questions - Cup of Zhou

June 2, 2025June 2, 2025

THE Most Entrepreneurial LP Out There | Narayan Chowdhury | Superclusters | S5E7

“This is one of the big issues of a bunch of data work on venture is insights from some periods don’t mean anything or are not translatable to present time. It’s really frustrating. So we go back to people, reputations, and experience.” – Narayan Chowdhury

Ritujoy Narayan Chowdhury is the co-founder and Managing Director at Franklin Park, where he focuses on private equity investment opportunities, monitoring clients’ portfolios and conducting industry research. He also plays a key role in the development and implementation of Franklin Park’s technology platform, and regularly interacts with clients on investment and portfolio matters.

Prior to Franklin Park, Narayan worked with Hamilton Lane and Public Financial Management. He is a CFA Charterholder and a member of the CFA Institute. Narayan received a B.A. in Mathematics and Economics from Bucknell University.

You can find Narayan on his socials here:
LinkedIn: https://www.linkedin.com/in/narayan-chowdhury/
X / Twitter: https://x.com/RNC76

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

OUTLINE:

[00:00] Intro
[02:27] Why my parents moved to the US
[03:43] Narayan’s dad
[08:54] The friction that Narayan has with his team
[11:59] Why current analyst training creates bad habits
[15:00] What Narayan does when his family goes to bed
[16:37] When did Narayan first start playing with code?
[17:34] Narayan’s entrepreneurial origins and how much he got paid
[19:54] “Never sit alone at lunch”
[22:54] The Mike Maples story
[25:48] When Narayan realized VC is very different from PE
[30:05] The difference between underwriting VC and buyout
[34:28] What do you do when you’ve pigeonholed yourself in one industry?
[37:02] How do you know if a GP is a core part of an alumni network?
[38:32] A 2025 micro trend of misleading operating metrics
[43:40] How has VC changed in the past few decades?
[53:58] What do most people underappreciate about hockey?

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Every moment that [my daughter] is here and I’m not with her is a moment we’ll never get back.” – Narayan Chowdhury

“Every action should not be a wasted action, should not be duplicative, should be the best use of a person’s time. So any tool that we build that is contrary to that should be reevaluated constantly.” – Narayan Chowdhury

“What do you do when you don’t know anything, you haven’t met anybody, you have no context, the human brain starts inventing rationale.” – Narayan Chowdhury

“Never sit alone at lunch.” – Alan Patricof

“Looking backwards on track records in venture can be very scary decisions. It could be that the prior funds were completely passive throw-ins on a cap table where they were following some social cues in a ZIRP environment and perhaps they got lucky. Whether they were part of a giant outcome [or not], it sort of meaningless for the future because neither the syndicate nor the founder really know who that person ever was. And so, the go-forward benefit of that investment decision is zero versus ‘We were the trusted investor for that founder.’ Not all prior track records are the same. We have to go back to why, going forward, are founders going to seek out or accept those dollars.” – Narayan Chowdhury
*ZIRP: zero interest-rate policy

“I’d rather go bankrupt than lose this AI race.” – Larry Page

“The problem is that the barriers to entry on that strategy [to deploy a lot of capital] are pretty low. And you get killed – death by a thousand cuts – when you’re not the only one trying to flood the market with capital and outcompeting on price.” – Narayan Chowdhury

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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.

May 30, 2025May 30, 2025

The Danger of Pivots

Mike Maples Jr. once said that 90% of Floodgate’s exit profits come from pivots. Hell, 50% of my angel investments have pivoted from the idea I first invested in. Pivoting is a constant norm of the entrepreneurial ecosystem. Many investors know it’ll happen. Great founders instinctually prepare for that possibility. Being married to the problem, not the solution is the direct reflection of what it means to prepare for pivots. By definition, Meriam Webster defines the word as:

pivot (n) – a usually marked change, especially an adjustment or modification made (as to a product, service, or strategy) in order to adapt or improve

As such, small feature improvements, changes and additions, even omissions rarely count as one. But a large product shift, where the core product is no longer the product you once sold, is one. In general, the common advice on the street is that you should embrace pivots, until you find product-market fit. But also knowing that you can always lose product-market fit, even after you obtain it. A pivot should either help you catch lightning in a bottle, or help you keep lightning in the bottle.

