I’m building The Discoverability Company and backing pre-seed founders. I also speak and write about early-stage startup life.

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 started working on The Discoverability Company in 2024.

Most early-stage companies are built without a lawyer anywhere near the founding team.

I’m orienting my work in the program around those early decisions: how founders can think more clearly about the legal choices they’re making (before they even realize they’re legal choices), and how new ventures think about engaging their first real counsel.

I started the MLS program in fall 2026.

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.

I joined the Angel Squad in 2024 and completed the Venture Fellowship, in its 5th cohort, in 2026.

Completed Perplexity’s AI Business Fellowship, a cohort program on applying AI inside a working business. It sits close to the day job: what I do is make people and companies findable in AI answers, so understanding how these systems actually retrieve and cite is the work.

I completed the Perplexity AI Business Fellowship in 2025.

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

I worked with the team at Birthday App from 2023 to 2024.

Business analytics, economics for managers, and financial accounting.

After a few false starts, I finally completed the CORe in 2021.

Helped build the business from a single Twitter account into a leading independent sports-media brand with real revenue and a shop.

I worked with the team at Jomboy from 2017 until December 2020.

Early mover in shoppable media, with a personalized shopping app, a proprietary ad format, and DTC stores. The company failed and filed for corporate 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 and the patterns of startup failure.

I founded Benja in 2014 and ran it as CEO until 2020.

First business hire. Built the company’s revenue plan and recruited and led its founding sales team.

I worked at Feathr from 2013 to 2014.

Led all marketing for the distillery and made it the official spirit of the Vermont Ski Association.

I led marketing there from 2011 to 2013.

Ran campus user acquisition for the Sequoia- and Bain-backed video platform, which Apple acquired in 2012.

I worked at Color Labs from 2011 to 2012, until Apple acquired it.

Drove small-business and education adoption of Windows and Office across the territory as a field sales-marketing manager.

I worked at Microsoft from 2009 to 2011.

President of the Lyndon Student Government Association (2008 to 2010) and the Lyndon Student Investment Group (2010 to 2011).

I graduated in May 2011.