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

Episode Transcript
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Speaker 1 (00:00):
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 start
at a nine to five right now, which is really

(00:21):
a nine to nine, which is just funding someone else's
dream when you could be building your own. Recent reports
show that nineteen percent 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,

(00:41):
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
four billion dollars. You're going to hear from Michael Rubin,

(01:06):
founder of Fanatics, the sports apparrel company that was last
valued at thirty one billion dollars. You're also gonna hear
from Snira, who sold her last company for just over
a billion dollars, Brian Chesky, the founder and CEO of Airbnb,
and from Cody Sanchez, who's a self made millionaire specializing

(01:28):
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

(01:49):
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.

Speaker 2 (02:07):
You the number one health and wellness podcast.

Speaker 3 (02:10):
Jay Seti Jay Shetty Set.

Speaker 1 (02:16):
In this first clip, Emma Greed dives into how she
launches purpose driven brands rooted in real problems people face
every single day. This is a great lesson for you all.
Start with what's missing. The best business ideas come from
solving your own unmet needs. Design for the overlooked customer,

(02:38):
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 if your background or walk

(03:01):
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.

Speaker 3 (03:16):
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

(03:39):
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 and business

(04:02):
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 as just
completely left out of the fashion conversation. And why is

(04:24):
there dollar any less valuable than anybody else's. And so
I had worked in marketing for all of these years,
for fifteen 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.

Speaker 1 (04:43):
You know.

Speaker 3 (04:44):
It's like you have a group of cars, you need
a black girl and an Asian girl and then 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 side, and the boardrooms
were just all made up of typically like white men

(05:04):
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.

Speaker 4 (05:25):
That's just good business, right.

Speaker 3 (05:27):
Forget d E and I forget like, you know, this
idea of diversity, equity and inclusion doing 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

(05:48):
best serve customers the most amount of people. And then
when there's an acknowledgment 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.

Speaker 4 (06:05):
Directly to them.

Speaker 3 (06:06):
And I think that it's such an underthought about part
of business.

Speaker 4 (06:11):
You know, people usually bolt.

Speaker 3 (06:12):
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 thirty two sizes, it's in
doing nine different shades. It's in the very very beginnings
of what you're creating, and then you can dress it
up and make it look nice and put the right
kind of branding on it. But actually it starts way
earlier than that, And so I actually think about customers

(06:37):
in a way that I think most people don't.

Speaker 1 (06:40):
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 come?

Speaker 3 (06:55):
Believe 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 literally, like phone them
because you don't understand this, because.

Speaker 4 (07:14):
It's not for you, you know.

Speaker 3 (07:16):
And so I think that decisions are made in such
an abstract way in most companies. And you know you
see this when you know companies make mistakes, right, There've
seen a lot of like big fashion brands and big
consumer brands make mistakes that have seemingly kind of come
across as like insensitive, racist, completely misogynistic. That's just where

(07:38):
a decision is made. A company isn't inherently racist like
the whole company, it's just the decision making process is flawed.
I 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

(07:58):
and who's making the decisions? And I know that the
more people you bring around to 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.

Speaker 1 (08:10):
Yeah, that is such great. I love what you just
said about asking someone to call their partner or their
daughter or whatever it may be, because you're so right, Like,
I think so many people sit in meetings and they're
looking around, going these people don't know what they're talking about,
or like they just don't understand totally. How have you maintained?
Like I guess the question is how many of those

(08:32):
meetings have did you have to sit in until you
felt like I'm just going to do this or we're
just going to figure it out, or did you look
for someone who agreed with you and had your values
and did the research or was it kind of like
we're just going to build it ourselves. Like how much
give us a.

Speaker 4 (08:47):
Bit of that?

Speaker 1 (08:47):
Because I think a lot of people.

Speaker 4 (08:48):
Know, you know, it's so interesting.

Speaker 3 (08:51):
I'm at that point in my career now where I
don't sit in a lot of meetings. Now they pitched me,
which is lovely. I'm like, come over here and I'll
let you know if you can come in. But in
the early days, you know, I think that I sat
in a lot of situations feeling like, you know, the

(09:13):
great thing is I never doubted myself or any of
those ideas.

Speaker 4 (09:17):
I just thought I hadn't found the right people yet.

Speaker 3 (09:19):
It's a little bit like, you know, I'm happy to
kiss a lot of frogs, and I always have been
because again, I don't think it should be so easy
when you're doing something that is new and without so
much definition and unproven, like it's supposed to be hard.
And again it's like anything. I never let it get
to me. I just was like, poor poor chicken. He
doesn't get it yet, and he will do and he

(09:41):
will kick himself, you know, And that's fine, you know,
it's just it's part of it. And I don't mean
that in a smug way. But I never I never
doubted what I was doing. I was very very clear,
especially when we started Good America, and I was like,
this thing people don't understand, and we'll just get them
to understand it.

Speaker 1 (10:00):
Yeah, definitely, yeah no. And I think that's such a
great mindset to have and to not have the smugness
or bitterness because exactly that person just wasn't in the
right space.

Speaker 4 (10:08):
You don't know what, you don't know totally.

