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.
I’m sure every founder has heard that line at least 50 times every time they’re in fundraising mode. Hell, even outside of it. Pshhh, I’m guilty of saying it myself, while I do try to catch myself when I do. You’d think being helpful is table stakes as an early-stage investor. Surprisingly, being helpful as an investor is actually a huge differentiator.
Most investors are only as helpful as their check size, despite pitching their value-adds a million and one times. Some investors are extremely helpful only within the funding window(s) they are participating in. For instance, a seed investor is largely helpful during the 12-18-month funding window between the seed and the Series A. Others are helpful when they are asked. And a small handful of investors are true champions by being proactively helpful.
One of my favorite stories when I was interviewing LPs for the emerging LP playbook was when Brent invested in a GP who had a track record for being proactively helpful. This GP “was one of [Brent’s] first investors. He would often come into our office, and without being prompted, proceed to write code against our APIs.” Unprompted. Unsolicited, but insanely helpful.
Earlier this week, I was also reading the October investor update from a founder I love, and in it, he was talking about how much he loved the team at Sequoia (who have yet to invest), and shared that he had learned more about product in the last “3 days than [he had] in the last 3 months.”
A big part of the reason I joined the On Deck Angels team last year was to be a part of a community bringing the world’s most helpful investors together. As such, I’ve been lucky enough to be a student to our community on how they’re helpful — whether they choose to invest or not. Some examples include:
Writing a 3-5 page bug report for every founder you take a meeting with. This teaches an investor two things: 1/ to be judicious of one’s time and only take meetings with founders that you are truly likely to invest in, since these take a while to research and write up, and 2/ to always think in a “give first” mentality.
Record a Loom breakdown of why you decided to pass and what would get you over the fence. I’ve shared this before, but one of my favorite VC quotes and has been since the day I learned of it is: “There is no greater compliment, as a VC, than when a founder you passed on — still sends you deal-flow and introductions.”
Being able to admit how you can’t be helpful. As an investor, you don’t have to be good at everything, just really, really good at one thing, or a small handful of things.
Sharing their memos publicly on why they’re excited about a startup. This helps build a startup’s reputation, and also your own brand as a thought leader.
Sharing your deal memos and founder asks with your LPs (if you run a fund or syndicate). For this, admittedly, it’s best to get the founders’ approval, given the confidential nature of certain details.
Make an intro for every pitch meeting you take. Intros are often extremely high leverage. It takes you 1-2 minutes to write something up and send a double-opt-in intro. And oftentimes, can save the founders from at least tens of thousands of dollars worth of decision-making mistakes or costs. Of course, that requires you to have either photographic memory (which I don’t have) or a really good CRM. For the latter I use Airtable, and I track small details like: ideal catch-up frequency, preferred medium of communication, chill factor (yes, some of my intro emails can get a bit wonky depending on the person), and what makes them the best dollar on a founder’s cap table.
Many of the above aren’t necessarily hard to do, but just requires a consistent commitment to do them well. And of all the many ways one can help, they all fall into three buckets:
Introductions
Strategy, decision-making, and tactical advice
Downstream and co-investment capital
The last is the most obvious. The second is easy to understand, but often the hardest to execute on, and often comes from being an active or former operator yourself. Hunter Walk of Homebrew has this line, “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.” Advice is just as helpful as it is dangerous. Something I’ll likely dive into in a future blogpost.
But for the purpose of this one, I’ll focus on introductions.
Network liquidity
I was recently reading Shawn’s chronicled reflections from his time as a Partner at On Deck — someone I am deeply fortunate to have worked alongside. In it, one line immediately grabbed my attention:
“Network liquidity is table stakes. […] This refers to how successful we are at connecting founders to people that are relevant to their needs and asks. The most important dimensions to consider are accuracy (how relevant was an introduction) and speed (how fast did you deliver).”
In 2022, and I imagine even more so, in the next few decades, it’s not about who you know — ’cause frankly, everyone will know everyone else. Social media, the metaverse, web3, the Zoom-ification of everything, and the rush back to IRL will only make this easier. I don’t believe any investor — or in fact, anyone, period — will have a “proprietary network.” So instead of who you know, it’s about how well you know them, and your ability to leverage that relationship.
We see this especially in the venture markets. In my recent blogpost, Sapphire’s Beezer shared: “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 ).”
I wrote quite a relevant essay a few months ago about how to write email forwardables. In order to tap into someone else’s network liquidity, there are two things you must establish:
Your rapport with the person you’re asking it from
Their rapport with the person you want to get to know
Requester and matchmaker rapport
I can’t speak for everyone, but my willingness to make intros depends strongly on both of the above, especially the former. Selfishly speaking, even if I don’t know the person who will receive the intro nearly as well, to put it bluntly, if I know I can look good to that person when I make it, that’s a strong motivator to do so. For that to happen, I need to fall in love with something about you — the person who would like to be introed. It could be you (usually the greatest motivating factor) and your passion. Even better if your passion is contagious. It could be your product. Or your insight. Usually, it’s some permutation of the afore-mentioned.
