The story so far.
My mom raised three of us. My stepdad sold headstones. I caddied at Indian Ridge. The rest of this is what followed.
Where I'm from
Andover, Mass. Irish on my dad's side, all from Lowell. My mom grew up in Amesbury, near Newburyport. My dad passed from cancer when I was five, so my mom Nancy raised Brad, Lindsay, and me on her own. She worked as a teacher's aide at West Elementary. My stepdad Dave sold headstones at Colmer Monument Works. He's the reason Headstone Hub exists.
Caddied at Indian Ridge Country Club as a kid. Hired a bunch of friends there, including Pat Toomey, who's now a partner on the MA AI Coalition. The golf course is where I learned to shut up and listen. You grow up fast carrying a bag for a 50-year-old guy smoking cigars and telling you the truth about business.
Career arc
- Campus Live — early employee with Boris and Jared. Highland Capital + Charles River Ventures. 4.5 years.
- Wayfair — Product Lead, Search & Discovery. 15 engineers. 2.5 years. Through the IPO.
- One Good Meal — sandwich side-business I sold to Wayfair employees. Stepped out briefly as full-time founder/CEO.
- Drizly — VP Product. 3.5 years.
- The Operators — founder/CEO. Sports agency for tech talent. Still going.
- AnyQuestion → Whoop — joined Ed Baker, built the team, got acquired. Still at Whoop running AI and Community Engagement.
What I stand for
Champion mindset. Lead from the front. Disciple of the game. Take the final shot. The full list:
- It starts with you — mental, physical, emotional, spiritual.
- Bostonian transparent — say what others won't, with good intentions.
- Move with urgency — indecision kills dreams and companies.
- #WORKETHIC — nobody outworks me.
- Get curious — "I wonder why…"
- Self-awareness — maximize strengths, hire for weaknesses.
- Be a magnet for talent — winners attract winners.
- 24/7/365 service — always on for clients, partners, team.
- Flourish in adversity — when the world burns, my hands stay steady.
- Take care of the team — high standard for me and everyone around me.
What I believe
Economic-liberty techno-optimist. Entrepreneurs are heroes, not piggy banks. Supply-side beats price caps. Hard money is better than inflation-as-policy. AI and automation are generational unlocks. Help people transition, don't preserve obsolete jobs. Individual responsibility. Merit-based immigration. Disrupt K-12. Politics is service, not career.
How I work
Starting a task: write goal + recipient in plain text first. Scope before build. Review: I read work aloud as the recipient. If they'd have to ask a question to act, it's not done. "Done" means the recipient can act without coming back to me. A great week is a launch or event that landed.
Great work has clarity. One reading, no ambiguity. Re-reads mean failure. I respect work that has a clear POV. A side. No hedge. I hate corporate mush. If it could've been written by anyone about anything, it failed.
Now
Day job: VP of AI and Community Engagement at Whoop. I built the "AI at Work" department to train employees on how to use AI tools day to day.
Primary focus: the Massachusetts AI Coalition. Building the physical, cultural, and human infrastructure that makes Boston the #1 AI city. North Star by 2030: 200+ MA companies worth $1B+, 50+ worth $10B+.
Everything else lives on the portfolio page.