But that’s not the purpose of me writing this piece. It’s about the opposite. The quiet thing no one explicitly talks about when it comes to pivot. The TL;DR version is each time you pivot, you lose trust. You lose trust because you didn’t have conviction in your product. You lose trust because you didn’t have conviction on where the market will go. Hell, you lose trust because you didn’t do what you said you were going to do. You were not a person of your word. You lose trust because you made someone else lose trust. Because of you, they looked stupid. To their peers. To their bosses. Sometimes to their friends.

Once you lose trust, it’s really, really hard to get it back, if at all. In the age of information excess and product surplus, you won’t have the time or the attention from your customers to rebuild that trust. They’ll just move on to the next solution.

Slow Ventures’ Yoni also recently tweeted:

“Pivots almost never work:

You need an actually good idea. These are rare and hard to come up with in real time.
You need resources sufficient to test it. You’ve already spent much of the money you raised.
You need the energy and excitement to keep going RIGHT NOW. Struggling is exhausting and you’ve been struggling for a long time.”

You don't your investors (or yourself) a pivot.

We make a deal about spending money to prove/disproven something. Once you've done that (even if the answer is "false") your obligation is done.

You held up your side of the bargain. pic.twitter.com/BuJ7tT5wbt
— yoni rechtman (@yrechtman) May 27, 2025

All of which are true. But many truly great companies, as we know them today, have gone through their pivots. The idea that put them on the billboard was not the idea that was first funded. Instagram. Google (not their initial business model). Slack. Twitch. Lyft. Shopify. The list goes on.

That said, if you want investors who haven’t funded you to fund you after the pivot, you need a damn good reason as to why you’re doing so. And why it makes sense.

If you’ve known these investors for a while, great! You already have the pre-requisite of trust. You need it. The age of AI wrappers getting thrown left and right and startups going through their 28th pivot destroys trust. How do I know this is the one? How can I believe you when you say this is the one? Why should I have faith when you say this is the last time? There’s a great recent Hiten Shah tweet on this I really like, albeit from the customer perspective, but the analogy holds.

I just got off the phone with a founder. It was an early Sunday morning call, and they were distraught.

The company had launched with a breakout AI feature. That one worked. It delivered. But every new release since then? Nothing’s sticking.

The team is moving fast. They’re…
— Hiten Shah (@hnshah) May 25, 2025

“Once belief slips, no amount of capability wins it back.

“What makes this worse is how often teams move on. A new demo. A new integration. A new pitch. But the scar tissue remains. Users carry it forward. They stop expecting the product to help them. And eventually, they stop expecting anything at all. This is the hidden cost of broken AI. Beyond failing to deliver, it inevitably also subtracts confidence. And that subtraction compounds.

“You’re shaping expectation, whether you know it or not. Every moment it works, belief grows. Every moment it doesn’t, belief drains out.

“That’s the real game.”

Just as with customers, it is with investors. Although investors can be more forgiving, knowing that this is part of the game. But no amount of faith is infinite, so choose how you voice your actions intentionally. Choose your interactions carefully. And if you do choose to interact, communicate proactively and deliberately. Notice how many withdrawals you’re taking from the bank of social capital, from your karmic bank account. And don’t forget to regularly deposit.

Photo by Bambi Corro on Unsplash

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May 26, 2025May 26, 2025

How to Bet on the Underdog | Matt Curtolo | Superclusters | S5E6

“The bigger you get, the more established you get, the more underwriting emphasis goes into how this team operates as a structure rather than is there a star?” – Matt Curtolo

Matt Curtolo, CAIA is a seasoned private markets investor and allocator with over two decades of experience at leading financial institutions. Throughout his career, he has been directly responsible for allocating more than $6 billion in commitments to private market investments and maintains relationships with hundreds of general partner relationships across the full spectrum of private capital strategies.

