The 2025 Milly Awards! | My First Million

All right.

So, Steph, welcome back.

You've been on, I don't know, a dozen times or so.

You're a great friend of the pod.

We wanted to do this with you.

So we have categories, a bunch of categories for the year, and we're going to go rapid fire through them and we'll do it that way.

Okay, so Steph, you've been given the categories, but we don't know what you said.

Sam, I don't know what you said.

This will be a surprise for all of us.

I wish I actually would have recapped some of the numbers, but over the last 12 months Sean, I don't know if you've known this, but we've had something like 90 million views across everything downloads and views.

So, pretty wild.

We crossed, I believe.

I think we're close to 2 million subscribers across YouTube, Spotify and Apple or whatever, which is bananas.

I mean, that number, 90 million, that's a lot of view time, a lot of views.

It's a lot.

And like there's definitely like one or two shorts that got like 10 million, I think last year.

I think we had last year there was one where we told the story maybe you told the story of Elon Musk, I think got 30 million.

So like some go really heavy, but it's been been pretty crazy.

So we've reached 10s of millions of people in the last 12 months, which is astounding.

And now we do this at the end of every year.

And it's one of my favorite things.

We do mostly the same categories each year.

But it's always like so fun to go through your phone and like look at old photos and see what's going on from your trail in 12 months.

So I'm excited to do this.

So, category number one, the best investment that you made this year is that right, best investment you made this year.

So uh sam, you want to kick this off.

Yeah, so my, if this just says investment, it doesn't say best money investment.

My best money investment is always boring because i just do s p 500 bonds, but my best real investment uh, that i made was i moved to new york city, and let me tell you the story.

So i was living in the suburbs, i decided to move to new york city, i moved here and i found an apartment that i loved.

It was furnished amazingly and i go to the previous tenants i go, i want to move in this apartment.

Um, do you guys just want to sell me all your furniture?

And so I had them itemize all of their furniture and it added up to be very expensive 80000 or 90000 worth of stuff.

I said, I'll give you 10%.

They took it.

So I ended up moving to the city in a furnished apartment where I get to see my in-laws four days a week.

I go to my office five days a week and it's made me so happy.

So that's been my best investment was moving to a furnished place.

I sold all my cars.

I don't own basically anything and I love it.

Owning less stuff. moving to the city, being near your family, working in person in an office.

That's actually a pretty big change overall.

Huge change.

And it's definitely made me a lot happier.

Questionable if it's an investment, but it is a huge change.

I will give you that.

It's an emotional investment.

I'm emotionally invested in this city now.

See, this is why I don't do index funds and bonds because imagine if I'm one day on a podcast and they ask me what best investment of the year and I have to start talking about seeing my mother-in-law.

That's why I pick stocks, baby.

That's why I do it.

What am I going to say?

My net worth went up by 30% this year through boring stuff?

Yeah.

Steph, what do you got?

Best investment of the year.

Tell me it's an actual investment and not like- Sean, I'm about to disappoint you, man.

Oh my God.

The only time I check the S&P is to gauge my husband's mood for the day.

So he invests all our money.

And so I got to come up with something else.

My investment is also not really an investment, but it's Accutane.

You guys know what Accutane is?

What?

Yes.

Yeah.

Is that like acne medicine?

What is that?

Yes, yes, yes.

So backstory real quick.

I've had acne my whole life, like truly since I was 13.

I'm 32 now.

So what is that?

That's nearly two decades of just unnecessary pain, time applied, just the worst.

Anyone who's had acne knows it sucks.

So I spent forever just being like, it'll go away.

I'm getting older.

And then I was influenced by the king influencer, Mr. Beast.

He was on, I can't even remember what podcast, but he just slipped it in.

One day he was like, yeah, I took Accutane a few years ago.

Didn't really tell anyone, but one day my acne just disappeared overnight.

I don't know why more people don't talk about this.

And I was like, first of all, yes, why don't more people talk about this?

And second of all, I'm going to call up my dermatologist and ask why.

I'm not on Accutane and I took it for six months this year and I'm clear.

And I think it's like you know, obviously your mileage may vary.

Go talk to a doctor, but I'm just like this is the best thing ever.

People, the internet can do the comparison.

I mean, I always wear makeup.

So take right now, go back to like V1 of me on my first million.

It's going to look different.

You should post a tweet of a true before and after.

Well, I think that's the thing.

People are so embarrassed to like.

You know, if I were to actually take, I'm sure I've got some images of me.

No makeup during those periods.

It's embarrassing.

So we have another category called biggest personal L you took.

And maybe there will be some photos that might be shared during that time.

Okay.

So you also didn't do the category.

We're off to a rough start here.

All right.

So my investment.

So it is actually kind of funny.

A year ago to the day, so December 17th today, I tweeted out on December 16th this tweet.

So I said, I'm going Christmas shopping this morning.

I'm Xmas shopping assets this morning.

And I tweeted it out.

So basically what I did was that day I took –

Something like $1.5 million, and I spread it across these stocks, and I tweeted it out that day.

I said I'm putting 20 into Shopify, 20 into Tesla, 20 into Eli Lilly, 20 into Bitcoin, 20 into Coinbase.

The one I forgot to put on here, I also put 20% Google.

Sorry, not 20% Google.

Basically, I put $250K into each one.

So I think the total was $1.25 million invested. on the same day on December 16th.

No dollar cost averaging, no research, no nothing.

I was just feeling like these are things I would like to gift myself for long-term ownership.

And if I look, so the results of these now are what?

So I just looked this morning because I haven't really been checking too aggressively.

So I had a couple that were flat.

So Coinbase and Bitcoin are essentially flat.

Coinbase is up 1%, Bitcoin's down 8% in that total year span.

But everything else, Shopify's up 53%.

Tesla's up 16, 17%.

Eli Lilly's up 35%.

Google's up 50%.

And so my public stock bet that I put out there is my best investment of the year.

Because I think the blended average here is something... What is that?

Let me... I thought I pulled it up somewhere.

I think it's something like 35% for the year.

And so that was a good return on a one-day shopping spree.

I...

You use these words, like shopping spree and things like that, as if they apply here, which is hilarious.

I was supposed to be Christmas shopping gifts for others and instead I bought stocks for myself.

I thought you committed to the index path last year.

I distinctly remember you saying that.

If I did, these are false promises.

I am part of this degenerate lifestyle for now and for always.

So Sean, what do you do?

Do you keep those five or do you pick five new ones?

The one part that's not, I'm not trading these.

These are like What companies do I, what companies or assets do I want to own for like a 10 year period?

10 years, my sort of default hold period.

And that's what I graduated in college in 2010.

And it's basically what I've been doing since then.

So I had one thing that I bought for 2010 to 2020.

And then in 2020, I bought a bunch of stuff which wasn't so great, because that was when COVID was happening.

And it was like a really crazy time.

But in general, when I buy things, I try to hold them for 10 years.

That's the goal.

Why Eli Lilly?

Because they do Ozempic?

Because you told me that they had some drug that was incredible.

And you were like, what is it?

You texted me something.

And I was like, listen, I didn't listen when Sam said the Ozempic thing.

Um, but literally it was one.

It was literally the only that.

It was just you telling me that this drug is incredible and it puts us empty to shame.

And it wasn't fully out yet, or something.

I don't know what, I don't know.

You had some early around this.

Yeah, I had a guy basically.

So I like to biohack.

So I test all types of crazy stuff.

A lot of times it's like compound stuff, meaning like it's like, stuff from China.

And I don't know what I'm allowed to admit to right now.

I don't want to go to jail.

But yeah.

Your friend does all this.

Your friend also named Sam.

And it did all of the stuff that Ozepic does other than make your stomach feel sick.

And I started taking it and it's amazing.

It's so good.

I mean, I don't take this stuff like regularly.

And just anytime something new comes out, it's sort of like, oh, what's a DVD player?

I got to buy one.

You know, that's what I do with drugs.

Like you learn about new technology.

And it was amazing.

So you told me this.

Did you research it though?

No, no.

Dude, you told me I think that day and I was like, you know what?

I'm putting Lily in here.

It's up 34%.

I didn't say I researched these, by the way.

I operate on gut and swagger, okay?

And so since then the CEO of Eli Lilly has come on, because Lily has turned into like a trillion dollar company.

It's like the first pharmaceutical company to do that and he's explained all the incredible things that they do differently than the others and how they're using ai and i.

I feel better about it now.

There's more to like, but i can't say that any of those were the reasons why i did it like yeah, they do operate like more of a tech company now, but uh, i don't know, it just seemed like people were gonna want.

I just sort of was like people are gonna.

Ozempic is like the best product ever And Sam says they have a better Ozepic coming.

All right, great.

That's enough.

Sean's investment thesis just says Sam tried some drug.

That's it.

Well, historically, that's been all right.

I missed three or four of Sam's other ones.

And so I thought, well, for once, I'll do this.

Like, for example, like, do you remember when we invested in the mobility trend on Instagram?

No payoff, but yeah.

Yeah, like there has been a few things.

We invested in Andrew Huberman early on.

We've got a couple investments, right?

It just turns out this one was financial.

That's cool.

That's great.

Steph, you have some offer for people who are listening.

What is the offer?

What is the thing that you're giving people if they go in the comments or the description and click?

What is it?

Oh, yeah.

HubSpot and you guys at My First Million were very kind and generous to offer.

Internet Pipes is a project I've worked on for the last two years.

Probably heard about it on the pod before.

So if you go to the link, I guess, in the show notes, you can enter and get one of 10 copies.

And if you enter, you get my digits database.

So it's like 100 plus generation defining trends that hopefully will mean something meaningful in the future.

Things like, what did Elon see?

He saw that it was possible to exponentially decrease The cost to send a kilogram to space.

What does that mean?

Well, it means like completely rethinking our communication system.

Start link.

Right.

What does it go in?

They definitely get the database and then 10 people will also get free access to pipes.

Exactly.

All right.

Go get it.

OK, so does that mean that worst investment of the year is also going to have no answers for you guys?

Are we?

Yeah, I have one.

You know, when I sold my company I got a bunch of HubSpot stock and I held on to a lot of it and then I saw how multiples are getting crazy and I had to like even out because it was making up too high of a percentage of my net worth, but I still kept some of it.

So I got my ass kicked on that one.

How about you stuff?

Sean's not going to like my answer, but it's not financial.

It's a vitamin?

Is it a vitamin or a supplement of some kind?

Worst investment, a vitamin.

No, I did get a notice that a bubble tea company I invested in a few years ago during peak SERP went under unsurprisingly.

Oh, dude, I've got like 20 of those this year.

What do you mean a bubble tea?

It was literally these founders who were on one of those crowdfunding sites who was like just had no, no real evidence that they would make a great bubble tea company.

But i was like bubble tea is great and invested in that.

But my actual answer for worst investment that is not financial is just uh, networking events.

I feel like you guys already know this, but like it's taken me way too long to name names.

Which conferences do you regret this year?

Let's, let's put them out there, all of them.

Uh yeah, I think that's that's my worst investment going to all these things that you, just like you know beforehand are going to suck.

You're not going to like them, but there's some sliver of you that thinks like there might be something good there.

And then were you required to go or it was an optional attend, and then you've regretted it was it was an optional attend.

It was a lack of judgment.

Gotcha.

What about you?

Okay.

I like it.

Um, Sam, anything you want to add to her, uh, her networking event answer?

No, I agree with you.

But yeah, I'm on board.

What about yours, Sean?

