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

anurag chandra

โ€œThere are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. Iโ€™ve only seen five or six because Iโ€™ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.โ€ โ€” 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 Personnelย 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 onย Apple Podcastsย andย Spotify. You can alsoย 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

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SELECT QUOTES FROM THIS EPISODE:

โ€œYou seem like a good guy. Iโ€™d love to find ways to work with you, but Iโ€™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 Iโ€™m in a board meeting and thereโ€™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 youโ€™re working on. But do not make them long. I donโ€™t need dissertations.โ€ โ€” Mark Stevensโ€™ advice to Anurag

โ€œThere are a thousand ways to put lipstick on the pig and there are a thousand skeletons [in the closet]. Iโ€™ve only seen five or six because Iโ€™ve only seen three startup experiences. And so you need to deputize as many people as you possibly can to essentially triangulate.โ€ โ€” Anurag Chandra

โ€œYou can do two weeks or two years of due diligence on a company, in particular if youโ€™re a mid-stage or later-stage investor. And itโ€™s after the first board meetingโ€”I have a friend who affectionately refers to it as the โ€˜Oh Shit!โ€™ board meeting where you show up, and now youโ€™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 youโ€™re still going to end up with skeletons you were unable to uncover? No. I still think process matters.โ€ โ€” Anurag Chandra

โ€œLook for GPs who are magnets, as opposed to looking for a needle in a haystack.โ€ โ€” Noah Lichtenstein

โ€œProcess drives repeatability.โ€ โ€” 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
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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.

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 Partnersโ€˜ 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 bachelorโ€™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 onย Apple Podcastsย andย Spotify. You can alsoย 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:

โ€œWhatever the evolution of venture is if youโ€™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.โ€ โ€” Beezer Clarkson

โ€œIf youโ€™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 youโ€™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.โ€ โ€” Beezer Clarkson

โ€œIf youโ€™re competing for the deal, youโ€™ve already lost it.โ€ โ€” Beezer Clarkson

โ€œI 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?โ€ โ€” Stephanie Palmeri

โ€œRecycling is incredibly important, but incredibly hard to plan for, especially as early as youโ€™re coming in, unless youโ€™re seeing evidence of acqui-hires today and you know youโ€™re going to have those dollars coming in. Obviously, really hard. So I would not bank your farm on that.โ€ โ€” 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

โ€œYou need to make space for weird types of conversations to happen on the fringes that really inform you whatโ€™s going on at the frontier.โ€ โ€” 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 3xโ€“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 atย 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 onย Apple Podcastsย andย Spotify. You can alsoย 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:

โ€œYou need to make space for weird types of conversations to happen on the fringes that really inform you whatโ€™s going on at the frontier.โ€ โ€” Thorsten Claus

โ€œRisk is the probability of a fatal outcome within given resources.โ€ โ€” Thorsten Claus

โ€œIs it really out of conviction that theyโ€™re acting on [the advice] or is it just a belief? You know, I believe in many things, but do I act accordingly? Thatโ€™s the difference between belief and conviction.โ€ โ€” Thorsten Claus

โ€œThe self audit of our actions, behaviors, processes, and decisions is so important.โ€ โ€” Thorsten Claus

โ€œWhat I find more interesting than the question about โ€˜whatโ€™s the one thing you donโ€™t want me to know about youโ€™ 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 Iโ€™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.โ€ โ€” Thorsten Claus

โ€œIf 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.โ€ โ€” Thorsten Claus

โ€œThere are no bad teams, only bad leaders.โ€ โ€” Jocko Willink

โ€œThere 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.โ€ โ€” Thorsten Claus

โ€œCapital formation is a design principle. Fundraising is a sales process. Without true design around a customer base and a product, you will fail eventually.โ€ โ€” 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 รœmit 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


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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.

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 whoโ€™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 onย Apple Podcastsย andย Spotify. You can alsoย 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

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โ€œIf that fund deployed over a year versus a manager of ours that deployed over four years, theyโ€™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.โ€ โ€“ Kelli Fontaine

โ€œTeam risk is the biggest risk in venture.โ€ โ€“ Kelli Fontaine

โ€œThe same top ten firms are not the same that they were 15 years ago, and probably Silicon Valley. Generational transfer is very hard.โ€ โ€“ Kelli Fontaine

โ€œIf 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 thereโ€”so once that brand is made, the other team members embody that brand as well. Thatโ€™s the way to do it. Itโ€™s really empowering other team members to own a part in that brand-buildingโ€”outwardly and inwardly in decision-making.โ€ โ€“ 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

โ€œ19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.โ€ โ€“ 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 firmโ€™s venture fund pipeline, manager sourcing, due diligence, and external events. Before launching NVNG, Grady worked with the Wisconsin Alumni Research Foundationโ€™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 onย Apple Podcastsย andย Spotify. You can alsoย 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

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โ€œI wrote down everyoneโ€™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 theyโ€™ll act with conviction. โ€˜Why is this stupid? Tell me why. Letโ€™s go deeper and deeper.โ€™ And oftentimes these reasons are very rational and slowly over time, what if I derisk this by doing that?โ€ โ€“ Vijen Patel

โ€œ19% of our GDP attracts about 55% of capital inflows, aka venture activity, and 81% is underinvested.โ€ โ€“ Vijen Patel

โ€œThereโ€™s this crazy stat we recall often: the 50 richest families on Earth, who often build in this 81, theyโ€™ve held, on average, their business for 44 years.โ€ โ€“ Vijen Patel

โ€œWe invest in only amazing managers; we will not invest in every amazing manager.โ€ โ€“ Grady Buchanan

โ€œAlphaโ€™s three things: information asymmetry, access, and, actually, taxes.โ€ โ€“ 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.

