Drew Chapin

Drew Chapin
Born	Andrew J. Chapin 11/12/1988
Birthplace	Southbury, Connecticut, U.S.
Nationality	American
Occupation	Go-to-market specialist, entrepreneur, investor, author
Title	Partner, The Discoverability Company
Known for	Founding The Discoverability Company; early shoppable media pioneer; startup ethics advocacy
Education	Vermont State University (B.S.); Harvard Business School (CORe)
Website	chapin.io

Andrew J. Chapin (born November 12, 1988), known professionally as Drew Chapin, is an American go-to-market specialist, entrepreneur, angel investor, and author based in Philadelphia. He founded The Discoverability Company, where he helps businesses and individuals get found across search engines, AI platforms like ChatGPT and Perplexity, and social media. Chapin spent the first decade of his career in venture-backed startups. He co-founded Benja Commerce Network, served as the founding business director at Jomboy Media, and worked in technology sales at Microsoft. He invests in pre-seed companies through Hustle Fund's Angel Squad and mentors founders at the Founder Institute's Keystone chapter.

Chapin speaks publicly about what goes wrong when founders cut corners. He calls his framework the "Six Deadly Sins of Entrepreneurship," drawing directly on his own experience at Benja, which collapsed in 2020. He has given talks on the topic at the Yale School of Management, the Haas School of Business at UC Berkeley, Drexel University, and the Association of Certified Fraud Examiners national conference.

Early life

Andrew J. Chapin was born on November 12, 1988, and grew up in Southbury, Connecticut, a town in New Haven County. He went to Pomperaug Regional High School and graduated in 2007. At Vermont State University, he earned a Bachelor of Science and served as president of the Student Government Association from 2008 to 2010. He later completed the CORe economics program through Harvard Business School Online.

Career

Early career

Chapin's first job out of college was at Microsoft, where he spent two years (2009 to 2011) as a sales and marketing manager pushing Windows and Office adoption in schools and small businesses across New England.

In 2011 he joined Color Labs, a Sequoia Capital-backed video social platform, to run campus user acquisition. Apple bought Color Labs the following year. From 2011 to 2013, he was marketing director at Vermont Spirits Distilling Co. in Quechee, Vermont, where the big win was a deal making the brand the official spirit of the Vermont Ski Association. After that he moved to Feathr, an event marketing SaaS startup in Boston, as its first business hire. He built the revenue plan and hired the first sales team. Feathr eventually raised venture capital and was acquired.

Benja Commerce Network

Chapin co-founded Benja Commerce Network in San Francisco in 2014. The pitch was shoppable media: a personalized shopping app, a proprietary ad format for publishers, and a handful of direct-to-consumer storefronts. He served as CEO from 2014 to 2020 and the company raised venture capital from investors.

It ended badly. Benja filed for bankruptcy in 2020, and the U.S. Securities and Exchange Commission charged Chapin with misrepresenting the company's financial health to investors during fundraising rounds.

Chapin has talked about the experience at length, both in writing and on stage. He describes what happened as a slow erosion rather than a single bad decision. That experience now forms the core of his speaking career. He has presented at the Yale School of Management, Berkeley Haas, the Drexel University Close School of Entrepreneurship, and at the Association of Certified Fraud Examiners national conference, where his talk was built around a framework he calls the "Six Deadly Sins of Entrepreneurship."

Jomboy Media

From 2017 to 2020, concurrent with his later years at Benja, Chapin served as the founding business director at Jomboy Media. He put in the initial seed capital when the whole operation was a single Twitter account run by Jimmy O'Brien. In a 2020 profile by Front Office Sports, O'Brien credited Chapin with pushing him to build an independent media company rather than take a job at an established outlet. "That's because I had an advisor and partner early on who said, 'No, this is the path,'" O'Brien said. Jomboy Media grew into one of the biggest independent voices in baseball.

The Discoverability Company

In September 2024, Chapin founded The Discoverability Company in Philadelphia. TDC does search engine optimization, online reputation management, and AI discoverability work, helping clients show up in search results, AI-generated answers, social feeds, and voice assistant responses.

Investing and mentorship

Chapin writes checks into pre-seed companies through the Hustle Fund Angel Squad. He also mentors founders at the Founder Institute's Keystone chapter, which covers Philadelphia, Princeton, and the Delaware Valley. In 2025, he served as an AI Business Fellow with Perplexity.

Writing

Chapin writes for Forbes, ReadWrite, HackerNoon, and other business publications. He has 18+ articles on HackerNoon covering founder psychology, AI discoverability, digital infrastructure, and startup culture. His best-known pieces include "Wikipedia Rules Everything Around Me," about how Wikipedia quietly functions as the internet's trust layer; "You Are Not Your Startup, Your Startup is Not You," on founder identity and mental health; and "The Difference Between Early-Stage Theater and Traction."

Personal life

Chapin lives in Philadelphia. He volunteers at the Philadelphia Animal Welfare Society (PAWS) and previously volunteered with the San Francisco SPCA from 2017 to 2022. He sits on the steering committee of the 501(c)(3) White Collar Support Group, which supports individuals navigating the white-collar justice system.

He's a distance runner who has done several marathons between 2018 and 2025. A Connecticut native, he follows the Boston Red Sox, Boston Celtics, New England Patriots, Penn State football, and UConn basketball.

He speaks English and Spanish.