The Exchanges

Q passions and your interests in ways that have led you to do not just interesting things, but things that have been lucrative that have worked out like your podcast was just kind of a started out as just a fun little project, which turned into a real business. Now you're doing A card game, which is totally out of left field. Tell me about how you, what inspired this idea?

A So I tend to explore these off menu out of left field things for skill development, learning, and new relationships, right? So the podcast, I launched it as a lark, but I basically wanted to ask myself, how could this win even if it fails? And I did the same thing with angel investing, just treated it as paying for A business degree. So in this particular case, I'm looking at it the same way, and it came about because I have seen in my audiences sorely needed as an antidote to digital malaise and loneliness, which is in-person social time with something that is a light lift. So how could I design a game that takes about two minutes to learn, 10 minutes to play, that can help people Offset their screen time and all of the things that come with excessive screen time with family, with friends, that hopefully makes you a little bit smarter, right?

AI assessment note: “came about because I have seen in my audiences sorely needed as an antidote”

Q I remember that. What was it, what was a thing that, that kind of changed?

A Oh, that's easy. Uh, I mean, I remember, uh, The last day of fifth grade, I had this amazing teacher named Mrs. Talmadge, and I was sitting up in the front of the class. I was the last kid left in class. This was the bell right at the beginning of summer breaks. Everybody had run out, and I had terrible sunburn, and these two bullies walked out, and one of them goes, have a good summer, Tim, and slaps my back really hard with an open palm, and I held it together until they got outside of the classroom, And then I just started bawling, because it hurt so badly, and Mrs. Talmadge, who had this kind of raspy voice, she had a bunch to say that I couldn't really absorb, so I was crying, and then she said, one day, you'll show them, you'll show them, Timmy, and I was like, ok, ok. I went away to camp that summer, and I grew something like five inches, and gained like 40 pounds of muscle, because puberty hormones just flooded my system, and Came back, and sixth grade was just my year of joyful vengeance. I mean, so, the bullying stopped pretty quickly in the beginning of sixth grade.

AI assessment note: “I went away to camp that summer, and I grew something like five inches”

Q Yeah. But presumably you still wanted to make money. You still wanted the business to operate. So what kind of things did you put in place to, to allow you to do that?

A Well, there were some really simple things. For instance, that I sent out an email to my fulfillment center and said, from this point forward, in effect, please assume that if a problem can be fixed, For less than a hundred dollars, just go ahead and fix it, charge it to my account. That type of providing of guidelines for autonomous decision making. Uh, and the fixes required a lot of hard thought, but the implementation of most of them was actually very, very simple. Firing a bunch of my high maintenance customers. That was another thing. Uh, you know, a handful of my 20 Wholesale customers were producing like 90% of the negative emotions that I felt with my customers. So, but they were really lucrative. So I had, uh, I put up with a lot of nonsense and bad behavior and basically sending a letter to those folks saying, here are the policies going forward. If these terms don't work for you and your company, we're happy to make a referral to another company who can blah, blah, blah, blah, blah. And almost all of those belligerent customers did a complete one 80 about face and went on best behavior. One or two cursed me out, and I fired them, and just with that decision alone, the emotional experience that I had working completely changed, but what's really important is that I had arrived at a point where I'd committed to either untangling the mess and extricating myself as a bo…

AI assessment note: “I sent out an email to my fulfillment center and said... Firing a bunch of my high maintenance customers.”

Q I read that, um, when you were 15, you went to Japan for a year as an exchange student, which is pretty cool. I mean, those programs existed, but, like, tell me about that year. What did that, what did that do for you?

