Before
Investment banking at Merrill Lynch, then vice president at a venture-backed startup called Breather. He left in October 2019 after a leadership change, with a child on the way and no plan.
The move
He took a writing course and started a hobby newsletter, then launched an in-person debate and social club called Not Boring in January 2020. COVID killed it within weeks. Broke, he merged the dead events business into the newsletter on 2 April 2020 and kept writing under the same name. A Product Hunt launch that June compounded it to tens of thousands of readers.
The turn
His first angel check went out in July 2020. That same summer he ran a syndicate that put roughly two million dollars into fourteen companies. A year later the syndicate became an eight million dollar fund.
Timeline
- October 2019 leaves his last salaried job
- January 2020 launches an in-person club, killed by COVID
- April 2020 merges the club into the newsletter
- July 2020 first angel check
- July 2021 Not Boring Capital Fund I at 8 million dollars
- 2022 Fund II at 30 million dollars
- 2023 Fund III at 30 million dollars with a 50 million dollar cap
What this route asks
Readers, and the nerve to keep publishing through the period when it is clearly not working. Once several thousand people read you every week, turning informal angel checks into a fund is paperwork rather than networking.