#92 If I Wanted To Become A Millionaire Creator in 2025, This Is What I’d Do

In today's day and age, you don't need more information. You need the exact right information at the exact right time and nothing else. If you want to make money online and become a millionaire in 2025, I'm breaking down the exact step by step playbook for how to do it. Every single media company that has become very large has struggled financially to the point of either going under or having to be bought by a billionaire. I'm going to sit down with John Yusay, who is one of the best known journalists about creators.

How do you approach your business as a creator so you can scale much more quickly than a lot of the you may see out there?

You don't always have to be the expert if you can borrow somebody else's 10,000 hours. I want to build like a lasting company. I have to build it out in a way where I am not the single point of failure. So we're going to break down not ideas about how to go viral and make money, but my actual playbook. Let's get into it. Hi and welcome back to the Big Deal podcast. I'm Cody Sanchez. This show is growing at such an insane rate. Like, no, seriously, it's kind of crazy. And yet over half of our regular viewers haven't actually subscribed. It's a free way of supporting the show and it helps helps us to grow the show and bring you even better guests. So if you could double check that you've hit that subscribe button, I would be so grateful, from the bottom of my heart. Thank you. And as my friend Andy says, don't be a hoe. Share the show.

You know, it's funny, as I've been doing more interviews with big creators, they've shown me a lot of stuff behind the scenes. I've seen their brainstorming documents, I've seen their notion docs or processes. And I kid you not, when your team showed me your notion page and some of your projects, like, at like, I felt like a part of my brain that didn't even existed, like, started to like blow open because it's the way you approach it and some of the systems. I wanted to ask you about that because I think a lot of folks, myself included, just do things and we don't have a system around it, so we end up recreating the wheel. How do you approach your business as a creator to make it so you can scale and grow much more quickly than a lot of the other folks you may see out there?

Yeah, well, the first thing overall we do before the Tools and tactics is really like a mindset thing. Like, haven't you heard a ton of creators say, like, well, I got burned out, so I didn't want to do it anymore? I think burnout actually happens because we don't have processes.

Yeah, well said.

So if we had processes and systems and people and ways that we followed along to things, we wouldn't burn out. So one, like, don't believe what other creators say because they say that stuff. Because a lot of times we creators want to mimic artists, I think. And artists have this, like, ethereal nature to them, right? They're like, oh, I have to find the muse and I have to create. And, like, they've got this whole thing. And I kind of think that's bullshit. I think you show up and you keep working and then the muse finds you and, like, you just. That's how it goes. And so I think it sounds much cooler to like, have this ethereal, mysterious way that you create. But I think that's the same thing that people do when they make money. They're like, oh, you know, it's just. It found me how big this business got. I just. I could barely. And that's not true. And it's the same with creating. Anybody who's, like, famous or rich worked really fucking hard at it for a long time and wanted it really bad. Nobody get it by accident, even our, like, most famous actors, et cetera. Now I know a lot of them and they. Not one of them has ever said, like, I just stumbled on all this money and fame. They fucking fought for it. I also really like this rule in finance, which is the rule of thirds. Have you heard of this?

Well, tell me about it. I know the rule of thirds in terms of cameras and like.

Oh, interesting.

Yeah, yeah, yeah.

So, like, the rule of thirds in business is basically, like, you get taught kind of early that, like, one third of your time you're going to be. You're going to be great. It's going to be awesome to be a creator or whatever job you have. You're going to really like it. Then one third of your time, you're going to be kind of neutral, or it'll be. You'll be slightly stretched, but you'll be kind of fine. And then one third of your time, you're going to be miserable. Like, dark, awful, miserable, overwhelmed, inundated. But the cool thing is they cycle. So, like, when you're in one, just know, like, you're not going to stay there. So just the next one's coming. The next One's coming. And so if I know all of that, then I don't burned out because I have the right mindset. I realize this is just going to happen for a period, and I keep going. And then the way that you keep yourself sort of honest on all this is I think the only way to build a big business is with people. And I realized that early on, which meant that, like, I had to get the things that I saw out of my head and into a process. Otherwise I was going to go crazy with people asking me again and again what I think.

Yeah.

And so we also have. We have. This is the rule of three instead of the rule of thirds. But anytime something that we do has more than three steps and we do it more than three times, we try to write it down and create an sop. Now, are we perfect at it every time? Absolutely not. Tanner and I were just talking in the car about, like, one stupid thing we had never processized. But for the most part, you know, I joke with. With the team, and sometimes I'll be on stage and I'll be like, what's my love language? You know, and they're like, SOPs, you.

