The Tim Ferriss Show Transcripts: The Man Who Taught Me How to Invest — Mike Maples (#286)

Please enjoy this transcript of my interview with Mike Maples, Jr. (@m2jr), a partner at Floodgate venture capital firm, an investor who has been on the Forbes Midas List since 2010 and one of my favorite people and a personal mentor. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the interview here or by selecting any of the options below.

The Man Who Taught Me How to Invest


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Tim Ferriss: Hello, boys and girls. This is Tim Ferriss, and welcome to another episode of the Tim Ferriss Show and my brand new podcast, Tribe of Mentors, because this guest is suitable for both. Mike Maples, he’s one of my favorite people, one of my oldest mentors, not in biological age. But he goes back probably 15 or 20 years teaching me. And he is the man who, effectively, taught me how to invest. And the audio you’re going to hear was recorded in front of a sold out audience at the Castro Theater in San Francisco.

It was a blast. Thank you, everyone, for coming out. And it takes us a few minutes to warm up, and then, we get into not only investing but also his life philosophies, parenting. He is such a splendid human being and has a very, very wide set of skills. So, I hope you enjoy this conversation with Mike Maples. Thank you so much for coming, everybody. This is going to be great. And I’ll read some suggested introductory remarks first. Thank you all for coming tonight. Welcome to tonight’s program with Inform at the Commonwealth Club. And what I’m not going to do is sit here and regurgitate stuff that is already in the book that you just bought because that’s very boring.

So, what I thought I would do instead is invite one of my friends who is in this book to join me on stage and to dig into some of the old stories, the stuff you guys haven’t heard.

And to really just banter because he is one of my favorite people. So, who is this favorite person? Kevin Rose is one of my favorite people, but he has a brand new human being to take care of. So, he is not here to booze it up with Ferriss I’m very sad to say. Mike Maples, Jr. You can find him on Twitter at Mike Maples, Jr. is a partner at Flood Gate, a venture capital firm that specializes in micro cap investments and startups. He’s also the person responsible for introducing me to tech investing, in general. And we go way, way back. He has been on the Forbes Midas List since 2010 and named one of Fortune Magazine’s eight rising stars.

Before becoming a full time investor, this is very important, Mike was an operator. He was involved as a founder and operating executive at back to back start up IPO’s, including Tivoli Systems, which was acquired by IBM, Motive, IPO Motive acquired by Alcatel-Lucent.

Some of Mike’s investments include Twitter, Twitch.TV, ngmoco, Weebly, Chegg, Bizarre Voice, Spice Works, [inaudible], Demand Force, and many, many, many others. Please help me welcome to the stage Mike Maples.

Mike Maples: I thought we were just having a little chat at like a book store or something today. I guess you tend to draw a crowd. I keep forgetting that.

Tim Ferriss: So, I was trying to put us connecting on a timeline. And I think we’ve had a number of interactions beginning it had to be back pre-2000 maybe.

Mike Maples: And I think, when we first started catching up, it was right before you had done the Four Hour Work Week. So, Tim wasn’t sure what to call this book. And I – just anything goes?

Tim Ferriss: Anything goes. I may regret that, but yes.

Mike Maples: So, Tim – and I’m a little bit less over my skis sometimes than Tim is. Well, it depends on the area. But whatever. But so, Tim was deciding whether to call the book the Four Hour Work Week or Drug Dealing for Fun and Profit. And I was like, “Tim, why do you want to write a book about being a druggie? This is just a terrible idea. It’s just a terrible influence, just a bad idea.” And Tim was like, “Well, you know, you really want to get people provoked, point of departure to get access to the ideas.” And so, we did this thing. I think we called it ghetto testing where we said let’s not argue.

Let’s not your opinion versus mine. Let’s just test the two titles and just say, hey, buy the Four Hour Work Week. Hey, buy Drug Dealing for Fun and Profit. And neither book exists yet, so, people would click on it, and they’d get a 404 error. But we could understand what got the better response. And so now, it was no longer your opinion versus mine. It was just like what do people respond to.

Tim Ferriss: So, we did this –

Mike Maples: That’s my recollection.

Tim Ferriss: Yeah. So, we had this testing, but it goes even further back. So, you had appeared, I was more of a spectator, in a class that I took in college.

Mike Maples: Oh, when you were undergrad.

Tim Ferriss: Back when I had more hair on my head. And Mike came to talk about thunder lizards, which we’ll talk about in a moment. And that was part of what piqued my interest in Silicon Valley, the Bay Area, the excitement certainly of the time, ’99. Granted, it was an exciting time to be running towards the precipice also. But got me out here. And then, our conversations around the time that the Four Hour Work Week came out involved, to my recollection, many things. But we would sit at, and I might be getting this wrong, but Hobie’s.

Mike Maples: Hobie’s, yeah, and Town and Country, which is, unfortunately, no longer with us. They have [inaudible].

Tim Ferriss: And we used to just eat omelets and talk about marketing and PR but also about the deals that you were becoming involved with. And the testing, for people who don’t know, was very simple. We had a number of different titles and used Google Ad Words, which it was the golden age of Google Ad Words. You could just shoot fish in a barrel. It was so inexpensive. And so, we took the prospective headlines as the actual ad headlines, and then, the prospective subtitles as the ad text, and then, had all of these unique URL’s that, like you said, went nowhere because all we really cared about was the click through rate.

What I also did, if we want to talk about businesses going out of business, there are a lot of them to point to, is went to Paulo Alto, University Avenue, to the Border’s that existed at the time. And to test covers, I had mock ups that I printed out. And I would wrap a book that was roughly the same size I thought mine would be, put it up during what I perceived to be rush hour at Border’s.

I’m not sure how I figured that out. And I would stand there like a bouncer keeping track of fire code like click, click, watching the number of people who picked it up like every 15 minutes, so, I could try to look at the visual appeal of different covers. Now, it’s a lot easier. You don’t have to quite do that.

Mike Maples: I’m going to steal this wine.

Tim Ferriss: Oh, yeah. Maybe I need some booze up here. We’ll get to that. But what I wanted to do –

Mike Maples: So, could I just interject one other thing about these things.

Tim Ferriss: You should interject with many other things.

Mike Maples: So, I went to Keppler’s Book Store and Printer’s Inc., I guess, because they were well known as Bell Weather Book Stores. And I was I went and bought $1,000.00 worth of his book, the Four Hour Work Week, at both book stores. And we didn’t really now, at the time, but Bell Weather Book Stores kind of trigger supply chains. And so, it’s a little bit like before the App Store happened because iPhone wasn’t out yet. And so, I’d go into these book stores, and I’d be like how many copies do you have in the book store?

I want to buy them all because this book is going to be hot. And I’m doing this off site. And I need every copy you’ve got because I doubt you have enough copies for all the people in this organization I run. And so, it was just me, at the time. But it turned out it was true. It becomes oh, wow, Keppler’s Book Store, Printer’s Inc., they’re selling out like crazy, this Four Hour Work Week. And that is a hot, heat seeker on the New York Times. And then, more people read it, and it becomes – and, obviously, it was a good book. That helped. But it was like, just looking back on it, how crazy that was.

Maybe you thought it was going to be this huge break out bestseller. But I remember I was just like, hey, I’ll read these drafts and help however I can. And like I hope it works out, but whatever.

Tim Ferriss: I think you offered one of the very first blurbs in the first edition of Four Hour Work Week after you read additional copies, I go, okay. Maybe I made it up. I’m not sure –

Mike Maples: Yeah. You’re like, “I need somebody to do a quote.” It was like, “Okay, I’ll do one.”

Tim Ferriss: But when we’re talking about this alchemy, for instance, Keppler’s let’s just say, unbeknownst to me, there are certain stores that trigger certain other things. And then, there’s this I’m not going to say black magic, but there’s these tipping points. So, now, people look at what you’ve accomplished and the investments you’ve made and the Midas List and everything. And it’s, oh, my God. Mike Maples sort of in quotation marks. But my understanding is that you had a tough time getting hired as a venture capitalist when you first got here.

Mike Maples: Yeah.

Tim Ferriss: Can you talk a little bit about that?

Mike Maples: It’s like in Coach Bill Campbell – how many people have heard of Coach Bill Campbell before? A fair number? For those of you who haven’t, I’ll just give the quick version. Bill was an early executive at Apple. And then, he ran a company called Claris and then, Go, which flamed out, and then, he was CEO of Intuit. But probably more significantly, he became kind of the most famous coach in Silicon Valley.

He had been a football coach before he was a business guy. And so, he was on the board of Google and Apple. And, actually, I had gotten a chance to work with him in Twitter and in Demand Force, which were two companies he got involved with that we invested in. And Bill’s favorite song was “You Can’t Always Get What You Want,” by the Rolling Stones. And it always struck me that, and we won’t do too much of the book, but that, sometimes, the stuff you’re not getting right now that you think you want wasn’t the thing you really wanted. And so, I couldn’t get any venture firms to hire me coming to Silicon Valley.

I was just this random guy who had moved to Silicon Valley from Austin, Texas, never done an angel investment in my life. And Kevin Rose, one of your favorite guys, one of my favorites, too, the first two entrepreneurs I ever backed were Evan Williams who ended up doing Twitter, and then, Kevin Rose. And by the time I met Kevin, no venture firm would hire me.

Nobody thought I knew consumer internet because I was an enterprise software guy. Nobody thought I knew how to invest. And I was like, “Kevin, look, I really need you to take my money on this thing.”

Tim Ferriss: That’s what we call a high leverage opener.

Mike Maples: “And I’m afraid that I’m going to have to go on hunger strike in your apartment if you don’t take my money in this Digg deal.” And he ended up letting me – Kevin and then, Jay Adelson let me invest in Digg. And Digg had a kind of circuitous path. But I look back on it. That was sort of the booster rocket. It’s funny. People talk about who backed them or whatever. I think that it was Kevin’s generosity that sort of got me. I’m sorry. I get caught up in this stuff. Sorry about that. So, you and I share a similar affection for the same guy.

Tim Ferriss: Kevin is a sweetheart of a guy. Also, one goofy mother fucker, as you guys know.

Mike Maples: Well, you know more about that stuff

Tim Ferriss: I know more – well, we won’t get into that. But how did you connect with Kevin? How did that meeting end up happening?

