Jay’s Must-Listens: Want to Quit Your 9-5? 5 CEO’s Share the Exact Steps to Start Your Own Successful Business (No Business School Needed!)

27:40I hope you got introduced to some great deals. Let's pick up where we left off. In order to break your frame and to see businesses all around you, don't assume that the same things you value other people do. It's like, I've never really believed in the golden rule, which is treat others how you want to be treated. It's like, by and large, treat them how they want to be treated, unless that breaks how you want to be treated. And I think that's the same with business owners. I mean, my Uncle Eb, which is one of the main reasons I started publicly talking about businesses online, he had a business, did a couple million dollars a year in revenue.

28:12And it's called Eb Homes Plumbing. It was in Phoenix, Arizona. And he got sick with cancer and decided he wanted to shut the business down. He's in his 70s and was like, I'm ready to be done. And what he didn't know at the time is that a business that is doing a couple millions of dollars in revenue and a couple of millions of dollars in profit is worth millions of dollars. And so this man who spent his life building up a plumbing company that probably would have thought, honestly, like if he was here, he would say, Cody, I couldn't have sold that thing. Like that wasn't really, you know, it was sort of, and this is what most baby boomer business owners think.

28:51They're like, who's going to buy this? Because how many times have you had a business where you didn't want to be in it before? Have you ever had that before? Yeah, absolutely. Of course. Like if you're in a room, sometimes I go out to speaking stages and just for shits and giggles, because people will always go, if a business was profitable and it was going to continue to be profitable, nobody would sell it. And I go, okay, let's play a game. Business owners, raise your hand. Everybody raises their hand. That's a business owner. I go, cool. Keep them up. If you would sell your business at the right price and the right terms, if it came along, Keep your hand up.

29:22What happens? Everybody's up. Not one. If you go down and I go, liars. And I laugh. Because the truth of the matter is, you haven't been in the game long enough if you put your hand down. But if you've been in the game long enough, you go, absolutely. Now, I wouldn't sell every one of my businesses. Of course. But there is at some point one business. And if you call me on the right day, maybe I would. So I think we have to change our programming to realize all around us, every business has a value. That book selling business that shut down, I bet there was a value in the lease that they had. It might have been in California.

29:55Sometimes they have leases that are locked in. There could have been value in just the lease contract to transfer it. There could have been value in the assets, the books. There could have been value in the employees because you can do an acquihire. There could have been value in the website listing. What about the Yelp and Google reviews? There could have been value in the IP. What about the logos and the brand and the name? What if they had one of those old school, original, you know, cody.com websites before, like we now have to have websites that are like 452 words, right? And so every single business has some value.

30:26And if you can find the business where the value to the owner is not as much as the value is to you, then you got a really good deal. Next up, Brian Chesky speaks on how to transform ambition into meaning and how to build with heart. Maybe you want to help the world. Maybe you want to build something powerful. Maybe you have a voice that you want to share, but you've got to turn that into execution. You've got to turn that into impact. That's what Brian focuses on. Brian talks about how your company has to reflect your inner world and how leadership starts with knowing yourself. He talks about how he views Airbnb as a form of art and how to transform your creative passions into a successful company.

31:10This clip is all about how do you take an idea How do you take a concept? How do you take a thought and turn it into something real? I want you to stop dreaming and start building. What makes you happy today? And how does it differ from what made you happy 16 years ago? I think that I'll start with what I thought would make me happy. And I'll tell you what does make me happy and how they're different. When I started this company like 15 years ago, I started my co-founders. I was totally broke. I had no status, had no power, no money, nothing. And I felt like what would make me happy was climbing a mountain and becoming incredibly successful.

31:53And the challenge is that, well, what do you do when you get to the top of the mountain? You've achieved it. And what I've realized is, at this point, like I'm 41 years old, and a lot of people ask me, like, why don't you just retire? Like, why don't you do it all over again? And for me, I would tell them because the fun is just starting. But the fun of just starting isn't to get the next billion people. I kind of think of myself maybe more than a business person. You're kind of who you are growing up, and I was a designer growing up. And I kind of think of Airbnb as one of the world's biggest canvas.

32:35Almost never has a designer been given so much responsibility. so much opportunity. And what I love is, you know, like a musician wants to play music, a painter wants to paint, a builder wants to build, a climber wants to climb. And as an entrepreneur, I want to create and connect things and try to like defy the notion of what a business person could be or what a designer could be. Because I never met someone like me growing up. And I'm not saying anyone's going to try to be like me. But if I can remind people that there's leadership comes in many different faces, many different flavors, and that a creative person, you know, can run a company and it can run a really big company, a fortune 500 company, then that's, that's the very beginning.

