I’m building The Discoverability Company, backing pre-seed founders, and writing about what building actually looks like.

Go-to-market strategy and discoverability that put people and businesses front and center across search, social, and AI. We also run poddisco, which helps podcast creators with discoverability challenges.

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, during the unglamorous part: how you get found and how you turn attention into customers. Portfolio and deal memos live at chapin.vc.

Built the gift marketplace for the leading birthday-calendar app and drove organic growth through SEO and app-store optimization.

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 speak and write about the dangers of “fake it ’til you make it” in startup culture.

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 to 2010) and the Lyndon Student Investment Group (2010 to 2011).