I meet with 10-15 net new founders per week. 25-30, if it’s accelerator season. Given my job description, almost every single founder asks me for intros. Sometimes, even without context.
Matchmaker and intro recipient rapport
The other side of the equation is the rapport I have with the person you want to get to know. The truth is the world of intros is like any other asymmetric game. The most well-known, busiest, and often hardest-to-reach people are the ones bombarded with the most intro requests. But like any other human being on this planet, they only have 24 hours in a day.
As a matchmaker myself, I have to cognizant not to overwhelm incredibly busy individuals with a flood of intro requests. And it is my job to triage requests. Sometimes, it’s also helping, in the case of fundraising, founders recognize not what they say they want, but to help them figure out what they really need.
In making requests to famous friends
There are times when the busiest people I know are the only people are capable of fulfilling the ask. So, it also comes down to your accumulation of social capital with the intro recipient. I have two columns in my Airtable CRM, labelled:
Why I am useful to them
Is my usefulness a priority to them? (on a scale of 1-5)
With the former, have I given before I have taken? Have I helped them before? Additionally, is the intro request more of a give or a take? A great startup with a strong team and traction for an investor is more of a ‘give.’ It’s deal flow from them. On the flip side, a founder asking for free advice is more of a ‘take.’ In general, ‘takes’ require more social capital than ‘gives.’
With the latter, priorities change. You may be useful in one phase in their life, but no longer so, in another. For example, when an emerging manager is fundraising for their Fund I, I am someone who is extremely top of mind for them, but when they’re not, I slip in importance. But regardless of the phase in their life, if someone is kind and thoughtful AND you’ve helped with a major decision or inflection point in their life, they’ll always be around. That said, I never try to abuse that goodwill. Personally, I hate being in debt and having others be in my debt.
You can also be “useful” in many different ways. For instance, doing interesting things is one way. One of the most famous people I know with millions of followers across his socials is willing to entertain any ask I ask of him under the condition I invite him to every social experiment I host in LA.
In closing
The more relevant an ‘ask’ is to the recipient, the more likely they’ll respond positively. The more top of mind you are and the more social capital you have with someone, the faster they’re likely to respond. We live in a saturated market of attention. Everything in the world is asking for ours — social media, kids, friends, work, portfolio companies, chores, Netflix, and sleep. And by no means all encompassing.
As you scale yourself as an investor, it’s important to think critically about who is in your network and how well you know them. If you’re a syndicate lead with 500 LPs, how many of them are passive capital? How many of them want to actively help your portfolio?
If you’re an investor who’s a Xoogler and wants to leverage the Google network, who do you know will go out of their way to help you? How many of them have you on speed dial? Which vintage were you a part of?
The great Richard Feynman once said, “You must not fool yourself, and you are the easiest person to fool.” One of the greatest fallacies an investor or even a founder can make is to assume they have a larger leverageable network than they actually do. Only to realize that when you do need to draw on these connections, you’re unable to.
So, if you have the time this weekend or the next, sit down with a critical eye and ask yourself: How liquid is your network?
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.
When I first jumped into venture, there was a wave of founders who believed that a great product will sell itself. But in the past few years, under the proliferation of startup content, discourse and amazing Twitter threads, while anecdotal, I’m happy to have seen far fewer founders who believe in that extreme.
Nevertheless, that dogma hasn’t completely disappeared. Rather than sales and marketing, I’ve realized this to be more the case on the fundraising front.
How often are you in the batter’s box?
This past week, a handful of pre-seed founders asked me for fundraising advice. On Monday, a founder I had chatted with at the beginning of the pandemic reached back out to let me know he was now starting to fundraise for a new idea. Naturally I asked him what he learned from the last idea.
To which he responded, “There weren’t enough investors interested in my last idea.”
I followed up, “How many did you talk to?”
“Twenty.”
That’s not nearly enough. Especially for what was his first institutional round. Moreover, like most other founders, he wasn’t an insider. As such, I believe he should have pitched to more. A lot more.
He’s not alone. Two other founders I chatted with felt they had already tried everything after getting rejected by 30 and 40 investors, respectively.
I mentioned in a blogpost back in April that if you’re an emerging fund manager raising a Fund I, think of it like raising 10 Series A rounds. For most Series A rounds, a founder talks to about 50 investors. So for a Fund I, you’re likely to talk to 500 LPs to close one. An LP I talked to for a blogpost that will soon come out chatted with a GP who pitched 625 investors to raise her first $18 million fund.
Why do I mention this? While this is equally true for emerging fund managers raising a Fund I — a fund that’s pre-product market fit, if the average Series A founder needs to pitch 50 investors, as a pre-seed founder, you need to talk to double that number. If you’re lucky, you can stop pitching sooner. But at the very minimum, you should expect that ballpark number. And that’s also why fundraising is a full-time job.
The more realistic your expectations, the more efficiently you can set up your pipeline, the faster you can get back to building your world-changing idea.
The takeaway
Never run out of leads. You never want to be in the position where you have to go back to someone who passed on you. Keep your funnel open. Every time you pitch a VC or an angel, especially those that say “No,” ask them: Which investor would you recommend who might be interested in what I’m building?
