Drew Chapin, startup guy and go-to-market engineer
I'm building The Discoverability Company, backing pre-seed founders with Hustle Fund, shipping side projects, and writing about startup culture.
experience 11
Go-to-market strategy and discoverability that put people and businesses front and center across search, social, and AI. We also run poddisco for podcast visibility.
Completed the 5th Venture Fellow cohort and work with the Angel Squad on supporting hilariously early pre-seed founders.
Built the gift marketplace for the leading birthday-calendar app and drove organic growth through SEO and app-store optimization.
Incubated and operated early-stage media and e-commerce companies, running projects from concept through launch and growth.
Helped build the business from a single Twitter account into a leading independent sports-media brand with real revenue and a shop.
Early mover in shoppable media, with a personalized shopping app, a proprietary ad format, and DTC stores. The company failed and filed for bankruptcy, and I was convicted for misrepresentations I made while fundraising in 2020. I now speak openly about it.
First business hire. Built the company’s revenue plan and recruited and led its founding sales team.
Led all marketing for the distillery and made it the official spirit of the Vermont Ski Association.
Ran campus user acquisition for the Sequoia- and Bain-backed video platform, which Apple acquired in 2012.
Drove small-business and education adoption of Windows and Office across the territory as a field sales-marketing manager.
President of the Lyndon Student Government Association (2008–2010) and the Lyndon Student Investment Group (2010–2011).
investing
I write checks into pre-seed companies, and I completed the Hustle Fund Venture Fellowship in its 5th cohort in 2026. I am most useful before there is traction, on the unglamorous part: how you get found and how you turn attention into customers. Thesis, portfolio, and deal memos live at chapin.vc.
speaking & writing
I speak at business schools and conferences about startup failure and ethical fading, including Yale, UC Berkeley Haas, Drexel, and ACFE. The short version: good people rarely snap, they drift. I write at chapin.blog and on HackerNoon about being found online, founder psychology, the patterns of startup failure, and the many experiments and learnings we run at The Discoverability Company.
expertise
- Go-to-market strategy and customer acquisition
- Search engine optimization
- AI discoverability and visibility
- Online reputation management
- Early-stage startup scaling