The 2025 Milly Awards!

All right, so, Steph, welcome back. You've been on 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. OK, 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 recap sub 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.

I know it's- I believe we're close to 2 million subscribers across the YouTube Spotify and Apple or whatever, which is bananas. I mean, that number 90 million, that's a lot of- that's a lot of views. It's a lot. And there's definitely one or two shorts that got 10 million.

I think last year, I think we had last year. There was one where we told the story of the YouTube story of Elon Musk. I think that's 30 million. So some go really heavy, but it's 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 so fun to go through your phone and look at old photos and see what's going on for your trillion 12 months. So I'm excited to do this.

Category number one, the best investment that you made this year, is that right? Best investment you made this year. So Samuel, you want to take this off? Yeah, so my, this just does 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 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. 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, $30,000 to the 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. It 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 office. That's actually a pretty big change overall. Huge change. Definitely made me a lot happier.

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 the 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. Yeah, what am I going to say? I'm not worth about 30% this year, through boring stuff.

Like, stuff, what do you got? Best investment of the year? Tell me it's an actual investment, and not like an investment of the self. 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.

Is that like acne medicine? What is that? Yes, yes, yes. So back story, 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 at 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 like, 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 gonna 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, 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 gonna 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, 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 coming up. I'll just be sure 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 was actually kind of fun.

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 actually shopping assets this morning. And I tweeted 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 out that day, I said, I'm putting 20% into Shopify, 20% into Tesla, 20% of the UIL, 20% of the Bitcoin, 20% Coinbase. The one I forgot to put on here is also by 20% Google. And sorry, not 20%, I put 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 look 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%, UILIL is up 35%, Google's up 50%.

And so my public stock bet that I put out there is my 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.

You'd 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 ones? The one part that's not, I'm not creating these. These are like, what companies do I, what companies are asked to do I want to own for like a tenure period? 10 years might 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. I held, I had one thing 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 I do ozempic. Because you told me that they had some drug that was incredible. And you were like, retruded time. What is it?

You texted me something. And I was like, listen, I didn't listen when Sam said the ozempic thing. But literally it was one, it was literally the only that. It was just you telling me that this drug is incredible.

It puts ozempic to shame. And it wasn't fully out yet or something. I don't know what. You had some early stuff around this?

Yeah, I had a guy basically. So I like to biohack. So I test all kinds of crazy stuff. A lot of times it's like compound stuff, meaning 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.

Yeah. That's all this. And your friend also named Sam. And it did all of the stuff that ozempic 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 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 my deal with drugs. Like you learn about new technology.

And it was amazing. So you told me this. And then since then, did you reach out? No, no, dude.

You told me that day. And I was like, you know what? I'm putting the link here. It's up 34%.

It's up there for a second. I didn't say I researched space. I operate on Gut and Swagger. OK?

And so since then, the CWI really has come on. And because Lily has turned into 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.

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 did operate like more of a tech company now.

But I don't know. It just seemed like people were going to want. I just sort of was like people are going to go to the best product ever. And Sam says they have a better zepic coming.

All right, great. Sean's investment thesis just says, Sam tried some drug. That's it. Well, that's been a part of Sam's other ones.

And so I thought 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.

Sure. There has been a few things. We invested in Andrew Heberman early on. We've got a couple of investments.

Right? Just another 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 were giving people if they go in the comments or the description and click? What is it?

Oh, yeah. HubSpot and you guys, I might personally, and 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 centochillogram to space. What does that mean? Well, it means like completely rethinking our communication system.

Start link. Right. What does it mean? They 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 were getting crazy, and I had to like even out, because it was making up to high of a percentage of net worth.

But I still kept some of it. So I got my ass kicked on that one. How about you, Steph? Sean's not going to like my answer, but it's not financial.

I did get the vitamin. Is it a vitamin or like a supplement of a vitamin? Worst investment of 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, I've got like 20 of those this year. Oh, it was literally these founders who were on one of those like crowdfunding sites, who was like just had 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 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 put them out there. All of them? Yeah, I think 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 you required to go or it was an optional attend and then you regret it. It was an optional attend. It was a lack of judgment.

Gotcha. What about you? Okay, I like it. Sam, anything you want to add to her networking event answer?

