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{{Infobox person
{{#seo:
| name = Drew Chapin
|title=Drew Chapin - Philadelphia entrepreneur, speaker, and go-to-market specialist
| occupation = Go-to-market specialist, Digital discovery strategist, Entrepreneur
|titlemode=replace
| residence = Philadelphia, Pennsylvania
|keywords=Drew Chapin,Andrew Chapin,The Discoverability Company,Philadelphia entrepreneur,Benja,Jomboy Media,AI discoverability,Center City Philadelphia
| known_for = Founder of The Discoverability Company, Former executive at Benja Commerce Network
|description=Drew Chapin is a Philadelphia-based entrepreneur, public speaker, and go-to-market specialist. He founded The Discoverability Company in Center City in 2024 and speaks publicly about startup ethics drawn from his time leading Benja Commerce Network.
| alma_mater =  
|og:image=https://discoverability.co/drew-chapin-2025-horizontal.png
| website =  
|og:type=profile
}}
}}
{{Infobox Person
| name        = Drew Chapin
| image        = Drew-chapin-2025.png
| image_size  = 220px
| caption      = Chapin in Philadelphia, 2025
| birth_name  = Andrew J. Chapin
| birth_date  = {{birth date and age|1988|11|12}}
| birth_place  = Southbury, Connecticut, U.S.
| residence    = [[Center City, Philadelphia]], Pennsylvania
| nationality  = American
| education    = [[Vermont State University]] (B.S., 2011)<br/>[[Harvard Business School]] Online (CORe, Economics)
| alma_mater  = Pomperaug Regional High School, Vermont State University
| 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
| employer    = [[The Discoverability Company]]
| title        = Founder & Managing Partner, The Discoverability Company
| website      = {{URL|chapin.io}}
}}
'''Andrew J. Chapin''' (born November 12, 1988), known as '''Drew Chapin''', is an American entrepreneur and public speaker based in [[Center City, Philadelphia|Center City]], [[Philadelphia]].<ref name="tdc-about">{{cite web |url=https://discoverability.co/who-is-drew-chapin |title=Who is Drew Chapin |publisher=The Discoverability Company |access-date=2026-04-23}}</ref> 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.<ref name="tdc-home">{{cite web |url=https://discoverability.co |title=The Discoverability Company |publisher=The Discoverability Company |access-date=2026-04-23}}</ref> 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]].<ref name="hackernoon-profile">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Drew Chapin on HackerNoon |publisher=HackerNoon |access-date=2026-04-23}}</ref>
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 [[Haas School of Business|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.<ref name="yale-talk">{{cite web |url=https://chapin.io/talk-hubris-ethical-fading-ethics-in-negotiations-at-yale-school-of-management/ |title=Hubris and Ethical Fading: Ethics in Negotiations at Yale School of Management |publisher=chapin.io |date=2025-02-11 |access-date=2026-04-23}}</ref><ref name="haas-talk">{{cite web |url=https://chapin.io/talk-dangers-of-hubris-over-confidence-at-berkeley-haas-don-a-moore/ |title=The Dangers of Over-Confidence at Berkeley Haas |publisher=chapin.io |date=2025-10-02 |access-date=2026-04-23}}</ref><ref name="drexel-talk">{{cite web |url=https://chapin.io/talk-drexel-close-entrepreneurship-what-happened-to-benja-commerce-network/ |title=Afraid to Fail at Drexel Close School of Entrepreneurship |publisher=chapin.io |date=2024-10-29 |access-date=2026-04-23}}</ref><ref name="acfe-talk">{{cite web |url=https://chapin.io/talk-isolation-the-founder-friendly-trap-at-acfe/ |title=Isolation: The Founder-Friendly Trap at ACFE |publisher=chapin.io |date=2025-05-21 |access-date=2026-04-23}}</ref>
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.<ref name="linkedin">{{cite web |url=https://www.linkedin.com/in/drew-chapin |title=Drew Chapin on LinkedIn |publisher=LinkedIn |access-date=2026-04-23}}</ref><ref name="wcsg">{{cite web |url=https://whitecollarsupportgroup.org |title=White Collar Support Group |publisher=White Collar Support Group |access-date=2026-04-23}}</ref>
== 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.<ref name="linkedin"/> Pomperaug Regional High School was where he finished high school, graduating in 2007.<ref name="linkedin"/>
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.<ref name="linkedin"/> After completing his degree, he worked through the CORe (Credential of Readiness) program in economics from [[Harvard Business School]] Online.<ref name="linkedin"/>
== Philadelphia career ==
=== The Discoverability Company (2024-present) ===
September 2024 is when Chapin launched [[The Discoverability Company]] in Philadelphia.<ref name="tdc-home"/> The basic idea behind TDC is this: being "findable" now means far more than just showing up in Google. Clients need visibility across [[Google (search engine)|Google]] results, AI-generated answers from tools like [[ChatGPT]], [[Perplexity AI|Perplexity]], and [[Claude (language model)|Claude]], social media feeds, and voice-assistant responses.<ref name="tdc-home"/><ref name="tdc-about"/>


