In short
How to build a “millionaire creator” business in 2025 using systems (SOPs), process-driven scaling, content repurposing frameworks, and dealmaking (equity + risk transfer) instead of relying on ads/info alone. It also covers trust, transparency, and differentiating business content.
Guest
John Yushe, a journalist known for covering creators and creator business strategy; he discusses scaling via processes, SOPs, and content “hooks”/pillars.
Key claims
Burnout comes from lack of processes; success isn’t accidental; “rule of thirds” mindset helps endure cycles; any repeatable workflow should become an SOP; repurposing needs defined “hooks” and content buckets; info/adsense-only models are vulnerable to scraping/AI; creators should “obsess on dealmaking” and learn money language.
Notable examples
Laminate podcast SOP checklists to avoid phone distractions; Picasso analogy for “shot and goal” perfection; content “shiny vs shitty” approach; Ray Dalio being criticized as a “fake” despite Bridgewater; toilet-cleaning business example; deal structures (affiliate, equity, distributing equity) and output-based deliverables.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Importance of Systems in Creating
1:21 to 2:24
Understanding how systems and processes can prevent burnout and enhance creativity.
“Hi, and welcome back to the Big Deal Podcast.”
The Rule of Thirds in Business
2:24 to 3:46
Learn about the emotional cycles in business and how to manage them effectively.
“Well, the first thing overall we do before the tools and tactics is really like a mindset thing.”
Creating Effective Standard Operating Procedures (SOPs)
3:46 to 4:56
Explore the significance of SOPs in streamlining business processes.
“I know the rule of thirds in terms of cameras and light.”
Using Checklists for Success
4:56 to 6:45
The benefits of using checklists to minimize errors and increase productivity.
“Tanner and I were just talking in the car about like one stupid thing we had never processized.”
Embracing High Standards in Content Creation
6:45 to 9:35
How maintaining high standards in all content can impact long-term success.
“And so then we have our little lamination and we check it off as we go.”
Repurposing Content for Maximum Impact
9:35 to 13:24
Strategies for effectively repurposing content to reach wider audiences.
“I also want to ask about this SOP for how you repurpose podcast clips and speeches.”
Building a Lasting Media Company
13:24 to 14:01
Insights on creating a sustainable media business that thrives beyond its creator.
“Because in today's day and age, you don't need more information.”
Building a Lasting Company
14:01 to 14:50
Learn about the importance of creating a sustainable business model.
“And these days, it's like, where do you go?”
Income Breakdown and Business Ventures
14:51 to 17:42
Explore various income sources and business strategies for success.
“And I think you probably see it even more in creators.”
Critique of Traditional Education
17:43 to 21:42
Understand the limitations of traditional educational institutions versus practical experience.
“like the holding company where you buy and sell other boring businesses.”
Show all 17 chapters
Critique of Traditional Education
21:43 to 22:35
Understand the limitations of traditional educational institutions versus practical experience.
“I think NYU Stern is like second, but it's not Harvard.”
Critique of Traditional Education
22:44 to 23:14
Understand the limitations of traditional educational institutions versus practical experience.
“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.”
The Reality of Business Education
23:15 to 26:56
Discussion on the actual value of business education and real-world application.
“to and he says i am a um independent sponsor which is a fancy wharton-esque way yeah i'm saying, I'm buying a business.”
Creator Business Models and Equity
26:57 to 28:00
Insights on how creators can leverage business equity for success.
“Tell me more about that because we get approached with a lot of deals.”
Understanding Equity and Deal Making
28:00 to 33:32
Learn the nuances of equity distribution and how it relates to deal-making.
“They give you equity, but you also ask for distributing equity.”
Navigating Challenges in Business
34:36 to 42:01
Hear real-life challenges faced in business and the lessons learned.
“That was four weeks from running out of cash.”
The Importance of Financial Literacy
42:01 to 42:39
Learn why discussing financial success openly can empower others and promote literacy.
“we can push back on the people who have it.”
