my family beyond with things way. Remember, just because you're doing a lot more doesn't mean you're getting a lot more done. Don't confuse movement with Progress. Way living, a paradoxical time where we have more comfort but less peace, more connectivity, less connection, more information, less wisdom. The purpose of this podcast is to explore these natural tensions with independent voices. Who will push our thinking tha This is the paradox. Podcast was getting just good enough. You know, I'm not good at it. You can learn quite a lot from experience. That's one thing.

Something after that have the will and determination to do anything about it. Everyone welcome to another episode of the Paradox podcast, I'm your Coast, Kyle Tibbits. Joined by my fellow Coast Alex Con for episode number three, we met up with James Bashira at his house in San Francisco. James is a modern day Renaissance man, an entrepreneur, angel, investor, podcaster, author, musician. He's a prolific creator who operates with passion, and he's probably one of the most honest entrepreneurs I've ever met. James founded three startups,

including Till, which was acquired by Airbnb in 2017 where he became global head of Airbnb music. James's Angel invested in dozens of startups like Gusto, Mercury Bank, Halo, Top Face, Cream, Bolt and many others, including several multibillion dollar companies, and is now full time Angel Investor. This year he launched the Below the Line podcast, which is without any exaggeration, my favorite new podcast of 2019. James is an advocate for mental health, lover philosophy and someone who's always willing to help. He's personally been very helpful in the launching of Paradox Podcasts,

and now he's our third guest. James has a book coming out next month called Beyond Coffee, which you can check out beyond coffee book dot com, and you can follow him on Twitter at James Bashira before we dive in. This exciting episode wanted to give some context on how the paradox podcast came to be so Alex and I go way back. We actually met at age 16 working as congressional pages in the U. S. House of Representatives and have been great friends ever since. A little background about me. I've worked in Silicon Valley for over 10 years, doing marketing for a number of different startups. I'm a husband and a father to a one year old daughter and family is super important. There really two reasons why I wanted to start this podcast first. Alex and I've been talking about how societies become this place where there's certain things you can't really say. There's certain people you're not supposed to talk Thio. There's certain ideas you can't fully debate,

and we think that's fundamentally wrong. Way strongly believe in the marketplace of ideas and want this to be a space where we explore a wide range of perspectives. Second, we live in this paradoxical, somewhat strange time where, for example, we have huge amounts of abundance in certain areas of life, and that actually leads to scarcity, indirectly related aspects of our lives. And we want to go deep on those topics when we can ultimately want this podcast to be a series of conversations with bold independent thinkers who really open our minds and expand the way we think. And hopefully do the same for anyone listening. Alex, why don't you introduce yourself? Hey, everyone. My name is Alex con.

I currently work in the California State Legislature. I'm focused on health care policy. A little bit of background. I'm a kn attorney and I've worked in politics pretty much since I was eight years old. One of the reasons I really wanted to do this with Kyle is over the 16 or so years that we've known each other. We've always been able Thio disagree in a friendly way, and recently we were talking about how that's kind of missing in our society, and we realized more and more people are forming tribes of folks who are like minded, who agree with them not really challenging their own beliefs. And so well, we're really setting out to do is have conversations with extraordinary folks from all different fields who will hopefully expand the way we think expand our point of view and maybe have that impact on our audience as well. Now that we've got insurance out of the way, let's jump right into today's conversation with James Bashira. We hope you enjoy the episode. James. Thanks for carving out time on your Saturday of all days to have us over. This is extremely generous of you. So thank you for of course, joining the paranoia like Alex.

Thank you for Ah, for the invite. I told you this was we were walking up, but ah really love what? What you're doing with Paradox podcast and y'all's angle is actually my preferred type of podcast. Where you go into these really dark corners of topics that just you don't go into in a business podcast or you don't go into an A, I don't know, a true crime podcast. Yeah,

like that. Yeah, I think there's inherent tension there between going a little bit deeper into one area and having a little more of a clear target, and we're a little bit broader, so that's that's a bit of a challenge, but what kind of charade is as we go as you do with any sort of a project, right when we grow up, we want to be below the line,

but that is a super kind, and I think you guys air well on your way there and for listeners. Kyle sent me, though the premise for Paradox podcast maybe one or two months ago, and I love that it married a couple of different subjects together in one podcast because life is not these. Like bifurcated silos, subjects that don't interact with each other, life is obviously it is the inter weaving of all of these things, Rand and I love that. Ah, that your podcast is built to do that from the get go.

Well, thank you. So one thing I really love about your podcasts and we won't spend the whole episode talking about podcasts.

You know, I I love not only obviously listening podcast love creating podcast, but I just think it's so wildly under discussed. How crazy of a medium. This

is crazy, my mind. He talked about new media for a long time, and it was their own. New media is coming, and now it's moment really has arrived. Yeah. I mean, you have the big podcast. You have Joe Rogan of all that type of stuff, but it's long or the fat tail of podcast creators that air creating all these different pieces of content. I think, like you said in your threat, I think the way that we learned the way that we process the world's events the way that we think through issues, well, probably more likely in the future to be doing that with a podcast to process what's going on. And so I think we are early,

too. I don't think we're anywhere near the peak, and I think that it's gonna keep going for a little while. And it's exciting to be a small part of it, for sure. I remember, um,

thinking Amazon is still just getting going 14 or 15 years. And when I realized my parents didn't really use in 2010 11 they'd never really used Amazons like, man, this is still just beginning the fact that you have these major consumer classes that still don't use this thing and, um and I made a prediction that it was gonna I was gonna double in in, ah, market cap in 18 months. And it was a 14 year old company. Doubling and market you have in 18 months would have been, uh, pretty, pretty crazy. But I thought it was what was going to happen and and looked at at buying options in the company and didn't know what I was doing. Never really bought stocks, couldn't buy it because I think the furthest out I could buy it was like 15 months. I was like, Okay,

that's way too great. I'm already being kind of, ah, stupidly aggressive. There's no way to be 15 months, and, uh and if you want to look it up, he has 2012. You can even see this on Facebook. I was writing about it for months. I was like, This is just getting going. And, um, it was 19 months. There you go.