33:25And I feel like what makes me happy now is working with people I love. Like the, one of the great things about success is you can choose the people you surround yourself with. And I get to work every single day with people I love on ideas that I'm obsessed over. And I'm just so obsessed. I think my motivation's changed. I think when I started, my motivation was about myself becoming something. And once you achieve that, your motivation often turns outward. It's starting to be about giving to other people, to letting them experience a small part of what I was able to experience. And it becomes just about the work.

34:08So when you're not successful, you get validation when people praise you. But eventually, you do it for yourself, that you're not doing it for status or success, because at some point you've gotten all of it. How much more is going to make you happy? And so just doing things I love with people I care about, that's what makes me happy today. That's beautiful. I can see that it's true for you too. I can see that it's real for you as you're saying it, which is such a special place to be. And it was interesting when you were talking about this idea of climbing a mountain, I've often thought that there's one journey in life that we take that's upwards up a mountain, and then there's another journey we all have to take that's inwards to the valley.

34:54And that's a journey that not everyone gets to take or everyone thinks about taking because we're so busy trying to get up that we don't often get to go in. And it sounds like you've been excavating that internal part for some time. You can learn a lot about yourself through this journey. And you're right. The biggest journey I've probably embarked on is the one inside of myself. The brightest days of my life and the darkest days of my life have been in the last 15 years. The highs are incredibly high. The lows can be incredibly low. The amount of stress can be unrelenting. The rewards are hard to even grapple with.

35:34When you go on a journey like this, you learn a lot about yourself. And you start to also learn what's important to you. Starting a company, one of my first investors said, Brian, starting a company is jumping off a cliff and assembling the airplane on the way down. Maybe another way of saying it is playing a video game and it's like a thousand levels and each level gets harder. In each level, you learn something about yourself. You do something that's uncomfortable. In each step of the game, you learn something. And the problem with success is it tends to amplify things. I mean, that can be good, but it all can still can amplify holes you have in yourself.

36:13People that are a little bit paranoid get very paranoid. People that are a little deceitful become like completely fraudulent liars. People that are a little narcissistic become like egomaniacs and stuff. And so this stuff can tend to amplify tendencies inside of yourself. And so if you're afraid of conflict, that's going to actually manifest in like not actually dealing with things. If you're not decisive, there's going to be an element of bureaucracy. If you get overwhelmed and you get paralyzed, there's going to be an action in the company. And so you learn so much about yourself. and I, through this process, I probably learned more about myself than I even have about business and it's been an incredible journey and yeah, it's like incredible lessons and the company is like a mirror about you, right?

37:00Like when you see a company, it's like I walk in your house and by walking your house, I can step a little bit in your mind because the house, you bought the house, you furnished the house, you made a thousand decisions and it would take a while for me in conversation to understand you but I walk in this house and I can understand the thousand decisions you made. A company is like that, but it's like a hundred thousand decisions or a million decisions. And so by seeing the company, you can like see into the person's mind, everything they do, and not even everything they do, but everyone they surround themselves with and the culture they create and what they, and that's the thing that's like so crazy.

37:36I'm intrigued. You said something there that really stood out to me. You said that the happiest thing and the best thing about being successful is that you get to choose the people you worked with you obviously built this with friends yeah and that's how it started it started in a place of being around people you love with what was the biggest point of challenge in building something with people you love as you grow it and what is it that you experienced and what was the biggest lesson that you took away that actually kept it going because i can imagine as you're describing highs and lows all of this changed for 16 years but here you are still building it together.

38:13Think about how many stories you've heard of founders. It's like a band. They come together and then eventually the band breaks up and people don't stay together. They resent each other. Maybe things end very ugly. It's like a band except like it's become so much bigger than a band because it's not just the three of you. Imagine a band that starts three people and ends as 3 ,000 people. And that amount of pressure, the amount of spotlight, the money, the changes in people's status and positioning, it can do a lot to break people up. But also, unlike a band where maybe, not to say you just have to agree on where you perform and what you sing, with a company you have to agree on who we're going to hire, what we're going to call, what markets we're going to go into, what's the prioritization, who we're going to raise money from.

38:58I can go down the list of the thousands of things you have to agree to. And with Joe, Nate, and I, I often say it's really good to start a company with friends. Not everyone has friends to start a company with. but you want that reservoir of goodwill. And we made a decision. The decision was that no one decision is gonna supersede our friendship and our relationship, that we're never gonna have, well, debate, we'll argue, but we'll never allow a situation where winning an argument is the most important thing. Because if you think about a company as 100 ,000 decisions, it could also be 100 ,000 arguments.

39:32And if you get stuck on the first debate or you like somebody won a debate, okay, great. you have 99 ,999 more things to discuss. And so the lesson I learned is, I mean, first of all, Jay, I was lucky. And a lot of people, when I say I was lucky, they think, oh, you were at the right place, the right time with the right idea. And I said, well, maybe. But there's something I was much luckier about. And what I was most lucky about, what made me most fortunate was I met Joe and Nate, that we had this unbelievable chemistry. One time we had to do like some personality test. It was like one of those core wheels.

