Dan Cates Back-to-Back Poker Champ, Philanthropist, Investor, and Podcast Host

Interview on the Jason Hennessey Podcast 09-14-2022 - Episode 37
Dan Cates

How Two-Time Poker Champ Dan Cates Follows the Flow of Life

Today we get the chance to sit down with two-time World Series of Poker champion, Dan Cates.
Known to many as “Jungleman Dan,” and regarded as one of the leading poker players today. Dan recently secured one of the most coveted titles in the game for a second time in a row as he made history by winning back-to-back $50,000 poker championship titles in both 2021 and ’22.
This extraordinary win broke records and totaled his live cash earnings to well above $11 million, a drastic shift from his humble beginnings working at McDonald’s to offset thousands of dollars in debt.
So, join us as we broach everything from the lessons Dan learned from hiking Mount Kilimanjaro, his experience with his strip-poker-playing alter ego, and the beauty that comes along with surrendering to the flow of life.
Please hit the play button at the top of the page and thank you again for tuning into The Jason Hennessey Podcast.

In this Episode

[01:18] Jason and Dan Cates spark today’s show discussing Dan’s inspiration to follow the “flow of life,” and the irony of Dan dropping out of college to play poker professionally. They also tease a future segment regarding Dan’s views on education.

[07:35] Dan describes climbing Mount Kilimanjaro, the steps he took to prepare for the challenge, and the many extraordinary people, places, and lessons he encountered on his venture.

[14:13] Dan details the places and opportunities the world of poker have opened. He remembers his Christian Baptist school upbringing in Maryland, being diagnosed with Asperger syndrome, and beginning to play poker at the age of 17.

[21:11] Jason asks about Dan’s poker origins, and recalls the reasons he stopped high-stakes gambling. Dan emphasizes the difficulty of earning a living playing poker, and how learning to loosen control and making things fun are the key to success.

[31:50] Dan reveals how a playfully arrogant mindset and a Dragon Ball Z persona enabled his back-to-back World Series of Poker championships. He also expresses his regret of filming a strip poker video with Playboy models.

[43:40] Dan lists a couple poker players he admires and breaks down game theory, his beliefs on analysis versus intuition, plus, he shares tips to use on the poker table.

[50:53] Jason is interested to know if Dan splurges after big wins. Dan confesses that a lot of his cash goes into property investments that may not always return a profit. Jason is reminded of the time he bought a palm tree on a whim.

[55:25] Jason and Dan play a game of “Never Have I Ever” where they tell revealing stories about choosing gambling over sex, lying about what they do for a living, saying the “three little words” first, and much more.

[01:09:26] Dan reflects on what he wanted to be when he grew up, his idea of a perfect vacation, people’s misperceptions of him, the best and worst phases of his life, online poker’s Black Friday, and more in our signature segment of “Hennessey Heart-to-Heart.”

[01:22:20] Jason squeezes in one last question about Dan’s vision of reforming the educational system. Dan expounds upon his ideas of creating more positive and energizing schools through entertainment and altruism.

[01:25:46] Jason promotes Dan’s podcast, “Winning the Game of Life,” and his Instagram to wrap today’s rewarding conversation.


Jason Hennessey: “Jungleman” Dan Cates, thanks for coming down to Hennessey Studios.

Dan Cates: Thank you for having me, and thank you for- Finally, this worked out.


And yeah. Great to meet you.

Likewise. I know we’ve been trying to put this on the calendar, but it seems like you’ve been doing a whole lot of traveling.

That is true. I’ve been trying to do lots of things. And in order to do a lot of things, there’s lots of traveling involved, but as it turns out, some of the things, you’ve got to stay in one place.

So I’m thinking, “Okay, how do I make that work?” I got to stay in one place, but I still got to travel. And here I am. The energy of the universe brought me to Los Angeles.

And I thought, “Maybe there’s something to this energy of the universe stuff. If there is, I should just try it out for a few weeks. Let’s try out this energy of the universe stuff. It  sounds pretty good.”

So, that’s the story of why I’m here right now, basically.

But we’re on the same frequency, man, because that’s my whole life. 

And I teach my son Zach too, sometimes when the universe starts to speak with you, you have to listen to it.




And there’s examples that happen every single day. 

I like to tell my son that I’m a big believer that when you get into an elevator, there’s also a reason why you’re in that elevator with that somebody else. 

And you don’t know why, but you just have to be curious and just explore it.

Okay. I’m almost on your wavelength with that.

I wouldn’t say I’m fully committed to the energy of the universe, but I’m exploring this idea that maybe this could be a thing.

In my view, it’s not exactly irrational. As long as something’s within some kind of- If it could make some sense or something, why not? But maybe I’ll end up being full-blown energy of the universe.

I read this book called The Surrender Experiment. Do you know about this book?

No. I’ve heard of it, but I haven’t read it yet.

Okay. Well, in this book, this guy, the way he puts it is he surrenders to the flow of life. And the flow of life had a lot of great surprises in store that were outright miraculous. Straight up miracles every other page.

And I’m just reading this and I’m like, “What is going on? Is this actually real? Is this guy real?”

He would have to have passed a test for the sake of the greatest good in the next two days and he hadn’t studied, and he would flip the book and just magically it would be right- And just read two pages or something, and the only few questions on this test would be from this book.

And just things like this would happen over and over. And I’m just like, “What is going on? Is this real? I guess it could be. I don’t know.”

Re-looking at other events, if you look at them in certain ways, events that appear negative, it might be the case that they were just- What I’m saying is, I don’t know if it was applying to other people in the past or not, but some events that appeared negative for them may not necessarily have been.

I think it’s an interesting idea. At the very least, it’s entertaining to go with the flow of life for me. If it’s true or not true, either way, the result is entertaining.

Yeah. So can you think of something that happened in your life where it seemed like a coincidence, but it really wasn’t a coincidence?

Yeah. Or at least I re-looked at it. Going back into the past, I can think of quite a lot of things actually.

One that comes up to my mind is I actually dropped out of college. I dropped out of college and I failed the same class twice that I would’ve had to take again. It would basically have forced me to take two years. But the irony was, it was called “Game Theory.”

A very conspicuous coincidence because poker’s all about game theory. That is the topic that it’s all about. But ironically enough, almost nothing in that class I really used for poker.

There were some principles you could say that I remember, vaguely, that were interesting, but none of the theory was just at all relevant to actually playing a game, which is funny.

It also alludes to the big issue that I believe is an issue with the current education system, which now I in fact am trying to change. I’m working on that. It’s a daunting process and people have tried to solve this obviously.

So, got to rethink how to do it. Yeah.

So you failed these two classes and you think that’s the whole reason why your poker journey began or what?

No, but it made it easier for me to drop out of college, period. I was determined to finish college.

By the time I had finished I had a solid, solid, solid career in poker. I was legit successful at poker and it made no sense for me to go to poker. It was either write book reports and go to these classes that I’m never going to learn anything from or travel the world and play poker. A tough spot.

Sometimes you gotta just, I don’t know, figure it out, but not because of that. It’s just an ironic twist of the story.

And it’s an ironic pointing- It’s a funny way of alluding to the failure of the education system is that many of these topics don’t actually help you to perform these jobs. f

This is the common theme of today’s education is becoming less and less relevant to actually living in the real world is the funny thing.

Oh yeah. I’m a big believer. I think that the school system is antiquated. They teach you how to learn, not so much what to learn. 

And when you don’t really get in tune on what- If you don’t have an interest in French class, but you have to take it- 

Why not look at my strength and maybe give me more support in that? 

