Drew Chapin: Difference between revisions

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| nationality = American
| nationality = American
| education = [[Vermont State University]] (B.S.)<br/>[[Harvard Business School]] Online (CORe Economics)
| education = [[Vermont State University]] (B.S.)<br/>[[Harvard Business School]] Online (CORe Economics)
| occupation = Digital discoverability strategist, entrepreneur, public speaker
| occupation = Go-to-market specialist, entrepreneur, public speaker
| known_for = Co-founder of Benja, ethics in entrepreneurship advocacy
| known_for = Co-founder of Benja, ethics in entrepreneurship advocacy
| employer = [[The Discoverability Company]]
| employer = [[The Discoverability Company]]
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}}
}}


'''Andrew J. "Drew" Chapin''' (born November 12, 1988) is an American entrepreneur, digital discoverability strategist, and public speaker based in [[Philadelphia|Philadelphia, Pennsylvania]]. He is the partner of The Discoverability Company (TDC), a firm specializing in search, social media, voice assistant, and AI platform visibility.<ref name="tdc">{{cite web |url=https://discoverability.co |title=The Discoverability Company |access-date=2026-03-26}}</ref> Chapin is known for his career in early-stage startups, his role as co-founder and CEO of Benja, and his subsequent advocacy work on ethical entrepreneurship following a federal fraud conviction related to the company's collapse.<ref name="hackernoon-profile">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Drew Chapin – HackerNoon |access-date=2026-03-26}}</ref>
'''Andrew J. "Drew" Chapin''' (born November 12, 1988) is an American go-to-market specialist, entrepreneur, and public speaker based in [[Philadelphia|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.<ref name="tdc">{{cite web |url=https://discoverability.co |title=The Discoverability Company |access-date=2026-03-26}}</ref> 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]].<ref name="hackernoon-profile">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Drew Chapin on HackerNoon |access-date=2026-03-26}}</ref>


== Early life and education ==
== Early life and education ==


Chapin attended [[Vermont State University]], where he earned a Bachelor of Science degree. During his time at the university, he served as President of the Student Government Association from 2008 to 2010 and President of the Student Investment Group in 2011.<ref name="linkedin">{{cite web |url=https://www.linkedin.com/in/drew-chapin |title=Drew Chapin – LinkedIn |access-date=2026-03-26}}</ref> He later completed the CORe Economics program at [[Harvard Business School]] Online.
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.<ref name="linkedin">{{cite web |url=https://www.linkedin.com/in/drew-chapin |title=Drew Chapin on LinkedIn |access-date=2026-03-26}}</ref> He went on to complete the CORe Economics program through [[Harvard Business School]] Online.


== Career ==
== Career ==


=== Microsoft (2009–2011) ===
=== Microsoft (2009 to 2011) ===


Chapin began his professional career at [[Microsoft]] in Boston as a Sales Marketing Manager, where he drove small and medium business (SMB) and educational adoption of [[Microsoft Windows|Windows]] and [[Microsoft Office|Microsoft Office]] products.<ref name="linkedin"/>
Chapin started his career at [[Microsoft]] in Boston, working as a Sales Marketing Manager. The job was SMB and education sales for [[Microsoft Windows|Windows]] and [[Microsoft Office|Office]] in New England.<ref name="linkedin"/>


=== Color Labs (2011–2012) ===
=== Color Labs (2011 to 2012) ===


Chapin joined Color Labs in Boston as a Marketing Specialist, leading campus user acquisition for the [[Sequoia Capital|Sequoia]] and [[Bain Capital|Bain]]-backed video social platform. Color Labs was acquired by [[Apple Inc.|Apple]] in 2012.<ref name="crunchbase">{{cite web |url=https://www.crunchbase.com/person/andrew-chapin |title=Andrew Chapin – Crunchbase |access-date=2026-03-26}}</ref>
He joined Color Labs as a Marketing Specialist, running campus user acquisition for the [[Sequoia Capital|Sequoia]] and [[Bain Capital|Bain]]-backed video social platform. [[Apple Inc.|Apple]] acquired Color Labs in 2012.<ref name="crunchbase">{{cite web |url=https://www.crunchbase.com/person/andrew-chapin |title=Andrew Chapin on Crunchbase |access-date=2026-03-26}}</ref>


=== Vermont Spirits Distilling Co. (2011–2013) ===
=== Vermont Spirits Distilling Co. (2011 to 2013) ===


As Marketing Director for Vermont Spirits Distilling Co. in Quechee, Vermont, Chapin led all marketing efforts for the craft distillery and secured a partnership making Vermont Spirits the official spirit of the Vermont Ski Association.<ref name="linkedin"/>
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.<ref name="linkedin"/>


