhiraj Bhal says. “If you are a category-defining company, you will always have a TAM question, if the category is defined by somebody else, you will not have a TAM question.” You want people to question you. And as humans, we like to fit in. But to create something transcendent, external doubt is your best friend.
As such, your promise of the future must seem bizarre.
Don’t start with the product, start with your customers
When you have a promise, admittedly, the easiest way is to start engineering it right away. Without market validation. Without stress testing. Which pigeonholes a number of founders. I forgot the origination, but there’s a great line that says, “The only difference between a hallucination and a vision is that other people can see the latter.”
And in order to test that, you need to get in front of potential users and customers first. Max, someone I had the joy of working with, once wrote the below timeless tweet:
My hot take of the day:
Most aspiring startup founders who think they should learn to code would be better off learning to write well instead.
As Elizabeth once shared: “We decided that we’d start with no product. We would not build anything. And, we just started selling ads. We manually brokered deals with publishers and advertisers and took a cut in between. We got our customers by emailing people and setting up the copy and links ourselves. People would pay me through my personal PayPal account. It was only when we realized we were onto something that we started building technology to remove bottlenecks.”
On the investor side, it’s building a thesis where great investments fall into. It’s a way of looking at the world in a perspective that may seem foreign to others, but almost obvious in retrospect. The thesis should elicit the response, “Why didn’t I think of that first?” But no matter how obvious, you are the best positioned to bring the thesis to life. That doesn’t mean you need returns yet. Although good graduation rates certainly help as a leading indicator.
In that regard, it’s quite similar to how David Maisel foretold of the Universe to come. Obvious once explained, yet still met with resistance from legacy players.
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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Voila, the fourth installation of 99 soundbites I’ve been fortunate enough to collect over the past year. The first four of what I imagine of many more to come. Each of which fall under one of the ten categories below, along with how many pieces of advice for each category:
You can also find the first three installments of 99 pieces of advice for both founders and investors here. Totaling us to a total of 396 pieces of advice.
But without further ado…
Fundraising
1/ If you’re an early stage startup, expect fundraising to take at least 3-4 months to raise <$1M. If you’re on the fast side, it may take only 2 weeks. – Elizabeth Yin*timestamped April 2022
2/ If you’re going to raise a round over 6-12 months, it often doesn’t seem fair that your first commits have the same terms as those who commit 6 months later, since you’ve grown and most likely have more traction at the time. As such, reward your early investors with preferred terms. Say you’re raising a $1M round. Break the round up to $300K and $700K. Offer a lower cap on SAFEs for the $300K. “Tell everyone that that offer will only be available until X date OR until you hit $300k in signed SAFEs. And that the cap will most likely go up after that.” Why? It lets you test demand and the pricing on the cap – to see if you’re cap is too high or too low on the first tranche. – Elizabeth Yin
3/ As a startup in recessionary times, you have to grow your revenue faster than valuations are falling to make sure you raise your next round on a mark up. Inspired by David Sacks and Garry Tan. *timestamped April/May 2022
4/ There’s only going to be 1/3 the amount of capital in the markets than in 2020 and 2021. So plan accordingly. If you’re not a top 0.1% startup, plan for longer runways. Fund deployments have been 1-1.3 years over the past 1.5 years, and it’s highly likely we’re going to see funds return back to the 3-year deployment period as markets tighten. *timestamped May 2022
5/ B2B startups that have the below disqualifiers will find it hard to raise funding in a correcting venture market:
No to little growth. Good growth is at least doubling year-over-year.
Negative or low gross margins. Good margins start at 50%.
CAC payback periods are longer than one year.
Burn multiples greater than 2 (i.e. You’re burning $2 for every dollar you bring in). A good burn multiple is 1 or less. – David Sacks
6/ Beware of “dirty term sheets.” Even though you’re able to get the valuation multiple you want, read the fine print for PIK dividends, simple “blocks” on IPO/M&A, and 2-3x liquidation preferences. Inspired by Bill Gurley.
7/ “This came at a very expensive valuation with certain rights that should not have come with it — like participating preferred, which is they first get their money out and then they participate in the rest, which was OK for the earlier rounds, but not for the later ones.” – Sabeer Bhatia in Founders at Work
8/ In a bear market, public market multiples are the reference points, not outlier private market multiples. Why? Public market multiples are their exit prices – how they return the fund. It matters less so in bull markets. – David Sacks
9/ Don’t trust the “why”, trust the “no.” Investors don’t always give the most honest responses when they turn down a company.
10/ If you inflate your projections, the only investors you’ll attract are dumb investors. They’ll be with you when things are going well and make your life a living nightmare when things aren’t, will offer little to no sound advice, and may distract you from building what the market needs. By inflating your projections, you will only be optimizing for the battle, and may lose the war if you can’t meet or beat your projections.
11/ VCs will always want you to do more than you are pitching. So if you’re overpromising, they’re raising their expectations even more down the road.
12/ Five questions you should answer in a pitch deck:
If you had billboard, what 10 words describe what you do?
What insight development have you had that others have not?
How you acquire customers in a way others can’t?
Why you?
What you need to prove/disprove to raise next round? – Harry Stebbings
13/ The longer you’re on the market, the greater the differential between expectations and reality, and the harder it is over time to close your round. Debug early on in the fundraising process (or even before the fundraising process) by setting and defining expectations through:
Leveraging market comparables. You don’t have to be good at everything, but you have be really really amazing at one thing your competitors aren’t. It’s okay if they’re better than you in other parts.
14/ You should reserve 10% of your round to allocate to your most helpful existing investors. Reward investors for their help. – Zach Coelius
15/ If your next round’s investor is willing to screw over your earlier investors out of pro rata or otherwise. After they leave, the only one left to screw over is you. – Jason Calacanis
16/ “Nobody’s funding anything that needs another round after them.” – Ben Narasin quoting Scott Sandell
17/ “When a VC turns you down for market size, what they are really saying is: I don’t believe you as the founder has what it takes to move into adjacent and ancillary markets well.” – Harry Stebbings
18/ When raising from corporates, be mindful of corporate incentives, which may limit your business and exit opportunities. “I’ve often seen the structure just simply be a SAFE with no information rights. No Board seats. Check sizes that are worth < 5% ownership. No access to trade secrets.” – Elizabeth Yin
19/ LOIs mean little to many investors, unless there’s a deposit attached to it. A customer must want the product so much they’re willing to take the risk of putting money down before they get it. 1-5% deposit would be interesting, but if they pay the product in full, you would turn investor heads. – Jason Calacanis
20/ “The most popular software for writing fiction isn’t Word. It’s Excel.” – Brian Alvey
21/ “Ask [prospective investors] about a recent investment loss, where the company picked someone else. See how they describe those founders, the process, and what they learned. This tells you what that investor is like when things don’t go their way.” – Nikhil Basu Trivedi
22/ “Founders, please hang onto at least 60% of the company’s equity through your seed raise. Series A or B is the first time founder equity should dip below 50%. I’ve seen cap tables recently where investors took too much equity early on, creating financing risk down the road.” – Gale Wilkinson
23/ “One of the worst things you can say to a VC is ‘we’re not growing because we’re fundraising.’ There are no excuses in fundraising.” – Jason Lemkin. Fundraising is a full-time job, but when you’re competing in a saturated market of attention, it’s you who’s fundraising, but not growing, versus another founder who’s also fundraising and is growing.
25/ The goalposts of fundraising (timestamped Oct 20, 2022 by Andrea Funsten):
Pre-seed: $750K-1.5M round
Valuation: $5-10M post (*She would not go over $7M)
Traction:
A working MVP
Indications of customer demand = have interviewed hundreds of potential customers or users
2-5 “Design Partners” (non-paying customers or users)
Seed: $2-5M round
Valuation: $12-25M post (*She would not go over $15M)
Traction:
$10-15K MRR, growing 10% MoM
6-12 customers who have been paying for ~6 months or more, a few that would serve as case studies and references
Hired first technical AE
Series A: $8-15M round
Valuation: “anyone’s guess”
Traction:
$1.5M in ARR is good, more like $2M
3x YoY growth minimum, but more like 3.5x • 12-20 customers, indications of ACV growth
Sales team in place to implement the repeatable sales playbook
26/ Don’t take on venture debt unless you have revenue AND an experienced CFO. – Jason Calacanis
27/ When you are choosing lead investor term sheets:
For small VC teams (team <10ppl): Make sure your sponsoring partner is your champion. Why does investing in you align with their personal thesis? Their life thesis? Which other teams do they spend time with? How much time do they spend with them? When things don’t go according to plan, how do they react? How do they best relay expectations and feedback to their portfolio founders?
For larger platform teams (team >10ppl): Ask to talk to the 3-5 best people at the firm. And when the investor asks you to define “best”, ask to talk to their team members who best represent the firm’s culture and thesis. Why? a/ This helps you best understand the firm’s culture and if there’s investor-founder fit. b/ You get to know the best people on the team. And will be easier to hit them up in the future.
28/ “If you are a category-defining company, you will always have a TAM question, if the category is defined by somebody else, you will not have a TAM question.” – Abhiraj Bhal
29/ “[Venture] debt typically has a 48-54 month term, as follows: 12 months of a draw period (ballooned to 18 months over the last few years), to which you can decide to use it or not 36 months to amortize it after that 12 months. The lender at this stage is primarily underwriting to venture risk, meaning they are relying on the venture investor syndicate to continue to fund through a subsequent round of financing.” This debt is likely to be paired with language that allow the fund to default if investors say they won’t fund anymore and/or just not to fund when asked. “They typically are getting 10bps-50bps of equity ownership through warrants. Loss rates must be <3-4% for the model to work.” If there’s less than 6 months of runway or cash dips below outstanding debt, then as a founder, expect a lot of distracting calls. – Samir Kaji
30/ The best way to ask for intros to investors is not by asking for intros, but by hosting an event and having friends invite investors to the event. There’s less friction in an event invite ask than an investor intro ask. The reality is that the biggest investors are inundated with intro requests all the time, if not just by cold email too.
Cash flow levers
31/ The bigger your customers’ checks are (i.e. enterprise vs. SMB vs consumer), the longer the sales pipeline. The longer the sales pipeline, the longer you, the founder, has to stay the Head of Sales. For enterprise, the best founders stay VP of Sales until $10M ARR. For SMB, that’s about $1-2M ARR, before you hire a VP of Sales. Inspired by Jason Lemkin.
32/ “‘I have nothing to sell you today — let’s take that off the table and just talk,’ he would say. ‘My goal is to earn the right to have a relationship with you, and I know it’s my responsibility to earn that right.'” The sales playbook of David Beirne of Benchmark Capital fame, cited in eBoys.
33/ “All things being equal, a heavy reliance on marketing spend will hurt your valuation multiple.” – Bill Gurley
34/ If you were to double or triple the price of your product, what percent of customers would churn? If the answer is anything south of 50%, why aren’t you doing it?
35/ Getting big customers and raising capital is often a chicken-and-egg game. Sometimes, you need brand name customers, before you can raise. And other times, you need capital before you can build at the scale for brand name customers. So, when I read about Vinod Khosla’s advice for Joe Kraus: “We had $1 million in the bank and we didn’t know what we were going to bid. We sat down in my office, all on the floor. Vinod said we should bid $3 million. I was like, ‘How do we bid $3 million? We only have $1 million in the bank.’ And he said, ‘Well, if we win, I’m pretty sure we can raise it, but if we don’t win, I don’t know how we’re going to raise.'”
36/ “Your ability to raise money is your strategy. If you’re great at it, build any business with network effects. If you’re bad at fundraising, it’s strategically better to build a subscription business with no network effects.” – Elizabeth Yin
37/ Be willing to fire certain customers (when things get tough or in an economic downturn). If they aren’t critical strategic partners or are loss making, figure out how to make them profitable. If you can, renegotiate contracts, like cheaper contracts for longer durations. If not, let them go. Make it easy to offboard.
38/ An average SaaS business, that doesn’t have product-led growth, is spending about 50% of revenue on sales and marketing. Those that are in hyper growth are spending 60%. – Jason Lemkin
39/ “The only thing worse than selling nothing is selling a few. If you sell nothing, you stick a bullet in it and move on. When you sell a few, you get hope. People keep funding even though it’s really not viable.” – Frank Slootman
40/ If your customer wants to cancel their auto-renew subscription to your product, you should refund them a 100% of their cost. – Jason Lemkin
41/ “Your price isn’t too high. Your perceived value is too low.” – Codie Sanchez
42/ “15-20% of IT spend is in the cloud.” And it’s likely to go up. – Alex Kayyal
43/ If your customers are willing to pay you way ahead of when your service is executed, you have an unfair and unparalleled cashflow advantage. – Harry Stebbings
44/ If you’re in the CPG business, it’s better to negotiate down the contract. “You buy 75, and you sell 60, they’re going to go, ‘Ah, I got 15,000 in inventory, it’s not a success.’ If you give them 40, and then they have to buy another 20, and they sell 60, they go, ‘Wow, we ordered 50 [(I think he meant 20)] more than our original order.’ You’re still at 60, but one, they’re disappointed, and one, they’re not. You’re still playing some weird mind games a little bit so that they feel good about whatever number was there.” – Todd McFarlane
45/ “If you are under 100 customer/users, get 20 of them in a Whatsapp Group. You will:
Get much higher quality feedback, faster, on the current product.
They will be WAY more proactive in suggesting future product ideas and helping you shape the product roadmap.
It will create a closer relationship between you and them and they will become champions of the product and company. People like to feel they had a hand in the creation process.” – Harry Stebbings
46/ Create multiple bank accounts with different banks to keep your cash, to hedge against the risk of a bank run. The risk is very unlikely to occur, but non-zero, especially in a recessionary market. Inspired by SVB on March 10, 2023. More context here, and what happened after here. Breakdowns here, here and here.
47/ “Keep two core operating accounts, each with 3-6 months of cash. Maintain a third account for “excess cash” to be invested in safe, liquid options to generate slightly more income.” – A bunch of firms
48/ “Maintain an emergency line of credit. Obtain a line of credit from one of your core banks that can fund the company for 6 months. Do not touch it unless necessary.” – A bunch of firms
49/ In case of a bank run: “1/ Freeze outgoing payments, let vendors know you need 60 days, 2/ Figure out payroll & let your investors know exactly when cash out, 3/ Attempt emergency bridge with existing investors; hopefully reasonable terms or senior debt (but given valuation reset this is a HARD discussion for many), 4/ Figure out who can take deferred salary on management team, which will extend runway, 5/ Make sure you communicate reality to team honestly so they can make similar plan for their household, 6/ Make sure you talk to HR about legal issues around payroll shortfall — which hopefully this doesn’t come to, 7/ In future, keep cash in 3 different banks.” – Jason Calacanis
50/ “Whenever a CEO blames their bad performance on the economy, I knew I had a really crappy CEO. ‘Cause it wasn’t the economy, it was a bad product-market fit. The dogs didn’t wanna eat the dogfood. Sometimes the economy can make that a little worse, but if people are desperate for your product, it doesn’t matter if the times are good or bad, they’re going to buy your product.” – Andy Rachleff
51/ General reference points for ACV and time to close are: $1K in 1 week. $10K in 1 month. $100K in 3 months. $300K in 6 months. And $1M in 12 months. – Brian Murray
52/ A B2B salesperson’s script from Seth Godin. “Look, you’ve told me you have this big problem you need to solve. You have a five million assembly line that’s letting you down, blah blah. If we can solve this problem together, are you ready to install our system? Because if it’s not real, let’s not play. Don’t waste my time, I won’t waste yours. You’re not going to buy from me because I’m going to take you to the golf course. You’re not going to buy from me because our RFP is going to come in cheaper than somebody else’s. You want my valuable time? I’m going to engage with you, and tell you the truth and you’ll tell me the truth. You’re going to draw your org chart for me. You’re going to tell me other complicated products you’ve bought and why your company bought them. And I’m going to get you promoted by teaching you how to buy the thing that’s going to save your assembly line. Let’s get real or let’s not play.” – Seth Godin
53/ “The job of a pre-seed founder is to turn investor dollars into insights that get the company closer to finding product-market fit.” – Charles Hudson
Culture
54/ Deliver (bad) news promptly. Keep to a schedule. The longer you delay, the more you lose your team’s confidence in you. For example, if your updates come out every other Friday, and you miss a few days, your team members notice. Your team is capable of taking the tough news. This is what they signed up for. Explain a stumble before it materially impacts your bottom line – revenue. Inspired by Jason Lemkin.
56/ “It’s easier, even fun, to do something hard when you believe you’re doing something that no one else can. It’s really hard to go to work every day to build the same thing, or an even worse version, of what others are already building. As a result, there was a huge talent drain from the company.” – Packy McCormick
57/ Lead your team with authenticity and transparency. “Employees have a ridiculously high bullshit detector, more so than anyone externally, because they know you better. They know the internal brand better.” So you have to be honest with them. “Here’s what we’re going to tell you. Here’s what we won’t, and here’s why.” Set clear expectations and leave nothing to doubt. – Nairi Hourdajian
58/ When someone ask Jeff Bezos, when does an internal experiment get killed? He says, “When the last person with good judgment gives up.” – Bill Gurley citing Jeff Bezos
59/ “Getting too high on a ‘yes’ can prepare you for an even bigger fall at the next ‘no.’ Maintaining your composure in the high moments can be just as important as not getting too down in the low moments.” – Amber Illig
60/ “Most have an unlimited policy paired with a results-driven culture. This means it’s up to the employee to manage their time appropriately. For example, no one bats an eye when the top performing sales person takes a 3 week vacation. But if someone is not pulling their weight and vacationing all the time, the perception is that they’re not cut out for a startup.” – Amber Illig
61/ “Whenever we’re dealing with a problem and we call a meeting to talk about the problem, I always start with this structure. We are here to solve a problem. So the one option that we know we’re not going to leave the room doing is the status quo. That is off the table. So whenever we finish this meeting, I want to talk about what option we’re taking, but it’s not going to be what we’re currently doing.” – Tobi Lutke
62/ “[Peter Reinhardt] would put plants in different parts of the office in order for the equilibrium of oxygen and CO2 to be the same. He would put noise machines in the perfectly placed areas and then reallocate the types of teams that needed to be by certain types of noise so that the decibel levels were consistent. What I don’t think people realize about founders is that they are maniacal about the details. They are unbelievable about the things that they see.” – Joubin Mirzadegan
63/ “Leadership is disappointing people at a rate they can absorb.” – Claire Hughes Johnson
64/ Page 19 Thinking: If you were to crowdsource the writing of a book, someone has to start inking the 19th page. And it’s gotta be good, but you can’t make it great on the first try. So you have to ask someone else to make it better, and they have to ask another to make their edits even better. And so on. Until page 19 looks like a real page 19. “Once you understand that you live in a page 19 world, the pressure is on for you to put out work that can generously be criticized. Don’t ship junk, not allowed, but create the conditions for the thing you’re noodling on to become real. That doesn’t happen by you hoarding it until it’s perfect. It happens by you creating a process for it to get better.” – Seth Godin
Hiring
65/ Hiring when your valuation is insanely high is really hard. Their options could very much be valueless, since they would depend on the next valuation being even higher, which either means you grow faster than valuations fall (market falls in a bear market) or you extend your runway before you need to fundraise again.