'''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. After gaining experience building companies and revenue teams in San Francisco's competitive startup environment, Chapin relocated to Philadelphia where he founded The Discoverability Company and became an active participant in the region's entrepreneurial community through angel investing, mentorship, and thought leadership.
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.<ref name="tdc-about"/> 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.<ref name="tdc-home"/>


== Background ==
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.<ref name="wikipedia-rules">{{cite web |url=https://hackernoon.com/u/drewchapin |title=Wikipedia Rules Everything Around Me |publisher=HackerNoon |access-date=2026-04-23}}</ref> 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.<ref name="tdc-home"/>


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. His experience in Silicon Valley provided him with a comprehensive understanding of startup operations, from initial concept development through scaling challenges and potential failure scenarios.
=== Founder Institute Keystone (2025-present) ===


== Career ==
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.<ref name="linkedin"/> 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.


=== Early Startup Experience ===
=== Angel investing ===


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.
Through [[Hustle Fund]]'s Angel Squad, Chapin invests in pre-seed companies alongside the Hustle Fund partners.<ref name="hustle-fund">{{cite web |url=https://www.hustlefund.vc/squad |title=Angel Squad, invest alongside Hustle Fund |publisher=Hustle Fund |date=2025 |access-date=2026-04-23}}</ref> In 2025 he also served as an AI Business Fellow at [[Perplexity AI|Perplexity]].<ref name="linkedin"/>


=== Benja Commerce Network ===
== Earlier career ==


Chapin's most significant early-stage experience came through his leadership role at Benja Commerce Network, a shoppable-media startup that provided him with what he describes as a "360-degree view of early-stage entrepreneurship from idea to growth to failure." The company initially found success with its ad network platform, but eventually encountered significant challenges during fundraising efforts.
The decade and a half before he started TDC. It was spent in venture-backed startups and enterprise sales.


In a 2023 interview with Failory, Chapin candidly discussed the company's trajectory and the ethical challenges that arose during its later stages.<ref>{{cite web |title=The Danger of Fake It 'Til You Make It |url=https://www.failory.com/interview/benja |publisher=Failory |access-date=2026-03-15}}</ref> He has since used this experience as a foundation for his advocacy against the "fake it 'til you make it" mentality prevalent in startup culture, emphasizing the importance of authentic business practices and transparent communication.
=== Microsoft (2009 to 2011) ===


=== The Discoverability Company ===
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 [[Microsoft Windows|Windows]] and [[Microsoft Office|Office]].<ref name="linkedin"/>


Following his experiences in San Francisco, Chapin founded The Discoverability Company in Philadelphia, focusing on helping both early-stage startups and established brands improve their online visibility. The company 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.
=== Color Labs (2011 to 2012) ===


== Philadelphia Startup Community Involvement ==
Next came Color Labs, a [[Sequoia Capital|Sequoia]]- and [[Bain Capital Ventures|Bain]]-backed video social platform. He joined as a Marketing Specialist running campus user acquisition.<ref name="crunchbase">{{cite web |url=https://www.crunchbase.com/person/andrew-chapin |title=Drew Chapin, Crunchbase Person Profile |publisher=Crunchbase |date=2025 |access-date=2026-04-23}}</ref> That role didn't last long. In October 2012, [[Apple Inc.|Apple]] brought in the Color Labs team in an acqui-hire.<ref name="tc-color">{{cite web |url=https://techcrunch.com/2012/10/17/color-labs-talent-grab/ |title=Apple acquires Color Labs team |publisher=TechCrunch |date=2012-10-17 |access-date=2026-04-23}}</ref>


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. Through this role, he helps identify and support promising startups both locally and nationally.
=== Vermont Spirits Distilling Co. (2012 to 2013) ===


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.
After Color Labs, Chapin took the title of Marketing Director at Vermont Spirits Distilling Co. in [[Quechee, Vermont|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.<ref name="linkedin"/>


