Jay Shetty PodcastTop Entrepreneurs Reveal the 4-Step Rule Book to Make Your First Million!
EVERY SPOKEN WORD
75 min read · 14,702 words- 0:00 – 3:06
Intro
- JSJay Shetty
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 nine-to-five right now, which is really a nine-to-nine, 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 gonna hear directly from five of the best entrepreneurs that I know. You're gonna be hearing from one of the co-founders of Skims, Emma Grede, 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 gonna hear from Suneera, who sold her last company for just over a billion dollars, Brian Chesky, the founder and CEO of Airbnb, and from Codie 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 gonna 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.
- SPSpeaker
The number one health and wellness podcast.
- MRMichael Rubin
Jay Shetty.
- SPSpeaker
Jay Shetty.
- BCBrian Chesky
The one, the only Jay Shetty.
- JSJay Shetty
In this first clip, Emma Grede 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.
- 3:06 – 6:40
Start With the Problem Only You Can See
- JSJay Shetty
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?
- EGEmma Grede
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, uh, 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 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 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, a Black girl and an Asian girl, and then this and then 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.
- JSJay Shetty
Mm.
- EGEmma Grede
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?
- JSJay Shetty
Mm-hmm.
- EGEmma Grede
Forget DE&I. Forget like, you know, this idea of diversity, equity, and 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 themAnd 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.
- JSJay Shetty
Yeah, yeah.
- EGEmma Grede
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- I actually think about customers in a way that I think most people don't.
- 6:40 – 8:10
The Power of Who’s in the Room
- JSJay Shetty
Where did you, not learn that, but where did you learn to look to understand that? Obviously, it started with yourself.
- EGEmma Grede
Mm-hmm.
- JSJay Shetty
But I'm like, "Why didn't people do that before?" 'Cause like you just said, it's better business. It's better financially.
- EGEmma Grede
Yeah.
- JSJay Shetty
It makes more sense. It makes more people happy. What do you think blocks companies-
- EGEmma Grede
I think it just comes from where decisions are being made.
- JSJay Shetty
Yeah, yeah.
- EGEmma Grede
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."
- JSJay Shetty
Mm.
- EGEmma Grede
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? That we've seen a lot of, like, big fashion brands and big consumer brands make mistakes that have seemingly kind of come across as, like, uh, 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, i.e., there's not enough people in the room of a different background-
- JSJay Shetty
Mm. Mm
- EGEmma Grede
... 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- 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 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
- 8:10 – 10:44
Believe in Your Vision Before Anyone Else Does
- EGEmma Grede
will be.
- JSJay Shetty
Yeah, that is such great... I- I love what you just said about asking someone [laughs] to call their partner or their daughter-
- EGEmma Grede
Totally [laughs]
- JSJay Shetty
... or their 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-
- EGEmma Grede
No
- JSJay Shetty
... they just don't understand.
- EGEmma Grede
Totally.
- JSJay Shetty
How have you maintained, like... I guess the question is, how many of those meetings have, uh, 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?
- EGEmma Grede
Mm-hmm.
- JSJay Shetty
Or was it kind of like, "We're just gonna build it ourself"? Like, how m- give- give us a bit of that because I think a lot of people sit in rooms.
- EGEmma Grede
You know... [laughs]
- JSJay Shetty
[laughs]
- EGEmma Grede
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.
- JSJay Shetty
Yeah, of course.
- EGEmma Grede
Now they pitch me. [laughs]
- JSJay Shetty
Yeah, yeah. Go on.
- EGEmma Grede
Which is lovely.
- JSJay Shetty
Congrats. I love that.
- EGEmma Grede
The shoe's on the other foot. I'm like, "Come over here, and I'll let you know if you can come in." Um, uh, but-
- JSJay Shetty
[laughs] Good for you. I love that.
- EGEmma Grede
In-
- JSJay Shetty
I love that
- EGEmma Grede
... but in the early days, you know-
- JSJay Shetty
Yeah
- EGEmma Grede
... I- I think that I sat in a lot of situations feeling like, um... Uh, 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.
- JSJay Shetty
Mm.
- EGEmma Grede
It's a little bit like you c- 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."
