- Yo!
- No way.
- Oh my gosh.
- That's epic!
- Plot twist. Hah!
- [Phil] What does success look like?
(upbeat electronic music)
We found two millionaires and asked 10 strangers
to tell us who they think is the more successful one.
But we asked our entire audience the same question.
If our strangers choose the same as our audience,
they win cold, hard cash. (cash register ca-ching)
If they choose the opposite, they win nothing.
Welcome to Crossing the Line.
- Hello, everybody. Welcome to crossing the line.
If the game ends and you've chosen the same person
as our audience, then you win.
But every round you will have a chance
to switch to the other side.
Although, switching to the other side
comes with a penalty that will decrease your cash prize.
Every round, that penalty doubles.
- We're all absolutely terrified middle class people.
(upbeat music)
- The first guy's in front of wall street.
That's the wall street bull behind him.
- Yeah, but here's the thing,
other guy has a tyran-
has a literal dinosaur skull next to him, bro.
- Oh, that's true.
- That's a dinosaur skull?
- Yes!
- Could be a fan of Jurassic Park, so...
- The first one's serious,
which I expect a millionaire to kind of be.
- But the second one is welcoming.
- Well here's the thing,
the second one, the guy in front of the wall street bowl,
it looks like it's like, Photoshop.
- What is his watch? Does anyone know watches?
- Oh. No.
- Oo, watches, okay, he does wear a...
- The first one looks like a LinkedIn profile,
(click sound effect)
like, picture, like a headshot.
- First one looks younger, too.
- The first one reminds me more
of like a YouTuber rather than, I don't know.
It's like the whole pose kind of thing that, like,
if I were to go to YouTube and like, watch someone-
(alarm dings)
- It's funny to listen to this. Geez.
- It's hilarious. You got the dinosaur bones.
(Graham laughs)
- [Phil] First person, Sam?
- I am going with Person Two.
- [Phil] Jonathan?
- Person Two.
- [Phil] DA? (DA screams)
- I have a good feeling about Person Two.
I'm feeling it in my soul.
- [Phil] Adrian?
- I'm going with the majority, Person Two.
- [Phil] Ronnie.
- I'm gonna go with Person One.
- [Phil] Storm?
- Going Person Two.
- [Phil] Bryce?
- Going with Person One.
- [Phil] Tristan?
- Sticking with Person Two. I like the dinosaur.
- [Phil] Darian?
- I'll go with Person One.
- [Phil] Sowad?
- I'll be going with Person One.
- [Phil] Alright, everybody.
So, your initial votes are locked in.
Any switching after this point
is going to result in a penalty.
(upbeat music)
- Okay. I'm looking at gpstephan,
and he's with the guy from Shark Tank.
I think it's Kevin from Shark Tank?
- First guy has 1.5 million followers, which is crazy.
- Yeah, he has 1.5 million followers.
- Oh!
- Second guy is a realtor. Real estate investor.
- Oh, I turned 12k into 5.6 million.
- No, but his YouTube has 2.4 million subscribers.
- Traveling all over the place.
- He's in a private plane. The first guy.
- Oh no.
- There's a lot of things happening right now.
- Okay. I think the first guy does stocks.
Like, that's all I can find, but he does charity.
- You guys, Oppenheim is selling Sunset on Netflix.
- Oh.
- Wait, what?
- Oh. - The Oppenheim group,
I'm pretty sure.
- Yeah. No. The second guy, he is,
his real estate company is selling Sunset. It says that.
- And that's like a TV show.
- Yeah. He just got a Tesla. I can see that.
- I will say, I will say GP Stephan has more photos
with like, other people.
He looks like he has more of like a successful life
not in money, which is something to consider.
- The first guy seems like he travels a lot.
So there's lots of access of money.
- Yeah. The first guy travels a lot.
- And he has a highlight on donations.
- Do you think that the audience likes that?
Like, someone who's doing charity?
I feel like that could be.
- I think so. - Charity work is always nice.
- I think so. I think so, a lot.
- Does the other guy not do charity?
- It's not, I mean-
- It's not on his profile.
- He doesn't highlight it. - It's not as like, stated.
Lots of cars on the second guy's...
Lots and lots of cars.
- Very nice house. The second guy.
(clock ticking)
- [Phil] Alright, and time is up.
(alarm dings)
- Oh!
- [Phil] Now, would anybody like to cross the line?
- I... I'm crossing the line to Timothy.
- I'm crossing the line to Timothy.
- I think that I might cross the line to Timothy.
(happy strummed guitar music)
- What's up, Sam? How's it going?
- Alright. It's going good. I have rapid fire questions.
- One minute and 30 seconds?
- Gentlemen, there's a lot riding on this.
- Beyond formalities, let's get right to it.
- What is it that you do? Your official titles?
- I'm a YouTuber, real estate investor,
and real estate agent.