Doubled in, Ah, market cap. I've been wrong so many times on things, but I felt really strongly about that. I also feel like equally my parents just discovered podcast because of mine. Weren't for mine that wouldn't have, wouldn't have discovered him. And it's Ah, I think it is just getting going. And probably the biggest sign, um, for me personally is about a month or two ago. I swear I love music, but I think podcasts are my favorite medium over. I mean over even music.

I think one of the things I probably love the most about your podcast is sort of the refreshing level of honesty. I feel like one of the more positive trends in Silicon Valley. I've noticed Hopefully you've noticed in the last maybe 3 to 5 years is ah, lot more openness about the rial side of building a company, not just kind of the used the phrase above the line, that kind of PR prove version. And I guess I'm curious. Has that sort of level honestly been something that has always been a value. That's something that you kind of came into through the process of learning about building a company. Where did that honesty come from? And why did it become such a core part of kind of who you are and certainly what your show's about?

You? I, um it was just telling a friend. Yes, sir. Another founder friend. And he was asking for advice on stress mitigation. And so I said, a lot of the stock answers, um, of practice, the art of under committing like we're especially founders, very optimistic and and how much time they really have and what they can get done. So practice the art of under committing, um, meditation practices. I mean,

the researchers keeps coming out the effectiveness of meditation practices. Um, blocking off time to think it was the third thing in the fourth thing. I said it. Perhaps the most helpful thing you can do for reducing stress is being honest, and, um, I was writing the email really fast. sent it off to him, and he replied, He was like, It's so funny said that it's someone just recommended Lying by Sam Harris, a book about honesty, and I had read that book years ago. And, um,

that was one of a few different inflection points where I was like, Okay, the key is so simple. It's what we've been told. 3456 years old. Um, be honest. Everywhere you go.

Honesty really is the best policy.

It really it really isn't. I think for my twenties I don't I did not, um, believe it was the best policy I thought was one of one of 71 of 14 different policies, and it's helpful but had, um I think over the last 45 years Maur and more appreciation for just how powerful being being honest is. And I think what I think about when I say, uh, honesty being so powerful, it's not obviously you. We should avoid mistruths because it's it gets you into. I mean, that's that's That's kind of the above the line view on honesty has avoid mysteries because it gets you in the hot water. It of Rhodes, Um, you know reliability, it Rhodes Trust reputation the Warren buffet style,

you know, 20 years to build trust AnAnd a second to lose it. There is that above the line version. But then there's the below. And I think 90% of the value of being honest is that elicits the right circumstance, the right scenario, the right stimuli for the right response for what you need from someone, what you could use from someone. And that's that's the rial intention behind honesty with With below line is I realized when I was really honest about what I was going through. Oh my God. It was just It was no nature boars a vacuum. And it was very similar type of, ah type of response where I would just say what was going through. And then solutions, comfort, empathy.

Ah, you know, multiple heads working on the same problem just would manifest out of thin air just by being honest about what you're going through. And I was not that way in the first, probably 90% of of Tilt, a company that I built in, and, um, my first kind of major ambitious entrepreneur project 90% of the time it wasn't that I was going around lying, but I certainly was keeping it close to my offensive. Someone asking me, you know, how's ex wires he going? You're crushing it. Yeah, it sounds kind

of like, Ah, most of what you're talking about is being honest with yourself. I mean, when we're told, you know, always tell the truth as kids, that's, you know, tell your parents the truth. Tell your teachers of the truth. But meditation is really just about reality getting rid of the bullshit, right, and really coming to grips with the words around you. Um, the other thing you mentioned under committing well over committing is just lying to yourself, right,

that you can do more than you probably can. So, I mean, this is kind of an internal and external. I think

it sounds like it really is. It's ah, you know, just having a clear lens on the world and yourself. It's, um it is. I mean, you you wouldn't purposely had dirt to the windshield. Um, and I think that's what we do. When when were you lying to ourselves or lying? Thio? Two others. Um, you're just adding so much shit and the way of you being able to see the world and then being

able to see you, you're almost each time you're doing. You almost forking off a whole new reality that you have toe maintain. And you have to remember, What did I say here? What did I say there in the content of load and again the stress, the anxiety, the all that stuff comes crashing down on you because there's no way humans not designed to do that? No, it's not a multi processing computer, right? And so

and we're not even designed to work individually, were designed to work socially. And when you when you're on, I just learned this just late in my entrepreneurial career. Have been doing start up stuff for for 12 years now and and, you know, it took me 789 years to realize just being honest about the situation. Invites that social help that social, um, coordination to find the best answer and also just in common on one of ah ah, earliest episodes, Um, I talked about it a little bit in the episode. He talks about on on Twitter to share the burden, and this is something I think he similarly, um, just learned later in his entrepreneur career to where it's like,

don't try to keep it all contained. Uh, when you really can lean on your team, people want to help when invited, and you can really lean on your team to share the burden of whatever you're going through or whatever your massive challenge there is, I think, and this is just where they thought always goes, is whatever I'm doing that is self sabotaging. It's usually related to an insecurity. And I think early in my entrepreneur career I wanted to do whatever was superhuman. Whatever was some feat that it would be very clear. James went out and did that because I was so insecure of, you know, in my providing value. Am I really the leader of this incredibly smart team? Everyone's doing so many great things around me.

Let me go show that I could do these great things, and and that's just, ah, the omelets, a never ending

a hero complex. And you just you resort to doing things that are that are not sustainable, which is problematic, right?

