Columbia sent me a book before I ever set foot on campus. Homer’s Iliad, in the mail, over the summer. I remember thinking, with real optimism, that this was how it was going to work from here on out. They were just going to send us our books.

They did not send us our books. That was the only one.

But you were supposed to read it before you arrived, because the first day of Literature Humanities (Lit Hum IYN) was not a syllabus review. It was a discussion.

I walked in ready. I had done the reading. I was in college now, I was taking this seriously, and I had the distinct sense that the whole thing was going to be a breeze because I was putting in more effort. The professor, a grad student, asked a question. I do not remember the question. I remember my hand going up high and straight, the way it does when you want to be picked. He pointed at me. I gave my answer.

He said, “No.”

Then he moved to the next person.

I did not speak in that class again for two or three weeks.

What that “no” installed in me was a rule I did not choose and could not see. I have to be a thousand percent sure I am right before I open my mouth.

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The last time Chris Schelling was on the show, the episode carried a title I still think about: Private Detective to Private Investments. He is back, and the seat has changed. Chris recently made the move to Aksia as a Managing Director, which hands him the kind of cross-asset vantage point over private markets that most of us only get to guess at. Alexa and I took full advantage.

What struck me this time is how much of the AI conversation happened on the allocator’s side of the table. Everyone asks how AI changes the companies we underwrite. Chris is just as interested in how it changes the underwriting. He gets into using AI for diligence and memos, training analysts with it as a kind of behavioral coach, and what it would actually mean to seat an AI agent at an investment committee. That last one sounds like a bit until you hear him walk through it.

On the bubble question, Chris threads it the way only someone who has lived a few cycles can: “You can have a bubble without true technological disruption occurring.” Both things get to be true at once. The technology is real. The prices can still be wrong. And he applies the same discipline to the fashionable short thesis of the moment: “It’s not legacy SaaS goes boom. Like that’s way too simplistic.”

Then there is the section I suspect people will replay. Chris walks through SPV sandwiches, layers of access stacked on layers of fees, and why the structure rhymes uncomfortably with 2008. He even sketches the start of a checklist for evaluating SPVs and the access claims that come with them. I will not spoil it here. If you have wired money into an SPV in the last couple of years, that stretch alone is the episode. Nick Cassin, who heads Sidley’s secondaries practice, joins the episode as well, and the back half moves through how the mega RIAs are building private markets platforms and what product diversity across the wealth channel actually requires.

The line I keep coming back to is the one Chris lands near the end: “In a world of AI tools, differentiated relationships, networks, and deep domain expertise matter more than ever.” If you read The Delusion Requirement last week, you can guess why that one stayed with me. The tools are getting evenly distributed. The human parts are not.

If the show has been useful to you, the best thing you can do is leave a rating and review wherever you listen. It matters more than most people realize.

with gratitude,
earnest

I’ve had one improv class (maybe two) in my life, usually at a Kauffman Fellows module. There is a rule they teach you in the first week of improv, before you are allowed to try to be funny. Two people walk onto a bare stage with nothing. No script, no set, no idea where any of it is going. The first person makes an offer, and it is usually a bad one. The scene does not survive on the quality of the offer. It survives on whether the second person accepts it and adds something. Yes, and. I’m sure you have heard of it. The moment somebody blocks, corrects, or waits for a better scene to arrive, the whole thing dies where it stands.

I have been thinking about that rule since Santosh Sankar and I sat down to record the first three episodes of Carry On. Santosh opened with the math. Over the last couple of years, something like 75 percent of everything LPs put into venture went to the top thirty funds. Everyone else, and that is not just emerging managers, that is everyone else, split the quarter that was left. Then he asked the question the math begs for: why would anyone start a venture fund right now?

My answer, on the record, was that you have to be delusional. Not kind of delusional. Definitely delusional. And I meant it as a compliment, because delusion is the exact trait we screen for in founders. Someone who can see every problem in front of them, assess all of that information honestly, and still expect to be the exception. We ask founders to carry that contradiction every single day. Starting a venture firm is just finally taking your own medicine.

Santosh has a story about this. A few years into building Dynamo, his wife looked over at him and asked, casually, so you think this is going to work? Then she answered it herself: what a dumb question. Of course he believed it was going to work. Why would he be doing it otherwise? Your self belief is a different thing from the actuality of what happens. Holding both of those at once is the job.

But delusion alone is not a strategy. It is noise with confidence. The thing that has to sit underneath it is a why, and this is where the episode got uncomfortable in the useful way. An allocator friend of mine recently passed along what another allocator told her: she needs one more venture firm the way she needs another bullet in the head. That is the room every new manager is walking into. Your why is not marketing copy for that room. It is your right to exist in it.

Differentiation is the same conversation wearing a suit. It is the word we all use and never define, and as this industry matured it collapsed into a sterile monoculture: identical websites, identical value add, identical posts, everyone quietly afraid that the tallest flower gets cut. Real differentiation is not a slide. It is the compounding of all the small ways you approach the craft differently. A 24 hour response rule. How you actually run diligence. What you still do for a founder in month nine that you promised in the first meeting. Most of us are some shade of blue. The work is knowing exactly which shade you are and saying it out loud.