A That year, for me, completely changed the trajectory of my life and the way that I looked at the world, because I'd never spent any extended time outside of the United States. And, um, Went to Japan speaking very basic Japanese, and I was the Where's Waldo American in this school of, let's call it, a few thousand Japanese students wearing a school uniform. And that year helped me to see how many of the rules that we follow are really social constructs and kind of arbitrary, right? Driving on the right side of Of the road versus the left in Japan, or bathing rituals, right? Even the grammar of Japanese is so different from English and the sentence structure. All of these behaviors and habits that I never questioned before became this comparison, side by side comparison, with everything I noticed in Japan. So when I came back, I was looking at everything in the U.S. and in my life with very fresh eyes.

AI assessment note: “completely changed the trajectory of my life and the way that I looked at the world”

Q When this became a phenomenon, you became famous overnight. I mean, pretty quickly, not overnight, but pretty quickly and much in demand as a speaker or As a consultant, um, you really became this kind of iconic figure, certainly in, among a certain type of, of Silicon Valley tech worker. Did you like that? Did you like all of a sudden becoming kind of famous?

A I liked aspects of it. I was bewildered and flattered. It just shot so far beyond anything I could have anticipated that I was Also caught very unprepared. I don't, I don't know if you can prepare for something like that, even if you knew that it was coming, but the amount of inbound that you get when a book hits the New York Times bestseller list and stays on that list for a period of time is incredibly exciting. Speakers, bureaus, interviews, foreign rights, movie rights, I mean, all of these things. And I had no idea how to handle any of it. So there's part of me that thought I finally reached escape velocity, this is what I've always wanted, and quickly learned that there were a lot of downsides and compromises, privacy issues, crazy people, stalkers, death threats, I mean, nuts. Not so experiences that I would not have envisioned being part of the package.

AI assessment note: “I liked aspects of it. I was bewildered and flattered.”

Q about this, um, when I was a guest on, on your show, um, about this period in life, this, like, late teens to mid to late twenties, this particularly vulnerable situation. Period. For a variety of reasons. There's societal pressures, and our brains are changing, and there's a bunch of bunch of things happening. Do you think for you that that was why you were in that state of mind?

A Well, I think it was a combination of darkness, meaning seasonal depression, plus, uh, feeling everything has been building up prior to Princeton to getting into a school like Princeton. And now my parents, extended family have all helped me to attend this expensive school, um, This has been a significant, huge commitment and sacrifice on the part of not just my parents, but other people in the family, and now it seems like I'm gonna fail. I felt just helpless and hopeless. But let me add a note on the light side, which is, I have not suffered an extended depressive episode in, let's see here, something like six to eight years now. So, There are, I, I have found tools and approaches that really seem to mitigate a lot of this.

AI assessment note: “Well, I think it was a combination of darkness, meaning seasonal depression, plus,”

Q But, but you were also, like, not just taking tango classes. Like, you then eventually would compete in the tango world championships, and, uh, Got an entry in the Guinness Book of World Records for most consecutive tango spins. Like, that's like taking it to a different level, like a competitive level. Is that, what, where did that come from?

A It came from a few things. I wanted to get better at tango, and for me, getting learning skills has a blueprint, and it's, there are certain approaches that just improve your rate Of learning. So, I collected video clips of myself dancing, of other instructors dancing, teaching certain techniques, and then each night, I would take that footage, and I would put them into different folders based on the type of technique. Then, based on the video, I would take notes in a tiny little notebook that I could fit in my back pocket, and I would try to use these techniques in the wild, which often backfired. Then I would take notes on what went wrong, And, I mean, I, I practiced like six hours a day. I mean, I had to take days off because my feet would get bruised because the shoes are really, really thin. And, uh, I loved it. I really, I really loved it.

AI assessment note: “It came from a few things. I wanted to get better at tango”

Q So, so, all right. So you're having this experience, and while you're overseas, you, you realize you can have a much richer, more fulfilling life without having to work on this, this all-consuming business all the time. And, and is this when you start to think you might write a book about this whole experience?