66/ It’s easier to retain great talent in a recession, but much harder to retain them during an expansionary market. Talent in a boom market have too many options. There’s more demand than there is supply of talent in a boom market.
67/ If you’re a company with low employee churn, you can afford to wait a while longer to find someone who is 20% better in the role. – Luis von Ahn
68/ “[Fractional CMOs and CROs often] want to be strategists. Tell you where to focus, and what to do better. But the thing is, what you almost always just need is a great full-time leader to implement all the ideas.” – Jason Lemkin. The only time it works is when the fractional exec owns the KPI and the function, where they work at least 60% of the time OR they work part-time and help you hire a full-time VP.
69/ Hire your first full-time comms person after you hit product-market fit, when you are no longer finding your first customers, but looking to grow your customer base. – Nairi Hourdajian
70/ “Ask [a high-performing hire] if there’s someone senior in her career that’s been a great manager, and if so, bring them on as an equity-compensated advisor to your company. If there’s someone in industry she really admires but doesn’t yet know, reach out to them on her behalf.” Give her an advisor equity budget, so they can bring on a mentor or someone they really respect in the industry. As a founder, create a safe space for both of them. Monthly 1:1s and as-needed tactical advice, introductions, and so on. And don’t ask that mentor to give performance feedback “because if so it’s less likely they’ll have honest, open conversations.” – Hunter Walk
71/ Hire talent over experience for marketing and product. “In marketing and product I prefer people with less experience and a lot of talent so we can teach them how we do things. They don’t have to unlearn anything about how they already work. We teach them how we work. For developers it might be different because it takes a lot of time to be a really good developer, and it’s relatively easy moving from one environment to another.” – Avishai Abrahami
72/ If you’re going to use an executive search firm to hire an exec, ask the firm three questions: “1/ Walk me through your hardest search? 2/ Walk me through a failed search? 3/ Why did it fail? 4/ How do you assess whether an exec is a good fit?” You should be interviewing the firm as much as the candidate. Watch out for “a firm with a history of candidates leaving in a short timeframe. Avoid firms that recycle the same execs.” – Yin Wu
73/ Before signing with any recruiting agency, ask “What happens if the person hired is a bad fit? (Many firms will restart the search to align incentives.) Is there a time limit for the search? (Some firms cap the search at 6 months. We’ve worked with firms without caps.)” – Yin Wu
Governance
74/ “The higher the frequency and quality of a young startup’s investor update, the more likely they are to succeed in the long run.” – Niko Bonatsos
75/ Five metrics you should include in your monthly investor updates:
Monthly revenue and burn, in a chart, for the whole year
Cash in the bank, at a specific date, and runway based on that
Quarterly performance for the past 8 quarters, in a chart
Target for the quarter AND year and how you are trending toward it
76/ Another reason to send great, consistent investor updates is that when prospective investors backchannel, you want to set your earlier investors up for success on how they pitch you.
77/ If you don’t have a board yet, still have an “investor meeting.” “Create investor meetings where you invite all your investors to do an in-person + Google Hangout’ed review every 60 days. They don’t have to come. But they can.” – Jason Lemkin
78/ “[The] most important measures of success for a CEO [are] internal satisfaction, investor relations and consumer support.” – Bob Iger
79/ “Entrepreneurs have control when things work; VCs have control when they don’t.” – Fred Wilson
80/ If an investor really wants their money back (usually when VCs have buyer’s remorse), there are times when they force you to sell or shut down your companies. Instead, ask them, “What would it take to get you off my cap table?” – Chris Neumann
Product
81/ “The ones that focus, statistically, win at a much higher rate than the ones that try to do two or three things at once.” – Bruce Dunlevie, cited in eBoys
82/ Once you launch, you’re going to be measured against how quickly you can ramp up to $1M ARR. One year is good. Nine months is great.
83/ The more layers of friction in the onboarding process (i.e. SSN, email address, phone number, survey questions), the better you know your user, but the higher the dropoff rate. For PayPal, for every step a user had to take to sign up, there was a dropoff rate of 30%. – Max Levchin in Founders at Work
84/ “Product-market fit can be thought of as progressively eliminating all Herbies until there are no more Herbies. Then, you’re in a mode where you can invest in growth because it’s frictionless.” – Mike Maples Jr. (In the book, The Goal, the trek is often delayed by a large kid called Herbie. As you can imagine, the group only moves as quickly as their weakest link.)
85/ “There’s a ruthlessness in the way Dylan finds sources, uses them and moves on.” – No Direction Home. Be ruthless about how knowledgeable you can be about your customers, about your problem space, and about your product. The knowledge compounds.
Competition
86/ “If you patent [software], you make it public. Even if you don’t know someone’s infringing, they will still be getting the benefit. Instead, we just chose to keep it a trade secret and not show it to anyone.” – Max Levchin in Founders at Work
87/ If you know you’re building in a hot space, and your competitors are being bought by private equity firms, share that with your (prospective) investors. The competitors’ innovation slows, and optimizing for profit and the balance sheet becomes a priority when PE firms come in. – David Sacks
88/ “As a startup, you always want to compete against someone who has ‘managed dissatisfaction at the heart of their business model.” – Marc Randolph
89/ “You cannot overtake 15 cars in sunny weather… but you can when it’s raining.” – Ayrton Senna. It’s easier to overtake your competitors in tough markets than great markets.
90/ “Having a real, large competitor is better than having none at all!” – Anna Khan
Brand/Marketing/GTM
91/ If you’re a consumer product, your goal should be to become next year’s hottest Halloween costume. Your goal shouldn’t be fit into a social trend, but to define one.
92/ Don’t be married to the name of your company. 40% of NFX‘s early stage investments change their names after they invest in the seed.
93/ The viral factor doesn’t take into account the time factor of virality. In other words, how long it takes for users to bring on non-users. Might be better instead to use an exponential formula. “Think of a basic exponential equation: X to the Y power. X is the branching factor, in each cycle how many new people do you spread to. Y is the number of cycles you can execute in a given time period. The path to success is typically the combination of a high branching factor combined with a fast cycle time.” – Adam Nash
94/ In a down market, you may not need as big of a marketing budget as you thought. Your competitors are likely not spending as much, if at all, to win the same keywords as before.
Legal
95/ “Nothing is more expensive than a cheap lawyer.” – Nolan Church
The hard questions
96/ “I’d love to kill it and I’d hate to kill it. You know that emotion is exactly the emotion you feel when it’s time to shut it down.” – Andy Rachleff, cited in eBoys
97/ “Inexperienced founders are usually too slow to fire bad people. Here’s a trick that may help. Have all the cofounders separately think of someone who should probably be fired, then compare notes. If they all thought of the same person…” – Paul Graham
98/ When you’re in crisis, find your OAR. Overcorrect, action, retreat. Overcorrect, do more than you think you need to. For instance, lay off more than you think you need to. Actions can’t only be with words. Words are cheap after all. And retreat, know when it’s time to take a step back. “Sometimes you just have to do your time in the barrel. When you’re in the barrel, you stay in the barrel. And then you slowly come out of it.” – Nairi Hourdajian
99/ “A half measure is usually something a management team lands on because it’s easy. If a decision is easy, it’s probably a half measure. If it’s hard, if it’s really damn hard… if it’s controversial, you’re probably doing enough of it. The other thing is a half measure often doesn’t have an end result or goal in mind. If you have a really specific goal, and implementing that goal is difficult, that’s probably doing your job. That’s probably what’s necessary.” – Tom Loverro
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Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
Before we dive into this blogpost, I’ve been asked by my legal friends to include the below disclaimer. I have a version of this at the bottom of every blogpost, but nevertheless, it doesn’t hurt to reiterate it again.
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
One of my favorite scenes as a kid was in Harry Potter and the Sorcerer’s Stone when Harry visits Diagon Alley for the first time. As the stone wall parted like the Red Sea, we saw a world unlike any we’ve seen before. With that, the audience along with Harry (Kudos for Director Chris Columbus‘ artistic direction) watched in wonder, excitement, and mystery. And Harry and I alike (Admittedly, I didn’t start reading the books till after the first movie) was hit with an overwhelming load of new information to absorb.
Raising your first fund is very much like that. While there are still some elements of familiarity, like investing in great people and winning great deals, you are taking other people’s money (OPM) for the first time. As such, it begs the questions: Who do you take money from? And how do you manage those relationships?
And like the stone wall in Diagon Alley, there’s more than meets the eye.
I have to thank Shiva for first bringing this topic to my attention, one that deserves a more nuanced breakdown than what is currently out there. And when Rebekah brought the below notion up for the Emerging LP Playbook, I knew I had to dedicate a blogpost to just this topic.
“GPs often have some flexibility on their minimum check size. I’m a pretty small check (particularly since I’ve been living on a founder salary!), but I can bring other things to the table to help the GPs I invest in (e.g. I highlighted Janine Sickmeyer from Overlooked Ventures in my Forbes column, I’m an advisor to Zecca Lehn from Responsibly Ventures, I send them deal flow from my AuthenTech community of founders). I’ve had luck with reaching out and saying ‘I really believe in what you’re doing. Please let me know if you get enough large checks and have room for some smaller LP investments.’ They’ll usually need to get enough big investments first since there are SEC limits on how many LPs they can have, and then they can let in some smaller, value-add LPs.”
The LP landscape is rapidly changing. What we knew in the last decade won’t get us to the next. The opacity in the LP world is getting undone by new, emerging LPs hungry to get involved and to learn. Folks, like Nichole at Wischoff Ventures have also shared publicly what her LP base looks like, with a level of transparency that’s foreign, yet refreshing for this industry.
Regulation has moved the needle, allowing for greater allocations to equity crowdfunding, as well as introducing more retail and high net-worth individual investors, to join the foray. Platforms, like AngelList, Republic, Twitter, Allocate, and Revere, just to name a few, are creating engines for better GP discoverability. There have been conversations on raising the ceiling on the number of accredited investors in a fund to 600. Which, if passed, will allow for smaller checks into funds, whereas the previous decades only allowed for family offices and institutions, as well as close friends. Anecdotally, I’ve also seen a lot of angel investors starting to allocate to funds rather than just purely startups.
And at this inflection point, as a GP, you need to be ready for this market shift that’s still early now, but starting to move. And hopefully, the below insights from 11 amazing GPs will serve as your wand, potions, owl and broom as you embark into the magical world of being a fund manager.
My methodology
To be fair, LP construction is more of an art than a science. So, I asked GPs who were on Funds I, II, or III. Why? Emerging GPs would best be able to relate a lot more to the hustle of finding and persuading different kinds of LP personas than someone who was on a Fund X or XV, who already have a long track record that speaks for itself.
I’m also a firm believer in tactical mentorship — mentors who are just 2-3 years ahead of you. People who have just been through the trenches you’re in and can share the lessons they learned. At the same time, not too far ahead where they are no longer the best people to check your blind side. After all, the lessons they picked up are still fresh in their mind. As a function, every one of these amazing GPs started their current fund in the past decade. The only caveat is that this may be the first recession they’re investing other people’s money (OPM) into, although they may have invested their own in the previous decade. And while that may be true, their lessons are timeless.
In the world of baseball, there’s the idea of breaking the catcher’s mitt. In other words, a new glove must be worn and used several times before it can achieve its full potential. Pitching to LPs and LP construction as a whole is no different. Just like a founder needs to pitch to several friends, colleagues, and investors, before they can hit their full stride during fundraising, raising from LPs requires many conversations and many iterations. Even Felicis’ brilliant Aydin Senkut got his first yes from an LP in Felicis after 107 iterations of his pitch.
So, in embarking on this topic and to get the best insight I could, it came down to two core pillars: the people I asked and the questions. I’ll start with the people.
Don’t get me wrong, there are a lot. And the folks included here are by no means all-inclusive. Many who had gone on to raise a Fund IV or higher. In effect, a few years or more out of the emerging manager game. Quite a few I didn’t know well enough. That’s on me. And some who, for all their goodwill and insight, unfortunately, were busy in the weeks prior to this blogpost coming out.
The questions
Building a firm with multiple funds is, in many ways, like driving a car through fog. Not my best analogy, but gets the point across. You see the rough outlines of the road just a few meters ahead, but you won’t see the sinkholes and the cracked concrete until you’re right in front of it, nor do you see any part of the road further than a few meters away. Or as Warren Buffett says, “The rearview mirror is always clearer than the windshield.”
Things are often painfully obvious in hindsight, but are scary, mysterious and unknown in foresight. Sometimes, you just don’t know what you don’t know. And as such, I write and I ask, in hopes to help the ones starting off, to develop foresight from the below cast’s hindsight. And to each, I had five overarching questions, coupled with follow-ups for more depth:
As you embark on your fundraise, note that different LPs resonate with different pitches. Additionally, when you choose out to reach out to each persona, be aware of what each of these LP personas’ incentives are. As a seasoned LP once told me:
High net-worth individuals seek to learn and rarely have a financial incentive.
Small and medium-sized family offices seek to learn and access top decile deal flow.
Larger LPs, like institutions and fund-of-funds, seek financial return.
From my conversations, it seems most GPs raising a Fund I start with individuals, then target larger check sizes as their fundraise matures. For Fund IIs, many seem to start with finding an anchor LP first, before reaching out to individuals and family offices.
The truth is there’s no silver bullet. And you’ll see exactly why below. So what might be more useful to you, an emerging GP, are anecdotes of what worked for different funds. As I call it, tools for your toolkit.
I will note that the one LP persona I won’t touch on as much since I have a lack of data here are corporates who usually seek technology, as well as information access, largely for acquisition opportunities.
Individuals
Start with people close to you.
“You should always target friendlies first. Welcome your references and first believers who might be founders, individuals, former coworkers, classmates.”
— Sarah Smith, Sarah Smith Fund
“It all depends on which Fund you are raising, how much you are raising, track record, team, and many more variables. If you are an emerging manager that is not spinning out of a brand named fund with a significant track record, you are going to have to be scrappy and start with people who know and trust you. “
— Steven Rosenblatt, Oceans Ventures
“You should always start off with your network – from the closest circle and outwards through the various concentric circles. At the beginning, you want to focus on finding your first believers. Those are your first-degree and maybe second-degree connections. So it’s less of the archetype of LP, but more so the depth of relevant relationship that matters. After the first close, that’s when you explore emerging manager programs or talk to more traditional asset managers — still largely within your first- and second-degree networks and/or those of your close early LPs and advisors.”
— Arjun Dev Arora, Format One
“The first $5 million is the hardest. Go to your friends and family. Build some momentum. After you get the initial momentum, it builds off of that. Everyone back channels everyone.”
— Vijen Patel, The 81 Collection
“For the beginning of a fundraise, I’d recommend asking for advice (before money) from people you’ve worked with for an extended amount of time. Your earliest checks may often be smaller but meaningful amounts from colleagues, co-investors, and GPs at other firms.”
— Paige Finn Doherty, Behind Genius Ventures
“The thing is my fund wasn’t oversubscribed from the beginning since I found it hard to raise. It’s a game of momentum, and in the beginning, I didn’t have any. In the beginning, it was about reaching out to the folks that you know. So, I mostly reached out to GPs and fund managers I knew and getting them through.”
— Shiva Singh Sangwan, 1947 Rise
“At the beginning, always start with people you have relationships with — people who’ve known you for a very long time. They not only want to invest in the fund, but invest in you. My first LPs would have likely invested in anything I created, but they knew I wanted to build a track record in venture. I’ve known one of my LPs since we were kids. Another was one of my best friends in university. Another was a friend of his.”
— “Mr. Huxley”, GP with two funds
Beware of relying too much on publicly available data to find LPs.
“The challenge with a purely data-driven approach (i.e. on LinkedIn or Pitchbook) is that you don’t understand the full rationale for why certain LPs invested in a fund. On paper, it may look like a family office is an LP in venture funds, but the principal at that family office could just be the brother- or sister-in-law of the GP. Most LPs also don’t explicitly say they’re LPs on LinkedIn. They could be an asset manager or a CEO of a Fortune 500 company. They almost always don’t want to be inundated with asks. Only after understanding why the industry is opaque, can you then understand LPs and find them.”
— Arjun Dev Arora, Format One
For potential MVP LPs, check size doesn’t matter.
“At the beginning of the fundraise, anyone that knows you and trusts you already AND can easily part with some money. Our first close was $20 million, and it was almost all people who knew us already – either directly or through our brand. We only had one new investor. In that group, we were lucky to have some fairly common names, which helped build the momentum for the rest of the fundraise.
“We did think about check sizes a little bit. There were some people we wanted to have involved for sure, and for them, the check size didn’t really matter. In our first close, we thought of people who could write a $250K check. And if there was someone we really wanted, we’d reduce it to $100K. I’m also an LP, and I do the same. If I plan to invest, I always negotiate down as well. The GP tells me X and I say I’ll invest X, divided by three.”
— Sheel Mohnot, Better Tomorrow Ventures
Persistence also speaks for itself.
