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.

Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

Send me a message to let me know what you think!