On Purpose with Jay Shetty - 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!)

Episode Date: July 30, 2025

Have you ever thought about being your own boss? What kind of business would you start if you could? In this special compilation episode of On Purpose, Jay Shetty curates powerful insights from five extraordinary entrepreneurs: Emma Grede, Michael Rubin, Codie Sanchez, Brian Chesky, and Suneera Madhani, offering a dynamic, behind-the-scenes look at what it truly takes to build something meaningful from scratch. Each guest brings a unique lens to the entrepreneurial journey: Emma Grede reminds us that the most powerful companies are born by solving real problems for underserved communities; Codie Sanchez breaks down how grit, financial fluency, and deal-making are more crucial than a flashy idea; while Brian Chesky reveals that building a world-changing company like Airbnb starts with seeing your business as a reflection of your inner world. Jay weaves these stories into a powerful masterclass on purpose-driven entrepreneurship, showing that success doesn’t come from confidence, funding, or perfection. It comes from grit, learning through failure, and showing up again and again. Michael Rubin drives home the power of obsession and adaptability, while Suneera Madhani brings it back to reality, reminding us that the biggest risk isn’t failing, it’s never starting. It’s a powerful reminder that stepping out of comfort and into aligned action is where true transformation begins.  In this episode, you'll learn: How to Build a Purpose-Driven Brand from Scratch How to Master Deal-Making and Speak the Language of Money How to Stay Innovative When Success Hits How to Start a Business Without Industry Expertise How to Scale a Company Without Losing Your Values How to Take Risks Without Letting Fear Lead the Way The most meaningful work often comes from solving problems close to your heart, staying curious, and showing up even when it’s hard. You are not too late, underqualified, or behind.  With Love and Gratitude, Jay Shetty. Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here. What We Discuss: 00:00 Intro  03:06 Start With the Problem Only You Can See 06:40 The Power of Who’s in the Room 08:10 Believe in Your Vision Before Anyone Else Does 10:44 What Really Motivates You Every Day? 13:26 Three Essential Skills for Building a Business 18:33 How to Master the Art of Deal Making 28:03 Redefining What Success Means to You 31:10 Life’s Greatest Lessons Start Within 34:17 Surround Yourself With the Right People 38:54 Can Hustle and Drive Be Taught? 40:46 Learn by Observing Others’ Mistakes 41:30 What is at the Heart of Entrepreneurship? 42:52 Bringing Innovation to What You Love 47:14 Avoid These Common Mistakes when Building a Business 49:44 Pattern Recognition Is a Business Superpower 52:05 Why Hard Conversations Build Stronger Foundations 55:34 Courage Is the First Step Toward Risk 59:46 Start by Solving a Real, Specific Problem 01:03:49 What Got You Here Won’t Get You ThereSee omnystudio.com/listener for privacy information.

This is an I-Hart podcast, guaranteed human. I'm Ibel Ongoria. And I'm Maite Gomes Rejoin, and this week on our podcast, Hungry for History, we talk oysters, plus the Miambe chief stops by. If you're not an oyster lover, don't even talk to me. Ancient Athenians used to scratch names onto oyster shells to vote politicians into exile. So our word ostracize is related to the word oyster. No way.

Bring back the omniscience. Master Khan. Listen to Hungry for History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Radhdi Dvlukaya and I am the host of a really good cry podcast. This week, I am joined by Anna Runkle, also known as the crappy childhood fairy, a creator, teacher, and guide helping people heal from the lasting emotional wounds of unsafe or chaotic childhoods. Talking about trauma isn't always great for people. It's not always the best thing. About a third of people who are traumatized as kids feel worse when they've been. talk about it, get very dysregulated.

Listen to a really good cry on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. I'm Jonathan Goldstein, and on the new season of heavyweight. And so I pointed the gun at him and said, this isn't a joke. A man who robbed a bank when he was 14 years old. And a centenarian rediscovers a love lost 80 years ago. How can a 101-year-old woman fall in love again? Listen to Heavyweight on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Have you ever felt like there's something bigger you're meant to do, but you have no idea where to start? Do you have an amazing idea for a product or a company? Or you've come up with an incredible solution to a problem you feel could help people, but don't know what to do with it. Or maybe you're stuck at a 9 to 5 right now, which is really a 9 to 9, which is just funding someone else's dream. When you could be building your own, recent reports show that 19% of the US adult population is actively engaged in either starting a new business

or currently running one. Whether you've been thinking about starting a side hustle, quitting your job and building a company of your own, or whether you're in the process of doing it, this episode is for you. You're going to hear directly from five of the first. the best entrepreneurs that I know. You're going to be hearing from one of the co-founders of Skims, Emma Greed, which is a company now valued at over $4 billion. You're going to hear from Michael

