He did not hesitate and gave me three things.
Be curious about everything.
Be nice to everyone.
And schlep.

Schlep was the Sesame Street answer. It was not like the others. And it is the one word on that list you cannot fake.

We are in a moment where information is cheap and getting cheaper. Two people looking at the same market can now produce a decent synthesis in minutes (or their AI model can). That is no longer the edge. The edge is in what you do after the summary runs out. It is in getting on the plane. Going across the country or globe when everyone else is waiting for the deck. Asking one more question. Showing up somewhere you were not expected and paying attention.

That is schlepping. And fewer people are willing to do it because our screens convince us that access to information is the same as doing the work.

The kindness part is easy to underestimate too. Not the absent-minded politeness of glancing up from your phone when someone walks in. Real presence. Learning names. Looking people in the eye when they have nothing obvious to offer you. The allocator reiterated it costs you nothing to be kind and it compounds quietly over a career. I believe him.

Curiosity keeps you open. Kindness keeps you grounded. Schlep keeps you honest.

I have been trying to articulate why I want to build the most analog firm in a digital age. This one conversation this week got me closer than a year of thinking about it. The framework is not new. The willingness to actually live by it is what is getting rare.

With gratitude,
earn

This came out of a prep conversation for Swimming with Allocators. New episodes are out every Wednesday on Apple Podcasts, Spotify, and YouTube.

* * *

Twelve days ago, my paternal grandfather, Earnest Sweat Jr., passed away. Yesterday, an “Earnest Sweat” Google alert pinged my inbox with his obituary. I clicked it, started reading, and something about the math stopped me cold.

Read more

About halfway through the conversation, one of the co-founders said something that I have not been able to shake. The hardest part of design has never been execution. It is deciding what it should be. AI, right now, is largely pattern recognition. It can generate, remix, and approximate your preferences. But the question of what a thing needs to communicate, and what it needs to feel like to someone encountering you for the first time, that is a judgment call. And judgment calls require someone who has actually lived something.

Because of how my mind works, that concept sent my mind in three directions at once.

Three Reference Points

The first was a documentary called Exit Through the Gift Shop. It was supposed to be about Banksy. Instead, it became a portrait of Mr. Brainwash, a man who rode proximity to real artists and an instinct for replication into something that looked, at a distance, like a career. Whether he was a fraud, a genius, or just a mirror held up to an art world that had already lost the plot is a question the film never answers, which I think is the point. He forces you to ask whether the system itself is complicit in elevating replication. And in doing that, even he becomes useful.

The second was Andy Warhol. The first time I really encountered his work was in my (required) Art Humanities course at Columbia, and I remember sitting there thinking, this is not art in the way I have been taught to recognize it. He was not grinding pigments or obsessing over perspective. He was selecting, repeating, and amplifying. At the time, I thought maybe he was just vampiring culture, attaching himself to whatever was already popular. But decades later, the soup cans still stand. The Marilyns still stare back at you. He was not just copying. He was diagnosing something about celebrity and consumerism that most of society had not yet learned to see.

The third was Nora Ephron. There is a documentary about her life called Everything Is Copy, which was her thesis about how to live and work. Her argument was simple: life is material. Conversation, heartbreak, awkward dinners, and even betrayal. Nothing is wasted. Everything can be transformed into something that makes another person feel less alone.

Which leads to the question that connects all three. If AI can remix everything documented on the internet, and Nora Ephron remixed everything that happened to her, what is actually the difference? That is when I pulled Baldwin off the shelf.

Baldwin Sets the Bar

That is the line between slop and soul.

Baldwin is not talking about style or technical craft. He is talking about extraction. Art is not the rearrangement of available inputs. It is the relentless forcing of meaning from lived experience, taking the disorder of a life actually lived and compressing it into something ordered and intentional, something that carries weight precisely because you can feel the pressure behind it.

AI can remix what has been documented. It can recombine what has been digitized. It can produce something that looks like design or reads like prose. But it cannot suffer. It cannot metabolize. It cannot extract the last drop, sweet or bitter, from a life it has actually lived. That is not a limitation that gets patched in the next model update. It is a categorical difference.

