Sahil Lavingia
Information Technology Specialist at Internal Revenue Service
About
I founded Gumroad and ran it for 14 years. Now I build taxpayer-facing tools at the IRS.
Experiences
- Information Technology Specialist at Internal Revenue ServiceWork on technology for the IRS in New York
I'm working inside the federal government now, as an Information Technology Specialist based in New York.
- New York → Hong Kong → SingaporeGrew up in Singapore shipping iPhone apps
Born in New York, I moved to Hong Kong at 4, then Singapore. By 16 or 17 my apps made me financially independent.
- FlexileBuilding a way to pay contractors in equity
It goes back to missing my Pinterest cliff. In September we went from 31 to 45 customers.
- Founder & CEO at GumroadGrew to $20M in revenue with only freelancers
We had no meetings or deadlines, everyone billed hourly, and creators watched our board meetings in public.
- Investor at SHL CapitalRan a rolling fund of almost $7M a year
I invested in basically anything super early stage. Being someone's first check is my dream moment.
- Founder & CEO at GumroadRaised $8M, then laid off 75% of my team
After 9 months failing to raise more, I let go many good friends in October 2015 and couldn't stay in Silicon Valley.
- Software Engineer and Designer at PinterestBuilt Pinterest's iPhone app alone at 18
I was employee #2. I was out 9 months in, before my cliff, so none of my 0.75% of Pinterest vested.
- ProfessionalWrote a book on unlearning the unicorn chase
It grew out of my 2019 essay on failing to build a billion-dollar company. I also taught it in 6-week cohorts.