(Not) Relationship Advice

relationships, biking

Earlier this year, when catching up with a friend and talking about love, he shared his greatest relationship advice. “You want to marry someone who believes the world happens because of them, not to them.” And it really stuck with me. Both he and I are people who have big dreams. That in order to make our dreams happen we need every oar rowing in the same direction. That includes the people we surround ourselves with. More than anyone else, our romantic partner is likely the one we spend the MOST time with. But that in itself is a slight digression.

In a somewhat parallel sequence of events, at the end of last year, I had the opportunity to join a much, much larger shop. And while I ended up choosing not to join, the primary question I was asking myself was: If I were successful here, would I be successful in spite or because of the institution? The truth was from an outsider’s perspective, maybe even personally, it’d be really hard to tell.

Now why do I share the above? And where the hell am I going with all of this? What does love have to do with career opportunities?

So… this won’t be my most graceful transition between thoughts, but in my head, they all orbit the same genre.

One of the questions I used to ask LPs during my time in investor relations was: “What was the last investment you made that didn’t work out? Without naming names, what happened?”

And there are two reasons I ask that:

  1. Oftentimes, knowing what an LP doesn’t or won’t ever invest in again is more telling than asking them what they do invest in. LPs are, by definition, generalist. And under that premise, they technically invest in “everything,” so you’ll end up getting very broad answers, especially if they cover more than one asset class.
  2. Do they describe an investment that didn’t work out with active or passive verbs? Did it happen to them? Or do they own up/exhibit agency over their own decisions? Are they arbiters of their own destiny? “I made this investment decision, learned, and this is what I won’t do in the future. Or will still continue to do.” is different from… “This mishap happened to me. How could I have known? It is what it is. It’s not my fault. It was out of my control. It was someone else’s decision.”

For the latter point, people who don’t seem to be able to own up to the decision will likely not be your greatest champions if you’re an emerging manager. If at all. To them, life happens to them. They can’t control it. They have a narrative they keep telling themselves that they have no power. Some might be true. But these folks rarely stick their neck out for you.

By default, most emerging managers look less than pretty. A million reasons (most of which likely true) of what could go wrong. And it’s actually in the best interest of a capital allocator’s career and income that they stick their neck out for risky bets. Many institutions don’t compensate their team based on outlier performance. So incentives won’t be aligned. But to borrow an adage of Jobs, “the people who are crazy enough to think they can change the world, are the ones who do.” And at the very minimum, they have to believe they can change their own world.

When things are non-obviousโ€”from a returns perspective or strategy or anything elseโ€”you need people who can and will invest courageously and own that decision.

Photo by Everton Vila on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

“How do I prove to an LP that I have good deal flow?”

So, this is the first blogpost I’m cross-posting from my brand new Substack, Superclusters After Hours. Don’t worry, I’ll still write here weekly. This blog has always started as a personal blog. I write about what I want to write about on a weekly basis. Sometimes, it’s about venture. Other times, it’s about food, adventure, and random things I think about. The goal of the new blog is to become the primary catalog and archive for ephemeral LP content that I post on LinkedIn, with event invites whenever I do them. Events, for those of you reading this blog and know me, I have almost never publicized them before or after the event. And it’ll continue to stay that way. But I’m going to start playing around with the idea of doing Superclusters-only webinars with a very strict rule of confidentiality. TBD.


Hereโ€™s a question I got from a GP recently, which to be fair, took me much longer than I initially intended to respond to.

To the GP who sent this to me, and I know youโ€™re reading this, thank you. Itโ€™s a great question. And one Iโ€™ve heard frustrate many a good GP out there.

So Iโ€™m going to include below what I wrote to that GP โ€” word for word. So apologizing ahead of time for typos and grammatical errors.

Ok, this is an awesome question! Took some time here so I could better process my answer for you. Apologize for the delay and ramble ahead of time.

So I think there are 2 questions here: (a) how do you stand out as a GP who actually has deal flow when everyone claims they do, and (b) in a broader scope, how do LPs diligence deal flow?

Iโ€™ll start with the former.

(a) How can you prove to LPs you have deal flow thatโ€™s different/better than others?

So first off, most people say the same thing: โ€œI get deal flow from founders in my network and co-investors.โ€ But if everyone says that than even if itโ€™s true, how does yours look any different? The truth is most LPs donโ€™t know either. And in some ways, it might be easier to guide LPs how to think, that not only helps them diligence your fund, but also makes them a better LP, period. Keep in mind, most LPs cover a wide variety of asset classes and venture, much less emerging managers, is the smallest of the smallest chunk. And so they donโ€™t have the incentive or the experience to really dedicate all their time to try to figure out how to better underwrite venture.