Speaker 1 (10:11):
It's totally cool. I feel like that all the time.
I'm like, I'm trying to find the people who want
to be part of this story, yes, and if they
don't want to be a part of this story. That's
totally cool, of course, because.

Speaker 4 (10:19):
They won't be great partners to you down the line.

Speaker 3 (10:21):
Right, It's like you either get it and you want
to be part of it, and you are happy to
know that you don't know it all right, because it's
about new space. It's like if we were all doing
the same thing and trying to set up the same companies,
we'd never find the skims exactly.

Speaker 4 (10:36):
You know, It's like you'd never land on it.

Speaker 3 (10:38):
You'd be like, that's too complicated, that's not how we
do things, and you skip over the great stuff.

Speaker 1 (10:44):
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, but wanted to
get out. You know, milk was outdoors, I was. You know, like,
there's a pain that pushes you in a better direction.
I'm not saying you don't have pain anymore. Of course,
there's stresses.

Speaker 3 (11:02):
I don't have that much pain. I have daily dramas,
but the pain has gone.

Speaker 4 (11:08):
You know what it is? You are fueled every day by.

Speaker 3 (11:14):
A piece of it is competition, right, It's like I
look at everything, there is no one who knows more
about jeans and nickers than I do. I look at
every competitor I go out in the market.

Speaker 4 (11:27):
I see it.

Speaker 3 (11:27):
I know, like the promotional cadence. I know everything everybody
else is doing.

Speaker 4 (11:31):
And I think.

Speaker 3 (11:32):
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 had successes for six and for three years. I

(11:52):
don't think that's the end goal. The end goal is
to build, like you know, generational or generationally defining business,
and that doesn't happen quickly. And also I'm not stupid
enough to think like, oh, 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,

(12:16):
you know, really taking the foundations of what we've felt,
not sacrificing any of your principles, and still being able
to grow and to thrive and to hire people.

Speaker 1 (12:28):
The next clip comes from Cody Sanchez, Well she breaks
down her top tips on what it really takes to
build and buy businesses that lost. Remember that business is
long term grit. Success is enduring low level pain longer
than others will. Here's what I want you to focus
on in this clip. You're going to fail, You're going

(12:48):
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

(13:10):
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 to people need to be able
to run those businesses. How much industry knowledge do they need?

(13:33):
What business skills are core and important? Because I think
the mistake is, again with the kind of world we
live in right now, it's someone goes I love what
Cody saying, I get it. I'm going to go buy
vening machines and then all of a sudden you've got
a garage full of like twenty vending machines and you
don't what to do with them because you don't understand business.
So what core business skills are needed in what should

(13:54):
we be developing in order to run any of these businesses?
How much industry knowledge do we need?

Speaker 5 (13:58):
Yeah, that'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

(14:20):
decent amount of up front 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?

Speaker 1 (14:34):
Well?

Speaker 5 (14:34):
Where we don't know what we're doing, but we plow
a bunch of money into it because we want to
just go do the thing. It doesn't work out, So
spend your time learning how to execute first. Now that said,
I really think there's just three key skills that we
need to learn to grow a business. The first one
is deal making. We got to understand how to do
a deal. The second one is really the mixture of

(14:55):
grit and endurance. So it's actually not tactics, it's how
hard am I willing to work? What am I willing
to sacrifice for the things that I want? And for
how long am I willing to do that? And so
Angela Duckworth famously University of Pennsylvania popularized grit is the
most important thing to measure success. So it's basically like

(15:15):
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.

(15:36):
Often you're like messing around with marketing. It's kind of
like low level pain. And so that's the second point.
And the third point is actually maybe a little rare too,
which is just a lot of people obsess on how
so what skills do I have to have? Exactly? How
do I start a business? How do I tax? Structure,
structure at the business? How do I get my first customers?

(15:58):
All important and good questions, but the real pros, No,
you don't ask how, you ask who? Who can I
go to who already has ten thousand 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

(16:18):
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

(16:39):
is really about your connections. And so I think if
you understand deal making, you are honest with yourself about
how much work you're willing to do one where 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?

Speaker 1 (16:59):
No?

Speaker 6 (17:00):
Not?

Speaker 5 (17:00):
Could anybody run your businesses which are quite big? No,
of course not. It's really like the level of skill
to the level you're at. But we don't say to people,
you know, well, not anybody could buy an individual apartment
apartment and live in them. We ask like, what do
you want and how are you willing to work in

(17:20):
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 DELFI says, no, 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

(17:42):
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, you know, because we
could go well fifteen ways from sideways on, Like we
have something called the nine p's, which are like the

(18:04):
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.
Like if you have those three things, you can at

(18:25):
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.

Speaker 1 (18:33):
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.

Speaker 5 (18:52):
Right, well, you probably already know this. How many people
offer you businesses or stakes and businesses? Now, yeah, I've
been a lot lot. 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

(19:13):
the trust transference. So the higher level of skill you have,
the easier it is for you to find businesses. In fact,
they'll often come to you. The thing is, though, even
when we have a higher level of skill, we often
don't really know what to do when it comes to us.
We don't know how to do zero risk deals to us.
And so I like learning deal making even if you
have a ton of skills and a ton of money,

(19:34):
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 tech Jeff Bezos engineering
capability or labor you have access to, so employees or

(19:56):
people that will work with you, the better deals you
can do. And that's like the two two three Toho
three 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

(20:17):
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 insteadive aligned with them long term,
and so they end up getting screwed. Like it broke
my heart when I watch that documentary with Val Kilmer,
like it, Oh God, First of all, you would love it.