Right? Exactly, exactly a hero complex, and it's just on that I think you know, probably comes from these stories were told us this individual figure that that goes in ah captures the treasure, and it is just in life. It is never, ever an individual figure. Totally.

So you talked. Ah, and I think in the intro episode about being raised Catholic and kind of that Western philosophy, tradition, But how you've gravitated more and more to kind of Eastern philosophy. Will you go into that a little bit and maybe talk about either the contrast there or how they might actually work together?

Yeah, sure. It sze um I always paradox you might say yes, that it's very paradoxical. Um, in like any paradox, you I don't know. It just feels natural, actually, um, when you get down down to it. Um, So I grew up Catholic, like Alex mentioned. And, um, when I was eight, my dad took me to a transcendental meditation class and and would have books on Buddhism around the house. And I mean 19 eighties and nineties Dallas, Texas. It was

an eccentric, not hot, better hot yoga and meditation

Eventually are are you Bible Belt neighborhood. And, um and it was this fun and he was so comfortable being kind of just different. And it's just he felt so much benefit from meditation. And I remember we had this book on Ah, the Buddhism of Christianity and and it's sort of answer your question. I think there's quite a lot of overlap. And if you take kind of the traditional ism out and you just go to the four Gospels that you could just views, you know, historical documents. I mean, Christina was the most Eastern thing in the Roman Empire at the time. So it quite literally was in Eastern, um, philosophy back then and the idea of union with God God coming down, being on the same plane as us, um,

and and imploring us to be on the same plane as you know, capital h him. It is very Eastern Farm or Eastern than Roman art Greco polytheism. So, um, it felt like complete contrast at the time. You know, when I was a teenager or when my friends would be like, Why is your dad always nap at two PM outside and and um, had to tell him it's not napping? Is doing this other weird thing but fast forward to my twenties. I really just took to the practice of meditation, and it was just the practice of meditation that I really loved. And then I I became pretty fascinated with the philosophies. Ah, not necessarily the R word in Silicon Valley religion.

Ah, people avoided at all costs in Eastern philosophies in general. Other, much more like psycho therapies, then religions. And they're not should and shouldn't, um, as much as they are, Hey, avoid self sabotage by practicing this or practicing that it's not do this to make some deity proud or or avoid. You know, some, um, hellish fire. And when I started to really look at it beyond just a practice of mindfulness or meditation in the mornings from from what I'd learned early in my childhood, what what I think I developed an appreciation for was the psychotherapy with within Buddhism or,

um, you know, Zen Buddhism all the way to Hinduism or my favorite Eastern philosophy is actually a philosophy called Vedanta that is more or less the underpinning. So, um, they say Buddhism is is Hinduism made for export was simplified as it went from India to to China um, and so underpinning Buddhism. You have Hinduism in underpinning Hinduism. You have Vedanta and it really is just a philosophy on how to think and how to not engage in self sabotage. So that philosophy ah, are psychotherapy was really therapeutic when I was going through a really, really stressful times in building company. And ah, and I just developed Ah, I think a psychotherapeutic appreciation for it really need my Ah, my dad did

something very similar to what your dad did, but kind of the two thousand's version and got me Ah, online subscription to the Deepak Chopra Oprah Winfrey meditation website. And so I've dabbled. But, you know, as finally as kind of an adult and a little bit settled into my career, I keep thinking I wanna revisit it more in earnest and so that's really, really

need to hear your experience. Yeah, in many ways, I think, um, we can completely oversimplify these things. But in many ways I grew up with a version of religion which was, um, do this to get X and whether it was, you know, to get God's capital g grace or whether it was do this for for a place in this paradise of heaven. It was do this to get X and what I found very therapeutic, um, psychotherapeutic about Eastern philosophy and specifically Vedanta in. But, you know, Zen Buddhism and Hinduism have these two.

Ah, to certain degree is ah, just the pacification of my mind that is creating so many problems. So it's almost instead of do this to get X. It's take try this out and see what happens. It's much more kind of the y than the what it is much more like Yeah, exactly. It's much more like try this out for your own past. Occasional. Just see what actually happens tomorrow. Not see what happens in this judgment day that could be in ah, 70 years Or it could be the, you know 1000. And I just found It's tighter. Ah, development cycles.

Yeah, start sure, Yeah, it's interesting for my perspective. I grew up in a Christian household, went Thio Christian High School in Southern California, and I would say, my twenties. I kind of largely walked away from a least the organized religion aspect of Christianity. I found myself getting into meditation, not on any level like you in terms of researching Eastern philosophy but just becoming more interested in that school of thought. I think part was a surprising for me actually coming back Thio Faith in Christianity More recently, maybe in the Left 3 to 5 years is how, actually pretty compatible a lot of these things are. I sort of had in my mind this idea that, like you said, that religion sort of a set of rules and trying to attain some sort of an outcome that's distant in the future versus this thing that you can practice day today and get better day by day.

And so it's a little bit of a paradox for me that so much of what I thought was sort of true about Christianity, sort of with fresh 30 something year old eyes turned out toe look quite different when I came back to it after getting into meditation, and we sort of like oddly unbundled and secularized all these things, whether it's fasting, whether it's meditation, these are all things that have deep religious roots in history, that we're sort of seeking out some of us in the cycle of contacts. But they're very highly compatible, which is sort of weird realization that I had more recently, right?

Yes, It's actually, um, you and this innit? Ties to both traditions or philosophies. And I, you know, I still attend church every Sunday and and really love our church that we attend here in San Francisco and Noto, obviously one of the most countercultural or secular cities in America. It's far from the Bible Belt, phenomenal sermons each Sunday from Ah, from my pastor, I've had on on my podcast of just an incredibly talk about honest deep

That was one of the most honest episodes. I think I've ever heard of any podcast. Well, that was the hole. Deeper level of honesty.