Know, can you define SOP for people who don't know what that stands for?

It stands for a system and process. System and processes. And.

And maybe, Cody, to put that in context, like, you have this great saying of, like, you should have more SOPs than a PIL when they're taking off, because a pilot is like, they have to check so many different things, and it's a repetitive process. What are some of those SOPs that you have? Or, like, talk to me about it. Cause I feel like a lot of creators don't even know what that stands for, let alone how to implement it.

Yeah, it's definitely a business particular thing, but yeah, if you think about a pilot, they have a little checklist they do every time. Even right now for our podcast, I was annoyed because I'm sure people can relate. Like, we were making the same mistake again and again. And I was like, why? We have an sop? So we have a checklist for, like, all right, you schedule the guest. What happens? You send out a text to the guest. What text is it? You ask them what their drink order is. You ask them how soon they need to be out. You ask them what, like, what is their website? What is their contact information. You check in with them the day of the lights go on in the room, the AC goes on like 15 minutes before, because sometimes it gets cold in there. Like, Every single thing you can, and you build it. It's like a living, breathing document. But the problem is your documents are only good as what's called your implementation. So you actually taking the thing and using it. And so for our podcast, for instance, this is like a little sneaky hack. Our generation is so technological that a lot of times our SOPs or our processes go on our phones, right? So you're like, yeah, we'll check it off on there, but what else is on our phones? Like, every distraction known to man ever. And so I had the team print out and laminate sop. And I'm like, before we do anything, where is it? And so then we have our little lamination and we check it off as we go. Why? Because there's no distractions. It's like, where's the thing? This is it. I get to look at it. The best SOP is ideally you take a screenshot or you take a picture of it and everybody signs off what they did. And this sounds kind of annoying and over the top, but I learned it from boring businesses because that's what you have to do with technicians and the trades.

I am like listening to this and I'm like, okay, we got to do this with our process, the laminated.

I mean, the team at first was like, why would you do something so weird? And I was like, I promise you it will change your life because it'll just be there. Like, you can't. You can't not do it. It's right in front of your face.

Cody, I also went through your contrarian creed, and you had these like, 13 principles, which, by the way, I love that you had 13, because you're like, we're going to embrace the unlucky because we're going to make our own luck. But you had this one that you're like, even our notes will be mini masterpieces, which I interpret to say, like, even things you do internally, like, have to be like super high quality. Can you elaborate on what you meant by that?

Yeah. Well, you know, they talk about Pablo Picasso being one of the best artists of all times, or at least one of the most well known artists of all times. And. And there's two things I think are interesting about Picasso. One is he is also the most prolific artist of all time, right? So he had more pieces of art created than any other known artist of time. He had a lot of shots on goal.

Oh, yeah, 50,000 pieces of art fitting last night, Right.

The second is he famously had the story where he was at a table With a friend. A young woman came up to him, asked him to do a drawing for her. He did one in 10 seconds, handed it back to her and said, $10,000. And she said, that took you 10 seconds? And he said, no, it took me 50 years, or however old he was, because it was shot and goal, shot and go, shot and goal to perfection. And so I remembered those two things, and I wanted to apply that to our business. Um, and the. The last thing, I guess with the notes in general, I say to the team a lot, like, imagine if the piece of content that you create, like, the worst thing that you ever do, is the only thing that your. Your, like, biggest inspiration ever gets to see. What if, you know, say, John is a huge Demi Lovato fan, It's probably the.

Oh, my God. Wow. How do you know?

And. And Demi gets to see one piece of your content, and it wasn't one that you were proud of. And I think about that a lot because on the Internet, you know, you are going to do stuff you're not proud of, but I want to at least try.

Yeah.

And so I talk about that a lot with the team. Like, what you are doing is building a Rolodex of pieces of content that are your life resume. And so let's make sure that it's really good and that what we do is so interesting that when somebody else sees it, they want to steal even the napkin that we left behind at the bar, like Picasso.

That's cool. I also want to ask about this SOP for how you repurpose podcast clips and speeches. I think this is super relatable to a lot of folks who may go on podcasts or just the level of detail in that checklist that you went through, maybe to talk through it so people fully understand what these checklists look like for you guys.

