questions - Cup of Zhou

November 24, 2025November 23, 2025

“Venture Should Play More Like Moneyball” | Carson Monson | Superclusters | S6E9

“The limiting downside is actually something a lot of emerging managers don’t think about. If you can turn all of your portfolio companies that don’t hit that exit velocity, if you can find a soft landing for those companies versus that’s a writeoff and they’re dead and done, that’s extra effort, but that’s an extra turn on your fund’s performance.” — Carson Monson

Carson Monson is a seasoned allocator with nearly a decade of experience backing emerging and spinout GPs across large institutions, government entities, and family offices. After stints at Greenspring, SITFO, and building a fund of funds strategy for a large European single family office, he now runs the fund of funds at CrossRange, which focuses on supporting top-tier emerging and spinout GPs.

Carson has backed everything from micro funds to high-profile managers spinning out of tier-one firms. He is deeply committed to being a thought partner and strategic resource to the GPs he supports, helping them navigate the complexities of fund building and long-term success in the VC industry.

You can find Carson on his socials here:
LinkedIn: https://www.linkedin.com/in/carson-k-monson/
X / Twitter: https://x.com/Monsson_

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

OUTLINE:

[00:00] Intro
[02:08] Wildlife and wholesome trouble
[06:03] The journey to being an LP
[10:54] How did Carson join Greenspring?
[13:55] Lessons across Greenspring
[15:46] How many deals did Greenspring do per year?
[18:46] An example of a qualitative metric worth measuring
[20:16] How many off-thesis bets is a VC allowed to make?
[21:25] When do GPs move from thematic bets to opportunistic bets?
[25:45] How much AUM should any one GP have?
[29:46] Why does Carson liked concentrated portfolios?
[30:32] The case for concentrated portfolios
[36:40] Relationships with GPs should stay at the LP partner level
[39:49] Fund strategy at Fund (n) vs Fund (n + 1)
[45:19] What the hell is ‘critical node theory?’
[49:54] Examples of great references
[52:58] The halo effect of mega funds
[58:48] How does Carson get to inbox zero
[1:02:09] Why is CrossRange different?
[1:08:17] The last time Carson had a pinch-me moment
[1:10:17] Carson’s ricotta gnocchi
[1:12:28] Post-credit scene: Ramen, gluten, Tokyo, and Tonkatsu Suzuki Pt 2

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On if 20% of the fund is focused on opportunistic bets… “Wealthy is a nice word. I would say [20% is] egregious. […] 10%, it’s not like it’s the right number, but it’s the number most LPs won’t contest.” — Carson Monson

“In the past, there have been GPs who are truly excellent at one thing or a couple of things, whether that’s a thesis, strategy, or an approach. And that approach makes a ton of sense at the fund size that they’re operating at or maybe a little bit larger. In the 20-teens especially, people were able to raise more and more, and strategy drift became a huge issue. That is something managers have to face the music on now. It’s almost like the idea of being a professional baseball player and grinding and working your way up and becoming excellent and an all-star baseball player. Then being, ‘Well, the motion is similar in cricket, so I’ll just go play cricket now.’ Ya some of the motions are similar, but it’s a fundamentally different sport. Strategy drift, fund size drift; it can be a really easy trap to fall into. The motions are similar, but you lose that competitive edge when you start to play a different sport.” — Carson Monson

“If you’re more concentrated, there is an ability to impact outcomes more meaningfully. I like GPs that play a critical role in the ecosystem in which they operate in. If you play a critical role—whether that’s in go-to-market motions, whether that’s in commercialization, whether that’s in branding and storytelling—there are so many ways you can play that role. Those types of GPs tend to have an ability to move the needle for their founders more—both on the upside and limiting the downside.” — Carson Monson

“Venture should play more like Moneyball. If you can get your companies on base and limit strikeouts, that is actually so impactful at a fund level. More emerging managers should try to think like CIOs, and less like individual investors, like being a portfolio manager and managing outcomes. Obviously, venture is a game of minority positions. You do not have sole control. Playing that role for your founders, it impacts performance. It impacts reputation and, in fact, your ability to win in the future.” — Carson Monson

“You cannot say, ‘I’m going to be SV Angel today, so I can be USV tomorrow.’” — Carson Monson

“A multi-billion dollar mega fund has to have a portfolio of companies whose aggregate equity value outstrips the GDP of most small nations on this planet.” — Carson Monson

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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.