“There are two types of investors: those who will commit to your fund now, and those who will invest after building trust. A lot of investors don’t like to invest in a Fund I. To keep them engaged, you either take a tiny check they’re comfortable with or you share regular LP updates that showcase your proof of work.
“In addition, you have to be clear with expectations. I bucketed potential LPs into four buckets:
High net-worth individuals
Founders and operators
Family offices
And GPs
“With each meeting, my pitch evolved and did a lot of follow ups. I had to show I was getting access to good deals and how I was getting access to those deals. You have to share the story behind that. That’s how you attract other investors. For instance, I remember sending my proof of work and an additional ten follow-ups to an LP. And each time I followed up, there has to be some new substance, value, and proof of work. It was a long process, but he ended up becoming one of my largest checks.
“Investors who were or are hustlers tended to gravitate towards my pitch. They became high-functioning people because of their hustle and respect me for my follow-ups and my persistence. They saw themselves in me. Similarly, founders are most likely going to get a reply from me who follow-up at least 2-3 times.
“The lesson here is that being persistent shows that you care. 99.9% of people won’t follow up, and by doing so, you’re already standing out.”
— Shiva Singh Sangwan, 1947 Rise
There are different ways to get in front of LPs: events, Twitter, deal flow, etc.
“Throw events for your LPs — a nice dinner or a cool experience — and ask them to invite their friends. Host events in a thoughtful way.
“Share relevant SPVs. Even broader, it’s content. Having founders be big fans of yours is also helpful. It’s a positive signal and creates buzz.
“That said, having co-investors who like you is a more direct path. LPs often ask VCs: Who are you co-investing with? Which emerging managers are you excited about? These LPs are looking for names. Some GPs are more generous with intros; while others prefer not to share but that’s OK as long as some do.”
— Arjun Dev Arora, Format One
“Looking back at my experience, a majority of our LPs from both Fund I and II actually came from Twitter and warm intros. I’m on Twitter a lot, mostly because I raised Fund I during the pandemic, so Twitter was where I hung out with many of my friends. I love to tell stories and as an extension I help founders tell their stories. And I host events and have done so since elementary school when I was on the student government event planning board. People are interested in my story because I don’t come from a traditional background. They invested mainly because they realize ‘she’s putting so much into the ecosystem, so it’ll eventually come back to pay dividends.'”
— Paige Finn Doherty, Behind Genius Ventures
Some individual LPs are not financially motivated.
“I want to preface that we only have foreign LPs, not US LPs. So, sophistication is very different. With European investors, while running a fund investing in the US, you can play the access game. In other words, you can sell access to great US companies. It’s something I lean on quite a bit.
“My LPs are quite sophisticated outside of the world of tech. They’re finance-savvy wealth managers, founders, high net worth individuals with net worths greater than $50 million, where they invest out of leisure and pursuing a mission, rather than for financial returns. They don’t understand venture, but want exposure to venture.”
— “Mr. Huxley”, GP with two funds
Start with HNW individuals, and end on family offices.
“Let’s make a few assumptions here. Let’s assume this is a Fund I and an emerging manager who doesn’t come from an extreme pedigree. Not from Sequoia or the like. This person is a decent operator-turned-VC, investing with a cool thesis. I’m going to also assume they’re not going to raise a $50 million Fund I or greater. They’re staying small and only raising $10-20 million.
“So I break down LPs into four categories.
High net-worth individuals – These are your angels.
Family offices – They have a lot more assets, usually $100 million or greater.
Fund of funds – They have a mandate to invest in other funds.
Endowments – These are very large institutions, maybe even sovereign wealth. They tend to write big checks into big funds.
“The big mistake I see many GPs make is that most GPs try to target the big ones out of the gate. Rather, in the beginning, focus on the high net-worth individuals. This is similar to asking angels. Their conviction and speed is quick. Their typical check size is no greater than $100K.
“Once you get a few million in the bank, then focus on the family offices — the $1-5 million checks. They tend to operate a lot like angels, but have just accumulated a lot more wealth. Around Fund II or III, then you target larger institutions.
“So, my recommendation is that as an emerging manager, start with angels, end with family offices.”
— Eric Bahn, Hustle Fund
“When you get closer to a final close, and you have a small fund, you can always welcome 1-2 family offices who can write small checks as well as individual investors who can be really helpful.”
— Shiva Singh Sangwan, 1947 Rise
Family offices
Find LPs by optimizing your search with certain keywords.
“Ask your existing LPs if they know anyone. Search LinkedIn to make their life easier. To find LPs, I would recommend looking up the keywords: Venture capital, asset manager, family office, emerging manager, startup (or venture) ecosystem, allocation, active allocator. All the above implies someone is putting money to work.”
— Arjun Dev Arora, Format One
Ask each person for just one intro, nothing more.
“Hustle Fund today has hundreds of LPs in our pipeline. But when we started off, we didn’t know a single family office. So, at the risk of sounding unintentionally mean, here’s how I think about it. Finding a family office is kind of like finding a cockroach. It’s always hard to find the first one. But once you find one, you’ll find a whole nest.
“I’ll share a tactical networking tip of how we found family offices over time. So, let’s say we chat with David. He likes us and decides to invest in the fund. We then share our fundraising blurb and deck and ask, ‘Do you mind sending this to one person you think would be a good fit for our fund?’
“The mistake I see a lot of other fund managers make is they ask, ‘Do you mind sharing this to anyone you think would be a good fit?’ Don’t ask for too much. There’s just too much paradoxical choice. There’s too many in their network to choose from and that overwhelms them.
“So, we change the question to just ask for one. That’s it. Generally, they think of the richest person they know. With just one intro, you’re magically in the family office world. A rich person tends to be friends with a lot of other rich people. It is secretive, but they also talk amongst each other a lot. When they invest, they like to bring their own friends in too.”
— Eric Bahn, Hustle Fund
Ask for intros to LPs who backed GPs who look like you.
“Another big filter is to find LPs who have backed GPs that look like you or have a similar investment strategy. For me, it was finding LPs who have backed solo GPs. To be fair, it’s not easy to figure out, since it is a rather opaque industry. So, I had other solo GPs I knew well and have co-invested with help make intros to their LPs.
“For LPs that I’ve never talked to before, a question I always ask LPs is: ‘Have you ever backed a solo GP?’ If not, don’t waste your time as you’re extremely unlikely to be their first. They likely have strong philosophical reasons to not back solo GPs so your meeting time is better spent elsewhere.”
— Sarah Smith, Sarah Smith Fund
Institutional LPs
Don’t underestimate the power of an anchor LP.
“If possible, having a respected entity who could anchor 5-10% of the fund would be ideal. In my case, my former partnership Bain Capital Ventures anchored my fund which was ideal because it keeps us connected and they are well known in the industry. Just like for a founder, having a lead is important. Having an anchor early helps you build momentum to close the rest of the fund.”
— Sarah Smith, Sarah Smith Fund
“For Fund II, I wanted an anchor LP to provide stability and credibility in the fundraise. Cendana was my number one pick. As a function of fund size at the seed stage, they’re definitely the best. The Harvard of LPs. To become part of their community, for me, was really important.
“It was a hard process, but was doubly as difficult, since Josh and I went our separate ways for Fund II. We had to communicate that decision to our 120 LPs in Fund I before starting the fundraise.
“In Fund I, some LPs believed in me. Some believed in Josh separately. I remember fondly of our first $10K check of belief capital. BGV’s most expensive decisions were our investment decisions. We made all our decisions together in Fund I. We also tried doing a few SPVs via Assure. While it was a great start to our career in VC, it required more work than we thought made sense. But for Fund II, it was going to be different. It was just me. No more SPVs, just checks out of the fund. The story itself wasn’t hard to communicate, but when we got to our 70th call, it was hard to sell the same emotional story.
“So, once we did, I put in the work. I flew to Australia to get introductions and to meet his teammate. Whenever I chatted with other GPs that were backed by Michael [Kim], I’d ask them to say hi to him.
“Pitching to Cendana, and most importantly, Michael, was the longest sales process I’ve ever gone through. He passed on Fund I, but he finally said yes to BGV’s Fund II. Along with Michael, GREE also doubled down on Fund II, along with operator checks from folks at Dropbox and other companies.”
— Paige Finn Doherty, Behind Genius Ventures
Bigger LPs have the ability to write smaller get-to-know-you checks.
“At the end of Fund I, we ended up with Cendana, Greenspring, Industry, Vintage, and Invesco. All fund-of-funds, but they all wrote relatively smaller checks than they typically do. For all the afore-mentioned funds, they wrote $1-3 million checks. It was a get-to-know-you check. They would talk to other companies in our portfolio and other managers we co-invested with. And so the best way to get in front of them was to get intros from other managers these fund-of-funds invested in.”
— Sheel Mohnot, Better Tomorrow Ventures
Talk to LPs whose minimum check size is 20% or less of your fund.
“Some CIOs like being in Fund I’s; others don’t. There’s a lot of alpha in Fund I. At the same time, there are others that won’t consider you seriously until Fund III. The challenge is figuring that out as quickly as possible.
“The best filter for this is figuring out what their minimum check size is. And, is that greater than 20% of your fund size? If so, it won’t be a good fit.”
— Sarah Smith, Sarah Smith Fund
“Biggest thing is their own AUM and the amount they need to deploy. First barrier to entry is the size of the fund you are raising as the GP. If you are raising sub-$75M (give or take) it wouldn’t be big enough for their minimum check size. LPs don’t want to be even close to a majority of your fund, or likely more than 20%.”
— Nichole Wischoff, Wischoff Ventures
“Some institutional LPs also cannot write small checks since they are dealing with other variables around their asset allocation models.”
— Steven Rosenblatt, Oceans Ventures
Start conversations early with LPs who can invest in the ideal fund size you want to raise.
“It’s not just about what your fund size is today, but where you aspire to be. Say you have a $25 million fund today, but aspire to have a $150 million fund where you lead Series As by Fund III or IV, then you should still talk to LPs who are able to write checks that are 20% or less of that future fund. It’s important to know there may be incredible university endowments or foundations who really like you as a GP but in order to run their business efficiently, they have to be able to write minimum checks of $25M or even $50M+ which means they only seriously consider funds of $150M+.
“The question for you, the fund manager, is: Are you going to grow your fund size over time? Or are you going to stay consistent with your current fund size? If the former, then you need to spend a fair bit of time in your deck about how your strategy will shift over time and some views into those larger future funds.”
— Sarah Smith, Sarah Smith Fund
“I started having conversations with institutions while I was raising Fund II knowing they wouldn’t come in until Fund III at the earliest. You need a lot of touchpoints and time with these types of LPs before they invest. I am very focused on LPs that want to underwrite me/the fund for years. I want long lasting relationships and partners that can come in fund over fund.”
— Nichole Wischoff, Wischoff Ventures
“So, when I speak to institutions that are more data-driven — they think about the scalability of AUM — I knew many of those folks were not going to be the best fit. That’s why raising Fund I was so hard.”
— Paige Finn Doherty, Behind Genius Ventures
“We have been cultivating relationships with a large amount of institutional LP’s over the last few years. Investors invest based on trust and relationship and in our mind that doesn’t happen overnight.”
— Steven Rosenblatt, Oceans Ventures
LPs hate surprises.
“There are some institutional LPs who will give you transparent feedback and transparency about their process but most do not. The #1 thing that rules them all is track record and performance. Institutional LPs don’t want surprises; they want to see a multi-year established track record in what you are investing in.”
— Steven Rosenblatt, Oceans Ventures
And even if they disagree with you, LPs like consistent LP updates, even prior to their investment.
“We have a couple institutions that have invested in Hustle Fund. What I didn’t appreciate out of the gate is how long it took to build those relationships. They want to see at least one fund cycle, ideally two. That’s usually anywhere between two and four years. But we’ve nailed how we do it passively.
“We have a newsletter that goes out on the first day of each month at midnight — every month for the past 5.5 years. Each issue has two things: a state of the market and a deal memo on each deal we’ve invested in.
“Today we have 150 investors across three funds and an additional 450 investors who have not invested yet. Think of it like a monthly drip campaign for these prospective investors. Investors get to see what we execute against what we say we’re going to do.
“In some cases, these investors like what they see and choose to eventually invest. In other cases, they find themselves totally disagreeing with how we run our process so they don’t invest, and that’s okay, too. Drip campaigns are always a great marketing tool to close customers. That’s no less true for Hustle Fund. So, at some point, when we mention we’re going to raise a Fund IV, all the meetings will just line up.
“I’ll share a story. Our biggest LP, Foundry Group — Jaclyn and Lindel run their LP initiatives — initially didn’t like our thesis and approach. To them, our investment model was a little too spray and pray. But at the end of our Fund II, they told me, ‘Even if we’re a little uncomfortable with your thesis, you’ve been so consistent with sharing how you’re learning and developing, and we love it. So, we want to invest now.’ They invested because of our newsletter, and witnessing our exact fund thesis. You gotta put in the work. And if you do, the money will follow.”
— Eric Bahn, Hustle Fund
Give LPs a compelling reason not to back an established fund. Otherwise, they will.
“Every institution is different, but it’s also really important to realize that with most institutions, the decision maker is not making the decision based on their own capital. So, risk is a huge point. No one is going to get fired for backing Sequoia. They could potentially get fired for putting a huge check into a new emerging manager that isn’t proving anything and going backwards. It’s important to understand the incentives of who you’ll be working with. So institutions are a completely different beast than individuals. Anything they do there’s usually 5 to 10 back references. It’s a small world. For pushback, they want to see a track record, which is really hard for emerging managers. And they want to see some sort of pedigree.”
— Vijen Patel, The 81 Collection
“I’m the horrible anomaly of being able to raise from institutional LPs in my first fund. I’ll chalk up timing, privilege, and reputation as being the reason we were successful in doing so. While not all of this is relevant to emerging managers today, 100 Days of Fundraising was a blog post which detailed how Homebrew ran its process.”
— Hunter Walk, Homebrew
Author’s Note: Of particular note, in Hunter’s alluded blogpost, is when he writes:
“What we also had was a point of view as to where we’d be investing: the Bottom Up Economy. This set us apart from other funds with broader or non-descriptive investment principles. We also had given extensive thought to our portfolio construction strategy around playing lead roles in rounds, the number of deals we would do each year, how much capital we’d hold back for follow-on, etc. The combination of these two meant that a fund could see how we’d be differentiated in the marketplace and where we’d fit against their current exposure.”
Should your LPs be active?
The truth is, and you’ll read this below, most LPs are passive. But in a world where you take so many different types of risk as an emerging GP, it helps to have people you can lean on. So, it really comes down to two questions:
What can you ask of your LPs?
What is the upside and downside to having active LPs?
The bull case for active LPs
HNW individuals are just waiting for the ask.
“The LPs I love working with are the ones who are going to be actively involved. They share their expertise with the portfolio, answer our questions, and are willing to jump on random calls with me. A lot of our LPs are high net-worth individuals, and they’re just waiting for the ask. They’re waiting for the GPs who they invested in, to engage with them. Sometimes, all it takes is a 20-minute call to share deals or thoughts or questions.”
— Paige Finn Doherty, Behind Genius Ventures
Your LPs will make LP intros if you have a good story.
“I think you can do a good job of getting LPs to send intros. If you can build trust and tell a good story, your LPs will naturally tell others because it comes up at a cocktail party organically. A VC fund is more interesting than ‘Hey I invested in a new ETF.'”
— Vijen Patel, The 81 Collection
Incentivize your LPs with additional carry.
“With Fund II, my Fund I LPs opened the door to other LPs in their network. Additionally, I am quite generous with my 20% carry for running the fund. I share 5% of the carry pool with other founders and LPs who send me deals, help with diligence and introduce me to other LPs.”
— “Mr. Huxley”, GP with two funds
Leverage your LPs’ brand to win deals.
“In my case, I had smart and well-connected LPs, and I was able to win deals because of them by inviting them into deals I wanted to get into. Some of my LPs happened to be fund managers as well, and I have been able to learn a lot from them.”
— Shiva Singh Sangwan, 1947 Rise
Build communities alongside LPs.
“I do believe there is room for LPs to provide value on top of what we expect today – better ways to tap their networks on behalf of our portfolio companies for example. At Screendoor for example, a fund of funds that backs underrepresented emerging managers, we strive to create a community among these VCs to support each other, and also pair them with VCs (like me) who can be coaches along the way when they have questions about firm building.”
— Hunter Walk, Homebrew
If you’re doing something for the first time, ask institutional LPs how other managers they’ve backed have done so.
“Since their investment offices have decades of experience in the venture sector and exposure to top managers across all stages, we often turn to them to gut check our reality against their perspective of the market. And when we encounter a type of situation for the first time, understand how other managers have approached the solution.”
— Hunter Walk, Homebrew
Author’s Note: Paige’s anecdote on how she engages her LPAC below is a great +1 to this point.
Let your LPs choose the kind of LP they want to be.
“I have no preference here. Rather, I’m open to what my LPs want their experience to be like. I have LPs that want to be more passive, as well as operator LPs who want to learn more about investing, lend expertise during diligence, facilitate customer intros, and even help out portfolio companies with hiring.
“After my LPs wire their money, I send them an intake form where I ask the question: How would you describe yourself as an LP? I have a number of statements they can select to indicate whether they are a newer or more experienced LP, if they’d like to be more active with founders, how often they’d like to communicate with me, and if they are interested in co-investment opportunities and events. I have another question following that: If you want to be more active, what are ways you enjoy helping?”
— Sarah Smith, Sarah Smith Fund
“I leave it completely up to them, but they typically opt to be more active. I host monthly one-hour office hours, share quarterly updates and deal reviews. For office hours, while we mostly chat about interesting deals I’ve been seeing in the last 30 days, my LPs can ask me anything. I try to be as communicative as possible – valuations, deal memos, and diligence. Sometimes they ask me to set up an additional SPV if they’re interested in putting additional capital in. I have a separate Airtable for deals we’re diligencing at the moment which LPs have access to. If they’re interested in a deal, they can reach out and ask. If not, they don’t have to.”
— “Mr. Huxley”, GP with two funds
The bear case for active LPs
Having engaged LPs is a lot of work.
