619: Mike Maples Jr. - Practicing Reckless Optimism, Betting On Founders, Bill Gates Hiring Mike Sr at Microsoft, Being Overprepared, & What It Means To Do YOUR Best

Go to www. LearningLeader.com https://www. LearningLeader.com for full show notes. The Learning Leader Show With Ryan Hawk This is brought to you by Insight Global http://www.insightglobal.com/learningleader. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My Guest: Mike Maples Jr is a co-founding Partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade and was recently profiled by Harvard Business School for his lifetime contributions to entrepreneurship. Some of his early investments include: Twitter, DemandForce, Twitch, and Applied Intuition. Mike is also the bestselling author of Pattern Breakers: Why Some Start-Ups Change the Future. Notes Chance favors the prepared mind. We are all visited by luck, but most of us don't answer the door. We need to become a professional noticer. That is Mike's favorite verb. Noticing. Most people don't have prepared minds. Be intentional about noticing the world around you and being prepared for when luck visits you. Mike's dad died 7 days before we recorded. "He was a mentor, a friend, and one of the greatest inspirations of my life." His advice: Do your best. There's only one of you. Decide what to do with your gift of time, be intentional. Have gratitude for your time. Make the most of it. Don't waste it trying to be someone else. Focus - Fishing competition when Mike was 5 or 6. Let's find a good spot and stay there the entire time. While everyone else moved constantly, Mike and his dad stayed in their spot, caught a big carp, and won. Bill Gates begged Mike's dad to "be the adult in the room" at Microsoft. Mike Sr would say to the people he led at Microsoft, "I want to know that you're thinking about what you're doing." He used a Socratic method. He was not prescriptive. Be proactive. Have an intentional strategy. Be intentional. Jonathan Livingston Seagull - The biggest limits in the world are the limits of your mind, your imagination, and your actions– not the limits of the world itself. Have to get over that voice in your head that says, "You're not good enough." We get told to be realistic or stay within the lines. Everybody is figuring it out as they go. Everyone is "winging it." Only by being radically different can you make a radical difference. Great founders are like Patrick Mahomes and Steph Curry. You don't know how they're going to score, but you know they will. Practice Reckless Optimism – The world is built by Optimists. You need to be FOR something. Bet ON something, not against it. Mike sees himself as a co-conspirator more than an investor. There can't be a recipe for a breakthrough because by definition breakthroughs haven't happened yet. "Chance favors the prepared mind." We are all visited by luck but most don't answer the door. Chris Rock - Forming unexpected connections. Sam Beskind (Stanford basketball player where he played for Rob Ehsan) - Time management strategy. Stanford coaches had a one-pager with 3 keys to winning. Not 20. 3. If you have 20 keys, you have none. Nobody can remember all that. Life/Career Advice: Internalize what it means to do your best. Gratitude for your time. Avoid the trap of mimetic desire. The "T" of knowledge. Charlie Munger. Try to know what the best ideas that have ever existed in a wide range of fields. Then choose one field to know about more than anyone else in the world. Have one area where you are fanatically obsessed. For Mike, that's startups.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Everyone in this world has an opportunity to be the very best at a certain thing that's matchable to who they are as a unique individual. What I've learned is that a lot of people try to say, compete by being the best. Not the same thing. What is the intersection of what you're passionate about, what you're good at, what you could get paid for? And if you do that well, you're impossible to compete with. You won't be the best, you'll be the only.

• 0:30Ryan Hawk?

  This episode is brought to you by my friends at Insight Global. Insight Global is a staffing and professional services company dedicated to providing amazing people to their clients and taking great care of them. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global can get you the people you need and help you develop them to reach their full potential. Developing your people can be tough, but having productive employees can be magic. Visit insightglobal.com/learningleader.

• 1:11Ryan Hawk?

  That's insightglobal.com/learningleader to learn more. Welcome to the Learning Leader Show. I am your host, Ryan Hawke. Thank you so much for being here. Text HAWK to 66866 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email from me each Monday morning to help you start your week off right. You'll also receive details about how our book, The Score That Matters, will help you become a more effective leader. Text HAWK to 66866 now.

• 1:55Ryan Hawk?

  On to tonight's featured leader. I loved this conversation with Mike Maples Jr. He's a co-founding partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade and was recently profiled by Harvard Business School for his lifetime contributions to entrepreneurship. Some of his early investments include Twitter, demand force, Twitch, and applied intuition, among others. Mike is also the bestselling author of Pattern Breakers, Why Some Startups Changed the Future. During our conversation, we discussed the many lessons that Mike learned

• 2:35Ryan Hawk?

  from his dad, who just passed away seven days ago. I especially enjoyed when Mike shared the deeper meaning behind the phrase, "Do your best." Then we discussed how to manage that voice in our mind that says we aren't good enough, or aren't capable of achieving that massive goal. Then Mike shares why he invested in Twitter, and also why he missed and didn't invest in Airbnb. And then later in the conversation, I loved

• 3:13Ryan Hawk?

  his favorite verb, noticing, and how we all can become better noticers of the world, and why that will help us as leaders. Ladies and gentlemen, you're in for a treat. Please enjoy my conversation with Mike Maples Jr.

• 3:35Ryan Hawk?

  So, to start, I know this is very fresh and new, and your dad passed away a week ago, but I loved, loved reading the kind words you had to say about him, as well as others that poured in online. And you started by saying he was a mentor, a friend, and one of the greatest inspirations of my life. I would just love, Mike, to hear more about the impact, and maybe even a story or two about your dad and how he influenced you so much.

• 4:07Speaker 00

  Oh, man, there are so many, and it's a little bit, it's a little bit fresh right now, right? Because he passed away a week ago, almost exactly. There were a few things about him that were really remarkable.

• 4:23Speaker 00

  This is the meta lesson I learned and then I could, I could tell kind of a fun story or two, but he used to say, do your best and most people, when they say that they mean it in a platitude sort of way, but he meant it in a very deep way. So what he understood was that there's only one you and you don't know how much time you're going to have in this life. You might have a short life, you might have a long life, but you've got to decide what you want to do with the gift of your time. And the best way to honor the gift of your time is to be the best version of you that you can be. You know, so there are a lot of people that I admire in business. I admire Elon Musk. I admire, you know, Mike

• 5:05Speaker 00

  Maritz at Sequoia Capital. There's a lot of people that are really smart, talented people, but I shouldn't try to be like them because they, they, they already have a monopoly on being who they are. And so I can't do better than my best. That's all I can do. But, but the thing that's inspiring about it to me is that everybody has a unique strand of DNA. No two people who've ever existed in the history of humanity are exactly alike. And so what that means is that everyone in this world has a comparative advantage. That everyone in this world has an opportunity to be the very best at a certain thing that's matchable

• 5:49Speaker 00

  to who they are as a unique individual. And so like what I've, what I've learned is that a lot of people try to say, compete by being the best. Not the same thing, right? It's, it's, it's kind of understanding, you know, what is the intersection of what you're passionate about, what you're good at, what you can get paid for. And, and if you, if you do that well, you're impossible to compete with. You won't be the best. You'll be the only. And so that was the main lesson I learned from him. But, but it wasn't just about doing your best from an achievement point of view. Doing your best is about gratitude. It's about expressing the gratitude for the time that you're given. It's about honoring the gift of your time.