Rubin, founder of fanatics, the sports apparel company that was last valued at $31 billion. You're also going to hear from Seneira, who sold her last company for just over a billion dollars. Brian Chesky, the founder and CEO of Airbnb. And from Cody Sanchez, who's a self-made millionaire, specializing in small to medium-sized businesses. Whether you're fascinated by fashion, tech, apparel, or whatever it may be, we've got you covered. You're going to hear from them directly

about how they navigate innovation, how they dealt with rejection, how they focused on scaling their businesses and the deep personal journey of balancing gut instinct with strategy. Do not miss this episode. No matter where you're from, you have the opportunity to transform your life right now. This is a true masterclass in what it takes to building something from nothing. And I've put it together just for you. The number one health and wellness podcast. Jay Shetty. Jay Shetty. In this first clip, Emma Greed dives into how she launches

purpose-driven brands rooted in real problems people face every single day. This is a great lesson for you all. Start with what's missing. The best business ideas come from solving your own unmet needs. Design for the overlooked customer. There are parts of society that don't get seen, don't get heard, build for them. Acknowledging the unseen audiences builds unshakable loyalty. One of the things I love that she talks about

is that better business begins with better representation and diverse voices lead to better decisions. If you're someone who's always felt restricted because of your background or walk of life, this episode will empower you to think differently about your differences. How do you select problems to solve?

How do you choose which problems you want to work on and then make sure that you build something that actually solves that problem? I think about it in the sense of myself. I think it would be very difficult for me, and I'm not saying other people can't do it, but to do things that you can't relate to, right? So I always start with the idea that if it's a problem for me, likelihood is it's a problem for other people like me, whether that be other young women or other women in the middle of America, but it's like the starting point,

it's always, what do I find problematic? And then I think the lens and the, the kind of red thread that goes through all of my companies is this idea that, and again, I hate saying it because in the last kind of five years, it's almost become like this sort of buzzword. But when we think about inclusivity in business and what that actually means, including and thinking about the most amount of people possible, when I started Good American, it was actually a reaction to this idea that so many women, women of colour, plus-sized women, are just completely left out of the fashion conversation.

And why is their dollar any less valuable than anybody else's? And so I had worked in marketing for all of these years. For 15 years, I grew this incredible agency. And I'd done castings and, you know, put projects and collaborations together for the biggest and best brands in the whole world. And I'd been part of actually falsifying an image of inclusivity. You know, it's like you have a group cast,

you need a black girl and an Asian girl, and then this and this and this, And actually when you thought about the product and when you thought about the senior management of those companies, it looked nothing like that, right? It just the product didn't work for anyone over a certain size. And the boardrooms were just all made up of typically like white men making the decisions usually for women. And I just sort of thought to myself, there must be a better way to start a company. But it came from problem solving for myself. And I go back to this idea of like, you know, when you think about businesses, it makes more sense that they would be geared towards serving more people.

That's just good business, right? Forget DE and I. Forget like, you know, this idea of diversity, equity, inclusion, being something that companies need to do now. It's just good business. And when I talk about it, this idea of inclusivity and diversity being a superpower in business, it's not something that I just say. is something that I do. That's where the process actually starts. I'm thinking about how can I best serve customers the most amount of people. And then when there's an acknowledgement of someone who isn't usually acknowledged, of course it goes without saying that suddenly they feel seen,

they feel heard. And they're like, I'm going with this girl. I'm going with this brand because it's the first time anyone's spoken directly to them. And I think that that's such a, it's such an underthought about part of business. You know, people usually bolt it on at the end. And I'm like, no, no, no, no, it's right where you start. It's in the inception of those products. It's in making 32 sizes. It's in doing nine different shades. It's in the very, very beginnings of what you're creating.

And then you can dress it up and make it look nice and put the right kind of branding on it. But actually it starts way earlier than that. And so I actually think about customers in a way that I think most people don't. Where did you not learn that, but where did you learn to, look to understand that obviously started with yourself but I'm like why didn't people do that before because like you just said it's better business it's better financially it makes more sense it makes more people happy what do you think blocks companies just comes from where decisions are being made right because it's like you don't know what you don't know and I've sat in enough rooms trying

to pitch enough businesses to a group of people that aren't my end audience and I have actually said in in meetings before maybe you should phone your wife or daughter like literally like phone them because you don't understand this because it's not for you, you know? And so I think that decisions are made in such a abstract way in most companies. And, you know, you see this when, you know, companies make mistakes, right? They've seen a lot of, like, big fashion brands and big consumer brands make mistakes that have seemingly kind of come across as, like, insensitive, racist, completely misogynistic. That's just where a decision is made.

A company isn't inherently racist, like the whole company. It's just a decision-making process is flawed, i.e., there's not enough people in the room of a different background to say, hey, perhaps put the t-shirt on the other kid, like, then it won't be an issue. So I think that this just comes from the idea of, like, where are the decisions made in that company and who's making the decisions?