Most recently, as Head of Investments at Allocate, a venture-backed fintech startup. Matt built the investment capability from the ground up, broadening access to top-tier venture capital opportunities for the private wealth market. Prior to this, he served as a senior leader at MetLife, serving on the investment committee, co-managing their global alternatives portfolio and leading the firm’s US Buyout portfolio. Earlier in his career, Matt led all private equity activities as Head of Private Equity at Hirtle Callaghan, a large independent outsourced Chief Investment Officer (oCIO). Matt’s foundational experience was gained at Hamilton Lane during its early growth phase, before it became the world’s preeminent private markets allocator, in research, investment and client-facing roles. Matt currently holds several advisory positions that span start-ups, asset management firms and fund of funds. He also manages his own advice practice, providing GPs with strategic guidance on strategy, fundraising and investor relations.

You can find Matt on his socials here:
LinkedIn: https://www.linkedin.com/in/matt-curtolo-caia/

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

OUTLINE:

[00:00] Intro
[04:24] What town did Matt grow up in?
[04:37] Why is that town significant from a sociological perspective?
[08:43] Why is Matt fascinated with the Detroit Lions?
[11:08] What is it like cheering for the underdog?
[13:02] How does Matt break down deal attribution in partnerships?
[18:04] GPs’ karmic bank account
[21:29] What is the kindest thing anyone’s done for Matt?
[23:24] How did tennis enter Matt’s life?
[26:35] Historical examples of VC management/leadership structures
[29:33] Underwriting track record between senior and junior investors
[32:23] How Matt approaches diligence after reading the data room
[39:30] How do you know when you’ve asked enough questions?
[42:37] The three classes of questions for GPs that influence investment decisions
[45:34] Remote culture
[50:16] Cadence of in-person gatherings in remote teams
[52:48] The two (and a half) types of conversations to always host in-person
[58:37] The last great idea Matt had on a walk
[1:02:05] The legacy Matt wants to leave behind
[1:04:37] Post-credit scene

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Partnerships are incredibly hard to evaluate because not only are you evaluating each of the individual’s capabilities independently, but is it a one plus one equals three situation?” – Matt Curtolo

“The bigger you get, the more established you get, the more underwriting emphasis goes into how this team operates as a structure rather than is there a star?” – Matt Curtolo

“Data gives me questions, not answers.” – Matt Curtolo

“The dopamine you get from planning something versus the actual experience itself are wildly different.” – Matt Curtolo

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!

May 21, 2025May 21, 2025

On Writing

I’m not a good writer.

As a kid, I wrote poetry because it was easier to express myself in short form than long form. I also used to start writing fictional books, but stop after chapter one because I didn’t know how the story would develop. I was also the kid who would find five different ways to say the same thing in grade school, just so that my essay would hit the page limit. Yet still, my lowest grades among any subject was still English, particularly writing.

David Ogilvy, the namesake for the legendary advertising firm, Ogilvy & Mather, now just Ogilvy, once said: “Woolly minded people write woolly memos, woolly letters and woolly speeches.” The truth is I was, probably still am, a “wooly minded person.” But I try to be better.

That was the genesis of this blog. I didn’t have grand hopes of becoming famous. Or that I was going to make a career out of this. Still so, as it is still the reason why I haven’t said yes to any sponsors to this blog.

I write to think. I write whatever comes to mind. Simply, I write what I want. In fact, when the fact I have this blog comes up in conversation, I still actively tell me to unsubscribe. This isn’t an LP blog. Nor a VC blog. Nor a startup blog. It’s just my train of consciousness. Something I commit to every week. So, I’m extraordinarily honored to have a few thousand of you read this on a regular basis.

Thank you.

I don’t say that enough on this blog. But to all of you reading, I am deeply grateful you’re on this journey with me.

But… over the years, people have said I’m not as bad as I say I am at writing. Which might be true. We are all, after all, our own harshest critics. While I’m nowhere near the level of David Ogilvy or Brandon Sanderson or Maria Popova or Neil Gaiman or Susan Cain, in case it might be helpful, here are the gentle reminders I give myself when it comes to writing:

Write as I talk. Incomplete sentences. One word sentences. Short, easy words occasionally sprinkled in with a $10 word I like. Tenacious. Idiosyncratic. Judicious. And yes, I’m conscious that I use ‘bandwidth’ instead of ‘time.’
Write only when I’m inspired to. I don’t have a strict regimen of writing. I’ve met authors who have four-hour morning writing routines. I don’t. This is not my full-time job. But I enjoy writing. And I’m not publishing daily. I’ve committed to weekly. That affords me an immense amount of latitude for ‘productive time to be bored.’ I’m more often inspired by ‘touching grass’ as the kids call it than I am staring at my monitor or journal.
In case I’m on a deadline and I’ve been uninspired up till the deadline, I have a very specific doc I reference. The metaphorical ‘break glass in case of emergency.’ It’s called the Emotion Catalogue. In it, I’ve tracked every single time I’ve consumed a piece of information that led to a specific emotional reaction. Happiness/joy. Sadness. Regret. Guilt. Jealousy. Anger. Inspiration. Fear. Creativity. Not sure if the last one is an emotion, but to me, it is. And if I’m supposed to write about a certain emotion, I need to feel that emotion. So I go to that catalogue, pick one or two of the inspirations within a section. And I consume it. Read it. Watch it. Listen to it.
Use productive time to edit. Use inspired time to write. For me, that’s usually (not always) writing in the evening. And editing in the morning.
I ‘idea-journal’ every day. If I can’t think of a new idea to write on, the journaling prompt I have to answer, “What is the most important question I should be asking myself today?” or “What did I really not want to do today? Why?”
Write for one person. You. Or for me, the person I was yesterday. I am always guaranteed one happy reader. But also, if it’s helpful for me, there’s a good chance I’m not alone. And it’s helpful for someone else out there as well.
Rewrite things often. The first idea is usually not the best, nor is it the most refined. Even if it’s five years from now.
Be comfortable with dropping ideas. Sometimes I’m motivated to write something, but I lose motivation halfway through. Instead of making it homework for myself, it’s easier to mentally drop it. This is different from ideas I’m still motivated to write about, but can’t find the right concepts or words to put it into play. Those I mull over for a while. Sometimes, years.

Photo by Yannick Pulver 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!

May 19, 2025May 19, 2025

You’re Looking at Networks Wrong | Albert Azout | Superclusters | S5E5

“Networks are more persistent than performance.” – Albert Azout

Albert Azout is the Co-Founder and Managing Partner of Level Ventures, a technology investment firm built on software and data science and invests in both entrepreneurs and venture capital managers, including the likes of Air Street Capital, Emergent Ventures and Work-Bench, just to name a few. Prior to Level, Albert has been a serial founder, starting analytics businesses and even a social media company before Facebook.

You can find Albert on his socials here:
LinkedIn: https://www.linkedin.com/in/albertazout/
Substack: http://albertazout.substack.com/

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

OUTLINE:

[00:00] Intro
[02:36] The origin of Albert’s blog
[04:45] How did Albert first start coding?
[07:43] Albert’s interest in networks
[13:10] Entrepreneurship around Albert
[16:27] What is collaborative filtering?
[22:18] How complexity economics affect the networks of VCs?
[27:14] Fear and greed regimes
[28:51] Telltale signs that inform the kind of regime you’re in
[30:31] Why it’s the wrong time to be investing in defense tech
[34:53] What are most LPs missing about GP networks?
[37:31] How is Level Ventures looking at networks differently?
[44:42] Archetypes of GPs that Albert likes
[46:43] The 3 advantages GPs need to have
[55:02] How does Albert balance over- vs under-diligencing?
[57:15] Albert’s view on luck
[57:47] Albert the “consciousness expert”

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“You have to have an understanding of the regime you’re in for you to make good decisions as an investor.” – Albert Azout

“Price reflects the inefficiencies of the market.” – Albert Azout

“What really matters is what you’re hearing around you. When you hear overly coherent narratives, that’s a big thing for me. And it happens in subcycles as well. […] But when people are behaving and making decisions based on narratives that are overly coherent, that’s a big sign. That’s a very social problem.” – Albert Azout

“What you want to see in a venture company which you’re looking for huge outliers, is you want to see increasing returns to scale. You want to see demand-side feedback loops, where you have very low marginal costs of distribution. And that requires mostly winner-take-all, or winner-take-most kinds of markets.” – Albert Azout

“You want to be pre-narrative. You want to position your capital in an area where the supply of capital increases over time and where those assets will be traded at a premium.” – Albert Azout

“Networks are more persistent than performance.” – Albert Azout

“Venture is simple but hard.” – Albert Azout

“We look for GPs who have one, a network advantage and two, a knowledge advantage – both of which have to be not redundant and economically important. And the third thing is the fund strategy itself. There’s a lot of nuances but there are two things that are important. One is that it has to be an outlier. […] It has to have the right construction for us. […] My second point is more important. It involves game theory, which is the competitive dynamics in the market. ” – Albert Azout

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!

