I’m Sean. I’ve spent the last decade and a half building and investing in companies, from inception through growth.
Work & background
- Merit Holdings — Long-term ownership & applied AI.
- Racepace — Coaching and community for endurance athletes.
- Pathlight Ventures — Inception and pre-seed through early Series A.
- OpenView — Growth investing. Series A, Series B, and beyond.
- Dispatch — Company building in field services software.
Across product, go-to-market, fundraising, and corporate development. B2B and consumer; mostly vertical software.
Questions I keep coming back to
- Data as float. Can a data business fund a permanent capital vehicle whose ambitions outlast the original business?
- Learning from real-world work. How do recorded workflows, verifiable outcomes, and proprietary data become training grounds for AI and robotics?
- Who captures AI’s value? Does AI strengthen existing software businesses—or route around them? Where do customer value and durable profits accumulate?
- Distribution when agents do the buying. What happens to discovery, advertising, and competition when businesses sell to a customer’s agent?
- Capital allocation & ownership. How do cash flow, control, incentives, and capital structure give companies room to make ambitious bets?
Writing
Capital Markets RoundupSubstack ↗My archive of writing on markets and companies.
Outside work
- Cycling, training, and racing. Leadville 100 finisher.
- Former president and captain, Boston College men’s rowing.