• 6:36Speaker 00

  Yeah, so, so that was a, there's a lot of things I learned from him, but that's the higher order bit. Um, that, you know, the other thing that I learned from him was that just the power of focus. So like one time I was like five years old and I'm in this fishing competition in Oklahoma, in Oklahoma City. And I was just above the age that you're allowed to even be in this thing. And there were all these other competitors, you could be up to 16 years old. So I'm sitting there and it's this hot lake in the summer of Oklahoma. And my dad says to me, and I think that you'd be smart to pick one spot and stay there the

• 7:18Speaker 00

  whole time. So how do you think we should pick a spot? Do you think we should pick a deep part of the lake or shallow part of the lake? Do you think we should pick a part of the lake that's shaded or that's, you know, exposed to the sun? Do you think we should, you know, he starts asking me all these questions like Socratic method. And he, and so we go to this part of the lake and cast the line. And he goes, you know, the, you may not win. There's a lot of people in this contest. And, you know, there are all these 16 year old kids running around in their overalls, you know, different parts of the lake. But we stayed in one spot the whole time. And I end up catching this carp and I end up winning this competition. And I'm like five or six years old. I can barely

• 8:03Speaker 00

  hold the trophy. It's almost as big as I am. And, you know, it was such a great lesson in the power of focus and sort of playing your game. You know, everybody else was, everybody else would like cast their line and they don't catch a fish in 15 minutes, they're off to the next spot. And everybody's running around all across the lake, scurrying about, hardly even keeping their, their bait in the water, most of the time. And my dad was just like, hey, you know, usually you win by just being prepared and focused and disciplined. And so that was a, just a classic example of how he would teach you things. And he wasn't, he wasn't saying, here's the lesson I'm trying to impart. It was just

• 8:45Speaker 00

  more like just the way he would interact with you. He would just ask you questions and try to get you to think about what you were doing. So he was really good about that. And, and I think this is part of why he was so successful at Microsoft. So, you know, my dad ended up, Bill Gates invited him to join Microsoft and run products for-

• 9:04Ryan Hawk?

  Hang on one second. I heard that Bill Gates begged, begged your dad to be the adult in the room at Microsoft. Did I read that right?

• 9:12Speaker 00

  I don't know. Gates isn't necessarily the begging type, but he's-

• 9:16Ryan Hawk?

  That's what I read. I don't know.

• 9:17Speaker 00

  He's very persuasive. But, but, um, you know, like my dad gets to Microsoft and you've got all these really smart young people who've been to MIT and Stanford and the top schools and they knew tons. And it was a culture where, you know, you want to be the smartest person. And, and my dad was sort of like, hey, look, all I care about is that I know that you're thinking about what you're doing. And so if you're going to ship Microsoft Word, I want you to describe for me a process for how that happens. And it could be your process. You can make it up. I don't care if you write it on a slide or a piece of paper and crayon, but I just want to know that you have a thought process here, that you're not just coding

• 10:00Speaker 00

  like a banshee for a hundred hours a week and we'll see where it goes someday. And so he was very good at sort of not being prescriptive, but he would be very Socratic. And in the, in the conversation, he would force you to reckon with the fact that you hadn't really thought about what you were doing yet. You were just kind of just jumping into the fray and just trying to overpower the problem by outsmarting the problem. And so my dad used to say to me, sometimes it's more important to be proactive than smart. And then, you know, if you have an intentional strategy about how you're going to go about something, you'd be surprised how few people really do. You'd be surprised how few people, most people, life

• 10:42Speaker 00

  just comes at them every day. And, and, you know, he was always like, you should, you should be very intentional about how you choose to spend your time and your energy and what you want to focus on.

• 10:55Ryan Hawk?

  Sounds like an amazing man. So cool.

• 10:57Speaker 00

  You know, he impacted a bunch of people and it was just, you know, it's sad to see him go, but it was fun to see all these people emerge, you know, from 30 years ago or more who'd said, oh, man, you know, I really missed him.

• 11:09Ryan Hawk?

  A celebration, a pure celebration. I appreciate that. So I want to pivot to something I read that you had written in Pattern Breakers, and I'm going to actually go to the back of the book or close to the back of the book. What did you learn? I think, I believe you were in second grade. What did you learn from Jonathan Livingston Segal when you were in second grade?

• 11:30Speaker 00

  Oh, yeah. It's a great book, right? By this guy named Richard Bach. And so it was popular in the early 70s. You know, that book, and there was another few that I really liked at the time, Be Here Now by Ram Dass and Zen in the Art of Motorcycle Maintenance by Robert Persig. And, and so, okay, but Jonathan Livingston Segal is a seagull and he's in a flock. And he says, I want to fly faster than any seagulls ever flown before. I don't want to just eat scraps off of the surface of the ocean and be a dirty, yucky looking bird. I want to achieve perfect flight. And all the other seagulls are like, dude, you're crazy. We're seagulls, right? This is how we're meant to live. You know, just quit having

• 12:12Speaker 00

  these goofy fantasies about what you could be. And eventually they get so tired of them that they cast them away from the flock. So, you know, I saw this book on my dad's table, and it was a small book. And I asked him what it's about. And he said, well, you know, it's classic. My dad is like, well, why don't you read it and tell me what you think it's about. And so I read it and I said to him, and I doubt I had the words, but, but, but this is kind of what I got from it was that. So, so by the way, Jonathan Livingston Segal does achieve perfect flight. But, but like the, the, to me, the theme of the book was that the limits that you experience in this world are not really limits of the world itself. They're really limits of your own mind and, and your own self-imposed limitations.

• 12:58Speaker 00

  And so if you want to break limits, you have to break the chains of the limits that you've created for yourself in your own mind. It's not about necessarily the world stopping you. The world is actually a surprisingly malleable place, but most people are limited in their capacity to affect change because of their limited beliefs about their ability to do so.

• 13:25Ryan Hawk?

  Why do we put these self-limiting beliefs on ourselves?

• 13:32Speaker 00

  Yeah, I think without realizing it, we're our own biggest critic. You know, if you think about just the mind chatter that goes on, and I'm guilty of this as much as the next guy, maybe you've found a way, Ryan, to solve for this, but like, probably within a minute of time, there's some background noise in your mind saying, you're not good enough. This isn't going to work. What if you say the wrong thing here? What if you do this wrong? It's there all the time. And what I've kind of learned is that I've never found a strategy to make it go away. You know, you could meditate, you could do a bunch of things. So what I do now is I just say, oh, well, that's my mind being rude to me and saying those things, but I don't have to listen to that. I don't have to buy into

• 14:17Speaker 00

  what that voice is saying. I can choose what to do in this moment. And I can just kind of like, you know, almost look at that voice like it's a comedy and not a tragedy. And just say, oh, there you go again, saying your negative stuff. Well, who says you get a say? And so like, that's, I think, a reason that a lot of us, a lot of us are self-critical all the time as a background part of our operating system in our mind. And we start to buy into those beliefs of the self-doubt. But then I think also, we get told, You know, as we grow up, you know, when you're a little kid, you know, you, you, you turn a box into

• 15:01Speaker 00

  a fantasy rocket ship and pretend that you're an astronaut and you imagine that you could do all kinds of things. But then as you grow up, you get told that you need to stay within the lines and this is the rules and you, you get good grades when you give the teacher answers the questions they want to hear. You get rewarded for achieving in the existing status dominance hierarchy, according to the rules that govern that status. And so I think you just start to become much more tuned into the opinions of the other than your own independent ideas about what's possible. And so I think that that's another thing that gets beaten out of us over time, unfortunately.

