DGQ 25: Were you successful because or in spite of your last firm?

There’s a story that Simon Sinek shared that I’ve always really liked.

I would highly recommend watching the full video. Only two and a half minutes. But in case you choose not to, the story goes… there was a former Under Secretary of Defense giving a speech at a large conference who interrupts his own remarks while drinking out of Styrofoam cup. He smiles as he looks down and he shares an anecdote.

Last year, when he was still the Under Secretary, they flew him there business class, picked him up in a car from the airport, checked him into his hotel for him, escorted him to his room. And the next morning, there was another car waiting to pick him up from the hotel that drove him to the venue, showed him through the back entrance, then green room. In the green room, there was someone waiting for him with a hot cup of coffee in a ceramic mug.

The following year he went (the year he was giving the above speech), he was no longer the Under Secretary. He flew to the city on coach, took a taxi from the airport to the hotel, checked himself in, took another taxi to the venue the next morning, found his own way backstage after arriving at the front door. When he asked where he could get coffee, someone pointed him towards the coffee machine in the back corner and told him to serve himself in a Styrofoam cup.

The intended lesson here is that the ceramic cup was never meant for him, but the position in which he holds. He deserved the Styrofoam cups, everyone does. And that no matter how far you go in life with all the perks that come with promotions and status and power, never forget that that will last only for as long as you hold that position.

There are obviously rare exceptions. But that is also the question that us as LPs ask. Hell, I’m sure it’s what a lot of VCs ask themselves about the founders they could back. Were you successful because or in spite of your last firm/company?

For founders and founding GPs, the attribution and causation is clearer than if you were an operator or other team member at a VC firm. We begin to peel the onion with questions like: What did you do in your last job title that no one else with that job title has ever done? For operators, did you create something and meaningfully lead something that created mass societal value and/or independently change the course of the company? For non-founding GPs at VC firms, did you individually drive disproportionate returns for the overall fund at your last firm? Attribution is often harder than one would think at prior institutions since many institutions succeed as teams, as opposed to individuals. So if success came as being a core member of the team, how much of your last team are you bringing with you? If not, how can you ramp up quickly to be a top performer?


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


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 Most Frequent VS Most Important LP Conversations | El Pack w/ Adam Marchick | Superclusters

adam marchick

Adam Marchick from Akkadian Ventures 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.

Cocoa VC’s Carmen Alfonso Rico asks what belief Adam held firmly for years but changed his mind recently on.

Good Trouble Ventures’ AJ Thomas asks about how GPs can better communicate risk to first-time LPs.

1517 Fund’s Danielle Strachman asks about the world view Adam has that shapes his investing thesis.

Over the past twenty years, Adam Marchick has had unique experiences as a founder, general partner (GP), and limited partner (LP). Most recently, Adam managed the venture capital portfolio at Emory’s endowment, a $2 billion portfolio within the $10 billion endowment. Prior to Emory, Adam spent ten years building two companies, the most recent being Alpine.AI, which was acquired by Headspace. Simultaneously, Adam was a Sequoia Scout and built an angel portfolio of over 25 companies. Adam was a direct investor at Menlo Ventures and Bain Capital Ventures, sourcing and supporting companies including Carbonite (IPO), Rent The Runway (IPO), Rapid7 (IPO), Archer (M&A), and AeroScout (M&A). He started his career in engineering and product roles at Facebook, Oracle, and startups.

You can find Adam on his socials here:
X / Twitter: https://x.com/AMarchick
LinkedIn: https://www.linkedin.com/in/adammarchick/

And huge thanks to Carmen, AJ, and Danielle for joining us on the show!

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

OUTLINE:

[00:00] Intro
[01:22] The anatomy of a good story
[02:26] The job of an annual summit
[05:35] How often does VC change?
[07:25] Narratives LPs are looking for at GPs’ AGMs
[08:25] “20% overall revenue growth in the portfolio is NOT exciting”
[09:01] What founders talk about at an AGM
[14:01] How does Adam spend time at an AGM
[17:48] Enter Carmen and Cocoa VC
[19:35] What did Adam change his mind about
[21:09] How does an LP assess GP NPS?
[22:16] Picking on-sheet references
[24:33] The origin of Cocoa VC
[26:08] What is Carmen’s superpower?
[27:09] What does Carmen want from her LPs?
[29:09] The best answers to “what do you want from your LPs?”
[31:29] Controversial decisions for the LPAC
[33:39] Enter AJ and Good Trouble Ventures
[34:25] Communicating risk to your LPs
[35:58] What about to first-time LPs?
[38:06] Where do first-time LPs come from?
[39:50] What inspired AJ’s question?
[42:14] Is the convo different if LPs reach out vs you reach out?
[43:45] The timing of LP conversations: most frequent vs most important
[45:59] The trust equation
[47:45] How to scale trust with LPs
[51:35] How has GPs built trust with Adam?
[53:29] How often does Adam keep in touch with his GPs?
[56:06] Enter Danielle and 1517 Fund
[58:38] What is Adam’s mental model?
[1:01:43] How does Adam define low entry prices?
[1:03:25] Tracking trends as an LP
[1:06:55] 80-20 portfolio construction
[1:10:37] Would 1517’s thesis 15 years ago count as market risk?
[1:14:12] Adam’s last piece of advice
[1:15:46] Akkadian Ventures and RAISE Global
[1:17:06] David’s favorite moment from Adam’s earlier episode

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Venture is made on the exception, so if each company is growing at 20%, it’s not an exciting portfolio. If 3 companies are growing at 300%, that’s an exciting portfolio.” — Adam Marchick

“I always go back to tenets of venture. It’s backing great people, tackling large markets at low entry prices.” — Adam Marchick

“Similar to a founder, their job is to communicate upside potential. At worst, you can lose 1X. At most, the returns can be inspiring. I think your job is to talk about what can go right and what are the inputs required to make it go right.” — Adam Marchick

“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.” — Adam Marchick

“Trust equals credibility, reliability, and intimacy and the dividing factor of building that trust is whether or not you feel that self-orientation is only geared for the other person’s agenda or actually something that you’re co-creating together.” — AJ Thomas

“When something is getting really heated, it’s a great time to learn because so many people are working on something.” — Bryne Hobart

“When there is hype, you have to look at metrics that can’t be hyped.” — Adam Marchick

 On portfolio construction… “80% should be on-thesis, and 20% should be ‘you couldn’t sleep at night if you didn’t do it.” — Adam Marchick


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.

