The Tim Ferriss Show - Episode 1: Kevin Rose

Episode Date: April 18, 2014

I consider Kevin Rose one of the best "stock pickers" in the early startup game, and he can predict even non-tech trends with stunning accuracy. Kevin is a tech entrepreneur who co-founded Digg, Revision3 (sold to Discovery Channel), Pownce, and Milk (sold to Google). Since 2012, he is a venture partner at Google Ventures. He's also a hilarious dude, and this episode involves heavy drinking.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This is episode one of the Tim Ferriss podcast. My name is Tim Ferriss. For those of you who don't have any context on me, I'm the author of The 4-Hour Workweek, The 4-Hour Body, and The 4- to dissect that skill and test it all myself. And that can range from performance-enhancing drugs, to hacking the NFL combine, to outsourcing my life to India, to cramming two years of culinary school into 48 hours, or trying to learn a foreign language in a few days well enough to go on live television and be interviewed. And it's in search of a toolkit. You do not have to be superhuman to get superhuman results. And to that end, this podcast is going to be a lot like Inside the Actor's Studio, but not limited to actors. We will have in-depth conversational interviews with actors, investors, hackers, professional athletes, black market chemists, and everybody in between. It'll be very wide ranging, but

covering it all is really the 80-20 analysis. And in the process of speaking with these people, we'll try to suss out what are the critical few things versus the trivial many? What are the 20% of tactics, philosophies, principles that they use to get 80% of the results they've had? And there should be a lot of actionable bits hidden in there or not so hidden in there for you to use in your life life or at least to inspire you. So it'll range from tactics to strategies to philosophies to motivations that they use to become the best in the world. Without further ado, I would like to introduce you through the interview to our first guest, who is Kevin Rose, a very good friend of mine, a world-class investor and entrepreneur in his own right. And his thoughts on investing

translate to many different areas in life. So I hope you enjoy it question? Now would have seemed the perfect time. What if I did the opposite? I'm a cybernetic organism, living tissue over metal endoskeleton. The Tim Ferriss Show. Alright, so, hold on, hold on, hold on. Let's start over. This is experimental, we're figuring it out. So, Kevin, would you mind doing the honors? I'll do the intro as long as you promise I don't have to do this every single time.

You do not. Okay, thank you. Once it's recorded, I can just use it repeatedly. Tim Tim Talk Talk, Episode 1. Welcome, everybody. Sexy and smart, ladies and gentlemen. This is not Tim Tim Talk Talk. We have to think up a better name for the podcast.

I know, that was the original joke name. I do like the idea of calling it T4. T4, I love that. Which stands for Tim Tim Talk Talk, but it cannot be. Well, it also sounds like a Terminator. It sounds like you're hardcore like that. T4, or thyroid hormone.

But less active form. But that's too boring. Nobody knows that. So, everybody out there, this is Tim Ferriss, author of a few books that all sound like infomercial products. You'll see, uh, after the rotisserie chicken at three in the morning. Uh, this is an experimental podcast. I have my good friend, Kevin Rose with me to make it a low stress, no stakes experiment for my episode one. Thank you, Kevin. No problem. You know, it's funny. You, you said that we should do this. And I said, why do you want me as your

first guest? Cause we do the random show together, which appears on your blog from time to time. That's right. And it's like, I think your audience would be like, oh, this is just the random show on audio. Oh, it's going to be so much better. Number one, because the audio is going to be incredibly impressive. High bitrate. High bitrate. Assuming I don't mouth the mic and screw it up with my spittle.

And I'm going to ask you questions that I normally wouldn't ask on the, on the random show as well. One thing I want to ask you is like, why did you want to do this? What, what's the inspiration behind this? So the, the inspiration behind doing this is multifold. Number one, I over the last year, I've had a chance to be on a couple of podcasts that I really enjoyed, like the Joe Rogan experience, Mark Maron, WTF Podcast, Brian Callen, Adam Carolla.

And I really enjoy the longer format, having the time to deep dive and also be really informal. I assumed it had to be very produced and edited and involved a lot of labor after the fact. And with, for instance, the Joe Rogan Experience, I was able to see that it could be done really easy, casually, and still be fun for everyone involved. I have a great time as a participant and also seemed like over the next few months, I'll be doing a lot of travel. I can't say all too much, but doing a primetime TV show on maximizing human performance using myself as the guinea pig, which starts filming very, very soon.

And I'll be on the road a lot. So I figured this would be a fun way for me to get to know people I want to get to know. Just spend two hours drinking wine and digging in. The other purpose of the podcast, and this might evolve over time, but is to very similar to all three books, kind of deep dive with people and try to extract small, actionable bits that people can use. Yeah, it seemed to me like you're on the road so much and you're constantly bumping into obviously really interesting folks. It's just a shame that you're not capturing those conversations that you're having anyway. Yeah. And just put it out there for people to consume. Right.

Because I'll go to these dinners or have wine and we'll get to that in a second and learn so much. And I'm like, God, you know, it's a shame there are only two people here, three people here, four people here. Nothing super confidential was said. I mean, it would be amazing to just offer people the opportunity to be a fly on the wall listening to some of the people I bump into who are far smarter than I am. So what are we drinking, Kevin?

So we are having a glass of or a bottle of wine from a friend of mine, Chris, who owns a little tiny, tiny, tiny, tiny wine bar in San Francisco. And when I mean tiny, I mean you can probably fit like 35 people in place. Um, it's a little hole in the wall down an alleyway. It's actually where I met my wife for our first date. I didn't know that. Yeah. And, uh, it's called hotel B Rone B I R O N. And if you're ever in San Francisco, go there and say hi to the owner. His name is Chris. If he's there and, uh, tell him that you heard this on Tim, Tim talk, talk, and you will get a discount. No, I i'm just kidding but you probably could say that he probably would give you this because he's a cool guy like that um but yeah he just thought i was just there actually meeting another uh friend hanging out and um he gave me he's like do you want a bottle to go and i was

like yeah i'm going to do tim tim talk talk i need a bottle of wine so uh my god i'm the reason i'm saying the name over and over is i wanted to stick stick. I know. You're incepting people. You're a fucker. I know. I know how you operate. So anyway, the name of the bottle of wine is Gambling and McDuck. As in Scrooge McDuck. Scrooge McDuck. The thing is, what you'll find there is that he is a really, he's a fanatical, like kind

of crazy wine connoisseur that likes really rare, obscure wines and great stories. So every wine that he'll pour you, he's like, oh, I got this crazy story. I met this winemaker, blah, blah, blah. They live in this little region and I like it because it's really obscure, hard to find grape. And so it's not really expensive wine. Like you'll go in there and like that thing. I mean, they don't have like multi hundred dollar bottles of wine. It's like standard, you know, just good prices and heavy pours. Anyway good he's a good dude he's a good should be his tagline and also for

people who are say visiting san francisco it is right around the corner from a restaurant called zuni cafe awesome which is very very well known judy rogers originally i believe out of shape of nice uh they do incredible things with their food. And you could look into something called dry brining, which they do with their roast chicken, which is amazing. So, Kevin, for those people who are listening and do not know who you are, let's start at the beginning. Ah, at the beginning.

You know that phrase because you use it. I've been doing my little podcast. But why don't you tell people a little bit about your background, where you grew up, et cetera? Sure. You know, I grew up kind of a boring life in Las Vegas, of all places, which I don't like to admit to many people because it's a fun place to visit, but it's not really a place I consider home anymore. I do like going and hanging out with friends.

Obviously, the occasional bender out in Vegas is always fun. But so, you know, I moved out to the Bay Area in 2000 and started working at, you know, dot coms at the tail end of that in the tech space. Ended up working at Tech TV and starting there in 2002, late 2002, kind of behind the scenes. Eventually ended up doing segments on a show called The Screensaver. So I was actually on-air talent. And where was this?

This was in San Francisco. Got it. And how did you end up in SF? I just moved out here working with, I was actually doing some marketing. I was doing ad buys and helping them track the conversions on. For Tech TV? No, for a little startup, a CMGI-funded startup. It was an online furniture store. We thought we were going to make billions.

But it turns out people don't like to pay the shipping for really heavy furniture on the internet. Kind of like kettlebells. Yeah, it didn't work out. Yeah, it was very heavy stuff. So anyway, I ended up hosting a television show on the screensavers. The name of the show was called The Screensavers on Tech TV. And then started my own first startup, which is called Dig, which is a social news site.

And that grew that to a pretty decent size. Started a couple other companies. Ended up angel investing, sold a few companies, got acquired by Google. Long story short, had a big long 7, 8, 9, 10 year run in the tech space, and then eventually ended up as a venture capitalist at Google Ventures. So I'm a VC there that is funding companies and helping find the next big thing. That was a very efficient self- big thing. That was very efficient. Self introduction.

Thank you for that. No problem. A couple of questions. Well, actually I should give some, some background, I suppose, or just my personal views on things since that's,

I guess, part of the podcast. I think you're one of the best product guys in Silicon Valley, meaning your ability to not only conceptualize and come up with product ideas, which you do all the time, and then you just give them away or drop them or whatever. But you come up with a different company idea that could work ostensibly, I think, every week, just about. And you're also extremely good at betting on the right horses. And of course, no investor is 100%. I mean, they can't bat a thousand but what what do you

think makes you good at that i mean i because i i think many people would share that same opinion you're you're good at guessing what's coming next or predicting what will pop or what will not pop is that just genetic ability i mean you're like uh it's, you know, LeBron James of angel investing, uh, or is that, are there characteristics that you see in yourself or in other people who are also good at it? Uh, that, that you can explain it. It's, that's a great question. I think that, um, for me, you know, I, I can remember, uh, analyzing people and trends all the way back in high school. The first time I remember it, I remember there was this one kid in my class that he wore a fluorescent orange jumpsuit to school. It was like a garbage man, like what the garbage man would wear.

Or an inmate. Yeah, or an inmate, exactly. And so he was wearing that, and I remember everyone thought that was the coolest thing. And everyone's like, oh, he's got that jumpsuit on and blah blah and like kids started going out and like literally buying these you could buy them um they weren't made by dickies but a very similar brand and they sold them actually i think that maybe they were made by dickies but they sold them at kmart and so kids started buying them wearing the high school and i remember at that point i realized that there are certain very early adopters like tastemakers i was like if you could only like this person can spread a

trend and at the time i was thinking about fashion right because like this kid was like considered by by many other classmates to be like the cool kid right and so once he did something he would influence all these other people and so i started thinking about like it just made me think like what could i make that he would think was cool? And then it would spread throughout the class. That was, like, what I got excited about. And then I just realized that I just, like, I kept coming up with all these ideas. And I've always been the kind of person that just, like, starts to think about.

