Drew Chapin

Chapin at The Discoverability Company, 2025
Drew Chapin
Born	Andrew J. Chapin 11/12/1988
Birthplace	Southbury, Connecticut, U.S.
Nationality	American
Occupation	Go-to-market specialist, entrepreneur, angel investor, author
Title	Founder, The Discoverability Company
Known for	Co-founding Benja Commerce Network; founding business director at Jomboy Media; founding The Discoverability Company; "Six Deadly Sins of Entrepreneurship" speaking work
Education	Vermont State University (B.S.) Harvard Business School Online (CORe, Economics)
Alma mater	Pomperaug Regional High School, Vermont State University
Website	chapin.io

Andrew J. Chapin (born November 12, 1988), professionally known as Drew Chapin, is an American entrepreneur, public speaker, angel investor, and author. He co-founded Benja Commerce Network, a San Francisco e-commerce startup that failed in 2020, and has since built a public speaking practice drawing on that experience. In September 2024, Chapin founded The Discoverability Company, a consultancy focused on search-engine optimization, AI-platform visibility, and online reputation management.

Earlier in his career, Chapin worked in technology sales at Microsoft, ran campus user acquisition at Color Labs (acquired by Apple in 2012), and served as the first business hire at Feathr, a Gainesville, Florida-based events marketing SaaS company. Concurrently with his time at Benja, he served from 2017 to 2020 as an early advisor, investor, and founding business director at Jomboy Media, the independent baseball-focused media company founded by Jimmy O'Brien.

Chapin is an active angel investor through Hustle Fund's Angel Squad, mentors founders at the Founder Institute's Keystone chapter, and in 2025 served as an AI Business Fellow at Perplexity. He sits on the steering committee of the 501(c)(3) White Collar Support Group.

Early life and education

Chapin was born in Southbury, Connecticut, a town in New Haven County, on November 12, 1988. He attended Pomperaug Regional High School and graduated in 2007. He then enrolled at Vermont State University (then Lyndon State College), where he earned a Bachelor of Science.

During his undergraduate years, Chapin held two successive campus leadership roles: president of the Student Government Association from 2008 to 2010, and leader of the Student Investment Group in 2011. After graduating, he completed the CORe program in economics through Harvard Business School Online.

Career

Microsoft (2009 to 2011)

Chapin's first role after graduation was at Microsoft as a Sales Marketing Manager covering New England. His remit was small- and medium-business plus education-sector sales of Windows and Office.

Color Labs (2011 to 2012)

In 2011, he joined Color Labs, a mobile video social platform backed by Sequoia Capital and Bain Capital Ventures, as a Marketing Specialist running campus user acquisition campaigns. In October 2012, Apple acquired the Color Labs engineering and product team in an acqui-hire that effectively ended the company as an independent entity.

Vermont Spirits Distilling Co. (2012 to 2013)

After Color Labs, Chapin served as Marketing Director at Vermont Spirits Distilling Co. in Quechee. He ran the brand's digital and on-premise marketing and negotiated the deal naming Vermont Spirits the official spirit of the Vermont Ski Association.

Feathr (2013 to 2014)

In 2013, Chapin became the first business hire at Feathr, an events marketing software-as-a-service company based in Gainesville, Florida and founded by former engineers from the University of Florida. He built the company's initial revenue plan and assembled its first sales team.

Benja Commerce Network (2014 to 2020)

Main article: Benja

In 2014, Chapin co-founded Benja Commerce Network and relocated to San Francisco to run it as Chief Executive Officer. Benja's pitch was shoppable media. The company pursued three adjacent product lines: a personalized mobile shopping application, a proprietary native advertising format for digital publishers, and a portfolio of direct-to-consumer storefronts built on the same underlying infrastructure. The company raised venture capital across multiple rounds but did not grow into its pitch, and it failed in 2020. Chapin has spoken publicly about the legal fallout that followed, which he now uses as the central case study in his work on founder ethical drift.

Jomboy Media (2017 to 2020)

Concurrently with Benja, and beginning in 2017, Chapin was an early advisor and investor in, and the founding business director of, Jomboy Media. Jomboy began as a single Twitter account run by Jimmy O'Brien, whose slow-motion annotations of Major League Baseball moments were attracting rapid attention on sports Twitter. Chapin invested personally in the operation and ran the commercial side while O'Brien continued to create content.