A lot of founders try to optimize for warm intros. But most people who say No to you won’t go out of their way to help you, especially asynchronously. They’d much rather spend time on their own portfolio companies. So, don’t add in asynchronous steps that would increase friction. You don’t need warm intros. You just need names. And if any investor gets recommended more than three times, it’s worth just cold messaging that person sharing that they came highly recommended from the investors you’ve chatted with so far.
For those who say “Yes” to you, it is likely you won’t ever reach profitability with the capital they gave. Early-stage investing, for instance, the pre-seed, luckily, is very collaborative. If you’re raising a $1M pre-seed round, that leaves room for a lead investor of $500K, $3-4 $100K checkwriters (emerging fund managers, syndicate leads, or active angel investors), and a bunch of smaller, but extremely valuable investors. Ask each for who they’d like their co-investors to be. Even if those recommendations don’t commit this round, collect the names for your next round.
During your first institutional raise — hell, even prior to that — you’re an outsider. No one’s heard of you. But there are still people out there who believe in the world that you want to create. You just have to find those early believers. Believers in you. Believers in the future you see.
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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.
“Readily available quantitative information about the present is not gonna give you they key to the castle. […] If everyone has all the company data today and the means to massage it, how do you get a knowledge advantage?
“The answer is you have to either:
Somehow do a better job of massaging the current data, which is challenging; or you have to
Be better at making qualitative judgments; or you have to
Be better at figuring out what the future holds.”
Those are the words of the great Howard Marks on a recent Acquired episode.
When most of us first learned economics — be it in high school or college, we learned of the Efficient Market Hypothesis. In short, if you had access to both public and private information, you would be capable of generating outsized returns that outperformed the market.
The truth is that reality differs quite a bit. And that’s especially in early-stage investing. Investors often make investment decisions with both public and private information at their disposal. There is admittedly still some level of asymmetric information, but that depends on deep of a diligence the investors do. Yet despite the closest thing to a strong efficiency, there’s still a large delta between the top half and bottom half of investors. The gap widens further when you compare with the top quartile. And the top decile. And the top percentile. Truly a power law distribution.
Massaging the data
I’m no data scientist, although I am obsessed with data. But there are people who are, and among them, people I deeply respect for their opinion.
There’s been this relentless, possibly ill-placed focus on growth (at all costs) over the last two years. Oftentimes, not even revenue growth, but for consumer startups, user growth.
I want to say I first heard of this from a Garry Tan video. The job of a founder pre-product-market fit (pre-PMF) is to catch lightning in a bottle. The job post-PMF is to keep lightning in that bottle. Two different problems. Many founders ended up focusing on or were forced to focus on (as a function of taking venture money) scale before they caught lightning in that bottle. They spent less time on A/B testing to find a global maximum, and ended up optimizing for a local maximum.
Today, or at least as of September 2022, there’s this ‘new’ focus on retention and profitability (at all costs). But there’s no one-size-fit-all for startups. As a founder, you need to find the metric that you should be optimizing for — a sign that your customers love your product. Whether it’s the percent of your customers that submit bug reports and still use your product or if you’re a marketplace, the percent of demand that converts to supply. Feel free to be creative. Massage your data, but it still has to make sense.
From a fund perspective, equally so, it’s not always about TVPI, IRR, and DPI, especially if you’re an emerging fund manager. Or in other words, a fund manager who has yet to hit product-market fit. You probably have an inflated total-value-to-paid-in capital (TVPI) — largely, if not completely dominated by unrealized return. The same is true for your IRR as well. In the past two years, with inflated rounds and fast deployment schedules, everyone seems like a genius. So many investors — angels, syndicate leads, and fund managers — found themselves with IRRs north of 70% for any vintage of investments 2019 and after. Although an institutional LP that I was chatting with recently discounts any vintage of startups 2017 and after.
So the North Star metrics here, for fund managers, isn’t IRR or TVPI. It’s other sets of data. I’ll give two examples. For a fund manager I chatted with a few weeks ago, it was the percent of his portfolio that raised follow-on capital within 24 months of his investment because it was more than twice as great as the some of the best venture firms out there. Another fund manager cited the number of his LPs who invested in his fund’s pro rata rights through SPVs.
Making qualitative judgments
In this camp, these are folks who have an extremely strong sense of logic and reasoning. When a founder has yet the data to back it up, these investors go back to first principles.
In my experience, these investors are incredible at asking questions, like how Doug Leone asks a founder for their strengths and weaknesses. But more than just asking questions, it’s also about building frameworks and knowing what to look for when you ask said questions.
For instance, every investor knows grit is an important trait in a founder. More than knowing at a high level that grit is important, what can you do to find it out? For me, it boils down to two things.
Past performance. In other words, prior examples of excellence that they worked hard to get.
Future predictors. I ask: Why does this problem keep you up at night? Or some variation. Why does this problem mean so much to you? Why are you obsessed? Are you obsessed? Why is this your life’s calling? And I’m not looking for a market-sizing exercise here.