- JSJay Shetty
[laughs]
- EGEmma Grede
"And he will do, and he'll kick himself," you know? [laughs]
- JSJay Shetty
Yeah, yeah, yeah. Yeah.
- 10:44 – 13:26
What Really Motivates You Every Day?
- JSJay Shetty
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."
- EGEmma Grede
Mm-hmm.
- JSJay Shetty
You know, Milk was outdoors. I was... You know, like, y- 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, challenges.
- EGEmma Grede
I don't have that much pain. [laughs]
- JSJay Shetty
[laughs] You know, you know what I mean, but-
- EGEmma Grede
I have daily dr- 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?
- JSJay Shetty
Mm-hmm, mm-hmm.
- EGEmma Grede
It's like I- I look at everything.
- JSJay Shetty
I love that.
- EGEmma Grede
There's 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.
- JSJay Shetty
Yeah.
- EGEmma Grede
And I think that that, that natural, um, inquisitiveness is part of what keeps me good. Um, but at the end of the day, it's like I just wanna win.
- JSJay Shetty
Mm.
- EGEmma Grede
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.
- JSJay Shetty
[laughs]
- EGEmma Grede
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.
- JSJay Shetty
Mm.
- EGEmma Grede
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, [laughs] you know?
- JSJay Shetty
Yeah, yeah.
- EGEmma Grede
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-
- JSJay Shetty
Mm
- EGEmma Grede
... and still being able to grow and to thrive and to hire people.
- JSJay Shetty
The next clip comes from Codie 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 gonna 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 Codie Sanchez says, when you focus on financial fluency because it's a non-negotiable for ownership. One of the things I love that Codie 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.
- 13:26 – 18:33
Three Essential Skills for Building a Business
- JSJay Shetty
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 Codie's saying. I get it. I'm gonna 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? Uh, how much industry knowledge do we need?
- CSCodie Sanchez
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, uh, buying businesses or growing businesses, and the first thing is you've gotta learn how to do deal making and how to actually speak the language of money, which is what we talk a- 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, um, but spend a decent amount of up t- front time learning. I promise you'll make more money that way. You know, I kinda 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, d- 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 'cause we wanna 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 gotta understand how to do a deal. The, 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 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, 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 kinda like low level pain.
- JSJay Shetty
Mm-hmm.
- CSCodie Sanchez
And, um, 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 s- tax structure, structure the business? How do I get my first customers? All, 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, um, 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, uh, second. And then the third tier is buy. So the, 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?"
- JSJay Shetty
Mm.
- CSCodie Sanchez
Um, 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 deal making, you, 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 a, 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?" And 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, uh, in business, you basically wanna 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 w- we don't know what we want, so how is it gonna help us, 'cause we can't tell it one way or the other, and I think it's the same with business.
- JSJay Shetty
Yeah.
- CSCodie Sanchez
You know, 'cause we could go 15 ways from sideways on, like, we have something called the nine Ps-
- JSJay Shetty
Mm-hmm
- CSCodie Sanchez
... which are, like, the nine ways you scale a business to nine figures. But I don't wanna stop people.
- JSJay Shetty
Yeah.
- CSCodie Sanchez
I want t- 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, to stop because they don't have XYZ leadership skill. Like, I believe in your ability to figure it out.
- 18:33 – 28:03
How to Master the Art of Deal Making
- JSJay Shetty
How do you find someone who wants to sell a business?
- CSCodie Sanchez
Mm.
- JSJay Shetty
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.
- CSCodie Sanchez
Right. Well, you probably already know this. How many people offer you businesses or stakes in businesses now?
- JSJay Shetty
Yeah, a lot.
- CSCodie Sanchez
I bet a lot.
- JSJay Shetty
A lot, yeah.
- CSCodie Sanchez
Why? Because you have a very high value skill stack that's very evident. Uh, 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. Uh, the thing is, though, when 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.
- JSJay Shetty
Mm-hmm.
- CSCodie Sanchez
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, the richer you are and the more audience you have, uh, 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'll work with you, the better deals you can do.
- JSJay Shetty
Yeah.
- CSCodie Sanchez
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, um, and learning it because it is the ultimate positive form of leverage. So, um, I wish that we learned this earlier. This is how so many celebrities get screwed-
- JSJay Shetty
Mm-hmm
- CSCodie Sanchez
... 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-
- JSJay Shetty
I haven't seen it
- CSCodie Sanchez
... oh, God. W- 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. Um, but also, he lost everything. I mean, he has basically no money now.
