35 Biggest Investing Lessons from 4 Seasons of Superclusters

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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. โ€œEntrepreneurship is like a gas. Itโ€™s hottest when itโ€™s compressed.โ€ โ€” Chris Douvos
  2. โ€œIโ€™m looking for well-rounded holes that are made up of jagged pieces that fit together nicely.โ€ โ€” Chris Douvos
  3. โ€œIf you provide me exposure to the exact same pool of startups [as] another GP of mine, then unfortunately, you donโ€™t have proprietary deal flow for me. You donโ€™t enhance my network diversification.โ€ โ€” Jamie Rhode
  4. โ€œSell when you can, not when you have to.โ€ โ€” Howard Lindzon
  5. โ€œWhen you think about investing in any fund, youโ€™re really looking at three main components. Itโ€™s sourcing ability. Are you seeing the deals that fit within whatever business model youโ€™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 mightโ€™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?โ€ โ€” Samir Kaji
  6. โ€œ85% of returns flow to 5% of the funds, and that those 5% of the funds are very sticky. So we call that the โ€˜Champions League Effect.โ€™โ€ โ€” Jaap Vriesendorp
  7. โ€œThe 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 โ€“ that invest in companies that need to go to the stock market maybe in 7-8 years. Then Series A and Series B equal โ€˜early stage.โ€™ And everything later than that, we call โ€˜growth.โ€™โ€ โ€” Jaap Vriesendorp
  8. โ€œ[When] youโ€™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 โ€“ not the funds, but portfolio companies, return sometimes multiples of our fund of funds.โ€ โ€” Aram Verdiyan
  9. โ€œIf youโ€™re overly concentrated, you better be damn good at your job โ€˜cause you just raised the bar too high.โ€ โ€” Beezer Clarkson
  10. โ€œ[David Marquardt] said, โ€˜You know what? Youโ€™re a well-trained institutional investor. And your decision was precisely right and exactly wrong.โ€™ And sometimes that happens. In this business, sometimes good decisions have bad outcomes and bad decisions have good outcomes.โ€ โ€” Chris Douvos
  11. โ€œMiller Motorcars doesnโ€™t accept relative performance for least payments on your Lamborghini.โ€ โ€” Chris Douvos
  12. โ€œThe 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.โ€ โ€” John Felix
  13. โ€œIn venture, we donโ€™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.โ€ โ€” Evan Finkel
  14. โ€œThe average length of a VC fund is double that of a typical American marriage. So VC splits โ€“ divorce โ€“ is much more likely than getting hit by a bus.โ€ โ€” Raida Daouk
  15. โ€œHistorically, 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. [โ€ฆ] In 2021, that number hit 42 times. [โ€ฆ] Last year, that number was around eight.โ€ โ€” Rick Zullo (circa 2024)
  16. โ€œThe job and the role that goes most unseen by LPs and everybody outside of the firm is the role of the culture keeper.โ€ โ€” Ben Choi
  17. โ€œYou can map out what your ideal process is, but itโ€™s actually the depth of discussion that the internal team has with one another. [โ€ฆ] You have to define what your vision for the firm is years out, in order to make sure that youโ€™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 theyโ€™re learning and theyโ€™re contributing as part of the brand. And so much of what happens there, it does tie back to culture [โ€ฆ] Thereโ€™s this amazing, amazing commercial that Michael Phelps did, [โ€ฆ] and the tagline behind it was โ€˜Itโ€™s what you do in the dark that puts you in the light.โ€™โ€ โ€” Lisa Cawley
  18. โ€œIn venture, LPs are looking for GPs with loaded dice.โ€ โ€” Ben Choi
  19. โ€œIf I hire someone, I donโ€™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 whoโ€™s been yelled at. [โ€ฆ] I donโ€™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 itโ€™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 mattersโ€ฆ High quality output can help you gain so much trust.โ€ โ€” Jaclyn Freeman Hester
  20. โ€œLPs watch the movie, but donโ€™t read the book.โ€ โ€” Ben Choi
  21. โ€œIf itโ€™s not documented, itโ€™s not done.โ€ โ€” Lisa Cawley
  22. โ€œIf somebody is so good that they can raise their own fund, thatโ€™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 theyโ€™re not that great.โ€ โ€” Ben Choi
  23. โ€œWhen you bring people in as partners, being generous around compensating them from funds they did not build can help create alignment because theyโ€™re not sitting there getting rich off of something that started five years ago and exits in ten years. So theyโ€™re kind of on an island because everybody else is in a different economic position and that can be very isolating.โ€ โ€” Jaclyn Freeman Hester
  24. โ€œNeutral references are worse than negative references.โ€ โ€” Kelli Fontaine
  25. โ€œEverybody uses year benchmarking, but thatโ€™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. Youโ€™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.โ€ โ€” Kelli Fontaine
  26. โ€œWe are not in the Monte Carlo simulation game at all; weโ€™re basically an excel spreadsheet.โ€ โ€” Jeff Rinvelt
  27. โ€œA lot of those skills [to be a fund manager] are already baked in. The one that wasnโ€™t baked in for a lot of these firms was the exit manager โ€“ the ones that help you sell. [โ€ฆ] If you donโ€™t have it, there should be somebody that itโ€™s their job to look at exits. โ€ โ€” Jeff Rinvelt
  28. โ€œGetting an LP is like pulling a weight with a string of thread. If you pull too hard, the string snaps. If you donโ€™t pull hard enough, you donโ€™t pull the weight at all. Itโ€™s this very careful balancing act of moving people along in a process.โ€ โ€” Dan Stolar
  29. โ€œGoing 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 donโ€™t really get executed on till the first of April. So thereโ€™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 youโ€™re raising money, two to three years of relationship-building with clients.โ€ โ€” David York
  30. โ€œMany pension plans, especially in America, put blinders on. โ€˜Donโ€™t tell me what Iโ€™m paying my external managers. I really want to focus and make sure weโ€™re not overpaying our internal people.โ€™ And so then it becomes, you canโ€™t ignore the external fees because the internal costs and external fees are related.ย If you pay great people internally, you can push back on the external fees. If you donโ€™t pay great people internally, then youโ€™re a price taker.โ€ โ€” Ashby Monk
  31. โ€œYou need to realize that when the managers tell you that itโ€™s only the net returns that matter. Theyโ€™re really hoping youโ€™ll just accept that as a logic thatโ€™s sound. What theyโ€™re hoping you donโ€™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 isย where most of the profits in the investment industry are capturedย and captured by GPs.โ€ โ€” Ashby Monk
  32. โ€œI 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 โ€˜cause that actually is, in my experience, the magic of the culture in these organizations that you donโ€™t want to lose.โ€ โ€” Ashby Monk
  33. โ€œThe 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.โ€ โ€” Nakul Mandan
  34. โ€œI only put the regenerative part of a wealth pool into venture. [โ€ฆ] That number โ€“ how much money you are putting into venture capital per year largely dictates which game youโ€™re playing.โ€ โ€” Jay Rongjie Wang
  35. โ€œWhen investing in funds, you are investing in a blind pool of human potential.โ€ โ€” Adam Marchick

