“Ten years ago this month, I started this business,” he wrote. ” I was excited-nervous as could be. Worried I didn’t belong in the venture capital world, I figured I’d keep my head down and work hard, ignore all the nonsense as much as possible, focus on what I loved and where I could help.”
Dearing has indeed kept his head down over the years — as announcing his own new fund on Twitter suggests. (Most venture firms seek out media attention, with the belief that stories about their fresh capital will attract founders.)
Reporter Kara Swisher even dubbed him years ago the “hottest angel investor you’ve never heard of.”
Things haven’t changed much. Dearing — a former senior VP at eBay who joined Stanford’s faculty in 2006 as a consulting associate professor and taught off campus for eight years — has quietly backed a long string of highly successful companies.
More distantly, he funded AdMob, a mobile advertising start-up acquired by Google for $750 million in late 2009. He also backed Aardvark, a social search engine that was also acquired by Google, for $50 million 2010. (Aardvark cofounder Max Ventilla has since created AltSchool, a richly funded, somewhat controversial network of schools and maker of educational software that Dearing has also backed.)
Dearing had another big win when Acompli, which made a mobile email application, sold to Microsoft for $200 million in cash in 2014. It had raised just $7.3 million from investors.
But Dearing doesn’t have to look too far back into the archives to be proud of his portfolio. Among his “active” bets are such buzzy companies as Harry‘s the shaving company, PagerDuty, and MasterClass.
Harry’s just announced $112 million in funding last month, money it wants to use to take on not just Gillette but Proctor & Gamble, too.
PagerDuty, which sells digital operations management services, is doing well enough that its privately held shares have become a hot commodity to secondary buyers.
MasterClass, which last raised $35 million a year ago, has meanwhile become hugely popular if our spectrum of friends is to believed. Many of them seem to be taking some online course or another by MasterClass, which has enlisted tens of “masters” in their respective fields — tennis great Serena Williams, screenwriter Aaron Sorkin, and chef Thomas Keller, among them — to teach people eager to learn how to succeed in the same industry.
It’s perhaps no wonder that Dearing likes to fly low. Several years ago in StrictlyVC, a newsletter published by this editor, he told interviewer and fellow investor Semil Shah that in his view, the “very best early-stage investor in the business is Steve Anderson” of Baseline Ventures, who also happens to prefer operating in the shadows. (We were able to pull Anderson out of them just once for a story.)
Said Dearing of Anderson in a description that some might say also suits Dearing: “His track record is exceptional, obviously — and he’s well known for it. But I mean ‘best’ in the broadest sense. Tells the truth. Focuses on making the pie big first. Crazy supportive of his founders in good and bad times. He’s honest and hard-working. He’s the very first person I would go see if I were raising money. There are some truly exceptional people in the early-stage business, but he’s at the top of my list.”