The Archive Was Never Neutral

There was a second thread in my conversation with Civilization that also resonated with me. The researcher and strategist at the firm was explaining a design library one of the co-founders has been building, focused on the history of modernist design with particular attention to resistance and protest movements, documenting the visual culture of communities that were never centered in the dominant archive. Her observation was pointed: pattern recognition can only work with what has been documented, and what has been documented is not evenly distributed.

Everything AI generates is made of what was put into it. The likelihood of any specific design choice is weighted by how often something similar appeared in the training data. Which means that generating from the dominant archive tends to reproduce dominant patterns, dominant aesthetics, and dominant assumptions about what looks credible or innovative or trustworthy. The bias is not always visible, but it is always there.

This matters beyond design. It matters for anyone trying to signal something genuine in a marketplace about to be flooded with content drawn from the same underlying archive. When the floor of acceptable output rises for everyone simultaneously, the thing that differentiates you is no longer access to tools. It is provenance. The undocumented story. The perspective that was never in the training data because it came from somewhere the algorithm did not know to look.

What the Premium Shifts To

AI will make the average acceptable, and that is already happening. A competent pitch deck, a functional brand, a passable strategy memo, all of these are now within reach for almost anyone with a subscription and a good prompt. The floor has risen and it will keep rising.

But when the floor rises, the premium shifts. Right now, I think it is moving toward three things that cannot be generated: provenance, conviction, and coherence. Provenance asks what it actually cost you to arrive at an idea, what you have seen and survived that gives your perspective weight. Conviction is the difference between someone who decided what something should be and someone who generated options and picked the one with the best metrics. Coherence is the quality of something that feels integrated, like it came from a sensibility that has been tested against reality rather than assembled from available parts.

In venture, I see an enormous amount of output right now. Pattern matching, hot takes, this-looks-like-the-next-X analysis. We are very good at recombination. The firms and founders that endure are not just recombining. They are extracting from cycles they have survived, from customers they have actually sat with, from markets they misunderstood and had to relearn the hard way. That extraction is the work. And it is work that cannot be outsourced.

So maybe the future of design, and of venture, and of any work that requires judgment, is not a battle between humans and machines. Maybe it is a sorting mechanism. The average will be easier to produce. The noise will get louder. But the exceptional will become priceless, because the exceptional will carry evidence of a life behind it. It will feel like someone actually paid attention, actually suffered the question, and actually forced from their experience the last drop it could possibly give.

That is not something you can scrape from the internet or prompt.

That is something you have to survive.

With gratitude,
earn

What I loved was how unromantic and disciplined Erik was about the tradeoff. This isn’t a branding exercise. It’s a daily operating system: stay professional as an investor, stay honest about the political momentum, and don’t confuse “good intentions” with durable outcomes. It reminded me of every great corporate VC seat I’ve seen. Strategic value and financial value aren’t separate lanes. They’re the same road. The difference is whether you can hold both truths at once without getting sloppy.

Somewhere in the conversation, my brain went back to why I attended Columbia in the first place. Not just New York, though that was a real perk given my love of East Coast hip hop, but the core curriculum. Being forced given the opportunity to read the canon and wrestle with Western history was my early attempt to understand why the world was the way it was before trying to predict what it would become. I doubled down on that curiosity and chose economics and political science because I couldn’t stop noticing how superpower nations and multinational companies were starting to behave like city-states, with their own incentives, alliances, and gravity. Listening to Erik talk about a country of 6 million people with a strategy in a shifting order made that whole mental model feel less academic and more alive.

And that’s the field note: even in a world getting more insular and polarizing, the opportunity is still in building bridges. When globalization strains, it doesn’t end. It decentralizes. It becomes person-to-person, firm-to-firm, state-to-state. The winners won’t just be the biggest or the loudest. They’ll be the ones who can form real partnerships, build trust across borders, and make the relationship itself a strategic asset. Find the bridge-builders. Invest in the bridge-builders. Be the bridge-builder.

Swimming with Allocators is back soon, and you can hear all of Erik’s great insights.
Catch up on past episodes here: https://www.youtube.com/@AllocatorsPod/videos

Her point was simple and heavy at the same time: the way a lot of us are operating right now is probably not healthy, and we will likely see strange downstream effects from it. Not just burnout. Not just anxiety. Real physical stuff. The kind of outcomes that make you stop using the word “lifestyle” and start using the word “risk.”