And I think it was, honestly, it was just something that actually hurt me in school. Because I was always daydreaming about different things. And I actually got really crappy grades and just like, you know, didn't do well in school because my mind was always someplace else. And I think that it was always, um, once I got connected up with computers, um, and I got really into computers, uh, it was always about what I could build with software. And so, you know, I built a couple little things that I launched as Shareware and had on Shareware blogs and stuff like that

and made some money. And then it kind of clicked that, you know, you write the software once, you charge for it, and you don't have to keep paying to have it made. You can just make more and more copies. Money while you sleep. It was insane, you know? And so, like, that clicked.

And then i started thinking about like what are the things that that i would like as a consumer and that that i feel could spread and like really take off and then you know it was kind of like analyzing these companies and looking at these different things and seeing them and and being that early adopter where you want to play with everything i think you have to have like a natural, yeah. The number of apps you have on your phone is incredible to me. You have to have like a natural curiosity. You have to like say, okay, I want to like, I get excited. I get a hit of like freaking dopamine and like my, like flutters in the stomach when I see something that is new and original and has never been done

before. And so like, I feel that what would be a few examples of that? Well, I think that, you know, what are a few companies you've invested in or missed for that matter, where you got the flutters in your stomach? Well, I mean, so Twitter, for example, um, you know, it was very early days when I invested in Twitter and, um, and, and you were shortly thereafter, we were both investors early on two weeks later, I managed to come in after around a financing closed. You got screwed. The person selling it to me was very smart, very shrewd. They held off. We got two very different valuations. I got really lucky on that one and Tim kind of got screwed. But the thing is, when you were looking at Twitter, there was two things that really caught

my attention. One was that Jack Dorsey, the guy that that created it had created a model that was not about mutual friendship so up until this point it was about you know facebook and myspace and others you had to send a friend request and someone had to accept your friend request and that's the way that a social relationship happened on the internet jack was smart enough to think like hey well maybe it doesn't have to be like that. Maybe you can tail and kind of like follow someone that you don't actually know. And so when he created that, I remember thinking like, wow, this is crazy. Like there was a bunch of like influential people that started to sign up, you know, and I was like, I can kind of like peek over their shoulder and kind of be with them on

this journey that they're going on and like watch what they're up to without actually knowing them and i was like wow okay what if celebrities actually figure out how to use this thing and it's really easy because all you have to do to tweet is send a text message and then you know you saw a celebrity or two sign up and i'm like okay this is gonna be pretty huge because if this keeps happening and more and more celebrities sign up it's gonna be their platform because they don't know how to blog. They don't have low, it's low labor, low, like the barrier to entry is extremely low. You can misspell everything and it can be two sentences and it's still like content.

Right. And so seeing that, and then also figuring out that a follower account wasn't portable. So if you think about like you have an email newsletter, you can move that from email provider to email provider. Right, Aweber to MailChimp to whatever. You can't move your followers to Facebook. You can't move your followers so that it was very defensible in that way. And seeing those couple things and thinking like, okay, well, this could be something.

And again, I didn't know. It was just like it was a gamble. And a lot of angel investing for me is going on your gut. And so I placed a bet and just happened to win there. But I think that for me, it's like hopefully finding an insight like that and then also finding something that you yourself plays to me as a consumer. I think I'm kind of an every man, every woman, every... I don't know if I'm a woman, but I didn't mean that. You are like every woman. I man like every woman every i don't know i'm a woman but i mean like i didn't

mean that but you aren't like everyone like every woman uh but no seriously though i i think that like i i kind of feel like if if it's something that will appeal to me and i can see myself using it on a daily basis like i'm going to open my phone to do this two to three times per day right it could be a big deal and i think that like you know that's what i look for that's when i'm trying to you know find the next instagram or whatever it may be it's deal. And I think that like, you know, that's what I look for. That's when I'm, I'm trying to, you know, find the next Instagram or whatever it may be. It's like, I'm looking for something I'm going to use on a daily basis, something that's going to sit in my, you know, there's like 20 spaces on your iPhone and the default screen. Like what are one of those icons going to be? Is there going to be something that's that, that prominent that, that, that is that

important that it will take up some of that real estate, some of the default real estate on my home screen. What, what are some examples of, uh, and we'll talk about a lot more than investing, but I think it's a good way to look into how you think about people and companies and just creation in general. What are examples of companies you've invested in that other people did not invest in, where you were not necessarily investing alone, but going against maybe the consensus and why did, and why did you, what were the factors that led you to decide to go in, in investments that worked out? We'll also talk about ones that didn't. Yeah. I mean, I think that it's, there's always investors that say no, including myself,

and a lot of things that actually end up being really successful. So you can't really blame somebody. It's like, I feel like, and I'm sure there's this case for you. It's like you look at 20, 30, 50, and now as a professional venture capitalist, like hundreds of deals per year. And you're going to say no to a lot of winners out there so um you know it's it's for me it's like i don't feel as though i've gone into something all in into something that like totally has um everyone was against because there's always somebody

willing to invest in that startup sure look i guess a startup where it wasn't the like hottest girl at the dance of the moment. Because you know exactly what I mean by that. There are some deals where it's like, everybody wants in. Everybody thinks it's amazing. Not one of those deals. A deal that had less hoopla surrounding it. Yeah, I mean, I think that there's been a few of those within the last even year and a half or so i i've gone into a handful

of deals that are now starting to work out like next door i think is a great example yeah of one that i invested in maybe a year and a half ago we both invested in yeah so it was like it's a neighborhood social network and i think that uh there was a lot of people that were like i just you know i don't know what that's all about or what it means and and for me um you know it's funny it's like i don't want to come off on this podcast sounding like i'm like i'm a know-it-all because like i've been wrong on a lot of deals yeah but like every once in a while you you you kind of like see a market before it's about to happen and then sometimes you just miss it all together like pinterest i i had an opportunity to invest very early on saw it liked it ended up passing and i'm kicking myself every single day right but um you know

next door was one where i saw it i was like okay well this is connecting neighbors on a very social level which i like because it's something where in san francisco in big cities we don't know our neighbors it's not like you can walk across the street and be like, Oh, Hey Jim, how's it going? You know, like you might know one house in any direction, but not two or three houses. You don't know who those people are.

So the idea of like creating that social fabric so that you can have like ad hoc things come together, like social, like a neighborhood watch programs, like, and, and eventually like commerce on top of a neighborhood graph, which I think is really interesting.

Like types of commerce, like, like on top of a neighborhood graph, which I think is really interesting. What types of commerce? Like goods, goods being sold. Like I see couches for sale on Nextdoor, which were for sale on Craigslist, you know, six months ago. So things like that, like that trusted neighborhood network are starting to create really unique opportunities for people to exchange goods and services. You know, there's like a plumber that was on there last week being like, hey, I'm a plumber. I live in the neighborhood. Does anybody ever need me?

It's just a different platform that was created out of neighborhoods that have people getting to know each other in their local neighborhood that I thought was interesting. And I think that a year and a half ago, nobody was really talking about it. Nobody just really thought it was that exciting. What do your investment mistakes have in common if anything if you were to if you were to say like you know what i should have known better because x i did x i didn't do x

such and such happened shouldn't have done it well i I did. Well, I think there's, for me, it's the mistakes that have occurred, I think, are one in passing on deals. Like, I think that when you're using your own money, especially when you're an angel investor, you are very, extremely picky, almost too much so in that you know on a one to ten meaning ten is like you're just over the over the moon excited about doing this deal when you're an angel and you have limited capital you're thinking like okay well i have to be a nine or higher to make this happen to actually want to put money into this company um and i think that there was a lot of great eights in there that i just passed on yeah and, you know, had I had more cash at the time, I probably would have done those deals. And some of those, that's also because, I mean, as an angel, you have very significant

downside, meaning you're, you can lose all of your own capital. Right. Uh, and then you have the potential upside of a relatively say small investment because you're on cash. Whereas if you're working at a fund like Google ventures, you have hundreds of millions of dollars to deploy. Sure. And so you can put a hundred K bets all day long,

right? And then it's zero personal downside and ride the winners. Right. Um, so I think a lot of, a lot of mistakes have been there. A lot of mistakes have been, you know,

there's always the, the deals that you fund because you're, you're friendly with with you know as an angel you're friendly with some some people and it's not necessarily and you're backing them as an entrepreneur because you you really like the person and there's nothing wrong with that you just you you you're betting on a person you don't might not necessarily like the the general space that they're in but you're betting they can kind of figure it out yeah and sometimes you sometimes you lose, uh, on those and that's fine. I mean, you just kind of,

that's, I mean, that's true. Also, even with the example you gave, which is Twitter, I mean, if we're looking at audio and I mean,

it's, uh, or for people that don't know, audio was the startup that, that became Twitter. Right. And I mean, Ed has had a lot of businesses as,

as you've mentioned in interviews before, or he's mentioned interviews before. I mean, VHS tapes to teach people how to use the internet. Right. What was your first business? Uh, my first business was, um, a piece of software. Um, well, I mean, it goes way back before that when I was like 12, I had a little software company called foliage software. Um, and it wasn't actually a software company, but had business cards made so it felt like a software company but i i basically uh how old are you uh i'm maybe 12 something like that and i and i and i basically wrote little programs uh in basic and then i would actually i found this program that would that would compile actually

wasn't basic i wrote i wrote some like tricky little utilities uh actually using batch like in batch files and then i wrote i got some software that compiled them to exes and then tried to sell them to shareware but anyway it was uh that was super geeky but uh i've always been tinkering for a long time what if you were not in tech actually no that's fine if let me dial back actually it's probably not 12 years old so maybe it was later what was the shittiest job you've ever had uh working in olive garden i made breadsticks there i smelled like garlic all the time i think it's important uh this is something uh a mutual friend of ours has said uh as well uh chris saka that it, that I think it's important to have had at least one shitty job,

preferably in the service industry. I think it really teaches you a lot about yourself and service and humankind in general. So you were making the breadsticks in the back. Did you ever have a busboying or waitering job or anything like that uh if not i forgive you no not really i was never a waiter i mean i would see people at tables at olive garden as well but like the the don't don't hate on my breadsticks breadsticks were a tough job dude like those waiters would get pissed at you if you didn't have the breadsticks out on time because they get made their tips on breadsticks they made their way how do they make their tips you had to have breadsticks on the table dude breadsticks always have to be on the table i still have dreams about this breadsticks. They made their way. How do they make their tips on breadsticks? You had to have breadsticks on the table, dude.

