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{{#seo:
|title=Drew Chapin - Philadelphia entrepreneur, speaker, and go-to-market specialist
|titlemode=replace
|keywords=Drew Chapin,Andrew Chapin,The Discoverability Company,Philadelphia entrepreneur,Benja,Jomboy Media,AI discoverability,Center City Philadelphia
|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.
|og:image=https://discoverability.co/drew-chapin-2025-horizontal.png
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{{Infobox person
{{Infobox person
| name = Drew Chapin
| name         = Drew Chapin
| image =
| image       = Drew-chapin-2025.png
| image_size =
| image_size   = 220px
| caption =
| caption     = Chapin in Philadelphia, 2025
| birth_name = Andrew J. Chapin
| birth_name   = Andrew J. Chapin
| birth_date = {{birth date and age|1988|11|12}}
| birth_date   = {{birth date and age|1988|11|12}}
| birth_place =
| birth_place = Southbury, Connecticut, U.S.
| residence = [[Philadelphia]], Pennsylvania
| residence   = [[Center City, Philadelphia]], Pennsylvania
| nationality = American
| nationality = American
| education = [[Vermont State University]] (B.S.)<br/>[[Harvard Business School]] Online (CORe Economics)
| education   = [[Vermont State University]] (B.S., 2011)<br/>[[Harvard Business School]] Online (CORe, Economics)
| occupation = Go-to-market specialist, entrepreneur, public speaker
| alma_mater  = Pomperaug Regional High School, Vermont State University
| known_for = Co-founder of Benja, ethics in entrepreneurship advocacy
| occupation   = Go-to-market specialist, entrepreneur, public speaker
| employer = [[The Discoverability Company]]
| 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
| website = {{URL|chapin.io}}
| employer     = [[The Discoverability Company]]
| title        = Founder & Managing Partner, The Discoverability Company
| website     = {{URL|chapin.io}}
}}
}}


'''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>
'''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> 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]].<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>
 
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 [[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>
 
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.<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 ==
== 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.<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.
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.<ref name="linkedin"/> He went to Pomperaug Regional High School and graduated in 2007.<ref name="linkedin"/>
 
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.<ref name="linkedin"/> After Vermont, he completed the CORe (Credential of Readiness) program in economics through [[Harvard Business School]] Online.<ref name="linkedin"/>
 
== Philadelphia career ==
 
=== The Discoverability Company (2024-present) ===
 
In September 2024, Chapin founded [[The Discoverability Company]] in Philadelphia.<ref name="tdc-home"/> 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 (search engine)|Google]] results, in AI-generated answers from tools like [[ChatGPT]], [[Perplexity AI|Perplexity]], and [[Claude (language model)|Claude]], in social media feeds, and in voice-assistant responses.<ref name="tdc-home"/><ref name="tdc-about"/>
 
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.<ref name="tdc-about"/> 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.<ref name="tdc-home"/>
 
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.<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 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.<ref name="tdc-home"/>
 
=== Founder Institute Keystone (2025-present) ===


== Career ==
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.<ref name="linkedin"/> 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,<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> and in 2025 served as an AI Business Fellow at [[Perplexity AI|Perplexity]].<ref name="linkedin"/>
 
== 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) ===
=== 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 [[Microsoft Windows|Windows]] and [[Microsoft Office|Office]] in New England.<ref name="linkedin"/>
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 [[Microsoft Windows|Windows]] and [[Microsoft Office|Office]].<ref name="linkedin"/>


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


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>
He then moved to Color Labs, a [[Sequoia Capital|Sequoia]]- and [[Bain Capital Ventures|Bain]]-backed video social platform, 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> In October 2012, [[Apple Inc.|Apple]] acquired 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>


=== Vermont Spirits Distilling Co. (2011 to 2013) ===
=== Vermont Spirits Distilling Co. (2012 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.<ref name="linkedin"/>
After Color Labs, Chapin served as Marketing Director at Vermont Spirits Distilling Co. in [[Quechee, Vermont|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.<ref name="linkedin"/>


=== Feathr (2013 to 2014) ===
=== 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.<ref name="linkedin"/>
In 2013, Chapin joined [[Feathr]], an events marketing SaaS company headquartered 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> He was the company's first business hire, built its initial revenue plan, and assembled its first sales team.<ref name="linkedin"/>


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


{{main|Benja}}
{{main|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.<ref name="crunchbase"/>
In 2014, Chapin co-founded Benja Commerce Network and moved to [[San Francisco]] to run it as Chief Executive Officer.<ref name="crunchbase"/> 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.<ref name="crunchbase"/> 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.<ref name="failory"/>


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>
=== Jomboy Media (2017 to 2020) ===
 
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 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.<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 joined in 2017, when the operation was not yet a company but 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. 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.<ref name="fos-jomboy"/>


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"/>
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.<ref name="fos-jomboy"/> The company has continued to grow into one of the largest independent voices in North American baseball media.


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


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


=== Birthday App (2023 to 2024) ===
=== 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.<ref name="linkedin"/>
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.<ref name="linkedin"/>


=== The Discoverability Company (2024 to present) ===
== Speaking and advocacy ==


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"/>
Chapin speaks at business schools and industry conferences 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> His signature talk, "Six Deadly Sins of Entrepreneurship," uses his time at Benja as a case study in how founders drift into ethical failure.