We also get into the part I keep having to relearn: none of this works if you wait to be perfect. Somebody prominent in this business, I heard it secondhand so I will not name them, said the optimal level of cringe is not zero. The best firms right now, as Santosh put it, operate like media companies with investment capabilities attached, which means the reps are public, and some of the reps are bad, and the bad reps are where the feedback lives. That is improv again. You do not get to workshop the scene in private first.

There is more in the episode than I can carry into one essay. Sam Heshmati of Citizens Private Bank joins in the middle and traces the white glove lineage from First Republic, which is itself a case study in a why surviving a change of jersey.

So here is the ask, same as last time, because it worked. Listen to the episode. Then tell us where we got it right and, more usefully, where we did not. Reply to this post, comment wherever you listen, or send me a note directly. If there is a question about this craft you think two GPs owe you a straight answer on, that is how episodes get made.

The cards are stacked. The scene starts anyway. Yes, and.

Grateful to AngelList, WilmerHale, KPMG, and Citizens Private Bank for backing this from the start, and to the Heard Media team for turning two people talking into something worth your time.

with gratitude,
Earnest

Listen on your favorite platform.

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• Full episode page

A few weeks ago I got on a call with a founder friend of mine who spends most of his waking hours actually building things. He is a universe of technical depth ahead of me, and the whole reason I asked for his time was that my agent setup, which I had cobbled together over the last several quarters, had started to feel clunky in a way I could not diagnose. Too many gears, not enough grip.

About fifteen minutes in, he stopped me and said this:

Friend: So question. Because it’s going to help me identify, like, how I talk to you about this. How technical are you on, like, elements and agents?

Me: I’m just like a self-taught. I’m not that technical. I actually don’t.

Friend: Do you know what a sub-agent is? Do you know what an agent harness is?

Me: No.

Friend: Do you know what a system prompt is?

Me: A system prompt?

Friend: Yeah.

Me: No. What is that? I’m awful. I’m not technical at all.

Friend: Yeah, I know. Yeah, I’m just trying to gauge, like, what terms I can use and not. What about, like, a context window? Tokens?

Me: Yes.

Friend: Okay, damn. So, okay, yeah. So, like, if it’s not in a headline somewhere, you don’t know what it means.

I laughed. He was right. If it was not in an article or a post I was already reading, I did not know it. I am not out here reading technical documents or research papers like Chris Dixon, though I do read the Substack called Technically, and the only reason I made it to that call at all was that I was willing to say so out loud to someone with the vocabulary and the receipts to explain, with a lot of grace, that I had been running my entire operation the wrong way.

I want to talk about what he showed me. But more than that, I want to talk about what it implies for the future of labor. Because I think the individual contributor as a category of worker is about to become endangered, and the people who do not see it coming are going to be the same ones who have spent the last cycle telling themselves they were just a little behind on the technology and would catch up once the disruption settled. They will not catch up. The tools are not the thing. The builder mentality coupled with the (in)organic chart is the thing.

Where I was stuck

I run a small operation with a lot of surface area. I am building a Fund. Two podcasts. A newsletter. Convenings. Consulting. It looks like more than it is because I built agent scaffolding underneath the whole thing to keep action items from falling through the cracks. Every meeting drops a transcript, every transcript gets scraped for to-dos, every to-do gets assigned or drafted or flagged. It runs while I sleep. And when it works, it works well enough that I forget it is running at all.

But it had started to break in the small ways that always add up. Duplicate drafts. Missed follow-ups. Two agents chasing the same task in two different tabs, neither aware of the other. Sand in the gears.

My instinct was to slice the tasks thinner, so I did. One agent for to-dos, one for the partner meeting, one for reengagement, one for intros, each of them polite and focused and operating with a sliver of the picture. Which sounded like discipline, and was actually the opposite. I was treating every agent like an employee I could dispatch, and I was staying in the loop between all of them, checking their work, nudging their progress, rerouting their outputs, playing the role of switchboard operator between a bunch of well-meaning digital ICs who could not see each other.

I was the manager. I had built myself a bullpen of ICs. And I had made myself the bottleneck.

What he actually drew

After I walked him through my misjointed workflows, he stopped me and drew what I should be doing instead. He drew it for me on a whiteboard app while we talked, and I have the screenshots. I keep looking at them because they are the simplest version of a thing I had been failing to see.

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There is a moment early in this conversation when Senia Rapisarda describes how she spent years educating Canadian pension plans on what venture actually is. Her line stuck with me. Venture is agriculture, not geology. A bigger drill does not help you find a nugget that was never buried there. You plant kernels at the university level, at the incubator level, and then you provide a continuum of capital and wait. Twelve years later, Canada has managers on fund two, three, and four, and companies that stay home instead of heading south.

Senia joined Alexa and me from Toronto, where she leads HarbourVest’s Canadian strategy. Before that she was at BDC, where she helped design the Venture Capital Action Plan, a program built with one party and adopted by the next. In a moment this polarized, a policy that survives a change in government might be the strongest signal of all that innovation capital has become infrastructure.

