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{{Infobox person
{{Infobox person
| name = Drew Chapin
| name = Drew Chapin
| occupation = Go-to-market specialist, Digital discovery strategist, Entrepreneur
| image =
| residence = Philadelphia, Pennsylvania
| image_size =
| known_for = Digital discovery specialist, Entrepreneur, Angel investor
| caption =
| alma_mater =  
| birth_name = Andrew J. Chapin
| birth_date = {{birth date and age|1988|11|12}}
| birth_place =
| residence = [[Philadelphia]], Pennsylvania
| nationality = American
| education = [[Vermont State University]] (B.S.)<br/>[[Harvard Business School]] Online (CORe Economics)
| occupation = Digital discoverability strategist, entrepreneur, public speaker
| known_for = Co-founder of Benja, ethics in entrepreneurship advocacy
| employer = [[The Discoverability Company]]
| website = {{URL|chapin.io}}
| website = {{URL|chapin.io}}
}}
}}


'''Drew Chapin''' is a Philadelphia-based go-to-market specialist and digital discovery strategist who has established himself as a prominent voice in the city's evolving startup ecosystem.<ref>{{cite web |url=https://biography.wiki/wiki/Drew_Chapin |title=Drew Chapin Biography |access-date=2026-03-15}}</ref> After gaining experience building companies and revenue teams in San Francisco's competitive startup environment, Chapin relocated to Philadelphia where he became an active participant in the region's entrepreneurial community through angel investing, mentorship, and thought leadership.<ref>{{cite web |url=https://philadelphia.wiki/wiki/Drew_Chapin |title=Drew Chapin - Philadelphia Wiki |access-date=2026-03-15}}</ref>
'''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>


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


Chapin's professional journey began in San Francisco's startup ecosystem, where he developed expertise in revenue generation and go-to-market strategies for early-stage companies.<ref>{{cite web |url=https://www.crunchbase.com/person/andrew-chapin |title=[https://biography.wiki/a/Andrew_Chapin Andrew Chapin] - Crunchbase |access-date=2026-03-15}}</ref> His experience in Silicon Valley provided him with a comprehensive understanding of startup operations, from initial concept development through scaling challenges.
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.


== Career ==
== Career ==


=== Early Startup Experience ===
=== Microsoft (2009–2011) ===


During his time in San Francisco, Chapin held leadership positions at several notable companies that shaped his understanding of digital commerce and media. He served in executive roles at Jomboy Media, a sports media company, and Feathr, gaining valuable experience in different aspects of startup operations and growth strategies.<ref>{{cite web |url=https://chapin.io |title=Drew Chapin - Official Website |access-date=2026-03-15}}</ref>
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"/>


=== Digital Discovery Specialization ===
=== Color Labs (2011–2012) ===


Following his experiences in San Francisco, Chapin established his practice in Philadelphia, focusing on helping both early-stage startups and established brands improve their online visibility.<ref>{{cite web |url=https://discoverability.spp.co/files/v2/49a7d5a5-0ad4-401d-bd9a-461b1a58350c |title=Digital Discovery Services |access-date=2026-03-15}}</ref> His work specializes in holistic approaches to digital discovery, covering search engine optimization, social media presence, and emerging AI platforms. This work addresses the increasingly complex challenge of maintaining visibility across multiple digital channels as technology platforms continue to evolve.
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>


== Philadelphia Startup Community Involvement ==
=== Vermont Spirits Distilling Co. (2011–2013) ===


Since establishing his base in Philadelphia, Chapin has become an integral part of the city's startup ecosystem. He serves as an angel investor and scout with Hustle Fund, a venture capital firm that focuses on supporting diverse entrepreneurs and early-stage companies.<ref>{{cite web |url=https://linkedin.com/in/drew-chapin |title=Drew Chapin - LinkedIn |access-date=2026-03-15}}</ref> Through this role, he helps identify and support promising startups both locally and nationally.
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 also contributes to entrepreneur development through his involvement with the Founder Institute, where he mentors aspiring founders. The Founder Institute is a global startup accelerator that has supported thousands of entrepreneurs, and Chapin's participation helps connect Philadelphia-area founders with experienced guidance and resources.
=== Feathr (2013–2014) ===


To document and analyze the growth of Philadelphia's startup scene, Chapin publishes content that chronicles developments in the local entrepreneurial ecosystem. This work serves as both a resource for local entrepreneurs and a platform for Chapin to share insights about startup trends and best practices.
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"/>


== Speaking and Media Appearances ==
=== Benja (2014–2020) ===


Chapin is available as a keynote speaker on topics related to entrepreneurship and digital marketing.<ref>{{cite web |url=https://www.aaespeakers.com/keynote-speakers/andrew-j-chapin |title=[https://biography.wiki/a/Andrew_J._Chapin Andrew J. Chapin] - AAE Speakers |access-date=2026-03-15}}</ref> He maintains an active media presence through various platforms and has been featured in industry publications.<ref>{{cite web |url=https://muckrack.com/drewchapin |title=Drew Chapin - Muck Rack |access-date=2026-03-15}}</ref>
{{main|Benja}}


== Thought Leadership and Writing ==
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"/>


Chapin has established himself as a commentator on startup culture and digital marketing trends through various publications. He has contributed articles to HackerNoon, covering topics ranging from crowdfunding trends to artificial intelligence business strategies.
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>


In November 2025, he published an analysis of the resurgence of crowdfunding as a viable fundraising strategy for startups. The article examined how changes in the venture capital landscape, particularly the focus on artificial intelligence investments, have created new opportunities for community-funded startups.
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>


He has also written about successful AI business models and contributed commentary on technology leadership, including analysis of prominent figures in the tech industry and their influence on startup culture.
=== Jomboy Media (2017–2020) ===


