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August 28, 2025 52 mins

This week, Maria interviews reality TV legend Boston Rob. Rob has been on Survivor six times, and has also appeared on The Amazing Race, The Traitors, and Deal or No Deal Island. He’s a master strategist with a psychology background. He and Maria discuss how to build trust strategically in a competitive environment, how to read your opponents’ motivations, and why it’s so important to play to win.

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Episode Transcript

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Speaker 1 (00:15):
Pushkin. Welcome back to Risky Business. I'm Maria Konnikova. Nate
is out today, but we are joined in his stead
by a very special guest, a reality TV legend, the

(00:37):
only person to appear on Survivor six times, five times
as a contestant, one time as a winner. Although I
would say twice as a winner because even the time
that he lost, he met his future wife and they've
now been married for over twenty years, so that to
me counts as a win. He's also been on The
Amazing Race Traders and Deal or No Deal Island, and

(01:01):
Rob is a fellow poker player. He's known as a
master strategist who blends cutthroat gameplay with irresistible social line stinks.
Robert Mariano aka Boston Rob. Welcome to the show, Rob.

Speaker 2 (01:16):
Thank you so much. Maria. I'm a huge fan as well.
I've been following your journey for the last few years.
I actually came across your book and I know formerly
we've never really interacted, but I'm looking forward to it
at some point here in the future.

Speaker 1 (01:31):
Yeah, likewise likewise. Oh, and on a more personal note, Rob,
I am a fellow Bostonian, though I grew up in
the suburbs. Oh, not in the city, not a true Bostonian.
Everyone's like, you don't have an accent. I was like, yeah,
I lived in the suburbs.

Speaker 2 (01:44):
Sorry.

Speaker 1 (01:46):
And you and I both studied psychology in college in Boston.
So you went in a different direction with psychology, but
we're both using it, I think, in very interactive and
interesting ways. So let's start at the beginning of your journey.
If that's okay with you. How do you get from
you know, a psych major at BU to Survivor and

(02:08):
to kind of the career that came to define you.

Speaker 2 (02:12):
So it's kind of a wild Glorian journey. But like,
actually I went to Boston University five years graduated with
a degree in psychology and made my parents really proud,
and went to go work in construction because I love
to work with my hands. I started off as a
laborer for a stonemasonry company out in framing him and

(02:37):
it just so happened that Survivor had just started. It
was the year two thousand and it was the biggest
hit and it was on TV and I had a
girlfriend at the time who loved the show and wanted
me to watch it. And I remember one day after work,
we're watching the show and there was a kid that
was on it. His name was Colby. It was the

(02:57):
second season. He was like the all American guy and
he was out there and he was doing the challenges
and doing a great job. I remember sitting on my
couch with my dad being like, I would kick his ass.
My dad was just like, oh, yeah, you think you
could do it, why don't you try? So I was like,
all right, maybe I will, you know, so I sent
in the application. One thing led to another. Who could have,

(03:21):
like I would have never predicted twenty five years later,
you know, the journey that it's taken me on. But
I think I didn't actually use my psychology degree in
the traditional way, but I kind of did use it,
you know, through reality TV and poker and yeah, all
these other competition games.

Speaker 1 (03:41):
Absolutely absolutely, it's funny. So you kind of started So
let's put this in poker terms. You started as the
chat pro, right, who's watching the professionals play on stream,
and you're like, oh, I know how to play that
hand so much better. And most chat bros, you know,
they'd suck, right if you actually.

Speaker 2 (03:58):
Put the money.

Speaker 1 (03:59):
You were the one who actually was like, you know
what I could do better? And you went and you
kick their ass, So you actually did.

Speaker 2 (04:06):
I mean it was it did not. It took a
little bit of time, but like I understood the meta
of the game kind of before everybody else, even like
the producers. I understood like not only the math of it,
but the psychology behind it. And I think that's like
really important and understanding these games that include not only

(04:29):
the physical aspect but the social and the strategic aspects
as well. And in that respect, I feel like I
was a little bit ahead of you know, my peers
from the beginning for sure. For sure.

Speaker 1 (04:42):
Well that's what interests me about you and about this
is kind of the game theoretic aspect of it, right,
kind of the meta strategy behind it. So when you
were watching what was it? You know, what was your
kind of big aha insight where you were like, Okay,
I know what game this is and I know how
to play it strategically on a higher level, because it's
not like you were, oh, you know, I'm the best

(05:04):
at survivor skills, right or something like that. Yeah, you
understood kind of the actual mechanics the game. So can
you talk me through a little bit about how you
thought about it back then, and then I'd love to
kind of talk through the evolution, you know, twenty five
years later.

Speaker 2 (05:18):
Of course. Yeah. So in the beginning, you know, the
game was fairly new, and it was two tribes of
people on an island, and there was a survival aspect
where you had to forage for your food and everything.
But beyond the survival aspect of it, even though the
name of the show is Survivor, there's a strategic aspect
where whoever wins the challenge, the person that loses their

(05:42):
team has to vote someone out. So traditionally, up until
the point where I played the first time, the first
three seasons had gone by My first season was the
fourth season. The first three they tended to keep the
strong athletic players because they felt that, you know, they
would help to provide for the team the strength and
the challenge. And I was kind of like the first

(06:06):
one to realize it didn't matter how strong the team was.
I needed people that I could control like chess pieces
in order to get myself further. Because like the game,
even though on the surface it looks like it's a
team game, it's an individual game. The entire game is

(06:28):
an individual game. So what was different was like in
the beginning, there was a guy his name was Hunter
this first season, and he was the All American Colby
kind of guy, the fighter, pilot, the strength guy, the
guy with the muscles, the voice of reason. He probably
went to an IVY League school. He was a pilot.

