35 Biggest Investing Lessons from 4 Seasons of Superclusters

piggy bank, investing, coin

The title says it all. I’m four seasons in and I’m fortunate to have learned from some of the best and most thoughtful individuals in the LP industry. I often joke with friends that Superclusters allows me to ask dumb questions to smart people. But there’s quite a bit of truth there as well. I look back in Season 1, and I’m proud to see the evolution of my questions as well.

There was a piece back in 2022 where Johns Hopkins’ Jeff Hooke said that “75% of funds insist they are in the top quartile.” To my anecdotal knowledge, that seems to hold. I might say 75% of angel investors starting their first funds say they’re top quartile. And 90% of Fund IIs say their Fund Is are top quartile. So the big looming question as an LP is how do you know which are and which aren’t.

And if we were all being honest with each other, the first five years of returns and IRRs really aren’t indicative of the fund’s actual performance. In fact, Stepstone had a recent piece that illustrated fewer than 50% of top-quartile funds at Year 5 stay there by Year 10. 30% fall to second quartile. 13% slip to third. 9% fall from grace to the bottom quartile. But only 3.7% of bottom-quartile funds make it to the top quartile after its 10-year run (on a net TVPI basis).

I’ve enjoyed every single podcast episode I’ve recorded to date. And all the offline conversations that I’ve had because of the podcast itself. Nevertheless, it’s always fascinating when I learn something for the first time on the podcast while we’re recording. Excluding the longer lessons some of our guests have shared (I’m looking at you Evan, Charlotte, and much much more), below are the many Twitter-worthy (not calling it X) soundbites that have come up in the podcast so far.