Well, I think Gary Vee is really big on repurposing content and has different frameworks for it. But what I found is that you can have an idea, but an idea without a plan is really just hopefully right. And hope is not a great strategy. And so I found that one. In the beginning, you do everything and you learn everything from doing that, and it's incredible. And then at some point, you will burn out if you don't bring somebody on to do the things that you're not uniquely skilled in the world to do. And so I think one of the worst things you can do as a creator is hire the thing you think the business needs, not the thing you want. And so take your Pain off as the creator before you add in to the need of the business. And so one of the. The early things that I didn't want to do was, was first I didn't want to waste the 50 speeches I give a year or whatever when I'm promoting a book, let's say. And so what I found is I was like, God, we have this Rolodex. We're traveling all over the country. I'm taking my team with me. What are we doing with these things? Why aren't we doing more? And in the beginning, we did a few of them, but then I realized that, like, listening for the right hook and exact moments in them is tough. And so Tanner and our team really took. I mean, I don't remember how many bullets this is. Yeah, so 10 bullets on just the setup. Like, just what you have to do every single time to do single execution. When it comes to finding the hooks, we didn't want to just tell people, find the viral part because what does that mean? What is viral? How do you define that? We had to define it. And so we kind of came up with a bunch of different ideas about what viral might be. And usually with our content, we place them in buckets. Like, we have pillars of content. We create. We have buckets. And so some of them might be, is there an audience specific pain point or desire? Like, how do you make a million dollars when you have zero audience wants it? Plus, it's kind of painful, Right. Evoke emotion. You know, I think young people don't work hard enough today. Well, that's going to piss some people off. Moment specificity and numbers. So I found a study where 100,000 people said that if they do this one thing, you will be more successful. Right. Study. We motivate. So is there a line in there where you're like, ooh, that line's so good, I almost want to tweet it. Hook, credibility, hack. So this one's kind of interesting if you're a new creator. So if you're a new creator, you probably already noticed this, but maybe you don't have a lot of credibility. Can you steal somebody else's? And that's what a lot of young people do when they're like, here's how Elon Musk made his why here's how Jeff Bezos. Here's the secret to Amazon's first million. Whatever. So you don't always have to be the expert if you can borrow Somebody else's 10,000 hours. So we use that as well. And then maybe the only one that I think is really useful is it's why use 5 when you can use 1? Which means if you're going to say something, let's say it cleanly and concisely and directly. And every time we look at a script or it's something we're going to create, I want to value my audience so highly and their time even more than them that I'm xing out anything that isn't absolutely necessary. And so a lot of times our team, especially, like, for instance, you know, Christian, he'll get a first draft of a script for something, and the second draft is basically just, can we cut 30% of it? And even with the book I started with the book, there's probably 390 pages and whittled it down to 270.

Yeah.

Because in today's day and age, you don't need more information. You need the exact right information at the exact right time and nothing else.

Yeah.

The other thing I think is important, too, is like, we want to build. I mean, I'm trying to build something kind of giant here. I want to build, like, the 21st Century Media Company. And I don't know that I've really ever talked about all this stuff publicly, because we're very focused on, like, what serves job working John. Right. And that's who we're trying to serve. But when I think about it, I'm like, I think my generation, the finance company of me was like Bloomberg. They were where you went to for news. You also logged in and financed your Bloomberg terminal. Like, that's where you went. And these days, it's like, where do you go? Like, most of the finance news is kind of trash, or it's about the stock market. I'm like, nobody should be day training. That's a terrible idea. So we're trying to build that. And if I want to build, like, a lasting company that can exist beyond my time, I have to build it out in a way where I am not the single point of failure. And I think the moment that you do that, too, is the moment you unlock all this creative ability, too. Because then, I mean, we're talking about. Tan and I are like, okay, what documentary are we going to do next? Like, do we want to do some full feature films? Who's the next talent we want to bring in? But it all started with, like, hey, I just don't want to edit this video. And so can I make a process where somebody else could follow that? And that's a beautiful thing. If that's where you are today.

I mean, so many people say that. To see you do it is really interesting in the behind the scenes.

Yeah, there's no. There's no accidents in success.

Yeah.

Like, and I think you probably see it even more in creators. They're like, the thing is, I'm authentic. You're like, yes.

But like, yeah, no, let's go a little bit deeper. Like, let's get all those humble answers out of the way.