And I know that the more people you bring around a table from different backgrounds, we're not just talking about race here, we're talking about age, education, the full gambit, like the better the company will be. Yeah, that is such great. great. I love what you just said about asking someone to call their partner or their daughter or son or whatever it may be because you're so right. Like I think so many people sit in meetings

and they're looking around going, these people don't know what they're talking about or like they just don't understand. Totally. How have you maintained like, I guess the question is how many of those meetings have, did you have to sit in until you felt like I'm just going to do this or we're just going to figure it out or did you look for someone who agreed with you? and had your values and did the research, or was it kind of like, we're just going to build it ourselves? Like, how much, give us a bit of that

because I think a lot of people sitting there. You know, it's so interesting. I'm at that point in my career now where I don't sit in a lot of meetings. Yeah, of course. Which is lovely. The shoes on the other foot. I'm like, come over here and I'll let you know if you can come in.

Good for you. I love that. I love that. But in the early days, you know, I think that I sat in a lot of situations feeling like, you know, the great thing is I never doubted myself or any of those ideas. I just thought I hadn't found the right people yet. It's a little bit like, you know, I'm happy to kiss a lot of frogs.

And I always have been. Because again, I don't think it should be so easy. When you're doing something that is new and without so much definition and unproven, like it's supposed to be hard. And again, it's like anything. I never let it get to me. I just was like, poor, poor chicken. He doesn't get it yet.

And he will do, and he'll kick himself, you know? And that's fine. You know, it's just, it's part of it. And I don't mean that in a smug way. But I never, I never doubted what I was doing. I was very, very clear, especially when we started Good America. And I was like, this thing people don't understand and we'll just get them to understand it. Yeah, definitely.

Yeah, no, and I think that's such a great mindset to have. And to not have the smugness or bitterness because that person just wasn't in the right space. You don't know what you don't know. Totally. It's totally cool. I feel like that all the time. I'm like, I'm trying to find the people who want to be part of this story. Yes. And if they don't want to be a part of this story, that's totally cool. Of course, because they won't be great partners to you down the line, right? It's like you either get it and you want to be part of it and you are happy to know that you don't know it all, right? Because it's about new space. If like if we were all doing the same thing and trying to set up the same companies, we'd never find a skims. Exactly. You know, it's like you'd never land on it. You'd be like, that's too complicated.

that's not how we do things. And you skip over the great stuff. How have you managed to continue to stay hungry and also stay innovative when things are good? Like before you were talking about, I didn't like my job, I wanted to get out. You know, milk was outdoors. I was, you know, like, there's a pain that pushes you in a better direction.

I'm not saying you don't have pain anymore. Of course, there's stress. I don't have that much pain. I have daily dramas, but the pain is gone. You know what it is? You are feeling. every day by a piece of it is competition, right? It's like I look at everything.

There is no one who knows more about jeans and knickers than I do. I look at every competitor. I go out in the market. I see it. I know the promotional cadence. I know everything everybody else is doing. And I think that that natural inquisitiveness is part of what keeps me good. But at the end of the day, it's like, I just want to win.

You know, it's like I don't feel satisfied. And also it's like, how could you? It's just been a couple of years. There's loads of people that have had successes for six and for three years. I don't think that's the end goal. The end goal is to build like, you know, generational or generationally defining businesses. And that doesn't happen quickly. And also, I'm not stupid enough to think like or to let a few years success get to me.

There's a lot of people that had a few years success, you know? That's not the end game. And so I think about now it's about, you know, really taking the foundations of what we feel, not sacrificing any of your principles and still being able to grow and to thrive and to hire people. The next clip comes from Cody Sanchez, where she breaks down her top tips on what it really takes to build and buy businesses that lost. Remember that business is long-term grit.

Success is enduring low-level pain, longer than others will. Here's what I want you to focus on in this clip. You're going to fail. You're going to get rejected. You're going to get pushed back. Business is not going to be easy. But here's what you need to learn. All of that failure is helping move you forward when you take it as feedback.

When you learn the language of money, as Cody Sanchez says. when you focus on financial fluency because it's a non-negotiable for ownership. One of the things I love that Cody emphasizes here is mastering the art of deal-making. If you're one of those people who struggles with how to make a deal, how to make a good one, how to negotiate, this clip will actually help you do that. What skills and talents do people need to be able to run those businesses? How much industry knowledge do they need? What business skills are core and important? because I think the mistake is, again, with the kind of world we live in right now, it's someone goes, I love what Cody saying, I get it, I'm going to go buy vending machines,

and then all of a sudden you've got a garage full of like 20 vending machines, and you don't know what to do with them because you don't understand business. So what core business skills are needed and what should we be developing in order to run any of these businesses? How much industry knowledge do we need? Yeah, it's a great question. Well, first of all, what I would think about is there's two different things we need to know in buying businesses or growing businesses. And the first thing is you've got to learn how to do dealmaking and how to actually speak the

language of money, which is what we talk about in the book, before you buy a business. So please don't just hear me and go buy a business. Read the book or go to a free newsletter online, but spend a decent amount of upfront time learning. I promise you'll make more money that way. You know, I kind of think about sometimes people go, well, why don't I use X amount of dollars I have instead of learning, just buying the business? And I go, does that ever work out well? Where we like, don't know what we're doing, but we plow a bunch of money into it because we want to just go do the thing. It doesn't work out. So spend your time learning how to execute first. Now, that said, I really think there's just three key skills that we need to learn to grow a business. The first one is

