Drew Chapin

Founder, The Discoverability Company | Philadelphia, PA

About

Drew Chapin runs The Discoverability Company out of Philadelphia. The short version: he helps people and businesses get found. On Google, in AI answers from ChatGPT and Perplexity, on social platforms, wherever their customers are actually looking. He's been doing some version of this for over a decade, across five startups, a stint at Microsoft, and one very public failure that he now talks about at business schools.

Before starting TDC in September 2024, Chapin was the founding business director at Jomboy Media. He joined when the company was literally a single Twitter account run by Jimmy O'Brien out of a bedroom. By the time he left, Jomboy had millions of followers and multiple revenue streams. That early-stage-to-scale experience, figuring out how to get attention and then turn it into money, is basically what he does now for clients.

He also co-founded Benja Commerce Network in 2014. Raised venture money, built a shoppable media platform, signed deals with major publishers. Then it all fell apart in 2020. Chapin doesn't hide from that story; he built an entire speaking career around it. Yale, Berkeley Haas, Drexel, the ACFE Global Fraud Conference. He shows up and tells founders what went wrong and why.

Other stops along the way: first business hire at Feathr (events marketing SaaS, later acquired), Head of E-Commerce at Birthday App, Marketing Director at Vermont Spirits where he got the brand named official spirit of the Vermont Ski Association. Started his career at Microsoft in 2009 selling Windows and Office to schools in New England. He was also a 2025 Perplexity AI Business Fellow.

Experience

The Discoverability Company (September 2024 to Present)

Founder & Partner

Started TDC in Philly after spending 15 years watching companies struggle to get found online. The firm handles SEO, AI discoverability (getting clients into ChatGPT/Perplexity/Claude answers), reputation management, and go-to-market strategy. Clients are a mix of pre-seed startups that need their first customers and established names that need to clean up what shows up when you Google them. The work is unglamorous and specific: fix the search results, build the profiles, get the content ranking.

Hustle Fund (October 2024 to Present)

Angel Squad Member

Invests in pre-seed companies through Hustle Fund's Angel Squad. Hustle Fund's whole thing is backing founders absurdly early, sometimes before they've even incorporated. Chapin contributes deal flow and helps portfolio companies with customer acquisition, which is what he knows.

Founder Institute (January 2025 to Present)

Startup Mentor

Mentors founders through the Keystone chapter, which covers Philly, Princeton, and the Delaware Valley. It's a 14-week program. Chapin focuses on business model validation and customer acquisition. The core question: "Do people actually want this, and if so, how do you reach them?"

Birthday App (August 2023 to August 2024)

Head of E-Commerce

Built the gift marketplace from zero. The app itself was a birthday calendar with millions of users; Chapin's job was to figure out how to sell them gifts. Organic growth via SEO and App Store Optimization, vendor management, product curation.

Commerce Media Studio (2020 to 2022)

Project Manager

Incubated media and e-commerce companies. Content-driven commerce models, DTC brand development, affiliate partnerships.

Jomboy Media (April 2017 to December 2020)

Founding Business Director

Showed up when the entire company was Jimmy O'Brien posting baseball videos from a Twitter account called @Jomboy_. Chapin was the first business hire. He handled everything on the money side while Jomboy handled the content side. By 2020 they had millions of followers, a podcast network, merch, and ad revenue. It's now one of the biggest independent voices in baseball media.

Benja Commerce Network (July 2014 to November 2020)

CEO / Chief Revenue Officer

Co-founded Benja in San Francisco. Shoppable media was the pitch: a shopping app, a proprietary ad format for publishers, and DTC storefronts. Raised venture capital, landed publisher partnerships. Then it collapsed in 2020. Badly. The company filed for bankruptcy and Chapin faced SEC charges related to misrepresentations made during fundraising.

He doesn't dodge any of it. The whole experience became the foundation for his speaking work. He calls his framework the "Six Deadly Sins of Entrepreneurship," and it's about how founders drift into bad decisions incrementally, not all at once. He writes about it regularly on his newsletter. The tagline he uses: "Founders don't snap. They drift."

Feathr (July 2013 to July 2014)

VP Business Development

First business hire. Event marketing SaaS company in Boston. Built the revenue plan, hired the first sales reps, set up channel partnerships. Feathr kept growing after Chapin left and was eventually acquired.

Vermont Spirits Distilling Co. (December 2011 to July 2013)

Marketing Director

Ran all marketing for a craft distillery in Quechee, Vermont. The big win was landing a deal to make Vermont Spirits the official spirit of the Vermont Ski Association, tying the brand directly to the state's outdoor culture.

Color Labs (November 2011 to July 2012)

Marketing Specialist

Campus user acquisition for a Sequoia- and Bain-backed video social platform. Apple bought the company in 2012.

Microsoft (August 2009 to November 2011)

Sales Marketing Manager

First real job out of college. Sold Windows and Office to SMBs and schools in New England.