  1. “Entrepreneurship is like a gas. It’s hottest when it’s compressed.” — Chris Douvos
  2. “I’m looking for well-rounded holes that are made up of jagged pieces that fit together nicely.” — Chris Douvos
  3. “If you provide me exposure to the exact same pool of startups [as] another GP of mine, then unfortunately, you don’t have proprietary deal flow for me. You don’t enhance my network diversification.” — Jamie Rhode
  4. “Sell when you can, not when you have to.” — Howard Lindzon
  5. “When you think about investing in any fund, you’re really looking at three main components. It’s sourcing ability. Are you seeing the deals that fit within whatever business model you’re executing on? Do you have some acumen for picking? And then, the third is: what is your ability to win? Have you proven your ability to win, get into really interesting deals that might’ve been either oversubscribed or hard to get into? Were you able to do your pro rata into the next round because you added value? And we also look through the lens of: Does this person have some asymmetric edge on at least two of those three things?” — Samir Kaji
  6. “85% of returns flow to 5% of the funds, and that those 5% of the funds are very sticky. So we call that the ‘Champions League Effect.’” — Jaap Vriesendorp
  7. “The truth of the matter, when we look at the data, is that entry points matter much less than the exit points. Because venture is about outliers and outliers are created through IPOs, the exit window matters a lot. And to create a big enough exit window to let every vintage that we create in the fund of funds world to be a good vintage, we invest [in] pre-seed and seed funds – that invest in companies that need to go to the stock market maybe in 7-8 years. Then Series A and Series B equal ‘early stage.’ And everything later than that, we call ‘growth.’” — Jaap Vriesendorp
  8. “[When] you’re generally looking at four to five hundred distinct companies, 10% of those companies generally drive most of the returns. You want to make sure that the company that drives the returns you are invested in with the manager where you size it appropriately relative to your overall fund of funds. So when we double click on our funds, the top 10 portfolio companies – not the funds, but portfolio companies, return sometimes multiples of our fund of funds.” — Aram Verdiyan
  9. “If you’re overly concentrated, you better be damn good at your job ‘cause you just raised the bar too high.” — Beezer Clarkson
  10. “[David Marquardt] said, ‘You know what? You’re a well-trained institutional investor. And your decision was precisely right and exactly wrong.’ And sometimes that happens. In this business, sometimes good decisions have bad outcomes and bad decisions have good outcomes.” — Chris Douvos
  11. “Miller Motorcars doesn’t accept relative performance for least payments on your Lamborghini.” — Chris Douvos
  12. “The biggest leverage on time you can get is identifying which questions are the need-to-haves versus nice-to-haves and knowing when enough work is enough.” — John Felix
  13. “In venture, we don’t look at IRR at all because manipulating IRR is far too easy with the timing of capital calls, credit lines, and various other levers that can be pulled by the GP.” — Evan Finkel
  14. “The average length of a VC fund is double that of a typical American marriage. So VC splits – divorce – is much more likely than getting hit by a bus.” — Raida Daouk
  15. “Historically, if you look at the last 10 years of data, it would suggest that multiple [of the premium of a late stage valuation to seed stage valuation] should cover around 20-25 times. […] In 2021, that number hit 42 times. […] Last year, that number was around eight.” — Rick Zullo (circa 2024)
  16. “The job and the role that goes most unseen by LPs and everybody outside of the firm is the role of the culture keeper.” — Ben Choi
  17. “You can map out what your ideal process is, but it’s actually the depth of discussion that the internal team has with one another. […] You have to define what your vision for the firm is years out, in order to make sure that you’re setting those people up for success and that they have a runway and a growth path and that they feel empowered and they feel like they’re learning and they’re contributing as part of the brand. And so much of what happens there, it does tie back to culture […] There’s this amazing, amazing commercial that Michael Phelps did, […] and the tagline behind it was ‘It’s what you do in the dark that puts you in the light.’” — Lisa Cawley
  18. “In venture, LPs are looking for GPs with loaded dice.” — Ben Choi
  19. “If I hire someone, I don’t really want to hire right out of school. I want to hire someone with a little bit of professional experience. And I want someone who’s been yelled at. […] I don’t want to have to triple check work. I want to be able to build trust. Going and getting that professional experience somewhere, even if it’s at a startup or venture firm. Having someone have oversight on you and [push] you to do excellent work and [help] you understand why it matters… High quality output can help you gain so much trust.” — Jaclyn Freeman Hester
  20. “LPs watch the movie, but don’t read the book.” — Ben Choi
  21. “If it’s not documented, it’s not done.” — Lisa Cawley
  22. “If somebody is so good that they can raise their own fund, that’s exactly who you want in your partnership. You want your partnership of equals that decide to get together, not just are so grateful to have a chance to be here, but they’re not that great.” — Ben Choi
  23. “When you bring people in as partners, being generous around compensating them from funds they did not build can help create alignment because they’re not sitting there getting rich off of something that started five years ago and exits in ten years. So they’re kind of on an island because everybody else is in a different economic position and that can be very isolating.” — Jaclyn Freeman Hester
  24. “Neutral references are worse than negative references.” — Kelli Fontaine
  25. “Everybody uses year benchmarking, but that’s not the appropriate way to measure. We have one fund manager that takes five years to commit the capital to do initial investments versus a manager that does it all in a year. You’re gonna look very, very different. Ten years from now, 15 years from now, then you can start benchmarking against each other from that vintage.” — Kelli Fontaine
  26. “We are not in the Monte Carlo simulation game at all; we’re basically an excel spreadsheet.” — Jeff Rinvelt
  27. “A lot of those skills [to be a fund manager] are already baked in. The one that wasn’t baked in for a lot of these firms was the exit manager – the ones that help you sell. […] If you don’t have it, there should be somebody that it’s their job to look at exits. ” — Jeff Rinvelt
  28. “Getting an LP is like pulling a weight with a string of thread. If you pull too hard, the string snaps. If you don’t pull hard enough, you don’t pull the weight at all. It’s this very careful balancing act of moving people along in a process.” — Dan Stolar
  29. “Going to see accounts before budgets are set helps get your brand and your story in the mind of the budget setter. In the case of the US, budgets are set in January and July, depending on the fiscal year. In the case of Japan, budgets are set at the end of March, early April. To get into the budget for Tokyo, you gotta be working with the client in the fall to get them ready to do it for the next fiscal year. [For] Korea, the budgets are set in January, but they don’t really get executed on till the first of April. So there’s time in there where you can work on those things. The same thing is true with Europe. A lot of budgets are mid-year. So you develop some understanding of patterns. You need to give yourself, for better or worse if you’re raising money, two to three years of relationship-building with clients.” — David York
  30. “Many pension plans, especially in America, put blinders on. ‘Don’t tell me what I’m paying my external managers. I really want to focus and make sure we’re not overpaying our internal people.’ And so then it becomes, you can’t ignore the external fees because the internal costs and external fees are related. If you pay great people internally, you can push back on the external fees. If you don’t pay great people internally, then you’re a price taker.” — Ashby Monk
  31. “You need to realize that when the managers tell you that it’s only the net returns that matter. They’re really hoping you’ll just accept that as a logic that’s sound. What they’re hoping you don’t question them on is the difference between your gross return and your net return is an investment in their organization. And that is a capability that will compound in its value over time. And then they will wield that back against you and extract more fees from you, which is why the alternative investment industry in the world today is where most of the profits in the investment industry are captured and captured by GPs.” — Ashby Monk
  32. “I often tell pensions you should pay people at the 49th percentile. So, just a bit less than average. So that the people going and working there also share the mission. They love the mission ‘cause that actually is, in my experience, the magic of the culture in these organizations that you don’t want to lose.” — Ashby Monk
  33. “The thing about working with self-motivated people and driven people, on their worst day, they are pushing themselves very hard and your job is to reduce the stress in that conversation.” — Nakul Mandan
  34. “I only put the regenerative part of a wealth pool into venture. […] That number – how much money you are putting into venture capital per year largely dictates which game you’re playing.” — Jay Rongjie Wang
  35. “When investing in funds, you are investing in a blind pool of human potential.” — Adam Marchick