Itโ€™s similar to a question a friend of mine recently asked me. My friend is someone who eats to live (as opposed to lives to eat. Yes, those people exist in the world). And recently he found himself in love with someone who loves to eat, and by function of that, lives to eat. And so he asked me, despite having eaten at a bunch of restaurants, โ€œhow do I know which fine dining restaurant to bring his girlfriend to for their 6-month anniversary?โ€ And I gave him a whole list of things I look for when it comes to picking restaurants. For instance, reading Google and Yelp reviews, but specifically the 3 and 4-star ones, not the 5- or 1-star ones because theyโ€™re so biased. And on top of that, I gave him recs of date-ish things to do pre- and post-dinner as well based on proximity to the restaurant. I also told him in the reservation to ask for a 10-15 minute kitchen tour after the dinner as an extra special experience. And after giving him all of that, he stares blankly at me. Not because he didnโ€™t hear or understand what I told him, but because, really, he was just looking for a name. One name. He would then book it, and move on with his life. Because food, for him, was and is not his focus area. He had other โ€œmore importantโ€ things to focus on in his life and in the relationship.

Similarly, most LPs are the same when they look at venture. They do it because they need to think about total portfolio allocation or the David Swenson model, but they donโ€™t do it because they love it or that they believe in it. And so they need to know a name, and thatโ€™s all they need.

So to get off my preamble, assuming that an LP has committed in their mind to spend time and do the work in emerging manager land, then you proceed with the next step. And unfortunately, most wonโ€™t. And thatโ€™s okay. Theyโ€™re just not the right fit for you now.

So, the next step is really to guide them. One thing Iโ€™ve found to be helpful (if you have it) is to take your strongest few co-investors that you think you have the best relationship with, and ask the LP, โ€œLetโ€™s take X firm. What are the best investments they made in the last 12 months, say by revenue growth or headcount growth? And I will tell you if I saw them before they made their investment and who shared it with me.โ€

Conversely, you should look at who else you know well in their existing portfolio, and have them vouch for you and the type of deals you see. Also potentially more importantly, the kind of person you are. The strongest co-signs are often GPs in their existing portfolio and institutional LPs that specialize in venture that theyโ€™re really close to.

Another thing Iโ€™ve seen a GP do (paraphrasing here): โ€œIโ€™m going to give you a list of folks who send me deals, short list, and I can give you a longer one if youโ€™d like. And I havenโ€™t told them youโ€™re going to call, so please use your best judgment when asking for their time. But ask them how many other VCs they passed the last 5 deals they shared with VCs to? If theyโ€™re doing their job right, theyโ€™ll likely pass to more than one. But see if my name comes up. If it doesnโ€™t, you have your answer. If it does, you have your answer.โ€

Going a step further, and I donโ€™t think Iโ€™ve seen any GP do this yet, but I feel like it should be more of a thing: Take all the deals youโ€™ve gotten from your โ€œnetworkโ€ (i.e. founders, investors, etc), and segment them by, who sent you a deal because:

  • You co-invested with them in the past
  • You invested in them
  • You didnโ€™t invest in them (compliment to an investor to get strong deal flow from someone they passed on) – anti-portfolio, but keep in mind this only matters, if the people you receive it from are successful founders in the eyes of an LP, maybe you asterisk these
  • You had no prior economic relationship with them
  • You used to work with them
  • Theyโ€™re a fan of you/your content/etc
  • Iโ€™m sure there are other segmentations, but you get the gist.

And in addition to that, when you pass on a deal that someone refers, categorize the deal into why itโ€™s a pass:

  • Not a strong founder
  • Too expensive, but good founder
  • Good founder, but not in sector/thesis
  • Not raising at the time

And all the above you would show to an investor and I think should be a good snapshot as to the quality of your deals. Then if youโ€™re comfortable with them, challenge them to try the same exercise with other investors. Part of proving something to an LP is to help them become a better investor, period. Whether they invest or not.

(b) How do LPs diligence deal flow?

The simple answer is: they do references. In terms of how many, Iโ€™ve heard everything from 3 to 40. The highest end being Cendana. Most institutions

For those that do 5 or less, primarily either use an oCIO/RIA (i.e. Cambridge, Stepstone, Hamilton Lane, some kind of MFO, etc.) or they primarily bet on firms that are hard to get but also wonโ€™t get them fired, largely because they donโ€™t just have the time/resources/team members to specifically underwrite emerging managers in venture. Because of the optimization of โ€œI need to see โ€˜everythingโ€™โ€ and I donโ€™t have the time to go deep and assuming they choose to do (in some parts) their own work, they:

(i) talk to a lot of spinouts โ€˜cause easier to reference and draft a memo to get buy in

(ii) talk on stage at conferences with the perception that they are open for business, which they technically are, but very selective

(iii) have you go through really long ODDs and DDQs in front of a (large) panel of stakeholders and decision makers in the organization. Ranges for 3 to 20-something people all listening to you answering questions. At that point, itโ€™s your word against your word, but a committee will nitpick on everything. The upside is that itโ€™s easier to share something you do that youโ€™re 1 in 5 or 1 in 10 who do (as opposed to FoFs and venture-focused MFOs or institutions who need you to be 1 in 100 or 1 in 1000). The downside is you need to appeal to a larger group of people, and it takes more time outside of meetings (up to 350 question ODD).