Transcript
Automatic transcript. May contain errors.0:00This episode is brought to you by Accenture. When your advertising operations fall out of sync, everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result? Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. 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.
0:35If 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 Yushe, 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 other folks you may see out there. You don't always have to be the expert if you can borrow somebody else's 10 ,000 hours.
1:06I 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, say. 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 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.
1:41Thank 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 processes, I felt like a part of my brain that didn't even exist, it started to blow open. Because the way you approach it in 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.
2:13So 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.
2:53And 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 found me how big this business got. I could barely. And that's not true. And it's the same with creating.
3:26Anybody who's famous or rich worked really fucking hard at it for a long time and wanted it really bad. Nobody got it by accident. Even our most famous actors, et cetera. Now I know a lot of them and not one of them has ever said, 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 light. 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 is slightly stretched, but you'll be kind of fine.
4:02And 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 burn out because I have the right mindset. I realized 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.
4:37Otherwise, I was going to go crazy with people asking me again and again what I think. And so we also 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 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.
5:09Can you define SOP for people who don't know what that stands for? It stands for a system and processes. agencies. And, um, and maybe Cody, to put that in context, like you have this great saying of like, you should have more SOPs than a pilot does when they're taking off. Um, because a pilot is like, they have to check so many different things and it's a repetitive process. Um, 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.
5:41Even right now for our podcast, I was annoyed because I'm sure people can relate. 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 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 everything, single thing you can, and you build it.
6:15It'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 an 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.
6:51Why? 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 in the trades. I am like listening to this and I'm like, okay, we got to do this with our process. 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.
7:23Like 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 interpreted 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, 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.
7:58And 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. I think 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. She said, that took you 10 seconds. He said, no, it took me 50 years or however old he was because it was shot and goal, shot and goal, shot and goal to perfection.
8:32I remembered those two things and I wanted to apply that to our business. The last thing I guess with the notes in general, I say to the team a lot, 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 top of your list. How'd you know? Oh my God. Wow. How'd 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.
9:15And 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 on that checklist that you went through, maybe to talk through it so people fully understand what these checklists look like for you guys.
9:52Well, I think Gary V 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 hope. And hope is not a great stretch. 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.
10:27And so take your pain off as the creator before you add in to the need of the business. And so one of the early things that I didn't want to do 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 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.
11:07Yeah. 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?
11:44Audience wants it, plus it's kind of painful, right? Right? Evoke emotion. 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 you do this one thing, you will be more successful. Right? Study we found. 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.
12:24Can 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 five when you can use one, 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 at something we're going to create, I want to value my audience so highly and their time even more than them that I'm X-ing out anything that isn't absolutely necessary.
13:03And 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 was probably 390 pages and whittled it down to 270. 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. 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.
13:40And 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? 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.
14:12And if I want to build 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.
14:45I mean, so many people say that to see you do it is really interesting in the behind the scenes. Yeah, there's no accidents in success. 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, you know, let's go a little bit deeper. Like, let's get all those humble answers out of the way. 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 could ask, you're very open about finance. How much money do you make last year? A lot. Are you the IRS? Do I have to report it?
15:18I 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, it varies. It can go up and down. It's going up quite a bit right now. But sometimes we sell a company. So I get cagey sometimes with sharing exactly how much we make because what if we sell a company and then 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. It's safe to say we're making eight figures a year pretty healthy every year.
15:52and uh contrarian thinking our media company is the same that business definitely makes good eight figures a year in revenue 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 um there's garage up in there there's um 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 businesses.
16:31We have some sponsorships and partnerships in there. That's probably like seven figures a year.
16:41Let's see, what else do we make money? AdSense, small amount. 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. Um, the, and what else do we do? Oh, and, and then we're working on more affiliates. So where do we own a portion of a company 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.
17:16that'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 BizScout. But that company just cost me millions of dollars. And that's our small business buying and selling marketplace, sort of like Zillow, but for 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 top line businesses, like the holding company where you buy and sell other boring businesses. Yep. The contrarian thinking, which is the media company, the YouTube channel, like all the stuff we've been talking about.