• 15:43Ryan Hawk?

  You know, Mike, I have a thought on this that has been helpful to, I think, get rid of that voice in my head. And I wonder if you've experienced the same thing. So I'll, I'll surface a thesis and then you can respond. After 618 of these conversations over the past decade, I've been so fortunate to meet some of the greatest leaders in the world, people who have accomplished massive, massive things. And I'm often asked, what do they have in common? What do they share? And that's some stuff that we're going to talk about with pattern breakers and things that you've learned as well. And there's a lot, but one of them that comes up so frequently is we

• 16:24Ryan Hawk?

  are all figuring it out as we go. Every once in a while, I'll meet the genius who does have it more figured out than most every once in a while. But almost across the board, once you really get to know the people and you get inside a little bit more and you, and you dig deeper and maybe you have multiple conversations and you get, you have dinner or something like that.

• 16:49Ryan Hawk?

  We're almost all figuring it out as we go. And to me, that is massively inspiring. That is like, there are no limits to what I can do. Why not have like, one of the crazy things I'm thinking about now was like, creating the biggest, best leadership development festival of all time. That is a stupid, crazy idea. Who am I to think I could do that? But then I think, why not? Why not? Somebody's got to do it. You know what I'm saying? So why not me? And that's because of talking to so many people who have done massive things that figured it out as they went. And I'm curious, and from your life, I mean, you're backing people who have crazy ideas,

• 17:32Ryan Hawk?

  and some of them hit. So some of them probably are like actual geniuses. But I bet, I don't know, you tell me, a lot of them just kind of have been really good at figuring it out as they go.

• 17:43Speaker 00

  Yeah, and it's funny, the expression I use colloquially is, everybody's winging it.

• 17:50Speaker 00

  You know, like even most successful people, like I remember when Trump first ran for president the first time. I'm like, you know, we're, I was talking to somebody about him and, you know, I'm not all that political, but I'm just like, he's winging it. And, and he, and they're like, well, do you think that means he's gonna lose? And I'm like, not necessarily. That may be why he wins. But like, you know, everybody's winging it. And they, and they're like, not everybody's winging it. I was like, no, everybody's winging it. Everybody. And the sooner you figure that out, the better. And he ends up winning. This friend of mine goes, oh, my gosh, Trump was winging it and he won. And I was like, I told you.

• 18:32Speaker 00

  But, but everybody's winging it. And that doesn't mean you don't have a plan. That doesn't mean you're not prepared.

• 18:38Ryan Hawk?

  Yeah.

• 18:38Speaker 00

  But sometimes you have to believe even when you don't believe. And, and it's like, you just have to, you have to have faith that you'll get through it. And just because you don't know how the dots are going to forward connect, doesn't mean they won't connect. You live close to the Wright brothers, right? Who, who, you know, all the scientists in the world were saying it was going to take a thousand to a million years for flight and it was a waste of time to even try to do it. The science couldn't let it happen. Well, the Wright brothers realized that they don't get to decide who invents flight. The person that does the job gets to decide who invents flight. And so it's the person who gets on the playing field and plunges ahead through the uncertainty that gets to define what the future is going to be.

• 19:23Speaker 00

  And they get to define the, the patterns that we're going to all have to react to. But it's, it's not like they're all that different, other than just the fact that they're willing to stand up and try to make a difference. They're like that seagull, right? Who's willing to pursue perfect flight without knowing exactly how he's going to get there.

• 19:42Ryan Hawk?

  Yeah, you're right. In pattern breakers, George Melville, who was the US at the time in 1901, was the United States Navy's chief engineer. He called aviation, quote, "a useless dream." And the Wright brothers were flying an aircraft two years later. I am juiced by people that think that crazy, that, that are like, no, we're going to go do this. And that's kind of like, like what your life's about, right? You're backing people, you're putting your money behind people who have crazy beliefs and thoughts like that. I'm just curious, what made you want to get into that line of work to back people who are crazy enough to invent something or to try to create something that others say,

• 20:28Ryan Hawk?

  what are you talking about? That doesn't make any sense or that will never work. And they say, oh, I think it will. And then away they go.

• 20:35Speaker 00

  Yeah, it's funny. I like to say to people that I have a, a specific set of skills. So like, most business people are probably more along the sensibilities of somebody like Warren Buffett, right? So Warren Buffett would say, what's a good company? A good company has a competitive moat, you know, has a, a brand, it has persistent advantages and it compounds over decades. A startup doesn't have any of those things. Startup doesn't have a moat, doesn't have customers. All it is, is the founders and their idea. And so what I realized is that startup capitalism is different. So a startup capitalist doesn't create value by persistently compounding. A startup capitalist creates value by changing the subject.

• 21:21Speaker 00

  You know, they, they create something radically different that's never been seen before. And that's how they add value to the economy. And so when it comes to startups, I like to say better doesn't matter. Only by being radically different can you make a radical difference. And so I, I just got really excited and inspired by people who do that, by people who are daring enough to create these legendary, radically different ideas, most of which won't work. But it's like, you know, we would all be still living in caves if somebody wasn't always willing throughout human history to imagine that there is a better explanation for how the world could be. And so those people inspire me, right?

• 22:06Speaker 00

  I think you can be a very successful go with the flow type of person. But the people that I get excited about show up in the world differently. They're not people who want to go with the flow. They're people that want to be like Jonathan Livingston Segal or Jack Dorsey or, you know, I wish I'd been smart enough to invest in Brian Chesky when I met him at Airbnb. But those are the kinds of people that get me excited.

• 22:28Ryan Hawk?

  Well, let's compare and contrast that. So you were on the Forbes Midas list, I believe, eight of the past 10 years. And that's the list of the essentially the best investors in the world. Is that what, is that accurate?

• 22:40Speaker 00

  Well, people have had some good wins in venture capital.

• 22:43Ryan Hawk?

  Yeah. So, so best investors in the world, you're on that list, eight of the past 10 years. So undisputed and you, you talk around this industry and Mike Maples Jr., like everyone's like, that's the dude, that's the, that's the guy. So let's compare and contrast Twitter, which I believe was called Odeo when you invested versus Airbnb and Brian Chesky, which it sounds like is one that you passed on. Can you take us inside your mind, the meetings, the conversations for Twitter slash Odeo, as well as Brian Chesky and Airbnb?

