Background
About
Drew Chapin is a Philadelphia-based go-to-market specialist and digital discovery strategist who helps early-stage startups and established brands get found on search, social, and emerging AI platforms.
Chapin founded The Discoverability Company, where he focuses on holistic online visibility and reputation, and regularly writes and speaks about startup culture.
Previously, Chapin held leadership roles at Jomboy Media, Feathr, and the shoppable-media startup Benja Commerce Network, a set of experiences which has given him what he calls "a 360-degree view of early-stage entrepreneurship" including successes and catastrophic failures.
Chapin is also active as an angel investor and scout with Hustle Fund, mentors founders through programs like Founder Institute and Temple University, and publishes a newsletter chronicling the evolving startup scene in Philadelphia.
Experience
- The Discoverability CompanyFounder — 2024–PresentSEO, AI discoverability, online reputation management
- Hustle FundAngel Squad Scout — 2024–PresentPre-seed venture investing
- PerplexityAI Business Fellow — 2024AI search and discovery
- Birthday.AppHead of E-Commerce — 2023–2024Gift marketplace, organic growth strategy
- Commerce Media StudioPartner — 2021–2023D2C e-commerce and media incubation
- Jomboy MediaFounding Business Director — 2017–2020Revenue models, e-commerce, digital discovery; scaled to millions of followers
- Benja Commerce NetworkCo-Founder & CEO — 2014–2020Shoppable media platform; raised multiple funding rounds
- FeathrVP Business Development — 2013–2014First business hire; nonprofit marketing platform
- Color LabsMarketing Specialist — 2011–2012Video social platform; acquired by Apple 2012
- Vermont Spirits Distilling Co.Marketing LeadCraft spirits brand marketing
- MicrosoftSales & Marketing Program
Expertise
- Go-to-market strategy for early-stage startups
- Digital discovery and SEO optimization
- Online reputation management
- AI platform visibility (ChatGPT, Perplexity, Claude)
- E-commerce and organic customer acquisition
- Startup mentorship and advisory
- Angel investing and venture scouting
Education
- Harvard Business School Online
- Vermont State University
- Google Project Management Certification
Speaking
Drew speaks at universities and conferences about entrepreneurship, ethics in startups, and the lessons learned from failure. His signature talk, "The Six Deadly Sins of Entrepreneurship," examines ethical drift in startup culture.
- Yale School of Management
- UC Berkeley Haas School of Business
- Drexel University
- ACFE New Jersey
- ACFE Pittsburgh
For speaking inquiries: drew@chapin.io
Community
- Mentor, Founder Institute (Keystone Chapter)
- Mentor, Temple University
- Volunteer, PAWS Philadelphia (Philadelphia Animal Welfare Society)