Deep Thoughts.

Ideas on marketing, business & growth

The Point Guard
Apr 29, 2026

The Point Guard

I spent part of today trying to explain to myself what exactly I'm building. Here's what I landed on: I'm building a point guard.

The Sport Was Never Really About the Sport
Apr 28, 2026

The Sport Was Never Really About the Sport

I've been playing pickleball for a couple of years. Somewhere along the way, it stopped being about pickleball.

The Day You Stop Being Curious Is the Day You Start Going Backwards
Apr 27, 2026

The Day You Stop Being Curious Is the Day You Start Going Backwards

My dad didn't grow up with computers. Tonight I helped him find ticket receipts on his phone. He figured it out. It got me thinking about what it really means to stay curious as you get older.

The Part of Sales Nobody Talks About
Apr 23, 2026

The Part of Sales Nobody Talks About

Every new client has a story. A business they built, a risk they took, a hustle that became their life. I connect with that — and it turns out, that connection might be worth more than the deal.

The Podcast That Made Me Think About Voice and Memory
Apr 21, 2026

The Podcast That Made Me Think About Voice and Memory

I fell asleep listening to a podcast about voice cloning and woke up thinking about what we're really preserving when we preserve a voice.

The Best Use of a New Skill Is Helping Someone You Love
Apr 20, 2026

The Best Use of a New Skill Is Helping Someone You Love

I have been building things with AI tools for months. This weekend I stopped pointing that at my business and pointed it at my sister instead. That felt different.

What My Dog Knows About Focus That I've Forgotten
Apr 19, 2026

What My Dog Knows About Focus That I've Forgotten

Watching Raffi chase a soccer ball — completely locked in, zero distractions — made me realize how badly I have lost the ability to focus on one thing. Some thoughts on attention, devices, and what we gave up.

Beating Myself Up for Exercising the Wrong Way
Apr 18, 2026

Beating Myself Up for Exercising the Wrong Way

I carry a little guilt about not being a morning exerciser. But if it were anyone else, I'd tell them they're doing an amazing job. I should be nicer to myself.

The Uneven Math of Investing in People
Apr 18, 2026

The Uneven Math of Investing in People

You give more than most — to clients, to people just starting out, to relationships. The returns do not always match the investment. That is not a reason to stop. It is just the actual math of operating that way.

Three Ladders in a Row
Apr 17, 2026

Three Ladders in a Row

Three ladder wins in a row against younger, faster players. That does not happen by accident — it is anticipation, skill, and shot recognition. A reflection on finding pickleball.

What RallyLeagues Taught Me About Assumptions
Apr 16, 2026

What RallyLeagues Taught Me About Assumptions

I spent six months building a sports league platform around one big bet. This week that bet shifted. Here is what I learned about building around assumptions and what I actually built.

Tuesday, April 14 — The Weird Feeling of Doing Enough
Apr 15, 2026

Tuesday, April 14 — The Weird Feeling of Doing Enough

I built a whole website solo today. And still, somewhere around 10 PM, I had that familiar feeling: I didn't quite get enough done.

I Built an AI Operating System for My Life (Over a Weekend)
Apr 15, 2026

I Built an AI Operating System for My Life (Over a Weekend)

How a rabbit hole turned into a personal AI assistant running on a Mac Studio in my house.