That was the argument that landed hardest for me. Innovation capital is sovereignty. We tend to think of sovereignty as borders and defense budgets. Senia’s frame is that a country that cannot fund its own champions ends up de-risking companies at home and exporting the returns abroad. By her count, roughly 90 percent of late-stage Canadian tech rounds have been led by international managers. The talent is Canadian. The upside mostly is not. Breaking that cycle is the work.

The part of the conversation I keep replaying is her guidance for emerging managers. HarbourVest runs an open door policy, but the door is a starting line, not a finish line. Come back every six months with a fifteen minute update. Bring a co-investment before you ask for a fund commitment. She jokes that a fund commitment lasts longer than the average North American marriage, so date with a deal first. And know that everything gets logged. HarbourVest tracks what she calls your say/do ratio. Tell them what you will do, then do it, and you are building a track record before they ever wire a dollar. That framing feels right to me. Trust is not claimed in a pitch meeting. It accrues in the gap between what you said last time and what you did since.

She also gave the most honest answer I have heard to a question I have been asking a lot lately. She has four filters for durable companies: mission critical, big moat, capital efficient, and non-greedy founders. I asked her to pick the one that predicts survival through this cycle. Her answer was that it depends on your cash position. If you have cash, the moat matters most. If you do not, founder greed at the last raise is what kills you, because a too-high valuation destroys value in the round you cannot avoid.

Nick Cassin of Sidley closes the episode with a clear-eyed explainer on continuation vehicles, including why disclosure and equal information are the whole ballgame when a GP sits on both sides of the table.

Worth a listen.

With gratitude,
Earn

There is a version of a basketball player who never stops moving and never actually gets anywhere. Always cutting, always talking, always going east and west, and somehow the ball ends the possession in the exact same spot it started. Coaches have a phrase for this, and it is not a compliment: motion is not the same thing as movement. Most people confuse the two anyway.

I have been circling that same confusion in venture for a while now. Plenty of activity. Term sheets, panels, LinkedIn posts, another fund closing, another logo added to a deck. Not always much progress underneath it. I did not have a clean way to talk about that difference until Santosh Sankar and I sat down to record, and it turned out to be the first real conversation of the show we are calling Carry On.

Santosh runs Dynamo Ventures. I have known him long enough to trust that he will tell me when an idea is not as sharp as I think it is, which is most of what you want from a co-host and most of what is missing from venture capital content generally. We did not start this because the podcast market needed another one. We started it because the honest conversations about what it actually takes to build a firm mostly happen off the record, in DMs and side rooms, after the panel ends. We wanted to put more of that on the record.

Episode one is called Motion ≠ Movement. We get into why urgency and momentum get treated as the same thing when they are not, and what it looks like when capital and attention concentrate into a narrow set of AI deals and mega funds. We also spend real time on something less comfortable: the erosion of intellectual honesty in this industry, and what it costs a firm when kingmaking dynamics start doing the work that judgment used to do. Santosh walks through the eras of venture, the pendulum between concentration and unbundling, and why craft still matters even when capital alone can buy you a seat at the table.

None of that is a finished argument. Some of it we are still working out in real time, which you can probably hear. That is the point. We would rather practice this in public and be wrong on the record occasionally than polish something into a highlight reel that does not tell you anything you could not have guessed.

So here is a genuine ask: listen to the episode. Tell us where we got it right and, more usefully, where we did not. Reply to this post, comment wherever you are listening, or just send me a note directly. If there is a topic you think two GPs owe each other an honest conversation about, tell me that too. We are building the list of episodes off of exactly that kind of feedback.

Grateful to AngelList, WilmerHale, and Citizens Bank for backing this from the start, and to the Heard Media team for turning two people talking into something worth your time.

with gratitude,
Earnest

Listen on your favorite platform.

Youtube:
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Spotify

Last week on Swimming with Allocators, we welcomed Teddy Repko of the Yuhaaviatam of San Manuel Nation, who shares how his global upbringing, risk-aware personality, and early trading career shaped his investing approach, and how a shift at Columbia University’s endowment from hedge funds to relationship-driven venture gave him a front-row seat to the asset class.

During the conversation he also breaks down how LPs really underwrite managers, balancing base rates, power-law math, and portfolio construction with deep people and relationship assessment, and flags both opportunities and risks in today’s market, from mega funds, AI-driven valuations, and rapid funding cycles to concentrated DPI, late-stage growth, and crypto.

A great episode that I hope you all enjoy.

In the summer of 2011, the Miami Heat had a welcome party for their three free agent signees, Dwyane Wade, Chris Bosh and of course LeBron James. James had recently made “the decision” to leave his original team, the Cleveland Cavaliers, for a chance to win the championship in South Beach. The clip that is laughably used to mock this moment in NBA history is when LeBron responds to the question, ‘how many titles can this team win?’ He responded, “not 1, not 2, not 3, not 4…”, eventually tailing off around 8.

They won 2 titles. Which is a hard achievement. But when your expectation is so high, 2 titles is “not 5, not 6, …” and feels like a failure. Even at the time it felt like the Miami Heat players and fans were literally celebrating the offseason like it was the championship parade.

And for a while now something similar has been going on in venture capital. Some misplaced sense of achievement. This has been sitting with me after a stretch of conversations with founders, pre-seed and seed investors, and a steady diet of consolidation headlines.