A The book was nowhere on my radar during the travel period. But, um, I had taken notes along the way, because I have always taken notes, and I ended up with this huge stack of, of material, so I, at one point, emailed Jack Canfield, who was co-author or co-creator of Chicken Soup for the Soul, because I had gotten to know him by volunteering at non-profits, and I reached out to him, and I was like, Jack, here's what's going on, Do you think there's anything here to chew on? Should I even look into this? Hoping that he would just kind of snuff it out. If that makes any sense. I didn't really want to write a book, but it was on my mind.

AI assessment note: “The book was nowhere on my radar during the travel period.”

Q But how did you, given that you were an unknown writer, right? You did not have access to national media. You were not a celebrity. I mean, how were you going to convince these, or how did you even get these outlets to cover the book at all and to cover you?

A Well, it was a progression, right? So I think when people try to launch, oftentimes they think that the more customers I have, the more prospects, the better. So everyone's going to be my customer, right? And when everyone's your customer, no one's your customer. You don't have any focus. So for me, I thought to myself, well, really my first target is let's just, let's just call it. 20 to 35 year old tech savvy males in a handful of major cities like San Francisco. And I know how to reach those people because I'm being highly specific. If I knock over that domino, then the next domino to fall will be 20 to 35 year old tech savvy females in the same cities. So I went after the bloggers first, and what I would do is just go to these events, I'd kind of loiter around, I'd try to end up in a small group of people who were talking, I would buy drinks when I could, and eventually somebody in the group would say, Who the hell are you again? Like, you've been sitting here for an hour listening to everybody else. Like, what do you do? And I go, oh, I'm working on my first book, and, um, I'm here trying to learn more about blogs, right? I would leave it at that. This is really important. And then if anybody followed up and said, well, what's the book about? Then I would tell them, and then maybe give them an example. And at the end of it, if they seemed interested, I would say, if you'd …

AI assessment note: “I went after the bloggers first, and what I would do is just go to these events”

Q This is really where you kind of, I think, begin to, I mean, you'd always been experimenting on yourself, right, with supplements and different things, and, but this is really where you Kind of become, for a while, known as, as like a human guinea pig. Did that annoy you? Did you think that that was, it wasn't really explaining, describing what you do or did?

A I was all for it. I described myself that way, also. One peculiar aspect of my hardwiring is that I enjoy figuring out the puzzle. I enjoy being the human guinea pig who tries a thousand things and then puts together the Cliff Notes index card version for my friends or readers. I get a high out of that. Yeah. I will say a lot of the things that I do also are just to see if it's possible. So for instance, I, I have reduced capacity in my left lung from complications when I was born premature. And the story I've always told myself is I, I, Can't hold my breath as long as so-called normal people, but then I spent time with David Blaine, who had learned how to hold his breath for, I want to say, 14 plus minutes, and was able to get to a point, combining practice and technique, I got to the point where I could hold my breath for five minutes plus.

AI assessment note: “I was all for it. I described myself that way, also.”

Q kind of got it to the point where you, you were able to travel and then you, you ended up traveling for like the next 18 months or so, like starting in London and then Ireland and Berlin and then Argentina. And was that, I mean, was that your idea? To kind of do like a total reset on the way you'd been living your life up to that point?

A Yeah, while I was traveling, so what I'd done up to that point is scheduled my entire life in 10 or 15 minute outlook increments, right? Or calendar increments. And everything was extremely regimented. And when I landed in London, I wanted to do the opposite of what I'd done up to that point. You know, I went to an Irish pub and liked the music, and somebody said, if you really like this, you should go to Dublin. And I said, okay. And I got on a EasyJet flight or a Ryanair flight, landed in Dublin, and went to another pub, and they said, what the hell are you doing in Dublin? Galway has the art festival about to start. You should go to Galway. And I said, okay. And I got on a bus and went to Galway, knowing nothing about Galway. And Bounced around like that, determined by chance encounters with people along the way. And a friend of mine, who was born in Panama, invited me to Panama. I go to Panama, and one of his best friends was half Argentine, and said, if you want the best wine, the most beautiful women, and the easiest ability to live like a king on dollars, you should go to Argentina. And I said, Good sales pitch. I initially planned on being in Argentina for four weeks. I was not planning on being there for a long time.