Breadsticks always have to be on the table. I still have dreams about this. Breadsticks need to be on the table. If the customers don't have their breadsticks, they are not happy.

They're pissed. Yeah. It's all you can eat breadsticks and salad. That's a lot of breadsticks. I mean, dude, it's a lot of breadsticks. I was cranking out,

like, at any given time, there's two big-ass trays of breadsticks going on in the Olive Garden in the oven. All right. All right. Let's, uh, I'm going to do a couple of rapid fire questions just to mix things up. Actually, let me, I wanted to also just add a bit of context to the angel investing discussion

because it may seem outside of the scope of your daily life, but things are going to change very dramatically very soon. Oh, yeah, absolutely. Jane, so to speak, the public will have access to deals that are advertised by or promoted by angel investors, venture capitalists, hedge fund managers, and so on and so forth. This is something that's unprecedented and related to the JOBS Act, which means that deals people previously had to be part of a very small club to have access to, they will see promoted on the internet and elsewhere. Who knows? Television, perhaps. So I think the mechanisms for determining your own risk tolerance and deciding on investing will become in some ways more complex because people are going to get hit with a lot of

promotion. So just a passing recommendation to people would be to read the annual letters by Warren Buffett, which are compiled and gathered in paperback form. And of course, the first rule of investing is do not lose money. Rule number two, see rule number one, according to Buffett. But as an angel, I that's important i mean you need to develop rules you're going to miss some winners but develop rules so that you can at least avoid losing a large chunk of capital and uh that is all i have to say about that yeah i mean it's interesting to think that um there's going to be this this act is going to open up new worlds for for everyday investors to come in and do more angel style investing. Yeah.

So the way that people go on a Kickstarter and give money to people for prizes or rewards of different types, they'll be able to do that. But for equity, actual percentages in a company, it's crazy in that, like, you know, when, when you hear about most of the stuff you think like, Oh, it's those people out in Silicon Valley in California doing all this stuff. And it's like, and, and you're right most of the stuff you think like, oh, it's those people out in Silicon Valley and California doing all this stuff. And it's like, and, and you're right to be thinking that like, there's obviously a lot of that stuff gets funded and everything out here, but like this, this, when this happens and eventually the tools that form around it will enable anyone anywhere to really participate

and get involved at a much earlier stage, which is exciting. I mean, there's a, you know, I mean, there's a lot of risk, but there's also potentially a lot of reward on that stuff. Definitely. I mean, we've talked about this before, but I mean, I tend to take personally, at least as sort of a barbell, that's the Nassim Taleb term,

barbell approach to investing, which is say 20% highly speculative startup stuff. And then 80% is just safe cash-like equivalents of some type. So don't gamble with more than you can afford to lose is a, I think a good way to go about it. All right. So let's, let's do a couple of rapid fire questions.

Uh, borrowing these from all over the place. If you could be a breakfast cereal, what breakfast cereal and why? Oh boy. It's these kinds of questions. This is like the Google interview questions. Like when they're like, what breakfast cereal and why? Oh, boy. It's these kind of questions. This is like the Google interview questions. They're like, how many ping pong balls can you fit in a 747?

Yeah, exactly. McKinsey style. This is easier. What kind of breakfast cereal? I hate the and why part. I mean, I can easily be like some nice like... Okay, you can just give a cryptic answer. No why report.

Okay, breakfast cereal. You know, I'm going to go with the steel cut oats. It's very Amish of you. Well, I, are we talking like kids cereal? I mean, it can be whatever, man. I don't want to like suggest something that's bad for people's health out there. Then they start consuming it. And all of a sudden we're like double fisting wine here.

You can't suggest cereal. Okay. You're fine. it and all of a sudden we're like double fisting wine here you can't suggest cereal okay you're fine so i would say like straight up kids breakfast cereal would probably be um like the choco puffs okay now i'm gonna go back on my word why why choco puffs well i mean just because i really like chocolate cheers but i don't really have any like oh cheers i don't have any like great great answer other than just like that was a terrible question even worse answer all right let's continue this is a beta man this is a beta this is a bit never again will the breakfast cereal question come up

that was a shitty lead on my part complete this statement my favorite time of day is and why uh probably evening just because i i get to decompress a little bit how do you decompress in the evening um you know it's it's dinner with my wife and just kind of like hanging out and having you know a glass of wine or something and especially like wine with with good food is is awesome we cook a lot at home what is your favorite meal and wine to decompress so without a doubt and uh i found this little uh little charcuterie place around the corner from my house that sells like aged beef okay and um 100 day dry aged big old chunk of beef uh sous vide uh in the water bath like at medium rare and then just like flash grilled.

So you like render all the fat and like, and then just a big old tasty cab. I mean, I, I, that sounds great. That just, I know you'd like that,

right? I would like that. I would, I would. So medium rare would be what? Like one 25, uh, one 30 to one 35 is medium rare.

Uh, okay. How do I know that? And you don't, and I have a, you have a cooking book. You're going to cut this out of the podcast. I'm not gonna cut it out 125 is fine 125 that's on the rare side yeah i know but if it's thin and then you are it doesn't matter with your flash sear it no hold on though if it's thin and then you sear it yeah you're gonna have

some carryover you're gonna carry enough jesus freaking chafing my ass already. All right. As you've gotten older, this is a two-parter. As you've gotten older, what has become more important to you? And what has become less important to you? Oh, gosh. So more important to me as I've gotten older is probably just honestly time to like stay in shape there's a good more gym time more time to actually like actually keep the beer gut down uh you know it's harder as you get older and less important i would say is like some of the hardcore tinkering like i used to like to build computers from scratch.

I just want my computer to work now. I put freaking OS X Mavericks on my laptop, which is the beta version of OS X, and it's crashing shit. And I'm just like, are you kidding me? What am I doing? I don't know why I had to have it, but I did. Now I can't even write an email.

My browser locks up. So I think I just, you know, it's like write an email my browser locks up so uh i think i just you know it's like they get off my lawn like i want you to grandpa i just want you to work but you know it's weird how that happens yeah i have the same thing i mean there's a point where you just fear you feel the scarcity of time yeah and the value of time increasing because you start, you start seeing gnarly shit happen to people or like friends dying or, Oh, I know that's the scariest part,

man. It freaks you out. I didn't know anyone. And then you're like, you know what? I'm not gonna spend a week figuring this like beta out. That's bullshit. I just want this to work. You know what's funny is when you're a kid,

like you just don't know anyone. You think like everyone's just healthy. Right. And then all of a sudden you become an adult and like you know i gosh man i've had some really bad experiences and then like i've seen friends of mine that aren't that older that like you know a friend a good friend of mine's wife has cancer now and like he's only a few years older than me and i'm like that's scary as hell yeah so yeah you start to value time a lot more uh who's the first person that comes to mind when you hear the word successful and why is that?

Successful, I would say that, you know, I think that it's Philip Rosedale is the first person to come to mind. Philip's awesome. Do you want to tell us a little bit of just to so people know who philip is so it's interesting in that it's weird that actually when i think about that i would pick philip and the reason being is that philip so thank you for the wine i wonder if that's picking them by the speaker it sounds like i'm aggressively pouring so thank be picked up by this mic. So, Philip created a virtual world back in the day that was really popular way before its time called Second Life. And it became extremely popular.

And later, like all Internet things, eventually declined in usage because it just wasn't as cool as it was when it came out. And he then went on to start a company that, you know, he tinkered around with a handful of different things that didn't quite work out. And now he's on to his next thing called High Fidelity. But the reason that I say Philip is that success in my mind doesn't necessarily mean like huge IPOs and exits and things like that. The thing that I like about him, and I shot a couple of video interviews with him on my series on Foundation, that you can search Philip Rosedale Foundation on Google and find. Foundation.kr. Foundation.kr. Because you let the.com slip.

No, yeah, right. Foundation.com was not available the dot net which one is this dot busy or something like that i like dot kr slip but i got it back so uh anyway the thing i like about philip is that he is such a rare person to to discover i feel like i'm lucky that i even know him because he's a big thinker he's a crazy mad scientist when you watch his interview you realize that his ideas and his passion and just where his head takes things is so unique and so big picture like bigger than you could ever dream up on your own like when you think of ideas we're like oh wouldn't it be better if there was a better way to keep our you know like and it's something like super stupid that you want like

you know like like i feel like our ideas are like you know just improvements of the incremental like pre-existing like little problems that we have that like my toilet paper runs out i'd like to get a notification like it's like dumb stuff right you talk to him and like you realize that like he is thinking about things like virtual economies and like currencies and using your iphone as a miniature computer while you're sleeping that does little virtual tasks and assist people like in other places and you're like dude you like they will someday when you finally have that moment, that idea, that is the right idea at the right time, when it hits, they will write books about this guy and movies about this guy. It's rare to find those people. Nikolai Tesla of the internet age.

It's the Tesla. It's potentially like an Elon Musk is another one of those. I was just going to say, what do you think enables them to think that way? Is it something that can be taught? I mean, is it something that they learned how to do? Or are they just genetically predisposed? I think a lot of it comes down to fear. A lot of it comes down to fear.

How so? When people don't have fear, they aren't scared of big ideas. I meet a lot of entrepreneurs every single day, and all they want to do is do incremental improvements on preexisting stuff because it's safe. Sell a company for 20 million. They can sell it for 20 million to Yahoo. They can sell it for 10 million to Google, whatever it may be.

There is a, there's a safety net there. Who wants to go and create electric car company? Who wants to go and create a freaking next generation, like, like spaceship company? Like these are, these are just,

these are hard problems, you know, it takes a certain kind of person and they're binary to it. Right. I mean, you either, you don't partially succeed, right. You either succeed or fail. And it's like, and Philip is one of those guys that he's just like, I have a crazy idea. I'm going to go build it. And I don't care what nothing's going to get in my way. I can just do it. Like, and I don't know how to do it right now, but I can figure it out because i'll surround myself with smart people and that's that's what he does and it's like those people are really rare man like i see so many just um you know it's it's not a lot of like willing to throw everything out

and just start from scratch and tackle something that is is is going to change the world and and when you find those people and i've only met a couple you know i i then you get really excited and you feel lucky just to know them who uh any other examples immediately jump to mind besides uh philip and elon uh you know i think that um reed hoffman is another really big idea guy i think that he's really like i'm excited to see if he eventually decides to get back in it like you that he's really like i'm excited to see if he eventually decides to get back in it like you know he's chairman at linkedin and if he ever decides to go and and tackle something like what that will become do you have any idea what uh philip if he

did i don't know his educational background but did he did he finish school did he study anything in particular yeah i mean he's he's like super hardcore like machine code he is computer science guy okay because i mean i don't know if he dropped out or not or just trying to see if there are any commonalities because i mean reed many people don't know this but uh i think he has either a master's or phd in in philosophy i mean very big thinker as you know is regarded as one of the oracles or the Oracle of Silicon Valley. I mean, the guy's brilliant. Yeah,

absolutely. Hmm. What is your, it's not policy really, but do you keep in touch with friends from back in the day? I mean, childhood friends, any of them or?