To document and analyze the growth of Philadelphia's startup scene, Chapin publishes a newsletter that chronicles developments in the local entrepreneurial ecosystem. This publication serves as both a resource for local entrepreneurs and a platform for Chapin to share insights about startup trends and best practices.
=== Feathr (2013 to 2014) ===


== Thought Leadership and Writing ==
Feathr came next. It's an events marketing SaaS company based in [[Gainesville, Florida]] and founded by former [[University of Florida]] engineers.<ref name="feathr-about">{{cite web |url=https://feathr.co |title=Feathr |publisher=Feathr |access-date=2026-04-23}}</ref> Chapin joined in 2013 as the company's first business hire. He built out the initial revenue plan and assembled the first sales team.<ref name="linkedin"/>


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.
=== Benja Commerce Network (2014 to 2020) ===


In November 2025, he published an analysis of the resurgence of crowdfunding as a viable fundraising strategy for startups.<ref>{{cite web |title=Crowdfunding Your Startup Is Making a Big Comeback |url=https://hackernoon.com/crowdfunding-your-startup-is-making-a-big-comeback |publisher=HackerNoon |access-date=2026-03-15}}</ref> 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.
{{main|Benja}}


He has also written about successful AI business models, including a case study of Creati, a company that achieved significant revenue growth in the artificial intelligence sector.<ref>{{cite web |title=How Creati Quietly Hit $10M in AI Revenue |url=https://hackernoon.com/how-creati-quietly-hit-$10m-in-ai-revenue |publisher=HackerNoon |access-date=2026-03-15}}</ref>
In 2014, Chapin co-founded Benja Commerce Network and moved to [[San Francisco]] to run it as Chief Executive Officer.<ref name="crunchbase"/> 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.<ref name="crunchbase"/> 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.<ref name="failory"/>


Additionally, Chapin has contributed commentary on technology leadership, including analysis of prominent figures in the tech industry and their influence on startup culture.<ref>{{cite web |title=Sam Altman: The Next Big Cult Hero in Tech |url=https://hackernoon.com/sam-altman-the-next-big-cult-hero-in-tech |publisher=HackerNoon |access-date=2026-03-15}}</ref>
=== Jomboy Media (2017 to 2020) ===


== Impact on Philadelphia's Business Community ==
While still CEO at Benja, Chapin was also an early advisor and investor in [[Jomboy Media]], and served as its founding business director.<ref name="fos-jomboy">{{cite web |last=McCarthy |first=Michael |url=https://frontofficesports.com/jomboy-media-jimmy-obrien/ |title=After Viral Astros and Yankees Videos, 'Jomboy' Looks To Build Media Brand |publisher=Front Office Sports |date=2020-03-05 |access-date=2026-04-23}}</ref> He got involved in 2017 when Jomboy wasn't yet a company. It was just a single [[Twitter]] account run by [[Jimmy O'Brien (podcaster)|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.<ref name="fos-jomboy"/>


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 with The Discoverability Company addresses a critical need for businesses of all sizes to maintain effective online presence in an increasingly complex digital landscape.
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.<ref name="fos-jomboy"/> The company's continued to grow into one of the largest independent voices in North American baseball media.


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


Chapin's advocacy for ethical business practices, informed by his direct experience with startup failures, provides valuable perspective for the local entrepreneurial community. His willingness to discuss both successes and failures openly contributes to a more mature and sustainable approach to startup development in the region.
After Benja closed, Chapin worked as Project Manager at Commerce Media Studio, a firm incubating media and e-commerce companies.<ref name="linkedin"/>
 
=== 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.<ref name="linkedin"/>
 
== Speaking and advocacy ==
 
Business schools and industry conferences get talks from Chapin on founder psychology, startup culture, and entrepreneurship ethics.<ref name="chapin-speaking-archive">{{cite web |url=https://chapin.io/tag/speaking-talks-workshops/ |title=Talks & Workshops by Drew Chapin |author=Drew Chapin |publisher=chapin.io |date=2025 |access-date=2026-04-23}}</ref> "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.<ref name="drexel-talk"/>
* [[Yale School of Management]], "Hubris and Ethical Fading: Ethics in Negotiations," February 11, 2025.<ref name="yale-talk"/>
* [[Association of Certified Fraud Examiners]] Greater Pittsburgh chapter annual conference, keynote, "Founder-Friendly Really Means Isolation," delivered with [[Jeff Grant]] on May 21, 2025.<ref name="acfe-talk"/><ref name="grantlaw-acfe">{{cite web |url=https://grantlaw.com/drew-chapin-jeff-grant-to-keynote-acfe-greater-pittsburg-chapter-annual-conference/ |title=Drew Chapin & Jeff Grant to Keynote ACFE Greater Pittsburgh Chapter Annual Conference |publisher=GrantLaw |date=2025 |access-date=2026-04-23}}</ref>
* [[Haas School of Business|UC Berkeley Haas School of Business]], "The Dangers of Over-Confidence," October 2, 2025, presented with Berkeley Haas professor [[Don A. Moore]].<ref name="haas-talk"/>
 