What's your biggest loss?

I went to one networking event with you, and I thought you did great.

I was like, wow, she's such a natural at these events.

Not because you weren't trying.

And I was like, oh, people just seem to gravitate towards Steph.

They want to hang out with her.

She seems like a safe space for everybody who's exhausted from the networking part of this event.

And uh, i just remember thinking i don't know how she did that, but i like that that was.

By the way, i had a great year at networking events.

I went to an email newsletter conference.

We went to uh, sean's basketball thing.

Uh, i went to the hubspot conference.

Like, somewhat recently, i had a great year.

Did you have?

Like, i guess i only sounds much better than the others, what?

Um, so so you had a great?

Uh, like you, i like going to networking a good time.

Yeah like, if i pick it.

Yeah, because i like seeing old friends.

I've been in the industry for long enough that it's the only time that i see old buddies.

That's fair.

Yeah, that's true.

Did you go into HubSpot?

I didn't really go to anything this year.

You went to Inbound.

Well, that was in San Francisco.

I just showed up, I gave my talk, and I left.

So it was a very quick thing.

I hung out with Dharmesh, actually, at the event.

That was kind of the only thing I did.

Yeah, that sounds awesome.

Okay, I'll give you my worst investment of the year.

Once again, I...

Took these literally.

So here's my... This wasn't... Okay, so I guess there's a little less literal.

I didn't lose money much in any investments this year, which was nice, because in prior years, if you go back and watch these awards, it's like hey invested in this Crypto Ponzi scheme.

What's up with that?

You know, that was pretty bad.

You know, I've run into some trouble along the way.

This year, I didn't have any.

But I will say this.

I realized, I found out this year that I passed on three different...

$10 billion startup investments that were right in my wheelhouse.

Which ones?

And unbelievable.

So the first one was Polymarket.

I was one of the early users, probably the first 5,000 users of Polymarket.

I'm a degenerate gambler.

I...

You know, my college GPA is like half a point lower than it should be because I used to go gamble on riverboats in international waters and stuff instead of going to class.

Like, I am a degenerate gambler.

I was using Polymarket.

I was VPNing to pretend I'm in Morocco to place bets, allegedly.

And so, you know, I'm using Polymarket.

I love the thing.

The founder is in my DMs.

He screenshotted his phone and posted one of my blog posts as the background of his phone.

He's like, I thought you'd like this.

This is my background of my phone this week.

And I was like the ultimate in and didn't somehow end up making an investment just like, didn't go actively try to do it until it was too late.

Kalshi, same thing, another prediction market, same product.

If I didn't hit the winner you know the first winner, Polymarket maybe I could have hit the second winner.

I go back, I check my DMs.

They've been DMing me since 2020.

Hey, huge fans of the pod.

Would love to do something with you.

You know, all I needed to do was answer.

And guess what?

I did answer.

And here's what my great answer was.

So pretty similar to Polymarket then, huh?

That was my son of a gun answer.

How much would you have made?

The valuations of those were probably sub $100 million for sure at that stage.

And now they're both above $10 billion.

So no public math, but somebody at the chat can tell me how much money I lost.

And the last one was whatnot.

So I get acquired by Twitch, the number one live streaming platform.

When I'm at Twitch, guess what I do?

I tell Twitch, Hey, we're losing the battlefield on mobile.

I become the leader of mobile at Twitch to do mobile live stream.

Dude, we talked about these guys on the pod too.

You had a great spiel on them.

Talked about on the pod.

I actually meet with them.

I try, I asked to invest.

I'm like, guys, I could help you.

I know this space inside and I know all the talent you need to recruit.

I know the best people from Twitch.

We'll go poach them.

We'll raid the pantry.

This is going to be amazing.

And they were like, he was like, yeah, you know, we're pretty oversubscribed.

And I was like, It's me.

Make some space.

And he's like, all right, let me get back to you.

He did not get back to me.

And I did not get back to him.

And I did not invest in Whatnot's first round.

And now it's a $10 billion company also.

And it was literally the thing I was doing, the thing I know probably, you know, there's not 100 people on earth that know that space better than I do.

You know, and missed it, how many of your investments went under this year?

Because i, this was the year where uh, i probably got 10 emails of different angel companies that i uh, angel investments that i made that they went under.

It took about three years.

Well it's, it's the worst phase, right?

So we're i, i we're probably both since we started like angel investing.

You, you had a syndicate, i had a fund like 21.

The worst phase is going to be like year three, year four, because the only companies that are exiting are either small exits or just shutdowns.

At this stage, your winners are going to ride for another five years.

So it's like AngelList you got a distribution and you go check and it's like 341 from this company.

And then the founder's bragging about their acquisition on Twitter and you're like just shoot me now.

Would you, going back, how many angel investments have you done, Steph?

I don't know, like 15?

Okay so, going back, and okay so, first of all, let's look forward in the future.

Five years from now, let's say you invested 100.

What do you think that $100 is going to turn into for both of you?

Or what IRR?

I don't know how you want to measure it, but.

It's hard to say.

I think it'll three, three to four X basically over the 10 year period.

So it'd be something like a, it was a guess.

You know, if I was, my personal guess would be like something like a, something like a three to four X over over that, over the 10 year lifespan.

That does not seem worth it.

That doesn't even seem worth it for the K-1s I have to deal with.

Honestly, I don't know if you guys are different.

My learning from Peak Zerp was I never want to angel invest again.

Unless it's a company that I want to be involved with actively.

It depends.

I use a conservative estimate just to not get my hopes up or just false promise myself.

But the thing with these is it depends on basically your bet.

I did 110 deals.

It just depends on your top four deals.

So it's like I have these four companies.

Right now, they're doing amazing.

They're, you know, like whatever, 100x returns on each of them or 50 to 100x.

But like will they last?

Will they exit?

Are they going to go up another order of magnitude from here?

Like that's what you need in angel investing is to get like this sort of like multi-100x or 1000x type of return.

And then you look like a genius.

But you don't really know for a while, to be honest.

Like even the companies that are kicking ass right now, the breakouts, they were, you know –

It's hard to know.

Can they sustain it?

Will they time the exit?

Will they actually IPO?

What's going to happen?

It's hard to know.

I've done 56.

My first two or three were pretty great, maybe 10x or plus.

Then my last two were 100x or something crazy like that.

Basically, I had to go through 50 of them to get the one or two winners, which is pretty wild.

It's the normal hit rate.

It's normal, but it doesn't feel good when you're on number 48.

The trick isn't even out of 100, can you get 12 instead of six?

It's are your six as big as the big winners are in any given cohort of companies, right?

And it's also hard to know.

I invested in Replit and it had like 2 million in revenue.

It now has 250 million in annual revenue.

It's growing like crazy, like it's unbelievable, but like, where does this all go?

It's hard, it's hard to know, you know, if that's sustainable to keep keep growing as fast as they've been growing.

All right, so next category is the biggest personal l that we took.

Okay, i'm gonna tell you what mine is and it's gonna make you guys all just like uh, cringe.

So basically, i was at a party it's about six months ago and i overhear this group of people talking about being pregnant and this one lady i i can't even tell it, tell you, i asked her when she was due.

I've done that one.

She wasn't due.

And I said.

I said, what do you do?

Dude, I spent.

Why are you looking at me like that?

I spent 30 seconds looking for now.

Oh, I thought I had been in front of five other people.

I just apologized.

I said, sorry.

And I walked away.

I said, I'm so sorry.

That is so bad.

I try.

I was like a guy falling off a cliff grabbing for trees and i couldn't grab a branch and i was like i uh, i i thought you said you were pregnant.

I didn't see your kid with you, but so i didn't know like you had a kid, you left him behind and then eventually it just was.

I'm sorry, i've really.

Yeah, i just apologized.

It's so funny because on podcast, you know you self-deprecating is good, But like what's full deprecating?

Don't go full deprecating.

You went full deprecating there.

I just like, I'm not joking.

And then my nanny was with me.

Like we went to a party and she was like, you really blew that one.

I was like, I could tell.

I did that at a Christmas party in 2013.

I could tell you the exact place and date.

And then it was like, I've just never, it's never left me.

I knew not to do that.

I knew not to do that, but I just like, I told you about when I did it.

I knew not to do it, but it's sort of like, I don't know when you instinctively stop at a red light.

I just thought I heard her say that she was pregnant.

And I just said, wait, what do you do?

I don't know.

It was horrible.

And it's one of these things that I'm gonna remember for the next 50 years.

Wait, I'm so curious.

What do these women say when you apologize?

Are they like, oh, it's okay.

Like people do this to me all the time.

Or are they like, you're an asshole.

No, she rubbed it in my face.

She basically just smiled like smugly.

You know, screw this lady actually, because it's her fault.

No, she like looked at me and just like, she like acted disappointed in me.

Which she was.

So I don't know.

She looked pregnant.

She looked like a normal person, just had a big belly.

Doubling down.

Wow.

That's outrageous.

Amazing.

We should segment to a HubSpot ad.

Sean, you go next.

All right.

So I have a bad one, too.

So I got jury duty this year in April.

And I was like, I've never had to go.

Sometimes you call in, because it's an every year thing, but it's like Russian roulette.

So you call in, they're like, you don't need to come in.

Or you go in and right away, they're like, hey, you're good to go.

I've used a hardship thing, like I got to be at work.

I got out before.

So this year, I expect it's going to go swimmingly again.

And I show up and...

All of a sudden it's like, no, no, you're definitely going to be needed.

You're definitely going to be seen.

There's a really big case.

And I'm like, what?

I don't want a big case.

This is bad.

And so I get into the jury duty like where they're like vetting people, right?

And the judge gives this big speech about civic duty.

And like there's a presentation, like not even a presentation.

Remember Prezzy?

The judge had a Prezi going on.

The judge is like proud of his animations.

He's like, check this out.

Everybody is the first time they use Prezi.

They're like, holy shit.

This is better than Avatar.

And so the judge is doing a Prezi about, like the founding fathers and how this is.

The jury duty is the bedrock of society and all this shit.

As you might guess, I'm completely unmoved.

I'm completely unpatriotic in this way.

I do not care.

And so I'm like just formulating my idea of like how I'm going to get out of this.

So I'm like, oh, I'll just say I have a work trip.

Easy.

They gave the dates.

Funny enough, I got a work trip.

So I'm in the row.

So there's like seven people ahead of me.

First person stands up and says, your honor, I have a work trip.

I'm not going to be able to attend.

And he says, do you have the booking information?

Can you please show it to me?

And I'm like, what?

And so that guy starts to.

So I go on my phone and I'm like so I book a flight and person number two goes.

I don't hear him.

I'm booking a flight.

Person three goes, I'm booking a flight.

Uh, the judge has reviewed that person's booking and says um, this was booked today and the you got your.

This was booked in the like the window after you were served.

Notice, the flight needed to be booked before that.

So now i've got a booking and my lie is gone.

So i'm like okay, what am i gonna do next?

So i, the next person, goes and they say like i'm really important at work.

So i'm like i have this podcast and i'm like that's not gonna work.

So i'm like that's not gonna work.

What do i do next?

So eventually comes to me and i'm like uh, i have a.

I do have a baby at home.

So i was like i have a baby at home, i need to be there to take care of the baby.

My wife works.

And so judge is like does your wife work at home?

And i'm like it's a personal question.

But uh, so i'm like do i lie?

Do i not lie?

I'm like she is at home, but but, but i'm like trying to figure out like, how do i like, can i, can i muddy the waters a little bit?

