Becoming a venture capitalist is a very weird story for almost everybody. It’s a rare subset of finance where people stumble into it rather than taking a well trodden, planned path, for the most part. That was true for me.

My investing career started in earnest when I discovered AngelList in 2015. I started to invest small checks into SPVs, got obsessed with researching and finding new companies myself, and decided that I should be the one leading the SPVs.So I launched a few SPVs on AngelList, and suddenly I was considered to be an investor. My operator profile was growing quickly too - at this point, I was also leading revenue at Tinder as it became the top-grossing app in the world. A few of my SPVs started to do well, and I was building my brand online primarily through sharing a bunch of random things on Twitter. Index Ventures asked me to become a scout.

I was flattered because my 19 other peers in the program were really incredible operators, including Dylan Field from Figma. I knew that I had to take this seriously if I ever wanted to become a venture capitalist, and so I became pretty competitive about the entire thing and presenting like a professionalised venture firm. I created a firm name, which was Chapter One, did a little bit of branding work, and launched a website. I also developed a thesis and began to publish my investing ideas online.

It paid off because people started to look at me as being more than just an operator. I was still at Tinder but some even saw me as being an investor first. My scout program portfolio at Index Ventures was very successful. I invested in the seed rounds of Mercury (now at $3.5B+ valuation), Turing (now at $2.2B+ valuation) and The Graph.

The fund was marked at a 14x MOIC (multiple on invested capital) with 4x DPI (distributed to paid in) in 3 years — one of the the top performing funds in the program. Those results mattered because they proved to LPs that I could actually do this when it came time to raise capital for Chapter One.

I’ve always thought of that scout program as the moment I became an investor. It took me from operator-who-angel-invests to someone with a real portfolio and a real track record. And ever since, I've been thinking about what was missing from the experience, and how to build on it. The path from operator to investor is opaque and exclusive and there needs to be a better way to surface investing talent.

Most scout programs have three problems:

1. Access is closed (you either know a GP who invites you, or you don’t)
2. Performance is hidden (scouts can’t build public track records or reputations)
3. The programs are designed to create leverage for firms, not for scouts.

That’s what we’re changing.

Today we’re launching Scout Program: www.scoutprogram.com.

The big twist is that we’re letting everybody apply. No GP invite required. We select 10 scouts each season from a global applicant pool, and each scout gets $100K in real capital to deploy into early-stage startups.

This is a season-based competition. Every scout creates a public profile with their own fund name, investment thesis, and real-time performance tracking - just like I did during my own scout days. There’s a live leaderboard that tracks value throughout the season.

Beyond deal performance, the leaderboard rewards the full picture — how you build your brand, how you run your back office, how you operate like a real firm. The top performer walks away with carry, a track record that speaks for itself, and a clear path to managing their own fund.

We also want to make this more social and give scouts a real platform to build their careers. Think of the profile as the best resume an aspiring investor could have by showcasing investments, thesis, and portfolio updates all in one place.

We’re surrounding our scouts with a world-class mentor group from firms like Khosla Ventures, Union Square Ventures, and Kleiner Perkins. We’ve brought together some of the most legendary investors in the business, and a group of LPs who can offer perspective on firm-building, for the scouts who ultimately want to go that route:

• Mamoon Hamid, Partner at Kleiner Perkins

• Keith Rabois, Managing Director at Khosla Ventures

• Rebecca Kaden, Managing Partner at Union Square Ventures

• Kyle Samani, Founder at Multicoin Capital

• Roger Ehrenberg, Managing Partner at Game Changers

• Gokul Rajaram, Founding Partner at Marathon

• Tomasz Tunguz, General Partner at Theory Ventures

• Ashton Kutcher, General Partner at Sound Ventures

• Laura Andron, Managing Director at Pathstone

• Kelli Fontaine, Partner at Cendana Capital

Season One kicks off March 14th, 2026. Applications are open now at www.scoutprogram.com.

Aspirationally, this is the Thiel Fellowship for investing. Let’s see if we can get there.

I’ve been reading Who Knew by Barry Diller this week. He’s the chairman and senior executive of IAC and Expedia Group, and before that he founded Fox Broadcasting with Rupert Murdoch and built USA Broadcasting, essentially shaping modern television.

I had the chance to meet Barry twice during my early days at Tinder.

The first time was three days before Christmas in 2015. I was still new at the company and trying to make a name for myself, so I showed up on December 22nd with just a few others.

“Who’s that guy in the tracksuit?” one of our youngest engineers asked, looking up from his monitor.

I glanced over and saw Barry Diller, owner of IAC and one of Tinder’s biggest shareholders.

I didn’t know it at the time, but Barry — then 75 years old — had a tradition of visiting the Tinder office right before Christmas every year. He’d walk the floor asking questions, genuinely curious about what everyone was building.

I watched him approach one of our engineers and ask, “What are you working on?”

The engineer started explaining what he was doing in very technical terms, and Barry listened without interrupting. I don’t think the engineer knew who he was because if he did, I’m pretty sure he would’ve been a lot more nervous explaining his code!

A year later, in 2016, I made sure to be in the office those same few days before Christmas. The office was mostly empty again and we had just moved into a much larger space.

Sure enough, the guy in the tracksuit showed up again, right on cue. Barry Diller.

He made his rounds, saying hello and asking the few of us still in the office the same question: “What are you working on?”

One of the central themes of Who Knew and of Barry’s career is his obsession with understanding how things work at the most fundamental level.

Only if I slowed everything down could I begin to understand all the parts and then try to rearrange them into something coherent. I tend to make things worse in the beginning as I fumble around trying to get to basic truths. Instinct, which I prize almost all else, doesn’t work very well for me in abstruse matters.

I have to get to the core DNA on any matter, its logical essence, before I can add anything of value. This takes a lot of time, often to the irritation of faster thinkers, but when it does crystallize, I can’t be deterred.

I listen with an extra ear, highly attuned to hear a new truth among the cacophony of voices in the room. When I catch that note, no matter what I might have thought before, I’ll change course in a second.

If I’ve ever had any kind of secret sauce, it’s the ability to hear conflicting, creative ideas bombarded around the room and extract something valuable. Recently in a meeting, someone complained that I wasn’t being consistent. I replied that I’m never consistent; I’ll turn on a dime if I hear a better truth.”
- Barry Diller, Who Knew

Looking back, I realize that when he asked what we were building, it wasn’t about big timing us or management control. It was pure curiosity.

Most leaders want to look smart. Barry wanted to get smart and understand the smallest molecule of what we were building as engineers and product people, even on the sleepy days before Christmas.

Because the best investors and leaders don’t chase outcomes. They want to understand the wiring underneath.

Show up, ask questions, and keep asking until it makes sense. The tracksuit is optional.

Sunday morning, and my neighborhood WhatsApp is at it again.

Citizen screenshots. Garage break-ins. Strangers loitering on Ring.

Not long ago, these friendly neighborhood chats were about escaped Bengal cats, second-hand car seats, and block parties. Life was good!

But unfortunately our babysitter board has become a digital precinct patrolled by parents who tuck kids in at night, then moonlight as amateur detectives.

Welcome to the new neighborhood watch.

If you live in a major U.S. metropolitan city, you probably already know what I’m talking about.

Chances are you’re part of your own “neighborhood watch” group and if you’re not, maybe you should consider starting one.

For us, our neighborhood watch started a year ago, after a mother was brutally attacked while pushing her newborn through a nearby alley.

Three local moms knocked on doors, asking neighbors to chip in for round-the-clock private security. Sixty households signed up at $400 a month. Now patrol cars sweep the streets day and night, and a fragile sense of safety has returned.

Another neighbor donated part of their yard to mount a Flock Safety license plate reader. Frustrated people in in our neighborhood (mostly parents) passed the hat so we could split the subscription.

At my own house, I swapped Ring for Deep Sentinel. 24/7 remote surveillance with live guards backed by AI that makes Ring look like a toy. Yes, another subscription. Yes, worth it.

We started arming up with the best tech we could find to keep the block safe. Most of it came from scrappy startups.

Defense tech isn’t just for governments anymore. It’s coming to the cul-de-sac.

After “arming up” with tech, we thought we were okay.

But this summer, at 7 a.m., a homeless man randomly attacked a neighbor’s gardener with a piece of lumber and sent him to the hospital, on a family street where kids ride scooters.

Yes, that sentence sounds absurd if you read it again. But it’s real and happening in a city where we pay the nation’s highest taxes.

My friend Braden (the homeowner) quickly shared a Ring camera image of the guy in our neighborhood WhatsApp group. He’d fled the scene and we needed everyone to be on the look out.

Six hours later, a different neighbor spotted the attacker in a nearby park during their commute home from work and sent our group chat a message with a photo.

Braden linked up with private security and literally ran him down like something out of a superhero movie, while another neighbor dialed 911 and gave his location. Security beat the cops to the scene and held him til they made the arrest.

Without our modern day neighborhood watch, he’d probably still be out there.