But I digress. For the purpose of your question of your question and what I believe your frustration might be, Iโ€™m going to focus on diligencing deal flow when youโ€™re not in the room. Assuming itโ€™s an LP who is actually intentional about diligence AND is open-minded enough to not bring too many of their own biases in…

  • On-list
    • Founders: sticking to the facts. How did you meet the GP? What did you talk about in the first meeting? How long did they take before they committed? What questions were asked? Did other VCs ask the same questions? How competitive was the round? If you offered any special terms, why and who else did you offer it to? Did they all take it? Have you introed any other founders or people to the GP? Has the GP provided you value post-investment?
    • Co-investors: Who gives you the best quality of deals? Intro to meeting ratio? Meeting to diligence ratio? Meeting to commitment ratio? How does this GP stack rank against other relationships/other verticals? Did the emerging GP intro you to the deal youโ€™re co-investors in?
    • LPs: How many other firms of a similar strategy did you talk to? What were the sourcing strategies for the other firms? Compare and contrast.
    • Former employers/misc: deal flow isnโ€™t really diligenced here. The best thing these folks can attest to is your character + network.
  • Off-list (a lot of off-list is done with people who, in the words of an LP, โ€œowe you [the LP] more favors than they owe the GPโ€)
    • Founders: Rank your favorite investors on the cap table. Who are your top 3? Why? If you were to start a new co, who would you take with you again?
    • Co-investors: How much signal is a deal if that GP sends it to you? Compare with other GPs. Why?
    • LPs: Have you gotten co-investments from the GP? How is their level of communication post-investment?
    • Others: Same as above.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Nemawashi

early morning, nemawashi

I learned a new word today. Nemawashi.

The Japanese word for the business practice of building consensus and hearing people’s opinion before the decision or change is formally proposed.

And I don’t think I know the English parallel to that.

I’ve always told the GPs and founders I work with/have invested in that they should involve their investors in major decisions before they’re proposed and discussed. That no board meeting or LPAC (LP advisory committee) topics should ever be a surprise. It also shows that you’re not talking at people and you’re trying to involve them as a true partner for your business. Both LPs and VCs (to founders) highly prefer that. Conversations should never be out of convenience, but they should feel intentional. You also don’t have to be perfect, neither should you pretend to be with the people who’ve chosen to be with you long-term. Just as you shouldn’t hide any trauma, sentiment, and harbored feelings from your romantic partner and family.

The quarterly board meeting and the LPAC meeting are merely formalities. You should be able to trust your investors outside of those structured events. You may not need to bring up certain topics because it’s not written in the term sheet or limited partner agreement, but that doesn’t mean you shouldn’t. Partner struggles. Off-thesis investment opportunities. Major hires. Or layoffs.

There are a lot of VCs and LPs who would love to be true partners with you, but sometimes they don’t know how to help unless you ask for help before you make the decision. Have the conversation early on about how they would like to be involved in your business. And for those who do, go to them before you propose a decision or change.

Now I know there’s a word for it.

Photo by Jasper Graetsch on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

DGQ 26: Which Slide in my Deck Stood Out the Most?

slide

One of my most used lines in my diction is: “Your mileage may vary.”

Maybe because of what I’ve written historically about. Maybe ’cause of my previous life in investor relations. Or maybe, it’s because of the interesting node I sit at in the venture ecosystem. I often get asked by GPs and founders alike for fundraising advice. Now before you come to any conclusions, I don’t have a silver bullet. I’m not even sure if my advice when it comes to fundraising is any good. While I’m lucky to have heard back from a number of people I’ve shared my thoughts with on the result of their fundraise after employing my “advice,” I’m still not completely sure how much of it was the fundraiser themselves and how much of it was the advice. And how much the color of the jersey matters.

And so when I share what I’ve seen or done, I always caveat with that first line. That said, what I think is more useful than any advice I could give pre-mortem is listening to the feedback of the market. The people you’re pitching to. When someone says no, why do they say no? When someone says yes, why do they say yes?

Inspired by a conversation I had the previous week at a summit, getting feedback from someone who passed is tough. Through the archives of fundraising, you’re more likely to get no’s than yes’s. And when you do, do you know why? Very rarely do you get much feedback. Investors (LPs and VCs) are either too busy or have too much to go through to give feedback as intimately as you probably like. And so I’ve always found it useful to make it easy for people to give feedback. Naturally, it’s never guaranteed you’ll get a response, but usually, the below question I like to ask reaches less deaf ears than “Can you give me feedback?”

I know you’re busy, and you simply don’t have the time to give every pass a share of feedback. But if I could ask for 30 seconds of your time (no more than that), which number slide on my deck did you most notice (good or bad)?