What hit me is how quickly “connecting” with others has drifted into “performing.” Adults do it all day.

Zoom calls that feel like webinars.
Group chats that replace real conversation.
Quick voice notes that keep things moving but never really let anything settle.

Even the way we FaceTime now can feel like a broadcast. I’ve watched it with my son. He’s seven, and when he calls his grandparents or aunts, half the time he’s not even catching up. He’s in webinar mode. He wants to show them tricks from his media class. He screen shares. He’s presenting.

It’s funny.
And it’s also a mirror.

Because we’re training a generation (and ourselves) to equate connection with demonstration.

It’s less of that slow back-and-forth where you learn someone’s mood. Where you sit in a little silence. Where you ask the second question after the first answer. I’m not blaming him. It’s probably generational. Going through Covid as a young child. Having access to devices early. Being raised by millennials.

But I’m hopeful, especially when I look at the success of a consumer product company a friend invested in called Tin Can. The pitch, as I understand it, is almost laughably old school, where kids ages roughly 5 to 12 want a regular phone experience again. Not a smartphone. Not another feed. Something closer to what we had with corded phones. Just calling people. Just talking. The fact that something like that is “ripping” says more than a thousand op-eds. It suggests the demand for unoptimized connections is not romantic nostalgia. It is a market signal. We miss being with people, and we miss being reachable in a way that does not require us to perform.

The LP also made a second point that connected the human health angle to the private markets angle in a way that should make every fund manager lean in.

Private markets are network-based. Trust-based. Pattern recognition-based. The comfort of home, and your social bubble, is real. But deals do not get made at home. Early stage, especially. The work is embodied. It is eye contact. It is shared context. It is the after, not just the meeting. And if you believe, like I do, that attention is the scarcest resource now, then the analog path is not a retreat from the future. It is a way to compete for attention without contributing to the fatigue of constant digital interaction. Boots on the ground, done thoughtfully, is suddenly differentiated again.

So when I say “most analog firm in a digital world,” I’m not just talking about notebooks, phone calls, and dinners. I’m talking about building a system that respects human limits and human biology. That is where good judgment lives. I’m talking about conversation as a craft, not content as a substitute. I’m talking about a life where I can do the work without frying my central nervous system. And a firm where founders feel something steady when they are around us.

If we are heading into a decade where the body keeps the score for how we lived through this screen era, then the contrarian play might be simple: do as the Gen Z cool kids say, “touch grass.” Or used to say it. I’m old enough now that the slang changes while I’m still using it. Which is basically that SNL bit in real time.

But the advice holds.

Touch grass.

Get in rooms.

Talk with people, not at them.

Build trust where the algorithm cannot follow you.

with gratitude,
e

Lately, I’ve been thinking a lot about talent.

Not hiring.
Not org charts.
Not comp bands.

Talent.

Specifically, whether founders still know how to see it early enough.

And whether they’re brave enough to let it be great, even when that greatness eventually moves on.

Automation is raising the floor everywhere.

Tools are faster.
Execution is cheaper.
Access is wid…

Read more

Last week, a few people sent me a speech from Davos.

I didn’t watch the video.
I read the transcript.

One line stayed with me: Nostalgia is not a strategy.

It sounds obvious. Almost trite.

But the longer I sat with it, the more it felt like a diagnosis.

Not just of geopolitics.
Of venture.
Of investing.
Of leadership.
Of this moment we’re all standing in, whether we want to name it or not.

The speech referenced an essay by Václav Havel, The Power of the Powerless.

Havel tells a story about a greengrocer who hangs a sign in his window every morning:
“Workers of the world, unite.”

The shopkeeper doesn’t believe it.
No one does.

But he puts the sign up anyway.
To avoid trouble.
To signal compliance.
To get through the day.

And because every shopkeeper on every street does the same, the system persists.

Not because it is true.
But because people keep performing it as if it were.

Havel called this living within a lie.

That phrase landed hard.

Because once you see it, you start seeing signs in a lot of windows.