This isn’t just Los Angeles.

Across America, taxes are up and public services are down. Anyone who actually lives in a major US city feels it, no matter how many press conferences insist “crime is down” and “the data proves it.”

Parents in our neighborhood don’t expect perfection. We know cities are messy, and we’re not naive enough to think it’s ever going back to some 1950s postcard. But we do want safe sidewalks, clean parks, and kids who get to grow up as kids. Too often, even that feels out of reach.

So we build our own solutions. If we can’t fix the world, we’ll start with the sidewalks and streets where our kids take their first steps.

Our neighborhood watch wasn’t meant to be the cavalry. But when no one else rides in, you fire up the group chat and saddle up.

I ran into an investor friend who was summering in California. He ordered a glass of Santa Barbara pinot and told me: “I didn’t drink for a year. Then on New Year’s I woke up and realized how boring my life had become. So I had a few drinks that day, and suddenly life had color again.”

When I asked why he quit in the first place, the answer was simple: better sleep, fewer distractions, full immersion in work.

He’s the type who goes all in, which is part of what makes him world-class. So when he discovered longevity, he didn’t dabble. He installed a hyperbaric chamber, bought an infrared sauna, and swapped happy hours for tennis matches.

A year later, he’d landed on a middle ground. Still disciplined, but now sipping a couple of glasses of wine. Nothing extreme. And he seemed lighter, even happier.

Listening to him explain his new regimen, I realized how far we’d drifted from our twenties. Back then it was shots of top-shelf tequila. Now it’s top-shelf supplements and IV shots of NAD+.

In Los Angeles, status used to mean a G-Wagon in the driveway, a Nobu reservation, a Riviera golf membership, or a Bird Streets house “next to Leo.”

That game isn’t gone, but the subtler flex now looks less like Rodeo Drive and more like a medical lab.

The question isn’t “What car are you driving?” It’s “What’s your protocol?”

Designer closets have given way to microdosing GLP-1. Hollywood Bowl tickets have been swapped for Hyrox race entries that sell out faster than Coachella.

Bryan Johnson, Andrew Huberman, and Peter Attia are the new A-listers. Nobody’s quoting movies anymore, but everyone’s comparing T levels.

In tech WhatsApp groups, biomarker screenshots now circulate with the same energy Porsche waitlist confirmations once did.

Even the biggest celebrities have joined in, turning their “health journeys” into content. In August, the Kardashians flew to Mexico for stem-cell therapy banned in the U.S., a ban that only made it more exclusive. Naturally, it became both an Instagram flex with a million likes and a tabloid headline.

Part of it is just age. My friends are getting older, and the ones with early-adopter instincts—and money—have found a new playground in personalized medicine.

The same people who once hunted obscure apps or underground music are now swapping supplement stacks and sleep hacks.

COVID accelerated it. Locked indoors, people built home gyms, experimented with diets, and turned longevity from a fringe hobby into a mainstream obsession.

The old signals also got boring. A Ferrari says money. A cold plunge says enlightenment.

And it’s not only millennials and middle age.

For younger New Yorkers, longevity isn’t about hacking DNA. It’s about escaping the chaos of city life and maybe finding a date.

On Saturdays, Bathhouse in Tribeca is the new brunch table. Forget bottomless mimosas. The real weekend move is sweating with strangers and hoping your soulmate shows up somewhere between the sauna and your third cold plunge. Contrast therapy is the new Tinder.

Sure, the longevity craze might look ridiculous from the outside at times. But it’s ridiculous with benefits. A Patek Philippe watch tells you the time, but an Apple Watch tells you your heart rate, sleep score, and how much stress you’re under.

At some point in my thirties, I realized health is the best ROI. Lose it and you’re only half-present at home, at work, and everywhere in between. I’d take a Prenuvo scan over another luxury purchase any day. Health compounds; things depreciate.

But like my friend who found a middle ground, I’ve come to see that joy matters too. Sometimes longevity means the glass of wine, the night out, the moment that keeps you human.

The old adage was that money can’t buy time. These days, that may no longer be entirely true.

Now excuse me, my biomarkers are waiting.

Every weekend, there’s a new “hero” tweet that takes over venture capital group chats.

This past weekend was clearly slow on the news front, because what I initially read as a fairly standard take ended up dominating my timeline.

The tweet came from Martin Casado, GP at Andreessen Horowitz, who runs their $1.25B infra practice:

The idea that non consensus investing is where the alpha is, is actually quite dangerous in the early stage. Follow on capital tends to be more and more consensus aligned.

For whatever reason, this concept triggered a bunch of investors.

We’re living in an era where the “consensus categories” like AI, robotics, crypto, bio, defense, autonomous systems, manufacturing are big enough to carry entire generations of startups. You don’t need to invent a new category to generate massive outcomes.

It wasn’t always like this. For decades, VCs sat around waiting for the one platform shift (PC, internet, mobile). Now? We have five or six happening simultaneously.

When I started angel investing in 2014, venture capital felt predictable.

Mobile was exploding, on-demand apps were raising boatloads of money (usually with terrible unit economics), and cloud was starting to compound. It was the perfect era to learn the ropes and see how quickly categories get crowded.

Martin’s larger point, as I read the tweet and the replies, is that very few categories are truly non-consensus anymore. Our industry has matured.

Some investors are better at sourcing, picking, and winning. That doesn’t make them “non-consensus”. It just makes them great.

Yes, you can still find non-consensus companies inside consensus categories. But at some point, calling ourselves “non-consensus investors” is just glamorizing the job.

Take American Dynamism as an example, a venture category branded just a few years ago by A16Z that now feels like an industry in itself.

Palantir (2003)
Truly contrarian. Nobody else was building forward-deployed CIA software. Palantir was a one-of-one company that probably only Alex Karp, Joe Lonsdale, and Peter Thiel could have created. Two decades later, it’s more relevant than ever with a $370B market cap.

Anduril (2017)
Equally contrarian, but for different reasons. At the height of Trump-hate in Silicon Valley, backing autonomous defense systems was a career risk. Elad Gil has said he actually got furious emails from friends after his Anduril investment became public. Today Anduril is a decacorn. Only eight years ago, it was radioactive.

2025
Fast forward and American Dynamism is a full-blown investment category. Hundreds of startups and dozens of funds are chasing defense, aerospace, and manufacturing. I live 15 minutes from El Segundo which has famously become a dense hub of these companies.

Today’s defense investors aren’t contrarian. It’s one of the most consensus categories you’ll find.

Does it matter? Not really. Some companies will hit. Most won’t. That’s venture capital.

Today, being non-consensus means cutting through the noise, tuning out VC group-chat gossip, and backing the startups that still feel too weird or risky, even if their category already feels crowded.

In other words: being a non-consensus investor inside consensus.

Crypto is the perfect example. It’s a $2.5T market, Bitcoin’s been running for fifteen years, and BTC + Ethereum already settle trillions annually. By any standard, it’s consensus, yet still widely misunderstood.

Plenty of VCs (especially in the Bay Area) still can’t see past the FTX blow-up in 2022 even three years later.

Meanwhile, Stripe is betting its roadmap on stablecoins, even building its own payments-focused L1. And Robinhood, now a $95B company, is basically a crypto company in disguise.

The paradox is that crypto is consensus as a category today to those who pay attention, but the opportunity is to be non-consensus about its timing and trajectory while making bets that most investment committees are too slow or scared to underwrite.

Peter Thiel is piling money into Ethereum right now while most of Silicon Valley is still trauma-bonding over FTX.

Martin’s observation hit a nerve because it points to something structural:

“Follow on capital tends to be more and more consensus aligned.”

Growth investors aren’t less imaginative, they’re more efficient at finding outliers, and they have massive funds to deploy. Sure, that makes venture feel less romantic. When you’re managing tens of billions, romance doesn’t scale.

More importantly, the best companies are known earlier than ever. Scouts spray $25K checks, report back to their multi-stage overlords, and any information edge evaporates within minutes of a founder update.

Sub-verticals become consensus at lightning speed. AI legal, AI healthcare, AI customer service. There are few secrets in Silicon Valley anymore.

VC right now is noisy AF. If you’re running a contrarian playbook and it works, you deserve the win. But most VCs aren’t Peter Thiel.

I came across a thread last week reviewing 61 (!) AI coding agents and sent it around to my teammates at Chapter One.

We already knew the category was crowded, but seeing dozens of venture-funded startups lined up with screenshots made it feel ridiculous.

“I’ve tried all 61 AI coding agents & IDEs: Emergent, CodeRabbit, Cursor, Copilot, Replit, Devin, Github Spark, Figma Make & more.”

The author included this emoji in the headline:

Accurate. That’s exactly how it feels to be a seed investor right now.

After about two minutes of that thread, I wanted to clear my head and jump in the Pacific Ocean for a cold plunge (though at this point, does taking cold plunges make me consensus?).

I can count the number of truly non-consensus investors on one or two hands. Not because the rest aren’t smart (in fact many are really f’ing smart), but because venture is now hyper-networked, hyper-efficient, and hyper-competitive.