Yeah, yeah, I agree.

Cody, can you break down your income pie chart? Like, what are all the different ways you make money? And if I get asked, you're very open about financing, how much money do you make last year?

A lot. Are you the irs? You're going to. Do I have to report it? I mean, a couple of ways we could talk about this. So how I make the most money is through our Main street holding company. So that company does nine figures a year. And more than that, like, it varies. It can go up and down. It's. It's going up quite a bit right now. But sometimes we sell a company. So I get cagey sometimes is sharing exactly how much we make. Because what if we sell a company that it's not nine figures? So sometimes I think about that. But that's Main Street Holding Company. That's where we make most of our money. You know, it's safe to say we're making eight figures a year, pretty healthy every year. And contrarian thinking, our media company is the same. That business definitely makes good eight figures a year. So that's our media business and how we make money there. So Main street holding company owns like Resi Brands, which is a trade services franchise. So that's like a company called Pinks and that one painter and there's garage up in there. There's, you know, a couple defense companies. There's. So that that thing is probably where we make most of our cash. The second is contrarian thinking. So contrarian thinking is a media company that owns our education business, which is where we teach people how to buy businesses, build businesses, and eventually sell.

Yep.

We have some sponsorships and partnerships in there. That's probably like seven figures a year. The. Let's see, what else do we make money? Adsense. Small amount. Like I don't know how much we make. How much do you think we make in ad dollars a year? Yeah, a couple hundred K. Yeah. A couple hundred K. Yeah. And what else do we do? Oh, and then we're working on more affiliates. So where do we own a portion of a company? And inside Of Contrarian Thinking. Not the Main street holding company that we get paid a percentage in revenue share and distributions and we own part of that company. And then we have Contrarian Thinking Capital, which is our venture capital company. And there we mostly don't make any money. That's a cost center, not a profit center. And that business maybe will become a profit center as we continue to grow. And then we have one independent company that's big called Biz Scout. But that company just cost me millions of dollars and that's us. That's our small business buying and selling marketplace. Sort of like Zillow, but small businesses. And we hope to make a lot of money on that business one day. But right now it just, it costs me money instead.

So almost like three like top line businesses like the holding company where you buy and sell other boring businesses. The Contrarian thinking, which is the media company, the YouTube channel, like all the stuff we've been talking about. And then Biscout is almost like the software that kind of goes along with all of your teachings and where you maybe have transacted some of these businesses that you bought and put in your holding company. Is that right?

Not transacted any on them yet. We just launched this marketplace. So this is what I think Biscout and Main street holding company are like my multi billion dollar place like Main Street Holding Company I think will get to a billion dollars. And you know, there are a few billion dollar businesses in both Contrarian Thinking Capital and Main street hold company, but we just don't own 100% of them.

Yep.

The contrary thinking capital is kind of interesting because I always used to think that venture capital, I still think this, I still think venture capital is something you should not do. You shouldn't angel invest in like high growth unless you're already a millionaire. Like if you can afford to lose money, then I think angel investing makes sense. But that one might be a sleeper because we have like, I think we have $5 billion companies in that one. So. And they're, they're boring businesses. Like our thesis is basically that venture capital ignored boring businesses. They focused entirely on like dating apps and AI. And that's okay. But there are companies like Nouveau Cargo, that's worth a couple hundred million bucks. That's just like, like port, big ship technology, right? Or like figure which is kind of a sexy business, but is humanoid robots, right? That's worth a couple billion dollars. So. So we'll see. But at this stage, you know, the idea is for most of the money we make, can we Plow as much as humanly possible back into both content to continue to grow our investments to continue to grow them. And then I'm not like that flashy probably. Like, I mean you don't see me really posting anything flashy on the Internet. It's not really my deal. I just want to see us grow.

How do you think about courses and like info products? That's another area where like I feel like there's a lot of baggage. But you've done a great job of like selling, you know, like, like, I mean these numbers kind of like stood out to me. You have a hundred dollar course, a $2,000 accelerator and you have a $10,000 coursing community. Like how did you think about the price points? Like how well are those doing? Like, I feel like a lot of creators can also package up what they say into these courses, but maybe not a lot of them do because it's hard to price yourself in many ways. How have you thought about that?

