I said something on the record I have mostly kept to private conversations. When I moved to San Francisco after business school and started interviewing for associate and principal VC roles, I was grateful that nobody could tell how old I was. My genes bought me cover. I needed it, because I heard over and over something I called the rule of 27. If you had not done something exceptional by 27, why would a top tier firm take you.

I do not think I was wrong that the rule existed. I was wrong about what it measures.

Santosh opened by asking whether there is a sweet spot age for a high functioning VC. I swapped the word almost immediately. Not age. Lifestyle. This work feels a lot like life. You meet people and nothing comes of it. You back people and it goes to hell or heaven. What the job asks for is room to think and the willingness to keep showing up, and both of those track with age without being caused by it.

Then he brought numbers that cut against the folklore. Across roughly three million U.S. founders the mean age is 42. Among the highest growth one in a thousand it is 45. Founders at 50 and over are twice as likely to deliver a top tier outcome. The industry that invented the rule of 27 writes its checks to people who are, on average, fifteen years past it.

An aging curve is a population object and we keep using it to price a person. Basketball solved this a while ago. The curve says a wing declines after 30. LeBron at 40 does not refute the curve. He is the residual, and the residual is the whole business. I said on air that the goal is to be an exception that invests in exceptions. You are trying to be the weird dot on the chart, the one that should not be there. If that is the job, a hiring band is a strange instrument to run it through.

Three things I took.

Risk tolerance may be inherited rather than aged into. Santosh gave the standard version. You will never be more risk seeking than right out of school, because responsibility becomes liability. I pushed on where that belief comes from. We were raised by boomers, personally and professionally, and that generation was handed a world that mostly went up and to the right. Some of what they taught us was true then and is not true now. I am not sure the risk curve is a fact about human beings. It may be a fact about one fifty year run.

Staying too long is a franchise cost before it is a personal one. Santosh is the youngest of four partners at Dynamo and the firm is coming up on eleven years. He looks at other professions carrying partners at 65 and 75 and 85 and sees damage. "It doesn't matter if your name's on the door," he said. "That's still net negative for you and your legacy if you're a founder of a firm." He raised Jordan going to the Wizards and was honest that ego sits underneath the whole question. LPs ask him how many funds he has left in him. It is a rude question and it is the right one, asked badly.

Experience might be the depreciating asset. I did not walk in with this one, and it went against me. NVCA data shows the share of partners at their current firm ten years or more has risen over the last four or five years. I offered the flattering read. Founders want expertise, pattern recognition compounds, the market is finally paying for people who have seen a few cycles. Santosh agreed that every firm benefits from someone who has seen multiple cycles, because history rhymes. Then he kept going. "Experience alone, I don't think, will be valuable because in the age of intelligence, you can tap into experience in a non-humanistic way that's still sufficient."

I have been sitting with it since. If experience is retrievable, the ten year tenure number stops being evidence of compounding and becomes a question about what those ten years still buy.

Where I am not settled. I still believe pattern recognition compounds. What I can no longer defend is the assumption that it compounds faster than it commoditizes. That is the same clock Santosh put on every other venture advantage on episode four, and I did not notice he had turned it on us.

I wrote in Everyone Shoots Threes Now that a weakness is a hiring problem and not a prompting problem. The other half of that showed up here. Knowing precisely what you spike at beats being adequate at three things. When you are young you try to spike at all of them and dilute the one you are actually good at.

There is no perfect age. There is a weird dot, and the work is getting yourself onto it.

Listen here.

with gratitude,
earn

I asked Michael Wooten a question I have been chewing on for months, and he answered a better one.

My question was about telling versus showing. I keep meeting emerging managers who are excellent at telling, and whose response to a hard fundraise is to tell more. I keep meeting others who are quieter, who have something real, and who cannot get it across a table. I wanted to know how a manager shows differentiation when it is not obvious, not early, and not loud.

Michael did not take the communication framing. “Sometimes people want you to be differentiated, but they want you to be on the edge of the box,” he said. “If you’re too differentiated, then that’s probably going to be tough for the investment committee.”