Energy, Intelligence, and Integrity

lion, integrity

Recently, I met an LP who told me an interesting framework, derived from something Warren Buffett once said. “Every pitch needs to have energy, intelligence, and integrity. And without the last, the first two can lead bad outcomes for the LP.”

  1. Energy — Why now for the world? Why now for your LPs? Why is now the time for you? Why do you have to do this and nothing else? Can your pitch get people really excited about the opportunity? About you? When they wake up the next morning, are they still thinking about your conversation, or have they moved on with their morning to focus on sending the kids to school or what their schedule looks like for the day?
  2. Intelligence — Do you know what you’re talking about? Have you done so much research and have so much lived experience here that you are the one of the world’s foremost experts here? Are you a thoughtful and intentional person around all aspects of your life?
  3. Integrity — Can I trust you? Why should I trust you? Do you have a track record of maintaining long friendships? What’s the longest friendship you’ve maintained? Do you have an strong moral compass? How is it exhibited in even the smallest actions you take? If your and my interests ever clash, what is your course of action? Where do you sit in the Maslow’s Hierarchy of Needs? What set of needs are you primarily motivated by?

Interestingly enough, just a few hours later, I was catching up with a good old friend who’s putting together a pitch for his new venture. And he was telling me one of the pieces of feedback that he got was that there wasn’t enough dopamine induced from his pitch. Which was an interesting piece of commentary. The person giving him that piece of feedback believed that all pitches should induce three types of hormones:

  • Dopamine — known for joy, excitement, and motivation. To draw a parallel, “energy” under Warren Buffett’s framework.
  • Oxytocin — known for building trust and empathy. Or “integrity.”
  • Serotonin — known for calmness, well-being, but in the context here: optimism. I’m not sure if this draws a strict line of correlation to Warren Buffett’s framework, but nevertheless, something useful to think about. Why will the world tomorrow be better than the one today? What can I look forward to?

In my buddy’s pitch, he included a lot of facts and research, promoting oxytocin in the reader. But the pitch lacked excitement and an urgency to take action. In other words, dopamine.

Most decks charting new territory and betting in the non-obvious carry too much oxytocin, responsible for creating trust (i.e. data, information, synthesis of market trends, why the GP is legible, testimonials, track record, etc.). So much to prove factually why this should exist. A very left brain approach.

Most decks betting on a hot topic, industry or idea index heavily on dopamine. Why this is exciting? Why we have to do this now?

The best decks have both.

Photo by Zdeněk Macháček 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.

NO Diligence is Ever Enough | Anurag Chandra | Superclusters | S6E2

anurag chandra

“There are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. I’ve only seen five or six because I’ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.” — Anurag Chandra

Anurag Chandra has spent over two decades in Silicon Valley as an investor, operator, and allocator. He has helped lead four venture capital funds, managing over $2.0B in aggregate AUM. Anurag has also been a senior executive in three enterprise technology startups, two of which were sold successfully to public companies. He is currently the CIO of a single-family office with an attached venture studio and a Trustee for the $4.5B San Jose Federated City Employees Retirement Fund, serving as Vice Chair of the Board, and Chair of its Investment and Joint Personnel Committees.

You can find Anurag on his socials here:
LinkedIn: https://www.linkedin.com/in/anchandra/
X / Twitter: https://x.com/achandra41

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

OUTLINE:

[00:00] Intro
[02:10] Why is what Anurag is wearing a walking contradiction?
[06:08] The man without a home, but comfortable in everyone’s home
[10:17] The Stanford Review
[12:55] The four assh*les of America
[20:13] How did Anurag schedule regular coffee with Mark Stevens?
[25:31] Mark Stevens’ advice to Anurag about staying top of mind
[26:42] How often should you email someone to stay in touch?
[30:33] Why should you be an asymmetric information junkie?
[34:21] Where should you find asymmetric information in VC?
[36:02] The ‘Oh Shit’ board meeting
[40:09] How San Jose Pension Plan views GPs
[43:55] Defining the ‘venture business’
[49:09] Process drives repeatability
[54:06] How San Jose Pension Plan built their investment process from scratch
[58:43] What is a risk budget?
[1:01:52] What did San Jose Pension Plan do about their risk budget?
[1:05:05] The people who changed Anurag
[1:11:10] Post-credit scene

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“You seem like a good guy. I’d love to find ways to work with you, but I’m going to forget you in two or three weeks. And you got to make sure that you stay in the front of my mind when I’m in a board meeting and there’s a company that could use your money. The best for you to do that is to shoot me an email from time to time and let me know what you’re working on. But do not make them long. I don’t need dissertations.” — Mark Stevens’ advice to Anurag

“There are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. I’ve only seen five or six because I’ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.” — Anurag Chandra

“You can do two weeks or two years of due diligence on a company, in particular if you’re a mid-stage or later-stage investor. And it’s after the first board meeting—I have a friend who affectionately refers to it as the ‘Oh Shit!’ board meeting where you show up, and now you’re on the inside and you learn all the bad stuff about the company that was hidden from you. Now is that to suggest you should just invest after two weeks because even after two years you’re still going to end up with skeletons you were unable to uncover? No. I still think process matters.” — Anurag Chandra

“Look for GPs who are magnets, as opposed to looking for a needle in a haystack.” — Noah Lichtenstein

“Process drives repeatability.” — Andy Weissman


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.

The Question-Off

flowers, plains

One of my favorite questions as of late has been: “What is it you do to train that is comparable to a pianist practicing scales?” To me, it is fascinating to deconstruct a practice, or an action, or a set, and just drill on only one element of that practice. Every accomplished musician, athlete, veteran, chef, just to name a few, is uniquely familiar with the concept of repetition and refinement.

For example, part of my job, as now a podcast host, on top of doing research, prepping and making sure the guests are comfortable, getting involved in the editing room, just to name a few, is to ask questions. And because of the way I host Superclusters, my goal is to ask guests questions they’ve never been asked before. Admittedly, tall marching orders to those individuals whose job is to ask questions to get to the bottom of something in ways the recipients of their capital and their network may not expect. But alas I try. That said, I thought, how cool would it be if I could practice asking novel questions to someone who’s seen it all?