(06:48):
And I just said to myself, this guy's on my team.
Everybody's listening to him. If I hide in the shadows
behind him, eventually it'll get to the point where too
many of people that I can become allied with, aligned
with won't be there for me to get the numbers.

(07:08):
So why not just get him out early? And nobody
saw it, you know, And I knew by targeting him,
I could gain respect and loyalty from other people in
my tribe and use that strength moving forward. Now, Ultimately,

(07:28):
that first season, there was a twist that happened. And
sometimes this is a lot like poker too. Sometimes things
happen throughout the course of your tournament or your game
that you can't control and there's nothing you can do
about it. And it was a twist where they decided
to switch the tribes. So when they did so I
got put on another tribe, and my numbers were I

(07:50):
didn't have the strength and alliance numbers, so things kind
of you know, went awry, and I wasn't able to
execute all the way through that first season. But I
understood the bigger picture, and I made myself a promise
after that first season that if I ever got an
opportunity to go back and play again, you know, because

(08:13):
you have to understand, I was also twenty five years old.
I was a kid from Boston. I went to an
island in the middle of the South Pacific in the
middle of the winter, and there's a lot of girls
running around in bikinis and everything else. So I was
distracted a little bit also, But I made myself the
promise that if I went back, that I would execute

(08:34):
on the correct game play. And I guess I chased
a bikini that season two, which ultimately ended up being
my wife. But I did so. I mean, specifically, I
don't think there's one thing. I think I just understood
the overall better than my competitors.

Speaker 1 (08:57):
Well, I think there's a really key insight in there
that you mentioned right at the beginning, which is kind
of a misunderstanding of what game you're playing. Right, So
if people think that they're playing a cooperative game, that's
very different from if you realize that you're playing kind
of something that is a little bit more zero sum.
Right at the end, there is only one survivor, and

(09:19):
that's what you're of course, what you're gunning for. And
so I'm interested though because obviously you need to see
some of it in positive some terms, right to kind
of build those alliances and kind of get people to
trust you. How do you how do you balance that
right in your mind knowing that at the end you're

(09:41):
playing just for yourself and it's an individual game, and
yet you need to kind of have those cooperative elements
along the way. How do you kind of how do
you square that circle? And how do you kind of
make it work for yourself.

Speaker 2 (09:54):
Yeah, so as I played different seasons and as my
game evolved, the strategy also evolved. Right. You got to
remember I didn't win the first time I played. I
am win the second time. It took me four times.
I eventually won, but I never quit and I never
gave up. Now you can make the argument, you know
I did win the second time because I got to
the end with my wife and we figured out a

(10:16):
way to you know, game the system a little bit.
But I think different people need to be treated differently
in terms of how to quote unquote manipulate them. Different
people are motivated by different things. If you want to
understand how to get someone to do something, you have

(10:37):
to understand what motivates them and what drives them. You know,
almost all people are emotional to a certain level, but
some people respond more to logic. Some people are ego based,
you know, they're driven by their ego, So different people.
I think the skill that I possess is being able

(10:58):
to accurately identify which what I need to be for
each person and who needs what, and give them what
they need so that I'm able to build trust and
do it in a way that they don't realize I'm
doing it. And when I'm able to, then you know,

(11:19):
you eat and they eat out of your hands and
you do what you need to do. And I think
some of that is intuitive and some of it is learned.
I mean, I don't think you can go to school
and study psychology and just know this. I think a
lot of my background growing up in Boston, you know,
coming from a street smart background and understanding people is

(11:45):
what has helped me more than it helps other people. Additionally,
I think you know, certain people are able to adapt
to their situation and have more self awareness than others.
I think those are the two skill sets which reign

(12:08):
supreme not only in survivor and competitive reality, but also
in poker. Right. It's a little bit philosophical by nature.
It's not who I think I am. It's not who
you think I am. It's who I think you think
I am. And that literally translates into are you accurate
about what your opponent thinks about you? And you have

(12:31):
to be able to know it, and to know it
to a certainty to be able to execute on it
in order to manipulate without them knowing. I mean, the
easiest way to tell if someone's lying to you, right
is ask them a question you already know the answer
to and see how they respond. It's so simple, right,

(12:53):
and you set these little traps, you do it, and
then it becomes second nature. The other thing I think
that helps me a lot is I'm okay with confrontation.
Like on Traders, I loved the table. I loved going
to battle. Other people feared it, you know, and like

(13:16):
you know, like at the poker table, you got to
be a killer, right and you you have to have
that aggression. Aggression one is dominant over being passive. If
you sit there and wait for the game to come
to you, sometimes you'll win sometimes, like people win Survivor

(13:36):
by letting the game come to them. But for the
most part, you're gonna get close and you're gonna taste it,
but you're not going to get that victory as much
as if you're aggressive. And I'm not afraid to be aggressive.
I know when I need to take the shot, and
a lot of that comes with experience, but like I
also know, you know when to not worry about stuff

(14:00):
you can't do anything about, like twisting the game. A
long time ago, there was a poker show on TV
called Poker After Dark and Doyle Brunston like did like
the open monologue, and I remember he said, poker is
not about winning or losing, It's about making the correct decision.

