Darrell Silver

Running 503 Corp to launch tech companies with undiscovered founders. They generally solve the problems we hit building Thinkful. I also serve as board member, advisor, and investor across EdTech and child advocacy.

I've co-founded+CEO'd+sold two companies: Thinkful (acquired by Chegg) & Perpetually (acquired by Dell). Before that a quant.

I'm married to @stephenfoley and live in NYC. Don't work in crypto.

503 Corp

Our view is that durable businesses start Service First: Bootstrapped for the first few million then raise money when we can become a monopoly.

  1. Union – Your dedicated People Operations and Recruiting partner. Co-founder Ben Aronowicz, former Head of People at Thinkful.
  2. FaaS – Growth modeling for startups once reserved for public cos. Co-founder Parniyan Cagatay, former FP&A at Chegg.
  3. GoodGig.work – Upwork without the bad clients. Co-founder Blake Gillette.

Boards & advisory

Find me

Special projects

  • freeCodeCamp provides wonderful online learning for millions for free. In 2021 I was lucky enough to help fund its expansion into a new math curriculum.
  • Host the non-profit fundraiser StartupXmas, the holiday party for startups too small to host their own holiday party.