Oct. 8, 2025

Who Is The Greatest American Entrepreneur Of All-Time?

Who Is The Greatest American Entrepreneur Of All-Time?

Tim Chermak, founder/CEO of Platform Marketing, shares why he believes Walt Disney is the greatest entrepreneur of all time. Recorded live at the LevelUp Conference.

Tim Chermak, founder/CEO of Platform Marketing, shares why he believes Walt Disney is the greatest entrepreneur of all time. Recorded live at the LevelUp Conference.

Tim Chermak: The importance of building a brand and having that brand mean something. A brand is not a logo. A brand is what people think about you based on the totality of the work you've done. So, it's build a brand. I think Walt understood that the phrase “creative risk” is redundant. Risk is creative, and creativity is taking an emotional risk. And so you're never gonna get ahead in life unless you're willing to risk something.

Tim Chermak: This is The Platform Marketing Show where we interview the most creative and ambitious real estate agents in the country, dissect their local marketing strategy, and get the behind-the-scenes scoop on how they're generating listing leads and warm referrals. We'll dive into the specifics of what marketing campaigns are working for them, how much they're spending on those campaigns, and figure out how they have perfected what we call the Platform marketing strategy. This is your host, Tim Chermak. I'm the founder and CEO of Platform. I love marketing and I talk too much, so let's dive in.

Tim Chermak: If I were to ask you to name who is the greatest American entrepreneur of all time and you just kind of sit with that for a minute and think, “Hmm, of all the business titans, what some people may call the robber barons of American capitalism, who is the greatest of all time? Or even who's on the Mount Rushmore, like the top four or five capitalists of all time?” 

Tim Chermak: Most people are going to think of names like Rockefeller and Carnegie. Perhaps J.P. Morgan, maybe Cornelius Vanderbilt. More recently, you might say Elon Musk, perhaps Steve Jobs. One name that does not get enough credit is Walt Disney. So, I wanna try to convince you that Walt Disney is in fact the greatest American entrepreneur of all time. And that's largely because unlike all of the capitalists I mentioned, Walt transformed multiple, entirely different, new industries from scratch, inventing both products that didn't previously exist, business models that didn't previously exist, and he did so largely in an industry that didn't exist before Walt Disney. 

Tim Chermak: Most of the greatest entrepreneurs of all time, like I said, the Rockefellers, Vanderbilts, Fords, they had very large industries to start with. Rockefeller in oil, Ford obviously helped pioneer automobiles, Carnegie with railroads and then steel. If I could describe what Walt Disney, what industry he built or transformed, it was something as intangible as storytelling, and yet he built a multi-billion dollar company out of storytelling. And Walt, I think, proved that creativity itself could be a business. 

Tim Chermak: Now, in any endeavor, creativity obviously helps and enhances and accelerates your business. Rockefeller clearly applied creativity to the refining process. He applied creativity to his business model and the trust structure that made standard oil so effective, in how they refined byproducts from the oil, everything from kerosene to gasoline. Vanderbilt employed creativity in the business model of lowering the fares on all the steamships, and thus operating at a lower cost than everyone. He basically pioneered what we now consider the idea of a loss leader. So if you've ever enjoyed a dollar-hotdog at Costco, thank Cornelius Vanderbilt for that business model. He practically invented that. Same with Morgan with financing, Carnegie, all these guys. Henry Ford, of course, it wasn't just automobiles that's the lasting legacy of Ford, it's the assembly line. 

Tim Chermak: So clearly, creativity is present in any business, but Walt proved that creativity itself could be a business. Furthermore, I just think it's so interesting that up until the age of Walt Disney, if you wanted to succeed in business, you needed either capital or access to people who would loan you capital. Walt kind of proved that, hey, I don't need a ton of money to start a factory, or a ton of money to buy a bunch of inventory or land to lay railroad track. Creativity, in some instances, can be a substitute for capital in capitalism. Of course, even the word capitalism was a name given to our free market system by its opponents. It was supposed to be a pejorative, kind of just assuming that, oh, the only people who can thrive in a capitalist system are people who inherit wealth. Walt's journey really proves that to be complete nonsense. It's especially spicy because his father was a card-carrying member of the American Socialist Party. 