Admittedly, there are very few souls out there who would make great sparring partners for this drill. One that’s seen, heard, and thought of almost every known question out there. And even less I have had the chance to personally interact with. Of my limited Rolodex, luckily, the first person I asked was game. And that person happens to be this guy called Kevin Kelly.

The exercise would be, over a 30-day period, for me to ask him one question every day with the hopes that at least half are ones that he’s never been asked before. He then one-upped me and said he’d do the same. As such, it resulted in 60 queries that go beyond the obvious. While I’m not here to share the results of this “question-off”, I wanted to share the below as I hope this inspires you in ways that you might not have considered before. And if nothing else, fun journaling prompts for yourself. As such, I’ve bolded some of my personal favorites.

Kevin’s questions for me:

  1. What would you do with a billion dollars? (After you gave your family cars, houses, yachts, and vacations, you would still have a billion dollars.)
  2. Do you see yourself as part of an intellectual heritage? Who is on your tree?
  3. What is a prediction you made that was very wrong?
  4. What is the occupation that is the opposite of what you do?
  5. You get to relive one day of your past life. You could either return it as was at full volume, or you could change it. What day do you choose?
  6. If your life has a motto five words or less, what would it be?
  7. What significant law do you think should be changed?
  8. What do your friends get wrong about you?
  9. What influential person would you most appreciate a compliment from?
  10. What is something you can’t do that you’d give up 10% of your current wealth to do exceptionally well?
  11. What do you know more about than anyone else you have met?
  12. What is special about the neighborhood you live in?
  13. What question do you wish people would ask you?
  14. You get a 2-way ticket in a time machine. Do you go to the past or future? How far?
  15. What is a rule you gave yourself as a child that you still keep?
  16. What is the most recent thing you did for the first time?
  17. Who is a thinker more people should know about?
  18. What’s the strangest compliment you’ve ever received?
  19. What widely accepted “fact” do you think will be proven false in the next 50 years?
  20. What’s the most useless skill you’re proud of?
  21. What is one non-obvious piece of advice you would give to someone who wanted to get rich?
  22. They are making a film about you. What should the theme song be?
  23. What is a famous book you think everyone should read, but for a reason other than the one it’s famous for?
  24. What is something everyone you know of has done, but you have not?
  25. What is the most profound thing you’ve learned from a work of fiction?
  26. What is a popular piece of advice that you think is completely wrong?
  27. What part of you is a mystery to you, the part of that you least understand?
  28. What memory do you return to most often?
  29. What’s the most persistent myth people have about you that you’ve never bothered to correct?
  30. What’s a small thing you lost that still bothers you?

My questions for Kevin:

  1. What was your earliest relationship with money?
  2. Was there any specific groundswell in your early childhood and early life that led to the highest rate of change and growth? Were they largely technological, political or cultural in nature?
  3. If you had a billion dollars to create a secret society that will last 200 years into the future, how would you go about doing so and what would they be working on?
  4. As someone who’s used ChatGPT to write a novel you’ll never publish, yet has been an original thinker, thought-provoking writer for decades, what parts of your writing — no matter how far into the future, no matter how good the AI gets — will you never AI touch?
  5. One of the pieces of advice you once gave was to be able to learn from those you disagree with or offend you. Has there ever been a relationship that has most challenged the grounds of which your ideals stand on? How do situations that have led you to refine your ideals differ from those that reinforce what you believe in?
  6. If you were the main character of a movie about your life and you had an audience watching said movie, what would the audience be screaming at you to do?
  7. Kevin, you’re a futurist. You see the world beyond the horizon. But to take a step back, there’s a quote from the show The Office that I really like: “I wish there was a way to know you’re in the good old days before you’ve actually left them.” With all the doom and gloom around us today, what are the reminders you keep close to your heart that today, we’re still in the good old days?
  8. There’s so much gravitas and leniency given to a founder and their crazy ideas, but I’m curious, in your opinion, what were the greatest innovations at WIRED that weren’t a Kevin idea?
  9. Has there been a habit or practice you’ve observed from an interviewee of yours that you’ve worked into your own rotation?
  10. What, if anything, do your peers oversimplify about being a writer? And what, if at all, do they often overcomplicate?
  11. What was your first failure? How did you know when to quit?
  12. If you were to put together the perfect interviewer piece by piece Mr. Potato-Head-Style, how would you go about it? Who’s the researcher? Who opens the interview? Who’s the one in charge of going deep in questions? Who closes out the interview? Who’s responsible for the in-person interview setting?
  13. What is the question that has taken the most mental calories for you to answer? Why?
  14. You took a variety of roles across your career — some of which you’ve co-created and started, others you joined. Were “what’s best for the company” and “what’s best for Kevin” aligned the whole time?
  15. When you have time to wonder, what’s the thought of idea you regularly find yourself coming back to because you find it so interesting, but most of the world may not?
  16. What about your past do you desperately not want your children to know about?
  17. One of the great Kevin Kelly-isms out there is “Don’t be the best. Be the only.” How much time and discipline do you think is necessary for an individual to fully appreciate that they themselves are the only one doing something? At what point does it become part of their identity?
  18. As an enthusiast who’s been enamored by photography since you were in high school and took a deep dive into it in 1970, if you had a camera that could only take three photos total starting from today, what three moments would you photograph?
  19. When was the last time you adopted the habits, wisdom, or advice from someone you disliked or held very little respect for?
  20. What is an example of a mentorship relationship that you’re particularly proud to have your fingerprints on?
  21. What’s something others would believe you’d be highly proficient in, but no matter how hard you’ve tried in the past, you’ve found it extremely difficult to raise your skill level at that?
  22. What is it you do to train that is comparable to a pianist practicing scales?
  23. If you lived your life 1000 times, would would be true in 999 of them?
  24. What is the greatest accomplishment that you regret having achieved?
  25. What was the harshest piece of criticism you gave where you knew that that individual or project was providing more meaningful value to the world than your criticism gave it credit for?
  26. What coffee table books best encapsulate Kevin’s personality today? And would your coffee table have looked different today than in your 30s?
  27. If you could only choose 2 personality traits to pass on to your grandchild — 1 strength and 1 weakness, which 2 would you pass on?
  28. What was one major life decision you’ve made where it was better to not over-intellectualize the decision-making process and shoot from the hip?
  29. You’ve had a non-traditional path to your life and your career. The stuff that typically goes in movies. And in so much of what you do, you’re a dreamer. You’re a visionary. How much did they first pay you to first give up on your dreams? Why did you say yes or no?
  30. As someone who’s once recommended people to go to funerals, what is your biggest fear around what someone might say at yours?