deal making. We got to understand how to do a deal. The second one is really the mixture of grit and endurance. So it's actually not tactics. It's how hard am I willing to work? What am I willing to sacrifice for the things that I want, and for how long am I willing to do that? And so Angela Duckworth, famously University of Pennsylvania, popularized grit is the most important thing to measure success. So it's basically like how much pain can you tolerate? And if you can tolerate a lot of pain, turns out you have a higher likelihood of making money. Business is really just like elongated periods of low-level pain. Sometimes you have like what's called an acute or like a big jump in pain. But for the most part, you know this. It's like, what is running a business or

starting a business? It's like, well, you're looking at your statements pretty much often. You're like messing around with marketing. It's kind of like low level pain. And so that's the second point. And the third point is actually maybe a little rare too, which is just a lot of people obsess on how. So what skills do I have to have exactly? How do I start a business? How do I tax structure structure the business. How do I get my first customers? All important and good questions. But the real pros, no. You don't ask how. You ask who. Who can I go to who already has 10,000 hours where I can steal their homework? So now in business, if I go, hey, I don't know how to do our taxes. I go find somebody else who has done taxes for us. And it doesn't mean you have to pay for them.

It just means you have to talk to them and often people will help you. And so I find my who second. And then the third tier is buy. So the really, really rich, when they have a problem, they don't think, how do I fix it? They don't think who can fix it. They think, how do I buy the solution to my problem? Because if I can buy the business, if I can buy the solution, then it's almost, it's a higher guarantee of winning. And so that last one is really about your connections. And so I think if you understand dealmaking, you are honest with yourself about how much work you're willing to do one way or the other. And you are willing to ask people for help, I think just about anybody can run a business. Now, can anybody run Amazon? No, of course not. Could

anybody run your businesses, which are quite big? No, of course not. It's really like the level of skill to the level you're at. But we don't say to people, you know, well, not anybody could buy an individual apartment apartment and live in them. We ask like, what do you want and how are you willing to work in order to get it. So I think the same thing with businesses. It's like, okay, we have what's called the deal box, which is a little slightly technical, but basically the idea is,

Oracle of Delphi says, know thyself, right? Most important thing we can do. And in business, you basically want to have your little deal box of what you want. So do you want income of X amount? Do you want it to be located in L.A.? Do you want it to scratch an artistic itch and make you money?

And you sort of fill out this box, you know what you want. And then again, you know, the universe, I think a lot of times wants to help us out, but we don't know what we want. So how is it going to help us? Because we can't tell it one way or the other. And I think it's the same with business. Yeah. You know, because we could go 15 ways from sideways on like we have something called the nine peas, which are like the nine ways you scale a business to nine figures. But I don't want to stop people. I want them to start small and reasonable and know that the biggest thing in between you and the thing that you want is the knowledge on learning the language. of money on getting after it kind of intensely, and then on asking for help. And like, if you have those three things, you can at least start. And I don't want people to stop because they don't have XYZ leadership skill. Like, I believe in your ability to figure it out. How do you find someone who wants to sell a business?

Because, yeah, I feel like that would be my next question of like, how do I even know someone? How do I find someone? Because it must be going great for them. Why would they sell it to me? especially when I maybe know nothing about owning a hair salon or vending machines or whatever it may be. Right. Well, you probably already know this. How many people offer you businesses or stakes in businesses now?

Yeah, a lot. I bet a lot. A lot, yeah. Why? Because you have a very high value skill stack that's very evident. People can directly attribute if I partnered with Jay Shetty, then he's probably going to market my stuff. He's going to give me brand recognition. There's a high level of trust.

So there's what's called the trust transference. So the higher level of skill. you have, the easier it is for you to find businesses. In fact, they'll often come to you. The thing is, though, even when we have a higher level of skill, we often don't really know what to do when it comes to us. We don't know how to do zero-risk deals to us. And so I like learning dealmaking, even if you have a ton of skills and a ton of money, because you can do a deal that seems unfair, but because you recognize your value, the deal is incredibly fair. In fact, the richer you are and the more audience you have, money you have, which I call capital,

the more coding ability you have, aka, like tech Jeff Bezos, engineering capability, or labor you have access to, so employees or people that will work with you, the better deals you can do. Yeah. And that's like the 202-303 level. And anybody who's listening who actually has access to money and capital, you are crazy if you're not thinking about doing deals and learning it because it is the ultimate positive form of leverage.

So I wish that we learned this earlier. This is how so many celebrities get screwed, by the way. And, you know, they get screwed because they do a deal. They don't understand the terms they signed.

