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Jay Shetty
This is an iHeart podcast.
Emma Greed
Have you ever gotten sick on a very expensive, very non refundable family trip? AmazonOne Medical has 247 virtual care so you can get help no matter where you are. And with Amazon Pharmacy your meds can get delivered right to your hotel fast. It's kind of like the room service of medical care. Thanks to Amazon Healthcare just got less painful. We talk a lot about alignment, mind, body and spirit, but rest plays a big part in that too. I've been thinking more about how I sleep and what I sleep on. Avocado Green Mattress stood out to me because their mattresses are made with certified organic latex cotton and wool. No chemical flame retardants, no petroleum based foams, just clean breathable comfort. Their best selling Avocado Green mattress comes in firm, medium or plush so you can find the feel that's right for you and wake up. Well, head to avocadogreenmattress.com today and check out their mattress and bedding sale Avocado Dream of Better Lately, I've been trying to be more intentional, even with small decisions like cooking at home instead of ordering out. It's simple, but it helps me save for things that truly matter. That's why I love the State Farm Personal Price Plan. It lets you bundle home and auto insurance to create an affordable price that fits your needs. It's one of those thoughtful choices that support the life you're trying to build. Talk to a State Farm agent today to learn how you can choose to bundle and save with the Personal Price Plan. Like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state. Coverage options are selected by the customer, availability, amount of discounts and savings and eligibility vary by state. 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 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 Sanira, who sold her last company for just over $1 billion 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 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.
Cody Sanchez
Jay Shetty Jay Shetty he won the.
Jay Shetty
Only Jay Shetty.
Emma Greed
In this first clip. Emma Greed dives into how she launches purpose driven brands rooted in real problems people face every 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 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?
Cody Sanchez
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 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 color plus size 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 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 saw 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 D E. And I forget, like, you know, this idea of diversity, equity, inclusion, doing some 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, it's 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 under thought 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. 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.
Emma Greed
Where did you not learn that? But where did you learn to look to understand that? Obviously it 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?
Cody Sanchez
It 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 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. And so I think that decisions are made in such a abstract way in most companies. And you see this when companies make mistakes, right? They were seeing a lot of people, 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 the decision making process is flawed. That is, 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 decision? And I know that the more people you bring around the 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.
Emma Greed
Yeah, that is such 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. 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 gonna do this, or, we're just gonna 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 gonna build it ourself? Like, how. Give us a bit of that. Because I think a lot of people.
Cody Sanchez
Sit in the meeting. 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. Now they pitch me.
Emma Greed
Yeah.
Cody Sanchez
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.
Emma Greed
Good for you. I love that. I love that.
Cody Sanchez
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. 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, oh, 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 will just get them to understand it.
Emma Greed
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.
Cody Sanchez
You don't know what you don't know, Right?
Emma Greed
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, and if they don't want to be a part of this story, that's totally cool.
Cody Sanchez
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. It's about new space. It's like, if we were all doing the same thing and trying to set up the same companies, we'd never find a skims.
Emma Greed
Exactly.
Cody Sanchez
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. Yeah, and you'd skip over the great stuff.
Emma Greed
How have you managed to continue to stay hungry and also stay innovative when things are good? Like before, you talk 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. 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 stresses.
Cody Sanchez
I don't have that much pain. I have daily drama. I have daily dramas, but the pain is gone. You know what it is? You are fueled 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, like, the promotional cadence. I know everything everybody else is doing. And I think that 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 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've built, not sacrificing any of your principles and still being able to grow and to thrive and to hire people.
Emma Greed
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 last, 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's 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 business, 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?
Michael Rubin
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 deal making 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 our 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. 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 gotta 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 as the most important thing to measure. 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 the business? How do I get my first customers? All important and good questions, but the real pros know 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 connection. And so I think if you understand deal making, 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 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 a 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 la? 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.
Emma Greed
Yeah.