I think it’s an antiquated system and I’m curious to hear how you’re solving that, and we can maybe talk about that later in the episode.

I have many different ways and it looks like you have a glimpse of the answer on your paper.

Yes. You can see it here. 

So it looks like- This is what I was going to get at. You did something that most people would never try to do and that’s climb Mount Kilimanjaro

So what made you do that and how did you train for it and did you make it all the way up? I’m curious.

Okay. Why did I do it? Thinking about it, I just thought it would be a good adventure and I heard that it’s life changing in this positive way.

And some of my friends were doing it. In fact, all of them. Well, actually one of my friends was doing it. I made another friend this way and it would be a good way to connect with people.

And actually all the people that I met on the trip were, in my opinion, amazing people, which is a nice byproduct of that.

You know what? That was one of those things that I’ve done that was more of a curiosity thing. It just seemed like a great adventure and it seemed like it would give me a new perspective on life, which I’ve slowly come to value as more valuable even though I don’t know necessarily what that is a lot of the time.

So it was one of these things that I do sometimes just to get a better sense of direction for a lot of things.

It was a bit more of a commitment than I thought. It was quite expensive. Over $10,000 and a decent amount of training. I was trying to build muscle at the time, but I had to put that to the side to lose weight and to only do work with legs.

So, I did quite a lot of walking uphill and things like that, but it turns out that a lot of this was fairly pointless. I also had an issue with one of my calves. It had been hurting for many months, and so I just decided to get it stretched, my calves stretched.

Or excuse me, my heel hurt for many months so we thought that it was because my calves were too tight so I got them stretched the entire time because the last thing you want is to have your legs cramp up on the top of the mountain.

But it turns out that basically everyone that climbs Mount Kilimanjaro, almost all of them fail because- Okay, 50% fail, 51%, and all of those percent fail because of- What’s it called? Altitude poisoning, which is a thing that I very much experienced.

I was very nauseous towards the top and I had a slight headache at nearly the summit. And because of that, it was deemed too dangerous by the guides to go to the top, but I would’ve absolutely otherwise gone to the top. They just told me not to.

So, that was very frustrating. I made some mistakes related to that.

How long does that take from the start to the climb?

Well, we took a long route, which was 5 days to the top and 2 days down. And the reason why they go slowly to the top because it’s quite scenic, it’s beautiful. You’ll see things that you’ve never seen before.

There’s a special flower that grows on the way up there. There’s a little jungle too. And you’re in the middle of the clouds and everyone’s singing and talking in Swahili and calling each other “kaka,” that sort of thing. There’s massive cliffs and there’s the Devils Tower and whatever.

Also, because of the altitude poisoning, which was the only thing that really mattered. Everything else was easy.

And in fact, the heel that had been hurting for 6 months, ironically, became healed as I walked up the mountain, which is a strange thing because it got better as I walked up the mountain. Maybe I just wasn’t using it enough. It just magically got better after day three.

Who would’ve thought that would happen?

It’s so funny. When he’s sitting there and he’s describing his experience at Mount Kilimanjaro as you’re walking up and the flowers, and people speaking Swahili, it reminds me of the scene from Good Will Hunting where Robin Williams is sitting there with Matt Damon

He’s like, “You know what? I just thought about this, and you’re just a punk kid. You probably have never seen a war. You’ve probably never held somebody die in your arms. You probably have never seen the Sistine Chapel. You can cite it, you can tell me books that you read about it, but it’s just so-” 

Because I’ve never been to Mount Kilimanjaro. That might be something that I do in my lifetime, but just experiencing it is so much different than reading about it in books and stuff like that. 

That’s so awesome that you did that. Yeah.

Yeah. I’m really summarizing it as much as I can. There’s many details of it. I can say it was very, very frustrating not going to the top.

I just sat there. Laid in the tent for hours. That was the most frustrating thing but hopefully it has some positive impact and that makes me make sure I get every little detail right.

I want to also say that one interesting thing was that the service- There were all these guys that were helping us get to the top. It’s part of the service of climbing Mount Kilimanjaro. It’s not a fully fledged professional climb. It’s something everyone could do.

But the service there was some of the best I’ve ever had. Which I thought was conspicuous because it’s in the middle of Tanzania.

And I just thought, “Why is this the case? Why is the service and the camaraderie of this place with no law, et cetera, so good?”

But my understanding was that basically the guide that we had- I don’t know if they’re good to everyone, but the guide that we had, his name is Sean Swarner.

He’s climbed Mount Everest 20 times and he has only one lung and quite old. He’s done a lot of things. There’s actually a documentary on him, but he’s been treating them well for 10 years or whatever.

And I thought to myself, “Why- Could this just exist everywhere? Maybe we can just treat everyone better and no more problems.” But that was just my observation.

And what else? Oh yeah, we also went to the Serengeti afterwards and to- Where else did we go? This big crater called- What was this crater?

There’s a crater in the middle of Tanzania with a bunch of animals; with lions and gazelles and hippos and stuff like that. Very beautiful.

I forget the name of the crater though.

Got it. We’ll find it and link to it from the page here

So, your poker career has taken you all over the world, it seems. Sounds like you went to Dubai too recently?

Yes. Yeah, Dubai’s, one of the places I’ve been to.

Okay. Going skydiving I hear?

I have been skydiving. Yeah.

Where else have you been as far as travel goes?

Let’s see. This year I’ve been to Mozambique. I’ve been to Ghana. I’ve been to India. I will actually post these on my Instagram. I’ve been to an Indian wedding there. I also was briefly in the Himalayas. I went to a Ghanaian wedding, actually. That was cool.

Let’s see, where else have I been? I’ve been to Spain. Yeah, I didn’t post anything from Spain either.

So now when you travel, are you playing poker as you’re traveling or-


You are. Of course, right?

Quite a lot. I’ve been working on other aspects of my career and also flow-of-life-ing it up, man.

And I have a foray into charity as well, into effective altruism ideally. Charity is one part of that. Using charity in an effective way, ideally. So that’s a new thing.

@thedanielcates 2 month ago I decided to use my poker millions and start a charity …🌏🙏🏻 #like #recommendations #рекомендации #charity #Africa #poker ♬ оригинальный звук – Daniel Cates


Let’s see. What else am I doing? Fun stuff. Yeah, there you go. I’ve been doing- Let’s see. What do we do?

Well, let me ask you this. If I were to mail you a postcard, where do I send it? Where do you live? Where’s home?

Is there a flow of life service? Is there a service that just says, “Here’s this guy, he’s traveling and just will figure out where he is in two weeks,” or something?

That’s it. Okay.

They’ll text me and ping me and you’ll just send me what it is, because I’ve been changing it a lot. And it depends on when you’re sending it, but I’m going to Cypress soon.


Yeah, Cypress.

Okay. Got it. 

Well, first of all, where’d you grow up?

I grew up in Maryland near Washington, D.C. It was kind of merry I guess.

Yeah. And what was your childhood like?

A bit different from most people’s childhood. I don’t remember a whole lot before the age of 10 or so. Remember a couple things. But other than that, around the age of 12, I realized I wasn’t like most people.

I was diagnosed with Asperger’s Syndrome and I was a bit aloof. I was very socially unaware. And the social skill stuff didn’t happen naturally for me. A bit of a journey for me in many different ways.

Let’s see. I went to a school for the gifted and talented for high school. I was in a Christian Baptist school and actually something happened there that I thought that seemed to have a big impact in my life.

My heart was broken at the age of 12, and it started this- Because we were in a Christian Baptist school, I believed essentially God was mad at me. This was my interpretation as a 12 year old kid.