On GP Commits

backflip, commit

1% GP commits have been a part of investing history for as long as most people can remember. But actually finds its origin as a vestigial part of IRS Revenue Procedures from 1974, more specifically Rev. Proc. 74-17, which stated “the interests of all the general partners, taken together in each material item of partnership income, gain, loss, deduction or credit is equal to at least one percent.โ€

And yes, technically, in 1989, Rev. Proc. 89-12 also created a lower bound of 0.2%. “In no eventโ€ฆ may the general partnersโ€™ aggregate interest at any time in any material item be less than .2 percent.” But all of that was overturned in 2003.

Ever since then, the 1% GP commit has withstood the test of time.

But… I’ve always felt that to be a weird checkbox that LPs have for GPs. I get the element around incentive alignment. But why is incentive alignment a static number? If a college student is just starting a Fund I, still with student loans, and raising a $10M fund, $100K is a meaningful proportion of their net worth. Hell, they may not even have it. At the same time, a successful spinout who used to be a GP at a large established fund who’s received distributions already and raising $100M fund will likely have more than just $1M. And $1M alone is not a meaningful proportion of her/his net worth.

So, I think GP commits should be a function of a GP’s net worth, not the fund size.

I want to know that the GP is betting their career over on this next enterprise. I want to know that the GP is more motivated today than they were ever before. Even if they’ve already hit that career-defining success.

I’m looking for the fire under their belly. Why does this upcoming fund matter so much to them?

Personally, it’s not that I only choose to focus on Fund I’s and II’s. I’m open to the idea of other Roman numeral-ed funds, but I usually get the sense that the economics of commitment are misaligned with the intentions and motivations of the GP themselves.

Photo by Drew Farwell 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 Many Exceptions Are Too Many? | El Pack w/ John Felix | Superclusters

john felix

Pattern Ventures’ John Felix 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.

Atria Ventures’ Chris Leiter asked about the common mistakes LPs make when underwriting solo GPs.

Garuda Ventures’ Arpan Punyani asked how quickly do most LPs get to conviction. First 10 minutes? First meeting?

Geek Ventures’ Ihar Mahaniok asked how LPs evaluate Fund IIs when the Fund I has no distributions.

John Felix is a General Partner and Head of Research at Pattern Ventures, a specialized fund of funds focused on backing the best small venture managers. Prior to Pattern, John served as the Head of Emerging Managers at Allocate where he was an early employee and helped to launch Allocate’s emerging manager platform. Prior to joining Allocate, John worked at Bowdoin College’s Office of Investments, helping to invest the $2.8 billion endowment across all asset classes, focusing on venture capital. Prior to Bowdoin, John worked at Edgehill Endowment Partners, a $2 billion boutique OCIO. At Edgehill, John was responsible for building out the firm’s venture capital portfolio, sourcing and leading all venture fund commitments. John started his career at Washington University’s Investment Management Company as a member of the small investment team responsible for managing the university’s now $13 billion endowment. John graduated from Washington University in St. Louis with a BSBA in Finance and Entrepreneurship.

You can find John on his socials here:
LinkedIn: https://www.linkedin.com/in/johnfelix12/
Twitter: https://x.com/johnfelix123

And huge thanks to Chris, Arpan, and Ihar for joining us on the show!

Listen to the episode onย Apple Podcastsย andย Spotify. You can alsoย watch the episode on YouTube here.

OUTLINE:

[00:00] Intro
[02:20] What’s changed for John since our last recording?
[04:08] What is Pattern Ventures?
[06:22] Why is Pattern’s cutoff for funds they’re interested in at $50M?
[07:32] How does John define noise?
[09:34] Do non-sexy industries require larger seed funds?
[11:36] How does think about overlap in the underlying startup portfolio?
[15:22] Enter Chris and Atria Ventures
[18:03] Should solo GPs scale past themselves?
[24:14] Partnerships have more risk than solo GPs
[26:10] How does John think about spinouts from large VC firms?
[27:53] The psychology of being a partner at a big firm versus your own
[30:38] Enter Arpan and Garuda Ventures
[31:26] Geoguessr
[32:52] Garuda’s podcast, Brick by Brick
[34:52] How quickly do LPs know they intuitively want to invest in a GP?
[38:02] The analogy to what GPs do to founders
[43:50] There are many ways to make money
[44:57] Quantifying intuition as an investor
[49:12] Enter Ihar and Geek Ventures
[49:36] How do LPs evaluate Fund IIs when Fund I has no DPI?
[53:01] How do you know if a GP did what they said they were going to do?
[54:47] What if the key value driver is off-thesis, but everything else is on-thesis?
[56:21] Is signing 1 uncapped SAFE per fund reasonable?
[57:14] What is the allowable percentage of exceptions in a fund?
[1:01:32] Good vs bad exceptions
[1:06:06] Reminders that we are in the good old days
[1:07:31] John’s last piece of advice to new allocators
[1:09:00] David’s favorite moment from John’s last episode

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โ€œIn life, itโ€™s always easy to justify โ€˜why nowโ€™ is not the right time. I think itโ€™s hard to justify โ€˜why nowโ€™ is the right time to do something.โ€ โ€“ John Felix

โ€œWe love investing in things that are contrarian and non-consensus, but there has to be a path to becoming consensus because something canโ€™t remain non-consensus forever. There has to be a catalyst that the market eventually realizes this or else the companyโ€™s not going to be able to raise venture capital. Itโ€™s not going to be able to sustain it and continue to grow and survive.โ€ โ€“ John Felix

โ€œThe type of spinouts we want to back are the people who are successful in spite of working at the big brand, not because they worked at the big brand.โ€ โ€“ John Felix

โ€œYou need to earn the right to start your new firm to do your own thing. I donโ€™t think enough people realize that.โ€ โ€“ John Felix


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.