The Learning Leader Show With Ryan Hawk - 214: Jason Calacanis - How To Turn $100,000 Into $100,000,000 (Angel Investing)

Episode Date: July 16, 2017

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.  

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Starting point is 00:00:00 I came home and I just wrote two checks for $50,000 to Tesla, and I put him in an envelope, and I said, looks like an awesome car, I'll take two. And I FedExed 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, yeah, it's my friend, so I've got to try to help them. It would make them feel good to open the FedEx envelope at the very least.
Starting point is 00:00:28 and he wound up cashing the checks like nine months later a year later he had gotten the funding for Tesla and then two or three years later I got an email congratulations oh just you know your reservation number zero zero zero zero zero one and then I got a second email two seconds later your reservation number seven three and so I told them that you don't have to give me number 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 pay for it and you deserve it. This episode is brought to you by my friends at Callaway Golf. Calloway's business and marketing approach has turned heads over the last several years,
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Starting point is 00:01:55 over the last three years from the 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 Instagram. My team will gather all of the quotes and you can enter as many times you like the more times that you enter the better chance you have of winning. And over the course of a few months, we will gather them all and then we will draw a random winner and my friends at Callaway will send you the GB epic driver. Thank you so much. I look forward to seeing all of your great responses on Twitter and Instagram at Ryan Hawk 12. And thank you to my friends at Callaway Golf. Hey and welcome to the
Starting point is 00:02:42 Learning Leader Show. I am Ryan Hawk. Thank you so much for being here. It is Mindful Monday. Go to learning leader.com. Enter your email address. Join thousands of other learning leaders who receive a note every Monday morning to discuss the latest trends and topics and leadership. Converse with each other as well as me. I'd love to have you. Go to learningleader.com. Enter your email address. My featured leader tonight is Jason Callicanis. He is an investor in more than 150 companies, including four multi-billion dollar unicorns. He has also built and sold multiple companies for tens of millions of dollars. We discussed his most recent work, his book titled Angel,
Starting point is 00:03:29 How to Invest in Technology Startups, timeless advice from an angel investor who turned $100,000 into $100 million. Jason certainly has a number of fascinating stories, and he told them to me tonight, a few other topics, the common traits that the successful founders all have, then the questions he asked the founders in pitch meetings, and then why he believed in Elon Musk and the story behind him having model number 0-0-0-1 of the Tesla Model S. It is such a cool story.
Starting point is 00:04:06 Ladies and gentlemen, without further ado, it's Jason Kalakanis. All right, Jason, thank you so much for being here on The Learning Leader Show. Welcome. It's a pleasure to be here. Thanks for taking the time to have me and for reading my book. Absolutely. Angel, how to invest in technology startups, timeless advice from an angel. investor who turned $100,000 into $100 million. It's incredible.
Starting point is 00:04:33 A great book. I recommend it, but I expect us here throughout the course of this conversation to really learn about you and your thought process. I love speaking with people who are really thoughtful about the decisions they make, about some of their routines, rituals, things that they do that help them lead to sustained excellence. That leads me, Jason, to really my first question because you are surrounded by people who have sustained excellence.
Starting point is 00:04:59 You've invested in some of these founders. You've done some really incredible things. You're early on a lot of unicorns. I mean, Uber being one of them, they're really in the news a lot right now. And there's others. But I'm curious from your perspective, when you look at the common themes amongst those entrepreneurs who sustain excellence, what are some of the commonalities amongst them? That is a great question.
Starting point is 00:05:25 And it turns out that what I'm, I've learned about angel investing in companies, and I meet with, you know, I'd say a dozen or two dozen companies a week and get hundreds of emails a week asking me to invest. So I'm looking at literally 100 companies a week in my email box and then meeting with a dozen or two dozen of them a week for the past five years. You get a lot of signaling, right? And you start to see which companies you bet on and you thought would win, fail, which ones win, which ones go sideways. And then the ones you passed on, if you're a considered person and you do a little bit of forecasting, like have a pen in a journal and write why you're not investing, you can go back and look at your forecasting and say, why did I miss Twitter? Why did I miss Zinga? Why did I miss Zendesk? These are all companies that I missed. And Eventbrite, you know, there's a whole series of the anti-portfolio, unicorn companies that I could have invested in that I didn't. And that's when you start to actually. realize what I consider my key insight into angel investing, which is the most early stage investing is, I don't need to know if your product is going to succeed.
Starting point is 00:06:40 I need to know if you're going to succeed because most people, when they start a company, they have a product that is very awkward, right, like a teenager. It's not designed well. It's broken in some ways. It's awkward and it's not super polished. It needs a lot of work. But eventually it grows up and becomes something tremendous. So I think most great founders figure out how to make their product work, how to create a market or serve a market.
Starting point is 00:07:15 And what I'm really looking for is that very specific traits in a founder that I think will lead to breakout success. What are some of those traits? Yeah, so this is where it starts to get really interesting because you are looking for certain traits and you're looking and you're trying to determine if you can actually judge them, right? So I play a lot of poker and I think one of my gifts or just one of my skills has been over time learning how to read people over a decade or so of playing poker and being terrible at it and then getting better at it and then maybe being good or maybe even. on my best day, very good at reading people. And if a person has craftsmanship, in other words, when they make something, they put a certain intention to detail into it, and they're good at making a product. That seems incredibly basic, but when you're looking at companies over and over again,
Starting point is 00:08:15 you'll find that you go to one website, or you look at one logo, or you look at one product's navigation, what we call in our industry, UX or UI, user interface, user experience. And you say, wow, this seems very considered. It seems like some thought went into it. And then you ask a question, hey, why did you put, why did you place the buttons where they are? Or what is this feature, why is this feature so prominently displayed? And when you hear from the person a level of passion and a level of thoughtfulness and they've
Starting point is 00:08:49 really thought about it and they have a reason why they designed it in a other. other words, intentionality. So I threw out a couple of words. They're craftsmanship, passion, intentionality. And these are things that people who are great at making product have. They have a passion for what they're doing. They're very intentional with how they do it. They know why they're doing it, right? And they're good at how they execute. It doesn't have to be perfect. But I remember an early investment in a company called Thumbtack. When you're doing angel investing at the level I do it, when there's two, three, four, five people in a company and the company's a couple of months old, typically, and you're one of the first five investors, really true angel investing, not seed investing, but angel investing. There's not a lot to go on, but I remember with Thumbtack, I was talking to Marco Zappacosta, the founder, and he's a first-time founder, and I said, hey, what is, where are these two icons down here?