No, I mean, no, I agree with you. But yeah, I'm on board. What about your Sean? What's your biggest help?

Or sorry? You're biggest. 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 staff. 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 I just remember thinking, I don't know how she did that, but I like that.

By the way, I had a great year at networking events. I went to an email newsletter conference that we went to Sean's basketball thing. I went to the HubSpot conference like somewhat recently. I had a great year.

Did you have it? I guess I own those sounds much better than the others. So you had a great, like, you went into networking at a time? Yeah, like if I pick it, yeah, because I'd like to see an old friends.

I've been in the industry for long enough. That's the only time that I see old buddies. That's very, that's true. Like, did you go to?

I didn't really go to anything this year. You went to? Well, that was in San Francisco. I showed up a game.

I talked to it. I left. So it was like, you know, a very quick thing. All right.

Hang out with Dartmouth actually. I think that was the only thing I did. Yeah, that's awesome. Okay.

I'll give you my worst investment of the year once again. So here's my, this wasn't, okay. So I guess it's a little less little. I didn't lose money much in any investment this year, which was nice because in prior years, if you go back and watch these awards, it's like, hey, invested in the script of Ponzi scheme.

What's up with that? You know, that was, 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 had, I passed on three different $10 billion start investments that were right in my wheelhouse, which was unbelievable. So the first one was Polymarket. I was one of the early users, probably the first 5,000 users on 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 one class. Like I'm 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's screenshotted his phone and posted one of my blog posts as the background of his phone.

He's like, I thought you like this. This was 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 didn't go actively try to do it until it was too late.

Call she same thing, another prediction market, same product. If I didn't hit the winner, you know, the first winner, probably 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. We'd love to do something with you. You know, all I needed to do was answer. And guess what?

I did answer it. Here's what my great answer was. Oh, so pretty similar to Polymarket then, huh? That was my son of a gun answer.

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 Jack and tell me how much money I lost. And the last one was what not.

So I get acquired by Twitch, the number one live stream of platforms. And 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. We talked about these guys in the pod too. You had a great spiel in them. Talk about them.

I'm actually meet with them. 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 and the best people from Twitch will go and coach them. We'll raid the pantry. This is going to be amazing. And they were like, yeah, you know, we're pretty oversubscribed.

And I was like, it's me. He makes up space. And he's like, all right, let me get back to you. He did not get back to me.

And I did not invest in whatnots first round. And I would say $10 billion company also. And it was literally the thing I was doing. The thing I know probably, you know, there's not a hundred people on earth that know that space better than I do, you know, and miss it.

How many of your investments went under this year? Because I, this was the year where I probably got 10 emails of different angel companies that I, angel investments that I made that they went under. It took about three years. It's the worst phase, right?

So we're probably both since we started like Angel. You had a syndicate. I had a fun. 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 shut downs at this stage.

The winners are going to ride for another five years. So it's like, Angel, you got a distribution and you go check and it's like $3.41 from this company. And then the founders bragging about their acquisition on Twitter and you're like, just you know, just you know, would you, going back, how many angel investments have you done stuff? I don't know, like 15.

Okay. So going back and okay. So first of all, looking 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 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 ten years period. So it'll be something like a, 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 that over the ten year lifespan. That does not seem worth it.

That doesn't even seem worth it for the K ones I have to deal with. Honestly, I don't know if you guys are different. My learning from PXURP was I never want to angel invest again. I, unless it's a company that I want to be involved with, actively.

It depends. So like, I use a conservative estimate just to keep not like get my hopes up or just like false problems myself. But the thing with these is it depends on basically your bet. Like I did a hundred and hundred and ten 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, 100 X returns on each of them or 50 to 100 X. Like, will they, will they last?

Will they exit? Are they going to go up another order of magnitude from here? Like that's what you need an angel investing is to get like, don't it like multi hundred X or 1000 X 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 get the time? Will they actually IPO?

What's going to happen? You know, it's hard to know. I did. I've done 56.

My first two or three were pretty great. Like, you know, maybe 10 X or plus. And then my last two were like a hundred X or something like crazy like that. So basically I had to go through 50 of them to get like the one or two winners, which is pretty, pretty wild.

And so it will be normal. It's the normal. It's normal. It doesn't feel good.

But 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?