Tim Chermak: This is a photo from the early 1920s of Walt and his brother, Roy, who founded the Disney Brothers Studio together formally in 1923. Now, he had started his first studio, which ended up going bankrupt actually when he was 18. Technically, before age 18, and he was given the choice when that first business failed. Do I declare bankruptcy, or could I escape via basically a paperwork loophole of saying, “I was a minor and I didn't know what I was signing when I took on all this money and debt?” and he chose to go through formal bankruptcy. 'Cause even though people were telling him, “Hey, you can get out of this by saying you were a minor and you didn't know what you were doing,” he believed in just doing business the right way, and that his reputation and his brand as a person, as an individual, a personal brand, that actually mattered. And we'll get more to that in a second. 

Tim Chermak: But the first main contribution I think that Walt made, not just to the entertainment industry, but to business as a whole, is this idea of brand and that your brand matters. He's not the person who invented the idea of a brand. That had existed over a hundred years prior. If you would go in the mid-19th century to a general goods store and you'd say, “Hey, I want some flour and some eggs,” branding kind of came to be because people realized there's just a giant barrel of flour over here or boxes of eggs. I don't really know what eggs I'm getting or where the flour came from or where this milk came from. And eventually, the owners of these stores started realizing if we could create a brand and say, “Hey, you're buying this brand of toothpaste, or you're buying this brand of soap,” people would pay a price premium.

Tim Chermak: What they were buying was certainty, that they knew that this is the soap I get when I buy this brand, or this is the quality of flour I get when I buy this brand. That's how brands started really as a risk mitigation strategy to just know that it was a sense of quality control, that this is what I'm getting when I buy this type of soap. And if I go to any store in the country that carries this brand of soap, I know I'm gonna get this certain quality of soap, or eggs, flour, etc. Walt applied that to the idea of a person. He wanted the name Walt Disney to mean something. And it goes back to how he got into Hollywood. 

Tim Chermak: So he goes bankrupt in Kansas City, moves out to Hollywood. This is classic Walt. He doesn't have money for a suitcase. He literally just went bankrupt, so his suitcase is literally fashioned out of cardboard and tied together, and yet the money he did scrounge up, he bought a first class ticket out to California, which would be the equivalent of using a Walmart bag as your carry-on, but flying first class out to California. And he shows up and wants to get into the movie-making industry, 'cause this is the early 1920s, kind of entering the golden age of Hollywood, but he has no contacts. I guess he was the founder of a failed film company. He really has no network. He wants to get into feature movie making, but he realizes, I don't have any advantage there. So the only reason to this day that he went into animation was he figured there's a lower barrier to entry there. There's less competition there. Less people are interested in animation, therefore, I'll do that to break through. But what he really wanted to do was make feature length movies. 

Tim Chermak: So he gets into animation and quickly realizes that it's hard. At the time, there was no such thing as a feature length cartoon. The animated shorts were typically five-minute shorts that played before a movie. So today, if you go to a movie, you have to sit through all the previews before the actual movie starts. We watch trailers before a movie, that's what they used cartoons for. Before the actual movie you were paying for, there'd be a bunch of just kind of juvenile, amateur, slapstick humor, very rough. There wasn't any storyline or anything. It was just dumb cartoons for five minutes to just give you a quick giggle before the movie started. They were not serious, and not a lot of thought went into them. Like I said, not really any plot or character development, just five-minute slapstick humor shorts before the actual movie started. And so because of that, the movie distributors were not really willing to pay a premium for people making these cartoons because it didn't really affect the demand of ticket sales. What cartoon they threw before a movie did not change, at the end of the day, who was gonna go see that movie, how many people were gonna show up. 

Tim Chermak: So this is one of the first times that Walt, I think, realizes that if I can find a way to create a character, create a brand where people will actually go out of their way to go see this movie because my cartoon is attached to it, then I would have a little bit of pricing power in my negotiation with the distributors 'cause I can actually show data and say, hey, people want to see this character, therefore I'm gonna charge you more for the rights to use my cartoons. 