• 23:17Speaker 00

  Sure. And, and they'll probably, it'll be useful also in illustrating, you know, like in. When people describe startups, sometimes it sounds like a case study that's tidy somehow. And startups are wild. They're like capitalist mutations. It's like spotting a new kind of bird in the Galapagos archipelago, right? And so, you know, Twitter started out as a podcasting company called Odeo. And I was very excited about podcasting and I met Evan Williams. He had started a company called Blogger before that got bought by Google. And so he'd already had a success. And he had a very elegant product. And I was like, okay, I want to do

• 23:58Speaker 00

  this. First ever angel seed investment I'd ever made. And so a week after, yeah, a week after my check clears, Apple decides to give podcasting away on iTunes. You know, this is before the iPhone, right? So like, there weren't any devices to play podcasts on other than iPods to speak of. So Apple has a monopoly on the playback device. And they're giving podcasting away on their iTunes service. You're like, okay, that's a real problem, right? Like, I'm not sure we have a business. And so Ev tries to figure out a business for the better part of a year. And he can't find one. And so eventually, he calls me

• 24:42Speaker 00

  and says, I've just decided I'm going to give all the investors their money back. And, you know, because some of the investors were disenchanted and, you know, why am, why do I still have my money in this thing? It's not going to work. It's not, not a good startup. And so, so I was like, look, you know, you don't owe me anything. You win some, you lose some. He goes, look, I'd just rather give everybody their money back and I'll just own all the intellectual property and all that. And so I said, okay, that's cool. Do you have any other ideas? And he says, well, working on this thing, it's a side project right now. We're either going to call it voicemail 2.0 or TW TTR. And I, and I said, well, what, what, what does Twitter do? You know? And he says, well, you say what you're

• 25:23Speaker 00

  doing. And I'm like, okay, then what happens? He goes, that's it. Oh, I forgot. 140 characters or less. Because we want to be able to do it with SMS messages. And I was like, okay.

• 25:37Speaker 00

  What's the revenue model for something like that? And he goes, there is no revenue model. And I was like, well, what, what other features do you have in mind in the future? What's on the roadmap? He goes, there is no roadmap. And I said to him, Ev, you know, why do you think this is even a product, much less a business? And he said, oh, I have no idea if it's a business or not. But I figure that when I wrote blogger software, that a million people wrote blogs. And podcasting is a little hard, right? You got to upload audio, you got to have the right equipment, stuff. I figure that if you made it really easy for people to write a tiny little blog, like in the form of a tweet, that maybe 10 million people would do that.

• 26:20Speaker 00

  And if that happened, then the burden of proof would be on the people who are negative about the idea. And so, so I was like, okay, I want to invest in this, you know? And he says, well, there's nothing to invest in. There's no company, there's no product. And so then it blows up at South by Southwest. And all of a sudden it becomes kind of a, an early phenomenon. And I'm like, well, now I'm probably not going to get to invest in it. Everybody's going to be chasing it. One day Ev calls me and says, hey, did you mean it when you said you wanted to invest? Cause if that, if you meant it, now's the time. I've reserved an allocation for you if you're interested. So, you know, he was honorable to me twice, right? Giving me my money back and then letting me invest the next time.

• 27:02Speaker 00

  And, and you know, it was one of those things where there's so much drama, right? There was the fail whale, there was like, who's going to be the CEO? Is it going to be Ev? Is it going to be Jack? Is it going to be Dick? Is it going to, you know, who, what's going to happen? But it was just like, it was just a great idea. You know, some, some ideas are just, it's like you trapped lightning in a bottle. It doesn't matter how you execute. It just destined for greatness. So that was Twitter.

• 27:29Ryan Hawk?

  How much are you investing in the idea versus how much are you investing in the person or the people involved?

• 27:37Speaker 00

  I'd say it's more biased towards the people involved, but with a caveat like it turns out in my experience, they're not independent variables. So a great founder will be discerning enough to allocate their limited time to an idea that's worthy of their time. And so if, if a founder that you think is great is pursuing something not so great, that's a yellow flag that you overestimated the founder. But what's interesting is the very, very best founders that I work with, they have an authenticity to them where you're like, oh, man, if anybody in the world was going to do this idea, it would be this guy. They're just the perfect

• 28:22Speaker 00

  person to do it. You know, Ev was the perfect person to be a co-founder of Twitter because he'd done blogging software before. He, he just had a very natural set of instincts around self-expression. He was early in web 2.0. He was just from central casting to be part of something like that. You know, you can't fake authenticity. And most of the, most of the great startups come from very authentic founders. And their authenticity gives them a competitive advantage. It gives them a first mover advantage into the future because they, they have a better set of instincts about what needs to be built. And they're more likely to convince other people to follow them because their authenticity is contagious.

• 29:05Ryan Hawk?

  They just have such a core belief in the thing that they're doing that it just almost rubs off on you that they have this confidence and belief in something that doesn't, because like, looking back, it's easy. Well, obviously Twitter works, or obviously you should have invested in Uber or Airbnb or, you know, all of them. It's so easy looking back. At the time, though, none of these things that you invested in were, were quote, working. They, they were just an idea with a person or people. That's the thing that's so hard because then we're trying to look into the future. We're trying to make these strategic bets in the future. It's easy looking back, but so hard looking forward. So you're saying a guy like Ev, you just felt was the right person at the right time with the right

• 29:50Ryan Hawk?

  idea, with the right amount of conviction that the thing would work?

• 29:54Speaker 00

  Yeah. And, and you know, if some of your fans are like NFL football fans.

• 29:59Ryan Hawk?

  Yep.

• 29:59Speaker 00

  It reminds me of like, so unfortunately I rooted for the 49ers last year. I was at the Super Bowl rooting for the Niners and we're playing against the Kansas City Chiefs. And it's towards the end of the game and it's overtime. And it's like the Chiefs have the ball. And I'm sitting there thinking, oh crap, it's Mahomes. What's he gonna do to us this time? I don't know what play he's gonna run next, but I know that I just am like, my whole body is clenched up. Because oh God, it's that Mahomes guy again. And it's like, you know, the great founders are kind of like that, right? You just want to hand them the ball and wait to be amazed. And they just have this ability to just overcome whatever circumstances are in front of them.

• 30:43Speaker 00

  And part of how they do that is through their authenticity. You know, they're, they're just so obsessed with the idea that they're pursuing. That they come up with the right product ideas because they're genuinely interested in what they're working on. But then they also just have this determined view of what the future needs to be. And that determination is contagious, right? And it gets, I'm sure part of why Mahomes succeeds. Is the players on his offense are like, okay, this is our time. This is our moment. We got this. Mahomes is gonna take us there. Oh, we're in the red zone now. We score and we're in the red zone. And I'm sitting there thinking, oh crap, now they're in the red zone. And it's like, he's got to score. No. It's like watching a slow motion train wreck if you're on the other side.

• 31:28Speaker 00

  If you back founders who have that set of skills in their domain. You don't need to know how they're gonna succeed specifically, just that they will, or that they're likely to.

• 31:38Ryan Hawk?

  It's so cool to see the Mahomes type of MJ's back in the day, Kobe had it. Where their belief.

• 31:46Ryan Hawk?