So I read the Bible twice. But from this, it started my contemplation of many spiritual ideas and the idea of seeing is the Bible real sort of thing? This idea of connecting spiritual ideas to reality, which would later revisit me.

Well, these ideas would follow me until around the age of 15, in which case I said- No, they would actually follow me throughout my life and I just have these thoughts that I would be thinking about that were partly aligning these ideas.

And then around the age of 29, I had a bit of a paradigm shift, but we can talk about that later.

As far as the rest of my childhood, I was pretty aloof. I was very, very introverted. Making friends did not come so naturally to me as it does with many other people.

And then I found poker at around the age of 17. I became really, really obsessed with it and I was not very good at it, actually. I got my ass kicked pretty badly for a while.

That’s where I got the nickname “Jungleman.” No one knew where I came from.

I got the nickname ‘Jungleman’. No one knew where I came from.

At around what? 17, 18 years old?

Yeah, 17, but because I got good at other games, and every time I practiced other games, I always was able to surprise myself at what I could do with them.

So, because of that emotional experience, even though I sucked at poker for a while and always lost, I decided, well, eventually maybe I can be good and make money and not have to work a day job. I can be free and do what I want.

So through this, through 18, I started to win at poker and then I had to work at McDonald’s for a month to make money in order to play poker.

I had lost a lot of money from my savings that my parents gave me, but they locked it up because they didn’t want me to spend all my money gambling or what they interpreted to be gambling. I didn’t interpret it that way.

What did you interpret it as?

I interpreted it as fuel to learn and learn how to do something that would’ve been benefiting me. Fuel to make money in the future. Something like that.

Yeah, yeah, yeah. Did you have brothers and sisters or do you have brothers and sisters?

I have two sisters. Yeah.

Two sisters. Okay.

We’re on good terms. I would say I’m not super close with my family, but-


We’re on pretty good terms. We connect about some things.

I’m the odd one out of the family. I think that’s indisputable.

Okay. What did your mom and dad do for work?

My mom worked for the Bureau of Printing and Engraving in the government. She was a chemist. And my dad had a few jobs. But generally speaking, he worked as management for technology companies, generally speaking, such as Motorola. He’s one of the higher level management executives and worked with a lot of people there.

Motorola is one company that he worked for. Lockheed Martin as well. I think he works for a different one now. Or no, they’re retired now. Excuse me. But he worked for a couple.

And so, how did you first learn- I guess, who introduced you to poker?

I was playing a lot of video games when I was younger. Big surprise.

My friends were- Yeah. Some of them played poker and because poker was a game, I was excited about the idea of playing a video game for money, or game for money. However you want to look at it.

A lot of these things are just titles.

I had the inspiration just from that idea, essentially. It wasn’t like someone formally introduced me to it. And that was how I learned.

So you were playing online poker?



Actually, excuse me. I played live first because I didn’t know that I could play online poker.

I see. Okay.

And in fact, I remember specifically, I thought it was illegal for me to play online poker because I was 17 at the time and you had to be 18. And I just didn’t look into the idea, but I didn’t realize they didn’t really care and you could just basically sign up and play.

So I started online poker, you could say prematurely, but I really wish that I had started it before because you could play small stakes, which I really wanted to do to learn.

And instead, I just dumped a lot of money to these guys who were more experienced than me at $100 buy-ins where you could lose $100 or a few hundred dollars in a night pretty easily. Especially if you’re not as good as them.

And that was a lot of money for a 17-year-old at the time.

Of course it was. Yeah. My story was somewhat similar. 

I was into sports betting younger and I was following a friend of mine. His name was Dave. “Vegas Dave” is his name. And he’s a big sports better. And he just was like a savant. He just knew everything about football.


Yeah. And I just followed him one year. I was maybe 20 years old, maybe. 

And I took out $5,000 of money that I didn’t have, and I just followed him every step of the way and I turned it into $300,000.

All right. Well, that’s a good strategy.

Yeah. Suncoast Casino in Las Vegas. I was living there at the time. I had just got out of the Air Force, but then what happened was, for me, I then had children and I was gambling. 

I wouldn’t walk around with less than $10,000 in my pocket. We would just go buy things whenever we wanted, my wife and I. It was a good life. 

And then I started to become good at it. But then it started to interrupt my family and just stress.

I remember I’d be sitting down Christmas morning looking at my phone seeing, “Am I going to lose this $25,000 or win it?”

And then if you lose it, then you start having all this regret. “What could I have done with that $25,000? I could have put that into my kids’ child- Their schooling system.” You know what I mean? 

You just have all this remorse, but when you’re winning, you’re on this super high. 

So you have to have this emotion too, right?

Yeah. Well, a couple things. I do and I don’t.

And I also want to ask, do you bet while the game is going, or do you-

No, I didn’t at the time. They didn’t have that I don’t think. I mean you could bet on halftime. But I would bet at the beginning of the game and just ride it through.

Okay. Yeah.

So it’s different.

If you’re watching it would be very stressful and get your emotions all worked up, especially sports.

Yes. [laughs]

Imagine being the one’s playing. The stakes are even higher. They’re under immense pressure.

Oh yeah. And I’ve lost in the last seconds of a game because of a fumble and stuff, and it’s like a $50,000 swing. That’s probably not a lot of money. 

But I mean, it is for me. But when you’re betting millions-

It’s a lot of money for I think most people. Ninety-nine-point-nine percent of them or so. For me, it’s a lot. Yeah.

So you have the same kind of emotion though?


When you lose a big hand or tournament, right?

Yeah. I do and I don’t.

So for me, the more my perceived control is, the more my emotions look like what you’re saying.

For example, if I perceive that I have a lot of control over something, then you’re really stressed, if- doesn’t work out that way. That’s my own personal thing. But if I perceive that I don’t have control, then-

I want to add something to this, but if I perceive that I don’t have control, I don’t really care usually. But then it’s perhaps important to ask the question, “What is control?” “What is control?” is the biggest question. “What do you actually control and to what extent could you have changed it,” maybe is an important question.

Looking into this and also applying spirituality to this subject, I want to say that what you think is control, is actually a bit of an illusion in many instances. and there’s lots.

What you think is control, is actually a bit of an illusion.

A lot of things are essentially inevitable or more inevitable than they seem in a way. Not in the strictest sense of that word, but more that certain variations will happen. There’s always a better way of doing things, basically. And there’s always essentially more mistakes to happen.

And it’s just more how you perceive what control is. And I haven’t mastered at all. I get upset over things that are irrational all the time.

I got upset at one recently. I was trying to- Just anytime something doesn’t go the way that I expected, I might get upset, even if it’s something trivial.

And I want to also add that it appears that there’s a way to get over those negative- to have the positive side, but not necessarily feel the pain of the negative sides, or at least master it or tame it, if that makes sense.

I see.

Through spirituality or through whatever practices or through other life ways of altering emotion, if that makes sense.

Okay. Yeah. I wasn’t looking at it that deep, I guess at the time. I was just like all the crap I could have bought. 

You’ve been playing since you were, you said, 17 years old. So how old are you now?

I’m 32.

So a long time. And made a lot of money. Probably lost a lot of money. Made a lot more money. 

You probably have an advantage. If you really wanted to, you could probably walk into any game and make $3,000 and go home that day, and make a pretty good living if you really wanted to do that right?

Not really, actually. I’m actually curious what it would be because it feels like when I sit down at these softer games, it feels like sometimes it’s impossible to lose, but I know that’s not true.

It’s easy to get sucked into that-

That mindset.

Yeah. That mindset or that trap.

Realistically, I actually lose- I don’t know how often I lose at soft games, but in competitive games, I lose about half the time. A little bit less. That’s normal.