Their agent understands the terms they signed. Their agent isn't actually incentive aligned with them long term. And so they end up getting screwed. Like, it broke my heart when I watched that documentary

with Val Kilmer. Like... I haven't seen it. Oh, God. First of all, you would love it. It's beautiful. The documentary is beautiful. He wrote it.

produced it and directed it and started it. And it's just a beautiful piece of art. But also, he lost everything. I mean, he has basically no money now. No way. And the reason why is because of a series of deals that he did were other people made it and he didn't. And so even if you have a ton of money, you got to be really careful about how you structure things in order to keep it. And the bigger that you get, the bigger target you have. And so it's important to think about that. And like the Russian proverb, trust but verify, which is like trust nobody, I'm sorry, trust everybody, but verify that they are actually on your best terms, which is why I always doesn't count unless you've signed on the line that is dotted in the words of Alec Baldwin. So if you don't have

deals coming at you because you don't have massive, you know, fame or money or whatever, like a normal person, then the easiest way is to find deals, it's called origination in private equity. So in private equity, if you think about what they do, they go around and they cold call small businesses. So they literally will cold call a plumbing company. up all over the Midwest and ask like, hey, you guys want to sell or I get them all the time because I own these. So our small businesses, hey, can we buy your landscaping company? So one, one way you find deals is called off-market deal searching. So you basically turn on what I call your reticular activating system, which is basically just a system inside of your brain

that is trained from the African savannah to say, if I keep repeating this thing brain, it means it's important and I might die if I don't pay attention to it. And so in real life, what happens to you is once you play the game of business enough, then once you like deals, have you ever gone into somebody else's podcast studio and because you probably are obsessed with podcasting, you walk in and you're like, hmm, that's an interesting way to do that setup?

I don't think I would do that. Oh, I like that they did that. Let's steal that, right? Your reticular activating system is so turned on to podcasts that you can't help but notice all around you things you would do differently or that you like. The same thing happens with business and deals. So now when I go into like a corner store

or when I go into a restaurant, I go, or a gym. Jim, Jim's get me for some reason. It's like, you have me, you have my credit card. You have recurring revenue. I come in here every single day. Sell me more shit. Why don't you sell me more things? You definitely should.

And so one, I will say, as you learn dealmaking, I can promise you only really one thing when it comes to you becoming a better dealmaker, your reticular activating system comes on. So what's going to happen in deal finding, yes, you could cold call, just like private equity, but instead kind of steep yourself in the type of deal you are looking for.

Steep yourself in what skills you actually have, and then you're going to see them all around. You won't be able to turn it off. It'll be like when you buy a car, all of a sudden, the car's all over the place after you bought it. You're like, did everybody? Was it a sale? No, your brain starts making you notice it.

And so the best way to find deals is you start just having conversations with guys, because again, Cash loves curiosity. Every time you go into a small business, you just go, oh, amazing. You go, I mean, L.A. is full of them. into a cool retail shop, oh, that's cool, man, this is your store? Oh, it is. I mean, probably 50% of the time it's theirs. And then you say to the guy, like, how long have you been doing this?

A while? Do you want to keep, you want to keep doing this? Like, how's business going? You guys make a lot of money? How long you've been around? Is a kid going to take over? Are you going to keep going? Oh, this is so cool. I love this. Maybe I buy a little something. And then maybe I decide I want to own one of these businesses with them. All of a sudden, I get to know the owner, and I start getting into the curiosity where I get them to maybe consider that a young hustler, who is really aggressive might be good for their business. Absolutely. Before we continue, let's take a quick breather

and listen to some of our sponsors. Here we go. Hey, I'm Cal Penn, and on my new podcast, Here We Go Again, we'll take today's trends and headlines and ask, why does history keep repeating itself? You may know me as the second hottest actor from the Harold and Kumar movies, but I'm also an author, a White House staffer,

and as of like 15 seconds ago, a podcast host. Along the way, I've made some friends who are experts in science, politics, and pop culture. And each week, one of them will be joining me to answer my burning questions. Like, are we heading towards another financial crash like in 08? Is non-monogamy back in style? And how come there's never a gate ready for your flight when it lands like two minutes early? We've got guests like Pete Buttigieg, Stacey Abrams, Lili Singh, and Bill Nye. When you start weaponizing outer space, things can potentially go really wrong.

Look, the world can seem pretty scary right now because it is. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to Here We Go Again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm I'm Yvalongoria. And on our podcast, Hungry for History, we mix two of our favorite things. Food and history. Ancient Athenians used to scratch names onto oyster shells, and they called these Ostercon to vote politicians into exile.

So our word ostracize is related to the word oyster. No way. Bring back the Ostercon. And because we've got a very Micasa and Su Casa kind of vibe on our show, friends always stop by. Pretty much every entry into this side of the planet was through the El Golfo Mexico, no America. No, the America.

The Gulf of Mexico, continue to be forever and ever, especially in the place. It blows me away how progressive Mexico was in this moment. They had land reform, they had labor rights, they had education rights.