Starting point is 00:09:47 And he said, oh, and at the time they were a directory of local service providers. And they said, oh, well, that tells you if we know that this person is insured and that they have a business ID, like a tax ID, and then we've checked that they're insured. This one is that they have a tax ID. And this one is that we know their address and have their driver's license on file. Driver's license on file. I said, well, why do you need that for a gardener or for, you know, somebody who's going to paint your house? And they're like, well, most people go on Craigslist. And when we did our user research and we talked to people, they were a little nervous.
Starting point is 00:10:20 They didn't know who they were inviting into their house. And what if they get hurt while they're working and they're painting the house and they fall down? Are they insured? And is this person going to rob me or is there something I should be scared about in their past? And I was like, oh, wow, I never really thought about that. And oh, wow, they're really considered. They must have done some user interviews. They must have talked to the customers.
Starting point is 00:10:41 They thought about, hey, what's the unique solution to this problem? and they also had designed it very well. So these beautiful little icons along the bottom that when you hovered over, they explained what they did. And I said, wow, I could see that working. And over and over again, when I have a conversation with the founder, I ask short questions. And I get into this in the book a lot. I ask very short questions. In other words, I have a very small mouth.
Starting point is 00:11:04 And then I have very big ears, which is a sort of expression we have here in the valley, which is small mouth, big ears. When you're an investor, you really want to let the founder talk because they can either talk to you, out of investing or talk you into investing. You want to see, you know, why they're doing what they're doing. Does it have true meaning to them? Are they a missionary or a mercenary, right? And I always ask people a very short set of questions. And one of the questions I ask them is, why are you doing this?
Starting point is 00:11:32 And why are you doing this? Why are you doing, Ryan, this podcast? Like, what's the why? And you'll be amazed that, you know, some significant double digit percentage of the time, people say, well, because I think I'll make a lot of money. And boy, is that a terrible answer. While it's great that you want to make a lot of money and have a huge return for us investors, startups are so hard that if you're doing it just for the money, you're going to wake up one day and go, holy shit, this is fucking hard. And there are many easier ways to make a lot
Starting point is 00:12:02 of money. I should go work at Google as a developer and get a million dollars a year programming some very obscure piece of technology. Or I should work as a banker, Goldman Sachs. That's an easier way to make money more consistently. So is all of these little subtle questions you can ask and then really listening to the answers is the key. Well, why do you do what you do? Why choose this route? I mean, you could, I would assume you could be, any number of companies would want to hire you full time to have your brain beyond staff every day all day. And instead, you choose to invest in technology startups.
Starting point is 00:12:43 instead of joining one full time. So why do you do that? Yeah. So self-awareness is probably one of the most underrated life skills for individuals. And this goes for founders, investors, and just everybody. If you're aware of who you are and how you function in the world, and the world's a complex place, and people are different, people are biologically different, and people have different upbringings. They're behaviorally different. They have different things they like to do.
Starting point is 00:13:15 Brain chemistry is different from individual to individual. We're finding it out more and more that there's a lot of differences. And one of the differences I have is I think I have a very compulsive, gambling, risk-taking approach and brain chemistry. And it gives me great pleasure to take risk. that's not and when I talk to people who don't take risk I hear from them that they're very scared of the downside and I think that I would have been a full-time professional gambler if I wasn't an angel investor and I loved running companies but there's something really fun about picking the winners and then trying to help them win and have an unfair competitive advantage
Starting point is 00:14:06 and build up an unfair competitive advantage, having an edge, which anybody in poker, like you're in gambling, you're looking for your edge. Now, edge sometimes means to some people like cheating. I'm not talking about cheating edge. That's an edge too far. But there are people who are very good at reading people in poker. There are people who have tilt control.
Starting point is 00:14:25 They don't get out of control if they lose five hands in a row that they should have won. There are people who have the ability to lay down very big hands in poker because gosh, they don't have an ego about it. And there's other people who have an ego about it, gets them in trouble. So I think when you start to understand who you are and what you enjoy, that's when you can find this incredible moment in your life where you become very good at something that you very much enjoy and that very much matches who you are. I love being the guy who writes the check for somebody who nobody. else believes in or most people don't believe in. That to me is the most exciting check in the
Starting point is 00:15:08 world. When I can give a founder 25 or 50 or 250,000 or say, I know everybody thinks that you're going to fail, but I actually believe that you're going to make this happen. It's like being able to draft somebody in the NBA and say, you know what, I know Steph Curry is lanky and nobody believes that this person should be picked seventh in the draft or even in the first round, but I'm going to take them. And there were six people in front of them, right? But, you know, somebody just decided, screw it. We can see that this is a special person.
Starting point is 00:15:45 It's very exciting to me. It may not be to other people, but to me, it's extremely exciting. And then to be able to talk to the founders, these people who want to change the world, and then have them call me or text me on the phone and say, hey, Got a minute. And I get these texts at 1230, 1 o'clock in the morning, 7 a.m. on a Saturday. Hey, are you up? Hey, got a minute.
Starting point is 00:16:12 And then we have some conversation about changing the world and about taking on the giants and taking this little rag tag team of 12 people and having them take on a company with 12,000. And then they win? I mean, this is like for me, it would be. the equivalent of winning a bracelet at the World Series of poker. It's like winning the lottery, but I get to do it. I get to win the lottery every 40 investments. Like literally right now, I have four companies that become unicorns in close to 150 investments. And it's literally like I win the lottery every 40 investments so far. And to me, that's why I wanted to write the book,
Starting point is 00:16:54 because for a kid from Brooklyn who grew up poor, lower middle class at best, and whose parents were constantly, you know, in debt and fighting over money to suddenly become extremely wealthy. And I'm super humbled and excited and thrilled that I have hit, you know, seven lottery tickets in my life and four big ones. I want to pass it on. I know that sounds crazy. But I wrote the book specifically because I found a casino called Silicon Valley. And in this casino, if you invest $100,
Starting point is 00:17:29 in a company, the chances are that, you know, eight out of ten times you're going to get back zero. But maybe in that ninth or tenth time, you might get back five X, 10x, and then there's the outside chance you might get 25, 50, or 100x. And almost everybody I see who does angel investing in Silicon Valley, and that's a very important qualifier in technology startups, another important qualifier. I'm not talking about movies. I'm not talking about dry cleaners. I'm not talking about Boise, Idaho.
