Renowned “Angel” Jason Calacanis shares advice on entrepreneurship, investing

When he nailed his first major exit, Jason Calacanis sat at his computer, refreshing the screen on his Bank of America account. When the balance changed from $3,000 to $30 million, he began to cry. His wife asked what was going on, and Calacanis turned the monitor to her and said, “We don’t have to worry about money anymore.”

Calacanis told the tale of AOL’s $30 million buy of Weblogs, a blog network he created with childhood pal Brian Alvey, along with other stories of entrepreneurship and investing while visiting Montclair State on July 25. Nearly 150 people attended the event where Calacanis, a renowned serial entrepreneur and angel investor, was interviewed by David Sorin, a partner at McCarter & English. The event was presented by the Feliciano Center for Entrepreneurship, and it was Calacanis’ only appearance in New Jersey for the launch of his first book, “Angel.”

“We had an engaging, lively conversation that reveals the pivotal role of technology and entrepreneurship, politically, socially and, of course, economically,” said Sorin, whose firm sponsored the event. “Jason was generous with his time and insights, with honest and provocative responses to my questions and those of the roughly 150 attendees at Montclair State University.”

Although Calacanis has been extremely successful, resulting in financial windfalls, he wanted the audience to know he was just “a kid from Brooklyn” who if he wasn’t a rags-to-riches story, was perhaps a Toughskins-to-riches tale. Calacanis talked about his family making tough financial decisions while he grew up, and said he wrote “Angel” so others could use it as a playbook to see what’s possible. “Doing hard work and trying to be successful is a good thing,” he said.

Calacanis went to Fordham University at night, while working as a waiter and fixing laser printers. He pondered how people get rich and powerful, and gravitated to journalism, figuring the editor who puts people on the front cover of a publication is the one with the power. After launching and selling VentureReporter.net (born as Silicon Alley Reporter) and Weblogs, Calacanis moved into investing, scoring unicorns—or investments of more than $100 billion—in two of his early funding ventures, which included Uber. Calacanis’ unicorn track record is six among his first 100-150 investments, a score he compared to hitting three half-court shots during a basketball game.

For tips on how he invests, Calacanis said people assume if he invests in something it will automatically succeed, but that’s incorrect. “It’s not causation, it’s correlation,” said Calacanis.

Calacanis said he prefers to invest in someone who has a prototype, because anybody can have an idea. He wants to fund people who are dogged, hard-working, indefatigable and willing to add new skills. “If I find a founder who won’t give up, that’s the magic.”

When a 26-year-old attendee asked about the most important skill to have, Calacanis said it’s the ability to acquire new skills, and always be thinking: where can I find the hack to add this skill to my toolbox. “Have a habit of learning, just like a habit of working out,” he said.

When he hires for one of his companies, such as Inside.com, Calacanis looks for “missionaries, not mercenaries,” because the latter are just a skill-for-hire who will jump to a higher salary at any time, whereas missionaries support the mission of the company.

Calacanis spoke of advocating for more women in the startup world, especially in tech. When an attendee asked how to find diversity in a co-founder, Calacanis advised first to find someone who is passionate about the problem you are trying to solve, even if the person looks like you, but make sure they value diversity. A founder might have to wait until your third hire to find the right, diverse fit but can also be creating a culture of diversity in the startup, he said. Regarding the sexual harassment allegations that have been roiling Silicon Valley lately, Calacanis said there must be zero tolerance. “It is so front and center in our industry,” he said. “It’s career-ending at this point. … It’s one-and-done now.” He also credited that there are so many powerful women in tech who won’t tolerate such behavior any longer.

“I’m happy he touched on the diversity and gender issues,” said attendee Kavell Taylor, co-founder of Homeowners Hub. “It’s being discussed in an open forum, and was met with such warmth from the audience.”

Learn about Women Entrepreneurship Week.

Calacanis, who was generous with his time as he chatted with each attendee during the book signing, was genuinely curious to learn from the people in the audience. When a man in a wheelchair asked how there could be more startups serving people with disabilities, Calacanis answered: “I would look to you to tell me. You tell me how I can help, how entrepreneurs can help people with disabilities live full lives” and then offered to talk further with the man.

Calacanis delved into politics, leaving some to wonder if he might run for office someday – a scenario he jokes about on his “This Week in Startups” podcast, and he owns the domain MayorJason.com (which redirects to his @Jason Twitter account). With a liberal streak, Calacanis also said that if attendees thought he was a “marauding free-market monster,” they’d be half correct.

“We have the most open meritocracy in the world. … This meritocracy draws the best people in the world,” said Calacanis, objecting to limits on which immigrants can enter the U.S. He said he decided, “I need to get more involved because if we don’t get more involved, things can go way off course.”

Calacanis talked about a coming “jobpocalypse” in which everything from baristas to lawyers will be replaced by artificial intelligence and robots. He predicted no one will be working at a McDonald’s register in three years, because customers will place orders at kiosks.

“This future is inevitable. We have to be the first ones there, as American companies,” he said.

Calacanis even opened the possibility of darker consequences, noting there could be a revival of Occupy Wall Street protests, and that wealthy people he knows are building houses off the grid in New Zealand or Montana as prep for the 1 or 2 percent chance of a class revolution. “As all these jobs will go away, there will be riots in the street,” Calacanis said, adding he believes there is an “80 percent chance we’re teetering on unrest.”

Despite the dismal prediction, Calacanis overall is an optimistic guy. He said our phones, with their constant stream of news and info, allow us to know about the worst thing happening on the planet at any given moment, yet in so many areas, life has improved.

“Actually, net-net, it’s getting better,” he said.

Whether Calacanis’ comments were sunny or serious, attendees were eager to soak up his advice and tips.

“I thought he was very insightful and entertaining. I think he captured the imagination of the crowd on how entrepreneurship is going to solve this country’s problems and move us forward,” said Peter Chmiel, a serial entrepreneur who traveled from Sayreville for the event.

Abhisek Vyas, president of Rutgers Entrepreneurial Society, said, “It was incredible because it’s not every day you get to meet a tech leader on the East Coast.”