Mustard seeds were so valuable to the ancient Egyptians that they used to place them in their tombs for the afterlife. Listen to Hungry for History as part of the My Cultura podcast network, available on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hi, I'm Radhiy Dvlukaya and I am the host of a really good cry podcast. This week I am joined by Anna Runkle, also known as the crappy childhood fairy, a creator, teacher, and guide helping people heal from the lasting emotional wounds of unsafe or chaotic childhoods. We talk about how the things we went through when we were younger can still show up in our adult lives, in our relationships, our reactions, even in the way we feel in our own bodies. And Anna opens up about her own story, what helped her notice the patterns she was

stuck in and how she slowly started teaching her body that it is safe now. So when I got attacked, it was very random. Four guys jumped out of a car and just started beating me and my friend. And they broke my jaw on my teeth. I was unconscious. Then I woke up and I screamed. And I screamed because even though I didn't know who I was or where I was, something in me was just like, hold on, wait, they could kill me and I'm not going to let that happen. I'm not going to let that happen. I'm going to get through this and I did. Listen to a really good cry on the I Heart Radio app Apple Podcasts or wherever you get your podcast. I 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 about businesses, talking about businesses online. He had a business, did a couple million dollars a year in revenue. And you can, it's called Eb Holmes plumbing. It was in Phoenix, Arizona. And he got sick with cancer and decided he wanted to shut the business down. He was in his 70s and was like, you know, 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, it was sort of, and this is what most baby boomer business owners think. They're like, who's going to buy this? Because how many times if 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. What 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 like 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. Sometimes 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 aqua hire. 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. And 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 He views Airbnb as a form of art and how to transform your creative passions into a successful company. This 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. 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. And the challenge is that, well, what do you do when you get 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 or 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, like, get the next billion people. I kind of think of myself, maybe more than a business person, you know, you're kind of who you are growing up. and I was a designer growing up. And I kind of think of Airbnb as like one of the world's biggest canvas. Almost 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 a painter wants a painter wants a painter, a builder wants a build, a climber wants to climb. And as an entrepreneur, I want to create and connect things. and try to 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 the very beginning. And I feel like what makes me happy now is working with people I love. Like one of the great things about success is you can choose the people you surround yourself with. And I get to like work every single day with people I love on ideas that I'm obsessed over. And I'm just so obsessed.

Like I think my motivation's changed. I think when I started my motivation was about myself becoming something. And once you cheat. 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. So when you're not successful, you get validation when people praise you. But eventually, like, 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, like how much more is going to make you happy? And so just doing things

I love a people I care about, that's what makes me happy today. That's beautiful. That's, 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, upper mountain, and then there's another journey we all have to take that's inwards to the valley.

and 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. Right. 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 like hard to even grapple with. When you go on a journey like this, you learn a lot about yourself. And you start to also learn like what's important to you. Starting a company, you know, one of my first investors said, Brian, starting companies like jumping off a cliff and assembling the airplane the way down. Maybe another way of saying it is like 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 that tends to amplify things. I mean, that can be good, but Alkins still can amplify holes you have in yourself.

People that are a little bit paranoid get very paranoid. People that are a little deceitful become like completely fraudulent liars. there's people that are a little narcissist to become like egotomaniacs and stuff. And so the stuff can tend to amplify tendencies inside of yourself. And so if you're afraid of conflict, that's going to actually manifest and not actually dealing with things. If you're not decisive, there's going to be an element of bureaucracy. If you're like, 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 learn 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? Like 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 100,000 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. I'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 change for 16 years, but here you are still building it together. Think 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 becomes so much bigger than the 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 that changes in like 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 like where you perform and what you sing, with a company, you have to agree on like who we're going to hire, what we're going to call, what markets we're going to go into, what's the prioritization, like who are going to raise money. I can go down the list of like 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 going to supersede our friendship and our relationship, that we're never going to 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. And if you get stuck on the first debate or you, like, somebody won a debate, okay, great, you have 99,999 more things that are you.

us. 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. And we took this, like, personality test to see about our chemistry. And they plotted our personalities and they formed a perfect equilateral triangle. Not always you're going to find people that are perfect compliments to you. I'd say a couple things. Number one, you want to 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 going to probably spend more time of 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, because you can debate anything so long as you're trying to climb the same mountain in the same flee system. You have different values, eventually those are going to become irreconcilable conflicts. But you probably also want complimentary skills. The worst case is people with different values and same skills, right? We do the same job. We step in 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 like even as CEO, I wanted to try to make sure that like Joe and Nate, you know, were included in things. And I wanted to always make sure that people referred to us together. We thought of us as a unit. When I like when public, you write a founder's letter and a lot of people write the letter and they just signed 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 and they have a mutual love and respect from another, that's going to permeate the company, just like it permeates the health of a child. And Joan and I kind of thought ourselves as parents in the company as a child. I'd never have had kids. But, you know, there's something about that. And I think who you are in that relationship permeates every single thing. If the founders fight, the employees fight, if they have respect from one another, that is going to be a role, a model that other people throughout the organization are going to 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. Too 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 entrepreneur or a hustle. I think I came out of the womb, like just, you know, wanting to be an entrepreneur. 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. 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 their mindset? Or is it born with as you are? So I think I was definitely born with it. That 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 learning 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 the stuff just what 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 by the way figure out what they do that you don't like and ignore that like 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 got lots of bad habits I mean like I'm myself that's right that's all I ask for that's