I had been treating differentiation as a storytelling problem. He handed it back to me as an underwriting problem.

In basketball (yes another basketball anology) the corner three is the best shot on the floor and the tightest one. Twenty two feet instead of twenty three point nine, worth the same three points. That foot and a half is the entire edge. It is also the spot where the sideline crowds your heels. The efficiency and the out of bounds line sit on the same piece of floor. You do not get one without standing next to the other.

That is the edge of the box. It is where the return lives and it is where a committee stops being able to price you.

Three things I took from the hour.

Differentiation has to be legible, not just real. Michael’s point was not that managers should sand down their edges. It was that an LP has to be able to write you up. Storytelling is necessary and it is not sufficient. He was direct that execution has to back it, and that at the earliest stage you are selling the sizzle because the steak does not exist yet. By growth you have the steak and you had better lead with it. The failure I see most often is not the manager who is too plain. It is the manager who is genuinely differentiated in a way that has no comparable, and who reads a committee’s inability to underwrite them as a lack of conviction.

Sourcing is the product, and the product is for founders. Michael walked through why SignalFire stood out to him. They built proprietary data early, used it internally for sourcing, then turned the same thing around and gave it to their founders. That second move is the one that mattered. It stopped being a sourcing edge and became a winning edge. He said they took him through the track record and showed where they beat tier one firms already on the cap table, and ended up with more ownership than they had rights to. Underneath it is a claim I now think is just true. Of capital, he said, “that’s not going to be enough because that’s a commodity.” Founders want three things from an investor, in his telling. Introductions to customers, capital, and help recruiting. Two of the three are not money.

The thesis push may be eating the thing it was meant to prove. This was his hot take and it is the part I am still turning over. He thinks sector theses work at growth and do not make sense early. “I think your thesis should be to find great founders who are trying to tackle hard problems.” Then he closed the loop. LPs want managers in a box. Managers reverse engineer a thesis to get into the box. “you’ve crowded out that market and now you’re no longer differentiated because everybody else is doing that.” The differentiation requirement manufactures sameness. That is a mechanism, not a complaint.

Where I am not settled. I let that one sit in the room without pushing on it. I have watched sector focus do real work at pre seed, but the work it does is access, not picking. A narrow lane gets you into founder networks a generalist never sees. Michael would probably say fine, that is a sourcing edge, call it what it is and stop calling it a thesis. He may be right. I have not landed.

One more thing worth saying plainly. When I asked what he actually watches in diligence, none of it was the deck. He watches how a manager treats waitstaff. He hands them a question thirty minutes early, teach me something, anything, and then watches whether they can carry a conversation while it sits in the back of their head. He built that from hiring people at a former job and thinks manager selection is not that different. And his pet peeve was not a bad quarter. It was silence. The manager who stops responding after the money is in.

I wrote in The Songwriting Credit that sourcing is the part of this business people credit last and depend on most. Michael got there from the other side of the table and landed in the same place. That is usually a sign the thing is true.

Listen to the full conversation with Michael Wooten here.

With gratitude,
earn

Two years ago I spent a lot of money on Replit trying to build a Cerebro, an agentic CRM that would let me blow past Dunbar’s number. My family asked what I was doing. The best answer I had was that it was cool. Vibe coding, just vibes.

I started that story on episode four of Carry On, and Santosh cut in with the specifics before I got to them. Five hundred plus. Over a weekend. I finished his sentence. That you’re not even using. Everybody building has one of those.

I brought the pattern; Santosh supplied the part I did not have. My list was firms that focused on data, firms that built platform services, firms that specialized in one industry. Each started as a reason an LP should pick you and ended as a line in every deck. What I asked was what happens to whoever shows up late.

He answered with a clock. In the prior cycles, novelty commoditized in roughly one to two fund cycles. He claims that AI accelerates that, because commoditizing defensibility is what AI does to the industries it enters. Then he ran it forward. We are sitting here in 2026; three years ago was 2023, and by his read the cycle has arguably run once already. He kept the hedge and so will I. On adoption, he is not hedging. “You cannot do it.”