Alpha is still out there. But it doesn’t come from LARPing contrarian. It comes from knowing what you believe in and moving faster than others.

It comes from sitting through thousands of meetings that mostly feel like wasted time. From enduring dry spells where you wonder if you’re even good at this.

Then one day, you meet a truly special founder. That’s when it matters to move faster than the funds waiting for their Monday partner meetings. To decide, commit, and win the right to invest before the market catches on.

And it will catch on fast if you don’t.

In the rarest cases, you’ll back founders who invent categories so big they look obvious to Sand Hill Road only in hindsight. But that isn’t usually about being “consensus” or “non-consensus.” It’s a messy mix of hard work, skill, and luck.

In 2025, venture capital is hyper-networked and hyper-efficient. Scouts live-tweet deal flow. Firms pitch LPs on “unique access.” Everyone swears they’re contrarian.

Behind the noise, the truth is it’s harder than ever to be non-consensus. But it’s also the most exciting time to invest.

There were years when we all sat around waiting for the next platform shift. The number of incredible companies being built right now is staggering.

Anyway, I should stop writing and get back to work. Another legal AI deck just hit my inbox.

Loyalty.

By now you've likely heard the news: Windsurf was acquired—not once, but twice—in a single week.

If you somehow missed the headlines, here's the quick rundown:

Last week, Cognition AI, the startup best known for its AI-powered coding assistant, announced its acquisition of Windsurf.

This came on the heels of Google's controversial $2.4 billion deal the previous Friday, acquiring Windsurf’s top executives and licensing its core technology, while leaving the company itself and most of its employees behind.

Loyalty.

The Windsurf saga—two rapid-fire acquisitions, executives parachuting out, employees left stranded—isn't just another juicy Silicon Valley story. It exposed a deeper fracture in how we think about commitment and trust in startups.

At the center of controversy is Windsurf’s CEO, Varun Mohan, accused of negotiating deals that richly benefited himself and an inner circle while leaving loyal, early employees out in the cold.

It must be noted that Varun faced limited options: OpenAI’s acquisition attempt had already collapsed due to Microsoft’s contractual IP entitlements, which left Windsurf effectively “unacquirable” by any major player.

You've probably heard multiple perspectives by now, and I don't pretend to know all the details. Passing judgment on Varun’s decision isn't my intent, nor is it my place as a venture capitalist. But I do think we should examine how the incentive structures—not just the individual choices—shape these outcomes.

Loyalty.

Today’s AI startup ecosystem mirrors professional sports more closely than many realize.

Consider college basketball: In 2025, over 2,300 players entered the transfer portal—nearly half of all men's college basketball players. Five years earlier, it was fewer than 1,000.

Silicon Valley reflects a similar transformation, where top AI researchers and engineers are entering the tech transfer portal everyday.

The dopamine rush of perpetual free agency is more enticing the satisfaction of sticking with one team. And the potential of overnight wealth creation, especially during the current AI gold rush, encourages founders and employees to maximize short-term individual returns rather than build enduring value.

But this dynamic becomes troubling when it fractures the unspoken social contract between founders and their teams.

Founders are uniquely privileged to convince top talent to spend their most valuable years helping build their own visions and dreams. Often, this means asking them to walk away from higher salaries or more secure paths—anchored only by the promise of equity and long-term upside. When that contract breaks, it undermines the trust that startups are built on.

In Windsurf’s case, the Google licensing deal and Cognition’s follow-on acquisition ultimately delivered partial payouts and preserved jobs for remaining employees—but only after lots of uncertainty and backlash. The precedent is slippery: if future founders believe they can extract value via licensing or team lift-outs without a full exit, it could normalize a model where employees are last to benefit. Similarly, when tech giants like Facebook poaching AI talent, it underscores why employee loyalty has waned so dramatically in the AI era.

Loyalty.

AI’s free agency era is here.

Imagine a 22-year-old OpenAI researcher yelling “SHOW ME THE MONEY!”—not at Tom Cruise, but at Mark Zuckerberg, mid-DM, while wearing a Meta headset.

My friends at TBPN have fully embraced the “AI free agency” era—posting real-time updates of top researcher moves on Twitter like they’re Shams Charania reporting blockbuster trades. All that’s missing is a Woj bomb and an Arxiv highlight reel.

But honestly—why should employees stay loyal when founders are the first to jump ship for a bigger payday?

The problem isn’t just individual—it’s structural. If a founder can cash out by licensing IP instead of building the company to a real exit, the system doesn’t just permit it. It incentivizes it.

Silicon Valley’s game of musical chairs now includes everyone, even founders of billion-dollar startups with hundreds of employees and nine figures in the bank. The same founders who once sold a “lifelong mission” are now stepping away the moment a better seat opens up.

In the race to AGI, careers have become liquid assets—negotiable, transferable, and always up for sale to the highest bidder. Founders and employees alike are just playing the market.

Still, I believe loyalty—especially from founders—is essential if Silicon Valley wants to preserve what once made it special.

But loyalty won’t return through nostalgia or wishful thinking. It requires structural change: aligned incentives, real employee protections, and deal terms built on transparency, not clever loopholes.

Without that, we risk losing the collaborative spirit and shared upside that once set this industry apart.

I spoke yesterday with one of the most talented product designers I've ever collaborated with, and something he said stuck with me: "I feel old."

He's 37 years old, an age when professionals in most fields are entering the prime of their careers.

But today he's witnessing the AI-driven product design landscape reinvent itself in a language he hasn't yet learned.

He arrived at my desk seeking advice. Two near misses for executive roles at the center of AI had him reeling and downtrodden over espresso. Should he target Series A startups? Update his resume? Find something this summer?

My answer: Start designing again.

Pick a model on Hugging Face.

Experiment with GPT-4, Claude, or Gemini.

Take an app from 2015 and reimagine it with an AI-native products lens. What does Evernote look like with a super intelligence behind it? How will restaurateurs experience the next Yelp? And what might influence look like on the next Instagram?

The punchline: build whatever inspires you, but start experimenting again.

Do you feel the world accelerating past you? It is. My first awakening to this two years terrorized me until I started building. So now I wake up every day and choose to build.

Sergey Brin recently came out of retirement recently and said:

"This is the most fun I've had in my life.” Also that “this is the greatest transformative moment in computer science ever.” Not one for hyperbole he added, “is the most exciting thing of my life technologically."

Did you see Jony Ive is teaming up with OpenAI to create new consumer hardware and go after Apple?

Those guys love the game. They’re competitive athletes.

They’re wondering if they still have the skills to win in this new AI world. And they can’t know without building things. So they’re trying.

The coolest part about this moment is that one great product idea can make you relevant again.

You see it almost everyday now on X.

Someone builds a product using new technology in their free time. Messing around, they release it online. People love experiments. One goes viral. The product design community starts talking about it. Boom. They’re back in the game.

It’s like a musician releasing a song that makes them popular again. That’s what you need to do if you’re feeling lost as a product person or designer right now.

We’re living in historical times and the game is just getting started. Now is your time to fall in love with technology again.

—

Thank you to reader William Johnson for the feedback and edits. You improved this essay immensely.

It’s now obvious to most builders and investors that AI Agents are the new platform shift.

We’re in the early innings and seeing major breakthroughs in reasoning and chain- of- thought (CoT) everyday.

Frameworks like LangChain are driving rapid agent development, while software giants like Anthropic and Google are explicitly exploring agent-to-agent (A2A) communication paradigms.

From my vantage point as an investor, what’s most fascinating is how agents are beginning to operate with real autonomy. They aren’t just copilots anymore—they’re becoming decision-makers, even in enterprise software procurement.

Agents selling software to other agents sounds dystopian, but it’s not far off.

The traditional B2B sales cycle—built around human relationships, months-long funnels, and enterprise steak dinners—will give way to A2A transactions, where procurement is algorithmic, fast, and deeply rational.

We’re already seeing glimpses of this future.

Companies like Replit, Lovable, Bolt, and V0 have strong opinions about the infrastructure best suited for AI-driven applications. But the next step is agents deciding on that infrastructure without any human involvement. They’ll pick the tools that solve the problem fastest, cheapest, and most securely—no procurement team required.

Chapter One portfolio company Supabase is a perfect case study.

Just yesterday at Figma Config—now arguably the design conference of the year—Figma announced Figma Sites, with Supabase as the default backend.

In just over three years, Supabase has gone from open-source Firebase alternative to the database of choice for over 2 million developers. But more importantly, it’s begun winning embedded integrations inside app-building platforms. That’s a new level of distribution.

Look at the insane Supabase growth chart over the last 6 months as they’ve reached 2m developers:

Now imagine when infrastructure decisions—like picking a database—are automated by agents.

Supabase isn’t just the human choice. What happens when it becomes the agent’s choice, too?

That’s what makes the Supabase growth chart so interesting.

It doesn’t just show developer adoption. It marks the decline of enterprise sales theater.