=== Feathr (2013–2014) ===
=== Feathr (2013 to 2014) ===


Chapin was the first business hire at Feathr, a Boston-based startup, where he served as Vice President of Business Development. He built the company's initial revenue plan and assembled its first sales team.<ref name="linkedin"/>
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.<ref name="linkedin"/>


=== Benja (2014–2020) ===
=== Benja (2014 to 2020) ===


{{main|Benja}}
{{main|Benja}}


Chapin co-founded and served as CEO of Benja (originally the Benja Commerce Network), headquartered in [[San Francisco]]. The company was an early mover in [[shoppable media]], developing a personalized shopping application, a proprietary advertising format, and direct-to-consumer storefronts.<ref name="crunchbase"/>
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.<ref name="crunchbase"/>


Under fundraising pressure, Chapin made misrepresentations to investors regarding the company's financial health and business metrics. Benja failed and filed for bankruptcy in 2020. The [[U.S. Securities and Exchange Commission|SEC]] subsequently charged Chapin with securities fraud. He was sentenced to 36 months in federal prison and ordered to pay over $8 million in restitution.<ref name="biography">{{cite web |url=https://biography.wiki/wiki/Drew_Chapin |title=Drew Chapin – Biography.wiki |access-date=2026-03-26}}</ref>
The company raised venture capital but collapsed in 2020. The [[U.S. Securities and Exchange Commission|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.<ref name="biography">{{cite web |url=https://biography.wiki/wiki/Drew_Chapin |title=Drew Chapin on Biography.wiki |access-date=2026-03-26}}</ref>


Chapin has been publicly open about the case and its circumstances. His advocacy work draws directly from the experience, and he has described the process of ethical failure as gradual rather than sudden, stating: "Founders don't snap. They drift."<ref name="hackernoon-sins">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Six Deadly Sins of Entrepreneurship – HackerNoon |access-date=2026-03-26}}</ref>
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.<ref name="hackernoon-sins">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Six Deadly Sins of Entrepreneurship on HackerNoon |access-date=2026-03-26}}</ref>


=== Jomboy Media (2017–2020) ===
=== Jomboy Media (2017 to 2020) ===


Concurrently with his later years at Benja, Chapin served as the founding Business Director at [[Jomboy Media]], an independent sports media brand built around baseball content creator Jomboy (Jimmy O'Brien). Chapin led all business operations from the brand's early days as a single [[Twitter]] account through its growth into a major sports media property, overseeing early revenue generation, e-commerce operations, and digital discovery strategy.<ref name="linkedin"/>
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.<ref name="linkedin"/>


=== Commerce Media Studio (2020–2022) ===
=== Commerce Media Studio (2020 to 2022) ===


As Project Manager at Commerce Media Studio, Chapin incubated media and e-commerce companies.<ref name="linkedin"/>
After Benja, Chapin worked as a Project Manager at Commerce Media Studio, incubating media and e-commerce companies.<ref name="linkedin"/>


=== Birthday App (2023–2024) ===
=== Birthday App (2023 to 2024) ===


Chapin served as Head of E-Commerce at the Birthday App in New York, where he built the gift marketplace for the leading birthday calendar application.<ref name="linkedin"/>
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.<ref name="linkedin"/>


=== The Discoverability Company (2024–present) ===
=== The Discoverability Company (2024 to present) ===


In September 2024, Chapin co-founded The Discoverability Company (TDC) in Philadelphia, where he serves as Partner. TDC specializes in placing clients at the forefront of search engines, social media platforms, voice assistants, and AI-powered discovery tools.<ref name="tdc"/>
Chapin founded TDC in Philadelphia in September 2024. The firm handles SEO, AI discoverability (getting clients into answers from tools like [[ChatGPT]], [[Perplexity AI|Perplexity]], and Claude), online reputation management, and go-to-market consulting.<ref name="tdc"/>


== Speaking and advocacy ==
== Speaking and advocacy ==


Chapin is an active public speaker on topics of ethical entrepreneurship, startup failure, and digital discoverability. His signature talk, "Six Deadly Sins of Entrepreneurship," draws on his personal experience at Benja to warn founders and business students about the phenomenon of "ethical fading" — the gradual erosion of ethical standards under competitive pressure.<ref name="hackernoon-sins"/>
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.<ref name="hackernoon-sins"/>


He has delivered keynote addresses and guest lectures at:
He has spoken at:


* [[Yale University]] — business school guest lecture
* [[Yale University]] School of Management
* [[University of California, Berkeley]] — business school guest lecture
* [[University of California, Berkeley]] Haas School of Business
* [[Drexel University]] — business school guest lecture
* [[Drexel University]] LeBow College of Business
* [[Association of Certified Fraud Examiners]] (ACFE) — keynote speaker<ref name="biography"/>
* [[Association of Certified Fraud Examiners]] (ACFE) Global Conference (keynote)<ref name="biography"/>