40:06and we took this personality test to see about our chemistry and they plotted our personalities and they formed a perfect equilateral triangle. Not always you're gonna find people that are perfect compliments to you. I'd say a couple of things. Number one, you wanna have a team with people that you are friends with or could see yourself becoming friends with that you have a deep love and respect for, that you're gonna probably spend more time with your co-founders than your spouse or your family if it goes well, If it doesn't go well, then maybe not. But that's the best case scenario, that people that have shared values.

40:40Because you can debate anything so long as you're trying to climb the same mountain and the same fleece system. If you have different values, eventually those are going to become irreconcilable conflicts. But you probably also want complementary skills. The worst case is people with different values and same skills. We do the same job. We step on each other's tolls, and we're trying to go in a different direction. And then I think the final thing is just this mutual love and respect and never losing sight. One of the things I tried to make sure of is even as CEO, I wanted to try to make sure that Joe and Nate were included in things.

41:14And I wanted to always make sure that people referred to us together. We thought of us as a unit. When I went public, you write a founder's letter. And a lot of people write the letter and they just sign the name of the CEO. I made sure that it was from all of us and was representing all of us. I feel like they are the heart and the soul of the company. And it's like, you know, parents, like, you know, not every child has the fortune to have multiple parents. Not every company has the fortune to have multiple founders. But if they're together, they're not fighting, they have a mutual love and respect from another.

41:46That's going to permeate the company just like it permeates the health of a child. And Joe and I kind of thought ourselves as parents of the company as a child. I'd never have had kids. but there's something about that. And I think who you are and that relationship permeates every single thing. If the founders fight, the employees fight. If they have respect for one another, that is gonna be a role, a model that other people throughout the organization are gonna copy. And that's what I've learned from that. In this conversation, Michael Rubin shares how staying obsessed, learning fast and staying hands-on drives success.

42:21Too many of us don't learn fast. Too many of us don't test enough. He talks about how entrepreneurship is learned in action. A lot of us are thinking, we're theorizing, we're planning, we're preparing. Rather than diving straight in, we're focused on trying to feel ready. We're trying to focus on being confident. His point is just do it. He talks about how pattern recognition is a superpower. Spotting what others miss is your competitive edge. I think it's something for me I was born with like I was born with that entrepreneurial hustle I think I came out of the womb like just you know wanting to be an entrepreneur like just loving the hustle and you know to me you know I've been at this a long time I work harder than I've ever worked today I love it's an honor to do it's fun it's an opportunity like I'm never tired I'm never worn out like I'm just always I just want to go yeah can it be learned can you teach people to hustle and grind and develop that mindset or is it born with as you are so I think I was definitely born with it.

43:20That said, I do think, you know, for me, the way I learned is by being a sponge from people. So I'm always picking things up from different people. Like if you just look at the diversity of people I have around me, like I'm always taking so much learnings from them to, you know, be better in what I do. And I try to give those back. So yeah, I think you can definitely learn a lot of this stuff. Just, you know, find people you respect, find people that you admire, find people that you want to be like, and then, you know, take the good from them. And by the way, figure out what they do that you don't like and ignore that.

43:47Like I see good and bad in each person i try to take the good and learn from the bad and same thing with me i've got lots of bad habits i mean like i'm myself that's right that's all i asked for that's all i asked for there is no judgment here there's no it's a safe space i just want people to be their authentic selves and so so please continue to be yourself and uh what's so what i love that idea of learning from people being a human sponge what's the most recent or most memorable thing you think you took away from someone a conversation a moment uh something you read or heard or learned was there anything that kind of stuck with you?

44:19Yeah, for sure. I mean, look, I'm in LA for the week. I'm doing six to 10 meetings a day in my house. And, you know, two of the people I met with in the last two days have been through some real challenges and just watching the challenges that they've been through. I'm like, okay, I need to be that much more careful about how I conduct myself and everything that I do. So to me, I'm always taking learners away from people. I think if you're not like, you know, you have no chance of like, you know, getting better at what you do. I mean, it's like life is no different than sports. You just got to keep getting better at your sport.

44:47So to me, I keep working in everything I do. Yeah. What do you think? Obviously now, like when you started 43 years ago at eight years old, entrepreneurship wasn't as touted as this incredible opportunity. No, it wasn't touted. It was actually weird. Right. Like to be clear, like I was a nerd, like that I loved business. Like entrepreneurialism came cool really around technology. Like I don't think it became cool till almost the, from my perspective, I think it was really the birth of the dot-com era. Or, you know, kind of late 90s is when entrepreneurialism became cool. I think before that it was kind of nerdy and weird.