Speaker 4 (20:38):
It's beautiful.

Speaker 5 (20:38):
The documentary is beautiful. He wrote it, produced it and
directed it and started it and it's just a beautiful
piece of art. But also he lost everything. I mean
he has basically no money now, no way, 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. 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

(21:01):
bigger that you get, the bigger target you have. And
so it's important to think about that and like the
Russian proverb trust but verify, which is like trust nobody.
I'm sorry, trust everybody, but verify that they are actually
on your best terms, which is why I always doesn't
count unless you've signed on the line that is dotted
in the words of Alec Baldwin. So if you don't

(21:22):
have deals coming at you because you don't have massive
you know, fame or money or whatever like a normal person,
then the easiest way is to find deals. It's called
origination and 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,

(21:43):
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 and out
of your brain that is trained from the African Savannah

(22:04):
to say, if I keep repeating this thing brain, it
means it's important and I might die if I don't
pay attention to it. And so in real life, what
happens to you is once you play the game of
business enough, then once you like deals, 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 set up. I

(22:24):
don't think I would do that. Oh I like that
they did that. Let's steal that.

Speaker 4 (22:27):
Right.

Speaker 5 (22:28):
Your reticular activating system is so turned onto podcasts that
you can't help but notice all around you things you
would do differently or that you like the same thing
happens with business and deals. So now when I go
into a corner store, or when I go into a restaurant,
I go or Jim Jim's get me. For some reason,
it's like you have me, you have my credit card,
you have recurring revenue. I come in here every single day,

(22:48):
sell me more shit? Why don't you sell me more things?
So 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, reticular activityding system comes on. So what's
gonna happen in deal finding? Yes, you could cold call,
just like private equity, but instead kind of steep yourself

(23:10):
in the type of deal you are looking for, steep
yourself in what skills you actually have, and then you're
gonna 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 love's curiosity.

(23:34):
Every time you go into a small business, you just
go like, ah, amazing, you go, I mean, LA is
full of them. You walk into a cool retail shop, Ah,
that's cool, man, this is your store. It is I
mean probably fifty percent of the time it's theirs. And
then you say to the guy, like, how long you've
been doing this? A while? Do you want to keep
you want to keep doing this?

Speaker 6 (23:51):
Like?

Speaker 5 (23:51):
How's business going? You guys make a lot of money?
How long you've been around? Is a kid gonna take over?
Are you going to keep going?

Speaker 1 (23:56):
Oh?

Speaker 5 (23:56):
This is so cool. I love this. Maybe I buy
a little something, and then maybe I I want to
own one of these businesses with them. All of a sudden,
I get to know the owner and I start getting
into the curiosity where I get them to maybe consider
that a young hustler who is really aggressive might be
good for their business.

Speaker 1 (24:12):
Absolutely. Before we continue, let's take a quick breather and
listen to some of our sponsors. I hope you got
introduced to some great deals. Let's pick up where we
left off.

Speaker 5 (24:25):
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, buy 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

(24:46):
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 Holmes 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
seventies and was like, you know, I'm ready to be done.

(25:07):
And what he didn't know at the time is that
a business that is doing a couple of 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 it
was sort of And this is what most baby boomer

(25:31):
business owners think. They're like, who's going to buy this?
Because how many times have you had a business where
you didn't want to be in it before have you
ever had that before?

Speaker 1 (25:38):
Absolutely?

Speaker 5 (25:39):
Of course, Like if you're in a room. Sometimes I
go out to speaking stages and just for shits and giggles,
because people will always go If a business was profitable
and it was going to continue to be profitable, nobody
would sell it. And I go, okay, let's buy a game.
Business owners raise your hand. Everybody raises her hand. That's
a business owner. I go, cool, keep him up. If
you would sell your business at the right price, the

(26:00):
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 a laugh because the truth of
the matter is you haven't been in the game long
enough if you put your hand down. But if you've
been in the game long enough, you go absolutely. Now
I wouldn't sell every one of my businesses, but there
is at some point one business, and if you call

(26:20):
me here 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

(26:41):
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 acqui hire. There could have
been value in the website listing. What about the Yelp
and Google reviews. There could have been value in the IP.
What about the logos and the brand and the name.
What if they had one of those old school original
you know, cody dot com websites before like we now

(27:01):
have to have websites that are like four hundred and
fifty two 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, and then you've got a
really good deal.

Speaker 1 (27:15):
Next up, Brian Sheskey 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

(27:37):
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

(27:58):
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 sixteen years ago.

Speaker 6 (28:09):
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 fifteen years ago, i started my co founders, I
was totally broke. I had no status, had no power,
no money, nothing, And I felt like what would make
me happy was climbing a mountain and becoming incredibly successful.