For the last 15 years, software buying has been shaped by steak dinners, Warriors suite invites, and Napa boondoggles. Fun? Sure. But efficient? Not at all.

That world is fading.

Software procurement is becoming algorithmic, precise, and refreshingly impersonal. The best product wins, not the best schmooze.

My friend Tomasz Tunguz (Theory Ventures) captured this shift perfectly this week:

If I ask an AI agent to create a web application, I want it to select all the components : the front end framework, the database, & the hosting service. I just want the website to work.

The agent won’t pause to ask, “Do you have a preferred vendor?” busy reasoning about the task at hand, it will continue on its code path, hurtling towards an answer

It’s tempting to assume agents will optimize purely for performance-to-price—like today’s cloud pricing wars. But it’ll be far more complex.

These decisions will hinge on model compatibility, explainable actions, regulatory compliance, and privacy guarantees.

Securing these interactions—especially when proprietary algorithms or sensitive datasets are involved—will drive real innovation in applied cryptography.

Expect zero-knowledge proofs and blockchains to move from niche crypto tools to essential infrastructure for trust, verifiable identity, and seamless value exchange in an agent-powered world.

Take CRM, for example.

If you were building an agent-first CRM today, it wouldn’t resemble anything we use now. It would be designed from the ground up for machine-to-machine interactions.

The APIs would be lightning fast. No UI overhead. No human latency. Just clean, efficient data exchange.

It would integrate natively with major AI ecosystems so agents could coordinate across teams and platforms.

Analytics would be built not for dashboards, but for agents to evaluate and improve their own performance.

Compliance wouldn’t be manual. It would be encoded in the system so agents could self-regulate based on pre-defined policy.

Pricing would be dynamic and negotiated in real-time between agents.

This is what it means to stop building for human operators, and start building for agents.

Many assume AI’s economic upside will be captured by a handful of tech giants.

But if you’ve worked inside a place like Google, you know how innovation gets buried—under legacy code, bloated org charts, and teams too far from the frontier.

As Tom said: “AI will be the Chief Procurement Officer.”

Software won’t be sold over drinks. It’ll be selected, evaluated, and integrated by agents.

Most incumbents won’t adapt fast enough.

That’s the opportunity for founders and investors who see what’s coming.

If you’ve got product instincts, this is the most exciting moment in startup history to build.

We build beautiful narratives about our values. We tell stories about what matters—local manufacturing, sustainability, ethical production.

We imagine ourselves as conscious consumers, making choices aligned with our highest principles.

But what happens when the checkout page appears?

One of the most important lessons I've learned in my product career is that when getting user feedback — people’s words rarely match their actions.

Maybe you’ve heard the concept of “stated preferences vs. revealed preferences” before. It took me years to fully understand this, but now I think about it all the time.

Stated preferences are the feel-good stories people tell themselves—and us—about what they value and what they will choose.

Revealed preferences are the blunt truths exposed by their actions, especially when money or convenience is at stake.

I was again reminded of this framework last week amid growing conversations about bringing manufacturing back to America.

Ramon van Meer, a former Shark Tank contestant, shared an A/B test that captured a lot of attention.

His company, Afina, sells a popular filtered showerhead made in China for $129. When tariffs surged to 170%, Ramon’s team explored reshoring production.

They found a domestic supplier, but the price jumped significantly to $387, nearly triple the original cost. They tested it anyway and even subsidized some of the cost by listing the USA-made version for $239.

The results were striking:

• Not one person chose the American option

• Less than 1% even considered it worthy of their cart

• 3,500+ people chose the cheaper import

We're all unreliable narrators in the economic stories we tell. We craft identities as ethical consumers while our fingers tap "add to cart" for the cheaper option.

Consumers might be willing to pay a premium for the "Made in America" label, but clearly not a 3x markup.

Of course, not all industries carry the same weight. Domestic manufacturing in critical sectors—like medicine or semiconductor chips—might justify the higher cost in exchange for greater security and control over our own destiny.

Consumers might readily accept paying more for medicines or gradually absorbing embedded costs in technology components. Showerheads, shoes, and everyday goods, though? That's a tougher sell.

Van Meer summed it up candidly:

We want to bring back domestic manufacturing. But when faced with the real cost, consumers didn’t bite. It’s not that they don’t care—it's simply that they’re not willing to pay the premium. At least, not yet.”

The most fascinating question isn't whether manufacturing should return to America.

It's whether we can evolve into consumers whose actions align with our aspirations—or whether we'll continue living in the comfortable space between what we claim to value and what we're actually willing to pay for.

Many Americans wave the flag for domestic manufacturing until confronted by the price tag. Patriotism feels good, but apparently, saving $258 on a showerhead feels even better.

Next time you're at the checkout page, ask yourself: Which preferences am I revealing?

Zoom in on this photo. Look at every single face in the crowd. What do you see?

Pure joy. Elation. Excitement.

And then there’s this guy:

The photo is from last Sunday at The Masters in Augusta, Georgia. 2025.

If I hadn't mentioned that, you'd probably think this scene was straight out of an old movie. Caddyshack, Happy Gilmore, or something.

But no, that's just a group of people being present in 2025, celebrating sports history.

Charles Robinson put it perfectly:

"One of the coolest parts of this moment is seeing a crowd watch it completely through their eyeballs rather than through their phone camera."

Famously, The Masters bans cell phones at the tournament.

Fans have no choice but to focus on the golf, eat $1.50 sandwiches, and track scores the old-fashioned way on a manually updated scoreboard.

Ask anyone who’s attended, and they'll say something like: The Masters is the greatest sports event I’ve ever been to.

Compare that to the scene when LeBron broke Kareem’s NBA scoring record in February 2023:

A historic moment, reduced to an Instagram story.

Zoom in, and you'll notice nearly everyone experiencing history through their phones.

Zoom in again at the LeBron photo, and you'll notice one exception to the sea of phones: a guy watching through his own eyes.

His name? Phil Knight, founder of Nike.

Maybe the Shoe Dog knows something the rest of us don’t.

We need more spaces like The Masters, and not just in sports.

Team meetings, dinners with friends, date nights, concerts, holidays, time with your kids.

Places where putting your phone away and being present feels like a privilege.

Venture capital constantly debates the value of operational experience.

That badge of honor—"I was an operator"—once opened doors and closed deals.

Investors wore their battle scars proudly: I’ve been in your shoes.

ChatGPT arrived in 2022, and everything sped up.

Smaller teams. Faster revenue. Product cycles in days, not weeks.

Today's startups operate differently.

Operating Skills

When builders stop building, skills erode.

The instincts that once set them apart slowly lose relevance.

A handful of operators-turned-investors could return to a C-suite tomorrow and dominate.

But they are the exception. Most lose their edge far sooner than they admit.

The lost edge can be technical skills, risk tolerance, or willingness to grind — many startups today are on “996” schedules (9 a.m. to 9 p.m., six days a week).

Staying Relevant

I wake up every day paranoid about losing my edge in product.

Tech is more like Hollywood than we admit. No one remembers your hit from a decade ago.

You're either building or decaying. No middle ground.

That applies to PMs, designers, engineers. I spent years at the top of the App Store. It doesn’t matter now.

Maybe you're reading this from a completely different industry, but you know exactly what I mean.

Because the truth is universal: if you care about your craft, you’re either getting better or falling behind.

Self-Awareness

The most underrated skill for operator-turned-investors is self-awareness.

Knowing when your past experiences no longer apply, and resisting the temptation to offer generic, outdated advice

That SXSW 2011 go-to-market strategy —free tacos for downloads or whatever it was—is probably irrelevant today.

Spend weekends building something instead of writing your 500th IC memo.

You won’t regret it, and you’ll become a better investor.

OpenAI's memory upgrades signals the start of what may become the most transformative shift since GPT-3’s debut.

Until now, AI has felt like chatting with a brilliant but forgetful friend. The absent-minded professor type who'd crush it on Jeopardy but never remembers your birthday.

Memory is the breakthrough that changes everything for enterprise and consumer AI—marking the end of manual prompting and the start of truly personalized, proactive experiences that anticipate your needs and take action.

Research from Stanford's AI Lab indicates that memory-enabled systems demonstrate a 62% improvement in task completion rates for complex, multi-session projects. In other words: embrace memory, and you’ll get a lot more done.

AI will now remember the details that make you you—your habits, your thought patterns, your preferences—and become a lifelong companion and assistant.

If this sounds like a Black Mirror episode, that feeling won’t last. The productivity gains from giving AI more context and personal data will be too big to ignore.

Personalization: the new network effect

From an investment perspective, memory challenges the frequently repeated Silicon Valley belief that AI lacks defensibility. Spend five minutes at a Bay Area investor dinner and you'll hear that take. Lazy thinking.

OpenAI and others who win memory will unlock retention, defensibility, and the most powerful network effects we’ve seen since social graphs.

Memory, and the deeply personal context that comes with it, will make Facebook Connect’s 2008-era social graph look primitive.