Yeah, there's a couple. Okay. So I mean, that friends, any of them? Yeah, there's a couple. Okay. So, I mean, that's been, I'd be curious to hear what your experience has been as you've had more and more success in various ways and entered new peer groups and so on and so forth. How has that affected your relationships with people that you grew up with, if at all? And from what period of time yeah it's hard because you know growing up in such a a city like las vegas like no one really stayed there so it's not like when i go back to town i see all my friends from high school or whatever it may be or college like it's um we all split off and went to different places i have one friend that's still there.

But other than that, everyone's in different cities. Some are back east. Some are in LA. They're just all over the place. But I try and keep in touch. I'll trade texts. There's certain times of the year, certain things that come up in your head that pop in your mind. You're like, oh my gosh, that was so crazy when we did this.

And he's like texting your buddies right i remember when we you know broke the law this way something like that you know so there's like there's that kind of stuff um but uh you know uh what was the i mean i know the question was like i mean maybe maybe it seems like an odd question is this something that you're having a hard time with i it's it's a challenge in some cases for me i've just found that I grew up in a very odd place. I grew up on the eastern end of Long Island in the Hamptons, where you have two groups. Actually, there are more than two groups,

but for simplicity's sake, you have the city people, who are rich Manhattanites, typically, who come out to summer in the Hamptons, and then you have the townies and the townies uh range but typically include people involved in service industries so uh let's just say landscapers waitresses waiters uh real estate brokers although they're getting pushed out by people like sotheby's are based in manhattan and there's a lot of alcoholism not very good education uh it's a pretty dismal picture so i i i found it very difficult for myself uh to transition from having more in common with the townies to having more in common with the

city people it's been like a real existential issue so you don't have things in common with the city people anymore no no i i had i as i went through say high school and then uh left long island i initially was 100 percent townie and then i started to move where i'm like okay 90 percent townie 10 city person as i went to undergrad right and then like 70% townie, 30% city person. What do you think you are now? You know, I can empathize with the city people now. And I feel like I'm straddling both, right? So I go back and it's like I have some of my closest friends who have died in the last two years of drug overdoses.

That's crazy. And so I feel like I'm kind of trapped in between these. Not trapped, that's the dramatic word. But I'm straddling these two worlds where I grew up hating people who came in from Manhattan. I mean, they were just like so rude and entitled and annoying and irritating. Part of it was that I was working as a busboy, so I saw the worst that humanity had to offer. And now it's difficult for me sometimes to identify

and let's say have a conversation about shared interests with some of the friends I grew up with. It's not because I'm better by any stretch of the imagination we're just in such different tracks I still feel more at home with my younger friends old then I will I feel like a fish out of water in the Bay Area well okay so I would caveat what I just said with the fact that I left Long Island to go to actually petition my parents to do this to go to, actually petitioned my parents to do this, to go to a boarding school in New Hampshire.

And that's where I forged my closest friendships that I still have to this day. So I am absolutely closest to those people. When I went to college, didn't have a lot of close bonding experience because I already had the away from home scenario. But it's, I don't feel like a fish out of water in the Bay area, but it's, it's, it's proven harder to develop really close friendships.

I think the further you get along in a certain professional track not always. I mean, I do have close friends in the Bay area, uh, but, um, not to, not to meander too far, but it's just, it's, it's something that I've seen. Some people have a lot of challenges with and other people don't have any with. Yeah. I think that for me, um, you know, I grew up in a pretty lower middle income family. Um, and, uh, I do, I feel that, um, that's always felt at home. And I have a bunch of really crappy 90s tattoos. What's your worst tattoo?

Can you explain to someone? Like freaking flames on my leg. I've got really bad tattoos. They're in the process of getting removed. I will pay you $10,000 if I can put a tramp stamp on your lower back. I'll give you $20,000 and we'll do the same thing. You'll give me $20,000 if I put a tramp stamp on your lower back? I'll give you 20 and we'll do the same thing. You'll give me 20 if I put a tramp stamp on your lower back? I can't.

Here's the deal though. I feel like I feel at most home with people that understand that. Because I go to the gym. I go to this really meat-heady gym. That's perfect.

I'm surrounded by dudes with really crappy 90s tattoos. And I'm like, oh, I feel at home here. They have like Tasmanian devil tattoos on their arms. Oh, what's up, bro? Hell yeah. Like, it's the best. Allison Shands, what's up? Yeah.

What did you want to be when you were growing up? I always knew I wanted to be in computers ever since I was probably 10 or 12 years old. Nothing else? I knew. I knew the second I in computers ever since I was probably 10 or 12 years old. Nothing else? I knew. I knew the second I got a computer that I was hooked. I moved the computer into my bedroom, and my parents thought it was weird. And I was like, I need to have this machine as close as possible so I can hear the fan at night. It makes me sleep.

I'm serious. I loved it, dude. Everything about it. I'd leave it on all the time. I'd get on it. I learned every single DOS command. You can ask me how to do anything in DOS right now. I can tell you how to do it. I loved it. I learned every single DOS command. You can ask me how to do anything in DOS right now. I can tell you how to do it.

I loved it. I wish I could. I definitely have non-engineers insecurity when it comes to, or non-coders insecurity when it relates to tech and startups. I really should learn how to code at least in one language. Everyone's, not everyone, but a handful of friends have been telling me I should go after Python first, which I'm inclined to do i get to it eventually natural languages first programming languages second i guess interesting uh outside of computers if you could study with any expert

in the world who would you study with and what would you study um i would probably pick some type of meditation guru. Hmm. And, uh, and I know this is totally doable, but like, I think that like the issue that I have now, um, is that I feel that all of this computer, like the computers and the constant like stimulus and, in all this like you know i don't know about you but like there's no such thing as it's extremely blurred the personal time versus work time and so like you know i'll be at dinner and like you know it's not this bad because daria makes me shut down the laptop at dinner but like you know what i mean it's like

it bleeds into everything that you do and so because of that i feel like my brain is being slowly scrambled like i feel like your brain is always on edge it's being fragmented and i feel that like we're gonna realize in short order here in the next 10 20 years that like all this distraction and stuff is really messing with our brains. And I feel like I need to find that balance and I haven't done that yet. So I think if I, if I could study with anyone, it would probably be like a, a two or three month, like just straight up retreat with like some like awesome Buddhist monk

somewhere that would teach me, uh, you know, walking meditation or whatever it may be like some, some way to like like gain my soul back kevin has lost his soul that would be the title of this podcast no kevin rose loses his soul as long as it's like tim tim tok tok kevin rose no but seriously though i i feel like it's it's it's so hard it's easy to feel lost i mean i've we've i i don't think

i've talked about this all too publicly but um it's been uh i feel like i'm an aa or something wording it this way but it's been it'll be 11 weeks as of this sunday that i've meditated twice a day every day for that period of time which is it would have been incomprehensible to me that I would actually meditate that consistently. You're not counting masturbation as meditation, though? No, no. Because if you are, then that wouldn't count. Then you're like four a day.

You're like once a week then? I've never masturbated. I have no idea what you're implying. It's a late night show, people. It's a late night show. Sorry all you seven-year-olds listening, but in three years you'll learn. I'm not counting masturbation. Is this a late night show though, seriously?

Because we talk about more vulgar stuff. Yeah, what do you want to bring out there? There's nothing else I want to talk about. You want to talk about penises? What's going on? No, there's nothing else. I was just worried. You always talk about penises. You might as well admit it to everybody. You know what I heard? Yes. Say what you want. Say what you didn't want to say. No, I mean, it's nothing that's, that's interesting. That's fine. Sounded, it sounded defensive. So you should bring up my buddy that, that, uh, that, that owns this wine bar. We were just like talking about it. He got square, you know, that card swiping system i'm explaining to the users out there so square is basically like this little tiny dongle that

you can plug into your ipad or iphone and you can swipe your card and dongle is a little square that you plug in sounds very pornographic you swipe your card and that's how you pay for things everyone's kind of seeing this now so basically he was telling me that 30% of his signatures, like, you know how you have to sign the iPad with your finger. Like you said, 30% are penises. That is awesome.

I'm going to start doing that. Because then if the credit card company, I guess this is your signature. I'm like, what the fuck do you think? It's a penis. And of course, I see more scribbled penises than like,

he's like, you even believe he's like, people are drunk and they just sign a penis. I thought that pretty awesome why have i never done that i don't know i'm embarrassed to admit that i've never signed a penis before uh so if you go there yeah and you see chris and you get that discount sign with the penis sign with the penis uh so speaking of balance technology and so on as so i don't count masturbation, just to come back to that. 20 minutes a day, twice a day, transcendental meditation, blah, blah, blah. I'll talk about it more another time.

I want to focus on you, Kevin Rose. Technology. It does cause a lot of blurring. So you get this work-life blending instead of balance. What is one technology you think you could live without or two television absolutely okay except for football okay and now what if we can't now let's just say because there are a lot of self-righteous san francisco techies and i'm sure they're elsewhere who are like oh i never watched television i don't even have a television and then watch five hours of fucking youtube every day right and that's just

ridiculous yeah you can't say you don't watch television no no that's fine but if you're watching like jaguars attacking crocodiles and like kitten videos sure parkour for four hours on the internet like it's the same thing yeah i mean if it time wise yeah i mean they talk about how much like the average American household watches TV. And don't get me wrong. I do enjoy a great movie. I enjoy a miniseries like About Star Galactica or something like that. But only once it's been a few seasons in and people are like, oh, you got to see this.