In venture, we have our own versions.

We repeat sourcing and diligence playbooks that worked in 2014 and call it discipline.
We cling to pattern recognition long after the patterns have decayed.
We talk about differentiation while funding sameness.
We say the market will “come back” as if markets have memory or loyalty.

None of this is malicious.

It’s human.

Nostalgia feels like wisdom.
But a lot of the time, it’s just fear with good branding.

The hardest part about this moment is not that things are changing.

It’s that the old stories still half-work.

Brand still opens some doors.
Capital still attracts capital.
Reputation still buys time.

So it’s tempting to keep the sign in the window.

To perform confidence.
To perform certainty.
To perform continuity.

But performance is not the same as truth.

And in investing, living within a lie is expensive.

Being a great investor today requires real adaptability.

Not slogan-level adaptability.
Not “AI-first” adaptability.
But the kind that forces you to re-underwrite your own instincts.

You have to be a real stock picker again.

You have to understand why something is working, not just that it worked before.
You have to get comfortable saying “I don’t know yet” and doing the work anyway.
You have to let go of old signals that no longer predict outcomes.

That’s uncomfortable.

It’s much easier to repeat what once made you feel competent.

But the market does not reward nostalgia.
It rewards intellectual honesty and curiosity.

This is showing up everywhere I look.

In how venture firms are being built.
In how capital is concentrating.
In how trust is being allocated faster and with fewer chances.
In how founders decide who to spend time with.

The old rituals still exist.
But they don’t carry the same weight.

And pretending they do doesn’t make you principled.
It makes you late.

What struck me most about the Davos speech wasn’t its politics.
It was its posture.

A refusal to accept inevitability.
A refusal to confuse realism with resignation.

There was a line about “taking the sign out of the window.”

About naming reality instead of performing comfort.

That feels relevant far beyond geopolitics.

I feel it in venture conversations every week.
I feel it in how founders talk when the cameras are off.
I feel it in how LPs ask questions they didn’t used to ask out loud.

There is turmoil. There is uncertainty.

But I refuse to be hopeless.

Not because hope is naive.
But because hopelessness is passive.

Adaptation is an act of agency.

So is rebuilding.
So is reframing.
So is choosing to create instead of retreat.

That applies to investing.
To firm-building.
To how we show up in our communities.
To how we think about this country and world, even when it’s hard.

We are not obligated to accept decline as destiny.
We are not required to keep performing stories we no longer believe.

Taking the sign down doesn’t mean you have all the answers.

It means you’re willing to tell the truth about the moment you’re in.

And from there, to act.

Slowly.
Imperfectly.
But honestly.

Nostalgia is comforting.

But it is not a strategy.

And I’d rather live in the work of adaptation than in the performance of certainty.

With gratitude,
E

I’ve fallen back in love with this stretch of the calendar.

Late December. Early January. Janus time.

I’ve written about it before, the Roman god with two faces, one looking back, one forward. But this year it’s hitting differently. Maybe it’s age. Maybe it’s responsibilities. Perhaps being wired as a helper for so long makes it easy to forget the experience itself, in favor of the outcomes.

At my best, people have described me as having a kind of boyish joy. Not naive. Not unserious. Just genuinely energized by the work and the people and the possibility of things turning around.

Somewhere along the way, that joy can get crowded out by scorekeeping.
Did I do enough last year?
Did I miss something?
How fast do I need to make up ground?

Culture does not help. Dopamine everywhere. Instant feedback. Everything is framed as urgent, critical, existential, and unprecedented.

And yet.

There’s something beautiful about this season. My birthday is January 9th. Capricorns are the best. I won’t apologize for that. But what I really love is that everyone becomes a Capricorn this time of year.

New year, new discipline.
New plan.
New gym membership.
Strong convictions.
Tickets already bought.
Diet started yesterday.

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Last year, around this time, I did something I don’t do often enough.

I asked for encouragement.

Not the vague kind. The real kind. Stories. Anecdotes. Quotes. Books. Podcasts. The wisdom people carry around and reach for when life gets loud.

I was turning 40, and instead of throwing a big party, I wanted something more useful: a stack. A set of lenses. A few anchors for the next decade.