- JSJay Shetty
No way.
- CSCodie Sanchez
Uh-huh. And the reason why is because of a series of deals that he did where other people made it and he didn't.
- JSJay Shetty
Wow.
- CSCodie Sanchez
And so even if you have a ton of money, you gotta be really careful about how you structure things in order to keep it. And the bigger that you get, the bigger target you have.
- JSJay Shetty
Mm-hmm.
- CSCodie Sanchez
And so it's important to think about that. And like the Russian proverb, trust but verify, which is like trust nobody... or I'm sorry, trust everybody, but verify that they are actually on your best terms.
- JSJay Shetty
Mm-hmm, mm-hmm.
- CSCodie Sanchez
Which is why it always doesn't count unless you've signed on the line that is dotted-
- JSJay Shetty
Yeah
- CSCodie Sanchez
... 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, uh, 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 wanna sell?" Or I get them all the time 'cause I own these. So our small business is, "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 savanna 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, "Hmm, that's an interesting way to do that setup."
- JSJay Shetty
Yeah, for sure.
- CSCodie Sanchez
"Huh, I don't think I would do that. Oh, I like that they did that. Let's steal that," right?
- JSJay Shetty
Mm-hmm.
- CSCodie Sanchez
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 I- when I go into, like, a corner store or when I go into a restaurant, I go, "Ah." Or a 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?"
- 28:03 – 31:10
Redefining What Success Means to You
- BCBrian Chesky
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 to the top of the mountain? You've achieved it. And what I've realized is at this point, like I'm 41 years old, and a lot of people ask me like, "Why don't you just retire? Like why don't you, 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, 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 to paint, a builder wants to build, a climber wants to climb. And as an entrepreneur, I want to create and connect things and, um, and try to like defy the notion of what a business person could be or what a designer could be because I never met someone like me growing up. And I'm not saying anyone's going to try to be like me, but if I can remind people that there's leadership comes in many different faces, many different flavors, and that a creative person, you know, can run a company and can run a really big company, a Fortune 500 company, then that's, that's the very beginning. And I, I feel like what makes me happy now is working with people I love. Like the, one of the great things about success is you can choose the people you surround yourself with. And I get to 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 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 gonna make you happy? And so just doing things I love with people I care about, that's what makes me happy today.
- JSJay Shetty
That's beautiful. That's... I, I can see that it's true for you, too. I, I, I can see that it, it's, 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
- 31:10 – 34:17
Life’s Greatest Lessons Start Within
- JSJay Shetty
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.
- BCBrian Chesky
Right.
- JSJay Shetty
And it sounds like you've been excavating that internal part for some time.
- BCBrian 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 the last fifteen 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 a company is 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, and 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 also 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 gonna actually manifest in, like, not actually dealing with things. If you can't-- If you're not decisive, there's gonna be an element of bureaucracy. If you're, like, get overwhelmed and you get paralyzed, there's gonna be inaction 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, um, yeah, it's, it's, like, incredible lessons. And a, a 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 in 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, and that's the thing that's, like, so crazy.
- JSJay Shetty
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.
- BCBrian Chesky
Yeah.
- 34:17 – 38:54
Surround Yourself With the Right People
- JSJay Shetty
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 sixteen years, but here you are still building it together.