(14:23):
There's a lot of truth in that, and there's a
lot of truth in reality TV competition about making the
correct decision and not worrying about what you can't do
anything about. So that's always kind of been my philosophy,
and it's like it's not like I knew everything from
the beginning, Maria, but like, over time I've learned it

(14:45):
and now I know it as fact.

Speaker 1 (14:47):
You know, yeah, for sure, for sure now a lot
a lot of what you're saying rings true for the
poker player, some of what you're saying rings true. It's
very funny. There's a thin line between a persuasion in
the setting and con artists. So my second book was
about confidence men, right, people who tricked people for a living.

(15:07):
And obviously the main difference is when you do it
in real life, it's nasty, right. If you're doing it
in a game, it's part of gameplay, right, it's it's.

Speaker 2 (15:16):
Part There's a lot of a lot of parallels to
relationships as well, And you gotta remember Survivor is a
game of relationships, especially where you vote the people off
and then after you vote them off, you have to
ask them to vote for you in the end. So
usually the way people win a one or two ways.
Either a they're too mad at the other person, right

(15:39):
and you're the lesser of the two evils, or or
you know you've figured out a way to like gain
their trust in some way, and they're the bigger person,
but for the most part they run parallel the relationships,
and you know, psychology and manipulation.

Speaker 1 (16:01):
We're gonna take a quick break and then more own
strategy and game theory with Boston Robb. It seems like

(16:24):
your psychology background has actually served you remarkably well, right
like that, that's actually probably the biggest tool that you have.
And in this particular case, this is something that that
poker doesn't have, but that you've think alluded to multiple
multiple times. There's also attention, right and the ability to
manipulate people's attention. And I think that that's really interesting

(16:47):
because you know, that is such a crucial skill. I
think in the present day, when there are so many
things buying for attention, how do you actually influence people
to pay attention right to what you want them to
pay attention to and not to what they might be
gravitating to you in the moment, like you So.

Speaker 2 (17:07):
In order for me to figure out how I get
somebody to pay attention to someone something, I have to
do it in a way that they're interested in it
or they what would benefit them. So every story you
tell when you're trying to push a theory one way
or another, or an alliance or a vote or something.

(17:30):
You have to do it through their eyes. A lot
of people look singularly at a problem and they don't
see it through their opponent's eyes. I think that's the
biggest key to being able to do well in poker.
You're supposed to think about what would they think right,
what would my opponent think I'm doing in this spot.

(17:52):
So you have to see the game through their eyes
and what would benefit them. I can't propose a theory
to you or a vote to you if it doesn't
make sense to you. If I want to get someone
get rid of somebody that's in your alliance, I have
to either a create distrust in your mind, like that
person came to me was coming to me to get

(18:13):
you out, or be like, listen, I know you're aligned
with her, but we have this other thing here and
if you come with this, I promise we are going
here and you have to actually believe it. So whatever
theory I propose to you, it has to be good
in your mind. And I don't think I don't think

(18:34):
a lot of people are able to see the game
through what's best for your opponent.

Speaker 1 (18:40):
I think that that's a crucial skill to have in
any game, including poker. And also the self awareness to
know what is your image to this particular person, right,
not just what is your image at the table, but
how does this person perceive you? I think that that
is an absolutely crucial insight. You know something that I
learned from my mentor Eric Sidell, when I'd ask him

(19:02):
how would you play this spot? Right, like how would
you play this hand? He said, that's the wrong question
because I'm not you.

Speaker 2 (19:08):
Yes, So for me, this.

Speaker 1 (19:11):
Spot isn't the same as the exact same spot is
for you. If I am in your seat with the
same cards and the same action, it's a different spot
because I'm a different person. I'm a different player, and
people are thinking about me differently. Their strategy is different,
their response is different. I can get away with some
things you can't get away with. You can get away

(19:32):
with some things I can't get away with. Right, different
things look different coming from the two of us, And
so that's how you have to think about, not how
do you play the spot? And actually most players, even
very good ones, not the best ones, but like solid
ones don't go that extra step and they just look
at you know the solver computerized output. This is how

(19:52):
you play the spot, not realizing that in live poker
that doesn't exist.

Speaker 2 (19:56):
That's why GTO is not like is not the end
all be all, And that's true for in Survivor and
stuff too. What maybe the correct decision right now might
not be correct decision five minutes from now because your
emotional state may have changed. There may be something going

(20:16):
on where this is the move you would have made.
This would have made the most sense to you now,
but because XYZ happened all of a sudden, that's not
true anymore. Like the biggest example of that I can
give you is a lot of times when someone's blindsided

(20:36):
on a vote at tribal console, meaning they were left
out of the vote. They come back to camp that night.
That is a super emotional and vulnerable time for them.
And I know because I've had a lot of experience
knowing that in that moment, depending on how I treat

(20:59):
that person, I can either one hundred percent get them
with me for the rest of the game, or I
can alienate them for the rest of the game. I
did it with Andrea Belki in Redemption Island the season
I won. We ended up blindsiding her island boyfriend Matt.