I think there's two reasons people don't do info products. One is because people on the Internet tell you that it is better to go invest somebody else's money than teach them how to do the investing. There's a lot of people that look down on education products and I can see why. Because one universities are a huge institution that has sort of monopolized the idea of teaching another person. I think it's criminal and they're totally overrated. And if you look at the actual numbers for educational institutions today, we have had a 3-4x incline in the cost of universities and we have had a flat line of return, meaning our salary increases after university. So for me I got like on my, again on my moral high ground here. It was like why did I go to an MBA at Georgetown? I mean if I want to climb a corporate ladder, it's very useful. Having that on there is much better than Arizona State Harvard of the west where I went to undergrad. Right. Like way better. But if I don't want to climb the corporate ladder, that 160,000 doll degree or whatever it was that really didn't teach me much of anything. And I'm, and I then, then they say, well it's for the network, I don't know, better network by meeting people like you guys at conferences than that. I think it's, I think that's a scam. And so once I started to realize that my mom's a 30 year special education teacher, I was like, I think we can, I think we can go to War with those guys. I think we can be a better financial education company and we can teach people more about getting financial freedom than a Wharton degree.

Wow, you're targeting my ultima.

Is that yours?

Yeah, I went to Wharton undergrad.

Well, I use Wharton because I think they are the best finance school out there. Yeah, I think NYU Stern is like, second, but it's not Harvard. And MIT and Stanford are actually incredible for entrepreneurship and engineering degrees, but Wharton's like the cream of the crop in finance, and I can't tell you. Sorry. Wharton grads. I can't tell you how many of them I meet who come up to me. One came up the other day and I just. It just tickles, my little taint. But this guy came up to me and he's like, what was he? Oh, no, this was to Chris, my husband. Moral of the story. Dude comes up, we're like, hey, how's it going? Who are you? He's like, oh, you know, I'm so and so. What are you up to? And he says, I am a independent sponsor, which is a fancy Wharton esque way.

Yeah.

What does that mean? I'm buying a business. Oh, that's literally fake vernacular about I'm buying a business.

Come on, dude. Who is that guy giving. He's a bad rap. Come on.

Yeah, so anyway, I'm like, oh, okay, cool. You're going to buy a business. That's awesome. He's like, yeah, you know, I've been doing it for 14 months. You know, it's going really well. My gosh. All right, cool. I'm like, well, we do a little bit of that. If I can help at all. Like, here for you. He's like, no, I don't need any help. I'm nailing it. And of course, my husband's kind of a smart ass, so he goes, 14 months search. Awesome. You're nailing it. And thank God Chris is a rascal, because I'm not as much. But the point being, like, I think they give people a false sense of the real world. Like when I left Georgetown and I was, you know, at Goldman and some of these other places. Yeah, it helped people maybe take me more seriously. But, like, you going to Wharton or me going to Georgetown does not mean that I know more than a guy who's actually run a real P and L business.

Oh, yeah. And I feel like I've learned more, like afterwards, like, running this business with Amanda than, like, I don't know. There's so many things and I never fully felt like I Was studying marketing, entrepreneurship, less finance. But yeah, I think you're spot on.

Yeah, no, I mean, and I think that's where people go sideways. So anyway, so I feel good about us creating that education business a thousand percent. Even though there are people that don't like that online. And I think a lot of people don't like it online. I don't really understand why, except that there are people who are scammy. But I think the ultimate scam is six figures in debt that you can never shake off because the government doesn't allow you to, which is what happens with student loans. And so that's a hill I'll die on. So I feel really good about what we do there. It's a big business, you know, that's an eight figure business a year and we're working on accreditation with some local universities. And my plan is that I want to build that out to be a real institution, but at 100th of the cost, which I think is actually doable and feasible.

In your book you talk a lot about like how to build buy a business, which is even a concept that like just. It didn't really feel accessible and started until I started going through with this. And I see a lot of creators trying to start these flashy businesses that, you know, you get, you see the headlines when they launch, but then when you check in on them a year later, they've gone out of business. What are some of the most interesting examples of creators who are starting businesses that you feel like are smart, they're extensions of what they're doing. The content kind of like amplifies it. Like take me into that world of it because I know you also said like, making money off of content alone is one of the worst ideas in terms of business.

It's a terrible business model. It's a really bad business model. I mean, what do I mean by it's a bad business model? Every single media company that has become very large has struggled financially to the point of either going under or having to be bought by a billionaire for the most part. So, so we know that in fact playing the game of attention with purely information is highly problematic.

