Drew Chapin

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

Andrew J. Chapin (born November 12, 1988), known professionally as Drew Chapin, is an American entrepreneur, digital strategist, angel investor, and author based in Philadelphia. He is the founder and partner of The Discoverability Company, a firm specializing in search engine optimization, online reputation management, and digital visibility across search engines, artificial intelligence platforms, and social media. Chapin's career has spanned roles in technology sales at Microsoft, early-stage startup leadership, sports media, and venture investing. He is a member of the Hustle Fund Angel Squad and serves as a startup mentor with the Founder Institute's Keystone chapter. Chapin speaks publicly about entrepreneurial ethics and the dangers of "fake it 'til you make it" culture in the startup world, drawing on his own experience founding and ultimately losing a venture-backed company.

Early Life

Andrew J. Chapin was born on November 12, 1988, in Connecticut. He was raised in Southbury, Connecticut, a town in New Haven County, and attended Pomperaug Regional High School. Chapin went on to attend Vermont State University, where he earned a Bachelor of Business Administration degree. During his time at the university, he served as president of the Student Government Association from 2008 to 2010. He later completed the CORe economics program through Harvard Business School and lists several professional certificates on his LinkedIn profile.

Career

Early Career

Chapin began his professional career in 2009 at Microsoft, where he worked as a sales and marketing manager for over two years, focusing on driving adoption of Windows and Office products among small and medium-sized businesses and educational institutions.

In 2011, Chapin joined Color Labs, a Sequoia Capital-backed video social platform, as a marketing specialist leading campus user acquisition. Color Labs was subsequently acquired by Apple in 2012. From 2011 to 2013, Chapin served as marketing director for Vermont Spirits Distilling Co. in Quechee, Vermont, where he led all digital and on-premise marketing efforts and secured a partnership making the company the official spirit of the Vermont Ski Association. He subsequently joined Feathr, an event marketing technology company in Boston, as its first business hire, building the company's initial revenue plan and sales team.

Benja Commerce Network

In 2014, Chapin co-founded Benja Commerce Network, a San Francisco-based technology company that was an early mover in shoppable media. Benja developed a personalized shopping application, a proprietary advertising format, and several direct-to-consumer storefronts. Chapin served as chief executive officer from 2014 to 2020, overseeing all business operations.

The company ultimately failed and filed for bankruptcy in 2020. The U.S. Securities and Exchange Commission charged Chapin with making misrepresentations to investors during the company's fundraising efforts. Chapin has spoken openly about this experience, describing it as a case of gradual ethical erosion rather than a single decision, and has used it as the basis for public advocacy around founder accountability. He has delivered talks on the subject at the Yale School of Management, the Haas School of Business at the University of California, Berkeley, the Drexel University Close School of Entrepreneurship, and at the Association of Certified Fraud Examiners national conference, where he presented a framework he calls the "Six Deadly Sins of Entrepreneurship," identifying warning signs of ethical decline in founders.

Jomboy Media

Chapin served on the board of directors at Jomboy Media from its inception, providing the initial seed capital when the company was a single Twitter account. He served as the founding business director from 2017 to 2020, concurrent with his later years at Benja, leading all business matters through its early growth phase, including initial revenue generation, an e-commerce operation, and digital discovery strategy. In a 2020 profile by Front Office Sports, Jomboy Media founder Jimmy O'Brien described Chapin as "an advisor and early investor since the company's early days," crediting him with reinforcing the vision of building an independent media company rather than seeking employment 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 has since grown into one of the most recognized independent voices in baseball media.

The Discoverability Company

In September 2024, Chapin founded The Discoverability Company (TDC) in Philadelphia. The firm provides search engine optimization, online reputation management, and digital discoverability services, helping individuals and businesses establish and maintain their online presence across search engines, social media platforms, voice assistants, and AI systems. TDC's services include go-to-market strategy, customer acquisition consulting, and reputation repair.

Investing and Mentorship

Chapin is a member of the Hustle Fund Angel Squad, a venture capital community that invests in early-stage companies. He also serves as a startup mentor with the Founder Institute's Keystone chapter, which covers the Delaware Valley, Philadelphia, and Princeton regions. In 2025, Chapin served as an AI Business Fellow with Perplexity.

Writing

Chapin's writing has been published in Forbes, ReadWrite, HackerNoon, Entrepreneur, and other technology and business publications. His work covers topics including AI discoverability, founder psychology, digital infrastructure, and startup culture. Notable pieces include "Wikipedia Rules Everything Around Me," "You Are Not Your Startup, Your Startup is Not You," and "The Difference Between Early-Stage Theater and Traction."

Personal Life

Chapin resides in Philadelphia. He is an active volunteer with the Philadelphia Animal Welfare Society (PAWS) and previously volunteered with the San Francisco SPCA from 2017 to 2022. He serves on the steering committee of the 501(c)(3) White Collar Support Group, a group which serves individuals who are navigating the realities of the white collar justice system in the United States.

Chapin is a distance runner who has completed several marathons between 2018 and 2025. Based on his personal social media posts, he is an avid fan of Boston sports teams, including the Boston Red Sox, the Boston Celtics, and the New England Patriots, as well as Penn State football and UConn basketball.

He speaks English and Spanish.