While I don’t claim to hold all the truths in this world, nor can I yet count myself in the highest echelons of startup investing, the most I can do here is share my own qualitative frameworks for thinking:
One of my favorite thought pieces on the internet is written by a legendary investor, Mike Maples Jr. of Floodgate fame. In it, he illuminates a concept he calls “backcasting.” To quote him:
“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.”
Early-stage investors must have the same genetics: the ability to see the future for what it is before the rest of humanity can. And they back founders who are capable of willing the future into existence and create reality distortion fields, a term popularized by Bud Tribble when describing Steve Jobs.
When I first jumped into venture, one of the first VCs I met — in hindsight, a futurist — told me, “Some of the best ideas seem crazy at first.” A visionary investor is willing to take the time to detect brilliance in craziness. Paul Graham, in a piece titled Crazy New Ideas, proposed that it’s worth taking time to listen to someone who sounds crazy, but known to be otherwise, reasonable because more than anyone else, they know they sound crazy and are willing to risk their carefully-built reputation to do so.
For 10x founders and investors alike, the more you hear them out, the more they make sense. That said, if they start making less and less sense the more you listen, then your time is most likely better spent elsewhere.
In closing
As you may already know, a great early-stage investor requires a different skillset than a great public equities trader or a hedge fund investor. You’re more likely to work with qualitative data than quantitative data. Regardless of what archetype of a venture investor you are, you have to believe that we are capable of reaching a better future than the one we live in today. It is then a question of when and how, not if.
Of course, I don’t believe that these three archetypes are mutually exclusive. They are more representative of spectrums rather than definitive traits. Think of it more like an OCEAN personality test than a Myers-Briggs 16 personalities.
To sum it all, I like the way my friend describes venture investors: pragmatic optimists. Balance the realities of today with how great the future can be.
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.
On the second half of a late summer Friday, as I was overlooking the singed blades of the parched grass in our front yard, I found my good friend, Andrew, in my inbox. An inbox that was about to be empty from filing an eclectic collection of investor updates, food science analyses, tech articles, and my weekly subscription of Substack extraordinaires into my Read Later folder.
An email headline in boldface. All it would take would be two clicks. Two clicks to add to my party of internet writers I would be conversing with over a Saturday morning of roasted hojicha tea. Instead, I clicked once. Just once. And I’m glad I did.
Andrew started writing again. Pen to paper. Or rather, finger to keyboard. And that, that was worth celebrating. I, like many of his other friends, had been starved, deprived, relieved of his prose given his busy schedule. In it, he postulated the relationship between commitment and conviction.
“Commitment helps you stay on the path. Conviction is what calls you to the path in the first place.”
In sum, the pre-requisite for commitment is conviction. And so, it got me thinking about the source of conviction…
From inspiration
For decades, athletes have tried to break the 4-minute mile. According to British author John Bryant, since 1886. “It had become as much a psychological barrier as a physical one. And like an unconquerable mountain, the closer it was approached, the more daunting it seemed.”
But it wasn’t till May 6, 1954, did Roger Bannister break it with a time six-tenths under the mark. As soon as Bannister did it, 46 days later, another did. One year later, three runners broke the once elusive 4-minute barrier in one race.
The thing is, nothing technological had changed in the world when all these runners post-Bannister broke the four minutes. Nutrition hadn’t drastically improved. Neither was there drastic evolution in the technology of shoes. Yoram Wind and Colin Crook argues it was a mindset shift. The impossible was possible.
We see the same notion today in the world of emerging markets. In these markets, the first wave of unicorn founders is usually spearheaded by Harvard and Stanford grads building X for Latam or Y for Africa. For instance, both of Grab’s founders are HBS graduates. Gojek’s Nadiem is no exception. Nubank’s David Velez holds a similar Stanford GSB degree. So does Cabify’s Juan de Antonio. Rappi’s founders are also Stanford alumni. And the list goes on. They come with the Silicon Valley mindset in a market underestimated by not only the broader world but by the homegrown talent themselves. I like the way a Midwest founder-turned-investor once put it, “My mind is in Silicon Valley, but my feet are in the Midwest.” The same is true for this first wave.
And once they’ve proven it’s possible to reach unicorn status, the second wave follows quickly after.
Most people follow in the footsteps of our predecessors. Older siblings are the same for their younger siblings. Parents are that for their children. While I’m not a parent yet myself, I do aspire to be that for my children. Equally so, that’s why we need diverse representation in media, in positions of power, and in stories.
For many, conviction comes from examples to disprove the limitations of our own imagination.
From emotion
For a handful of others, conviction comes from a deep desire to prove or disprove.
When Michael Phelps’ eight gold medals in Beijing were on the line, their coach Bob used what the French team was boasting on the papers as motivation in the locker rooms. “The Americans? We’re going to smash them. That’s what we came here for.” And soon after, the world was blessed with one of the greatest races to date. A race of which the Americans — the underdogs — pulled a miraculous spectacle of conviction and resolve.
For founders, you need obsession, not just passion. Many of the best ones have a personal vendetta — a deep, unquenchable desire borne out of time spent in the idea maze. Every successful founder needs to perform 10-15 miracles in the startup to household name journey. Trials by fire that are meant to deter the fainthearted.