What came back was a reminder I needed. Momentum is rarely a solo act. The best people I know build in public, but they learn in community.

This year, I read 16 books. My goal is always to get as close to 20 as I can, and I mean real reading, not audiobooks. The number matters less than what it did for me.

Reading slowed my brain down enough to think straight. It sharpened my exceptions recognition. It gave me language for what I was seeing in markets, in venture, and in myself.

Three books stood above the rest.

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A few years ago, I was catching up quarterly with a friend who was a VC based in Austin. We’d trade notes on deals we were seeing. Same cadence. Same markets. Same general stage.

A pattern started to emerge.

She’d bring up a company and say something like, “I love this, but the valuation is insane. It’s basically a coastal deal. Probably makes sense for you in San Francisco, but not for me.”

I heard some version of that sentence multiple times across 2020 and 2021.

And eventually I told her what had been quietly dawning on me.

There is no such thing as a coastal deal anymore.

A “coastal deal” is wherever Sequoia or Benchmark decides to invest.

If that’s San Francisco, fine.
If it’s Louisville, Little Rock, or Minneapolis, that’s fine too.

Once a top-tier founder is building something truly differentiated, geography stops being the defining variable. Capital, conviction, and speed take over.

The borders didn’t disappear overnight.
They just stopped mattering.

COVID made this obvious in hindsight. The moment investors realized they didn’t need a flight to issue a term sheet, regional advantage started to decay. Zoom didn’t just change meetings. It collapsed distance as a gating factor.

What used to be “our backyard” quietly became “anywhere with signal.”

I started thinking about this again recently while watching what’s happened in college football.

Conference realignment and NIL didn’t just reshuffle logos. They erased the idea of protected recruiting territory. There used to be an assumption that certain programs would always dominate their regions. USC gets California. THE (so annoying) Ohio State gets Ohio. Georgia gets Georgia. Alabama gets Alabama. Florida gets Florida.

That logic doesn’t hold anymore.

Now it’s simpler and harsher. If you’re a top program, you recruit five-star and four-star players wherever they are. The internet exists. Money exists. Exposure exists. Borders are optional.

Venture works the same way now.

Regional access is not a moat. It’s a starting point at best.

This doesn’t mean place is irrelevant. Early incubation still has local texture. Communities still matter. Trust still forms in physical rooms.

But the idea that great outcomes are constrained by geography is a relic of a slower market.

What matters now is judgment.

Can you recognize real signal early?
Can you move with conviction before consensus forms?
Can you support founders when the path is still ambiguous?

Those questions travel far better than any ZIP code.

We didn’t lose regional advantage because Silicon Valley got greedy.
We lost it because speed, information, and ambition went global.

And once that happened, the game stopped caring where you were standing.

— e

This week I had a long conversation with my friend Olga, who provides capital formation advisory services for a wide range of experienced and emerging venture and private equity managers. She has the same vantage point LPs do. She sees across strategies, fund sizes, personalities, and performance curves. Her job is to translate a manager’s story into something LPs can evaluate.

And she told me something that keeps replaying in my head.

“Track record matters less than people think.”

It reminded me of what Jay Rongie Wang told me on Swimming with Allocators: LPs really want congruence, but most GPs never show it.

What Olga shared was subtle but powerful. Most managers do their most important work by leaning all the way into what they are best at. Yet the moment they start pitching LPs (and founders), they abandon that center. They widen their story. They generalize their strategy. They contort themselves into something safer. And in the process, they lose their edge.

Olga sees the disconnect every day.
A GP will describe a sourcing loop that is genuinely unique. Or a diligence question set they developed over ten years. Or a post-investment ritual that founders consistently rank as best in class. But when it comes time to pitch, all of that disappears into the same four slides everyone else has. Market. Sourcing. Selection. Portfolio construction. Branding built by committee.

It is the same phenomenon I saw when applying to business school. Stanford GSB had the (in)famous essay: “What matters most to you and why.” Every year, someone would tell you, “Admissions really wants X this cycle.” And people would contort themselves into that shape. But the admissions team did not actually want X. They wanted the most honest and differentiated version of you.

