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.

This week on Swimming with Allocators, Alexa and I are back for another DDQ episode, this time digging into founders, fraud, and the dangerous line between ambition and deception.

Venture has always rewarded belief before proof. That is part of what makes the industry powerful. But it also creates room for narrative to outrun reality. We get into where “fake it till you make it” becomes a problem, how investors should think about diligence, and why trust is still the most important currency in the business.

This one is a timely conversation for founders, GPs, and LPs alike.

This week on Swimming with Allocators, Alexa and I welcome Zach Ruchman, Shareholder and Managing Director of Private Investments at HB Wealth, for a conversation on private markets, differentiation, and what it takes to stand out when everyone’s materials start to look the same.

This is one of the core tensions in venture fundraising right now. The market is full of smart people with polished decks and reasonable strategies. But LPs are looking for evidence of real edge: sourcing, judgment, discipline, alignment, and a reason to believe this GP is uniquely suited for the work.

For GPs, this episode is a useful mirror.

This week on Swimming with Allocators, Alexa and I welcome Marcia Mitchell to trace her path from FF Venture Capital to New York venture and fund investing.

What stood out to me in this conversation is the blend of problem-solving and people work. Venture is often described as pattern recognition, but the best investors are also translators, coaches, relationship builders, and steady hands in uncertain situations.

Marcia’s perspective is especially useful for emerging managers and LPs thinking about what kind of partnership actually helps a firm grow beyond capital alone.

This week on Swimming with Allocators, Alexa and I welcome Iliana Oris Valiente, a Fortune 500 corporate executive, independent LP, and founder of the Venture Forward Institute.

This conversation is for the next generation of LPs, but it is also useful for GPs who want to understand how capital allocators are being formed today. Venture is full of unwritten rules, but the market is changing fast enough that the next generation cannot simply inherit the old playbook.

Iliana brings a thoughtful perspective on what new LPs need to learn first, and how they can build judgment without getting lost in the noise.

This week on Swimming with Allocators, Alexa and I welcome David Clark, CIO at VenCap, for a conversation on data, venture returns, and what it takes to build a durable view of the asset class.

Venture can sometimes feel allergic to structure. But great allocation requires both judgment and evidence. This episode gets into how data can sharpen manager selection without pretending that the numbers alone can do the whole job.

For anyone thinking about how LPs evaluate venture at scale, David’s perspective is a valuable one.

This week on Swimming with Allocators, we wrap up our “Best of 2025” reflections with more of the moments, lessons, and conversations that shaped the season.

What I enjoy about these recap episodes is that they let the audience hear the throughline. The venture market changed. The allocator market changed. But the fundamentals kept coming back: trust, discipline, differentiated judgment, and the ability to stay thoughtful when the market tries to make everyone reactive.

Part 2 is a strong listen for anyone who wants the year’s lessons in one place.

This week on Swimming with Allocators, we take a step back and revisit some of the best moments from the year.

Part of the value of doing this show is that the lessons compound. One episode gives you a window into a particular LP, GP, or institutional perspective. But when you stack the conversations together, themes start to emerge: patience, alignment, manager selection, liquidity, portfolio construction, and the human side of capital.

This first “Best of 2025” episode is a chance to hear the patterns that kept showing up across the year.