After chatting with a number of limited partners (LPs, folks who invest in venture funds) over the past two months, I’ve realized the thread of founder obsession continues here. That investor-market fit is not just a function of professional experience but also of life experience. Once again, a deep desire to change the world from personal frustrations and the hope that no one will ever have to go through what they went through.
In closing
Earlier this year, Reed Hastingsshared a profound line with the graduating class, “[stories are] about harnessing the human spirit.” Conviction starts from the story we tell ourselves. The story itself is bound by the limitations of our own imagination. And conviction happens to be the belief that we can will our imagination into existence.
Michelangelo once said, “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.” Commitment is the dedication to your conviction. A devotion to say no to distractions and yes to the person you want to be.
We live in a world filled with shiny objects. So, ask yourself, do you want what others want? Or what you truly want? Is your conviction inherited or innate?
I was listening to the latest episode of the All-In podcast, and David Friedberg echoed a similar notion for the greater human race, “What differentiates humans from all other species on Earth is our ability to tell stories. A story is a narrative about something that doesn’t exist. And by telling that narrative, you can create collective belief in something. And then that collective belief drives behavioral change and action in the world.”
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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.
I forget where I heard this recently, but I thought it was a great breakdown of how we are all a function of our past.
When I first jumped into the action-packed world of venture, the most daunting part of the job wasn’t the spreadsheets or the modeling or asking great questions to founders or being a thought leader. It was the seemingly sustained extroversion that was necessary to be successful in the field.
Everyone, but especially the best investors, seemed naturally extroverted. And, well… I wasn’t. And neither did I want to be. To me, being an extrovert just seemed so exhausting. That said, it didn’t mean I didn’t enjoy every second chatting with amazing founders and investors. I was just — still am — the person who taps out two hours into a party. Three, max. In fact, I used to be a stereotypically shy introvert back in grade school. Comfort and safety were my best friends.
So, the reason I’m sharing all this in the first place is that we are all a product of our history. In the world of startups and VC, it seems like the best founders and investors were born extroverted and with great charisma. They were daring, rebellious, and ambitious from the start. They have these wild stories of how they broke the rules as kids and how each of those anecdotes made them who they are today. And somehow they turn each of the afore-mentioned into great Twitter threads. But I digress.
I, for one, have not had those same experiences. But when I finally entered college, I let what would have been some of my most formative experiences slip through my fingers – a freshman year crush, the opportunity to invest in a classmate who became a world-class founder, just to name a few. All of the above opportunities I was deeply curious about but didn’t have the courage to speak up. And I beat myself up over it. So today, my spurts of extroversion isn’t a trait I was born with, but motivated by the deep regret I used to and probably still do carry of my past inability to seize the moment. A past I am rebelling against.
And I know I’m not alone. Having chatted with numerous introverted founders and investors I deeply respect, I know I’m in good company. For those reading who fall under the same cohort, you are too. We just don’t speak out much, so it may be hard to tell that we exist. Of course, this is only one example among many in a cosmos of life experiences and characters.
So, as you’re charting your life’s journey and sharing it in an interview, coffee chat, or fundraising pitch:
Which part of your past are you rebelling against? Which part are you running towards?
And be honest. If you can’t be with the world, be so with yourself.
As a result of writing a soon-to-be-published blogpost on how limited partners (LP) think about investing in VC funds, one LP shared a similar line of thinking. For emerging fund managers (equally true for founders), why does this product/space mean so much to you? The answer isn’t just because you worked X number of decades in it, but something more fundamental. If you don’t have one, you might find your founder-market fit elsewhere.
The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.
Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.
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.
When I was in New York last week, I had the fortune of catching up with one of my favorite people inside the rustic walls of Il Buco. Needless to say, an hour and a half was not enough to contain months of development and change. So, to continue our tea, the next day, after she met up with the one of the heavyweights in her industry, she asked:
“How do you keep your enthusiasm in check but show it to the extent that shows respect to the person and also have a conversation as equals?”
In sum, how do you fangirl/fanboy without losing your composure?
I don’t. It happens less frequently now, but I still do.
In fact, even when I try not to or attempt to convince my conscious self, this is just another human being doing their best to live the life they want, there’s something that my eyes do without fail every single time. Here’s to hoping it’s not painfully obvious to the other person.
In fairness, I actually don’t know what I look like when it happens. I can just feel and SEE it through my eyes every time. In fact, I don’t even know what this phenomenon is called. Or if there’s a word for it. If I were to describe it, it’d be if the thousand-yard stare and diplopia had a baby.
It’s completely involuntary. All my other senses and cognitions work just fine. And when it happens, I start blinking a lot more which usually recalibrates my gaze.
Physiological response aside, over time, I’ve simmered down my ability to respond into two ways, especially when my brain decides to turn off. One for each situation.
I’m prepared. For instance, this is a scheduled meeting, or I know I will see this person at an upcoming event.
I’m unprepared. The canonical serendipitous elevator ride. For instance, bumping into them at an event. Or true story, we happened to both be helping to carry A/V equipment backstage post-show.