Or… was there a particular slide in my deck that piqued your interest the most that led you to schedule our initial meeting?

The goal of this question is to triangulate attention and mindshare. When you get the answer, then you can come to your own (hopefully intellectually honest) conclusion about whether the message shared on that slide is strong or weak. Controversial or not.

Moreover, you’re not overstaying your welcome. The advice and feedback you’re asking for in pointed and doesn’t consume a lot of time for the other party to answer (yet will feel to them as if they’re doing you a favor and/or being helpful).

Only once you know why people say no can you actually iterate on the pitch. Of course, there are many different ways to ask for feedback, and… your mileage may vary. Usual fundraising advice gets you through the first 10 pitch meetings. After that, you need to course-correct based on the feedback you get back.

One thing I will note is that in the age of agentic venture firms and tools that can be built within hours that cover every stretch of the imagination. One thing an LP told me that a GP told them was that some founders are getting smart. Preparing two decks for investors: one for the human eye, the other for the agentic audience. The latter with more appendices than the former. I imagine that it’s only a matter of time before VCs do the same to LPs as LPs are building agentic deck readers. In that sense, asking for deck feedback may not hold as much weight as it used to. Who knows?

Nevertheless, if there’s one takeaway from this blogpost, it’s that if you want help, if you want feedback, make it specific, low friction, and direct.


The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. Itโ€™s an inside scoop of what goes on in my nogginโ€™. 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. Iโ€™ll let you decide which it falls under.


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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.

The Currency of Trust

Recently, I had three conversations about trust. So forgive me, but that’s the soup du jour today, as their comments are still swimming in my mind.

I spent some time with the Head of Investor Relations at a high nine-figure AUM firm. And he said something that echoed much of the reality of fundraising these days. “Fundraising is all about trust. It’s not about the performance metrics. It’s about who believes in you.”

Then, immediately after, I caught up with an LP friend, who said, “Investor relations is a wasted job title in VC. They’re glorified note takers and relationship managers. I won’t invest in any fund where I haven’t met the GP.” Only to later share how much we both admired a certain Head of IR at a large multi-stage fund.

At first glance, the irony is blinding. The funny thing is that both are equally as true. GPs have a bank account where they can deposit trust. They withdraw trust every time they make an ask. Whether it’s for capital or special terms on the term sheet or for a certain ownerships target or for a guest speaker for an event they’re hosting. Before a GP starts a firm, they need to bank a lot of trust. They should give more than they take. And to run a firm, there are three types of primary customers you need to bank trust with:

  1. Founders,
  2. Co-investors,
  3. And LPs.

You also can’t take a loan on trust (in other words, outsource trust) before you’ve deposited enough trust in your own bank account. Or else, you’ll be in debt. If you’re in too much debt (i.e. have a negative balance), your reputation takes a hit. But when you’ve banked enough trust, you can have a separately managed trust account managed by others. An IR professional who manages the trust account with LPs. A community/platform person with co-investors and talent. And so on.

Having others manage these accounts too early in the firm lifecycle means taking debt and impacting reputation. So when my buddy who’s the LPs says he doesn’t like most IR folks, it’s because before the IR person was hired, the GP didn’t bank enough trust.

And the truth is trust is built not in grand gestures and one-off deals. It’s in the small interactions. How fast do you respond? Even when you’re busy, do you make time for people important to you? Do you remember what you talked about last time? Do you close the loop on advice you get from LPsโ€”whether you use it or not? Do you remember their answer to ‘What did you do last weekend’ 15 weekends ago? Do you follow through with what you promiseโ€”even if it’s a restaurant recommendation you mentioned in the call?

In a conversation with a Fund I GP yesterday who successfully raised his 8-figure fund in 8 weeks (and yes, part of that duration was over the holidays), he said something I really liked: “Every LP is looking for returns. That’s a given. But every LP is also looking for returns plus X. Your job during the fundraising process is to find out what X is, and it may be less obvious than you think it is.” For some, X is undoing boredom. For others, it’s the front row seat to learn. Others still, it’s the prospect of social capital that will come with making an investment. And you can’t find any of these out, if you don’t spend the time to build trust with the other party.

Photo by Marek Piwnicki on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

The Third Leg of Firm-Building

marathon, race, third leg

Five years ago, I wrote a piece about the third leg of the race. From my time as a competitive swimmer, the lesson our coach always had for us was if you’re swimming anything more than two laps, the most important part of every race is the third leg. Everyone’s tired. Everyone’s gasping for air. Yet everyone wants to win. The question is who wants it more. And by the time you get to a decently high level, everyone’s athleticism is about the same. All that matters is the mentality you have on that third segment of four of each race.

We often say, that starting a company or a fund is a marathon, not a sprint. True in a lot of ways. But also, it’s a series of sprints within a marathon.

