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Episode 214: Jason Calacanis – How To Turn $100,000 Into $100,000,000 (Angel Investing)

Episode 214: Jason Calacanis – How To Turn $100,000 Into $100,000,000 (Angel Investing)

Jason Calacanis is a technology entrepreneur and an angel investor. The founder of a series of conferences that bring entrepreneurs together with potentials investors, he was a scout for top-tier Silicon Valley venture capital firm Sequoia Capital and frequently appears in the media. He is the author of a new book, Angel: How To Invest In Technology Startups – Timeless Advice From An Angel Investor Who Turned $100,000 into $100,000,000.

Photo credit: Calacanis.com

Episode 214: Jason Calacanis – How To Turn $100,000 Into $100,000,000 (Angel Investing)

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The Learning Leader Show

“I don’t need to know if your product will succeed.  I need to know if you will succeed.”

Show Notes:

  • Sustained Excellence/Key Traits in the greatest Founders
    • Craftsmanship — Making something, having attention to detail, understanding the why
    • Passion
    • Intentionality
    • Thoughtful – Do they know why they do what they do
  • As an investor, you need to ask short questions
    • “Small Mouth, Big Ears” — LISTEN. Let the founder talk
  • Are they a missionary or a mercenary? Need to know
    • Why are they doing this?
    • They need to understand that it is really hard
  • Self awareness is a must — Jason knows that he is a compulsive gambler. He has a risk taking approach. He likes having an edge.
    • But he also has “tilt control.” He knows when to lay down a big hand (poker speak for when you have a big hand but still know it’s not enough)
    • You need to know who you are and what you enjoy
  • “I love being the guy cutting a check for a founder that nobody else believes in”
    • “I win about once in every 40 investments. I was a poor kid from Brooklyn and now I’m extremely wealthy”
  • “I found a casino called Silicon Valley”
  • “There are a lot of really dumb people who are fabulously wealthy in Silicon Valley”
  • “Investing in this market is like being dealt the Ace of Spades”
  • Winning big poker hands against Daniel Negreanu and Phil Hellmuth
  • Jason covered Travis Kalanick while he was at Scour
  • When Travis showed him Uber, Jason immediately said, “Can I invest?”
  • Were some of the qualities that led to Travis and Uber’s success also what led to the problems?
    • He has a fighter mentality. That’s why he’s been so successful. It’s a fair question to ask if that’s what has led to these problems as well…
    • Sometimes you have to take a step back and analyze what’s happening
    • Getting from A to B, you need to fight.  Going from B to C, you need empathy
  • How do you get paid as an Angel Investor?
    • Go public — IPO
    • Secondary Shares — Company buys back shares from early investors (this happened for Jason with Facebook)
    • Company is bought — WhatsApp, Oculus, Instagram — Get cash/stock
  • Investing practices
    • How much of your bankroll do you put in play?
    • Build a network — Technology is the future
  • Ways that everyone can invest
    • Syndicates
    • Angel List
    • Seed Invest

“Elon is a good friend. He was broke. I asked how much the Model S cost. He said, “$50,000.” I wrote him two $50,000 checks and said, “I’ll take 2.”

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Episode 179: How To Sustain Excellence – The Best Answers From 178 Questions

Episode 107: Simon Sinek – Leadership: It Starts With Why

Episode edited by the great J Scott Donnell

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