So i was like but you know she's.

And basically the only idea that comes to my mind is to I'm like.

I'm like yeah, I'm like, do I just say she's a bad mom?

Like that's not going to work.

She's a drunk, sir.

So I'm like, I'm the primary caretaker of this baby.

And then like, you know, like I even remember the baby's middle name at this point.

And then she's like, she's like, so could your wife take care of the baby?

And I'm like, Oh God, like I'm going way deeper in than I thought I was going to go.

And so I'm like, Yeah, but I just wouldn't feel comfortable with it.

And then she's like, why?

You're like, look, your honor, it's, what is it, noon?

She's already about eight Xanax deep.

Okay.

I basically made my wife sound like either a bad mom or like a drug addict or something.

I like, she's a drunk.

And so I was like, you know what?

I'll be fine.

I'll be here.

Can't wait to, can't wait.

I'll be, I'll be there.

And so I just let it pass.

Girl next to me, she goes, the lady asks, she's like, can you do it?

And she's like, no.

And the judge goes, why not?

She goes, it's against my religion.

I don't believe you should judge anyone.

And she's like, what religion is that?

She goes and she cited a Bible passage which was like like, basically about like don't, don't judge anyone.

Therefore, you know, because they don't judge you or something.

And the judge was like, okay, thank you.

You're dismissed.

Couldn't you have just told them you're racist or something?

Yeah, i thought about that, but i was like i was in a very diverse crowd and i was like i still have to like in case i don't get off with that.

I don't want to be around these people where i'm saying a lie that i'm racist.

So i you know it was a tough in the moment, but it was a big.

The biggest l i had was uh, just embarrassing myself and, by the way, it was so fun.

Jury diddy was a great time and i'm glad i got to do it.

It was a great opportunity.

Uh was did you make him guilty or innocent?

I didn't get picked in the end for the actual eight in the box or whatever, like the people who actually go sit there.

I just didn't get dismissed early.

So you spent the day.

I spent three days there.

You should wear a purple heart, man.

Look at you.

You're really just taking one for the country.

It was true.

What's yours, Steph?

Guys, I swear my answers get better from here.

My biggest personal L was staying in a job too long.

No shade to my previous employer, but I think... Sounds like a lot of shade.

No, no, I promise.

I promise.

Sounds like a canopy.

I just... You guys know I was working on a podcast for three years.

It was a really cool opportunity but, I think, the epitome of when other people think you should be good at something and you think therefore, you should be good at something and that you should figure it out, versus driving full force towards a thing that you love doing.

So...

And it was a pretty prestigious job.

I think a lot of people would have been drunk off that as well.

Yeah.

And so now I'm at Grok working on growth and it's just, for me, way more fun.

And Steph, did we not have a conversation about this?

Did I not tell you that this was the case?

Did I not try to tell you to don't carry this guilt or this feeling like you need to prove whatever and that you're a superstar and you should be doing superstar things?

I think I gave you that.

You're a superstar.

You should be doing superstar things.

Talk.

You 100% did about a year in.

And it took me two more years to make the call myself.

It didn't land.

Yeah.

I'm not very persuasive.

All right.

Next category we have is... Coolest moment.

Coolest moment of the year.

I've got a good one.

Actually, can we skip to... Let's do a couple of the non-personal stories.

We'll come back to that one.

So let's do...

You want to do Billy of the year or favorite guest?

Which one you want to do?

Let's do Billy of the year.

OK, Billy of the year.

Sam, you go first.

Yes, I did this podcast with this guy named Steve Houghton.

Steve Houghton is a billionaire via real estate and oil and gas, which is very vague, but I can explain.

But at the end of the pod I like made like a joke because we had talked about this whole podcast about how he was a billionaire.

But it seemed like his kids really loved him.

And I made an offhanded comment like yeah man, I got to come out and see how you manage your family sometimes

It's an inspiration.

And without skipping a beat, he was like, how about in four weeks?

We're going to be at our ski house.

We have a room for you.

And I was like, all right.

And I just said yes.

And I had to go downstairs to my wife.

I go, pack your bags, Sarah.

We're going to Utah.

She's like, with who?

I was like.

I met this guy.

I just did a podcast with him.

I've only known him for 60 minutes.

I don't know anything about him, but we're going to his house.

And I got to his house and it was amazing.

And it was amazing for a bunch of reasons, because I got to see how he worked with his family and it was really amazing.

But it was pretty funny.

They say money doesn't buy happiness, but I was very happy being in the 17000 square foot home with his entire family.

And I mean, this sounds like I'm being a D-bag, but this is the truth.

I do think that wealthy people see their grown kids more than non-wealthy people, simply for the fact that there was room for all of us to be there and be comfortable.

And it was amazing.

And I've since like stayed in touch with his kids and he had another family there as well.

And it was such a fun experience.

And so Steve Houghton was my Billy of the week, Billy of the year.

Billy of the year.

Love it.

Steph, who you got?

Billy of the year.

All right.

So I tried to start from the perspective of what is a piece of technology that I think is just incredible and mattered this year.

That piece of technology for me was Waymo.

A lot of people are familiar with it.

I got to interview their chief product officer a few years ago in a Waymo.

And it's kind of crazy when you actually think about it.

I think that was max two years ago, maybe three years.

And when we were riding in that car in San Francisco, people at that time were still like, peering into the windows like, oh my God, look at that crazy thing.

And in the last few years, at least in San Francisco, Phoenix, a few other cities, it is so normal.

There's Waymos upon Waymos.

I've been at intersections where there's eight Waymos at that intersection.

Does it make traffic faster?

No, not necessarily.

But I think if you could have all the cars on the road, it would make traffic faster for sure.

But the person I chose, the Billy I don't know if he's actually a billionaire, so I'm cheating a little bit, but he's for sure a hundreds of millionaire is Sebastian Thrun.

He was one of the early billionaires.

He's like the father, godfather of self-driving.

Exactly.

So let me throw out a few different pieces of his timeline.

So he was motivated by personal tragedy.

His childhood friend was killed in a car accident when he was 18.

That got him invested in trying to figure out this self-driving equation in 2005.

So 20 years ago, DARPA had a grand challenge funded by the U.S. government.

His team won.

Then, 2007, he goes and he joins Google.

And he didn't just create Waymo, he also co-founded and led Google X, their moonshot factory.

He co-developed Google Street View.

And, of course, he was one of the creators of Waymo way back when.

But here's the thing.

He left in 2014 and he's also gone on to do some really cool shit.

So in 2011, he put out this introduction to artificial intelligence course online for free.

160,000 students enrolled.

Um, because he saw how people could learn online.

You don't need to be at Stanford to learn about AI.

He created Udacity in 2011.

And then since then, he's also led the Kitty Hawk Corporation.

They were building electric flying cars, didn't ultimately end up working out.

But that's another thing that he's been like super early to.

We're now seeing these EV tool companies, you know, get off the ground.

I just think this guy is super cool.

Like he's been early to all of these trends and is just like continuing to build, even though he's already.

You know he was early to Waymo.

He's rich and he's just continuing to dabble.

This guy's prolific.

Good find.

There's a.

There's like a lineage, i think, of people under him.

Like he had his initial lab, maybe at stanford or whatever, and somebody who was doing self-driving.

I was describing, like you know, basically all the modern self-driving kind of like leaders.

If you just trace their kind of lineage, it's like he had six people or seven people under him.

It was that school of thought, that sort of like branched out and created like all the different people in the industry today.

Um, so he's very much like uh, what was was a sort of grandfather or godfather to that, to the industry.

He's also he's got some range because like he created a you know these cars, things which is like the most brilliant thing on earth.

But then also he has a course business and that's I'm being silly a little bit.

But that's like not, in my opinion, in the same category of flying cars.

But it's Udacity to me is a very respectable, like amazing thing.

And so it's pretty cool how much range he has.

Yeah, so all of us who create courses, we're just like these self-driving car guys.

Right, you have to do the other same range, but usually range is like wide.

This is almost like up and down.

Yeah, our barbell doesn't have the weight on the other side yet, so it's a little awkward to hold.

So we definitely have to go and do that, but that's pretty cool though.

All right, mine um came down to a coin flip between john morgan and jesse cole.

I went with jesse cole so We did an episode with him on the podcast and I was incredibly inspired by this guy.

So he's done what I think is basically impossible.

If somebody had told me that, like 10 years ago, like hey, there's going to be somebody who is going to make a minor league baseball team have more followers on social media than the Yankees and, by the way, and all other MLB teams combined.

They're going to have like a 3 million person wait list and be selling out 80,000 person stadiums.

And that he bootstrapped the business with his wife to, you know, 100 million plus.

I just think that is like, that is playing business on like such hard mode.

That is like the equivalent.

If you're non-technical, that's the equivalent of rockets that land themselves.

It's to take a minor league baseball team that nobody gives a shit about, in a league that nobody gives a shit about, with players that nobody's ever heard of, and turn it into this incredible entertainment thing.

And the way he did it was just so like, I don't know, from the soul and passionate, right?

Like there's a lot of creativity in the, you know being basically a modern day.

Like PT Barnum, There was a lot of this like passion and soul to like the hustle to do this.

Like, you know, he's on the pod.

He's written four books behind him.

They do a show every weekend, you know, like they're traveling the world.

He's just doing everything.

And it's just like, man, I would, I would never, ever, ever be able to do something like that.

And then the last thing was like, I don't know.

He was just a sweetheart when he was on the pod.

He's such a nice guy.

So genuine.

I think Sammy told me like they foster like kids as well.

I was just like, geez, how good, like how good is this human being?

And I just feel like we are lucky that there's somebody as kind of creative and such a like force of creativity.

And as this guy like walking the earth, I think I even told him that on the pod, like yeah, I'm glad you are walking the earth, which I've never like felt the need to say to another man.

But I did that day.

We used to joke and have this concept of like the total man.

And it was like, what does it mean to be like a great man?

And he is one of the maybe three people we've had in the podcast that I would go in that category, where he's like I felt I was, like you are.

You are a very special human being and you are the epitome of what it means to be a man.

We should have just been like, can you lift your shirt up?

If you've got a visible ab, you're if you have visible abs, you are in the club, my friend.

Like that's the only thing that is like the fitness side is the only other part of the Total Man franchise that we don't know about him yet.

I think that you know we've talked about this podcast on living a rich life, which means like there's business, there's family, there's there's having a good life, there's treating people wonderfully.

I think that he is one of the richest people that we've ever had in the podcast in terms of a holistic rich life.

He felt like a very special person.

If you look through his Instagram, like he like pays tribute to his wife.

He talks about his team.

You see him like giving these inspirational talks to his, to the players, and I was just like this guy's got no flaws.

It's kind of intimidating.

The one little nugget that just kind of showed a lot was they don't charge, they eat the sales tax on ticket prices.

So they're like, it's $25 for a ticket, flat.

And it's like, okay, but there's always tax, plus tax.

He's like, no, no, no, we pay that.

We eat the cost of that.

It's like, at the scale that they operate at, That's just millions and millions a year, just so that the average customer, when they're checking out, feels like they were kind of taken care of versus, you know, being stuck at two, which is how you know Ticketmaster and these other you know things Live Nation, like when you go buy from them, you just feel like you're just being, you know mugged, basically at the checkout counter, right.

It's like oh, and then here's the service fee, convenience fee, parking fee and this fee, and like it's now triple the cost.