OpenAI is perfectly positioned to introduce a "Sign in with OpenAI" product, enabling third-party developers to tap directly into its memory layer.

If Facebook Connect was about who you knew and your surface-level likes, memory is about who you are and the deepest thoughts you carry every day.

Work goals. Relationship doubts. Health concerns. Every passing thought, every quiet worry.

Of course, OpenAI will build many of these apps themselves. Their insane product velocity right now is increasingly focused on the application layer.

Founders need to shift gears. The game isn’t about spinning up ChatGPT wrappers or testing narrow use cases anymore.

It’s a war to capture memory faster than everyone else.

Shout out to my writing friend signüll, who dropped a piece this morning that’s worth your time if you’re interested in diving deeper: memory is the deepest moat.

Reflexive AI usage is now a baseline expectation at Shopify.

In the memo, he outlined 6 expectations for all employees going forward at Spotify.

1. Using AI effectively is now a fundamental expectation of everyone at Shopify. It's a tool of all trades today, and will only grow in importance. Frankly, I don't think it's feasible to opt out of learning the skill of applying AI in your craft; you are welcome to try, but I want to be honest I cannot see this working out today, and definitely not tomorrow. Stagnation is almost certain, and stagnation is slow-motion failure. If you're not climbing, you're sliding.

2. AI must be part of your GSD Prototype phase. The prototype phase of any GSD project should be dominated by AI exploration. Prototypes are meant for learning and creating information. AI dramatically accelerates this process. You can learn to produce something that other team mates can look at, use, and reason about in a fraction of the time it used to take.

3. We will add AI usage questions to our performance and peer review questionnaire. Learning to use AI well is an unobvious skill. My sense is that a lot of people give up after writing a prompt and not getting the ideal thing back immediately. Learning to prompt and load context is important, and getting peers to provide feedback on how this is going will be valuable.

4. Learning is self directed, but share what you learned. You have access to as much of the cutting edge AI tools as possible. There is chat.shopify.io, which we had for years now. Developers have proxy, Copilot, Cursor, Claude code, all pre-tooled and ready to go. We’ll learn and adapt together as a team. We’ll be sharing Ws (and Ls!) with each other as we experiment with new AI capabilities, and we’ll dedicate time to AI integration in our monthly business reviews and product development cycles. Slack and Vault have lots of places where people share prompts that they developed, like #revenue-ai-use-cases and #ai-centaurs.

5. Before asking for more Headcount and resources, teams must demonstrate why they cannot get what they want done using AI. What would this area look like if autonomous AI agents were already part of the team? This question can lead to really fun discussions and projects.

6. Everyone means everyone. This applies to all of us—including me and the executive team.

Every year or so, a CEO publishes a manifesto that significantly reshapes tech company cultures across the industry.

Recent examples include Brian Armstrong’s influential 2020 article"Coinbase is a mission-focused company” and Mark Zuckerberg’s “Year of Efficiency”.

Tobi is a trendsetter among CEOs across the industry, and yesterday's memo will shape how founders approach using more AI and hiring less people in 2025, especially with the recent downturn in the financial markets.

That’s likely great news for founders building AI tools aimed at developers, PMs, designers, and marketers—increased AI adoption should benefit their products (though, on the flipside, they might end up selling to fewer seats).

We've observed a notable "pull forward" effect in revenue for AI applications industry-wide, with companies hitting remarkable ARR milestones faster—and with smaller teams—than ever before.

Some people are calling it “vibe revenue” which is meant to say that companies and employees are experimenting with many AI products right now and subscribing to many similar products at the same time.

We recently illustrated this phenomenon in a slide for a Chapter One deck, and notably, many of these ARR numbers have grown since we created it a few weeks ago.

Some memos become cultural moments for our industry, giving CEOs the "green light" to reimagine their own orgs.

Tobi’s memo feels like one of those moments.

Reflecting on today's market crash—driven by escalating tariffs and global financial tensions—I can't help but notice the significance of timing.

April 7th, 2020. April 7th, 2025.

The end of one crash and the beginning of another. Exactly 5 years apart.

April 7th, 2020 marked the moment when collective terror transformed into something unexpected—a strange, intoxicating optimism.

The COVID-induced market crash ended, marking the beginning of an unprecedented bubble driven by stay-at-home optimism, boredom, and excess liquidity.

Recent frenzied AI investment rounds echo some of those wild days, yet nothing quite matches the unique intensity of that era.

Now, on April 7th, 2025—exactly five years later—we find ourselves at the start of another market crash, this time driven by tariffs instead of a virus, and our portfolio trackers flash a sickly shade of red.

When markets fall, time stretches. Each day of decline expands to contain multiple lifetimes of worry.

The 47 days of the Covid crash felt eternal while we lived through them. Only in retrospect do they compress into a brief prologue to what followed.

• March 9th, 2020 (Black Monday I): Dow Jones fell 2,014 points (7.79%)

• March 12th, 2020 (Black Thursday): Dow Jones dropped 2,352 points (9.99%)—a historic decline

• March 16th, 2020 (Black Monday II): Dow Jones plunged nearly 3,000 points (12.9%)

During these 47 days, the Dow lost 37% of its value; the S&P 500 declined by 34%.

But numbers alone can't capture the midnight anxieties or the compulsive dread with which we repeatedly check our portfolios.

We’re on the brink of another downturn, asking familiar questions: How deep will it go? How long will it last?

The most honest answer remains the simplest: nobody knows anything.

On Friday, April 4, 2025, the Dow fell by 2,231.07 points, or 5.5%, marking one of the most significant single-day losses in recent history.

This drop was slightly less severe than the 7.79% decline on March 9, 2020, but today's crash suggest we will experience losses similar to March 12, 2020, when the Dow plunged nearly 10%.

What's especially disorienting about this crash is that on January 20th, 2025—just 77 days ago—we were entering what many predicted would be a new "Golden Age" following Trump's re-election.

Today feels eerily reminiscent of early 2020, when our optimism about entering the "Roaring Twenties" vanished almost overnight as COVID emerged just weeks into the new year.

I remind myself that on February 20th, 2020, it felt as though the financial world was collapsing—but that crash lasted only 47 days.

The real question isn't if markets will recover—they always do—but whether we'll use this downturn to emerge as better investors and operators, maintaining financial discipline even when markets bounce back, unlike what happened in 2020.

My friend and investor Geoff Lewis describes my feelings today: It’s macro moments like our present one when I feel most energized. Volatility clarifies opportunity—bring on the chaos.

Five years ago, one crash ended.

Today, another begins.

Last week, I wandered through Noe Valley with a close friend & we talked about family, investing, and everything in between while drinking a coffee.

Our friendship began years ago on the back of a tour bus winding through the ancient landscapes of Israel in 2018. He is one of those seed investors who always seems to know what's happening in the industry. Every deal, every whisper, every trend. You probably know someone like him.

He mentioned one of his 2022 investments that's now become one of this year's biggest breakout success stories. The current product is much different from the original concept he supported as a seed investor.

I was curious what he was thinking when he invested in the company.

When writing the check, he actually suggested they consider pivoting. The founders' technical talent justified the investment regardless of their initial direction.

"I wasn't investing in their first idea," he said with conviction. "I was investing in the idea that they might pivot. They were just that good."

Early-stage venture investing is undergoing a profound shift and we are seeing more successful pivots.

With software becoming commoditized through AI-driven code-generation tools and platforms like Bolt, v0, and Lovable, the initial product idea matters less now than at any time in the past.

Instead, product velocity—the speed at which teams can build, iterate, and adapt — will define success at the seed stage going forward.

We romanticize visionaries who never waver, who push through resistance with stubborn certainty. But that narrative is increasingly obsolete.

Consider Captions, one of our portfolio's fastest growing companies. When we invested in 2021, they pitched a social network, but I suspected a pivot was inevitable.

Their founders' adaptability was the real asset I was betting on—not the product on their pitch deck. Today, they've become the category leading short-form video editor and are now building best-in-class voice-to-video models.

What made them so special? Founders Gaurav Misra and Dwight Churchill invented the now popular "design engineer" role while leading Snap's experimentation team. Their hybrid design and engineering skills allowed them to compress product development cycles that typically take months into days.

They were also comfortable discarding ideas and beginning anew, drawing from their experience building over 50 products at Snap.

Our Captions investment marked a significant philosophical shift in my approach to early-stage investing. For the first time, I deliberately prioritized the team's adaptive potential over the specific product they presented—investing not in what they'd built, but in their capacity to evolve beyond it.

That said, I've made my share of mistakes when underwriting potential pivots — it’s a difficult skill to master.

I met the Stackblitz team during their seed round while they were developing what was essentially "Figma for developers" - a browser-based IDE for collaborative development. Though impressed by both the founders and their technology, I believed they would eventually need to pivot, and questioned whether browser-native development tools could capture sufficient developer market share to generate venture-scale returns.