May 12, 2025May 12, 2025

When an Olympic Daydreamer Becomes an LP Whisperer | Asher Siddiqui | Superclusters | S5E4

“What I hear from LPs is that the market is important. And of course, the market IS important. And I think that that’s true. But if you truly believe in venture as a purist, then all of it is irrelevant because at any point in time, someone will come and have this unique insight. And the timing is against them. The world is against them. They’re in the wrong place at the wrong time, and yet, they have this unique insight at this point in time. They have the opportunity to invest at this point in time. And so, just because the timing is wrong doesn’t mean you shouldn’t be backing them. Because they might be right. And you might be missing out on the best opportunity in your lifetime.”

Asher Siddiqui is a global tech investor, M&A dealmaker, and venture fund builder with over 25 years of hands-on experience across venture capital, entrepreneurship, and more than $15B in executed M&A transactions.

He began his career as a software engineer and entrepreneur in the US and UK before spending a decade leading M&A and corporate venture at Etisalat Group (now e& Group), one of the world’s largest listed TMT investment groups. There, he led acquisitions, exits, and strategic transactions across multiple continents.

In 2016, Asher joined the global leadership team at 500 Startups in San Francisco, helping scale the platform to $2B+ AUM, with a portfolio that includes 35+ unicorns and 160+ centaurs.

Since then, he has helped launch and scale several institutional VC firms—including Race Capital, Lumikai, Sukna Ventures, Zayn VC, and Humanrace Capital—and serves on the advisory boards of funds such as FootPrint Coalition Ventures, Merus Capital, and The Treasury.

To date, Asher has made 100+ venture investments (both direct and LP), raised hundreds of millions in LP commitments, mentored hundreds of emerging VC managers globally, and advised countless founders.

You can find Asher on his socials here:
LinkedIn: https://www.linkedin.com/in/ashersiddiqui/
X / Twitter: https://x.com/ashercdkey

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

OUTLINE:

[00:00] Intro
[03:36] Why doesn’t Asher like the saying ‘The sky’s the limit?’
[07:20] The launch of CNBC Africa
[15:25] How do two competing personalities create one of the largest media empires in the world?
[17:39] Combining vision and execution
[21:22] Asher’s framework for executing on a vision
[31:00] Why Asher was the youngest Global Head of M&A of a major telecom business
[43:57] What sets a great investor apart from a great fund manager
[45:27] Roleplaying a GP thinking about secondaries
[51:44] What do most LPs underestimate and overestimate
[58:24] Most telling predictors of outperforming GPs
[1:07:13] The best wine and food for each situation
[1:12:25] Asher’s Vinod Khosla story

SELECT LINKS FROM THIS EPISODE:

The Non-Obvious Emerging LP Playbook
500 Global
Sukna Ventures
Race Capital
Footprint Coalition
Robert Downey Jr.
SHUAA (formerly known as Abu Dhabi Financial Group)
e& (also known as Etisalat)
CNBC Africa
Carl Sagan
Zafar Siddiqui
Rakesh Wahi
Dubai
Johannesburg
Forbes Africa
Lancaster University Ghana
KPMG
Michael Phelps
McKinsey & Company
“‘There’s something happening here. But what it is ain’t exactly clear.’ –Buffalo Springfield, For What It’s Worth”, a December 2024 Stepstone report on the venture market
Jensen Huang
University of Michigan
Rioja wine
Pinot grigio / gris
Vinod Khosla
TechCrunch Disrupt SF 2011
Kleiner Perkins
Khosla Ventures

SELECT QUOTES FROM THIS EPISODE:

“The best opportunities are the opportunities that aren’t obvious to anyone.” – Asher Siddiqui

“Execution is nothing without a vision, and vision is nothing without execution.” – Asher Siddiqui

“If only there was an Olympic sport called daydreaming, then Asher will be a gold medalist every time.” – Asher Siddiqui’s mom

“What was less relevant was the number; what was more important was the process.” – Asher Siddiqui

“If you ask the baseline obvious questions, you get the obvious responses.” – Asher Siddiqui

“You have to be thinking about exits because if you’re so laser-focused on building your portfolio and not thinking about exits, then maybe you’re a great investor, but not a great fund manager.” – Asher Siddiqui

On investors selling secondaries… “You may choose to take some off the table. And this is a market risk, not a specific lack of belief in the founder. I cannot tell you what the right answer is. What I can tell you is what I’m interested in backing are fund managers that are in the pursuit of truth, and they’re making the best judgment calls in the pursuit of truth that they can at this point in time, based on the data they have available.” – Asher Siddiqui

“There is no right or wrong answer. Because you may get it right this time – you may get it wrong this time – what matters is-… This is Fund III, right? What about Fund VI or Fund VII or Fund VIII? Are you building a culture for you to continue to build a team that has this culture to continuously follow and pursue this pursuit of truth for the best outcomes based on the process that you have, as opposed to just shooting from the hip and gut instinct, which is great while you’re around. But when you retire and your firm’s going on, you’ve basically created a culture where people shoot from the hip and maybe the people who come after you are not as good as you.” – Asher Siddiqui

“Exiting a position in a company to return DPI to LPs is not a reflection of your stance on the company, but your stance on the market.” – Asher Siddiqui

Why LPs should go to annual meetings… “I’m looking for a minimum of one insight that I can take away, and I’m hoping to ask one intelligent question that will stand out as a credible LP in the minds of the GP.” – Asher’s Swedish pension allocator friend

“So, when I hear people talk about scaling venture, what the fuck are you talking about? Venture is not scalable. There are things that you can scale. There are processes that you can scale. But ultimately, you still have to rely upon finding those people and finding them at the right time – and the right time could be the ‘wrong’ time – but finding them when they find that opportunity and when they see that meaningful insight. I’ve heard people say it’s not thesis-driven; it’s market-driven. No, I disagree. I think it’s both of those. But actually it’s individual-driven if you can find that person.” – Asher Siddiqui

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!

May 5, 2025May 5, 2025

Why Individuals Can Be Better than Teams | Sean Warrington | Superclusters | S5E3

“Some of the best investments, as we look back in history, were never obvious at the moment the investments were made. You may not have to be contrarian, but you have to have a variant perception than the rest of the market. Maybe you saw the team differently. You saw the space growing differently. That, to us, inherently, is a single decision maker-type thought process at the earliest stage, when it’s less about metrics. It’s more about how you evaluate the talent and the team.” – Sean Warrington

Sean Warrington leads private market investing at Gresham Partners, a $10 billion multi-family office based in Chicago. Known for being a transparent and user-friendly LP, he and the Gresham team aim to simplify the fundraising process — offering single-check investments, a streamlined diligence process, and prompt, candid feedback to GPs.

You can find Sean on his socials here:
X / Twitter: https://x.com/srwarrington
LinkedIn: https://www.linkedin.com/in/srwarrington/

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

OUTLINE:

[00:00] Intro
[03:29] Who is Jeff French?
[05:26] The metrics for success for a junior LP
[07:20] The 3 chapters of Sean’s evolution as an LP
[11:05] Sean’s first investment
[14:44] When GPs put LPs on strict timelines
[16:53] One archetype of GP that Sean is excited about
[19:37] What it looks like to be thoughtful when growing AUM
[23:16] What most LPs don’t understand about solo GPs
[25:58] What happens when a GP leaves a partnership
[27:33] The definition of LP/GP alignment
[30:47] Reference archetypes and how to find them
[35:32] How to manage bandwidths in a small team
[38:58] Frameworks for taking calls
[42:26] How much does Sean travel?
[43:25] Why coffee chats don’t work
[45:30] What Sean’s changed his mind on about investing
[47:12] What did Jason Kelce’s retirement mean to Sean?
[49:36] Post-credit scene