“Candidly, I don’t want LPs that want to be super engaged outside of maybe one or two. It’s enough work as it is with quarterly reporting, etc. I want LPs focused on returns. Cendana is the most active with me and in great ways because they have so many emerging managers. I can strategize on fund size, raise timing, first hires, etc.”
— Nichole Wischoff, Wischoff Ventures
Emerging LPs want to learn from you, but remember you’re an investor, not a professor.
“Emerging LPs want that education. For emerging LPs who write a $5 million check or greater, they might like for you to jump on a call every quarter to educate them and share your current portfolio and what else you are seeing out in the field.
“Also, be thoughtful about how you’re managing your time, so that you don’t turn into a full-time venture professor. You’re an investor, a GP. That’s what you’re getting paid to do.”
— Arjun Dev Arora, Format One
Then again, most LPs are just passive.
“Most LPs are pretty passive. Sometimes they are helpful by making intros to our portfolio companies. We also like getting a pulse on the market from them.”
— Sheel Mohnot, Better Tomorrow Ventures
“Mostly passive. Most of the time, when the deals are good, they require little involvement.”
— Shiva Singh Sangwan, 1947 Rise
GP-LP fit: Red flags and things to watch out for
Avoid LPs who ask for special terms.
“These are long-term marriages, really long term. If you are going to be partners for the next 10-20 years, you better like each other. We have a no-asshole rule. We want investors who believe in our approach and ethos. My mentors at some of the top VC funds of the last 20 years have also coached us to keep the terms clean and I think a lot of emerging managers feel pressure to give special terms and ownership of their management company or GP, and long term, that might be something you regret.”
— Steven Rosenblatt, Oceans Ventures
“While I haven’t said no yet, I have selectively not followed up. For example, after talking with other GPs, I’ve heard some LPs were tricky to manage – outside the norm. It’s okay to expect quarterly communications, but when people start pushing an agenda, that’s too much.
“Avoid LPs who ask you to give up economics as a GP or change your terms. LPs who want to negotiate lower management fees, a different carry structure, or they want to own 20% of the general partnership for the next three funds are best avoided if possible. They want to change the terms that everyone else has. I wouldn’t allow that. If other LPs find out (and they eventually do), it would cause my LPs to lose trust in me and rightfully be frustrated that they got worse terms.”
— Sarah Smith, Sarah Smith Fund
Do your LPs’ goals align with your fund goals?
“As we got into the process we realized there was, at the time (2013) some other attributes we needed to take into consideration. One for example was the LP’s definition of success.
“We wanted LPs who were investing in us solely because they thought we’d be good stewards of their capital and return above-benchmark results. If there was a second agenda that they made obvious we typically declined the opportunity to work together. Our mindset was that there’s so much risk in trying to build a new firm, let’s focus all of our energy on a single definition of success: cash on cash returns. That precluded taking capital from LPs who were emphasizing direct co-investment (some of our LPs have direct practices and we love to bring them in to portfolio company cap tables when there’s mutual interest but we didn’t want it to be an expectation) or strategic investors who had interests in our portfolio different than our own (e.g. corporates that wanted access to market information).”
— Hunter Walk, Homebrew
Do you have the bandwidth to teach?
“If someone wants to learn, that can take a lot of time. Time that, for you, might be better spent elsewhere. If you’d rather spend the time elsewhere, like with your portfolio or investing, be clear with expectations. And if they don’t budge, don’t take that money.”
— Arjun Dev Arora, Format One
Beware of round tripping.
“I actually couldn’t take any Indian capital due to regulations. There’s a thing called ’round tripping.’ If a fund in India invests in a fund that’s built in the US, then invests back into Indian startups, that’s round tripping. And unfortunately, not allowed.”
— Shiva Singh Sangwan, 1947 Rise
Check your CFIUS rules.
“Before you say yes to LPs, check the CFIUS rules. Under those guidelines, you may not be able to take money from certain countries and parties.”
— Arjun Dev Arora, Format One
Did you take the right capital from the right people?
“Even though we heard ‘no’ a lot during our first fundraise we also turned down some offers. We’d already done a good job of pre-screening out LPs who we didn’t think were values aligned with Homebrew (e.g. money came from sources/institutions we wouldn’t want to work on behalf of).”
— Hunter Walk, Homebrew
“If they’re asking for things that you’re not comfortable with, then you probably shouldn’t work with them. The key is that there should be zero second-guessing. You need to be in a relationship with partners you won’t regret, during bull and bear markets. Ask yourself, ‘Did I take the right capital from the right people? Sometimes, it’s about where that capital came from and if you feel good about that. If there’s any inkling of doubt, don’t take the money or it’ll come back to haunt you.”
— Steven Rosenblatt, Oceans Ventures
“You need to communicate your clear values as a fund and long-term platform. Any LPs not aligned on your mission and values would be people to say no to quickly.”
— Arjun Dev Arora, Format One
“So, I did say no. I turned down a million dollar check because I didn’t feel comfortable with him being in front of a founder. And we’re very geared on our community. Money’s nice, but it’s not everything.”
— Vijen Patel, The 81 Collection
“Another thing to be mindful of is if an LP has a history of making verbal commitments and then changing that number at closing. You want a reliable and trusted relationship. If you did a reference with another GP, and heard that an LP cut their commitment by 50% at the last minute, that capital’s just not worth the risk to me.”
— Sarah Smith, Sarah Smith Fund
Don’t tolerate disrespect.
“I said no to a few LPs in Fund II. This was largely because they were super disrespectful during the raise process. I had an LP fly in from the UK after already committing and was so insanely rude to me in front of his all-male team that I decided not to work with them. I also try to be very transparent for folks that might not be a great fit for the fund.”
— Nichole Wischoff, Wischoff Ventures
“Small things I look for include off-color jokes, like ‘Look at that hot chick,’ or asking stupid questions. Some LPs have said this to Elizabeth, ‘How do you balance being a mom and being a full-time investor?’ I dare people to ask me that question. I’m a dad and I’m still doing it, but no one does.”
— Eric Bahn, Hustle Fund
Author’s Note: Eric goes into much more detail on ten reasons why you shouldn’t take LP money here, which I highly recommend a read.
Are your LPs disengaged during the diligence process?
“There are people who are disengaged in the diligence process. Those are people who are usually a bad fit.”
— Paige Finn Doherty, Behind Genius Ventures
Look for complimentary experience and diversity of opinion and experiences.
“Like any cap table or LP base, what is important to us is to have partners who can grow with us for a long period of time and where we have diversity of thought, experience, and exceptions. It was really important to Oceans and our ethos to have amazing founders and tech execs as LPs early on who could be great to lean on for diligence and additional leverage to support our founders and entrepreneurial family offices. At the same time we have LPs who are extremely valuable on the finance side and who have a long history of investing in venture. Complimentary experience and diversity of capital is really important to us.”
— Steven Rosenblatt, Oceans Ventures
“I also want to put it out there that GPs should be intentional about their LPs. For me, I aim to have my LP base include at least 50% who identify as women or non-binary, 10% black or Latinx, and 10% LGBTQ. Be intentional and solicit a diverse group of people. People talk about the diversity of founders and venture investors, but not about LPs. I think a lot about wealth creation, and it starts from the very top. I think people should be thinking about that a lot more.”
— Sarah Smith, Sarah Smith Fund
Don’t discount vibe.
“For Fund I, we had a chance to close $30 million worth of LP capital, but we only chose to raise $11 million. That’s a lot of people we said no to.
“It comes down to say a single word: vibe. It’s kind of like a marriage. ‘You’re trusting me with your wealth for a decade, if not more. It’s not a relationship we take lightly.’ I also share all the reasons why it won’t work out. So our LPs know what they’re getting themselves into.
“If something feels off, I don’t have to explain it. No one on our team has to explain it. If your gut feels like this could be off, we should just always trust that. Those one or two LPs your gut tells you is off are likely going to be super annoying,
“People like to logos their way out of things, but you really have to go back to gut feel. It’s almost never worth it. I can’t explain what an asshole feels like. But when you meet one, you know it.”
— Eric Bahn, Hustle Fund
“If I have a gut feeling that something is weird, then I trust that.”
— Paige Finn Doherty, Behind Genius Ventures
Big checks prevent you from bringing in other LPs you want.
“We haven’t had to say no to that many LPs. In our case, we either told them, ‘It’s too late – we’re full now and don’t have room for you.’ Or we talked LPs down from how much they wanted to commit. We had an LP who initially committed $22 million. And we told them, ‘Hey, we want to add more investors to our fund, so we don’t want to have any investors who commit more than $15 million.’”
— Sheel Mohnot, Better Tomorrow Ventures
Sometimes, the check size is just too small.
“I’ve said no because people wanted to invest below the minimum. To which, I told them to wait until they could meet the minimum. I’m not in the business of putting people in financial distress. And if my minimum, which is modest by design, $100K, called over two years, puts people in a position where they are stressed out, they shouldn’t invest in me or perhaps venture as a whole.”
— Sarah Smith, Sarah Smith Fund
“As the fund grew, I would turn down certain individuals due to check size.”
— Paige Finn Doherty, Behind Genius Ventures
But check size can vary based on an LP’s value to you or the portfolio.
“I also only reached out to people I wanted to have on board. The minimum check size did vary from individual to individual, which I largely based it off of the value they could provide for the fund and my portfolio companies.”
— Shiva Singh Sangwan, 1947 Rise
Or don’t settle and aim high.
“I hate the word ‘oversubscribed.’ It’s something I was lucky to learn very early on. Early in my career I had a board member say to me that if you hit your goals every quarter, your goals aren’t high enough.”
— Steven Rosenblatt, Oceans Ventures
Author’s Note: As you might realize even more after the last three pieces of advice, there’s really no right answer.
How do GPs think about building an LPAC?
Your anchor and other major LPs will ask you to create one.
“On the LPAC, I think I can confidently say that no fund manager wants an LPAC and proactively creates one. It is usually the ask of an anchor LP as you scale fund size. For example, for my second fund, I was asked by an LP to create one, and I was told a good number of LPAC members is three. You want the anchor LP in the LPAC because they are your biggest investor, and the two others should be trusted partners who want to help you. It’s up to me who I ask assuming not many have asked to be a part of it.
“I’ve been told most managers will have a bi-annual quick check-in call just to talk about how things are going. TBD if I ever do this. On the other hand, a lot of managers try to wait until they have at least $100M in AUM to give into an LPAC. But I didn’t say no.”
— Nichole Wischoff, Wischoff Ventures
“I think it’s, in large part, who wants to be on it. A lot of your larger LPs, in exchange for 10% of your fund, want to be on your LPAC. There are some investors who committed 10% but don’t want to be on it. It’s not like a board. If people want to be on it, it’s okay.
“We have five on our LPAC, and it’s a good number. We give them an early look by sharing with them our plan and fund deck. So, they gave us early feedback, like on carry structure.”
— Sheel Mohnot, Better Tomorrow Ventures
If a smaller LP wants to be on the LPAC, push back by giving them options that fit what you’re looking for.
“There are no real rules about how you approach them. We typically like to have our largest investors in it, at least symbolically. They’re putting in the most risk, so they should have a say in the direction of the firm.
“If someone does ask for it, and if they aren’t a large enough check, we tell them, ‘We like to reserve this spot for our largest LPs because they have the largest exposure in our fund. We’re open to you being a member in our LPAC, if you increase your check size.” That way, you can leave the ball in their court. Either, they won’t push further or they’ll commit more capital to the fund.”
— Eric Bahn, Hustle Fund
Evaluate a potential LPAC member on five different dimensions.
“So I will preface that emerging funds — Funds I to III or IV — are different from established funds, which have a mostly institutional base. Those who tend to write large checks may also be more inclined to want a seat on the LPAC.
“We look at it from these different dimensions, which we categorize into:
Flexibility,
Complementary skills,
Ability to give honest feedback
Value, and
Capital
“So, flexibility is important because we’re not an institutional fund yet. The construction of the committee depends on the ebbs and flows of fundraising. Some investors don’t want to be on an LPAC — conflicting interests, not wanting to be actively involved, or just don’t want the time commitment. This’ll admittedly look very different for an institutional LPAC down the road for someone who has several hundred million in AUM. Institutional LPs will ask to have a seat on the LPAC, especially if they’re writing a check that accounts for 20% or more of the fund.”
— Steven Rosenblatt, Oceans Ventures
Go to them if you plan to go off-thesis.
“You go to them for things you might think are a conflict. For example, if I say I write $1M checks and I am considering going off-thesis and writing a $250K check, I might want to gut check and get a thumbs up that I’m not being an idiot. It would be a super simple email saying: ‘Hey team, here’s the scoop – please share thoughts.’ It’s very loose.”
— Nichole Wischoff, Wischoff Ventures
Ask your LPAC what they’re seeing in other managers they’ve backed.
“I didn’t expect to negotiate my LPA with Cendana. I have Michael [Kim] and Yougrok [from GREE Capital] on my LPAC. Youngrok is someone I meet with very often. And since GREE backed us since Fund I, he’s seen my growth as a fund manager. Our LPAC offers a great and critical lens into the industry.
Individually, I chat with both quite often. Together, as an LPAC, we meet quarterly. We’re also going to have our first general annual meeting on April 21st.
What’s great about Michael and Youngrok is that I’m not afraid to ask questions I think are dumb. If you’re in your Fund I or II, like I am, you’re still figuring shit out. You’re still testing what works and resonates and what doesn’t. I ask them, ‘what have you seen other managers do in this situation?’ They’ve worked with so many other managers, and in learning from their deep knowledge, I’m better off as a manager. It’s about building BGV as a long-term institution.”
— Paige Finn Doherty, Behind Genius Ventures
Your LPAC is your LP base’s chief influencer.
“One useful note about having an LPAC is that sometimes you want to make a minor change to the LPA. Say you originally planned to only invest in North American companies, but now you want to invest 5% of the fund in African startups. If you don’t have an LPAC, you have to go back to all your LPs each time you change the parameters of the agreement. If you have an LPAC, they can approve those minor changes for you on behalf of the rest of the LPs.”
— Sarah Smith, Sarah Smith Fund
“To be honest, I’m still confused about the purpose and concept of an LPAC. I like to think of the LPAC as the influencer of the LP base. They keep the investors’ interests in mind and help you communicate hard decisions to your investors.”
— Eric Bahn, Hustle Fund
Consult your LPAC for tough decisions.
“It definitely matters more at the end of the fund life. For instance, if we want to wait an additional year for Stripe to IPO. Then we consult with our LPAC to figure out the best way to message that to our LPs. Additionally, we can ask them what they think about a deal we’re about to do. It can also be useful in corporal situations. Hypothetically, if Elizabeth was beating me up, I can ask our LPAC to help me remove her.”
— Eric Bahn, Hustle Fund
“Since we’ve got a very small group of LPs that make up 95%+ of our funds, there isn’t much difference between our relationship with our LPAC and the other LPs. That said, we do have an LPAC and it’s composed of the largest investors in our funds. We meet with them once a year – typically a lunch before our annual meeting. And share the materials/discussion with the rest of the institutional LPs as well, so it’s less about anything confidential and more about a group of stakeholders we can get feedback from. Of course there are sometimes administrative aspects (approve us raising our recycling limits for a fund) but more often than not Satya and I are seeking feedback on questions we’re facing about how we want to manage the firm, tradeoffs between short and long-term thinking, and such.”
— Hunter Walk, Homebrew
“For us, when we constructed our LPAC, the questions we asked ourselves were:
Who do we think would be valuable in helping us balance short term decisions with long term thinking?
Who do we think will give us honest feedback and engage in honest conversations?
And who do we know has complementary DNA?”
— Steven Rosenblatt, Oceans Ventures
Find LPAC members who come from diverse experiences.
“I use it as a mini-board. I won’t go to it for big decisions, but I like the idea of surrounding myself with people who have different experiences than me, who have dissent, and make me a better investor.”
— Vijen Patel, The 81 Collection
Build an LPAC of different LP personas.
“If you have a great LPAC, they’re almost like a board of directors. You have some kind of cadence to get advice. If I did have one, I would like to do it with a group that represents my LP base – a few family offices, individuals, and people who could give really good advice.
“For first-time funds, you don’t want it to be any more than three to four people. And four to six for more established funds.”
— Sarah Smith, Sarah Smith Fund
“My advice to other VCs in building their LPAC would be to remember it’s about institutions, not individuals – your LPs representative might change over the course of the years. And, if applicable, to make sure you have a mix of LP types – for example, if your fund LPs are a mix of evergreen investment offices (such as most endowments) and folks who think of returns on a different cycle (fund of funds), include both.”
— Hunter Walk, Homebrew
The tech stack of engaging LPs
While I didn’t ask everyone this question, thought I’d share what notes I did have on some firms’ tech stack for engaging their LPs and managing their investor relations.
Wischoff Ventures — Airtable, Figma
“A spreadsheet/Airtable — I have everyone’s emails and copy-paste when I’m ready to send a quarterly update. I only talk to most once per quarter and it’s for my update. I built that in Figma (wouldn’t recommend it).”
Oceans Ventures — Affinity
“We use Affinity to manage our LP CRM. Our existing LPs get quarterly reports. And we try to write an LP update at least two times a year but will also often put out memos especially during key market moments. Also, since day one, we have a newsletter that keeps people up to date. It goes out every two to three weeks. And we have a personality. We’ve had other VCs tell us how excited they are to read it and we have LPs tell us they love our newsletter. We try to over-communicate and keep them heavily engaged.”
The 81 Collection — Streak, Airtable, Hubspot, Excel/Google Sheets
“We use Airtable, Hubspot, Excel and Google spreadsheets, but Streak is our main thing.”
“We’re pretty software-heavy — something I picked up from my time at WorkOS. We use:
Cloze — as our CRM, where we track what cities folks are in in, who’s in the pipeline and more
Airtable — for portfolio management
Google Drive
Webflow — for our website
Zapier — but there’s only so much you can automate
1Password — we’re pretty big on security
Calendly — but we’ve gone back and forth on that. I’m trying to spend more time with people who’ve invested in our fund, as well as the founders we invested in.