AI assessment note: “I wanted to do the opposite of what I'd done up to that point.”

Q And I wonder whether some of that came out of your own experience. Like, did you find yourself, maybe at certain points in the last decade, just being, you know, a slave to, to screens, to your phone, to whatever was in front of you? Oh, for sure.

A This is basically creating what I want more of in my own life, certainly. For the last, I'd say, two, maybe three years, I've had no social media apps on my phone, because if you think, if you think you're going to use discipline to beat teams of, you know, computational neuroscientists and statisticians and, uh, computer scientists, uh, Who are, have billions of dollars at stake in ensuring that they can overcome any type of resistance you have to using their program or platform compulsively, you're just bringing a butter knife to a gunfight. And I think it's uncontroversial when you look at scientific literature, these technologies, in fact, there are costs. So my thought is, Just offset it. Try to offset it a little bit, and I think that in-person still counts. We are not evolved for two-dimensional screens at 18 inches 10 hours a day. That is not what we're evolved to handle at all, but I really think that there is a quality of life value to in-person, and we see some Countervailing trends. So for instance, in New York City, these massive game nights in person have become a big thing. Running clubs, people getting off of dating apps. I think that at the very least, you know, micro dosing analog is a good idea.

AI assessment note: “This is basically creating what I want more of in my own life, certainly.”

Q trying to think about, about this from like the, using an analogy as a journalist, I would have written a profile about you, right? And I would have done all of that work. I would have looked at videos. I would have Studied you. I would have followed you. But it's almost like you did that about yourself. Like you told yourself the entire time that you were studying yourself.

A Yeah, I mean, how do you, the real question I was trying to answer and implement was, how do you observe yourself? Because most of us are so wrapped up in our own experience that we can't really deconstruct what went well or what went wrong. And there are some really simple fixes to that. And I learned a lot of this through languages, honestly, including the fact that you're always going to have plateaus when you try to add more difficult skills. And then you'll have another inflection point, then a plateau, maybe a dip, and then an inflection point. So that became something I expected rather than something that discouraged me. In the case of sports, use a video camera. It seems so obvious, but like how many people have taken tennis lessons or fill in the blank lessons and have never seen video of themselves?

AI assessment note: “the real question I was trying to answer and implement was, how do you observe yourself?”

Q and I may, Um, throw you for a little bit of a curveball, but, but you've talked about your parents' support. You know, clearly you have a, they were really important to you as a child, and clearly you have a good relationship with them. And, uh, I wonder, um, I mean, you know, did you ever think that by this point in your life you would be a parent?

A Uh, no, I didn't. Uh, thinking about kids was off the table for me up until very recently, and quite frankly, I felt up until a few years ago that I was too flawed to, in good faith, bring another life into this world. So I took it off the table. I should say first and foremost that for A long time, certainly with my close brush with suicide in college, I assumed I wouldn't make it past 30, and then there was a point where I assumed, eh, I'm probably not gonna make it past 40, whether it's these dangerous hobbies that I have, or something else. Probably won't make it to 40, so I should really make this time count. And it's really only with the support of my girlfriend, who I love very dearly, that I've arrived at a point where I feel like that's a possibility. So I would, I would like to have kids, and I think that I've taken that emergency break off only because I have reached a certain level of self-acceptance and self-love, which are things I never would have taken seriously in my twenties, or maybe even in my thirties. I mean, I viewed those, the idea of self-love as self-indulgent, a recipe for complacency, and, uh, I've Certainly changed my mind. I think that if you don't love yourself completely, how are your kids gonna learn to love themselves completely? So that's, that's a project that I certainly don't impose on anyone else, but I take it very seriously for myself.