== Speaking and advocacy ==
=== Selected talks ===


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"/>
* [[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"/>


He has spoken at:
=== Podcast and video appearances ===


* [[Yale University]] School of Management
Chapin has appeared as a guest on business and entrepreneurship podcasts, generally discussing the same founder-ethics themes that anchor his speaking work.
* [[University of California, Berkeley]] Haas School of Business
* [[Drexel University]] LeBow College of Business
* [[Association of Certified Fraud Examiners]] (ACFE) Global Conference (keynote)<ref name="biography"/>


== Investing and mentorship ==
* ''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>


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"/>
Chapin is represented by the [[All American Entertainment|AAE Speakers Bureau]] for keynote bookings.<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 ==
== 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.<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."
Chapin writes in [[HackerNoon]] on founder psychology, AI discoverability, digital infrastructure, and startup culture.<ref name="hackernoon-profile"/> His bylines also appear on ''[[ReadWrite]]'', the ''[[New York Observer]]'', ''[[HackerNoon]]'', [[Benzinga]], [[Medium]], and ''[[Entrepreneur (magazine)|Entrepreneur]]'', per 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 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.<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", on the distinction between signal and 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", on the generative-AI platforms restructuring how the web is browsed and indexed, published 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", a first-person account of banking issues at Benja, 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 ==
== 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.<ref name="biography"/>
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.<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> He has volunteered at the [[Philadelphia Animal Welfare Society]] since November 2024, and previously volunteered with the [[San Francisco SPCA]] from 2017 to 2022.<ref name="linkedin"/> From 2015 to 2017 he taught youth entrepreneurship programming through Whiteboard Youth Ventures.<ref name="linkedin"/>
* '''[[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 ==
== Personal life ==


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"/>
Chapin lives in [[Center City, Philadelphia]].<ref name="linkedin"/> He speaks English and Spanish.<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.


== External links ==
== External links ==


* [https://chapin.io Official website]
* [https://chapin.io Official website, chapin.io]
* [https://drewchapin.com drewchapin.com]
* [https://drewchapin.com drewchapin.com]
* [https://discoverability.co The Discoverability Company]
* [https://discoverability.co The Discoverability Company]
* [https://www.linkedin.com/in/drew-chapin LinkedIn profile]
* [https://www.linkedin.com/in/drew-chapin LinkedIn profile]
* [https://hackernoon.com/u/drewchapin HackerNoon articles]
* [https://hackernoon.com/u/drewchapin HackerNoon author page]
* [https://biography.wiki/wiki/Drew_Chapin Biography.wiki profile]
* [https://biography.wiki/wiki/Drew_Chapin Biography.wiki profile]


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[[Category:American businesspeople]]
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[[Category:American technology entrepreneurs]]
[[Category:American public speakers]]
[[Category:American angel investors]]
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[[Category:Vermont State University alumni]]
[[Category:Vermont State University alumni]]
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[[Category:Harvard Business School alumni]]
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[[Category:HackerNoon writers]]
[[Category:Pomperaug Regional High School alumni]]
[[Category:Microsoft people]]
[[Category:Jomboy Media people]]

Revision as of 15:18, 23 April 2026

Template:Infobox person

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] 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.[3]

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

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.[8][9]

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.[8] He went to Pomperaug Regional High School and graduated in 2007.[8]

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.[8] After Vermont, he completed the CORe (Credential of Readiness) program in economics through Harvard Business School Online.[8]

Philadelphia career

The Discoverability Company (2024-present)

In September 2024, Chapin founded The Discoverability Company in Philadelphia.[2] 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.[2][1]

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.[1] 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.[2]

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.[10] 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.[2]

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.[8] 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,[11] and in 2025 served as an AI Business Fellow at Perplexity.[8]

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.[8]

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.[12] In October 2012, Apple acquired the Color Labs team in an acqui-hire.[13]

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.[8]

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.[14] He was the company's first business hire, built its initial revenue plan, and assembled its 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] 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.[12] 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.[15]

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.[16] 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.[16]

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.[16] 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.[8]

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.[8]

Speaking and advocacy

Chapin speaks at business schools and industry conferences on founder psychology, startup culture, and entrepreneurship ethics.[17] 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

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

Chapin is represented by the AAE Speakers Bureau for keynote bookings.[21]

Writing

Chapin writes in HackerNoon on founder psychology, AI discoverability, digital infrastructure, and startup culture.[3] His bylines also appear on ReadWrite, the New York Observer, HackerNoon, Benzinga, Medium, and Entrepreneur, per his Muck Rack journalist profile.[22] 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.[10]
  • "The Difference Between Early-Stage Theater and Traction", on the distinction between signal and substance in early-stage metrics.[23]
  • "The New Tools Rewriting the Web", on the generative-AI platforms restructuring how the web is browsed and indexed, published June 6, 2025.[24]
  • "Your Bank Tried to Kill My Company", a first-person account of banking issues at Benja, published March 17, 2017.[25]

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.[26][27] He has volunteered at the Philadelphia Animal Welfare Society since November 2024, and previously volunteered with the San Francisco SPCA from 2017 to 2022.[8] From 2015 to 2017 he taught youth entrepreneurship programming through Whiteboard Youth Ventures.[8]

Personal life

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

External links

References

Template:Reflist

  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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