He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress

Episode notes

For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3. Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel. Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round. But then things changed: 2018: $1.5M ARR 2019: $5M ARR 2020: $10M ARR 2021: $20M ARR 2022: $40M ARR 2023: $70M ARR 2024: $100M+ ARR Huntress is valued at $2B. The investors who backed his $1M bridge are up 140x. Now every VC wants to invest—and Kyle's the one saying 'no'. Why you should listen: How to know whether you should keep going or quit. What it takes to get through the first few years at a bootstrapped startup. Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention). How starting a startup can impact your personal life and relationships. How to work with partners to sell to long tail SMB customers.