November 21, 2025November 20, 2025

Underwriting Things That Don’t Change

One of the most interesting lines I heard on a podcast that Mike Maples was on was: “90% of our exit profits have come from pivots.” Which I first wrote here. Then here. It’s a line that lives rent free in my mind. Ideas, startups, roadmaps, and goals change all the time. I get it. That’s life. Very, very few folks are folks who unilaterally pursue one thing their entire lives. And of those who do, they’re not all successful.

Another friend of mine whose track record speaks for itself, having invested and involved herself in multiple boards before those companies became unicorns and even after, once told me that the idea she invests in is irrelevant. As long as it has grounds and can be adjacent to a large market. The primary thing she looks for is the founding team.

Early-stage investors obsess about people. They’re not wrong. Some are misled by these “VC-isms.” Others still have their own way of underwriting them. I don’t have a crystal ball. I’m also not the smartest person to be dishing out predictions. I have a rough idea of what will change, though I may not always be right. But I don’t know how they’ll change. Or when. So I’ve lived an investing career obsessing over things that don’t change. Or as Naval Ravikant puts it: “If you lived your life 1000 times, what would be true in 999 of them?”

I’ve written about flaws, limitations and restrictions before. But to quickly surmise:

Flaws are things you can overcome. Limited track record. Never managed a team. Never scaled a product. Limited access to capital.
Limitations are imposed by others and/or the environment. Gravity dictates that objects don’t fall upward. There are only 24 hours in a day. If you’re not based in the Bay Area, it’s harder to raise capital. Certain investors prefer co-founders and partnerships. Certain investors care about warm intros. The list goes on.
Restrictions are rules imposed on yourself by yourself. Batman can’t kill. You only invest in solo founders. You only invest in healthcare. You don’t invest in anyone outside the Ivy League schools. But some restrictions go deeper. You’ll never hire from a job portal again. You never hire or invest outside of your network. You won’t invest or hire having never met someone in person. You need to meet their spouse before you make a hiring decision. You don’t invest in single parents. You don’t hire anyone who doesn’t read at least one book per month. You micromanage. You don’t hire anyone who cannot curse. And yes, I’ve heard all of the above and more. My curiosity is always: Why do you impose such restrictions on yourself? What is the story you’re not telling me? Is out of a fear or admiration?

All that to say:

Flaws will and can change if it is a priority. But won’t change if they’re not.
Limitations might change, but it’s outside of your and my control. And I don’t get paid to pray to the weather gods.
Restrictions often don’t change.

Whether you admit it or not, certain habits are hard to change and unlearn. It’s possible. But that requires you to not only be aware of it, but also actively want to change it. Other habits are second nature. How you treat others. How you start each conversation. Why you look both ways before crossing even an empty street. Why you’ve sold yourself a particular personal narrative. Why you have to invest a certain thesis.

The world seems to always be trying to stay on top of things, but there seems to be far less dialogue around how to get to the bottom of things. To me, when it’s underwriting a person and their team, it’s about underwriting what doesn’t change rather than underwriting what could.

Photo by Hc Digital on Unsplash

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November 17, 2025November 23, 2025

Can Your Check Size Win You Board-Level Transparency? | Apurva Mehta | Superclusters | S6E8

“A manager doesn’t generally fit into their ultimate quartile until Year 6.”

Apurva Mehta is the co-founding Managing Partner of Summit Peak Investments, a fund-of-funds that boasts a portfolio of both venture fund investments and direct investments, including the likes of Affirm, Anduril, Airtable, Opendoor, and Wish, just to name a few.