Like a buzzfeed.

A buzzfeed, A New York Times. You know, we see this again and again. And if you think that it's bad now in the age of Google scraping all of our stuff, wait until AI comes for us. You know, we're going to have AI Johns all over the place. We're going to have AI Cody's, we're going to have content ripped off, duplicated, and increasingly, I think relevancy is going to be hard. So that's what you can look forward to.

Yeah.

And while I think if you're a creator today and you're not thinking about acquiring businesses and how to get equity and what's called distributing equity, keep paying you over time, you're making a huge mistake. If you are only living off of AdSense and you are only lifting off even info products or education or anything like that, you're in trouble. Because I think that is very easily scrapable. So instead I would obsess on becoming a deal maker, which is why I wrote the book.

Tell me more about that. Because we get approached with a lot of deals. They're like, hey, we'll give you this equity. And we, we've become wiser to kind of diversify that. And we believe in the company. We'll take equity, but we try to get cash flow as well.

So most deals for creators look like option one, which is brand comes to you and they say, I'm going to pay X dollar for Y action. But instead of just taking money up front, 50 bucks for a video for Y action, you say, I want money plus I want a percentage of revenue that I drive. So you could say, okay, if I, you pay me 50 bucks and as an affiliate partner, I want a percentage of revenue. That's called an affiliate deal. Right. So standard partnership affiliate deal. So the third way to do it would be, okay, Brand wants you to do Y again, you're going to ask for money from them, plus you're going to ask for equity. This would be like a stock. Right. So give me some money now and then give me some equity later.

Yeah.

Another way you do it might be Brand gives you money, they give you equity, but you also ask for distributing equity. For why, what is distributing equity mean? That means. Could mean a few different ways to slice. It could mean when you, the owner of the business, take out money from the business, I get a percentage of it. So if, if the equity I get is 10%, when you take a hundred thousand dollars out of the business, John, because you run the business, I get 10k from the business because I have 10% of what's called a pro rata distribution. But that's a little nerdy. The other way that you could do it is let's call that option 5. You could go business dollar equity, distributing equity for Y outcome. And the distributing equity might actually instead be business makes, I don't know, $10,000 a year. I get Either a profit, a percentage of the profit, the net money they make or a percentage of the revenue of the business. Of the entire business. So it's not just if you take money out of the business.

Yeah.

It's if you make money overall. And then the sixth way is brand asks for why Outcome. And you ask for equity and distribute in equity, but you ask for more of it because you're not taking any money up front. This one is probably like likely what Logan Paul did because he wants as much of the equity in the businesses with Prime. Get with Prime.

I've never seen it broken down like this. This is, this is amazing. For each of these six things. So the Y is like an output. Like, like you have to post this many times about it or you have to bring in this many referrals or like you kind of have to define what those deliverables are with the brand.

Yeah. And there's two ways to do that with a brand. So why is your deliverables? You're exactly right. Oh my gosh, I should have been a doctor with his handwriting. But how you can also mess with deal making a different way is you can have either input related deliverables or output related deliverables. So an input related deliverable might be something like 2 IG posts, 3 lives. These are things that you can are activity based, input based.

Got it.

Output goals are things like 100,000 views, 10,000 customers, $10,000 in value, you know, 100 new customers. Which one do you think brands pay more for?

The latter output. Yeah.

Which ones do we usually negotiate for as creators? Input the first one. So if you're confident in your ability to deliver to results, you'd probably want to do output goals and you'd want to say, I think I'm going to crush this. I want to get a percentage of every customer I bring over 10k because I'm going to kill it. In the beginning when you don't know what you're doing, you probably say dah, I don't know. I probably want to have input related because I don't know how this is going to land with my audience. And so basically everything in deal making comes down to risk transfer.

Yeah.

So like who holds the risk and who has more of it and the person that has less risk typically gets less reward and the person with more risk gets more reward.

Yeah.

I think what you should take away from all this if this feels like fuck me, we're looking at so many numbers and we got pie charts. And I thought I left finance what you might want to take away is just if you can learn the language of money, which is really deal making, you'll never be poor. I truly believe that, because you will understand how wealthy people think, and you will understand how companies make money and you make more money when you understand how people who make money make money.

Yeah.

And so what I would do is obsess on deal making, which is why I wrote the book and why I won't shut up about it on the Internet.