Photo by Ahmet Yüksek ✪ 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 to Not Get Fired When Changing Your VC Strategy | El Pack w/ Beezer Clarkson | Superclusters

beezer clarkson

Beezer Clarkson from Sapphire Partners joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on four GPs at VC funds to ask four different questions.

Precursor Ventures’ Charles Hudson asks what is the one strongly held belief about emerging managers that she no longer believes is true.

NextView Ventures’ Stephanie Palmeri asks how much should an established firm evolve versus stick to their guns.

Humanrace Capital’s Suraj Mehta asks what the best way to build brand presence is.

Rackhouse Venture Capital’s Kevin Novak asks if you’ve deployed your capital faster than you expected, what’s the best path forward with the remaining capital you have left?

Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Since, she has held various direct and indirect venture investment roles, as well as operational roles in software business development at Hewlett Packard. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide.

In 2016, Beezer led the launch of OpenLP, an effort to help foster greater understanding in the entrepreneur-to-LP tech ecosystem. Beezer earned a bachelor’s in government from Wesleyan University, where she served on the board of trustees and currently serves as an advisor to the Wesleyan Endowment Investment Committee. She is currently serving on the board of the NVCA and holds an MBA from Harvard Business School.

You can find Beezer on her socials here.
Twitter: https://twitter.com/beezer232
LinkedIn: https://www.linkedin.com/in/elizabethclarkson/

Check out Sapphire’s latest breakdown on if venture is broken: https://www.linkedin.com/pulse/venture-broken-what-2000-priced-early-stage-rounds-tell-clarkson-sjvjc/

And huge thanks to Charles, Suraj, Steph, and Kevin for joining us on the show!

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

OUTLINE:

[00:00] Intro
[01:22] Where does Beezer’s advice come from?
[04:03] Charles and Precursor Ventures
[04:47] What’s something Beezer used to believe about seed stage venture that she no longer believes in
[08:04] Why did Charles choose to bet on pre-seed companies?
[10:21] What did LPs push back on when Charles was starting Precursor?
[12:18] Definition of early stage investing today
[14:38] Steph and NextView Ventures
[18:13] When do you stick your knitting or move on from the past as an established firm?
[30:48] Is venture investing in AI fundamentally different than investing in other types of companies?
[32:52] Does competition for a deal mean you’ve already lost it?
[36:09] Suraj and Humanrace Capital
[36:54] How should emerging managers build their brand?
[38:38] The audience most emerging managers don’t focus on but should
[40:39] How much does visible brand presence matter?
[43:47] Useful or not: Media exposure in the data room
[45:40] Backstreet boys
[46:37] Kevin and Rackhouse Venture Capital
[47:28] What Kevin is best known for
[48:03] Updated fund modelling when you’re ahead on your proposed deployment period
[58:00] The typical questions Beezer gets on LPACs
[1:03:22] Is venture broken?
[1:06:41] David’s favorite Beezer moment from Season 1

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Whatever the evolution of venture is if you’re just following someone else, the odds of you doing as well as them is just harder and that is probably a truism about life.” — Beezer Clarkson

“If you’re going to get a 2X in venture over 20 years, frankly, as an LP, there are alternatives from a pure dollars in the ground perspective. But if you’re looking at trying to capture innovation, which AI is now one of the great innovations, where are you going to capture that if not playing in venture? So is venture broken is a question of who are you.” — Beezer Clarkson

“If you’re competing for the deal, you’ve already lost it.” — Beezer Clarkson

“I think the competition is more: Did I see it with enough time to build the conviction and build the relationship relative to the other people that might be coming in?” — Stephanie Palmeri

“Recycling is incredibly important, but incredibly hard to plan for, especially as early as you’re coming in, unless you’re seeing evidence of acqui-hires today and you know you’re going to have those dollars coming in. Obviously, really hard. So I would not bank your farm on that.” — Beezer Clarkson


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
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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.

On Re-Ups

elevator, lift, re-up

A good friend of mine recently asked me a question for an article he was writing (Stay tuned for his masterpiece which I’ll be sure to share on socials.): “What makes you more likely to reinvest in Fund II or III?” Which is a really good question and something I’ve been thinking out more and more in the past few months as a number of my bets have come back to me for that conversation.

Before I share my thoughts in full here, couple caveats:

  1. I’m a small check. Let’s never forget that fact. Whether I invest in the fund or not, it will not make a meaningful dent in the final fund size. But it looks great when X% of your LPs re-up into the next, and some GPs like to highlight which.
  2. I’m a nobody. If you’re a friend reading this piece, I know what you’re going to say, but in the grander scheme of things, I’m a nobody. And hopefully some day, I will be a somebody, but that’s not the reality today. Meaning unless you don’t have any real institutional backing who’s committing to a re-up, my name reasonably won’t impact your ability to raise your next fund. Two reasons:
    • Again, see Exhibit 2’s first sentence.
    • If a manager in my portfolio is about to go back to market, I would have known months, possibly a year, ahead of the raise. And by that time, I would have put you in touch with many of the LPs in my network at that point. So, anyone who does know who I am would have already met with said GP before the fundraise, and any namedropping of my name would be old news by the time they see the deck.

Alright, I’ve delayed my answer long enough.