Mike Maples: Well, Ron Conway was really generous. So, I heard about this guy named Ron Conway. I reached out to him.

Tim Ferriss: Who, probably still, but was thought of as the godfather –

Mike Maples: The most famous angel investor in the world. And so, we go to the Oasis. Was it the Oasis? Maybe the Goose.

Tim Ferriss: What are those, massage parlors?

Mike Maples: No, no, a restaurant in Paulo Alto. No, I think it was the Goose. And so, Ron is like, “Hey, great to meet you.” And I said, “Ron, I just want one chance, just one chance to work with you on one thing.”

“Just give me one chance. That’s all I need.” And he’s like, “Okay, whatever. You get your chance. What does that mean?” And I said, “Well, there’s this company that I’m interested in called Digg.” And I had come up with my own independent conviction about it. But there’s no way, like how am I ever going to get in touch with Kevin Rose? I’m just some random dude. And so, Ron is like, he looks at his spreadsheet, and he’s like, “Oh, yeah, I’m meeting with him next week. Do you want to come with me to see Digg?” And I’m like, “Sure, let’s do it.” And I just knew what they were trying to do. I heard a lot about their mission.

And I wasn’t talking about things like cohort analysis or like what was the retention and the decay factor of the users. It was more like you guys are transforming journalism. And this is like super important. And it’s like the wisdom of the crowd is applied to stories. And so, it was just I think that part of why Kevin gave me a shot and Jay was that they just knew I just cared a lot about what they were doing for my own reasons.

Tim Ferriss: Well, I think that, from the opposite side of the Hobie’s brunch table, when I heard you talking about startups, you were always genuinely personally vested and excited about the products. And you spent a lot of time not just looking at the deal structure and the this and that and the particulars of whatever the projections might be but the product itself. And knowing Kevin as well as I do now, I would see that as a key factor, and also many other things to him than gravitating to you in that way. And when I think back to our lunches, we would talk about all of these various things. And I would pepper Mike with all of these questions.

Like wait, what’s a claw back? What’s a pro rata, I don’t know what that is? What’s this? What’s that? And, eventually –

Mike Maples: Like any of it matters.

Tim Ferriss: Yeah. It’s all blindfolded monkeys throwing darts. But I really wanted to know how the best blindfolded monkeys threw the darts. So, we’re digging into it. And I remember, at the time, I was pretty – this was before the Four Hour Work Week popped because, keep in mind, that book had initial print run of between 10,000 and 12,000 copies. Not even national distribution. No one expected it to do really much of anything. And I was eager to take a little vacation. And I thought this two year vacation called an MBA might be interesting. So, I was looking at Stanford Business School, and I made all of these visits. And there were some great classes. One was taught by Pete Wendell, venture capital, inside the trenches. A really great class by an operator. But then, there was all of this theoretical stuff that I just couldn’t quite stomach.

And after, I don’t know, four or five of these lunches, I said, “Wait a second. Maybe I could put together a real world MBA and make this Tim Ferriss fund, in principle, and spend $120,000.00 over 2 years and learn all of these and develop all of these relationships, and view the $120,000.00 as sunk costs.”

Like that’s gone. It’s tuition. But I don’t know if you recall, but right off the bat, what do I do? So, I ask Mike if he’d be willing to let me piggyback on a couple of deals to co-invest and be really sort of cheap labor to try to over deliver to these companies. And if you want to mention it, you can. But I’m not going to bring up the name of the company. But there was this company that you were very measured in assessing. And he told me about it. And it was super popular, I think, in Taiwan or somewhere. And I got so over enthused. I was like I want to put in $50,000.00. Now, keep in mind, that’s $50,000.00 of $60,000.00 for my first year.

And the first deal, I wanted to do $50,000.00. And I remember what you said to me, at the time, in your very Mike way. You said, “Well, Tim, don’t you think that might be a little aggressive?” And I was like, “No, man. This is going to be the next Google.”

And okay. And then, yeah, that didn’t – that forced me though, if you want to talk about life saving you from what you want, losing – it wasn’t immediately lost. That’s part of the tricky – one tricky aspect of the startup stuff is like you might have a clean loss for many, many, many years. You just might have like –

Mike Maples: You saw that quickly.

Tim Ferriss: Yeah. So, you might have the walking dead scenario where it’s just like I am legend, and you’re like now what do I do. Kind of like certain areas in SF past 6:00. Anyway, so, I need more alcohol, so, I can excuse all of the things that I’m going to say. Where was I? Oh, yes. So, the point was I had to then figure out something called advising because I was already out of money in Year 1. And that led to, in that period of time, a lot of the absolute best connections that I made, including, just to highlight something that comes up over and over again in Tribe of Mentors, it comes up over and over again in conversations with you. 

There are these catastrophes or business failures that really end up, in no uncertain terms, sowing the seeds of really huge later success. Like you mentioned the circuitous path of Digg. But who cares because you befriended and became an ally of Kevin Rose who knows everyone, just about, in tech and is very generous with making introductions. And if he cares about you and believes in you, he’ll make those introductions. Similarly, I ended up, at one point, introduced to Garrett Camp, and I advise Stumble Upon didn’t work out. But we had a chance to work together extensively.

And then, what did Garrett Camp go on to do? He started this thing that people laughed at called Uber Cab LLC, which then got renamed and became Uber. So, that, at least on paper, has worked out very well.

Mike Maples: That’s more important than claw backs.

Tim Ferriss: Yeah. More important than claw backs. So, first and foremost, thank you for shepherding me, even as –

Mike Maples: You were a quick study, it seems.

Tim Ferriss: As much of a blunt instrument as I was, into all of that. But could you tell us about some of the responses from the venture capitalists, these rejections? Like what happened? Can you tell us about – you don’t have to name names, but how did these meetings go?

Mike Maples: Well, I don’t blame them. I’d never made an angel investment before. I was from Austin, Texas. I had no network here. I’d just show up saying hey, I think I want to be a VC. And that’s not a very straightforward path. And so, I would call up Sequoia Capital and say, “Hey, I’d like to interview for a job at Sequoia Capital.” And that’s just not how it really works. And so, I have no animus towards anybody. They probably made the right decision, at the time, for what their parameters were.

Tim Ferriss: So, you have a characteristic, it seems, at least in the way you express yourself, that I don’t see in a lot of people. And that is you seem to hold very, very few grudges. I don’t think I’ve ever heard you express ill will towards anyone, especially in this day and age. That’s a rarity. Is that something that you’ve always had by birth, or is that something you’ve developed? Why is that?

Mike Maples: It’s a waste of time.

Tim Ferriss: But how did you learn that?

Mike Maples: How did you embody that?

Tim Ferriss: It just is because, if you – I don’t know. I kind of look at it like life is short. You don’t have much time. Every day is a gift. And the part of the secret of happiness is to figure out what your gift is and to offer it to the world. And to not worry about all of the noise and the hype around you that says what you should do. Think for yourself, and don’t waste any energy on the stuff that doesn’t matter to you. And holding a grudge is a symptom of not knowing how you want to spend the gift of today.

And so, it’s hard to hold a grudge. If you’re so focused on I’m excited about these things, I can do a good job at this, I can’t wait to do this stuff, how do you have time for grudges? It just doesn’t make sense. It doesn’t make sense. I mean, there’s a few people, just to be honest.

Tim Ferriss: So, you land in Silicon Valley. Sequoia is like –

Mike Maples: And it wasn’t just Sequoia. It was everybody. I’m not singling them out. I probably shouldn’t have singled them

Tim Ferriss: I’m not trying to shave their nuts for an undo reason.

Mike Maples: I’m singling them out because I was taking a fling at an impossible dream.

Tim Ferriss: And Sequoia is like hey, Harvard, I want early acceptance, and I want to start in the middle of the year, even though I don’t have the pre-reqs, in a sense

Mike Maples: And I had no resume, no grades.

Tim Ferriss: That’s a hard pitch. And they’re really good at what they do.

Mike Maples: It turns out it was, yeah, a hard pitch.

Tim Ferriss: But you land here, you don’t get the jobs.

You are given this gift of an introduction through Ron with really smart wordsmithing. I hope you guys are listening. Like the pitch is really, really important and nuanced. You end up meeting Kevin Rose. So, you invest in Evan. Now, at the time, was it Twitter, or was it?

Mike Maples: It was Odeo podcasting.

Tim Ferriss: So, walk us through how that unfolded.

Mike Maples: Well, I thought – I was in Austin, and what I would do is my kids were in grade school, and so, we weren’t sure whether to move yet. So, I would come out every Sunday night and stay until Thursday. And it’s funny because, when you’re on that pattern on the plane, some of the same people are on the plane like system integrator, consultant people from Deloitte and stuff. And I’d be like, oh, it’s the brothers. Hey, buds, what’s going on? So, I’d be on these plane flights with all of these people. And I’d go from Monday to Thursday.

Tim Ferriss: This is always dangerous when I get the bottle.

Mike Maples: Liquid courage, yeah. And so, I thought, okay, I’m going to take nine months and figure out if I can find something exciting in Silicon Valley. So, I just, basically, immigrated here. And the reason that I did that is that I thought the web was shifting from an internet of connected pages to a platform that would connect people. And it just felt like it was kind of time to get the party started again on the internet. The bubble had burst. The meltdown had happened. And I saw things happen. I saw Tim O’Reilly talk about Web 2.0. I saw stuff about podcasting and broad catching and stuff like that. And I was like hit’s just clear to me this is just obvious that something major news happening.

And I just have to go to California. I have to go right now, not wait another day. And so, I do that. And Ev, had the best podcasting company. And so, Jeff Huber at Google introduced me to him. He said we just ran him off because he doesn’t want to work at a big company. But it’s going to do something interesting podcasting. And, somehow, Evan took my money his first time ever.

Tim Ferriss: So, now, he took your money, but walk us through, briefly –

Mike Maples: By the way, that’s a pretty good start at investing.

Tim Ferriss: That’s a fantastic start

Mike Maples: Evan Williams and then, Kevin Rose, it’s not bad. You could argue that the secret to venture is to get lucky in your first five years, which I think is a pretty strong argument.

Tim Ferriss: I think it’s a huge argument.

Mike Maples: Yeah.

Tim Ferriss: But you’ve, since then, been quite consistent. I should – now, correct me if I’m wrong, but with Odeo, was there a point when Ev, who is a very good guy, decided to offer investors the ability to get their money back?

