Helpful is a 10-Letter Word | Eric Sippel | Superclusters | S6E3

eric sippel

“I hate checklists. I like outlines. I don’t like checklists. A checklist says ‘I have to have this, and then I’m good. An outline is ‘This is my starting point. These are the kinds of things I want to talk about or kinds of things I need to look at.” — Eric Sippel

Eric Sippel currently runs his family office and is an active investor in and adviser to many venture capital, private equity, hedge and real estate funds. He is a member of the RAISE Global selection and steering committees (the premier emerging VC manager conference) and often speaks to emerging venture manager groups. Previously, Eric was the COO of Eastbourne Capital Management, a multi-billion dollar hedge fund firm, and a Partner at Shartsis, Friese & Ginsburg, where he was a nationally recognized hedge fund and venture capital lawyer. Eric serves on more than a dozen LPACs and has served on many for profit and non-profit boards.

You can find Eric on his socials here:
LinkedIn: https://www.linkedin.com/in/eric-sippel-976770/

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

OUTLINE:

[00:00] Intro
[02:13] Why Eric’s name on LinkedIn is lowercase?
[02:44] Oceanside [04:18] Eric’s grandfather and education in the family
[07:06] Basketball
[07:58] Eric’s first venture fund investment in 1996
[12:05] How does Eric invest below the minimum check size requirement?
[14:51] How to decide your LP check size
[17:47] Today, when does Eric invest in a new GP?
[21:14] Time x capital 2×2 matrix
[24:32] Tough conversations with Eric
[27:00] The minimum viable value-add for LPs who write small checks
[32:02] Eric’s most impactful mistakes
[35:11] How do you know if a GP is GOOD at adding value?
[43:42] How many other funds in the same space does Eric look at before investing?
[46:36] Breaking down Eric’s deal flow
[49:35] How many references does Eric do?
[50:27] Who does Eric trust for LP references?
[52:34] Other references for diligence
[55:23] How does Eric approach a founder reference?
[59:09] Biggest lessons from CIA training
[1:05:16] Mike’s Pizza
[1:06:18] If everything were to change tomorrow, what would Eric photograph?

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“The best way for an LP to construct a venture portfolio is to be diversified across a large enough number of firms and funds. And in particular, those funds should be concentrated. 20-30 companies per portfolio, maybe less in some cases. And they should be diversified across sectors, geographies, vintages, and firms/GPs. You need to have a minimum of 15, but 25-40 feels right to me.” — Eric Sippel

“When I’m thinking about who am I going to say yes to, I’m comparing that to the people I’m cutting out who I think are great and I’m comparing it to the other people who would love to have my capital who I think are great. One of things that drives me is the relationship I have with a GP.” — Eric Sippel

“Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.” — Hunter Walk

“My advice to GPs is to do what they believe is right for maximizing performance and not to listen to their LPs.” — Eric Sippel

“The best way to make money in any asset class is to think differently.” — Eric Sippel

On references… “I’ll talk to as many founders as I can get my hands on that are not on-list. I do not want GPs to introduce me to founders.” — Eric Sippel

“I hate checklists. I like outlines. I don’t like checklists. A checklist says ‘I have to have this, and then I’m good. An outline is ‘This is my starting point. These are the kinds of things I want to talk about or kinds of things I need to look at.” — Eric Sippel


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 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.

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.

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
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.

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
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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.

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.

Gratitude and Deal Flow

thank you, gratitude

A few months ago, my good friend Sam hosted a happy hour for LPs, which he invited me to. There I caught up with a former fund-of-funds (FoF) manager who has booked some of the most impressive returns I’ve ever heard of for a pure FoF play. For context, more than one fund generated over 15X net distributions to their LPs. The numbers were enough to impress me. But I had to ask: “Across all the funds you were a part of, what is something that you look for that you’re reasonably confident others don’t?”

He said two things, but one stood out. “Gratitude. I look for managers who never forget who put them in business.”