Photo by Andre Taissin 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 Value of Being an Outsider

fence, inside, outside

In 1968, NASA tasked the late George Land to create a test that would help NASA hire more creative geniuses. Does genius and creativity come from nature or nurture? As such his job was to create a test so simple that even children could take it. And he found that for children ages 4-5, out of 1,600 children, 98% of them qualified to be a genius. Divergent thinkers. Then, he waited five years to assess these same children. To which he found, only 30% qualified. Then another five years later, only 12% of the same children were what he counted to be geniuses.

It begged the question: What percent of adults are geniuses?

The answer, 2%.

For those curious, I’d highly recommend George’s 2011 TEDx talk about the topic.

Of course, the lesson from all of this is the fallacy of modern-day education. And the same is true for the adult world between convergent thinkers and divergent thinkers. I believe in the world of venture at least, we have terminology that’s little less palatable (at least for me, although on occasion I’m guilty of using them myself): insiders and outsiders.

My friend Anne sent me this piece by Auren Hoffman recently on insiders and outsiders. An incredibly well-written piece, and quite thought-provoking. I’ve largely thought about how outsiders can become insiders, but silly me, less about the value of staying an outsider or an insider aiming to become an outsider. Moreover, that to be successful as an insider, there’s actually a rather predictable path to become one. Or at least to help your children become one. Go to Harvard. Play insider sports, like gold, or horse-riding, or sailing. And son. But in Auren’s words, to be successful as an outsider, well, “being [an outsider] is MUCH higher beta. They could end up changing the world for the better. They also could blow it up. Or just never be accepted and live less happy.”

And while I may not agree with everything that Auren proposes, a lot of it makes sense. In fact, 11 words definitely caught my eye. “Outsiders take things from insiders.  Insiders inherit things from other insiders.” And as such, insiders play the status quo; outsiders change the status quo.

It’s interesting. Every generation of VC, there’s a changing of the guard. Many of the new regime are outsiders. People who think different. People who exhibit a level of creativity that is uncommon in VCs. Either in the form of business models or how they provide value. How they build brand. Or simply how their brain works. People that in bringing a fresh perspective were able to find the next great companies unlike any other.

Interestingly enough, in my buddy and Superclusters guest Jaap’s recent study of 2,092 North American and European VC funds, he found that these are the folks who are more likely to hit fundraise targets than any other GP persona. Aka 45% success rate. And perform highest at 2.4X net TVPI, but only average on DPI and IRR.

Source: Jaap Vriesendorp’s cluster model on 2,092 VC funds. Find a more interactive one here.

