David - Cup of Zhou

October 27, 2025October 26, 2025

$80M vs $800M vs $8B Endowment | Trish Spurlin | Superclusters | S6E5

“Once you hit a billion dollars, you should probably consider some sort of internal team. Just to mitigate risk. There’s audit risk involved when you have such a small number of people managing a huge pool of capital. It’s going to differ for everyone. That’s probably a good benchmark.” — Trish Spurlin

Trish Spurlin is the Investment Director at Babson’s $800M endowment, covering private markets investing with a large focus on venture. In fact 70% of their private equity portfolio is venture capital. Quite a unique strategy for an endowment to take. Why? An endowment is required to provide, in this case, the university money every single year, anywhere from 5% to 60% of a university’s annual budget. And to invest in an illiquid asset class aka venture capital that doesn’t return capital till a decade later, if not longer, takes courage.

You can find Trish on her socials here:
LinkedIn: https://www.linkedin.com/in/trishspurlin/
X / Twitter: https://x.com/trishdigi

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

OUTLINE:

[00:00] Intro
[01:45] Sports in Trish’s life
[05:10] How does success fuel inhibit ambition? How does it inhibit ambition?
[07:35] How do you underwrite long term motivation?
[13:21] How fast you order something might matter
[16:04] Can Trish angel invest outside of Babson?
[17:08] Endowment with a $80M budget
[19:54] Should you hire an outsourced CIO?
[24:18] Endowment with a $8B budget
[27:47] Babson’s liquidity requirements
[30:33] How to ask about a senior partner leaving
[34:05] How does Trish build trust with her GPs?
[37:48] Trish’s interests vs Babson’s interests
[45:24] Hank Sauce
[47:26] Why is Ocean City Boardwalk special?
[48:51] What serves as a reminder to Trish we’re still in the good ol’ days?

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“What have [ambitious people’s] transition periods looked like? A lot of times when people do really cool things, there are 2-3 years after where they just don’t know what to do with themselves. That’s very normal. You see that with Olympians. You see that with astronauts.” — Trish Spurlin

“If you want to be told things when they aren’t going well, you can’t freak out when somebody tells you something that’s not going well. No emails in caps. No yelling. Take a moment to digest what you’re being told. You’re collecting information. You can discuss that information when the time is appropriate.” — Trish Spurlin

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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.

October 24, 2025October 24, 2025

Fundraising ≠ Capital Formation

I was chatting with a GP last week about the highlights and lowlights of having a multi-stage fund or just a VC fund as an LP via their fund-of-funds. The obvious synergies of access to downstream capital and branding, especially if the individual running the fund-of-funds is known for their institutional track record as an LP. As well as access to the GPs at those funds for mentorship reasons.

But the downsides also exist. You’re one of many of other GPs who have access to the same team. More often than not, there’s no institutional diligence. And the investment happens largely for strategic purposes. Same is true for multi-stage GPs investing through their own family office. But you also have to think through the tough conversations you need to have when you take checks from more than one of these funds. Assuming all else equal, and they write the same check size, when your portfolio companies are outperforming, do you pass them to Big Fund A or Big Fund B? Equally as true for any LP who wants co-investment opportunities. Family offices. Fund-of-funds. The classic question of: Do you like Mom or Dad more?

And there’s one more. Consider a multi-stage fund who’s an LP in your fund. You share one of your stellar portfolio companies with them, and they loved the deal so much they also invested. Not only invested, but led the following round at a much, much higher valuation. For the sake of this thought experiment, let’s say the Series A valuation is a solid nine figures. As such, they take a board seat. A year later, your portfolio company has the opportunity to exit for $800M. A phenomenal exit for everyone on the cap table, including yourself, your other co-investors, the founders, and the employees. And for you in particular, this would return meaningful multiples of your fund. But not your Series A lead, who is also your LP. The math isn’t inspiring for them. $800M would only be a shy 4-8X on their initial investment.

So, the Series A lead/your LP blocks the acquisition deal and pushes the founders to go for more. You push back on the motion as everyone else’s incentive, including the founders, is the same as yours. Whether the deal happens or not at this point is irrelevant. This Series A lead, who’s also your LP, ends up telling a number of other LPs that you’re difficult to work with. To the effect that they would also no longer re-up in your next vintage. And that makes your fundraise for the next fund even harder than you expected.

You’ve not only lost a $500-2M check (on average), but worse, you’re likely to have a tarnished reputation with prospective LPs. If they like you already, they may look beneath the surface. If they haven’t gotten to know you, they’ll likely surmise on limited information that the juice isn’t worth the squeeze.

Before you dismiss this as just a hypothetical case study, note that this is a true story.

As my buddy Thor once told me, “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.”