When their runway dwindled to just three weeks last year, they executed a remarkable pivot by launching Bolt, an AI-powered app builder that rapidly emerged as one of the year's standout products. Within months, they were generating eight-figure revenue and secured a $105M funding round in January.

The outcome reveals a nuanced truth about early-stage investing: sometimes the initial product direction matters less than the adaptive capacity of the founding team.

Our investment thesis has evolved through both successful bets and missed opportunities, with a more nuanced understanding of founder potential. We've increasingly gravitated toward the Design Engineer archetype - founders who combine technical and design skills, like Gaurav and Dwight at Captions.

These types of founding teams seem to move with impossible velocity. While others debate, they build. While others plan, they ship. While others perfect, they iterate. They compress time itself.

What makes this profile particularly compelling in today's landscape is how it addresses a growing market inefficiency. As technical implementation becomes increasingly commoditized through AI, the competitive advantage shifts towards taste and iteration speed.

And in this moment of accelerating technological change, the founders who embrace creative destruction may be the only ones who survive long enough to win.

Hidden gems on the internet are hard to find, but one of my favorites, Patently Apple, offers a fascinating peek into Apple’s most secretive ideas.

The site won’t win any design awards with its throwback 2005 aesthetic, but it delivers a rare behind-the-scenes look at Apple’s upcoming projects.

Jack Purcher, the author of Patently Apple, diligently tracks every Apple patent filing and approval, offering detailed product sketches accompanied by concise commentary.

Despite Apple's renowned secrecy, patent filings offer a valuable window into its inner workings and are perhaps the most reliable way to predict its roadmap.

Over Thanksgiving weekend, I found myself with a rare bit of free time (a luxury with a 2-year-old daughter!). I decided to dive into Apple’s latest patent filings and approvals, and share a few of my favorites with you.

Upgraded Apple Watch Experience

Apple's commitment to health and fitness tracking is no secret, but recent patents suggest a big leap forward.

Patent 12133743 describes a huge upgrade for future Apple Watch models: stretchable fabric bands embedded with an array of sensors into the straps.

These smart bands could potentially monitor blood pressure, respiration rates, and even capture electrocardiogram (ECG) readings.

The patent suggests these sensor-rich bands might not be limited to wrist wear — and proposes applications for stretchy fabric in products including hats, shirts, pants, and athletic wear.

Imagine a future where Apple-branded fitness apparel could track your vitals from your forehead, chest, or bicep. With more data being collected, we’ll get better insights into user health, and combining that with large language models will make the insights even more powerful.

One of the inventors listed on this patent, Daniel Podhajny, previously worked on Nike's legendary Flyknit material. This hints at a future where Apple's wearable tech integrates with high-performance athletic wear.

Modular iPhone on the Horizon

In a surprising move, Apple has filed a patent application for a potential modular iPhone design. This concept features a removable back panel that users could swap out to add functionality.

Imagine being able to slide in an extra battery pack for extended use or upgrading your camera system without buying an entirely new phone.

This modular design aligns with recent Right to Repair legislation, which has pushed Apple to make its devices more user-friendly and serviceable.

It's a significant shift from their historically closed ecosystem, potentially allowing users greater control over their device's capabilities and lifespan.

While not all patents lead to actual products, this filing shows that Apple is exploring the idea of more flexible and customizable designs for future iPhones.

Smart Glasses: Next Iteration of Apple Vision Pro

The launch of the Apple Vision Pro did not live up to expectations, but that doesn’t mean Apple is stepping away from smart glasses.

The rave reviews for Meta's Ray-Ban Smart Glasses have been hard to miss—they’re getting praise across the board. Apple is surely taking note, and it will be interesting to see how they approach smart eyewear going forward.

At Apple, an internal project known as Atlas is reportedly in progress to evaluate the company’s current smart glasses offerings.

I find it interesting that Apple is only doing focus groups and research with their own employees, instead of also including external users. Classic Apple—keeping things private. The strategy is to prevent leaks and keep their roadmap under wraps.

To be clear, Apple isn't playing catch-up in the smart glasses category. As you can learn from reading Patently Apple, they have been filing smart glasses technology patents for over seven years.

I’d guess Apple’s smart glasses (EyePods, perhaps?) will be much more laid-back than the Apple Vision Pro—more like Meta’s Ray-Ban sunglasses.

They’ll of course integrate with Apple’s ecosystem, including features like augmented reality, hands-free Siri, and new ways to create and consume photos and video while on the move.

Siri: The Large Language Model Upgrade

Speaking of Siri, Apple is racing to develop a more conversational version of its digital assistant.

Siri has always been an underwhelming product, and the current surge in AI innovation is an existential moment for Apple to elevate its capabilities.

This revamped Siri will leverage advanced large language models (LLMs) to enable more natural, back-and-forth conversations with users — with greater agentic capabilities.

To succeed, Siri’s AI assistant will need to handle more sophisticated requests quickly and efficiently. The current Siri product is unreliable and the outputs are much less impressive than what we are seeing with natural language prompts at OpenAI and Anthropic.

Apple knows this is a critical moment for Siri and the upgrade is part of Apple's broader push into artificial intelligence.

The launch of Apple Intelligence this year had much room for improvement, and iOS 18.2 (announced last week) will include upgrades including:

• Image generation capabilites called Image Playground. The new feature allows users to input a text prompt, and the AI generates an image in a cartoon style.

• New writing capabilites built into Siri that integrate directly with ChatGPT. You will be able to use Apple Intelligence to help write emails, essays, and more.

The upgraded Siri will potentially transform how we interact with Apple devices, by shifting us toward using our voices more than typing. It could also help Apple close the gap with competing AI assistant applications like ChatGPT and Google’s Gemini.

I anticipate that an LLM-powered Siri upgrade will significantly impact the broader AI startup ecosystem as well.

Users will grow increasingly accustomed to voice-first product experiences and there will be a lot of voice innovation in the coming years.

Apple’s Roadmap

From health-tracking fabrics to modular phones, smart glasses, and conversational AI, Apple will continue to push the boundaries of consumer technology.

As always, take patent filings with a grain of salt. Not every idea evolves into a product, and when it does, the final version often looks quite different from the original concept.

As a venture capitalist and founder, staying ahead of the curve is key, and sites like Patently Apple are super helpful for that.

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Author’s note: here is the X account for Patently Apple: https://x.com/PatentlyApple. Following this might be more convenient than bookmarking the site.

The premise was simple: Create content. Build an audience. Monetize.

Millions of creators on YouTube, Instagram, and TikTok leveraged their skills to build massive audiences, with many rising to internet fame almost overnight, thanks to algorithms.

They then marketed digital and physical products to their audiences—earning revenue directly, through affiliate links, and via sponsored posts.

The content race during Covid was intense.

YouTube channels, TikTok clips, Instagram posts, Substack newsletters, Spotify podcasts, Patreon subscriptions, and Cameo shoutouts. (We'll skip mentioning OnlyFans.)

The monetization options truly seemed limitless.

Jimmy Donaldson, better known as Mr. Beast, is the breakout star of the recent creator economy wave.

Growing up in Greenville, North Carolina, Jimmy dropped out of college to obsess over cracking YouTube's recommendation algorithm with his friends. No Stanford degree, no Y Combinator pedigree—just raw determination and creativity.

By 2022, MrBeast became YouTube's most-subscribed creator, amassing 112 million followers and leveraging his massive audience to launch venture-backed companies—all before turning 25.

While his ventures focused on consumer packaged goods (CPG) rather than software, they achieved staggering success. Take Feastables, his chocolate and snack brand co-developed with Night Ventures. Launched in 2022, it now generates $100 million in annual revenue.

I had the opportunity to consider an investment in Feastables before it launched but passed on the introduction, doubting the venture-scale potential of a chocolate brand.

Maybe I should’ve dreamed bigger.

Creators like Jake Paul have launched CPG brands—like his men’s personal care line, W—but most focused on monetizing their content and time, not building tech companies.

Meanwhile, VCs were pouring money into platforms designed to help creators grow and monetize their audiences—the so-called "creator stack."

If you were a VC in the early 2020s, your inbox was drowning in pitches with “creator economy” in the subject line (today, it’s all about AI). A glance at a 2022 creator economy market map is enough to make your head spin.

Every venture capital firm was trying to get a piece of the creator economy action — because it was supposed to be a very big economy for creators and platforms, which would result in public companies, M&A, and venture scale outcomes.

While creators grew their audiences and found ways to monetize, investments in the sector struggled to achieve venture-scale returns. Few companies scaled to sustainable billion-dollar valuations and there has been little liquidity via IPOs or M&A.

Platforms faced challenges with compressed margins as they fiercely competed to attract top talent. Building a venture-scale business becomes difficult when your share of digital subscriptions is limited to just 10%.

Most venture capitalists have quietly moved on from the creator economy. While they may not publicly acknowledge that the 2020-2022 creator economy boom was a bubble in the tech industry, get them talking over a glass of wine at a cocktail party, and they'll likely admit as much.