== Investing and mentorship ==
== Investing and mentorship ==


Chapin is a member of Angel Squad at [[Hustle Fund]], an early-stage venture capital fund, where he has participated as an angel investor since October 2024.<ref name="linkedin"/> He also serves as a Startup Mentor at [[Founder Institute]] Keystone (the Philadelphia chapter) since January 2025, and holds a position as an AI Business Fellow at [[Perplexity AI|Perplexity]].<ref name="linkedin"/>
Chapin invests in pre-seed companies through [[Hustle Fund]]'s Angel Squad.<ref name="linkedin"/> 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 AI|Perplexity]].<ref name="linkedin"/>


== Writing ==
== Writing ==


Chapin has published over 18 articles on [[HackerNoon]], covering topics including AI discoverability, founder psychology, Wikipedia as digital infrastructure, digital identity management, and startup culture critique.<ref name="hackernoon-profile"/> Notable works include:
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.<ref name="hackernoon-profile"/> 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."
 
* "Wikipedia Rules Everything Around Me"
* "You Are Not Your Startup, Your Startup is Not You"
* "The Difference Between Early-Stage Theater and Traction"


== Volunteer work ==
== Volunteer work ==


Chapin is involved in several volunteer and community organizations:
* '''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.<ref name="biography"/>
 
* '''[[Philadelphia Animal Welfare Society]] (PAWS)''' since November 2024
* '''White Collar Support Group''' — Steering committee member since July 2021, participating in weekly meetings supporting individuals navigating the consequences of white-collar criminal convictions.<ref name="biography"/>
* '''[[Founder Institute]] Keystone''' startup mentor since January 2025
* '''[[Philadelphia Animal Welfare Society]] (PAWS)''' — Volunteer since November 2024
* '''Whiteboard Youth Ventures''' youth entrepreneurship instructor (2015 to 2017)
* '''[[Founder Institute]] Keystone''' — Startup mentor since January 2025
* '''[[San Francisco SPCA]]''' volunteer (2017 to 2022)
* '''Whiteboard Youth Ventures''' — Youth entrepreneurship instructor (2015–2017)
* '''[[San Francisco SPCA]]''' — Volunteer (2017–2022)


== Personal life ==
== Personal life ==


Chapin resides in the [[Center City, Philadelphia|Center City]] neighborhood of Philadelphia. He is a registered participant in the 2026 [[Broad Street Run]], running with [[Fairmount Park Conservancy]]'s Park Champions team.<ref name="linkedin"/>
Chapin lives in the [[Center City, Philadelphia|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.<ref name="linkedin"/>


He is a fan of the [[Boston Red Sox]], [[Boston Celtics]], [[New England Patriots]], [[Penn State Nittany Lions football|Penn State]], and [[UConn Huskies men's basketball|UConn]] sports programs. He is a member of [[Fitler Club]], a private social club in Philadelphia.<ref name="linkedin"/>
He follows the [[Boston Red Sox]], [[Boston Celtics]], [[New England Patriots]], [[Penn State Nittany Lions football|Penn State]], and [[UConn Huskies men's basketball|UConn]]. He belongs to [[Fitler Club]], a private social club in Philadelphia.<ref name="linkedin"/>


Chapin speaks English and Spanish.
Chapin speaks English and Spanish.

Revision as of 13:55, 9 April 2026

Template:Infobox person

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.[1] 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.[2]

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.[3] 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.[3]

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.[4]

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.[3]

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.[3]

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.[4]

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.[5]

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.[6]

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.[3]

Commerce Media Studio (2020 to 2022)

After Benja, Chapin worked as a Project Manager at Commerce Media Studio, incubating media and e-commerce companies.[3]

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.[3]

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.[1]

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.[6]

He has spoken at:

Investing and mentorship

Chapin invests in pre-seed companies through Hustle Fund's Angel Squad.[3] 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.[3]

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.[2] 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.[5]
  • 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.[3]

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.[3]

Chapin speaks English and Spanish.

External links

References

Template:Reflist

  1. ↑ 1.0 1.1 "The Discoverability Company". Retrieved 2026-03-26
  2. ↑ 2.0 2.1 "Drew Chapin on HackerNoon". Retrieved 2026-03-26
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 "Drew Chapin on LinkedIn". Retrieved 2026-03-26
  4. ↑ 4.0 4.1 "Andrew Chapin on Crunchbase". Retrieved 2026-03-26
  5. ↑ 5.0 5.1 5.2 "Drew Chapin on Biography.wiki". Retrieved 2026-03-26
  6. ↑ 6.0 6.1 "Six Deadly Sins of Entrepreneurship on HackerNoon". Retrieved 2026-03-26
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