Jason Calacanis (@Jason) is Silicon Valley royalty, the most successful angel investor today, and author of Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000.

What We Discuss with Jason Calacanis:

  • What venture capitalists are looking for in startup founders.
  • How Jason bounced back after losing everything (something to which we can personally relate).
  • How to make yourself more marketable, whether you’re a founder or an angel investor yourself.
  • What Jason considers “the greatest skill of all.”
  • The impersonations Jason can do to make your blood run cold when you’re miles away from any semblance of civilization.
  • And much more…
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Worksheet for This Episode

Episode 100 of The Jordan Harbinger Show was recorded in front of a live forest audience in the Canadian wilderness at Fireside Conference 2018. No limbs were frostbitten in the making of this program, though a few poutine may have given their lives for the cause, eh?

Joining us is someone who would spin a good yarn if his own real life tales weren’t fascinating enough to share: far-famed angel investor and author of Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000, Jason Calacanis. Listen, learn, and enjoy!

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More About This Show

As a young man, Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 author Jason Calacanis resolved to never fail when he saw his father’s business taken away after landing in the crosshairs of the IRS.

Jason waited tables and worked his way through college (at a time when such a thing was possible), eventually finding an opportunity to exercise his computer skills and gain traction as the nascent World Wide Web was taking its first baby steps. He founded the Silicon Alley Reporter in 1996 and the future seemed bright — so bright that he turned down a buyout offer for $20 million.

“And then the dotcom crash happened,” says Jason. “And the Internet went from being the hottest thing in the world to being a bunch of charlatans and con artists. And I had to have a really deep look in the mirror and say, ‘Am I a charlatan? Is this real? What just happened?'”

Most of his magazine’s advertisers went out of business overnight. His regulars couldn’t take out any more ads, and there wasn’t any money to pay for ads that had already run.

“We went literally from $12 million revenue in one year to $500,000 the next. It was really brutal. I had to lay off 80 people; people cried. It was a really trying experience and I just thought to myself…’I promised myself I would never fail. And now I am on the precipice of failure because the stock market crashed.'”

Listen to this landmark 100th episode in its entirety to learn what Jason did next to resurrect from the failure he promised himself he’d never endure, the authenticity of blogging in the early 2000s that appealed to Jason and set him up for his next business venture, what it was like to go from being $10,000 in debt to never having to worry about money again, why Jason prefers to work as an angel investor rather than at the venture capitalist level, why businesses really fail, the lists Jason makes to weigh the pros and cons of a pitch, why most people are risk averse (even when the rewards far outweigh the risks), why Jason believes the ideal startup founder is someone who is delusional — but has skill, four must-ask questions Jason puts to founders, and much more. Make sure to stick around for the Q&A at the end!

THANKS, JASON CALACANIS!

If you enjoyed this session with Jason Calacanis, let him know by clicking on the link below and sending him a quick shout out at Twitter:

Click here to thank Jason Calacanis at Twitter!

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