45:20So I was definitely born before it all. Yeah. And I'd say even after the financial crisis in like 2007, 8, like that recession, which is because I grew up in the era where we still aspire to be investment bankers or consultants. So when I was at college or when I was growing up, that was seen if you were into business, my goal was to go into that world because that's what I aspired for. Whereas I think the generation after me and the one after me, they were like, I'm not going to go work for someone. when I want to build something on my own. I think that's amazing. For me, I love, one of the things that I'm fortunate enough to do is really, I think in a lot of ways, you know, encourage entrepreneurialism.

45:54And, you know, one of our biggest businesses, the collectibles business, which is trading cards and memorabilia. And that's all about entrepreneurs. There's so many entrepreneurs in that business. It's probably the business in a lot of ways that I, I actually relate to all three of our businesses, but it's the business that's maybe the most relatable for me because I grew up selling trading cards as an eight-year-old, but also it's all about entrepreneurialism. Talk to me through that business because, So I remember, so back in London, obviously, where I grew up, I collected football stickers, right?

46:18Soccer stickers. So that's what we'd have. We'd have the big, you'd have the spread with all the Premier League clubs and you'd collect the little stickers. And that was a big part of collectibles. How has that industry evolved as technology's grown or has it stayed the same? Were people still collecting cards and like Top Trumps and things like that? Yeah, well, I'll say we got into the business about three years ago in a really significant way. And today we own Topps, which is the, you know, kind of preeminent brand in trading cards. I'd say that, you know, until our arrival in the industry a little less than three years ago, I said there hadn't been, you know, a tremendous amount of innovation.

46:49There hadn't been a tremendous amount of marketing. You know, we kind of looked at the business and said, wow, like this is such an incredible collector base, such an incredible fan base, yet it hasn't changed for like decades here. And you go to a, you know, the big trading card show where there's more than a hundred thousand people that come to Chicago this past summer. It's called the National Trading Card Show. Yeah, it looks like something from 20, 30, 40 years ago. So for us, that just meant opportunity. It meant if you actually make innovative products, you actually really market these products, you build a better consumer experience and bring people forward into 2023, like what an opportunity.

47:22So for me, we do that in all of our business. We love finding great opportunities, big challenges and kind of being unrelenting about going after them. Yeah, how has that changed? How has that practically changed? Like are people still buying cards and trading? Yeah, physical cards are the biggest part of business. In a lot of ways, it's very similar to art. But I can tell you, just as one quick example, this year, our team came in and actually the CEO of our business, Mike Mahan, said, hey, I got a great idea. Every time a player debuts for the first time, I want to put a patch on their jersey.

47:50And then as soon as they get done the game, I want to put that patch off and put it in a one-on-one trading card. Oh, that's sick. So you have the card from the first. So think about for us, maybe I grew up in the Michael Jordan era. Or had I had, you know, Michael Jordan or, yeah, if I had Michael Jordan or Kobe's first one-on-one cards, yeah, that could be the most valuable keepsake that I could ever have. And so, you know, that innovation, like for us, it was really simple. Like, yeah, why would you not want to put a patch on someone's jersey, stick it into a card and make this a one-on-one card?

48:17But no one did that until we created it. And by the way, it's already live. We came up with the idea this past December. It was live in April with all baseball players. It's going to be 300 to 400 baseball players debut this year, you know, with this debut patch that we put into a one-on-one card. That's just like one of dozens of examples of innovations because you have to be aggressive. Like we have to be great entrepreneurs. We have to push in whatever we do. Yeah, no, what I love about that though, for everyone who's listening is, I think we're stuck in this world now that believes that all innovation has to be digital or technological or virtual or some sort of AI.

48:48Whereas this is like the most tangible physical change, but it's still so valuable because it's what people want. Look, we're in three business there. First business where we started is what we call Finax Commerce. That's a merchandise business. We own Lids, the retailer. We own Mitchell Ness. We own Fanatics, which operates, you know, obviously all of the different league, you know, the NFL shop, the NBA store. And we sell, you know, more than$6 billion of mostly fan apparel and headwear, okay, about, you know, more than 100 million units of merchandise a year. That's a very physical business, okay?

49:19But AI is helping us to do things more effectively. In the collectibles business, AI is going to help us to be more effective. And then our third business is the online sports betting and iGaming business. So, you know, for me, we still do a lot of physical things, but there's so many things in the digital world that help us to be better. Yeah, no, but I love that collaboration and thinking about it that way, because sometimes the greatest value to someone is a physical change, but you're learning that through the AI. I'm excited to keep this conversation going. But first, let's take a short break for our sponsors.