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“If you’re 60-70% of the time picking good managers, I think you’re pretty good at this industry.” – Sean Warrington

“Frameworks are not foolproof. What they’re designed to do is help us focus on places where we can get to an eventual yes.” – Sean Warrington

“We don’t want a slow no. A slow no is bad for everybody.” – Sean Warrington

“One thing LPs are bad at remembering is we are exceptionally diversified investors. For us, to have anything even be 1% – even a manager being a single percent of the overall pool of capital – is very difficult to do. Many times we’re talking about basis points.” – Sean Warrington

“The big risk that LPs don’t appreciate… There’s this view that these two- and three-person teams coming together create this better judgment. What they’re not factoring in is that these are somewhat forced marriages. These are people who may or may not have long histories together. They may not have great bedside manner when they’re in the thick of it.” – Sean Warrington

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!

April 30, 2025April 25, 2025

Happiness

I had a number of people ask me what I’m doing next. So I told them.

One of the key pillars of what I am doing now is content. It’s why I write this blog. It’s why I produce Superclusters. It’s why there are a few new projects I’m working on that will shed light to this opaque world in which we’re in. Particularly in venture. In the allocator world.

I don’t hold anything back. There are no other cards I’m hiding up my sleeve. When a friend, an acquaintance, a stranger ask me how I do something, I tell them. Unfiltered. Without restraint. Without reservation. Without hesitation.

And for some reason, recently I’ve had more people ask me why. “What’s in it for you?” “What’s your master plan?” “Do you make more money this way?” “Why not just do X?” “You know you can get people to pay you a lot of money for this.” “Aren’t you afraid of being obsolete?”

Some questions come from a place of fear. Others, a place of greed. None of it from a place of joy.

There’s nothing in it for me, except for one thing. If I can help one more person not fall through the pitfalls I went through, or help one more person live a more meaningful life, or help one more person smile, I’d do it in a heartbeat.

There’s a great line I remember watching in the show After Life. “Happiness is amazing. It’s so amazing it doesn’t matter if it’s yours or not. A society grows great when old men plant trees the shade of which they know they will never sit in.”

I just want a better world. I want to make people happy. And I don’t care if it’s my own. But making another person truly happy makes me happy.

Whether you believe me or not, that’s up to you. But that’s all I have to say.

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!

April 28, 2025April 28, 2025

You’re Doing Diligence Wrong | Raviv Sapir | Superclusters | S5E2

“Most references will not give a negative reference about someone, but you will have to understand and listen between the lines. What is a good or a bad reference? They might say, ‘I really like him as a person. He’s really nice.’ But this is a person that’s worked together with you in a team, and you’re not saying he’s great with founders or finding the best deals. Maybe he’s not that good.” – Raviv Sapir

Raviv Sapir is an early-stage investor at Vinthera, a fund of funds and venture firm with a hybrid strategy that combines VC fund investments with direct startup investments. With a background in tech and finance, an MBA from HEC Paris, and years of experience mentoring startups and supporting LPs, Raviv brings a sharp eye for high-conviction opportunities and a practical approach to venture. He previously held product roles at leading Israeli startups and served in a technological unit within the Israeli Defense Forces. His work across geographies, sectors, and investment stages gives him a uniquely holistic and global perspective on the venture ecosystem.

You can find Raviv on his socials here:
LinkedIn: https://www.linkedin.com/in/raviv-sapir/

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

OUTLINE:

[00:00] Intro
[03:31] Swimming since he was 7
[09:49] Breaking down each GP’s track record and dynamics in a partnership
[11:25] Telltale signs that a partnership will last
[12:50] An example of questionable GP dynamics
[21:45] Virtual partnerships
[25:43] GPs working out of coworking spaces
[28:30] Commonly held LP assumptions
[32:16] A big red flag GPs often say
[34:27] What does Raviv look for during reference calls?
[39:41] How does the diligence change for a Fund I/II vs Fund III/IV?
[42:26] Qualitative traits Raviv likes to see in a Fund I GP vs Fund II+ GP
[44:04] Ideal cadence of reporting and LP/GP touchpoints
[46:03] Role of the LPAC across different funds
[48:47] Diligence as a function of check size
[54:37] What’s Raviv’s favorite episode of Venture Unlocked?
[56:23] The podcasts that Raviv listens to