When I’m prepared…
The goal here is to know the other person better than they know themselves at the point in time. This is the same mentality I carry into both conversations in public and private spaces. The former with interviews, fireside chats, and panel discussions. The latter in the form of coffee chats, dinners, happy hours, and the like.
Depending on the timeframe, I come prepared with a different number of questions. But generally, for every 30 minutes, I come with three questions.
The first question is to establish rapport. And it’s always a personal one. I almost never start the conversation with pure “business.” This sets the tone for the rest of the conversation, as well as how candid they will be with you.
You’ll have to do your research. Some may require more digging than others. That said, don’t take it too far by finding their home address or social security number. Here, I usually look for fun facts. Like they did street dancing back in high school or they love going to stand up comedy shows.
If you’re going to take away one thing with this question, it’s to surprise and delight.
For the second one, which is usually the optional question if we’re short on time, I love understanding people’s inflection points. For example, why did they go from consulting to acting? Or from an art gallerist to a VC?
Not just the fact that they went through a massive delta, but I love understanding what they were thinking before, during and after they made the transition. Was it a decision that was supported by their family and/or peers? Was it a difficult decision to make? What got them over the activation energy to commit to this new lifestyle?
The third question is akin to the one I always advise founders to think about when talking to investors. Why would this investor be the best dollar for your cap table? Similarly, even if you’re not raising money, what kind of question can only the person in front of you answer? Or very few others can? It’s usually a function of their work or life experience, where they end up becoming uniquely positioned to talk about that topic.
As a prelude to this last question, I usually preface why this question means a lot to me. Why do I need this answer? Show that you have spent time in the idea maze. Time thinking deeply about the topic already. Naturally, anything that is googleable is off-limits here.
You have one chance to make a great first impression. Don’t waste it.
Cutting it short
Just as it’s important to start the conversation on a high note, in my opinion, it’s even more important to end the conversation on a higher note. As such, I have a three rules of thumb:
Never overstay your welcome. It’s always better to cut the conversation short than to end with awkward silence. Be extremely acute to where the clock is compared to how much time you’ve asked of them.
Have a go-to phrase (or phrases) to end the conversation. One of my favorites is, “As with all great conversations, we ran out of time before we ran out of topics.” (The cat’s out of the bag, so now I need a new one.)
Follow up within 12 hours of the conversation with notes from the conversation, and action items on your end. For instance, if the other person shared advice with you that you solicited, be sure to act on it. Come back two weeks to a month later and share the results of your findings. As you might suspect, bring a pen and paper for the conversation. People really respect it when you take their thoughts seriously. During, and even more so, after.
If possible, pay it forward, and when that time comes, don’t be afraid to share it with the source of the advice.
When I’m unprepared…
While still worthwhile in the former situation, you need to be able to break the ice quickly and give others a reason to listen to you for just two more minutes. People are naturally busy. And if you disrupt their normal flow of life, their whole goal while you are speaking to them is not how they can talk to you more, but about how they can get back to doing what they were doing.
Just as much as you will be unprepared, they will be too. As such, you need to disrupt their flow even momentarily. Your short 10-second bio needs to generate emotion and curiosity. Oftentimes, that is not your title. For instance, one that I like using with folks who I know to be lighthearted and have no context to the startup world is, “I get paid to be the dumbest person in the room.” Self-deprecating humor really does help for folks who can and have time to take a joke.
Other than your short bio, always have 2-3 questions handy via muscle memory that are good to ask in almost any situation AND would give you immense insight. I’ll share one of mine, and likely many more in the future with my DGQ series on this blog.
In your line of work, what differentiates the great from the good? Not just the good from the bad, but how do I tell the very best from the ones that have yet to get there but are still a cut above the rest?
Practice these again and again. In front of a mirror. In the shower. Or while you’re driving. Until they become second nature.
In closing
The important thing to remember is these people don’t owe you anything. And sometimes, while you can’t give them what they want, you can make that amount of time you have with them amusing. Insight doesn’t just come in the form of answers but also questions that get others to think in ways they didn’t before. Going back to one of my favorite Kurt Vonnegut lines:
“Use the time of a total stranger in such a way that he or she will not feel the time was wasted.“
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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.
I am by no means the best equipped to talk about this topic, nor have I achieved any modicum of success that I can call my life’s work yet. But the beauty about being insatiably curious is that I’ve gotten to know some incredible individuals, like…
Multi-time New York Times best-selling author
Founder of a household corporate brand
Investors who have consistently returned their investors over 10 times their investment
Individuals who have achieved insane, superhuman feats (i.e. climbing Mt. Everest, Olympic medalist, etc.)
Creator of a popular TV show
Chefs will multiple Michelin stars
A mother who serves as the role model for her children
A war refugee turned serial venture-backed founder
A veteran with multiple Purple Hearts
Unfortunately, while this isn’t true for all world-class performers I’ve met — to borrow one of Tim Ferriss’ phrases, many continue to stay curious, studious, restless, and most of all, humble. For those who continue to stay humble, how do they do it? After all, they have every right down to their bone to exhibit a large ego. To be full of themselves. They’ve made it.
What powers their humility? A question I find fascinating and telling of character.
Admittedly, I wish I could’ve been less obtuse about how I asked the above question.