(28:34):
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 that at this point, like
I'm forty one years old and a lot of people
ask me like, why don't you just retire? Like or
why don't you do it all over again? And for me,
I would tell them because the fund is just starting.

(28:56):
But the fund 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

(29:17):
never has a designer being given so much responsibility, so
much opportunity. And what I love is, you know, like
a musician wants to play music, a painter wants to paint,
a builder wants to build, a climber wants to climb,
And as an entrepreneur, I want to create and connect
things and try to like defy the notion of what

(29:41):
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 paces, many different flavors, and
that a creative person, you know, can run a company,
and it can run a really big company, a fortune

(30:02):
five hundred company, then that's the very beginning. And 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 stround
up with, and I get to like work every single
day with people I love on ideas that I'm obsessed over,

(30:25):
and I'm just so obsessed. I think my motivation has changed.
I think when I started with my motivation was about
myself becoming something, and once you achieve that, your motivation
often turn turns outward. It's about its starting to be
about giving to other people, to lending them experience a
small part of what I was able to experience, and

(30:47):
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 us, because at some point you've
gotten all that, 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.

Speaker 1 (31:09):
That's beautiful. That's I can see that it's true for
you too. I can see that it's real for you
as you're saying it, which is such a special place
to be. And it was interesting when you were talking
about this idea of climbing a mountain. I've often thought
that there's one journey in life that we take that's
upwards up a mountain, and then there's another journey we

(31:32):
all have to take that's inwards to the valley. And
that's a journey that not everyone gets to take or
everyone thinks about taking, because we're so busy trying to
get up that we don't often get to go in right,
And it sounds like you've been excavating that internal part
for some time.

Speaker 6 (31:48):
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 fifteen years. The highs are incredibly high,
the lows can be incredibly low. The amount of stress

(32:09):
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
in the way down. Maybe another way of saying it

(32:32):
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 that tends to amplify things.
I mean that can be good, but it all still
can amplify holes you have in yourself. People that are

(32:54):
a little bit paranoid get very paranoid. People that are
a little deceitful become like completely fraudulent liar, 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 and like not actually dealing with things if

(33:16):
you can't, if you're not decisive, there's going to be
an element of bureaucracy. If you're like get overwhelmed and
you get paralyzed, there's going to be an action in
the company. And so you learn so much about yourself
and I through this process, I probably 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

(33:40):
the company is like a mirror about you, right, Like
when you see a company, it's like a 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

(34:01):
is like that, but it's like one 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 in everything they do, but everyone they
surround the self with and the culture they create and
what they And that's the thing that's so crazy.

Speaker 1 (34:17):
I'm intrigued. You said something there that really stood out
to me. You said that the happiest thing and the
best thing about being successful is that you get to
choose the people you worked with. You obviously built this
with friends. Yeah, and that's how it started. It started
in a place of being around people you love with
What was the biggest point of challenge in building something

(34:38):
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.

Speaker 6 (34:54):
Think about how many stories you heard of founders. It's
like a band. They come together other 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 becomes so much bigger than
the band because it's not just the three of you.
Imagine a band that starts three people and ends is

(35:16):
three thousand people. And that amount of pressure, the amount
of spotlight, the money that changes in like people's status
and positioning, it can do a lot to break people up.
But also, unlike a band, where maybe I'm 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,

(35:38):
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
going to supersede our friendship in our relationship, that we're

(36:00):
never going to have well debate, will argue, but will
never allow a situation where winning an argument is the
most important thing. Because you think about a company as
one hundred thousand decisions, it could also be one hundred
thousand arguments. And if you get stuck on the first debate,
or you like somebody won a debate, okay, great, you
have ninety nine ninety nine more things to discuss. And

(36:22):
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're at the
right place, the right time, with the right idea. And
I said well maybe, But there's something I was much
luckier about. And what I was most lucky about. What
made me most fortunate was I met Joe and Nate.
That we have this unbelievable chemistry. One time we had

(36:43):
to do some personality tests. It's 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 equal Adimble triangle. Not always you're going
to find people that are perfect compliments to you. I'd
say a couple things. Number One, you want to have
a team with people that you are friends with or

(37:06):
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 in the same Folle system. If you have
different values, eventually there's going to become irreconcilable conflicts. But

(37:29):
you probably also want complimentary skills the worst case is
people with different values and same skills. Right, we do
the same job. We step in each other's tolls, and
we're trying to go in a different direction. And 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

(37:50):
try to make sure that like Joe and Nate, you know,
were included in things. And I wanted to always make
sure that people referred to us together. We thought of
us as as a unit. When I like when 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

(38:12):
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 have multiple founders. But if they're together,
they're not fighting, and they have a mutual love and
respect from another, that's going to permeate the company, just
like it permeates the health of a child. And joan
A and I kind of thought ourselves as parents and

(38:33):
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 and that relationship permeates every single thing.
If the founders fight, the employees fight, if they have
one respect from one another, that is going to be
a role a model that other people throughout the organization
are going to copy. And that's what I've learned from that.

Speaker 1 (38:54):
In this conversation, Michael Rubin shaz how staying obsessed, learning fast,
and stay saying hands on drive 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,

(39:15):
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.