So there are few things I look for, opportunistically, though some more intentionally than others. And in no particular order:

  1. Are the people I meet through the GP impressive and/or thought-provoking and/or thoughtful people?
    • This includes the founders they back. The founders they think about backing and ask me to help them diligence. The people they plan to hire or have hired. Other LPs in the same fund. Friends of theirs I meet over game night. Their spouse we do a double date with. Again, all of these are casual connections for the most part. And no, I am not assessing with a clipboard, binder, and monocle every single person I meet via the GP. But my rough litmus test here is: Do I feel more inspired, less, or net neutral when I interact with the afore-mentioned individuals?
  2. Over time, do I gain more conviction in my initial bet on the manager or less? Am I getting more and more impressed with the manager’s ability to grow and learn over time?
  3. What does the quality of revenue, talent, funding, and milestones in the underlying portfolio look like? How involved has the GP been in each company’s revenue, talent, funding, and milestones? How much of their portfolio company’s success did they will into existence?
    • I should note that this really matters when you want to build an institution. In almost all ways, the fund I initially invest in should be the worst version of the firm that anyone ever has to see again. Each fund should get better than the last. Each fund should have more surface area for luck to stick than the last. And one of the most reliable ways of doing so is to be there for your companies when they need it. And for your founders to be grateful for your support.
  4. Did the GP do what they said they were going to do? If not, how much were they off and why?
    • Not everything goes your way I get it. Ideally, as an LP, things do. But the second best result is that it doesn’t, but you learn some really powerful lessons that sets you better up for the next fund.
  5. With the next fund, does the strategy change significantly? Does the team change significantly? Does the fund size grow dramatically?
    • When making non-GP or partner hires, are you outsourcing responsibility and learning or mentoring the next generation?
    • For fund size, I don’t have hard numbers I look at, but growing from a $10M to a $25M to a $50M fund is reasonable. But going from a $5M to $100M is not.
  6. Over the course of the last two or so years, have I met someone who is a lot more impressive than the GP I’ve already backed?
    • Admittedly, marginally better is not enough for me.
  7. Is my communication line with the GP still as strong (ideally stronger) than when I initially committed?
    • I’m not here to bug a GP every single week or even every single month. And I am always aware that I shouldn’t be taking too much time up from a GP for a selfish reason. But if I do need to make a call, email or text, how quickly do they get back to me?
  8. Five years from now, can I confidently say this person is one of the top 5 most impressive people I’ve met in the last five years? What about 10 years from now?

Photo by Possessed Photography 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 to Read Investors Like a Book | Thorsten Claus | Superclusters | S6E1

thorsten claus

“You need to make space for weird types of conversations to happen on the fringes that really inform you what’s going on at the frontier.” — Thorsten Claus

Thorsten Claus is a venture investor and builder with more than 15 years of private equity and venture capital experience. He has raised nine funds, managed over $4.8B across global platforms, and led or overseen more than 120 direct investments, generating returns of 3x–7x net to investors.

His current work focuses on dual-use technologies at the intersection of defense, security, and national resilience. Guided by the discipline of Howard Marks, the systems-level thinking of the Consilience Project, and a commitment to internalizing externalities, he invests in teams and technologies that strengthen sovereign capability and long-term societal stability.

Beyond capital, Thorsten is a hands-on builder. He machines defense-critical and space components, restores historic race engines, and writes on production systems and resilience at blog.thinkstorm.com. This grounding in physical production complements his investment practice, keeping judgment tied to real-world constraints.

You can find Thor on his socials here:
LinkedIn: https://www.linkedin.com/in/thorstenclaus/
X / Twitter: https://x.com/thinkstorm

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

OUTLINE:

[00:00] Intro
[02:31] Downhill skateboarding
[05:58] How do you see behind a corner when downhill skateboarding?
[07:42] Hill hunting
[10:15] How long does it take to go down the Sierras?
[11:41] The most important part of the body for downhill skateboarding
[16:02] David’s dumb question of the day
[17:25] The accident that pivoted Thor’s life
[19:34] The first race car Thor bought
[20:51] Why Thor is a terrible race car driver?
[23:52] How did Thor come to use the race oil that Porsche Racing uses?
[24:59] The 3 things you need to welcome fringe conversations
[27:07] Just another David misattribution
[27:34] Truth is difficult these days
[29:20] How do you prioritize which advice to take?
[30:33] Thor’s weird definition of risk
[31:59] How do you know if someone is giving you authentic advice?
[34:40] How does Thor understand someone’s past without asking about it?
[39:42] Lessons from fictional storytelling in diligencing GPs
[43:22] Questions and responses that reveal a GP’s past
[46:10] Books that Thor read to ask better questions
[49:18] What is the USMC Christmas Tree?
[53:40] The Christmas Tree in an investor’s portfolio
[57:49] Can beggars be choosers?
[1:00:41] The difference between capital formation and fundraising
[1:03:00] Production vs product for a GP
[1:06:54] Thor and cardistry
[1:10:21] What are moments that reminds Thor we’re still in the good old days?
[1:13:50] The post-credit scene

https://open.spotify.com/episode/6InM0JXlg7LjWy0QViJsmk

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“You need to make space for weird types of conversations to happen on the fringes that really inform you what’s going on at the frontier.” — Thorsten Claus

“Risk is the probability of a fatal outcome within given resources.” — Thorsten Claus

“Is it really out of conviction that they’re acting on [the advice] or is it just a belief? You know, I believe in many things, but do I act accordingly? That’s the difference between belief and conviction.” — Thorsten Claus

“The self audit of our actions, behaviors, processes, and decisions is so important.” — Thorsten Claus

“What I find more interesting than the question about ‘what’s the one thing you don’t want me to know about you’ is what it reveals about what you think about me. So, a social interaction is always with me with others, or you with me as well, and a group with others. If I’m worried that you know something about me, that reveals something more about what you fear my attitude is or how this is seen or how you would think I would act. And that is super insightful.” — Thorsten Claus

“If you want to find out something about the why and the what, you ask open-ended questions. If you confirm bad news, you voice it for them.” — Thorsten Claus

“There are no bad teams, only bad leaders.” — Jocko Willink

“There was a whole time when I grew up here in America where everything was great. […] Everyone gets a participation prize. I hated that because it really devalues people who are truly great. And the fact is that there are only very few truly great people.” — Thorsten Claus

“Capital formation is a design principle. Fundraising is a sales process. Without true design around a customer base and a product, you will fail eventually.” — Thorsten Claus


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.