After a number of conversations over the years, there are four chief themes:
Their greatest achievement is still ahead of them. They know what is possible, and continuously seek the adrenaline of doing the impossible. As long as the impossible is ahead of them, they are fighting a war against antiquated, yet widely-adopted mindsets. And the thing with the impossible is that it’s impossible to do it alone.
They fear they are unable to outdo their last greatest achievement. That fear either slides into depression or a burning fire to prove themselves wrong. That fire continues to keep them on their feet, anxious of the day they disappoint others, but most of all, themselves.
They have friends and family they deeply trust. They value the opinion of their confidants to keep them grounded. Confidants who prevent the hype get to the individual’s head, without discounting his/her achievement.
They themselves meet with exceptional people who show them the world is bigger than their pond. Exceptional people who challenge what they themselves know and what they think they know, helping them realize the limitations of their own world.
Regardless of what stage of life we are at, I believe there are life lessons here for everyone else as well.
Your greatest achievement is ahead of you. Don’t spend too much time on the past, even if you are proud of it.
Find a support group who’ll be with you even when times are tough — when your faith in yourself falters.
And, hopefully that same support group of friends and family will keep you grounded, even when the world tells you, you are a god.
Meet with people who challenge you, who inspire you, and who motivate you to act.
Of all the above, I’d love to double-click that last lesson in particular. There are two kinds of lives that great people live:
A life to envy
Or a life to respect
A life to envy is a life you would love to live instead of your own. It is often easier and more privileged than your own. A life born with a silver spoon in their mouths already. And if not that, a life of fairly few struggles or of extreme luck uncorrelated with their ability to hustle. These individuals often live only briefly in the limelight and find it difficult to repeat the “success” they’ve had. For instance, winning the lottery or being born into a well-off family.
A life to respect is a life where the individual overcomes seemingly impossible odds. One built with sacrifice — blood, sweat, and tears. It wasn’t an easy one. But where they are today is a testament to the scar tissue they’ve built over the course of their life. There are chapters in these lives that could and would rip apart the average person. This life is a life best viewed in a cinematic theater, but not one most people would want to live themselves, even though the status quo may be something they desire for themselves. I often find the world’s best founders in this category. And these lives often stand the test of time.
Most of these people won’t forget the past they came from. They continue to have insatiable curiosity and a bias to action. As such, they continue to learn at an astonishing pace. They continue to inspire us and motivate us to be better. And even before they succeed, many of their peers who don’t join them for the perilous journey merely comment on how they’re “built different.”
These are the same people I love spending time with. And hoping that when I do “make” it, I won’t forget their wisdom.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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.
Over the week, I was revisiting some of the Instagram posts that I had saved over the years, and I re-discovered one of my favorites by Christoph Niemann sharing his kudos to the late Kurt Vonnegut.
Most of all, Vonnegut’s advice on writing applies just as much to other forms of storytelling. And if you know me, I was immediately reminded of pitching.
Teach your investor something they didn’t know before.
A lot of investors claim to be experts, and even more are seen as experts. Too often, founders blindly listen to what their investors tell them to do. As Hunter Walk of Homebrew once said, “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.”
YouTuber Derek Muller just came out with a great video on the ideal variables that manifest expertise. Two of such variables are:
Valid environments – environments that are predictable and have minimal attribution to luck
Quick feedback loops
The problem with venture is that our feedback loops are incredibly long and drawn out. Oftentimes, it takes 7+ years to fully realize any kind of financial outcome, although there are many red herrings of outcomes in between, like new funding, brand-name investors, users (rather than customers, or people who actually pay for your product), mass hirings, and so on. Because our feedback loops are slow and luck plays a huge role in success, it’s hard to differentiate true experts in the field. All that to say, every investor is learning to be better, to have more data, to make better judgments than the next.
And if you can show that you know something worth our time again and again, it’ll be worth paying our tuition money to you.
That said, I don’t want to discount how some investors can be really helpful in particular areas that have valid environments and fast feedback loops. For instance, code, A/B testing distribution strategies, ability to help you raise your next round within a certain timeframe, or get you into Y Combinator. The determinant of success in the afore-mentioned has clear KPIs versus their own financial success in the fund.
Give the listener someone to root for.
Aka you. Why you?
Mike Maples Jr. once said, “We realize, oh no, this team doesn’t have the stuff to bend the arc of the present to that different future. Because I like to say, it’s not enough. […] I’d say that’s the first mistake we’ve made is we were right about the insight, but we were wrong about the team.”
“I’d say the reverse mistake we’ve made is the team just seems awesome, and we just can’t look past the fact that they didn’t articulate good inflections, and they can’t articulate a radically different future. They end up executing to a local maximum, and we have an okay, but not great outcome.”
There’s a category of founders that are going to win no matter if an investor chooses to invest or not. Most typically like riding this train. They have to do little to no work to be recognized as a great investor.
Then, there’s the cohort of founders that may or may not win on their current idea, but their investors really, really, really want these founders to win. These founders are the underdogs. They’re also the ones with often the craziest of ideas. Even more so, they’re the ones that if they win, these founders will redefine the world we live in today.