The fear is not about losing. The fear is about ‘winning’ the wrong way.

There is a moment in early-stage venture that looks like a breakthrough and is actually a trap. A marquee firm comes downstream, sees something they like, and writes a check that skips two stages of price discovery. The round closes at a number that requires everything to go right. The founder celebrates. The seed investors celebrate. And somewhere underneath all of that, quietly, the outcome distribution narrows.

That’s the kingmaking problem nobody talks about loudly. The brand-name firms have enough momentum capital and enough platform pull to set a valuation that the market has to treat as real. Which means the founder is now playing a different game than they signed up for. And the early investors, who did the hard work of finding them before anyone else was paying attention, are now along for a ride they didn’t choose.

A well-capitalized company raises at a number that requires generational scale to justify, stumbles on product-market fit, and then has to pivot the entire thesis just to keep the lights on. Meanwhile, a scrappier competitor, operating with less runway and more discipline, is quietly winning on the ground. The first company raised 10 to 20 times more and still lost.

The math on this is not complicated, but the psychology of it is hard. More capital feels like more options. It buys time, it buys talent, it buys distribution. But it also buys obligation. The moment you take money at a valuation you have not earned, you stop being a company navigating toward product-market fit and start being a company defending a number. Those are very different jobs. The first one leaves room to learn. The second one does not.

What I keep coming back to is how much of this is a timing problem. The capital is not the mistake. The sequencing is. Raise too much, too early, before you know what is actually working, and you lose the middle. The good-not-great outcomes, the ones that still build real companies and return real capital, mostly disappear. You are either returning the fund or you are a cautionary tale.

The investors I keep learning from are not asking “how do we get to the Series A?” They are asking “what does the Series A make possible, and what does it foreclose?” That orientation tends to produce founders who find fit before they find the big check.

The consolidation headlines keep coming. The mega-rounds keep landing at pre-revenue multiples. The pressure to participate is real on every side of the table. But the companies that feel durable right now are not the ones that raised the most confidence. They are the ones that earned it. They won the right way before anyone was watching.

That’s the only way the foundation holds.

with gratitude,
E

For two decades, we’ve heard that data is the new oil. It was a clean line, the kind that makes its way into every keynote, every board deck, and every LP deck, and like most punchy lines, it skipped a step. Oil is not valuable because it exists. Oil is valuable because somebody built refineries, pipelines, and tankers, and established a global price for the barrel. Until that infrastructure showed up, oil was a thick, corrosive sludge that ruined boots and poisoned the wells around it.

Data, for most of the last two decades, has been unrefined crude oil. Companies sat on enormous reserves of it and treated it like exhaust from the real business. Logs, tickets, transcripts, internal Slack threads, edit histories, the back-and-forth between a customer success rep and the engineer she escalated to at 11pm. Nobody was buying those interactions. These activities and data points were just the price of doing business. The refinery did not exist.

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Kate Simpson started her career as a history major. No finance background, no roadmap. The UNC endowment took a chance on her anyway, and she spent the first stretch of her career doing exactly what a non-finance person does in that seat: listening, asking questions, and building mental models from scratch. She took intro accounting classes at night to supplement what she was learning during the day. She went deeper inside private assets because that was where her team spent most of its energy. And she kept going, from Parish Capital to TrueBridge, where she spent twelve years watching the venture industry scale and evolve in real time, to now leading the venture strategy at GEM, a multi-asset OCIO firm that has been around since 2007.

What struck me about Kate’s path is that it never looked like the fastest way to the top. It looked like someone trying to genuinely understand the craft before assuming they had mastered it. That patience, which is different from caution, runs through how she thinks about everything from building a new venture program to evaluating an emerging manager for the first time.

There is a concept that came up early in our conversation that I want to dwell on before we get to the barbell. Kate described what she looks for in any venture manager as three things: how they source, how they pick, and how they win. The sequence matters. You cannot pick or win consistently unless you are sourcing in the right places. That means the first thing she wants to walk away from an initial meeting understanding is the manager’s network, specifically what ponds they are fishing in and whether those networks carry a real edge.

That is a different question than most GPs think they are being asked. Most people walk into an LP meeting ready to talk about portfolio performance or investment thesis. Kate is asking something that comes earlier: where are you finding things that other people are not finding yet? The answer to that question is more predictive than almost anything else.

The barbell idea is where GEM’s strategy gets interesting. Kate is clear that access to scaled platforms still matters, but argues that the alpha in today’s market is increasingly at the edges. On one end, a handful of top-tier, established platforms retain real competitive advantage. On the other end, the small, craft-driven funds that most institutional programs cannot or do not prioritize are generating the kind of right-tail skew that makes the math work. The middle, the firms that are too big to win at the seed stage but too small to compete with multi-billion-dollar platforms at Series A, is where she is spending proportionally less time.

The math point is not abstract. GEM builds what Kate calls a “what you need to believe” model for every manager who advances in their pipeline. It overlays fund size against target ownership, number of positions, reserve strategy, and a practical range of outcomes to pressure-test whether it is reasonable to expect a 3x, a 5x, or better. One strong outcome returning the fund, not necessarily a unicorn, is the baseline they are testing for. The point is not to find reasons to say no. The point is to know, specifically, what has to be true.

