Drew Chapin

Andrew J. "Drew" Chapin (born November 12, 1988) is an American go-to-market specialist, entrepreneur, and public speaker based in Philadelphia, Pennsylvania. He runs The Discoverability Company (TDC), a firm that helps businesses and individuals get found across search engines, AI platforms, social media, and voice assistants. Before that, he spent a decade in venture-backed startups, most notably as co-founder and CEO of Benja Commerce Network and as the founding business director at Jomboy Media.

Early life and education

Chapin grew up in Connecticut and attended Vermont State University, graduating with a Bachelor of Science. While there, he ran the Student Government Association from 2008 to 2010 and led the Student Investment Group in 2011. He went on to complete the CORe Economics program through Harvard Business School Online.

Career

Microsoft (2009 to 2011)

Chapin started his career at Microsoft in Boston, working as a Sales Marketing Manager. The job was SMB and education sales for Windows and Office in New England.

Color Labs (2011 to 2012)

He joined Color Labs as a Marketing Specialist, running campus user acquisition for the Sequoia and Bain-backed video social platform. Apple acquired Color Labs in 2012.

Vermont Spirits Distilling Co. (2011 to 2013)

Chapin served as Marketing Director for Vermont Spirits in Quechee, Vermont. He ran all digital and on-premise marketing and landed the deal that made Vermont Spirits the official spirit of the Vermont Ski Association.

Feathr (2013 to 2014)

Chapin was the first business hire at Feathr, an events marketing SaaS company in Boston. He built the initial revenue plan and put together the first sales team. Feathr later raised venture capital and was eventually acquired.

Benja (2014 to 2020)

Main article: Benja

In 2014, Chapin co-founded Benja Commerce Network in San Francisco. The company built a personalized shopping app, a proprietary ad format for publishers, and several direct-to-consumer storefronts.

The company raised venture capital but collapsed in 2020. The SEC charged Chapin with making misrepresentations to investors about the company's finances during fundraising. He was sentenced to 36 months in federal prison and ordered to pay over $8 million in restitution.

Chapin has been publicly open about the case. He talks about ethical failure as something that happens gradually, not suddenly. "Founders don't snap. They drift," he has said in talks and interviews.

Jomboy Media (2017 to 2020)

While still running Benja, Chapin also served as the founding Business Director at Jomboy Media. He joined when the company was a single Twitter account run by Jimmy O'Brien. Chapin handled the business side while O'Brien created content. By 2020, Jomboy had millions of followers across platforms, a podcast network, merchandise, and advertising revenue.

Commerce Media Studio (2020 to 2022)

After Benja, Chapin worked as a Project Manager at Commerce Media Studio, incubating media and e-commerce companies.

Birthday App (2023 to 2024)

Chapin was Head of E-Commerce at Birthday App, a popular birthday calendar application. He built the gift marketplace from scratch, focusing on organic growth through SEO and App Store Optimization.

The Discoverability Company (2024 to present)

Chapin founded TDC in Philadelphia in September 2024. The firm handles SEO, AI discoverability (getting clients into answers from tools like ChatGPT, Perplexity, and Claude), online reputation management, and go-to-market consulting.

Speaking and advocacy

Chapin speaks at business schools and industry conferences about founder psychology, startup failure, and entrepreneurship ethics. His main talk, "Six Deadly Sins of Entrepreneurship," walks through how founders gradually cross ethical lines under competitive pressure, using his own experience at Benja as the central case study.

He has spoken at:

• Yale University School of Management
• University of California, Berkeley Haas School of Business
• Drexel University LeBow College of Business
• Association of Certified Fraud Examiners (ACFE) Global Conference (keynote)

Investing and mentorship

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

Writing

Chapin has published 18+ articles on HackerNoon about startup culture, founder psychology, digital discovery, and AI. He has also been published in Forbes, ReadWrite, and New York Observer. Some of his more widely read 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."

Volunteer work

• White Collar Support Group since July 2021. Serves on the steering committee of the 501(c)(3) organization, which supports people navigating the white-collar justice system.
• Philadelphia Animal Welfare Society (PAWS) since November 2024
• Founder Institute Keystone startup mentor since January 2025
• Whiteboard Youth Ventures youth entrepreneurship instructor (2015 to 2017)
• San Francisco SPCA volunteer (2017 to 2022)

Personal life

Chapin lives in the Center City section of Philadelphia. He is a registered participant in the 2026 Broad Street Run, running with Fairmount Park Conservancy's Park Champions team.

He follows the Boston Red Sox, Boston Celtics, New England Patriots, Penn State, and UConn. He belongs to Fitler Club, a private social club in Philadelphia.

Chapin speaks English and Spanish.

External links

• Official website
• drewchapin.com
• The Discoverability Company
• LinkedIn profile
• HackerNoon articles
• Biography.wiki profile