[photo of Chuck]
circle headshot, 200px

Hi, I'm Chuck 👋

Two-time exited founder. Author of Startup to Sold. Currently most curious about AI.

I keep showing up in new industries, learning fast, and trying to build the best version of the thing. Sometimes that's a scooter company. Sometimes that's a pickleball platform. Right now most of my energy is going into AI.

Right now

May 2026

  • Building a 3-layer standing-context system for AI agents
  • Drafting Skills Are the Prefrontal Cortex of Software
  • Hosting the first East Bay AI Meetup on June 10
  • Taking on fractional COO engagements at Startup to Sold
  • Running DailyPB, ~25K monthly views
see past months →

Things I've built

a quick career map

2006 → 2013

DVD Your Memories

Founder & CEO. Bootstrapped to four locations. Sold because "it worked without me."

2017 → 2018

Happy Moose Juice

COO. Tripled revenue by landing and executing the Peet's partnership.

2019 → 2022

Electric Scooter Ventures

Content + commerce platform. Sold to Unagi after a payroll-save pivot.

2023 → now

DailyPB

Pickleball event platform in the East Bay.

2024 → now

Startup to Sold

Fractional COO consultancy for founder-operated businesses.

Writing

essays I'm proudest of, and what's recent

Things I'm building with AI

a working list, not a portfolio

Standing-context system

3-layer memory architecture for AI agents.

In use

Browser Agent

Logged-in browser automation for any site.

In use

News Brief

Daily AI news, diarized and triaged.

In use

Automation Analyzer

One-task automation-fit assessment.

In use

Valuation Calculator

5-pillar SMB business valuation tool.

In use

GTD Triage

Voice-capture inbox triaged into GTD.

In use

Hermes

Always-on remote agent for scheduled work.

In progress

WhatsApp daemon

Read-first WhatsApp from the terminal.

In progress

Listings filter

BizBuySell candidates, AI-prefiltered.

Thinking about

The book

if you only read one thing

Startup to
Sold

Startup to Sold

The story of how I built DVD Your Memories from a side hustle into a four-location business and got the call from an acquirer who told me "the business actually worked without you."

Exit-readiness as an operating philosophy, not a sale-day event. Inc. Magazine Imprints, 2023.

Read on Amazon

Also doing

Teaching Go-to-Market Strategy at UC Berkeley Extension. Starting the East Bay AI Meetup — first event June 10, 2026.

About

I live in Albany, California with my wife Vienna and our two kids. I think about life as health bars across domains; the goal of any good day is moving the lowest bar up by one. Right now that bar is professional reputation in AI — which is why most of my building energy is pointed there.

I hold both sides of every decision at the same time, which makes me slow to commit but careful when I do. I read everything you send me.