Michael Rubin
You know, because we could go 15 ways from sideways on like we have something called the nine Ps, 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.
Emma Greed
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.
Michael Rubin
Right. Well, you probably already know this. How many people offer you businesses or stakes and businesses now?
Emma Greed
Yeah, a lot, I bet.
Michael Rubin
A lot.
Emma Greed
A lot, yeah.
Michael Rubin
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 a 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 deal making. 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. 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.
Emma Greed
Like, I haven't seen it.
Michael Rubin
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 starred in it. And it's just a beautiful piece of art. But also he lost everything. I mean, he has basically no money now.
Emma Greed
No way.
Michael Rubin
And the reason why is because of a series of deals that he did where 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 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 ways to find deals, it's called origination and private equity. So in private equity, you, 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 on 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 and once you like deals, like, 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, that's an interesting way to do that setup. Yeah, for sure. 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 think you would do differently or that you like. The same thing happens with business and deals. So now I, when I go into like a corner store or when I go into a restaurant, I go or gym. Gyms 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 deal making, I can promise you only really one thing. When it comes to you becoming a better deal maker, your reticular, reticular activating system comes on. So what's going to happen in deal finding? Yeah.
Jay Shetty
Yes.
Michael Rubin
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 like, oh, amazing. You go, I mean, LA is full of them. You walk 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 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 been around? Is the kid gonna take over? Are you gonna 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. 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.
Emma Greed
Absolutely. Before we continue, let's take a quick breather and listen to some of our sponsors. When you start a business, it's not just about selling a product. It's about sharing something you truly believe in. Every decision from choosing a name to launching your first product feels massive because it is. It's a reflection of your values, your passion and your purpose. That's why having the right platform matters. You need something that understands the journey that grows with you. Shopify gets it because they started small too. Shopify powers millions of businesses worldwide and handles 10% of all US E commerce. From big names like Mattel and Gymshark to brands like Jooni, our sparkling tea company. Shopify provides everything you need to build and grow your business. With Shopify, you can manage inventory, payments and analytics all in one place. So you're not juggling multiple tools. It also makes it easy to reach new customers with built in social media and email marketing tools helping you reach new customers and keep them coming back. If you're expanding beyond the U.S. shopify supports selling in over 150 countries. And if you have a physical store or sell at events, their award winning point of sale connects your online and in store sales seamlessly. Plus with 99.99% uptime and the best converting checkout on the planet, it you'll never miss a sale. Only with Shopify. Get all the big stuff for your small business right with Shopify. Sign up for your $1 per month trial and start selling today at shopify.com j that's shopify.com j shopify.com j.
Michael Rubin
It's.
Emma Greed
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Michael Rubin
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 business, talking about businesses online. He had a business, did a couple million dollars a year in revenue, and you can. 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. You know, he's 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. That wasn't really, you know, it was sort of. And. And this is what most baby boomer business owners think. They're like, who's gonna 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?
Emma Greed
Yeah, of course.
Michael Rubin
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.
Cody Sanchez
And I laugh.
Michael Rubin
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, 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 acqua 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, kodi.com websites before? Like, 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.
Emma Greed
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. 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?
Brian Chesky
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, I 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 paint, a builder wants a build, a climber wants a climb. And as an entrepreneur, I want to create and connect things and. 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 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 motivations changed. I think when I started, my motivation was about myself becoming something. And once you achieve that, your motivation often turn. Turns outward. It's about. 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. See, 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 of people I care about, that's what makes me happy today.
Emma Greed
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, 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.
Brian Chesky
Right.
Emma Greed
And it sounds like you've been excavating that internal part for some time.
Brian Chesky
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 on 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 it tends to amplify things. I mean, that can be good, but it all 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. 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 can't, if you're not decisive, there's going to be an element of bureaucracy. If you, 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 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? 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 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 the what they. And that's the thing that's, like, so crazy.
Emma Greed
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.
Brian Chesky
Yeah.