Mike Maples: Yeah. So, what happened was I invest in Odeo. I’m like, okay, great, best podcasting company, first angel investment I’ve ever made. I just wired the money in. A week later, Apple decides they’re going to give away podcasting on iTunes. And, at the time, it’s hard to remember now, but 85 percent of all playback devices were iPods. It’s like what are we going to be? The one you pay for on the Zoom? It’s like you don’t have a business.

Tim Ferriss: There’s still people trying that.

Mike Maples: And so, Ev, to his credit, tried, for about a year, to figure out another business. And we couldn’t. And we’d go brainstorm, and we’d look at each other, and we were like, yeah, this is pretty tough. And so, one day – some investors were getting pretty disenchanted because they’re like you’re just wasting our money. There’s no business here. And so, Ev decides to give it back to everybody. And so, I’m like, “Look, Ev, you don’t owe me anything. Venture capital is the word adventure as venture in it. And you win some, you lose some.” He goes, “Well, this is kind of the deal I’ve struck with some bigger investors. It would help me a lot if you just went along with it.”

And so, I said, “Well, as long as you let me invest in your next thing.” And he goes, “Well, part of this deal is I get to keep this IP that I’ve been working on on the side.” “And we’re trying to decide whether to call it Voicemail 2.0 or TWTTR. And Jack is working on it along with Noah, and we’re figuring this out.” And I’m like, “What is – come on, Voicemail 2.0? And why don’t you put the vowels back in? Twitter without the vowels sounds like Flicker, and that’s a derivative and whatever.” So, I don’t think I had anything to do with that, by the way, but that was just my gut reaction. So, he goes, “You say what you’re doing.” And I’m like, “Okay. Then, what happens?” “In 140 characters or less because we wanted to do cell phones and stuff.”

And this is before the iPhone, right? So, I’m like, “Okay. And then, what happens?” And he’s like, “That’s it. That’s all it does.” And I say, “What’s the roadmap?” “There is no roadmap.” “And what’s the revenue model?” “There is no revenue model.”

And so, I say, “Ev, like why do you even think this is a product much less a business, a company?” And he goes, “Oh, I have no idea if it is.” But he goes, “Here’s the way I’m thinking about it. Blogger, a million people use Blogger software.” And this is Ev’s first company was Blogger. He was one of the pioneers of blogging. He goes, “Podcasting is kind of hard.” You had to use Odeo Studio, you had to record stuff. You had to put it on RSS feed. He’s like, “It just took more effort.” He’s like, “What happens if you had micro blogs, and rather than a million people did micro blogs, 10 million people did micro blogs?”

He’s like, “I think if 10 million people did micro blogs, the burden of proof would be on the people that were negative.” And so, I was like, “It sounds good to me. I’d like to invest in Twitter or Voicemail 2.0, whatever you call this thing.” And he says, “Well, it’s not a company. There is no investment.” And then, a few months later, maybe six months later, Twitter blows up at [inaudible], which is such a delicious irony because it’s from Austin, the town I just came from. And a couple of weeks later, Ev says – and I thought by then, it’s like a hot air balloon drifting away. There’s no way I’m going to get to invest. Ev has forgotten, and everybody is going to be chasing him. And he calls me up one day, and he says, “Hey, did you mean it when you said you wanted to invest in Twitter?” And I said, “Yeah.” And he goes, “Well, we’re about to take our first money. And if you want to do that, now is the time.”

Tim Ferriss: Wow. Ev is a good guy.

Mike Maples: He is. So, I remember that because both of those guys were good to me. Like I was just some random Joe Schmoe guy. And both of them gave me a chance to be in their companies. And yeah.

Tim Ferriss: They’re good guys. And the –

Mike Maples: Yeah. I try to remember that every time an entrepreneur pitches us. I try to remember the grace those guys showed me.

Tim Ferriss: And our stories intertwine in so many ways because that’s –

Mike Maples: Yeah. I met him right around the time we were hanging out on this book.

Tim Ferriss: Exactly. And 2007, South by Southwest, I begged and pleaded with Hugh Forest who was running South by Interactive, or at least the programming side –

Mike Maples: Still is.

Tim Ferriss: Still is. And now, a neighbor of mine, effectively. And I begged and pleased. I said, “If you have any last minute – I know you don’t have any spots because I’ve already been rejected multiple times. But if you have a cancellation, if there’s anything that moves and there’s a spot, please let me know. I’d love the opportunity.” And low and behold, there was this chance, in 2007, which, at the time, to put it in perspective, all of the tweets in the world were being displayed on these big screen TV’s that were positioned around the conference hall. Just one feed moving kind of slowly, every Twitter user. I was briefly in the top 100. I was very proud of that, until Ashton Kutcher came along and just kicked my head right off.

Mike Maples: I never cracked the top 100.

Tim Ferriss: Well, you only needed like 500, at one point, and then, it was gone.

Mike Maples: I should have been mike@Twitter. But I was like, come on, how far is this going to go?

Tim Ferriss: Well, there’s so many people who have that story. They were like I just chose hawaiisteak5.0 as my user name because it’s not going to become anything. And they’re like, yeah, now, I’m stuck with that for the rest of my life. But I ended up getting an email from Hugh. And he’s like, “Hey, if you meant it, we have an overflow room that had a cancellation. A sponsor isn’t going to do their schtick. So, if you want it, you have 45 minutes.”

Mike Maples: So, you blew up at South By, too?

Tim Ferriss: I did. And what was really funny about it is I was so nervous. I was so nervous. It was my first presentation really about the book. And it was before the book came out. The book came out in April of 2007. This was in March. And I was staying at a friend’s place because I wasn’t going to pay for the hotels. They were all sold out. also, if you get a room, it’s like $1,000.00 a night during South By. So, I stayed in my friend’s house. And I would go into his garage. And I rehearsed my talk in front of his three chihuahuas. And I’ll explain why. A) My friend had other things to do, and he had a real job. So, he wasn’t going to be there. But the chihuahuas, you had to be at least 10 percent Tony Robbins to keep them engaged. And these dogs were –

Mike Maples: Is that your secret?

Tim Ferriss: If I could be 10 percent Tony Robbins, I’m doing pretty well.

Mike Maples: If you were in Tribe of Mentors, that would be your talk like it’s a chihuahua?

Tim Ferriss: Yeah. My secret trick for networking is to practice with dogs because they don’t care about the content so much. But if you’re monotone, they just kind of go – and turn around and walk away. So, I was in the garage, and I’m kind of doing this hand wavy stuff to keep them engaged.

Mike Maples: I totally believe this

Tim Ferriss: Oh, no, it happened. I remember the garage. And then, I got to the event, and I had all of these fancy slides and everything prepared. And what happens? Blue screen of death. My computer dies. And so, I’m like I guess I’m just going to have to do this without any of my prompts.

And I did it, but I’d rehearsed so much that I had it in my head. And yeah, so, Hugh, also one of those people. It’s like, to this day, if Hugh ever asks me, “Hey, could you help us with X, Y, Z?” It’s like of course, I will because it’s just like that one opportunity. And I also want to emphasize one thing. People could say, well, the luck was there with Twitter, at the same time. And it was absolutely lucky. But it’s like, every year, there is something to draft on. Every month, there is something like that that you can draft on. You just have to look for it. But you were going to say?

Mike Maples: Well, the other thing is it’s kind of – I guess we talked about grudges earlier. To me, the opposite of having a grudge is to enjoy seeing somebody do well. And when I was a founder, you’re just trying to do real company stuff and make the company happen. And you’re like, okay, we’re going to go on this ride. And hopefully, it works out. But one of the fun things about being an investor is you get to see people do well. You get to see – like Logan and John from Lyft ate beans until they raised their seed round.

And when we had our first board meeting, Anne looks at the financials and says you guys aren’t paying yourselves minimum wage, and that’s illegal in California. They’re like we have to fix that. And so, and now, people talk about how much money Lyft has and how Carl Icahn has invested and Google capital. But I remember them when they were eating beans. And it’s just fun to see them do that well. It’s fun to see you do this well. It’s like we had no reason to think the Four Hour Work Week was going to be that big a deal. You hope it will.

Tim Ferriss: We had a lot of reasons to believe it wouldn’t be a big deal after 27 rejections.

Mike Maples: But it’s just like every time I see – I’ll get a call from somebody like a reporter that says, “Hey, would you do a quote for this article about Tim,” in some major publication. I’m like wow, he’s just killing it. That’s awesome. It’s just fun to see – it’s a lot more fun to spend your energy on deriving joy from that and seeing your friends do well, especially friends who are worthy of doing well and won’t be changed by it. That’s a lot more fun than remembering who wasn’t nice along the way, you know?

Tim Ferriss: Yeah. It’s a drag. I’ve been working on the grudge piece. I don’t have many. But it’s good to see you. It’s been a while.

Mike Maples: Yeah, like the Arab Spring or when I’d pick up Sloane on a play date, my daughter, Sloane, and the parents at the play date would say, “Is it true you invested in Twitter? I saw them on Oprah.” And then, the Arab Spring happened. And I was like, wow, this company is kind of working. We’ve got a chance to do well on this one.

Tim Ferriss: So, you mentioned your daughter. I want to bring up something that I’ve thought a lot about since you mentioned it to me. And, as context for folks, what I’ve really tried to do in the last at least five years is to look at the lives of people I look up to in a holistic way before modeling them.

So, what I mean by that is it’s tempting to look at the business success of Person X and then, replicate everything they do. But all you may see is one tiny piece of the puzzle. And then, in actuality, they walk around in shambles in every other capacity. So, I’ve tried with the interviews and the books and Tribe of Mentors to really look at things holistically. And I remember asking, and I ask, even though I don’t have kids, I ask parenting advice of friends a lot because I’m curious to see how they look at it.

And, at one point, I asked you, we were on a hike, and I asked you what advice you would give to a new parent or something thinking about becoming a parent. And please correct me if I’m getting this wrong, but –

Mike Maples: My earlier versions could be better.

Tim Ferriss: But, to my recollection, there were two main points that you made. And there could be more, but you said, 1) really teach your kids and train them to be optimists because, without that, you’re lost. And with that, you can at least look for or see solutions and silver lining and so forth. And then, the second part was remember that your kids owe you nothing. They didn’t ask to be born. You chose –

Mike Maples: You did remember, wow.