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Cities used to treat innovation like a recipe.
Watch what Silicon Valley was cooking, write down the ingredients, and hope the dish tastes the same.

New incubators. A startup week. A couple of a

ngel groups. A co-working space in an old bank building.
Everyone wanted the same thing. Everyone tried to imitate the same playbook.

But the truth is that most cities never had a Silicon Valley problem.
They had a self-awareness problem.

Because imitation creates strings, I have seen the same pattern repeat for fifteen years.

First, the region decides to invest only in local companies. Then they loosen the rule a little and say outside investors can join, but they must invest inside the region. Then they relax it again and bring in coastal investors, but limit them to only backing local founders. Each step feels like progress, but each step is still anchored to the wrong belief.

You cannot imitate your way into a thriving ecosystem.

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There is a moment on some of my favorite albums where the music fades and the artist just talks. No bars. No polish. Just a thank you track.
That is what this note is.

We are a little over two years into Swimming with Allocators. Eighty plus conversations. Eighty-plus screenshots that will be flying by in the video you see above. And if you look closely, you may notice a running theme. At least ten episodes where I forgot we were recording video. Times when I looked tired in a very real way. And a surprising number of appearances by that gray sweater. It is not even my favorite sweater. I do not know how it ended up becoming the unofficial uniform of Season 2 and 3, but here we are.

What surprises me most is how many people told me not to do this show. They said LPs were boring. They said no one would watch long-form conversations with allocators. They said this part of the industry did not have stories worth telling.

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I had a conversation this week with a technical founder turned VC named Caleb. We started where most technical people start: what’s real and what’s vapor. But quickly, we got to the question that matters for Series A investors right now.

What should diligence look like in an AI world where almost anything can be built and everyone can generate revenue?

The old SaaS metrics don’t hold.
ARR isn’t reliable.
Logos lie.
And the categories blur fast.

So what actually matters?
What cuts through the demo shine, the inflated numbers, and the temporary excitement?

Four markers kept surfacing in our conversation, and they should anchor every traction-stage evaluation today.

1. Token usage as the early smoke test

If your product is actually solving a daily pain point, customers burn tokens.
A lot of them.

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When I first broke into venture, everyone talked about the mafias. PayPal. Facebook. Airbnb. Uber. Stripe. If you wanted to back a breakout founder, you just traced the family tree, found the alumni, wrote the check, and let compounding do its thing. The sourcing map was tight, almost cozy. Predictable.

That era is gone.

AI didn’t just disrupt product cycles. It blew up the sourcing manual. The next generation of founders isn’t spilling out of five familiar mafias. It’s forty-five different companies, labs, collectives, and weird in-between places you’ve barely heard of. Some of the sharpest founders I’ve met lately aren’t ex-FAANG, not YC, not even from the “usual suspects.” They’re coming out of research labs, open-source Discords, insurance API startups that pivoted, or failed consumer apps that somehow turned into infra. The old “who’s your prior” test? It’s broken. Or better yet, more complex.

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There was a time when only the legacy corporates would admit they couldn’t keep up. “We’re too slow, too siloed, too far from the edge,” they’d say, usually right before launching another innovation program destined for the graveyard six quarters later.

This year, something changed. I started hearing the same line from the hyperscalers and high-growth vendors, the folks who used to set the pace. A friend at a leading cloud provider pulled me aside: “We’re getting surprised by where the next AI founders are coming from. Even large pre-IPO private companies and well-known public tech companies are scrambling to map the new crop of native AI enterprise customers.” When the picks-and-shovels crowd starts losing line of sight, you know the market’s moving faster than any one company’s radar.

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Last week, two stats caught me mid-conversation and made me set my coffee down (and almost do a spit take).

1️⃣ There are now more PE and VC firms than McDonald’s franchisees.
2️⃣ In 1994, there were about 120 GPs in venture. Today? Try 30,000.

Let that land for a second. We’ve got more people picking winners than there are golden arches.

And yet, most pitch decks still open with the same hand-me-down script:

“We back great founders.”
“We have unique access.”
“We’re hands-on.”