Starting point is 00:18:00 I'm not talking about Brooklyn, where I'm from, or Los Angeles. I'm talking about Silicon Valley and tech startups. The people who are investing in those really dumb people I've met have gotten fabulously wealthy. People who are lazy. I've watched them get fabulously wealthy. There is a rigged casino in my belief. I have to be very careful about giving financial advice. But my experience has been investing in this market is like,
Starting point is 00:18:28 going to a poker game and getting the ace of spades every time as your first card in Texas Hold'em. No matter what the second card is, you've got a pretty good starting hand, right? Anybody who plays, you know, if you look at that first card and you see Ace of Spade, you're like, all right, here we go. I'm going to play a hand maybe. And God forbid, you know, you get another spade or you get Jack Queen King or Ace. We're going to have some fun. And that's how I feel it is to be an investor in Silicon Valley.
Starting point is 00:18:58 One of your unicorns is Uber. You were, what, third or fourth in? Is that right? That's what I'm told. I was told I was in the first, like, four investors or something. And I think, so in addition to reading your book to prepare for our talk, I also am in the middle of reading Brad Stone's book called The Upstarts, and he followed Uber and Airbnb.
Starting point is 00:19:18 You're quoted it and talked about quite a bit. I'm not sure if you read it or not. I haven't read it, and I didn't participate in it, but I hear it's great. It's good. A couple of people have told me that I'm featured prominently. You are. You are. And so, and Travis, obviously, he's in the news a lot now. And so I'm curious about, it's not all good news, but I'm curious about your thought process. If I was trying to pick up an example of where you could share the what you were thinking then as when you were one of the first people in, when I think most, the overwhelming majority of people, I believe you said you emailed 20 different VCs and 18 of them immediately said no. And a couple said yes. about Uber and you you got in very early when a lot of people were saying, are you kidding? That would never work.
Starting point is 00:20:05 There's all these negatives about how could that possibly work. And now we look at them and it's wildly successful globally. So what was your thought process at the beginning the first time you talked to Travis and about your thought of investing in Uber? Yeah. I had known Travis from his first two companies when I was a journalist. Some people listening might remember I did a magazine in New York called Silicon Alley Reporter. I did a smaller one in Los Angeles called Digital Coast Reporter. And I was kind of an impassario with print magazines in the 90s.
Starting point is 00:20:41 And I covered Travis's first company, which was called Scour, which was a peer-to-peer piece of software. I had it in college. Yeah. Yeah. Sort of like Napster. But Travis had thought, well, if you can trade MP3s, why not trade any files? So you could trade a PDF for a JPEG or a movie. And he wound up getting sued for a quarter of a trillion dollars
Starting point is 00:21:03 because a bunch of people traded the Last Action Hero and a bunch of other movies. And then he did something called Red Swish, which was sort of the white hat version of it. It was peer-to-peer data sharing like CDNs. And he did okay. That was like a single or double. And when he showed me Uber and he said, hey, can I show you what I was working on, what I'm working on. And we were at the Embarcadero coming out of a party and we're just catching up.
Starting point is 00:21:29 And before he showed it to me, I just said, can I invest? He said, sure. And I said, okay, now show it to me. Because I just knew, like, whatever he's doing, he's going to be successful, just a matter of how successful. I thought it could be a billion dollar company. I never thought it could be a $70 billion or $40, $50, whatever people believe it's worth. Some people believe it's worth $150. Some people think it's worth $40.
Starting point is 00:21:49 You know, the truth will be probably between those two numbers. And it was just, again, back to. I don't need to know if your idea is going to succeed. I need to know if you're going to succeed. And it turns out, you know, two out of three, three out of four startups fail. They fail hard. What that means to me, in my risk-taking insane brain that loves to gamble is, if you fail twice, I really want to talk to you about your next idea.
Starting point is 00:22:16 Because in my bizarre mind, I think you're going to hit the nuts on the next one or the next one, right? I'm the kind of guy who's like, oh, there's the roulette wheel and seven reds came up. I have the chances 15 reds come up in a row. Screw it. I'm going to Martin Gallen and just double my bets until I see a block. I know that it makes no statistical sense. You know, and people could fail continuously. And every time the odds are 50-50.
Starting point is 00:22:41 But I just look at it and go, God, you have to have learned something in getting your ass kick the first time. And getting a single or double by getting hit by the ball, essentially. you know, getting on base in a, you know, a challenging way. I just knew Travis was a winner. Now, nobody could predict the breakout successes. You know, Airbnb being another perfect example you brought up, like, really sleeping on couches, like, I looked at that business and I was like, I am not going to be murdered by a serial killer or rent a room with 17 hidden cameras in it.
Starting point is 00:23:18 Like, Airbnb to me was the stupidest idea I ever heard. I just thought, this, I mean, and that. I realized, you know what? Schmuck, it's not about you. What I think about the idea does not matter. And this is where there's a big difference between the great investors and the good investors and just the great and everybody else. I think the great investors divorce themselves from being able to determine what's going to work in the market. You can have an idea.
Starting point is 00:23:46 You can do research. But I actually think at these early stages, nobody knows how big these things can get. And in a lot of cases, the market that an Uber or an Airbnb or a Pinterest or a house or Facebook or Twitter, a lot of these companies, they're building, they're actually making a market. There wasn't a, what was the market for sharing photos before Instagram? Polaroids, you know, people emailing photos to each other. you know, like Kodak was the company, you know, in Polaroid, were like the companies before Instagram. And they have this long, you know, arduous, you know, startup march with flip cams and other digital
Starting point is 00:24:33 camera companies and Ophoto and all different flicker where people are just trying to figure it out. And some of them did figure out some things. But then you have a company like Instagram that figures out mobile first filters. and social media and a social graph equals something bigger than anybody had ever anticipated that photos could be. This is an incredible why now. It could not have happened if you didn't have the software and the GPU capable of doing that. If you look at Uber, really the reason Uber worked so well is because modern phones had GPS on them. And the GPS was accurate.
