A Thanksgiving Letter to the Builders

Most early stage investors have never built anything. I'm grateful I did.

“The people who are crazy enough to think they can change the world are the ones who do.” — Apple, (1997)

The best credential in early stage investing isn’t an MBA or a track record. It’s scar tissue.

This Thanksgiving, I’m grateful I earned mine.

Most early stage investors have never built anything. They’ve studied builders, funded builders, advised builders. They’ve sat in pitch meetings and asked sharp questions about unit economics and founder-market fit. But they’ve never made payroll when the math said they couldn’t. Never looked a team in the eye after a launch that flopped. Never lain awake wondering if they’d have to say the words no founder ever wants to say.

They’re war correspondents who’ve never been on the front line. And they’re giving advice on combat.

I was a builder first. 25 years in the trenches. I wrote angel checks along the way, hoping and rooting more than investing. But I never did this professionally until I’d earned the right to sit across from a founder and say, honestly, I know.

The only skill that matters in this work is judgment. Judgment about people under pressure. Which founder has the vision to see around corners and the spine to keep standing when everything hits back. You don’t learn that from a deck. You learn it by building something yourself, watching it almost die, and figuring out how to keep it alive.

POPSUGAR wasn’t a case study. It was 15 years of my life. Lisa’s life. Our family’s life. The early chaos. The scaling years when every solution created two new problems. The exit, with all its complexity and weight and relief. Every lesson paid for in full.

Those angel checks I wrote along the way? Hope dressed up as strategy. I wasn’t investing. I was rooting. And rooting is just wishing in a better suit.

Real conviction is earned. It comes from pattern recognition, from watching hundreds of companies and thousands of decisions, from being wrong enough times that you recognize the shape of wrong before it arrives.

That’s what I’m thankful for. Not the wins. The sight. The ability to recognize something extraordinary in someone else’s dream because I once dreamed that recklessly myself.

When a founder sits across from me now, I’m not evaluating. I’m remembering. The loneliness of building something no one believes in yet. The weight of people counting on you. I’ve been in that chair. That memory is a lens that lets me see what others might miss.

So here’s to the founders.

The ones who leave safe jobs to chase something they can barely articulate. The ones who hear no ninety-nine times and show up for the hundredth pitch anyway. The ones who fail and start again, who get knocked down by markets and timing and bad luck and somehow find the will to stand back up.

You are not reckless. You are brave. There’s a difference.

This Thanksgiving, I’m thankful for a career I couldn’t have started and had to earn. Thankful for founders who trust us with a spot on their cap table, which isn’t a spreadsheet. It’s a record of everyone who looked at a dream and said yes.

But I’m also thankful for what’s waiting at home.

Katie’s back from Wake Forest. First night home, Cane’s on the coffee table, the whole family talking about everything and nothing. I watched her laughing with her sisters and for a moment saw her at six, at twelve, at seventeen. You blink and the girl on your shoulder is a young adult with her own life.

The Moatz family is in from Aspen. Lisa’s parents and Aaron’s parents are in from the east coast, continuing a tradition that started in 1971. Fifty-four years of the same families at the same table. Some chairs have changed. Some faces exist only in photos now. But we keep showing up.

That’s not a tradition. That’s a foundation.

The work matters. The founders matter. But the people who knew you before any of it, who’ll know you long after, who don’t care about your portfolio, they just want you present. They want you there. That’s the real cap table.

I’m not a war correspondent anymore. I’m a veteran who gets to stand behind the next generation heading into battle. And when a founder looks at me, wondering if I understand what they’re about to go through, I can tell them the truth.

I’ve been where you are. I believe in what you’re building.

Let’s go.

Happy Thanksgiving.