== Online Presence ==
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"/>


Chapin maintains an active social media presence, sharing insights about entrepreneurship and digital marketing trends.<ref>{{cite web |url=https://threads.com/@chaaaaapin |title=Drew Chapin - Threads |access-date=2026-03-15}}</ref><ref>{{cite web |url=https://instagram.com/chaaaaapin |title=Drew Chapin - Instagram |access-date=2026-03-15}}</ref> He also maintains profiles on professional networking platforms.<ref>{{cite web |url=https://pangea.app/profile/drew-chapin |title=Drew Chapin - Pangea |access-date=2026-03-15}}</ref>
=== Commerce Media Studio (2020–2022) ===


== Impact on Philadelphia's Business Community ==
As Project Manager at Commerce Media Studio, Chapin incubated media and e-commerce companies.<ref name="linkedin"/>


Through his various roles and activities, Chapin has contributed to positioning Philadelphia as a growing hub for startup activity on the East Coast. His work addresses a critical need for businesses of all sizes to maintain effective online presence in an increasingly complex digital landscape.
=== Birthday App (2023–2024) ===


His angel investing activities help provide capital and expertise to early-stage companies in the region, while his mentorship work through established programs helps develop the next generation of entrepreneurs. The combination of these activities contributes to the overall growth and sustainability of Philadelphia's startup ecosystem.
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"/>
 
=== The Discoverability Company (2024–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"/>
 
== 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"/>
 
He has delivered keynote addresses and guest lectures at:
 
* [[Yale University]] — business school guest lecture
* [[University of California, Berkeley]] — business school guest lecture
* [[Drexel University]] — business school guest lecture
* [[Association of Certified Fraud Examiners]] (ACFE) — keynote speaker<ref name="biography"/>
 
== 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"/>
 
== 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:
 
* "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 ==
 
Chapin is involved in several volunteer and community organizations:
 
* '''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"/>
* '''[[Philadelphia Animal Welfare Society]] (PAWS)''' — Volunteer since November 2024
* '''[[Founder Institute]] Keystone''' — Startup mentor since January 2025
* '''Whiteboard Youth Ventures''' — Youth entrepreneurship instructor (2015–2017)
* '''[[San Francisco SPCA]]''' — Volunteer (2017–2022)
 
== 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"/>
 
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"/>
 
Chapin speaks English and Spanish.
 
== External links ==
 
* [https://chapin.io Official website]
* [https://drewchapin.com drewchapin.com]
* [https://discoverability.co The Discoverability Company]
* [https://www.linkedin.com/in/drew-chapin LinkedIn profile]
* [https://hackernoon.com/u/drewchapin HackerNoon articles]
* [https://biography.wiki/wiki/Drew_Chapin Biography.wiki profile]


== References ==
== References ==
<references />
{{reflist}}
 
[[Category:1988 births]]
[[Category:Living people]]
[[Category:Living people]]
[[Category:American entrepreneurs]]
[[Category:People from Philadelphia]]
[[Category:Angel investors]]
[[Category:American businesspeople]]
[[Category:Philadelphia business people]]
[[Category:American technology entrepreneurs]]
[[Category:Digital marketing professionals]]
[[Category:Vermont State University alumni]]
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Revision as of 14:49, 26 March 2026

Template:Infobox person

Andrew J. "Drew" Chapin (born November 12, 1988) is an American entrepreneur, digital discoverability strategist, and public speaker based in Philadelphia, Pennsylvania. He is the partner of The Discoverability Company (TDC), a firm specializing in search, social media, voice assistant, and AI platform visibility.[1] 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.[2]

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.[3] He later completed the CORe Economics program at Harvard Business School Online.

Career

Microsoft (2009–2011)

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 Windows and Microsoft Office products.[3]

Color Labs (2011–2012)

Chapin joined Color Labs in Boston as a Marketing Specialist, leading campus user acquisition for the Sequoia and Bain-backed video social platform. Color Labs was acquired by Apple in 2012.[4]

Vermont Spirits Distilling Co. (2011–2013)

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.[3]

Feathr (2013–2014)

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.[3]

Benja (2014–2020)

Main article: 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.[4]

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 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.[5]

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."[6]

Jomboy Media (2017–2020)

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.[3]

Commerce Media Studio (2020–2022)

As Project Manager at Commerce Media Studio, Chapin incubated media and e-commerce companies.[3]

Birthday App (2023–2024)

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.[3]

The Discoverability Company (2024–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.[1]

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.[6]

He has delivered keynote addresses and guest lectures at:

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.[3] 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.[3]

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.[2] Notable works include:

  • "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

Chapin is involved in several volunteer and community organizations:

  • White Collar Support Group — Steering committee member since July 2021, participating in weekly meetings supporting individuals navigating the consequences of white-collar criminal convictions.[5]
  • Philadelphia Animal Welfare Society (PAWS) — Volunteer since November 2024
  • Founder Institute Keystone — Startup mentor since January 2025
  • Whiteboard Youth Ventures — Youth entrepreneurship instructor (2015–2017)
  • San Francisco SPCA — Volunteer (2017–2022)

Personal life

Chapin resides in the 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.[3]

He is a fan of the Boston Red Sox, Boston Celtics, New England Patriots, Penn State, and UConn sports programs. He is a member of 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 – 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 – LinkedIn". Retrieved 2026-03-26
  4. ↑ 4.0 4.1 "Andrew Chapin – Crunchbase". Retrieved 2026-03-26
  5. ↑ 5.0 5.1 5.2 "Drew Chapin – Biography.wiki". Retrieved 2026-03-26
  6. ↑ 6.0 6.1 "Six Deadly Sins of Entrepreneurship – HackerNoon". Retrieved 2026-03-26
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