In all honesty, I found that odd. Not because I disagreed. I love folks who recognize and are grateful to the people who got them to where they are today. But because it didn’t occur to me that it should be the top two things one should optimize for when picking managers. Naturally, it kept gnawing at me.

In my own experience, gratitude seems to compound. Grateful individuals thank you often and sometimes when you least expect it, and more often than not, assuming you’ve done real work to help them, they compliment behind your back. The people they talk to end up learning about you. Their teammates learn about you. And you’ve earned multiple occasions to meet their teammates and those close to them. When a GP or founder’s teammates leave and start new things, those people often think to call you first.

Grateful GPs often hire talent who are just as humble, and in turn, as second nature, extend their appreciation often. Those same GPs are more likely to invest in people who have similar traits as well. So, it begins this flywheel.

As an LP, I look for emerging GPs whose network and deal flow compounds over time. That the first moment I meet them is the smallest network they will ever have again. So I expect and underwrite a GP’s ability to compound deal flow over time. So Fund n+1 is better than Fund n, and Fund n+2 is exponentially better than Fund n. Gratitude is one way GPs can increase the surface area for serendipity to stick. For there to be more quality inbound opportunities in the future.

Photo by Jonny Gios 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 Increase Dialogue with your LPs | El Pack w/ Kelli Fontaine | Superclusters

kelli fontaine

Kelli Fontaine from Cendana Capital joins David on El Pack to answer your questions on how to build a venture capital fund. We bring on three GPs at VC funds to ask three different questions.

The Council’s Amber Illig asked what happens when a solo GP is incapacitated or passes away.

Oceans Ventures’ Steven Rosenblatt asked why most LPs follow the decision-making of other LPs.

NeuCo Academy’s Jonathan Ting asked what LPs think about GPs asking for help.

From investing in great fund managers to data to investor relations, Kelli Fontaine is a partner at Cendana Capital, a fund of funds who’s solely focused on the best pre-seed and seed funds with over 2 billion under management and includes the likes of Forerunner, Founder Collective, Lerer Hippeau, Uncork, Susa Ventures and more. Kelli comes from the world of data, and has been a founder, marketing expert, and an advisor to founders since 2010.

You can find Kelli on her socials here:
X/Twitter: https://x.com/kells_bells
LinkedIn: https://www.linkedin.com/in/kellitrent/

And huge thanks to Amber, Steven, and Jonathan 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
[01:26] Kelli’s new data discoveries
[04:32] How did Kelli underwrite a manager with no LinkedIn?
[06:19] Is too much data ever a problem?
[08:18] Vintage year benchmarking
[09:49] Telltale signs on GPs’ social profiles
[10:57] Data Kelli wishes she could collect
[15:59] Enter Amber and her new podcast
[18:08] Amber’s background and The Council
[19:08] How does Amber define top companies?
[24:25] How can a solo GP set the firm up well in case they’re no longer there?
[26:11] Kelli’s number one fear with solo GPs
[28:30] Best practices for generational transfers
[32:28] Solo GPs and their future plans
[36:51] Enter Steven and Oceans
[42:38] Would Kelli ever include AI summaries as part of the get-to-know-someone phase?
[44:18] Why do LPs follow other LP’s decision-making?
[48:43] What are the traits of an LP who is likely to have independent thinking?
[51:16] Why don’t LPs talk directly with founders?
[57:59] Enter Jonathan and NeuCo Academy
[1:00:05] Is Kelli seeing more secondaries firms?
[1:01:56] How often should GPs lean on LPs for help?
[1:07:22] Are most LPs helpful?
[1:12:21] What kinds of questions does Kelli get from her own GPs?
[1:15:39] Kelli’s last piece of advice

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“If that fund deployed over a year versus a manager of ours that deployed over four years, they’re going to look very different. So we do vintage-year benchmarking to see how their MOIC stacks up against how the revenue of companies stack up.” – Kelli Fontaine

“Team risk is the biggest risk in venture.” – Kelli Fontaine

“The same top ten firms are not the same that they were 15 years ago, and probably Silicon Valley. Generational transfer is very hard.” – Kelli Fontaine

“If you make the brand bigger than just you that it comes from DNA, support systems, things that you stand for that have had support to get there—so once that brand is made, the other team members embody that brand as well. That’s the way to do it. It’s really empowering other team members to own a part in that brand-building—outwardly and inwardly in decision-making.” – Kelli Fontaine


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.