Emma Greed
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.
Brian Chesky
Think about how many stories you 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 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, 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 gonna hire, what we're gonna call, what markets we're gonna go into, what's the prioritization, like, who we're gonna raise money for 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. We'll debate, we'll argue, but we'll never allow a situation where winning an argument is the most important thing.
Michael Rubin
Thing.
Brian Chesky
Because 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 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 at the right time at 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 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 complements to you.
Jay Shetty
You.
Brian Chesky
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 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. Because you can debate anything. So long as you're trying to climb the same mountain and the same footage belief system, 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. Right? We do the same job, we step in each other's tolls, and we're trying to go in a different direction. And so I think. And then I think the final thing is just this mutual love and respect and never losing sight. You know, 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 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 went public, you write a founder's letter, and a lot of people write 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 parents. 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. For 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 of 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 for one another, that is going to be a role, a model that other people throughout the organization are going to come. And that's what I've learned from that.
Emma Greed
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.
Sunira Madani
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 ever worked today. I love. It's an honor to do it.
Brian Chesky
It's fun.
Sunira Madani
It's an opportunity. Like, I'm never tired. I'm never worn out. Like, I'm just always.
Emma Greed
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?
Sunira Madani
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, 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 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 and, 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've got lots of bad habits. I mean, like, I'm myself. That's right.
Emma Greed
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 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?
Sunira Madani
Yeah, 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 in everything that I do. So to me, I'm always taking learnings 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 gotta keep getting better at your sport. And so to me, I keep working at everything I do.
Emma Greed
Yeah. What do you think? Obviously now, like, when you started 43 years ago, at 8 years old, entrepreneurship wasn't as touted as this incredible.
Sunira Madani
No, it wasn't touted. It was actually weird.
Emma Greed
Right.
Sunira Madani
Like, 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 that really the birth of the dot com era, you know, kind of late 90s, is when entrepreneurialism became cool. I think before that was kind of nerdy and weird. So I was definitely born before it all.
Emma Greed
Yeah. And I'd say even after the financial crisis in like 2007, eight, like. 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. I want to build something of my own.
Sunira Madani
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, 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 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.
Emma Greed
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 biggest 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 where people still collecting cards and like top trumps and things like that?
Sunira Madani
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 kind of preeminent brand in trading cards. I'd say that until our arrival in the industry a little less than three years ago, I said there hadn't been any, been, you know, tremendous amount of innovation, there hadn't been a tremendous amount of 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 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 was just. That just meant opportunity meant if you, 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. So for me, like we do that in all of our business. Like I look like we love finding great opportunities, big challenges and kind of being unrelenting about going after them.
Emma Greed
Yeah. How has that changed? How has that practically changed? Like Are people still buying cards and trading?
Sunira Madani
Physical cards are the biggest part of the business in a lot of ways. Very similar to art. But I could tell, like just as one quick example, this year, you know, 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. And then as soon as they get done the game, I want to put a patch off and put it in a one on one trading card. So you have the card from, from the first. So think about for, for us. You know, maybe I grew up in the, in the Michael Jordan era. Had I had, you know, Michael Jordan or. Yeah, if I had Michael Jordan or code first 101 cards, yeah, that could be the, 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? But no one did that until we created. And by the way, it's already live. We came up with the idea this past December. It wasn't, it was live in, in April with all baseball players. It's gonna be 3 to 400 baseball players debut this year. You know, with this debut patch that we put into a one on one card. So 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 whatever we do.
Emma Greed
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.
Sunira Madani
Look, we're in three business day. Our first business where we, 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, 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 bet 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.