17:53And then BizScout 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've 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 BizScout 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 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.
18:27The Contrarian 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 high-growth startups 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. And they're boring businesses. Like our thesis is basically that venture capital ignored boring businesses. They focused entirely on like dating apps and AI.
19:00And that's okay, but there are companies like Nuvo Cargo that's worth a couple hundred million bucks that's just like port, big ship technology, right? Or like figure, which is kind of a sexy business, but is humanoid robots, right? It's worth a couple billion dollars. So we'll see. But at this stage, 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.
19:34I 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$100 course, a$2 ,000 accelerator, and you have a$10 ,000 course in 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.
20:08How 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 three to four X incline in the cost of universities.
20:41And 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 degree or whatever it was that really didn't teach me much of anything. And 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.
21:18I 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 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 alma mater. Is that yours? Yeah, I went to Wharton undergrad. Well, I use Wharton because I think they are the best finance school out there. I think NYU Stern is like second, but it's not Harvard. And MIT and Stanford are actually incredible for entrepreneurship and engineering degrees.
21:55But 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. Right now, get up to 15 % off select storage solutions. Put heavy duty HDX totes to good use, protecting what's important to you. The solid impact resistant design prevents cracking and the clear base and sides make items easy to find. Even when the totes are stacked, find select shelving and tote storage up to 15 % off at the Home Depot.
22:30to organize every room in your home, from your garage to your attic. Visit homedebo.com. How doers get more done. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome? That's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? there's no place like chrome check responses set up required compatibility and availability varies 18 plus uh what was he oh no this was to chris my husband moral of the story uh 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 um independent sponsor which is a fancy wharton-esque way yeah i'm saying, I'm buying a business.
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23:26That's literally fake vernacular about I'm buying a business. Come on, dude. Who is that guy? It's a bad rap. Come on. Bad rap. So anyway, I'm like, oh, okay, cool. You're going to buy a business. That's awesome. He's like, yeah, I've been doing it for 14 months. It's going really well. I'm like, 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.
23:54But the point being, I think they give people a false sense of the real world. When I left Georgetown and I was at Goldman and some of these other places, yeah, it helped people maybe take me more seriously. But 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 &L business. Oh, yeah. Yeah. And I feel like I've learned more afterwards running this business with Amanda. 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.
24:29And I think that's where people go sideways. So anyway, I feel good about us creating an 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. That's an eight-figure business a year.
25:01Wow. And we're working on accreditation with some local universities. Cool. And my plan is that I want to build that out to be a real institution, but at one hundredth of the cost, which I think is actually doable and feasible. In your book, you talk a lot about how to buy a business, which is even a concept that didn't really feel accessible until I started going through with this. And I see a lot of creators trying to start these flashy businesses that 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 their 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 why 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.
26:05So 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. 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. We're going to have AI johns all over the place we're going to have ai codies 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 well 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 where they keep paying you over time you're making a huge mistake if you are only living off of adsense and you are only living off even info products or education or anything like that you're in trouble because i think that is very easily scrapable.
26:56So instead, I would obsess on becoming a dealmaker, 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'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 you X dollar for Y action. But instead of just taking money up front, 50 bucks for a video for why action. You say, I want money plus I want a percentage of revenue that I drive.
27:33So 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 why 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. 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 does distributing equity mean?
28:12That 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 the equity I get is 10%, when you take$100 ,000 out of the business, John, because you run the business, I get 10K from the business because I have 10 % of it. It'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 five. 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.
28:56I 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, John, it's if you make money overall and then the sixth way is brand asks for why uh outcome and you ask for equity and distributing 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 business as you can get with prime i've never seen it broken down like this this is um this is amazing for each of these six things so the why is is like an output 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.
29:43Yeah. And there's two ways to do that with the 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 dealmaking a different way is you can have either input related deliverables or output related deliverables. So an input related deliverable might be something like two IG posts, three lives. These are things that you can, are activity-based, input-based. Output goals are things like 100 ,000 views, $10 ,000 in value, 100 new customers. Which one do you think brands pay more for? The latter. Output.