And I just thought like that little nugget of like how they – don't just leave money on the table, but they put money back on the table.

I thought told a lot about, like you know, actions versus words.

Everybody says they're customer friendly.

He also actually.

Who actually does that?

Very few people we made.

We talked to him.

We were like um, he made a comment where he was like whatever you see, that you've seen for predictions on how big our business is, it's much bigger and so, like i thought that was really cool too.

And he didn't even say it as a flex.

I think we like teased it out of him, but he didn't talk about numbers at all, other than that one comment and i thought that was really cool.

Yeah, that was amazing.

All right.

Next category we'll do is we'll do the one we were about to do, which was what was the biggest personal

Coolest moment in life.

Coolest moment.

I've got one.

So Sean organizes this thing where we go to Mr Beast's house and or his town and we like tour his property and play basketball with a bunch of successful people.

Last year, he had someone that was like the 90th richest person in the world.

He had all these powerful people.

He had Mr. Beast and Mr. Beast was giving us a tour of his campus.

So it felt like a movie studio.

And all of these guys there were trying to kind of be cool, a little bit imposter and not.

And like mr beast was was saying the most ridiculous things that you could imagine, like where you have this guy living in this home for one whole year and he can't leave the home until he loses a hundred pounds and he's like i spent this much money on this studio and like we're doing this and he's just saying like ridiculous stuff.

And everyone was trying to be cool, like yep, this is what it takes to be the best, totally get it.

And justly, jesse itzler, who was there, was in the back and he was like This is the craziest thing.

He's like, why isn't anyone calling this guy out?

This is the most ridiculous stuff I've ever seen.

I can't believe this.

How does one person live this way?

This is just insane.

And Jesse Itzler was like the most sane person there, which he wasn't like insulting Mr Beast, but he was like he and he was like a very reasonable person.

And Jesse Itzler, I think him and his family are billionaires or near billionaires.

He's very successful.

And we've met, Sean, a lot of people on the Internet who appear a certain way.

We've met him in real life.

And there's some oftentimes there's a gap.

Or if you do meet them in real life, you think I don't want to be like you.

Jesse Itzler.

It was one of the coolest moments of my life to meet that guy because he was better than he appears on the internet and he was very inspirational.

And he was like, can we acknowledge that this is just insane and ridiculous?

It's cool, but it's just like, this is insane.

And then there was a funny thing where, Mr Beast, he parks his car in front of the entrance of the building.

He drives his car over the parking lot and Jesse made fun of him.

He's like, dude, there's an open spot right there.

What are you doing?

And I just thought it was funny that he was like, A, teasing him.

And B, he was just... He didn't get swept up in it like the rest of us did.

No, no.

And it was so funny.

And we were talking about some ridiculous stuff.

Like we had a billionaire there who was talking about how aliens are real.

And he knows this because he hangs out with like White House people.

Like it was like pretty funny stuff.

It felt like... Did you see that new documentary, by the way?

No.

About that topic in particular?

I've been wanting to watch this.

Yeah, there's like a...

There's like a documentary.

What is it called?

Do you remember the name?

Let me pull it up.

When we were there, it was.

It was.

I don't know if I won't say who it was, but it was a very powerful person who goes tomorrow.

You're going to see a news story about aliens.

I know all about it.

And they're real.

Like he was talking about it.

Yeah.

It's called The Age of Disclosure.

I watched it.

Color me not fully convinced, but, you know, you should watch it.

Partially convinced.

Did you agree that Jesse Esler was just the man?

Yeah, so my coolest moment is also Jesse.

We didn't plan this, but I was at his house yesterday.

I flew to his house.

I spent all yesterday with him.

Um, and my coolest moment, uh, has to do with that.

So what were you doing with them?

Recording a podcast?

Sam's Sam's jealous.

You knew we were doing it.

Sam's coolest moment was meeting the guy and you just dunked on him, being like I hung out with him yesterday.

Well, he did a, he did a talk in Manhattan just the other day, but I already had plans.

So I didn't even get to go.

So it just shows how much I really care, but no, he was.

So, uh, so I just flew to his house.

And so, uh, so the coolest moment of the year, uh, All right.

So last year, this time last year, Jesse came on the podcast and he explained his New Year's planning process and philosophy how he attacks the new year.

And Sam, I don't know if you remember, but we were both pretty inspired by it.

And one of his core concept is this concept of a Misogi.

So he says, you know, the years fly by.

You know, if you ask me right now, what did you do in 2018?

I don't know.

I'd have to really think, how old was I?

Where was I living?

What was it doing?

Whereas what he does is he picks a misogi, which is a Japanese ritual of a challenge, a hard year defining thing.

So you'll always remember, oh, that was the year I hiked, you know, this, I hiked Everest.

That was the year I did my first Ironman.

That was the year I did XYZ.

And he could tell you 2015 2016, 2017.

You know 2015, that's the year that David Goggins lived in my house and I trained with Goggins.

2016, that was the year I lived with the monks.

2017.

That was the year I did my first whatever, and so after the pod i was trying to, i was like pretty inspired.

I was like, what am i gonna do?

And um, you know, jesse's really adventurous.

He's big into these like endurance races.

That's never something i've been like drawn to.

So i had the, i had the will, but i didn't have the idea.

And that night i'm uh, before i went to bed, i was watching.

I was on youtube and i saw this recommended video of this.

I don't even know why i clicked it.

It was like this dude playing the piano and it was this uh guy.

Who's?

He's this italian composer.

He's basically the most famous piano player in the world at this point.

Um, he's like a modern day composer and he was playing this song and he was playing a performance he did at the Steve Jobs theater, which was like 10 minutes away from where I was.

I was at my sister's house, 10 minutes away from her house where I was that night.

And I saw it and I was like, what if I did this this year?

Like forget business, forget it.

I was like, what if I, what if this was the year I learned, you know, I can't dance, I can't sing.

I've never played a musical instrument.

Like I don't have that innate talent, but like what if this was?

What if that's a thing I picked up?

What if I could just jam out on the piano specifically?

What if I could play this song?

And so, as you know, Sam, I've been practicing all year and I love the Instagram stuff.

I've been learning to play.

And.

But you know, the one thing I didn't do was, like the way Jesse's philosophy is, is that you, when you decide you're going to do something, you don't just make it a wish or like a goal.

You plan a date.

It's like I'm going to run this race on this day.

I'm going to take my kids here on this day.

It's on the calendar.

It's a thing I'm working towards.

So that was the one part I never did.

I was like, I don't know, what am I going to do?

A piano recital?

Like I'm not like seven years old.

I don't know what to do.

So yesterday I'm at his house and he's giving us a tour and I'm there to do a podcast with him another annual planning thing.

And we're walking by, he's like, oh, this is my favorite thing in the house.

This is a piano my mother gave me before she died.

And I was like, do you play?

He's like, no, I've never, nobody's ever played this piano.

Like, you know, since we got it, it's here, but I love it.

And in my head, I'm like, oh, this might be the perfect thing.

That was my Misogi last year when we did our annual planning.

We're doing it this year.

He doesn't know that he kind of triggered me to actually go do something.

So I was like, I'm going to do this.

So when we were talking about it, I go, can I show you mine, my Misogi?

And he's like, well, what do you mean?

I was like, let's walk over here.

And so we go, and I play this song.

Now, I'm playing this song.

Did he sing?

No, no, it's not a singing thing.

It's just a, it's just a piano song.

I'm playing this song.

And just the context here is like, I've been playing this every day at my house.

I play upstairs in my room.

And honestly, like nobody particularly gives a fuck.

Like my wife is like good for you, but can you come help with dinner?

Like, you know, like, you know, she's like in the middle of three little kids.

Like, you know, it's not like I'm getting a pat on the back for this thing.

My kids don't really care about classical piano music.

My wife doesn't really care.

I have never really played for anybody else.

So this is my first time ever playing for anybody and I turn when I was done and It was like the craziest thing.

So Jesse's there he's crying, his head of strategy.

There she's crying, holding the phone, and Sarah, his wife, who I'd never met she's the founder of Spanx had come downstairs because she heard somebody playing the piano.

She's like weeping.

It's going to be crazy.

It's all on camera too.

I happen to have a camera guy there because we're recording the podcast.

So basically, there's this full circle moment of Last year, he planted the seed.

I worked hard on it all year.

There was no real payoff for it.

There's no purpose for doing it.

I just wanted to do it.

And then there was this amazing payoff moment where they actually gave a shit about what I was doing.

They appreciated it.

They were like, that was amazing.

And I had never felt that ever.

And so for me, it was not only the coolest moment of the year.

It was one of the coolest moments of my life, if I'm being perfectly honest.

I'm a little embarrassed to say it, but it really was this incredible moment Like, hi.

And it was totally serendipitous.

I didn't plan for any of that to happen.

It's this song called, I don't even know how you say it properly.

It's Italian, but it's Nouveau Bianche.

I don't know how you spell this.

It's pronounced a second word, but I'll put it in the description.

That's awesome.

It's this great song.

And I was like, I was like, I don't know what's happening.

I don't know why everyone's crying.

I don't know what's going on.

But like, I feel like my parking pass just got extremely validated just now.

Thank you guys for that.

That is so cool.

What did they say afterwards?

Dude, he couldn't even continue the pod for like 20.

He's like, dude, I'm blown away.

He's like, I need like a minute.

And he's like, he was like, that is so cool.

He's like, you know, you're 37 years old.

You pick up an instrument like.

You can do that in a year?

He's like, if you could do that in a year.

And his son had come down to listen while we were doing it.

And he's like I'm just so happy my son saw and heard that because I hope it planted a seed with him of like yo, you can, if he can do that in 11 months or whatever, like dude, you could do anything.

Like anything is on the table for you.

And he was just like very inspired by it.

And I was like, here's a guy who I admire.

Like you and I have both talked about this.

Like he's our kind of like entrepreneurial North star, like a guy who lives a life well lived, all around.

You know four kids, beautiful relationship with his wife.

Does all these adventurous trips with his friends.

He's in great shape.

He runs a hundred mile marathons.

He's had incredible business success.

He's a great, you know, content creator.

You know, he's just a prolific guy.

You know, he's built brands like Zico coconut water and sold a company to Warren Buffett.

It's like, what more do you want out of life?

Right?

Like this guy's done.

He's played a game in a way that I would love to play the game, the game of life, um and so to kind of get like that moment with somebody who i kind of admire, that was that was definitely my coolest moment of the year.

That's really great.

That's a very yeah sean, i gotta say i, when i first saw that you were learning piano, i thought that was the coolest thing i had ever heard about you.

So i think there's something no, genuinely like.

That's not to dismiss any of the other stuff, but i was just like When you're a creator online, as we talked about earlier, people make these assumptions about you.

They kind of sometimes dictate what is in your orbit.

And for you to be like, no, no, no, this is something I want to learn.

I might not even be sure exactly why, but I'm going to go do it.

It's not what people expect.

And then to do what you just did.

I actually think that is so cool.

Yeah, I commented on this podcast.

I was like You know, all this business stuff is great, but the piano thing it's for some reason oddly inspiring.

Well, the funny thing is like in the moment, it never feels that way.

Right.

Because like I'm walking out of my piano teacher's class.

There's only like our Brandon.

Good luck, buddy.

You know, there's only seven year olds there.

You know, their parents are there.

They're looking around like, where's your kid?

I'm like, no, no, it was me.

Like I was the one getting the lesson, the piano lesson.

And it was just kind of an odd thing to be doing pretty regularly.