81% of America is Underfunded | Vijen Patel & Grady Buchanan | Superclusters | S5PSE1

vijen patel, grady buchanan

“19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.” – Vijen Patel

We’re back with one of our crowd favorite formats, where we bring on one LP and one GP, and share why that LP invested in this GP. This time, we have Grady Buchanan, co-founder of NVNG, and Vijen Patel, founding partner of The 81 Collection.

Vijen Patel is an entrepreneur and investor. He founded The 81 Collection, a high growth equity firm in boring industries. Previously, he founded what is now known as Tide Cleaners. He bootstrapped what eventually became the largest dry cleaner in the country (1,200 locations) before selling to Procter & Gamble in 2018. Before Tide Cleaners, he worked in private equity, McKinsey & Company, and Goldman Sachs. He lives in Chicago with his wife and two kids.

You can find Vijen on his socials here:
LinkedIn: https://www.linkedin.com/in/vijenpatel/
X / Twitter: https://x.com/itsvijen

Grady Buchanan is an institutional and risk-based asset allocation professional with a passion for bringing venture capital to those who have the interest. He founded NVNG in late 2019 and oversees investment strategies, the firm’s venture fund pipeline, manager sourcing, due diligence, and external events. Before launching NVNG, Grady worked with the Wisconsin Alumni Research Foundation’s (WARF) $3B investment portfolio, focused on private equity and venture capital initiatives, including fund diligence, investment strategy, and policy. Grady is based in Milwaukee, WI.

You can find Grady on his socials here:
LinkedIn: https://www.linkedin.com/in/gradynvng/
X / Twitter: https://x.com/GradyBuchanan

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

OUTLINE:

[00:00] Intro
[02:41] The pressure of quitting a PE job for dry cleaning
[05:09] Vijen’s self talk as a founder
[06:50] How to overcome doubt
[09:00] How Vijen learned customer success
[10:35] What did Pressbox become?
[12:41] The dichotomy between society’s needs and what gets funded
[14:19] How did Grady go from selling pancakes to being an LP?
[23:51] Why did Grady think he bombed the LP interview?
[29:15] What is The 81 Collection?
[32:22] How did Vijen meet Grady?
[34:39] How is Vijen fluent in Spanish?
[36:40] How did Grady meet Vijen?
[42:21] How did Grady underwrite 81 Collection?
[44:44] What about Vijen made Grady hesitate?
[48:35] What’s one thing about 81 Collection that could’ve gone wrong?
[50:33] The 3 things that create alpha
[52:42] Why does NVNG have the coolest fund of funds’ names?
[53:47] The legacy Grady plans to leave behind
[56:06] The legacy Vijen plans to leave behind

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“I wrote down everyone’s concerns, and I just sat on it. A lot of the founders we like to work with, the ones who we really love are the ones who take it in and listen, write it down, then take some time to synthesize everything and then they’ll act with conviction. ‘Why is this stupid? Tell me why. Let’s go deeper and deeper.’ And oftentimes these reasons are very rational and slowly over time, what if I derisk this by doing that?” – Vijen Patel

“19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.” – Vijen Patel

“There’s this crazy stat we recall often: the 50 richest families on Earth, who often build in this 81, they’ve held, on average, their business for 44 years.” – Vijen Patel

“We invest in only amazing managers; we will not invest in every amazing manager.” – Grady Buchanan

“Alpha’s three things: information asymmetry, access, and, actually, taxes.” – Vijen Patel


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.