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
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Episode edited by the great J Scott Donnell
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