Like, and it's also hard to know. I invested in replant and it had like two million in revenue. And now it's 250 million in revenue. It's growing like crazy.

Like it's unbelievable. But like, where does this all go? It's hard to know, you know, if that's sustainable to keep growing as fast as I've been growing. All right.

So next category is the biggest personal L that we took. Okay, I'm going to tell you what mine is. And it's going to make you guys all just like 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 could even tell it. I asked her when she was due.

She wasn't due. She wasn't due. And I said, what do you do? What do you do?

I spent 30 seconds looking for now. Oh, I thought I did in front of five of the people. I just apologized. I said, sorry.

And I walked away. I said, I'm so sorry. I said, okay. I was like, oh, I was falling off a cliff grabbing for trees.

And I couldn't grab a branch. And I was like, 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 and you let him.

And then eventually it just was, I'm sorry. I really. Yeah, I just apologized. It's just funny because I'm podcasting.

You know, 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 did that at a Christmas party in 2013.

I can tell you the exact place and date. It's never left me. I knew not to do that. I knew not to do that.

But I just like told you about when I did it. I knew not to do it. But it's sort of like, I don't know. Like when you, it's thickly stopped at a red light.

Like 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 like it's one of these things I'm going to remember for the next 50 years. Wait, I'm so curious. What do these women say when you apologize? Are they okay?

Like people do this to me all the time or are they like, you're an ash? No, she rubbed it in my face. She basically smiled like smugly. You know, I'm scared of this lady actually because it's her fault.

No, she looked at me and just like, she acted disappointed in me. Which she was. So I don't know. She like pregnant.

She looked like a normal person just had a big belly. Wow. That's outrageous. Amazing.

We should, we should send it to a host right now. 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 got, I've never had to go. Like they call, you know, sometimes you call in, because it's an ever year thing, but it's like Russian roulette. So, you know, you call in, you don't need to come in or you go in and right away, they're like, Hey, you're good to go. I 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. I'm like, what? I don't want to be cases 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. I'm not a prezi.

And I'm like, I've had a judge had a prezi going on. And it's like, he's like, I'm just like proud of his animations. He's like, check his out. Like everybody is the first time they use a prezi.

They're like, Holy shit. This is better than Avatar. Like, 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 the 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. I'm like, Oh, I'll just say I have a work trip.

Easy. They gave the dates. Funny enough, I got to work trip. So I'm in the row.

I'm like, seven people ahead of me. First person stands up and says, uh, your honor, I have a work trip. I'm not going to be able to attend. He says, um, 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 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.

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 going to do next? 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 going to work. That's not going to 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, do you have your wife at home?

And I'm like, it's personal question, but, uh, so I'm like, do I lie? Do I lie? Do I not lie? I'm like, she is at home, but I'm like trying to figure out like, how do I like, can I, can I, can I muddy the waters a little bit?

And then 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 a. You see her? Yeah. Like, what she says is a bad mom.

Like that's not going to work. She's a drunk sir. I'm like, I'm the primary caretaker of this baby. And then like, you know, like I remember the biggest middle name at this point.

And then she's like, she's like, so quit 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 want to feel comfortable with it.

And then she's like, why? You're like, look, you're on her. It's what is it? noon.

And basically my wife sounds 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. I'll be there. I'll be there. I'll be there.

I'll just let it pass girl next to me. She goes, the lady asks, she's like, can you do it? And she was like, no. And the judge goes, what up?

She goes, it's against my religion. I believe you should judge anyone. And she's like, what religion is that? She goes, and she's cited a Bible passage, which was like basically about like, don't judge anyone there because they don't judge you or something.

And the judge is like, okay, thank you, you're dismissed. I'm like, whoa. Couldn't you have just told him you're racist or something? Yeah, I thought about that.

But I was like, I was in a very diverse crowd. I was like, in case I don't get off with that, I don't want to be around these people where I'm saying I lied that I'm racist. So, you know, it was a tough in the moment. But it was the biggest I had was just embarrassed myself.

And by the way, it was so fun. Jurtity was a great time. And I'm glad I got to do it. It was a great opportunity.

Sorry. Did you make him guilty or innocent? I didn't get picked in the end for the actual eight in the box or whatever that like the people who actually go sit there. I just didn't get dismissed early.

