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.

Stress and Ambition

stress, founder stress

“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.”

It’s something Nakul Mandan from Audacious said in a Superclusters episode earlier in Season 4. And a line that’s been gnawing at me for the past few weeks. Particularly, “your job is to reduce the stress in that conversation.” So it got me thinking… Are the entrepreneurs I back stressed (enough)?

I know what you’re thinking. But before you come at me with pitchforks and torches, here me out. If you get to the end of this essay and still feel as strongly, feel free to take a swing at me.

First off, let me define some terms in the above question. An “entrepreneur” is someone who starts something that doesn’t exist in the world already. To me, that is a startup founder, a local restaurant, an emerging fund manager, and so on. I use this term pretty liberally. “Enough” is in moderation. A balance of feeling the pressure and urgency, but not enough to make one go insane. By definition, entrepreneurs — people who dare challenge the world and create something that hasn’t existed before — are ambitious. And ambitious, action-oriented doers are, to Nakul’s point, often hard on themselves. So everything in moderation. As a friend once told me, if you’re doing anything ambitious, a third of your days will be epic. A third will be okay. And a third will absolutely suck. As long as your days feel like that proportionally, you’re on the right track.

So… are the entrepreneurs I back stressed (enough)?

Let’s start with no. Are they the underdog still, pre-product-market fit, stagnating, losing market share, and/or in a crisis?

If not, carry on. It’s okay to not be stressed all the time. In fact, it’s probably not helpful to be stressed all the time.

If so — that they are the underdogs, stagnating or in a crisis — AND they’re not feeling stressed, I do wonder from time to time. And I’d be lying if some part of me didn’t feel buyer’s remorse. Because that means one of three things:

  1. They’ve lost their ability to care. About the product. The market. The team. Or simply, their own ambition. That’s the worst.
  2. Conversely, they don’t feel comfortable enough to be vulnerable with me. And that, in part, not to sugarcoat things, is because of me.
  3. They never cared enough or were ambitious enough in the first place. And that’s something I have to take back to the drawing board so that I learn the next time around.

Nevertheless, regardless of which of the three, it warrants a conversation. A difficult one. One where I try to understand their current motivations, what’s changed. If their motivations still hold true, then I, in Danny Meyer’s words, add “constant, gentle pressure.” For those curious, Chapter 9 of his book. Nevertheless, my job is to give them the activation energy to hopefully get them back on track.

If things change, great. I eventually go back to the first question. Are the entrepreneurs stressed? If not, then I let them on a few things:

  1. I’ll spend less time time with them to prioritize the rest of my portfolio.
  2. If they have any of the money left, they can keep the money. FYI, if it wasn’t my personal angel money, but someone else’s capital (of which I’m a fiduciary), depending on how much they have left, it may lead to a different conclusion. But in general, I view it as a write-off.
  3. Wish them the best of luck in their next chapter.
  4. If they feel the fire burning again (for good reason), they should let me know. And I’m happy to have another conversation.

Now… what happens if the entrepreneurs are stressed. Then I try to figure out if it’s anxiety or stress. Let me define.

Anxiety is caused by things you cannot control. For instance, the market. Other people you cannot control. Or black swan events. Stress, on the other hand, is caused by things you can control. Your own mistakes. Mistakes made by people you hired. Volume of work that needs to be done. Procrastination. Mistakes that can be actively mitigated. For instance, missing the deadline for a quarterly report. Missing payroll due to insufficient funds. Layoffs. Bad performance. Media, publicity, and perception. Something Danny Meyer calls, “writing a great last chapter.” As Danny Meyer puts it, “the worst mistake is not to figure out some way to end up in a better place after having made a mistake.”

If it’s anxiety, my role is to calm the founders. Be the mental support they need. Help them see the bigger picture. Build contingency plans.

If it’s stress, my role is to help them build an action plan. Help get key decision-makers and doers in the same room. Get the founders in front of advisors who can help them think through key considerations and check their blind side (assuming it’s not me. Most of the time it isn’t.). Of course, you need to timebox “thinking” time. There’s a great saying. “There are no right choices; only choices we make right.”