(21:19):
And she came back and she had no idea where
to go, this way, this way, this way, like she
had no idea, and she felt super vulnerable. But I
went to her and I was like, listen, I know
that you were tight with Matt, but I just got
to tell you. We couldn't tell you about what was
happening because we knew if you did that you'd react
emotionally to it. But I promise you, he wasn't good

(21:40):
for your game. He wasn't good for my game. He
wasn't good for anyone. I still want to work with you.
I still want to be in your alliance, and I like,
you know, so being the comfort person even though she
just had that happen and now being able to for
the next three or four five votes in the row,
build trust with her to show that that's actually true,

(22:01):
you know, versus the other way she comes back, she's
super vulnerable. We turned everybody against her. I mean, it's
a super manipulative game, right if you know, if you
understand it, and not everybody out there is thinking on
that same level. But some people are so the people
that are like yourself I could tell you're super in tune.
You understand the psychology, you understand the gameplay. I would

(22:25):
size you up real quick and either work with you
or get rid of you right away well out of
the depending on whether or not I felt like I
could trust you and you'd work with me, or if
you were going to be threatening to me. You know,
that's how That's what we do at the poker table.
That's what you do as soon as you hit the island.
Every time you have to make judgments about people that

(22:48):
you really don't know anything about. So you look at
things beyond what there's coming out of their mouth. You
look at their body language, their actions, because I truly
believe the actions speak louder than words every time, you know, yeah,
for sure.

Speaker 1 (23:04):
And it's interesting because you know, you talk about building trust,
and in that moment, do you actually have to kind
of believe you're building trust even if you know like
at the end you're going to be traitor right that
you're doing it strategically?

Speaker 2 (23:19):
Well, I mean, look like you said, we all signed
up for the same game. We all know one person's
gonna win, so eventually everybody's gonna build trust except for
the one person you're sitting there at the end with.
But here's the thing. If you understand the game on
a basic level, you know, when you sit at the end,
you want to sit at the end with two people
that you can beat. Nobody wants to sit at the

(23:41):
end about the person that's going to be a coin flip.
You know, you want some of the you're eighty twenty,
you got asis and they got kings, and you want
to be a huge favorite at the end. So like,
in a way, no, it's.

Speaker 1 (23:54):
Really interesting because you know, I'm just thinking about it,
like in poker terms. Again, like if you're at a
final table and there's like there are two recreational players
and like some very good players, you're rooting for the
recreational players, right because you want them to have the
chips because you want to be against them at the end.

Speaker 2 (24:12):
You want to be a favorite against them at the end.

Speaker 1 (24:14):
You don't want one of the great players to win.
Who you want to win change is obviously, you know
in poker, it's different in the sense that you can't
force them to get the chips, like it depends on
depends on what happens. But in your mind, you can
root for their success because it's always better to be
heads up against the fish than to be heads up
against the crusher.

Speaker 2 (24:35):
And there's a lot of luck in all of the
games as well, and I think that's often understated. You know,
the one thing about me and the way I play
is I understand the parameters, I understand the rules, I
understand what I'm signing up for before I play. This
is the game. Only one person's gonna win. So when

(24:56):
it's over, I've always been like a good sport, I'll
shake your hand. It's good I won, I lost, I
did my best and that's all you can do.

Speaker 1 (25:05):
That's such a great attitude. Is that kind of would
you say that that's kind of the secret or are
there other things to your kind of resilience and your
ability to kind of come back after you've lost. Right
as you said, it took you four times to come
back and a lot of people would just say screw
this right like I'm done being humiliated on TV? How
do you you know? Mentally? Is it just kind of

(25:28):
enough to say, you know, I've been playing my best
and I keep doing better and I'll just keep preparing.
Is that how you frame it? Or do you have
kind of other tricks for dealing with when you lose
and when you know when it doesn't go your way,
even though your strategy seemed to be solid.

Speaker 2 (25:44):
Yeah, I think a lot of it has to do
with how I was raised. You know, like growing up
in Boston, nobody's patting me on the back. You know,
you didn't you don't win. Get in there, kid, and
fight again. You know, get up, you get knocked down,
get up. You gotta be tough. My parents raised me
to be resilient. And you know, like I went out

(26:06):
there the first time and I played my heart out,
but I was also not as focused and then like
I realized, oh man, I missed a big opportunity. Luckily,
I made enough of an impact that I was given
the opportunity to come back and play again. So I think,
you know, like it's the same skill set in lessons

(26:27):
I try to teach my own kids now, and that
is like, if you want something, you have to fight
for it, and you have to do your best. And
if you do your best, if you really do, and
the only person that knows if they do their best
is themselves. And if you do do your best, that's
all you can do. You can be proud of yourself.
So like with Traders, like I knew I was up

(26:50):
against it, they did me no favors the way they
started the game. They put me on a pedestal like
I have a target anyway. And at first I'm like, oh, man,
like this is gonna be really hard. It's like yeah,
but it's gonna be really hard. And the truth is
like I love the challenge and I feel like I
don't know, it's like a sickness or whatever, but I

(27:12):
do better under pressure. Like a lot of people don't
like the pressure. I need the pressure like I do.
I needed to perform.