Education

Harvard Business School Online CORe Economics Program

Vermont State University Bachelor of Science (2007 – 2011)

  • President, Student Government Association (2009–2011)
  • President, Student Investment Group (2011)

Pomperaug Regional High School Southbury, Connecticut (Class of 2007)

Google Project Management Certificate Professional Certification

Languages: English (native), Spanish (conversational)

Writing

Chapin has 18+ articles on HackerNoon and has been published in Forbes, ReadWrite, and New York Observer. He writes about startup culture, founder psychology, and digital discovery. The tone is blunt. No guru energy, no hustle porn.

A few pieces that got traction:

Speaking:

The talks all come back to the same thing. Why do smart founders make terrible decisions? Chapin uses his own Benja experience as the case study. It's not theoretical.

Investing

Chapin writes small checks into pre-seed companies through Hustle Fund's Angel Squad. He likes the ones that are still just an idea and a founding team. Consumer marketplaces, media companies, B2B SaaS with organic distribution baked in, founder-led brands where the founder actually has something to say. He helps where he can on customer acquisition and digital discovery, which is the overlap with his day job.

Volunteering

Founder Institute, Keystone Chapter (January 2025 to Present) Startup mentor for the 14-week pre-seed accelerator. Business model validation, customer acquisition, and trying to keep first-time founders from making the mistakes he made.

PAWS Philadelphia (November 2024 to Present) Volunteers at Philadelphia's largest no-kill shelter. Animal care and adoption events.

San Francisco SPCA (August 2017 to February 2022) Volunteer. Animal welfare and community outreach.

Expertise

Go-to-Market & Growth: Customer acquisition, growth marketing, SEO, SEM, B2B marketing, DTC strategy, App Store Optimization, content marketing

Business Operations: Business development, sales management, fundraising, team building, project management

Digital Discovery: SEO, AI platform visibility, online reputation management, Wikipedia strategy, social media optimization

Startup & VC: Early-stage startups, venture capital, angel investing, founder mentorship, due diligence

FAQ

What does The Discoverability Company do?

TDC helps businesses and individuals get found online. That means SEO, AI discoverability (showing up in ChatGPT and Perplexity answers), reputation management, and go-to-market strategy. Most clients come in with a specific problem: they're invisible on Google, they have bad search results they need to push down, or they're launching something and need customers to find them.

What is AI discoverability?

When someone asks ChatGPT or Perplexity a question, the AI pulls from sources across the web to generate an answer. AI discoverability is about making sure your information is in that mix. It's a different game than traditional SEO because the ranking factors are different. TDC handles both.

What happened with Benja?

Drew co-founded Benja in 2014 and ran it as CEO until it failed in 2020. The company raised venture capital and built a shoppable media platform, but it didn't work out. The SEC brought charges related to misrepresentations during fundraising. Drew has talked about the whole experience openly and uses it as the basis for his speaking work at business schools and conferences.

What does Drew speak about?

Startup failure, founder psychology, and why good people make bad decisions under pressure. His main talk is called "The Six Deadly Sins of Entrepreneurship." He's given it at Yale, Berkeley Haas, Drexel, and the ACFE Global Fraud Conference. He uses his own story as the case study.

Is Drew an angel investor?

He is. He invests through Hustle Fund's Angel Squad, mostly in pre-seed companies. Consumer marketplaces, media, B2B SaaS with strong organic distribution. He likes companies where the founder is still figuring it out but has a real insight about the customer.

Does he mentor startups?

Through the Founder Institute's Keystone chapter (Philly, Princeton, Delaware Valley). It's a 14-week program for pre-seed founders. He focuses on business model validation and customer acquisition.

Why Philadelphia?

Drew moved to Philly in 2024 to start TDC. He's plugged into the local startup scene through Hustle Fund and Founder Institute Keystone, volunteers at PAWS (the city's largest no-kill shelter), and writes a newsletter at chapin.io.

What is online reputation management?

It's about controlling what shows up when someone searches your name. Pushing down bad results, making sure good profiles rank high, cleaning up data broker listings. Some of it is content creation, some is technical SEO, some is direct outreach to platforms.

Can TDC help with bad search results?

Yes. Reputation management is one of the firm's core services. The approach combines content creation, profile building, SEO, and where appropriate, takedown requests to platforms and data brokers.

What companies has Drew worked at?

Jomboy Media (founding business director), Birthday App (Head of E-Commerce), Feathr (first business hire, VP Business Development), Vermont Spirits (Marketing Director), Color Labs (acquired by Apple), and Microsoft. Plus angel investing and advising through Hustle Fund.

What are the Six Deadly Sins of Entrepreneurship?

It's Drew's framework for understanding how founders drift into unethical behavior. Not a sudden snap, but a slow slide. The talk examines the psychological pressures that push founders past their own ethical lines, using the Benja collapse as the central case study.

Does Drew do speaking engagements?

Yes. Universities, conferences, corporate events. Topics: startup failure, founder psychology, entrepreneurship ethics, digital discovery, AI and marketing. He's represented by AAE Speakers Bureau. Contact: drew@chapin.io.

Contact

For go-to-market consulting, speaking engagements, or angel investment opportunities, reach Drew at drew@chapin.io or connect on LinkedIn or Threads.

Professional Profiles

Social Media

Company & Writing

Contact

For inquiries, please contact Drew Chapin via email: drew@chapin.io