We put out an episode last week with the amazing Ben Choi, which I really can’t stop recommending. Just because I learn something new every time I talk with Ben, and this time especially so. But that’s my own bias, and I get it. But more interestingly, he said something that I couldn’t get out of my mind since we recorded. “The first three fundsโ€”not just the first two, the first threeโ€”are that ‘working-out’ process. Most pragmatically, there’s very little performance to be seen by Fund III. So it’s actually Fund IV for us to hold up the manager as no longer emerging and now needs to earn its own place in the portfolio.” The timestamp is at 16:21 if you’re curious.

And it got me thinking… is Fund III that third leg of the race?

When most GPs raise Fund III, they’re usually four, maybe five years, out from their Fund I. And that’s assuming they started deploying as soon as they raised their fund. And within five years, not that much changes. Usually, that’s two funding rounds after your first investments. But lemons ripen early, so only a small, small subset move to Series A or B. Most have raised one or less subsequent round since the GP committed capital.

Even accounting for two funding rounds later, that’s usually too early to consider selling into the next round. And if one does (unless it’s a heavily diversified portfolio and the GP has no information rights, and somehow is so far removed from the company that no one at the company talks to the GP anymore), then there’s signaling risk. Because:

  1. No matter what portfolio strategy you run, not staying in touch with your best performing companies is a cardinal sin. Not only can you not use those companies as references (which LPs do look for), you also can’t say your deal flow increased meaningfully over time. No senior executive or early employee knows who you are. So if they leave the company and start their own, they wouldn’t pitch you. Your network doesn’t get better over time. See my gratitude essay for more depth here.
  2. Not having any information rights and/or visibility is another problem. Do the founders not trust you? Do you have major investor’s rights? How are you managing follow-on investment decision makingโ€”whether that’s through reserves or SPVs? Are the blind leading the blind?
  3. And if you do run a diversified portfolio, where optically selling early may not be as reputationally harmful to the company, you are losing out on the power law. And for a diversified portfolio, say a 50-company portfolio. You need a 50X on an individual investment to return the fund. 150X if you want to 3X the fund. As opposed to a concentrated 20-company portfolio, where you only need 20X to return the fund and 60X to 3X. As such, selling too early meaningfully caps your upside for an asset class that is one of the few power law-driven ones. As Jamie Rhode once said, โ€œIf youโ€™re compounding at 25% for 12 years, that turns into a 14.9X. If youโ€™re compounding at 14%, thatโ€™s a 5. And the public market which is 11% gets you a 3.5X. [โ€ฆ] If the asset is compounding at a venture-like CAGR, donโ€™t sell out early because youโ€™re missing out on a huge part of that ultimate multiple. For us, weโ€™re taxable investors. I have to go pay taxes on that asset you sold out of early and go find another asset compounding at 25%.โ€ Taking it a step further, assuming 12-year fund cycles, and 25% IRR, โ€œthe last 20% of time produces 46% of that return.โ€ And that’s just the last three years of a fund, much less sooner.
  4. Finally, any early DPI you do get up to Fund I t+5 years is negligible. Anything under 0.5X, and for some LPs, anything sub-1X, isn’t any more inspiring to invest in than if you had absolutely no DPI.

Yet despite all of the above, the only thing you can prove to LPs are the inputs. Not the outputs. You can prove that you invested in the same number of companies as you promised. You can prove that you’re pacing in the same manner as you promised. And you can prove that founders take the same check size and offer the same ownership to you as you promised. And that is always good. As you raise from friends and family and early believers in Fund I, Fund III’s raise usually inches towards smaller institutions, but larger checks than you likely had in Fund I.

  1. Fund-of-funds care about legibility. Logos. Outliers. Realistically, if you didn’t have any before Fund I, the likelihood of you having any while raising Fund III is slim. They need to tell a story to their LPs. A story of access and getting in on gems that no one else has heard of, but if everyone knew, they’d fight to get in.
  2. Any person you pitch to who has any string of three to four letters (or is hired to be a professional manager) attached to their name (i.e. MBA, CAIA, CFA, CPA, etc.) has a job. For many, their incentive unless their track record speaks for itself (likely not, given how long venture funds take to fully return capital) is to “not get fired for buying IBM.” Some of their year-end bonuses are attached to that. Some lack the bandwidth and the team members to fully immerse themselves in the true craft of emerging manager investing. Many times, the incentive structure is outside of their immediate hands. For every bet they make that isn’t obvious, they risk career suicide. At least within that institution.

I’m obviously generalizing. While this may be true for 90%+ of LPs who fit in these categories, there are obviously outliers. Never judge a book by its cover. But it’s often helpful to set your expectations realistically.