Starting point is 00:25:13 Without GPS being accurate on phones and without the app store, it could never have happened. happened. In fact, there were companies before Uber and Lyft where you could order a taxi over SMS. You would SMS what your address was and they would SMS you that the car was coming. So you could do it over text messaging. The why now for that company was text messaging, but that wasn't enough. It was the why now with GPS on phones. That was the one that made Uber breakout. So why now is just a critical question. What other ones? Did you get the very first Tesla? So a good friend of mine, Elon Musk, who I knew when he was thinking about starting a rocket ship company and was researching rockets in Russia.
Starting point is 00:25:59 He had gone with a friend of mine a day over to Russia to look at rockets. He was going to buy a rocket from the Russians and then or buy the payload and put it on a Russian rocket and put, I think his original plan was to put to back up the biosphere, to put plants up in space and like, geodomes. And so if anything happened to Earth, you'd have all these plants in outer space. It's a pretty awesome idea. But then he was like, oh, wow, rockets are not that complicated. I could make some. That's like how Elon's mind works.
Starting point is 00:26:31 It's like, that's not so complicated. You and I would look at it and go, oh, my God, that's too complicated. But talk about a guy who, you know, I would never teach Elon. I told him I would never teach him poker because talk about a person who likes to gamble and likes to take risk. I don't, I think in terms of understanding who you are, I don't think that he has a fear gene. I think he literally has no fear of failure.
Starting point is 00:26:52 So he's like, yeah, rocket seemed like something I could work on or electric cars seem like something I could work on. He just plows ahead and, you know, engineers the heck out of those projects. But he was thinking about, he had seen this electric car company and had been pitched on it and he put $50 million into it, I think is the story. And then I remember meeting with him and the company was a total disaster. The people who are running it were just completely incompetent. And he's like, I got to find a CEO for this company that I invest all this money.
Starting point is 00:27:24 And he's like, I'm going to take over temporarily. But, you know, they're spending $200,000 to make $130,000 car. We're going to lose our shirts if we actually produce these cars. And he had to redo the entire supply chain and redo everything. Anyway, we were out one night during the financial crisis. And just the two of us and we were having stakes in Los Angeles. And he was pretty, I don't want to say depressed, but he was pretty beside himself with the financial crisis occurring. And there were reports that he had less than a, he had a month of payroll left in the bank at Tesla.
Starting point is 00:28:00 And he was personally broke. Like literally Elon Musk was negative. When was this? 2008, nine? Yeah, this is during the financial crisis. And I'm not speaking out of school here because he's told these stories. I would never tell it unless he had told it already. But yes, he's told very publicly.
Starting point is 00:28:15 he had a loan from a mutual friend of ours and he was broke and I said well I can lend to like a million or two million dollars and he's like don't worry about it it's not going to help and I said well it's got to be some good news and he said yeah can I show you something you can't can't tell anybody I said sure and he started flicking on his back Blackberry this is to date the conversation yeah through the clay models for the model S well what would become the sedan and I had number 16 of the roadster he's was driving P1, the production, or P2, the first two production versions before they had the signatures. And I said, wow, that's amazing. What do you think you can make it for? And he's, I think I can make it for 50 grand. So I went home. It was like Monday.
Starting point is 00:29:01 And then Sunday. And then I was talking to my wife. I said, Elon's not in good shape. Like, I think Tesla's going to go under. And I had asked him, like, what if you blow up another rocket? Because I think he blew up the first two SpaceX rockets. He said, if we blow up a third rocket, the company's over. So it was pretty dark.
Starting point is 00:29:18 And I came home and I just wrote two checks for $50,000 to Tesla. And I put him in an envelope and I said, looks like an awesome car. I'll take two. And I fed X it to him. And the checks weren't cleared, were never cashed because I had asked them, did 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.
Starting point is 00:29:41 But, yeah, it's my friend. So I got a try to help him. It would make him feel good to open the FedEx envelope at the very least. And he wound up cashing the checks like nine months later, a year later. He had gotten the funding for Tesla. And then two or three years later, I got an email. Congratulations. Oh, just, you know, your reservation number is your zero, zero, zero, zero, zero.
Starting point is 00:30:03 And then I got a second email two seconds later. Your reservation number zero zero, zero 73. And so I told them, you don't have to give me number one. And he says, I kind of want you to have number one because. when we were going to go out of business, you paid for it and you deserve it. And I was, oh, that's very touching. And so I still drive the car to this day, but I'm going to stop driving it soon and put it in a museum somewhere. But, you know, there's another example of a founder who nobody believed in or very few people believed in.
Starting point is 00:30:33 And, you know, a lot of these VCs are just complete idiots. And their VCs for a reason, like they either couldn't cut it in the real world or, you know, they just, they were not operators. there is a contingent of venture capitalists. And venture capital is very different than angel investors. Angel investors are putting in their own money typically very early. Venture capitalists are putting their money in much later when things are still very risky, but a little bit tighter. The venture world's changed to have many more operators, people who've run businesses
Starting point is 00:31:04 as venture capitalists, but there were a lot of people who were like pure venture capitalists. And I remember they were trying, one of them was trying, who had invested in Tesla, They were refusing to continue investing, and they were demanding that Elon not make a car. They literally wanted Tesla to just sell the power train to Mercedes and Toyota and just be a supplier. Now, imagine how much that company would have been worth. Maybe if they did everything right, they could be a billion or $2 billion company. You know, now they're 20, 30, 40, maybe they'll end up being a $400 billion company. that's even though that's only 20 or 30 or 40x or 200 x that's 20 30 40 200 x a very big number a billion dollars so and the same thing happened with uber one of the vc who said jason can you take
Starting point is 00:31:59 Travis aside and tell him that he's making a huge mistake competing with cab companies what he should be doing is making enterprise software and empowering the cab companies with this software so that you could download a carry car service app and you could have a music app and you can have an 888 888 in New York car service app and there would be 50 different car service apps in each city and he would make $500 a month for each and he get a dollar per car per day per each network or whatever and he would be a software company like Salesforce and I said wow that's a really interesting an idea let me think about let me let me talk to Travis about that and you know what I did I never even brought it up with Travis I was like this person's a fucking idiot Jesus Christ
Starting point is 00:32:44 Like, do you not understand the cab companies were the ones who were taking 60 cents or 70 cents of every dollar, the medallion owner, the person renting the car? They were taking the lion's share of the money and then charging this extraordinary fee. It was $125 to go from San Francisco airport to San Francisco. And then the cab company would take $75 of it or $50 of it. They were just taking all of the money. And then Uber comes out and it's whatever, $15 to get from San Francisco to the airport if you take a pool and maybe $20 or $30 if you take, you know, and the 75 cents on every dollar goes to the driver. And you don't need to have all this infrastructure in between. You don't have to have corrupt medallion systems that are owned by millionaires putting cab drivers into indentured servitude.