Tim Ferriss: I do remember. It was meaningful to me. It really made an imprint. And your job is to give them love. It is not there not to give you love.

Mike Maples: That’s right. I chose to have them. They didn’t choose to have me. They owe me nothing. And I find it helpful to think about that. But the hope part, I think, is important for them. The way I look at it is, unfortunately, unless we solve some breakthrough problem, we’re all going to die. So, you can choose to be defeatist about that, or you can choose to say the fact that we get to live at all is just this huge gift. And so, I think that one of the things that you can do for your kids is you can help them feel optimistic and happy about the fact that they have the gift to be alive.

And that don’t be defeatist about this world. You had the gift of today. And as long as you have the gift of today, like you’re on the path to the light. And if you can give your kids the gift of being optimistic and hopeful about the future and grateful that they have the time they’re going to have, I think that’s helpful for them because kids get judged. And all of us are unkind to ourselves in our own mind, and we’re judged by people all of the time. And it’s easy to just forget that today is a gift. Be grateful for that gift. Be optimistic that tomorrow is going to be another day where you have another gift.

Tim Ferriss: So, when your kids or one of your entrepreneurs – startups are a full contact sport, right?

Mike Maples: Yeah.

Tim Ferriss: People take their lumps in major ways. And bad things happen all of the time. Whether it’s with your kids or some of the founders you’ve worked with, when they’re going through a really rough time, what do you say to them? And you could give a specific example or just a general principle. But I’d be curious just to hear how you would think about that.

Mike Maples: Well, so, these founders that we’ve worked – some of them are just extraordinary. And so, I’m reluctant to say we had much of an impact. I think the thing that sometimes I’ve done that I’ve been proud of is when they’re in the depths of despair. Entrepreneurships like this where there’s no even path. And there are times where you’re just like everything is against you, and you’re just like how did I get myself into this. And this is so terrible. And I think I’ve been better than most at those times at kin of saying you’ve got this. And, sometimes, they need to hear that.

Tim Ferriss: Is it just the words? Or how do you deliver it? Like what makes it stick?

Mike Maples: No, I tell them, look, Twitter, we couldn’t keep the servers running. We couldn’t decide who the CEO was. Twitch, it was Justin TV. Chegg was Craigslist for colleges. And then, Facebook decided to compete with us, and we pivoted to textbook rentals, and we only had 30 days left of cash. And like ngmoco, we had 45 days of cash when we pivoted from app downloads to free to play. And Lyft started out as Zimride. And when we launched Lyft, we weren’t even sure it was legal. So, I’m like, guys, I’ve seen way crazier than this. You got this. And, sometimes, a founder needs to know, look, entrepreneurship – I like to say I like to invest in people I would enjoy getting in trouble with because it happens every time.

And when you’re in trouble with these people, what’s it going to feel like? Is it going to feel like, okay, it’s us against the world? Or is it going to feel like how did I get myself involved with these people? And so, I like people where I’m like we’re in the fox hole together. Screw the rest of the world and what they think. We’re right. They’re wrong. Let’s rock and roll. And so, that’s kind of – I think that we’ve been – when I was an entrepreneur, one of the things I learned is that my early customers, they didn’t just buy what I was selling. They bought because they believed what I believed.

We were in on a secret together. And when I work with founders, I like to say I’m in on a secret. I believe their secret. And we think the rest of the world is just wrong. We think we’re right. And we’re going to prove it. And so, when stuff goes wrong, we’re like it’s just a setback, speed bump, whatever. But in the end, it’s like we still believe in our insight. We’re right. Let’s prove it. Let’s prove it.

Tim Ferriss: What about for yourself? If you can think of, in the last decades, it could be anything, but could you give us an example of maybe a tough time that you went through and how you found your way out of it? Or what helped you find your way out of it? It could be any facet of life.

Mike Maples: Gosh. There’s a fair number. Liz and I broke up. We’d been married for 17 years, and things didn’t work out. And that just felt like I had really failed as a person, and I was about to fail as a dad. And what else was there, if I failed at those things? Then, what could I even think I was successful at? So, that was a tough time. But, fortunately, kiddos turned out okay. And I tried the hardest I could to navigate that time the best I could. And kids turned out great. And Liz and I get along just fine. And you win some, you lose some. But, at that point in time, it just felt like everything I had done in this life was screwed up, and I had just totally blown it.

Tim Ferriss: How did you not just succumb to the depths of despair and stay there?

Mike Maples: Yeah. And, someday, we need to have some more wine to talk about this because I know you’ve said that you’ve struggled, at times, with feeling depressed.

Tim Ferriss: I have, yeah.

Mike Maples: And I’m like the worst person to talk to depressed people because I just don’t understand the concept. And it’s like I’m not judging, but I’m just like today is a gift. And I have to make the most that I can out of it. And if it doesn’t work out, make the most out of tomorrow. And, by the way, I don’t think that my way of thinking is better than your way of thinking. It’s sort of like you’re leaner than I am. You could probably run faster, jump higher. I don’t sit there and say give me your legs. I just realize that we’re all different. And I realize that I’ve had a few blessings in life, and one of them is to be grateful for every day. And for that to be the high order bit. No matter what’s happening, I’m like you got to have today.

Tim Ferriss: So, was that just a life raft that you had throughout that entire period that each morning you would remind yourself of? Or how did it manifest on a daily basis?

Mike Maples: It’s just ever present. It’s just obvious to me. It’s like breathing oxygen.

Tim Ferriss: Man, I need to borrow your code. All right.

Mike Maples: But I don’t say that as listen to me and my advice, I’m so smart. It’s just I was lucky enough to be configured and wired that way.

Tim Ferriss: So, I want to make a suggestion to everyone in the audience. And this is based on observing Mike over and over again. When someone says to you, “Well, you can explain it to me. I’m not a fast thinker. I’m from Texas.” When someone pulls that, you should really be careful. And I actually borrowed that from you. And I was like I think I can use this because most people think people from Long Island are idiots. Great. So, I’ll be like explain it to me again because I’m not clear. My brain doesn’t move that fast. I’m from Long Island. And everyone is like what? So, thank you for allowing me to steal that.

Mike Maples: I’m glad I could help you act simple.

Tim Ferriss: So, I wanted to bring up, and this is actually something we have not spoken about publicly or privately before, but Commander John Boyd.

Mike Maples: Yeah.

Tim Ferriss: Can you explain who Commander John Boyd is and why you’re a fan?

Mike Maples: Yeah. So, Commander John Boyd was a flight instructor for the Air Force. And there was this expression that, in a simulated dog fight, he could beat any pilot in like 30 seconds or some outrageously quick amount of time. And people were like well, how does he do that. And he taught this form of combat, which was about moving very quickly. And so, if you place yourself in the time I was reading about John Boyd, it was also when I was working with Eric Reese and Steve Blank. And so, Eric Reese was a consultant at Floodgate before he wrote The Lean Startup. He’s famous just like I – I have this magnetism for famous, future to be authors, I guess. So, we were talking.

And we were like something really important is happening here. Offshore labor, search engine marketing, open source software, broadband penetration, global markets. And it seems like you can get a product to market for less money. You can do it faster. And Steve Blank started talking about this guy named John Boyd. And so, John Boyd is this flight instructor in the Air Force.

And he could beat anybody at a dog fight super fast. And Boyd’s fundamental insight was that, sometimes, you could win a battle purely by being faster. So, like let’s say you’re in a Russian MiG, and I’m in an F16, and I make the wrong move, but you haven’t moved yet. And then, I make the right move before you’ve moved yet. Just the mere fact that I was able to make a move and course correct before you made your counter move means two things. I can get in the right position relative to you. But, more importantly, it’s very disorienting to you because you don’t know where I am. I was here, and, now, I’m there.

And so, the philosophy of John Boyd that was inspiring to me back in 2005 and one of the reasons I started Floodgate was I was like you can do this as an entrepreneur and an investor. And so, the F16 fighter jet was designed to John Boyd’s spec. An F16 doesn’t fly faster than a Russian MiG, but it changes directions faster.

And so, the F16 fighter was a system. It wasn’t just the plane, which could change direction faster. It was the mind of the pilot. And the mind of an agile pilot with an agile plane would beat a Russian MiG all day long. And so, I was like that’s what’s going to happen with startups. And that’s why $500,000.00 is the new $5 million. And that’s why we need to go fund these agile entrepreneurs because they’re going to be able to force multiply. And the big competitors who have raised a bunch of money are going slower and doing waterfall development, they’re going to be disoriented by how fast these companies move. And so, what I really learned from Boyd was kind of this idea that, if you are a speed based competitor, you can be wrong but still be right quicker, which makes you right.

Tim Ferriss: Right. Which translates very directly to Blank and Eric Reese and minimum viable product and iterating.

Mike Maples: Yeah.

Tim Ferriss: You could be totally off base in the beginning, which a lot of your biggest hits have been.

Mike Maples: Right. So, 93 percent of our exit profits have come from pivots. And so, you look at that, and you say, gosh, when we invest, should we even care what the business is? I mean, it’s a legitimate question. Like cruise automation, that’s one of our recent wins. Kyle had started Twitch. We made a bunch of money on Twitch. And he starts this company called Cruise. It’s like a roof rack that does auto pilot, self driving. I’m like, “Kyle, that’s a bad idea because you’re going to only have 20 customers in the world. There’s only 20 car companies that matter, and they have concentrated buying power, and they can design you out, unless you’re like 10 times better. There’s going to be competition.”

Blah, blah, blah. So, six months later, he’s like, “Okay, you’re right. The roof rack idea was dumb. I’ve got this new idea.” I’m like, “What’s your new idea?” He’s like I’m going to make Nissan Leaf self driving.”

And I’m like, “Then, what are you going to do?” He’s like, “Well, you know, there’s a lot of ways you can monetize that. You can do a fleet of cars. You can sell the cars to people.” So, I’m like, “Okay, let me get this straight, Kyle. Now, you’re just going to be compete against everybody. You’re going to compete against Uber and Lyft and Tesla and GM and everybody, Bosch.” He’s like, “Yeah, but, you know, I’m passionate about this. I’ve been doing this since MIT. It was my research project. And I just think this is the way to go.” And I sat there, and I thought about it. And I was like this guy made me 84 times my money last time I wrote him a check.