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51:09Equal housing opportunity. Okay, we're back. Let's dive right back in. I still want to wear my Kobe jersey. Yeah, exactly. I want my Bron card. Yeah, that's the same thing. I'm still buying, I support Manchester United. That's my soccer team. And I'm still buying, you know, soccer jerseys every single year. Well, we appreciate that because that's a fanatic side. That's the next door. Even though I absolutely, even though we absolutely suck right now. But it's, you know. But that's what being a sports fan is about. Sometimes you're going to have great years and you're getting those championships and other times you're going to suck and you got to stay with your team.

51:40You got to feel the pain. I'm a real fan now. I grew up as a glory hunter because we just won everything. and now I'm going through real fandom of 10 years. We're going to test you now. We're going to see what you're made of. Are you really committed to Man United here? Yeah, I'm being tested right now. I'm being tested. But we were talking about people not being, entrepreneurship not being touted when you started. When you look at it today, now it's become the cool, sexy, interesting, fascinating thing for people to want to try. It's not necessarily things people are good at, like you said you were.

52:08It's not necessarily a skill that we honor or give it the kudos that it deserves. what are the mistakes people are making when they think about being an entrepreneur today well first of all entrepreneurialism isn't for everybody but if you think it's for yourself you better go out there and try it put your best foot forward you know for me look the biggest mistakes i see people make in building a business are kind of a couple common themes one is first you have like are you even going to take the at-bat so many people tell me i've got this great idea but like i don't want to hear about but like let's go for it let's if you have an idea you want to do something you know I love the story you were just telling me before we went on here that you came over here and you know you worked one place for six months then you're like I want to go out and do this you went out and did it like part of being an entrepreneur is to have the courage to fail like you just have to go out there and try and by the way when you fail which many times you will you're gonna learn from that failure you're gonna grow from that failure you think the best you talked about Kobe being your favorite you know athlete well guess what how many times did he fail and then he got better and he pushed through and so that's what being an entrepreneur is so from my perspective, it's really all about first and foremost, if you have something you want to do, if you believe in it, go for it.

53:17Don't worry about whether you succeed or not. Go out and take the swing. And if, guess what? If you strike out, if you fail, just go back again. And I know some people are going to say, oh, well, he's really successful now. So it's easy to say, but I got to tell you something. I've like, I've seen death in its eyes. You know, I've almost gone bankrupt multiple times. You know, I've had epic failures and every one of those led me to be better in what I do. So that's my first thing. Second thing I'd say is you need great people around you to succeed. Like whether it's great people you're learning from that you want to be a sponge from, whether it's you build a great team to do what you do.

53:48Like I know for fanatics, we have 18 ,000 people that get up and go to bed obsessed with how do we improve the fan experience each day. But like I collect and work with the best people on the planet. Like if you don't work with great people, you will fail. Like you can't win a championship if you don't have great talent, but that talent also works, needs to work together. And then the last thing, and this will sound corny but like have fun in what you do like i love what i do i have the greatest you know job in the planet i get to wake up you know work 18 hours a day go to bed thinking about you know what's next i dream about my work nearly every day like i'm having work dreams all the time because i'm obsessed with what i'm doing it's like it's it's fun it's like i should pinch myself it's so awesome what i get to do i think pattern watching is is an ability whether it's an algorithm whether it's the stock market whether it's you know crypto whatever it is for people watching patterns is such an unbelievable skill.

54:35Would you say that's a skill that you've honed and developed and built? Well, I think it's a really important skill in business because I think it's very predictive of the future, okay? So the reality is when someone comes in and I'm interviewing a top executive for a role in one of our businesses and they could seem great. And then I'm gonna go out and I'm never gonna ask anybody for a reference ever. I've never asked somebody, hey, can you tell me who to call? Like that's the, you asked me for reference on myself, I'd call each other's people and say, hey, I gave you as a reference, make sure you say great things about me, right?

55:01So the reality is I'll interview somebody. The first thing I do is if I like them, as soon as they leave, I go out and I start calling people that I knew we had in common to recognize patterns. Because to me, 50 % is the interview and 50 % is what I learned behind the scenes. And that's probably the more important 50 % because someone can blow me away and then you'll find out in one minute, that person sucks, that person, people don't like working with them. Or you can find out that person was a little bit understated, but they're a beast. They've got huge followership. they're super smart, they've got an unrelenting work ethic.

55:35So to me, pattern recognition is everything I use in everything that I do. By the way, I use pattern recognition when I go play blackjack with my friends. You know, there's three types of cards you're going to get. Cards are either going to be, you know, you're either streaking hot, you're streaking cold, or you're kind of in between. And, you know, when you're cold, you should not do what sometimes I'll do if I'm misbehaved, which is be aggressive when you're cold because you got a pattern going on. So you got to recognize patterns in whatever you do. In our final clip, Sunira Madani reflects on building a billion dollar fintech by embracing risk, clarity, and consistency.

