Darrell Silver

Making awesome cost centers so you don't have to with Unbundle.Studio. 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.


Our view is that companies by 2030 will hire great experts that come bundled with best in class software, so we're seeing where that's most true. We build Service First: Bootstrap for the first few million then raise money when a product 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.