As such, despite not much changing from your investment side, from the eyes of most LPs, you are graduating to larger and larger LP checks. Usually because of the need to provide more proof points towards the ultimate fund strategy you would like to deploy when you’re ‘established.’ But to each new set of LPs, prior to an institutional 8-year track record, you’re still new. On top of that, as your fund size likely grows a bit in size from Fund I, to some LPs, you are drifting from your initial strategy by no longer being participatory and now leading and co-leading. You also might have added a new partner, like Ben talks about in the afore-mentioned episode. And a new strategy and a new team requires new proof points related to on-thesis investments. So, Fund III is where you begin to need to whether the storm. For some, that may start from Fund II. Altos Ventures took four years to raise their Fund II. Many others I know struggled to do the same. But if you really want to be in VC long term, this is the third leg of the race.

And this is when a lot of GPs start tapping out. Will you?

Photo by Victoire Joncheray on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

When Do You Know If You’ve Grown Up as a VC? | El Pack w/ Ben Choi | Superclusters

ben choi

Ben Choi from Next Legacy joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on 3 GPs at VC funds to ask 3 different questions.

Gilgamesh Ventures’ Miguel Armaza, also host of the incredible Fintech Leaders podcast, asks Ben what is the timing of when a GP should consider raising a Fund III.

Similarly, but not the same, Strange Ventures’ Tara Tan asks when an LP backs a Fund I, how do they know that this Fund I GP will last till Fund III.

Arkane Capital’s Arkady Kulik asks how one should think about building an LP community, especially as he brings in new and different LP archetypes into Arkane’s ecosystem.

Ben manages over $3.5B investments with premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning three decades in the technology ecosystem.

Benโ€™s love for technology products formed the basis for his successful venture track record, including pre-PMF investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobeโ€™s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an alum and Board Member of the Society of Kauffman Fellows (venture capital leadership) and has also served his community on the Board of Directors for the San Francisco Chinese Culture Center, Childrenโ€™s Health Council, Church of the Pioneers Foundation, and IVCF.

Ben studied Computer Science at Harvard University before Mark Zuckerberg made it cool and received his MBA from Columbia Business School. Born in Peoria, raised in San Francisco, and educated in Cambridge, Ben now lives in Los Altos with his wife, Lydia, three very active sons, and a ball python.

You can find Ben on his socials here:
X / Twitter: https://x.com/benjichoi
LinkedIn: https://www.linkedin.com/in/bchoi/

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

[00:00] Intro
[05:05] Ben’s 2025 Halloween costume
[06:44] Jensen Huang’s leather jackets
[07:24] Jensen Huang’s answer to Ben’s one question
[10:05] Enter Miguel, Gilgamesh Ventures, Fintech Leaders
[14:43] What are good signals an LP looks for before a GP raises a Fund III?
[22:35] Why does Ben say ‘established’ starts at Fund IV?
[25:08] Who’s the audience for Miguel’s podcast?
[27:52] In case you want more like this…
[28:32] Enter Tara and Strange Ventures
[32:46] How does Ben know a Fund I will become a Fund III?
[36:53] How does Ben know if a GP will want to build an enduring career?
[40:58] How does Tara share a future GP she’d like to work with to Ben?
[42:43] Marriage and divorce rates in America
[43:34] What should a Fund I do to institutionalize?
[46:28] Should you share LP updates to current or prospective LPs?
[48:57] Enter Arkady and Arkane Capital
[51:09] How does one think through LP-community fit?
[1:01:31] What’s Arkady’s favorite board game?
[1:03:08] Ben’s last piece of advice to GPs
[1:09:50] My favorite Ben moment on Superclusters

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œThe dance of fundraising is when you do have [your thesis], the LP has to figure out is this a rationalization of the past or is it actually what happened? Was this known at the time? Because if it was, we can have some confidence in the future going forward. But if it was just a rationalization of some randomness, then itโ€™s hard to know if Fund IV or V or VI will benefit from the same pattern.โ€ โ€” Ben Choi

On solo GPs bringing in future partners by Fund IIIโ€ฆ โ€œThe future unidentified partner is the largest risk that we have to decide to accept. So there actually isnโ€™t a moment where we decide this GP is going to be around for Fund III. Itโ€™s actually the dominating risk we look at and we get there, but itโ€™s a preponderance of other things that we need to build our conviction so high that weโ€™re willing to take that risk.โ€ โ€” Ben Choi

โ€œItโ€™s brutal. Itโ€™s a 30-year journey. For any GP who raises a single dollar from external LPs, itโ€™s a 30-year journey.โ€ โ€” Tara Tan

โ€œI donโ€™t think anyone goes into this business to raise capital, but your ability to raise capital is ultimately what allows you to be in this business.โ€ โ€” Ben Choi

On communityโ€ฆ โ€œYour core question is how much diversityโ€”in the technical term of diversityโ€”can you tolerate before you lose the sense of community.โ€ โ€” Ben Choi

โ€œMost letters from a parent contain a parent’s own lost dreams disguised as good advice.โ€ โ€” Kurt Vonnegut

โ€œFundraising is a journey of finding investors who want what you have to offer; itโ€™s not convincing somebody to do something.โ€ โ€” Ben Choi


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Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Woe is Me

sunset, alone, dock, woe

I was talking to an emerging manager raising a $10M fund recently. He shared a comment, likely off-the-cuff, but something I’ve heard many other emerging managers echo. “This year, most of the dollars deployed into venture has concentrated in only a few big funds.”