- BCBrian 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's become so much bigger than a band because it's not just the three of you. Imagine a band that starts three people and ends as three thousand 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. 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 gonna supersede our friendship and our relationship, that we're never gonna have... We'll debate, we'll argue, but we'll never allow a situation where winning an argument is the most important thing. Because you think about a company as a hundred thousand decisions, it could also be a hundred thousand arguments. And if you get stuck on the first debate, or you, like, somebody won the debate, okay, great, you have ninety-nine thousand nine hundred and ninety-nine 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 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, 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, like, personalities, and they formed a perfect equilateral triangle. Not always you're gonna find people that are perfect complements to you. I'd say a couple things. Number oneYou wanna have a team with people that you are friends with or could see yourself becoming friends with, that you have a deep love and respect for, that you're gonna probably spend more time with your co-founders than your spouse or your family if it goes well. If it doesn't go well, then maybe not, but that's the best case scenario. That people that have shared values, because you can debate anything so long as you're trying to climb the same mountain in the same belief system. You have different values, eventually those are gonna 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 toes, 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, you know, were included in things, and f- we... I wanted to always make sure that people referred to us together. We thought of us as a, uh, as a, as a unit. When we, when I, like, went public, you write a founder's letter, and s- a lot of people write the letter and they just sign the name of the CEO. I made sure that it was from all of us and was representing all of us. I feel like they are the heart and the soul of the company. And it's like, you know, parents. Like, you know, not every child has the fortune to have multiple parents. Not every company has the fortune to have multiple founders. But if they're together and they're not fighting and they have a mutual love and respect for one another, that's gonna permeate the company, just like it permeates the health of a child. And Joe and I, and I [laughs] kind of thought of ourselves as parents and 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 o- a respect for one another, that is gonna be a role m- a model that other people throughout the organization are gonna copy, and that's what I've learned from that.
- JSJay Shetty
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
- 38:54 – 40:46
Can Hustle and Drive Be Taught?
- JSJay Shetty
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.
- MRMichael Rubin
I think it's something for me I was born with. Like, I was born with that entrepreneurial hustle. I think I came out of the womb, like, just, you know, wanting to be an entrepreneur, like, just loving the hustle. And, you know, to me, you know, I've been at this a long time. I work harder than I've ever wor- 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 wanna go.
- JSJay Shetty
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?
- MRMichael Rubin
So I think I was definitely born with it. That said, I do think, you know, for me, the way I learn is by being a sponge from people, so I'm always picking things up from different people. Like, if you just look at the diversity of people I have around me, like, I'm always taking so much learnings from them to, you know, be better at what I do, and I try to give those back. So yeah, I think you can definitely learn a lot of this stuff. Just w- you know, find people you respect, find people that you admire, find people that you wanna be like, and then, you know, take the good from them. And by the way, figure out what, what they do that you don't like and, 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.
- JSJay Shetty
Yeah. That's all I ask for. That's all I ask for. There is no judgment here. There's no... It's, it's a safe space. I just want people to be their authentic selves, and so, so please continue to be yourself. And, uh, what's... So what... I love that idea of learning from people, being a human sponge. What's the most recent or most memorable thing you think you took away from someone? A conversation, a moment, uh, something you read or heard or learned.
- 40:46 – 41:30
Learn by Observing Others’ Mistakes
- JSJay Shetty
Was there anything that kinda stuck with you?
- MRMichael Rubin
Yeah, for sure. I mean, um, 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, 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 the, 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.
- JSJay Shetty
Yeah. What, what do you think? Obviously now, like, when you started 43 years ago at eight years old, entrepreneurship wasn't as touted as this incredible opportunity.
- MRMichael Rubin
No, it wasn't touted.
- JSJay Shetty
Yeah.
- MRMichael Rubin
It was exa- it was actually weird.
- 41:30 – 42:52
What is at the Heart of Entrepreneurship?
- JSJay Shetty
Right, yeah.
- MRMichael Rubin
Like, to be clear, like, I was a nerd at, like-
- JSJay Shetty
Yeah
- MRMichael Rubin
... like, that I loved business. Like, entrepreneurialism became cool really around technology. Like, I, I don't think it became cool till almost the, the... From my perspective, I think it was the, really the, the birth of the dot com era.
- JSJay Shetty
Yeah.
- MRMichael Rubin
You know, kinda late '90s is when entrepreneurialism became cool. I think before that it was kinda nerdy and weird, so I was definitely born before it all.
- JSJay Shetty
Yeah, and I'd say even after the financial crisis in, like, 2007, '8, like, that recession, which was... Because I grew up in the era where we still aspired 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 gonna go work for someone. I wanna build something on my own."
- MRMichael Rubin
I think that's amazing.
- JSJay Shetty
Yeah.