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When I was growing up, my dad loved the show MacGyver. For those who don’t remember, MacGyver was the kind of hero who could stop a bomb from exploding with nothing but duct tape, bubble gum, and whatever else happened to be lying around. The point wasn’t that he had the best gear. The point was that he could improvise, adapt, and win with whatever was in front of him.

That show stuck with me. A whole generation of us learned the same lesson: sometimes the bomb is ticking, the clock is running out, and all you have is the stuff in your pockets. What matters is whether you can make something work.

Right now, venture capital (and most other client service functions) feels like it’s in its own MacGyver era.

Everyone’s improvising

Most investors I talk to, from emerging GPs to established fund managers to family offices, are duct-taping together systems just to keep their relationships, insights, and deal flow from falling apart. We’ve all got a CRM (or three). We’ve all got some Slack (or Discord) groups, maybe a Notion doc or Airtable base, maybe a Zap or two firing in the background. And now AI (from note-taking to analysis) has entered the mix.

The result is messy. But it’s also a signal: we’re in a moment of improvisation that usually precedes a new category of infrastructure.

Finance had its version of this in the 1970s and 80s. Before Bloomberg standardized financial data, traders were scribbling notes, calling friends, and hacking together whatever feeds they could. The improvisers who survived that era didn’t just make money. They shaped what became the next operating system of the industry.

I think that’s where we are in venture right now.

Relationship arbitrage has never been more valuable

Venture has always been a business of relationship arbitrage. Who you know, who trusts you, and who you can connect has always mattered. But in today’s environment, it matters more than ever.

Markets shift in 30, 60, 90 days. Pricing changes at large enterprise tech companies that used to take a year now happen in a quarter. Founders and LPs are harder to reach, harder to win, and harder to keep close. The noise is relentless.

Which means this: being able to connect more worlds faster is the real advantage. Anyone can read TechCrunch. Anyone can scrape LinkedIn. But not everyone can remember the family office contact who loves applied AI in insurance, introduce them to the operator building a claims platform, and bring in the right co-lead GP who knows the backchannel.

That’s relationship arbitrage at scale. And it’s the only thing AI won’t replace. But maybe it can enhance personal context?

Why CRMs are only 60% solutions

Here’s the reality I’ve come to: off-the-shelf CRMs are only ever going to get you to 60% of what you need. They’ll store contacts, maybe log emails, and spit out some reminders. But relationships aren’t static. They’re living, dynamic, and deeply personal.

Every investor has their own workflows, quirks, and style. Some want tags, some want lists, some want nudges. No two people track relationships in exactly the same way. Which means no static CRM can ever give you the full picture.

But now, with AI, we’ve finally got the tools to build to 90%. Personalized, adaptive, evolving systems that actually work the way you think.

I’ve seen this firsthand. For roughly $200, in about nine days, I hacked together my own system I call Constellation, with Replit. My CRM plus Notion plus my Fathom AI notes plus GPT plus a few zaps. It’s duct tape and bubble gum, but it works (like a 6-year-old) to remind me of what I’ve learned and who I should connect with or what I should ask for. And the deeper I go, the more I see how much energy it gives me to keep moving through the uncertainty of building Stresswood.

Because here’s the truth: I always assumed I should use technology to patch my weaknesses. Missed follow-ups, scattered notes. But what if the real advantage is using technology to amplify your strengths?

That’s the revelation.

A long obsession, coming full circle

This isn’t a new fascination for me. My failed founder attempt fifteen years ago was a startup built around cultivating better networks. At the time, we had predictive analytics, some data scraping, maybe a LinkedIn export. It wasn’t enough. The tools weren’t there yet.

But I’ve never stopped being obsessed with this question: how do you actually connect and cultivate relationships at scale? How do you bridge the worlds that don’t talk to each other, and do it with intention?

That’s what pulled me into equity research at the start of my career. That’s what I’ve carried into venture. And now the technology finally exists to make it real.

Why this matters for the next cycle

The MacGyver era won’t last forever. The duct tape and bubble gum solutions will give way to more standardized platforms. But the improvisers who are experimenting now will be the ones who define the blueprint for what lasts.

In venture, that means:

• LPs and GPs who build relationship intelligence into their DNA will have an edge that compounds.