And it wouldn’t make sense for me to really walk into any casino- Certainly I wouldn’t be able to average $3,000 every time I walked in for a few hours. In which case that would mean I’m making what, $3,000. No. Yeah. $3,000, let’s say, every 8 hours of the day.

Then hypothetically- What is that? If I worked my ass of I could make-

Twenty-four-thousand in an eight-hour period, right?

Yeah. Yeah. Wait, no. Three-thousand in eight hours.

Oh, $3,000 in 8 hours.

That’s the number that I gave. It wouldn’t be for any casino. Let’s put it that way. Most casinos, not nearly anything like that is exactly possible.

It might be more like $500. And it would also have a lot of swings.

And a not as good player would still make something like $300-something dollars or whatever or maybe more, I guess. I don’t know.

I’m not a poker player. I’ve played poker before. I didn’t know what I was doing. 

I remember one time I played with Larry Flynt and Ben Affleck on the same table in the Bellagio one day. I shouldn’t have been sitting there with those guys. I’m not saying they’re good poker players, but they had a much bigger bankroll than I had, and I got my ass kicked that day. 

But it was a cool story. Make for a good story now, right? 

And the problem for me is I don’t have patience. You know what I mean? Here you are playing two cards off suit just because you want action. 

So, patience is definitely a big part of poker.

Yeah. I guess you could say. Patience is a part of anything. Patience is necessary I’ve come to realize- I would say I’ve got that problem a lot myself in other areas. Not exactly poker. But I find that it depends on what it is.

Probably you have something that if you have the proper incentive, you’re really patient, is my guess.

That’s right.

Is there a specific thing? I’m curious.

I don’t know. For me, when I’m just at the table, sometimes you just get bored. It’s like, I haven’t had a good hand in six deals, I guess, and I want action. 

“I want to try to play this. I’m going to play this round,” right?

Oh yeah.

You know?


So I think that’s it for me. Just wanting to play.

Okay. Well, I feel that too a lot. I find it really hard to pay attention. I’ve been trying to appease my boredom by making lots of jokes and dressing up, as you saw…


…into characters. This is apparently a thing.

I see that. Yeah.

Now I have some new ideas. It’s like, why stop there? They let me do anything at the poker table and there’s a lot of possibility.

And okay, maybe there’s more that can be done, and now I have more ideas of things to do.

So, for those that don’t know that story, let’s talk about that because your character was quiet, not really a very vocal player, and then all of a sudden you totally flipped the script and went a little bold. 

So, what are some of the things that you’ve done for those that might not have heard?

In what sense do you mean?

Meaning at the table where you changed the character, changed your persona a little bit.

Well, a mix of that was, as I’ve said, it’s one of the positive sides of boredom is like, how is this boredom going to be, what’s the word? Reconciled, I guess.

So, one of the things I did was I just started making many jokes and being a bit more facetious. I’m not 100% done with that. If a number of bad things happened, that might change, but maybe that can be mastered.

What was I going to say?

Okay. So that was one thing. At some point, it occurred to me that for these interviews, that, for one, if I want to build my brand, I need to stand out in many ways. And also that many of the interview questions could be- It was more fun to answer them in ways that were a bit more unpredictable.

And somewhere along the lines, I realized, whatever, let’s play with this.

And somewhere along the lines, I thought it would be really funny if- Well, you know how when everyone’s interviewed for a tournament and they’re asking questions like, “Are you confident?”

This is a flow of life thing.

“Are you confident? What have you done to win? What’s your edge?” Or whatever question it is like that.

Every poker player says something like, “Yeah, I’m confident, but there’s lots of luck and you gotta work hard and know all the-”

They don’t even say something like you got to know all the pre-flop ranges and all these technical details. No one wants to hear all that obvious stuff. Even though, yes, it’s technically the truth.

I decided it would be really funny if out of a cartoon, I said, “Oh, it’s my destiny to win.”

[both laugh]

They probably weren’t expecting that one.


[both laugh]

If I kept saying it. I was thinking to myself, I could make a joke and if I’d kept saying it, then eventually I would win one, and then eventually it would be like, “Oh, it was my destiny. I said it was my destiny.”

There it is. Yep. You proved it.

This was the original idea, but this isn’t exactly what happened. What happened was a little bit different.

So the first time I said that was- The only tournament I ever said that in fact was for The Poker Players Championship and I got sixth place.

And then I decided next year to say- “You know what? Actually I was talking about this year. I wasn’t talking last year.” And just decided to run with a joke.

And hilariously enough, I made the final table, and in the back of my head I’m thinking, “Am I really going to win this thing? Is that what’s about to happen?”

But on the camera I’m saying, “No, I’m going to win.”

And I said, “You know what? Forget it. I’m dying my hair blue. I’m going full cartoon. This is already crazy enough.”

And also I managed to- Well, we have a saying in poker called “going God mode,” or someone’s in God mode where they seem to get a string of cards where they’re unbeatable and just everything’s going perfect.

And it’s a strange, strange thing that happens. It’s almost mystical what happens.

And I decided, “All right, you know what? Screw it. I’ll dye my hair blue.” That’s where the blue hair comes from.

Going God mode, like in Dragon Ball Z. And I dressed like a Dragon Ball Z character and talked a lot of shit and I just put on a show a bit.

Funnily enough, while I was strolling through Fashion Show Mall in Las Vegas, I went into a candy store because maybe they had some candy that would taste good.

I was curious. Every once in a while I’ll get a snack. And I ran into- Well, there’s these beans in this cartoon that heal you. They’re called senzu beans. If the characters eat one of those beans, they get healed and they actually regain their strength and that kind of thing.

Sure enough, of course, there were senzu bean candies in this shop. So I bought these.

In addition, there’s an energy drink that’s literally called a Power Boost, which is what would happen. That the characters would get energy out of nowhere. This became a bit of a joke for the final table.

I would keep eating a senzu bean, and my friend, I’d give one to him, and in fact, we’d both get a boost of chips if we did that.

At some point I ran out of senzu beans and almost out of chips, but secretly-

And then the arch nemesis started talking shit. The guy who was winning the whole time. And then he made obviously a massive blunder like in the cartoons and then a hand that he’ll never forget, neither will I.

And then I started winning because they forgot that I actually had a power boost behind. I had a Power Boost energy drink. They didn’t plan that one out really right.

So you won the tournament or what?

Yeah. I did win the tournament. I said that it was-

You manifested it.

My destiny to win.

Thanks to the power boosts and the beans.

Yeah. Did you see what happened the next year?

I don’t know. Tell me.

You didn’t see?


I won it again.

You won again.

[both laugh]

I did something similar, but this time I didn’t really plan on winning. I just talked a lot of shit. Most poker players don’t talk shit and they’re actually quite modest.

But that was part of the joke, was to go full arrogant-person and dress completely outrageous.

So now, do you have to keep that persona or what? So now, is that what they expect of you when you play now?

Whoa, whoa, whoa. I don’t only have two personas. Listen, I would like to not be limited to just two personas, no matter how crazy they are.


Yeah, I would not like to be controlled please. No controlling me.

No controlling you.

No putting me in boxes. No controlling me.

There you go. [laughs] I love it. 

And it’s funny, when Jenna was putting the information together and I was familiarizing myself with your story and your background, there was a link and I clicked on the link and I’m like, “What the heck is that?” 

I’m like, “Where’s my daughter? Make sure she’s not here. What’s going on?” 

Yes. So what was that?

I thought I got rid of those.

What was that all about? The video with you and beautiful women everywhere, and yes.