But rather than that, I would rather spend time working on businesses or building my own stuff. I think that's one of the key. You were talking earlier about like traits that entrepreneurs like successful entrepreneurs have and like no all the great entrepreneurs i know like they they work their projects bleed into their personal life and it's it's sad but it's true and they they they're focused on that and so like you know when i was building several some of the companies i built in the past, like it has always been about cutting out that type of stuff, like figuring out where you can prune and cut and create more space so that you can actually have the time to put in the 10,

12 hour days. And it doesn't feel like it, especially when it's something you're really passionate about. It doesn't feel like you're putting in that much time, but like it's, you can't expect to be a successful entrepreneur just working at nine to five like it just doesn't work that way and you don't just to address a common i think misconception with the whole four-hour shit that uh that everyone's gonna i know i said that they're

like oh you haven't tried i know tim ferriss the fuck so let me address that the for people who haven't read it uh the four-Hour Workweek is about optimizing per hour output. That's it in the story. So you maximize your per hour output, increase it 5 to 10x. Then if you're, let's say, a VC or an investment banker or whatever, you still work the same number of hours, but you have improved volume of output. Same for startup people. The objective is to use your time wisely and allocated to the things that you're passionate about. And in that case, for you, it would be, let's say, some of your startups that you've worked on. For me, where I feel like I am

an Archimedes lever or can utilize the Archimedes lever to really have the broadest impact is, say, with the book. So I'll spend three years on a book that's a serious investment of time but uh the the objective is not to be idle so just to emphasize that and i think that once you you should be looking for something that consumes you in a way and i know that might sound negative to some people but it's like if you're not a hell yes about what you're doing then why are you doing it uh or should you be looking for something else yeah uh i think that's a good point so television all right fair enough speaking all right let's let's drop tv you mentioned documentary any favorite documentaries um yeah i mean there's oh gosh i have to go back and look at the stuff that uh

i've watched like um what is it uh like uh food ink food inks food is a good one that's a great one i really enjoyed that one to kind of like shed some light on like the industrial food process and how nasty and horrible it is um that's definitely top of my list um i don't have any that jump out as being super exciting that man on wire is worth watching that's fun have you seen who killed the electric car no is that any good i i heard that was pretty good graham's giving the thumbs grammar this three-person podcast who killed the electric car what's it about uh well just the the how the electric car died the first time around when they try to get off the ground yeah the yeah the gmv one interesting who was it that came out with the nova at one part at at one point uh thank you wine for that

english fuck up uh and the nova the nova and then they tried to sell it in spanish-speaking English. Fuck up. The Nova? The Nova. And then they tried to sell it in Spanish-speaking countries, and it was the Nova. It doesn't go. And so they couldn't sell the car. Oh, that's funny. Oops. Okay. If you could stop the clock and live forever at a particular age, what age would you choose?

Man, that's a good one. Probably. I mean, that's a good question, because obviously you don't know how things are going to feel in the future, but I would say as far as like my general spunk. I'm sure your joints and muscles will improve as you get older. Spunk, eh? Your spunkiness and just ability to recover from... You're doing a shitty job on your wine. Dude, I told you I had a I had two glasses before I got here.

No, no, no. I'm not trying to be an enabler. I'm just saying you're doing a shitty job on your wine. If you're trying to promote alcoholism or your shit, first podcast, it's a little hardcore. I'm waiting for the alcohol brands to sponsor me for my third episode. Yeah, so what was the question again? You want to know. Any age. Oh, 24. 24, okay. Yeah, so what was the question again? You want to know.

Any age. Where were you born? 24. 24, okay. Yeah, that sounds about right. I think the 24, I mean, your mid-20s are kind of like your prime, right? Yeah. Physically.

What are some of your pet peeves? What are things that drive you insane? Pet peeves, one of the things that drives me insane is that I feel as though in our industry, there are a lot of people that are tech, that aren't really direct. It drives me nuts when people beat around the bush. And really, you just need to say the truth. Because like, even though it's painful, and it stings now, at least people know where you stand. Yeah, it saves everybody a lot of time. It saves everyone a ton of time and i feel that that's like what would be an

example of that what circumstance it just feels that you know i i see this all the time and even my world in the venture capital world like a lot of people will say i i recently changed the way that i say no to people now this is of great. I would say that the majority of the time, like venture capitalists, when you go out and you're an entrepreneur and you're looking to raise some money and you meet with someone at a VC firm and they sit down and they say,

oh, show me your idea, and then you go through it. And then typically you get an email 24 to 48 hours later saying, this is how we want to proceed or not proceed. And oftentimes the email on not proceeding is like you know i talked with our partnership and i don't think it's a good fit at this time or you know um i i'm so busy with my current investments that i i don't think i have time

to take on anything new but thank you for your time and like it really let's talk let's talk six months or whatever it's such bs man it's off to maybe slash no and it's just like i was like it's funny i i just the other day i was sitting there i was writing a no like saying no to someone email which for me in the past has typically been like you know thought about it really don't think it it's it's something that that that we want to invest in thanks but i'd love to talk to you in the future, blah, blah, blah. The typical one that you read everywhere else. And then I just started thinking, gosh, there's got to be – I'm going to try and be very direct with the entrepreneur and just see what the response is like.

Because I feel like that's just like – I might come off as a dick, and that's the worry. The concern is that you just come off like you're just being a dick and they should talk to you at other places. But you know what? But I think that like, at least people will be like, you know what? We know where he stands. Yeah. Yeah.

And so I tried it for the first time last week, actually. And the entrepreneur wrote back and he was like, dude, thanks for being honest. I appreciate it. What was your wording? I'm curious. Cause this is something I think a lot of people battle with i had to say no so i liked the idea i thought that the space was generally really boring yeah i didn't know how big a business it would become um i thought that they had decent traction they were clearly going to get their next round of

funding because of that traction um but it wasn't something where i was going to be over the top excited about to answer their emails and get pumped up about. Right. And so I wrote the guy an email and I was like, listen, I don't think I'm the right partner for you. I think the idea is sound, but I am not excited about this space at all. It doesn't get me excited. And I just don't think like when you need someone to reach out to and to help you out, like I'm going to be the one that's going to jump back and be the the the right partner you know more or less and he wrote back and he's like dude thanks for the the direct feedback or honest feedback and you know look forward to see you next time you're in town because he's out of town cool and it was like it

was the first time where i was like wow i actually like it's also a good founder you know and you can take it i've done that before on and working with some engineers. And I feel like it just, it always, I kind of like, I want to start living by that because I think it's the right thing to do. So I think, I think you're a very good communicator. You're also a very good negotiator. I've seen you live. I think both are very interrelated. Do you think you're a good communicator? And why or why not?

Yeah, let's do that first. And then obviously the overarching question is, what makes a good communicator slash negotiator? I think they go together. I think that's hard because it's funny. I was just negotiating a car lease today, and I don't think I'm that good of a negotiator because this guy just mopped the floor with me.

Yeah, but you don't give a shit about your car lease that's why yeah that's i've seen you negotiate things you care about and you're good no that's that's probably true um so on the communications front i i feel that like plus that guy's done the same fucking negotiation a million times he's really good he's like i'm so glad you asked that blah blah bullshit let me know like verbally i literally walked out of the place today walked down the street and the guy's texting me like come back like we can talk about this and i'm like why didn't we talk about this 20 minutes ago when i sat in your office for 45 minutes like he's like oh we could there's wiggle room now and i'm like how is there there wasn't wiggle room 45 minutes ago and you brought me that crappy coffee and i'm like sitting there in the office sweating my ass off because it's hot.

Anyway, it was just like, I hate, I wish I needed to invent a new car startup because like there needs to be like straight, transparent, real talk, like no negotiation. I don't know. There's a lot of car companies out there, but communication wise, I feel that, um, you know, I don't know that I'm, I'm, I'm, I appreciate the compliment, but I think for me, it's, it's what people have said is that, um, I don't really, sometimes I get in trouble for this. I always did when I was doing PR at a dig and I was like, I would just say whatever was the truth and not necessarily the best thing to say, but just really the honest thing.

So like when we were having user revolts on our site, um, when, when I was running, uh, dig the very, like it was a very social site. So we had like millions of users revolting against us on online. Like, you know, I would get in front of the camera and just be like, yeah, it sucks. Our servers are falling over. We're getting crushed right now. And like, you know, PR would be like, okay, you can are falling over we're getting crushed right now and like you know pr would be like okay you can kind of like say like this and like you should word it like this

next time and it's like i don't know man i think like a lot of that too but that's the thing is like because people don't trust you if you're reading exactly exactly and that is an old like process an old way of thinking like people nowadays can see right through that crap. And so like literally just, you have to tell the truth. I mean, it's like you just have, whether it sucks or it doesn't suck. Like,

you know, I got in trouble one time, uh, another time when I was on stage, I was talking about our engineering problems that did. Who chastise you? This is board of directors. No,

this was, um, um, this was like actually, i mean well i'm sharing some insider information here but we had like we had this like group on facebook that was a bunch of ex dig employees and um you know i first of all for dedicated to being ex dig employees they they they were but like they i was also a member of that group because I had since left dig. And, you know, the blame is definitely on me from the get go because I'm the one that founded the company.

So like I can I can't really the buck stops with me. Right. But, you know, I'm allowed to tweak and figure out what I did wrong so I can hopefully avoid those mistakes in the future. And so I was saying a lot of what I thought I did wrong, including not like as Jack Dorsey puts it in an interview that I did with him, he says that you need to constantly be pruning and editing your team to make sure that you have the right people in the right roles. And that's like something that you as a successful entrepreneur, he is constantly done. That means sometimes having very difficult, tough conversations with employees and letting people go. And so I talked about that on stage and talked about how I would have done things differently, blah, blah, blah. And I upset a lot of past employees.

What upset them? Well, just that I would put the blame on engineering when they thought the blame was on upper management and blah, blah, blah. And don't get me wrong, the blame was absolutely on upper management. And there was, there's, I think that there's, you know, there's, you, there's, there's blame to be put all over the place. Like it's, it's like I could point to a thousand different things that we would do differently next time around. Well, if I were to just try to bring it back to this original question, it seems like you're surprisingly comfortable having uncomfortable conversations. And I've seen you do this live a couple of times where you're asking for things that perhaps other people wouldn't ask for, but that you should ask for. Or you're saying things that maybe you shouldn't say by some politically correct standard, but you do. for a raise or negotiating any type of deal or asking for anything they want or coming clean and avoiding some huge fucking pr scandal just by being honest at the outset they're not willing to have those uncomfortable conversations so why do you think you're so comfortable doing that

um i think it's probably because i want to avoid an even more difficult conversation down the road if i'm caught not speaking the truth the first time around yeah it's a lot more difficult to have the conversation to say like oh yeah i kind of wasn't like fully bringing everything to light in this original conversation so and i feel like i just i don't know man like if you admit your faults then other people can't point them out in you do you know what i'm saying yeah definitely like if i get if i get if you admit your faults then other people can't point them out in you do you know what i'm saying yeah definitely like if i get if i get if you make i mean it's the same thing with like stand-up comics who take who take the piss that's a really fucking commonwealth expression

but uh make fun of themselves before the audience can right to just like steal the thunder in that way so they can run the show and do what they want to do yeah maybe that's that i think yeah i never thought about this before it's funny that you bring it up but like i feel like that's probably the reason why because i want to say everything there is to be said that's negative so that we can get that out of the way so i don't have to be ridiculed in some way like i think that at dig especially we were under a lot of scrutiny all the time. Yeah. Because we had such a very vocal audience that was taking down sites and servers because we had so much traffic. Took down my server. First time my servers got taken down, I remember very clearly. It was in New York City.