  In themselves, their preparation, their work ethic, their history creates, it almost raises the level of the people around them because they want to be able to hang with him, be a teammate who adds value. And so those people are so, I remember Pat McAfee made this great point when the Tampa Bay Bucks signed Tom Brady. They said, what I don't think everybody understands is he's going to raise the level of performance of every single person in the entire building. The equipment guy will be better. The trainers will be better. The person making the food and the cafeteria will be better. The general manager will be better. He'll go get more players. The

• 32:29Ryan Hawk?

  coaches will raise their level to, the people like that, not only are they excellent at their craft, but they're also really good at raising the expectations and their performance, I think, of others around them. And that is leadership. Like that is being a leader is raising the level of performance and expectations of those around you. I feel like that's where you've probably got the experience in the startup world.

• 32:56Speaker 00

  Yeah. And it's, and it's really not fun to compete against people like that. Right? I remember a few years ago, so I like Steph Curry a lot, right? The Warriors. And so they're playing against Oklahoma City and there's this film of him going up, it's like the very end of the game, they're just barely down and you hear a fan in the audience who's filming it saying, not him, don't let him have the ball. Not him, not him, not him. And he goes across the half court line. He's like, not him, not him. And he just heaves this ball up from downtown and hits a three on the buzzer and he goes, no, not him, not him. Or, you know, that's what the French were saying, you know, in the Olympics.

• 33:40Ryan Hawk?

  Olympics.

• 33:41Speaker 00

  Why did they keep giving it to that devil? You know, he would just, every time, you know, he would just heave it from, you know, he, they'd be, it's not like it wasn't occurring to them to try to stop him, but it is just like, you know, you get into that zone where you, you just know you can't be stopped. And, um, you know, and that, you're right, it feeds, that energy feeds on everybody else on the team. You know, the team starts to develop a belief that they just can't be stopped. And that's really hard to compete against.

• 34:11Ryan Hawk?

  Yep. Let's flip it to the opposite side of things. I don't know this story. Brian Chesky. Looking back, obviously, Mike, you should have invested in Airbnb. What are you thinking? You're you're you're stupid. What do you mean? Oh, why not? Yeah. So what happened there?

• 34:26Speaker 00

  Well, so this was kind of a funny thing. So the prior week, we've been pitched by a company called Mojo Mix, which was you go to a website and you specify ingredients that you want in your cereal. And then it assembles those ingredients and chips it to you in a box. And my partner, Ann, and I are looking at this thing. And and at the end of the meeting, Ann's like, why did we take this meeting? This isn't something we invest in. We don't invest in cereal companies. We have no business even talking to these people. I mean, I wish them well, but it's not our business. And I was like, well, it's technology enabled cereal. She's like, come on. And so so a week later, I take this meeting with, at the time, it's called Airbed and Breakfast.

• 35:06Speaker 00

  And we walk into the conference room and it's full of cereal boxes, Obama O's and Captain McCain Crunch. And, you know, people don't remember this, but he financed the company in the early days by selling cereal boxes. Because he couldn't raise money. So we walk in there. And Ann kind of looks at me like, Maples, what the hell? Another cereal company. And I'm looking at her like, you know, they didn't say it was cereal. You know, like, so I'm like, hey, Brian, what's like, what's going on here with this cereal? He goes, Well, you know, we're funding the company by selling cereal. Would you like to buy a box at $30 for a box? And I made my first mistake. I declined. So so then then he says, Okay.

• 35:50Speaker 00

  We're, you know, Michael Seibel, who introduced us. Says that you don't really like slides, you like demos. So we're going to show you the software. I was like, great, that's right. So he tries to get the the software to run. And he can't get it to work. For some reason, the server's down. So I'm like, that's okay. Slides are okay. We'll just look at slides. He goes, well, I didn't bring any slides because I heard you like demos. So we're sitting there, 20 minutes into the meeting, room full of cereal boxes, and I still have no idea what they do. We're just looking at each other, right? This conference room. And so then he says, you know, air bed and breakfast, we let you rent an extra room in your house. And then you serve, you give

• 36:34Speaker 00

  the person an air mattress and you serve them Pop-Tarts the next morning. And so I'm like, okay, I like, I'm not sure I get this. Isn't there something already called couchsurfing.com? And it's free. Why are people going to pay for your thing that costs money when it's free with couchsurfing.com? And he goes, well, because, you know, it's not about price, it's about trust. And people are gonna want good pictures of the place that they're staying at, and they're gonna want a trust rating mechanism. And that's where I made the mistake. I didn't realize what his insight was. His insight was about the internet and trust mechanisms

• 37:15Speaker 00

  and Facebook Connect. We're gonna make it possible for you to create a substitute for the trust that people had in hotels. He was right. It wasn't about price. It was about trust. But the meeting was just so convoluted and screwed up that I just didn't, I just didn't see it, you know? And so I missed it. It was the biggest miss of my career by a wide margin. So I would have made, God, it hurts to say, I would have made over 5,000 times of my money if I had said yes to it. Yeah.

• 37:48Ryan Hawk?

  Yeah, I guess those are the ones you learned from. But did you feel something special in Brian Chesky, though? I mean, because now you look at him like this dude's amazing. Like every time he speaks, we're all taking notes, every podcast he goes on, whatever he's talking. I think he's almost universally admired by all who study this stuff of as being one of the best CEOs in the world. Could you sense that years ago in him?

• 38:10Speaker 00

  Yeah, I mean, I thought even then that he definitely had this X factor to him. And to kind of give you a sense of that, I ended up introducing him to Reid Hoffman, right? Who was the founder of LinkedIn. And I said, Reid, I don't, you know, I don't know if this is a fit for me, but this guy is interesting and he's somebody you should know. And I don't know if you're going to want to invest in airbed and breakfast or not, but I think this is somebody you need on your radar because he's, he's, he's going to do something. And, you know, I should have known, right? I just should have known better.

• 38:45Speaker 00

  But, you know, sometimes you just, you have so many meetings and you meet with so many companies and, you know, the, the meeting was so convoluted and screwed up and you did, I just wasn't awake enough to the possibilities. And I, you know, failure of imagination.

• 38:59Ryan Hawk?

  Yeah. No, it's part of the game though. That's part of the, the, the pain. And that's how we learn from that. Mike, I'm looking behind your left shoulder and I see a sign that says, practice reckless optimism. What does that mean to you?

• 39:15Speaker 00

  Yeah. Well, it was given to me by a founder, actually. So somebody that I worked with twice, a guy named Dominic Zane, gave it to me for Christmas one year. And, you know, kind of the, the idea is that you want to believe that a different future is always possible, always around the corner. And, you know, so I like to think of myself not as an investor, but as a co-conspirator. I think of a startup as an optimistic conspiracy theory to make a better future. And, you know, most people, we haven't really talked about this, but most startup ideas that are great are disliked by most people at first. Because if, you know, human beings are conditioned to like things. So if everybody likes your startup idea, it's too similar to what they already like.

• 39:59Ryan Hawk?

  Yep.

• 40:00Speaker 00

  The, the best startup idea is force a choice and not a comparison. You know, this is not a startup, but it's an example of the thinking, the Tesla Cybertruck. You know, you may want one, you may not want one, you might think it's ridiculous. I, when I first saw the Cybertruck, I thought maybe Elon was joking. Is he really going to ship that, you know? But like, nobody, when they see a Cybertruck ever says, how does that compare to a Ford F-150? Right? It's like, live in Elon's future or don't, but there's no comparison between the two. You can't reconcile the two things. And so that's what, what I find startups are that way when they're great. They start out by being non-consensus and right.

