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July 4, 2025 19 mins

Everyone wants the freedom of being their own boss—but no one talks about the cost. In this episode, I break down the real pros and cons of business ownership. From building wealth and designing your dream team to dealing with lawsuits, loneliness, and sleepless nights—I’m sharing the truth behind the glamor.

Whether you’re thinking about quitting your job or you’re already deep in the trenches, this conversation will help you get clear on what it really takes to build something that lasts—and why, despite everything, the tradeoffs are still worth it.

Join me August 1st in AZ

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
S1 (00:00):
Welcome to business and the podcast for people making it
all happen. Running a successful business completely takes over your life,
but I'm a believer that there is still room for
some ands like health, wealth, beauty, and maybe even some fashion.
On this podcast, I'll share with you what's working for
scaling my nine figure business while keeping you up to
date on the latest trends, news and fun finds. This

(00:23):
is a place for business and let's dive in!

S2 (00:26):
Welcome back to business and it sounds so sexy to
own a business. The Instagram, the TikTok, the YouTube. Oh,
make it so exciting. Oh, you too can own a
business for free 99. The reality is, there are a
lot of upsides to owning a business and it can
be spectacular, it can be wonderful, and if you do

(00:48):
it right, it can really help people. It can benefit
the world, it can benefit your community, and you become
a totally new version of yourself that you admire and respect.
But it can often go very wrong. And actually 97%
of businesses fail in the first ten years because they
don't know what they're doing, and it is difficult. Instagram
shows the highlight reel. It does not show the angst,

(01:10):
the pain, the suffering, the indecisiveness, the lack of confidence,
the lawsuits, the fraudulent activities of your team members. Like
it just doesn't show that stuff. No one talks about
that stuff. So today in this episode, I am going
through the pros and the cons of owning a business.
Let's dive in. Everyone wants to be their own boss,

(01:33):
but no one tells you that success can't be like
a prison. You see, I went from working a job
that I hated making $55,000 a year to building my
dream business and becoming a millionaire. I work with business
owners every single day, so if you've ever dreamed of
quitting your job to do your own thing, here's the good,
the bad, and the ugly of being a business owner

(01:54):
first is the biggest benefit of working for yourself. There
is unlimited upside. You see. Once I started believing in myself,
I realized that I wanted to be in control of
my life and what my work looked like. Today I
can travel on a whim. I can attend a fashion
show if I want to. I can build teams, and

(02:15):
I can do this because I'm able to. Through owning
a business, what's crazy about working for yourself and owning
a business is that the upside is truly unlimited. You
can spend just as much time as you might be
spending in a job where you're working for somebody else,
but actually create however much income you want to make.
If you want to have $1 million business, you can

(02:36):
create $1 million business for the same 40 hours of
work that somebody else is putting in, making $80,000. If
you want to have a $10 million business, you can
have a $10 million business. You could make $1 billion
if you wanted to. Because the upside is truly unlimited
when you own your own business. Now, that doesn't mean
that there isn't downsides to owning your own business. There
are pros and there are cons, but there really is

(02:58):
no cap on what the upside is for the time
that you are spending, growing and scaling your business. So
as a business owner, you get to remind yourself that
you are gaining flexibility, but that doesn't come without weight
because that flexibility can be reduced quite quickly. When you
realize how much responsibility you have for other people. You see,
you don't just build $1 billion business and get to

(03:20):
ride off in the sunset with $1 billion worth of revenue,
you have to figure out how do you keep your
team engaged? How do you keep people inspired around you?
How do you solve customer issues at massive scale so
you have a lot larger problems, but your upside isn't
capped and every pro has a con. And this next
con is that you're likely going to feel trapped. Being

(03:42):
a business owner means that you are never off duty.
I always laugh at people who say that they want
to be a business owner because they have time. Freedom.
This is a really nice thing to think about, but
it is not real in practice. The time freedom that
you have meaning. Nobody is telling you that you have
to work. Nobody is telling you when you show up
actually means that you have to show up earlier and

(04:04):
stay later and never shut off the responsibility. It is
not just showing up and having no risk. You actually
have to show up every single day, take on enormous
amounts of risk because it's your responsibility. So sure, there
is huge upside, but there is also massive responsibilities. And
right now, if you work for somebody else, you can
hate your boss and you can go home and do