But again, trusted my gut, went with it, just leaned into it.

It was like, all right, I'm having fun.

So I'm not forcing myself to do something I don't want to do.

Why does everything have to be with an agenda?

And, you know, this kind of like validated, like, yeah, just keep doing that.

Good things do happen when you as you keep doing that.

Don't worry.

Like you'll also get the rewards you seek in life, even when you're doing the stuff that seems like it has you know no rewards.

You're just doing it because you like it.

Next podcast.

I want to know all of what it was about hanging out with him.

Yeah, we'll do.

What about you, Steph?

My coolest moment.

I was in between two.

I did a big trip to Africa.

And if you haven't done gorilla trekking, it is one of the most incredible things I've ever done.

Gorilla trekking?

What did you say?

Trekking.

Yes.

Yeah, trekking, tracking, you do both.

Are you tracking down a gorilla or are you doing something, you're trekking?

There's families of gorillas that live.

We did it in Rwanda, they have it in Uganda not many countries other than that and they're wild.

So yeah, they live in the wild and they move every night.

So they have these trackers who go out every day and try to locate them.

And then you trek through the rainforest truly like there's mud up to your knees at points, and trying to find them in Rwanda.

But super cool experience.

But my actual answer is going to see the World Series with my dad.

He's been a Blue Jays fan since before I was born.

The last time they won the World Series was in 93.

They had a double year, 92-93.

And then I was born and ruined it all.

And so he, he kind of makes fun of me for that every year and is like also, the person who goes and is like, is their year, is their year, they made these trades watches every game, you know, 160 plus, and he's also where i get every ounce of my cheapness from, and so he would never ever, buy tickets for himself.

And so um yeah her, you know, once they hit the world series, i flew home, bought him tickets for game six when they had their first chance to win, didn't win, then yielded it for game seven.

Totally worth it.

Like, can't really think of a better way.

Oh, you did two in a row.

That's awesome.

Yeah, I mean, I wish they had won either of them so close because they lost but um yeah, that's amazing, that's it.

That's a.

That's a great thing to do.

That's a really great thing to do.

I could see why all NBA players like their first thing is like I bought my mama a house.

It's like I think there's probably like very few things you could do that will, like you know, feel as good as like taking your dad or your mom to like To do something that they would love to do they'd never do for themselves.

Yeah.

And like, you know, get to do that with them when you're a grown up.

Do you guys want to combine frame breaking person and favorite guest?

Okay.

What you got?

So, well, do you have a favorite guest?

Well, let's explain what frame breaking is.

Okay.

So me and Sam use this term a lot.

Frame breaking.

Everybody walks around with some frame and frame is like a border, right?

And everything that's inside the border is what you sort of, I'm used to that.

I've seen that.

I expect that.

That's what's in the picture.

That's how wide my lens goes.

And then occasionally, you'll meet these people who will just completely break your frame and it's like oh, i didn't like.

It's like, imagine a painting where somebody starts drawing past the frame onto the wall.

You're like what, you can't go out there.

And so this is maybe somebody with like extreme ambition, or they live life to the fullest in this way that you don't really do, or they're really you know, really intentional about their time, or you know there's these things that people do that you thought you knew what level 10 looked like in that category and then you realize oh, what i thought was a 10 is a 7.

And now I know what a tent looks like.

I actually like somebody's broken my frame.

They've turned the volume knob up further than I thought it could go in that aspect of their life.

So that's the setup.

Who is your frame breaking person?

So there's this Aristotle quote that I've been thinking about for like a year now.

I think last last time when we did this, I was saying I was trying to use my phone less.

And there's Aristotle quote.

It says excellence is never an accident.

It's always the result of high intention, sincere effort and intelligent execution.

And the reason I think about that all the time is because I don't know about you guys but like, if I'm on a Zoom meeting, I'm probably browsing the Internet.

If I'm watching TV, I probably have my phone up and I'm doing something like.

There's this constant pattern of interruption and never focusing on something.

And it's kind of been tearing me apart.

It's kind of making me gone mad.

And so I've been working so hard on being intentional about my attention and focusing on excellence, but in a very few amount of things.

So just picking a couple of things and being great.

And we had this guy.

I don't think you were here Sean, but we had this guy named Will Godera who wrote this book called Unreasonable Hospitality.

And the story is if you guys have seen The Bear, it's one of the inspirations for The Bear, the TV show.

But basically the story is that he owned this very famous restaurant in New York called Eleven Madison.

And they're famous for going above and beyond.

For example.

Uh, someone was wasn't it the top rated restaurant in the country, or what's like the claim to fame.

It was the top rated restaurant in the country in part because the food was was special.

It was a michelin star place, so it was like fancy.

But the other part was that they were known for being unreasonably hospitable.

So i'll give you an example.

They had this couple or a family from europe.

Uh, come to the restaurant that they had planned for months to attend And Will or a waiter overheard them say we're leaving tomorrow.

But the one thing we didn't get to experience was a New York street hot dog.

And so Will has this guy at his company who they call them the dream weaver.

And his only job was to make dreams come true to their customers.

And so this guy ran outside and he bought a street hot dog or a couple of them, and they chopped them up and put like a cute garnish on it.

So it sort of looked like it was a fancy restaurant food, but it was actually a street hot dog.

And they said right, we heard you talk about you wanting a hot dog.

Here you go.

Your dreams have come, become a reality and that's rooted in like unreasonable hospitality, but the reality is it's about being excellent and he gave this amazing spiel.

And it's crazy, this did not i think this hit on spotify, but it did not hit on youtube.

But this was the best podcast i'd ever recorded based uh, just of what he told me, of the idea of.

He was like we are going to go above and beyond and we are going to be excellent, and i found that to be kind of overfilling my cup, not just in the business category, but in life of just pursuing excellence for the sake of just trying to be great at a couple things.

And I found that to be a very inspirational book.

And I find him to be a very inspirational person.

He kind of broke my frame.

That was awesome.

That was an awesome rant and summary of it, too.

I love that.

Thank you.

It was awesome.

That scene in The Bear is the best.

They recreated that idea in The Bear.

And it was like, Peak television.

It was the best.

And then my favorite guest, sleeper of a guest, Sean Frank.

So Sean Frank's this guy who's the CEO of Ridge Wallet, which is a popular wallet company.

Guys, this guy's so funny and so interesting Sean, because he's kind of like you and I like he's silly and everything.

But his silliness is that I think he's actually a very serious person.

And I found this blog that he wrote last year.

Listen to this.

He said, my goal is to sell Ridge for a billion dollars in the next three years.

I have to time it right because we're coming out of a bubble and interest rates are going to go up.

And then they're going to come back down, hopefully by 2025.

And then by 2026 or 27, I'm going to sell this company.

And I just thought it was hilarious that this guy like called his shot like that.

And if you listen to the podcast that we had with him, he was a very direct person.

And I find that to be incredibly refreshing.

So I think Sean Frank was my favorite guest.

He's a great follow on Twitter as well.

Dude, he's like a wholesome guy, but he's very blunt.

And I find that to be a very cool combination.

Yeah, he's funny.

So that's my favorite guest, my favorite frame breaking people.

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Steph, you want to go next?

Sure.

Have you guys heard of Fiona Oaks?

No.

Who is that?

Frame-breaking person.

Okay, so I discovered her because I've gotten into running lately and I watched this documentary.

Can you spell her name?

Fiona Oakes.

O-A-K-E-S.

This documentary was about her.

It's called Running for Good, the Fiona Oakes documentary.

Okay, so get this.

She has been a vegan since she was six.

She lost her kneecap at age 17 due to an injury and medical complications.

Yet...

She is this crazy marathon woman.

She lives in some farm area in England.

She just runs a crazy number of miles.

Doctors to other patients who have lost their kneecaps are like, you can't even walk downhill.

She's running these marathons.

She has multiple world records.

And the craziest part is she does all of this because she just loves animals so much.

She didn't grow up running and like, you know, enter competitions.

She wasn't on cross country.

She just one day realized, oh, I'm pretty fast.

And then started entering marathons to win money so that she could go fund her farm business and take care of her animals better.

So this woman was just like, The most frame breaking because I'm just like, who is this?

And how is she running 248 marathons?

That's like 624 minutes per mile.

And she just does it like no one knows who she is, until you know, someone discovered her and they're making documentaries about her.

But she just just the craziest combination of things.

And she's just like she's a world record holder.

She ran marathons before she lost her kneecap also or she started this hobby after?

I don't know how much running she was doing before the kneecap, but all of the records, all of the marathon wins.

She lost a knee at the age of 16.

Post, yeah, post kneecap.

And she's 56 now and she's doing this shit.

It's pretty wild.

Yeah.

It's crazy.

The documentary is funny, too, because they start out and they don't share any of her times.

They're kind of hyping her up and you see her.

She looks kind of old and you're like, OK, sure.

You know, like she might be fast for a 50 year old, but she's not.

No way she can be that fast.

And then you actually look up her times and you're like, holy shit, this woman is a legend.

I don't know how these guys run so much.

The more I run, the more hurt I get.

She doesn't have the kneecap.

That's the trick.

Are you not willing?

Remember that guy with the fake legs who ran the 400 meter in the Olympics?

Yes oscar, is that legal?

Yeah, he also went to jail for like, killing his?

Yeah, he killed his wife.

Yeah uh, i always thought that was nonsense.

Why do these guys broke a frame or two?

Well yeah like, why do they get to be in the olympics like?

They don't?

Like, they don't have any in the normal olympics.

Yes, he was in the normal olympics, which is nonsense.

He doesn't have any like legs that can get full of lactic acid.

They're like metal legs.

Like, why does he get to go like?

You know what i mean?

It seems ridiculous.

That is ridiculous.

It's ridiculous.

I'm enraged.

Yeah, it's ridiculous.

Fiona Oaks, what's the documentary called?

It is called Running for Good, the Fiona Oaks documentary.

Did you have a favorite guest also, or do you want to just use her for both?

No, I've got a favorite guest.

You mentioned him before, so maybe he's your favorite guest.

He's recent, John Morgan.

I listened to a bunch of the episodes and there were people like there was the Exploding Kittens guy, there was Eric Ryan, there was Sheil.

All of those people I went into the episode expecting to like.

I went into this episode expecting to not like John Morgan.

And he just was incredible.

The number of businesses that he's gone into whether it's his attraction stuff apartments, ad agency tech company is insane.

But it was his one-liners that I was just like, dude, this guy simplifies everything.

All of this shit that us tech company people overcomplicate into just the best lines.

He's like, I don't hunt deer, I hunt money.

When he's talking about his URL, he's like, I went for...

Justice for all.

Yeah.

He was like, basically, I was worried people couldn't spell justice.

For the people.

Yeah.

He went with for the people.

He also had this line where he's like, I'm good at sharing the profits.

And I was like, you know what?

There's actually something to that.

So many people are so bad at spreading the wealth.

And he's just like, look, I treat my people good.

I share the profits.

So he got on.

Yeah, crazy number.

He got on and sharon and i i think i don't know who booked him, but we didn't know, i don't think we entirely knew what we were getting into, because he's now he's on this tour but uh, like there wasn't a lot of information about him and we i don't think we knew what we were getting into.

I know i was going into it like we'll see the first sentence he goes, i got these attractions, this upside down museum, and he goes and let me tell you it, Prince money.

No, he didn't say money.

Prince.

Yeah, he goes, with Prince.

He said the F word so hard.

And we don't say the F word really on this show.

