VCs vs. Angels: Different Perspectives

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.

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

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"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

Social Media:

• See why over 286,000 people follow Jason on Twitter: @Jason
• Read: Angel - How To Invest In Technology Startups - Timeless Advice From An Angel Investor Who Turned $100,000 Into $100,000,000
• Connect with me on LinkedIn
• Join our Facebook Group: The Learning Leader Community
• To Follow Me on Twitter: @RyanHawk12

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Episode edited by the great J Scott Donnell

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