This Ain't Check Cashing Country

Welcome Note

Thanks for reading the twenty-ninth issue of The Advantage. This past week, I was lucky enough to be featured on The School of Hard Knocks. You have almost certainly seen the Instagram or YouTube channel, even if you do not know it by name. It is the guy who walks up to strangers and asks:

The interview brought a wave of new followers and subscribers my way, so first: thank you and welcome.

It also brought a question I hear a lot from ambitious people:

Or, more directly:

The answer is hidden in a riddle:

Keep reading.

Three Different Worlds, Same Lesson

This week I am combining Worth Watching and The Practical Edge into one longer piece.

It starts with three short clips that all make the same point.

The first is Nick Saban. Saban is a football genius, but he is also a machine for sound bites that apply well beyond football.

This one is only nine seconds:

The second clip is from my School of Hard Knocks interview. Nick and I are basically saying the same thing. Yes, even though Coach Saban and I have never met, I like to think we are on a first-name basis.

My version was:

The third is a song: Midland, "Check Cashing Country."

The song was written about the band's grind long before they were famous, before they had a single on the radio, and before they were playing sold-out arenas.

Midland's lead singer, Mark Wystrach, also happens to be my twin brother. More on that later.

The song includes this line:

Football, country music, and entrepreneurship.
Three different worlds. Same lesson.

The wrong end of the question

Success, money, recognition, the exit, the sold-out arena: those are outcomes. You cannot build your life around wanting the outcome while ignoring the process required to produce it.

When someone asks me how to become a successful entrepreneur, I usually turn the question around:

For my brother, the answer was music.
For me, it was business.

I started reading The Wall Street Journal in high school and have barely missed a day since. I was fascinated by companies, founders, deals, strategy, and why some businesses worked while others failed.

Once my brother picked up a guitar, he never put it down. Family dinners, college parties, wherever he went, the guitar came too.

It was not discipline at first, although the discipline came later.
It was obsession.

That obsession is what powers the process. And the process is what eventually produces the outcome.

You cannot skip straight to the outcome.
And if you truly love the work, you will not want to.

My brother started seriously playing music at 20. He did not sign his first record deal until he was 35.

I started my first business at 25. I did not experience real success until I was around 40.

Roughly 15 years each.

People see the record deal, the arena, the successful company, or the exit. What they usually do not see is the decade and a half before it.

Before either of us reached the promised land, we spent a long time in the desert.

But the desert was not dead time.
It was where we got good.

For me, it was 15 years of learning business the only way it can really be learned: up close.

I learned how to sell, hire, raise money, manage cash, make bad decisions, recover from them, and keep moving when the original plan stopped working.

My brother spent those years playing for anyone who would listen. House parties became dive bars. Dive bars became better rooms. One van, one town, one show at a time.

For both of us, it was years of repetition with no guarantee that the big outcome would ever arrive.

And we loved it.
That is the part people miss.

When you truly love the process, you tend to outwork the people who only want the reward.

Not because you have more discipline.
Not because you wake up every morning forcing yourself to grind.

You outwork them because you would rather be doing this than almost anything else.

You take more swings.
You have more conversations.
You make more mistakes.
You spend more time close to the problem.

Over months, the difference may not look dramatic. Over 10 or 20 years, it compounds into an enormous advantage.

The love is the unfair advantage.

But with love also comes sacrifice.

Obsession has a cost. There are birthday parties you miss, weekends that disappear, time away from family, late nights, early mornings, and moments you do not get back. Loving the work does not eliminate the trade-offs. In many cases, it increases them.

For most of the last 15 years, I have worked every weekend and almost every vacation. I am often absent at the dinner table, even when I am present. I am up at 4:15 am and out of the house before my kids are awake.

Not because someone required it.
Because I wanted to.

Obsession does not turn off on the weekends or vacation.
It does not turn off at the dinner table.

I have stood backstage while my brother played to a sold-out arena and thought:

Of course I did. The arena is the destination.

But because I watched the entire journey, I also knew something else:

I did not want his process.

I did not want the years packed into a white van with eight guys, driving from town to town, playing for 30 people, and working two side jobs to fund a guitar habit.

I did not want to spend years playing shows with no proof that a sold-out arena was waiting at the end of the road.

But that process is what produced the arena.
One does not come without the other.

That is the test most people never perform.

They ask whether they want the result.
They do not ask whether they want the 15 years of process required to create it.

Everyone wants to own the great company.
Do you want to spend seven days a week cooking, packing, and shipping meals while making less than minimum wage?

Everyone wants to build a category-defining product.
Are you willing to make the 101st pitch after receiving your 100th rejection?

Everyone wants the exit.
Do you want the years of payroll pressure, missed forecasts, broken systems, employee problems, tough board meetings, and lying awake at night because you are about to run out of cash?

Do not ask whether you want the peak.
Ask whether you want the climb.

Remove the money.
Remove the recognition.
Remove the impressive title, the press coverage, the valuation, and the applause.

Now picture the actual work.

The customer complaint.
The sales call that goes nowhere.
The product that still is not right.
The employee who quits.
The cash forecast.
The tenth attempt at solving the same problem.

Would you still choose it?

You do not need to love every task. Nobody does.
But you need to love the game enough to keep returning to it.

And be careful not to confuse loving a subject with loving the business required to build around it.

Loving food does not mean you will love running a restaurant.
Loving fashion does not mean you will love managing inventory, returns, margins, and customer acquisition.
Loving animals does not mean you will love building and operating veterinary clinics.

The real question is not only:

It is:

Most people do not stay with anything long enough to become exceptional at it.

They get excited about the possibility, run into the reality, and start searching for another possibility.

The field thins.
This is true in music, sports, and business.

Most individual businesses will not survive for decades. But entrepreneurship is not a one-attempt game.

Freshly was not my first company.
Midland was not Mark's first band.
Alabama was not Saban's first coaching job, although he did go 9-2 in his first season.

The point is not that staying with one exact company forever guarantees success.
It does not.

The point is that staying in the game allows your judgment, relationships, reputation, skills, capital, and pattern recognition to compound.

A failed company does not have to erase those gains.
You carry them into the next attempt.
Then the next.

The longer you remain in the arena, the more the odds can begin to bend in your favor.

Will somebody skip the line?
Of course.

There will always be a musician whose first song goes to number one, a founder whose first company explodes, or an athlete who looks destined from the beginning.

But planning to be the outlier is a terrible strategy.

A better strategy is to find work you can stay with long enough to become unusually good.

Start early.
Stack the reps.
Stay close to the problem.
Let time do what time does.

If you already know your thing, go all in and stay in the game.

If you do not know it yet, your job is not to sit around waiting for your passion to reveal itself.

Go test things.
Build something.
Take a job close to the work.
Sell.
Write.
Create.

Try enough paths to discover which problems keep pulling you back.

Then ask yourself:

If the answer is yes, you may have found your advantage.

And there is the answer to the riddle.

Football, country music, and building a business all reward the same type of person:

The one who loves the process enough to keep going after the people chasing the prize have left.

Thanks for reading.

Founder · Operator · Investor

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