Capital formation is thinking through the types of conversations you want to have when you’re in Fund n+1 and n+2, 5-6 years from now. As Adam Marchick once said, “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.” These are the conversations about extending recycling periods, early distributions, fund extensions, and so on. Many of which revolve around the return incentives of your LP base (if decisions are made by majority approval) or by LPAC approval. A family office who has no immediate liquidity needs might not want early distributions and wants you to hold out. Another who’s starting a new business line or pulling completely out of venture (because they were misinformed or set the wrong expectations initially) will want early liquidity and/or someone to buy their stake. An institution with a high leadership turnover rate will likely have a new CIO who’ll want to redo the whole portfolio. So what used to be obvious re-up decisions will need to be re-underwritten altogether.

So I’m not here to say, “Don’t take LP checks from fund-of-funds whose core business is being a VC.” I just want to remind you to consider the incentives of each LP you have on your cap table. Ideally, your LP base’s incentives are homogenous. Not only to themselves, but also to yours. Realistically, for the average emerging manager, it won’t be. But if you know it won’t be, prepare guardrails for future conversations. Don’t walk in blind.

Photo by Dan Meyers on Unsplash

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October 20, 2025October 19, 2025

The Seneca of Investing | Jacob Miller | Superclusters | S6E4

“There’s this thing called alpha, which is returns driven by skill not market return. And when you start to think about what does that mean, skill means you’re doing something that other people aren’t. You have to be different from the average. What can drive that? How are you going to have that be positive expected value? You need to have unique information, unique insight, unique access, or get uniquely lucky.” — Jacob Miller

Jacob Miller is the Co-Founder and Opto’s Chief Solutions Officer, a key figure in its leadership team and central to its growth strategy. He spearheads initiatives for Opto’s fiduciary partnerships and the systemization of institutional-quality private markets investment techniques and programs.

Before co-founding Opto, Miller spent nearly five years as an investor at Bridgewater Associates. Miller has a passion for sensible long-term investing, systematizing investment processes, and distilling complex market dynamics into clear, logical linkages that help people better understand their investments. Having managed money for family and friends since he was 16, Miller is a certified market junkie. While he has a background in macroeconomics and high-yield debt, he finds the challenges and opportunities in the private markets space far more interesting and important, both for investors and society.

You can find Jacob on his socials here:
LinkedIn: https://www.linkedin.com/in/jacob-m-08b32967/

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

OUTLINE:

[00:00] Intro
[01:49] Why did Jacob start investing at 8 years old?
[07:20] The fallacies of storytelling
[08:49] Inputs, framework, and outputs
[09:21] Jake’s mental framework for alpha
[12:31] Pete Soderling’s unique access
[13:49] Jacob on defense tech VCs
[14:57] How does Jacob underwrite relationships in defense?
[16:30] How do you know if someone’s been preaching a story before it became a story?
[20:16] The difference b/w an opinion and an insight
[23:07] Why does Jacob write?
[25:42] Running with Joe Lonsdale at 8:30AM
[29:12] 2 wildly different billionaires
[31:48] What does Jacob want for the world?
[36:23] What keeps Jacob humble?

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SELECT QUOTES FROM THIS EPISODE:

“A jack of all trades is a master of none, but oftentimes better than a master of one. — William Shakespeare

“If you didn’t have stories or branding, it would take you four hours to choose which cereal to get based on solely merit — if you did cost comparison versus ingredients, nutrition, et cetera. You need the story to make a decision in two seconds rather than six hours.” — Jacob Miller

“You need to know what are the assumptions that underpin those stories so you can know if and when they’ve been invalidated.” — Jacob Miller

“You have inputs; you have a framework; you have outputs. The story is the output. You can be wrong on your inputs. You can be wrong on your framework. Better to be wrong on your inputs than your framework. Because if you were wrong on your framework—and it’s garbage— it’s garbage in, and garbage out.” — Jacob Miller

“As investors, we probably don’t want to bet on getting uniquely lucky. And access and information counts as insider trading in public markets. And so if you’re going to a public market asset manager who claims to have alpha, you need to be defending why you have unique insight. Why can you take information that everyone else has and derive conclusions that other people won’t, which is a very high bar. […]

“But in private markets, we can look to what are unique sources of access and information. Are you in founder networks that other people are not in? How can you show me you see deals before other people do? Do you have benefits as an LP or GP that you can bring to founders that might lead to preferential pricing that would lead to them choosing you first? Do you have a reputation that will attract the right kind of talent? And then on top of that, do you have really insightful frameworks about what makes a great founder, about how to assess TAM, about how to help a company scale through product-market fit to expansion and et cetera? I always start a private market analysis with: ‘Let’s talk about access and information. What do you see that others don’t? What do you know that others don’t?” — Jacob Miller

“Too much source-citing is honestly a red flag for me. This should be stuff you’re learning in the market that’s evidence of your unique access to information.” — Jacob Miller

“The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn.” — Alvin Toffler

“That which Fortune has not given, she cannot take away.” — Seneca

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!