And it's and it's why he's been It's probably the fastest growing church in on the West Coast or the in the country because he knows his audience. He knows it is, Ah, pretty intellectual, skeptical San Francisco secular audience and and he just brings hey brings that noise when it comes to the deep richness of a capital and mythical character. And Jesus, um, and it is so rich. So, Alex, your question about Eastern philosophy. I love it for philosophy. I love it is guidance for avoiding self sabotage. Um, and I love it as a psychotherapeutic, um, rumination,

but I I'd say I have more appreciation now, um, in my life, in someone like Jesus to your point column then than I ever have, because it is not. The character tries dhe version

of the cartoon version, but a much more 360 degree version of someone who was talking about a paradox. Fully God fully, man. I mean, wrap your head around

that. I mean, it's so, uh, I love talking about this, um, but I'll keep it thio 60 seconds. But it's ah, if you talk about paradox, he's the best of us, the most perfect of us. And this is this is not the history city of whether you think that there are miracles and just think about it from the ah, the mythology. And I mean this in a very respected mythology sense. But in that mythological sense, maybe, really,

is the perfect ideal myth of the perfect person. The most perfect character, God comes down to be man who is perfect again, not the History City. But just think about this as, ah abstract concept of the perfect character comes down who then has betrayed, tortured, killed for shit. He never did. And he literally is going through it all for us, who we are betraying, torturing and killing this character. And it's not this idea of a king, but that is the most ideal of what you would ever want from a king. So, therefore,

is king right there? Therefore it is Ah, it's the ideal for a king or for, ah, for any one of us and then, you know, comes clean on the other side, having saved us from what, what we have collectively, you know, caused in terms of of self sabotage. So, uh, that's so rich and it's yeah, to your point. They make you read Great Gatsby in eighth grade and you don't appreciate it all. You got to read it when you're 25 you're like, Holy shit, this

is really, really deep thinking about, right,

right? It's the same for Christianity.

We can come back to this. I think there's a lot of rich stuff here, but just to switch gears a little bit, it seems like you've always been super create ever. You make music, you've built several companies. Ah, you're making a podcast. You just give us your new awesome book beyond coffee. Have you always been created? And what are some of the earliest memories you have of maybe as a child, creating things from scratch, Kind of going from 0 to 1?

It's, um I think, like a lot of things in life and what we just touched on, I think there was a threat of it early. And then I moved away from it for for a little while and then came back to it. So when I was young, 567 I loved to draw and would always draw was entering different contests. Um, remember, I won a contest to draw our little school, um, directory that cover for it for elementary school. And I thought it was so cool. And then you know what? 89 10? Um, there's nothing specific, but I remember being more and more encouraged into sports and into academics, and it probably hit me. Maybe only two years ago that I did not know a single artist growing up until I was maybe 25 or 26.

This is not like I didn't like you ever know personally, I outside

of the artists that you would read about it in a book or that you'd hear people talk about I did not know the concept of what an artist was like, literally, It was you got Picasso, maybe some Mozart and Beethoven. I still am just so blown away by that it's like a satisfactory of growing. But I did not know a single riel artist. Now, kids in my class, you know, Drew. But I had no ah example in my head that you could pursue art, musician or, you know, painter Ah, as ah as a profession at all. And my wife is an artist. We met a 2024.

So, um, she didn't start pursuing it professionally until she was about to 26. But, um but I think that started awakened. Just my desire to create knows, I think, subconsciously just thought out of, especially in Dallas, Texas, um, are growing up there and thinking through Okay, lawyer, doctor, real estate, oil and gas oil tycoon Oil taik.

It's like Oh, entrepreneur, that's what I'll be sure. And I think I just on Lee maybe two years ago put it together. I was like, Oh, that's the professional artistic thing I can go into And, um and yet it's the last 10 years or so, uh, lean into entrepreneurial activities. But then in the last few years, maybe less. 34 got back into making music that I used to make when I was younger and a little bit in college. And then ah yeah, the podcast. I think it's my favorite creation today. Awesome. So the

Social Network, the film in 2010 or so kind of really popularized the idea of this founder CEO made it really trendy and cool, but you've actually done it. Unlike most people out there, what are some of the biggest misconceptions about what that's like? Especially as it pertains to your experience building tilt over five years or more and then ultimately being acquired and merging with Airbnb?

Yeah, well, even the real version of that was, you know, we use the word acquired, um, or entrepreneurial or, you know, being a founder. And we think we have this. This image of what is the conception is that you own your destiny or you're your own boss or you have freedom and I know for me that was my conception of it was it's freedom writ large like that's being an entrepreneur. You're your own boss, and that just is not my experience. It's never been my experience in creating any of these things. Um, and you're always beholden to the audience here, customers,

Whoever you're communicating with, Whoever you're creating four with the company, you quickly learn within like, Oh, no. After you buy to monitors at home and you set up your desk completely for the startup that you're gonna build and you're like all right, I quit two weeks ago, and now we're doing it for real, and you're setting up the L L C fast for, like, three months and you realize, okay, no one is really digging what I would have created so far, and you realize it really is. Conversation is communication. And then,

if you're lucky enough to fast forward a year 23 years later and and you have many customers, you're like, Oh my God, I need to keep a conversation with 10,000 different customers going and the product is never good enough, the number of customers has never never large enough. And so I, uh, quickly learned it's just not, you know, instead of one boss, you have 70 employees, their bosses or 10,000

customers. Better bosses have aboard even vessel board. Quite

literally, I have 345 board members that are your bosses and, uh, the social network not only was a mistake conceptual or just ah, it just was, ah, false notion of entrepreneurship as a movie. I remember watching it, too, and being like, Wow, that's freedom. He's two years older than me. Must you must be on top of the world. Ah, even though obviously the the movie is about him screwing people over and being alone and having this one character and ah, the ah who played Shawn Parkins,

Justin Timberlake was Sean Parker. Yeah, exactly like that's who he has. Ah, next time by the end of the movie and And it's not a heroic tale where you'd want to be that person, but it sze So easy, I think, is a ah young person. Be like while those offices look cool, we know how the story ended, goes public for $100 billion let me disregard what's being obviously the kind of written into this this screenplay and go for that, That idea of freedom, It just it's

not that great as it pertains to till what would you say was kind of the the peak moment of that whole endeavor for you, where you felt like you were really on top and what was maybe the lowest moment you had.

