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.

Three E’s of Fund Discipline

railroad, discipline

At a dinner earlier this week, a Fund I GP shared how she had recently hosted her first AGM (annual general meeting). Of which, she spent a few hundred dollars to plan the whole thing. She called in favors on venue. Sponsors to cover food. And the only thing I believe she spent money on were gifts for her LPs. For comparison, when I caught up with a firm with 10+ active funds, they said they spend about $2M on their annual summit.

For the uninitiated, the annual summit or AGM is typically the event VC firms hold once a year for their investors, as well as for their portfolio to recap the year and share what’s next. I won’t go too deep here, but for those curious, I wrote a post last week on this.

Naturally, I had to tip my hat off. Not only is hosting a large event like an AGM time-consuming, to minimize the damage to one’s wallet to only a few hundred is a Herculean feat. And yes, she single-handedly pulled it off. While I wasn’t there myself, A+ for executional discipline.

One of three kinds of discipline that LPs expect of GPs. What are the three?

  1. Entry discipline
  2. Exit discipline
  3. Executional discipline

The three E’s.

Did I force myself to find three words that start with E’s that fit? I’m glad you noticed. Originally, called it: investing discipline, exit discipline, and operational discipline. But I digress.

Let me elaborate.

Entry discipline is all about what and how you invest. It’s the one GPs talk about the most. While it is important – one of the three legs of the stool, it’s not the only one that matters. Nevertheless, it’s a bet on the investor.

These include:

  • Entry prices (pre-money versus post-money valuation)
  • Ownership on entry
  • Sourcing / picking / winning
  • Due diligence process (references, legal diligence, tech diligence, operational diligence, etc.)
  • Prepared mind
  • Terms of investment (you’d be surprised the number of
  • Pro rata rights, and drag along, and right of first refusal (ROFR)
  • Information rights
  • Portfolio governance (board versus board observer seats)

In the words of Renaissance’s Jeff Rinvelt, “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.”

Exit discipline is all about how you think about portfolio construction on a broader sense. And of course, how and when to exit positions. It’s the one LPs care about most in a liquidity-starved environment. It matters especially so for venture that’s known for long illiquidity periods. Still matters for buyouts and other assets, but those have shorter time horizons. When am I going to get my money back? Is there a plan? And while mileage will always vary fund to fund, are you at least primed to react when there are opportunities? Will it be consistent or will you suffer from opportunistic whiplash? It’s a bet on the fund manager. Or really in Jeff’s words, the exit manager.

These include:

  • Strategy on when AND how to sell. Simply, how much upside to cap to protect your downside.
  • Proactive and explicit communication on fund lifespan and extensions
  • Relationships with secondary buyers
  • Recycling
  • Early distributions (after the recycling period)
  • Enterprise value to breakeven. To 3X. To 5X.
  • The exit manager, if applicable

To quote the amazing Ashby Monk, “the difference between your gross return and your net return is an investment in their organization.” In other words, executional discipline is a bet on the team. Is the team uniquely positioned to scale execution? Are they incentivized in the long-term to do the right thing for both founders and LPs? How is knowledge passed down?

These include:

  • Fees on capital committed versus capital deployed
  • Fund expenses (travel, meals, hotels, fund admin, legal, accounting, etc.)
  • Talent
  • Events, AGMs, brand-building exercises
  • Content engine, if one pays for such
  • GP salaries
  • Culture (deal attribution, short and long-term incentive plans, manifestos, succession planning, promotions, vesting schedules, etc.)
  • Carry
  • Reporting (Monthly, quarterly, or annually. It doesn’t matter which, just stick to it. Be consistent.)
  • Valuation Policy / Marks (FYI, SAFEs and convertible notes are not marks. But also, if a portfolio company is overvalued, what’s your valuation policy?)
  • LP Advisory Committee (LPAC)
  • LP Agreement (LPA) / Subscription Agreement
  • Capital calls
  • Cybersecurity policy / Information policy (Who gets access to what information?)
  • Compliance / PR

Obviously, as your track record and returns grow and speak for themselves, you accumulate a new type of currency in the karmic bank account: trust. You should always never exceed your means to pay. That your credit balance never exceeds your debit, but you undeniably have a greater credit line to operate the institution.

To simplify…

Entry DisciplineExit DisciplineExecutional Discipline
The betThe bet on the investorThe bet on the
fund manager
The bet on the
team

Note that for an emerging fund, these three disciplines are expected of the same individual. In many ways, much harder than if you had a fully staffed team.