And finally, help the entrepreneurs execute the plan. Sometimes, that requires getting my hands dirty. And that’s what I’m here for. To increase the metabolism of the organization. Or at the very minimum, leadership. Stress is often caused by indigestion of tasks that need to be done.

Alas, the job of an investor, given we’re not in the driver’s seat, that we don’t always have complete information, is to reduce the stress of the founder when we have that conversation. More often than not, ambitious founders are hard enough on themselves.

Photo by Francisco Moreno 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 Holiday Special | Nakul Mandan and Ben Choi | Superclusters | S4PSE1

ben choi, nakul mandan

“VC is more about the ground game than the air game.” – Nakul Mandan

“Entrepreneurs think it’s going to be like the Michael Keaton version, and the good ones, they actually have to work through the Christopher Nolan version of Batman.” – Ben Choi

Nakul Mandan is the founder of Audacious Ventures. Audacious is a seed stage venture firm managing ~$250M. Audacious’ foundational belief is that ultimately startup success comes down to two key ingredients: Large markets and A+ teams. Accordingly, the Audacious team focuses on two jobs: 1/ Invest in force of nature founders; 2/ Help them recruit an A+ team. Then they get out of the way. Prior to founding Audacious, Nakul was a GP at Lightspeed.

Some of the companies Nakul has backed over the last decade include: Gainsight, People.ai, WorkOS, Multiverse, Marketo, 6Sense, BuildingConnected, Vartana, Tezi and Maxima, amongst others.

You can find Nakul on his socials here:
X / Twitter: https://x.com/nakul
LinkedIn: https://www.linkedin.com/in/nakulmandan/
Personal Website: https://www.nakulmandan.com/

Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses. Ben’s love for technology products formed the basis for his successful venture track record, including early stage investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe’s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an engaged member of the Society of Kauffman Fellows and has been named to the Board of Directors for the San Francisco Chinese Culture Center and Children’s Health Council. 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 Palo Alto with his wife, Lydia, and three very active sons.

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

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
[04:14] Why is Nakul fascinated by Batman?
[06:41] Does entrepreneurial motivation often come from inspiration or frustration?
[10:33] Nakul’s childhood and early upbringing
[14:37] How Nakul grew from introvert to extrovert
[16:19] Did Ben see the ambition in Nakul from the day they first met?
[18:19] How did Ben’s parents’ work in Chinatown influence Ben as a teenager?
[22:47] How did Ben and Nakul meet?
[28:50] Would Nakul have raised in 2020 if he knew how hard it would be?
[33:49] Why did Next Legacy not invest in Fund I, but in Fund II?
[37:49] How did Nakul react to the pass on Fund I?
[39:56] The kinds of people at Next Legacy’s dinners
[43:49] Why Audacious kept a low profile in 2021
[49:01] Why Audacious deployed Fund I over 4 years, instead of 3
[51:46] Balancing the paradox of one of Audacious’ cultural values
[55:14] The difference between pitching individuals and institutions
[1:00:42] What is it like to be married to an interior designer?
[1:02:40] Nakul’s favorite coffee shop, bar, and restaurant
[1:05:56] What makes a sock special to Ben?
[1:07:17] Why does Ben still like venture?
[1:08:10] Why does Nakul still like venture?
[1:11:36] Thank you to Alchemist Accelerator for sponsoring!
[1:12:37] If you enjoyed this holiday episode, and want more like this, do let me know!

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The risk is slow failure. And actually that’s the worst kind of failure even for entrepreneurs that we back. They’re all talented people. Some ideas work; some don’t. It’s when they end up spending seven, eight years and then it doesn’t work. Then it takes out seven, eight years of their life.” – Nakul Mandan

“Entrepreneurs think it’s going to be like the Michael Keaton version, and the good ones, they actually have to work through the Christopher Nolan version of Batman.” – Ben Choi

“If you don’t wear ambition on your sleeve, how do people know you’re ambitious?” – Nakul Mandan

“VC is more about the ground game than the air game.” – Nakul Mandan

“Always remember there’s a human on the other side of every conversation.” – Nakul Mandan

“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

“If you have an understated personality, wear something really bright.” – 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.