As a founder, you have two jobs when fundraising:
You need to find the partners who really, really want you to win. As the great Tom Landry says, “A coach is someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be.”
You need to give these partners the ‘why.’
And I promise you that ‘why’ is not because of straight facts, but because of a story. Why should people help you get what you deeply want?
Every character should want something, even if it’s a glass of water.
Speaking of what you deeply want, almost every founder I chat with pitches me their raison d’etre. A selfless reason to cure the world of cancer. Metaphorically speaking, of course. That’s cool. You can tell that to the press. It’ll make great PR.
Rather I care about the exact opposite. What is your selfish motivation? This is a question I personally like asking founders. Your selfless motivation keeps you going during the day, during peace-time, when things are going just right. Your selfish motivation keeps you up at night, when s**t gets tough. When no one else believes in you except for yourself.
I want to know that you want that so badly, that you’re able to go the distance. And if that same thing is something that your investor can relate to, then you have a match made in heaven.
Every sentence must do one of two things — reveal character or advance the action.
Let me revise the above. Every slide must do one of two things — reveal character or advance the action. Anything else is superfluous. That means, outside of your core slides — problem, solution, action plan/financial projections, rising conflict (aka competition, blockers and risks), and your team slide, everything else is superfluous. Or at least, save it for your data room.
I’m sure some investors would debate me on this, but every investor has a slightly different framework. The above is my own perspective. That said, every slide should give an investor 10% more conviction towards investing in your business — capping out at 70%. ‘Cause after 70, any additional information (in the first meeting) has diminishing returns.
Start as close to the end as possible.
No investor cares about which hospital you were born in, but they do care about when the fire first started. And they care about your inflection points, even if that’s still ahead of you.
Be a sadist. Show awful things that happened to the characters.
Grit is one of the hardest founder traits to measure over a 30-minute meeting. Even after prolonged and deliberate interaction, most of the time it’s still hard to grasp this amorphous quality. But if you ask most investors what is the number one trait of a great founder, it’s either grit or passion. The latter of which often serves as a proxy to grit.
If you’re regular here, you know one of my favorite quotes of late is Penn and Teller’s. “Magic is just spending more time on a trick than anyone would ever expect to be worth it.“
Past performance is not a predictor of future progress. But it really does help. A lot. In a startup’s lifespan to becoming a leading business, there are 10-15 trials by fire. And for each one of those, the founders are required to pull off nothing short of a miracle. In fact, this next year will be exactly one of those tribulations for 99.9% of companies.
So, show moments in your life where you were able to pull off a miracle. And a miracle, by definition, is when the odds are heavily stacked against you.
Show excellence. Walk your listeners — your investors — through the journey of how you tasted glory. How you were able to achieve the seemingly impossible. Personally, this is why I love backing professional athletes, veterans, and chefs. Three fields (of, I’m sure, many more) that you really need to eat s**t to be one of the greats.
Write to please just one person. Don’t get pneumonia.
Every pitch should be tailored. Why would this investor be the best dollar for your cap table?
No investor (even if it’s true) wants to be just another investor. They want to be THE investor. Make them feel special. When you propose to your partner for marriage, you tell them why they’re the one for you, not why you’re the one for them. You get down on one knee and tell them why they are amazing. Not the other way around.
Give your readers as much information as possible as soon as possible.
The one-liner matters. It is the first point of interaction with your startup, and oftentimes, may be the last. Don’t shroud it in mystery and jargon. If you’re ever stuck here, remember Brandon Sanderson‘s First Law of Magic:
“Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.“
Equally so, the subject line of a cold outreach email serves the same purpose. This is especially true, when you’re reaching out to someone who you can reasonably assume has hundreds of emails in their inbox per week. For reference, and for the most part I’m a nobody compared to the partners at a16z of Lightspeed or Benchmark, and I get about 50 cold inbounds per week.
So, in my opinion, your subject line should have no buzzwords (well, because everyone’s using them). Think of it this way. Say you’re an author selling your new self-help book. And say your greatest distribution channel are likely bookstores in airports. If everyone in the self-help section has an orange cover with bold blue words, you want to be the one black and white cover book. And if everyone has black and white sleeves, you bring out the neons.
In the context of email subject lines, instead, you should include numbers. What is the one metric that you are killing it at? Just like what I recommend folks write in their email forwardables. Instead of “Invest in the Leading BNPL Solution in Latam”, use “BNPL startup growing 50% MoM”. Give the exact reason why your investor should be excited to invest in your company. Don’t save it behind eight clicks — Email, Docsend link, and another six clicks to get to the slide of importance.
People can only tell different, not better, unless it’s 10x. Mediocrity is a crowded market, so don’t waste your time there. Taking a quote out of Pat Riley‘s book, “You don’t wanna be the best at what you do; you wanna be the only one who does what you do.”
In closing
Storytelling is an emotional discovery. The facts don’t change, but a great pitch or story weaves seemingly disparate facts into a compelling narrative. One that inspires action and draws curiosity. In a saturated world of attention, you are fighting for minutes if not seconds of someone’s time. Make it valuable.
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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.