56:06Maybe you don't know when it's time to take a risk. Maybe you wonder about do you have enough clarity to move forward. This clip will help you make that make sense. She talks about how leaving security is often the first real entrepreneurial step. You will have to trade your comfort for courage if you want to succeed. she'll show you how to do that. She'll also show you how to bet on boring problems. We think that if we solve this sexy issue, if we come up with this sexy brand, that's what we need to do. Sometimes solving the unsexy issues can lead to massive success. Check it out. When I talk to my male friends today and I know a lot of their wives and partners and girlfriends and whatever else it may be, they all find that so many women are scared to go out there and start a company.

56:56they're scared to take that risk. They're fearful that they can't, or they're waiting till they have everything, like all their ducks in a row before they give themselves an opportunity. How did early on in your life, your dad saying this repetitive statement to you, how did that not become a pressure? And how did it feel empowering? Because I feel that sometimes if you're told you've got it, you can do this, a lot of people see that as pressure and then they feel they can't live up to it. What was different about the parenting aspect of that? Because I think a lot of parents listening may take a lot from what your dad did, right?

57:30I was always brought in on all the conversations. I think something that my parents did, we had struggles and we had challenges and we had to move and we had to various businesses, but we were always at the dinner table having the hard conversations. You know, if there were hard things that were, you know, taking place about money or about business or about family, we were solving problems together. So my parents would always ask our perspective. That is something that I do feel is very interesting. Just as a child, I try to do that with my daughters at the dinner table now is to ask them like what they think.

58:03So thinking about solutions versus, you know, how they would think about solving it. So I feel like I was really involved in hearing my voice felt heard. And I think that's important because as women, I do feel like we're, you know, our voice isn't heard. And so I grew up in a place where my voice was not just heard, it was really valued. And my perspective was valued. And there's just like so many memories that I can think of. I had such an amazing, amazing childhood. And I know a lot of people don't have that. On my 17th birthday, this is really crazy. So we went to Atlantic City for a Bollywood concert.

58:36It was like a Shah Rukh Khan concert when they would come out and do the shows. We went to Atlantic City for this concert and you know, there was a casino. I'm not even of legal age to great gamble. And my dad takes me to the blackjack table. Okay. And he was an avid, like he definitely had not the best habits as well. And it's, and it's important to see, like you can see both sides of your parents, things weren't perfect. I look back and I think about mostly the positive, but sitting at this blackjack table. So I'm all dressed up to go to this concert. I'm sitting next to him. My parents were also really young.

59:08They had me when they were like 20. And so people are probably assuming I'm like his girlfriend or something. And, you know, but I'm sitting at the blackjack table next to him and he hands me a pile of chips. And he's like, bet. And in my head, I'm like, how much is this? Like, am I going to lose the money? You know, what's the value? And his response, he goes, just feel it. He's like, if you feel like you're going to win, bet more. If you feel like you're not going to win, pull back. My ability to now take risks and listen to my gut and not worry about, you know, like scared money doesn't make money.

59:41as well. Right. So my ability to be able to say, okay, I feel like I'm going to win. I feel like look at looking at the hands or learning blackjack and I was great at math and I can get this concept. That was one of my, like a core memory that I can think of, but I was always involved in the conversation. I feel like it was more tactical with action, not just being told that you should go do this. I definitely feel very blessed that I, that I did have that. And now my mom lives literally across the street from me. She's like one rock away and we get to, she gets to raise my kids with me. So it's wonderful.

1:00:14It's amazing. When you, when you go from pitching your idea to all of your bosses and they kind of look at you like, this is going to fail, this isn't going to work. And then obviously your dad gives you that encouraging statement. You said that you moved back home then. Yeah. So I'm imagining that you were making a decent amount of money working at a financial services firm. And when you choose to start a company, I'm guessing you took a massive pay hit. And I assume you were living out and then you moved back home. Now, the reason why I'm pinpointing that moment is because I think those golden handcuffs that so many of us tie around ourselves with the safe corporate job.

1:00:51And when you've got a great degree and you finally get that job you've been waiting to get for like 18 years of your life and everyone respects you for it. It looks good on your LinkedIn in and your resume, I found so many people struggle at that point to say, well, I'm willing to take less money. I'm willing to downgrade my lifestyle. I'm willing to postpone and delay the gratification of having nice things because chances are, if I live with my parents and I'm not making the money anymore, life changes. Walk me through deeply that decision because I think for so many of our community listening and so many people that I mentor, coach, speak to, this seems to be one of the most pivotal moments of their life that were you willing to go two steps backwards in order to go five steps forward?