(04:25):
whatever the hell you want to do while still hating
your boss. Imagine if you owned a business. You hate
your boss because they're a jerk and they are demanding,
and they might even be a little bit lazy. And
your boss is you. You don't get to take a
break from yourself. You go to work with that person
and you go home with that person. It is the
same person. You are your own boss and it can

(04:46):
sound really sexy and really enticing. When you really are
your own boss. Prevent many people from being successful business
owners because all of a sudden you get to blame
nobody but yourself for your problems. So if you don't
deeply love your work. The burden of this job can
make you resent your own company, your own team, and

(05:06):
it's very easy to entirely lose yourself inside of it.
If you do love your work but you feel trapped.
What I tell myself is I need to stay focused
on my mission. So whatever your mission is, how do
you stay so laser focused on the mission and where
you're going so that it makes null and void the discomfort,

(05:28):
the frustration, and the pain that you might feel each
and every day working inside your business. On to pro
number two. Business ownership is the fastest path to insane
personal growth. What's wild about running a business is how
quickly you learn just by doing it. You can read
books and go to school, and I've taken courses on

(05:48):
all the best ways to lead people. You want to
know how quickly you can learn how to lead people.
Get a team. Start having one on ones. Do your
first set of performance reviews. Hold meetings. That is how
you learn how to create a business, that is how
you learn how to grow a business. And it doesn't
come without its many challenges and many surprises. And ideally,
you learn from other people what those challenges and surprises

(06:11):
could be. So you are protecting yourself before getting punched
over and over again unnecessarily. I will never forget one
of my favorite sucker punches was when I had hired
a team member who was working in our events team,
and she decided to take her entire family on a
trip to Hawaii on our company credit card. And then
she proceeded to lie and say that she didn't and

(06:33):
actually say, how dare you say that? Because my daughter
had mental health issues and because I had to take
days off from work, that you say that I took
my kids to Hawaii on our company credit card and
I'm like, hmm, well, I mean, wow, she's really committed
to this story. I have to figure this out. Well,
luckily for me, I had been cheated on two times
in my life, so that skill set of being cheated

(06:56):
on is nicely transferred as a business owner. Because I'm
a am a professional sleuth. I will find out anything
about anyone on the interwebs. And I found her and
her kids, but I couldn't find anything in Hawaii until
I found her maiden name and found her kids who
I didn't even know existed, who were also on this
trip to Hawaii. And there was a Facebook photo of

(07:16):
family Facebook photo of them in Hawaii on the dates
in question. So yes, she boldfaced lied to me. She
gaslit me and said, how dare I tell her that
she was on a trip to Hawaii? And this was
a new set of lessons that I learned. But as
a business owner, this education is invaluable because you make
your system and your process better so that this never
happens again. You learn how to do background checks. If

(07:38):
I would have done a background check, I would have
found that she had done this to companies before. No
classroom can match the stakes of real ownership. Embrace the
place of this learning curve and you will gain experience
that most people spend decades chasing in a very short
period of time. Con number two is next. Building a
team will wreck you if you're unhappy with the way

(08:00):
that your team shows up, if you're unhappy with the
level of effort they put in the solutions that they create.
Every problem in your business is a direct reflection of
you as a business owner. So if you're unhappy with
your results, you should be unhappy with the way that
you show up and the way that you structure things.
This is only a con because you're not having great
results in your business, you're not growing your business. And

(08:22):
if your team is making it harder on you to grow,
it's because you don't know a thing or two about
leadership and what's required to get people to buy in
to you, to buy into your company the products and
services that you offer and help propel them forward and
make your business a better place to work. Not a
crappy place to work. You see, I used to really
struggle to be a leader when I got the first

(08:43):
team that I ever ran at the age of 22,
I had no idea what I was doing. I thought
that everybody around me was an idiot. Well, really, I
was the idiot. I didn't know how to structure one
on ones and have great conversations with them. So we
just would shoot the shit, but then results wouldn't be
driven and I would wonder why and say that they
aren't working hard enough and get so frustrated. And really,
it was just a reflection of my own inability to lead.