So I spent the day. I spent three days there. You should wear a purple heart. And you look at you.

You really just take one for the country. It was true. What's your step? 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 something was made. No, no, I promise.

I promise. 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 like driving full force towards a thing that you love doing.

So 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 Grak 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? Did we, we did. 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 I took me two more years to make the comments. It didn't land. I'm not very persuasive. All right.

Next category we have is coolest moment. I've got a good one. Actually, can we, can we skip to, let's do a couple of the non-persalvers will come back to that one. So let's do, um, you want to do Billy of the Year or favorite guests?

Which one do you want to do? Um, Billy of the Year. Okay. Billy of the Year.

Um, Sam, you go first. Yeah, I did this podcast with this guy named Steve Houghton. Steve Houghton is a billionaire via a 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 he was a billionaire, but it seemed like his kids really loved him.

And I like made an offhand comment like, yeah, man, I got to come out and see how you manage your family sometimes. See how we have a room for you. And I was like, all right. And I just said, yes.

And I had to go downstairs. My wife had to go pack your bags there. We'll go to Utah. And she's like, I met this guy just to pack out of my window for 16 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 like 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 17,000 square foot home. It's his entire family. And I mean, this sounds like I'm being a, 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 of it. That's pretty good. 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 way.

And it's kind of crazy when you actually think about it. I think that was max two years ago, maybe three. 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 waymo's upon waymo's apartment. Like there's, I've been at intersections where there's eight waymo's at that intersection. Is it 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 billionaires. I'm cheating a little bit. I'm not sure.

A hundred of millionaire is Sebastian Thrun. He was one of the early founders. He's like the father of self driving. Yeah.

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 the self driving equation in 2005. So 20 years ago, DARPA had a grand challenge funded by the US 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 Wayback Wen. 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. Because he saw how people could learn online, you don't need to get 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 super early to. We're now seeing these EV tool companies get off the ground.

I just think this guy is super cool. He's been early to all of these trends and is just continuing to build, even though he's early to Waymo, he's rich and he's just continuing to double. That's pretty good to find. There's a lineage I think of people under him.

He had his initial lab, maybe say it for whatever. And somebody who was doing self-driving, he was describing basically all the modern self-driving leaders. If you just trace their lineage, he had six people or seven people under him. It was that school of thought that branched out and created all the different people in the industry today.

So he's very much like a sort of grandfather or godfather to the industry. He's also got some range because he created these cars, things, which is the most brilliant thing on earth. But then also he has a course business. And I'm being silly a little bit, but that's not in my opinion in the same category of flying cars.

But Udacity to me is a very respectable, amazing thing. And so it's pretty cool how much range he has. Yes, all of us who create courses, we're just like these self-driving car guys. We have to be the other half.

The same range is like wide. It's almost like up and down. Yeah, our barbell doesn't have the weight on the other side yet. It's a little awkward to hold.

So we definitely have to go do that. But that's pretty cool though. All right, mine 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 three million person weight 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 is 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 modern day, like PT Barnum. There was a lot of this like passion and soul to do this.

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

Like, man, 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 pot. 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 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 even told him that I'm glad you were walking the earth, which I 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? 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 fit inside is the only other part of the total man franchise that we don't know about him yet. I think that, you know, we 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. Like, he's like, he's a very professional person.

If you look to his Instagram, like he pays tribute to his wife, he talks about his team. You see I'm like giving these inspirational talks to his to, uh, the players, uh, I was just like, this guy got no flaws. It almost, it was intimidating. The one little nugget that just kind of showed a lot was they, um, 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, so, but there's always tax plus tax. No, no, no. We, we, we pay that.

We eat the cost of that. It's like, at the scale that they operate at, that says millions and millions of a year just So that the average customer when they're checking out feels like they were kind of taken care of versus being stuck it to. And which is how ticket master and these other things of live nation, like when you go buy from them, you just feel like you're just being mugged basically at the checkout counter. Right?

Oh, and then here's the service you can be in this meeting, 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 actually who actually does that. Very few people. We made we talked to him. We were like, he made a comment where he was like, whatever you see that you've seen for predictions on how big are businesses.

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 of life coolest moment.

I've got one. I've got one. So Sean recognizes 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 of a just person in the world. He had all these powerful people. He had Mr. Beast and Mr.