Not this manager in particular, but I’ve heard so many other Fund I or Fund II GPs say that. Blaming their struggle with fundraising on the world. It’s not me, but the world is conspiring against me. Or frankly, woe is me. But there is no LP who ever wants to hear that. Building a firm is hard. Building a startup, likely harder. No one said it’ll be easy. So let’s not pretend it’ll be all sunshine and rainbows. If you thought so, you’re deeply misinformed. If you’re going to be an entrepreneur of any kind, you need to take matters into your own hands. You cannot change the world (at least not yet). But you can change how you approach it.

And as an LP, that’s the mentality we’re looking for. Or as Raida Daouk once said on the pod, we like “GPs who can run through walls.”

That said, the mega funds who are raising billions of dollars are raising from institutions whose minimum check size is in the tens, if not hundreds of millions. These same institutions would never invest in an emerging manager. Their team, their strategy, and their institution isn’t built for it. When they have to deploy hundreds of millions, if not billions, a year into “venture” with a team of four or less, you’re not their target audience. So as an emerging manager, those mega funds are not your competition at least when it comes to LP capital.

You’re competing against all the other funds (likely emerging managers) at your fund size. Who can take the same check size you can take. That’s who you’re competing with. So whether you like it or not, billions going to the mega funds has, from a fundraising perspective, nothing to do with you.

If you are looking for reasons to fail, you will find one.

As the great Henry Ford once said, “Whether you think you can, or you think you can’t, you’re right.”

Photo by Johannes Plenio on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜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!


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.

Fundraising โ‰  Capital Formation

cash register

I was chatting with a GP last week about the highlights and lowlights of having a multi-stage fund or just a VC fund as an LP via their fund-of-funds. The obvious synergies of access to downstream capital and branding, especially if the individual running the fund-of-funds is known for their institutional track record as an LP. As well as access to the GPs at those funds for mentorship reasons.

But the downsides also exist. You’re one of many of other GPs who have access to the same team. More often than not, there’s no institutional diligence. And the investment happens largely for strategic purposes. Same is true for multi-stage GPs investing through their own family office. But you also have to think through the tough conversations you need to have when you take checks from more than one of these funds. Assuming all else equal, and they write the same check size, when your portfolio companies are outperforming, do you pass them to Big Fund A or Big Fund B? Equally as true for any LP who wants co-investment opportunities. Family offices. Fund-of-funds. The classic question of: Do you like Mom or Dad more?

And there’s one more. Consider a multi-stage fund who’s an LP in your fund. You share one of your stellar portfolio companies with them, and they loved the deal so much they also invested. Not only invested, but led the following round at a much, much higher valuation. For the sake of this thought experiment, let’s say the Series A valuation is a solid nine figures. As such, they take a board seat. A year later, your portfolio company has the opportunity to exit for $800M. A phenomenal exit for everyone on the cap table, including yourself, your other co-investors, the founders, and the employees. And for you in particular, this would return meaningful multiples of your fund. But not your Series A lead, who is also your LP. The math isn’t inspiring for them. $800M would only be a shy 4-8X on their initial investment.

So, the Series A lead/your LP blocks the acquisition deal and pushes the founders to go for more. You push back on the motion as everyone else’s incentive, including the founders, is the same as yours. Whether the deal happens or not at this point is irrelevant. This Series A lead, who’s also your LP, ends up telling a number of other LPs that you’re difficult to work with. To the effect that they would also no longer re-up in your next vintage. And that makes your fundraise for the next fund even harder than you expected.

You’ve not only lost a $500-2M check (on average), but worse, you’re likely to have a tarnished reputation with prospective LPs. If they like you already, they may look beneath the surface. If they haven’t gotten to know you, they’ll likely surmise on limited information that the juice isn’t worth the squeeze.

Before you dismiss this as just a hypothetical case study, note that this is a true story.

As my buddy Thor once told me, โ€œCapital formation is a design principle. Fundraising is a sales process. Without true design around a customer base and a product, you will fail eventually.โ€

Capital formation is thinking through the types of conversations you want to have when you’re in Fund n+1 and n+2, 5-6 years from now. As Adam Marchick once said, “The bulk of your conversations with an LP happen negative 6 months to time of investment. The most important conversations you have with an LP are Year 2 through 6 of your investment.” These are the conversations about extending recycling periods, early distributions, fund extensions, and so on. Many of which revolve around the return incentives of your LP base (if decisions are made by majority approval) or by LPAC approval. A family office who has no immediate liquidity needs might not want early distributions and wants you to hold out. Another who’s starting a new business line or pulling completely out of venture (because they were misinformed or set the wrong expectations initially) will want early liquidity and/or someone to buy their stake. An institution with a high leadership turnover rate will likely have a new CIO who’ll want to redo the whole portfolio. So what used to be obvious re-up decisions will need to be re-underwritten altogether.