The Work I Do with GPs

work, hands

I’m fortunate enough I get to work with some of the most interesting and stellar GPs out there. It’s never been a business I’m actively trying to grow. Outside of me backing managers myself, every so often I’ll get a friend who refers their friend to me and asks me to help them out with thinking through fundraising. It’s always been opportunistic. And even when I work with folks, it’s not primarily about intros. In fact, in all my working relationships, I never offer intros as part of the agreement. But more so working with them to understand how the GPs can better tell their story and run a more institutional fundraising process. Occasionally, I would get asked to advise when a firm should bring in an investor relations professional. But that last part, a piece for the future. So, all that to say:

  1. I’m not an expert in everything, but I do try to actively learn best practices in the market. If I don’t know something, I will find it out for you and/or put you in touch with the best practitioner on it.
  2. I’m now overcapacity. I don’t have the bandwidth to work with every manager that comes my way. I have other things I want to do and am working on.
  3. My primary job is still to support the GPs I back myself.

So, I’m just going to share below exactly what I do when I work with a GP, so that you don’t have to come find me for help. Because we do effectively the below. This approach has also evolved over time. And this is my current approach, circa September 2025. My job is also to help GPs better understand LPs and where they come from. So, while the saying goes as “If you know one LP, you only know one LP,” my job (and personal fascination) is to define and delineate the nuance. The only things I cannot help with if you’re only reading the below are:

  1. Be your accountability partner. Part of my role with GPs is also making sure GPs stick to their promises. Discipline. It’s easy to plan. Hard to execute.
  2. Debrief on LP conversations and pipeline management.
  3. And figure out your LP-GP fit, or your ideal LP archetype as a function of your fund size, your strategy, your experience level and your story.

This might also be one of the few pieces I write that some pre-reading may help contextualize what I will write below.

Most of the time I work with folks who are mid-raise. Not always, but most of the times. So I’m stepping in where there’s already some infrastructure, but not a lot, usually bootstrapped and duct taped together. Not a bad thing. As long as it works, I don’t touch much during the raise itself. Then we work on things and cleaning up systems post-raise or in-between raises. The best time to strategize and plan for a raise is at least six months in advance. But that’s neither here nor there. So what do I do?

  1. I ask the GP(s) to pitch me the fund. We simulate email exchanges, first meeting, second meeting, and due diligence as if I were the target LP persona. I offer no commentary. I am purely the observer. You can do this with most people who do not know your strategy well. Friendly LPs. Other GPs. But I find it most helpful if you can to do this with people who have a great attention to detail, specifically in the literary sense: lawyers, authors, therapists, podcasters, professors, editors, scriptwriters, showrunners, and so on.
  2. Then, I share all the risks of investing in said manager that I can think of. What are the elephants in the room? What parts of the GP, the GP’s story, the strategy, the track record, and the complexity of the story would make it really hard to pass the investment committee (IC)? What might be moments of hesitation? No matter how big or small. There’s a saying that a friend once told me, “When your spouse complains about you not washing the dishes, it’s not about the dishes.”
  3. Label and categorize each risk as a flaw, limitation, or restriction.
    • Flaws: Traits you need to overcome within 1-2 fundraising cycles (~2-5 years). The faster, the more measurable, the better. You can’t just say you’re going to overcome these flaws. You need to have KPIs against each of these.
    • Limitations: Risks that the world or that particular LP believes is true. Like being a Fund I. Or being a solo GP.
    • Restrictions: What you prevent yourself from doing. Think Batman’s no killing code. In GP land, it’s only investing in a particular demographic or vertical. It’s only investing in the Bay Area. And so on.
  4. Stack rank all of them. Depending on the LP you’re pitching, figure out the minimum viable risk list that LP may be willing to accept. It’s not always obvious.
  5. You should always address limitations as early on in the conversation. My preference is in the email exchange or at the very minimum, in the first two slides of the deck. In other words, “here are the primary reasons you shouldn’t invest in me if you don’t like…” Think of it like the elephant in the room. Make it explicit. Don’t wait for LPs to have private investment committee (IC) conversations without you in the room. Or worse, they implicitly, whether consciously or subconsciously, think of the limitations in their head. Having been in multiple LP conversations and a fly on the wall in IC meetings, sometimes an LP can’t fully describe why they’re passing, just that they are.
  6. Next, figure out for each LP in your existing and future pipeline when are flaws also limitations. When are restrictions also limitations?
    • When a restriction is a limitation, there isn’t an LP-GP fit. So, you need to go find LPs, who don’t see your restrictions as limitations. Another reason you should address elephants in the room as early as possible.
    • When a flaw is a limitation, you need to fire yourself before the LP fires you. You need to say “No” before an LP does. Be respectful of their time, but maintain that relationship for the future. Reaching back out every 1-2 quarters to catch up is something I highly recommend. Any longer, LPs will forget about you. And no, that does not mean, “Can I add you to my monthly/quarterly LP update?” No LP will say no, but almost always will your updates die in their inbox. If you don’t care about your relationship with them, why should they?
    • Are you ready for an institutional fundraise? How much of the institutional data room (use this as a reference if you don’t know what that means) do you have ready? And for each flaw and restriction, do you have something in the data room (even if it’s in the FAQ/DDQ) that helps hedge against it?
  7. All that said, you also need to figure out what your superpower is. And you usually only need just one, but you have to be god-tier in that one superpower. There cannot be a close second. Oftentimes, it’s less obvious than you think it is. With all the hedging of risks above, you also need to give an LP to be your champion. You must spike in something that impresses the LP and despite all your flaws and restrictions, that you’ll still go far. And the more closely your superpower is aligned with at least 2-3 of the five (sourcing, picking, winning, supporting, exiting), the better. And you must make sure that it is made explicit to the LP as early in your conversations as possible.

Photo by Ümit Bulut 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.

Goldilocks and the 3 Secondaries

3, three, hot air balloon

“We need to rewrite our early DPI blogpost.”

Two years ago, Dave and I sat down less than five blocks away from where we were sitting when those words escaped the clutches of Dave’s mindscape. That piece has since been cited a number of times from fund managers I’ve come across. And sometimes, even LPs. While each part of that piece was written to be evergreen knowledge, what we want to do is to add nuance to that framework, along with examples of how we might see the internal conflict of early distributions and long-term thinking manifest.

