How To Ruin Your Life with a Quest

28:57and the law is if you're bailed out, no matter what time it is, you could get bailed out and picked up and people would take this bus back and forth. Like their parents or their siblings or their friends would take the bus to bail them out and then they would come back on the bus. And at the bus stop would be all of their, you know, the pimps and the prostitutes and the drug dealers because it was their customers coming back from Rikers Island. and we spent like a month just gathering, you know, interviewing everybody, gathering information. And that was actually, we turned that into kind of a pilot of a TV show and it was really just beautiful.

29:35Wait, what is it called? What is the TV show called? 3 a.m. The whole project was called 3 a.m. Right, okay. No, I thought the pilot was for another show. No, no, no. We shot, we had a budget because eventually what happened was is that Sheila Evans, who's been on this podcast, I guess she wanted to, she wanted to replace the show real sex, which was a very popular show on HBO. And she, and she thought maybe 3am would be a replacement. And we did that segment and she loved it. She paid for, for me to have a producer, a real producer, a real cameraman, and she loved it. But then we, we did a segment that wasn't as good.

30:12She didn't love it. And I left HBO to start a business, but you know, So the whole point is, is that me going on this quest led to such an exciting experience in my life. And also it led to other companies approaching me and saying, hey, can you do something really creative for us? Like American Express came to me. Con Edison came to me. Every record label came to me. Other movie studios came to me. So I was able to start a company. My first company, Reset, I left HBO ultimately and started a company making websites mostly for entertainment companies. But we also did AmericanExpress.com, ConEdison.com.

30:48I had never had any money in my life. And suddenly I had this business because of this quest that I went on simply to find out what people were up to at three in the morning. Like I wanted to know for me. I didn't want to, I wasn't judging anybody. I didn't have any opinions. And I think that's why people spoke to me is because I just was really innocently curious. I mean, I would interrupt couples while they were arguing. Like, what are you guys arguing about? oh, I found some girl's phone number in his pocket. And the guy's like, I don't even know who that is. And, you know, some BS. Is there any good story come up from it?

31:26Like you said, like, you know, like, everyone up to no good. Any good story that you like heartfelt story from that? Oh, yeah. Many, many. I mean, there were people who were just, you know, mentally ill and struggling to survive. And they couldn't get jobs in the day. and they lived on welfare and they were addicted to heroin. And this was their culture. Their subculture was being out at three in the morning. And I got to know a lot of these people. But I'll tell you one story that was a crazy story. Interrupt me if I've told this on the podcast before. But at 4 a.m., we would stop for the day and we'd go to the Empire Diner just to kind of finish off the day, finish off the evening.

32:10And it's four in the morning, Empire Diner was on 11th Avenue and 22nd Street. And the waitress always knew who we were and she always helped us out. She said, oh, check out this table at the other end there. And so it looked like a bunch of guys and girls celebrating. And I went over to them and I'm like, what are you guys celebrating about? And this one guy with a British accent, he says, well, this lovely lady and I just got engaged. And I'm just, you know, we had the cameras on, my video guy always had his camera on. And I'm like, oh, I don't believe it. prove it, kiss each other. And so he grabs the girl and they start like making out.

32:47And I only found out later, like, you know, after we had been talking for like 20 minutes after that, they did not know each other at all. They were like, they had just, they hadn't even spoken ever and they had just met. And that was the first time they ever said anything to each other was they just started making out. And then about a year later, I ran into somebody who was sitting at that table and said, hey, you're the guy, you're that 3 a.m. guy. And he said, I was at the Empire Diner that one time and you got my friend kissing that girl. He was actually engaged to another girl in England.

33:25He broke up with that girl and the girl who he kissed moved with him to England and they were living together and dating for a while and then they just broke up. And he He said, but that was all because you got them to kiss. You like either helped their lives or ruined their lives forever. Well, because for all you know, he could be in a very happy engagement that because of you, he kissed another girl, ended up breaking up that happy engagement. Well, let's put it this way. It couldn't have been that happy an engagement if with one second notice, he's willing to make out with another girl. Yeah, you're right.

34:04So chances are that marriage would not have worked out. So at the very least, I helped the girl he had previously been engaged to. Yes. She should write to you and thank you. If she's listening to the podcast. If she's listening, I'm the reason your fiance kissed that random girl. I remember one detail. I can't remember what she looked like. I remember she worked at Microsoft. I do remember that. She was like a sales rep at Microsoft. But I had lots of stories like that. It was like, I was like the first podcaster on the internet. I was basically interviewing people and then putting the interviews on the worldwide web, just like we do with this podcast.