- MRMichael Rubin
Like, 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 businesses is the collectibles business, which is trading cards and memorabilia, and that's all about entrepreneurs. There's so many entrepreneurs in that business. It's probably the business in a lot of ways that I... I actually relate to all three of our businesses, but it's the business that's maybe the most relatable for me because I grew up selling trading cards-
- JSJay Shetty
[laughs]
- MRMichael Rubin
... as an eight-year-old, but also it's all about entrepreneurialism.
- JSJay Shetty
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.
- MRMichael Rubin
Yeah, of course.
- JSJay Shetty
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
- 42:52 – 47:14
Bringing Innovation to What You Love
- JSJay Shetty
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 are still collecting cards and, like, Top Trumps and things like that?
- MRMichael Rubin
Yeah. Well, I'll say we got into the business about three years ago in a really significant way, and today, uh, we own Topps, which is the, you know, kind of preeminent brand in, in, in trading cards. I'd say that, you know, until our arrival in the industry little less than three years ago, I'd say there hadn't been, you know, a tremendous amount of innovation. There hadn't been a tremendous amount of marketing. You know, we kind of looked at the business and said, "Wow," like, "this is such an incredible collector base, such an incredible fan base, yet it hasn't changed for, like-
- JSJay Shetty
Mm
- MRMichael Rubin
... 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 Card Show. Yet it looks like something from 20, 30, 40 years ago. So for us, that was just, that just meant opportunity. It meant if y- 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, I, we do that in all of our business. Like, I lo-
- JSJay Shetty
Yeah
- MRMichael Rubin
... like, we love finding great opportunities, big challenges, and kinda being unrelenting about going after 'em.
- JSJay Shetty
Yeah. How has that changed? How has that practically changed? Like, are people still buying cards and trading and-
- MRMichael Rubin
Yeah, physical cards are the biggest part of the business.
- JSJay Shetty
Yeah.
- MRMichael Rubin
It's in a lot of ways very similar to art.
- JSJay Shetty
So it's, yeah.
- MRMichael Rubin
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 Mahan, said, "Hey, I got a great idea. Every time a player debuts for the first time, I wanna put a patch on their jersey, and then as soon as they get done the game, I wanna pull that patch off and put it in a one of one trading card."
- JSJay Shetty
Oh, that's sick.
- MRMichael Rubin
So you have the card from the, from the first... So think about for, for us, you know, maybe I grew up in the, in the Michael Jordan era.
- JSJay Shetty
Mm.
- MRMichael Rubin
Had I had, you know-
- JSJay Shetty
Kobe for me
- MRMichael Rubin
... Michael Jor- or yeah, if I had Michael Jordan or, or Kobe's first one of one cards-
- JSJay Shetty
LeBron, yeah
- MRMichael Rubin
... 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 wanna put a patch on someone's jersey, stick it into a card, and make this a one of 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 in sh- it was live in, in April with, with all baseball players. There's gonna be 300 to 400 baseball players debut this year, you know, with this debut patch that we put into a one of one card. So that's just, like, one of dozens-
- JSJay Shetty
Yes
- MRMichael Rubin
... of examples of innovations, because you have to be aggressive. Like, we have to be great entrepreneurs. We have to push in whatever we do.
- JSJay Shetty
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.
- MRMichael Rubin
Look, we're a three business tier. Our first business where we started is what we call Fanatics Commerce. That's our merchandise business. We own Lids, the hat retailer.
- JSJay Shetty
Yeah.
- MRMichael Rubin
We own Mitchell & Ness. Uh, 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, um, 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.
- JSJay Shetty
Mm-hmm.
- MRMichael Rubin
In the collectibles business, AI is gonna help us to be more effective. And then our third business is the online sports betting, 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.
- JSJay Shetty
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.
- MRMichael Rubin
I still wanna wear my Kobe jersey.
- 47:14 – 49:44
Avoid These Common Mistakes when Building a Business
- MRMichael Rubin
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 gonna take the at bat? So many people tell me, "I've got this great idea, but..." Like, I don't wanna hear about but. Like, let's go for it. Let's... If you have an idea, you wanna 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 wanna go out and do this," and you went out and did it. Like, part of being an entrepreneur is to have the courage to fail.
- JSJay Shetty
Mm.
