The Part of Entrepreneurship No One Talks About (Until It Breaks You)

Let’s talk about what building a business really feels like.

In this episode of the Total Sum Game podcast,we get honest about the emotional rollercoaster of entrepreneurship.

We’re talking about the part no one warns you about:
 💸 The financial pressure that keeps you up at night
 🧠 The mental load of leading a team
 🫥 The invisible stress behind every big decision

We open up about what it’s like to support founders in their hardest moments—the times when everything looks fine from the outside, but inside it’s heavy.

We’ll share the unexpected connection between failure, growth, and freedom—and how the messiest moments often shape us the most.

If you’ve ever felt like you’re carrying the weight of your business alone…

You’re not. And you don’t have to.

We created this space to talk about the real stuff: the mindset, the pressure, the vulnerability, and the personal growth that goes hand-in-hand with success.

🎧 Listen in—and if you’re ready for support that honors both your ambition and your humanity, head to www.totalsumgame.com

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Episode Transcript

Speaker 1 (00:00):
When you're an entrepreneur, that reward to you
is so much more powerfulbecause you created that.
Without you in the driver'sseat, without your idea, without
your inspiration, without youremotional motivation, whatever
it is, you accomplished money,social impact, whatever wouldn't
happen had you not.

(00:20):
You're super upset why I lost$100,000 today.
That's a good way tocommunicate to somebody else,
like how shitty your day000today.
That's a good way tocommunicate to somebody else how
shitty your day really is.
That's a huge problem for mostpeople, right?

Speaker 2 (00:30):
No, that's a big deal .
But what really are you afraidof?

Speaker 1 (00:32):
Yeah.

Speaker 2 (00:34):
It's not the $100,000 .

Speaker 1 (00:35):
No, but that money and the dollar amount.
It's a way of submittingemotional impact.
There's other elements to thisbesides money.
We like money because it's away to gauge.
It's a way to measure If thatguy has a million dollars and I
have a hundred dollars, he has awhole lot more money than I do.
So it's a way to compareourselves and gauge.
But the truth is there's a soupof things.

(00:55):
The intent of this conversation,too, is to talk to people who
are on the fence or new toentrepreneurship.
We want you guys to hear thatyou're not alone, you're not by
yourself, and the way you feelabout these things is not unique
.
Everybody goes through highsand lows.
What Michelle is describing isa wonderful representation of
what it can be like insidebusiness emotionally, first of

(01:16):
all, because of how emotionallyintelligent Michelle is, but
also from her perspective.
If you think about it as anaccountant.
She's tied into all thesedifferent businesses.
When you have dozens, sometimeshundreds, of clients, every one
of those clients is in adifferent emotional state.
One's super happy because hejust got his first profit ever
in history after five years ofbeing on the grind.

(01:36):
Another guy's pulling his hairout because the technology came
along and it's undermining hisbusiness plan and he doesn't see
a way through it.
Imagine bouncing back and forthbetween those, from call to
email to message, throughout anentire day, and so that's one of
our things we want to talkabout is emotional roller
coasters.
You know we hear all too often.
Oftentimes as employees priorto being entrepreneurs bosses

(01:58):
can be very moody, but there's areally good reason for that.
I was very moody because thingsgo there's highs, there's lows,
and that's the first 10 minutesyou've been at work,
understanding that, when youtake this on, that's part of
what comes with it.
There's highs and there's lowsand it can be five minutes apart
, it can be five days apart, itcan be five seconds apart of how

(02:20):
that works.
So I can imagine in thebeginning highs and lows for you
are not only just in normalbusiness operations, but by the
incoming from all thesedifferent clients who are all in
very different emotional statesthroughout their day.

Speaker 2 (02:32):
Yeah, when you're directly responsible for
communicating the numbers tosomeone, you know how that's
going to affect their emotionalstate, and so you start getting
really emotionally overwhelmedjust invested in these people
that you work for, because youknow that this is their
livelihood.
And, yeah, you've got todeliver some bad news.

(02:54):
It's not a fun thing to do, butyet you're the source of the
information that can then helpthem make the decision to turn
things around, and so it's anincredible responsibility for
people that are in those roles,and if you have a really good
finance team that you're workingwith, they do care about that.
They care about what they'reproviding for you and they

(03:17):
understand the impact of theinformation that they're giving,
and I think that was one thingwhen you and I met.
And even one thing that Ireally enjoyed with working with
people is having themunderstand that they're not
alone.
When, as I got to theopportunity to work with so many
people in so many differentfinancial situations and also

(03:38):
different kinds of businesses,they all go through the same
emotional ups and downs, and theproblem is that and I think
that's this is like all parts oflife is that when you're going
through that, you think you'rethe only one.
You think that no one else everhas to go through this and
everybody else has it figuredout and you're the one that's
just missing something somewhere.
And the truth is, in lifethat's of course.

(03:58):
We know that's not the case.
But in business that'sdefinitely not the case.
We all walk around in businessand in life like we've got it
all figured out and so and a lotof times we don't wear that on
our sleeves.
We're not supposed to say, yeah, my business is losing money or
I'm barely making payroll.
But when you start a business,that's likely just how it goes

(04:21):
and that's part of it.
And you're not alone in goingthrough those different types of
situations.
Everybody goes through that andit's just part of being a
business owner.

Speaker 1 (04:32):
And something to consider too if you're
contemplating being a businessowner once in a great while.
It just goes smooth as glass orwhatever Some people.
God just shines on brighterthan other people For some
reason I don't know why, but themajority is that there is.
It's a struggle.
It's extremely difficult, butthere's a reason for that.
It's extremely difficultbecause the reward is so
powerful, the huge reward, notjust financially, it may not

(04:56):
even be financially, maybe it'ssomething else you're committed
to that you're trying toaccomplish.
It doesn't have to be money,whenever that thing, whatever
that is, comes to fruition.
When you're an entrepreneur,that reward to you is so much
more powerful because youcreated that Without you in the
driver's seat, without your idea, without your inspiration,

(05:16):
without your emotionalmotivation, whatever it is, you
accomplished money, socialimpact, whatever wouldn't happen
had you not.
It literally exists because youcreated it from really thin air
or from a dream.
And Michelle hits a reallyimportant point talking about
you're really not alone thateverybody suffers on some level,

(05:39):
and it's required as a symptomof natural law because the
reward is so good.
So some people lean into thesuffering, some people lean into
the grind, lean into theanxiety, because they know on
the other side of that is thisincredible reward.
And I think that's what happenswhen you've done the things
that Michelle and I have done.
Where you've had a business Ihad one to go completely
bankrupt, so I've been theentire spectrum Others that you

(06:01):
sell very favorably, whateverthat is.
But you start to get thatperspective, like now that we're
at TSG, when what we used tocall bad news may come, you get
some bad report or something'snot going the way you want it to
.
You're like oh yeah, this ispart of the game.

Speaker 2 (06:25):
I think that's part of what we really want to share
with people is now livingthrough that, knowing all the
emotional ups and downs, andthat you go through Coming
through that and then nowstarting over like we are.
We know that we don't have togo through that.
Right, we can choose to viewthings a different way because
that's all it is.
It's all your perspective.
Like you said, you don't knowwhether something is good news
or bad news.
You just never do, because youdon't know what that's going to
lead to next.
And getting to go start anotherbusiness together, like we're

(06:47):
doing now, whether things are upor down or whatever, that
doesn't really mean that it hasto affect us emotionally.
We can go through these things,understanding that we're clear
on our vision and what we'redoing and that it's part of the
process.