34:44Now I wouldn't put the audio because there wasn't bandwidth, but I would put photos. And then here's what I did. I didn't have designers to design everything. And if you look at 1990s web design, it was a little overdone. There was too much design. Now things are much more minimal and simple, which I like better. But I would basically open it up to the web design community and allow designers to compete with each other to design the pages that each interview was on. So I would do four interviews a week and each interview was designed differently. And then we'd put photos. And every once in a while, we'd put video.

35:22But there was no streaming the video. It was hard to download the video. Do you accidentally created 99design? You know 99design.com, right? They put a request out and then they have people compete to design for a website or a cover. Right. That's what I did, basically. So you accidentally created a 99 design. Right. I wish I had any business sense at all because it would have really worked out. I did so many things in the 90s that could have made me a lot of money, but I knew nothing about business. That's another topic. It's not just about creating a great product and making a profitable business.

35:57You really have to know what business means in order to make money. You can't just sell things and make money. You have to know what are the different types of businesses, how people value businesses, how to structure a business, how to scale a business. There's all these subtleties that I had no clue about, how to describe your business so that it is worth more than if you describe it a different way. But anyway, that's another topic. But I'm just describing this as this gave my life. Like I was really depressed at HBO actually at first because I was working in this cubicle. I was working on this stuff, this programming that was really awful.

36:39And I didn't even know how to program. Like I've gotten an undergrad for computer science and grad school for computer science. And I was such a bad programmer after all this quote unquote education. They had to send me to remedial classes on programming. and I thought I was going to get fired. And just going on this quest not only made me so much happier at work, and it also made me kind of known within the company. Like I was this 3 a.m. guy. So I was starting to get promoted. I was getting other offers and using that to get higher and higher salary. But then it even led to me starting a business.

37:12Like it changed my life. And it gave me this whole – I must have interviewed thousands of people. You know, for two and a half years, I would interview about 20 people a week or 15 to 20 people a week and then put four interviews, the best four up every week. And so, I don't know, I must have interviewed at least like a thousand people. So I got my interview skills and I learned so much about other people and about also making a great website. So it gave me this, going on a quest allowed me to not focus on my own problems, but actually I felt this pleasure of like, you know, it was difficult too because I was shy.

37:56How do you just go up to people in the middle of the night and say, hey, tell me what you're doing? So it helped me overcome shyness. It helped me get people talking. It helped me, you know, it gave me a lot of skills. and then it gave me things to look forward to and a different perspective on life. So it changed my life completely, just being curious and then going on a quest. And another quest was when I did stand-up comedy. I was just curious. I always was curious. How do these people make people laugh from stage? I'm funny at a party or whatever, but then making people, strangers, laugh from a stage, that's hard.

38:37How do people do it? So that was a seven-year quest that led to me buying part of a comedy club and going up on stage almost seven days a week and traveling around the world. I mean, I went to, I traveled with Tony Woods, one of the greatest comedians ever. He was just on Joe Rogan. Traveled with Tony Woods all over the world doing comedy. And that was a quest. Or more recently, you know, I was having kind of a down period after that New York City article came out, and I went on a quest again, which was to take just back off of social media where I was getting death threats every half second, and take this childhood love of mine, which was, you know, I was a chess master when I was much younger.

39:25Still am because the title is forever, but I wanted to get back to my old skills in chess. And this quest has been amazing. Like I've gone to Norway and had dinner with the world chess champion. I've, I've, I've traveled all over the place playing chess. I'm the Georgia senior chess champion about to compete in the U S senior championship. And, uh, all these friends from 25 years ago, I I'm meeting them and I don't know the quest is still ongoing, but it's been, a life-changing experience, also understanding the effects of aging on my brain and how to fix those things that are happening and be a better person for it.

40:07This whole experience, the quest is, again, still ongoing, but it's made me eat better, exercise better, sleep better, deal with loss better, deal with social media better, sharpen my brain. I've taken lessons from the World Memory Champion. So this has been a quest that's been life-changing.