AI assessment note: “no, I didn't. Uh, thinking about kids was off the table for me”

Q And also criticism. You got criticized. Um, hey, this is a, like, tech bro. A lot of critical negative reviews. Did you notice that? Did you ignore it? Did you internalize it? Was the positive response so overwhelming that it kind of shielded you from the negative response?

A I wasn't shielded. No, at that point, I wasn't shielded, and I didn't, in the beginning, I didn't make an attempt to shield myself. So, I felt like it was my job to, to answer questions and, uh, correct misperceptions, and, uh, felt very confident in the book. I think that, if I look back at a lot of the mistakes I made early on, there were moments when I wanted to convert the people who shouted the loudest that they hated my work, but they weren't actually People I admired in general. And fortunately, on the other side of the ledger, there were tech entrepreneurs and CEOs and people I respected tremendously who found something of value in the book. They found it compelling enough that they would speak positively about it. And that offset, I think, the, the criticism.

AI assessment note: “I wasn't shielded. No, at that point, I wasn't shielded”

Q you approach it with skepticism, and so I would have been mortified to do something like this, because I would have thought, God, people are gonna question me, and ask me about my expertise, and they're gonna wanna know how I know how to do this, and I, I'm just, you know, I, I'm not a scientist, like, Was any part of you, did any part of you have self-doubt?

A I didn't have a whole lot of self-doubt about the product just because I had effectively compiled the same motley assortment of ingredients and taken them myself as a competitive athlete in college. So I didn't have a whole lot of doubts about that. Did I have doubts about the company doing well? Oh yeah, absolutely. Absolutely. I mean, you know, I was, I was always very good about cash flow. I never took outside funding. I, it was all bootstrapped, but the feedback loop was really long. I was doing most of my advertising through magazines, and I mean, you're committing to the advertising, I mean, sometimes like a month before printing, then it's printed, then it goes out, then you sort of wait for people to buy this magazine until you think you've reached the The tail end, and then you look at your results, it's very slow, particularly compared to what you can do now online.

AI assessment note: “Did I have doubts about the company doing well? Oh yeah, absolutely.”

Q Did you like the operational side of it, or was that the part that, that you didn't like?

A I would have to say I didn't like it, just because that would have been a contributing element of having no time. I mean, I had no time. I was waking up Super early to communicate with customers in Europe and so on. I would stay up extremely late to communicate with clients in other time zones. The only breaks I would take are like, you know, can of beans in the morning, maybe lean cuisine for 45 seconds at lunch, and then, thankfully, some type of exercise for, you know, an hour, hour and a half, stop at Jack in the Box on the way back. Take a shower and then keep working. I mean, I just never stopped working. And, you know, when that relationship ended for me, it also just put into stark relief the fact that the objective isn't to have the money. The objective is whatever you, to have whatever you trade the money for, whatever it represents to you. And I telescoped out a few years, and I'm like, what does this look like a year from now, three years from now, five years from now? And it just, Everything gets worse. My health gets worse. My psychological well-being gets worse. Like, uh, so I need to change something.

AI assessment note: “I would have to say I didn't like it, just because”

Q Really smart, right? You started to recognize patterns, and you were studying different approaches that would then serve you well later, but I can't imagine you were thinking, one day I am going to be doing something like this, so I will need to know how to do this now. It sounds to me like you were just really interested in it. You were just like, how does this work?

A I think the drive to replicate it and the interest in doing it myself actually came up really early. When I was a kid, I Suffering from insomnia. I wasn't thinking that. I was just watching these things because they were on. But later, because, you know, my family didn't have much money, right? Like, money was a thing. It was a point of contention. It was sometimes a point of stress. It was not really a whole lot of conflict, but it was a concern, right? This was a subject that came up a fair amount. And I think in my mind, if you have money, all these issues and problems you might have in life For yourself or for your family, just go away. That was what I concluded. So the drive to make money came in early for me.

AI assessment note: “the drive to replicate it and the interest in doing it myself actually came up”