May 2, 2022

Kevin Mahaffey, a software engineer, founded his first startup at age 22. Today he's known as a cofounder of the security startup Lookout, now worth $1 billion. He's also backed 10 unicorns and ranks No. 3 on the Seed 100 list of the best early-stage investors. Kevin Mahaffey, an investor and serial entrepreneur, started building software when he was 8 years old, making screensavers for Apple II computers. So it should be no surprise that Mahaffey cofounded the mobile security startup Lookout — which is now valued at over $1 billion — at age 22, immediately after finishing his undergraduate degree at the University of Southern California. Mahaffey has also developed a Midas touch when it comes to seed investing, having backed 10 unicorns through the fund he founded, SNR Ventures — which stands for signal-to-noise ratio. This includes Lattice and People.AI, which both snagged unicorn valuations in 2021. Such successful bets moved him up 28 spots to No. 3 on Insider's 2022 Seed 100 list . He's also been an accredited "expert" for Y Combinator, advising multiple founders who graduated from the famed Silicon Valley accelerator known for helping Airbnb and Dropbox. What shaped Mahaffey the most as an investor was his own experience of raising money as a founder, he said, explaining that "almost everyone" rejected Lookout when he and his cofounders first tried to raise a Series A round in the summer of 2008. "We had no idea about really anything," he said. "I didn't know what a product manager was when we started the company. "  Eventually, Lookout secured funding, including from notable investors, such as Chris Sacca and Vinod Khosla, and it never struggled to raise another round again. But the rejection Mahaffey faced as an entrepreneur has shaped the way he approaches early-stage founders, both those he's looking to invest in and those he rejects. "If a company makes it to the point where a founder is using their valuable time with me, I try not to 'reject,'" he said. "I try to reframe as 'I would invest if' so that it's very clear where my stumbling block is. "  "After you were helped by people before you, you want to give back to the next generation of entrepreneurs," he told Insider. "I just found I really loved working with people, and there's nothing more satisfying than seeing somebody achieve a dream they've been working really hard for." The one part of VC culture that Mahaffey won't participate in though is punditry . He doesn't use social media much: He has a little under 3,000 Twitter followers, a scant number compared to other VCs who use Twitter and other social platforms as microphones for their beliefs on the industry (and to promote their investments). He also doesn't run a weekly podcast or write a Substack newsletter. "There's a Y Combinator phrase, which I love, which is 'More startups die from suicide than homicide,' which I find completely true," he said. "And the good thing is, it's in your control. It's okay if we don't know the answer, because if we knew all the answers, you wouldn't be raising a seed business. "  Sign up for notifications from Insider! Stay up to date with what you want to know. Subscribe to push notifications