Drew Chapin
About Drew Chapin
Drew Chapin (Andrew J. Chapin) is based in Philadelphia, Pennsylvania. He runs The Discoverability Company, which he founded in 2024. The firm helps people and businesses with AI, search, voice and social media visibility. His site describes him as a startup operator and go-to-market engineer.
He began his career at Microsoft in Boston. He later held early roles at Feathr, Jomboy Media and Birthday.App, where he was Head of E-Commerce. He also worked with Team, Assemble! and completed an AI Business Fellowship at Perplexity.
Chapin was founder and CEO of Benja Commerce Network, a shoppable media company he ran from 2014 to 2020. It filed for bankruptcy in 2020. He now writes and speaks about that experience and the risks of "fake it 'til you make it" culture. He also mentors early-stage founders through the Founder Institute's Keystone chapter in Philadelphia.
Chapin is a Hustle Fund Angel Squad member. His disclosures page says he has been in the Angel Squad since 2024 and completed the Hustle Fund Venture Fellowship (5th cohort) in 2026.
Crunchbase lists one personal investment, a seed round in Jomboy Media, with Chapin as lead investor. The round date and amount are not shown publicly. Crunchbase shows 1 portfolio company and no exits.
Chapin says he writes checks into pre-seed companies. He says he is most useful before there is traction, on how a company gets found and how it turns attention into customers. His own words describe go-to-market, search and discovery as the area he knows best.
He publishes deal memos and instructions for sending him a deck on chapin.vc. His check size, fund size and geographic focus are not public.
- Jomboy Media: independent sports media brand. Crunchbase lists a seed round led by Chapin, with no public date.
- NextPick: three-sided marketplace for college athletic recruiting. Listed on chapin.vc with a June 2025 memo.
- Rentaba: links the rental market with financial technology for tenants and landlords. Listed on chapin.vc with a June 2025 memo.
- Ideate: operational infrastructure for design teams. Listed on chapin.vc, no date given.
- Little One: domestically produced goat-milk infant formula. Listed on chapin.vc, no date given.
- Ujoin: online grassroots advocacy platform. Listed on chapin.vc, no date given.
Investing activity
Drew Chapin has made 1 investment according to Crunchbase across 1 portfolio company, and has led 1 round and founded 4 companies.
Deals
Frequently asked questions about Drew Chapin
Does Drew Chapin invest in AI startups?
No AI-specific investments are public. He works on AI search visibility through The Discoverability Company, but the companies listed on his investing site are in sports media, marketplaces, fintech, design operations, consumer goods and advocacy.
What stage does Drew Chapin invest in?
He describes his investing as pre-seed, before traction. He is part of Hustle Fund's Angel Squad, and Hustle Fund describes itself as backing very early-stage companies.
What is Drew Chapin's check size?
It is not public. He does not state a check size on his site or in the sources reviewed.
How do I pitch Drew Chapin?
His investing site, chapin.vc, says it explains how to send him a deck. You can also contact him through LinkedIn.
What can Drew Chapin help founders with beyond capital?
He offers go-to-market strategy, customer acquisition, SEO, AI discoverability and online reputation management. He also mentors founders through the Founder Institute in Philadelphia.
Has Drew Chapin founded companies?
Yes. Crunchbase lists 4 founded companies, including Benja Commerce Network, which he ran from 2014 to 2020. He now runs The Discoverability Company.
Is Drew Chapin an angel investor?
Yes. Drew Chapin invests personally as an angel and is Digital Discoverability Specialist at The Discoverability Company. Crunchbase counts 1 investment.
Where is Drew Chapin based?
Drew Chapin is based in Philadelphia, Pennsylvania, United States.
How can founders reach Drew Chapin?
Founders on Lounge can see Drew Chapin's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add Drew Chapin to their Investor Pipeline to track the conversation.