Yeah. Well, who would’ve thought a 30-year-old guy interested in women?


Yeah. Surprise.


It’s one of these things when- I guess you could call this a flow of life thing in some weird way.

So once upon a time, I had the opportunity to be part of a strip poker- No, excuse me. Yeah. Strip poker video. Cost about $5,000 and this famous Russian video guy- What is he? He makes videos. He’s an artist. He’s a photographer.

His name’s Sasha Tikhomirov. It was his idea I think. He wanted to make this video of strip poker. And somehow there were a lot of Russian and Ukrainian girls from Playboy in the vicinity, and we decided to make this video.

And his idea was to turn it into a bit of a softcore porno, which I did not know was part of the plan but, flow of life. I’m just going to blame it all on the flow of life.

Well, I shouldn’t do that 100%. This part I really didn’t know. This is one of those things where I just thought that it could open up many positive sorts of doors, and I didn’t really know which doors to open.

When you don’t know which doors to open, that’s when strip poker calls and maybe getting a little sexual is the thing you’re supposed to do.

When you don’t know which doors to open, that’s when strip poker calls.

The universe speaking again, right? Yes.

Yeah. The universe and its mysterious ways. That makes sense I think.

Anyway, that was my rough train of thought, was it was just one of these asymmetrically positive things I could do. It could open some bad doors, it could open many good doors. It’s just a different direction. It’s spicy. Spice it up.

No one saw it coming. I refuse to be boxed. Don’t tell me not to do it.

So as it turns out, it actually did open quite a few bad doors of sorts. But not so bad. It was just maybe not the right persona I’d like to build on, and I’m not really going down that road anymore.

But I guess you could say in a weird way, it’s still flow-of-life-ish in that it’s a route explored and also decided not to really pursue too much, as well as the playboy lifestyle, which I didn’t really-

I liked it in some ways, but not all the time. So you could say that it was part of my growth and made it a more interesting, colorful journey.

Yeah. Not the best Look, I think. I don’t think I want to go the Dan Bilzerian-esk route.

I decided that’s not for me exactly. At least in this sense. I like some of the crazy stuff he does, but not necessarily the being surrounded by women that are always naked all the time. Not really my thing.

Is Dan a friend of yours?

As it turns out. I mean, there are times and places for it. We’re friendly, I think.


I think we’re friendly. Yeah. Let’s put it that way. I think-

Head-to-head at a table, who wins?



I don’t think that’s a secret.

He didn’t make his money the same way that most poker professionals did, but I suppose in the sense that he makes- I presume he makes money from poker in the long run.

In the situation that he’s in, he may be considered a professional, but he’s not exactly the same as the guys that grinded it up from nothing. I think he had a different way of entering poker.

So who’s a poker player that you look up to?

Good question.

Well, I wouldn’t put it in such black and white words, but some of them have traits that I admire, at least to a certain capacity.

There’s a poker player that’s the living embodiment of the “Poker Terminator” of sorts named- Well, there’s at least one of them. Maybe there’s multiple ones. Maybe there’s multiple Poker Terminators out there.

There’s this guy named Stephen Chidwick, which you probably don’t know of. And this guy- I didn’t know this because I was watching this closely and I’m very different, but he’ll do the same damn thing every single hand.

He may even do this thing with his chips in order to randomize his decisions in certain situations. And based on where the chip falls, he’ll do something a third of the time or 75% of the time.

And he knows all the situations. He plays perfectly the perfect amount of bluffs in all the situations. And that’s his reputation anyway.

Certainly if I wanted to play perfect poker, I would take elements of that, I would say, but not all of that. If I wanted to be a poker robot, that might be my guy.

Let’s see. Who else do I admire?

Yeah, there’s a few not-so-obvious traits. There’s this guy, Phil Galfond, for example. He’s also known as my arch nemesis. His nickname is “Mr. Falcons.”

He’s incredibly nice in the sense of always polite and never gets mad at people and always treats them with kindness. I find that admirable. That would be nice to embody, I guess you could say.

Let’s see. If someone’s super disciplined and never gets scammed I think that would be- I don’t even know if I want to never get scammed. Weird. Maybe I want to just get scammed a little bit where it doesn’t matter.

That’s kind of funny because it’s funny to get scammed in ways that don’t matter. Because then they don’t matter. If they don’t actually hurt you that much. That’s okay.

But not to get scammed in bigger ways, or at least for there to be a twist where they actually get what’s coming to them somehow. That sounds like a better path than never getting scammed. It’s more interesting.

How much of your strategy is more data and analysis versus just your intuition?

What are we calling intuition?

Just your gut versus the data.

It depends on how you’re looking at that because there are many things that I do that are not necessarily data driven. That being said, I think there are ways that I can do some of them better when I’m really thinking about it.

The answer to your question is complicated because a lot of intuition is based off of experience.

A lot of intuition is based off of experience.

If we’re talking about just pure feeling and there’s no fact behind it, I don’t really work that way because a lot of the information that I have is I’ll have the intuition and I’ll be able to interpret it, if that makes sense.

I didn’t realize I was doing this. And the way that I look at the situations is a bit different. But I personally don’t necessarily get a specific feeling from someone too much. It’s completely nebulous and then I follow it, let’s put it that way.

And even so, there aren’t so many situations where this mystical one-time read can be too applicable, if that makes sense. It can be in the right situations but it’s only one part of the game I would say.

I would use a lot of intuition for when to bluff, and if people do certain things, you would get that read.

They also have to make a mistake themselves in some sense. Related to this question is the idea of analysis. I mean it depends on how analysis driven you want to be.

Also in a sense, I personally think there’s a point where there’s too much technical details and it makes sense to just take an action that’s good enough and not stress about the extra 10% of value that you’re missing, I guess you could say. Or look at things a bit differently. Something like that.

It’s basically if they consider how much strict analysis we’re really using because it’s more human nature to use heuristics and things like that, which relates to intuition.

Got it. Okay.

If that makes sense.

That’s a good way to put it. You mentioned the term “game theory.” For those that don’t play poker, what is game theory?

Game theory is just the theory of how games should be played.

It usually looks at the payoffs of certain actions and just decides, “Okay, which is the payoff that you’re actually looking for?”

It can apply to really anything depending on what your definition of a game is. It may be the case in many real-life examples that while real life often does not have definitive lines of the action to take, the actions are not so discreet.

You can essentially- I think the word is-

Well, you can just do something like box to actions to viable rough actions. Limit the number of actions taken, and so make some kind of game tree for what the best outcome should be, if that makes sense.

Got it. 

If you can give a piece of advice to poker players that are trying to improve their game, what knowledge would you drop on them?

Let’s see. If I was giving a piece of advice for poker players who wanted to improve their game, I would say, look for value where other people are not looking at it.


That’s where all the value always is.

And I would say look at both theory and practice, I would say, because theory is guidelines, but practice matters more. Real application matters more.

Theory is guidelines, but practice matters more.

What are pinch me moments in your poker career?

I’ve had quite a few. Depends on, again, how we’re looking at it.

Are you referring to improving at the game or-

No, I’m just saying, “I can’t believe this is my life. How cool is this? I’m sitting here with Spider-Man, Tobey Maguire, and I’m kicking his ass in poker right now. This is cool.” 

What are some pinch me moments for you?

I was in Asia playing with very rich, secretive Asian guys that didn’t speak any English, and I was playing with people that I had at one point looked up to like Tom Dwan and Phil Ivey. The legends.

Didn’t exactly see that moment coming. So there’s that.

And I was playing for monstrous stakes. Most of the money wasn’t mine, but there would be- Every buy-in would be something like a million dollars and you could lose multiple millions.