And I had this very odd blog post called From Geek freak how i gained 34 pounds of muscle i remember that 28 days yeah that hit the dig front page and took down my whole fucking site and it was like a big deal and that was a very uh important defining moment for me i remember i mean dig was extremely powerful for a very long time yeah it was um and because of a lot of that the press used to always love to like sit down with us and be like what do you think about your audience and like the fact that they make these types of comments about certain users and or there's a post about you know uh you know certain ladies in bikinis and they hit the front page and it got all these clicks and all these men are saying these really crude things like how does that make you feel and i felt like i was always being hit with all of these kind of like like you suck tell

us why you don't suck questions you know that i was just like you know what you're right we do suck you know that's the only thing you can do like look humanity's fucking brutal like i'm sorry i'm like if you have how many i mean how many monthly unique visitors do you have Humanity is fucking brutal. I'm sorry. How many monthly unique visitors do you have? 38 million was the highest. If you take a thousand assholes in an auditorium,

you're going to have a thousand people in an auditorium. Think of any school play or any Little League game. It's always going to be right and you have like 300 dads they're always going to be four fucking asshole dads are like yelling and screaming right in the face right so you take 38 million people and extrapolate it out of course you're going to have a fucking mess in your yeah it was so i just realized that like at that point you just got to

surrender and not fight and just be like listen and it actually helps out a ton because they people are like oh he's just human he's like he's well you know that's really important i think is to emphasize not emphasize but at least mention the things you suck at as a way of qualifying not like credentializing everything you say after that, but also qualifying the users that come to your site, right? So, or that use your product by explaining who should not use your product, if that makes sense. What would you say that you are world-class at? I would say

every couple of years, uh, I will come up with something idea wise that I have never seen done before. And so the thing that I enjoy more than anything else out of anything I've ever done in life, um, uh, outside of like the emotional side of like, you know, finding your wife and dating and things like that has to be things like that. Well, I'm just saying like, that's, that's another thing. Cause that's awesome too. But I'm saying like, career wise has to be those moments where you have those original ideas, you know, that they come to you, that you're just like, this has never been done before. And you, you prototype it and you build it and you look at it and you're just like,

wow, like, I don't know if this is ever going to be anything big, but I'm the first person that thought of this. Like that is a really cool idea. And like we had, you know, maybe 10 or 15 moments throughout digs history where we were the first ones to

do some of these things. And like, that is the coolest feeling man when you create something that like millions of people end up using and you're just like dude i made that like it's like you feel so emotionally tied to it and then you also you know it's funny it's because we built a lot of stuff very early days at dig that went on to be used in many other products including everything from you know stupid things like facebook using a like button when we like created social voting way back in the day and had it spread to profiles and a lot of the the kind of nuts and bolts of how that stuff

worked like a lot of that eventually you know some of the comment stuff that we did with the voting and like a lot of like really crazy stuff we did on like showing real time data around votes and like all this stuff eventually made it into showing real time data around votes and like all this stuff eventually made it into much bigger products than what we had created. But dude, to know that you were there for a minute and played a little role in that, that, you know, that was really cool. Like I can remember when like Zuckerberg came down to my office at dig, sat on my floor with his flip-flops on, know facebook at the time was like smaller than dig and was like shooting the shit with me about like what he wanted to build at facebook

and like you know thought we were the shit and i was like damn that was you know now that i look back on that at the time i was like who is this kid now i look back on that and i'm like dude that's so cool like that that was like a moment where like we had created something that he was like caught up in and thought it was really cool and baked some of those ideas into some of the stuff that he built and went on to to to obviously launch to an audience that's 100x what we ever were yeah but like dude just being a part of that like that whole movement was was something that i will forever cherish, you know? And it's like those, what I, so your question is like, what am I really good at? It's like, I enjoyed those moments.

And I think that like, if anything I can bring to my, my, like the people that have followed my work and that continue to follow the stuff that I do, I hope to have a few more of those in my lifetime. Yeah. And, and be able to actually launch some stuff that people are like, wow, he, he, it doesn't have to be big. It can be super small. It just, I want people to think like, wow, that's something I've never seen before. You know, I like that feeling.

So I feel exactly the same way. And I enjoy the newness, the inventiveness, the aha moment more than the scaling. And I think it's sometimes to my detriment right so you say look at the quantified self movement and so on it's like i was at the first meeting finished since the beginning did the four-hour body published 2010 which means that i was doing research in 2008 2007 uh recording did even before that and you see with the iphone announcement a couple days ago biometrics no no not that the new chip the what is it called the m7 chip no there's so they're building in to a chip they're offloading all the pedometer stuff they can tell when you're in a car when you're walking when you're running all that stuff is going to be built on chip super low power always on so it's

going to power like a whole nother like suite of cool quantified self stuff but like to your point like you're on that shit a long time ago right and and now it's actually like hitting mainstream right now it's hitting mainstream so you have i think people like uh dave asprey is quite smart uh bulletproof coffee and so on will probably generate more revenue for himself than i ever will personally but i enjoy being there at the inception at like the big bang moment more than the scaling and it's it's something that i struggle with because i feel like fuck like you know if i could have caught that wave of like a year or two later, let someone else do all the R&D. Right.

You could monetize it so much more effectively. Dude, it's not too late, man. But I enjoy the inception moment more than anything else. Yeah. Well, I mean, okay, so fine. So what do you think I should do? I mean, I think that. In terms of not being too late.

I'm curious. I mean, honestly, the quantified cell stuff, like just now in the last Android release, they're now automatically building in at the API level. They can tell whether you're walking, running, in a car. Apple just announced that in their latest chip like three days ago. Same thing. Like the APIs and the hooks for all this stuff are there. It's up to you what you want to build on top of it.

You could do so many different things on top of that. Yeah, I'm just... And it's up to you what you want to build on top of it you could do you could do so many different things on top of that yeah i'm just and it's early days man like if you think about all the stuff that you've looked at like as far as reading like real time i mean dude when i first yeah it's funny i'll tell a great story a tim ferris story like i think this is in your book too uh when we were hanging out and we're watching a movie do you remember what movie that was this is years ago it was uh it was inglor Do you remember what movie that was? This is years ago. It was Inglourious Bastards, right? Inglourious Bastards.

Oh man, that was such a great movie. I love that movie. It was a good movie. So we're watching Inglourious Bastards and like Tim's doing research for his book. No, this isn't my book. You were doing something for your book, right? Yeah. Well, I was. No, no.

We haven't talked about this though. Oh, okay. Yeah, yeah. So we're sitting there in the movie theater and and we sit down, and literally you didn't even think to say a thing to me until we sat down. We were hanging out before then or something, and you sit down, and you're like, dude, I'm doing this crazy experiment or something like that. I'm like, what's up?

And you pull up your shirt, and you had some kind of syringe in your side. I had a continuous glucose monitor implanted into my side in my abdomen you have but you had like a needle in you and then a wireless little thing three needles stuck under my skin implanted into a transmitter that then went to a a a wireless receiver that was on my belt yeah and i'm like what the fuck is this guy doing like that was like but like talk about quantified self stuff i mean this was years ago yeah and like a long time ago and and you think about like we don't we still don't have that data available to us but like there's there's a lot of talk in in at least in some of the startups that i've seen at external ways of gathering very

similar data like they're doing a bunch of new ways that like get it heart rate get it um that was the perspiration that you have coming off of you like a bunch of different things like galvanic skin response right exactly it's common yeah there's a startup i don't think i can talk about it yet basis is cool i'm an investor in basis uh so the basis watch is very cool there's another startup hopefully i can talk about sometime soon uh which is basically like a nicotine patch that tracks all that stuff 24 7 that's fucking cool yeah it's super super cool um but anyway what i'm getting at is like it obviously it's like i feel like especially in this sector like there's a lot of talk and like the origins of something

which obviously you were a big part of. And then there's that inflection point where the hardware catches up with the, with the, the general discussion. And then the hardware enables a whole slew. Harbor. We're getting to a great blood alcohol content point now. No, the heart, the hardware, but the hardware is finally up to speed now to where like,

you're going to see in the next few years, like a lot of this stuff that we thought was impossible actually make it into devices that we wear well exactly and the issue has been up to this point quite frankly data entry right because you have shitty devices or i shouldn't say shitty but very primitive devices that only capture accelerometer data and every other biometric data point that you want say blood values is really intrusive right you have to have someone come to your house or you have to go to quest labs or unless you're a cutter lab quest rather or unless you're a cutter right to uh watch the secretary everyone it's a great movie. It's hardcore. It's such a good movie. But the point being that you would have to have these intrusive, or I should say not intrusive, but invasive tests done to get the data that you want. Sure.

And there's time around that, too. It takes time to get the test back. Yeah, it does. It takes a lot of time. So I think that the latency on that is say three to seven days whereas as soon as that nut is cracked where you have something like a nicotine patch that you can slap on that's good for seven days that tracks why does it have to be nicotine no no no it's not nicotine it's just like a patch it's like i thought you were like as a twofer no no no as a twofer you get nicotine that stuff makes me so

sick nicotine's so strong i can't i yeah we can talk about that another time trim your toenails that one is really long yeah they're gross i know i have talons people because if you come to me those are literally like dragon talons i'll be like what's that what's that bird gram any any insight there's a bird in cassowary yes an australian bird that will like rip your heart open with a with a with a uh with hooves basically nails on it this should be the title of your first show that's my podcast the cassowary shit fucking no one will be able to spell it they'll be like 17 different seo versions that would suck uh hold on so let me uh if you could, this is such a non sequitur, but whatever. We're going for it.

You were a colored jelly bean. What color would it be? Suck my balls. Wow. Not literally. Figuratively, I want you to suck my balls. If you could outsource one of your daily tasks, what would it be and why? Because you have no fucking excuse, right?