=== 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.<ref name="failory">{{cite web |url=https://www.failory.com/interview/benja |title=The Danger of Fake It 'Til You Make It (interview with Drew Chapin) |publisher=Failory |date=2023-05-08 |access-date=2026-04-23}}</ref>
* ''Nightmare Success'' with Brent Cassity, "From Peak to Valley," January 24, 2024.<ref name="pod-nightmare">{{cite web |url=https://chapin.io/podcast-nightmare-success-when-your-worst-fears-become-reality/ |title=Podcast: Nightmare Success, From Peak to Valley |author=Drew Chapin |publisher=chapin.io |date=2024-01-24 |access-date=2026-04-23}}</ref>
* ''ShowUp'', "When Business Gets Messy," December 19, 2024.<ref name="pod-showup">{{cite web |url=https://chapin.io/interviewed-on-podcast-showup-when-business-gets-messy-enron-theranos-benja/ |title=Podcast: ShowUp, When Business Gets Messy |author=Drew Chapin |publisher=chapin.io |date=2024-12-19 |access-date=2026-04-23}}</ref>
 
For keynote bookings, Chapin's represented by the [[All American Entertainment|AAE Speakers Bureau]].<ref name="aae">{{cite web |url=https://www.aaespeakers.com/keynote-speakers/andrew-j-chapin |title=Andrew J. Chapin, Keynote Speaker Profile |publisher=AAE Speakers Bureau |date=2025 |access-date=2026-04-23}}</ref>
 
== Writing ==
 
On [[HackerNoon]], Chapin writes about founder psychology, AI discoverability, digital infrastructure, and startup culture.<ref name="hackernoon-profile"/> He's also published in ''[[ReadWrite]]'', the ''[[New York Observer]]'', ''[[HackerNoon]]'', [[Benzinga]], [[Medium]], and ''[[Entrepreneur (magazine)|Entrepreneur]]'', according to his [[Muck Rack]] journalist profile.<ref name="muckrack">{{cite web |url=https://muckrack.com/drewchapin |title=Drew Chapin, Journalist Profile |publisher=Muck Rack |date=2025 |access-date=2026-04-23}}</ref> 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.<ref name="wikipedia-rules">{{cite web |url=https://hackernoon.com/wikipedia-rules-everything-around-me |title=Wikipedia Rules Everything Around Me |author=Drew Chapin |publisher=HackerNoon |date=2025-08-28 |access-date=2026-04-23}}</ref>
* "The Difference Between Early-Stage Theater and Traction" examines signal versus substance in early-stage metrics.<ref name="early-stage-theater">{{cite web |url=https://hackernoon.com/the-difference-between-early-stage-theater-and-traction |title=The Difference Between Early-Stage Theater and Traction |author=Drew Chapin |publisher=HackerNoon |date=2025 |access-date=2026-04-23}}</ref>
* "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.<ref name="new-tools">{{cite web |url=https://hackernoon.com/the-new-tools-rewriting-the-web |title=The New Tools Rewriting the Web |author=Drew Chapin |publisher=HackerNoon |date=2025-06-06 |access-date=2026-04-23}}</ref>
* "Your Bank Tried to Kill My Company" is a first-person account of the banking problems Benja faced. Published March 17, 2017.<ref name="bank-killed">{{cite web |url=https://medium.com/hackernoon/your-bank-tried-to-kill-my-company-15ab35bd732d |title=Your Bank Tried to Kill My Company |author=Drew Chapin |publisher=HackerNoon (via Medium) |date=2017-03-17 |access-date=2026-04-23}}</ref>
 
