About Drew
Drew Chapin is the founder of The Discoverability Company, a Philadelphia-based firm that helps individuals and businesses control what shows up when someone searches their name. He has spent nearly two decades in go-to-market roles at technology companies, starting with Microsoft in Boston, moving through early-stage venture-backed startups including Feathr and Jomboy Media, and most recently completing an AI Business Fellowship at Perplexity.
He writes about how AI search has reshaped digital discovery, why Wikipedia has become infrastructure for brand recognition in the age of large language models, and the unglamorous operational work that actually moves the needle for individuals and small businesses. His work has appeared on HackerNoon and Medium, with 18+ published articles covering AI discoverability, founder psychology, Wikipedia as entity infrastructure, digital identity, and the honest realities of running an early-stage company.
Current Work
As founder of The Discoverability Company, Drew works directly with clients on online reputation management, AI search optimization, Wikipedia notability campaigns, court record removal, press placements, and search engine optimization. TDC operates on an a la carte, project-based model with no retainers.
He is a Venture Fellow in Hustle Fund's fifth cohort and an active angel investor, and mentors early-stage founders through the Founder Institute's Keystone chapter serving Philadelphia and the Delaware Valley. He sits on the steering committee of the White Collar Support Group.
Experience
- The Discoverability Company (2024–present) — Founder. Go-to-market strategy, online reputation management, AI search optimization, and digital discoverability for individuals and businesses.
- Hustle Fund (2024–present) — Venture Fellow, Angel Squad. Pre-seed investing.
- Perplexity (AI Business Fellowship) — Studied how AI search is reshaping brand discovery.
- Birthday.App (2023–2024) — Head of E-Commerce. Organic growth across SEO and ASO.
- Jomboy Media (2017–2020) — Founding business director. Built the business side of one of the leading independent sports media brands, from a single Twitter account through early revenue and e-commerce.
- Benja Commerce Network (2014–2020) — Co-founder and CEO. Early mover in shoppable media. The company failed and filed bankruptcy in 2020. Drew has written and spoken publicly about the ethical drift that led to the collapse, and uses the experience as a teaching case in talks at Yale, UC Berkeley, Drexel, and the Association of Certified Fraud Examiners.
- Feathr (2013–2014) — First business hire. Built the revenue plan and sales team.
- Microsoft (2009–2011) — Sales Marketing Manager, Boston. Drove SMB and educational adoption of Windows and Office.
Education
- Bachelor of Science, Vermont State University (Student Government Association president, 2008–2010)
- CORe Economics, Harvard Business School Online
Speaking and Writing
Drew speaks at universities, conferences, and founder communities about go-to-market strategy, AI search, and the ethical dynamics of early-stage startups. Recent appearances include Yale, UC Berkeley, Drexel University, and an ACFE keynote. Notable published work includes "Wikipedia Rules Everything Around Me," "You Are Not Your Startup, Your Startup is Not You," "It Finally Happened — I Consumed AI Content Without Realizing It," and "The Difference Between Early-Stage Theater and Traction."
Articles by Drew
All articles on this site are written and edited by Drew. See the full Resources library for current guides on AI search, reputation management, SEO, press strategy, and small-business discoverability.
Contact
Client inquiries: book a consultation. Speaking, press, and media: [email protected].