Twitter
Descript — for podcast transcriptions
Riverside — to record podcast episodes”
1947 Rise — Email, AngelList
“Regular LP updates, as well as my newsletter, have been my biggest engagement tool with LPs. I send the former out once a quarter, and the latter every few weeks. Luckily, I can also see all my LPs on my AngelList dashboard.”
“We used Carta, Affinity, Mailchimp, Aumni for analytics, and Anduin to bring LPs in. Fundraising is a bunch of chasing people down. Anduin’s a workflow tool. You can send people stuff and have people sign them all in one tool. Actually, several LPs told us that Anduin was the smoothest onboarding experience they’d ever had.”
“Mr. Huxley’s” Firm — Airtable, Notion, Whatsapp, Quickbooks, Google Drive
In closing
As I was writing this blogpost, a big part of me wanted a nice, easy linear narrative around LP construction. But I knew there wasn’t. In the many conversations that led to the above writing, it became quite evident there was no undisputed best way — no cure-all — to build an LP base.
Some believed in aiming high and never becoming oversubscribed. Others generated demand for their subsequent fund or was able to be judicious with their LPs by being oversubscribed.
Some built momentum by securing an anchor LP. Others started from individuals they knew the best.
Some didn’t budge on minimum check size. Others were flexible.
The list goes on and on. While there is no right answer, in knowing all of the above possibilities and strategies, I, and everyone who helped me make this blogpost a reality, hope you are armed with the knowledge to make the most informed decision for your fund. And to that, cheers!
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
It’s not often I get to work with someone I deeply respect on the content front. In fact, in the history of this blog, I’ve never done so before. But there are a rarified few in the world that if I was ever given the chance to work with them, I’d do so in a heartbeat. Tom White is one of them. As someone who I had the chance to work briefly with when our time at On Deck overlapped, he is someone I’ve been continually enamored with — both in how he commands the English language and in how intentional and thoughtful he is as an investor.
So when Tom reached out to collaborate on a blogpost for the Stonks blog, it was a no-brainer. And, the below is that product on how founders can own their fundraising process.
David’s note: Tom never ceases to amaze me on his ability to meme anything.
It’s a tale as old as time.
After a good meeting and a great pitch, the VC across the table (or on your screen in this day and age) offers a forced smile and utters: “Thanks again for making the time. Let me circle back internally and we’ll get back to you if we’re interested.”
If you have ever fundraised as a founder — hell, if you’ve ever fundraised, period — you have heard those fatal few words many more times than you care to remember. Though frequently said, the pangs of disappointment and frustration that they impart seldom fade away.
Fear not fellow founders!
To ensure you never hear those dreaded words again, we turned to the one and only David Zhou. A “tenaciously and idiosyncratically curious” writer and investor per LinkedIn, David pens the inimitable, brilliantly-named Cup of Zhou, scouts for a number of VCs, and helps run the On Deck Angel Fellowship.
Your ability to raise capital is directly proportional to your ability to inspire confidence in potential investors.
I’ll get into that, however, first a brief aside.
One of my favorite lines in literature comes from the seventh book of the Harry Potter franchise: Harry Potter and the Deathly Hallows. Inscribed on the golden snitch is a simple, but profound phrase: “I open at the close.”
In many ways, that line alone echoes much of the world of entrepreneurship. Whether backcasting from the future as Mike Maples Jr. puts it (i.e. great founders are simply visitors from the future) or breaking down your TAM to your SAM then SOM, the greatest founders — no, storytellers — start from the end. They share the future that they wish to see and distort today’s reality to fit into that predestined mold. Without further ado, my five tips on willing the future you want to see via successful fundraising.
1. Measure Founder-Investor Fit
Before you dive into talking with every investor under the sun, you must first understand there are more investors out there than you possibly have time for. You will never pitch every single one, nor should you. You need to be judicious with your time.
As you raise your first institutional round, you’re seeking out early believers. Julian Weisser — an investor with whom I’m lucky enough to work — calls this belief capital. You’re selling a promise, a vision.
And let’s be honest, at pre-seed there is no amount of traction that will convince any investor with numbers alone.
You see, it’s all about narrative building.
More on that below, but for early investors, it’s about whether they not only believe, but are also willing to fight for the future you collectively desire.
2. Close the First Meeting
I recommend that many founders with whom I work ask a two-part question heavily inspired by my conversation with Hustle Fund’s Eric Bahn for my emerging LP playbook: “Critical feedback is important to me in my journey to grow as a founder and a leader. So I hope you don’t mind if I ask, given what you know about my startup and myself: On a scale of one to ten, how fundable am I?”
To be honest, the number they give is inconsequential. That said, if they give you a ten, get a term sheet on the spot.
The more important question is the following one: “Whether I didn’t share it yet or don’t have it, what would get me to a ten? What would make this startup a no-brainer investment?”
Collect that feedback.
Put it in your FAQs.
Incorporate it into your next pitch.
Test and iterate.
I was listening to Felicis Ventures’ Aydin Senkut on Venture Unlocked recently and he mentioned that he iterated on his fund pitch deck every single time he got a no. And by the time he received his first yes from an investor, he was on the 107th version of the pitch deck.
As such, the answer to the second question should help you preempt and address concerns—explicit or implicit—in future pitches.
I discovered the below courtesy of the amazing Siqi Chen. Per a 2015 Harvard study, most people believe that people make decisions by:
Observing reality
Collecting facts
Forming opinions based on the facts collected
Then, making a rational decision.
But the reality is, people do not. People aren’t rational and investors are no exception.
Like everyone else, investors:
Are presented with facts.
Fit facts into existing opinions.
Make a decision that feels good.
Most of these opinions are not explicit. It’s neither on the website nor laid out in the firm’s thesis.
The good news is that most investors will share the same reservations. If one investor hesitates about something, another will likely do so. The best thing a founder can do is to address it before it comes up.
For example, if an investor tells you that if you have a better pulse on the competitive landscape, you would then be a ten. In the next version of the pitch, you might say “You might be thinking that this space is highly competitive, and you’re right. At a cursory glance, we all look like we tackle the same problem and fight over the same users. But that’s when this space deserves a double take. Company A is best in class for X. Company B is second to none in Y. But we are world-class in Z. And no one is offering a better solution for Z. Not only that, customers are begging for solutions for Z. One in every five posts on Z’s subreddit asks for a solution like ours. But if you look at the responses, no one has a perfect solution for it. In fact, people are duct taping their way across this problem. Not only that, in the past three months, since we shared our product on the subreddit, we’ve had 10k signups to the waitlist with 500 of them paying a deposit to get early access to our product.”
On that note, I don’t think it’s worth trying to change the original investor’s opinion after they share such feedback. Most of the time, you’ve unfortunately lost your window of opportunity. If it takes X amount of information for an investor to form an opinion about you, it takes 2-3X the amount of effort and time — if not more — for him/her to change said opinion and form a new one.
Lastly, per Homebrew’s Hunter Walk: “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.”
3. Schedule the Second Meeting during the First
Say the vibes are right and you get the impression that the investor really loves your product and/or your problem space and/or you as a person. When you’re raising your first institutional round, it’s either a “Hell yes” or a “No.”
Open up your calendar at the end of the first meeting and schedule your next meeting there and then, but be sure to give the VC enough time to talk with his/her team and also suggest where their firm might want to dive deeper. Give three options for topics to dive into the next meeting. For instance:
The team and future hiring plans
The vision and financial projections
The product, demo, and team’s current focus
From there, have the investor pick one of the above before your next meeting. If they don’t, say something along the lines of: “During this conversation, you seemed to love to hear about the product, so we’d love to dive deeper into the product the next time around unless you prefer one of the other two options.”
Also, start tracking which paths seem to convert investors faster. For example, if 30% of the investors you talk to jump into diligence after hearing the vision, but only 15% convert after the product path, lead with the vision one first next time. “Most of our investors fall in love with us after hearing about the vision, and would love to share more on that at the next meeting.”
The moral of the story is simple: make it easy for your investor to say yes to the next meeting.
4. Realize that ‘No’ is merely a ‘Yes’ in Disguise
If you get the feeling that it may be a no, ask the investor, “What firm/investor do you think I should talk to who might be a better fit for what I’m working on?”
Do not ask for introductions. An introduction will come naturally if an investor is really excited about you. Additionally, even if the investor who passed does introduce you, a natural question will be: “Why didn’t you invest?”
This sets you up for failure because the other investor’s first impression of you will be negative. The only exceptions are if the reason is outside of your control. For instance, they’re raising their next fund since they don’t have any more to deploy out of the current fund, or they’ve recently changed their investment thesis away from what you’re building.
But I digress. What you should do instead is collect a Rolodex of names.
Never ever run out of leads. You never want to be in the position to beg someone who turned you down for money.
When a certain investor gets mentioned more than once — ideally at least three to four times — that’s your cue to reach out to them. “Hey Tom, we haven’t met before, but I’m currently fundraising for David’s Lemonade Stand. And four investors highly recommended I chat with you on the product, given your experience in food-tech and how you helped Sally’s Lemonade Bar grow from 10 to 500 customers.”
5. Use Investor Updates
Send interested investors weekly investor updates during your fundraise and monthly ones after its conclusion. Share important learnings, key metrics, and your fundraise’s progress.
Be sure to induce FOMO in your updates. Not in the sense that your round is closing soon, rather, that you’re at an inflection point right now in both your product and the market. Two example prompts:
Why are you within the next 12-18 months “guaranteed” (I also use this word hesitantly) to 10x against your KPIs?
Is the blocker right now a market risk (which leaves a lot for debate, and most investors will choose to wait for a future round) or an execution risk?
How have you de-risked your biggest risks?
Taking this a step further, you need the courage to “fire” an investor. If an investor doesn’t get back to you after two emails, it could just be that they’re busy. If they don’t get back to you after eight or nine emails, they’re just not interested. My rule of thumb is always three emails each a week apart for each investor. I have seen founders who have done more, but I would not recommend any fewer.
Regardless, whatever number you decide on, the last email ought to try to convert them. For examples:
“Since you haven’t gotten back to me yet about your interest, I assume you’re not interested in investing. As such, this will be our last investor update to you. If we are wrong, please do let us know.”
Interestingly enough I’ve seen more investors start conversations by this last email than by the very first. Remember to treat your fundraise like a sales pipeline; A/B test different copy and see which lands the best.
Concluding Thoughts
Remember, fundraising is a lot like life: it’s simple, but far from easy. It requires grit, determination, and a healthy dose of elbow grease. Despite current market conditions, forge ahead! Follow Jim Valvano’s lead and “Don’t give up. Don’t ever give up!”
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
The past 2 weeks brought me a whirlwind of conversations with emerging managers and LPs, catalyzed by the emerging LP playbook. And of the former, I’ve come across two main themes:
Everyone — I kid you not… everyone — has top-tier VCs as their follow-on and/or their co-investors. What was once upon unique is no longer so.
Eric was right. There’s an overabundance of the word “signal” in venture wonderland these days — to the point the word itself has lost its meaning. By definition, it should mean that is unique and stands above a sea of noise. For many investors, that means either investing in brand-name startups (i.e. SpaceX, Figma, etc.) or investing alongside brand-name investors. The latter, unfortunately, is also a product of the ecosystem as many LPs seek social proof about your investment thesis from others’ who have a proven track record. The former gets a bit sticky. A lot of these logos are either off-fund-thesis or came as a Series B syndicate investment (but the fund itself is investing in pre-seed or seed).
After publishing the emerging LP playbook last week, I've been lucky to chat with quite a few emerging managers raising their Fund I's
And there are 2 common themes I see in their decks:
1. Tier 1 VCs as follow on investors are table stakes 2. There's a lot of logo shopping
To piggyback on the above, the notion of signal is worth elaborating on, likely a vestigial appendage of the past two years.
Let me preface by saying that it takes a lot to get to conviction.
In 2020 and 2021, many investors’ calculus of startup signal boiled down to three things: great investors, great traction, and great team. And in that order. That is first and foremost what I see a lot of professionalizing investors do. I can’t entirely blame them since the ecosystem itself propagates the belief that if a Tier 1 VC jumps in, you’re more likely to get to a great exit. Or at the minimum, get a great mark-up to make your IRRs and TVPIs look better. On paper, of course.
But what I believe a lot of investors are missing is that… venture is a game that’s not about your batting average, but about the magnitude of the home runs you hit. You’ve heard it before, and you’ll continue to hear more of it. Unlike other financial services, VC is driven by the power law. 80% of your returns will be driven by 20% of your bets. That’s the 10,000 foot view. Let’s be honest. Most of us, myself included, don’t take that panoramic view every day or even every week. In fact, I see many emerging managers only take that view when they’re forced to. In other words, when they’re in fundraising mode.
For many professionalizing angels and syndicate leads, that becomes trying to string a narrative from seemingly disparate data points. Or at least, it seems that way.
As Asher Siddiqui told me, “[after] you look at their whole life and career history, and look at their thesis, if the thesis doesn’t make complete and perfect sense, then I don’t think this is a ‘great‘ fund manager. If it fits like a glove, then yes, they could be.”
The best GPs are disciplined even before they start fundraising. They focus on the thesis they want to raise on when they do. That’s not to say they don’t invest off-thesis every so often. But they don’t pitch their off-thesis angel or syndicate investments as part of their thesis-driven track record. But I digress.
In chasing signal for the sake of signal, when you hear of a hot deal every other day, many investors forget to be that belief capital for founders. I’m not saying that an investor should do so for every founder out there. But to pick a few, or even just one. One that they’re willing to take the swing before others do.
The signal is their own conviction in the founder.
The first half
Because of this progression, there’s been a new two-part question I really enjoy asking emerging GPs. The first half:
Which company in your portfolio you think is still underestimated?
Which company in your portfolio didn’t get the investor attention you expected but are still extremely bullish on their growth? And why do you still believe in them? What are other investors missing out on?
It’s not about track record or social proof here. It’s about the ability to recognize exceptional talent and articulate it clearly. Hopefully, a rose growing in concrete.
Well, in terms of the odds, you’re likely to be wrong. But that’s okay. You need to be willing to be wrong to achieve outlier success.
Fund I is often the proof-of-concept fund for the emerging managers I’ve talked to. They start by writing small checks, don’t lead rounds, and don’t fight for ownership targets. They claim to be extremely helpful and hands on. Then again, expectation often differs from reality, especially if they’ve never been so before (where LPs discover through reference checks). And because they’re writing smaller checks now, I’ve seen many implicitly hold off on developing a framework to get to conviction until Fund III. Whereas the best GPs start thinking about it early on.
You can think about it this way. As long as you’re benchmarking on signal via other investors, why should an LP back your thesis when they can back your “signal”?
For individuals and smaller family offices, they’ll still back you. What they’re buying is access, since they can’t afford nor have the relationship to be an LP in the “signals.” Larger LPs have the optionality to do so. And if you’re an emerging GP hoping to grow as a professional manager by having larger and larger funds, you eventually need to raise from large LPs. At least, until the SEC changes their 99 limit. And to do so, from larger LPs, means you need to bet where their existing portfolio has not bet before. Plus do it well.
The second half
If you haven’t already, a great way to build a referenceable track record is to sweat the details. Yes. The details matter. Nate Silver, one of the best poker players of our generation, said earlier this year, “you can’t just get the big things right in poker. You have to get the small things right too. It’s too competitive of a field right now.”
Though he said venture is different, I believe he’s half right. Most investors don’t sweat the small things. But investors should. Today, that’s how you stand out.
It might not have been true a decade ago, but now it is. Just last year, in 2021, there were 730 funds created. To put that number into perspective, on average, that literally means two firms closed every single day last year, including the holidays and weekends!
Capital has become a commodity. In 2021, speed was a differentiator. Clearly, in 2022, it is not. Today, it’s tough being a founder. If you’ve raised in the last two years, you’re considering extending your runway. That means having tough conversations to reduce your workforce, your benefits, or your salaries. If you haven’t raised, it’s a hard market to be raising in now. And so the differentiator today, is in two parts:
Helping founders navigate these tough situations. In other words, being (proactively) helpful.
And helping founders raise their next round. Mac Conwell recently shared a great thread on how powerful a founders’ network is to get funding. The same applies to an investors’ ability to help their portfolio raise capital. How liquid is your network? It’s not about who you know, but how well you know your friends downstream, and how can you get them over the activation energy to invest. Don’t get me wrong. There still needs to be a certain level of hustle from the founders themselves. But a great investor often steps in to reduce as much friction as we can in that process.
Both of which have long been the job description of being a VC. It’s in the small things. Jump on a 2AM call. Help your founders figure out the wording for a reduction-in-force. Fix the sales copy to better close leads.
There are 10-15 character-building moments in a founder’s journey where the moat they build around the business (as opposed to just the product) is not IP or early product traction, but rather from the lessons obtained from scar tissue.
It’s hard to predict looking through the windshield when these moments are, but quite obvious via the rearview mirror. And the best an investor can do is be there as much as he/she can. Albeit hard to do for every company in your portfolio, and that’s the truth. The wealth of information creates a poverty of attention. The larger your portfolio, the harder it is to be truly helpful to every single one. So focus on founders who need you, rather than those who will do great without you. Reputation is built in wartime and realized in peacetime.
So, the second part to the above question is:
What did you do for this company that no other investor or advisor did?
… where I’m looking for answers on how this investor went above the call of duty to help a company they believed in grow.
In closing
In summary,
Which company in your portfolio you think is still underestimated?
What did you do for this company that no other investor or advisor did?
This is by no means original, but heavily inspired by the recent conversations I’ve had, as well as helps me build my own framework for analysis. In parts, this question is a derivation to the check size to helpfulness ratio (CS:H). How helpful are you as an investor? When you say you’re founder-friendly, do you mean it?
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
Before we dive into this blogpost, I’ve been asked by my legal friends to include the below disclaimer. I have a version of this at the bottom of every blogpost, but nevertheless, it doesn’t hurt to reiterate it again.
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Back in the hallowed halls of my elementary school, I had a principal whose presence was always larger than life. He was often the optimist and, with words alone, could figuratively turn water into wine, and any mistake into an opportunity. Ironically, there was a sign that hung above the door to his office that read: Opportunity is nowhere. An odd sign that seemed to be the Hyde to his Jekyll.