Starting point is 00:33:40 So it's really important, I think, to not listen to other people who think they understand your business as a founder. You have to be your own North Star. You have to have your own sense of mission and purpose. And I know these are kind of like yoga, mindfulness kind of words. But if you break down the words, if you have a mission, it means you have like a higher calling. You have a very specific reason you're doing this. And I think for Uber, they wanted everybody to have their own personal driver. They wanted everybody to be able to move around a city, point to point, anytime for an affordable price.
Starting point is 00:34:16 It's mind-blowing to think that transportation was a gating and limiting factor for people just five or ten years ago. And you notice if you go to another city, it's like, what are my options to move around the city? And they're like, there's a bus where you could take a cab to the train, take the train to where you're going, then take a bus, and then take another cab. We used to sit there and plot strategies of how we would get from point A to point B to point C. Now you go to any city that has Uber, you don't even think about transportation. You know it's going to be, you know you're going to get picked up in a couple of minutes, single digit minutes. You know it's going to be for a fair price. You know you're not going to get ripped off.
Starting point is 00:34:59 You know that you're going to be 10x safer than doing some random cab where you don't know who you're getting into and there's no tracking and there's no minute. by minute GPS coordination of the ride, right? Like all of these things have been either solved or made much safer and much cheaper. So I think it's important to look for founders who have that sense of mission and purpose because they're going to be dark days, like the dark days of Tesla when they were running out of money. And the dark days now for Uber where they've got a bunch of self-inflicted wounds that they don't have anybody to blame for themselves, but they'd have to work through, right?
Starting point is 00:35:38 and they have to work out, there are going to be dark days. When you have a sense of purpose and a sense of mission, you can continue on through the dark moments to get to the Promise Land. It's very much like somebody who's a great poker player, I'm good friends with a guy named Phil Helmuth, who's got 14 bracelets, he's the goat, as they say. And, you know, he'll bubble a final table. He'll come in 10th and not make the money in a tournament.
Starting point is 00:36:05 He'll make a bad play or he'll, make a mistake or miss an opportunity. And he just stays relentlessly positive. He knows he's got 14 bracelets. And he goes back the next day and says, I'm the greatest ever. I will get the 15th. And I'll just doggedly pursue my goal of being the greatest of all time. And he's already the greatest of all time. So that kind of doggedness, that kind of indefatigable spirit is what I'm always looking for in a founder. It's almost a willingness to sacrifice everything to win. And that can be off-putting at times to people, but these companies are so hard to run. They're just, it's so brutal.
Starting point is 00:36:47 It's so hard that it's not for everybody. Being an angel investor is easy by comparison, even though there are some difficult issues you have to get used to, like losing a lot. Yeah. What about, do you think some of those same qualities that a person like Travis or, dare I say, Steve Jobs could lead to some of the troubles, that Uber is going through right now. I read, I'm not certain. I mean, you probably know this better than me that he may be going on a leave of absence. I know he's got personal things, too, with his family that are tragic.
Starting point is 00:37:19 But do you think some of the great qualities that have made Uber what it is have also created some of the negatives that are happening right now? I think it's a fair point that, you know, a fighter's mentality, you know, may be necessary. early on in the life of a company, especially for a company where the incumbents are doing whatever it takes to stop them. And if you look at a company like Airbnb or Uber, the incumbents would use any dirty trick, any lobbying, any corruption, any antiquated legal law to reduce the options of individuals, consumers. And we see this over and over again, whether it's the telecom companies or the hotels or the medallion owners, they want to limit consumer choice.
Starting point is 00:38:12 And companies like Uber and Airbnb and Tesla with their trying to sell directly to customers and not have a dealership network, you've seen them have to fight in certain locations where they're like, you cannot open up a store in New Jersey or Texas. It's like, why can't we open a store? Oh, because it's this regulation that you have to have a dealer. It's like, why do we have to have a dealer? Which Apple doesn't have a dealer. They sell phones directly. What's the difference between a phone and a car? It's like, we don't know.
Starting point is 00:38:36 But that's the law. It's like, okay, well, we don't want to have dealer. So anybody in New Jersey, go to New York or Pennsylvania to buy your car. So if you get into that fighter's mentality and then you become the dominant company in your space, it takes a moment of consideration and it takes some personal evolution, let's say, to say, okay, to get from point A to point B took. the most hard, horrific, brutal, knockdown fight to get here. Okay, how do we get from point B to point C? And you're like, okay, well, I got to fight 10 times harder. It's like, nope, it's actually the opposite.
Starting point is 00:39:23 You now have to be magnanimous. You have to have empathy. You have to put down the sword, pick up the pen. You've got to become a statesman or a statesperson. You've got to be, you know, really empathetic and listen. and it's a whole different approach. And Steve Jobs had the same exact crisis. And interestingly, or notably, he was fired, left his company, created Next.
Starting point is 00:39:52 The company floundered Apple without him. Next floundered without, didn't flounder, but yeah, kind of floundered actually. Next went nowhere. And the two companies, the two entities, Steve Jobs and Apple were reunited. The board said, seems like Steve's evolved a whole bunch as a leader. He's got this incredible team at next. Let's get him back inside this company.
Starting point is 00:40:17 And then Apple went from being roadkill in most people's mind here in Silicon Valley to being, you know, the most, well, it was the most valuable. I think it's top three of the most valuable companies in the world today after Amazon, I think now has surpassed them. But they have more cash on hand than ever. I think that's exactly analogous to what we're seeing with Travis. I don't know that he's Steve Jobs yet, but I think he's definitely Steve Jobs-esque, having known him for 15 years. I think he could eventually be the caliber of Steve Jobs in terms of success in terms of the imprint he leaves on the world. He's still young. He's still got 20, 30 years left in the tank, at a minimum, to go work on projects. So I think he'll come back from, you know, the devastating loss of his mom who passed away unexpectedly and his dad getting injured pretty badly.