- MRMichael Rubin
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 gonna learn from that failure. You're gonna grow from that failure. You think the best... You talked about Kobe being your favorite, you know, athlete. Well, guess what? How many times did he fail, and then he got better, and he pushed through 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 wanna 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 y- and I know some people are gonna say, "Oh, well, he's really successful now, so it's easy to say." But I gotta 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 wanna be s- 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, my work nearly every day. Like, I'm having work dreams all the time 'cause I'm obsessed with what I'm doing. It's like, it's, it's fun. It's like I should pinch myself, it's so awesome what I get to do.
- JSJay Shetty
I think pattern watching is, is an ability, whether it's an algorithm, whether it's the stock market, whether it's, you know, crypto, whatever it is for people, watching patterns is such an unbelievable skill. Would you say that's a skill that you've honed and developed and built?
- MRMichael Rubin
Well, I think it's a really important skill in business 'cause I think it's very predictive of the future.
- JSJay Shetty
Mm.
- MRMichael Rubin
Okay?
- JSJay Shetty
Mm.
- MRMichael Rubin
So the reality is when someone comes in and I'm interviewing a top executive for a role in one of our businesses,
- 49:44 – 52:05
Pattern Recognition Is a Business Superpower
- MRMichael Rubin
and they could seem great, and then I'm gonna go out, and I'm never gonna ask anybody for a reference ever. I've never asked somebody, "Hey, can you tell me who to call?" Like, that's the... You ask me for a reference on myself, I call each of those people and say, "Hey, I gave you as a reference. Make sure you say great things about me."
- JSJay Shetty
[laughs]
- MRMichael Rubin
Right? So the reality is I'll interview somebody. The first thing I do is if, 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.
- JSJay Shetty
Mm.
- MRMichael Rubin
Okay? Because to me, 50% is the interview and 50% is, um, what I learn 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.
- JSJay Shetty
Mm.
- MRMichael Rubin
Or you can find out that person was a little bit understated, but they're a beast. You know, they've got huge followership, um, 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 'cause you got a, you got a pattern going on.
- JSJay Shetty
Yeah, yeah.
- MRMichael Rubin
So you got to recognize patterns in whatever you do.
- JSJay Shetty
In our final clip, Suneera Madhani 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. 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
- 52:05 – 55:34
Why Hard Conversations Build Stronger Foundations
- JSJay Shetty
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.
- SMSuneera Madhani
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 t- you know, taking place about money or about business or about family, we were solving problems together.
- JSJay Shetty
Wow.
- SMSuneera Madhani
So my, my parents would always ask our perspective. That is something that I, I do feel is very interesting. Just as a child, I try to do that with my, 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, f- you know, our voice isn't heard. And so I grew up in a place where my voice was not just heard, it was really valued, and my perspective was valued. And there's, 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 Shah Rukh Khan concert, then when they would come out and do the, the shows. We went to Atlantic City for this concert and, you know, there was a casino. I'm not even of legal age [laughs] to g- 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.
- JSJay Shetty
[laughs]
- SMSuneera Madhani
Um, and it's, and it's important to see. Like, you, 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, "Well, how much is this? Like, am I gonna 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 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.
- JSJay Shetty
Mm-hmm.
- SMSuneera Madhani
Right? So my ability to be able to say, "Okay, I feel like I'm gonna win. I feel like..." Look at, looking at the hands or learning blackjack, and I was great at math, and I can get this concept. That was one of my... like, a core memory that I can think of.
- JSJay Shetty
Mm.
- SMSuneera Madhani
But I was always involved in the conversation. I feel like it was more tactical with action, not just being told-
- JSJay Shetty
Mm
- SMSuneera Madhani
... that you should go do this. I definitely feel very blessed that I, that I did have that. And now my mom lives literally across the street from me.
- JSJay Shetty
Oh, wow.
- SMSuneera Madhani
She's, like, one rock away, and we get to, she gets to raise my kids with me, so-
- JSJay Shetty
Oh
- SMSuneera Madhani
... it's wonderful.
- JSJay Shetty
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 gonna fail. This isn't gonna work"-And then obviously your dad gives you that encouraging statement. You said that you moved back home then.
- SMSuneera Madhani
Yeah.
- JSJay Shetty
So I'm imagining that you were making a decent amount of money working at a financial services firm, and when you choose to start a company, I'm guessing you took a massive pay hit. And
- 55:34 – 59:46
Courage Is the First Step Toward Risk
- JSJay Shetty
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've 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-
- SMSuneera Madhani
[laughs]
- JSJay Shetty
... 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.