In effect, and the premise for this blogpost, you’re in Year 7 of the fund. You’re now raising Fund III. What do you need to do?

The urgency to sell at Year 7 is relatively low. Although booking some amount of DPI may motivate LPs to re-up or invest in Fund III. The urgency to sell at Year 12 is much higher. So, what happens between Years 7 and 12? If you do sell, do you sell to the market or to yourself via a continuation vehicle?

For starters:

  1. Knowing when to sell WHEN you have the chance to sell is crucial. The window of opportunity only lasts so long.
  2. Consider selling some percentage of your winners on the way up to diversify, but be careful not to sacrifice too much potential future DPI. Yes, this is something we’ll elaborate more on with examples of what exactly we mean.

At the moment the next round is being put together, you have no discount to the current round price. The longer you wait to transact, the more doubt settles in from outsiders, the deeper the discount as time goes on. And so, if you have the chance to sell, sell into the (oversubscribed) primary rounds in order to optimize for price efficiency. Unless maybe, you’re selling SpaceX, OpenAI, Anthropic, Anduril, Ramp, just to name a few. There is a BIG tradeoff in TVPI (versus future DPI) when selling a fast-growing asset early (assuming it keeps its pace of growth). There is also a BIG risk to holding on to a large unrealized gain if the company stumbles or the market crashes.

We live in a world now that multi-stage venture funds have become asset management shops. Their primary goal will be to own as much of an outlier company as possible to maximize their potential for returns. As such, they will choose, at times, to buy out earlier shareholders’ equity.

To sell your secondaries, you have a very small window of opportunity to sell. Realistically, you have one to two quarters to sell where you can probably get a fair market value of 90 cents to the dollar of the last round valuation. Ideally, you sell into the next round at the price the next round values the company. As Hunter Walk once wrote, “optimally the secondary sales will always occur with the support/blessing of the founders; to favored investors already on the cap table (or whom the founders want on the cap table); without setting a price (higher or lower than last mark) which would be inconsistent with the company’s own fundraising strategy; and a partially exited investor should still provide support to the company ongoing.” If you wait a year, some people start questioning the data. If you wait 2 years, you’re looking at a much steeper discount. And if it’s not a “Mag 10” of the private markets—for instance, Stripe, SpaceX, Anduril, just to name a few, where there is no discount—you’re likely looking at 30-60% discounts. As Hunter Walk, in the same piece, quotes a friend, “‘I think friendly secondaries are easy, everything else feels new.’” As such, Dave and I are here to talk through what feels “new.”

First of all, lemons ripen early. In Years 1-5, you’re going to see slow IRR growth. Most of that will be impacted by businesses that fall by the wayside in the early years. In Years 5-10, IRR accelerates, assuming you have winners in your portfolio. And in the latter years, Years 10 onward, IRR once again slows.

Before we get too deep, let’s address some elephants in the room.

Why are we starting the dialogue around secondaries at Year 5? Five things. Year 5, 5 things. Get it? Hah. I’m going to see myself out later.

One, most investment recycling periods are in the first four years of the fund. So, any non-meaningful DPI is recycled back into the fund to make new investments. While this may not always happen, it usually is a term that sits in the limited partner agreement (LPA).

Two, most investments have not had time to mature. Imagine if you invested in a company in Year 1 of the fund. Five years in, this company is likely to have gone through two rounds of additional funding. If you come in at the pre-seed, the company is now at either a Series A or about to raise a Series B, assuming most companies raise every 18-24 months. If you were to sell now, before the company has had a chance to really grow, you’re losing out on the vast majority of your venture returns. And especially so, if you’ve invested in a company in Year 3 of the fund, you really didn’t give the company time to mature.

Three, by Year 5, but really Year 7, venture’s older sibling, private equity, should have had distribution opportunities. And even if we’re different asset classes by a long margin, allocators will, even subconsciously, begin to look towards their venture portfolio expecting some element of realized returns.

Four, QSBS grants you full tax benefits at Year 5. And yes, you do get some benefits with new regulation sooner by Year 3. But if you’re investing in venture and hoping to get to liquidity by Year 3, you’re in the wrong asset class.

Five, you will likely need to show (some) DPI in Fund I, in order to raise Fund III or IV. It’ll show that you’re not only a great investor, but also a great fund manager.

Outside of our general rule of thumb in our writeup two years ago, let’s break down a few scenarios. The obvious. The non-obvious. And the painful.

  1. The obvious. Your fund is doing well. You’re north of 5X between Years 7 and 10. You have a clear outlier. Maybe a few.
  2. The non-obvious. Your fund is doing okay. This is the middle of the road case. You’re at 3-5X in Years 7-10.
  3. Then, the painful. You’re not doing well. Even in Year 7, you haven’t crested 3X. And really, you might have a 1.5-2X fund, if you’re lucky. 1X or less if you aren’t. But your job as a fund manager isn’t over. You are still a professional money manager.

In each of the three scenarios, what do you do?

It’s helpful to frame the above scenarios through four questions:

  1. How much do you sell?
  2. When do you sell it?
  3. What is the pricing efficiency of those assets?
  4. And what is the ultimate upside tradeoff?

The obvious (5X+ TVPI)

Here, it’s almost always worth booking in some distributions to make your LPs whole again. Potentially, and then some. At the end of the day, our job as investors is to—to borrow a line from Jerry Colonna’s Reboot—“buy low, sell high.” Not “buy lowest, sell highest.” As such, you should sell some percentage of your big winners to lock in some meaningful DPI. Selling at least 0.5X DPI at Year 7 is meaningful. Selling 1-2X DPI at Year 10 is meaningful. As you might notice, the function of time impacts what “meaningful” means. The biggest question you may have when you have solid fund performance is: How much should you sell knowing that in doing so, it might meaningfully cap your upside? Or if you should even sell at all?

Screendoor’s Jamie Rhode once said, “If you’re compounding at 25% for 12 years, that turns into a 14.9X. If you’re compounding at 14%, that’s a 5. And the public market which is 11% gets you a 3.5X. […] If the asset is compounding at a venture-like CAGR, don’t sell out early because you’re missing out on a huge part of that ultimate multiple. For us, we’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%.” Taking it a step further, assuming 12-year fund cycles, and 25% IRR, “the last 20% of time produces 46% of that return.” She’s right. That’s the math. And that’s your trade off.