Starting point is 00:41:10 I think he'll come back from his break, rejuvenated, evolved, focused. And I think we'll see the best is yet to come. I think although it's incredibly painful what we've seen at Uber, I've never seen a company take ownership and be as transparent and take. decisive action like this. So although I'm super disappointed that a lot of things happened, I'm super pleased with the reaction. I think they're working really hard to resolve the issues. And it's been six months of resolving, maybe six months of resolving all these issues or so, investigations, et cetera. And I think in another six months, we're going to look at it and say, that was a textbook, you know, business school case of how to transform a company and resolve
Starting point is 00:42:00 a lot of systemic issues that needed to be resolved. So for the people who are not in your industry at all and they're listening, like, wow, this Jason guy's really interesting. And you're like, he got in third or fourth at Uber. Well, how much, so how much, how does he get paid? How much money is that worth? When does he get paid? I mean, I think those are, those are normal questions that people seem to have.
Starting point is 00:42:21 How does it work? Like, how do you actually get the money in your pocket? And by the estimates of what they're worth now, how much will that be? So the title of the book is super subtle, how I turned $100,000 into $100 million, a little bit of a link baiting title. It's unlikely that an individual investor, including myself, would hit two of these what we call decade acorn companies. Some people call them decacorns, over $10 million in value. There's another category I call decade acorn, which is they come along approximately two or three. three times a decade. And a decade of corn is, you know, a company that could become worth nine figures,
Starting point is 00:43:08 um, sorry, 12 figures, over a hundred billion dollars, you know, like a Google level, Facebook level, Microsoft, Amazon level success, Apple. Now, they're not there yet, but they're, they're almost there. And it's the way it works typically in, uh, the angel investing businesses, you invest early in a company, 7, 8, 9, 10 years later, it's a long arc. And it could be as soon as three or four years. I've invested in companies and had a return in two, three, four years out. That's an outlier. That's not the normal case.
Starting point is 00:43:44 Somebody comes along, and one of three things happens. One, the company goes public. In previous cycles, companies like Airbnb and Uber would go public when they were worth $5 billion or $10 billion. In fact, we've seen a bunch of those like Box, Twilio, a bunch of companies, Netflix, you know, went public and became worth low billions of dollars. Companies stay private longer now because they have access to more capital and companies grow faster now because of the global market.
Starting point is 00:44:10 So IPO is the first, but that if companies don't IPO and they get very big, there is a second thing that's emerged that's very new, which is called secondary shares. Secondary shares mean that a company will buy back shares from early investors or employees if they want to sell some of their position, 10%, 20%, and some companies have regular secondary share processes, like my understanding is SpaceX every six months. Some employees are allowed to, if they've been there for three or four years, might be allowed to sell 5, 10%. And other parties, like say a hedge fund might want to buy those shares from them or the company,
Starting point is 00:44:50 if they've raised money themselves, might buy them back at a discount to the last price. So there are secondary shares that occur frequently. And then third, and that's something in the last, I'd say, since Facebook, secondary shares became a thing because people were trading Facebook shares in the secondary market a lot. And people who bought them in the secondary market may have bought them for $5 billion and then watch that turn into $150 billion. It's a pretty good return, right, 30X? And then the third possibility, and this is the most frequent, is a company gets bought by a bearer company. So if you look at WhatsApp or Instagram or Oculus Rift, the VR company, all three of those companies were bought for billions of dollars by Facebook. And if you look at Google, they bought YouTube.
Starting point is 00:45:34 So the investors in those companies just immediately get cash where they get stock in that new company. If you have a company, if that happens, you have a banker like whoever's running the IPO or somebody is sort of the clearinghouse of these shares. They take the cap table, the capitalization table from the attorneys at the company. So they take Instagram's cap table with all the shares. They let everybody know you had this many shares. The shares are being bought at a share price of $10 and you have a million of them. And you bought your shares for $0.10. And now they're being bought for $10.
Starting point is 00:46:07 So you got $100x and you can get $10 million and you paid $100,000, whatever it is. And all of a sudden they transfer the shares into your brokerage account. So if it was being done by Goldman Sachs, they might say, do you have a Goldman Sachs account? And you say, yes, here's my number. And all of a sudden, you get a little alert one day. You have. One day, I was an investor in a fund that invested in WhatsApp. And then one day, all of a sudden, I just got a little note.
Starting point is 00:46:34 Congratulations. Or you even say, congratulations. You now have 10,000 whatever shares of Facebook. And I was like, oh, wow, I have a million dollars on Facebook shares. That's nice. And then you get to decide what you do with them. And I decided, okay, I can. go invest this million dollars in startup.
Starting point is 00:46:49 So I think Facebook, when I sold my shares where it's $105, maybe it's $150 now. So I lost that 50%. But for me, I don't like being in the public markets because I don't have an advantage there. I have my advantage in the private market. So I was like, okay, sell those shares, pay my taxes, and then I'm going to go spend that money investing in the next round of companies hoping to get a 50 or 100x, not a 50% growth, right? I'm in it right now to take more risk.
Starting point is 00:47:14 Now, the percentage of your chip stack you spend on angel investing, is a critical topic I discuss in the book. So if you're into poker, like I know you are, you have a bankroll, right? And you have a chip stack. And so a chip stack might be how many chips you sit down at a poker table with. You sit down, if you have a million, let's say you had a scenario where you were worth $3 million. And you sit down at a poker table with $300,000. You've got a $3 million bankroll.
Starting point is 00:47:43 You've just put 10% of it in play. If you lose all of it, now you have two. $2.7 million. And if you make 5% on your money every year, you could reasonably think you're going to make 100,000 or so of that back every year in the increase in your portfolio. So losing $300,000 investing in startups, that 10% of your net worth. If you didn't need access to it for college or some other reason, it might be reasonable to risk up to 10% of your net worth, maybe 5% for people who are retiring soon, maybe 1%. But, but, But I think not taking risk with some portion of your net worth, not making some bets that could be transformative in this amazing casino here in Silicon Valley, I think that that is more risky than just leaving your money in bonds. Because even if you lose half your money or all of your money or two thirds of your money, these are likely scenarios. You could lose all of your money. You could lose half of your money. or you could break even, or you could just maybe double your money.