Prior to starting Summit Peak in 2018 with his co-founder, Patrick O’Connor, he previously served as Vice President and Deputy Chief Investment Officer for the Children’s Hospital Endowment Portfolio in Fort Worth, Texa. From 2008 to 2011, he was the Director of Portfolio Investments at The Juilliard School in New York City. Apurva began his career in investment consulting and investment banking at Citigroup and Lehman Brothers. He was recognized for his expertise when he was named to aiCIO Magazine’s Top Forty Under Forty in 2012 and 2013 and honored as a Rising Star by Institutional Investor. He holds a BBA in Finance from The George Washington University.

You can find Apurva on his socials here:
LinkedIn: https://www.linkedin.com/in/apurvaamehta/

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

OUTLINE:

[00:00] Intro
[01:40] Tennis
[02:45] Lehman Brothers’ impact on Apurva
[05:28] What AI is missing in investment management
[14:26] Underestimated qualitative metrics that impact a GP’s story
[22:10] Building Cook Children’s Hospital foundation portfolio from scratch
[30:24] Moving quickly as an LP
[31:32] What does Apurva look for in the first meeting?
[37:20] Ugly sweater Christmas parties
[39:56] Apurva’s favorite ugly sweaters over the years
[41:40] Post-credit scene: What does GFW mean?

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SELECT QUOTES FROM THIS EPISODE:

“A manager doesn’t generally fit into their ultimate quartile until Year 6.” — Cambridge Associates

“If everybody’s running the other way—running from the fire, let’s run into it and there’s an opportunity here.” — Apurva Mehta

“When you think about the brand-name firms, they are iconic firms, iconic names. We love the fact that they’re co-invested alongside us. Even if we could build relationships with those firms, we didn’t feel like we’d get the transparency—maybe it was because of our check size, but maybe that’s just because of how they operate—that we needed to go to an investment committee.” — Apurva Mehta

“The transparency at the brand-name firm level is not as high as it is with the kinds of firms we back.” — Apurva Mehta

“Back then, everything was white space, building around network and ecosystems […] It was easier then because the landscape was less crowded. There were 150 backable or quasi-backable seed funds in 2012. 2000 to 3000 now backable and quasi-backable funds in the market. But it was easier then to figure out what we were looking for because it was just brand new.” — Apurva Mehta

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November 13, 2025November 12, 2025

120 BPM

I was on a walk with an LP friend recently around Redwood City. And he told me a remark that another LP had about a mutual investor relations friend we had. That our IR friend started the conversation with, “What are your life goals?” And it alarmed that LP who was meeting our IR friend for the first time. To which, this LP told a few others that he was not only thrown off, but also felt offput by the interaction.

It led to a discussion between my LP friend and I where neither of us, knowing this mutual IR friend, would ever think less of our IR friend because that’s just how this person operates. But to someone who has no context of our friend, it would seem bizarre.

One of my friends who, at one point in time, was a full-time professional DJ, once told me, “The golden number is 120. 120 beats per minute. It’s the rhythm that when you strip all the noise away and you can get a heart to beat that fast, it feels like you’re in flow—flow state. Pure ecstacy.

“But you can’t start the set at 120. If your mix is at that pace, and the heart isn’t, it feels discombobulating. You need to work up to it. Start the set at 70. And over the course of a one- to two-hour set, you work your way up to it. And notice the audience. The crowd must be nodding their head to your beat. And if you ever lose that bob, slow the set down again. And try to catch that heart rate again.”

To this day, probably one of the best pieces of advice on how to hold a conversation I’ve gotten to date. And it was never meant to be so.

A question I get surprisingly often is: “Why did you start the podcast?”

Among many reasons — I get to ask dumb questions to smart people, refine my diligence skillset, get better at asking questions, and so on — one of which was that when I only have an hour and change with someone, I’d rather not spend 10-15 minutes on small talk. How are you? How was the weekend? Which seems to be the LLM that’s coded in us on how to start a conversation and hope eventually, you can get to the meat and potatoes of the conversation. And it makes sense.