That's what I ask for. There is no judgment here. It's a safe space. I just want people to be the authentic selves. And so please continue to be yourself. And 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, something you read or heard or learned? Was there anything that kind of stuck with you? Yeah, for sure. I mean, look, I'm in LA for the week. I'm doing six to ten meetings a day in my house. And, you know, two, 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 of what you do. I mean, it's like life is no different than sports. You just got to keep getting better at your sport. And so 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, what, wasn't as touted as this incredible opportunity. No, it wasn't touted. It was actually weird.

Right. To be clear, like, I was a nerd, like, 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 error. You know, kind of late 90s is when entrepreneurialism became cool. I think before that it was kind of nerdy and weird. So I was definitely born before at all.

Yeah, and I'd say even after the financial crisis in like 2007-8, like that reset 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. 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. And, you know, one of our biggest business, the collectibles business,

just trading cards in my mobility. 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 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, soccer 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 is that industry evolved as technology's grown or has it stayed the same where 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 uh we own tops which is the you know kind of preeminent brand and in trading cards i'd say that you know until our arrival in the industry little less than three years ago i said there hadn't been you know tremendous amount of innovation

there hadn't been a tremendous about marketing you know we kind of looked at the business 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 100,000 people that come to Chicago this past summer. It's called the National Trading Cart Show. Yeah, it looks like something from 20, 30, 40 years ago. So for us, that was just, 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 in 2003. Like, what an opportunity. So for me, like, we do that. We do that.

that in all of our business. Like I love like, like we love finding great opportunities, big challenges and kind of being unrelenting about going after them. Yeah. How has that changed? How is that practically changed? Like are people still buying cards and trading? Physical cards are the biggest part of business. In a lot of ways, very simple little art. But I can tell you like just as one quick example, this year, you know, our team came in and actually the CEO of our business, Mike Mayhan 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. And then as soon as they get done the game, I'm going to put a patch off and put it in a one-on-one trading card.

So you have the card from the first. So think about for us, you know, maybe I grew up in the Michael Jordan era. Had I had, you know, Michael Jordan. Yeah, if I had Michael Jordan or Cobb'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

sticking into a card and make this a one-on-one card? But 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 three to 400 baseball players debut this year, you know, with this debut patch that we put into a one-on-one cart. So that's just like one of dozens of examples of innovations

because you have to be aggressive. 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, you know, AI, whereas 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 Fanatics Commerce. That's our merchandise business. We own Lids the Hat 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. But 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 I gaming 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.

We'll be right back. Hey, I'm Kelly, and some of you may know me as Laura Winslow. And I'm Telma, also known as Aunt Rachel. If those names ring a bell, then you probably are familiar with the show that we were both on back in the 90s called Family Matters. Kelly and I have done a lot of things and played a lot of roles over the years. But both of us are just so proud to have been part of Family Matters. Did you know that we were one of the longest running sitcoms with the black cast? When we were making the show, there were so many moments filled the joy and laughter and cut up that I will never forget.

Oh, girl, you got that right. The look that you all give me is so black. All black people know about the look. On each episode of Welcome to the Family, we'll share personal reflections about making the show. Yeah, we'll even bring in part of the cast and some other special guests to join in the fun and spill some tea. Listen to Welcome to the Family with Telma and Kelly

on the IHeart Radio app, Apple Podcast, or wherever you get your podcasts. On this week's episode of the next chapter, I, Giddy Jakes, get to sit down with Oprah Winfrey, a media mogul philanthropist and global trailblazer. My life, although it may look like an anomaly, it has only been possible because I was obedient to the calls. This episode dies deep into how Oprah turned pain into purpose and what it really means to evolve with everybody watching.

Every decision I have ever made has come from sitting with the spirit and asking God, what would you have me do first? Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak directly to you. Listen to the next chapter on the I Heart Radio app, Apple Podcast, or wherever you get your. your podcast episodes drop weekly. This week on Dear Chelsea with me, Chelsea Handler, Nicholas Sparks is here. I would imagine that you've gotten a lot of feedback about setting a standard of love and

romance that a lot of men probably can't measure up to. I have heard such stories at my book signings, right? Where's my Noah? Where's my John from Dear John? And at the same time, in the course of my career. I've had seven marriage proposals in lines to sign my book. You know, they go up to the table, the doodle dropped to his knees. And I feel so bad for him, I'm like, dude, you're, you're in a Walmart in Birmingham, Alabama, you know, but it's happened. And, you know, you get a lot more of those kinds of stories than people coming up and saying, I've ruined, I've ruined men for them, for the rest, which I'm glad. I would feel bad if that was more common, actually. No, that's what you come to Dear Chelsea for.