40:42I wanted to talk about what is a quest? When you think of a quest, what do you think of, Jay? Well, it's funny. I was about to ask you, what's the difference between quest and purposes and missions, right? So for me, I felt like, you know, quest, it's someone that gives you the quest. So let's say if you're in a story, let's say your whole life is a story. The quest is all of a sudden, the world is ending, and then an old bearded Kung Fu master just show up in front of you and be like, hey, you have the potential. Here's your quest to save the world. Well, you still have to, remember, you still have to choose to go on the quest.

41:24Like Luke Skywalker didn't want to leave Tatooine at first. He had to, even after Obi-Wan Kenobi told him everything, he's like, I got to wait one more season because I promised my uncle. And it was only the uncle getting killed by stormtroopers that Luke finally went on his quest, which was to learn about the force and save princess leia and destroy the death star and on and on he he did not want to do it at first right you have to choose to go on the quest your curiosity has to be and here's the difference between a quest and a mission a mission you know what's going to happen i'm going to do this i'm gonna i'm gonna you know save all i'm gonna spread malaria nets mosquito nets to all the people in africa that's my mission and i'm gonna do it and save Africa from malaria.

42:13That's my mission. Or I'm going to teach people about leadership. So I'm going to write a book about everything I've learned about leadership. And that's my mission. A mission is almost kind of arrogant. Like the idea that you know you can do something and God put you down on this earth to do this purpose or mission. I don't really believe in those. A quest is you don't know what's going to happen. Luke Skywalker wanted to save the princess. He didn't know if he believed in the force, but he was ready for adventure, excitement. He had nothing left on Tatooine. He was ready to go on his quest. A quest is more like a nonfiction arc of the hero almost, whereas a mission is like an arrogant, like, oh, this is my purpose.

42:57I have a purpose that the overlords implanted in me and this is what my DNA is forcing me to do. Would you say mission has an end goal that you got to achieve or has an end goal target that you can see? Whereas quest is more like, it's more about the journey. It's more about, let's do this. It's about both. But, because look, a famous quest in fictional history is the Knights of the Round Table for King Arthur. They had to find something called the Holy Grail. Holy Grail. And they never actually found the Holy Grail. They never found it. So the quest didn't work or it did work because all of the stories and adventures around King Arthur are because of this quest.

43:44So yes, the journey is really important. And, you know, I've been thinking like, what are the components of that journey? First off, the quest is for you. There's something personal you have to find out about yourself when you go on this quest. Like, again, Luke Skywalker, he had to discover the force within himself. or me with this chess thing, I had to figure out, you know, I had to realize I'm no longer as good as I was when I was younger. And there's some things I can't get good at anymore. Like my memory is different or my calculation ability is different or my ability to stay up all night and then play well the next day, that ability is gone.

44:26So I have to figure out things about myself, as part of this journey. And then, so there's all these challenges. A mission doesn't necessarily have challenges. I have challenges. Like my first tournament back, I lost something like seven out of eight games. And these are obstacles. These are real obstacles. And then I have to find, like in the Ark of the Hero, I have to find allies, people to help me. So I had to find coaches and I had to find people who are my level to exchange ideas and notes. I had to find people who were going through the same thing I was, like older people maybe who were trying to play.

45:07And most people told me I was delusional. So along with these obstacles and these allies, there's also villains and people who are antagonistic to me. They're trying to stop me from doing my quest. And so then you go on the journey and the journey has trials like, oh, I'm going to play in this tournament. Oh, I lost this tournament. And then I lost this other one. And then, oh, I've got to somehow get to Norway to have dinner with the world chess champion. And on and on, there's a journey and adventures happen. And then you transform. Hopefully, you transform and you have growth. Like so that, oh, I realize I need to sleep better or I need to eat a little better, never drink alcohol.

45:50And instead of wasting time on social media, I'll study some more positions to get ready for the next tournament. And so I grow and transform and I sacrifice. So I sacrifice social media or sometimes you have to sacrifice things that are important to you. Like, oh, I haven't been writing as much or I might not spend as much time with this person so I can spend time doing this. And ultimately, you hopefully achieve the goal of the quest and then you return to tell the tale. but that altogether is a quest. And I encourage people, don't just live that cubicle life. Don't just be, or even if you're not living the cubicle life, let's say you're just, let's say you don't have a job and you're feeling down or depressed, or let's say your relationships aren't quite working for you at the moment, find what is it you're insanely curious about, or what is it that you were curious about when you were younger and test the waters, begin this quest.