And the main Chinese guy that didn’t speak one word of English was just ready to play for 72 hours straight. He did this actually. He played for 72 hours straight and forbid anyone from leaving unless they lost at least a million and a half of money. Those are his rules.

But to be fair, he doesn’t leave, usually, unless he has $0 on the table.

So yeah, I wouldn’t say he’s unreasonable. He’s quite reasonable in fact. I’d say he’s a very reasonable guy.

Did you ever play at Molly’s? Any of her games?

I met her, but I did not play in her games. Yeah, I met her in the Bahamas. She seemed like a business woman. That’s about all I remember. She’s very businessy.

She is. Yeah. I met her once too.

No bullshit. That was the one thing I remember about her.


Did you ever win and then just splurge and just go buy yourself something like a new car? 

Give me a story about where you just went big and you said, “Screw it. I’m going to treat myself to something I always wanted.”

I did get a car. I think my splurges are of a different nature generally speaking.

I’m trying to think of what would be something I’ve spent a lot of money on in terms of luxury.

I bought a condo, but it was an investment. I did do that after a very big win in Vegas. Very big week of winning. Or a couple weeks.

Let’s see. My splurges were more bad investments and things that seemed like great ideas, I guess you could say, but really weren’t.

Such as buying a house on a hard money loan in Los Angeles. That was really stupid. But it seemed like a great idea at the time for some reason. And then basically all the options were bad to get out of it.

I’ve for sure spent money in really stupid ways before.

That’s really my- I guess you could say my leak is just thinking things are good investments, but aren’t.

They’re not. Okay. 

Mine was, I remember I won $30,000 one day and I’m driving home and I see a palm tree. There’s a palm tree farm and they’re like, “Palm Trees For Sale.” 

And I’m like, “Why not? I’ve got $30,000. Maybe I’ll buy a palm tree. I always wanted a palm tree like this.” 

It’s like the ones in Beverly Hills, you know?

So I’m cruising along and I pull over to the side of the road and I’m like, “Yeah, how much for-” 

“Oh, this one’s $12,000.” 

I’m like, “Could you do it for 10?” 

”Yes, I’ll do it for 10.” 

“Okay, great. I’ll take it. Here’s $10,000 cash.”

Did he snap it off? Did he say, “Yeah, I’ll do it,” or did he like-

They did. That’s their whole business. They’re just palm trees. 

And so, next thing you know, I’m driving home with this big truck driving behind me. Pull up, my wife’s like, “What are you doing right now?” 

I’m like, “I bought a palm tree.”

Why not?

I bought a palm tree. So yeah, that was-

What’s wrong with that?

One of my splurges after winning some money.

I approve. I want a palm tree now too. This sounds like a great idea.

We’re going to play a game here. So you’ve got 10 cards.

I didn’t expect that. Okay.

Yeah, don’t look at them yet, but it’s just “Never Have I Ever.” We’re going to flip a card over and you just basically answer the question. 

I’ll go first. “Worked at a kid’s birthday party.” 

That one’s easy. Yes. As a kid, when I was 15, I was-

I’m going to shuffle them too.

I was a DJ. And so, I would DJ kids’ birthday parties. And so, I’ve done many birthday parties in my life. 

Go ahead. Your turn.

Oh, I see. Okay. Okay. I don’t know if I’ve done that.

“Gambled my rent money.” Have I done that?

Haven’t had an issue. I don’t think I’ve done that, but I’ve gambled my savings away. I guess that’s close.

As I explained, I had savings and my parents locked up my savings account, so maybe that counts, but I was fortunate enough to have the cushion of my parents, so maybe I’m a spoiled rich kid.

You haven’t had to gamble your rent money away. 

“Been in a crazy fight over a parking spot.” The answer to that is no. 

I’m the person that will drive to the back of the mall and not fight over the park. My wife will drive all around trying to find that spot that’s so close to walking entrance. 

I’m like, “Why do that? Just park in the back.”

Someone recently told me a little secret about that, by the way. You know how parking garages have multiple layers?


Well, what most people do is they try to find a parking spot on the lowest layers, et cetera, even if they’re far away from the door.

But it makes sense to go to one of the highest layers or levels and get close to the door. This is not my idea. There’s a girl that told me this idea, but it was a good one.

Maybe that could be a cool tip. I don’t drive, by the way.

Oh, you don’t drive?

Forget it. I don’t enjoy the fighting for parking spots. I’m out of that.

You’re done with that. Okay.

And traffic, not my thing.

Your turn.

All right. Let’s see. Okay. “Chosen to play video games over sex.”

I think I’ve done this indirectly. I’ve chosen to play poker over sex for sure. Does that count? I think that counts. It would be poker on a screen.

I remember I had this period where I was making an enormous amount of money very fast, and I would just be multi-tabling this poker on this tablet. I believe when I was about 27.

And I would be playing it every waking hour because I was making really- I made something like a million dollars in a week. It just looked like it was just flowing into my pockets.

I had a girlfriend at the time and I wasn’t a good boyfriend. Now my values shifted, but yeah, I just was just grinding my life away.

Chose poker over sex or over video games. 

“Driven off with the gas pump hose still attached to my car.” 

Yes, I have done that. And I did it- We were driving cross country. We were moving from Atlanta to Los Angeles. 

And this was back in 2015. And you’re driving for so long, you’re tired. You put the gas pump in, you go get a water or some coffee or something like that. You come out and driving down the road, and people are pointing at me. 

I’m like, “What?” 

And I look in the truck and the gas pump is still attached to the truck. I’m like, “Oh my God. I hope it’s not flooding at the gas station.” 

But I guess there’s a thing that shuts it off if that- I guess that’s a normal thing. People do it.

Okay. I didn’t know that was a normal thing.

But to be fair, I think I would eventually have done the same thing because those are the kinds of mistakes that I make. Too distracted and just forget to do something like that.

I have done similar things. Very similar things. So that gives me another reason not to get near the cars. I don’t want to deal with this running off with hoses or any such thing.

All right. Your turn.

“Broken up with someone via text message.”

I don’t think I have.

Ooh, my son had to deal with that recently.

Does this count in terms of friend-zoning someone?

Yeah. I’d say so. Yeah.

If you’re just dating someone casually and also you text them something.

Yeah. I’d say yes.

That would be a nice thing these days in the sense of, I don’t think that people text people this a lot of the time.

Come on. If you got a relationship with somebody, you don’t break up with them via text message. I don’t know. I think that’s wrong.

Well, yeah, if you have a proper relationship. I’m just saying that most people these days, in dating, don’t say anything. They just-

They just “ghost” them, right?


Or something like that. Yeah. I can see that. If you don’t have a relationship, sure. I guess the term is you block them.

Well, I don’t approve of ghosting at all. I would just say that relative to ghosting, breaking up with someone through a text message is an improvement.

That’s true.

Is the irony of the message here, because most people do not give any kind of feedback or courtesy or anything like that. They just kind of disappear and it’s like what just happened?

That’s the- Yeah. Dating 2022.

“Lied about what I did for a living just to get laid.” 

So, back when I was younger, I had fake business cards that said I worked in casting for the show Real World. [laughs]

It wasn’t my idea. It was my friend’s idea. 

And so, it made us a lot cooler than we really were because people would love to be on the show Real World at the time and they thought I was in casting. 

And so, yes, I did lie about what I did for a living at one point.

All right. Well, that was honest of you.

I don’t think that I have. I’m trying to think. I haven’t thought too deeply about that. I’m trying to think. Have I? I don’t know.

Go to the next question.