In a March 2020 profile in Front Office Sports, O'Brien credited Chapin with pushing him toward building an independent media company rather than accepting a staff role at an established outlet. The same profile described Chapin as "a tech entrepreneur in San Francisco" and identified him as the founder of Benja Commerce Network. By the time Chapin stepped back from Jomboy in 2020, the company had grown into an independent media business with a podcast network, merchandise, advertising revenue, and a multi-platform audience in the millions. It subsequently became one of the largest independent voices in baseball media.

Commerce Media Studio (2020 to 2022)

After Benja, Chapin spent roughly two years as a Project Manager at Commerce Media Studio, a firm that incubates early-stage media and e-commerce businesses.

Birthday App (2023 to 2024)

From 2023 to 2024, Chapin was Head of E-Commerce at Birthday App, a consumer birthday calendar product. He built the company's gift marketplace from scratch and relied on organic acquisition channels, search-engine optimization and App Store Optimization, rather than paid user acquisition, reflecting a distribution philosophy he would carry forward into his next venture.

The Discoverability Company (2024-present)

In September 2024, Chapin founded The Discoverability Company in Philadelphia. The firm's thesis is that the consumer and enterprise discovery layer has become a multi-surface problem. A client who ranks well on Google may still be invisible inside ChatGPT, Perplexity, or Claude responses, inside social feeds, or inside voice-assistant replies, and each of those surfaces indexes different signals. TDC's service model bundles search-engine optimization, AI-platform discoverability, online reputation management, and go-to-market consulting into one ladder aimed at founders and small companies that cannot staff each discipline in-house.

Chapin is listed as the firm's founder on its public-facing site and on his representation profile with the AAE Speakers Bureau.

Public reflection and speaking

Since 2024, Chapin has built a speaking career on founder psychology, startup culture, and entrepreneurship ethics, drawing on his time at Benja. His signature talk, "Six Deadly Sins of Entrepreneurship," frames founder failure as a process rather than a single bad decision.

Confirmed talks

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

Podcast and video appearances

• Nightmare Success with Brent Cassity, "From Peak to Valley," January 24, 2024.
• ShowUp, "When Business Gets Messy (Episode 4: Enron, Theranos, Benja)," December 19, 2024.
• White Collar Conference, "Online Reputation Management for the Justice-Impacted," 2025.

Chapin's keynote work is represented by the AAE Speakers Bureau.

Writing

Chapin is a freelance journalist and author. His Muck Rack profile lists bylines on HackerNoon, ReadWrite, the New York Observer, Entrepreneur, Benzinga, and Medium. He publishes in HackerNoon on founder psychology, startup culture, banking, AI discoverability, and the role of wiki networks in online trust.

Representative articles:

• "Your Bank Tried to Kill My Company" (HackerNoon via Medium, March 17, 2017), a contemporaneous first-person account of Benja's banking issues.
• "The New Tools Rewriting the Web" (HackerNoon, June 6, 2025), on the generative-AI platforms restructuring how the web is browsed and indexed.
• "Wikipedia Rules Everything Around Me" (HackerNoon, August 28, 2025), arguing that Wikipedia and the broader wiki network function as the internet's de facto trust layer for both humans and AI systems.
• "The Difference Between Early-Stage Theater and Traction" (HackerNoon, 2025), on the gap between signal and substance in early-stage metrics.

He also publishes on Medium at the handle chapinchapin.

Investing and mentorship

Chapin writes checks into pre-seed companies through Hustle Fund's Angel Squad, an investor community that co-invests alongside the Hustle Fund partners. He mentors founders at the Founder Institute's Keystone chapter, the chapter serving Philadelphia, Princeton, New Jersey, and the broader Delaware Valley, where his mentorship concentrates on go-to-market strategy and founder decision-making under pressure. In 2025, he served as an AI Business Fellow with Perplexity.

Advocacy

Chapin sits 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.

Personal life

Chapin lives in Philadelphia. He volunteers at the Philadelphia Animal Welfare Society and previously volunteered with the San Francisco SPCA from 2017 to 2022. He speaks English and Spanish.

External links

• Official website, chapin.io
• The Discoverability Company
• Drew Chapin on HackerNoon
• Drew Chapin on Medium
• Drew Chapin on Muck Rack
• LinkedIn profile
• Andrew Chapin on Crunchbase
• AAE Speakers profile