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There are no second winners, only first losers.

No-nonsense advice for young people: success is a zero-sum game

Aimee Groth
By Aimee Groth

Journalist, Author, Strategist

Angel investor Jason Calacanis—a Silicon Valley veteran who has invested in more than 60 startups—has some pointed advice for young people who are just starting their careers: Success is a zero-sum game. He writes in a blog post:

“Many folks will tell you that the world is not a zero sum game, with one person not having to lose at the expense of another winning. This is simply not true, as in most startups there is a very limited number of seats and they go to the people who work the hardest and who have the most skill. In your career you will find that life is a zero sum game: the winners get the prime positions and the person who comes in second place for that position is the first loser—not the second winner.”

Calacanis, a serial entrepreneur and first-round investor in Uber, advises young people to work at a startup and take on every project the CEO asks, because “CEOs love people who work hard and who refine their skills faster than everyone else … because those people remind them of themselves. How the f@#k do you think she got the CEO slot, by waiting in line? By random luck? No, she f@#king took that slot.”

Some other tips: “never leave work before she does,” and “don’t worry about your salary, just get enough money to live in a closet close to work.” Calacanis is worth listening to; he has been involved in the startup world since the dot com era, sold his second company to AOL for around $25 million in 2005, and has invested in a number of high-valuation companies—in addition to Uber, there’s Whisper, Evernote, Tumblr, among others.

Serial entrepreneur Jason Goldberg, founder of Fab and now Hem, tweeted:

“I just wish someone would have told me that people, not job titles, are the single best way to change the trajectory of your career,” Assist co-founder Shane Mac told Quartz. “Screw titles, go work for someone you want to be.” Mac described the article on Facebook as “the single best article I’ve ever read on career advice.”

What differentiates Calacanis’ advice is that it’s brutally honest, even raw, and very specific. Working in the startup world is hardly glamorous—something that venture capitalist Ben Horowitz encapsulates in his book The Hard Thing About Hard Things—and Calacanis gives young people a sharp tutorial on how to succeed in that world—one where the faint hearted need not apply.

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