I reached for basketball. When the Sloan people let us idiots know that a thirty-five percent three-point shot beats a fifty percent two-point shot, every team started shooting threes. The insight was correct, and it stopped being an advantage the moment the market was corrected. What separated the Warriors was not the math. It was Klay Thompson and Steph Curry, and Draymond Green, who survived the space they opened.

He put it as a maybe rather than a verdict. “If you don’t have anything unique and advantageous without AI in the equation, AI isn’t going to actually bring that to you.”

My framing has been that tools should magnify what you are already great at, by ten or a hundred times. I said it again on air. Santosh took it and added the half I had never stated. “Don’t use AI to help you improve a weakness that might be better done by actually adding to your team.”

That is a hiring rule wearing an AI costume. A gap in your firm is a person-shaped problem. Covering it with a model leaves you mediocre at that thing permanently, with better documentation. I said absolutely, and we moved on. I have chewed on it since. In the same stretch, he described asking his principal what she thought her superpower was, and framed his read as an argument rather than a finding: most funds probably have duplicative superpowers on the team and have done okay anyway.

The thing I keep returning to is the least glamorous. He thinks the skills file will become one of the more important artifacts inside a firm, along with every reference it reaches into. “A lot of how you get AI performant is not different than when you have new hires coming in. You need to document how work is done.”

At Dynamo, an agent drafts the portfolio update and headline numbers, then several people comb it for accuracy and completeness, which frees the quarter for the deep thesis piece. What I liked most is what AI did to his old process docs, some untouched for two years. Some he improved, because a model holds more context than a person. Others he decided did not need to exist, since they only existed to account for a human in the loop. That is operations hygiene in a new hat, and the least copyable thing in the episode.

Where I am still working it out is taste. Santosh asked whether you could teach it to a model. I said I never like to say never with technology, and then I said today, no. I believe both halves and know they do not sit together.

The bigger tension is with my own first episode. Motion is not movement. I argued in July that venture mistakes activity for progress, and spent a good part of this one advocating for activity. Tinkering that changes what you ship is movement. Tinkering that only changes what you use is motion. I am not sure the line holds. I have the Replit receipt.

The moment I keep coming back to landed before the harnesses and the agents. Santosh asked whether it was strange that we had circled back to what our parents were teaching us at eight, nine, ten years old. Just be a good dude. I said being a good person is an advantage, and I meant it as a claim about competitive dynamics, not a sentiment.

Then we spent the back half on harnesses and agents and skills files, and I closed by saying the individual contributor is dead forever. I wrote a version of that in Everyone (and Everything) Is a Manager Now and still think it is right. But we settled the human part first and spent the rest on tools. Either that is the joke, or it is the point.

Listen here: https://carryonpodcast.com/podcast/ai-wont-get-you-access-the-human-skills-that-still-matter-most/

With gratitude,

earn

Kelli Fontaine worked in the athletic media relations department at the University of Colorado. She described what you do after a bad football game. You go find the stat that is true. “We could say we had the longest punt in history.” The number is real. It is also a record of a loss.

That is the whole conversation, sitting there in the first three minutes.

Kelli is a partner at Cendana Capital and may be the most data-forward allocator we have had on. Her team runs 78 dashboards. What I did not expect was how carefully she keeps her own numbers from hardening into rules.

The conversation sharpened something I had been circling. In early-stage venture, a finding is not a law. It is a timestamp. A good analysis has a shelf life the analyst does not control.

Three things I took.

First, she dates her own findings instead of defending them. When Kelli joined Cendana she built the data systems, then ran the analysis on their own book. Pre-seed against seed. Same graduation rate. Same mortality, which she thinks was probably acqui-hires. Better multiple on the year of entry. More risk, better outcome.