• 40:41Speaker 00

  So it's, it's, it's almost like you're the Ocean's Eleven team trying to rob the Bellagio safe. Right. You're, you're like, you're trying to perpetrate something. And most people don't believe that it should happen. And so you're, you kind of believe that you're in on a secret about the future with a bunch of other like-minded crazy people. And I call that co-conspirators, right? And so I want to be more of a co-conspirator than an investor because I think that startup founders need a different kind of help. They don't need a buy low, sell high type of helper. They need someone who's in on the secret with them and who believes in the same crazy thing that they believe. And, and wants to be part of the different future, wants to be a reckless optimist, you know, alongside them.

• 41:27Ryan Hawk?

  Optimists are the ones who change the world, right? Pessimists sound smart. Morgan Housel said that on this podcast, but optimists actually make a difference. They're the ones who make it happen. They change the world. James Clear talked about on this podcast too, about the fact that he wants to be around, I do too. People who are for things, people who bet on something. The only way to achieve or to experience the upside is you can't just hate on things or be a pessimist. You're not, that, then you're not part of anything. You're just a hater. But if you want to be a part of the upside, if you want to have a chance to make a difference, to leave a dent in the world, you have to be for things. You gotta bet on something. You gotta commit to something.

• 42:12Ryan Hawk?

  And that's why I've loved studying your, your work, Mike, because I feel like that's your life. That's like your ethos that kind of pours out of you, even as we're just talking now, that you're this guy who believes in crazy ideas, changing something in a radical way. And you're willing to put your money where your mouth is. And that's how you've built your entire career.

• 42:37Speaker 00

  Well, we try, right? And I guess it's kind of a version of doing your best, right? But like, you know, it's sort of like, all right, you don't know how much time you're going to have. How do you want to use your time? Do you want to use your time succeeding by somebody else's conventional idea of success? And conforming to their dogma about how things should be? And trying to win within that status dominance hierarchy? Or do you kind of say, you know, like, there's a book that I really like called The Beginning of Infinity by David Deutsch? And he's this theoretical physicist who talks about how we're at the beginning of infinity of knowing what's knowable. But the good news is that all knowable things can be known.

• 43:21Speaker 00

  And so why not try? Why not always, you know? What is a theory really? It's a better explanation for how things work than all the explanations we have so far. Why not always seek a better explanation? Why not always believe that if this is the pattern, that somebody can break the pattern and impose a new better one? And then a better one after that, and a better one after that. And so, you know, that's something I can get behind, right? Is people who do that. Whereas, you know, the status quo has the word status embedded in it. And a lot of people try to protect the status quo because they're trying to protect their existing status. And I'm like, what fun is that? You know, that's a, that's not, that's not a fun way to honor the gift of your time.

• 44:06Speaker 00

  That's just passing the time.

• 44:09Ryan Hawk?

  I spoke with your chief of staff, Sam Baskin, who, by the way, he played for my friend, Rob Ehsan, at Stanford, basketball player. And Rob texted me and said, "That dude might be my all time favorite player and he's going to be the president of the United States someday." So just, just a heads up on Sam.

• 44:28Speaker 00

  I'm not sure I would wish that on him, but you know.

• 44:33Ryan Hawk?

  I don't know if he wants that, but one of the things he said, he sent me a list of your favorite quotes. And I want you to, to respond to one of them. We could have a whole conversation about all of these, but one of them is, "There can't be a recipe for a breakthrough because by definition breakthroughs haven't happened yet." Again, this is in line with what we've been talking about, but this mindset of there aren't really recipes, you have to, in a way, invent. The new thing or created not follow somebody else's quote best practices. Can you talk more about breakthroughs and the fact that there isn't a definition because they haven't happened yet?

• 45:13Speaker 00

  Yeah, and when you think about it, it makes intuitive sense. So let's say that you and I follow a recipe to make a cake. Uh, we might make an awesome cake, but we're not going to invent something in so doing. We're, we're, we're following somebody else's playbook. That's already been determined. Somebody else figured out how to create that cake and passed it down to us. And so if we're going to have a breakthrough, we have to do something nobody's ever done before. So there can't be a recipe by definition. So what I've learned is that it's the wrong question to ask, right? Like the, the question to ask is how do I become the type of person who's likely to encounter a breakthrough, right?

• 45:57Speaker 00

  And so, you know, you, you listen to some of the great people in history, the creative geniuses, Louis Pasteur, right? Who said, chance favors the prepared mind. Isaac Newton, the apple hits his head. Archimedes jumps out of a hot tub and says, eureka, I found it. When displacement occurs to him. The, the, the history is written in terms of them having this flash of insight, almost like a happy thought. You know, Einstein talks about how relativity crystallized for him when he was in a train and he was moving away from a clock and he saw it going off in the distance. But, but they asked Isaac Newton one time at a party, how is it that when that apple

• 46:40Speaker 00

  hits you on the head, all of a sudden gravity occurred to you? And he said, because I was thinking about it all the time. And so that's the thing that people don't get about breakthroughs is that chance favors the prepared mind. Because when you're thinking about the edge of something new for its own sake, independently, because you're intrinsically motivated by it.

• 47:09Speaker 00

  You're you're gonna get visited by luck often. You know, but the problem is, most of us are just trying to get through the day. We're trying to follow the recipe for what needs to happen next. We all get visited by luck, just most of us don't answer the door. Most of us don't realize that we've been visited by the muse. The great founders, the great scientists, the great artists. You know, that people have studied people who create these breakthroughs. And and I'm convinced that chance does favor the prepared mind. But the reason it does is that prepared minds say yes to luck more often. Right? Like, prepared minds know luck when they see it.

• 47:54Speaker 00

  Most people don't have enough agency to realize they're always being visited by luck.

• 48:01Speaker 00

  But they're not, they're they're too focused on what's in front of them to notice what's around them. And so, like, one of my favorite verbs about entrepreneurship is noticing. And it's like, you know, it's like the people that notice the surprising anomaly hidden in plain sight that changed the future. But when you realize that, it's kind of inspiring, you know, inflections are all around us all the time. Opportunities change the future are all around us, ever-present. The Wright brothers didn't have any unfair advantage in inventing the plane. They were just more curious. And so, you know, I think that that's that's the key, right? Is to not look for a recipe or playbook.

• 48:45Speaker 00

  But to try to try to be the type of person that is going to be visited by luck more often and is going to be awake to the possibility of answering the door when, you know, I like to say that I think that luck has a little bit of a feminine quality. You know, the Greeks talked about being visited by the muse. I think that, you know, sometimes you're visited by the muse. But you have to be open to the possibility that she's going to knock. And she's usually not going to come through the front door. She's going to come through the side door. And so, you know, you kind of just got to be awake to the possibility that she's visiting today.

• 49:21Ryan Hawk?