And we both, like, eyes went open.

And we were like, buckle up, baby.

We are going on a roller coaster.

This was something.

And there was 20 lines.

And I showed it to my dad because Morgan & Morgan, I think, they have an office in Missouri.

So that's where the commercial is.

And he was like, you can't air this.

This is going to ruin this guy's reputation.

And I was like, I don't know, man.

I think he knows what he was doing because I showed up.

He said the F word literally 15 times.

Another time he goes, do you know why we win?

Our competitors, they're lawyers.

They're shit.

And like and then he goes and then he goes there.

And then when we win, we go into a case and they don't want to settle.

But six weeks in, they see how serious they are and they want to settle.

And I go, you know.

And I take him for everything there were.

He was a very vulgar guy.

If I was a Netflix showrunner, I'd just be like I need to follow him around because I'm going to build Ari Gold-like characters around this guy's personality and the way he rolls.

And we go, why are you even... We said, why are you doing this?

He goes, because it's good for business.

I also love that he's not... I mean, he built a tech company, but he's not in our tech world.

So he'd be like...

I was on the Business Insider or he'd be like Sean.

Are you aware of this thing called first principles thinking?

And I was like, this guy's a G. He said my whole thesis was what would Google do?

So that was awesome.

Sean, what about yours?

Yeah, I mean, he was amazing.

Also, I would say one other thing about him, which is I had this opinion.

I don't know from where it came from, but just my default, never even thought about it again, was personal injury lawyers, sleazy ambulance chaser, blah, blah, blah.

And it's like, wait a minute.

So what's his actual story?

His brother gets basically paralyzed on the job, has poor representation.

He gets mad about that, decides i'm gonna go to law school, become a personal injury lawyer to fight for you know, fight for that.

And it's like wait yes, it's basically people who are.

You know, it's you're fighting for the common man against large corporations for the most part.

And it's like i wonder why this isn't seen as a more, as a more noble profession.

Like obviously there's aspects to it.

I get why it gets that bad rep, but like i don't know, i i think it's.

I think the public opinion is far overrated on negativity towards this profession in this way.

I totally agree, man.

Have you ever known someone who got hurt at work and you're like, this is a travesty.

These insurance companies should be paying you this much more.

There's nothing you could do.

I've been in a car.

My car got messed up.

And I was like, this car is worth way more than you guys are telling me, but I just got to take it.

Now, imagine if this was your mom who got hurt.

Exactly.

Yeah.

I think most of his cases are against companies like insurance companies.

Right.

So it's it's a little weird that they have their reputation.

All right.

I have a frame breaking person that you guys probably don't know.

Her name is Kristen Berman.

And Kristen is somebody I met at an event.

I went to one of that's I lied.

I did go to one event this year.

I went to the dialogue conference.

And honestly, I didn't love the conference overall, but there was one conversation I thought was really great and it was this conversation um, where kristen was there.

She is partners with dan ariely, so if you've ever read the book predictably irrational, he's like one of the famous behavioral economists in the world, like business partners or like married.

They run irrational labs, which i think is like a consulting.

So companies come to them and you know like panda express will come to them and be like hey, we want to provide healthy options, but like, how do we frame this in a way that will be like, you know, people make the choices that they want.

Or how do we get people to choose to insulate?

How do we get people to choose to insulate their water heater?

Cause it's good for the environment.

It'll save them money, but we can't seem to get them to do it.

What are, what are ways we could do that?

So they'll go to them and try to say, you guys understand how people's consumer brains works.

What are ways to do this?

So anyway, she's telling the story and um, The reason it's a frame-breaking story is she made some money.

So let's just, I don't know, I'll just make up some numbers.

But she made a couple million bucks, let's say.

And at the time her and her husband and I think maybe kid, but her and her husband were living in, let's call it, a two-bedroom, like a two-bed apartment.

And what everybody I know does is you make money and then you upgrade your lifestyle.

So you go from a two-bed to a three-bed to a four-bed to a five-bed, whatever.

And then soon you're at the Sam you talked about like a 17000-square-foot mansion and you know the more you keep going and that's how they use their money to improve their life.

She, being a behavioral economist, had a very different perspective and it was not out of like trying to be a good person or do something different.

She was just like well, this is what the data tells us matters.

And so she was like uh, what she did was she kept the same apartment she was in, but she bought the three or four units right around her and created a basic compound and then invited people who they really liked.

So you know people that they basically built their own little micro community.

So it's like who would be an amazing neighbor?

Like they rented.

She rented it at a below market rent and she's like you know, i just you know it didn't even matter.

We're not trying to make a rental property and get this cash flow.

I'm not trying to upgrade my own lifestyle, live in this baller place.

No, like the.

Basically, the data says that, like the people you have around you, your close knit community is the number one thing that will improve your happiness.

So we did that.

So we bought these other units.

We now have people you know like kind of like, who are friends or friends adjacent, like apply to come in.

We're really rigorous about who gets in.

And then when they're in, you know they're a part of our life, you know like we see them all the time and it's been amazing.

And she wasn't even really like preaching about this, but I was kind of like, Wait a minute.

That sounds simple.

Sounds simple to do.

I don't know anyone who's done that.

Do you know anybody?

We know a lot of rich people.

Do you know anybody who's actually done that?

Well, I kind of did that.

Me and Neville bought homes together.

Bro, you moved away.

Yeah, I moved away.

The opposite of doing that.

I moved away to be closer to family, but I will say we were intentional about it and it was freaking awesome.

Yeah, you might be the only person I know who's also kind of been like I'm going to live on the same block as this person and that's more important than getting the bathrooms with the marble and the way we want.

You know how most people, I think, pick and choose what they're going to do.

In fact, most people I know who make money, they isolate themselves.

They move into more private communities, bigger and bigger places with bigger and bigger lots.

And they basically like create a pocket of loneliness because maybe their family, they can't afford to live right next to them or their friends aren't also in the same.

You know, either category, or looking to move at the same time.

And they move into a place where other people are used to not talking to each other.

And it's like isolationist.

So I just thought this was amazing.

It kind of broke my frame, but it was very inspiring because, as much as I'm inspired to learn how to make money I think Morgan Hounsell said it best like you, can either use money in one of two ways.

Number one as a tool to improve your life or number two as a measuring stick to measure your self-worth.

And I.

You know it's so easy to get caught in the money as a measuring stick thing, but money as a tool to improve your life, that means you got to learn how to spend it just as much as you got to learn how to make it.

And so he's.

You know this.

This was an example of like how to actually spend money to improve the quality of your life.

We should have her on.

This sounds great.

Yeah, we totally should.

She was awesome.

That's cool.

That's a great one.

I'd never heard of this, this person.

That sounds badass.

Does she have a book or anything?

Or is her, or Dan is like... Well, I think Predictably Rational was kind of like part of their...

I don't know.

I don't know too much.

But yeah, let's have her on.

She's gonna be great.

This is for the folks out there who have a business that does at least $3 million a year in revenue.

Because, around this point, that's when you're able to look up after being heads down for years building your company.

And you realize two things.

One, you've done something great, but you're still alive.

And two, you look around and you realize, I am all alone.

I've outrun my peers, which means you're now making $10 million decisions alone by yourself.

And that is when mediocrity can creep in.

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We solve this problem by giving a room of vetted peers of other entrepreneurs who are going to hold you accountable, call you out on your nonsense and help show you the way.

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And they're hard to find.

The biggest risk is not failing.

You have a company and it's working.

You're going to be fine.

But the biggest risk is waking up 10 years from now and saying shit, I barely grew in business and in life.

And for people like you who are ambitious, wasted potential and regret is what we want to help you to avoid.

We have made so many of these groups and we have a thousand plus members.

And I know this stuff actually works.

It can change your life.

It changed mine.

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Joinhampton.com.

And what's your favorite guest?

Favorite guest was Nick Mowbray.

So this is basically the closest person to Elon Musk that I've ever met.

Not like closest as in like friends, but like closest, like, oh, wow, you're basically like Elon.

He just, you know, Elon was born in South Africa.

This guy's in New Zealand.

And he went into the toy industry.

And if you haven't heard it, the pod he did, he does very few podcasts.

I think when I was doing research, it was like one interview from like 15 years ago.

It was the only thing I could find.

And, um, it took like 30 emails to get him to come on.

And he was amazing, such a good dude.

And his story is like like a movie.

Um, you know, literally like sleeping in a bush.

Uh, you know, in China trying to, trying to make it happen.

Like it was just unbelievable.

Like the sort of sleeping on the factory floor mentality, the level of grit, living off a dollar a day until they made it.

And now, you know, the brothers are the wealthiest men in New Zealand.

They're built self-made billionaires own the whole thing.

Not only built one of the biggest toy probably a top three toy company in the world sitting in New Zealand, but also built, like you know, a top three diaper company.

Also built a top shampoo company.

Like this guy is insane.

Like you know, he was saying how when he he got like uh, you know that, living off a dollar a day in china eating mcdonald's, you know like kind of off the dollar menu type of thing, got you know caught up to him and he had to like get his like small intestine removed or something.

And he's like you know, when i was in recovery, sitting in the like hospital, i decided like i was watching tick tock and i decided like i'm gonna build one of the biggest brands on tick tock and he built like the biggest diaper brand as a side quest using tick tock.

And i'm like this guy Elon is an animal to the point where, after the pod I don't think we caught this on the pod, but he said something like I asked him.

I was like dude, you're like Elon.

Have you ever met Elon?

He's like, no, I've never met him.

I would love to have met him.

He's like you know, at one point me and my brother, we were the largest shareholders in the world of Tesla stock.

He's like, I'm a big fan.

And I was like, what do you mean?

He's like, yeah, I think we own, I think they own like, I forgot to say 1% or 4% of Tesla.

Just personally, they owned it.

And he's like yeah, we you know.

But then when COVID hit and like the world stopped and the factories had to shut down, we didn't know we were at such a huge position.

We, you know, we reduced during that time.

He's like huge mistake.

We left like $15 billion on the table by not holding for the next five years.

And he's like um, but to the point where his brother like flew to California and installed cameras on buildings that had an angle at the Fremont factory.

Cause they were like, this is such a huge position.

We should monitor the factory production.

And I was like, this is the most high agency person I've ever met in my life.

I was very, very inspired by Nick Mowbray.

It says on Wikipedia that they're both they're worth collectively 20 billion dollars.

I didn't realize I thought that he was a billionaire, like one billion.

That's incredible.

No.

And now they're like 3D printing houses like they're doing crazy, crazy, crazy stuff.

And the base is just the toy company.

Like that was the foundational of the wealth.

Yeah.

That is so insane.

When you hear these people who have side quests that are like orders of magnitude bigger and better than anything you've ever built.

Yeah, it's wow.

Wow, that was awesome.

I knew the story, but I didn't realize how successful they were.

That's really amazing.

Okay, we probably only have a couple more that we're going to do.

Which one do you want to do?

Biggest change you're making and then the meme of the year, maybe?

Yeah, what's yours?

What's your biggest change?

All right.

So uh, after hanging out with jesse, i was like what's my new misogi gonna be?

And we were both talking about um, he was.

He was he's written a lot of books, but he was like dude honestly, he's like i feel bad.

He's like i don't read that many books.

He's like i don't even read five books in a year.

He's like i can't believe it.

Ever something.

I really feel like i should change and i was thinking about this.

I've thought about it very similarly and i was like you know what, all right, and so i was like Took my phone and I just deleted X, deleted Twitter, deleted YouTube, deleted Reddit.