I think I’m just going to write him a check. And so, I go to the partner meeting at Floodgate. And thank God, we don’t have a voting system. And I say, “I think I’ve decided I’m going to do this Cruise deal.” And everybody reads me the riot act. And they’re like, “Mike, come on. I understand that a business model can be vague, but you cannot even articulate a path where this is a business. And neither can Kyle.”

And I was like, “No, but you don’t understand. He’s an awesome founder. And he’s got incredible insights. He’s very passionate.” Blah, blah, blah. So, everybody just is like talk to the hand, this is stupid, whatever. So, we had two new venture partners who became partners, Ryan and Arjun. And six months later, they get bought by GM for more than $1 billion. And Ryan and Arjun go, “Boy, it’s really a shame that we talked you out of this Cruise deal.” And I said, “Oh, we funded Cruise.” So, I was like, “Of course, we funded it.”

Tim Ferriss: I secretly have super voting rights on every deal.

Mike Maples: No. At Floodgate, there’s no voting system. It’s just somebody has to pound the table. And so, if somebody pounds the table and says I will take ownership of this, and I am responsible for the outcome of our returns, the deal happens. But if everybody around the table is an A- and says I think this is a good deal for you to do, Tim, or you to do, Anne, or you to do, Ryan, or you to do, Arjun, but nobody says I will pound the table, I am irrationally in love with this, it doesn’t happen.

So, we kind of think that, in the super early stage, love conquers all. And it’s like when you’re going through all of these times, you’re going to get in all of this trouble, it’s your love for the idea and the founder that will cause you to overcome whatever you face. And you have to have enough authentic love and passion for the idea and the founders that you’re willing to pound the table and say I will defend this. I will defend 140 characters or less, even though people say it’s stupid in 2007.

Tim Ferriss: So, you just need one person who is, in some cases, rationally exuberant and willing to defend the idea for a go signal?

Mike Maples: Yeah, for sure.

Tim Ferriss: And then, so, this is really fascinating to me.

Mike Maples: Yeah. We’re not exactly a private equity shop.

Tim Ferriss: No, but it strikes me that some of the best investors I know have a similar or close cousin approach to that.

Like if they have somebody who is willing to just put it all on the line, who has already been vetted because they were hired as a partner, like okay, kid. It’s on you then. But if they’re really willing to go to fight for it and –

Mike Maples: And, by the way, if you’re a partner at Floodgate, yeah, you pound the table. But guess what? We keep track of the deals you did. And if you lose tens of millions of dollars with no returns, it’s nothing personal, but you just don’t seem to be cut out for this.

Tim Ferriss: You’re not allowed to pound our table anymore.

Mike Maples: Right. So, when I pound the table for a deal, I know just as much as any other partner that I am taking ownership of pounding the table. And we’re going to all help each other. And we’re not going to say yeah, I told you so. But it’s like, if I pound the table, I’m saying I care enough about this idea that I’m willing to have some of my track record and credibility be tied to this.

Tim Ferriss: How do you differentiate? If you look at, for instance, 93 percent of the returns coming from companies that pivoted?

When you are observing a founder or trying to help, and just by way of giving the most convoluted question possible. The question I get a lot is how do I know when to persist with my idea? How do I know when to quit? Or how do I know when to pivot? That’s a hard question to answer. But when I spoke with Mark Andreesson a while back for the podcast, he said sometimes, people pivot so often, it’s like every time I see them, I’m paraphrasing here, it’s like watching a rabbit go down a maze. It’s like every two days, it’s a different company.

Mike Maples: Yeah. It’s like they think it’s a Mulligan, not a pivot.

Tim Ferriss: Right. So, how do you help guide or even assess a good pivot versus someone who is merely unfocused?

Mike Maples: Yeah. And it could be that I’ve just been – had a string of crazy beginner’s luck. And so, that is a very real, potential factor. But the way I see it is that you are right, not because people agree with you.

You are right or wrong based on whether your first principle’s thinking is right or wrong. And so, if I see a company where it’s not working, but I still believe in the first principles of the idea, I say this is great. We still believe in the first principles, and we know more than we knew a year ago. That’s a fundamental advantage. Like why would we not want to double down on that? And so, whereas what happens to often is you say this doesn’t work. It doesn’t have traction. We’re not going to be able to raise money.

Forget about it. And the problem with that is that, if you live with the results of other people’s thinking, it’s like if somebody really smart, like if I – I guess, if Reid Hoffman says to me this is a bad network effects idea because it doesn’t conform to network theory in these ways, I’m like, okay.

That’s data. He’s the smartest network effects guy I know, the best first principles thinker about network effects I know. And I offered a first principle to him that he said you’re wrong on first principles. I’m like I probably ought to listen to that. But if somebody, like with CHEG, when we did textbook rentals, people said people tried that before with varsity books. And who gives a shit? That was five years ago. Five years ago, isn’t today. And so, to me, it’s about what are just your first principles’ reasoning behind why you’re excited about something. And are your first principles’ reasons being refuted or doubled down on?

Because, to me, the valid definition of a pivot is the first principles are still true, but you learned something from the data on the ground that caused you to double down on a new aspect of that that nobody else knows.

Tim Ferriss: Got it.

Mike Maples: But that just may be me giving a good explanation for why I got lucky. That is perfectly reasonable point of view for you to take.

Tim Ferriss: Yeah. It’s certainly possible. I would tend to assess it as, certainly, a component of skill. But if you’re looking at, let’s say, you have the first principles. Maybe then, you have strategy. Then, you have tactics. And you have tools. You can look at a stack. Are the first principles, in your investing experience, mostly spotting converging trends that people haven’t spotted before? What would be an example of first principles, as it applies to one of these companies?

Mike Maples: Do you surf?

Tim Ferriss: Poorly.

Mike Maples: I surf even more poorly. But I like the metaphor of surfing because you could be a skilled surfer, but you don’t really control surfing. You can sort of control the board. Even if you’re good, you can only barely control it. But you can’t control the wave.

And I look at, to me, the magic that animates the tech industry is a combination of Moore’s law and Metcalf’s law. And so, I think we all benefit from the magic of Moore’s law and Metcalf’s law. And it’s like, literally, as powerful as the ocean waves below you when you surf. And so, I look at it like the job of a startup founder is to surf a valid wave. And the wave is usually bigger than the company. When we invest in Lyft and Cruise, we had this belief that network capitalism is supplanting vertically integrated corporations and that there would be network transportation just like I believe there’s going to be network real estate, network manufacturing, all of this stuff.

And so, we believe that those gathering waves are more powerful than any one company. And the job of the tech entrepreneur is to leverage the awesome, massive power of all of the fury of the ocean beneath them of Moore’s law and Metcalf’s law. Just surf into the beach.

And give Moore’s law enough time. It will breach the advantage of any incumbent. And give Metcalf’s law enough time, and it will create an insurmountable mode. Google tried to take out Twitter with Jaiku. It didn’t work. It didn’t matter because Twitter had a network effect. And so, to me, the tech industry is magical. There’s been tulips, in the past. There’s been the crash of ’29. There’s been the real estate bubble. There’s bubbles all of the time. There’s manias all of the time. But tech is animated by two valid exponential forces that are super powerful. And they are the asymmetric attack vector of the entrepreneur.

They are the rock in David’s slingshot. And so, I look for founders who have some type of fundamental contrarian insight about where a wave is about to gather. And then, hopefully, they have the stuff to surf it. And if they do, I’m like unconditional love, let’s go.

Tim Ferriss: Well, you gave me some related advice really early on. I remember –

Mike Maples: Do you need anymore, by the way?

Tim Ferriss: Anymore wine?

Mike Maples: Yeah.

Tim Ferriss: I think I have a wine deficiency, yes. I’d love some more wine.

Mike Maples: I got you.

Tim Ferriss: Thank you. You gave me some advice. I remember it was at a restaurant in Paulo Alto. There was an event gathering. Reid Hoffman was speaking. I was attending. And we were having wine, much like we’re having right now. And we were talking about some deal I was flummoxed by because I had certain primitive parameters for investing, and I was getting somewhat ridiculed for my simplistic parameters like I need to be a power user of the product. It needs to match with the demographic, the sort of core audience that I have.

And I got a lot of flak for it. And I remember you said to me, well, if those are say – you didn’t use these words then, but your first principles, those are your sort of criteria. You’re going to make, in some cases, really good investments when people are poo-pooing the idea, but it perfectly matches your criteria.

Mike Maples: Based on first principles.

Tim Ferriss: Right. Based on first principles. Conversely, if it doesn’t match your first principles, and you’re getting into a deal because it’s closing tomorrow, but we can –


Tim Ferriss: If you’re just following some consensus, however small, but it doesn’t conform to your first principles, that’s where you’re going to lose your money

Mike Maples: Yeah. This is where people talk about social proof. I think social proof is bullshit. I think that it’s – so, my favorite example is, actually, an Elon Musk example. So, I don’t know if some of you may have heard this.

Tim Ferriss: I thought you were going to say I think some of you may have heard of him. I was like fair to assume, yeah.

Mike Maples: Yeah. So, he talks about Space X. And most people think Space X is like a better NASA. But that’s not true. So, you think about a rocket. What 0.3 percent of the cost of the rocket is the fuel. And the rest of it is what gets burned up in space, what doesn’t come back. So, Elon says, okay, if you could have a reusable rocket, you could maintain 99.7 percent of the value of the rocket by bringing it back to earth.

And if you could do that, you could have a two orders of magnitude improvement of the economics of space travel. That’s first principles thinking. Or when Ev says if 10 million people write micro blogs, that’s 10 times more. The burden of proof is on the people who are negative. And so, I don’t have to see the business plan to say that’s an insight I can get behind. Conversely, I’ll see plenty of business plans that look incredibly straight forward, and I eliminate them immediately because they’re just not exponential enough, and they’re not first principles enough. And my whole business isn’t about how often I lose. It’s the magnitude of the rightness when I win. And so, when I win, I have to win super freaking big.

Tim Ferriss: This is such an important point because it applies to life and not just –

Mike Maples: Well, it depends. Like if you’re a PE guy –

Tim Ferriss: Private equity.

Mike Maples: You don’t want to have more than like a 15 percent loss ratio.