Emma Greed
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. This back to school season, spend less on your kids with Amazon. I was talking to one of my closest friends the other day. He has two kids and every year it's the same routine. One kid wants a very specific backpack. I'm talking not just blue, but navy blue with a neon green zipper and a galaxy print. The other lost their lunchbox before the first week of school even ended last year. He's like, jay, I swear they get more expensive every time they grow an inch. And I get it. Kids grow, seasons change, and somehow they always need five new things they didn't need last year. But what doesn't have to change, how much you spend on them. So remember, with Amazon's low back to school prices, just spend less on your kids because every dollar you don't spend on them is a dollar you haven't spent on them. Shop back to school at Amazon and spend less on your kids. Apple Gift Card is the perfect gift for back to school. Send it via email or send a physical card to your loved ones. Friends and family can use Apple Gift Card to get products, accessories, apps, games, music, movies, TV shows and more. They can also spend it on in app content, music subscriptions and even iCloud Plus. Visit applegiftcard.apple.com for details and to send Apple Gift Card. This back to school season Oikos presents 15 seconds of strength.
Sunira Madani
Here we go. Steve's got a trunk full of groceries.
Emma Greed
And no one to help him. Oh, that's tough.
Brian Chesky
Jim looks like a five trip load.
Emma Greed
At least. He grabs the first bag, the second bob. It looks like he's trying to do it all.
Sunira Madani
One trip.
Emma Greed
He shimmies the door, door open, steps over the dog. Oh, and he stumbles. Oh, right into the kitchen without missing a beat.
Sunira Madani
Jim, now that's a man who eats.
Emma Greed
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Sunira Madani
I still want to wear my Kobe jersey.
Emma Greed
Yeah, exactly, exactly.
Sunira Madani
I want my Bron card.
Emma Greed
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.
Sunira Madani
We appreciate that because that's a fanatics fanatic store.
Emma Greed
Even though I absolutely, even though we absolutely suck right now. But it's, you know, but that's what.
Sunira Madani
Being sports fan is about. Sometimes you're having great years and you get, you're getting those championships and other times you're going to suck and you got to stay with your team.
Emma Greed
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.
Sunira Madani
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?
Emma Greed
Yeah, that's. That's. I'm being tested right now. Perfect. 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?
Sunira Madani
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 a story you were just telling me before we went on here that you came over here and, 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 going to learn from that failure. You're going to 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 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 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 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 time 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. 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. 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 on 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.
Emma Greed
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?
Sunira Madani
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? Like, that's the, 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? 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 gonna get. Cards are either gonna 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, you got a pattern going on. So you got to recognize patterns whatever you do.
Emma Greed
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 issue 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. They'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.
Jay Shetty
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 Shahrukh Khan concert when they would come out and do the shows. We went to Atlantic City for this concert, and there was a casino. I'm not even of legal age to gamble. And my dad takes me to the blackjack table. And he was an avid. He definitely had not the best habits as well. And it's important to see you can see both sides of your parents. Things weren't perfect. I. 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. 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? Am I going to lose the money? What's the value? And his response, he goes, just feel it. He's like, if you feel like you're gonna win, bet more. If you feel like you're not gonna 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 gonna win. I feel like looking at the hands or learning blackjack, and I was great at math, and I can get this concept that was one of my. 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 one rock away, and she gets to raise my kids with me. So it's wonderful.
Emma Greed
It's amazing 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 delayed 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.
Jay Shetty
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 priority. 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. 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 accomplish. 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. 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.
Emma Greed
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. 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. Bit.
Jay Shetty
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, 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 in payments through this ecosystem that I almost didn't start if I didn't build it. We, we solved huge problems in this. It was so unsexy. Card present versus card 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 in 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. And if it's one of you, you're really like, it's resonating with you. Cause 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 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 give my 110? 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, 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. And 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 didn't make payroll. I had to put my mortgage on the line. We had to do. We didn't get the investors and 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.
Emma Greed
Yeah, I think you're the right person to ask this question too because you talked about working hard and working smart. But what was the mindset shift in building a million dollar 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?