And I was basically like I think I can give myself back 10 to 15 hours a week of time and mind space.

And I'm just going to not consume any social this year.

I'm just going to get off social completely.

I'll still post.

I'll have my team like post stuff like I can create for social.

I just can't consume.

I call this the Luka Doncic trade.

It's like what if I could get the best thing back, which would be like reading some of the best books of all time, and I'll give up some crappy assets.

I'll give up some problem riddled assets, like all these different social media apps.

And so that's my trade I'm making for this year.

Damn.

When did you make the change?

Delete the apps?

On the flight back.

Okay.

So how many days ago?

I was like, how's it going so far?

It's my change for next year.

I started early.

I used to use social media just like you guys yesterday.

I know exactly how you feel.

I can't wait to look down upon people who use social media.

Imagine how self-righteous I can be.

That's a great move.

Last year I used The Brick for it, or I think it's called Brick or The Brick.

It was really helpful.

And I actually don't have social media on my phone, but I do use it on my computer, which is not good either.

But that's a good move.

Yeah.

You already do this.

You read like 25 books a year and I think you're very like... I read a lot of books lately.

Putting your phone in a box.

I think you're very self-actualized in that, whereas I'm still like the mouse or the rat, like pushing the pedal trying to get a pellet of cocaine out of the thing you know.

Having a second kid has reduced my reading to like close to nothing because like I get up extra early and I go to bed and I'm like That makes me feel better.

I have to go to sleep.

No, so I haven't read a full book in months.

I'll get through something and I'm like It's taken me a month to read this thing because I basically have to get up at six and I'm like at 10 I have to go to sleep.

I'm so exhausted.

So yeah, having kids has basically ruined, a second kid has ruined my reading.

Wait, what are we doing?

Habit or change?

Change for next year.

I you're not gonna see this Sean, but lately I've been going a lot harder on Instagram and Hampton is gonna be.

We have this like YouTube channel called money wise and we're gonna rebrand it and call it Hampton, and we just rented a new office down the street from my current office and it has seats for 60 people and a big studio, so I'll be recording this from that new studio and we're gonna be creating a new YouTube channel.

I'm gonna be doing a lot more Instagram content and i feel like the other day i did a video and i was like recording and i'm like so i talk about this on my page and i'm like oh, my god, that's like such like a boomer.

I can't believe.

I just said that uh, but i, i i'm gonna be going a lot harder on um content and it's gonna start with me writing are you doing this to grow hampton, or are you doing this because you're like i want to be influential or i love creating content?

What's what's the what's the true why?

On this one Well, I started my career because I enjoyed creating content.

And then when it became a little bit of a job, I disliked it as much.

And so I put it away for a while.

And then I was like, look, the best way to grow my company is just to do this thing.

And I started like doing it as a job and lately i've been doing it and i'm like i love this, i love writing and figuring this out, and so um, i've been doing this stuff on instagram now for only about three or four weeks and i've got millions of views and i'm like this is actually a fun little uh game to figure out and i enjoy like can i, can i grow hampton via content that isn't slop?

And uh, i've enjoyed that.

So that's what i'm.

That's my big change uh, this year.

Another simple change is I've been doing it the past month to prepare for the new year.

I get my workout.

My workout is finished at 7 a.m.

I'm done by 7 a.m.

And I know that, again, we're doing like self-righteous stuff here.

But I hate getting up early.

But I love having gotten up early.

And it's been a huge difference in just my time.

Yeah.

Saul Hill had this great quote.

He's like, I don't know any loser who wakes up at 5 a.m. to work out.

It's like.

It's kind of true, right?

Have you ever met a loser who does that?

No, like being at the gym at 6 a.m. and done at 7 a.m., you're like, it feels amazing.

And it's so hard to do, though.

Do you think you can sustain that one?

Well, I have to because it's my job to my eldest kid.

I get her out of bed at 7.30.

So if I'm going to exercise, it has to be done by 7 or 7.10.

And so I've been doing it now for 30 days.

And I think I can say, you know, the secret is very dumb.

The secret is you have to go to bed at 10.

If you're in bed by 10, this is easy.

That's that's challenging to do.

But you have to be in bed by 10.

Right.

Every time I wake up at 5 a.m., I'm like, this is amazing.

I get so much done.

Why don't I do this every day?

And then a year later, it happens again.

My biggest change is maybe kids.

We'll see.

I'm feeling nervous about it.

Do you guys have any advice?

Is this an announcement?

Are you announcing it?

No, no, no, no.

Sam, are you going to ask me if I'm pregnant?

Are you pregnant, Steph?

No, to be clear, I am not currently pregnant.

We have not started trying, but it's on the radar.

Do you want us to give you...

Tips?

Like tips on how to be a pregnant woman?

No, not tips.

More like what do you feel great about with kids?

What makes you like, I don't know.

I think there's a lot of, especially when you're a woman, you have to like actually you know grow the kid and then you have to like provide for the kid for the first few years in ways that men don't.

It's a little daunting, but I love hearing from both men and women like the best parts of having kids, because I feel like I don't hear those.

Sean, how do you talk about this without saying the most cheesy like advice?

That's the problem.

It's every cliche, everything you've already heard, but it's actually true.

So that's why it's hard to, you know, it's like you feel lame even saying it because it's and it's so obvious to you when you're in it that like you know there's like whatever i thought life was before this was just like you know pre-game material for for the real game and that's that's kind of how it feels um in many ways like level of intensity level of like you know like love like all like a sense of purpose like but i would say like the good thing about little kids because me and sam both have little kids sam's are a little younger than mine so he might not even be fully in this phase yet yeah like my eldest is two by the time your kids are kind of like three four they're talking they're walking they're like they have a personality like they're it's a whole deal and um they're just like a little joy machine so imagine having like a jukebox in your house and every time you go you push the button and like your mood lifts and the reason why is because Kids are experiencing everything for the first time.

So you get to experience everything for the first time, with them being the excuse for you to like actually indulge it and actually care and be like your own version of, like a little kid.

And then there's also, like these incredibly satisfying moments, because it's like they are, you know, like whatever you feel about, like building a company or building a product.

The truth is like the ultimate product is this little kid you made and you get to shape it, and you get to see it grow and you get to see like all the amazing things happen.

So take any of the feelings you've had out of like entrepreneurship or creativity or creating and now like add some like 3000 years of biological, you know, hardwiring to love all those aspects, you know, at a much higher level.

At this stage.

When I see like Instagram stuff of like the dad coming home from the military and hugging the kid or whatever, like things like that, I cry.

I get so like emotional by it.

I was I hold my I put my eldest to bed at night and like she lays on my my stomach and I'm like.

This is you know, like you ever think about, like when your parents die, Like how, like if they go to heaven, or if like, you'd like think about them, like what age will you remember them?

And I with my little girl every night.

I'm like this is perfect.

I will remember this for forever and it's so important to be present Because this is.

I was like when I feel her stomach on my chest.

I'm like this is peak happiness.

I have never felt this good and I get to experience it every single day and it's very special.

I think that for a lot of men, You don't love your kid right away.

And it takes a little warming up too.

And I'm at the phase of my life now where I'm like... I say this as a joke, but it's sort of real.

Where I was like, when I got married, I felt like I'll kill someone to protect you.

And then when I had a kid, it was like, I will die for you.

And that's a very weird way to think of it.

But it is so fun to be or not, I don't know fun.

It feels so great to just know I'm willing to dedicate everything I can to this thing.

And it feels really good to feel that way, and the downside and the upside are both the same.

The downside is like oh my god, this is a lot of work and I don't have control over my time or my schedule the way I used to.

And for people like us who are like wow, there's always more projects I want to do and things I want to learn and stuff I want to go do and all of a sudden it's like oh, I can't, I don't get to.

You know, like I don't get to do that.

It's not my schedule anymore.

That's the worst part of it, for me at least.

Like unless, like there's like a health issue or whatever like that's the worst part of it on, just like normal life.

But also the best part of it is like, it's not about you anymore.

It's like actually, all the problems in your life, all the bad feelings you had, was like over, like just an over importance of the self.

And so the thing with kids that's great is like it's about them now.

And so you get like the highs from that, but you don't really get the same amount of lows, because you don't have that sort of self rumination, self like indulgence of like all the little things that bother you in your world, because it's really not about you anymore, you know.

Totally.

Yeah, I had a friend who had a kid recently and I visited her and she was just like your emotional spectrum is just stretched, but in the most beautiful ways, because you just yeah, you're responsible for this being.

When she was like walking out with her kids for the first time, she was like I've never felt more stressed because I just saw all the things that could, you know, maybe harm my child.

But at the same time, like you're saying, it's more of like a, it's like a new set of emotions.

It's maybe not as self-centered.

It's just like a more interesting thing aspect of life.

That like, if you don't have kids, you're never going to get to experience, is my sense.

I haven't had them, but like that's i.

I find that a good way of putting it.

Like oh, there's like three new colors you didn't know about.

You know, there's like, there's like this whole other thing you get to see, and i hate saying that.

I agree with you.

I hate saying that because when people don't have children, it's like it's an not a reversible decision.

So I don't ever want to make someone feel bad.

And, you know, so I don't love talking about that.

But I do feel like it's sort of like the first time I've ever felt like my, my purpose in life has is being fulfilled.

Like you think that way about work sometimes and then and then we had it and i don't i hate being high and mighty and shit uh, but you like have a kid and you're like oh, this is like, this is the like, because this is why i've tried to impress a girl and so she would like me and then i could reproduce with her.

And now i have this thing and it's like i am now connected to the 20, 50 billion people before me and it feels kind of special.

It feels very strange, but it's special.

Yeah, it is hard to talk about because it's just you feel, you feel lame and cheesy and you don't want to like, it's just your personal experience, you don't want to influence others, but like when you ask, you're like oh, like i think i won, i'm kind of on the fence, i want to hear about it.

Then like okay yeah yeah, permission to be, permission to cheese.

Well, we'll end on a light note.

We have favorite tweet slash meme of the year.

What do you have?

Let's start with steph Guys.

Mine is boring, but I just loved the May I Meet You meme.

It was so good.

What is this activist investor doing, giving dating advice, and just the versatility?

Can you give us a play-by-play?

You, as a woman who's also in business and tech, you get on Twitter, you see this happening.

What was going through your mind?

I thought it was truly hilarious because I think also I don't know as a woman there's So many times when, like men think that they know what women want.

And like, I'm sure Bill Ackman is a catch.

Like, I'm sure he's also like six feet.

Right.

Like he's got a bunch of money and like you know, he's going up to these women saying like may I meet you?

And he's gathering that that is what is happening.

You know the defining action that the women are liking.

Steph, so you saw that advice.

What would your advice have been?

If Bill Ackman, he meant well, right?

He was like, I heard that it's tough out there for young guys.

Here's a little bit of advice.

If May I Meet You was wrong, what's the right advice?

I feel like, well, I mean, he's right that you just got to approach a girl, right?

Because girls like confidence.

But I also think girls like humor and like you knowing... you being authentic.

And so even just going up to a girl and just being like Hey, like I'm really nervous, but like I got to talk to you,

This is not the best pickup line, but I just feel like you just walking up to a girl is what probably nine out of 10 guys will not do.

If you happen to say, may I meet you?

It's probably fine, but I don't know.

Just be natural.

I forgot what it is, but Lil Dicky has one that's great.

I wish I had this back when I was single.