But for a second, we want you to consider selling some. Not all, just some. A couple other assumptions to consider before we get math-y:

  • 20% of your portfolio are home runs. And by Year 5 of your fund, they’re growing 30% year-over-year (YoY). And because they are great companies, growth doesn’t dip below 20%, even by Year 15.
    • For home runs, we’re also assuming you sell into the upcoming fundraising round. In other words, perfect selling price efficiency. Obviously, your mileage, in practice, may vary.
  • 30% of your portfolio are doubles, growing at 15% YoY. And growth doesn’t fall below 10%, even by Year 15.
    • For doubles, just because they’re less well-known companies, we’re assuming you’re selling on a 50% discount to the last round valuation (LRV).
  • 20% of your portfolio are singles, growing at 7% YoY. Growth flatlines.
    • For singles, even less desirable, we’re assuming you’re selling on an 80% discount to LRV.
  • The rest (30%) are donuts. Tax writeoffs.
  • For every home run and double, their growth decays by 5% every year.
  • We’re assuming 15-year fund terms.

Example 1:
Say you have a $25M fund, and at Year 10, you choose to sell 50% of the initial fund size ($12.5M). If you didn’t sell at Year 10, by Year 15, you’d have a 5.7X fund. But if you did sell at Year 10, you’d have a 3.8X fund. To most LPs, still not a bad fund.

vc secondary

The next few examples are testing the limits of outperformance and early distributions. Purely for the curious soul. For those, looking for what to do in the non-obvious case, you can jump to this section.

Example 2:
Now, let’s say, in an optimistic case, your home runs—still 20% of your portfolio—are growing at 50% YoY in Year 5. All else equal. If you didn’t sell at Year 10, by Year 15, you’d have a 11.6X fund. If you did sell at Year 10, by Year 15, you’d have a 9.3X. In both cases, and even when you do sell $12.5M of your portfolio at Year 10, you still have an incredible fund. And not a single LP will fault you for selling early.

secondary sale on 50% growth

Example 3:
Now, let’s assume your home runs are still growing at 50% YoY at Year 5, but only 10% of your portfolio are home runs and 40% are strikeouts. All else equal. If you sell $12.5M at Year 10, at the end of your fund’s lifetime, you’re at 4.8X. Versus, if you didn’t, 6.6X.

secondary sale 10% outlier

Hell, let’s say you’re not sure at Year 10, so you only sell a quarter of your initial fund size ($6.25M). All else equal to the third example. If you did sell, 5.6X. If you didn’t, 7.4X.

vc secondary sale 25% at year 10

Example 4:
Now let’s stretch the model a little. And play make believe. Let’s take all the assumptions in Example 1, but the only difference is your home runs are growing at 100% YoY by Year 5.

If you sell at Year 10, by fund term, you’re at 108.8X. If you don’t sell at Year 10, you have 110.7X.

vc secondary 100% growth

And as we play with the model some more, we start to see that assuming the above circumstances and decisions, selling anything at most 1X your initial fund size at Year 10, at Year 15, you lose somewhere between 2X and 3X DPI.

If you sell three times your fund size, assuming you can by Year 10, you lose at most around 5X of your ultimate DPI at Year 15. If you sell five times your initial fund size (again, assuming the odds are in your favor), you lose at most 7X of your final DPI by Year 15.

Now, we’d like to point out that Examples 2, 3, and 4 are merely intellectual exercises. As we mentioned in our first blogpost on this topic, if your best assets are compounding at a rate higher than your target IRR (say for venture, that’s 25%), you should be holding. Even a company growing 50% YoY at Year 5, assuming 5% decay in growth per year, will still be growing at 39% in Year 10, which is greater than 25%. That said, if a single asset accounts for 50-80% of your portfolio’s value, do consider concentration risk. And selling 20-30% of that individual asset may make sense to book in distributions, even if the terms may not look the best (i.e. on a discount greater than feels right).

Remember what we said earlier? To re-underscore that point, it’s worth saying it again. There is a BIG tradeoff in TVPI (versus future DPI) when selling a fast-growing asset early (assuming it keeps its pace of growth). There is also a BIG risk to holding on to a large unrealized gain if the company stumbles or the market crashes.

If you’d like to simulate your own secondary sales, we’ll include the model at the very bottom of this post.

The non-obvious (3-5X TVPI)

This is tricky territory. Because by Year 7-10, and if you’re here, you don’t have any clear outliers (where it might make more sense to hold as the assets are compounding faster than your projected IRR), but you don’t have a bad fund. In fact, many LPs might even call yours a win, depending on the vintage and public market equivalents. So the question becomes how much DPI is worth selling before fund term to make your LPs whole, and how much should you be capping your upside. How much of your TVPI should you be selling for your DPI knowing that you can only sell on a discount?

We’re back in Example 1 that we brought up earlier, especially if you have a single asset that accounts for 50-80% of the overall portfolio value. Here if the companies are collectively growing faster than your target IRR—say 25% on a revenue growth perspective, hold your positions. If your companies are growing slower than your target IRR and are valued greater than 1.5X public market comparables, you should consider selling 20-30% of your positions to book meaningful distributions.

The painful (1-3X TVPI)

You’ve got a dud. No two ways about it. You’re really looking at a 1.5X net fund. Maybe a 1X. And mind we remind you, it’s Years 7-10. It’s either you sell or you ride out the lie you have to tell LPs. LPs will almost always prefer the former. And for the latter, let’s be real — hope is not a (liquidity) strategy. And if put less charitably, check this Tina Fey and Amy Poehler video out. I don’t have the heart to put what’s alluded to in writing, but the video encapsulates, while humorously framed, the situation you’re in. You’re going to have to try to sell your positions on heavy discounts.

If you made it thus far, first off, you’re a nerd. We respect that. We are too. And second off, you’re probably looking for the model we used. If so, here you go.

We also do cover how this blogpost came to be in the first ever episode of the [trading places] podcast. And if you’re interested in the topic of secondaries, the [trading places] podcast might be your new guilty pleasure.

Photo by Tucker Monticelli on Unsplash


Shoutout to Dave for the many iterations of this blogpost and building the model in which this blogpost is based around!


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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.