A Product Market Fit Show | Startup Podcast for Founders He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress
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Dec 22, 2025 
Kyle Hanslovan, Founder and CEO of Huntress, shares his remarkable journey from NSA hacker to leading a $2B cybersecurity firm. He reveals the harsh realities of bootstrapping, including sleeping in his car and facing 60 VC rejections before finally hitting $100M ARR. Kyle discusses the critical importance of understanding the SMB market, leveraging partners, and achieving impressive net revenue retention. He also speaks candidly about personal sacrifices and the grit required to transform setbacks into success.
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From Sleeping In A Car To $100M ARR
- Kyle slept in the back of his car during a 16-week accelerator stint while the team burned their savings.
- That near-bankruptcy moment preceded accelerating growth to $100M ARR years later.
Small Teams + Massive Automation
- NSA work taught Kyle to combine automated data analysis with targeted, small-team operations.
- That approach informed Huntress's model of focused detection plus automation.
Detect Footholds, Not Just Prevention
- Hackers constantly mutate tactics so prevention alone can't catch everything.
- Kyle positioned Huntress to detect footholds that slip past preventive tools, akin to early disease detection.