I mean, you're like, you're doing well. You can pay whatever for whatever. But what of your current daily tasks, your repetitive tasks, daily or weekly, would you like to outsource and why haven't you? You know, I don't think there's anything else left that i have to i want to outsource okay i think i'm actually pretty set okay so what do you bitch about that you don't want to outsource uh how's your wine by the way it's great i think i'm thinking i'm still working on it i'm good i'm like i'm like a three um Um, so I think that, you know, I don't know that I,

uh, I think that if anything, I complain that I don't have time to focus on some of the things I'd really like to get behind. Like I want to learn how to garden properly. I know this sounds lame, but like, are you kidding me?

That sounds amazing. What type of gardening? Well, I mean, I've got a vegetable garden right now. And both in the Dr. While you were his garden. Oh,

Dr. Wow. Dr. Wow. Is my freaking idol, man. That a vegetable garden right now. We both know Dr. Weil. You remember his garden? Oh, Dr. Weil. Dr. Weil is my freaking idol, man. Dude, that guy's garden is amazing. So we were lucky enough to go up to Dr. Andrew Weil. You probably know him as the dude with the big white beard on all the Whole Foods stores shelves. MD that looks like Santa Claus. He looks like Santa Claus.

He's amazing. We got lucky to go to his house up in Canada, in Canada and like freaking the dude is like the master. Um, he had an amazing garden. Yeah. So anyway, um, yeah,

I would like to learn more about that. I mean, I, I think that like right now it's a very, I have someone help out that comes by and like basically helps with the garden. And I just, I understand the basics,

but I need to understand, like, I want to get to the level of've like understand the soil composition and a bunch of other things. And like, you know, I just don't have the time to do it. I wish I did.

So I think there's a bunch of little hobbies. I think that you're getting that with the meditation and with the garden, like there's probably, you know, a handful of things I'd like to work in fast food again. Uh, elaborate please. I have this reality. I have talked about reality camp i have this really

weird thing where i want to go and work in like fast food again we talked about this reality camp until someone comes up and it's like kevin and then i'm gonna run out like i want i want chipotle line extra guacamole it's dollar 50 sir no i'm being dead serious like i would like to do do some of that like just we've talked about, like the cognitive tax that comes along with white collar work. Right. In the sense that when you're in front of an inbox constantly and you're on the phone and conference calls constantly, there is a like mental and soul tax that you don't interact with people.

It's like, it's not on your own. That does not allow you to interact with other people. And so we both have this fantasy of like working on the Chipotle line in this like. I will join Chipotle if you will. Meditative, repetitive. Yeah. Context.

How fucking awesome would that be? Also, I would really like to just analyze i want to understand businesses that are fine-tuned and all about like one of the things i i respect about these businesses i don't necessarily triple is decent in that i hear their ingredients are pretty good but like mcdonald's a place that i would never ever really want to work at but i kind of do and the reason i want to go work there is because i want to understand what processes they put in place to get the efficiencies that they do yeah and like i really would like to like you you gotta imagine that you're dealing with like 16 to 18 year old kids as a majority of your workforce these are like the most unruly crazy spit in your hamburger type of like like how do you manage that?

Like that's the kind of be the hardest segment of people to manage. Like, I know when I was 16 to 18, like I was doing all kinds of crazy, stupid stuff. And so like, I would imagine that they have systems in place when you're 16. No,

I know you wouldn't, you still wouldn't today. But like, I would imagine that like, when you look at like what they have in place, everything from like the ways that they monitor their employees to the system they have set up to like, here are the three things you have to do to make this burger. Here are the seven things you have to do to make this burger. Like I just want to understand that process so I can figure out how someone would successfully franchise and scale a business like that. I'm just curious.

And I also think it would be, you know, there's something about like, there's something about like actually serving people. Like, I think that's like a cool thing to do. Like I wouldn't mind. Yeah.

I would like to, and I actually, I'd like to talk to you about this. I wouldn't mind like donating some of my time. I actually want to join the boy Scouts again and help out because I was an Eagle Scout and I went, I was in Scouts all growing up and help out. Uh, because I, I was an Eagle Scout and I went, I was in Scouts all growing up and I, I feel that like I really miss one of the things that my dad did, uh,

when he was alive is that when I was a little kid, he was a mentor to a lot of other kids in our troop. And I think that it was really important and he enjoyed it because, um, you have to understand that the boy Scouts, even though there is one of the things that nobody ever really talks about is that at least in Las Vegas was that there was a lot of kids that were dropped off by their moms who didn't have father figures. And they were like, this is the only way they're going to get like a father figure in their life. And there were a lot of boys there that just like never knew their dads. And like my dad was like a father figure in their life. And there were a lot of boys there that just like never knew their dads. And like,

my dad was like a second dad. And like at my dad's funeral, there was like, you know, a couple of people, well, one in particular that was a good longtime friend of my dad's. And now I was in his,

you know, late thirties. That was like, you know, a scout that my dad kind of mentor because, you know, he considered him like a second father. And so,

you know, I, I would like to, to figure out like a way to like get back and involved in that and you know actually do something outside of the computer and just get you help help some people out dude I'll do that with you that'd be fine I uh I saw a poster today I went to a meditation class my check-in like o'clock's anonymous yeah exactly kevin's doing a jerk-off motion i did not well i'm left-handed but i was asking for more wine the universal more wine jerk-off gesture uh so i went to a meditation session

i.e as kevin would have it if it were up to him a masturbation session and there was a poster for the girl scouts so no more masturbation references please uh which said uh and i was really actually inspired by this today it was this it was a picture of this chick doing sorry chick what you know fuck you guys chick is fine uh it was a picture of this this like badass chick doing taekwondo and doing like a high kick and it said uh cleopatra ruled egypt when she was 18 years old what are you doing oh damn that's strong yeah and it was a girl scouts poster and i was like fuck that is a good poster. Now I feel like a lazy asshole. I need to go do something. But it was very inspiring.

And I feel like that's a place where you can have a huge amount of impact, certainly. And for me, I always thought I was going to be a ninth or 10th grade teacher because I felt like that was a really critical time for me where I was deciding where my life was going to go. And I had a lot of bad influences to choose from and a lot of good influences to choose from. Actually ninth grade, man, it's so key. That's the one. So key. And so I thought I was always going to go back and teach ninth to 10th grade or one of the

two. You'd be an awesome teacher, by the way, you should do it. I would enjoy it. You know, I always thought thought i was going to and it just turned out that the books and the blog and this and blah blah blah everything everything came up as a vehicle for teaching have you so here's one thing i just want to throw out there real quick there's a lot of people talking about this unschooled movement yeah where it's like open source school like where like the kids can pick like the different classes and in their own kind of like at their own leisure have you considered doing like you could put out episodes that are like some courseware and the class online that like you know that would as long as you adhere to like some of the unschooled stuff like you could basically create your own class for the same yeah you know age group i'd be open to doing that

uh gram i'd be curious to get your thoughts on this. Kevin, too. But I feel like the figures that had, and again, speaking as a male, so this may be unique to men or to me, but many of the people who had the biggest impact on me were males who were just like, here's the fucking way it is and like this is the program we're going to follow whether that was wrestling coaches or teachers in specific subjects who gave me structure that i lacked right so you needed a little bit more discipline you need a little bit i think it's i think it's very i think that in order to be a good leader, you have to learn how to be a good follower first.

I feel like that's a famous quote that you just took from somewhere. I may have stolen that from someone. learning to be a good follower or disciple or soldier underneath someone else is very useful training for them being a leader later. And I don't think that it would have been a service to me as a, say, 15-year-old. And I can very clearly identify this 14, 15, 16-year-old period where I was very lucky to encounter certain people who had a huge formative impact on my development. In that period, I feel like I needed good guidance. I needed good leaders. I didn't need, I didn't need, nor would I have in retrospect wanted someone to say, you decide what you want to do i don't know maybe that's me being

naive but i i really feel like at that point in time i need someone to show me how to follow a good structure as opposed to admit my own what are your thoughts um i think everyone's different i think that certainly that that approach is is one that uh is probably a little bit more traditional i mean that's the way things are today right like people are saying like this is the class you have to take this is the thing that you have well i mean but there's a difference between taking say four years of undergrad doing all the fucking bullshit i mean i you know and i finished and i got my degree from princeton great and fantastic and there are a lot of fucking retards who graduate from princeton and every other ivy league school but people think i'm smart because i have that on

my resume or whatever uh which is silly but that's the way it is i think there's that which is four years versus having a good like obi-wan kenobi and i do think yeah it's hard to go from like being born to being your own obi-wan Kenobi as opposed to having someone in between who really puts you in check when you're just being an arrogant prick as a 15-year-old. Which, perhaps it's not applicable to females. I can't speak to that because I'm not a woman. But every 15-year-old dude thinks he knows everything about fucking everything do you know what i mean yeah and you need like you need an elder just be like no that's great i'm glad you're confident but like let me show you how this shit actually works

and like i'm gonna push you to the breaking point and you don't think you can do it but i think you can do it so i'm gonna push you even further and i remember just having uh this particular mentor of mine mr buxton who's an amazing amazing amazing guy uh the ceo of donors choose for instance and founder of donors shoes i mean you just you look at my wrestling team and you can just you can telescope them out to these amazing outcomes and all of them without exception in my experience so far i attribute it back to mr buxton being a fucking like brilliant hard ass in wrestling like he would not you thought you could give seven he'd be like no no you can give 10 and he would just push you to the breaking point. And, uh, that was just, whenever I,

whenever I face anything that is difficult in my life, I look back on my experience when I was high school and it's like, all right, is this harder than what Mr. Buxton pushed me to do? No, it isn't. I can do it.

I think there's, um, there, there's something to be said about like choosing your own path, but I don't think, I think that once you've chosen that path, there there's i agree that like you can there's no reason why you can't have a hard ass under that particular like vertical of whatever you've chosen right like if you say okay i want to get into computer science like you you can have a badass like hard ass in computer

science that like drives you to be the best right like i feel the same way like i have a trainer at the gym and why because i'll push myself to freaking six if i'm left to my own devices if i go in with the trainer i'm going 11 and walking out of there sore as hell and can barely limp back to my vehicle you know and so like i i agree to this vehicle what's that back to your vehicle come on i didn't want to say scooter because I have a scooter. I like vehicles. It's very efficient. I take a little scooter to and from the gym. It's efficient. I love that you get fucking

super jacked at the gym and then jump on a Vespa. No, I'm really embarrassed because I got the wrong color. I got a freaking gold Vespa. It's so ugly. Dude, that's ball ballsy it's like being the fucking fat guy in like abyssa wearing the fucking man thong just walking around i wanted black and daria didn't like black and then i was like she's like gold's nice i'm like yeah gold's kind of nice then i'm getting the gold one who wants a gold scooter it's the worst that's very uh confident i like that anyway all right so so i mean if the if you could find a mentor we're not going to do too much

longer but if you could find a mentor of some type like what type of mentor do you think you need um you know i think that it's it's for it's, it's finding someone that fills in the gaps. I think that there is, you know, when, when you want to run a business or you want to start something new, the best thing that you can do. Um, and the thing that I kind of like was, I would say that one of the big learnings that I had when I was a lot younger in my early twenties and started dig was that I put my head down, I put my headphones on and I said, I'm going to focus on product because it was the thing that I was comfortable with. And it was the thing that I understood and I knew how to do well.