To use the DJ analogy above, most people’s resting heart rate is around 60-100. To take the middle of the road, 80. And for busy people who are constantly distracted by meetings and tasks that need their attention, a conversation with a stranger is among the lowest of their priorities. So I always believed that people would be near their resting heart rate when chatting with a nobody like myself. As such, they need icebreakers like “How are you?” to warm them up to the conversation, where their first impression of how you answer that question will indicate where the conversation might go.

On the flip side, most people haven’t been on podcasts. Much less, the guests I aim to have on. LPs. Many typically aren’t given the stage. And even if they are, it’s closed door discussions and private events. Rarely, do they get a public stage. So, the hypothesis was that on average, an LP will most likely be more nervous, excited, you name your fair share of anticipatory emotions jumping on a podcast as opposed to an offline 1:1 conversation. Six seasons in, I’d say we’re pretty close to the mark there.

As such, a faster heart rate means I am often given the privilege of starting the conversation not from “How are you?” but a question closer to 100-110 beats per minute, with hopes we can get into the questions that result in 120+ bpm sooner. And it’s almost always easier to ask a question “for the audience” than for yourself.

“Tell us about the time you proposed to your wife via a billboard. And how does that influence the way you think about pitches today?”

“Half your games on chess.com open with the Ruy Lopez. How do you think about opening gambits when you play white. And how much, if at all, does it influence the way you think about opening a conversation with a GP?”

“How does getting your first day in investment banking postponed, which was supposed to be Sept 11, 2001, influence the way you think about serendipity?”

All questions that I would hesitate to say, would be easy opening gambits in a 1:1 coffee chat. But your mileage may vary.

Photo by Tobias Rademacher on Unsplash

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November 10, 2025November 11, 2025

What does GP-Friendly ACTUALLY Mean? | Caroline Toch Docal | Superclusters | S6E7

“It’s a mathematical reality that the highest performing GPs in this part of the market often also have the highest kill rates, which means some things are incredible and other things are super wonky and you have to be cool with that. You can’t be doing a six across the board.” — Caroline Toch Docal

Caroline Toch Docal backs early stage fund managers as the lead of BCV’s Emerging Manager Program. She believes in investing in funds as early as the first close, which is a rare focus in the LP landscape. She’s a lifelong early stage enthusiast from her time at Venture for America to Techstars to Chief to Dorm Room Fund to now Bain Capital Ventures, where she runs the emerging manager program there which has seen quite the evolution since 2017.

You can find Caroline on her socials here:
LinkedIn: https://www.linkedin.com/in/carolinetoch/
X / Twitter: https://x.com/carolinetoch

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

OUTLINE:

[00:00] Intro
[01:33] BCV Emerge
[02:30] The 13-year summer camp experience
[07:46] From VC to LP
[09:50] Compare/contrast early stage investing to emerging GP investing
[12:51] Behind the scenes of Caroline chose to become an LP
[14:36] Caroline’s first investment
[16:24] What is a GP-friendly diligence process?
[21:27] How Caroline pre-qualifies an investment?
[24:50] Understanding if a GP REALLY believes VC is their life’s work
[26:25] Examples of long-term language
[31:05] The 3 Acts of BCV’s Emerging Manager program
[36:44] What the hell is BGH?
[38:03] Stand up comedy
[39:20] Dogs vs cats

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“One of the things that’s not really talked about in this part of the asset class is everything looks pretty good until you see a lot of stuff.” — Caroline Toch Docal

“Sometimes people use the referencing phase to get to know people they’d want to meet. I don’t believe that is necessarily the most GP-friendly thing to do.” — Caroline Toch Docal

An example ‘long-term language’: “They don’t celebrate fundraising; they celebrate outcomes.” — Caroline Toch Docal

“The average anchor check for a $10-25M fund today is $4.2M. In 2017 when we started, it was less than $3M. So that’s a huge change. Related, the LP base is just concentrating. Using that same size as a benchmark, they have 25% fewer LPs than in 2020.” — Caroline Toch Docal

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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

SELECT LINKS FROM THIS EPISODE:

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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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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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

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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!

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