  I love your favorite verb. When I think about the most interesting people that I've ever met and the most interesting people in my life, I think they are far and away the best noticer of things, have great spatial awareness of the world and understanding. They're usually very funny. Stand-up comedians, I've found, are probably to be some of the best noticers in the world. They're, they're, Nikki Glaser talked about that on this podcast. I feel like I'm name dropping the whole time, but that's just how my mind works is from these conversations because they're embedded in my mind. But she said that that's, that's like her whole life is she'll be in the middle of a conversation with a friend at a party or something and notice

• 50:04Ryan Hawk?

  something and say, hold on a second and take out her phone and put the note of the thing that she just noticed because the whole world at all times are, there's just, there's stuff happening that you're noticing. And I think if you almost rewire your brain to do that, that's how some of these breakthroughs can happen because you're always like chance favors the prepared mind, right? You're always on the lookout and noticing these things happening in the world.

• 50:32Speaker 00

  That, that's right. Most people don't have prepared minds. Unfortunately, most people let life come at them.

• 50:39Ryan Hawk?

  Proactive again, right? Be proactive again.

• 50:41Speaker 00

  Yeah, it's, and it's, it's interesting. I love the, the stand-up comedy example. We've never talked about this before, but like I read this book where they talk about Chris Rock and his technique and comedy, like all forms of creativity usually involves forming unexpected connections. So like what, you know, when you're doing a startup, you're, you're forming an unexpected connection between a new form of empowerment and a set of despirations that people have. But, and, and you're usually harnessing something that pre-existed. In addition, you're just connecting the dots differently. Comedy, from my understanding, is very similar. You're, you're connecting sort of the mundane, expected, everyday life

• 51:25Speaker 00

  and you're juxtaposing it with something unexpected. But the other thing that's similar to entrepreneurship, if Chris Rock is any guide, he'll practice his comedy lines on different audiences before he gets in front of a big audience. And startups are a lot like that, too. Like you're, you're not saying this product, it's either going to succeed or fail. I better raise some money and you're attached to whether it succeeds. You're sort of playing almost like a little kid would play soccer, just kind of kicking the ball forward without necessarily an idea where it's going to go. And you're, you're, you're not attached to being right, right away. You're willing to be just totally wrong. You're exploring a whole bunch of lateral possibilities because it's interesting. And if, and if you're wrong, so what? You know, it's a tiny little audience.

• 52:10Speaker 00

  The penalty cost isn't that high. You're not fixated on the cost of being wrong because you make the cost of being wrong zero. What you're focused on is finding a quicker path to being surprised about what's right. So then, then you can escalate your commitments as you increase your certainty that you're right. And that's true of comedy too, right? Like once, like Christopher Rock in this book I was reading was saying, like you can just tell when it lands, you know, you just, you could just see the way that their body language and their eye was on that one I'm going to use. And so I think risk taking is a lot like that. Like you want to, you want to make it so that you could take risks where the cost of failure is as near zero as possible so that you could take as many risks as you want.

• 52:55Speaker 00

  And then, and then double down only when it works, only when you're surprised to the upside. But it's kind of a different way of thinking about risk, right? It's, it's, it's about thinking about, I'm going to make the cost of failure so low that I'm just going to keep trying until I massively succeed.

• 53:12Ryan Hawk?

  That, that's the thing. It becomes a quantity and endurance thing. I was just reading about James Dyson, now Sir James Dyson, right? He got annoyed by the bag at his vacuum cleaner. And so he's like, I just got to get rid of this stupid bag. I need to create a bagless vacuum cleaner. Well, you know how many times it took him to get it right? Just over 5,100 tries that he messed up, but he learned after each one. And eventually he got there and became a billionaire. And I think he's the sole owner of that company. So it's like the combination of an idea, a willingness to experiment, a willingness to be okay when it doesn't go well, a willingness to be resilient and to respond and to learn

• 53:56Ryan Hawk?

  from that failure so that when you go back the next time, you are a little bit closer, you're a little bit closer. And most people are just not willing to endure all of that. They'll quit, they'll stop. That's the difference between a James Dyson and everybody else. And I think that though is a key learning for all of us as leaders is whatever the thing is that we're doing. A big part of it is just being willing to continue on, to push through and to make sure you learn from the small experiment before so that you're better the next time. And I have to guess though, that's got to be a commonality among the leaders that you have backed that have gone on to do really well.

• 54:35Speaker 00

  Yeah. And it's, but it's funny too. Like, you know, we're talking about noticing things and being awake to stuff. You know, earlier you mentioned my chief of staff, Sam Beskin, right? Who was on Stanford's basketball team and he, I think he played, you know, on other teams as well, graduate school. Not long ago, I was working with him to, to chart out my time management strategy for 2025. And I had a very comprehensive way of thinking about it. And he said, you know, when I was at Stanford, the, the basketball coach, they would, they would come up with a game plan and they would think about every play and all this intricate stuff. But then they would create a one-page, three keys to winning

• 55:20Speaker 00

  summary. And, and Sam said that the coach would say to us, if we do these three things, we will win this game today. And he's like, everybody on the team knew it. Everybody on the team knew the three things they had to do. The next team that he was on, the coaches would have this one page, but it would have like 20 things on it. And it would be like in tiny little, you know, footnote sized type. And he's like, the problem with that is there's no keys to winning then. If you have to win, if you have to remember 20 things, you remember zero things. And so I was like, dude, you're totally right. We need to redo

• 56:01Speaker 00

  this plan. We need to be thinking the three things because we've got a team at floodgate and like the associates need to know what they care about when they find the next Twitter, you know, the next Thunder lizard startup. And if I have some comprehensive, you know, spreadsheet of 20 different things classified.

• 56:23Speaker 00

  I might impress myself with how smartly arranged it is, but, but it's not executable. Right. It's not executable in the same way that that one page, three things to do game plan. It's, it's not enough to be smart about what should happen. What you want is the thing that everybody is willing to get behind and do. That's better than good enough, right? To win. And, and like, you know, Sam, like, I mean, you, you could have just said, okay, yeah, whatever. Let's do this spreadsheet, right? But like, you have to be, you, you have to be like, wait a second here. He's totally right. Right. He's, he's given me a helmet adjustment in a nice way, but like,

• 57:08Speaker 00

  he's just totally right that that's what we have to do. My problem is not that I need to be more precise. My problem is I need to, it needs to be addition by subtraction. Right. I, that's what I need to be focused on right now.

• 57:21Ryan Hawk?

  Yep. It's like the old saying that the word priority didn't used to be pluralized. And if that's even the right word, it didn't used to be a plural word. It used to be singular. What is your priority? And now it's become, these are our 12 priorities. And if you have 12 priorities, just like if you have 12 values, you, you pretty much don't have any. You don't have to list everything out that, that is important to you. I think you have to focus. I love that idea of the three keys to the game. I heard, I heard that's what the new New England Patriots coach, Mike Frable is very good at is three keys for the offense, three keys for the defense and three keys for the special teams. And everybody in the entire roster has to memorize those three keys before every game and they get quizzed on it. And so they understand it, just these three things, we're focusing on these three things.

• 58:06Ryan Hawk?

  If I play offense, defense or special teams, and I think simplifying that also, it's hard. It's part of partially why Twitter works. The forced constraints ended up being a great, great thing for it. And the same goes for time management for keys to winning a game or just in life in general. Mike, if you have time for one more question, and we're a little bit over, but I have one more.

• 58:28Speaker 00

  You bet.

• 58:29Ryan Hawk?