Tim Ferriss: Sure.

Mike Maples: So, you want to take out risk, and you want – but I’m not a risk taker outer. I’m a luck multiplier. I’m not asking what could go wrong because I’m investing when it’s worth zero. I’m asking what could go spectacularly right as a rare event. And I only have to be right a fair number of times, as long as the idea has the exponential awesome power to just take us to the promise land.

Tim Ferriss: Well, this is part of what appealed to me about the start up game as you explained it to me because it’s a hits driven business. You can be wrong a lot. But if you have decent rules that have some basis in reality –

Mike Maples: Maybe, yeah.

Tim Ferriss: Maybe, then, as long as your – we don’t have to get into portfolio theory and stuffy.

But as long as you’re investing enough in these bets that they can say return the fund or whatever the parameters might be, it’s a fun game. And, certainly, a dangerous one. But let me ask you this because I remember how impactful – and then, we’re going to go to audience Q&A, in my pink basket that I brought. If you were teaching – you can pick the age. It could be college freshmen, college senior, high school senior, doesn’t really matter, graduate school. If you were teaching a class on entrepreneurship, so, you’re not teaching people how to be investors –

Mike Maples: So, we do now. We teach one at Stanford.

Tim Ferriss: Oh, you do?

Mike Maples: Yeah.

Tim Ferriss: Well, that makes this easy. So, what do you teach? What are the differentiators of the class?

Mike Maples: What we try to do is help people understand that there are things that we can learn from these prime move entrepreneurs who create massive abundance.

And it’s about more than just having a good product. Product market fit, clearly important. But designing a company, what’s your culture? Are you going to define it up front, or just kind of let it happen? What’s your category? Are you going to design your category, or just let it happen? Are you going to chase revenue, or are you going to accumulate a track of customers? And so, what we try to emphasize – we try to emphasize a couple of things. One is great businesses truly are valuable.

And so, we should try to think about building a scalable business with the truth value in mind rather than what’s the latest fad, and how do we raise money, or what’s the paper unicorn or any of that stuff. But then, the other thing that we worry about some is that you look at some of these companies and the problems they’ve had with their culture, and a lot of these people come from Stanford or the top schools.

And it’s like how do we have some impact where, if only one person who might have gone off the rails is a founder in that dimension doesn’t because we’re like culture matters. Building a company foundation matters. How people treat each other matters. And some of this stuff is like a block chain transaction. You get it wrong, you can’t go backwards. Or like the metaphor I like to use is like the Hertz rental car parking lot. If you back up, the tires explode. And so, some of this stuff, you can’t really back up. And so, getting it right the first time, there’s a lot of counterintuitive lessons.

And it’s more about just having a good product. It’s about designing a company and a category in addition to the product. And having a point of view about how you’re going to bring abundance to the world and not just get rich. And so, the class is sort of about that and about just like – oh, the other idea is like, if you’re a prime mover, you don’t just have to be a tech entrepreneur.

You could be the French Laundry guy, Thomas Keller. You could be Elvis Presley, and you invent rock and roll. Or you can be Albert Einstein, and you could have a theory, or MLK had a dream. But it’s sort of the idea that we try to express to people is find your gift, and express it your way. And entrepreneurship is only one way to express that gift. But if they learn anything from the class, it’s not be an entrepreneur like these people. If entrepreneurship happens to be your calling, great. Here’s what great people do. But figure out your calling. Figure out your gift. You don’t have much time.

Don’t live someone else’s life. Don’t live by somebody else’s thinking. Live your gift and actualize it to the fullest.

Tim Ferriss: How do people who hear that, and I’m sure you go into much more detail in the class –

Mike Maples: Yeah, there’s 13 lectures.

Tim Ferriss: Yeah, 13 lectures. But for those people listening, if they wanted a place to start just to get a toe hold, and they say I want to do that, I just don’t know what my gift is, what would you say to them? What are the whispers through the ether they should pay attention to or any indicators?

Mike Maples: I’d say spend time with awesome people, and work on things with them. And you’ll find it. But most people fail to find their gift not because they can’t find it. It’s because they’re too busy worrying about what other people think. And one of the things that I find inspiring is that I wrote this post one time, and I was surprised that – so, I called it Finding Billion Dollar Secrets. And the point that I was trying to make was that billion dollar secrets are everywhere.

It’s just that people aren’t looking to pick them up off the ground. They’re looking at each other. They’re looking at status. They’re looking at when I was in high school, I got rewarded for giving the teacher the answer to the questions they way they wanted it. And then, I went to the right college and got the right graduate degree and got the right job at the right company and lived in the right neighborhood and had the right designer kids and sent them to the right designer schools and was in the right country clubs driving my right designer car.

And they get focused on Peter Thiel would probably call this mimetic behavior, this idea of people’s desires being defined by the people around them and what’s going to make a good impression on the people around them. The best entrepreneurs I know, they’re just like screw all of that. I know why I’m here in this world. That secret on the ground, that’s my gift. I’m picking it up. I’m doing this. And like that, to me, is the thing I’d tell my 20-year-old self, my 15-year-old self, my kids is figure out your gift, your gift. It’s not the world’s opinion of your gift. It is yours. It belongs to you. And figure out the gift that belongs to you, and express your gratitude for the time you have by offering that gift.

Tim Ferriss: I love it. You guys can see why I’ve bugged Mike so much over the years with questions. Speaking of questions –

Unknown: Speaking of questions, can I add one more?

Tim Ferriss: Sure. Wow. This is like the Willy Wonka golden ticket of questions. Thanks. Look at this. Rogue question givers. All right.

Mike Maples: I hope a lot of these questions are for you. I’m going to learn a lot more from your answers, I think.

Tim Ferriss: This is like the improv jazz of question receiving. So, I’ll start with the first one, and then, we’ll just kind of bounce between these. So, oh, God, a two part question always, which, by the way, means two questions. Where would you have moved besides Austin? There are a few places I looked. I love Austin. I’ve wanted to move there since I graduated from school, I just didn’t get the job at Trilogy Software, funny story. Founder of Trilogy –

Mike Maples: Was my roommate in college. I could have helped you out. I could have hooked you up.

Tim Ferriss: I didn’t know what to do. I was lost. A babe in the woods. So, Boulder, Colorado, I’m a huge fan of Boulder. I also looked at BC. I really like British Columbia and areas up in Canada. Sorry, Americans. And there were many different places that I considered, but Austin has this gravitational pull for me, so, I ended up there, which changed my mind on the significance of fiction versus nonfiction.

Really it was because I had onset insomnia, and I did not want to turn on my problem solving apparatus by reading business books and so on before bed. And I found that fantasy, Dune, Enders Game, Stranger in a Strange Land, The Name of the Wind – read that, but be prepared to wait like 17 years for the last in the trilogy.

Mike Maples: Have you ever read the Count of Monte Cristo?

Tim Ferriss: I haven’t.

Mike Maples: Oh, my gosh. Speaking of a book about grudges.

Tim Ferriss: So, since we’re on books, what books do you most recommend or gift to other people?

Mike Maples: Lately, I’ve liked there’s a woman named Bronnie Ware. She wrote a book called The Top Five Regrets of the Dying. And she was a hospice nurse who had spent time with people in the last 90 days of their life. And she would learn like what their regrets were. Or, sometimes, she’d learn what their happiness was.

So, there was an example of this woman who was from a super rich family, and she decided to marry an artist. And the family excommunicated her. And she’s like 32 years old. She gets cancer, and she dies. And she hasn’t heard from her family in years. And her mom comes to her, at the end, and says, to be honest, I was just jealous. You were living life on your own terms. And I’ve got all of these obligations. I don’t even like my life that much. And I was just kind of pissed off that you could go marry some artist and be this happy. And I realized how wrong I was. But this woman who is dying says I have no regrets.

I got to be with the person I wanted to be with. And I would have loved to have lived longer, but nobody knows how much time they’re going to have. At least I got to have the time that I got the way I wanted to have it, the best I knew how. And then, they would have another person who the opposite was true. They would be dying, and they’d say, “Promise me, Bronnie, that you will not live life according to other people’s thinking because I lived my whole life trying to please other people.”

“And if I could have it over again, I wouldn’t do that.” And so, she does a great job of having the example of the person who did it well with no regrets, and the person who is like fuck, I’m dead now, and if I could do it over again, I’d do it different. And so, it’s motivating to say, gosh, how am I measuring up against those five things? And so, I like that book because it kind of takes people out of the here and now and kind of forces you to confront a broader set of issues.

Tim Ferriss: Yeah. I think that, for me, in the last few years, I’ve had a lot of friends pass away in the last two years or so, including Terry Laughlin, rest in peace, who is in this book just a few weeks ago. And I found it really, in an odd way, reaffirming to familiarize myself with death and grief and grieving in almost a preemptive way. 

One of my favorite people, I’m sure you’ve spent time with him, Matt Mullenweg, incredible entrepreneur, but first and foremost, just a beautiful human being, and he lost his father in a very unexpected way. And he recommended On Grief and Grieving to me. And I think it’s a very useful exercise to familiarize yourself with the details of death and people passing.

Mike Maples: And I learned a lot of this from Julie who is the love of my life and puts up with me. And she’s helped all of these people who have had cancer. And so, as a result, she ends up seeing a lot of people pass. And I think more than anybody, she taught me that, in the last bit of time you have, all of the shit falls away. All of the expectations, all of the external stuff.

And so, you just hope that when that time comes, you’re like I did the best I could. I did it the way I could. And so, that’s why I find that book helpful. It’s not because I’m preoccupied with dying. I hope I live a long time. But it’s like when the time comes, I want to say I did it my way. I did the best I could. I honored the gift. So, that’s a good book. And there’s business books, too, but we’ll do that some other time.

Tim Ferriss: I think that’s a good place to move. Is everybody cool? If you have to leave, you have to leave. Are people cool with going a little longer? I’m having fun. I hope you guys – all right. So, here we go. This is a left turn from what we’re talking about. But I’m curious to hear your answer. What emerging technologies or theoretical technology, that could really go wide, do you believe are most promising for anti-authoritarian disruption similar to how Bit Coin disrupts government control of money, maybe? I’m very interested in crypto and block chain. You mentioned block chain earlier. So, I’m going to –

Mike Maples: It’s too bad we don’t have Naval here. That would be awesome.