I spent a whole year contemplating why. And on the last day of third grade, I finally mustered the courage to ask him.
“Mr. M, why do you have that sign above your door?”
“What sign?”
“The sign that says ‘Opportunity is nowhere.'”
He paused and chuckled, “David, it looks like I bought the wrong sign. It’s supposed to say ‘Opportunity is now here.’ But now that you mention it, you could say the only difference between no opportunities and endless opportunities is just one small space.”
In the venture market, that small space blossomed in late 2020. In a flurry of SPACs, secondary markets, and tech IPOs, exit opportunities for venture-backed companies were flourishing. There were multiple paths to liquidity. Tech employees saw their net worth grow, and more accredited investors were minted by the day. Alumni syndicates grew in membership and deal volume.
With a surplus of capital in the market, the money had to go somewhere. Not to savings accounts. But to goods and services. Crypto and NFTs. Startups. And other capital allocators.
Adjacently, the COVID days saw the (re)emergence of new markets. Ecommerce. Fintech. Remote work. Future of work. Web3 and the metaverse. Just to name a few.
In 2021, VC fundraising activity surpassed $100B in funds raised for the first time. $128.3 billion across 730 funds, to be exact. Carta also saw a massive jump in the number of Fund I’s created last year. More than ever before, there was an abundance in opportunities to invest in venture funds.
Anecdotally, in my work at On Deck Angels and at DECODE, I’ve seen a rise in the number of opportunities to invest into funds as well. Via various other platforms as well:
Revere — where you can discover and evaluate venture fund managers through a unique rating framework. They’ve also recently launched explorevc.com for those curious about who’s in their pipeline;
Allocate — an end-to-end platform that covers everything from discovery to capital calls and keeping track of your portfolio;
Arlan Hamilton famously raised $5M of her fund via Republic, an equity crowdfunding platform. More recently, Cathie Wood announced the opportunity for non-accredited investors to invest in the ARK Venture Fund through Titan.
There was and still is a wealth of noise, but a poverty of “signal” — a word that may have lost its true meaning in these past few years. When signal is everywhere, it is nowhere. So more than ever before, more than opportunities, what the world needs more of are frameworks. Frameworks on how to differentiate for yourself signal from noise.
There is a wealth of content and discourse in the broader world for investors, which include advice on personal finance, investing in stocks, option trading, and of course, quite a bit, in the world of startup investing. But surprisingly little in the realm of investing in venture funds. The only ones I could find were OpenLP and SuperLP, which if you know me I had to ask both of their authors for their latest insights here as well.
As we were wrapping up our conversation on a sweltering late summer day, Martin Tobias, founding partner at Incisive Ventures, told me:
“Somebody should write a book like Jason Calacanis’ Angels, but for LPs.”
And he’s completely right. While that is a larger endeavor altogether, hopefully, this blogpost serves as a preamble for a greater conversation.
Who is the emerging LP?
An LP, or a limited partner, in the context of this essay, is someone who invests indirectly, rather than directly into startups. While investors in syndicates and SPVs are also counted as LPs, for the purpose of this piece, I’ll focus on people who invest in funds.
If you’re an emerging LP, you’re most likely writing checks into Fund I’s. Maybe Fund II’s, if you’re lucky, can write larger checks ($250-500K+), you have something a GP wants, or some permutation of the above.
Effectively, this blogpost is dedicated to the investor looking to invest in fund managers who have yet to prove their institutional track record. And just like investing into a pre-seed founder, searching for product-market fit, the checks you are writing are… belief capital.
If it’s belief capital, assuming the GP has the underlying mechanics down (portfolio construction, fund strategy, etc.), it’s all about people. And if it’s all about people (I’m overgeneralizing), how you win as an LP is determined by your ability to differentiate the top decile from the top quartile. Part of that requires some level of intuition. But I am ill-equipped to speak on LP intuition, as opposed to VC intuition. So, I had to ask folks with more miles on their odometer.
Asher Siddiqui shared it best in our conversation from the perspective of an emerging fund manager:
“Here’s the problem that I have. Imagine you’re an emerging fund manager and you think you’re hot shit. How long do you think it takes before you figure out if you are?
“The average deployment period is 2-3 years. You launch Fund I in Year 1 and launch Fund II between Year 2 and 3. You close the second fund around Year 4. By Year 7-8, you now have some DPI from Fund I, early DPI from Fund II, and are now writing your first checks from Fund III.
“The truth is no one knows if you’re a great fund manager until you’re eight to ten years in. That means if you’re meeting a great manager, you’re meeting them when they’re already at Fund III, or when they’re raising Fund IV.”
Similarly, the truth is as an emerging LP, you probably don’t have the opportunity to invest in “hot shit.” Why?
Top-tier funds are oversubscribed, and have a waitlist to even get the chance to invest.
And if you could, due to the size of their funds, you need to be able to write checks on the magnitude of 7-figures and up.
Rather the buffet you have before you is the opportunity to support the best before they’re the best. So instead of looking for lagging indicators, like TVPI, DPI, and IRR, the conversations that sparked this blogpost is intended to look for leading, predictive indicators. But as you might guess, there is no one right answer in foresight. But I do hope the below serve as tools in your toolkit as you grow your arsenal of frameworks for investing in GPs.
As a quick note, wanted to share some quick definitions I wish I knew at one point in my life:
TVPI: Total-value-to-paid-in capital, aka paper returns
DPI: Distributions-to-paid-in capital, aka the actual money you get back, or Chris Douvos calls it: “the moolah in the coolah”
IRR: Internal rate of return, aka how fast your money appreciates per year
Net IRR: your IRR after fees, carry, expenses are accounted for, and what LPs care about more than gross IRR
GP: General partner of a VC firm, aka the head honcho at a firm
Finding the best LPs
The world of fund investing is, for lack of better words, opaque. There’s no public Rolodex of limited partners. If you stick around the venture world long enough, there are familiar names that regularly pop up in fund pitch decks or during VC happy hour. And outside of the big institutions who write $5M+ checks that you might find on ad hoc expeditions into the world of the internet, the two best places I’ve found so far for information on LPs is Sapphire Partners’ OpenLP.com. And scouring AngelList’s syndicates and PCN (Private Capital Network) for their LP networks, neither of which are public either.
At the same time, most individual LPs don’t go “shopping” for deals. They invest opportunistically into people they know and trust or alongside people they trust. In a way, this blogpost is also designed to help the individual LPs below shop for deals. By sharing the fact they LP publicly, my sell to them was that maybe this blogpost will the earliest semblances of fund deal flow to them.
Just as a fund manager brings smaller LPs on for very specific reasons, an LP should have a similar rationale to why they are investing in a GP. It’s a two-way street.
Methodology and a table of contents
I’m going to preface by saying: This isn’t an academic research paper. So as such, I may not have followed all the best practices in doing academic research. Nevertheless, I promise you won’t be disappointed. The below found its genesis scratching a personal itch that grew into:
How can I best support emerging GPs?
A first step into demystifying the black box of LP investing
Help individual LPs build thought leadership and discoverability, aka deal flow
And, building an investing playbook for pre-product-market fit funds
To each individual, I asked just four questions:
Apart from TVPI and IRR, what are leading indicators that differentiate the great GPs from the good GPs? In other words, the top decile from the top quartile?
In fairness, I iterated on the wording of this question the most because a few LPs I asked early on only had one answer: track record. And track record — in other words, TVPI and IRR, especially DPI, are lagging indicators.
Any red flags about emerging GPs that new LPs should be aware of?
What common pieces of advice should emerging LPs ignore, if any?
This was one that either completely hit or completely missed. The latter due to the fact, that there isn’t much advice, period, that is shared between LPs who don’t already know each other. One of the main reasons I believe this blogpost should exist.
Anything else you think first-time LPs should be aware of?
Some shared over text. Others over email. And a handful of others across calls and coffee.
As such, I’ve segmented this blogpost into five main sections:
In the words of my friend and colleague Gautam, “A big part of direct early-stage investing is more than just financial return. The same holds true as an LP, especially as an emerging LP. Be very clear about why you’re an LP. An investor who invested in the same fund as I did called his LP commitment the most expensive newsletter subscription he’s ever been a part of.”
Why you should be an LP
“The most important question to answer is why do you want to be an LP? To me, there are three reasons:
You want to build a career in this space – potentially a fund of funds, or manage someone’s family office.
You’re not the best at picking individually good startup deals to invest in, and you want to be strategic. For example, if David has the best deal flow in web3*, and I don’t, I want to invest in David.
This manager also has access to top deals – top deals that would otherwise be impossible for you to get into. If you invest in the fund, you also get access to the fund’s pro rata rights.”
— Shiva Singh Sangwan, 1947 Rise *Author’s Note: I don’t have the best deal flow in web3, but am flattered to be the example.
“I’m also a startup investor myself. My goal is still to uncover the best investments out there. So, there are 5 reasons as to why I invest in funds:
Investing in outliers: I invest in funds who have access to opportunities I may have missed myself. I don’t want to miss the next Gong.
Knowledge and network expansion: I want to expand my knowledge and network of what and who is out there. To become a better fund manager and uncover what’s happening out there in the market, I read other GP’s investor updates. I learn from what they learn.
Expanding my deal flow: I invest in others’ funds to get to invest in the companies they’ve invested in, and earning my right to, by being as valuable as an LP as possible.
Learning: I’m able to learn about areas that I’m very interested in. For example, I’ve spend the past year trying to learn more about web3, so I invested in web3 funds. I read the GPs’ investor updates and have effectively built a braintrust of GPs who are experts in web3.
Regional coverage: I LP into funds in emerging markets, namely, India, Southeast Asia, and Europe. I want to back someone who’s just starting with a Fund I, in a region I don’t have coverage on.”
— Sriram Krishnan, Kearny Jackson
Why you should NOT be an LP
“Venture isn’t a winning strategy for retail investors. Many investors cite that new funds outperform the S&P 500 or Russell 2000, but the truth is most venture funds have a low probability of beating the NASDAQ. Those that say otherwise are ignorant. Venture, as an asset class, is worse than the best public market alternative ($QQQ) unless you are getting the best outcomes. You need to be in the quartile, by looking for the top decile. Only then can you beat the public markets.
“If you don’t fully understand what that game is – one you’re not going to get your capital back for 10-12 years, then stick to public markets and small checks angel investing to satisfy startup investing curiosity. People are often insular to what they see and believe, especially on Twitter. Everyone is talking their own book. Do your homework.”
— @Cashflow_Cowboy
“Adjust expectations. People think that they’re going to always make 10x on their money, but I’m reminded of a story from early in my career.
“In the aftermath of the dotcom bubble, a time during which a looooottt of people made a lot of money, a big endowment that had one of the top venture portfolios looked at their relationships in their totality and found that only three of their managers exceeded a TVPI of greater than 2.5x for the whole of their relationship (across all the funds). And if you look at VC as a whole, returns have only very rarely met the lofty expectations that most people have. We’re looking back at an extraordinary time, but I think that when people look back, especially at a landscape littered with dilettante funds, that we’ll say that as the TVPI matured into DPI (the ‘moolah in da coolah’) times were pretty good, maybe even great, but not all the trees grew to the sky like some thought they would.”
— Chris Douvos, Ahoy Capital
“My biggest piece of advice for this audience is to actually not invest in venture. Most of the entrepreneurial network over-indexes investments to venture capital or start-ups. But our career is probably already over-indexed to this high risk asset class. I encourage entrepreneurs who start to invest to look at real estate, stocks, private equity, or private debt/BDCs. You can actually buy private debt on the public markets, called BDCs – business development corporations – that are loans out of companies and pay 10-15% yield. Or mid-market private equity generates ~20% IRR’s with far higher confidence than a venture fund. Asset allocation across these different profiles are key.”
— Vijen Patel, 81 Collection
What Makes a Phenomenal GP (As Opposed to just a Good One)
For the purpose of this section, I’m going to depart from the usual metrics – like a 3x net multiple, or a 25%+ IRR for funds longer than 5 years. Why? Since (a) if those metrics exist, these funds are no longer non-obvious, and the likelihood of you having access to these funds as an emerging LP is slim (and fund performance speaks for itself), or (b) if they don’t exist, you’re going to rely on qualitative measures — just as you would investing in most early-stage startups pre-PMF.
Consistent, clear, and preemptive communication
“Most managers are not that great when it comes to transparency around fund operations. Things like: What are your latest investments? What’s the thesis behind some of those investments? How are they performing over time?
“Some of these things get answered, if I’m lucky, on a quarterly basis, but often on an annual basis or less. So if you find a team that’s consistent about sharing progress on a monthly or at the very least on a quarterly basis and are really responsive to answering your emails and any phone calls, that’s a good sign behind a team that’s working very hard to serve the interest of its LPs and treating the job like a fiduciary.
“I’ll put a little bit of side note here. This kind of behavior is great with founders, too. When founders are really great about communications, it correlates very well to their performance over time.”
— Eric Bahn, Hustle Fund
“The six funds that I’ve invested in so far (listed here if that’s helpful) have all been communicative, stayed true to their thesis, and given me opportunities to learn and help to the extent that I had hoped for.”
— Rebekah Bastian, OwnTrail
“Sometimes things don’t perfectly line up — a GP might discover new opportunities or areas of interest as they start investing in a fund. Or increased competition. If strategy changes have occurred, ideally the GP would have been flagging this to their LPs over the course of the two years but for a new prospective LP being able to speak to the changes is important.”
— Beezer Clarkson, Sapphire Partners
The best have a unique perspective
“As an LP who also invests directly into startups, we seek GPs who have something unique – some kind of insight. It’s not always about having the highest net return. These days, there’s not enough GPs who have a unique angle on the market. It could be how they diligence deals, how they set their investment strategy, or what top investments look like.”
— Anonymous LP, $30B AUM Fund
“The funds we have known that are top decile have a point of view, this can be expressed as being thesis driven, but doesn’t have to be. It does though provide a reason for why they invest in what they do and why an entrepreneur picks them.
“They have also, in our experience, have had multiple fund returners within one fund. Not always, if an exit is large enough with respect to the size of the fund, it is possible to have a top decile fund with just one fund returner. The power law is alive and well in the top decile funds we’ve seen. This means swinging for the fences with respect to a fund’s investments as well as supporting this with a portfolio allocation and management strategy that enables a significant exit to provide for strong returns.”
— Beezer Clarkson, Sapphire Partners
“Every investor claims to have a value. There are very few cases where investors pitch otherwise. Sector specific funds may have a real value add for very early stage startups.
Uniqueness is not about investing into a vertical or type of technology, but about their ability to measure the size of an idea. Great managers know how to identify big ideas that others aren’t seeing. Even more true if you run a big fund; you must be investing in even bigger outcomes.”
— Itay Rotem, EdRITECH
Is this strategy repeatable?
“Differentiating between ‘top decile’ and ‘top quartile’ is really just going to be luck, for the most part. If you’re simply measuring and assessing ‘good GPs’ from the great ones, by track record, here would be my top few:
“What % of the portfolio comes from the top 1, 2 or 3? If you can deliver a top-quartile return WITHOUT your one winner / ‘lucky bet’, that’s really good.
What % of companies successfully got funded from investment to the next round?
Seed —> Series A should be >35%
Series A —> Series B should be >50%
Series B —> Series C should be >50%
Series C —> Series D+ should be >60%”
— Aman Verjee, Practical VC
“For GPs with young track records, we look at what the contributing companies are. Who are the fund returners? And can they replicate the same strategy? When diligencing GPs, we also talk to the founders they invest in. Essentially, whether there is founder/GP fit.”
— Anonymous LP, $30B AUM Fund
“I look for someone who’s very consistent. They have the integrity to stick to their word. They’re not deal-chasing, deploying all their capital in less than two years, and trying to raise their next fund too quickly. Typically, you’re signing up for multiple funds. If the deployment window is very small, the GP makes frequent capital calls, which means you’re committing more capital in less time.”
— Sam Huleatt, On Deck
“TVPI and IRR tend to be lagging indicators, not leading ones (for many reasons — including irrelevance of these metrics earlier than 5 years, changing motivations, engagement, and so on for investors, and shift in fund size/strategy, noting the Maples Dictum that your fund size IS your strategy).
“For me, the thing that tilts the odds in favor of a manager having the potential to be ‘great’ is that they are leveraging some sort of ecosystem. That can be an ecosystem built on years of success (Sequoia) or ‘prepared mind’ like Accel back in the day, or deep entrenchment in a mafia (Founders Fund). Additionally, some people build fertile ecosystems like First Round or True by investing time and attention in targeted and intentional ways. I try to look for people that are entrenched in some kind of robust ecosystem and match the moment when their upward-sloping line of experience as an investor intersects the (generally) downward sloping line of hunger. For more specifics on my thought process, see the most recent (five years old LOL) post on Super LP.”
— Chris Douvos, Ahoy Capital
“Over the long run of course, it’s DPI, but it’s about consistency of returns, which typically is a byproduct of them understanding where their definable edges (finding product/market fit), and ruthlessly exploiting those edges through building repeatable processes on sourcing, decision making, team building, etc.”
— Samir Kaji, Allocate
“This portfolio can’t be a one-hit wonder. Is there enough gold in the middle after you take the top two and the bottom two investments out?
“There’s a Rome in everyone’s future. You go up and then you go down. There are many funds that generated outsized alpha in the last decade but are not what they used to be.
“If you’re leveraging a network, is that alumni network today the same as it was yesterday. Did most of the smart, driven people leave? Are you borrowing or are you using that network? Were you there at the right vintage?
“Also, bet on people who do what they said they would do. Where did the returns come from? If the top returns came from their 20% discretionary funds, and not their 80% core fund, is that something worth betting on again as an LP? I would rather back a 3x return from an on-thesis fund than someone who gave me a 6x who came from off-thesis. The latter is because it came from sheer dumb luck. The question is, what do they do with that dumb luck? Do they pivot and learn, or continue to go rogue / play the roulette?
“Think about why LPs give money to GPs. Anyone can go into Vegas and play the roulette. The best GPs can do something I cannot do and they do it repeatedly.”