Tim Chermak: So prior to Walt having this realization, the idea of brand didn't really exist in Hollywood. And I would argue it still doesn't really exist today. Walt was the first person to realize what if a “Walt Disney picture,” that phrase before a movie actually meant something. So today, if we go see or we even hear about a movie, “Hey, there's a new Walt Disney movie,” already, without any context, you sort of know what that movie is going to be about. Or at a minimum, you know what it's not going to be about. It's probably gonna be family-friendly. If it's a Walt Disney film, it's not gonna have a bunch of sex or violence or gore. It's probably aimed at children. You know what a Walt Disney picture means. 

Tim Chermak: At the time, all the studios back then, there was Warner Bros. Still to this day, if, like, “Tim, what's your favorite Warner Bros. movie?” I'd be like, “I don't know.” I have no idea in my top 10 list of movies which one is a Warner Bros. film and which one is not. Probably the same thing for MGM, and you could go on, Paramount, all the studios. I don't honestly know which movies are made by which studios. You could copy and paste the intro into any movie and I would have no idea. 

Tim Chermak: This is, by the way, the Disney animation logo from the 90s, my childhood. And when I see that come on the screen, all sorts of nostalgia just floods. I think of seeing Hunchback from Notre Dame in theaters, or Pocahontas, or Toy Story. And that logo and that brand means something. At the time though, it didn't. Walt was the first person to kind of stumble on this idea of brand. What if the brand actually meant something where I could charge more? And because I have more money, then I could make better cartoons and better pictures, which would make more money, and then I could charge more, and it's kind of this flywheel of quality, creating more profits that builds a moat around your castle. 

Tim Chermak: So Disney really pioneered the idea of brand and entertainment. I have firsthand experience in this. I actually worked at Walt Disney World when I was in college. I joined the Disney College Program, and they are obsessed with brand. I probably was the most overqualified person to ever take a minimum wage job at Walt Disney World because I went there not wanting money, I wanted to learn how they trained their employees, which are by the way called cast members at Walt Disney World. Everything follows this theme of The Show. So you're a cast member, you're not an employee. You don't take your breaks in a break room, there's onstage and there's backstage. I had to go to costuming every day to pick up my costume 'cause they don't have uniforms, they have costumes. So everything at Disney is about this theme and this brand of The Show. 

Tim Chermak: So I went to the Disney Program just to learn how they train their employees. And the first three days that I get there, it's three days on the history of the company. So even for a minimum wage job, I'm working in attractions, which is a fancy way of saying, “I press the on button when you go on a ride at Disney World,” and I had to go through three, full-paid, eight-hour days on the history of the Walt Disney Company. Because they want someone in a minimum wage job to know if someone asked me, “Hey, what year was Mickey Mouse created?” I'd be like, “1928.” “What year was Disney Studio incorporated?” “1923.” “What year did such-and-such movie come out?” and you would know. They wanted even the lowest level employees, the lowest rung on the ladder, to actually be trained on the history and heritage of the company. Because an advantage to this day that Disney has over other entertainment companies is that sense of heritage and that brand. 

Tim Chermak: Can you imagine a Starbucks barista having to go through three, full, eight-hour, paid days of training on the history of Howard Schultz? I mean, no other companies do anything close to this. Even janitors have to go through this, which by the way, at Disney, there's no janitors, they're show keepers. They keep the show clean. So even a janitor has to go through three days of the traditions training. That's what they call it. Disney takes the brand seriously. 

Tim Chermak: Actually, on the first day, I was almost fired. I was sent home on my very first day because I showed up in violation of the Disney look, which is, again, the standards they have for the brand that you have to have this all-American, clean-cut look. So, no tattoos. Men weren't allowed to have earrings. Your hair has to be a totally natural color, so you can't show up with pink or purple hair. They want this kind of all-American, family-friendly look. And that also means no facial hair for guys, probably for women too. And I showed up, and the stubble I have right now would absolutely get me kicked out. They'd be like, “Go to Universal,” if I showed up looking like this. 