• Firms that treat relationships as infrastructure, not afterthoughts, will win the trust wars.

• Emerging managers who embrace messy improvisation now will grow sharper instincts for the next operating system.

I believe we’re on the cusp of a new category: the Bloomberg Terminal of relationships. It won’t look like LinkedIn. It won’t look like Salesforce. It’ll look like a living system built for how humans actually connect and compound trust.

Closing

So yes, right now, it feels like the bomb is ticking and all we’ve got is duct tape, bubble gum, and a half-working Airtable base. But that’s exactly how new eras begin.

Because MacGyver wasn’t about the tools. It was about the ingenuity to use them in ways nobody else thought of.

And in venture, that ingenuity isn’t optional. It’s survival. And survival is producing industry-leading returns.

Everyone in venture capital loves to talk about ambition.
Not enough people talk about runway. Personal runway. Emotional runway.

When I explain what I’m building with Stresswood, I break it into four workstreams:

1. Building a supreme team

2. Building trust with two stakeholder groups that matter most, elite founders and LPs

3. Adding to a clear, relevant track record through larger, targeted SPVs

4. And maybe the most important: building my own personal runway

That last one doesn’t get enough airtime.

Being a fund manager is often framed as a prestigious job for people who have already made it. For many of us, especially emerging GPs, we don’t have that flex. Venture Capital is a profession. And a high-stakes risk. Particularly if you’re the primary earner or the one in your family with the most economic potential. That’s many of our (read: emerging managers) realities.

I’ve said this before: you can truly test your ambition only when your basic needs are met. Maslow’s hierarchy is still the blueprint. Physiological needs, safety, belonging, esteem, and self-actualization. Most people only think about the top tier when they talk about entrepreneurship. But if the bottom layers are shaky, if you’re worried about mortgage or rent, burned out, or disconnected, your decision-making warps.

You rush.
You pick the wrong LPs.
You perform before you’re ready.
You take the safe, compromising deal over the risky, right one.

That’s not a strategy. That’s not intentional. That’s survival.

For me, personal runway is both financial and relational. It’s two years where I can breathe, bet big, and build Stresswood with intention. It’s why I’m advising, consulting, and doing targeted part-time work, not just to pay bills, but to deepen the relationships that will matter when it’s time to raise.

Your version of personal runway might be different, such as emotional stability, time with your kids, or time without them. Whatever it is, you can’t ignore it. You can’t borrow from your foundation and expect your firm to stand.

This work demands hustle, grit, and an obsession with the craft. It also demands margin.
And margin requires means.

That’s not weakness. It’s wisdom.

—Earnest

We spent a decade in the growth-at-all-cost era.
ZIRP, blitzscaling, DTC darlings, or whatever it took to go up and to the right.

Then the tide shifted.

Founders were pushed to grow without the infrastructure or discernment to build lasting businesses. From a venture perspective, that created companies too expensive to acquire and too shaky to take public.

You don’t want your exit to peak with the press release.

However, something else is now happening.

We’re entering what feels like a new era: productivity at all cost.
AI is powering a lot of it. Tools are smarter. Teams are leaner. Job reqs are held to new standards: “Don’t post it unless you can prove AI can’t do it.”

Productivity is good until it becomes the goal itself.
When we stop asking where humans still scale best, we risk erasing the layer that creates enduring value.

The human layer.

I was talking with a friend who works across marketing and AI, and he mentioned how much this moment echoes the 1950s and 60s.

GE. Disney. Those futuristic commercials that promised automated homes, robotic appliances, and dishwashers that would give you your life back.

The message?
You are brilliant, but your brilliance is wasted on the mundane.
Let machines handle the rest.

That dream lingered. But what we got instead was a rising productivity bar, intensified expectations, and deeper burnout, with no meaningful expansion of time to actually think.

So now the question is:
Will this era be any different?

As someone building a fund, I know where I’m placing my bet.

On leaders who know how to leverage technology in the service of human brilliance.
On founders who understand that creativity, resilience, and empathy don’t appear in LLMs, but they scale effectively when invested in.

We’ve automated the mundane.
Now let’s see if we can reclaim the sacred: time, presence, and the kind of thinking machines can’t do.

-e