30:26Which ones do we usually negotiate for as creators? Inputs. The first one. So if you're confident in your ability to deliver 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 in over 10K because I'm going to kill it. In the beginning, when you don't know what you're doing, you probably say, 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 dealmaking comes down to risk transfer. It's like, who holds the risk and who has more of it.
31:02And the person that has less risk typically gets less reward and the person with more risk gets more reward. 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.
31:33And 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're going to 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 uh you're facing a lot of this that goes on behind the scenes um 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 um business is so hard i think it might be one of the hardest games out there to play.
32:25Just this week, for instance, I was just writing a little video about this week, one of my company's 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. 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 called me flippantly about it. We're like, the thing is, we're a little cash strapped. I'm like, let's define little.
32:59They're like, man, 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, 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.
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34:15Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. And, you know, my fault, I thought they were 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 from running out of cash. Oh, wow. And so - This is the media company? Oh, wow. You put somebody else in charge of it at one point.
34:47Yeah, 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, 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 caught 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?
35:20And 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.
35:58Um, we actually, uh, are lower than some third world countries, which is usually the opposite. And so I think about that as creators too. Like we have a real responsibility to make sure it's a, let's see, what does Jordan Peterson says? He says, um, 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.
36:30I'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 was like super freaked out to talk on the Internet at first. If you think about it, if you look at my background, I was in finance and investing for 12 years. 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. 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 another one of our mutual friends, but I remember we were sending videos back and forth and it was this guy getting shit on.
37:10Like, 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'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, like, 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.
37:43And 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 historicals? 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, 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?
38:20And 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. And so I think that helps. I mean, we were like i mean we were climbing on top of a one ton waste uh 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 five million dollars 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 know who cares.
38:57Was 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.
39:25I find the cost of things fascinating. How much money do you make? 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. So at first it was just you follow your curiosity. And then the next thing I think I realized from it is a selfish thing, which is I want to invest in more businesses and I want to change the way investing is done.
40:00And so back in the day, I used to run like a multi-billion dollar asset management company, 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 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.
40:30And in fact, I think they would like it more. I don't think rich guys want more steak dinners. And so I think this is outdated. And he was basically like, I want to row left. You want to row right. Get your own boat. And I was like, oh, fuck. 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.
41:06But 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 money. Like the more money you have, the more you can assert your will on the universe. And I think 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'm a kid of an immigrant, so I think I view it a bit differently.
41:46Totally. But like why? If we were to ask a real, am I going to do these speaking events, money is the root of all and everybody goes evil. And you're like, who programmed that? 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 going to get more of it and then we can push back on the people who have 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.
42:13So 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.
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From the publisher
I sat down with my friend Jon Youshaei ( @youshaei ) to get real about what it takes to build content that actually drives business. We dug into how I face down public speaking fears, deal with critics, and why showing both the grit and the glam is essential. I also shared exactly how I make money—through my holding company of “boring” businesses, my media brand, and investments—plus the systems I use to scale it all. We talked deal-making, financial literacy as a moat, and the responsibility creators have to tell the truth. If you’re serious about building wealth and not just followers, this episode is for you.
00:00 Introduction
00:02 Navigating the World of Business Content
00:23 Overcoming Fear and Criticism
01:27 The Concept of 'Show Don't Tell'
02:41 The Moment of Realization
03:01 Curiosity and Financial Literacy
03:31 Changing the Investment Landscape
06:48 The Importance of Processes and Systems
12:38 Creating High-Quality Content
14:47 Repurposing Content and Finding Viral Moments
20:08 Building a Community with Cult Sayings
22:36 Consistency in Personal and Professional Identity
23:00 Building a 21st Century Media Company
24:31 Breaking Down Income Streams
29:05 The Challenges of Brand Deals
32:55 The Value of Education and Info Products
38:59 The Importance of Deal Making
44:44 Facing Business Challenges
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