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
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To Follow Me on Twitter: @RyanHawk12

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Episode edited by the great J Scott Donnell

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

The Learning Leader Show With Ryan Hawk