- Tim, can you explain what's your job?
Or how you made money?
- Yeah. So, I'm a stock trader and teacher.
I was in a reality show called Wall Street Warriors.
That was a hit and allowed me to really
get into my true love of teaching.
- Graham. Have you donated any of your money
to charities or anything like that?
- Absolutely, but I don't post about it.
- How important is money to you, really?
- It gives you time, you know, freedom.
Like, too many people are just working at jobs they hate
and they're kind of wasting their lives away
just trying to like, catch up.
- Would either of you categorize yourself
as more successful than the other?
I don't know how much you know about each other
or, you wouldn't say that...
Okay. That's not a good question.
- Your role model?
- Joe Rogan for me. Or Dave Ramsey.
- Elon Musk, Richard Branson.
- Have you had any like, struggles?
- Both of my parents went through bankruptcy
when I was a teenager.
- After I made my first 2 million in college
and I lost a third of it, it was splashed all over the press
and it made me an infinitely better
and more conservative trader.
- So, what is a fast food restaurant that is too expensive
for you to be like, eh, that's worth it.
- I think now Chipotle
because their steak bowls are like, seven, eight dollars.
- Sometimes I'm just starving, so I don't even care
if it's like five bucks or 50 bucks, I just eat.
- What is your net worth? Timothy?
- I mean, probably you could call it around 20, 25 million.
- Okay. Graham?
- Wow. About 7.3 million.
- And how old are you, Timothy?
- I am 39.
- And Graham?
- 30.
- What would you say your biggest accomplishment is?
- Building up a YouTube channel
has been one of the most rewarding and challenging things
that I have ever done in my entire life.
- Building 70 schools with my charity so far
and teaching other people now,
so I have five millionaire students so far.
It's a lot of work, but education changes lives.
(clock ticking)
- Okay.
- [Phil] Your time is up, Jonathan.
Time is up. I will see you soon.
- Come on!
- Seeya!
- Bye! - Bye!
She was strict. That was like a job interview.
- Yeah, that was rapid fire. (Phil laughs)
- I hope I pass.
- Ah!
I was too fast.
- Damn it, bro.
They might be millionaires, but I need this money bro.
- Yo, that guy said Chipotle.
I was like, yep.
Tim said he'll eat anything.
So I gotta switch sides
because Tim is too financially reckless.
Tim has a 20 something million net worth
and Graham has 7.6 net worth, something like that.
- Very good cue.
- I asked about like, their background
and they said they both like,
came from like, modest background.
'Cause that was one thing I was gonna do, criteria,
but they're basically the same for that.
- Timothy was talking about how he was on a TV show
called Warriors of Wall Street.
For me, he said that and I was like,
okay, well, he was already a Warrior of Wall Street
in general to have even been on the show.
- I also asked like, what they think
their biggest accomplishment is,
and Graham, I believe, said that his was like,
the YouTube channel, like, building a huge platform.
Timothy answered the question,
he dropped the bomb of being able to build 70 schools.
- Yeah. - Like, that's a huge...
I don't know about you, but that's a huge flex.
(Tristen, Darian, and Jonathon laughing)
I don't think anyone else can say like, oh yeah,
I built 70 schools.
- It's impressive. - And to say that casually?
- It's very impressive.
(ding sound effect)
- [Phil] Now's your chance to cross the line.
- I am crossing the line to Tim.
- I think I'm gonna cross the line to Tim, too.
- Sorry Graham, you were really nice.
I'm crossing the line to Tim.
- Ow, no, Tristan!
(electronic music)
- [Phil] Some of you crossed the line
and sacrificed some of your prize money
in the spirit of ending up on the right side,
and some of you stuck with your grounds all the way through.
But there's only one way to win,
and that is being on the side of public opinion.
I guess you guys kind of put yourself
in an all or nothing situation.
- Wow.
(intense music)
- No! - What?
(all yelling)
- Are you serious?
- Sorry!
- No!
- That's Epic!
- Even Graham's surprised.
- Oh no.
- Oh, I knew-
- I thought no way, even going into it.
I was like, it's gonna be- - What?
- ...based on his- - Oh no!
- I can't believe we all lost.
I'm kind of in shock that we all lost.
- Everyone wins in this group.
Everyone wins. No, one's a loser.
I'm personally gonna give you the money
that you would've won.
(cash register ca-ching)
(all screaming) - Oh, snap!
- There we go! That's how we do it!
- Plot twist. Hah!
- I got another fun one. I'll add on to that.
For everyone that voted me in the first round,
I'll give you $200.
- I did. - What?
(all talking)
- But I'm giving $201 'cause Graham doesn't beat me!
- Hoo! What?
- Wow. This was crazy.
- Well, that was a ride.
- Should I invest in stocks?
Should I get my realtor license?
- Thank you guys.
Seriously, thank you.
Thank you you guys. - Thank you!
(upbeat music)