Photo by Andre Taissin on Unsplash


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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.

Operational Due Diligence Like You’ve Never Seen Before | Evan Finkel | Superclusters | S3E4

Evan currently serves as Head of Venture Capital Investments and Research for Integra Global Advisors, a multi-family office. Prior to Integra, Evan served as Senior Manager of Data Science for Anheuser-Busch InBev where he oversaw data science and strategy for the US marketing organization. Prior to Anheuser-Busch, Evan spent two years as a Management Consultant at Marketing Management Analytics and held a technical role at Amazon. Evan earned an MS in Computer Science with a concentration in machine learning from Georgia Tech and studied computational and applied mathematics at the City University of New York and finance and psychology at the University of Miami.

You can find Evan on his socials here:
LinkedIn: https://www.linkedin.com/in/evanfinkel/

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
[03:27] What are the mechanics of a great cold email?
[07:54] Evan’s background in sports marketing
[10:54] The kinds of data to ignore as an LP
[13:01] Portability and replicability of track record
[19:57] How much thesis drift is too much?
[22:37] What happens when a partner isn’t pulling their weight?
[29:35] Why does Evan have two bachelor degrees?
[34:38] Why study quantum mechanics in applied math?
[38:25] Evan’s journey to Integra
[45:21] Buy vs Build at a fund-of-funds
[47:40] Questions to ask when choosing which vendor to work with
[51:24] How Evan thinks about operational diligence
[58:30] Setting up an information policy in your firm
[1:01:39] Valuation policy at a hedge fund vs VC fund
[1:11:12] Why doesn’t Integra have strict mandates for geographies to invest in?
[1:21:20] The fallacy with LPs overweighing DPI in 2020-2021
[1:27:15] Evan’s greatest life lesson
[1:28:14] Evan’s favorite kosher restaurants in NYC
[1:32:07] “Post-credit scene”
[1:34:24] Thank you to Alchemist Accelerator for sponsoring!
[1:35:25] If you liked this episode, it would mean a lot if you left a like and shared this episode with one friend!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

โ€œItโ€™s important to be data-informed, not data-driven.โ€ โ€“ Evan Finkel

โ€œNot only does [an investment] have to be the best in that geography, it actually has to be better than the incremental dollar we could put in any other geography.โ€ โ€“ Evan Finkel

โ€œThe way we think about VC is both on an absolute and a relative basis. On an absolute basis, we have to be able to underwrite a manager to 3X net or better, or ideally 4X net or better. Because otherwise the lockup doesnโ€™t make sense. It doesnโ€™t make sense to lock up your money for 10, 12, or 15 years with pretty limited distributions. In order to be able to consider a VC fund for our portfolio, we have to be able to underwrite it to at least 3X, but ideally 4X or better.

โ€œBut then thereโ€™s also a relative component. Weโ€™re not looking for the best relative managers. Understanding whether this is a really good year or weak yearโ€ฆ You might be the best manager of a given vintage, but in absolute terms, you actually might not be quite as impressive. […] It helps us contextualize the performance of a given manager.โ€ โ€“ Evan Finkel

โ€œDPI generated in a chaotic environment is sort of similar to TVPI generated in a chaotic environment. Itโ€™s great it happened, but letโ€™s contextualize it properly and donโ€™t overweight DPI when youโ€™re evaluating managers.โ€ โ€“ Evan Finkel

โ€œIn venture, we donโ€™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.โ€ โ€“ Evan Finkel


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