So I’m not here to say, “Don’t take LP checks from fund-of-funds whose core business is being a VC.” I just want to remind you to consider the incentives of each LP you have on your cap table. Ideally, your LP base’s incentives are homogenous. Not only to themselves, but also to yours. Realistically, for the average emerging manager, it won’t be. But if you know it won’t be, prepare guardrails for future conversations. Don’t walk in blind.

Photo by Dan Meyers on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Dear Emerging Manager

letter, dear

You are not all top quartile. Only 25% of you are.

You are not all top decile. Only 10% of you are.

I refuse to believe that I’m somehow seeing only the best in market. I’m not famous or lucky enough to have that fortune. Even the best known LPs I know are not so.

If your marks include companies held at last round valuation (LRV) for longer than two years, please consider proactive re-marks. This includes your angel portfolio.

SAFE rounds are not mark-ups. Do not conflate real marks with hypothetical marks.

If the founder doesn’t know who you are AND if you don’t know the company’s updates in the last two quarters, you don’t know the founder. Do not pretend you do. Your investment is not accretive to your future network. I dare say if I went to those founders right now, and asked them who their top five favorite investors are, you won’t come up. You’re forgettable. And that’s a cardinal sin of firm-building.

Let me caveat that firm-building means you plan to grow the firm. That where you are today is not where you want to stay forever as a GP. This matters far less if this is a one-and-done fund. That is okay. You don’t have to love venture forever. You don’t have to pretend you do.

Do not believe you are that special if you have a multi-stage GP as an LP. Many of the notable multi-stage GPs have invested in many. Some have invested in multiple dozens. Others hundreds. A handful we see in almost every deck. It is their job to see everything Or at least attempt to. The cardinal sin for a multi-stage GP is to not see the deal, worse than not picking or winning it.

Assume all your LPs will be passive LPs. I don’t care about their profile, how referenceable they are, how much they love you, how much they want to help. Give it a few months, a year at best, they will become passive. Human interest is fleeting. Especially since venture is the smallest bucket in our allocation (excluding funds-of-funds). And yes, they have day jobs. There are exceptions. For instance, someone who wants to start their own VC fund or someone who wants to be a VC themselves. That is not everyone.

When modeling, it is bold of you to assume that more than 10% of your portfolio will be outliers. It is bold of you to assume that more than 5% of your portfolio will be outliers. We are in a power law industry.

You will get diluted. More than you think. With how much longer companies are staying private, and how much capital is available in the later growth stages, you will get diluted. 80% is safe to assume if you have no reserves. Down to 65% depending on how much you have. There are very, very few cases you only have 50% dilution. Yet I see many GPs model their portfolio that way.

Pro rata is a legal right no successful capital will grant without a fight. If you get it without a fight down the road on a great company, ask yourself why you’re so lucky. And never forget to ask yourself that question.

In a market of exceptions, you are all more normal than you think. It sucks. In any other industry, most of you will have fairly little competition for greatness, but you chose one of the few industries where your competition is all exceptions.

How you react to a ‘no’ from an LP is a sobering fact and a great telltale sign of the strength of your relationships. I love chatting with other LPs who’ve passed on you. Not because I need to hear their whyโ€”most of our interests and mandates are different, but because I almost always ask how you react to their ‘no.’ And I am not alone here. Usually, LPs volunteer that information up quite readily. Of note, different LPs say ‘no’ differently. Most don’t. A fact I am aware of.

Many of us who do this as our primary job love you. We love venture. We love the romanticism that comes with this space. Do not play the hopeless romantic back. We need the truth.

There’s a great line that Elizabeth Gilbert credits her wife Rayya Elias. “The truth has legs. It always stands. When everything else in the room has blown up or dissolved away, the only thing left standing will always be the truth. Since thatโ€™s where youโ€™re gonna end up anyway, you might as well just start there.”

The best time to share the truth is in person. And immediately. The second best is a 1:1 call. If it’s not urgent, save it for the AGM. If it is, call us.

We should not learn about you or your portfolio for the first time via the news. If we are, you’ve lost our trust. Shit happens. We get it. How you respond and communicate shit is what makes or breaks a relationship.

Many of my colleagues try to be helpful even if they can’t invest. Understand because they’re human they can’t be so for everyone. So when they are, don’t take it for granted.

If you conflate any of the above, you’re either lying to yourself or you’re lying to us. The former means you’re never going to make it in this industry. The latter means we’re just not going to be good partners for you.

This is not a Bible. Do not swear by it. Do not pray to it by the bedside every night.

This is just a morning wake-up call. Some of you have already woken up. Many of you may not have.

Photo by รlvaro Serrano on Unsplash


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.