SELECT LINKS FROM THIS EPISODE:

SELECT QUOTES FROM THIS EPISODE:

“Some of the small funds perform better but a lot of them–… they perform much worse because the variance in their performance is so big. You might have good odds of succeeding with a small fund but very high odds of performing way worse than the bigger funds.” – Raviv Sapir

“GPs are great at selling. ‘Every time is the best time to invest.’” – Raviv Sapir

“Most [references] will not give a negative reference about someone, but you will have to understand and listen between the lines. What is a good or a bad reference? They might say, ‘I really like him as a person. He’s really nice.’ But this is a person that’s worked together with you in a team, and you’re not saying he’s great with founders or finding the best deals. Maybe he’s not that good.” – Raviv Sapir

“‘Interesting’, especially in the US, is used in a negative way.” – Raviv Sapir

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!

April 24, 2025April 24, 2025

#unfiltered #94 Is Conviction Black and White?

I’ve heard a collection of sayings around conviction.

“Do or do not; there is no try.” Yoda.

“Get to 70% conviction. 90% means you’re too late. 50% means you haven’t done your homework.” Keith Rabois.

“Do half-ass two things; whole ass one thing.” Ron Swanson.

But the one that stands out the most is: “You either believe or you don’t.” Which I’ve heard many an LP tell me on the podcast. But also across VCs I’ve met over the years. And in full transparency, I struggle with that. Theoretically it makes sense. Building 99% of a car still means you don’t have a working car. There are a thesaurus of synonyms alongside, “I just don’t believe in you.” We’ve all heard it.

“You were an amazing candidate, but unfortunately, the talent pool was really competitive and we decided to move on with someone else. But please do apply again for a job that may be a better fit for you.”

“It’s not you; it’s me.”

“We’re just in different chapters of our lives. And we deserve to meet someone who is where we are.”

“You’re too early for us.”

“You’re out of scope.”

“I just have too much on my plate now, and I just don’t have the bandwidth to focus on this now.”

“Let me run this by my hiring/investment committee/leadership.”

All that just mean “I don’t believe in you.” (But it makes me feel like an asshole if I said it directly to your face. And I don’t want to be perceived as an asshole.) Ashamedly so, I’ve used a few of these myself.

In the investing world, I wonder if there are varying levels of conviction. Phenotypically expressed in varying check sizes. In fact, we have terminology for it now. Core checks. And access checks, or discovery checks, or simply, non-core checks. A core check is a substantial position. A meaningful percentage of the overall fund size. At least 1%. But depending on the portfolio construction, it varies from 1-5% of the fund. A discovery check, on the other hand, is smaller. Oftentimes, less than 0.5% of the fund size. Dipping one’s toes into the water so to speak, as opposed to a headfirst dive or a cannonball to extend the metaphor.

But if conviction really is black and white, should there be varying levels of conviction? Is there such a thing as believing in someone, but only half as much? Or a third as much as someone else?

Moreover one of the greatest lessons we learn over time as investors is that we’re quite terrible, over large sample sizes, with predicting winners out of our portfolio. The three to five biggest winners that put you on the roadmap are often not our three to five “favorite” investments ex ante.

A really good friend of mine once told me (mind you, that both my male friend and I are heterosexual), “The conviction you have in someone to be your girlfriend is different from the conviction you have in someone who is to be your wife. You build that trust over time. And what you look for is different over time.”

So back to the original question: Is conviction black and white? Is there really only belief and disbelief? Is there such a thing as I kind of believe? Or I believe but…?

While I don’t have a black and white answer to this black and white question, I’m inclined to believe yes. It is black and white. It just depends where you put the bar. The bar for you to date someone is different from the bar for you to marry someone. The bar to approve an investment to return a $10M fund is different from the bar to return a $1B fund. And, the bar to invest in an asset in a power law-driven industry, like venture, is different from the bar to invest in an asset in a normally-distributed industry, like real estate or public markets. What’s black for one is white for another.

Photo by Jan Kopřiva on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

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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