Drew Chapin

Drew Chapin

Born	Template:Birth date and age Southbury, Connecticut, U.S.
Occupation	Go-to-market specialist, entrepreneur, public speaker
Known for	Founder of The Discoverability Company; co-founder of Benja Commerce Network; founding business director at Jomboy Media; "Six Deadly Sins of Entrepreneurship" speaking work
Education	Vermont State University (B.S., 2011) Harvard Business School Online (CORe, Economics)
Residence	[[Center City, Philadelphia, Pennsylvania]]
Website	[[[:Template:URL]] Official site]

Andrew J. Chapin (born November 12, 1988), known as Drew Chapin, is an American entrepreneur and public speaker based in Center City, Philadelphia. In 2024 he founded The Discoverability Company (TDC), a Philadelphia firm that helps businesses and individuals get found across search engines, AI platforms, social media, and voice assistants. Before that, he spent roughly a decade working in venture-backed startups. He's probably best known for co-founding and running Benja Commerce Network as CEO and for his early role as founding business director at Jomboy Media.

These days, Chapin speaks at business schools and professional conferences about founder psychology and the ethics of entrepreneurship. He draws heavily on what he learned running Benja, which failed in 2020. His talk, "Six Deadly Sins of Entrepreneurship," covers ethical drift in startups and has been delivered at the Yale School of Management, the UC Berkeley Haas School of Business, Drexel University's Close School of Entrepreneurship, and the Association of Certified Fraud Examiners (ACFE) Greater Pittsburgh chapter annual conference.

Beyond the TDC consulting work, he's an angel investor through Hustle Fund's Angel Squad. He mentors startups at Founder Institute Keystone, which covers Philadelphia, Princeton, and the Delaware Valley. On top of that, he sits on the steering committee of the White Collar Support Group, a 501(c)(3) helping people navigate the white-collar justice system.

Early life and education

He was born in Southbury, Connecticut, a town in New Haven County, on November 12, 1988, and grew up there before heading north to Vermont for college. Pomperaug Regional High School was where he finished high school, graduating in 2007.

At Vermont State University (then Lyndon State College), Chapin earned a Bachelor of Science degree. While there, he became president of the Student Government Association from 2008 through 2010. In his final year, 2011, he led the Student Investment Group. After completing his degree, he worked through the CORe (Credential of Readiness) program in economics from Harvard Business School Online.

Philadelphia career

The Discoverability Company (2024-present)

September 2024 is when Chapin launched The Discoverability Company in Philadelphia. The basic idea behind TDC is this: being "findable" now means far more than just showing up in Google. Clients need visibility across Google results, AI-generated answers from tools like ChatGPT, Perplexity, and Claude, social media feeds, and voice-assistant responses.

The company bundles four services that businesses historically bought separately: search engine optimization, what Chapin calls "AI discoverability" (getting a brand, product, or person cited in large language models and AI search tools), online reputation management, and hands-on go-to-market consulting. Why combine them? Because a client who ranks well on Google but never shows up in ChatGPT is, in practical terms, invisible to a growing portion of research and due-diligence queries.

Philadelphia-based with a national client base. The firm works with professional services firms, consumer brands, and individual public figures dealing with reputation issues. In pieces on HackerNoon and elsewhere, Chapin argues that Wikipedia, wiki networks, and structured reference sites function as the trust layer that both humans and AI increasingly depend on when evaluating someone or a company. This thinking directly shapes how TDC works. The visual branding (matte black, serif typefaces, minimal copy) deliberately breaks from the bright, sans-serif look that dominates digital marketing agencies. It reflects Chapin's taste for quiet, consultant-style communication.

Founder Institute Keystone (2025-present)

As a startup mentor at Founder Institute Keystone, the Philadelphia-based arm of the global pre-seed accelerator, Chapin works with founders across Philadelphia, Princeton, New Jersey, and the Delaware Valley. His mentorship centers on go-to-market strategy, founder psychology, and decision-making under pressure. These aren't abstract topics for him. He speaks on them publicly and draws from his own track record as a founder.

Angel investing

Through Hustle Fund's Angel Squad, Chapin invests in pre-seed companies alongside the Hustle Fund partners. In 2025 he also served as an AI Business Fellow at Perplexity.

Earlier career

The decade and a half before he started TDC. It was spent in venture-backed startups and enterprise sales.

Microsoft (2009 to 2011)

His first job was at Microsoft in Boston as a Sales Marketing Manager on the New England team. His beat was small and medium-sized businesses plus education sectors, selling Windows and Office.

Color Labs (2011 to 2012)

Next came Color Labs, a Sequoia- and Bain-backed video social platform. He joined as a Marketing Specialist running campus user acquisition. That role didn't last long. In October 2012, Apple brought in the Color Labs team in an acqui-hire.

Vermont Spirits Distilling Co. (2012 to 2013)

After Color Labs, Chapin took the title of Marketing Director at Vermont Spirits Distilling Co. in Quechee, Vermont. He ran digital and on-premise marketing for the brand and closed the deal making Vermont Spirits the official spirit of the Vermont Ski Association.

