$ drewchapin.com_

Drew Chapin

startup guy · operator, investor, writer, speaker

I have helped build companies from a napkin to eight figures, been around the table when startups got acquired, and run one straight into the ground. That is a 360-degree view of startup life most operators never get, and it is the lens for everything I do now: running The Discoverability Company, backing pre-seed founders with Hustle Fund, and writing and speaking about startup culture.

Philadelphia, PA · [email protected] · linkedin · book a call

experience 10

2024 – Partner The Discoverability Company
Go-to-market strategy and digital discoverability. Puts people and businesses front and center on search, social, voice assistants, and AI platforms. Tune-ups and reputation repair.
2024 – Angel Squad Hustle Fund
Investing in hilariously early pre-seed founders.
2023 – 24 Head of E-Commerce Birthday App
Built the gift marketplace for the leading birthday calendar app. Led organic growth through SEO and ASO.
2020 – 22 Project Manager Commerce Media Studio
Incubated media and e-commerce companies.
2017 – 20 Founding Business Director Jomboy Media
Built the business from a single Twitter account through early revenue, an e-commerce shop, and a leading independent sports media brand.
2014 – 20 Founder & CEO Benja Commerce Network
Early mover in shoppable media. Built a personalized shopping app, a proprietary ad format, and DTC stores. The company failed, filed for bankruptcy, and I was convicted for misrepresentations I made while fundraising in 2020. I now speak openly about the poor choices I made along the way and startup culture.
2013 – 14 VP Business Development Feathr
First business hire. Built the revenue plan and sales team.
2011 – 13 Marketing Director Vermont Spirits Distilling Co.
Led all marketing. Made the company the official spirit of the Vermont Ski Association.
2011 – 12 Marketing Specialist Color Labs
Campus user acquisition for the Sequoia and Bain backed video platform. Acquired by Apple in 2012.
2009 – 11 Sales Marketing Manager Microsoft
Drove SMB and education adoption of Windows and Office.

investing

I write checks into pre-seed companies and I am a Hustle Fund Venture Fellow in the fifth cohort. 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.io and on HackerNoon about AI discoverability, founder psychology, the patterns of startup failure, and the many experiments and learnings we run at The Discoverability Company.

expertise

faq 7

Who is Drew Chapin?
I'm Drew Chapin (Andrew J. Chapin), a Philadelphia-based startup operator and investor. I'm a partner at The Discoverability Company and a Hustle Fund Venture Fellow and Angel Squad member. I have built and helped sell companies, and I write and speak about startup culture.
What does The Discoverability Company do?
We help people and businesses control what the internet says about them and stay front and center across search, social media, voice assistants, and AI platforms. The work spans go-to-market strategy, search optimization, and reputation repair. More at discoverability.co.
Does Drew Chapin invest, and in what?
Yes. I'm an active angel investor and a Hustle Fund Venture Fellow in the fifth cohort. I'm most useful before there's traction, on the unglamorous part: how a company gets found and turns attention into customers. My thesis, portfolio, and deal memos live at chapin.vc.
What does Drew Chapin write and speak about?
Startup failure, founder psychology, and how discoverability is changing on an AI-shaped web. The short version of the talk: good people rarely snap, they drift. I write at chapin.io and on HackerNoon, and I'm spinning up a podcast at podcast.chapin.io.
Does Drew Chapin speak at events?
Yes. I've spoken at Yale School of Management, UC Berkeley Haas, Drexel, and ACFE conferences on startup failure and ethical fading. Talks and booking details are at chapin.io.
Where is Drew Chapin based?
Philadelphia, Pennsylvania. I work with people and companies anywhere, and I travel for talks.
How do I reach or book Drew Chapin?
Email [email protected] or book a 15-minute call.

contact

[email protected] · linkedin · threads · send a note