- SMSuneera Madhani
I actually ask myself, would I do it again?
- JSJay Shetty
Mm.
- SMSuneera Madhani
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.
- JSJay Shetty
Mm.
- SMSuneera Madhani
It is such an incredible book. It's this crazy concept of just taking risks, and you have your golden years of your life. Like, we should be spending our money doing our things in our prime, and that makes complete sense. 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 br- 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?
- JSJay Shetty
Mm-hmm.
- SMSuneera Madhani
So what is the risk if you don't do the thing? And that's kind of how I try to make those, the risky decisions today, and I'm, I know our, we're gonna talk more, and this journey's gonna 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 my, 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, um, you do have to take, 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 gonna go build a fintech. Less than, currently, 2023, less than 3% of, uh, 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 naiveté 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 [laughs] knew right when we were 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.
- JSJay Shetty
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
- 59:46 – 1:03:49
Start by Solving a Real, Specific Problem
- JSJay Shetty
become big." So, so walk us through that a little bit.
- SMSuneera Madhani
It's done so much good, but it's ruined us, right? Like, it's ruined us in so m- so many ways. We have to stop doing things for the 'Gram. We have to... Like, 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 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 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.
- JSJay Shetty
Mm.
- SMSuneera Madhani
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- I'm always finding... Like, you're in the shower and you're like, "This should be better. This could be better." Right? You're, you're always finding the next thing. But ideas don't make you an entrepreneur. Execution does.
- JSJay Shetty
Mm.
- SMSuneera Madhani
Right? Everybody has ideas.
- JSJay Shetty
Yeah.
- SMSuneera Madhani
It's really about execution, and that's the thing. I feel like that's the thing that I saw maybe in, like, Sal and I growing up, was like, you've got to put in the work. Even after everything that I have, I show up every single day and I work. I put my head down at night and I ask myself, "Did I, like, give my 110?" 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've just got to keep showing up. And like that mountain, the mountain's gonna be there, and then you're gonna climb it, and guess what? You're gonna get to the top, and you're gonna climb this thing. The next, the next day, there's another mountain, and there's another mountain. So you've got to love the- that challenge.
- JSJay Shetty
Mm.
- SMSuneera Madhani
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 founder's, 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. 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 am back again and, and building again. It's because I see, I see the problem, and I know we can solve it.
- JSJay Shetty
Yeah. I, I think you're the right person to ask this question to because you talked about working hard and working smart. But what was the mindset shift in building a million-dollar business, 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
- 1:03:49 – 1:08:32
What Got You Here Won’t Get You There
- JSJay Shetty
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?
- SMSuneera Madhani
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 c- 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 gonna break again. Your systems are gonna break. People are gonna break. It's gonna break because it's supposed to. Once you c- get, you know, you get things right, or you're, 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. It's... 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 m- you know, or the 100 million in value, they have multiple ri- lines of revenue, and so you're thinking outside of the box. So once we were acquiring small businesses, we've shifted to an enterprise strategy. Now I'm building again. We're selling directly to the banks. We're going directly to enterprise first because that was the one to many that I f- it took me seven years to unlock that next. And then I'm gonna go to small businesses. So you, 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 o- 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 f- that, me, it's me and my brother. We're one team. Was o- 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 c- the culture, the DNA value system, and those core values, those don't change.
- JSJay Shetty
Mm.
- SMSuneera Madhani
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.
- JSJay Shetty
Mm-hmm.
- SMSuneera Madhani
It's a different hard at the next level, but you can solve it.
- JSJay Shetty
Yeah.
- SMSuneera Madhani
And you can find people to solve it. And then at that next stage, we had amazing leaders at the, you know, $100 million mark. And when I started the company, the name of the company was Fat Merchant, by the way.
- JSJay Shetty
[laughs]
- SMSuneera Madhani
'Cause I was 25. You know, it was, 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 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, 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.
- JSJay Shetty
These founders didn't wait to be picked or wait until they felt ready. They created, they evolved, but most importantly, they continued 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.
- SPSpeaker
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."
Episode duration: 1:08:33
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