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. Chapin spent the previous decade in venture-backed startups; he is best known as the co-founder and CEO of Benja Commerce Network and the founding business director at Jomboy Media.

Chapin speaks at business schools and professional conferences on founder psychology and entrepreneurship ethics, drawing on his time as CEO of Benja, which failed in 2020. His talk, "Six Deadly Sins of Entrepreneurship," 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.

Outside of his consulting practice, Chapin is an angel investor through Hustle Fund's Angel Squad, a startup mentor at Founder Institute Keystone (which covers Philadelphia, Princeton, and the Delaware Valley), and sits on the steering committee of the White Collar Support Group, a 501(c)(3) that supports people navigating the white-collar justice system.

Early life and education

Chapin was born in Southbury, Connecticut, a town in New Haven County, on November 12, 1988, and grew up there before heading to Vermont for college. He went to Pomperaug Regional High School and graduated in 2007.

He attended Vermont State University (then Lyndon State College), where he earned a Bachelor of Science. On campus, he ran the Student Government Association as president from 2008 through 2010, then led the Student Investment Group in 2011. After Vermont, he completed the CORe (Credential of Readiness) program in economics through Harvard Business School Online.

Philadelphia career

The Discoverability Company (2024-present)

In September 2024, Chapin founded The Discoverability Company in Philadelphia. The firm is a go-to-market services company whose central thesis is that being "findable" now cuts across more than the traditional search engine, clients need to show up in Google results, in AI-generated answers from tools like ChatGPT, Perplexity, and Claude, in social media feeds, and in voice-assistant responses.

TDC's service model bundles four practices that clients historically bought from different firms: search engine optimization, what Chapin has publicly described as "AI discoverability" (the practice of getting a brand, product, or person cited by large language models and AI search tools), online reputation management, and hands-on go-to-market consulting. The firm positions this bundle as necessary rather than fashionable, arguing that a client who ranks on Google but never surfaces in ChatGPT is effectively invisible to a growing share of commercial and due-diligence queries.

The company is headquartered in Philadelphia and serves a national client base that includes professional services firms, consumer brands, and individual public figures dealing with reputation issues. Chapin has written in HackerNoon and elsewhere about his view that Wikipedia, wiki networks, and structured reference sites are functioning as the de facto "trust layer" that both humans and AI models increasingly rely on when evaluating a person or a company, an argument that feeds directly into TDC's methodology. The firm's public-facing branding (matte black, serif typography, minimalist copy) departs deliberately from the bright, sans-serif conventions of most digital marketing agencies and reflects Chapin's preference for a quiet, consultant-style presentation.

Founder Institute Keystone (2025-present)

Chapin serves as a startup mentor at Founder Institute Keystone, the Philadelphia-based chapter of the global pre-seed accelerator network, which covers Philadelphia, Princeton, New Jersey, and the broader Delaware Valley. His mentorship work there focuses on go-to-market, founder psychology, and decision-making under pressure, an area he speaks on publicly, drawing from his own record as a founder.

Angel investing

He invests in pre-seed companies through Hustle Fund's Angel Squad, a community of angel investors co-investing alongside the Hustle Fund partners, and in 2025 served as an AI Business Fellow at Perplexity.

Earlier career

Before returning to Philadelphia to start TDC, Chapin spent roughly a decade and a half in venture-backed startups and enterprise sales.

Microsoft (2009 to 2011)

Chapin started at Microsoft in Boston as a Sales Marketing Manager on the New England team, running small- and medium-business and education-sector sales for Windows and Office.

Color Labs (2011 to 2012)

He then moved to Color Labs, a Sequoia- and Bain-backed video social platform, as a Marketing Specialist running campus user acquisition. In October 2012, Apple acquired the Color Labs team in an acqui-hire.

Vermont Spirits Distilling Co. (2012 to 2013)

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

Feathr (2013 to 2014)

In 2013, Chapin joined Feathr, an events marketing SaaS company headquartered in Gainesville, Florida and founded by former University of Florida engineers. He was the company's first business hire, built its 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 moved to San Francisco to run it as Chief Executive Officer. Benja's pitch was shoppable media: a personalized mobile shopping app, a proprietary ad format for publishers, and a portfolio of direct-to-consumer storefronts built on the same underlying infrastructure. The company raised venture capital but did not grow into its pitch, and it failed in 2020. Chapin has spoken publicly about the legal fallout that followed the company's failure, using his own experience as a case study in his later work on founder ethical drift.

Jomboy Media (2017 to 2020)

While still running Benja, Chapin served concurrently as an early advisor and investor in Jomboy Media, and acted as its founding business director. He joined in 2017, when the operation was not yet a company but 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. In the 2020 Front Office Sports profile that documents Jomboy's rise, Chapin is identified as "a tech entrepreneur in San Francisco" who served as "advisor and early investor" in the venture.

Chapin put in early seed capital and ran the business side, commercial deals, ad sales, hiring, and structure, while O'Brien continued to create content. By the time Chapin stepped back in 2020, Jomboy Media had built a podcast network (including the flagship Talkin' Baseball), a merchandise business, advertising revenue, and a cross-platform following that numbered in the millions. The company has continued to grow into one of the largest independent voices in North American baseball media.

Commerce Media Studio (2020 to 2022)

After Benja, Chapin took a role as Project Manager at Commerce Media Studio, a firm that incubated media and e-commerce companies.

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 leaned heavily on organic channels, search engine optimization and App Store Optimization, to grow it, rather than paid user acquisition.

Speaking and advocacy

Chapin speaks at business schools and industry conferences on founder psychology, startup culture, and entrepreneurship ethics. His signature talk, "Six Deadly Sins of Entrepreneurship," uses his time at 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

Chapin has appeared as a guest on business and entrepreneurship podcasts, generally discussing the same founder-ethics themes that anchor 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.

Chapin is represented by the AAE Speakers Bureau for keynote bookings.

Writing

Chapin writes in HackerNoon on founder psychology, AI discoverability, digital infrastructure, and startup culture. His bylines also appear on ReadWrite, the New York Observer, HackerNoon, Benzinga, Medium, and Entrepreneur, per his Muck Rack journalist profile. His topic range clusters around three recurring themes: the mechanics of startup failure and founder ethical drift; the shift from search-engine visibility to AI and large-language-model discoverability; and the role of wiki networks and structured reference as an underappreciated layer of internet trust.

Selected articles include:

• "Wikipedia Rules Everything Around Me", an argument that Wikipedia and the broader wiki network function 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", on the distinction between signal and substance in early-stage metrics.
• "The New Tools Rewriting the Web", on the generative-AI platforms restructuring how the web is browsed and indexed, published June 6, 2025.
• "Your Bank Tried to Kill My Company", a first-person account of banking issues at Benja, published March 17, 2017.

Volunteer work

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. He has volunteered at the Philadelphia Animal Welfare Society since November 2024, and previously volunteered with the San Francisco SPCA from 2017 to 2022. From 2015 to 2017 he taught youth entrepreneurship programming through Whiteboard Youth Ventures.

Personal life

Chapin lives 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