All right. “Given a homeless person money just because they had a dog.”

I haven’t done that, I don’t think, but maybe that would work on me. I’m not sure. It’s a step up from doing nothing so maybe I would reward

Well, maybe on the way home today you give somebody $5 because they got a dog.

Well, now that you’ve given me this idea, I feel like you need a more interesting answer. So this will be the solution to that problem.

It is. The universe is speaking.

Yeah. I guess you could say it is.



Okay. “Had a crazy run on the craps table.” 

I have had crazy runs on the craps table just because I’m the person that just keeps pressing, pressing, pressing. And if you just keep rolling for an hour, you’re just going to make a lot of money.

Okay. Yeah. Guess it makes sense.

You play craps?

I don’t, but I have played it and I have seen this happen and I can see how the game is created in a way where this does happen and creates the kind of emotional thing like there’s money flowing in, kind of creates that kind of feeling, which is creative.

I don’t just press. What I’ll do is I’ll put money down on the whole table, basically all the numbers. And then every time I hit a 4, I match that with a 10. 

So I always basically take the winnings and I say lift the 4 and the 10. 

If I hit a six, I match the six and the eight. If I hit a five, I match the five and the nine. So every time I’m rolling, I’m kind of doubling two numbers instead of one. Not doubling, but I’m increasing. 

And so, if you just keep doing that with the expectation that you don’t care if you lose, you just start off with $200 bucks and then you just keep going, going, going. 

If you roll for an hour, you’re going to make a lot of money.

Oh, okay.

“Heard my grandparents say the F word.”

I don’t think so. I know they said curse words though.


“Had a fake ID taken away by a bouncer.”

Yes. I’ve had that. Got in trouble when I was in the Air Force because of that too. Oh yeah. They took it away. Not fun. Got in trouble.

I might have had that happen too.

“Hooked up with someone to get back at someone else.”

I have not done that, but I have done the opposite, meaning I didn’t hook up with someone to not piss off someone.

Got it.


You’re a good friend.


“Taken Adderall to be the most productive person ever.” 

So my story is, I actually took Adderall once in my life because my buddy, he’s so productive. 

And I’m like, “What is your secret, man?” 

He goes, “Oh, I’ve got ADHD and this and that.” 

And I’m like, “So I take these Adderalls.” 

And he goes, “And I take the next thing you know I’m cleaning my room, I’m organizing my desk. It just makes me super efficient.” 

And I’m like, “Really?” And so I’m like, “Let me try one.” 

And so, I took one and it’s the same thing. You end up talking to everybody. It makes you the lively person at the party. 

And so, yes, I’ve done that before.

“Lied about my occupation.”

I actually guess I technically have. I’m thinking.

Maybe people thought I have and I haven’t done it deliberately, but I’ve definitely said things like- I’m sure I would’ve said something like Professional Cuddler, some answer like that. So, I suppose I qualify.

“Showed up at the wrong airport or flight.” 

I have done that before with the family, with my wife and two kids at the time. It was New York, and so, for whatever reason I thought we were going to JFK, but we’re supposed to be in LaGuardia

And so, that’s pretty easy to do. And so, luckily we got there early and we were able to make it on time, but again, I got yelled at by my wife. 

Same energy level as when I bought the palm tree. Yeah.

I think your wife needs to be convinced about this palm tree. There aren’t too many guys out there with the palm tree.

That’s true.

I’m a little jealous.


“Said, ‘I’m never drinking again.’”

I have not said that, but I have said I’m never going to a club again and then promptly gone to a club 4 days in a row after that. And I’m not a club person, also. I was never a club person.

“Appeared as an extra in a movie or a TV show.” 

Yes, I was the DJ in the movie 21, which I’m sure you’ve probably seen that movie.

All right. 

Where the MIT students go to Vegas and they take them for a lot of money, but I got cut out. 

So, I spent 8 hours as an extra as a DJ and I bring all my friends to go to the movies to see me in the movie and they can’t even see me. So, yeah. 

You’re doing some acting right? Aren’t you trying to get into acting?

Yeah. Well, I think that’s going to take a minute.

“Written ‘boobs’ on a calculator.”

I have not done that, I’m aware of. Maybe I have done it and blocked it out of my memory, but-

I thought everybody did that. [laughs] That’s great. 

“Opened a beer with my teeth.” 

No, I’ve never done that. Although I’ve got friends that do it all the time.

“Said those three little words first.”

Technically I have, but I presume you were speaking of “I love you” or I’m thinking-

“I love you.” Yes.

Okay, good to get that right.

I was dating this girl that seemed to have a complicated past and she said things that I mistook for those three little words. I would not have said them otherwise, but she basically told my friend that she loved me, but was drunk or something.

And then she was kind of drunk and then said, “I think I love you.” And then I said, “I love you.” And she was like, “Yeah, I was drunk.” And then she said it again a different time.

It was very chaotic and it was a really annoying situation because from my understanding, it’s kind of dangerous to say these words when dating. Particularly for a guy.

But I could be mistaken somehow. Anyway, yeah. That’s my rant about that.

All right. Well, thank you for playing along. Learned a little bit about each other there. 

So, we’re going to end with something called “Hennessey Heart-to-Heart.” It’s where I ask you a question and the first thing that comes to mind, you just say it. Simple. 

So the first question is: What did you want to be when you were younger?

I wanted to be a lot of things.

I actually wanted to be a professor at some point, but I no longer want to be a professor, I think.

So you wanted to be a professor?

When I was younger, I wanted to be a professor at some point in time.

Got it. What was your favorite subject in school?

Just having funny ideas. I don’t know.

I had a class called “Gifted Students with Learning Needs,” and we did nothing. And I just sat there and did homework that I had to do. I liked that class. It was a good class to do nothing in.

Was there a chess class? I don’t know. That was kind of fun. I liked it when I was in middle school. I don’t know.

Didn’t you have a perfect SAT score in math?

I did. Yeah. I’m surprised you knew that.

That’s pretty impressive.

I did have a perfect one, but after a few not-so-perfect ones.

Oh, okay.

I got the perfect one eventually.

Huh. It’s pretty impressive. 

Let’s see here. What is your idea of a perfect vacation?

Define vacation. I’m kidding.

I think I want to go to some of these extravagant islands such as perhaps New Zealand or perhaps- What else? Yeah. What else?

Iceland or something like that, and just have something like that planned.

Maybe a massage at some point, maybe an evening with someone that there’s some kind of honeymoon love going on or that kind of thing.

Some beautiful views, pretty evening, sunsets, long walks on the beach, really tasty food, all those things.

Got it. 

What’s something that people always misunderstand about you?

Oh, well, people accuse me of being mad a lot because I can look serious sometimes, but I’m not mad. It’s very annoying. I would rather them not think that I’m mad specifically.

And yeah, that happens quite a lot to where they can think that because I’m quiet, I’m shy. It doesn’t work that way. Those are two different things.


What habit do you have that you think not too many other people have?

I have the habit of not forming biases and having a more fluid look of what- I don’t attach myself to judgments very easily.

And most people, I think, make judgments very fast and do not alter them very easily based on additional information or do not consider alternative perspectives or just basically make judgments too fast.

I don’t do that. I make more fluid judgments or ascribe percentages to something in my mind, but more intuitively.

Got it. 

What was the best phase of your life?

It was actually probably- What’s funny about that is that depends really on what is relative-

Okay, so I can give the cheesy answer. The cheesy answer is now.

And ideally that’s true, but for us less-than-enlightened folk, two other potential options would be one, the objectively best moment in terms of- Well, this is kind of stupid anyway, but where things appeared to be going on paper as well as possible.