1:01:38And so many of us are so scared to go two steps backwards because we've got so used to a certain level of lifestyle. So walk us through that key decision point. I actually ask myself, would I do it again? And I think that it also depends on, And it's the risk-taking ability, right? It takes courage to take risk. One of my favorite, most favorite books that I've recently read is Die With Zero. It is such an incredible book. It's this crazy concept of just taking risks and you have your golden years of your life. Like we should be spending our money, doing our things in our prime. And that makes complete sense.

1:02:15And the risk tolerance that you can take also changes with your age. Would I take these risks? If I had two daughters at home And maybe if I was a sole breadwinner or where, I don't know. And so I can look back and say, I didn't have much to lose. And it was a level of risk. I had a steady job. I was on a career path. I could have totally miserably failed. I think you have to think about not what is the risk in doing it. I think you have to think about what is the risk in not doing it, right? So what is the risk if you don't do the thing? And that's kind of how I try to make those, the risky decisions today.

1:02:51and I know we're going to talk more and this journey is going to come full circle in 10 years. I left my company at the most record high of the company. But the risk of me staying was a detriment to my health and my burnout and all the things that I had left to go accomplish. And so it's really about the risk of not doing the action. But at that time, I think I was young and I could. And you do have to take a step. back. And I would say, I think social media does a horrible job of showing us success. There's so much saturation of success. There's not enough failures that are being shown. It's not enough.

1:03:32It is hard to build a business. You know, less than 2 % of female founders ever even break a million in revenue. That is the most insane statistic. Men are eight times more likely to achieve that. Venture capital, right? I'm going to go build a fintech less than currently 2023, 23, less than 3 % of capital goes to women founders, less than 1%, it's in the decimals, goes to minority founders. What was I even thinking trying to go raise capital out of Orlando, Florida, not even Silicon Valley, right? And so I think there's a naivete when you're young and I think it's beautiful. I think that it's the most amazing thing.

1:04:10Like I even think about parenting, like, oh my God, now if I knew all the things that I knew, right, when we're young and doing the things. I think that having a little bit of not knowing what's on the other side is actually really beautiful too. Like embrace that. I feel like this generation might be missing out on the businesses that solve real problems that affect millions of people behind the scenes, that the opportunity to scale really, really fast because we're too busy trying to grow an online following. And so walk us through that understanding of how you encourage founders to find their niche and build their product and think about what they're doing.

1:04:47Because today it's been like, oh, well, if my brand hasn't had a viral video yet, it probably won't become big. So walk us through that a little bit. It's done so much good, but it's ruined us, right? Like it's ruined us in so many ways. We have to stop doing things for the gram. We have to, it is our mentality of building companies, products, services, that if it's not this, then it's not that. And I also think that it's important for us to have a social presence and to utilize all these tools that we have. So there's so much good that can come from it, but it doesn't have to be all of it. And so I do think it's important.

1:05:22There's so much opportunity out there. Most entrepreneurs that I know of personally that have been really successful came from a corporate position that like saw something and then they wanted to go tackle this one unique problem. And these unsexy businesses are solving the most complex problems for us. So we did$40 billion in payments through this ecosystem that I almost didn't start. If I didn't build it, we solved huge problems in this. It was so unsexy, card present versus card not present. So Stripe was focused on digital transactions. Square was focused on in-person transactions. Guess what?

1:05:57There was nobody bridging the gap for like dentist offices that needed both in-person and online transactions. Boom. There was the opportunity that nobody saw on building that tech. And it's not about, I didn't have the background. I wasn't a coder. I wasn't an engineer, but I could see where the world was going. And I think that's what entrepreneurship is. It's the spirit of solving for problems. It's not for show. Success will come if you just like let go of that. And you can also have a social following and build a great band and have the podcast and do the things to go reach more people. But you can solve, If you just focus on solving the problem and seeing it uniquely.

1:06:37And if it's one of you, you're really like, it's resonating with you. Cause you're like, I am that person. I I'm always finding like you're in the shower and you're like, this should be better. This could be better. Right. You're, you're always finding the next thing, but ideas don't make you an entrepreneur. Execution does. Right. Everybody has ideas. It's really about execution. And that's the thing. I feel like that's the thing that I saw maybe in like Sal and I growing up was like, you've got to put in the work. Even after everything that I have, I show up every single day and I work. I put my head down at night and I ask myself, did I like give my$110?

1:07:12I work so hard still. And it's just part of, and yes, I work smart too. So it's not that I'm not just grinding my way. I'm being intentional. But hard work is a huge part of it because there's no such thing as a billion-dollar idea. It's a billion-dollar execution. and to execute, it's every single day. You just got to keep showing up. And like that mountain, the mountain's going to be there and then you're going to climb it. And guess what? You're going to get to the top and you're going to climb this thing. The next day, there's another mountain and there's another mountain. So you've got to love that challenge.