Speaker 7 (39:33):
I think it's something for me I was born with,
Like I was born with that entrepreneur a 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.

Speaker 4 (39:47):
I love it.

Speaker 7 (39:47):
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.

Speaker 5 (39:52):
Just want to go.

Speaker 1 (39:53):
Yeah, can it be learned? Can you teach people to
hustle and grind and develop their mindset or is it
born with as you are?

Speaker 7 (39:59):
So I think I was definitely born with it. That said,
I do think, you know, for me, the way I
learned is by being a sponge from people. So I'm
always picking things up from different people. Like if you
just look at the diversity of people I have around me, Like,
I'm always taking so much learnings from them to you know,
be better on what I do, and I try to
give those back. So yeah, I think you can definitely
learn a lot of the stuff just what you know,

(40:19):
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 band 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 im myself.

Speaker 1 (40:35):
That's right, That's all I asked for, That's what I
ask for. There is no judgment here, there's no it's
a safe space. I just want people to be the
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.

(40:58):
Was there anything that kind of stuck with you?

Speaker 7 (41:00):
Yeah, for sure. I mean, look, I'm in LA for
the week. I'm doing six to ten meetings a day
in my house and you know, to the people I
met with the last two days has 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

(41:22):
no chance of like you know, getting better at what
you do. I mean it's like life is no different
than sports. You just got to keep getting better at
your sport. And so to me, I keep working in
everything I do.

Speaker 1 (41:30):
Yeah, what do you think obviously now, like when you
started forty three years ago at eight years old, entrepreneurship
wasn't as talted as this incredible it was.

Speaker 7 (41:40):
The time was it was actually weird right, 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 from
my perspective, everything was really the birth of the dot
com error. Yeah, you know, kind of late nineties is
when entrepreneurialism became cool. I think before that was kind
of nerdy and weird. So I was definitely born before

(42:02):
it all.

Speaker 1 (42:02):
Yeah, And I'd say even after the financial crisis in
like two thousand and seven eight, 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, the

(42:22):
one after me, they were like, I'm not going to
go work for someone. I want to build something on
my own.

Speaker 7 (42:26):
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 businesses, the collectibles business,
which is trading cards of my rebility, 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

(42:48):
I grew up selling trading cards an eight year old.
But also it's all about entrepreneurialism.

Speaker 1 (42:52):
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 stick Yeah, so that's what
we have. We'd have the big you'd have the spread
with all the Premier League clubs and you'd collect the
little stickers and that was a big part of collectibles.
How has that industry evolved as technology has grown on?
Has it stayed the same where people are still collecting
cards and like top trumps and things like that.

Speaker 4 (43:15):
Yeah.

Speaker 7 (43:15):
Well, I'll say we got into the business about three
years ago in a really significant way, and today we
own Tops, which is the you know, kind of pre
eminent brand in trading cards. I'd say that, you know,
until our arrival in the industry little less than three
years ago, I said, there hadn't been you know, a
tremendous amount of innovation. There hadn't been a tremendous amount
of marketing.

Speaker 6 (43:32):
You know.

Speaker 7 (43:32):
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 one hundred thousand people
that come to Chicago this past summer. It's called the
National Trading Card Show. Yeah, it looks like something from
twenty thirty forty years ago. So for us, that was
just that just mynt opportunity meant if you actually make

(43:55):
innovative products, you actually really market these products, you build
a better consumer experience. It's and bring people ford into
twenty twenty three. Like what an opportunity. So for me, like,
we do that in all of our business, Like I
love like we love finding great opportunities, big challenges and
kind of being unrelenting about going after them.

Speaker 1 (44:11):
Yeah, how has that changed? How is that practically changed?
Like people are still buying cards and trading cards are
the biggest.

Speaker 7 (44:17):
Part of business. It's in a lot of way, it's
very similar little cart 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
like man 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 that patch off and put it in a one
on one trading card, so you have the card from

(44:37):
the first So think about for us. You know, maybe
I grew up in the Michael Jordan, or had I
had you know, Michael Jordan, or yeah, if I had
Michael Jordan, or Kob's first one on one cards. Yeah,
that could be the most valuable keepsake that I could
ever have. And so you know that innovation, Like for us,
it was really simple, like, yeah, why would you not
want to put a patch on someone's jerseys sticking into
a car to make this a one on one card?

(44:58):
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 it was live
in April with all baseball Players's gonna be three to
four hundred baseball player's debut this year, you know, with
this debut pats that we put into a one to
one cart. 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.

Speaker 1 (45:18):
Yeah. Now, 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.

Speaker 7 (45:35):
Look, we're three business there. First business where we started
is what we call finax commerce. That's our merchandise business.
We own Lids, the hat retailer. We own Mitchell Nas.
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 six billion hours
of mostly fan apparel and headware. Okay about you know,
you know, more than one hundred million units of merchandise

(45:57):
a year. That's a very physical business. Okay, but AI
is helping us to do things more effectively in the
collectible's business. AI is going to help us to be
more effective. And then our third business is the online
sports better than I gaming business. So you know, for me,
we still do a lot of physical things, but there's
so many things from the digital world that help us
to be better.