— Asher Siddiqui, Sukna Ventures
Access > proprietary deal flow
“We have felt for a number of years now (including pre-COVID) that the concept of ‘proprietary deal flow’ is not really a thing. Proprietary access however is something we think is true, powerful and not simple to achieve (hence why powerful ).”
— Beezer Clarkson, Sapphire Partners
“I look for emerging managers who have a highly differentiated platform offering or differentiated deal flow. In addition, for someone who has won before, like winning great deals, they’re likely to win again.”
— Sriram Krishnan, Kearny Jackson
“For an emerging GP, it’s all about access. Do I have the confidence that the best founders will seek out this GP?
How I evaluate access for a solo GP is different from how I evaluated a platform. For platforms, their external brand plays a big role. What are other founders saying about them? I talk to founders they’ve backed because ultimately, founders are their customers.
For solo GPs, I evaluate the GP on their personal brand, and his or her own insight on how they are thinking about the fund as a product. Here, I think of it as more of a bet on the founder of the firm, and not a fund bet.”
— Gautam Shewakramani, Inuka Capital
“GPs also need to be able to quantify that unique access. I’m an LP in a fund that puts on a regular conference and runs a community of 30,000 [redacted job title]. Their thesis was that they’re going to fund the best ideas that come out of their [redacted] community.
“The same is true for Packy McCormick. His thesis is: ‘I help startups tell their stories. I have all these readers who are VCs and founders, and they’re going to invite me into their deal.’ So, the quantitative thing is how big is his mailing list and how fast is it growing.
“It’s the ability to quantify things that you as the GP think are proprietary about your particular access to this market segment. It’s more than just how many LinkedIn friends you have or how many Twitter followers you have; it’s specific to your thesis.
“For my thesis, I get referred deals because I’m an LP in 17 funds. I invest in deals that are too early for these other funds, and I can get them follow-on financing because I know directly the LPs in the follow-on funds. And the fact that I’m an LP in 17 funds gives credibility to that thesis.
“One of my theses is that I’m a really good pre-seed investor because my companies get a higher percentage of follow-on financing than your average VC. Mine is 72%. Techstars is 30%. I’m two and a half times better than Techstars at getting follow-on financing.”
— Martin Tobias, Incisive Ventures
“I’m an LP in 17 venture capital funds, and it’s very clear what separates the best from the good. Deal flow.
“I also think we are entering a new era where you’ll see specialized, smaller funds that will generate great performance because of domain expertise and proximity to the nucleus of innovation. I get really excited about this group, and think some of these <$50M funds could generate 5x+ returns.
“For this group, I look for two things:
The team climbing the hill: Why is this team special in being able to attract great deal flow? Examples could be knowledge expertise, distribution, prior experience, geographic coverage, but a compelling edge is critical.
The hill that team is climbing: Ultimately, macro matters a lot. We like to attribute performance to skill, but timing, sector, and luck play a large part of success. The worst manager in crypto in 2015 probably did pretty well. The worst fintech manager in 2010 probably crushed it. I think about what will be the area in 2030 that everyone wishes they had exposure to today.”
— Vijen Patel, 81 Collection
They don’t have to ask “How can I help?”
“Most investors are not helpful. I started a company, raised some VC money, then some from angels. And I realized that our most helpful investors were angels. I came to understand that there are two kinds of helpful investors:
Reactively helpful
Proactively helpful
“For the former, you would have a problem, reach out to your investor, and they would really help you. For the latter, it’s Alex. Alex was one of our first investors. He would often come into our office, and without being prompted, proceed to write code against our APIs. And I thought, if I were to be a VC one day, I wanted to be just like him — very hands on. I knew he would be a real value-add investor.”
— Brent Goldman, Lancelot Ventures *Alex is a fictitious name of a real person.
“It boils down to three questions that are all interrelated:
Does this fund manager have a brand?
Does he/she have access? Do founders need them more than the manager needs the founders?
And does he/she have something unique to provide to founders?”
— Shiva Singh Sangwan, 1947 Rise
“At the pre-seed level, where I invest, a great fund manager is someone who gets a startup to a ‘real’ round of funding. I think it’s like fording a river: a good fund attracts founders to their boat, then ferries them across to the other side. For this service, they are rewarded with allocation in a round that’s underpriced once they reach the shore.
“Great funds are ones that have a sustained, repeatable process for attracting founders and a reliable methodology to get them across. This can look like focusing on a geography, focusing on a sector, focusing on an underserved founder market, acting as a scout for a larger fund who likes your deals, or some combination of the above.
“The returns from pre-seed are really about getting early and cheaply enough to have made the risk worth it.”
— Paul Griffiths, 15 & Change
Are they hungry?
“I work with some good fund managers, but why are they not great? Why are they only in the top quartile, and not the top decile? They have all the ingredients of being great. They have amazing pedigree, and they went to the right high school, the right college, and worked at all the top startups in their vintage. But… they’re not hungry. They haven’t had enough adversity in their life.
“I have seen prospective LPs only look at a GP’s career history, and not their life history. You need that extra data point, that context. To take a holistic view of the unique set of experiences of a human being, and not just the professional. You look at their thesis, and their history; you look at it from birth to today; you look at their whole life and career history, and look at their thesis. If the thesis doesn’t make complete and perfect sense, then I don’t think this is a ‘great‘ fund manager. If it fits like a glove, then yes, they could be.
“I don’t believe in luck. I believe you create your own luck. How do you create your own luck? You create chaos, which creates opportunities — you then leverage your past experience and your drive to capitalize on that opportunity….”
— Asher Siddiqui, Sukna Ventures
The devil is in the details of their portfolio construction model
“They need to have thought about deployment (schedules) and fund size. One of the quotes we both like is ‘Your fund size is your strategy.’ A fund of $10 million should have a very different strategy than a $50 million or $100 million fund.”
— Sam Huleatt, On Deck
“To us, the difference between good and very good is portfolio management. How do they think about reserves to follow on? Do they look to increase allocation into the winners?
“There’s a big difference between managing a $5 million fund and a $20-30 million one and $500 million one. How you look at portfolio management and allocation is different. Everyone tells you they can give you a 5x return, but I only need 3x DPI! Even the best firms out there struggle to return 3x on certain funds.
“Your size is your strategy. We take into account the geography you invest into. In Israel, we don’t have decacorns. And because the exits are lower, the fund size should also be lower.”
— Itay Rotem, EdRITECH
Mixed references are not as bad as you think
“I’ve backed a lot of funds across the private markets, in both private equity and venture capital, and great investors may have divisive personalities. You want to back special talents, and they may rub people the wrong way. That said, there is a difference between a prickly personality and a bad actor not treating founders right, and not being ethical in their dealings.”
— Anonymous LP, Private Wealth Management Firm
Does the GP have investor-market fit?
“Success builds upon success in venture. I’m never going to attract the best talent in the neobank or fintech space. They don’t know who I am and I don’t have true domain expertise. But if you’re doing something in retail or in hardware, I can really help and you likely know what Tide Cleaners is. Folks in retail find a way to get in front of me, and likewise, I can meaningfully help these companies. Product market fit applies to VC’s, too. And we don’t talk about this enough, but also LP’s.”
— Vijen Patel, 81 Collection
The best have long time horizons
“Luck aside, I index greatly on energy, fire, thoughtfulness, and passion. Some founders or operators raise a fund after an exit because they don’t know what to do next and have money in the bank. LPs need to discern as best as possible how committed these people are to the job of investing. How much does the GP resonate with the founders they’re backing?
“GPs who are only building, but don’t understand roughly what they’re building towards tend not to resonate with me. GPs who have founder friendliness talking points, but few examples of hard conversations with founders don’t resonate with me. I get concerned when GPs don’t appear to have an understanding of what kind of bet they’re actually making. The great GPs have long-run perspectives and are willing to adapt. Startups have to execute miracles to achieve great financial outcomes. I want to see GPs have a rough mathematical understanding of their bets based on their assumptions and stories. What’s a reasonable amount of capital to startups to their milestones, knowing your home runs are going to go much further than your initial projections? What does SaaS multiples going down from 10-15x to around 8x mean? Was the GP banking on elevated multiples persisting for the math to work?”
— @Cashflow_Cowboy
“I want to invest in people who are going to build multiple funds, so the long-term commitment to the space is critical.
“Every fund thinks they’re solving a unique problem – most are not. A happy outcome is backing a GP that you believe in, so I’d prioritize character over potential returns. At the end of the day, you’re getting into a decade-long relationship, so you’d better like the GP as a person, not just the asset class.”
— Paul Griffiths, 15 & Change
Luck is a skill
“The thing is everyone’s smart, and between the top decile and quartile, luck is a big differentiator.”
— @Cashflow_Cowboy
“The difference between top quartile and top decile is one of luck. I believe that it is impossible to predict ex ante.”
— Chris Douvos, Ahoy Capital
“Outlier performance is a combination of luck and skill (luck is needed for massive outlier funds), but the best fund managers require less luck to consistently outperform because they have well constructed operating frameworks.”
— Samir Kaji, Allocate
“In my early days in venture, I spoke with several investors on the Midas list. And every single one of them attributed their success to luck and timing. They still view themselves as learning and actively track their anti portfolio to see what they missed. They’re humble, and still suffer from imposter syndrome. When I ask them these two questions:
Which were the startups that you thought were going to be winners?
What startups put you on the Midas list?
“There will be some overlap, but more often than not, it’ll be a different set of names. Investing in GPs is a bit like startup investing. It’s a bit of a roulette wheel. What you’re doing is improving the odds. Any LP or GP who says otherwise is full of shit.”
— Asher Siddiqui, Sukna Ventures
The best change the status quo
“I believe great GPs aren’t just impacting the success of their portfolio companies and their LPs, but are changing entire systems that are historically pretty broken in the VC ecosystem. The vast majority of LPs, VCs and funded founders have tended to be pretty homogenous in terms of the identities they hold and approaches they take to building & funding companies. By breaking through those biases and pattern matching, not only will a new kind of emerging fund manager see better returns, but they’ll also dismantle a lot of the systemic inequities that have prevailed. TL;DR: Good managers see healthy returns, great managers see those returns and leave things better than they found them. (I wrote a bit about some of those inequitable systems here if you’d like to link to it)”
— Rebekah Bastian, OwnTrail
GP Red Flags
Logo and trend shopping
“There is a concept of just logo shopping. A lot of decks are loaded up with a bunch of logos of great companies that the GPs have invested in the past.
“There are people who say they’re seed investors were able to get a slice of allocation of some hot company at the Series C or Series D for a $5,000 or $10,000 check. There’s nothing inherently wrong with that as an investor. But the way that it’s framed often looks like that they were seed investors in these hot companies as well.
“So, there’s some of that window dressing. I think that is a red flag. It just is on the edges of honesty that I’ve never really liked.”
— Eric Bahn, Hustle Fund
“When GPs claim to invest in a deal, one red flag is when they were only an angel in a syndicate, and the founders don’t even know the investor by name. We also look at deal attribution for GPs from bigger funds. How involved were they in winning deals at their last fund? So, we do backchannel checks.”
— Anonymous LP, $30B AUM Fund
“I’m wary of trend followers. People who follow trends without having anything unique to add to founders building in the space.”
— Martin Tobias, Incisive Ventures
Not playing the long game
“Another [red flag] is when GPs change the terms when fundraising. As a GP gets more interest, we’ve seen some GPs change the terms – from 2% fees to 2.5 or 3%. It raises some concerns that they are opportunists which might be viewed as a sign that they weren’t committed to building a long, durable fund.”
— Anonymous LP, $30B AUM Fund
“There is never a full alignment between LPs and GP. There are many potential conflicts when it comes to VC management. You don’t want to invest in people who will not hesitate to screw you. Don’t invest in people you don’t trust. There’s a thin line between greediness and discipline. We don’t invest in investors who are too opportunistic. Discipline and strategy consistency (with an amount of flexibility) is important.
— Itay Rotem, EdRITECH
“Too many GPs today are obviously dilettantes. The average fund lasts twice as long as the average American marriage, so it’s a long-term commitment to your partners. I get the sense that a lot of new GPs are becoming VCs in the same way a lot of college kids end up going to law school: it just seemed like the next obvious thing to do/the path of least resistance.”
— Chris Douvos, Ahoy Capital
“This is personal for each LP. I believe the GP’s job is to maximize returns for their LPs. So, there’s a tradeoff between GPs playing the long game and having a fiduciary responsibility to return money in the short run. So, a red flag for me is when the GPs don’t play the long game.
“There’s this weird nobility in venture, especially in the pre-seed. Sajith Pai wrote a great piece on this. Your first investor is almost like a priest. As the first check into a company, you should be a good priest. Is this person someone who will be a strong supporter of the founder, which could come at odds with short-term financial return? I won’t get immediate distributions. But at the same time, over a fund life, this could generate better financial returns across a portfolio of founders or in the form of access to better deals driven by reputation or founder friendliness.”
— Gautam Shewakramani, Inuka Capital
“People say they’re going to deploy over the next 2.5 years. But guess what everyone did in 2021. They deployed their entire fund. So LPs are asking, ‘What are you doing? We had all of this scheduled out, but you deployed so quickly, and so now we’re out of money. We can’t do your re-ups for next year, or we can’t back new managers right now.’ It’s been a real issue that has kept so much money on the sidelines.
“Saying you’re going to do something, then not doing it is a huge red flag. Do what you say you’re going to do. This is a relationship game. If you’re breaking trust, you’re playing the short game instead of the long game.”
— Vijen Patel, 81 Collection
Small funds, big reserves
“I’m wary of small funds with big reserves. For example, a $50 million fund with 50% reserves. What it means is you’re getting less shots on goals. For Fund I’s, it’s all about shots on goals.”
— Martin Tobias, Incisive Ventures
They lack honesty and self-awareness
“A big one is a lack of openness of what didn’t go right. Some GPs exhibit a lot of arrogance. They claim they’re great at everything. That’s not possible, and definitely not true. Everyone has flaws, but the inability to share them is a red flag for me.
“Good GPs are also very self aware of what they are and what they aren’t. These GPs manage their time well. They find partners to build a team that has complementary skill sets to their own. When I ask: Why are you not winning deals?, they have a great answer. If they can’t answer that, they probably have work to do understanding their own pitch. Moreover, the best GPs are consistent with their stories while open and willing to evolve.”
— @Cashflow_Cowboy
“For funds I declined to invest in, it came down to the person. They often take credit than share credit. I doubted their skills and ability to follow through. A lot of projects were often started but never finished.“
— Brent Goldman, Lancelot Ventures
“Managers that don’t appreciate that this is a journey, not a sprint. It’s the same as assessing a startup founder. We look for behavioral cues: approachability, willingness to accept feedback, and ability to go through pivots.
“At Revere, we share our ratings for GPs with our GPs. Say I give someone a four out of five on team, and they come back and insist on five out of five across the board. How receptive the GP is to constructive feedback (and address it) is a very telling indicator.“
— Eric Woo, Revere VC
“Usually GPs are really good at (typically) 2 or at most 3 of the following 6 things, in order to be top-decile:
Portfolio construction & management
Access to deals / networking
Ability to win deals
Company selection / financial analysis / assessing PMF and future value accretion
Active management to “add value” to those companies
Exits
“… And maybe fundraising / cost of capital.
“But if they aren’t aware of what they’re good at, that’s troubling. Once they know what they do to excel (and what they won’t) they usually become very good at focusing on what matters.
“Here are some examples:
Potential GP: ‘I am really good at all 6 GP characteristics above!’ Me: ‘Don’t call me, I’ll call you.’
Potential GP: ‘I am really good being a board member, I’m the best. I can make any shit company successful once I’m involved. I did this for three eCommerce companies in the 1980s, and I really think I can ‘turn around’ and exit eCommerce, adtech, fintech, digital health, AI / ML, beauty and fashion, etc. They’re all the same.’ Me: ‘Ummm…’
Potential GP: ‘I am great at deal sourcing from XXX network, and I specialize in AI. But vertical-wise, I see a lot of stuff, so I do a lot of stuff.’ Me: ‘Cool.’
“I also like to see more focused funds. A lack of ability to zero in on a particular thesis (e.g. B2B SaaS with certain characteristics) is at least a yellow flag, though if the GP’s core competencies support a generalized approach that’s fine.”
— Aman Verjee, Practical VC
The GPs are too founder-friendly
“Emerging GPs tend to be too founder-friendly. A great VC is like a personal trainer, not a cheerleader.”
— Chris Douvos, Ahoy Capital
There’s no follow-on strategy
“Another red flag is not having a follow-on strategy. If you’re a small fund, you are funding companies that will never get to profitability with the money you gave them. So they all have to raise additional financing. If you don’t have reserves in your fund, you need to prove that you know other funds or have an SPV or angel network that can fund your companies. If you don’t have an answer for how you’re going to be able to fund the companies in the next round or at least introduce them, that’s a flag.”
— Martin Tobias, Incisive Ventures
The follow-on SPVs take management fees
“They’re charging excessive fees on SPVs to LPs. Many LPs who invest in small emerging managers are in part doing so because they want the co-investment opportunities. And those co-investment opportunities should be at fairly favorable terms. The most favorable terms I’ve seen are zero and ten. I’m not saying everyone has to do it at that, but I have seen VCs try to do it at three and thirty – at premium terms relative to the fund. I think it’s a flag on the emerging manager if he/she is proposing to charge management fees on SPVs at all.”
— Martin Tobias, Incisive Ventures
They lack communication skills
“GPs sometimes don’t follow up with what the LP asked for. The follow up is very generic. For example, if the LP wants to co invest in XYZ sector, can you send names in the portfolio that might be interesting to them?”
— Anonymous LP, $30B AUM Fund
“Bad communicators who only answer with curt and short responses is a red flag.”
— @Cashflow_Cowboy
They don’t know the numbers or the rules of the game
“Plenty, but to extract one, we’ve found that managers that don’t know the numbers (i.e. what enterprise value within your portfolio will you need to get to a 3x+) is a huge red flag and leads to poor portfolio construction and decision-making. Saying you are going to return a 5X+ easily is not respecting how difficult it is, and probably comes with a lack of understanding of basic fund math.”