Starting point is 00:48:49 What if you do that with 5% of your net worth, if you lose half your 5%, you lose 2.5%, but what if you invest in 30 companies and you learn about where the future is going? And you now have a network of 30 CEOs who you text with and you talk to all the time. Now you're in the inner circle of the people doing the most important work on the planet earth right now in terms of driving humanity. I mean, technology is driving humanity right now. Every aspect of what we do is being driven by what's happening here in Silicon Valley. And for you to be able to invest small amounts of money in multiple companies and get this massive education to be part of it, I think that's worth it. If you think about all these students coming out of college, $100,000 in debt,
Starting point is 00:49:35 $200,000 in debt. If they go to law school, maybe they're $300,000 in debt by the time they come out or get their MBA. It's just insane. I think investing in startups would be a much more educational process. If one of my three daughters said, hey, dad, instead of giving me $200,000 to go to a school, $50,000 a year in expenses, will you give me the $200,000 to invest in, you know, 20 startups, 10K each? I'd be like, you're going to learn a lot more investing in 20 startups at 10K each and then meeting with them every other month. I would totally support you being an angel investor. And what if one of them, if one of my daughters hit and one of those becomes worth 100,
Starting point is 00:50:12 Now she got a million bucks, you know? Yeah. Now she's got life-changing money. So I, since I grew up so poor and since I always worried about money, this idea of finding a way to become, to move classes, to move from the, you know, middle class to move to the upper class, to move to the ultra-wealthy. It's very hard in America to move classes right now. In fact, a lot of people, generations now are going to do worse than their parents before them. And the millennial generation is, you know, kind of feeling like, wow, we kind of got screwed. Like we have less opportunity than our parents.
Starting point is 00:50:50 Well, what I do, angel investing in getting on a cap table, getting on that capitalization table, getting equity in high growth startups in Silicon Valley, that is the way. That is the clearest path to changing your station in life. not the NBA, not being Katie Perry or P. Diddy or not being an actor, all of those things could lead to break out success and your chances are one in a million. I think your chances here are much, much better, much better. Like, I think your downside risk is low. Even an idiot coming here and investing in these great companies if they're here in Silicon Valley. Even an idiot would have a hard time losing their money. I think that there's so many, if you diversify and if you spend a small amount of your net worth, I just think there's no downside risk.
Starting point is 00:51:39 The downside risk is you lose a couple of points of your net worth. The upside risk is you could become ultra wealthy. The only other possibility to become ultra wealthy like that is to play the lottery, and we know the odds there are horrific. So I kind of feel like I found the secret casino, and the whole point of the book is that in my ultimate scenario, I inspire 100,000 people. to become angel investors. They all start emailing the deals they're doing to me. I get to co-invest with them in some deals. They wind up being this army of angel investors who I gave some
Starting point is 00:52:15 secrets to and I gave them a competitive advantage so they're loyal to me in some way. They share their deal flow. I get in on some deals with them and then maybe 10 of them hit the next Uber, Airbnb, Microsoft, Google, Facebook. And if they do, they're going to invite me and say, Jason, I invested in this company. I became a billionaire where I've made $100 million. dollars. You want to come on my yacht and let's go, let's go to Santorina. I'm like, yeah, I want to go on your yacht to Santeria. Let's go hang out and do more deals.
Starting point is 00:52:42 Let's win more. I'm sorry to sound like, who's that guy on DJ Khalid? I'm sorry. I'm sorry. I'm telling you. Yeah, I got, so a question for, how about this, Jason? So maybe this could literally get practical for the people listening. So let's say there's somebody listening who has never done this before.
Starting point is 00:53:00 Their mind's a little bit blown. They, you know, they're like, man, this sounds. sounds great. I don't know if it sounds real because right now I am a guy who currently makes a really good living, not not not filthy rich. This is an average listener, not filthy rich, but definitely very comfortable, makes a great salary at a big company. They're, you know, moving up the ladder, so to speak. But they have some disposable income and they just kind of invest typically like most people do. And they're saying, well, what if I took out 100K or something or or 5,000 or 10,000 and started taking some adjacent advice.
Starting point is 00:53:36 What's the first few things? I know we're almost out of time, but what are the first few things you would tell that person that has never done this before that's going to take a certain percentage of their net worth out of whatever markets they're currently in? And they're going to, they want to angel invest. What do you tell them? Okay. First thing is buy the book, read it twice, get a pen, highlight and circle things.
Starting point is 00:53:59 In the book, I explain. the best first step for people who have a small chip stack. And what it is is to join a new category of investing that is called syndicates. Syndicates. What syndicates are are angel investors who are investing in a company like myself or Kevin Rose had one, Tim Ferriss had one, a number of high profile people have had them. They decide, I'm going to invest $25,000 in this company. company says great
Starting point is 00:54:32 the investor says you know what if you give me an allocation of a hundred to two hundred thousand dollars I'll offer it to my email list of other investors we'll each put a thousand they'll each put a thousand to five thousand dollars in and we'll create a little LLC
Starting point is 00:54:49 a little legal device a limited liability corporation and we'll create this LLC it's called an SPV special purpose vehicle and that little legal group will invest, let's say, $3,000 each on average, and there'll be 50 of us who do it, and we'll put that $150,000 in. If that, and the angel investor who round up that syndicate, they get 20% of the gain on that 150 if there's a gain.
Starting point is 00:55:16 So if the $150 turns into $10 million, they would get 20% of the return. That's their VIG in a way, to use a gambling term. That's their take. what you as the syndicate member, let's call you a micro angel investor in this case, what the micro angel investor in the syndicate get to do is invest a very small amount of money in a company that a notable or known investor has vetted to some level and also is putting 10 times as much of money in. You get dragged along. And there are sites like seed invest, angelist, funders club that all republics, republics, that all specialize in this. And then something very unique has happened.