Well, I'll tell you, it's a slight side story about Ah, a little bit of a connection between Tilton and Facebook or the social networking movie. So I I had built a started before that, uh, before tilt called Developed Out Organ. It was focused on crowd funding for nonprofit. So fund raising for nonprofits and 8 4010 and it was more of a nights and weekends project had to shut it down. Umm, after just lack of enough response from customers. And I remember just even that I was like, Buck, this is so, so stressful. I mean, I've just told all of my friends and family about this thing for thing I've worked on for 19 months.

I told you I was coming. It was launching. Was the launching was coming. It was cos it's gonna be awesome. It's gonna be awesome. Then it happens. And then crickets, crickets and then crickets and crickets. And then everyone that I had ever built you a good will or relationship or reputation with them, like we're shutting the doors. And it was so embarrassing and and just felt like, Ah, this is I built all this good will by doing all of these things right now, I got a big L. And it's a big Lawson. I just want to be useful,

and they're not gonna think that I'm very useful in the next thing I try. I thought it was pretty, you know, existential. And then, uh and then I saw the Social Network. So, to your question, I saw that I was like, That's what it can be like. I was 20 for maybe. And I previously said, I'm never starting anything ever again and then saw at the Social Network in that night. I was like, I'm back in back in. It was like maybe eight months after I'd wind down,

developed adoring. I was like, I'm back in. I'm gonna reuse the software, built out this amazing code base and reason software for for this other idea that I kind of have Ah, fast forward About maybe a year and 1/2 after that were we get through Goto y Combinator would get through y Combinator And Sean Parker wants to meet with us And he initially wants to buy, um, until we're, like five people and he wanted aah! Purchase us as a ah, as, um and until for listeners is basically a mobile version of crowdfunding. So instead of a $50,000 documentary, you throw up Ah ah, a tilt campaign for 1500 bucks for, you know,

a tailgate on Saturday for the college football game or the, uh, or $500 community fund raiser. And this was basically us go fund me and Kickstarter kind of off to the races tow Try to win the space. And we thought we had something unique with a mobile kind of Twitter esque version of Crowdfunding. And and Sean Parker thought it was somewhat interesting as well. And he, um, approach us originally toe by us of five people and and then we build it together and he'd be basically, um, you know, we sell the equity stake, but he would He would run it, which is really super flattering. Um, but we turned down and then three months later,

is like, all right, I want to invest, um, and come see me in New York and we'll talk about how we build tilt out to be, Ah, the Facebook of money. Go to New York in

a sushi restaurant and asked the restaurant, Yes. Let me make the move

you love. Yeah, exactly. This is so surreal. I've probably told this story 10 times, and every time I'm like, I cannot believe that that actually So, um, we're in a sushi restaurant until at that time was called crowd till sitting down him and his investment manager. Ah, Michael and I have, like, a backpack next time, like, what are we doing? We're at Nobu, um,

and really nice sushi restaurant. And he's getting, like, just the Sean Parker special, cause I think at this point, he's probably billionaire at this point. They're just like, bringing all of, like, just the nice. There's no menus. There's no ordering this bring, you know, And it was almost a ziff, like just the room was like spinning. I'm like this is just so crazy.

I'm gonna be like I'm in the movie right now. That is crazy. And

yeah, in New York with Sean Parker. And I swear to you, I'm not making this up It all He said, he looks me goes Have you ever thought about dropping the crowd and just going going by tilt?

Oh, my gosh. And I was robbed of the

and Yeah, exactly. And so just like the scene from the movie and wow for listeners that by not know the scene if you watch the movie, it is exactly like the scenes movie. And I was like, What the hell is having? I was 24 25. I was like, What the hell is happening right now? That's crazy. So story that was very uh yeah, that was probably the most surreal moment. But to your question, Alex, I'd say, out of five years of building the company, there's probably only four months the entire five years where I was like,

Hey, we're ahead of the April for the other four years and eight months. It was every night, every morning I mean, it's I I relive it in my mind. I just feel so bad for all of my friends, for for my wife, for my family. I was just always felt like we're behind a pill every day. And I And it's something that I think is poorly understood about entrepreneurship is the human mind in the human body Can go through pretty intense stress for two months. Four months, five months. It's not built. I mean, you know, he wouldn't have,

um, in nature or in civilization 1000 years ago, you just you wouldn't have three years, Four years? Five years. I mean, that you'd have a famine every 60 years or something, but nothing about her. Biology is built for 345 years of intense stress, and I did not appreciate that back then. Um, just cause you think like, oh, well, I mean, this isn't warfare.

This isn't, uh I'm not. My life isn't on the line, but psychologically, you really do feel like you Mentally. Your life is on the line for any entrepreneur out there. They, uh, any non entrepreneurs? I think they kind of scoff that any entrepreneurs like yes, that is exactly it is. Psychologically I feel like my survival's on the line,

and it's tough because so much of your identity is wrapped up in the company, the success of the company or the challenges of the company. You're attached to certain goals or outcomes. And you have people whether it's investors, advisers, employees, right that one to achieve a certain thing. And you feel probably solely responsible for at least guiding the ship in that direction.