(09:06):
So if you want to start a business and you
are thinking, oh, I would love to just show up,
get out of there as quickly as possible, not have
a lot of responsibility. Business ownership is not for you.
It's not the right place for you because you have
tremendous responsibility as soon as you become a business owner.
True success is measured by how many people you can scale,
not just how many people you can hire and always

(09:29):
working on yourself. You can absolutely attract and retain great people,
but only if you continue to work on yourself and
you continue to become a better version of you. That
process can't stop. So if you're not looking to continually
look in the mirror and say, what can I do better?
How can I show up differently? How can I drive results?
How can I be more inspirational? Business ownership is not
for you. Pro number three is you have ultimate control

(09:52):
over your environment. As a business owner, you get to
decide where you spend your time, which is exciting. Just
next month I'm going to go to Formula One in Monaco.
This has been a bucket list item for me, and
I'm doing it with a group of people that I
cannot wait to spend time with. Why can I do that?
I'm a business owner, and in fact, I just got
an invitation to spend five days on the front end

(10:14):
at the Cannes Film Festival doing some exciting things with Vogue,
and I would actually rather spend my time growing the
business than doing this Vogue event. But owning a business
still allows me to entirely shape my environment to what
I want it to be. I could go off and
do something and really, anybody could do that. Even if
you are a team member in an organisation, you could

(10:35):
spend your two weeks in PTO doing whatever you want
to go do. So you're not confined in any role,
but as a business owner, you get to choose what
things you show up to and how you can create
opportunities through those things to create on your business. I
can use my Vogue relationship to create on my business,
to draw attention to my business, to make people more
aware of what I do. And I get to do

(10:56):
it through this really cool, exciting, fun thing. All because
I created that opportunity. And that is such a perk
of being a business owner. Just this ability to fully
create your environment, to own the culture where people are
thriving inside your business and you're not ultimately stuck in
a role that you hate. So remember that you do
get to intentionally design your work life on your terms.

(11:20):
Con three is one that a lot of people do
struggle with loneliness. When you're a business owner, there is
nobody who shares the weight of leadership with you. You
have to make difficult decisions day in and day out,
oftentimes without any support from anybody around you. You can't
talk to your team members because they don't need the

(11:40):
level of problem that you're giving them, and they likely
don't have any more experience than you do in solving it.
It's isolating to talk to family sometimes because they don't
understand the implications. They don't get the pressure. They don't
understand what's at stake. And mentorship where you can really
go deep with somebody who has been through this through.
This experience can be challenging because people who are busy

(12:02):
building businesses doing great things don't often have a lot
of free time to just answer your questions and give
you advice on how you should or shouldn't handle a
specific situation. No one is coming to save you, but
you don't need somebody to save you. You're going to
make a decision because you know what is best, and
if you make the wrong decision, you will fix it.
You will find somebody who can help you, and you

(12:23):
will just create on whatever the new problem is that
you might have just accidentally created in your business. So yes,
it can be lonely and it oftentimes is lonely, but
life is lonely. No one is doing this with you.
You ultimately have to be your own best friend. You
have to understand what you want, how you want to
get there, and create what life you want to live on. To.

(12:45):
Pro number four business is a powerful microphone. You see
when you build a business, your results, not luck, allows
you to build a brand, allows you to write a book.
It allows you to create a platform that reaches people
who you can impact. You see, because business ownership isn't
just about money. It is about creating real influence. And

(13:08):
the fastest way to do this is to create something meaningful.
Some people have this ability to think about something that
doesn't exist and actually put it in the physical universe.
I want to write a book. Okay, great. What are
you going to write a book about? Just the fact
that you're able to finish a book and put it
to market and have it be in your brand, in
the way that you imagined it, is admirable and creates

(13:30):
a platform for you to be able to talk about
whatever that thing is that you're passionate about. And so
building a business is just this extension of you and
how you see things and how you want the world
to be and what your contribution is. I kind of
sometimes think about playing the game of Sims. Now, my
parents didn't let me play Sims growing up, but my
understanding of Sims is that you create your own world
and you're creating buildings and you're populating this place, and

(13:52):
it's how you want it to be. Well, that's exactly
what a business is. You are creating this whole ecosystem
of exactly what you want your life to look like,
and the products and services that you get to put
out in the world are a representation of you. That's
why most people at a networking event actually ask you,
what do you do? It's not because people are judgmental.
It's because as a society, we do want to understand

