When I met Jason Calacanis 22 years ago, he was a scrappy 20-something with big ideas, but not a lot of capital. He didn't have money to invest, but he had the entrepreneur's mindset, and also happened to be a poker player who learned a mantra in the game: "No gamble, no future." This idea led him to become one of the most successful angel investors in the tech sector.
While fixing computers to pay his way through college, Calacanis, the son of a bar owner, was so broke he had to save coins to afford to buy potato knishes — which he liked because they're cheap and filling — on the New York City streets. Years later, Calacanis is a multimillionaire in Silicon Valley who advises others on which high-growth technology companies to put their money into, and puts his own where he thinks it will multiply — like Uber, in which he was an early investor.
He appeared on "Salon Talks" this week to discuss the tactics and mistakes outlined in his new book, "Angel: How to Invest in Technology Startups," and how running for mayor of San Francisco and fixing the city's internal problems started out as a joke but has become a real possibility.
On getting his start as an angel investor:
I had started a company called Mahalo, which is now called Inside.com, and it's a news site. Sequoia was an early investor — Sequoia is the number-one venture capital firm in the world. And I had early success in the blogging space creating Engadget, Autoblog, Joystick, all part of a company called Weblogs, Inc. that I sold to AOL. Made a little bit of money, and then Sequoia backed my next company.
About a year or two into working with them, they said, "We have an idea — all our founders, the CEOs, know other founders. What if we gave you some money — would you consider investing it in your friends?"
It was like being anointed by the smartest people in the room.
Of the first four or five companies, I had two unicorns [companies valued at more than a billion dollars].
Your latest gamble is running for mayor of San Francisco. How did this come about?
It was a joke. Because when Trump was getting elected, my poker buddies and a bunch of friends in the industry said, "You could win!" It's obvious, because if Trump can win, the benchmark is now so low that people would consider it. I said, wow, let me think about that.
I bought the domain name MayorJason [this redirects to his Twitter page], and I started making jokes about how I would fix San Francisco, taking this approach of, Hey, let's try some crazy ideas. Let's try the 100-1 odds thing, and let's really become not a political party that's fighting with each other over some ideology that's outdated, let's just be a solutions-based party.
It went from being a joke . . . to people putting up millions of dollars to put together an exploratory committee.
I think it's worth doing, but who knows . . . San Francisco is just a disaster. The suffering in San Francisco and how poorly run the city is is stunning. As somebody who lived in Los Angeles and New York -- which are high-functioning cities, despite being challenged cities -- San Francisco is dysfunctional.
Watch our conversation for more on taking risks.