Hugely responsible, you feel you feel like you're you're you are in the driver's seat. Yes, the engine can still break down. The car can still ah, you know, veer off the road or or, you know the road itself can can crumble before you, but you're still the driver. You still have the most control. And as you know that, I think in your head you you it's is very clear that you have the most control. Maybe you're 30% of the equation, but that's by far the most control. And I think in my head what was so tough is I felt like I was 90% 100% the things that I do or don't d'oh and that was really, really tough. And I think it's just I mean,

I only understood this afterwards, but my bio physiology was so wrecked, like my cortisol. Ah, stress hormone was just had been elevated for five straight years. And that's what I mean when I say, like our bodies just not built for five years of stress. I mean, it's really tough to have 34 months of stress, but five years is really tough. And I think we don't have much of, ah, societal appreciation for ah, for how hard it is to to create. And yeah, Carl,

you mentioned just goals or these. This is future that you, creator you get attached to. That's the self sabotage that I think we we don't even realize we sign up for, um when we set some audacious crazy goal and tie it to a date, Then he miss it, and then you miss the next one of them. Then you miss the next one. You basically just like tying yourself on the train tracks, running over yourself, tying it again, running over yourself. You were the one tying yourself to the train tracks and setting up that situation that that you have elevated cortisol or that sleepless night because you, you slip right into it of like, Oh, yeah, it sounded so good when we said that big, audacious goal and everyone like cheered and everyone felt like Let's go and do it and ah, and yet you didn't realize what you signed up for when you raise expectations to the point where you feel like Oh shit Now we're behind the eight ball for 17 months in a row,

going back to kind of the threat on honesty From the beginning on, I've worked in start ups for the last 10 years, kind of similar time frame as an employee on the employees side, it's always interesting because you always sort of in your gut have a sense of how things were going. You don't have perfect information and look, there's things that executive team or or the leaders of the company may know that you don't know. But in general you have a sense of things were going well, or things, or maybe not going as well. And what I've always experienced on the employee's side is that when there is that level of honesty about, this is the challenge example could be we've been pedal to the metal on growth. But we really need to shift focus to unit economics. We just got to get our house in order so that we can build a durable business. I've always found that whenever the founders very honest, going back to the honesty thing again, the help, the empathy from employees starts to arrive in a pretty magical way.

And even though I can imagine that I've been a founder of a couple small projects with a couple employees, but you're worried about the employees like, Oh, they're lively hoods, you know, attached up in in this thing that I'm leading. But actually, they're probably very open toe wanting to to hear the truth, good batter, ugly and actually adjust their mindset in their expectations and kind of rally around whatever the situation may be. Because people I think are so hungry for that honesty, and they don't get it in the world that when they do get it, even when it's bad, there's something oddly refreshing about it. I don't know if you talk a little more about that, but I've I've certainly experienced that in a couple of different companies. Yeah, certain moments

that I've gotten tough. Yeah, it's It is. Ah, I love that about Brian Chesky at Arian Bees is just so honest about Aah! About and and continually, I was just even 10 years in of Airbnb being who knows what with evaluation is but certainly tens of billions of dollars in the in terms of being financially successful. It just was so honest all the time about what wasn't going well and with the things that he was worried about and that does it list it just the right. It's like, Okay, I can build my house. Pawn rock here like this is like, this is real And and I think we I know that I would that struggle to be vulnerable? Um, I think it goes back to just our preconceived notions of what is strong or what is cool like you. You don't want to be the person like talking about how you are ill equipped for this challenge ahead is not That would not make you cool in your in your group of friends. That would not make you seem strong on you know,

the basketball team that you play and in these, Nor would that make for a very compelling narrative arc and the bullshit stories that were told Talk about like the hero individual story that's you were told these stories, Um, that just now I feel like I I feel like I think there's more and more every month that these stories are just total total bullshit, like behind my podcast. Ah, big shoutout Thio Sam, Meghan J. A. They will help with this with a podcast that I'm the host, but it's really them thinking about things constantly, um, to to grow it to, to make it better with Tilt. It was a company of 70 people 100 people at our height. My co founder,

Caleb, was like he was the rock that I could really build the company on. It is your Airbnb is 5000 people strong, and yet it just gets reduced down to that guy who is the quote unquote founder or CEO. And it's just I mean, it's ah, it just never is the reality of this story. But what it does is the stories tell you it's an individual, and the stories also tell you it's like the Greco story of Achilles, like it's not him being like guys I don't think I could sign. Females help bad. It's like Let me go save the day and I'm gonna go be the hero. You know, that saves this this situation and that's really Ah, so far from the truth and really dangerous to do in a team setting. And I just found myself in my twenties just doing it and doing it over and over again of like, let me go try to save the day or thinking I need to rather than you to your point just saying it were We all got to step it up. And this is where I failed to swear,

You know, I'm I am not getting it done. I think to some extent I think that's sort of what you do in your twenties. You were in a very extreme situation and a high pressure role in your twenties, but I think I can speak personally for myself. I think in my twenties and I tried to start a company coming out of college at Berkeley and I was trying to sell fun and just be the hero, and we rented an office and hired a couple employees, and it was just it was all about putting it on my own shoulders. And you just can't do that and talk about building your house in the sand. That's a very quick way to do it when you're literally relying on your own human strength to do everything. And it's just it's just not scaleable. It's not healthy. It's not possible. It's not how we were designed where social creatures were spiritual beings, right? And so that's something that I didn't get at all in my twenties, that now on the other side of it in my thirties,

I have, ah, much deeper appreciation for and it's been a game changing to kind of have that journey, but so good to be on the other side of it. I would not want to relive any of my early twenties at all.

Totally it is, Yeah, I I am so thankful for ah, the wisdom that comes from just foolishly doing things the wrong way over and over again. Um and hopefully listeners listening and just, you know, circumvent that altogether because it's and hopefully we collectively and the way that we talked about entrepreneurship really move past the idea that it is these individuals that are super here. I mean, it's like it's just the Those are the narrative arcs that we and

they're similar to tell right there. They're much more simple. That's any kind of heroes and villains know.