Tim Chermak: So I showed up, and I knew all this. Keep in mind, even before I got the job, I had read all sorts of biographies about Walt Disney, watched every documentary. I was obsessed with the man, Walt Disney. And so I get sent home my first day 'cause the manager comes up to me and says, “You're in violation of the Disney look.” And I was like, “What?” He's like, “You have a stubble.” And I was just like, didn't know what to say 'cause it's 7AM and I had shaved the night before at 10PM before I went to sleep because I knew that you had to shave before you went in, but apparently my five-o’clock shadow at 7AM was too much. 

Tim Chermak: And so they sent me home. He just gave me a disposable razor and said, “Go shave,” and I was just mortified. Like, okay, what do I do if I work a 14? Because often during spring break, especially in the month of March, you're working 14-hour shifts. So you'll work six or seven hours, take a long lunch break, and then work a whole shift after that. I was like, by the end of my shift, I will logically be in violation. And he just put his arm around me and said, “We'll talk about that later. For now, you need to go shave.” And so I had that experience on my very first day. Can you even imagine a modern corporation taking that level of seriousness with their employee's look? For a minimum wage job. I was standing in the dark all day. People wouldn't be able to see. I was at an indoor attraction that I worked. So, that was my first experience in how seriously Disney takes their brand.

Tim Chermak: So this is another older photo of Walt and his brother, Roy. And throughout the 1920s, and really, frankly, throughout the history of their entire company, they were constantly almost broke. No matter how much money Walt made, his ideas that he would have of how to spend the money were always so much greater than the amount of money he made, that they were almost always going outta business. No matter if they were talking hundreds of thousands of dollars, millions, tens of millions, eventually, hundreds of millions, Walt would find a way to reinvest the money, and it was Roy's job to just find a way not to go bankrupt. So to say that Roy had a finance background, he eventually became the CFO of the company, but he worked as a teller at a bank. They started this company together. Neither of them had any formal business background, but what they knew was, like I said, they could crack through, they could find a way to carve out a name for this Disney Brothers Studio, is what it was first called, if they could find a way to convince distributors that their characters for these cartoon shorts were better than the alternatives, they could charge more. And Walt worked really hard to develop a character called Oswald the Lucky Rabbit. 

Tim Chermak: Most of you have probably never heard of Oswald the Lucky Rabbit because it was stolen from Walt Disney in kind of a paperwork contract, hostile takeover, where he got into negotiations with his distributor in New York. And frankly, they just knew more about contracts than Walt did, and Walt didn't realize that he had signed away the rights to Oswald the Lucky Rabbit. And so once, when a contract got particularly in a fierce negotiation, he found out that the distributor had actually hired away all of his animators from underneath him, also owned the rights to Oswald. And so this character that was kind of ascending in popularity, overnight, Walt finds out, “I don't actually own any of the rights to Oswald. They've hired my animators. I have nothing.”

Tim Chermak: So as the story goes, he's on a train ride home from New York City, coming back to California, and he calls his wife Lillian and says, “I think I have an idea. I'm gonna come up with this new character. It's going to be a mouse. I'm gonna name him Mortimer.” And Lillian says, “Oh my God, that is the literal worst name I have ever heard in my life. Please do not name him Mortimer.” And Walt Disney, whose family is Irish, says, “What about Mickey?” And so they said, “Okay, that's fine. We'll name him Mickey.” And the idea was Mickey was gonna be this mouse. It's really Walt in animated form. It's this kind of spunky, punchy, all-American character who you just can't help but want to root for. He's always doing things and getting into things he shouldn't be, but he finds a way. Kind of has this can-do, all-American attitude of, “I'm gonna figure out how to get what I want in life.” And Walt actually in the early Mickey shorts, Walt is the voice. So it's actually just Walt Disney in falsetto. So if you go on YouTube and just search “early Walt Disney shorts,” that is literally Walt's voice voicing Mickey. 

Tim Chermak: So they come out with the Mickey character and cash starts flowing in. Walt has finally achieved this brand where he can charge more money from the distributors because people are actually calling movie theaters and saying, “Is there a Mickey Mouse cartoon before this movie?” And if there's not, they're literally going to another theater because they want to see Mickey before the movies. This had never happened before. It totally caught the whole industry off guard because people didn't care what cartoon shorts, in the same way that none of you in this room, myself included, would ever call AMC before going to a movie and say, “What trailers are playing before the movie?”






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