Jay Shetty
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 0 to 6, from 6 to 7, 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 gonna break again. Your systems are gonna 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 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 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 gotta scale your people, you've gotta scale your process and you've gotta 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 a 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 over prepared 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 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, the 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 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. It was fun and we were disrupting the industry. But I knew fat merchant was $100 million 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. And so you've got to see where it's going and you've got to be willing to just throw it away and just 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.
Emma Greed
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. Success comes when you say I like this enough for other people to see it. American Public University is the number one provider of education to our military and veterans in the country. They offer something truly unique. Special rates and grants for the entire family, making education affordable not just for those who serve, but also for their loved ones. If you have a military or veteran family member and are looking for affordable, high quality education, APU is the place for you. Visit Apu Apus Edu Military to learn more. That's apu.apus. edu military want to feel more creative but don't have the right laptop? Lenovo.com can help. Look through our legendary lineup of AI powered PCs and devices and find the one that fits your passion. Our PCs, powered by Intel Core Ultra processors as well as cutting edge AI tools, allow students to focus, learn and create with ease. That's the power of Lenovo with Intel Inside. Plus, college students and teachers can get 5% off their order. Shop now on Lenovo.com the future's waiting and it needs you. Gatorade is the number one proven electrolyte blend designed to hydrate better than water so you can lose more sweat and raise your game. Gatorade. Is it in you?
Jay Shetty
This is an iHeart podcast.
On Purpose with Jay Shetty
Host: Jay Shetty
Release Date: July 30, 2025
Description: Jay Shetty hosts the world’s #1 mental health podcast, aiming to make listeners happier, healthier, and more healed through insightful conversations with experts, celebrities, and thought leaders.
The episode, titled “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!)”, is tailored for aspiring entrepreneurs looking to transition from traditional employment to building their own successful ventures. Jay introduces five prominent entrepreneurs who share their journeys, strategies, and personal insights on entrepreneurship.
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Timestamp: [04:14] - [16:02]
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Timestamp: [16:02] - [33:35]
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Timestamp: [33:35] - [45:13]
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Timestamp: [45:13] - [55:00]
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Timestamp: [55:07] - [76:17]
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The episode serves as an extensive masterclass on entrepreneurship, featuring diverse insights from five successful CEOs. Key themes include the importance of solving real problems, fostering inclusivity, mastering financial and deal-making skills, maintaining resilience, and upholding strong cultural values. Jay Shetty and his guests inspire listeners to take actionable steps towards building their own businesses, emphasizing that success stems from persistent execution and authentic leadership.
Emma Greed:
“Start with what's missing. The best business ideas come from solving your own unmet needs.” [04:20]
“Building for the unseen audiences builds unshakable loyalty.” [05:20]
Cody Sanchez:
“Inclusivity and diversity being a superpower in business is not something that I just say, it's something that I do.” [08:44]
“Business is long-term grit. Success is enduring low-level pain longer than others will.” [14:31]
Michael Rubin:
“Spend your time learning how to execute.” [16:02]
“Business is the spirit of solving for problems. It’s not for show.” [25:08]
Brian Chesky:
“Success will come if you just, like, let go of that.” [37:28]
“When you see a company, it's like I walk in your house, and I can understand the thousand decisions you made.” [40:37]
Sunira Madani:
“If you're in the game long enough, you realize that every business has a value.” [22:39]
“Entrepreneurialism isn't for everybody. But if you think it's for yourself, you better go out there and try it.” [50:35]
Jay Shetty:
“Ideas don't make you an entrepreneur. Execution does.” [68:34]
“There is no such thing as a billion-dollar idea. It's a billion-dollar execution.” [72:50]
“Success is enduring low-level pain longer than others will.” [14:31]
This episode is a treasure trove of actionable insights and motivational stories for anyone looking to transition from a traditional job to entrepreneurship. By listening to the experiences of Emma Greed, Cody Sanchez, Michael Rubin, Brian Chesky, and Sunira Madani, aspiring entrepreneurs can gain valuable knowledge on building, scaling, and sustaining successful businesses without the need for formal business education.