Yeah. To get uprated. Listen to Dear Chelsea on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Okay, we're back. Let's dive right back in. I still want my Kobe jersey. Yeah, exactly. I want my Broncard.

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 store. Even though I absolutely, even though we absolutely suck right now. but it's, you know. But that's what's being sports fans about.

Sometimes you're going to have the great years and you're getting those championships and other times you're going to suck and you've got to stay with your team. You 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, that's, 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. It'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 and 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 app 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. 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 it. And by the way, when you fail, which many times you will,

you're going to learn from that failure. You're going to grow from that failure. You talked about Kobe being your favorite athlete. Well, guess what? How many times he failed and then he got better and he pushed through it? 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.

Don't worry about whether you succeed or not. Go out and take the swing. And 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 should build a great team to do what you do. Like, 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. You can't win a championship if you don't have great talent, but that talent also 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 fun. It's like I should pinch myself. It's so awesome what I get to do. I think pattern watching 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.

Would 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 going to go out,

and I'm never going to ask anybody for a reference ever. I've never asked somebody, hey, can you tell me who to call it? Like, that's the, you ask me for reference to myself. I'd call each other and say, hey, I gave you as a reference, make sure you say great things about me. Right? So 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, okay? 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 know, you'll find out 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, you know, they've got huge followership. They're super smart.

They've got an unrelenting work ethic. So 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 whatever you do. In our final clip, Sunira Madani reflects on building a billion dollar fintech by embracing risk, clarity and consistency. Maybe 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. 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? I 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 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. So 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 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. It was like a Sharrock Con 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 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. They 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

as well, right? So my ability to be able to say, okay, I feel like I'm going to win. I feel like looking at the hands or learning black check 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 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. It'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 here. 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. And 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 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? And 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, like, 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, and our prime. And that makes complete sense. and 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 a risk if you don't do the thing? And that's kind of how I try to make those, the risky decisions today. And 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 accomplished. And so it's really about the risk of not doing the action. But at that time, I think it was, 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. It 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, 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. Like, 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 families. to find their niche and build their product and think about what they're doing. Because 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. There'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. dollars 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? There 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 engine. 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. And if it's one of you, you're really like, it's resonating with you because you're like, I am that person. 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 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 asked myself, did I like give my hundred and time? I 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 and 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 that challenge. That's what

entrepreneurship is. It's not, I didn't build a billion dollar. 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 like, what was the secret to the billion dollar success? I didn't give up. Like I just somehow kept showing up. I can name every founders, like every journey where we almost did to make payroll. I had to put my mortgage on the line. We had to do, 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. And for me, it was, I just love to solve really big problems. And that's why even after exit, right, it's like here I'm back again and in building again.

It's because I see, I see the problem and I know we can solve it. Yeah. I think you're the right person to ask this question to you because you talked about working hard and working smart. But what was the mindset shift in building a million, business, 100 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 100. I don't know what's, what do I need to do differently? Because 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 100, 100 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.

Going 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 wrong. 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. We had to, you know, 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 shift to an enterprise strategy. Now I'm building again. We're selling directly to the banks. We'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. Like I put so much intentionality behind working really hard to be the best leader that I could. And 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 my brother. We're one team. We one team, one dream. Like that's

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, those. Those don't change. Those evolve, but that needs to say grounded and the same as you're scaling. Then 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 fun. And we were disrupting the industry. But I knew fat merchant was a $100 million company. Stax was a billion dollar company. And I had to get comfortable, even though it was my, to make those pivots, to make those changes. And 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. It 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. On the podcast health stuff, we are tackling all the health questions that keep you up at night.

I'm Dr. Priyanko Wally, a double board certified physician. And I'm Hurricane Dibolu, a comedian and someone who once Googled, do I have scurvy at 3 a.m. And on our show, we're talking about health in a different way, like our episode where we look at diabetes.

In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is, is type 2. Extremely. Listen to health stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. No one is harm, no death, no trauma,

just a few cells grown in a dish. This is David Eagleman from the Inner Cosmos podcast, and this week we're tackling a tough question where brain science meets the future. Lab-grown meat is going to force us to confront the boundaries of our ethics. And what does this have to do with brain plasticity, social belonging, messed up boundaries between mental categories? What does this uncover about brain science and our calculations of morality?

Listen to Inner Cosmos on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when Reese Witherspoon calls up the king of thrillers, Harlan Coben, and says, let's write a book together? I was asking him basically to let me into his see. secret thriller writing world. This week, bookmarked by Reese's book club goes live from Apple Soho in New York City for the ultimate storytelling mashup. Reese Witherspoon and Harlan Coben on their new thriller, Gone Before Goodbye. Can you think you're going to read for 10 minutes? And next thing you know, it's four in a morning.

Get the story behind the season's most addictive read, already in New York Times bestseller. Listen to Bookmarked by Reese's Book Club on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. This is an I-Heart podcast. Guaranteed human.