The sub-$200M threshold GEM uses for their dedicated seed and micro fund vehicle is a version of that same discipline applied at the portfolio level. There is something they are protecting when they draw that line, and it is not just vintage diversification. It is the recognition that the fund math on a small, concentrated, high-ownership fund looks different from the math on anything larger, and that difference is worth constructing around deliberately.

Kate also talked about something I have been thinking about more lately, which is what this AI cycle actually looks like from an LP seat. Her read is that we are in early innings of a genuine paradigm shift, comparable to the move to mobile or the move to cloud but potentially larger in terms of the size of outcomes being created. Companies staying private longer has helped the secondary market grow into a real asset class rather than a niche workaround. That normalization changes what liquidity looks like for early investors and founders in ways that would have been unimaginable a decade ago.

Nick Cassin from Sidley also joined us to break down the secondary market side of this. The numbers alone tell the story: from roughly $20 billion in annual transaction volume when he started in 2010 to potentially north of $250 billion today. Continuation vehicles, once a niche exit mechanism, have become a mainstream strategy. The pool of buyers has expanded dramatically. That is not just a market structure observation. It changes how GPs should think about what they are building and how they are building it.

The through line I keep coming back to from this conversation is that the best managers Kate has worked with over her career share one characteristic above most others: they know what they are good at and they stay focused on it. Not because they lack ambition, but because discipline around the edges of your own competence is what lets you build a durable brand and a repeatable process. That is true for fund managers and, honestly, for anyone trying to build something that compounds over time.

If the show has been useful to you, the best thing you can do is leave a rating and review wherever you listen. It matters more than most people realize.

with gratitude,
earnest

In 1973, a USC physicist named Jack Nilles coined the word “telecommuting.” The original problem he was trying to solve was not talent, not flexibility, not work-life balance. It was the energy crisis. Americans were using too much oil driving to offices. His proposal was straightforward: keep workers closer to home by connecting them to their work electronically. The future of work, in 1973, was about the price of gas.

His catalyzing challenge came from an urban planner’s taunt: “If you can put a man on the moon, why don’t you do something about traffic?” Nilles secured a National Science Foundation grant in 1973, published his Final Report in December 1974, and ran a pilot with an insurance company that cut turnover to near zero and raised productivity 15 percent. The company declined to adopt the model, fearing union-organizing dynamics. As Nilles later recalled: “The experiment was a success. But the company said, no, we’re not going to do that.” For the next thirty years, the dominant frame remained congestion relief, clean air, and post-9/11 business continuity, not personal flexibility.

Then the internet arrived and the conversation accelerated. By the late 1990s and early 2000s, the promise of technology-enabled flexibility was everywhere. The vision was expansive: people would work from wherever they chose, hierarchies would flatten, knowledge would flow freely across organizations, and geography would stop being a constraint on talent.

When the major consultancies adopted the phrase in 2017-2018, they still meant automation, not location. McKinsey Global Institute’s landmark “A Future That Works” (January 2017) estimated about half of all work activities could be automated with then-current technology, equivalent to roughly $15 trillion in global wages. Deloitte’s 2017 Human Capital Trends framed the “augmented workforce” driven by AI systems, robotics, and cognitive tools. PwC’s “Workforce of the Future” (2018) built four scenario worlds around automation, AI, demographics, and globalization. None of the three flagship reports centered location flexibility. That reframing came only after 2020.

As a venture investment category, “future of work” was claimed early by Bloomberg Beta, launched in June 2013 with $75 million, describing itself as “the first VC to declare a focus on the future of work and the first to say we wanted to invest in AI.” Managing Partner Roy Bahat defined it broadly, “beyond productivity tools, to how work can serve everyone,” and pushed back when the press collapsed it into remote-work software alone. Emergence Capital similarly developed theses spanning coaching networks, the deskless workforce, and deep collaboration, noting in 2018 that less than 1 percent of venture investment had gone to deskless-worker technology despite that group representing 80 percent of the global workforce.

Somewhere around 2015 to 2019, the phrase became a VC category, a conference theme, a consulting practice, and ultimately a shorthand that meant: remote work tools, flexible scheduling, and the Slack-ification of the enterprise.

All of that was real. None of it was the full story.

I think about this now because the phrase is being used again, and again it is being used to describe something smaller than what is actually happening. The people who got it partially right in 1973, in 1999, in 2016, were pointing at a real direction but describing the first visible symptom rather than the underlying condition. The underlying condition is this: what work actually is has always been in the process of changing, and the changes have always been larger and slower and more consequential than anyone predicted while they were happening.

We are still inside that change. It is just that now the technology doing the changing is different in kind, not just in degree.

Era-by-Era Summary

II. Where I Started

In 2007, I was an equity research associate at BMO Capital Markets in New York. My workstation was a desktop. If I needed to work from home, I had a laptop available, but it required a BitLocker decryption sequence before it would open (a security protocol that also functioned, not coincidentally, as a mild deterrent). The office was where work happened, and that felt self-evident to everyone, including me.