Photo by Ales Krivec 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.

LPs Should Get Paid More | Ashby Monk | Superclusters | S4E5

ashby monk

“Innovation everywhere, but especially in the land of pensions, endowments, and foundations, is a function of courage and crisis.” – Ashby Monk

Dr. Ashby Monk is currently a Senior Research Engineer, School of Engineering at Stanford University and holds the position of Executive Director of the Stanford Research Initiative on Long-Term Investing.

Ashby has more than 20 years of experience studying and advising investment organizations. He has authored multiple books and published 100s of research papers on institutional investing. His latest book, The Technologized Investor, won the 2021 Silver Medal from the Axiom Business Book Awards in the Business Technology category.

Outside of academia, Ashby has co-founded several companies that help investors make better investment decisions, including Real Capital Innovation (acquired by Addepar), FutureProof, GrowthsphereAI, Long Game Savings (acquired by Truist), NetPurpose, D.A.T.A., SheltonAI, and ThirdAct. He is co-founder and managing partner of KDX, a venture capital firm focused on investment technologies.

He is a member of the CFA Institute’s Future of Finance Advisory Council and was named by CIO Magazine as one of the most influential academics in the institutional investing world. He received his Doctorate in Economic Geography at the University of Oxford, holds a Master’s in International Economics from the Université de Paris I – Pantheon Sorbonne, and has a Bachelor’s in Economics from Princeton University.

You can find Ashby on his socials here:
X / Twitter: https://x.com/sovereignfund
LinkedIn: https://www.linkedin.com/in/ashby-monk-208a479/

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
[03:44] “I don’t know what to do with my hands”
[04:44] The origin story of Ashby’s LinkedIn skills
[09:04] Ashby’s obsession with the worst title out there
[12:54] Titles at institutional investment firms
[17:05] Building the right incentives for institutional LPs
[20:54] The decision to buy or build for pension funds
[22:36] What’s a smart way to think about the difference of gross and net?
[23:17] When are management fees not justified?
[26:06] When managers charge fees on SPVs
[28:12] When are GPs still grateful for your LP capital?
[29:40] Challenges with the endowment model in PE and VC
[31:14] Why LPs misrepresent what budget fees come out of
[35:28] Compensation structure of a pension fund
[37:59] CalPERS compensation structure
[39:19] The highest paid employees in government jobs
[42:39] Traits of an incredibly talented investor
[47:06] Hire hard, manage light
[51:07] Ashby’s journey into the LP space
[56:05] Why should a young professional work at a pension
[1:00:24] Who outside of investments influences the way Ashby thinks about investing?
[1:02:28] What is organic finance?
[1:07:08] The post-credit scene
[1:12:32] Thank you to Alchemist Accelerator for sponsoring!
[1:13:33] If you enjoyed the episode, would love if you shared it with one friend who would enjoyed it as well!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The fastest way to become a billionaire in America today is to set up an alternative investment firm and manage pension capital. Literally. That’s the fastest path. Faster than starting a tech company.” – Ashby Monk

“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

“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

“[LPs] want to solve the problem for their sponsor by reducing the cost of a promise.” – Ashby Monk

“Innovation everywhere, but especially in the land of pensions, endowments, and foundations, is a function of courage and crisis.” – Ashby Monk

“The highest people paid in state jobs are football coaches.” – Ashby Monk

“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

“The job of an investor is to look at the same data that you and I are looking at, and be ready to make a different conclusion. That’s how you outperform.” – Ashby Monk

“Hire hard; manage light.” – Ashby Monk

“The way best practices are communicated in this industry is through role models. So, Yale model, Canadian model, Norway model… There are no schools of investing. […] And the way models emerge is you get an innovation that results in outperformance.” – Ashby Monk

“I do research projects on nothing.” – Ashby Monk on research into solutions that don’t exist in the world yet

“There are two types of innovation. There’s innovation as an invention. And there’s discovery. And a lot of what I do is discover and apply.” – Ashby Monk


Follow David Zhou for more Superclusters content:
For podcast show notes: https://cupofzhou.com/superclusters
Follow David Zhou’s blog: https://cupofzhou.com
Follow Superclusters on Twitter: https://twitter.com/SuperclustersLP
Follow Superclusters on TikTok: https://www.tiktok.com/@super.clusters
Follow Superclusters on Instagram: https://instagram.com/super.clusters


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.