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The Learning Leader Show With Ryan Hawk

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

The Learning Leader Show With Ryan Hawk

Ryan Hawk

Business, Careers, Management

4.9 • 1.4K Ratings

🗓️ 16 July 2017

⏱️ 64 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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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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

Social Media:

More Learning:

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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

The Learning Leader Show is supported by Rhone.  Use the code "Leader" for 15% off.  Rhone... premium activewear engineered with principle, performance and progress for the modern man.  Rhone builds clothing around 3 main tenants: Cutting-edge Performance, Premium Comfort, and Simplistic Style.

 

Transcript

Click on a timestamp to play from that location

0:00.0

I came home and I just wrote two checks for $50,000 to Tesla and I put him in an envelope and I said

0:06.6

Looks like a looks like an awesome car. I'll take two and I FedEx it to him and the checks weren't cleared were never cashed because I had asked him do you have a month I told my wife like I think this will pay for like three days of salaries at Tesla and so we're going to lose this money but it's my friend, so I got to try to help them.

0:25.0

It'll make him feel good to open the FedEx envelope at the very least.

0:29.0

And he wound up cashing the checks like nine months later a year later he had gotten the funding for

0:36.4

Tesla and then two or three years later I got an email congratulation, just you know000,0001, and then I got second email,

0:46.8

two seconds later, your reservation number 0,000, 73.

0:51.1

And so I told them, you don't have to give me number one, one and he says I kind of want you to have number one because when we were going to go out of business you you you paid for it and you deserve it.

1:02.0

This episode is brought to you by my friends at Callaway Golf.

1:07.0

Callaway's business and marketing approach has turned heads over the last several years,

1:11.0

helping the company make a dramatic

1:13.0

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1:17.4

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1:27.2

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1:29.2

And the coolest part about this partnership is we're doing a giveaway.

1:33.0

Yes, we're giving away the number one selling driver of 2017, the GBB epic driver.

1:40.0

All you have to do is put your favorite leadership quote pulled from an episode of The

1:46.6

Learning Leader Show on Twitter or Instagram.

1:50.4

So pull your favorite leadership quote that any of the greatest leadership minds over the last three years from the

1:57.0

Learning Leader Show has said quote them on Twitter or Instagram and tag my name at Ryan Hawk 12 at Ryan Hawk 1 2 on Twitter or

2:07.7

Instagram. My team will gather all of the quotes and you can enter as many times you like the more times that you

2:14.5

enter the better chance you have of winning and over the course of a few months we

2:19.0

will gather them all and then we will draw a random winner and my friends at

...

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