Writing a client-facing email back then took me roughly fifteen minutes. Not because I was slow. Because the standards were different, and the process reflected those standards. Every sentence had to be constructed, considered, and reviewed. The email was the work. Its clarity was a direct proxy for the clarity of the thinking behind it. A sloppy email was a sloppy analyst. There was nowhere to hide, and nobody expected anywhere to hide.

Nobody was measuring my output in emails per hour. They were measuring the quality of the thinking those emails carried. The email was just the container. The judgment inside it was the job.

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This week we published our hundredth episode. I want to use this post to do three things. Thank the people who got us here. Share what I actually learned along the way. And ask you, if the show has meant something to you, to do a couple of small things that help us keep going.

The thank you

The first thank you goes to the guests. Over a hundred conversations, we have had people in the water with us who had no obligation to spend an hour explaining how they actually think. Allocators do not usually talk like this in public. The ones who came on did it anyway, and they did it generously.

When I look back at the range of who “sat” across from us, I am still a little stunned. We had a senior investor from a Texas public pension managing more than forty billion dollars walk through what it really takes to win an institutional check. We had the chief investment officer of a Danish sovereign fund explain how a small country built a global technology engine almost from nothing. We have hosted allocators from institutions like StepStone, Top Tier Capital Partners, Altimeter, Sapphire Partners, Foundry, Screendoor, and Capricorn, alongside multi-billion-dollar foundations, university endowments, family offices that invest on behalf of more than a hundred families, state programs, secondary specialists, and emerging-manager backers. People running impact mandates. People building working capital products for first-time fund managers. People whose whole job is to tell the difference between a manager with an edge and a manager with a good deck. That is not a niche. That is the actual machinery of how capital finds the future, and these people opened it up for anyone willing to listen.

The second thank you goes to the partners and sponsors who made this a real production rather than a hobby. The recurring expert segments with legal and financial services executives gave the show a backbone of substance that a lot of investing podcasts never bother with. Thank you to Sidley, our anchor sponsor, and to every partner who has supported the show along the way, including SVB, Gunderson Dettmer, Passthrough, Canopy, Sydecar, Armstrong International, Vested, Camber Road, and Bottega8. You believed in a show about limited partners, of all things, before that was an obvious bet. And thank you to the people who actually make the episodes sound like episodes. Our producer Jonny and the whole Heard Media team turn two busy people and a pile of raw audio into something worth your time, week after week. None of this reaches you without them.

And the third thank you, the one that matters most, goes to you. The listeners. The people who message me at a conference to say a specific episode changed how they thought about portfolio construction, or fundraising, or their own career. The folks who are not in venture at all but listen because they like hearing smart people think out loud. You are the reason a niche show about the least visible layer of the venture stack found a real audience. We see the audience numbers, we read the DMs and emails, and we do not take a single one for granted.

What I learned

A hundred conversations will change you if you are paying attention. Here is some of what stuck.

People do not differentiate themselves by explaining their strategy. They differentiate themselves by who they are. Our podcast guests have heard managers over-explain their thesis in a way that makes them sound exactly like the fund that pitched the day before, same logos on the deck, same language about value-add. The ones who stand out are the ones who can tell you what they actually sourced, what they actually led, and why a founder picks up the phone for them specifically. Differentiation is not a slide. It is a track record of behavior.

Trust is the moat now. For years the moat conversation was about technology, and then everyone had access to roughly the same technology, and the question quietly changed. Across episode after episode I heard the same shift in different words. The durable advantages now look more like distribution, proprietary data, brand, and trust than like a pure technical edge. That is true for founders and it is just as true for fund managers. The thing that compounds is whether people believe you will do what you say.

Snapshots are not destiny. I wrote about this recently in another essay, and a hundred episodes only deepened it. A hot mark, a top-quartile ranking, a breakout fund, a buzzy round. These are timestamps, not verdicts. The market loves to turn a moment into an identity. Time is usually less generous, and the people who last seem to know the difference.

And the biggest one, the one that took a hundred reps to fully understand. The edge is in showing up. Not in being the smartest person in any single conversation. In being there for the next one, and the one after that, when there is no immediate reward and no guarantee anyone is listening yet. Curiosity keeps you open, but consistency is what builds the body of work.

The numbers, briefly

I am not going to pretend the metrics are the point, but a few are worth naming. We launched in October of 2023 and we have kept a weekly-ish cadence for more than two years to get here, which in podcasting terms is most of the battle, since the vast majority of shows never reach episode ten, let alone a hundred. The guest list spans public and corporate pensions, sovereign funds, foundations, endowments, family offices, fund-of-funds, secondary specialists, and emerging-manager backers, a wider cross-section of the allocator world than I expected we would ever get access to. And the show holds a five-star rating from the people who have taken the time to leave one. None of that happens without the three groups I thanked.

What this is really about

A friend of mine, someone who builds companies and venture firms, said something to me that is relevant to this podcast achievement. His point was that real confidence does not come from sounding certain. It comes from commitment and consistency. Most people can talk confidently for a day. Fewer people show up every day, especially when it is hard. For him, confidence is not a feeling you summon before a big moment. It is just the quiet fact of being committed today and tomorrow, and the day after that. He tied it back to his own routine, the same food, the daily training, the refusal to stop, as proof that the consistency is what produces the confidence, not the other way around.