46:55What do I need to do? What does this journey look like for me to achieve a certain goal? Maybe you want to write your first novel. Maybe you want to go to a yoga retreat in India and become a yoga teacher. Maybe you want to start your first business. You know, what are the, what are the, what do you think? You're going to be wrong by the way, but what do you think are the steps you need to take? And take that first step. I find a lot of people, They want to write that first novel and they go out at night with their friends every night and eat dinner and drink and have fun. And they're always saying, I'm going to write that novel.

47:29This year, I'm going to write it. But they never do it. Like, figure out what is the first step? What's the second step? Take those steps. Assume there's going to be obstacles along the way because you're not, the whole reason you're not at the goal is because you never did it. You don't know what to do. You don't know the things that are in between starting the quest and ending the quest. Luke Skywalker didn't know he'd have to learn the force. He didn't know he'd have to save the princess in the Death Star, in the most lethal weapon ever created. And assume some people, find the people who will help you, like the Han Solos and Obi-Wan Kenobis, or in my case, chess coaches, chess allies, you know, the really gracious people who have allowed me to write for them at Newin Chess and other places.

48:20And these are your helpers and allies. There's going to be villains, the people who tell me I'm delusional or the people who make fun of me, whatever. Or it could even be people who you know very well who are very skeptical. And now you begin the journey and have those trials and see the growth and make the sacrifices and you change as a person, it could be as the quest sounds, it doesn't even matter what the quest is. It could be as dumb as trying to get better at chess or it could be I want to make a billion dollars. Although I will tell you, whenever I thought I was on a quest to make money was probably the most unhappy time of my life because...

49:03I mean, I'm just curious. Like, you know, like just find quests and stuff like that. But like, how do you know you found the right quest? Like my quest is I want to win a Grammy. I'm like, okay. And then I was working in a studio and then now I'm in podcasting. I'm like, am I still on track to win a Grammy? You know what I mean? Well, this is a great question, Jay. And the truth is you don't really know. Nobody's going to come down and tell you, oh, Jay, you have found the right quest for yourself. You have, you know, just that's why it's so, that's why it's so much BS where people are like, oh, this is my purpose.

49:43This is my mission. You just don't know. And you don't, and by the way, you might halfway through the quest, it might be so frustrating. The challenges might be so great, you give up. And that's okay too. Again, this is where the journey is very important. It's not the only thing that's important. I don't believe when people say it's not the goal, it's the journey. It's both. The journey is, the goal is very important, but the journey is just as important. And so if you feel like quitting a quest and starting a new one, then do it. But if you truly, let's say you have a, like for me, if I have a horrible tournament, I think to myself, oh, that's it, I quit.

50:24I'm just, this is too painful. I'm not getting there. I'm not gonna do it and so on. But then the next day, if you wake up and you find yourself, huh, what's the next step? Like, it's because you love this quest so much. It's not even like I have fun sometimes playing in these tournaments, particularly when I'm losing. But if I love the quest so much that the next day, after I hit one of these obstacles, I'm still waking up with just as much energy. Or maybe it's not the next day. Maybe it's the next week. I'm waking up with just as much energy to keep pursuing the quest. Then you just stick with it.

50:59You let your body and your emotions tell you to stick with it. And you're going to feel like quitting sometimes too. And that's maybe times when you need to take a break. Because you get overloaded. So are you saying that if you feel like you're quitting, should just take a nap because you are cranky? No, I'm just joking. When you feel like you want to quit, you should take a day off, just slip it off and see how you feel the next day. Yeah, or take a few days off. Sometimes I'll take three or four days off from studying or interacting with people or playing or whatever. But you know what's been great for me is that it got me off social media.

51:40It got me to eat better. It got me to improve my memory. It got me to work hard at something again. I had forgotten what it was like to really... The podcast is hard. The podcast is a lot of work and other things I do are a lot of work. But this is like performing brain surgery on myself every day to get better at chest, particularly at this age. and uh but i was i i won the georgia senior championship for people over 50 i'm about to play in the u.s senior championship in a few days and it's been difficult and it's been excruciating sometimes but it's also been extremely fun and pleasurable and i've learned so much about myself and it it got me away from just the mire that i was being sucked into from that old article i and from some other things that were happening to me at the time.

52:30I had a kind of a negative period in late 2020, early 2021. And I just wasn't showing up for things. And a quest is something you show up for. And you're proud of it. And you love it. And you pursue it. And it's not always fun. But the pursuit is worth it. And that's really the thing. Now, for you, if it's your quest to win a Grammy, me, well, what is the next step? But here's the thing. You can experiment with lots of things. Like at the end of 2020, there were lots of things I was experimenting with. Chess was just one of them, but there were others too. Like I was, you know, trying to start different internet businesses.