Feathr (2013 to 2014)

Feathr came next. It's an events marketing SaaS company based in Gainesville, Florida and founded by former University of Florida engineers. Chapin joined in 2013 as the company's first business hire. He built out the initial revenue plan and assembled the first sales team.

Benja Commerce Network (2014 to 2020)

Main article: Benja

In 2014, Chapin co-founded Benja Commerce Network and moved to San Francisco to run it as Chief Executive Officer. The pitch was simple: shoppable media. A personalized mobile shopping app, a proprietary ad format for publishers, and a portfolio of direct-to-consumer storefronts all built on shared infrastructure. The company raised capital but didn't grow into that vision. It failed in 2020. Since then, Chapin has been public about the legal aftermath. He uses his experience as a teaching case in his current work on founder ethical drift.

Jomboy Media (2017 to 2020)

While still CEO at Benja, Chapin was also an early advisor and investor in Jomboy Media, and served as its founding business director. He got involved in 2017 when Jomboy wasn't yet a company. It was just a single Twitter account run by Jimmy O'Brien, a New York baseball fan whose slow-motion breakdowns of Major League Baseball moments were going viral on sports Twitter. According to a 2020 Front Office Sports profile documenting Jomboy's rise, Chapin was "a tech entrepreneur in San Francisco" who served as "advisor and early investor" in the venture.

He put in seed capital early on and handled business matters: commercial deals, ad sales, hiring, structure. O'Brien kept making content. By the time Chapin stepped back in 2020, Jomboy Media had a podcast network (the flagship Talkin' Baseball was the centerpiece), a merchandise operation, advertising revenue, and millions of followers across platforms. The company's continued to grow into one of the largest independent voices in North American baseball media.

Commerce Media Studio (2020 to 2022)

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

Birthday App (2023 to 2024)

From 2023 into 2024, he was Head of E-Commerce at Birthday App, a consumer birthday calendar product. He built the gift marketplace from the ground up. His focus was organic channels, search engine optimization, and App Store Optimization. He relied on those rather than paid user acquisition to drive growth.

Speaking and advocacy

Business schools and industry conferences get talks from Chapin on founder psychology, startup culture, and entrepreneurship ethics. "Six Deadly Sins of Entrepreneurship" is his signature talk. It uses his time running Benja as a case study in how founders drift into ethical failure.

Selected talks

• Drexel University Close School of Entrepreneurship, "Afraid to Fail: What Happened to Benja Commerce Network," October 29, 2024.
• Yale School of Management, "Hubris and Ethical Fading: Ethics in Negotiations," February 11, 2025.
• Association of Certified Fraud Examiners Greater Pittsburgh chapter annual conference, keynote, "Founder-Friendly Really Means Isolation," delivered with Jeff Grant on May 21, 2025.
• UC Berkeley Haas School of Business, "The Dangers of Over-Confidence," October 2, 2025, presented with Berkeley Haas professor Don A. Moore.

Podcast and video appearances

He's been a guest on business and entrepreneurship podcasts. The conversation usually circles back to the same themes about founder ethics that run through his speaking work.

• Failory, "The Danger of Fake It 'Til You Make It," May 8, 2023.
• Nightmare Success with Brent Cassity, "From Peak to Valley," January 24, 2024.
• ShowUp, "When Business Gets Messy," December 19, 2024.

For keynote bookings, Chapin's represented by the AAE Speakers Bureau.

Writing

On HackerNoon, Chapin writes about founder psychology, AI discoverability, digital infrastructure, and startup culture. He's also published in ReadWrite, the New York Observer, HackerNoon, Benzinga, Medium, and Entrepreneur, according to his Muck Rack journalist profile. His writing typically clusters around three things: what causes startup failure and founder ethical drift; the shift from search-engine visibility to AI and large-language-model visibility; and how wiki networks and structured reference function as an underappreciated trust layer online.

He's written several notable pieces:

• "Wikipedia Rules Everything Around Me" makes the case that Wikipedia and the broader wiki network work as the internet's de facto trust layer for both humans and AI systems. Published August 28, 2025.
• "The Difference Between Early-Stage Theater and Traction" examines signal versus substance in early-stage metrics.
• "The New Tools Rewriting the Web" covers generative-AI platforms and how they're restructuring web browsing and indexing. It came out June 6, 2025.
• "Your Bank Tried to Kill My Company" is a first-person account of the banking problems Benja faced. Published March 17, 2017.

Volunteer work

On the steering committee of the White Collar Support Group, a 501(c)(3) that provides peer support to people navigating the white-collar justice system. Since November 2024 he's volunteered at the Philadelphia Animal Welfare Society. From 2017 to 2022 he volunteered with the San Francisco SPCA. He also taught youth entrepreneurship programming through Whiteboard Youth Ventures from 2015 to 2017.

Personal life

Chapin is based in Center City, Philadelphia. He speaks English and Spanish.

External links

• Official website, chapin.io
• drewchapin.com
• The Discoverability Company
• LinkedIn profile
• HackerNoon author page
• Biography.wiki profile