Speaker 1 (27:22):
That's really interesting because I was actually going to ask
you about kind of your mental game and how you
maintain your cool under you under pressure right in those
lights is what I studied. So for my graduate degree
in psychology, I actually studied hot decision making, right decision
making under emotional conditions, and which is it tells you

(27:43):
a lot about a person. And it's very different right
from decision making when you have lots of time and
there are there is a subset of person who performs
really well right under kind of under the lights, under
those hot conditions. It's a really interesting skill, and I'm curious,
do you feel like you've improved at that or that's
something that you've just always been good at.

Speaker 2 (28:04):
I just think like in general, as time goes on,
people get more life experience. So once you have more
life experience, once you're adept at doing this stuff, and
it's like you playing poker against a bunch of people, Like, yes,
there's a chance they could get super lucky and win,
it's unlikely over the course of an entire tournament that

(28:25):
they'll beat you, because like you have the time to
be able to execute the correct moves and you're going
to catch them out there with two pair when you
have a set or whatever. It is like you know
enough not to put your whole game at risk against
a bunch of amateurs because you'll be able to find
the spots right. So as time has gone by, I

(28:46):
understand the nuances of not only the competition aspect, but
the production aspect too, Like the time it takes, how
long it takes to do this, Like when you have
to make a move. One of the biggest mistakes I
see time and time again with poker players that try
to translate to reality TV competition. It's like when you're

(29:09):
playing a tournament and trying to win the tournament in
the first level, like they play too good, too fast,
like they got something to prove. There's no way you
can't win. You play in a four day tournament. You
got to last four days to be able to win.
So I don't care how great your spot is. In
level two, someone puts you to the test, like you

(29:32):
have to ask, if it's not a rebuy tournament, is
it worth really the risk versus reward? And I think
that's a lot of what I'm able to bring to
the table when it comes to these competitions is being
able to balance and understanding the risk versus the reward
versus someone that's never done it before, they don't have

(29:56):
that experience.

Speaker 1 (29:57):
Yeah, now that's I think that's a absolutely crucial skill.
And in poker, you know, knowing picking those spots is
incredibly important, and you know, sometimes you find yourself struggling
with it because you really want to take the spot
and like you have two people in your head talking
being like no, like, don't do it. Especially you know,

(30:18):
if it's not a rebuy tournament, you do have to
think is it worth it? Even if it's a rebuy tournament.
You know, there's an element of luck, and I think
that we can translate this somewhat to reality TV. How's
your table, drap, Right? Who are the other people at
your table? There might be some tables of crushers and
you're at a table with all amateurs, right, And you
think about if I take this spot right now and

(30:40):
I bust, I'm going to rebuy onto a different table,
and my EV is going to go down because my
IV at this table is much higher. It's like the
first season of Traders, right, I'm playing against a field
of inexperienced players, and instead I might get you at
my table next time around, right, and be in a
much worse situation. And so sometimes emotion or the pressure

(31:04):
or whatever it gets the better of you and you
take a spot. Even that technically it's plus it's minus
CV in the long term, because the EV isn't just
the math, right.

Speaker 2 (31:14):
Being able to recognize that is super important because they're
also the opposite is true. So like to me, sometimes
there's an opportunity to take a spot where it's gonna
make all the difference, but other people are fearful of
taking that spot. And I've seen it time and time

(31:36):
again and survivor where this is your moment. Your moment
isn't at the final three. Your moment is at six
and you gotta do something now. But you know, if
you kne what you make this move that you have
to make now, it's gonna set you up to win,
where if you don't, the best you're gonna do is

(31:57):
second or third. You might get to the end, but
you lose it. So I think knowing when to take
the shot is the most important. Like you have to
can't be afraid. I've always said to me, it doesn't
matter if I finished seventh or tenth or fourteenth or second.

(32:19):
I'm playing to win. So you have to set yourself
up to win. With the bob the drag queen stuff.
People say like, yeah, you could have made it early.
You didn't have to make that move so early. Maybe
I didn't, Maybe I could have figured out another way,
But in my mind at the time, that was a
correct decision. And being able to know when it is

(32:41):
even if you're fearful of it and execute on it
is imperative.

Speaker 1 (32:47):
We'll be right back. It's funny, you know now that
I think about it, because I was like, oh, you know,
I don't do a lot of the stuff that you

(33:09):
know Rob does on reality TV. But now that I
think about it, I actually talk to players much more
than other people do at the table, but because I'm
friendly and you know, I want to be a welcoming,
good ambassador. But they also give me very valuable information
because they'll tell me, oh, you know, this is my
wife's birthday present to me to be in this tournament,
and like this is my one tournament of kind of

(33:30):
and I'm really excited versus you know, oh my god,
you know, tournament number twenty and right away you know
how important it is for them, right what the stakes are.