1:07:44That's what entrepreneurship is. It's not, I didn't build a billion dollars. It took me 12 years to build that business, 10 years to exit that business. It didn't happen overnight. It happened because I just kept showing up. It wasn't this magic formula. People ask, what was the secret to the billion-dollar success? I didn't give up. I just somehow kept showing up. I can name every founder's, every journey where we almost didn't make payroll. I had to put my mortgage on the line. We didn't get the investors. We lost the customers. But you just keep going. And so you have to find that why to really power you through.

1:08:15And for me, it was, I just love to solve really big problems. And that's why even after exit, it's like, here I'm back again and building again. And it's because I see the problem and I know we can solve it. Yeah, I think you're the right person to ask this question to because you talked about working hard and working smart. But what was the mindset shift in building a million dollar business, a hundred million, and then getting to a billion? Like what changed? Because I think there may be people listening who've like built the million and they're like, I want to get to 10 or a hundred. I don't know what's, what do I need to do differently?

1:08:50Because I think at every level, there's a different mindset, a different type of work that's required. And often we don't talk about that enough. And so you keep doing the same thing again and again, expecting a different result, as Einstein said, is insanity. What was different? What did you find that you had to up-level to go from one to a hundred, a hundred to a billion? You're brilliant because everything has to change. It's completely different. Going from your zero to six figures, you know, getting that validation of your, it's a completely different journey from zero to six. from six to seven, it's a completely different journey and everything breaks and it's supposed to break.

1:09:27Going from seven to eight figures in revenue, it's going to break again. Your systems are going to break. People are going to break. It's going to break because it's supposed to. Once you get, you know, you get things right, or you think you get these things right. If you're doing what you've set out to do, which is go get more customers, go get more revenue, there's pressure on that system. And then you've got to recalibrate. You've got to recalibrate the tools. You've got to recalibrate the next level of scale. And so it is supposed to break. But the one thing that's not different, if I look back, so we had to change our mentality on growth.

1:09:58We had to get new technology. Scale is, it's not simple, but if I were to boil it down, it comes to three things. It's people, process, and profit. You've got to scale your people, you've got to scale your process, and you've got to scale your profit. Most companies that go beyond that market validation of million in revenue and you're trying to get to the, you know, or the hundred million in value, they have multiple lines of revenue. And so you're thinking outside of the box. So once we were acquiring small businesses, we've shifted to an enterprise strategy. Now I'm building again. We're selling directly to the banks.

1:10:28We're going directly to enterprise first because that was the one to many that I, it took me seven years to unlock that next. And then I'm going to go to small businesses. So you have to be able to tap into that scale of people, process, and profit. But the one thing that I would say stayed exactly the same, and it was so important for me, I wanted to be the one to see the company through to exit. And I worked so hard being overprepared over all the things so that I could be the best CEO that I could be. I put so much intentionality behind working really hard to be the best leader that I could.

1:11:01And the thing that carried me through that was exactly the same was our values in the company. I think we hired the right people. We fired the right people. And those decisions are hard. And our culture was really built on the value system. I mean, I have one team tattooed here on my arm. It comes from that meets me and my brother. We're one team. We're one team, one dream. Like that's how it's been since we grew up. That's what I wanted our team environment to be like. And so building that culture, the DNA value system and those core values, those don't change. Those evolve, but that needs to stay grounded and the same as you're scaling.

1:11:42Then you just shift into, those are just like, it's just the next playbook. It's a different heart at the next level, but you can solve it and you can find people to solve it. And then at that next stage, we had amazing leaders at the$100 million mark. And when I started the company, the name of the company was Fat Merchant, by the way, because I was 25. You know, it was, it was fun and we were disrupting the industry, but I knew that Fat Merchant was a hundred million dollar company. Stacks was a billion dollar company. And I had to get comfortable, even though it was my, to make those pivots, to make those changes.

1:12:16And so you've got to see where it's going and you've got to be willing to just throw it away and to start again at that, you know, to bring in, we had to bring in new leaders. That's hard. Change is hard for organizations. and so you've got to go build and to be willing to, willing to change, it's supposed to break, so get comfortable with it breaking and you just get better. It doesn't get easier, but you get better. These founders didn't wait to be picked or wait until they felt ready. They created, they evolved, but most importantly, they continue to show up. Whether they built from passion, necessity, or grit, they remind us the world doesn't need more noise.

1:12:54It needs more builders. So if you've been waiting, start small Stay hungry, solve real problems And keep showing up If this is the year that you're trying to get creative You're trying to build more I need you to listen to this episode with Rick Rubin On how to break into your most creative self How to use unconventional methods that lead to success And the secret to genuinely loving what you do If you're trying to find your passion and your lane Rick Rubin's episode is the one for you. Just because I like it that doesn't give it any value like as an artist if you like it that's all of the value that's the success comes when you say I like this enough for other people to see it.

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1:14:56Toyota, let's go places. This is an iHeart Podcast.