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“Fries with dinner but no dessert counts as a win.” Who will build the first era-defining consumer AI company? Even the beloved AI tools we already rely on are only one model release away from obsolescence. The lasting advantage will come from products people…
Inside the private markets: Jacob Hodes on ten-year lockups, the retail push, and what Baltimore teaches you about finding value. 🎙️ Listen on Spotify, Apple, or wherever you get your podcasts. Jacob Hodes is a partner and Chief Investment Officer of Private…
Nan Ransohoff (Head of Public Goods at Stripe) recently published a sharp piece on what she calls the third wave of American philanthropy: the tidal change coming as AI wealth becomes liquid and a generation of founders gives it away. It’s a generous, clear-ey…
Tristan Walker is joining Collaborative Fund as a Partner. In that role, he’ll be a voice for the kind of company-building we stand for and a resource for the founders pursuing it. We’ve long believed that the best people to support founders are other founders…
Why we misunderstand odds and why it matters Everyone has a weakness. A blind spot. A vulnerability. For Achilles, it was his heel. Superman had kryptonite. Ted Williams struggled with pitches low and away. But what about the average person? I often think our…
What defines Collab Holdings future success isn’t the capital; it’s the stewardship. Few investors understand both the rigor of private equity and the nuance of what makes a brand actually matter to people. Parker Hayden does, and he is joining Collaborative F…
A few months ago I was in Northern California, visiting a company we’ve known for years. They make one product. They’ve made it the same way for decades. Their customers are borderline religious about it. The business is profitable, growing steadily, and has b…
Adam Smith, the 18th century economist, wrote that it’s not uncommon to meet a mother in the Scottish highlands “who has born twenty children not to have two alive.” That was life. And it hardly mattered whether you were rich or poor. Queen Anne of England had…
We are in the early innings of a fundamental shift in how we understand the human body. The current medical model is reactive and episodic — you feel sick, you see a doctor, you get a snapshot. But your body is a complex machine running 24/7, and it deserves a…
Everyone wants to be successful. Successful in our careers, our families, and our communities. I’ve certainly felt this way, that is until this past fall after attending two events, the first being a speech from someone who is more than a decade younger than I…
Today, NBC Sports owns the rights to many of sports’ “crown jewels,” including the Super Bowl, the NBA, the Premier League, Notre Dame Football, and of course, the Olympics. Yet, it hasn’t always been this way. In the early 1990s, NBC Sports was in trouble. Af…
Things I’ve been thinking about lately … I broke my back skiing when I was a teenager. It’s still screwed up and I occasionally tweak it, leaving me in agony for a few days. When I’m in pain I’ve noticed: I’m irritable, short-tempered, and impatient. I try har…
People often ask me where I get ideas for this Substack. The simple answer is everywhere, even a Christmas tree lot on a cold night in December. When my brother and I were kids, each year we would make the annual trip with our dad to pick out the family Christ…
A few weeks ago, I came across a letter Warren Buffett wrote in 1972 to Chuck Huggins, then president of See’s Candy. It’s two pages long, typed on letterhead, and quietly brilliant. Reading it now, more than fifty years later, it feels less like an internal m…
Like millions of others, I’ve been watching and playing with OpenAI’s new video model, Sora—and I keep thinking about how often technology outpaces permission. One week it’s coffee apps; the next, it’s cinematic worlds spun from text. Each innovation starts as…
After winning a Golden Globe in 2006, Phillip Seymour Hoffman replied to a question about how he got to this moment in his life. Nearly two decades later, his response is more relevant than ever. “Even if you are auditioning for something you know you don’t li…
The beginning of a new school year is a unique time in every kid’s life. A time full of expectations, and equal amounts of trepidation and excitement. The same could be said for their parents, which is why I was struck by this list of suggestions that a lower…
My new book, The Art of Spending Money, comes out Oct 7th. You can buy it here. Investor Chris Davis – who serves on the board of Berkshire Hathaway and Coca-Cola – says, it’s “not so much a sequel as the masterful, Oscar-worthy completion of” my first book, T…
The 2025 PGA Tour season wrapped up this past weekend with a great redemption story after Tommy Fleetwood won the Tour Championship at East Lake in Atlanta. The win was his first since joining the Tour eight years ago, netting him the biggest payday of his car…
A few things I’ve come to terms with: There is rarely more or less economic uncertainty; just changes in how ignorant people are to potential risks. You should obsess over risks that do permanent damage and care little about risks that do temporary harm, but t…
A few short stories: The CEO of Bronco Wine – which sells the Charles Shaw “Two Buck Chuck” wine at Trader Joe’s – was once asked how he’s able to sell wine for less than the cost of bottled water. He replied: “They’re overcharging you for the water. Don’t you…
Is Ferrari a car company? The obvious answer is yes, but not according to its CEO, Benedetto Vigna, who recently described the company’s business model saying, “We are not – we are not – a car company. We are a luxury company that is also doing cars.” That’s t…
Recently, I had lunch with Emmett Shine, co-founder of Gin Lane and a thoughtful voice in the conversation around AI and design. Among other things, we talked about the future of user interfaces and experiences in an AI-driven world. He said something that rea…