Speaker 1 (46:14):
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. Okay,
we're back. Let's dive right back in.

Speaker 7 (46:35):
I still want to wear my Kobe jersey, yeah, exactly, exactly.
I want my Bronz card.

Speaker 1 (46:39):
Yeah, that's the same thing I'm still buying. I support
Manchester United, That's that's my soccer team, and I'm still buying,
you know, soccer jerseys every single year.

Speaker 7 (46:47):
We appreciate that because that's a fanatics next door.

Speaker 1 (46:49):
Even though I absolutely even though we absolutely suck right now,
but it's you know, but that's.

Speaker 7 (46:53):
What sports fans about it. Sometimes you're great years and
you get you're getting those championships, and other times you're
gonna suck and you gotta stay with your team feel
the pain.

Speaker 1 (47:01):
I'm a real fan now. I grew up as a
glory hunter because we just want everything, and now I'm
going through real fandom of ten years.

Speaker 7 (47:07):
Test you now, I'm gona see what you're made of.
Are you really committed to man United here? Yeah?

Speaker 1 (47:11):
I'm being tested right now. I'm being perfect. But we
were talking about people not being entrepreneurship not being towed
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 kudosk

(47:32):
that it deserves. What are the mistakes people are making
when they think about being an entrepreneur today?

Speaker 7 (47:37):
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. For me, Look,
the biggest mistakes I see people make in building a
business are kind of a couple of common themes. One is,
first you have like are you even going to take
the app bat? So many people tell me I've got
this great idea, but I don't want to hear about

(48:00):
but like, let's go for it. Let's see if you
have an idea you want to do something. You know,
I love the story you were just telling me before
we went on here that you came over here and
you know, you worked one place for six months. Then
you're like, I want to go out and do this,
and you went out and did it. Like part of
being an entrepreneurs to have the courage to fail, Like
you just have to go out there and try. And
by the way, when you fail, which many times you will.
You're gonna learn from that failure. You're going to grow
from that failure.

Speaker 4 (48:20):
You think the best.

Speaker 7 (48:20):
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

(48:41):
if you strike out, if you fail, just go back again.
And I know some people going to 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 aemo, has gone bankrupt
multiple times. You know, I've had epic failures and every
one of those led me to be better than what
I do. So that's my first thing. Second thing I'd
say is you need great people around you to succeed.

(49:03):
Like whether it's great people you're learning from that you
want to be a sponge from whether it's build a
great team to do what you do. Like I know,
for fanatics, we have eighteen thousand 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

(49:24):
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 job of the planet.
I get to wake up, you know, work eighteen hours 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 when I get.

Speaker 1 (49:43):
To do I think patin watching is an ability, whether
it's an algorithm, whether it's the stock market, whether it's
you know, crypto or whatever it is. For people watching
patons is such an unbelievable skill. Would you say that's
a skill that you've honed and developed and built.

Speaker 6 (49:57):
Well.

Speaker 7 (49:57):
I think it's a really important skill in business. I
think it's very predictive of the future. Okay. So the
reality is when someone comes in and I'm interviewing a
top executive for a role in one of our businesses,
and they could seem great, and then I'm gonna go
out and I'm never gonna ask anybody for a reference.

Speaker 6 (50:13):
Ever.

Speaker 7 (50:13):
I've never asked somebody, hey, can you tell me who
to call?

Speaker 6 (50:15):
It?

Speaker 7 (50:15):
Like, that's the you ask me for reference? On myself,
I'd call each others people and say, hey, I gave
you as a reference. Make sure you say great things
about me.

Speaker 1 (50:20):
Right.

Speaker 7 (50:21):
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, fifty percents the interview and fifty percent
is what I learned behind the scenes. And that's probably
the more important fifty percent, because someone can blow me
away and then you know, you'll find out one minute

(50:43):
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 are beasts. 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 or play blackjack with my friends. You know,
there's three types of cards you're gonna get cars. You're

(51:04):
either going to be you know, you're either streaking heart,
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 it if I'm misbehaved, which is be
aggressive when you're cold, because you got a patterner going on.
So you gotta recognize patterns whatever you do.

Speaker 1 (51:17):
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

(51:39):
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. Some solving the un

(52:01):
sexy 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 in 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,

(52:21):
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

(52:43):
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.

Speaker 8 (52:50):
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 you know, taking place about
money or about business or about family. We were solving

(53:10):
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.

Speaker 2 (53:27):
So I feel like I was really involved.

Speaker 8 (53:28):
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 seventeenth birthday.

(53:51):
This is really crazy. So we went to Atlantic City
for a Bollywood concert. It was like a Charlotte Cohn
concert then when they would come out and do the show.
We went to Atlantic City for this concert and you know,
there was a casino. I'm not even of legal age
to great gamble, and my dad takes me to the
blackjack table. Okay, and he was an avid like he

(54:12):
definitely had not the best habits as well, and it's
and it's important to see, like you can see both
sides if 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.

Speaker 2 (54:26):
My parents were also really young.

Speaker 8 (54:27):
They had me when they were like twenty 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 that, and in my head, I'm like,
how much is this?

