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) Subscribe on iTunes  or Stitcher Radio 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: 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 More Learning: Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon Episode 071: NateBoyer - Green Beret, Texas Football, The NFL 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.