I love it. A lot of people will say you have the number one business channel on YouTube. Other people may say you're the most Powerful Businesswoman on YouTube. With your investments, you'll be able to bring exposure to them. But there's a quote in your book from your dad that really stuck with me in that, like, you're not in the game until you're in the dark of the night. Your hand is. Your head is in your hands, and you're facing a lot of the shit that goes on behind the scenes. What's a moment where, you know your head has been in your hands and you've kind of. We've talked about a lot of your success, a lot of the money you made. What's been some of those hard moments?

You know, business is so hard. I think it might be one of the hardest games out there to play. Just this week, for instance, I was just writing a little. A little video about this week. One of my companies, a payment processor, shut them down, and they took $200,000 in recurring monthly income from them and won't give them back their users. So that just killed a business of, like, $2 million a year in revenue, and we can't get our users back.

Oh, wow.

So I'm having a fun Twitter battle with that right now. And so that was awful. Another business was about eight weeks out from running out of cash. They, like, called me flippantly about it. We're like, the thing is, we're a little cash strapped. I'm like, let's define little. They're like eight weeks. We're basically insolvent. I was like, that's not. We can't have that. What's going on? And we had to spend kind of our vacation over the summer really diving into this business, turning the entire business around and making sure that it didn't die. Long nights, no sleep, sleep. Lots of stress, raised voices, people not wanting to do what they had to do, people getting fired. You know, I had another business of mine, actually contrarian thinking at one point, I put Somebody in charge of the business. And, you know, my fault, I thought, they're a really good operator. I was actually running the holding company and talent, which felt like a lot at the time. And my fault, I didn't catch it. But they were running the finances wrong, and we were almost out of cash. That was four weeks for money, not a cash.

Oh, wow. And so this is the media company.

Yeah.

Oh, wow. You put somebody else in charge of it at one point.

Yeah, well, yeah, it was like somebody else who was running a portion of it. I won't be too specific because I don't want to call them out, but if I hadn't literally been accum. Like, if you want to go and get loans for companies, they require an analysis of all your debt and your cash situations. And so if I hadn't been looking at our debt profile and thought, like, that number seems off from this, I wouldn't have contracted it. And, like, do we have plenty of cash and we could have pumped it in? Yeah, thankfully. But what if, like, our payroll had all just died one Friday and I didn't tell anybody? Like, would my employees have trusted me again with that? And so there are so many moments. But I think, you know, I do go back to the Warren Buffett adage, which is like, I'll forgive any. An employee, any mistake, except one that costs us our reputation. And so the thing that keeps me up the most at night is like, do I always feel like we're doing the right thing? You know, do I feel like we have enough checks and balances in place to make sure that we're compliant and we're being truthful and honest? Because I think we have a huge responsibility as creators. I mean, we saw the media fuck it up royally, right? Like, they literally. We have the lowest level of trust as a society of media ever. We actually are lower than some third world countries, which is usually the opposite. It. And so I think about that as creators too. Like, we have a real responsibility to make sure it's. Let's see, what does Jordan Peterson says? He says, tell the truth, or maybe at least just don't lie. And so I obsess on that a lot.

I want to talk about the elephant in the room because business content is, you know, like, gets a bad rap, especially on YouTube. You know, it's a lot of people who say they're influencers who have absolutely no influence at all. People who claim to have expertise, who don't have expertise. I'm curious, as you started to, like, navigate that world how did you think about differentiating? Because your content feels different and gets many more views.