== 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.<ref name="wcsg-prisonist">{{cite web |url=https://prisonist.org/ |title=White Collar Support Group |publisher=Progressive Prison Ministries / White Collar Support Group |date=2025 |access-date=2026-04-23}}</ref><ref name="wcsg-davisvanguard">{{cite web |url=https://davisvanguard.org/2025/05/white-collar-support-group-reform/ |title=White Collar Support Group Advocates for Criminal Justice Reform |publisher=Davis Vanguard |date=2025-05 |access-date=2026-04-23}}</ref> Since November 2024 he's volunteered at the [[Philadelphia Animal Welfare Society]]. From 2017 to 2022 he volunteered with the [[San Francisco SPCA]].<ref name="linkedin"/> He also taught youth entrepreneurship programming through Whiteboard Youth Ventures from 2015 to 2017.<ref name="linkedin"/>
 
== Personal life ==
 
Chapin is based in [[Center City, Philadelphia]].<ref name="linkedin"/> He speaks English and Spanish.<ref name="linkedin"/>
 
== External links ==
 
* [https://chapin.io Official website, chapin.io]
* [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 author page]
* [https://biography.wiki/a/Drew_Chapin Biography.wiki profile]
 
== References ==
{{reflist}}
 
[[Category:1988 births]]
[[Category:Living people]]
[[Category:People from Philadelphia]]
[[Category:People from Center City, Philadelphia]]
[[Category:People from Southbury, Connecticut]]
[[Category:American businesspeople]]
[[Category:American technology entrepreneurs]]
[[Category:American public speakers]]
[[Category:American angel investors]]
[[Category:Founder Institute people]]
[[Category:Vermont State University alumni]]
[[Category:Harvard Business School alumni]]
[[Category:HackerNoon writers]]
[[Category:Pomperaug Regional High School alumni]]
[[Category:Microsoft people]]
[[Category:Jomboy Media people]]


== References ==
== References ==
<references />
<references />
[[Category:Living people]]
[[Category:American entrepreneurs]]
[[Category:Angel investors]]
[[Category:Philadelphia business people]]
[[Category:Digital marketing professionals]]
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Latest revision as of 03:34, 27 May 2026

Drew Chapin


BornTemplate:Birth date and age
Southbury, Connecticut, U.S.
OccupationGo-to-market specialist, entrepreneur, public speaker
Known forFounder of The Discoverability Company; co-founder of Benja Commerce Network; founding business director at Jomboy Media; "Six Deadly Sins of Entrepreneurship" speaking work
EducationVermont 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.[1] 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.[2] 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.[3]

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.[4][5][6][7]

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.[8][9]

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.[8] Pomperaug Regional High School was where he finished high school, graduating in 2007.[8]

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.[8] After completing his degree, he worked through the CORe (Credential of Readiness) program in economics from Harvard Business School Online.[8]

Philadelphia career

The Discoverability Company (2024-present)

September 2024 is when Chapin launched The Discoverability Company in Philadelphia.[2] 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.[2][1]

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.[1] 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.[2]

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.[10] 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.[2]

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.[8] 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.[11] In 2025 he also served as an AI Business Fellow at Perplexity.[8]

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.[8]

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.[12] That role didn't last long. In October 2012, Apple brought in the Color Labs team in an acqui-hire.[13]

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.[8]

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.[14] Chapin joined in 2013 as the company's first business hire. He built out the initial revenue plan and assembled the first sales team.[8]

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.[12] 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.[12] 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.[15]

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.[16] 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.[16]

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.[16] 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.[8]

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.[8]

Speaking and advocacy

Business schools and industry conferences get talks from Chapin on founder psychology, startup culture, and entrepreneurship ethics.[17] "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

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.[15]
  • Nightmare Success with Brent Cassity, "From Peak to Valley," January 24, 2024.[19]
  • ShowUp, "When Business Gets Messy," December 19, 2024.[20]

For keynote bookings, Chapin's represented by the AAE Speakers Bureau.[21]

Writing

On HackerNoon, Chapin writes about founder psychology, AI discoverability, digital infrastructure, and startup culture.[3] He's also published in ReadWrite, the New York Observer, HackerNoon, Benzinga, Medium, and Entrepreneur, according to his Muck Rack journalist profile.[22] 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.[10]
  • "The Difference Between Early-Stage Theater and Traction" examines signal versus substance in early-stage metrics.[23]
  • "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.[24]
  • "Your Bank Tried to Kill My Company" is a first-person account of the banking problems Benja faced. Published March 17, 2017.[25]

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.[26][27] Since November 2024 he's volunteered at the Philadelphia Animal Welfare Society. From 2017 to 2022 he volunteered with the San Francisco SPCA.[8] He also taught youth entrepreneurship programming through Whiteboard Youth Ventures from 2015 to 2017.[8]