October 17, 2025October 17, 2025

Dear Emerging Manager

You are not all top quartile. Only 25% of you are.

You are not all top decile. Only 10% of you are.

I refuse to believe that I’m somehow seeing only the best in market. I’m not famous or lucky enough to have that fortune. Even the best known LPs I know are not so.

If your marks include companies held at last round valuation (LRV) for longer than two years, please consider proactive re-marks. This includes your angel portfolio.

SAFE rounds are not mark-ups. Do not conflate real marks with hypothetical marks.

If the founder doesn’t know who you are AND if you don’t know the company’s updates in the last two quarters, you don’t know the founder. Do not pretend you do. Your investment is not accretive to your future network. I dare say if I went to those founders right now, and asked them who their top five favorite investors are, you won’t come up. You’re forgettable. And that’s a cardinal sin of firm-building.

Let me caveat that firm-building means you plan to grow the firm. That where you are today is not where you want to stay forever as a GP. This matters far less if this is a one-and-done fund. That is okay. You don’t have to love venture forever. You don’t have to pretend you do.

Do not believe you are that special if you have a multi-stage GP as an LP. Many of the notable multi-stage GPs have invested in many. Some have invested in multiple dozens. Others hundreds. A handful we see in almost every deck. It is their job to see everything Or at least attempt to. The cardinal sin for a multi-stage GP is to not see the deal, worse than not picking or winning it.

Assume all your LPs will be passive LPs. I don’t care about their profile, how referenceable they are, how much they love you, how much they want to help. Give it a few months, a year at best, they will become passive. Human interest is fleeting. Especially since venture is the smallest bucket in our allocation (excluding funds-of-funds). And yes, they have day jobs. There are exceptions. For instance, someone who wants to start their own VC fund or someone who wants to be a VC themselves. That is not everyone.

When modeling, it is bold of you to assume that more than 10% of your portfolio will be outliers. It is bold of you to assume that more than 5% of your portfolio will be outliers. We are in a power law industry.

You will get diluted. More than you think. With how much longer companies are staying private, and how much capital is available in the later growth stages, you will get diluted. 80% is safe to assume if you have no reserves. Down to 65% depending on how much you have. There are very, very few cases you only have 50% dilution. Yet I see many GPs model their portfolio that way.

Pro rata is a legal right no successful capital will grant without a fight. If you get it without a fight down the road on a great company, ask yourself why you’re so lucky. And never forget to ask yourself that question.

In a market of exceptions, you are all more normal than you think. It sucks. In any other industry, most of you will have fairly little competition for greatness, but you chose one of the few industries where your competition is all exceptions.

How you react to a ‘no’ from an LP is a sobering fact and a great telltale sign of the strength of your relationships. I love chatting with other LPs who’ve passed on you. Not because I need to hear their why—most of our interests and mandates are different, but because I almost always ask how you react to their ‘no.’ And I am not alone here. Usually, LPs volunteer that information up quite readily. Of note, different LPs say ‘no’ differently. Most don’t. A fact I am aware of.

Many of us who do this as our primary job love you. We love venture. We love the romanticism that comes with this space. Do not play the hopeless romantic back. We need the truth.

There’s a great line that Elizabeth Gilbert credits her wife Rayya Elias. “The truth has legs. It always stands. When everything else in the room has blown up or dissolved away, the only thing left standing will always be the truth. Since that’s where you’re gonna end up anyway, you might as well just start there.”

The best time to share the truth is in person. And immediately. The second best is a 1:1 call. If it’s not urgent, save it for the AGM. If it is, call us.

We should not learn about you or your portfolio for the first time via the news. If we are, you’ve lost our trust. Shit happens. We get it. How you respond and communicate shit is what makes or breaks a relationship.

Many of my colleagues try to be helpful even if they can’t invest. Understand because they’re human they can’t be so for everyone. So when they are, don’t take it for granted.

If you conflate any of the above, you’re either lying to yourself or you’re lying to us. The former means you’re never going to make it in this industry. The latter means we’re just not going to be good partners for you.

This is not a Bible. Do not swear by it. Do not pray to it by the bedside every night.

This is just a morning wake-up call. Some of you have already woken up. Many of you may not have.

Photo by Álvaro Serrano on Unsplash

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October 13, 2025October 12, 2025

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

“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

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!

October 10, 2025October 10, 2025

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

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

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

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

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

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

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

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

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

October 6, 2025October 6, 2025

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

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

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!

October 3, 2025October 2, 2025

Energy, Intelligence, and Integrity

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

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

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

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

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

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

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

The best decks have both.

Photo by Zdeněk Macháček on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

September 29, 2025September 28, 2025

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

“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

“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

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!

September 26, 2025September 25, 2025

The Question-Off

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

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

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

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

Kevin’s questions for me:

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

My questions for Kevin:

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

Photo by Ahmet Yüksek ✪ on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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