I honestly think that that is the reason that because you can't say, Hey, look, it isn't Superman. Yeah, it's all 500,000 of us pulling to get. You cannot

tell that, and those stories don't spread. I mean, we're living in. I think there is a great quote from Jeff Bezos about how social media is like a nuance destruction machine. And we're living inside of the nuance destruction machine where all that nuance of how a company gets built, how a podcast gets created, just gets absolutely

destroyed. And that's why it's so great that way. I don't think we are. We're actually living, at least right now on what you're doing with the Paradox podcast. We're living in the nuance machine, which is podcasting. That is why I love this medium so much because it it is. It is a better medium than reading writing, then, then having to create visual ah visual medium like video, which is just such high costs of creation and high costs of distribution. It's just audio is so great, and conversation is so great for nuance. That's why probably the single biggest reason I love podcast because it is just, like so, replete with new ones,

and you can actually spend five minutes to explain out a concept. But then you put that in a I don't know. You put that in a to do list to do as a blogger post and ever gets done. Or, God forbid, you try to condense a five minute thought into, Ah, tweet. It's just damn near impossible.

There was a podcast that I loved that spent a whole season looking at a Kanye West album, which was also one of my favorite albums. Actually, Kyle and I were roommates when it came out of my beautiful, dark, twisted Venice. Yeah, in this day and age of you know, 32nd clips or five second clips, it was like, Wow, these people are taking the time to dive into something which maybe it's kind of silly, but I think it merits Cem riel consideration some real reflection. So I I absolutely share that, and it's like we went from this just extreme acceleration through technology. We had access to so much our attention span kind of contracted. We wanted everything at our fingertips,

and it seems like maybe there's some pushback on that where it's like, Well, wait a minute. I can't get everything from short sound bites. I'm not actually getting a full understanding. And I think podcasts are kind of the answer to that,

right? Yeah. Uh, nerve, all Ravic, it who I love. I love in a ball and he tweeted out yesterday, the day before this thought that it's, you know, it's, um it's essentially minimize everything, and and, uh, and it's the job of the communicator to minimize everything and

and a phone call could be an email, and he could be attacks. The female

are a podcast to be a snippet. Sure, actually, don't agree with that. Um, I think, yes, that is more convenient. But what I love about podcasts and where I personally So he you know, he's opposite media's four minutes like acid ideo er done like a three hour one before, and and most are around two hours. And that's because I really love um I really love going deeper and deeper into someone's story, and it's and it's I don't think it's for everyone, but I don't agree with the snippet. I think snippets are great for collection. If you're trying to collect factoids and, ah,

and little bits of information, then yeah, you want to be able to sift through things, find what you want, take it put in your pocket, collected and accumulate. But I don't think that's at least for me. I don't think that's what I want. I don't want to accumulate. I actually really want to go explore different worlds, and that's the difference between, um, I don't know. It's Ah different strata a block post in Dostoevsky. It's like No, actually, really want to go deep into this world that, ah, that this person has created or this podcast conversations

created Well, that was the first novel, Ravi Kant reference on the podcast. I'm amazed we got all the way to episode. The reasons I'm such a fan, how come

real quick? What were the things that you love about novel? I love him, too, but, um, I disagree with him on uncertain key things, but he really is the clip probably the clearest thinker in technology. I think

there's a level of boldness and, you might say, courage to say some things that maybe are actually pretty unpopular in the Valley and also just I think he's a champion for saying what you think. And it's okay if we disagree. Like you guys are obviously friends like it's not a big deal to disagree. And there's probably a world where involves four minute podcasts and your two hour nuanced discussions can co exist, right? And I think I started following him back in 9 4010 I think I heard him, maybe on a couple of podcasts, and I just Ah, yeah, just like the way that he thinks that the word contrarians like a joke. At this point in Silicon Valley, it's thrown around so much. Someone had a really great I didn't read the Post, but someone had a great title to block Post, saying I,

too, am contrarian making fun of just the ridiculous lemming like Ah, uh, sometimes model culture that we have in Silicon Valley. So I think he's been refreshing in that sense and similar to the way that your podcast, I think, is again cut through kind of this conventional narrative around, you know, the optics of running a company and actually going below the line towards honesty. I think there's there's some commonalities there. But but speaking of novel, in speaking of Angel investing, I didn't want to touch on Angel investing briefly. We're kind of in this era of the operator Angels with, you know, uber going public and Airbnb is gonna go public soon,

and slack went public. So it seems like you could really throw a term sheet on Market Street and hit like five Angel investors like there's a proliferation of capital but probably shortage of ideas to put that capital into. But you made your first angel investment. This is from your Lincoln profile, some assuming it's correct back in 2013. So before it was quite a ce hot. It's, you know, 67 years ago. Walk us through what writing that first check was like and and kind of what your first angel investment, what it was and what the fuck process was behind it.

We'll talk about how your stories are meaningless. It's Ah, I'll tell you this story, but there's there's nothing to really to replicate. I s Oh, we're in White Combinator And Josh Reeves, the founder of co founder of gusto, asked me to invest. And as 24 I did not have any capital to invest And why, I think I maybe had, like, $24,000 a savings. And, um and why commentary gives you 100 20 case? I was like, OK, I don't need to just keep no shelling out savings for for ah, for Tilton. And, um and I really loved

getting known during y

Combinator. I wrote them a $20,000 check and in gusto is now gone on Thio. Ah, well, over, um, a $2 billion evaluation and it's I just got really lucky in that first. But that first check was just me feeling like, all right, I'm decent at creating financial opportunities and and situations. I'm basically putting everything I have into another friend's company while I'm putting everything that I have into my own company. But yet, so funny, I just I didn't think I was angel mess anything. I was becoming

a I just thought helping

a friend. Yes, helping a friend, and I think

this is gonna diversify a little bit on some

level a little bit. Um, but, uh uh, Well, actually, I think I actually thought like, oh, shit, I'm like, putting everything

into start ups. I don't know if this is is I'm overexposed on start ups

right now, so I, ah, probably felt like it wasn't diversification, But I definitely look back. And I feel like that was just like and it was the right singular moment type of ah, situation and our type of decision, Where is like, okay, really smart founder.