Tim Ferriss: Yeah. But I would be curious to hear, first, your general thoughts on crypto and block chain, and then, any other emerging technologies that you think are promising for antiauthoritarian disruption.

Mike Maples: Okay. So, I hope this isn’t a shaggy dog answer, but –

Tim Ferriss: I don’t even know what that is, but it sounds good.

Mike Maples: A shaggy dog story is like a really long story. It never ends. So, for better or worse, I’m a little bit of a history buff when it comes to business. And so, I took this class when I was in business school. And only Harvard Business School would have a class called The Coming of Managerial Capitalism.

Tim Ferriss: Sexy name, rolls off the tongue.

Mike Maples: But it was a fascinating class because, for example, in the year 1820, there weren’t any companies in America with more than 100 employees because you had people selling muskets or fur. If you were a really big, monster company, you were like a spinning loom in Waltham, Massachusetts and spinning yarn and fabric. Well, then, the railroad and the steam engine come out, and that changes everything. So, what people don’t realize about people like John Rockefeller and JP Morgan and Andrew Carnegie, imagine you’re doing standard oil. And you want to compete with a guy in Pennsylvania on oil prices.

You don’t just whip out your cell phone and call the branch manager and say lower the prices, run this guy out of business. There’s no accounting. There’s no org charts. There’s no salary and managers. We don’t even have the telegraph yet. We don’t have shit.

And Rockefeller is building a company against that backdrop. And then, JP Morgan is like there’s nobody who has enough money to own a transcontinental railroad, so, maybe I should do this thing where you create these fractional units of ownership of a company. We’ll call it stock. You’re some guy who sells – you’re a blacksmith in 1820. And somebody says do you want to buy stock in a railroad. You’re like what good does that do me? Stock in some random company that doesn’t exist? Why would I want that? And so, but what happened was the modern corporation emerged.

And it drove the standard of living of humanity thirteenfold from the year 1820 to 2000. The richest man in American in 1870 was Cornelius Vanderbilt. He didn’t have flushing toilets. He didn’t have running water. He didn’t have electricity. You can have all of those three things now and be defined as poor.

And so, I look at it, and I’m like people say capitalism is screwed up. I’m like what are you talking about? I’m like it’s a freaking miracle. In 1800, you had to work one hour to get six minutes of reading light. Today, you work one hour, you get 300 days of reading light. It’s a miracle. And there’s a lot of stuff that is wrong with how people are practicing capitalism. But free trade and voluntary I have this to offer, you have that to offer. We get to trade without somebody interfering, that’s not the problem we have. Well, what I think is happening today, and this is where block chain gets in.

Tim Ferriss: I’m hearing a little Texas. Sorry for this –

Mike Maples: No, no, no. I believe that block chain and things like it and Moore’s law and Metcalf’s law are the fundamental animating forces of what I like to call networked capitalism. And I believe that someday, value is going to be created not by creating a large company where you have a lot of employees who work for you and produce a lot of stuff.

But, instead, it’s going to be the people who create and curate software to find networks. And I think that Tesla is a software network defined car company. I think that Apple was a software network defined phone company. Nokia thought they’d sell widgets. Apple thought, no, we sell software to find phone. The bet between Tesla and GM has nothing to do with who is selling more cars. It’s that will Tesla figure out manufacturing faster than GM figures out how to be a software defined network capitalist company. So, okay, now, back to block chain. There’s a book I like a lot called The Wealth of Networks by Yochai Benkler.

I read it about 10 years ago. And it influenced my investing a lot. And one of the things that Benkler talked about was we’re going to move from the tragedy of the commons to the wealth of the commons.

And the examples he used back then, he had Digg in the book, actually. And he had examples of user generated content and open source software. Well, what if, just like the stock market, there was a new way to practice capitalism for the modern cooperation animated by the railroad and steam engine that is a new way to create abundance? Because you couldn’t have had a national railroad, unless you had a stock market. You couldn’t have said, hey, who has enough money to build a railroad. There was no one person who did. And so, now, I believe that crypto has the opportunity to create the wealth of the commons.

And rather than a centrally organized equity capital structure, you have a set of people who contribute to your project on their own volition. And if the other people, their peers in the community, judge their value as compelling, they get rewarded. So, it’s kind of like the wealth of the commons. But I find it easier to think about crypto not through the lens of, oh, so, are you going to invest in a crypto company? How many shares are you going to own? That’s wrong. That’s like asking how many dollars am I going to own in the transcontinental railroad. No. stock units are a new thing.

Tim Ferriss: Yeah, it’s a different unit.

Mike Maples: Crypto tokens are a new thing. They are a new way to create wealth. They are a new way to leverage the wealth of networks rather than vertically integrated, top down owned companies. And so, I just believe that 100 years from now, tokens or something like them will be one of many ways that an enterprising capitalist can create abundance in the world. And the more ways we can create abundance, the better.

Tim Ferriss: Does that obliterate venture capital as we know it? Or does it just reconfigure it so that you guys are investing in the pick axes?

Mike Maples: Yeah. So, I don’t really – it’s funny. So, I’m friend with Vinny Ling [inaudible]. And the first time we net, he’s like, hey, ICO’s make you irrelevant. But I’m happy to give you courtesy of my time.

And I’m like, “Vinny, look, I’m just not afraid of what’s going to be done to me. The question I asked today is what would JP Morgan do if he was alive.” JP Morgan wouldn’t be like how am I going to get disrupted? Oh, gee. He’d be like how can I play offense with crypto, and how can I create new businesses rather than – like Elvis didn’t say I’m going to disrupt jazz. He wanted to create rock and roll. And when I look at crypto, I’m like what would Elvis think? What would JP Morgan think? I think disruption in tech startups is kind of bullshit.

None of the tech startups I’ve invested in had people who said – Logan and John didn’t say death to taxis. They were like ride sharing is going to be awesome. It’s going to bring people together and make things better. And disruption happens after you win almost by accident. And it doesn’t happen because you try to defeat taxis. It happens because you transcend taxis.

So, whenever people say I’m going to disrupt something, I’m like you’re not a real entrepreneur because entrepreneurship comes from love and creation, not from anger and disruption and what am I going to attack. And so, I’m not going to get disrupted by crypto anymore than the next guy will.

Tim Ferriss: So, just –

Mike Maples: Jamie Diamond might. By the way, I’d be happy to debate him any time and anywhere about it.

Tim Ferriss: Oh, I like this. It’s a rumble in the jungle with Jamie Diamond. I can’t wait for this to happen. So, just so nobody gets fired, I did get the wrap up smiley face sign. But I’m going to temporarily ignore that. I apologize. Just so everybody knows, someone has done their duty, and I’m going to continue for a few more questions. And then, we’ll wrap up. I appreciate it. Everyone okay with that? Because I’m having fun with my bud, Mike. Oh, my God, all of these questions. I wonder if this is the same person. What nascent tech could most disempower the state?

Where do you see tech potential for removing government control over the individual? Holy shit, we’ve got a bunch of tech enabled anarchists in here.

Mike Maples: By the way, this is one of the reasons I like The Wealth of Networks is that The Wealth of Networks, potentially, creates the opening to re-establish the idea of trade as a voluntary activity between people. And the government’s role is not to own everything or legislate everything or give everybody handouts or free Scooby snacks. It is to protect the rights of people. That’s why I believe the valid role of government is to protect the rights of people. And what we’ve allowed our government to do is to have unsound practices with how they treat money. So, the Fed is jacking with the money supply. And it’s hurting honest people. If we want to explore that, we can. But the Fed jacking with the money supply is picking the pockets of the middle class. And it isn’t right. And crypto has the opportunity to say money should have a price just like everything else. Just like we need to separate politics and religion, we need to separate politics and economics.

Tim Ferriss: Oh, my God, we can go down so many rabbit holes. It’s great. Man, I can’t wait for this rumble in the jungle with Jamie Diamond. It’s going to be great. I want front row tickets. All right. What were the traits you had early on that made you successful? I’ll just leave it at that. That’s from Jignesh – I’ll leave the last name out just so I don’t have to get permission for keeping you in the podcast.

Mike Maples: I just think that I was lucky that I was born with parents who were just really good to me and inspired me in ways that were surprising that I didn’t understand, at the time. Like when I was in the third grade, my dad bought me this book called How It Works at Illustrated for my birthday. It was all of these diagrams of how a product – how does a dishwasher work. How does a car work?

Tim Ferriss: I know this book. It’s a great book.

Mike Maples: It’s a great book. And he writes in the front, it’s like, “I know this is a little bit advanced for a third grader, but it will make you think differently about life. And someday, you’re going to invent things that are going to be in a book like this. Who has parents like that? I didn’t decide that. Just like, when you’re a parent, your kids owe you nothing, it doesn’t mean you can’t be grateful when you get lucky and have good ones. Yeah.

Tim Ferriss: Here, here.

Unknown: What’s your answer, Tim?

Mike Maples: Yeah. I’m curious about that, too.

Tim Ferriss: I also, I think, in a lot of ways, won the parent lottery. I wish I could give a better answer. But the one thing my parents did, there are a few things my parents did that I think were very helpful in retrospect. Now, it’s all kind of post hoc analysis. So, who knows? But I would say 1) we did have a flushing toilet and electricity, so, it’s not like my parents were poor.

Mike Maples: You were richer than Cornelius Vanderbilt.

Tim Ferriss: Yeah. But we didn’t have a lot of extra cash floating around. My parents never made more than $50,000.00 or so a year combined. Anyway, the point was two things. 1) They said no, you can’t have the new bike, can’t do it. Can’t do this. But they said – maybe it was by necessity and not by engineering, but they said the one thing we have budget for is books. So, if you really want a book, we’ll figure it out. And so, we used to go to the remainder table in this book store in our local home town and pick books. And I remember, to this day, some of those books, just like you do. Fishes of the World was when I wanted to become a marine biologist for 10 plus years because of this book.

And I bought it for 70 percent off. And I carried it with me to school every day because the playground, for me, I was a runt, I was a really small kid. I was born premature. I got the shit kicked out of me weekly until sixth grade. So, I would stay close to the teacher with this book. And I remember, I’ve never talked about this, but I remember this one substitute teacher, not my real teachers because they knew me, but the substitute teacher said to my mom, “You shouldn’t let him bring that book to school. He’s going to destroy it.”