I kind of, you know, close my eyes to every other aspect of the business, whether it was financials, whether it was running the business, whether it was hiring, firing people, whether it was, you know, scaling, like there was a bunch of pieces that I just was like, I don't understand those. I'm going to close my eyes and pretend they don't exist. I'm going to hire other people to run them. And I'm going to say, well, I know for a fact, I would be honest with myself about what I don't know and go and absolutely try and pair up with mentors that can help me out. I think if anything that I've learned in the last, you know, 10 years of doing this is that there is no shame in admitting that you don't understand something because you can either fuck it up. And that's when you act, act like you understand something and you actually't understand something because you can either fuck it up. And that's when you act, act like you understand something and you actually don't, or you can admit it one time, learn it and then move on and become a better person and just more well-rounded and actually,

you know, get serious about building a business. Like there's, there's, you can, you, if you ever going to be a founder and you're going to run that business, you have to understand that you can't just be good at one thing. You have to understand the whole gamut, the A to Z and, and at least have enough knowledge to be able to make an educated decision around certain things. And I think that I was very, uh, immature and I, I hid from the things that I didn't understand. And so even today, there's a lot of things I still don't understand. Um, when it comes to finance, like, uh, what do you worst at right now? I mean, what, if you could conjure the perfect mentor from the ether, like what, what are the things that you would want to most improve upon? I think that for me currently it, you know, I am decent at reading legal documents, but I'm by no means a pro. And so like, there's a lot of little weird things that attorneys like to throw on these little curve balls and weird things into, um, financing documents that

as a VC, you have to go through and pour through and like, look at, you know, certain terms, understanding how they might impact the company. And like, even today there was a term that I had never seen in a document. I thought it meant one thing and it actually meant something else. And our attorney, like I am to me and she's like, do you actually realize that this means this and not this? And I was like, oh shit, I didn't know that. Thank you. Like, that was awesome. Like I had no idea it really would impact us if we ever decided to do X, Y, and Z. And so, um, you know, just, just like sitting down and, and saying like, can you explain these things? And, and it just takes time, you know? And it's like, it's something that, that you can't be expected to know every little facet of every business,

especially because there's so many different, like you don't go and get a degree in, you know, business and finance and marketing and like all these different areas, you get one degree. If that plus none of those teach you how to analyze venture capital agreement. Oh yeah. No doubt about that.

I mean, there's, there is a very good book. Uh, I believe it's called venture deals by Brad Feld and his partner, Jason. I believe it is. Uh,

what's happening? Sorry. I just drank that. That was water. No, it's wine. Uh, which is very good at introducing people to some of the common terms,

venture capital, and just general startup finance agreements outside of that. What else? So we got that meditation mentor wise. Yeah. I mean the meditation, the gardening, you know,

the other thing I will say is it's really good to have an outlet to just vent. And that can be with your spouse. That can be with, you know, it's funny. It's like it's trying to, you know, I mean, this is we're getting really deep here. Do you want to keep going? Let's do it i mean it's it's one of those things where i think that you're like this too dude having known you long enough now that like you are a kind of a closed off person you know and so am i in that like you know you hide some emotional stuff and you keep it like you do because people will fucking kill you if you don't i mean yeah but like also you know it's like i

mean just dealing with like valley wagon shit you'll get fucking slaughtered. You don't have some degree of protective. No, I know that. I know that. But I'm saying like understanding the value in being able to freely vent to a significant other or to talk to someone or have like a good bro or even like seek counseling or whatever it may be like having an outlet to be able to go out there and, um, get gut checks on different things, I think is a really healthy thing. And so like, you know, for me, like I've had some, some good friends, uh, in, in the Bay area that like, you know,

like you, for example, we've talked about a bunch of deep stuff before I've done that with Prager and some other friends and things like that. And I think that like just having those, I think is a really healthy thing. And so like those act as mentors in a way, you know what I mean? Like, I think that like your close friends like that can act as, as mentors.

So here's a question for you. So I've, I've recently, this is nothing I've talked about before, but went to a therapist for the first time, maybe two or three months ago, and I found it extremely helpful to speak with someone who is completely non-biased. And I viewed it as a bit of a cop-out in the beginning

because I felt like it was an admission of weakness to go to a therapist. It absolutely is. For the same reason that I haven't used antidepressant. No, like I've never used antidepressants, even though I've, I've dealt with that shit in my own life. Like I've never taken Prozac or any,

uh, like SSRIs or anything like that, because I feel like it's, it's an admission of weakness and that I should be able to deal with it in other ways. So I'd never gone to a therapist per se, and many people might call it a business coach or whatever just to hide the fact but went to this therapist kind of very

helpful and have not gone to a second session even though i found the first session extremely helpful was why was it was it you just felt like afterwards you're like oh god i can't because there's a stigma attached to that there No, there was no overthinking it. I was just like, oh, I'm fucking busy. Like, no, I'm not going to do it. So why not, though? There's no reason not to. It's funny.

You should mention that. You know, it's like I did two hours of physical therapy today because I fucked up my right shoulder doing crazy fucking shit. I think we need to treat our brains like that, though. You need to treat it like another muscle that you would work out and you need to figure out like you know that that's actually a good positive thing what i wish there was a more casual therapist something that didn't something that didn't involve like ghost sitting in a chair right i mean like this could be like a like a friendist gutcheck.com like something where you're just like oh it's me for coffee and it's like somebody that's just like a friend that gutcheck.com. Like something where you're just like, Oh, let's meet for coffee. And it's like somebody that's just like a friend that,

but you'd pay them paid friend.co.uk. Do you know what I mean? There's gotta be a way to like lighten it up a little bit. So it's not like, I agree because there's so much, I think people have so much baggage associated with the title of therapist that it never happened. Oh,

no doubt. It was just useful. And it may have been quite frankly, just the fact that I was able to hear myself talk for an hour and think through shit without a friend who was subjectively trying to help me. Let's see. So what advice would you give to your like 20 or 25 year old self given everything that you've gone through and everything you've learned

uh 20 or 25 year old self i would say 25 i'd say drink a little bit less um that's a good question actually i haven't thought about I mean I think a lot of the things that we talked about today about like surrounding yourself with mentors and understanding to confront the things that you don't understand rather than hide from them I think that Um, um, I would say that if it's from a straight business point of view, I would say that do you can do more with less. I think that like, there's this temptation when you start seeing some success to like throw bodies and servers and more people at the problem. When in reality, it's like just making sure that the you

have the right people in the right roles i think they have this rule at google it's called uh i'm gonna screw this up but you get the gist that it's like the 10x rule and like the right person in the right role can do the work of 10 people in the wrong role and so like they they've got this thing where you know if you can if they can they can find that person for that right role, you'll get 10x the performance. And I totally believe that's true. I think that's – so that – there's a reason why Instagram grew to – I don't know when they sold it.

It was 50-plus million people or something like that using their product with 10 people. Kevin's a smart boy. What's that? Yeah, Kevin's sister. Kevin you know it's like it's a smart boy it's um what's that yeah kevin's sister yeah he's a smart dude uh but you know he was good like that the whole team did really well obviously what uh so all right last question because i want to be sensitive to obviously everyone's time you guys listening the fine Kevin Rose the third Esquire involved with this interview last question I am the third actually

yeah but not Kevin Robert Rose I got that right who do you think I should interview on this podcast in the future any nominations I've had a lot of people say Dana White of the UFCana white of the ufc interesting president of the ufc which uh i'd totally be down for obviously big ufc fan i think

that like the thing that that um that would be fun is if you just i mean you got to get outside of tech i mean obviously there's a lot of tech people um but in the in the bay area but i think that the thing that i would love to hear about is if you as you because you travel the world so much you're like always all over the place and weird crazy countries yeah you need to bring some of that culture to the show and i think like even if you could like if you did something where you splice together a bunch of different interviews to fill out like a half hour, 45 minutes, like if you were like,

if you were in freaking the Philippines and you are in Thailand and you met some phenomenal freaking like chef making amazing noodles and you're like, did a five minute like on the street interview about like what drives them, what they use in their ingredients, like what they love about their life. Like, I think that like, just like you, you see so much interesting stuff like that,

that I would love to get a little taste of that. That'd be cool. You know, it's like, I know that you're, you're always about like the really minimalist, like crazy, like getting the actual feel of the culture in like, you're not the, the average, like, I'm just going to go to like a third world country and stay in the four seasons, you know? So I think that like, like bringing that flavor to the show and like,

like bringing in some of those personalities that are outside of, of what we get here in the States, I think would be pretty awesome. Cool. I am up for all of it. Well guys, I want to be respectful to Kevin's time and Graham's time and your time. So I'm going to bring this to a close.

This three-hour podcast? This three-hour podcast to a close. How long was it? Hour 45. Hour 45, that's good. That's a little long. That's like half the length of Joe Rhodes' podcast.

I think we lost pretty much everyone. At reply me, at Kevin Rose on Twitter with TimTimGood good as the hashtag. If you even listen to it this far. All right. I bet you there'll be like four people, two or three people. And let me know what you think.

I would love to hear your suggestions, what you liked, what you didn't like, what you'd like to hear more of less of send me a note at T Ferris, T F E R R I S S. That's two S's, two R's for double religious, double sexy.

Just kidding. And let me know what you think. Thanks for listening so far and hope to do more of these, but only if you guys like it. So let me know what you think. And to that point, Kevin, cheers.

Cheers. Thanks for having me. Namaste. Namaste. Until next time. Good night, guys. F-O-U-R-H-O-U-R-B-L-O-T.com Where you'll find an award-winning blog, tons of audio and video interview stories with people like Warren Buffett and Mike Shinoda from Linkin Park, the books, plus much, much more.

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