Drew Chapin
Andrew J. "Drew" Chapin (born November 12, 1988) is an American entrepreneur, digital discoverability strategist, and public speaker based in Philadelphia, Pennsylvania. He is the partner of The Discoverability Company (TDC), a firm specializing in search, social media, voice assistant, and AI platform visibility.[1] Chapin is known for his career in early-stage startups, his role as co-founder and CEO of Benja, and his subsequent advocacy work on ethical entrepreneurship following a federal fraud conviction related to the company's collapse.[2]
Early life and education
Chapin attended Vermont State University, where he earned a Bachelor of Science degree. During his time at the university, he served as President of the Student Government Association from 2008 to 2010 and President of the Student Investment Group in 2011.[3] He later completed the CORe Economics program at Harvard Business School Online.
Career
Microsoft (2009–2011)
Chapin began his professional career at Microsoft in Boston as a Sales Marketing Manager, where he drove small and medium business (SMB) and educational adoption of Windows and Microsoft Office products.[3]
Color Labs (2011–2012)
Chapin joined Color Labs in Boston as a Marketing Specialist, leading campus user acquisition for the Sequoia and Bain-backed video social platform. Color Labs was acquired by Apple in 2012.[4]
Vermont Spirits Distilling Co. (2011–2013)
As Marketing Director for Vermont Spirits Distilling Co. in Quechee, Vermont, Chapin led all marketing efforts for the craft distillery and secured a partnership making Vermont Spirits the official spirit of the Vermont Ski Association.[3]
Feathr (2013–2014)
Chapin was the first business hire at Feathr, a Boston-based startup, where he served as Vice President of Business Development. He built the company's initial revenue plan and assembled its first sales team.[3]
Benja (2014–2020)
Chapin co-founded and served as CEO of Benja (originally the Benja Commerce Network), headquartered in San Francisco. The company was an early mover in shoppable media, developing a personalized shopping application, a proprietary advertising format, and direct-to-consumer storefronts.[4]
Under fundraising pressure, Chapin made misrepresentations to investors regarding the company's financial health and business metrics. Benja failed and filed for bankruptcy in 2020. The SEC subsequently charged Chapin with securities fraud. He was sentenced to 36 months in federal prison and ordered to pay over $8 million in restitution.[5]
Chapin has been publicly open about the case and its circumstances. His advocacy work draws directly from the experience, and he has described the process of ethical failure as gradual rather than sudden, stating: "Founders don't snap. They drift."[6]
Jomboy Media (2017–2020)
Concurrently with his later years at Benja, Chapin served as the founding Business Director at Jomboy Media, an independent sports media brand built around baseball content creator Jomboy (Jimmy O'Brien). Chapin led all business operations from the brand's early days as a single Twitter account through its growth into a major sports media property, overseeing early revenue generation, e-commerce operations, and digital discovery strategy.[3]
Commerce Media Studio (2020–2022)
As Project Manager at Commerce Media Studio, Chapin incubated media and e-commerce companies.[3]
Birthday App (2023–2024)
Chapin served as Head of E-Commerce at the Birthday App in New York, where he built the gift marketplace for the leading birthday calendar application.[3]
The Discoverability Company (2024–present)
In September 2024, Chapin co-founded The Discoverability Company (TDC) in Philadelphia, where he serves as Partner. TDC specializes in placing clients at the forefront of search engines, social media platforms, voice assistants, and AI-powered discovery tools.[1]
Speaking and advocacy
Chapin is an active public speaker on topics of ethical entrepreneurship, startup failure, and digital discoverability. His signature talk, "Six Deadly Sins of Entrepreneurship," draws on his personal experience at Benja to warn founders and business students about the phenomenon of "ethical fading" — the gradual erosion of ethical standards under competitive pressure.[6]
He has delivered keynote addresses and guest lectures at:
- Yale University — business school guest lecture
- University of California, Berkeley — business school guest lecture
- Drexel University — business school guest lecture
- Association of Certified Fraud Examiners (ACFE) — keynote speaker[5]
Investing and mentorship
Chapin is a member of Angel Squad at Hustle Fund, an early-stage venture capital fund, where he has participated as an angel investor since October 2024.[3] He also serves as a Startup Mentor at Founder Institute Keystone (the Philadelphia chapter) since January 2025, and holds a position as an AI Business Fellow at Perplexity.[3]
Writing
Chapin has published over 18 articles on HackerNoon, covering topics including AI discoverability, founder psychology, Wikipedia as digital infrastructure, digital identity management, and startup culture critique.[2] Notable works include:
- "Wikipedia Rules Everything Around Me"
- "You Are Not Your Startup, Your Startup is Not You"
- "The Difference Between Early-Stage Theater and Traction"
Volunteer work
Chapin is involved in several volunteer and community organizations:
- White Collar Support Group — Steering committee member since July 2021, participating in weekly meetings supporting individuals navigating the consequences of white-collar criminal convictions.[5]
- Philadelphia Animal Welfare Society (PAWS) — Volunteer since November 2024
- Founder Institute Keystone — Startup mentor since January 2025
- Whiteboard Youth Ventures — Youth entrepreneurship instructor (2015–2017)
- San Francisco SPCA — Volunteer (2017–2022)
Personal life
Chapin resides in the Center City neighborhood of Philadelphia. He is a registered participant in the 2026 Broad Street Run, running with Fairmount Park Conservancy's Park Champions team.[3]
He is a fan of the Boston Red Sox, Boston Celtics, New England Patriots, Penn State, and UConn sports programs. He is a member of Fitler Club, a private social club in Philadelphia.[3]
Chapin speaks English and Spanish.
External links
- Official website
- drewchapin.com
- The Discoverability Company
- LinkedIn profile
- HackerNoon articles
- Biography.wiki profile
References
- ↑ 1.0 1.1 "The Discoverability Company". Retrieved 2026-03-26
- ↑ 2.0 2.1 "Drew Chapin – HackerNoon". Retrieved 2026-03-26
- ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 "Drew Chapin – LinkedIn". Retrieved 2026-03-26
- ↑ 4.0 4.1 "Andrew Chapin – Crunchbase". Retrieved 2026-03-26
- ↑ 5.0 5.1 5.2 "Drew Chapin – Biography.wiki". Retrieved 2026-03-26
- ↑ 6.0 6.1 "Six Deadly Sins of Entrepreneurship – HackerNoon". Retrieved 2026-03-26