Speaker 2 (33:39):
It's important to know that on the beach. We do
that in the downtime where we learn about the people,
their families, everything. You know. I've been working a lot
with Chance Cornet over the last few years and he's
like a huge proponent of you make a day too.
You look up the people, you find out their stats,
you learn about them as much as you can. Yes,

(34:00):
So it's not like I think poker has moved away
from the social element as much in terms of like
there's not as much chattiness and conversations at the table
at the higher stakes anymore. I mean you still find
it in like the local like small wreck games and stuff.
So you have to be able to be willing to

(34:21):
put in the extra work to do that. And what
you're saying like that's unbelievable, like you're doing recon on
your opponents.

Speaker 1 (34:29):
You have to do it in the moment when you can.
And yes, absolutely, I think it's a huge You're just
leaving money on the table if you don't take the
time to research your tablemates from day two on. And
a lot of times people don't, right, they don't look
up their seat draft where they're lazy or they're tired
because you played to you know, one am and you
want to maximize your sleep. You don't want to take

(34:50):
that hour or however long it takes. But it's always
worth it, I know, every single time, because you learn
so much and that's what.

Speaker 2 (34:58):
You become obsessive about it. So let me ask you
a question, because you went from journalists to poker player, like,
do you think there's a point where it becomes too encompassing?
Because my relationship with poker has been like this over
the last you know, my whole life. Really, I love it.
I have time, I want to play, I want to
do it. I'm into it. But at some point, it's

(35:20):
like when I hear about like the eve of sleeping
in this hotel at that hotel, Like it becomes like
I'm like, Okay, I'm going to play a tournament that
costs ten thousand, I'm going to sleep in a good hotel.
I'm going to order room service. Like, you know, the
lifestyle itself, it can become too encompassing where every decision

(35:42):
outside of that becomes about it. Do you find yourself
falling into that now?

Speaker 1 (35:47):
I mean, I try to maintain balance because it isn't,
you know, my full time career. Like I'm working on
my next book right now, I have this podcast, I have,
you know, I read a weekly substock, Like I'm working
on a bunch of screen projects. So I have a
lot of other things going on at the same time.
So I think that helps me kind of maintain perspective.
And for me, I try to kind of think of

(36:07):
poker as something that I love that teaches me a
lot about decision making, and that's constantly helping, right because
it's still I think it is still teaching me things
about myself. About the decision making process. And I'm still
evolving as a thinker in ways that help outside of
the poker world. So I feel like it's still giving

(36:29):
a lot to me. And I think that it's a
game that is incredibly powerful for other people. Right, I
want it to be a popular game because I think
it could help me.

Speaker 2 (36:38):
Yeah. Right.

Speaker 1 (36:39):
I want you to teach your daughter's poker because I
think it would help make them smarter kind of better
players right at life?

Speaker 2 (36:46):
Right? Better? Yeah, of course it does. It does. Like
poker is a game that's super relevant in the business world,
in negotiating, in understanding discipline. There's so many different attributes
that the game helps in life. At the same time,
it has a horrible reputation it does, I know from

(37:09):
the world the television, Like any time I try to
bring up any project that includes it, it has this
stigma attached to it. And I think it's because and
you can tell me why you think. But like, there
are lots of great things about the game of poker,
but there are some people that ruin it for everyone

(37:29):
else in terms of collusion, cheating, real time assistants, all
these different other things that involve in it. And then
When people hear that, they don't want anything to do
with it, because, let's face it, on a basic level,
everybody understands risks verus reward. Smart people invest in the
stock market, some people are buying lottery tickets, people are

(37:52):
betting on football games with their friends. What is it
about poker that gives it such a bad connotation?

Speaker 1 (37:59):
So I think it's actually kind of historical, and I
think that it comes from kind of a puritanical kind
of background to American culture, where they bucket it in
with vice.

Speaker 2 (38:12):
Right.

Speaker 1 (38:12):
They see it as kind of a casino game where
it's not right. I always try to explain to people
that it's actually different from every other game in a casino,
because every game in a casino is gambling, and poker
at the end is a skill game with an element
of luck, because in poker, you can win holding the
worst hand and you can lose holding the best hand,
and that's the definition of skill, whereas in any other

(38:35):
game in the casino you have to have the best.

Speaker 2 (38:37):
Of it right. You can't.

Speaker 1 (38:38):
You can't beat the house if you don't have the
best hand.

Speaker 2 (38:41):
Right.

Speaker 1 (38:42):
It's just kind of their strategy, of course, but that
it's kind of how the chips fall, how the how
the ball rolls, how the cards fall.

Speaker 2 (38:48):
They have a built in edge obviously that makes it you.

Speaker 1 (38:51):
Know, negative exactly, but poker.

Speaker 2 (38:53):
So what needs to happen? Does it need to come
out of the casino?

Speaker 1 (38:56):
So I think that that's that's part of it. But
I think also having good spokespeople for it, who try
to explain to people that what it actually is and
what it can actually bring is part of the part
of the journey. But it's an uphill batter and it's
one that you know, with the biggest bluff I.

Speaker 2 (39:12):
Tried to fight. I was kind of the.

Speaker 1 (39:14):
Beginning of it, and I continue to do it my
next book, you know, to your point about kind of
the negative elements in poker, I think that's also a factor.
My next book is about cheating in games. And so
because I actually am a firm believer that sunlight, you know,
is the best disinfectant, that's actually a very good saying,
because it makes the game stronger and better if people

(39:36):
know that cheaters are held accountable, that this kind of
thing is actually frowned upon, that it's not an accepted
part of the game, and that the game, you know,
that you will be that you'll be safe because the
game cares right and it will and.