— Samir Kaji, Allocate
“Managers that don’t understand basic portfolio construction and fund modeling. You would be amazed how many don’t even have a spreadsheet that tracks current investments.”
— Eric Woo, Revere VC
“Emerging GPs tend to overestimate the value of prior experience and underestimate the value of investing skills like portfolio construction and discipline (not just on things like price, but also on things like security selection — for instance, not understanding the problems with SAFEs).”
— Chris Douvos, Ahoy Capital
“If they are carrying companies at valuations that seem out of whack, or indefensible (or if they can’t really articulate their valuation policy) that’s no bueno. That is ALWAYS a signal that the GP is not going to be aligned with me… I’ve known some very strong investors who have played this game and it’s a real problem for me personally.”
— Aman Verjee, Practical VC
They play the AUM and management fee game
“I think fund size is a real issue. The law of funds is really interesting. If you get a million-dollar allocation early on into a unicorn and it’s a smaller fund, you can return the fund multiple times over. If you do that with a $400 million fund, it’s harder to make those numbers work.
“So as an investor, you can play one of three types of games:
You can spit out rapid funds.
You can raise massive funds.
Or you can make massive carry.
“The amount of funds and management fees that have been raised recently are out of control. If you can think about taking 2% management fees on a $500 million fund – and obviously you got costs and expenses – you’re bringing home an annual income of $10 million. And that’s just one fund, and you do another and another. So, are you trying to create value or play the AUM game? And that is a red flag for me. I like small, steady, disciplined managers who are deeply passionate about early-stage and a certain sector. That typically means they won’t scale to a $1B fund.”
— Vijen Patel, 81 Collection
No investing experience
“Just like the only way to get good at wine is to drink a lot of wine. The only way to get good at investing is to see a lot of deals. A red flag would be a GP with no investing experience.”
— Lo Toney, Plexo Capital
Common Advice To Ignore
While far les prominent than investors advising founders on how they should run their business or startup investing advice at broad, there’s a small handful of commonly shared pieces of advice that new LPs often get. Certain pieces of advice might serve larger LPs who work with a different set of parameters than you do. The important part is understanding the why.
Having artificial timelines
“LPs also shouldn’t give artificial timelines. Most family offices and individuals don’t have deployment schedules. A big endowment, like Harvard, does.”
— Anonymous LP, $30B AUM Fund
The same is true for LPs as it is for GPs: Chasing logos
“Just because you spun out of a big firm doesn’t mean you’re going to do well as a new firm. These emerging managers are going to look good on paper, but they might not necessarily know what it’s like living in a chaotic environment. It’s not the same environment they grew up in when they were at a16z, or had another great name behind them. Different resources, different support, so different mentality. Connection with founders is incredibly important and you want to understand how that applies in a different environment.”
— @Cashflow_Cowboy
“I don’t know if this is advice that is shared, but many LPs over-index things like logos, GP commits, and early fund performance (which means very little within the first 3 years).”
— Samir Kaji, Allocate
“A big one is around geographic and pedigree bias. There is a trope that’s formed that if you’re a founder of GP that’s based in the San Francisco Bay Area — maybe went to Stanford or Harvard or MIT, that will position you into the very best networks to be successful.
“I’m not saying that just because you possess those characteristics that you can’t be successful. In fact, there are plenty that are. But there are also are a lot of really talented people outside of those networks too.
“I think a lot about this Warren Buffett rule: ‘To make a lot of money, you have to be both contrarian and right.’ Look a bit more widely in your funnel and invest in managers who don’t look like yourself and come from non-traditional networks and backgrounds. They’re identifying founders who may be working on some pretty amazing stuff that’s being overlooked.”
— Eric Bahn, Hustle Fund
Diversification for the sake of diversification
“Many emerging LPs are told to look for differentiation, but some things are differentiated in how bad (or mediocre) they are. Hedge fund managers say they’re seeking alpha, but sometimes you find it and it has a negative sign in front of it. What really matters is sustainable competitive advantage. How do you demonstrate and articulate your SCA? What is your unfair advantage in an extremely noisy market (and it’s gotta be more than just: ‘we’re part of the SF cool kid crowd/look at our AngelList track record of $50k checks’).”
— Chris Douvos, Ahoy Capital
Should you bet on emerging GPs?
“‘Stay away from Fund I/II.’ This is the wrong advice. Don’t underestimate new GPs. Being a new GP is like being a founder; it’s a long-term commitment. And two, stay away from GPs who don’t have resilience and are not hungry to win.”
— Cindy Bi, CapitalX
Do ownership targets matter?
“There’s a lot of surface level ‘buyer beware.’ Everyone talks about ownership targets. ‘Are you hitting your ownership targets?’ For large funds, that 15-20% ownership matters. You want the proceeds of the outcome to meaningfully impact the fund. Ownership is less important for a first or second time fund, which are smaller funds where a single great outcome, even at low ownership, can return the fund.“
— Eric Woo, Revere VC
Using fund-of-funds to get into emerging funds
“I would encourage a lot of emerging LPs to not go into fund-of-funds. As an emerging manager, I want fund-of-funds to invest in my fund. But as an LP, you get double-feed. If you’re going to invest into venture funds, invest directly in the manager yourself.
“What the fund-of-funds will tell you is that they can get you into funds you can’t get into. I’m also starting to see fund-of-funds for emerging managers, which I think is a great thing. For incredibly large LPs, I think it makes sense. They get access to someone else who’s going to do all the diligence on emerging managers. But that’s not for an emerging LP whose check size is $250K to a million dollar LP commitment. Fund-of-funds are for people with a billion dollars who are already invested in Sequoia and are writing $5-10 million checks.
“Typically you would pay one and ten for fund-of-funds. Then that fund-of-funds pays two and twenty. So you’re three and thirty behind as a fund-of-funds LP.
“For emerging LPs, it’s a good exercise to invest directly in emerging managers because it’ll help with your direct investment practices as well. If you invest in fund-of-funds, you’re never going to have those co-investment opportunities because you never build a relationship with the manager.“
— Martin Tobias, Incisive Ventures
Additional Tactical Tips
The below are tips that everyone were kind enough to share, but didn’t fit into the above categories. Nevertheless, I find them to be powerful in expanding how you think about being an LP.
You’re never too good to reach out.
“I will say about a third of my LP investments were into fund managers I never worked with before. I hear of these new GPs from talking with my network. If I like what they do, I’ll reach out via Twitter.”
— Sriram Krishnan, Kearny Jackson
“For every fund I’ve been in, I reached out to them, not the other way around. Every time I invest in a fund that’s either because I know the GP personally, or I know someone who knows the GP.”
— Brent Goldman, Lancelot Ventures
See if the GP has flexibility on the minimum check size
“One thing that can be helpful to know for first-time LPs: GPs often have some flexibility on their minimum check size. I’m a pretty small check (particularly since I’ve been living on a founder salary!), but I can bring other things to the table to help the GPs I invest in (e.g. I highlighted Janine Sickmeyer from Overlooked Ventures in my Forbes column, I’m an advisor to Zecca Lehn from Responsibly Ventures, I send them deal flow from my AuthenTech community of founders). I’ve had luck with reaching out and saying ‘I really believe in what you’re doing. Please let me know if you get enough large checks and have room for some smaller LP investments.’ They’ll usually need to get enough big investments first since there are SEC limits on how many LPs they can have, and then they can let in some smaller, value-add LPs.”
— Rebekah Bastian, OwnTrail
There are multiple ways to do reference checks
“There’s a two-part reference call check that I love that I learned from Scott Cook, who is the founder of Intuit. You ask, ‘I want you to tell me about David. Rate him from 1 to 10. 10 being absolutely perfect, and 1 being horrific.’ And you can basically ignore everything that is said. Most people say 8 or 9. You know they have their answer prepared.
“But then the second question is, ‘What will get David to a 10?’ And that’s where you hear the truth. That’s where you can pay attention.”
— Eric Bahn, Hustle Fund
“Investing into a fund is much like investing in startups. Why does this person have an unfair advantage over everyone else? I talk to the founding GP. I read VC Guide – think Yelp reviews for investors by founders. And if I think the team has an unfair advantage, I invest.”
— Brent Goldman, Lancelot Ventures
“Ask to talk to other current LPs – you can learn a lot about how you will be treated once the fund has your money.”
— Paul Griffiths, 15 & Change
“Being an LP is a ground game. It requires talking to founders and co-investors, and you won’t get much from surface-level reference checking.
“There’s no specific number that I shoot for. I once heard an LP claim to have completed 80 reference checks for one commitment. To me, that seemed like they were doing diligence for the sake of doing diligence. You could have gotten to the same answer well before 80. I reached close to 20 checks in diligence on a fund once, but I often need far less than that. The more important thing is you’re answering the questions you have that pop up in your diligence, that you only do whatever references that you need to get to a yes or no.”
— Anonymous LP, Private Wealth Management Firm
“We are all operating in the business of emotions and trust. It’s best to build trust by word of mouth or references. I’ve never invested in a fund without talking to another manager or entrepreneur in the portfolio. This is across the stack. Top $100B asset managers do 20 back references on $100M venture capitalists. $100M venture capitalists do 20 back references on $10M start-ups. And $10M start-ups do back references on employees. Together, with the bond of trust, this system creates an impact on the world.
“In practice, for example, I don’t have a lot of domain expertise in web 3, but I have plenty of friends who do. So before I invested in [name redacted], I called four people and they all told me this manager was one of the top five.
“This is the under-pinning of asset allocation, but unfortunately this also leads to systematic issues. In fact, I would say this referral network is part of the issue of neglected founders, industries, and geographies not being able to get funded. It’s a huge issue in our country that 2% of women get all VC dollars. That’s horrendous and that means that >50% of our population only gets 2% of funding. That isn’t right. We need more capital to flow to underrepresented or neglected founders or industries or managers. These new managers may not have the network to build traction, but I’m loving all the new amazing, specialized emerging managers doing great work with new strategies popping up.”
— Vijen Patel, 81 Collection
“Do reference calls. Talk to some founders they’ve invested in. Talk to startups in their anti-portfolio. And talk to some of the founders that didn’t work out. For the latter, how did they manage that? What do the founders think of them? If you only talk to the winners in their portfolio, they look like cheerleaders who got lucky and got into some great companies.”
— Asher Siddiqui, Sukna Ventures
Follow-on investors aren’t as big of a differentiator as you might think.
“Top-tier follow-on investors in the past 48 months are no longer a differentiator. Existing managers all talk about mark-ups. Most managers that aren’t incompetent have markups and brand name follow-on investors over the last three years.”
— @Cashflow_Cowboy
Get granular with a fund’s follow-on investors
“A lot of LPs act like they care about which funds are making investments alongside emerging managers. But who those follow-on investors and co-investors are will mean different things to different people based on the following factors.
Which partner at that established fund is actually leading the deal? Is it someone with a track record or a more junior partner?
Which fund are they investing from? Is it their core fund, or a satellite one they’re experimenting with?
“You ultimately need to get to know the people behind every investment decision.”
— Anonymous LP, Private Wealth Management Firm
March 30th is more important than you think
“Ask when you will get your K-1s and insist that it is before March 30th, otherwise you will be stuck extending every year and that’s just a pain.”
— Paul Griffiths, 15 & Change
Don’t rush into investment decisions
“We don’t rush into investment decisions. It takes us time to reach conviction. Unlike early stage VC, in a fund-of-funds, you expect returns from all your investments. Conviction is required to reach trust. We might not rush into the first vintage, but based on how well we get to know the fund manager, might jump into the second vintage.”
— Itay Rotem, EdRITECH
“There are also a lot of venture funds out there, take your time and meet with a range of GPs before you invest to get a feel for what the investment opportunities are and what feels right for you for your LP program.”
— Beezer Clarkson, Sapphire Partners
“Yes, meet at least 20-30 managers before you make an investment, or use a partner. Like anything, at first you will like almost everything, but it takes reps to truly start to build pattern recognition, and manager investing is a probability based exercise; meeting just a few won’t provide enough data points to have a good sense of what meaningful differentiation looks like (i.e.. meaningful differentiation increases the probability of consistent success, much like counting cards in blackjack. It doesn’t guarantee a payout, but you want someone that has their own version of ‘counting cards’.”
— Samir Kaji, Allocate
“Emerging LPs shouldn’t be taking any advice or making any decisions until they’ve met with at least 100 investment firms (and as many different types of firms as they can).
“The reality is that LPs don’t help each other as much as they should. There’s this cooperation versus competition dynamic, this friendly competitiveness, and LPs will be more helpful in less access-constrained deals. That’s something you need to understand as a new LP.”
— Anonymous LP, Private Wealth Management Firm
TVPI hides good portfolio construction
“When I do portfolio diligence, I don’t just look at the multiples, but I look at how well the portfolio companies are doing. I take the top performer and bottom performer out and look at how performance stacks up in the middle. How have they constructed their portfolio? Do the GPs know how to invest in good businesses?
“I’m not just bothered by my TVPI. I also try to look at the companies and the revenue they’re bringing in. Some of a fund’s portfolio companies that haven’t raised a subsequent round, which may not look as good in TVPI, but they may not have needed to raise any subsequent capital to scale further. The point is to assess the quality of the underlying portfolio of ‘businesses’ — so factor that in and look at likely exit opportunities for those companies.”
— Asher Siddiqui, Sukna Ventures
Don’t invest in ESG for the sake of ESG
“Avoid ‘ESG’ if they reduce financial returns, are comprised of unaudited made-up metrics that won’t get reported (e.g. ‘we love the environment, and will only invest in ‘green’ companies’ but the LPA doesn’t provide mention of reportable, audited environmental goals or KPIs, or define what ‘green’ means).”
— Aman Verjee, Practical VC
Past performance is not indicative of future performance
“It takes three funds worth of track record to make it meaningful. But even then, it’s even more complicated. Your strategy and risk-to-return profile for a $5 million Fund I will look meaningfully different than yours for a $150 million Fund III. I wouldn’t recommend relying on these blunt instruments for the emerging manager category. So the advice here is that LPs cannot rely on past performance of earlier funds if the latest fund’s strategy has shifted.”
— Eric Woo, Revere VC
Have an LP thesis
“LPs should have a portfolio construction model. What percent are you investing in generalist funds? What percent in thesis-driven ones? And also, what stages? Pre-seed? Seed? A- and B-funds? Multi-stage?
“You should take the total amount you want to put into funds and separate it with a portfolio construction model that makes sense for your risk tolerance.
“Is your portfolio allocation driven by financial returns or certain goals you have? A lot of LPs might want to invest for non-financial reasons – could be diversity, geographic coverage, verticals, or stage. They might want to support female founders, or ESG. Just like I encourage angels to have a thesis, LPs should have one too. Why am I doing this?”
— Martin Tobias, Incisive Ventures
Why are you helpful as an LP?
“As an LP, you also have to think of your unique value-add. If you have a brand, your name helps with credibility of the fund and helps the GP reach more LPs. On the other hand, you have to think about what kind of LPs a GP would offer their pro rata rights to? For an SPV strategy, those are LPs who:
Backed and believed in the GP from Day 1.
Has written big checks, and/or
Can help the fund’s portfolio companies.”
— Shiva Singh Sangwan, 1947 Rise
“We did have several of those established, persistent performers in the PE/VC portfolio in my prior role though, and that’s because those GPs look for more than just money. They may be looking for someone who’s strategic to their portfolio, but more so they’re looking for kindred spirits. Show why you’re also a convicted investor, like them, because they’re really just looking for true believers.”
— Anonymous LP, Private Wealth Management Firm
Don’t put your eggs in one basket.
“Putting money into an early-stage fund is a very, very high-risk alternative asset category. Every normal family office puts maybe 10 to 15% of their total net worth behind this asset category. Don’t concentrate behind a single manager. Spread it across five, possibly ten, managers who have truly varied networks.”
— Eric Bahn, Hustle Fund
“Invest in a larger number of fund managers than you might think is appropriate. Focus on smaller, tightly managed micro-VCs (I’m assuming that the LP can’t get into the Sequoia / Founders Fund / Benchmark types). Really dig into their strategy, their edge, and their pipeline. And, spend time with them and learn the trade, get into their co-investment program and be ready to execute!”
— Aman Verjee, Practical VC
“Does it make sense to have 17 funds all in web3? Or 17 funds in fintech? Or even 8 in web3 and 9 in fintech? My own fund is counter-cyclical, and I think an LP needs to build a portfolio of top managers across the economy. Healthcare, IoT, fintech, web 3, and other differentiated strategies can comprise an excellent portfolio.
“If an entrepreneur is building in climate tech, there are 10 amazing funds out there who really know climate tech. If you’re building in web3, there are several funds that are so close to the nucleus of innovation and that’s what it matters. But if you’re building in hard industries, we’re trying to become one of the ten. A portfolio that consists of a basket of these top ten funds makes a lot of sense if you believe in investing in venture.”
— Vijen Patel, 81 Collection
“LPs can get very excited about tech and venture. They still need to remember this is a high-risk asset class. They should have clarity of what their expectations are. Venture used to traditionally be 5% of private equity. This is funny money – play money. It’s less so now, but still is. LPs do it because it has the potential to provide outsized, risk adjusted, returns.”
— Asher Siddiqui, Sukna Ventures
Patience is a virtue
“It may take seven to ten years (or longer) to see any real return, so be patient.”
— Cindy Bi, CapitalX
“The reason I chose a lot of managers is also so I can start tracking data. I won’t do re-ups right away because I want to see how they’ll perform over a couple decades or even over 6 years.”
— Vijen Patel, 81 Collection
In closing
The above is by no means all-encompassing as you refine your craft as an LP. Nevertheless, if you’re looking to dive deeper into the art of investing in non-obvious capital allocators, I hope this blogpost serves as a launchpad for your career. Make new mistakes rather than old ones. The world is better off learning from and supporting each other.
If you learned something from the above, I urge you to reach out to any of the above legends and share your appreciation with them. And if you employ any of their tactics, let them know how empowering it was.
Trust me, it’ll go a long way.
*I’ve made light edits to the above quotes for clarity and since my hand can only take so many notes per second.
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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