And you're messing in the person of that point Anyway,

You know them really well, going through y Combinator, you know, I don't know aka mate too. Just what 200 different types of founders were like. And so I could see Ah, the differentiation off of him and Tomer and Eddie as founders And ah, so wrote that check and then ah, and then I think it's like, I don't know, doing well in your first hand of blackjack. You like All right, let me sit at the table a little while and ah, and just kept doing

it. And so speaking of continuing to do it. How did you make the transition? More recently, from doing this on the side as you're building your company to being now full time angel investor. So,

um, it was me. I was very linear for me. Was I built it. Tilt really failed in our attempt tow build that to be the Sean Parker's where it's a Facebook of money and social underground money. It's We ended up selling. So Ah, Alex, the word acquisition. Yeah, it's Ah, it seems like it's just this Ah, simple word. Such a painful experience. The last 18 months of tilts life was just trying everything we could for a revenue model around this way, this great viral growth. And I mean,

that was just growing year over year and triple digits. What you'd kill for as a startup founder, but similar to of emojis everything we were trying in 2015 and 2016 of different fee structures going after business clients building at a enterprise product, um, building our premium features. They just would not. They would not stick for a decent revenue model and and so we ultimately had to sell to Airbnb and, um And so we sold and basically was just fire sale was, like, 95% of our value. Ah, was was cut down and Airbnb um you know, I guess from beginning to end, I would have been happy with it. But we flew really close to the sun we got We got really close to building something really special. Um,

and ah, and had a really hefty valuation. High profile, all these things that you just talk about self sabotage because you just don't wouldn't come within 10 miles of doing again in my next ah company, but made all of these mistakes went through this painful process. And I was like, I just want to help prevent this from having other people as much as possible at that point, maybe had invested in 13 or 14 companies. And so it's like, All right, not only do I love guiding other young founders, but, um, I'm gonna do this. Maura's Ah, as I have a little bit more free time and in,

um and being an executive at Airbnb rather than the founder, so did a little bit more loved it honestly felt like it was God's work like I was like, This is perhaps the highest leverage thing I could be doing is helping other founders and thought I was gonna be an executive coach. Um, the reason I started the podcast was also just trying to understand founder, psychology or creator psychology, a concept that that we have sports psychology. But when we don't have business, psychology and and, um and I was and I wondered if the last few years why we don't study psychology of creation. What is normal? Why so many founders myself included you guys Probably the same with this podcast. You just have to piecemeal like, Oh, no, this is normal,

right? Oh, yeah. I think someone mentioned something like this And is this psychology or this feeling right? It's normal. Like, yo, and these these internal conversations just wanted externalize them with podcast and and, um, enjoy doing that in 101 settings with coaching. So I thought that was gonna be executive coach. And then, um, I thought, Well, you know,

I've invested ah to this point done decently. Well, actually financial. I could do that full time and use that as the transfers to advise other other founders and and then probably start something on my own again. It's

so interesting because you went through this very intense experience. You said there may be four months, a building tilt that felt like you're kind of on top of the world and the rest was kind of being behind the Eightball on being super stressed out. And it's so interesting because on the other side of it, on this side of that experience, people sometimes talk about like you go through something and it's not really about you. It's the people that you're gonna help through that experience on the other side. And I think that being able to sit down with founders have honest and real conversations, maybe invest, maybe enter them to other investors. But really get riel with them about bounder psychology, about the challenges. A building company. You would not be in a position to do that had you not gone through that experience, that experience enabled you to do that. Do you have that perspective now that wow, it actually has sent me on this whole other path helping other founders that I would not have been on how to not gone through that trial wolf. For sure, I never I

never went through it thinking, I wish I could avoid this just to be clear, I went through it and was like, This is I mean, there was There was a moment where I was just breaking down in tears in the bathroom, in my wife's parentshouse and and just breaking down in tears. I couldn't stand up and just was definitely thinking, What the hell is happening? This is how will I get through this? But the whole time I was never thinking. I wish I wasn't in this position. And I think it's, um I just was had already been to the really tough things in life early on that I had already somehow, um, somehow acquired the mindset of this. You know, things happen for you,

not to you. And so I was going through it. My wife and I talked about this to this day when there's no challenges and we're talking about this an hour ago. Ah, you can choose to to think about these things as as not that you chose them to happen. But you can always sit there and imagine what if I chose this What would be the blessing within this toe are would choose is in many of us choose to go to the gym and put your muscles through intense stress voluntarily. You on purpose. So why not put your spirit through through stress so that you could build up some muscle there as

well? So that was part one of our conversation with James Bashira, and we had such an in depth discussion that we decided to break it up into two episodes coming soon. In Part two. We dive deeper into this notion that mental health is wealth.

You know that phrase. Health is wealth. I think you and I or, you know, Alex. We could all be healthy but have a mental state of depression. And that's not wealth. So I don't think even health is wealth. I think you could actually be, uh I have, ah, paraplegic neighbor, one of the happiest people I know.

We also talked about James's passion for encouraging more people in society to create and how creation is something deep in our DNA as humans.

Probably the biggest ailment to our ability to solve things is that we're not a participatory culture. You go home. You order food in you watch four hours of TV a day of other people participating in life. If you were to film that person day today, no one would watch it because they're not participating in anything.

That's a wrap for this episode of the paradox Podcasts. If you like to connect, you can follow us on Twitter at Kyle Tibbets and at Mr Alex Con. If you enjoyed the episode, please rate in Review us and iTunes to spread the word until next time. Take care of yourself.