In our prep call she had put this to me as having grown skeptical of that conclusion, and I read that framing back to her on air. She did not repeat the word, and she did not defend the finding as durable either. She placed it: “it’s one of the things that worked in a market at that point in time.” Then she gave the mechanism that closed it. San Francisco filled with capital focused on early stage. Institutionalized angels became a category. Pre-seed, in her words, “probably arbitrage away in the Bay Area specifically.”

That is more useful than recanting. She keeps the analysis and puts a date on it. “That was a learning for me,” she said, and the learning was not that she had been wrong. It was about why a thing worked, and what that means now.

Second, a harder market argues for more shots, not fewer. I asked how the change in graduation rates shows up in diligence on a Fund I or Fund II, and said the part that seemed obvious: it is tougher now, a manager has to get so many things right to land even one or two fund returners.

She agreed, then went somewhere I did not expect. The instinct she keeps seeing in response is concentration, and she gets pitched a lot of 15 company portfolios. Her read runs the other way: “if graduation rates are lower, you know that would mean that you should probably have a few more shots on goal today, because things can look good at the early stages.”

Run the mechanics. Concentration only pays if your ability to identify the winner improved. A lower graduation rate does not improve identification. It lowers the base rate. Same shooting percentage, fewer makes, so you need more attempts. Her ask of a concentrated manager is not that they drop the structure. It is that they articulate why it is right, and why a prior hit rate repeats.

Third, acqui-hires are a return line. Looking back at Cendana’s historical returns, roughly 10% came from acqui-hires and roughly 10% from modest exits. Same contribution. I have spent years hearing acqui-hires described as what you settle for when the real outcome did not happen. In her math they pay about what a decent exit pays. She paired it with a colder point: it is very rare that a company comes back to life after year seven. Venture built enormous muscle around sourcing, picking, supporting, and winning. Portfolio management, she said, “has been missed along the way.”

Where I am still working it out is founder secondaries. I brought the alignment framing into the room, that founder selling should track GP selling. She came at it differently, and hers is better. Venture runs on hospitals, endowments, foundations, and pensions, so a founder taking cash ahead of those LPs is a fact about sequence, not only optics. Then read it as information. If a founder is de-risking, she said, “almost taking that as a signal is it’s time for you to de-risk some too.”

I prefer her reading to mine, and I am still not sure it resolves cleanly. She drew the line herself: is it enough “to buy a house and like give them some breathing room, or is it enough to make them extremely wealthy?” That line gets drawn by circumstance as much as by conviction. I have watched founders with no cushion make choices that looked like doubt and were just rent. I did not push on it in the room. I would want more resolution before treating sale size as a read on belief.

The phrase I keep sitting with is what she is not underwriting: “the king making marks.” I wrote about a version of this in The Motion Problem, that when capital concentrates hard enough, kingmaking starts doing the work judgment used to do. Kelli is running the LP-side version of the same worry, with dashboards. She would rather know the customer quality and the ACVs than know who led.

That is the data discipline I trust. Not the dashboard that answers. The dashboard that keeps asking whether last year’s answer still holds.

Listen here: https://swimmingwithallocators.com/podcast/finding-alpha-before-consensus-data-judgment-and-early-stage-venture/

With gratitude,

earn

Bands almost never break up over the music.

Ask anyone who has been in one. It does not end because the songs got worse or because somebody stopped being able to play. It ends over the credit. Who wrote the bridge. Whose name goes on the record. Who gets paid when a car commercial licenses the chorus eleven years later. Nobody has that fight in year one. In year one there is a van and a shared amp and nothing to split, so the question never comes up, and everyone tells themselves the silence is alignment. It is not alignment. It is an unpriced asset. The fight arrives on schedule the moment there is something worth arguing about, and by then the arrangement between the people is the fragile part, not the music.

Near the end of episode three I put three archetypes on the table, because I think every firm is one of them whether or not it has admitted it.