My guess here is that these outsiders, in being artisanal about their craft and — well, at least with respect to the VC industry at large, divergent thinkers — find their tribe rather quickly because LPs quick self-select themselves in or out of a relationship with them. They’re the round pegs in the square holes, to borrow a Steve Jobs moniker. So when most others look square, the few round holes instantly identify with these round pegs. And more often than not, they’re new to the asset management game, so have lower fund targets and a more precise strategy. Downside to that is they’re still learning the ropes of exit strategies and fund management. Which also explains the high volatility in returns.

And while there’s much higher beta in being an outsider, there’s plenty of research to suggest that there is also greater alpha. But it’s going to be unfair. The deck is rigged against you. There’s a great Marcus Aurelius line. “Mental toughness is knowing life isn’t fair and still playing to win.”

The outsiders who win exhibit exactly that mental fortitude against stacked odds. Besides, there’s joy in doing things differently.

Photo by Randy Fath 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.

Exit Windows Matter More Than Entry Windows | Jaap Vriesendorp | Superclusters | S2E6

Jaap Vriesendorp is one of the managing partners of Marktlink Capital, an investment manager from the Netherlands investing over $1b into private equity and venture capital funds. Marktlink Capital’s LPs are almost exclusively Dutch (tech) entrepreneurs from companies such as Booking.com, Adyen and Hellofresh. At Marktlink Capital Jaap focusses on selecting venture and growth funds across Europe and the US. Before Marktlink Capital, he spent the majority of his time at McKinsey where he was one of the leaders of McKinsey’s practice for Venture Capital, Unicorns & Startups in Europe. Besides work, Jaap enjoys sports, mountains, technology, comic books, music and art.

He holds an MBA from INSEAD and is a guest lecturer at the Rotterdam School of Management (Erasmus University). He occasionally shares his views on private market investing on Medium.

You can find Jaap on his socials here:
LinkedIn: https://www.linkedin.com/in/jaap-vriesendorp/
Medium: https://medium.com/@jjjvriesendorp

And huge thanks to this episode’s sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

Listen to the episode on Apple Podcasts and Spotify. You can also watch the episode on YouTube here.

Brought to you by Alchemist Accelerator.

OUTLINE:

[00:00] Intro
[03:04] The significance of Mount Pinatubo in Jaap’s life
[06:23] One Shell Jackets
[08:45] The entrepreneurial gene in the Vriesendorp family that dates back to Jaap’s grandfather
[14:32] The 1-year time constraint of starting Welt Ventures
[17:43] What did the transition to becoming an investor look like for Jaap
[20:28] The 3 traits that define a community
[24:03] How often does Jaap host events?
[25:30] How does Marktlink Capital have 1000 LPs?
[27:15] What was Marktlink’s pitch to their LPs?
[28:32] What is the typical individual LP’s allocation model to VC/PE?
[29:41] Why is VC/PE uncorrelated to the public markets?
[35:10] The 3 facts that define Welt Ventures’ portfolio construction model
[38:28] Exit windows matter more than entry windows
[42:15] Diversification in PE = Concentration in VC
[47:42] 3 types of emerging GPs that deliver alpha
[49:35] Which European fund has a really unique thesis?
[51:44] Which school did Jaap apply to but not get in?
[53:55] Thank you to Alchemist Accelerator for sponsoring!
[56:31] If anything resonated with you in today’s episode, we’d be honored to earn a like, comment, or share!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“We set out to achieve three things with the community:

  1. We wanted people to have fun with each other. And when entrepreneurs meet entrepreneurs, good stuff happens even if you don’t bring any content.
  2. We wanted to bring the absolute best type of propositions. So in terms of sales, it means sales almost without being sales where you offer something that people really want.
  3. Organized knowledge in a way that nobody does.” – Jaap Vriesendorp

“85% of returns flow to 5% of the funds, and that those 5% of the funds are very sticky. So we call that the ‘Champions League Effect.’” – Jaap Vriesendorp

“The truth of the matter, when we look at the data, is that entry points matter much less than the exit points. Because venture is about outliers and outliers are created through IPOs, the exit window matters a lot. And to create a big enough exit window to let every vintage that we create in the fund of funds world to be a good vintage, we invest [in] pre-seed and seed funds – that invest in companies that need to go to the stock market maybe in 7-8 years. Then Series A and Series B equal ‘early stage.’ And everything later than that, we call ‘growth.’” – Jaap Vriesendorp


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