Thanks. Well, you know what, I, I was like super freaked out to talk on the Internet at first. Like, if you think about it, like, if you look at my background, like I was in finance and investing for 12 years. I wasn't, I didn't even have an Internet presence before we started kind of blowing up three years ago. And so when I started making videos, I was like, ah, this is scary. Like, not talking about the thing, but being on video was kind of scary. But then I remember one time that made me chill quite a bit is. And I talk about this with like another one of our, our mutual friends, but I remember we were sending videos back and forth and it was this guy getting on like, like, just like they were like, who's this finance guru? What an idiot. Like, no way. And you know, you obviously don't know what you, what you're talking about. Like thousands of comments. And if you're in finance, you would know that that guy is Ray Dalio. And you're like, this is one of the best investors of all time. He's a billionaire multiple times over. He runs something called Bridgewater Capital and people still think he's a fake. So if that's going to happen to him, it's going to happen to all of us. Which I think gave me some chill on, like, all right, like, people just might not like you and that's okay. And then the second part of it is we try to do what we call show don't tell. So oftentimes we're on the site with a small business owner and they're showing us, like, how did you build this? Can I see the truck? How much did it cost? Can I see the return for that? Can we look at the spreadsheets you have for historical circles? Can we treat it a little bit maybe like the Wall Street Journal might have back in the day to validate anything these guys are talking about. And then the last component is we ask ourselves a lot of the time, like, are we just showing the shiny or are we also showing the shitty? And so the shiny is, hey, here's how much I made on stripe, right? And the shitty is like, here's how long it took me, here's how much I failed. Here's the really terrible parts about this business business. And so I think that helps. I mean, we were like, I mean, we were climbing on top of a one ton waste container that like had maggots crawling all over inside of it. And helping them clean out actually a toilet in order to see, like, how miserable is it owning a toilet cleaning business, even if it makes $5 million a year. So I think that mixture of like, show, don't tell, shitty plus shiny, and also people are just gonna hate you no matter what you do, and they're also gonna love you if you do it well. So, like, kind of, who cares?

Was there a moment that that light bulb went off where you're like, hey, there's something here with these unsexy, boring businesses that I should cover? Because, you know, I feel like conventional wisdom is like, let me go after the shiny thing. Let me talk about tech startups or the big names. And you just went in a total opposite direction and it's been really successful. Like, what was that moment where you're like, let me cover people in these videos for it to take off?

Well, I think in the beginning I just thought they were interesting. Like, if you met me, I think, didn't I ask you, like, how much things cost, like multiple times before we started shooting this? Yeah, I just, I find the, the cost of things, like, fascinating. And like, how much money do you make? Like, how did you do that? What happened there? And so it gave me an opportunity to ask totally inappropriate questions frequently. So I think that's how it started. I literally was just like, but I want to know how you made money on that so that I can. And that's very normal in finance, but I guess not that normal in life. Life. So at first it was just you follow your curiosity, you know. And then the next thing I think I realized from it is like a selfish thing, which is I want to invest in more businesses and I want to change the way investing is done. And so back in the day, I used to run like a multi billion dollar asset management company at a company called First Trust. And I built out our Latin American investment division. And I remember I got into it with the guy who heads the company, who I'm friends with to this day. But like, he was like, no, the way that finance and investing is going to happen in the future is we, we go to these centers of influence, we take them to steak dinners, we know their family, we have this long relationship with them. You're flying on a plane every single day. And I was like, I think that we could do all this on the Internet. And in fact I think they would like it more. I don't think rich guys want more steak dinners. And so I, I think this is outdated. Did and he was basically like, I want to row left, you want to row right, get your own boat. And I was like, well, but also, okay, fine. And so I did. And once I had my own boat and we had our own businesses and we were growing, I'm like, I want to do media for distribution. So now we have Main Street Holding Company, which is where we hold our boring businesses like the ones we own a big portion of. Then we have Contrarian Thinking Capital, which is our venture capital fund where we invest in small businesses. But those are tech based, smaller dollar amounts. And so now I don't really go out and try to find new companies. They come to me nonstop. And so I think I served the content, one, because I was curious about it, and then two, because it made us cash. And then maybe the last part is like my egotistical belief that I think one, freedom is actually green. It's just, it's money. Like, the more money you have, the more you can assert your will on the universe. And I think, you know, if I was to say money is the root.

Of all, I mean, the saying goes evil, but I think it's root of power, it can open things up. I mean, I mean, I'm a kid of immigrants, so I think I view it a bit differently.

Totally. But like, why, if we were to ask a room, I go and do these speaking events, money is the root of all. And everybody goes evil. And you're like, who programmed that? Like, who said that it had to be that way? How come it's scammy if we talk about money? How come it's scammy if we talk about business? Oh, of course, because if we talk about it, then we're gonna get more of it and then we can push back on the people who have it it. And so I just don't like that. So I'm like, no, I'm going to talk about it. Because when I was young and hungry, nobody told me how to make money. It was super confusing. So I never had any. And I didn't have any understanding of financial literacy. And I wish somebody would have talked about it in like simple terms instead of the second that you get money in this country, we're like, don't tell them how you got here, you know, because that would be gross. Or that would be scammy. Like, no, actually that's just like putting a hand down. So that's my moral high ground that I get on sometimes about cash.