  Yeah. Let's say you're meeting with somebody who's a recent college grad like Sam's age, or maybe a little bit younger. And they come to you and they actually don't fully know what they want to do, but they do want to leave a positive dent in the world. What are some general pieces of life slash career advice you'd give to that person?

• 58:50Speaker 00

  There's two. The first is to internalize what it really means to do your best. And so, you know, doing your best means being the best version of you that you can possibly be as a, as a way of expressing gratitude for your time. And comparing yourself to the best version of yourself you can be, rather than comparing yourself to others. You know, avoiding the trap of memetic desire and, you know, this tendency to define your thinking according to other people's thinking. People would be so much better off if they understood that early in life. People waste so many of their best years trying to succeed according to somebody else's idea of what success is.

• 59:35Speaker 00

  So that'd be the, the first thing. The second thing, and I, it took me a little while to figure this out, but, but eventually I got there. I call it the tea of knowledge. So I have a broad variety of worldly wisdom topics. I learned this from a guy named Charlie Munger. And, you know, so I try to know, like, in, in the fields of art, physics, economics, game theory, system level thinking, engineering, politics. What are the very best ideas that have ever existed in those fields?

• 1:00:17Speaker 00

  Because that, that's kind of like getting worldly wisdom. And, and I just think that, you know, if you, if you read Aristotle, if you read Machiavelli, if you read Sartre, if you read all these different people, Graham Wallace, the art of thought, all these different people. It's like they're your friend and you got to know them, you got to spend time with them. And you got to like, learn ideas that have stood the test of time for centuries sometimes. You know, Marcus Aurelius, you know, all these people. But then the, the reason it's a tea is I think you want to have one area in life.

• 1:00:57Speaker 00

  Where you are fanatically obsessed with knowing more about it than anyone knows. So like for me, that's like startup greatness, right? Like I have a database of every company that I know of in history in tech that would have made more than 100x on the first check. And I try to get a time capsule of those companies. I try to get the seed round pitch deck. I try to understand what the founder was like at the time you would have had to decide. I try to figure out whether our frameworks would have caused us to say yes, or whether we need new frameworks, or whether we need to discard some. But like, you know, is that going to lead me to the next great startup? I don't know, probably not, certainly not in the next week.

• 1:01:42Speaker 00

  But I just feel like if you do that, you know, over the course of 10 years, 20 years, you just have a gigantic database of greatness in the back of your mind of what greatness looks like. And if nobody else is willing to do that, I just think you have an advantage, right? You come by the advantage honestly, but like the, you know, in England, you have these guys, they call them train spotters, right? They have these journals and they look at trains coming and going and everybody thinks that that they're socially maladjusted. Why would anybody be so interested in spotting trains?

• 1:02:17Speaker 00

  I think everybody should try to be a train spotter in something that matters to them, you know, like I'll, I'll talk about what makes a great startup. I'll talk your ear off and, and you know, everybody around me will be like, hey, Maples, we're supposed to be having a party here. We're watching a football game. You don't have to talk about these detailed details of a startup nobody's heard of. But I'm just that interested, like I care that much. And so like I, I encourage everybody to have the broad worldly wisdom, but then the tea of knowledge where they're a train spotter. And the, the advantage to that is that, you know, like I understood when Bitcoin came out, I understood why a lot of what's profound about it could be understood by understanding

• 1:03:02Speaker 00

  equations of heat and energy and conservation of energy. And I understood that like fiat currency does not have conservation of monetary energy and that Bitcoin does. And I knew that because of that, it was a superior feedback loop system than any other currency that existed. You wouldn't have, you wouldn't have connected those dots, right? If you hadn't spent time understanding, you know, the equations that govern thermodynamics. But you would have never known that when you were studying it. You just had to decide it was worth your time to engage with that topic because it was a way to honor the gift of your time and do your best.

• 1:03:42Ryan Hawk?

  Mike, I could talk to you all day, man. I really appreciate this. We definitely need to do a round two. The book that I highly, highly recommend is called Pattern Breakers. Why Some Startups Change the Future. The reason why I liked it, there's many reasons. One, the guy who should write this book, wrote this book. Mike Maples Jr., you're the guy to write this book. But also the combination of the fascinating stories. And I don't think this is just for people who are into the world of startups or investing. I think this is into people who care about humanity, who are leaders, who care about excellence, which is really the avatar of the Learning Leader Show.

• 1:04:24Ryan Hawk?

  All about understanding excellence and becoming a better leader and impacting people in a positive way. And I think that's what Pattern Breakers is all about. And then you poured, you could tell your heart and soul. And I know you wrote it and rewrote it multiple times. I talked to Sam about that, that you weren't okay to release just a good book. It needed to be excellent. And that's what you done, man. So, thank you for being here. Thank you for writing Pattern Breakers. And I would love to continue our dialogue as we both progress, man.

• 1:04:50Speaker 00

  Cool. Thanks, Ryan. I, you know, I really appreciate it. It was an honor to be on your show. Some of your guests are, I'm, I'm big fans, like Coach Stoops not long ago, huge fan. So, you know, it's an honor to be included with that group of people.

• 1:05:04Ryan Hawk?

  Oh, man. Thank you so much. I appreciate it, man.

• 1:05:06Speaker 00

  See you soon.

• 1:05:10Ryan Hawk?

  It is the end of the Podcast Club. Thank you for being a member of the End of the Podcast Club. If you are, send me a note, [email protected]. Let me know what you learned from this great conversation with Mike Maples Jr. A few takeaways from my notes. I loved how emotional Mike got when he talked about his dad. And if you want to see it, go to youtube.com/RyanHawk. You can see the emotion. Pouring out of him as he talked about his dad and his message of do your best. There is only one you and it comes from a place of gratitude. How will you decide to spend the gift that is your time? Don't waste it trying to be someone else.

• 1:05:54Ryan Hawk?

  Do your best. Internalize what it means to do your best. Avoid the trap of memetic desire and copying others and figure out how you can make a positive dent in the world. And then chance favors the prepared mind. We are all visited by luck, but most of us don't answer the door. We need to become a professional noticer. Again, Mike's favorite verb noticing. Most people don't have prepared minds. Be intentional about noticing the world around you and being prepared for when luck visits you. And I love the story about his chief of staff, Sam Beskin.

• 1:06:38Ryan Hawk?

  Sam played basketball at Stanford as well as other schools. And at Stanford, the coaching staff would hand them a sheet of paper that had three keys to winning the game, just three. And another school he played for, they would hand him a same sheet. However, that would have 20 keys to winning the game. Nobody remembered any of the 20. Everyone remembered all of the three. And this is a great metaphor for life. If you try to value everything, you end up valuing nothing. And if you have 12 priorities, you have none. You have to decide what are those few things that absolutely must go right in order for you to win and then focus on those. Once again, I want to say thank you so much for continuing to spread the message and telling

• 1:07:23Ryan Hawk?

  a friend or two, hey, you should listen to this episode of the Learning Leader Show with Mike Maples Jr. I think he'll help you become a more effective leader because you continue to do that and you also go to Spotify and Apple Podcasts and you subscribe to the show and you're rated hopefully five stars and you write a thought for you by doing all of that. You give me the opportunity to do what I love on a daily basis and for that I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.