Enter: The Software Creator

So where does the creator economy go from here? Creators are still churning out TikTok videos. The numbers are staggering—there are over 207 million creators worldwide. 45 million of them identify as professionals.

Is it time to reconsider the concept as a viable venture capital opportunity?

In 2023, Slow Ventures unveiled a $20 million fund dedicated to individual creators, taking a unique approach. Instead of investing in "creator stack" platforms, they are directly investing in creators in exchange for a percentage of their future earnings.

Slow Ventures made a deal with Marina Mogilko, a language learning YouTuber and co-founder of the platform LinguaTrip. In exchange for $1.7 million in capital, she will give the venture firm 5% of her earnings for 30 years — plus, they keep that 5% stake in any IP she develops within those three decades. As she explained to VICE, “If I wrote a book in 2030, and it’s still selling in 100 years or whatever, they’re still getting 5% of that revenue.” (Techcrunch)

This approach gets to the heart of answering whether the creator economy is fit for venture capitalists. The answer is likely yes, but we are still in the experimentation stage.

At Chapter One, I’m genuinely optimistic about the creator economy today, driven by advancements in AI. Developing software and automating operational workflows is now easier than ever. Creators no longer need large engineering or operations teams to explore venture-scale ideas—just a modest amount of capital will do.

Large language models (LLMs) are becoming increasingly skilled at writing code, and we are witnessing a shift from creators selling products like chocolate bars (I should have invested!) to developing consumer-grade software applications.

The most impactful creators of the future won’t just produce content—they’ll create software as well. With AI-powered tools, creators can design, prototype, and scale software, expanding their influence far beyond selling digital subscriptions.

We’re quickly entering an era where internet-native users will have the ability to create consumer-grade software from the ground up.

Cursor and similar code generation tools will be used by many more people than today’s traditional developers.

While no-code tools initially held this promise—and platforms like Shopify partially delivered for e-commerce—most no-code solutions have fallen short of achieving a truly consumer-grade experience, often due to performance and UX/UI limitations.

That’s beginning to change.

Software Creators: Past and Present Examples

This week, Haliey Welsh (aka ‘Hawk Tuah’) launched Pookie Tools, an AI-powered dating advice app.

Haliey was just a normal person 3 months ago until she went viral for the Hawk Tuah video, but now she has 5 million followers on her social platforms. So why not build a dating assistant?

Welsh collaborated with a product studio to develop this product, and it seems likely that, in the future, she and a small in-house team could take over its development independently.

Is this the next venture-scale product? Unlikely. It’s more akin to "fast fashion for software" than a venture-scale business. Still, it’s a compelling example of how creators are increasingly exploring software development—and I’m confident it will drive revenue.

This trend isn’t entirely new. Back in 2014, Kim Kardashian introduced Kim Kardashian: Hollywood, a casual mobile game that allowed players to create and live the life of an aspiring virtual celebrity.

Within its first two years, the game generated over $157 million in sales. Glu Mobile, the game’s developer, never revealed its lifetime revenue, but the title generated hundreds of millions in in-app purchase (IAP) revenue before shutting down in April 2024 after an impressive 10-year run.

A notable example of a creator-turned-software entrepreneur is beloved parenting expert Dr. Becky.

During the COVID pandemic, Becky Kennedy, PhD, a clinical psychologist and mom of three, turned to Instagram to offer support and share tips for overwhelmed parents. Millions of followers flocked to her feed for her candid videos—such as those filmed on her closet floor—for her validating presence, warm yet sturdy demeanor, and pragmatic advice.

Good Inside, which began as Kennedy's social media movement and evolved into a New York Times best-selling book and a chart-topping podcast, has grown into a parenting-advice juggernaut that's attracting significant investor interest. In 2023, the company raised $10.5 million in its first venture capital funding round, led by Inspired Capital.

Good Inside is focused on using technology to expand upon the connection Dr. Becky has organically built with parents through various content channels and mediums. Their first product iteration included a subscription-based online community and content library ($279 annually), with a user experience centered around providing members with on-demand access to parenting solutions.

Supported by a talented team of technical operators, Dr. Becky and Good Inside have since taken it a step further, launching an innovative app with personalized, age-based parenting advice and an AI chatbot trained on Dr. Becky’s work and style. The AI chatbot is designed to feel like a direct conversation with Dr. Becky, leading to praise from Anthropic’s Mike Krieger. The company has been growing over 100% annually and reaches parents in more than 100 countries.

Another wildly successful recent example is Bryan Johnson, the anti-aging tech entrepreneur behind the "Don’t Die" movement. Bryan generated $20 million in sales within 24 hours of launching his Blueprint supplement products.

Blueprint was CPG supplements and not software, but Bryan created the Blueprint Protocol website, which went viral in 2023. He’s now developing the Don’t Die app, a subscription-based product aimed at helping users "slow their speed of aging together."

Bryan was the the founder and former CEO of Braintree—a payments company that acquired Venmo for $26 million and was sold to PayPal for $800 million in 2013.

He has taken the unconventional journey of moving from a successful founder to a prominent creator. Now, he’s back to building software, seamlessly blending the roles of creator and founder.

Content to Code: The Evolution Towards Software Creation

There are 2 million creators with over a million subscribers, but only a small fraction are currently able to develop software. That has changed.

We’re excited to meet content creators who are ready to build venture-scale software companies and services businesses that deeply connect with their audiences.

The ideal software creator is a content creator with millions of followers who feels burned out by the relentless content creation cycle and believes they can transform their creativity into something more enduring.

The companies they build might be social products, health and wellness platforms, online games, or dating apps — or entirely new concepts beyond our imagination.

At Chapter One, we are currently incubating a consumer application that leverages a large audience to give us a massive distribution advantage. This experience has been a real eye-opener to just how massive this opportunity could be—especially in a noisy world where winning on distribution is everything.

Our team has built products that have reached billions of users at companies like Twitter, Robinhood, Scale AI, and Tinder.

Now, we’re eager to work with future founders ready to evolve from Content Creators to Software Creators.

If you're a content creator with a cult-like following and want to become a software creator, reach out @jmj.

In 1980, Steve Jobs likened the personal computer to a modern form of the bicycle. Half a century later, consumer-grade AI has radically advanced the metaphor.

Now, those once-modest bicycles that Apple Computer built in Cupertino, California have transformed into high-performance sports cars.

With the explosion of AI, we gained the ability to predict and model complex scenarios, translate languages in real-time, automate everyday tasks with simple prompts, and enhance our decision-making with access to vast amounts of information.

Now, we find ourselves learning how to 'drive' our computers again, a historical moment that creates both new opportunities and existential questions for humans of the internet.

At Chapter One, we spent the past year doing thesis work in preparation for our next fund, Page Three.

One of our core thesis areas that I am leading is called Internet of Trust. The basic premise of our thesis is that:

• Consumer confidence in FAANG companies is at an all-time low.

• The increasing prevalence of AI will exacerbate this growing distrust.

• Consumers will ultimately spend time and money on software and internet services that can successfully secure their trust.

As I began exploring the Internet of Trust thesis in Q3 2022, OpenAI released GPT-3 and a thesis began to take shape.

One question I found myself deeply focused on was, “Will consumers care if the software and content they consume is created by a human?”

The romantic former English major in me wanted to believe that — yes, we care if a real human creates the content we consume and the software we use.

But at the end of the day, we just want to be entertained online. Whether the origins of that entertainment come from a human, might not be important.

And even if we want our content to be handmade, how will we be able to tell what is AI generated, created by a human, or a combination of both?

The image above was created by one of our portfolio founders, Pablo Stanley. I love the concept of content someday carrying labels like "AI-Free."

In 2005, I spent a semester in Florence, Italy. Each morning on my walk to campus, I passed a violin maker, hard at work in his workshop by 8 a.m., meticulously crafting custom violins by hand.

One day, I stopped to chat with him. He shared that the tools he used were the same ones his grandfather had relied on. His father had been a violin maker too, continuing the family tradition.

I remember being struck by the beauty of it all—that artisans like him still existed, keeping their craft alive in a fast-changing world.

The term "handmade" has always carried a distinctive significance, denoting a product or piece painstakingly crafted by human hands, as opposed to being mass-produced by machines.

In recent years, the term has evolved to "handcrafted" — an attempt to further emphasize the exclusion of machinery from the creative process. A handcrafted item is entirely created by human hands, using rudimentary tools such as knives, needles, and brushes.

The appeal of a "handmade" or "handcrafted" label lies in the assurance of quality, consistency, and immaculate craftsmanship. People favor luxury products made by human hands or with substantial human involvement in their creation.

Is the same true for what we consume online?

The internet has reached an important moment, with much uncertainty over the future of "handmade" digital creations like photography, blog posts, illustrations, applications, and code.

The rise and widespread use of generative AI is expected to diminish the presence of handcrafted digital creations—which unsettles many creatives. Living in Los Angeles, I hear this concern from writers all the time.

Internet native creators like engineers and designers are less worried for now.