Speaker 2 (39:49):
Every other aspect of life if you cheat their concerts
exactly exactly.

Speaker 1 (39:54):
And I'm not just writing about poker. I'm writing about
all games. And I think that you know, that's the
reason I'm interested in it is kind of the life
app applicability, right, because all of life is kind of
a game, if you think about it.

Speaker 2 (40:09):
The rules.

Speaker 1 (40:09):
We live in a society that has rules and you
live by those rules. And when the rules start changing
or people don't get punished for breaking the rules, you know,
that's eyebrow raising I'm concerning.

Speaker 2 (40:22):
Yeah, the problem is sometimes the rules are not so
well defined, right in a game like poker, where you're
rewarded for pushing the edge. It's like what is acceptable
what isn't acceptable? And I'm not talking about like what
beats what or whether you use something or not, but
like you know, a lot of areas are gray, and

(40:45):
sometimes things are frowned upon where other ways it's considered.
You know, they're applauded for their outside the box thinking.

Speaker 1 (40:51):
Absolutely, So it's you know the difference in sportsmanship versus gamesmanship. Right,
So are you a good sportsman, and sometimes gamesmanship flies
in the face of that. And there are areas of
gray right, shades of gray angle shooting and poker, for instance.
And you know what I say is I hate it.
I hate angle shooters. But change the rules if you

(41:12):
actually want to punish them, because when they're not breaking
the rules, they're technically still within the rules of the game.
I personally wouldn't do it and really look down on it,
but you can't do anything right if it's within the rules.

Speaker 2 (41:25):
I'm a strong proponent of whatever you can do within
the context of the game. I've done it on the
Amazing Race. I use their own rules against them with
the meat eating challenge and understanding what the penalty was,
and then knowing that if I got other teams to
also quit the challenge, that I would still be ahead.
And they're scratching their heads and they're mad on the sidelines,

(41:46):
and it's like I think, maybe after they change the rules,
but like they're you know, at one point I bribed
a bus driver. I took a collection of people's money
and bribed them with their money and didn't put my
own in. But I didn't say I was going to
It's funny.

Speaker 1 (42:02):
So you're very good gamesman as well. Right, So it's
a really interesting thing. I mean, some of the best
athletes are very good at gamesmanship. Right, I've written about
and he'll go in my buck Tiger Woods for instance.
You know, he's had some really eyebrow raising moments where
he's used the rule book technically correctly. You know, he
didn't cheat, but at some point, like he had a

(42:24):
boulder moved using the loose impediments rule. The rule ended
up changing after he did that, but it was like,
holy shit, dude, you know you can't do that, but
like he was technically within the rules.

Speaker 2 (42:36):
Yeah, it's so so much. I mean, it's like the
ballplayer on first base its fakes to throw it back
to the pitcher and then tags them out, like you know,
like I don't know. I think like if someone's ingenuitive
to figure out a creative way to gain an edge
with in the context of the rules, I personally think
that should be applauded. There's a lot of gray area,

(42:58):
but it depends.

Speaker 1 (42:59):
Yeah, absolutely absolutely, So what do you think kind of
you know, we just talked about poker and kind of
the huge value that it can give in terms of
thinking to say making So, since you're both a poker
player and I don't know a player of reality TV,
do you think that the reality TV has kind of

(43:20):
as much educational value or kind of value and decision making?
Like would you I just said you should, you know,
teach your girls poker if you haven't already, I'm sure
you have already, Like would you want them to like
do you think that would you recommend for them to
go on survivor for instance right as well? Like do
you think that that is something that is important or
or is it different?

Speaker 2 (43:41):
So I think this because the experience I had the
season that I won that was one of the youngest
girls ever was on the show. Her name was Natalie Tenarelli.
I think she was only nineteen at the time, and
I don't think she had enough life experience to be
able to navigate that situation, especially playing with someone like
me and other people that were older that understood that

(44:04):
kind of stuff, and she was very naive. I ended
up going all the way to the end with her
because I knew I a beater and everything, and I
just like it was still good friends to this day.
But I think my girls, I'm giving them the foundation
to make good decisions, to understand theory, to understand that.
But I think there's not a replacement for life experience

(44:28):
that would Let's put it this way, as soon as
they turn eighteen and they're able to go on it,
I wouldn't have them sign up. But if they wanted
to do it when they were twenty three, twenty four
to twenty five, I would absolutely encourage them to do it.
But I think there is a threshold where you have
to have some kind of ups and downs and experience

(44:49):
outside of the safety of my home with me, you know,
on your own, to be able to handle the adversity
that you're going to face out there with seventeen eighteen
different other personalities. That's really interesting.

Speaker 1 (45:03):
So poker in a way can be a training tool
for something like that as well, because poker is something
that gives you a lot of that kind of experience,
but not the other way around. I actually briefly chatted
with you, did not compete against her, but with another
member of traders who got really excited that I was
talking to you. Yenja Westgate. She's from Swedish. She did

(45:26):
the Swedish Traders. She kind of was interested in whether
how other games compare right, and how your background in
other games compared to that, and also kind of the
difficult things that the cameras don't capture right that go
on behind the scenes, which I think is really interesting,
Like the stuff that no one sees, I think is
probably just as important as the stuff that we do see.