Personal life

Chapin is based in Center City, Philadelphia.[8] He speaks English and Spanish.[8]

External links

References

Template:Reflist

References

  1. ↑ 1.0 1.1 1.2 "Who is Drew Chapin". The Discoverability Company. Retrieved 2026-04-23
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "The Discoverability Company". The Discoverability Company. Retrieved 2026-04-23
  3. ↑ 3.0 3.1 "Drew Chapin on HackerNoon". HackerNoon. Retrieved 2026-04-23
  4. ↑ 4.0 4.1 "Hubris and Ethical Fading: Ethics in Negotiations at Yale School of Management". chapin.io. 2025-02-11. Retrieved 2026-04-23
  5. ↑ 5.0 5.1 "The Dangers of Over-Confidence at Berkeley Haas". chapin.io. 2025-10-02. Retrieved 2026-04-23
  6. ↑ 6.0 6.1 "Afraid to Fail at Drexel Close School of Entrepreneurship". chapin.io. 2024-10-29. Retrieved 2026-04-23
  7. ↑ 7.0 7.1 "Isolation: The Founder-Friendly Trap at ACFE". chapin.io. 2025-05-21. Retrieved 2026-04-23
  8. ↑ 8.00 8.01 8.02 8.03 8.04 8.05 8.06 8.07 8.08 8.09 8.10 8.11 8.12 8.13 8.14 8.15 "Drew Chapin on LinkedIn". LinkedIn. Retrieved 2026-04-23
  9. ↑ "White Collar Support Group". White Collar Support Group. Retrieved 2026-04-23
  10. ↑ 10.0 10.1 "Wikipedia Rules Everything Around Me". HackerNoon. Retrieved 2026-04-23 Cite error: Invalid <ref> tag; name "wikipedia-rules" defined multiple times with different content
  11. ↑ "Angel Squad, invest alongside Hustle Fund". Hustle Fund. 2025. Retrieved 2026-04-23
  12. ↑ 12.0 12.1 12.2 "Drew Chapin, Crunchbase Person Profile". Crunchbase. 2025. Retrieved 2026-04-23
  13. ↑ "Apple acquires Color Labs team". TechCrunch. 2012-10-17. Retrieved 2026-04-23
  14. ↑ "Feathr". Feathr. Retrieved 2026-04-23
  15. ↑ 15.0 15.1 "The Danger of Fake It 'Til You Make It (interview with Drew Chapin)". Failory. 2023-05-08. Retrieved 2026-04-23
  16. ↑ 16.0 16.1 16.2 "After Viral Astros and Yankees Videos, 'Jomboy' Looks To Build Media Brand". Front Office Sports. 2020-03-05. Retrieved 2026-04-23
  17. ↑ Drew Chapin."Talks & Workshops by Drew Chapin". chapin.io. 2025. Retrieved 2026-04-23
  18. ↑ "Drew Chapin & Jeff Grant to Keynote ACFE Greater Pittsburgh Chapter Annual Conference". GrantLaw. 2025. Retrieved 2026-04-23
  19. ↑ Drew Chapin."Podcast: Nightmare Success, From Peak to Valley". chapin.io. 2024-01-24. Retrieved 2026-04-23
  20. ↑ Drew Chapin."Podcast: ShowUp, When Business Gets Messy". chapin.io. 2024-12-19. Retrieved 2026-04-23
  21. ↑ "Andrew J. Chapin, Keynote Speaker Profile". AAE Speakers Bureau. 2025. Retrieved 2026-04-23
  22. ↑ "Drew Chapin, Journalist Profile". Muck Rack. 2025. Retrieved 2026-04-23
  23. ↑ Drew Chapin."The Difference Between Early-Stage Theater and Traction". HackerNoon. 2025. Retrieved 2026-04-23
  24. ↑ Drew Chapin."The New Tools Rewriting the Web". HackerNoon. 2025-06-06. Retrieved 2026-04-23
  25. ↑ Drew Chapin."Your Bank Tried to Kill My Company". HackerNoon (via Medium). 2017-03-17. Retrieved 2026-04-23
  26. ↑ "White Collar Support Group". Progressive Prison Ministries / White Collar Support Group. 2025. Retrieved 2026-04-23
  27. ↑ "White Collar Support Group Advocates for Criminal Justice Reform". Davis Vanguard. 2025-05. Retrieved 2026-04-23
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