More than 40% of the code committed to GitHub daily is now created with the help of code generation tools. Designers are increasingly open to using generative plugins for Figma, although these tools have yet to match the effectiveness of code generation tools.

As the AI landscape continues to evolve, I often ask myself: what parts of the internet do we want to be handmade?

I’m guessing you don’t care if the Substack codebase hosting this content was built with the help of code generation tools. You probably also don’t mind if the UX/UI was designed with the help of generative tools, though a discerning eye might notice.

But you likely care if this article was written by ChatGPT because it comes from a writer whose content you chose to subscribe to—you didn’t sign up to read the output of large language models.

Ultimately, preserving the Handmade Internet will lie in finding the right balance between preserving the human touch and embracing the possibilities of AI.

Generative AI products are incredible at unlocking new creative superpowers. Take Suno, for example—if you’re curious about music, you can create a song in just a minute.

For most of us who aren’t professional musicians but have always dreamed of making music, it bridges the gap between aspiration and skill.

Still, I hope the internet will have its own Florence-like artisans—its digital violin makers. Writers, designers, and creatives who dedicate themselves to crafting entirely by hand.

Maybe it’s a romantic idea, but some things are simply better when they’re handmade.

Authors note:

The New Internet is almost entirely AI-free, and I’ll do my best to keep it that way. But would it matter to you if it wasn’t? Reply to this email and let me know—Jeff Morris Jr. (the real one) will respond.

One of the most successful dynasties in professional sports history ended yesterday.

Klay Thompson, one of the greatest Golden State Warriors ever, was traded to the Dallas Mavericks for two future second-round draft picks.

Two second-round picks. Is that really it? Are we done? This isn’t how anyone imagined the Steph, Draymond, and Klay dynasty would end.

This was the once-in-a-lifetime team that revolutionized the NBA by setting records for three-pointers, often shooting from incredible distances, and challenging the league with their innovative small-ball, positionless play style.

I remember reading an article four months ago when Steph stated that he was certain that he, Klay, and Draymond would end their career with the Warriors.

"A hundred percent," Curry responded when asked if he thinks the trio will be Warriors for life. "I think that's always been a motivator for us, and I think the way that we talk about it is we not only want to end our career as a Warrior, continue to compete at a high level, but you want to end it the right way.

Four months ago, this was Steph imagining the perfect ending. Just four months later, the dynasty is done.

You can never foresee these things when times are good. And the Warriors had it good for so long.

You don’t have to be a basketball fan or even a Warriors supporter to feel emotional about this announcement.

Maybe you grew up in the Bay Area, like me, cheering for the hopeless Warriors.

Or perhaps you lived in the Bay Area at some point between 2011 and 2024 and watched one of the worst teams of all time become one of the best. If so, you likely remember a time when life in San Francisco felt simpler and the tech industry was more optimistic.

Or maybe you've never lived in the Bay Area, but you've experienced something magical in your life that felt like it would never end.

A championship-winning sports team in high school, a perfect relationship, or a startup that achieved success.

I was fortunate to be part of a dynasty in my career.

I joined Tinder as the 55th employee in 2015. We grew into one of the largest consumer companies ever, breaking nearly every industry record.

On April 7th, 2018, I vividly remember celebrating the release of Tinder Gold, a blockbuster hit that boosted our market cap by billions in a single day.

The early morning champagne toast in Los Angeles marked the culmination of many years of hard work and success, along with some painful moments.

Our founders had been pushed out of the company. We faced numerous existential crises where it seemed like the company might not survive. This could be a book, but I’d never write it myself because I prefer to remember the good times.

One of my teammates, Brian Norgard, told a packed room, “We should enjoy the moment because it won’t be like this forever.”

Brian might not remember saying this, but his words sobered me up instantly that morning. I hadn’t imagined that our dynasty would one day end, but as soon as Brian said that, I knew he was right.

A few months later, there were changes in the management team, and teammates who had celebrated our record-breaking years in that room were gone.

The company continued to win, but things felt different. We didn’t dream as big, and my job shifted to optimizing what was already working rather than building the future.

I left the company 18 months later — and it really does end fast.

A sentimental email to the company. A five-minute visit to our IT team to return my computer. Some hugs.

Just like that, the record-breaking years ended faster than I could have imagined. That dynasty ended for me.

As the Klay news dropped yesterday, I saw many people debating when the Warriors dynasty actually ended. Was it…

June 10, 2019, when Kevin Durant tore his Achilles during Game 5 of the NBA Finals against the Toronto Raptors? He left us for the Brooklyn Nets about a month later.

June 13, 2019, just three days later during Game 6 of the NBA Finals, when Klay Thompson tore his ACL and tried to keep playing?

November 18, 2020, a little over a year later, when Klay tore his right Achilles during a workout while rehabbing the ACL?

Or was it October 5, 2022 when Draymond Green famously punched Jordan Poole during a Golden State Warriors practice. This was during training camp the year after Steph, Klay, and Draymond miraculously won a 4th championship as a third seed against the Boston Celtics.

Some people said that the Warriors dynasty ended yesterday when Klay was officially traded, but the truth is that dynasties end over the course of many years and many moments that you wish you could get back.

If you’re a diehard Warriors fan like me, you wish you could reverse time and change so many moments to watch the team you love play together one more time.

But then you realize that what makes a dynasty so special are the struggles, mistakes, and hardships you must overcome to build anything worthwhile.

Injuries and egos are part of being human, and few championship teams become a dynasty that wins again and again.

In your career and life, you will hopefully have moments where you feel championship level success.

You might even be part of a dynasty for many winning years. When that happens, remind yourself that it won’t last forever. And celebrate with champagne.

A dynasty ended yesterday — and now a new journey begins.

The attendees were mostly “mid career” investors who are rising stars at large funds, paired with emerging managers who aspire to create their own venture capital franchises.

There was a sense of camaraderie in the room. Over the past two years, most had experienced an industry meltdown together for the first time in their careers.

There is a longer and more articulate article about why venture capital was bloated and how every stage of the capital stack became frothy, but that has been written a thousand times.

So that is not what I want to write.

What I want to say, and the sentiment that I kept hearing last week was that: if investors make it to the other side of this bear market, they will be better capital allocators for the rest of their careers, so long as they internalize the emotions they’re feeling today.

There are two parts of that statement which are worth double clicking on.

1. If investors make it to the other side of this bear market, they will be better capital allocators for the rest of their careers, so they as they internalize the emotions they’re feeling today.
   
   This is a conditional statement because there will be investors who do not make it to the other side of this bear market. This might happen for a variety of reasons.

   
   Investors might find more productive and lucrative uses of their times. Yes, I said that correctly, there are likely easier ways to make money than being a VC.
   
   Being a venture capitalist is a long journey to liquidity via carry dollars (where you make life changing money) and most emerging VC’s are still searching for a career defining investment.
   
   So what could you do with your time instead of being a VC?
   
   You might start a business, join a hedge fund with a faster expected payout, acquire an HVAC company (the meme is real), go back to operating, or simply not raise your next fund.
   
   And all of those options are okay.
   
   There are many ways to make money and careers fly by faster than you think, so why stick around to save face with peers?
   
   The older you get, the more you realize that industry memories are short and if you make a big life decision such as pivoting your career, few people will notice or care.
   
   I don’t say this to be depressing, it’s just the truth. Do something else with your time that you’re more excited about if you are feeling uninspired or have low confidence in your fund strategy.
   
   But, if you love this industry, and you love the grind of investing, and you love helping founders achieve greatness - you can make it to the other side.
   
   And if you internalize this moment in a positive way, you can become a better capital allocator for the rest of your career.
   
   Which brings us to the second part of the statement.

   
   

2. If investors make it to the other side of this bear market, they will be better capital allocators for the rest of their careers, so they as they internalize the emotions they’re feeling today.
   
   Yes, it is possible to become a better investor. This isn’t a job where you wake up and become the next Doug Leone. I’ve seen people try.
   
   When I speak to venture capitalists entering the industry, I want to tell them all the weird stories I have after making almost 150 investments.
   
   They will eventually earn their own stories, and the only way to get better in this business is to make mistakes.

   
   But you have to internalize the emotions that you’re feeling today, otherwise those mistakes will go to waste and you will likely repeat your errors in the next bull market, with all its fomo and temptations.

   

   
   If you feel embarrassed about investment decisions, let yourself feel embarrassed.
   
   If you passed on a deal that would have changed your career forever, read the investment memo that you wrote and figure out why you said no — and what question you could have asked to say yes.
   
   Whatever mistakes you made, internalize them now and promise yourself that you will never forget the feelings that you are feeling.
   
   Bear markets are a moment for learning, so figure out what the fuck you’ve actually learned.

Being an investor and getting paid to do this job for a living is a privilege.

You have to enjoy waking up to painful news and realize that surviving and thriving during a bear market is why you get paid.

Otherwise, go acquire an HVAC business.

That could be a fun way to make money and few of your peers will notice or care. Those who do will be happy for you.

C’est la vie, make it to the other side.