That is the whole story of this podcast. We were never the most certain people in the room. We just kept getting back in the water. A hundred times now. And we are not stopping.

If the show has given you something, here is how you can give back, and all of it genuinely helps us keep going:

Follow and like Swimming with Allocators wherever you listen, on Apple Podcasts, Spotify, or YouTube. A follow and a rating do more than you would think to help new listeners find us.

And if you want to rep the show IRL, we have merch.

To the guests, the partners, and most of all the listeners. Thank you for a hundred. Here is to the next hundred, one episode at a time.

See you later, Allocator.

earn

This week on Swimming with Allocators, Alexa and I welcome Mike Kakenmaster, Director of Investments at Loyola University Chicago, for a conversation about what it really looks like to build a modern private capital and venture program inside a smaller endowment.

Mike brings a wide lens to the allocator seat. Before Loyola, he spent time across hedge funds, a family office, and multiple asset classes, which now shapes how he evaluates risk, opportunity, and cycles. That generalist perspective matters, especially in a market where LP attention keeps shifting between private markets, hedge funds, credit, buyout, and venture.

We get into how Loyola doubled its private capital allocation, why the team moved deliberately into venture instead of chasing brand-name access, and how Mike thinks about early-stage track records, manager quality, reserves, portfolio construction, access, networks, and the underlying quality of founders and companies.

One theme I appreciated: smaller and emerging managers can be compelling, but only when the strategy, discipline, and judgment are real.

We also hear from Chuck Daly of Sidley on what first-time fund managers need to understand about building operational and governance infrastructure from the beginning. That includes disclosures, conflicts of interest, LP communication, and the basic but important work of treating the firm like a real business before the market forces you to.

A sharp conversation for anyone thinking seriously about how endowments build venture exposure, how emerging managers earn trust, and how institutional discipline shows up long before a fund is “institutional.”

Check it out. - earn

The first time I remember really feeling the weight of rankings, I was somewhere around twelve or thirteen years old, sitting in the stands of a hot Memphis gym, watching a kid the room had already decided was the best. He had not done anything yet that morning, but the air around him was different. People nodded and started talking when he walked onto the court. The coaches in the bleachers leaned forward. The other kids on the floor adjusted, quietly, the way you adjust when you walk into a room where somebody has already been declared important.

That is what rankings do, before they measure anything. They tell the room where to look.

When you grow up around competitive youth sports, you learn that rankings carry strange power. Somebody is the best point guard in the state at twelve. Somebody else is top ten nationally before he is allowed to drive. The list circulates through camps and gyms and one or two older guys who seem to know which sixth grader can shoot from the top of the key in three different states. You hear the names and you start to believe them, even before you have seen the player. The ranking does the work the eyes have not done yet.

It takes a long time to understand what the rankings are actually saying. They feel like a verdict, but they are really a timestamp. They describe one moment, in one set of bodies parties, against one slice of competition, on the way to a destination nobody has reached yet.

Some of the kids ranked early stayed ranked. Some were prodigies whose athletic abilities caught up later, or whose work ethic caught up later, or whose situation never gave them another real chance. Some grew six inches in a year and changed the equation. Some were carrying a label that got heavier every season as everyone else got closer to their level. You only learned which kind of basketball player somebody was once enough time had passed for the truth to show itself.

I have been thinking about this lately because I think we make the same mistake in the business world, and especially in venture capital. We see a startup, an individual fund or a VC firm at one point in their life and quietly turn that point into a permanent identity. We talk about top quartile like it is a residence instead of a snapshot. We treat a hot markup like a decree. We assume that because somebody has been called excellent, excellence is now what they are.

But a ranking is not a residence. It is a timestamp.

That has two implications, and I think we usually only talk about one of them.

Read more

This week on Swimming with Allocators, Alexa and I welcome Yuri Lee, Director and Head of Venture Capital at TMRS, for a candid conversation on what it actually takes to win institutional LP commitments.

Most GP decks sound the same. The thesis feels sharp on paper, the team slide checks the boxes, and the market timing sounds urgent. But institutional LPs have seen enough pitches to know when a manager is performing conviction versus actually having it. That gap, between presentation and substance, is where most fundraises quietly die.

The antidote is not a better deck. It is a clearer edge. Yuri is direct about what she is looking for: differentiated sourcing, picking, or winning, not all three, but real clarity on one. Genuine product-market fit between a manager’s strategy and how they actually generate returns. And ideas that are non-consensus by design, not by accident. In a market saturated with AI theses that all rhyme, that last one matters more than ever.

Yuri brings a rare vantage point, she crossed over from growth investing into an LP seat, and is now building TMRS’s $3B+ venture and growth mandate from the ground up, including an ambitious 50/50 funds and co-investment program. She knows what it feels like to be on both sides of the table, and it shows.

I hope you enjoy.

Somewhere in Marketing 101 at Kellogg, Professor Julie Hennessy taught us the difference between a branded house and a house of brands. A branded house is Apple, Nike, or Google, where one name carries the trust, and new products borrow credibility from the mothership the moment they appear. A house of brands is more Procter & Gamble, Unilever, or LVMH. Conglomerates with different brands that speak to distinct audiences, with the parent company (or house) sometimes invisible in the background. Tide does not need to remind you it’s roommates with Pampers.