It would have helped me, but he's like, oh, I have the perfect pickup line.

He would go up to a woman and he'd be like what's your, what's your availability as far as being hit on right now?

He's like she would laugh and she would know my intentions and then like, i gave her it out and i gave her it in and i, like you know he's like, he's like it works every time.

Do you remember when you guys uh, sean or whoever um was screen sharing?

I just sent an example of one, but the the best content on social that i'm following this year.

Do you remember sean, when we talked about cinematic content?

I think we talked about um creator camp.

Is that what we talked about?

Yeah, So like, here's just one example of a podcast, but I can also do a few more examples.

But that's just one example of a podcast.

Who is this?

Mark Brazil.

Have you seen this guy's podcast?

I've seen this because it stands out, right?

Oh, my God.

It stands out.

It's like hostage podcast. negotiation situation.

And so we've talked about cinematic content.

So we talked about this company called Creative Camp.

And I'm noticing that like if you guys follow like these, there's a bunch of 22 23 24, 25 year old kids making like content that is not just like the talking head videos.

And it's beautiful.

And it's starting to transfer over into like podcasting, which is Normally, they don't do this.

And Chris Williamson has done this with his sets for Matthew McConaughey.

And I'm noticing that this type of cinematic content, where it's a beautiful background and it's not just I don't know your phone, it's way more popular.

And I love it.

I love this stuff.

I'm loving internet content at the moment because of this trend.

So not a tweet or a meme.

You said yeah, you're right, you did say meme of the year, but i think it's cool and you're right.

Dude, i don't know, do you pay attention to memes?

I don't pay attention to memes.

Anything's a meme these days guys, but it's always like a meme.

It's not like a long lasting thing, it's just like whatever was like the drake video, like the drake video or like all the trends on instagram that like yeah, it's cool for a week and i love it.

And then it's like move on, i'll give you uh, i'll give you two the first.

I'll give you a funny one first.

All right, can you put that?

Put it by a funny one.

Uh, this one's just.

It wasn't the most funny thing, but I got to say it's affected every day of my life.

So the tweet is a reminder that tapping your credit card is a spiritually passive and feminine behavior.

And men should pay via confident and penetrative thrust into the chip reader.

And I read this.

I laughed.

And now every time I pay for something, I can't help but think about this.

And I've been thrusting, my friends.

I've been thrusting.

You got to walk around with that wad of cash.

That's the most manly thing you can do.

That would be John Morgan.

You do need a lot.

That would be John Morgan right there.

You know what I mean?

Well, pulling out a wallet.

Give a finger lick before I start unfolding some bills.

Dude.

That's how you pick up girls.

Just count your bills.

Just in the corner.

My father-in-law did that.

He had $1,000 in 20s.

And one time he had it in a rubber band.

And I was like, I'm in.

So when I bring a wallet, I definitely like to have $500 or $1,000 of 10s and 20s.

It looks weird in the pocket, though.

They know.

They know, they know something, they know.

And then i have a wholesome tweet, and this is from uh, jay yang young, young guy, jay yang, who said something very wise um, is that that you could just do things guy?

He's the you could just do things guy.

And he said here's the hill i'm willing to die on.

He says real success is how many people thank you for theirs.

And i thought wow, that was actually really profound and i think i'm going to steal that as like, what's the point of all this kind of like?

What is the North Star as far as success goes?

And I was like, I think that's the best metric.

Can I say something that I've noticed?

Sean, with you and me is, and I'm wondering if this is true for everyone or a lot of people.

So inspirational, motivational, cheesy content.

There's like, I don't know.

It's so back.

I don't know if it's called a bell curve.

It's like an upside down bell where you're in the middle.

Yes, you're in the middle of your, you're in the beginning of your career and you use it like crazy.

So I read so many self-help books.

And I would listen to Tony Robbins audio books constantly.

Then you start getting in the thick of it.

And you're like, I just got to get this thing done.

I got to spend five or 10 years doing it.

Then you get past that.

And you're a little bit on Maslow's highest hierarchy of needs.

And it's so back.

I listened to so many like Jordan Peterson or how Alex Ramosi like compilation clips where it's just like yelling at me or like reading inspirational stuff.

Are you guys doing that same thing right now?

Love me a good quote.

Love me a good little, like, I don't know, give me some italics.

I need some italics in my life.

You know, that's how I feel.

I love a good quote.

I've actually realized that most smart people like look down upon classic quotes or cliches or motivation or inspiration.

Good.

More for me.

I'm all in on that.

That is the index funds of content for me.

Put me in.

I want it all.

Same.

I'm a boy with the you guys are into live, laugh, love.

Yeah, yeah.

Exactly.

I was going to say that.

This is the live, laugh, love version.

But you know what, Steph?

There's a reason why millions of basic Oklahoma and Missouri women have this on their walls.

Oh, I know.

I know.

I'm just two years away.

I see it coming.

Yeah.

Steph, are you like, I don't like fortune cookie stuff right now?

You're like, I want insights and analysis.

Yeah, I spent years reading personal development books.

And now I'm at that point where I'm like, I know it all.

I read a new personal development book.

I've seen it before.

But I know, I hear what you're saying.

In a few years, it's going to come back.

And I'm going to be like, these people were so wise.

Look, Steph, I'm going to be patronizing to you.

You're young.

You'll figure it out.

You'll get there.

I remember when I felt that way.

Two years older than me?

Something like that?

You'll get there.

You'll understand once you have a few kids, Steph.

How old are you now, Steph?

I'm 32.

And then when you have one kid, we're going to say...

Wait till you have two.

That's the most patronizing thing.

Wait, Sean, you've got three kids?

Sean's got a gaggle.

I got three.

You going for more?

So I get to do it to Sam.

Sam's got two.

So I'm like, oh, two.

Oh, so you're on vacation, huh?

Oh, that must be nice.

I'm not going to blow up her spot.

I'll let you decide, Sean.

But Sean's wife on Instagram is a great follow right now.

She does some wild elf on the shelf stuff and it is a great find.

Me and sarah will like be like look at what she did today.

It's incredible.

We went to like a kid's school performance today and this mom came over to her and she was like i just gotta say i live for your story right now.

She's like every day i'm checking when is she gonna post it?

She's like i'm not gonna do any of that stuff, but I love that you do it.

And I was like, oh, God, you never want to be in that position.

The other day she took a huge wall, like imagine a one bedroom wall and using post-it notes.

I think there are post-it notes.

She outlined the Grinch.

So imagine the Grinch's face.

But the art is like post-it notes.

That is so sick.

It was like a Monet.

It's still up.

We're not taking that down.

I don't think you can.

She must have used string to make the grid, right?

It looks like a pretty intense project.

It was hilarious because it was the only one of the season I did with her, because it was such a big one to do.

And we needed some bonding time.

And so I was like, okay, let's do this.

But she's a perfectionist and is good at things.

And I'm a good enough is good enough kind of guy.

It was just an awful experience for both of us to try to do that together, because she's trying to like, create a grid.

And if something was off, it's like putting together furniture with your girlfriend.

It's just like it doesn't.

And I'm like, I'm like, they're four years old.

They're not going to know.

They can't even see this high.

So it's like they will never know that there was this like one millimeter gap.

And, you know, she had to fix it.

She must have listened to the Will Guderipod that I did.

That was her inspiration for sure.

She must be a listener.

Wait, I want to hear it.

You guys, we didn't do Best New Habit.

Did you guys have a good one for that one?

I also partially just want to brag.

You're a runner now, Steph.

Oh, that you did this year?

Yes, we missed that one.

You're a runner and you're fast.

Sam's like, we missed it intentionally.

No, I think you've been running really, I assume you're going to say running, right?

Because your times are actually incredibly fast.

Yes.

I'm like, now we can finally talk about it.

What am I running all these miles for?

No.

Yeah.

My best life hack slash new habit.

That was the category was running.

And I just wanted to say that I started running about 14 to 16 months ago and I've run two marathons and I'm mentioning it because I feel like everyone runs now, but also there's a ton of people that have never done it because they they think it sucks and it's awesome.

And I think anyone can like get to the point where they're running marathons, running three miles a day.

That's how I started.

Um, and yeah, I feel pretty good about it.

What was your, uh, wasn't your time like sub eight minute miles?

Yeah, I just ran my second marathon, uh, three 30.

So just under eight.

That's incredible.

Sean, that's fast.

Why?

Yeah, I just said it there.

Why do people do this?

Why do all of you who are doing this do this?

That's how I feel about running marathons.

It is awesome.

I like to run.

I'm horrible at it.

I get more joy out of running than any type of weightlifting or any other exercise.

I think that it's less good for you than the other stuff, but it's the most enjoyable when it hits.

It's because you can.

I mean, you can do this weightlifting, but you can measure your progress so clearly.

And you can also progress really quickly, I think, compared to other sports or...

It's going to be one of those things for me.

Mustard, pickles, running, things I don't like.

Other people seem to love.

I just can't do it.

I don't know, man.

20 minutes into like a 50 minute run.

Like you go into like a little bit of a cave and it is like a special

It is kind of special.

It is cool.

You should try it.

Here's my pitch.

Everyone talks about this running high.

Don't chase the running high because it's far away.

Think about do you like walking?

Love walking.

Huge rocker.

So the feeling you get when you're walking is not, I can't wait for this to end.

It's like, I'm outside.

Look at this beautiful thing.

My body feels good.

There is a spectrum, not like a binary difference between walking and running, right?

So people talk about them like they're two separate things.

But there is some version of running.

It might be really slow right now where you feel like you're walking.

And so if you start there which is not where we're taught to start and you just run at that pace for a mile a day, and then two miles a day, and then, you know, do that for a while, you will get to a point where your body, you know, becomes more efficient.

And over time, you're going to be running 10 minute miles at that walking feeling pace.

And you're going to love running.

I'm telling you.

Okay.

Nice try.

Yeah.

The jury will consider what you said.

And he might be out for a flight.

I don't know.

Guilty.

All right.

That's it.

Did you have a habit you wanted to do or no?

No.

Waking up early.

All right.

Well, Steph, I hope you got that in.

That's great.

All right, guys.

Peace.

God bless America.

God bless this podcast.

Sean, good year.

Oh also, you guys didn't even catch this.

I can't see.

What does it say?

I'm on a small screen, is it?

Um backwards, it just is noodles.

That's a wrap.

I feel like i can rule the world.

I know i could be what i want to.

I put my all in it, like my days off on the road.

Let's travel, never looking back.

If you're someone looking to raise your income level, check out The Sales Evangelist.

You can find it wherever you get your podcasts.

[2023 Year-End Review: Investments, Personal Lessons, and Life-Changing Moments]-[The 2025 Milly Awards!]

📋 Summary

2023 Year-End Review: A Candid Look at Growth and Lessons

Unconventional Investment Philosophies

The "Biggest L": Lessons in Humility

Frame-Breaking Moments and Personal Growth

Looking Forward: Habits and Intentions

🎯Key Sentences

📝Key Phrases

📖 Transcript

[2023 Year-End Review: Investments, Personal Lessons, and Life-Changing Moments]-[The 2025 Milly Awards!]

📋 Summary

2023 Year-End Review: A Candid Look at Growth and Lessons

Unconventional Investment Philosophies

The "Biggest L": Lessons in Humility

Frame-Breaking Moments and Personal Growth

Looking Forward: Habits and Intentions

Deep Learning with ListenLeap

🎯Key Sentences

📝Key Phrases

📖 Transcript

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