(14:14):
what are the products that people produce. When you produce
something that you feel good about, it increases people's ability
to trust you. And when you have high trust, that
trust leads to influence. Convoy is next. Big dreams come
with legal nightmares. Listen, you do not create success without
haters and people who want to come after you. There

(14:35):
are evil people on this planet. There are people who
will just want to claw you back. Bring you down.
Point out any and every flaw you may or may
not have. Make up flaws. Legal troubles are not fun,
but it's just part of running a business. It's part
of having success. And so thinking that you want the success,
but not also recognizing that it comes with this other

(14:57):
thing is naive. Legal pressure is just part of scaling
and why it might be exhausting. It does confirm that
you're moving towards real influence and being able to impact
people because you're getting attention. Resilience is a required trait
for anyone who is serious about building something that lasts.
Our final pro is that owning a business is the

(15:19):
fastest way to build generational wealth. Business ownership is a
way to create generational wealth because you own part of
something that is valuable. That can create a return for
you that can't necessarily be destroyed. As long as you
are continuing to build value into this business, you are
able to have the return off of that value, off

(15:41):
of that asset. And so this idea of having something
ready for your kids through the generations exists through business ownership.
And you look at all of the biggest families that
have existed, especially over the last hundred years, and they
have been able to set up their families and their
children for success, all because they built a business. They
didn't do it through having a job. They actually did

(16:03):
it through building a business, if not multiple businesses. And
we could get in a whole debate about whether or
not generational wealth is a good thing, and how much
money people should be giving to their kids versus other causes.
But regardless of where you stand on that, wouldn't it
make sense and be a good thing to be in
a position financially for your kids to not have to

(16:23):
worry about where their food is coming from, to not
have to worry about man? My mom and dad can't
spend any time with me because they have to work
four jobs and we're barely making ends meet. And so
this idea of generational wealth happening and creating through business
ownership is a choice that you can make. You see,
entrepreneurship isn't just about paychecks. When you do it right,

(16:44):
it's about building something that does pay you for years
to come for multiples on your earnings in a given year.
You see, my husband actually sold his last business for
77 times EBITDA. What that means is the acquiring business
paid 77 years worth of earnings in his business all

(17:05):
in a day. 77 years in a day. Why? Because
the business was so valuable. It was worth 77 years
of those earnings to that business to acquire. So remember
that you are creating value every single day in your business.
And if you focus on this over the salary that
you're paying yourself, all of a sudden you're creating this

(17:26):
thing called generational wealth, all because you decided to own
a business. Our last con can be a big turnoff
for most people. Business ownership means risking your own money.
You see, tying to this idea of generational wealth, it
sounds really sexy. We just talked about having money for
our kids and maybe even their kids. But you don't
get money without risking money. And risking money can be terrifying.

(17:51):
There are banks, there are creditors, there are loan terms.
And it can be scary to not know what all
this means and the right way to access capital and
to use capital. And if you don't do this correctly,
you can end up filing for bankruptcy. You can end
up really damaging and hurting other people. And so this
isn't something that should be considered lightly. You might not

(18:12):
know this, but the definition of being an entrepreneur is
taking on greater than normal financial risk. So being an
entrepreneur isn't just creating a TikTok shop and having a product,
or launching your Pilates studio or buying an HVAC business,
it's actually taking on greater than normal financial risk. So

(18:35):
if you're not willing to risk your money on your business,
you actually have no business getting other people's money because
you aren't confident enough in yourself and your idea and
your ability to execute to put your money on the line.
This is what makes good entrepreneurs successful. They're willing to
go all in on themselves and put all of their
money into an opportunity because they're going to make it

(18:56):
go right. Those are the best entrepreneurs. The worst are
the ones that think it might be fun to own
a business. And maybe it would be cool to have
my own products. Those entrepreneurs never last, and they end
up hurting a lot of people, and they end up
having significant financial damage done. So if you are not
ready to risk your own resources, you are not ready
to own your future and build a business. So these

(19:19):
are the pros and cons of business ownership. If you
enjoyed this podcast, you are going to definitely not want
to miss out on my new newsletter. It just dropped.
I just started creating this content and I am obsessed.
Every single week in your inbox I am going to
send you business and which is exactly what it sounds like.
How do you fit business and all of the other

(19:40):
things in your life so that you are up to
speed on fashion, beauty, wellness, all things that really matter.
If you want to subscribe and get this special gift
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