At the time I probably filed this somewhere between useful and I hope she does not cold call me on this. Now years later, while building the institutional infrastructure of a venture firm before the fund officially exists, I keep returning to the competing concepts. Not as a marketing question exactly, but as a trust question. And those, I have found, are different things.

A few months ago, a private markets marketing and investor relations advisor I deeply respect gave me an honest read on how my work and pre-raising activity looks from the outside. She said something like: this guy is too scattered, he seems really smart, I’m just going to wait until he figures out what he wants to be when he grows up. She was not being unkind. She was being candid and providing useful feedback. The advice she and several others have echoed is to put everything under one name, build a branded house, make every podcast and dinner series and essay and advisory engagement point back to one logo, Stresswood, so people can track the through line without having to work through the complexity.

I understand that argument. But here is where my thinking keeps landing.

The name Stresswood comes from a concept in biology. When trees grow under natural stressors, wind, rain, gravity and humidity, they develop internal wood fibers that are structurally denser than ones grown in ideal conditions. In the late 1980s, scientists tried to create a perfect growing environment inside a sealed dome called Biosphere 2. Controlled temperature, ideal soil, abundant water, no stressors. The trees grew quickly and then fell over on their own weight because they had never been asked to develop the internal structure required to hold themselves up. I named the firm Stresswood because I think that pattern holds for people and institutions too, that pressure is not incidental to growth but part of what makes exponential growth durable. But the metaphor cuts in another direction as well. A firm built on announced ambition before earned trust has a version of the same problem. The pre-raise season, for me, is not about waiting. It is about building things that can actually hold weight.

An LP friend has reminded me that a fund manager is a capital entrepreneur, which means the job is not just picking companies. It is building a business around judgment, access, distribution, and trust across several different communities that do not naturally talk to each other. LPs and founders share almost no common interests. The upstream investors who feed deal flow and the downstream investors who might follow your rounds have different priorities still. The corporates and hyperscalers I spend significant advisory time with are operating in a different conversation altogether. One brand doing the work of earning trust in all of those rooms at once is probably asking something of the brand it was not designed to do, and I think that is the part of the advice toward simplicity that I have not been able to fully accept. It is less about aesthetics and more about whether a single front door can honestly serve rooms that open onto very different landscapes.

Swimming with Allocators has been the clearest proof of concept for me.

Read more

There’s a moment in the conversation when Erik Balck Sørensen describes the Danish startup scene he came up in. No venture funds. No ecosystem. No infrastructure for what he was trying to build. He figured it out anyway, founded a few companies, and a generation later he’s the CIO of Denmark’s Export and Investment Fund, a sovereign platform backing innovation at the country’s scale.

That arc is the through line of this week’s Swimming with Allocators.

Erik joined Alexa and me to talk about how Denmark went from a thin venture market to a global presence in biotech, green tech, and deep tech. What landed for me wasn’t the policy or the capital. It was the culture. Tight founder communities, a real ethic of giving back, the founders who had made it cycling back to help the next wave. The infrastructure followed the relationships, not the other way around.

We spent real time on what it actually means to run a sovereign wealth fund with a dual mandate. Financial returns for taxpayers on one side, societal impact on the other, and the steady work of holding both without one quietly swallowing the other. Erik was candid about the political momentum that shapes their work, the past missteps that have sharpened their discipline, and how a platform like theirs has to think about time horizons differently than almost anyone else in the market.

Then we got into what comes next. Denmark’s 2030 plan is about moving faster, professionalizing as an LP and as a direct investor, and doubling or tripling down on the verticals where they already have an edge: life sciences, selected green technologies, quantum computing, and European growth-stage capital. The strategy reads less like a pivot and more like a deepening.

Worth a listen.

This week on Swimming with Allocators, Alexa and I welcome Wes Panek, Head of Fund Investing at Astera Institute, for a conversation on deep tech fund investing.

Deep tech is one of the areas where the normal venture playbook can break down. The timelines are different. The technical risk is different. The talent networks are different. And the best opportunities often require investors to understand both scientific ambition and institutional constraints.

Wes brings an unconventional path and a thoughtful lens to how allocators can back deep tech managers with more clarity, patience, and conviction.

This week on Swimming with Allocators, Alexa and I talk with Avivar Capital co-founders Lisa Richter and Tina Castro about aligning capital with community impact.

This episode is a reminder that capital has consequences. The question is not whether money shapes communities. It does. The real question is whether allocators are being intentional about the outcomes they are helping create.

Lisa and Tina bring a grounded perspective on impact, accountability, and what it means to build investment strategies that serve both financial objectives and community needs.

This week on Swimming with Allocators, Alexa and I welcome Juan Diego Briceno for a conversation on venture co-investments and how LPs should think about the opportunity set.

Co-investing sounds simple until you actually have to do it well. Access, speed, adverse selection, relationship dynamics, and internal decision-making all matter. The playbook needs more nuance than “we want more direct exposure.”

Juan Diego brings a helpful perspective shaped by private banking, Latin American wealth, and the practical realities of building trust across markets.