questions - Cup of Zhou

November 3, 2025November 2, 2025

Where Does Intuition Come From? | Yiwen Li | Superclusters | S6E6

“The intuition part comes from activities of creativity that change your perspective.” — Yiwen Li

Yiwen Li is a seasoned investor with a successful track record of investing in AI, blockchain, and healthcare tech while developing global business partnerships to fast-scale the business.

Yiwen is currently Head of Venture Investments at Bayview Development Group, a global family office with diverse exposure public market, private equity, venture, and real estate. Prior, she was a Principal at Alumni Ventures, responsible for end-to-end multi-stage investments focused on blockchain and fintech. She was Director for Corporate Strategy at Masimo (Nasdaq: MASI). She built an innovation pipeline in healthcare connectivity and data analytics. She was Director for Corporate Development at NantHealth (Nasdaq: NH), where she established the international business division. Yiwen started her career at Capital Group in equity research.

Yiwen is an Advisory Board member of C-Sweet. She served on the board of Give2Asia as the chairman of the finance committee and a member of the investment committee. She was an advisory board member for the Asia Society where she co-founded the “Asian Women Empowered” initiative. She was recognized as the” Top 50 Women Leaders in San Jose 2024 and 2025”, “Top 50 Women in 2019” and the “Most Inspirational Women in Web 3”. Yiwen is also the author of one of the best sellers “Make the World Your Playground”, inspiring women to find their unique path. She is a frequent speaker on innovation and emerging technology trends.

Yiwen holds a Master from the London School of Economics and a Master from the University of Vienna. She also graduated from the Venture Capital program at UC Berkeley and the Private Equity Program at Wharton. She was selected to be one of the ” Young American Leaders” at Harvard Business School. Yiwen is a recipient of the European Union’s Erasmus Mundus scholarship. She is fluent in Mandarin and German, worked and lived in Europe, Asia, and US.

You can find Yiwen on her socials here:
LinkedIn: https://www.linkedin.com/in/yiwenli999/

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

OUTLINE:

[00:00] Intro
[02:07] Yiwen’s childhood
[05:00] Jazz singing
[06:14] The value of learning languages
[09:01] How to build intuition around emerging managers
[14:51] Getting to the bottom of a GP’s motivation
[16:33] What percent of GPs are not in VC for the right reasons?
[19:47] Does success fuel or inhibit ambition?
[24:17] The cost of knowledge is cheaper
[24:56] Competitive edges in the current world
[27:06] Why creative activities matter
[31:21] Advice to emerging LPs
[32:42] Post-credit scene

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SELECT QUOTES FROM THIS EPISODE:

“The entrepreneur’s [life] is a life where you’re eating glass every day.” — Yiwen Li

“For the first time, the cost of knowledge is becoming cheaper.” — Yiwen Li

“It’s the easiest time to create a company. It’s also the most difficult time to maintain the competitive edge of that company.” — Yiwen Li

“The intuition part comes from activities of creativity that change your perspective.” — Yiwen Li

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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 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

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 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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“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 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?

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“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

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“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

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“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!

September 22, 2025September 22, 2025

How to Not Get Fired When Changing Your VC Strategy | El Pack w/ Beezer Clarkson | Superclusters

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

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

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

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

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

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

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

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

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

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

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

OUTLINE:

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

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

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

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

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

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

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

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