And my mom is like, “What are you talking about? He’s not going to destroy that book. It’s the most important book he has.” And they were very good at training us to want books. So, that was a key. And then, the second was my parents, and my mom in particular, were really good at just exposing me to a lot of stuff. And it was free stuff. It was like we’re going to take a trip to the aquarium, when it’s free. We’re going to go to the beach, and we’re going to collect black sand with a magnet, and I’ll try to explain what magnetism is. And my mom threw so much against the wall, and every once in a while, something would stick. And then, she would just put everything behind it.

Mike Maples: Yeah, me, too. I read some book, and I said the best example of this dinosaur bones is in the Museum of Natural History in Washington, DC. And my mom would say, “Well, we live in Princeton, New Jersey,” at the time. There’s a Museum of Natural History in New York. I’m like but that’s not where the biggest one is. And that’s where – sure enough, we’d be going to Washington, DC to see the biggest – and Carolyn Maples, if I was interested in dinosaurs, and that’s where I wanted to see the biggest dinosaur, by golly, we were going to Museum of National History in Washington, DC.

And maybe, while we’re at it, we’ll go to Gettysburg and learn something about the Civil War. One other thing that I think is good, and then, on to the next thing. But my dad also told me don’t have heroes. And I think what he meant by that was that hero worship is a form of not thinking for yourself because heroes, first of all, a lot of times, they’re kind of a story.

And you don’t really know what they’re really like and what really happened and why they decided what they did. But the other thing is defining yourself relative to somebody else’s accomplishment or how somebody else acts causing you to not spend the time to discover how you can be your best self. And so, it’s okay to respect the way somebody thinks. Or it’s okay to respect a talent that somebody has that you could learn from. But that’s different from saying oh, my gosh, Bill Gates is awesome. I want to be like Bill Gates. Because Bill Gates is awesome. He’s awesome at being Bill Gates.

But you need to be awesome at being you. And having a hero can cause you to drift away from that. So, my dad was always very, whenever somebody famous on TV, Ronald Reagan was president was young, he’d be like be very careful not to have heroes. You don’t know their whole story. He’s like he may be a great person, but don’t have that person as a hero. Figure out what you admire that they do, and try to understand that. But don’t say I want to be like that person ever.

Tim Ferriss: That’s a good guideline.

Mike Maples: Yeah, it’s pretty good. I don’t know how he figured that out.

Tim Ferriss: This is a question from anonymous, very nice handwriting. What would you put on a billboard? It could be, I don’t know if you answered it in the book –

Mike Maples: I did, yeah.

Tim Ferriss: So, let’s hear – it could be that, or it could be something else. But how would you answer that? What would you put on a billboard that got out to millions and billions of people?

Mike Maples: There are two things. One would be integrity is the only path where you’ll never get lost. And that’s the one that I put in your book. And then, the other one would be think for yourself always. And thinking for yourself doesn’t mean don’t listen. But it means be willing to have first principles. And you’re right or wrong not because of how powerful the person is who challenges you. You’re right or wrong based on whether the content of your ideas and first principles is right or wrong. And you should seek out people who challenge your first principles like gold because they’ll make you better. And that’s like ego is about who is right, and truth is about what’s right. And, if you become an authentic truth seeker in life, to me, that’s kind of what it means to think for yourself. It’s for you. It’s yours.

Tim Ferriss: I’m not going to follow that up.

Mike Maples: Come on, no, everybody wants to know your sign.

Tim Ferriss: I know. But I’m like the broken record player that says the same thing over and over again. So, I would say I’m going to give a new answer. Actually, I’ll give two. So, the first would be, and this is advice I got really early on that has stuck with me for decades now. You’re the average of the five people you associate with most. And Drew of Drop Box, many other people would give similar advice. And I think it’s just so important emotionally, financially, psychologically. It’s very important that you choose the people you spend time with. It doesn’t have to be in person. It can be via podcast. It can be via books. They don’t have to be alive. It can be Ben Franklin. I’ve learned so much from Richard Feynman and Ben Franklin, for instance, as just two examples.

Mike Maples: And can I just double down on that? And it doesn’t even have to be five people that will help you succeed in your career. It’s like Julie who I was talking about earlier. One of the companies that we invested in, the founder’s son was 10 years old, got a brain tumor. And so, he has to be operated on in San Francisco. And Julie calls me and says, “When are you going to get here,” like a few days later.

And I’m like, “Sorry, I’m in this meeting. Where are you?” She’s like, “I’m here at the hospital. Hugo is about to be operated on. Where are you?” And I realized she never said hey, let’s meet at the hospital. But what I realized from her was that she’s like, “What else are you doing that’s more important than being here right now? Why did I have to tell you that?” And she wasn’t being judgmental about it. To her, it was just obvious. And so, part of it is not just five awesome business people or five Fortune 500 whatever. To me, it’s more like five people who, in their own way, make you appreciate the gift of life in a more deep way so that you practice it better. And where you say wow, that person changed my point of view about how to use my time.

Tim Ferriss: How to use your life.

Mike Maples: Yeah.

Tim Ferriss: We’re going to wrap up in a minute, folks. I said I would give something new. I’ve given you are the average of the five people you associate with most a lot. So, I’ll give you another one, which is relatively recent discovery for me, which is if you want to succeed in any holistic capacity, if you want to love the people you care for fully and have them feel that, you cannot do it if you merely tolerate yourself. You cannot do it if, on some level, you loath yourself or aspects of yourself. And I’ve spent decades of my life barely, at best, tolerating myself. I had some bad things happen to me. And I, as a consequence, decided to just hone myself into an instrument of competition.

That was it. And I found validation and purpose in that and being No. 1. And any joy I felt was really from observing other people experiencing joy. It wasn’t intrinsic to me. And forgiving yourself or loving yourself is not a nice to have. It is a must have, even if you’re doing it just for other people and the people you want to express your love to most fully. You need to solve that. And there are ways to do it. That’s the good news. So, I would just say whether it’s a book like Tara Brach’s Radical Acceptance, terrible title, great book, or –

Mike Maples: Kamal’s book, Love Yourself Like Your Life Depends on It.

Tim Ferriss: Yeah. Kamal Ravikant’s book, also exceptional. That is, I think, the root cause of so many things that we can perceive as 30 or 40 or 50 different problems to solve. And, in fact, there’s one or two things that happened to you that you need to unpack and content with.

Mike Maples: Can you double click on that for a second? I think people will sometimes say you should love yourself, and they will dumb down that – they won’t understand the subtlety of what you just said. And I think that’s important.

Tim Ferriss: So, the subtlety, if we were to drill down, I would say that, and this is borrowing from someone. Actually, it’s in the conclusion of Tribe of Mentors because it’s that important to me. Jim Loehr who is a performance coach has worked with a lot of incredible athletes, fascinating guy. And his book, Mental Toughness Training for Sports, really changed my life in high school. Don’t worry. I’m getting the stink eye. I’ll make it up to everybody.

Mike Maples: Tell the whole story, Tim.

Tim Ferriss: So, Jim expressed to me, when I met with him, to learn how to play tennis for the first time, just in the last year, which I’d always wanted to do my whole life, he said, “In effect, the most important voice we ever hear in our lives is the voice that no one else hears. It’s the voice in our own heads.” And for my entire life, really my entire life, it’s been the most merciless, brutal coach you would never wish on your worst enemy.

Mike Maples: Yeah. Raise your hand if you said something to yourself negative in your own mind today? Yeah.

Tim Ferriss: And you can create, even if externally, you have all of the material trappings or rewards of a financially successful career, if you have the nuclear family that everyone has dreamed of and painted in Norman Rockwell paintings. If that inner voice is just a demon on your back, you will not find the peace that you want. And nothing you buy, nothing you achieve will provide that. There are just things you need to unpack so that that voice becomes a different voice.

Mike Maples: Is it fair, Tim, to say that part of love is like you can love your country without thinking it’s perfect. And you can love your kids without thinking they’re perfect. And part of loving yourself is saying that doesn’t mean I’m perfect. I’m not going to be jingoistic about myself. It’s more about I’m going to hold myself in high enough regard that I’m going to do the best I can with the day that I have. And I’m going to forgive myself when I screw up honestly.

Tim Ferriss: Yeah. That’s a big part of it. And also, for people who are looking for maybe a tactical recommendation, one thing I found very helpful, and I don’t want to take too much time to go into it, but something called metta meditation or loving kindness meditation.

I went through a meditation retreat recently, which was very difficult for me. And I was practicing this, just Google it, you’ll find plenty, to convey, in my meditation, love and wishes for happiness to many different people who had helped me throughout my life. And I remember one of the teachers, at this retreat said, at the very end, I was about to walk out the door, and she said, “Wait a second. Have you done any loving kindness to earlier versions of yourself who experienced a lot of pain, who maybe felt unsafe?” And I was like it didn’t even occur to me to do that. I would encourage everybody here to explore that. And I know we’re running out of time. So, Mike, I have one more question. And then, I’ll have some closing thoughts. This is the tradition to ask what is your 60 second idea to change the world? No pressure.

Mike Maples: Okay. Think for yourself and be kind to yourself in your own mind because 90 percent of the unkindness that happens in the world is actually people being unkind to themselves. And, if you set out to make the world better, being kind to yourself, in your own mind, is probably the most straight forward, high return use of your time possible.

Tim Ferriss: Cheers to that. So, Mike, I just want to say that it’s been such a joy and a privilege to know you for as long as I have. And I really hope to spend more time with you. We’ve spent a lot of time together, but I’d like to spend more time. And I really, truly believe, and part of the reason I wanted to bring you out on stage tonight, you are one of the most genuine, unentitled, positive people who want to also impart the gift of positivity to the world I’ve ever met. So, I just want to thank you for that.

Mike Maples: All right. Well, it’s been fun to see you do so well.

Tim Ferriss: You, too, man. Ladies and gentlemen, Mike Maples.

Mike Maples: Tim Ferriss. Thanks.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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One Reply to “The Tim Ferriss Show Transcripts: The Man Who Taught Me How to Invest — Mike Maples (#286)”

  1. Hi Tim,

    Love your podcasts, i’ve been listener for many years.

    I have just thought about starting to invest and noticed that Wealth Front only take customers from the US. Is there any similar UK companies you can recommend?