Speaker 2 (45:46):
Well, you have to understand is you go on to
make a TV show. You're playing a game, but they're
going to film everything and to be cognizant of the
person that you want to be represented as. They don't
go outside of their way to make you a villain.
If you're not a villain, they're not going to in
the same sentence, like make you into this heroic character.

(46:07):
If you're not, they pretty much stick to the script
of what you give them to me. Definitely, all of
the games have helped different games because I've learned from
each of them. You know, I don't know that one
is perhaps the best training ground for the others. But
Survivor is the realist of any of the games. And

(46:28):
when I say the realist, I mean you're actually out
there starving. You go days without food, You're living on
an island, you get no help there's no production interference.
There is no time the camera's ever turned off. Yeah,
so it's like it is the real deal. There's never

(46:51):
been another show that I've done that's compared to the
immersive experience that Survivor is. Traders, on the flip side,
is filmed more like a movie. It's a production. There's
a lot of stopping and starting. There are still rules
and they're still in ten and production still you know,

(47:12):
maintains that. But they're twenty hour days sometimes if you're
a trader, eighteen to twenty hours. You know, like you
started eight in the morning and you go till three
and four in the morning on a lot of days.
But there's stops and starts. There's makeup, there's lunch, there's
other things, where with Survivor it's there's never an off button.

(47:38):
It's on until if you win or get it towards snuffed,
that's it.

Speaker 1 (47:43):
Yeah, I mean I would, I would. I would definitely die. Yeah,
I would not survive Survivor.

Speaker 2 (47:49):
I know that about me. I will because of the
physical part. Yeah. Yeah, you'd be surprised after three days
you're not even hungry. Most people don't miss a meal.
If you go three days the hunger pains go away,
and you're so focused on the strategy. I would always

(48:10):
like look around to be like there is other people
here that are doing it, Like you can't complain, Like
don't cry, Like these people are doing the same thing
you're doing. That's good.

Speaker 1 (48:22):
So I'm really curious to know kind of given all
of this, you know, and all of your background and
kind of how you how you're thinking has evolved. The
logical question is kind of the what's next. Are you
going to kind of continue this reality TV evolution, you know,
survivor fifty or whatever it might be, or are you
thinking about doing doing something of your own, you know

(48:45):
what's in your mind.

Speaker 2 (48:46):
I've always been a super spontaneous person and I kind
of always do what I feel like. I went to
go work construction after going to college, I tried out
for a show, and there have been times in between
like the reality TV stuff where like I still do construction.
I have houses, I renovate, did a renovation show on
teap which came up. But like, uh, I try to

(49:11):
balance my life and built a life where I do
and live exactly like what I want, and like for that,
I'm super fortunate you know, like I might go play
poker one weekend. I might you know, work on a
house or a project over here. I might do a
reality show. I might go on vacation with my family.

(49:32):
I don't know. I've never really planned, you know. I
just know that I'm not the kind of guy that
would ever sit in an office and go to a
nine to five. And there's something about not knowing what
I'm gonna do that's exciting and like it's wild. They say,

(49:52):
opposite's a tract. My wife is the complete opposite. He
works as an admissions director for a school. She goes
while the kids are at school, and it works. It
works for us, you know. And I think that balance
of figuring out and not knowing is like what, like, uh,
what I enjoy?

Speaker 1 (50:13):
I think that that's a that's a beautiful answer because
one of the skills that I try to get people
to embrace is embracing uncertainty, right and embracing the unknown.
I think that that's something that it's a gift that
poker gives you that ability. And I think that being
open and willing to kind of take the opportunities that
life throws at you without being married to any given

(50:34):
path is is incredibly important and probably one of the
reasons why you're so good at reality TV. Yeah, thank
you so much, Rob for for your time. This was amazing.
I feel like I have a million other questions that
I could ask you.

Speaker 2 (50:49):
Well, now that we're friends, we'll figure it out. Okay,
sounds good.

Speaker 1 (50:53):
Thank you so much for joining me, and good luck
on whatever comes next, even though you don't know what
that might be.

Speaker 2 (51:01):
Thanks Maria.

Speaker 1 (51:10):
Let us know what you think of the show. Reach
out to us at Risky Business at pushkin dot fm.
And by the way, if you're a Pushkin Plus subscriber,
we have some bonus content for you today. It's more
from our interview with Boston Rob that's coming up right
after the credits. And if you are not subscribing yet,
I mean, what's up with that? Please consider signing up

(51:31):
for six to ninety nine a month. You get access
to all that premium content and add free listening across
Pushkin's entire network of shows. Risky Business is hosted by
me Maria Kanikova and by my fabulous co host, Nate Silver.
The show is a co production of Pushkin Industries and iHeartMedia.
This episode was produced by Isabelle Carter. Our associate producer

(51:53):
is Sonia Gerwick. Sally Helm is our editor, and our
executive producer is Jacob Goldstein. Mixing by Sarah Bruger. If
you like the show, please rate and review us so
other people can find us too, Thanks for tuning.

Speaker 2 (52:06):
In a typical posting, Will foll
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