53:15As you remember, I was, I got really into betting on the election in 2020. Oh, you remember that? Yeah, I was really getting into, we had the guys from Predicted on, I was really getting into event betting. And you were into presidential too. Yeah, I started running for president and I thought I was going to take that really seriously, but it ended up being more of a joke. And this is the thing that survived. You experiment with a bunch of different quests and this is the thing that survived. So again, what's a quest? Quest is the first half of question. So it starts with you being really insanely curious about something where you really don't know the answer.

53:58And then what would it take for you to know that answer? What is the goal? How would you know you know the answer? Well, for me, if I reach a certain level, I think that will be the objective of this quest. We'll see. And then just prepare. What challenges and obstacles might you experience? Well, you're not gonna know all of them, but start going down the path and start having challenges. and then you find your allies to help you through these challenges. And then you find the people who are going to dissuade you or be against you on this quest. And you're going to be on the journey and have your trials and adventures.

54:32And then through this process, you're going to transform, grow, sacrifice, and hopefully get fully to the other side of the quest. Or not. It's enough to just simply have the experience, but hopefully you achieve the objective of your quest. Yeah. You know, you always say like, who are you? Why are you? And why now? Do you think those three questions will be able to apply to the quest? Yeah. Like for instance, who am I? I'm someone who's always loved games and love the challenges of competitive games, games like chess or other games that fall under that category might be poker or Scrabble or checkers or backgammon.

55:14So I've always loved those. I'm always a game player, Even day trading has kind of like a game. So why am I someone who at the time, at particular in like late 2020, early 2021, or mid 2021, I was kind of depressed for a lot of reasons. Not hugely depressed, but I was getting a lot of backlash from that article still, like even a year later. I had two books that came out and they didn't get, they were good books. Skip the Line was my favorite book I've ever written, but it didn't quite get the reception I would have liked. I was having, you know, I had moved, I was having some trouble making new friends.

55:56And I was worried about, you know, am I getting too old to pursue the things I love doing? And that solved the why now, which is like, okay, I'm in my 50s. And now if I'm going to do this, now's the time to do it, to get back to my old level. and particularly after the TV show, The Queen's Gambit came out, it reminded me of my love for the game and I started pursuing it. So that was the why now. So who are you, why are you, and why now are critical questions for this. And also the plus minus equals technique that I described in Skip the Line. You have an objective, find a coach, that's your plus.

56:36Find people you can teach, that's your minus because you don't truly understand something unless you could explain it simply. and find your equals. People are on the same quest as you so you can exchange notes and learn from each other. That's great. I think that's, I feel like that should be the next book you write. Maybe I already wrote it though. It skipped a line, but we'll see. But I am, you know, Robert Greene went on the podcast. When we had Robert Greene, author of Mastery and 48 Laws of Power, he said, oh my God, you have to write the book on this. And that kind of also kicked me off on the quest was his encouragement.

57:09You were listening. and so you do need some sort of validations halfway through yeah you definitely need validation somehow like i if i only if i only lost i would not be pursuing it at this point like that would be too hard but i've had i've got trophies in the room along the way so you know that's been good but i also have to say a quest can also ruin your life too how so like every quest i've had has completely 100 % changed my life. So this 3 a.m. thing, I ended up leaving corporate America and starting a business. This chess thing, I haven't been writing as much. It's distanced me from certain friends or family or work.

57:56I could have been starting a business instead of playing a board game the past year or so. So it's really, it messes you up a little bit too. and it screws up your life in a big way. Sometimes for the good, sometimes for the bad. But transform is not always a positive thing. You're going to transform. Some of it's going to be negative. Hopefully more of it will be positive. So I think we should title this episode actually, you know, how to screw up your life with a quest. How to ruin your life with a quest. How to ruin your life with a quest. So, because maybe I will ruin my life with this, but we'll see.

58:47Even the Rich is a podcast from Wondery that tells the jaw-dropping stories about the tumultuous lives of the world's elite, from the greatest family dynasties to pop culture superstars. Listen to Even the Rich on Apple Podcasts, Amazon Music, or wherever you get your podcasts. You can listen ad-free by joining Wondery Plus in Apple Podcasts or the Wondery app.