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.

This week on Swimming with Allocators, Alexa and I welcome Elizabeth Egan of TIFF Investment Management for a conversation that moves from consumer insight to AI upside and what LPs need to understand in the new economy.

The best allocators are not tourists in markets. They build a point of view, pressure-test it over time, and look for managers who can translate insight into durable advantage.

This episode is especially relevant for anyone trying to understand how AI fits inside a broader institutional portfolio rather than treating it like a standalone headline.

This week on Swimming with Allocators, Alexa and I welcome Apurva Mehta, Co-Founder and Managing Partner at Summit Peak Investments, to talk about what LPs really value in the fundraising process.

This episode is useful because it gets underneath the surface-level fundraising advice. LPs are not just evaluating a deck. They are evaluating clarity, judgment, trust, pacing, and whether the GP understands what kind of business they are actually building.

For emerging managers, this is a reminder that fundraising is not just persuasion. It is evidence. The best pitch is a strategy, a story, and a set of behaviors that all point in the same direction.

This week on Swimming with Allocators, Alexa and I welcome Jay Rongjie Wang, Founder and CEO of Primitiva Global, for a conversation on authenticity, AI, and the power of congruence.

Jay brings a perspective that is both strategic and deeply human. We talk about what it means for founders and investors to build in alignment with who they are, not just what the market rewards in the moment.

That matters more than people admit. Venture is an energy game as much as it is an intelligence game. If your firm, strategy, and daily work are out of alignment, the market eventually finds the cracks.

This week on Swimming with Allocators, Alexa and I are back with another DDQ episode, getting into due diligence, differentiation, and what venture firms actually need to prove in a market where everyone sounds increasingly similar.

We talk about whether LPs should go direct, whether storytelling is table stakes, and whether venture is becoming private equity in a Patagonia vest.

The real thread underneath the conversation is clarity. Who are you serving? What do you believe? What do you do when the market gets noisy and the easy language stops working?

That is the part of differentiation that never fits neatly in a deck.