But I would say that what would’ve been the case is when my view of the world was limited, ideally around when I was 17 or 18 or so, and my poker had begun to pick up and it was an exciting period.

No, it was when I was 20 and my poker world had started to ascend, and I was moving up very fast relative to other periods of my life. So that would actually be the real emotional best time or whatever point where the most acceleration in terms of succeeding or experiencing the positive sides of things would be the case.

But I found that usually people don’t look at things too narrowly.

Got it. And the flip side of that, what was the worst phase of your life?

There were moments in dealing with this girl that had these issues or seemed to have issues, or I don’t know what was wrong with her, that were very, very frustrating.

And when other things were going wrong and I’d been scammed, and I was failing at a lot of my goals, or it seemed like many of them were broken or had been broken, that was quite frustrating.

Probably in 2020, a while. I’m thinking. I’m thinking. Yeah, maybe 2020. If not that it would be something like 2015 when I had made this bad house investment and I had been doing everything that I could to get out of it, and basically everything just kept failing.

And on top of that, it just looked like there was a good solid chance that I would lose 90% of my wealth or so, which would’ve been really disastrous.

That would’ve been 2015 after buying this house, after getting all my money back from Full Tilt, $4 million and then blowing it all potentially. That would’ve been really, really frustrating.

Similar to me. 

So 2008, I had 12 houses. I was making investments, I was reading the book, Rich Dad Poor Dad. And then the market just collapsed and I was left with all these houses and on the verge of filing bankruptcy. 

And that wasn’t a fun period of my life, but-

Oh wow. That’s crazy.

But I survived it.

But if you have all the houses, don’t you still have assets of the houses?

No, because the houses were depreciating in value and I had negative amortization loans on them.

Oh, wow. Okay.

I was getting bad advice at the time.

Well, I had a very similar experience, I guess you could say. I don’t know what an amortization loan is, but I presume it is-

You’re paying basically less than in interest because the houses were appreciating so much. They were going up by $30,000 every month at the time. 

And so, they had all these loans for investors where you can basically- And you can just do what you want. 

Stated income loans, you can tell them what you make, right? Yeah. Whole different world now. They don’t do that anymore, but yeah.

Okay. I had something kind of similar happen. I took out a hard money loan and tried to build on top of a house, this one house, and it was this massive project.

And the hard money loan was incredibly stupid. And then I had to refinance, but then I couldn’t rent it out. And then I tried to rent it out and that didn’t work. And then I tried to get rid of it, and then the house depreciated by $500,000.

And basically it just got fucked in all sorts of ways.

And the people that were supposed to be my partners betrayed me, essentially. Or didn’t help me, really. And one guy basically betrayed me in one court case.

But yeah. Lessons.

Lessons in life. 

Do you consider yourself an optimist or a pessimist?

I would say optimist for multiple reasons. I would say rational and optimism, the intersection of those two things, because it’s rational to be optimistic for one thing.

Why would you choose pessimism unless it is useful?

That’s where optimism no longer is beneficial, but then it would still be for the sake of something optimistic.

I love that answer. 

Have you ever lost someone close to you?

I have, yes.

You have.

Actually, I would say he was, in reality, my best friend at the time. 2014, I think. Yeah, kind of mysteriously.

Sorry to hear that. 

What do you see as your best character trait?

I have thought that it is that I can perceive what the truth is. That’s what I’ve decided on as of lately because the answer’s a bit longer.

But to discern between what is truth and falsehood is very, very useful.

To discern between what is truth and falsehood is very, very useful.

Got it. 

What inspires you to be a better version of yourself?

I have an answer, but I’m not sure about it.

My best guess for that is for the sake of the experience. Well, the short answer is, and I think this is true, is that it will lead to more positive experiences in the future.

So, why not?

Got it.

That answer seems to work.

Okay. Is failing more important than succeeding?

I would say they’re equal, right?

Depends on how you look at it.

I would say succeeding is more important, but that they’re close to equal is what I would say.


That’s my guess, but yeah, as you said, it depends on how you look at it. What is success exactly?

Maybe even in that, you can look at it nonlinearly and say, you can find some ways of succeeding in failure even in that moment. Not even necessarily turning it into a success on paper.

It’s all a matter of perspective. 

Last question. Where were you on the day that Black Friday occurred?

I was in Austin, and a friend of mine woke me up and said, “A bunch of crazy shit has happened.”

And then I went to Vegas and played live poker.

Did you have money tied up on the sites that you didn’t know if you’d ever get back or what?

I had money on three sites, all of which were locked up.

And I had the biggest accounts. I think I had the unofficially biggest accounts on the site. I think it’s really hard for someone to have bigger. And I understood it was one of the biggest, if not the biggest amounts possible on the site.

So yeah, I did.

Wow. At the time I was doing digital marketing. I was doing work for Absolute Poker and Ultimate Bet, and I was getting them traffic and doing some things from an SEO, search engine optimization, perspective. 

And all of a sudden, I just woke up one morning and there’s a bunch of text messages, “Go to the internet now.” 

I’m like, “What?” 

And every single poker site was seized by the FBI. Yeah. It was a crazy day.


Yep. Not a fun day. 

I have one more question before we wrap up. Earlier in the show, you said you were trying to change schooling or you were making an attempt to change it. 

Tell me a little bit more about that.

I would say I’m in the beginning stages of that, but basically I believe that education should be something that’s more functional and also should be enjoyable for multiple reasons rather than forced.

And the way that I was hoping to change that is essentially combining education and entertainment, ideally. That sounds like a great, nice dream. And I would say I’m very, very far away from really doing that, but that is the direction that I want to go in.

And the idea of education that I want to emphasize is that, again, changing the perspective of it rather than learning a bunch of facts on paper that no one necessarily cares about. I mean, that can be good too sometimes, maybe if that’s someone’s thing.

But looking at education more in terms of, what I want to do is educate more in terms of values, and I want to educate something else. In terms of the values, or rather, I would say virtues, different kinds of values.

And I would like to educate a general principle of doing good, which by definition means educating that being beneficial for the rest of society. By definition, if the entire world does this, it seems to imply that it will lead to a much better situation for everyone. And I believe that that will lead to the solution to a lot of different problems.

And I think that educating these things can be- I think the idea of entertainment is actually more or less in line with that many forms of entertainment do in fact follow this format.

Storytelling, for example, is a greater than zero sum game. Improv, for example, is a greater than zero sum game. The principle’s literally, “yes and.”

What can we do together? And that is a big part of what I want to educate ultimately.

In addition, self-reliance, all that good stuff, being healthy, those things are cool too. I just think that if only those are focused on and not the idea of contributing to the society on the whole, it will result in both good and bad happening.

You can educate people to become super villains if they get all the neutral stuff right and then decide, “You know what? Let’s just take everything from someone else.”

If they’re good enough at those sorts of virtues and not good enough at- or they don’t see the value of contributing to the, you could say, “Greater good,” “greatest good,” however, spirituality likes to say it.

The flow of life seems to be into that stuff.

Yeah. Well, I wish you the best in accomplishing that.

I know for those that want to keep up with you, I believe you have a podcast called “Winning the Game of Life.”


Yep. Probably find it on Spotify, Amazon, Apple, iTunes, all the same places that you can find this show. 

And then for those that also want to keep up with you on social media, what’s your profile?



Yeah. Yeah.


Well, Dan, “Jungleman” Dan Cates, I guess, thank you so much for coming down, being on the show. Appreciate it and I’m excited for my listeners to hear this.

Well, thank you for having me, Jason.

Important Links

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