Speaker 6 (54:42):
Like?

Speaker 8 (54:42):
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, that more, if
you feel like you're not going to win, pull back
my ability to now take risks and listen to my
gut and not worry about, you know, like scared. He
doesn't make money as well, right, so my ability to

(55:03):
be able to say, Okay, I feel like I'm gonna win.
I feel like look at looking at the hands or
learning Blackchack and I was great at math, and I
can get this concept.

Speaker 2 (55:12):
That was one of my.

Speaker 8 (55:13):
Like a core memory that I can think of. But
I was always involved in the conversation. I feel like
it was more tactical with action, not just.

Speaker 2 (55:20):
Being told that you should go do this.

Speaker 8 (55:23):
I definitely feel very blessed that I did have that.
And now my mom lives literally across the street from me.
She's like one rock away, and we get to she
gets to raise my kids with me, So it's wonderful.

Speaker 1 (55:34):
It's amazing when you when you go from pitching your
idea to all of your bosses and they kind of
look at you like this is going to fail, this
isn't going to work, and then obviously your dad gives
you that encouraging statement you said that you moved back home. Then, Yeah,
so I'm imagining that you were making a decent amount
of money working at financial services firm, and when you

(55:55):
choose to start a company, I'm guessing you took a
massive pay here and as you are living out and
then you move 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

(56:16):
get for like eighteen years of your life, and everyone
respects you for it, it looks good on your LinkedIn
and your resume. I found so many people struggle at
that point to say, well, I'm willing to take less money,
I'm willing to downgrade my lifestyle. I'm willing to postpone
and delay the gratification of having nice things because chances

(56:36):
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?

(56:58):
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.

Speaker 2 (57:07):
I actually ask myself would I do it again?

Speaker 8 (57:11):
And I think that it also depends on It's the
risk taking ability, right.

Speaker 2 (57:16):
It takes courage to take risk.

Speaker 8 (57:18):
One of my favorite, most favorite books that I've recently
read is Die with Zero. It is such an incredible book.
It's this crazy concept of just taking risks and you
have your golden years of your life, like we should
be spending our money doing our things in our prime and.

Speaker 2 (57:33):
That makes complete sense.

Speaker 8 (57:34):
And the risk tolerance that you can take also changes
with your age. Would I take these risks if I
had two daughters at home? And maybe if I was
a sole breadwinner or where I don't know, And so
I can look back and say I didn't have much
to lose, and it was a level of risk. I
had a steady job, I was on a career path.
I could have totally miserably failed.

Speaker 2 (57:56):
I think you have to think.

Speaker 8 (57:57):
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.

Speaker 2 (58:14):
In ten years.

Speaker 8 (58:15):
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.

Speaker 2 (58:30):
And so it's really about the risk of not doing
the action.

Speaker 8 (58:34):
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.

Speaker 2 (58:51):
It's not enough.

Speaker 8 (58:52):
It is hard to build a business. You know, less
than two percent of female founders ever even break a
million in revenue.

Speaker 2 (58:59):
That is the most insane statistic.

Speaker 8 (59:02):
Men are eight times more likely to achieve that venture
capital right, I'm going to go build a fintech less
than Currently twenty twenty three, less than three percent of
capital goes to women founders. Less than one percent, it's
in the decimals, goes to minority founders.

Speaker 2 (59:17):
What was I even thinking trying to go raise.

Speaker 8 (59:19):
Capital out of Orlando, Florida, not even Silicon Valley, Right,
And So I think there's a naivete when you're young,
and I think it's beautiful.

Speaker 2 (59:28):
I think that it's the most amazing thing.

Speaker 8 (59:30):
Like I even think about parenting, like, oh my god,
now if I knew all the things that I knew
right when we were young and.

Speaker 2 (59:36):
Doing the things, I think.

Speaker 8 (59:37):
That having a little bit of not knowing what's on
the other side is actually really beautiful too, Like embrace
that I.

Speaker 1 (59:45):
Feel like this generation might be missing out on the
businesses that solve real problems that affects 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 woke us through that understanding of how you
encourage founders to find their niche and build their product

(01:00:05):
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 so woke us through that
a little bit.

Speaker 8 (01:00:14):
It's done so much good, but it's ruined us, right
like it's ruined us in so so many ways. We
have to stop doing things for the gram we have
it is it is our mentality of building companies, products,
services that if.

Speaker 2 (01:00:28):
It's not this, then it's not that.

Speaker 8 (01:00:30):
And I also think that it's important for us to
have a social presence and to.

Speaker 2 (01:00:34):
Utilize all these tools that we have.

Speaker 8 (01:00:35):
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

(01:00:58):
the most complex problems for us. So we did forty
billion dollars in payments through this ecosystem that I almost
didn't start. If I didn't build it, we solved huge
problems in this It was so unsexy. Card present versus
card not present, so Stripe was focused on digital transactions.
Square was focused on in person transactions. Guess what there
was nobody bridging the gap for like dentist offices that

(01:01:20):
needed both in person and online transactions.

Speaker 2 (01:01:23):
Boom.