Some firms are the Rolling Stones. This is the band. We are doing this into our seventies, or until we quit. We ain’t adding nobody new. Some are small market franchises. Utah, Oklahoma City. We are not getting top free agents, so we had better be excellent at the draft. And some are the Lakers. We do not care about draft picks. Once somebody proves they are amazing, our brand is better than theirs, and they will come. We are watching that one happen right now, with people folding firms they started themselves to go join a bigger name.

The taxonomy sorts firms by how they hold together and how they replace people, which is more useful than sorting them by AUM or stage. And the band is the one most people are actually building. It is also the only one of the three with no plan for its own failure. The franchise has a draft. The brand has a recruiting machine. The band has a handshake.

Most of the episode is about the least glamorous part of this job, which is sourcing. Santosh’s framing is that the shift already happened and a lot of firms have not noticed: you stop tracking companies and you start tracking people, sometimes years before they come to the realization that they want to go found something. At pre-seed and seed there is no database and no portfolio page to scrape. There is only whether they know your mettle before they need you. That is a different job than the one most of us were trained to do, and it does not produce a pipeline you can screenshot for an LP update.

At my stage the problem inverts. When I started in 2015, sourcing at Series A still meant something, because there were fewer firms and much less information moving between them. Now everything ends up in a database, so I am not sure proprietary deal flow at traction stage is a real thing anymore. Anybody can find it. Can you win it. Can you show a founder why you are the right partner, and then actually help them inflect.

Santosh’s answer for how you earn that is plainer than it sounds. Make a promise, know in advance which ones you can keep, and then keep them. Founders run the list afterward, and so does everyone watching. Which is really a conversation about brand. We learned it at Kauffman and I have never found a better version: your brand is what people say when you are not around.

The middle stretch of the episode is solo GP versus partnership, and the way that question usually gets asked is about economics and speed. The way it should get asked is about self-knowledge. Do you know how you behave when you are wrong in front of someone whose opinion you need. A partnership is not a structure for making decisions. It is a structure for surviving disagreements, and Santosh is right that the ones without a real conflict resolution process do not blow up. They poison slowly. Resentment compounds while everyone stays professional about it. In a firm the unpriced asset is carry splits, decision rights, and whose name is on the deal when it works. That is the songwriting credit again.

Do not run a partnership like a dentist’s office. One admin at the front desk, three dentists, one building, nobody talking to each other. That is not a firm, it is a lease.

Sam Heshmati from Citizens Private Bank sits down partway through, and his stretch is the best articulation I have heard of why problem solving beats product pushing. He says their job is not to be the reason a company succeeds, it is to slightly increase the probability of success, and to do that for a lot of people. Products and services get commoditized. People and relationships do not. He is describing banking, and he is describing our job.

There is more in the forty-four minutes than I can carry into one essay. We get into why the easy version of your strategy is usually just a different hard thing, and what an associate is even for when diligence takes ninety minutes.

So here is the ask, same as the last two times, because it keeps working. 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.

Write the songs. Then write down who wrote them.

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.

• Full episode page

• Apple

• Spotify

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.

• YouTube

• Apple

• Spotify

• Full episode page

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

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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.

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

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

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.

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.

This week on Swimming with Allocators, Alexa and I welcome Charlotte Zhang, Senior Portfolio Manager at Inatai Foundation, for a conversation on how LPs evaluate managers.

Every GP wants to know what LPs are really looking for. This episode gets into the checklist behind the checklist: strategy, team, portfolio construction, references, judgment, alignment, and the ability to explain why the firm deserves to exist.

For emerging managers, this is a practical episode. For LPs, it is a useful reflection on how disciplined underwriting can still leave room for conviction.

This week on Swimming with Allocators, Alexa and I welcome Anthony Giambrone, Partner at StepStone Group, for a conversation on power laws, secondaries, and the importance of consistency in venture allocation.

This episode gets into the mechanics that matter. Venture returns are not evenly distributed. Liquidity is not always clean. And great programs require a framework that can survive multiple cycles.

Anthony brings the perspective of an institutional allocator who has seen enough market turns to know that consistency is not boring. In venture, it may be the whole game.