Starting point is 00:55:59 People who are non-accredited investors, so there are two classes of investors in America. You can look this up or read about it in the book. Accredited, non-accredited. Accredited are rich people, essentially top 5% of the country or so. They have a net worth of a couple of million dollars. They make a couple hundred thousand dollars a year. Everybody else would all call civilians, non-accredited investors,
Starting point is 00:56:19 my mom and dad, my brothers, cousins, whatever, or some number of them. They can now invest as little as 50, or $500 in a company. When you invest like that, you can then pretend you're actually an angel who put it instead of $500,000 or instead of $5,000,000, and just try to support the company as best you can and give that company support by telling people about it, emailing introductions from potential customers, the CEO, and act like an angel investor, even though you've only put a small amount of money to work. And that micro angel investing is a couple of chapters in the book and how to do that. And in fact, even people with big chip stacks, I suggest for their first 10 investments, they do syndicates. They just invest alongside somebody who is a professional. Just like people jumping out of airplanes do tandem jumps before they do solo jumps.
Starting point is 00:57:10 I suggest when you jump into this, you do tandem jumps. You strap yourself to me or Kevin Rose or any of the angelist syndicates or funders club syndicate or seed invest syndicates. You're now strapped to another individual. And so if you crash, you know you're at least taking the more experienced person with you. You know, like that's why I like to get in airplanes when I get into like a small plane and it's like a 25-year-old. I'm kind of like, I don't really want to get in this tiny plane with a 25-year-old. I'd like the big plane with a lot of people in it and the two salty-haired, gray-haired, 50-year-olds. I know it's ages, but if you're 50 years old and you've been flying these planes, there's two of you and there's 300 people on the plane,
Starting point is 00:57:51 I don't think it's going down. I think you're taking as much precaution as possible. 25-year-olds who have just had their frontal cortex, you know, mature. I'm not interested in being a plane with somebody who has even had their brain mature. So this, yeah, I got you. I was in the British Virgin Islands at one point, and my wife had booked tickets. And she knows I don't like small planes. We literally walked up.
Starting point is 00:58:12 The plight was 22 because I asked them how old you was. Like, hey, how old are you? It's like, I'm like 22. It was 22, 23. I was like, how long are you flying for? It's like, oh, yeah, it's my third year or whatever. Second year. He's been doing it for a while.
Starting point is 00:58:21 And I was like, oh, that's great. I walked back to my wife. I told them, take my bags off there. I ripped up the tickets. We went on the next flight to the airplane. There's no way I'm getting on a fucking plane with a 23-year-old solo pilot in a plane that fits six people, like one of these puddle jumpers. Immediately went on the 50-person plane or 100-person, two propeller, two pilot, more redundant. So you're selective about what you're going to gamble with.
Starting point is 00:58:45 You're not gambling with your life on a young pilot. It's obvious. I have. Ryan. If you had my life, would you gamble with it? I mean, I have a pretty fucking great life right now. Like, literally, my life sucked for 30 years. I had to struggle.
Starting point is 00:59:00 I was broke. I was on the subway. I was like literally a waiter, a bar back carrying buckets of ice. Like, it sucked. I was like thousands of dollars in credit card debt. It sucked for the majority of my life. Now that it's good, I am not riding motorcycles. I'm not jumping out of planes.
Starting point is 00:59:16 And I'm not getting on small planes that kill rich people. No fucking way. I want to be safe. I want to, like, raise these daughters. I'm removing life risk. Like, and I'm adding financial risk and gambling and, you know. I see you trash talking. Yeah, trash talking Daniel Naganoo and Phil Helmuth on high-stakes poker games.
Starting point is 00:59:39 It's awesome. It's awesome. Well, you know, my superpower is talking. And so Daniel Negrano's superpower is also talking. I saw that one that you got them. You got them to pay up. up well it's interesting i knew daniel is a better poker player on his worst day than i'll ever be on my best um but i had studied every hand he plays i literally had one of my video editors cut every
Starting point is 01:00:02 hand of poker daniel negron who had played on television i mean talk about hundreds of hands and i watched them like three or four times and i realized god he always plays these like weird suited connectors or suited gap connectors it was eight six i believe right eight six of diamonds yeah knew he probably had something like that in his hand. And I was like, I also know that he loves to talk and people are quiet and then he gets to read. So I was like, if I just keep talking and keep saying everything, it's going to flood over. It's going to flood his circuits and it's going to discombobulate him. And it's exactly what happened.
Starting point is 01:00:37 He's like, I don't know what to do. You won't shut up. And I'm like, now I say nothing. Then I stopped talking after I just pounded him with every possible piece of information. is literally one of the highlights of my life is that $130,000 poker hand with Daniel Negrano. And I just, he's, he's, him and Phil Helmut are my two favorite poker players. I think Daniel is just, he is so, so good at reading people and he likes to have good time at the table. And then Phil, you know, is a slightly different player.
Starting point is 01:01:09 He's able to read people, but he's just so good at laying down big hands. I think Daniel has the call. Yeah, he has the call. And you got him to call in that one big hand. I got him to call for a Prius. It wasn't just a call. It was a call for a Prius. Yeah.
Starting point is 01:01:26 It was a lot of fun. Yeah. This has been great, Ryan. Well, hey, yeah, man, Jason, thank you so much. Again, I would encourage people. We talked about the book, but it's called Angel. I wrote it myself. Yes, it's obvious, obvious.
Starting point is 01:01:38 And I appreciate your team for sending me an early copy. It's really good. And Jason, I would, I'm really interested in this. this. I'm going to study it a lot more and want to understand the syndicates better to better build up my bankroll and talk with you more about it. So I'd love for us to continue this dialogue as we both progress, man. Yeah, it was great being on the program. I appreciate it. Awesome. Well, thanks so much, Jason. Talk to you soon. All right. Bye. Cheers. This episode of The Learning Leader Show is over, but we have plenty more to keep you locked in until next time.
Starting point is 01:02:11 Head over to LearningLeadershow.com for more information and to request your favorite entrepreneur, CEO, world-class athlete, or anyone else that inspires you. You can also talk to Ryan directly by reaching out to him on Twitter at Ryan Hawk 12. Thanks again, and we'll see you next time on The Learning Leader Show. This episode is brought to you by my friends at Callaway Golf. Calloway's business and marketing approach has turned heads over the last several years, helping the company make a dramatic turnaround from losing millions of dollars per year to being a leader in the industry. Products like the GB epic driver. Steelhead XR irons and Calloway's Chrome soft golf ball are aimed at avid golfers
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