Speaker 8 (01:01:23):
There was the opportunity that nobody saw on building that tech.
And it's not about I didn't have the background. I
wasn't a coder, I wasn't an engineer, but I could
see where the world was going. And I think that's
what entrepreneurship is. It's the spirit of solving for problems.
It's not for show. Success will come if you just
like let go of that and you can also have

(01:01:46):
a social following and build a great band and have
the podcast and do the things to go reach more people.

Speaker 2 (01:01:52):
But you can solve if you just focus on solving
the problem and seeing it uniquely.

Speaker 8 (01:01:57):
And if it's one of you, you're really like it's
resonating with you because you're like I am that person.
I 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.

Speaker 2 (01:02:12):
Execution does, right.

Speaker 8 (01:02:14):
Everybody has ideas, it's really about execution, and that's the
thing I feel like, that's the thing that I saw
maybe in like Salini growing up, was like 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 one hundred and ten? I
work so hard still and it's just part of and yes,

(01:02:35):
I work smart too, so it's not that I'm not
just grinding my way and being intentional, but hard work
is a huge part of it. Because there's no such
thing as a billion dollar idea. It's a billion dollar.

Speaker 2 (01:02:46):
Execution, and to execute it's every single day.

Speaker 8 (01:02:50):
You just got to keep showing up and like that mountain,
the mountain's going to 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.

Speaker 2 (01:03:00):
So you've got to love that challenge. That's what entrepreneurship is.

Speaker 8 (01:03:05):
It's not I didn't build a billion dollar It took
me twelve years to build that business, ten years to
exit that business. It didn't happen overnight. It happened because
I just kept showing up. It wasn't this magic formula.
And people ask like, what was the secret to the
billion dollar success?

Speaker 2 (01:03:19):
I didn't give up, Like I just somehow kept showing up.

Speaker 8 (01:03:22):
I can name every founders, like every journey where we
almost did to make pray Roll, I had to put
my mortgage on the line.

Speaker 2 (01:03:27):
We had to do. We didn't get the investors, we
lost the customers.

Speaker 8 (01:03:30):
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 I exit, right it's like here,
I'm back again in building again. It's because I see
the problem and I know we can solve it.

Speaker 1 (01:03:49):
Yeah, I think you're the right. President asked this question
to you because you talked about working hard and working smart,
But what was the mindset shift in building a million
dollar business one hundred million and 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 ten or one hundred. I don't
know what what do I need to do differently because

(01:04:10):
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 ad to up level to go from
one to one hundred hundred to a billion?

Speaker 8 (01:04:30):
You're brilliant because everything has to change. It's completely different
going from your zero to six figures, you know, getting
that validation of your it's a completely different journey from
zero to six, from six to seven, it's a completely
different journey.

Speaker 2 (01:04:44):
And everything breaks, and it's supposed to break.

Speaker 8 (01:04:47):
Going from seven to eight figures in revenue, it's going
to break again. Your systems are going to break, people
are going to break. It's going to break.

Speaker 2 (01:04:53):
Because it's supposed to.

Speaker 8 (01:04:55):
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, 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

(01:05:15):
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 you know, or the

(01:05:36):
one hundred million in value, they have multiple lines of
revenue and so you're thinking outside of the box. So
once we were acquiring small businesses, we've shifted to an
enterprise strategy. Now I'm building again, we're selling directly to
the banks. We're going directly to enterprise first, because that
was the one to many that it took me seven
years to unlock that.

Speaker 2 (01:05:53):
Next and then I'm going to go to small businesses.

Speaker 8 (01:05:55):
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, oh 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

(01:06:17):
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

(01:06:37):
team tattooed here on my arm. It comes from that
meets me, my brother. We're one team, we wan 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,

(01:06:58):
but that needs to say. Ground did end 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.

Speaker 2 (01:07:10):
To solve it.

Speaker 8 (01:07:11):
And then at that next stage we had amazing leaders
at the you know, one hundred million dollar mark.

Speaker 2 (01:07:16):
And when I started the company, the name of the company.

Speaker 8 (01:07:18):
Was Fat Merchant, by the way, because I was twenty five,
you know, it was it was fun and we were
disrupting the industry.

Speaker 2 (01:07:25):
But I knew Fat.

Speaker 8 (01:07:27):
Merchant was one hundred million dollar company. Stacks was a
billion dollar company. And I had to get comfortable, even
though it was 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.

Speaker 2 (01:07:44):
That's hard. Change is hard for.

Speaker 8 (01:07:45):
Organizations, and so you've got to go build and.

Speaker 2 (01:07:49):
To be willing to willing to change.

Speaker 8 (01:07:51):
It's supposed to break, So get comfortable with it breaking,
and you just get better.

Speaker 2 (01:07:54):
It doesn't get easier, but you get better.

Speaker 1 (01:07:57):
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,

(01:08:19):
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

(01:08:40):
what you do. If you're trying to find your passion
and your lane, Rick Rubin's episode is the one for you.

Speaker 5 (01:08:47):
Just because I like it, that doesn't give it any value,
like as an artist, if you like it, that's all
of the value. That's the success comes when you say
I like this enough for other people to see it.

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Jay Shetty

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