The Fort

The Monday blog · April 14, 2025

Leap of Faith

By Dan Trink, co-founder of The Fort · 4 min read

Fred was fucked.

He needed $24,000 to keep his company going and he needed it fast.

Problem was, he only had $5000 left in his bank account.

Everyone told him it wasn’t going to work.

His college professor, who was the first person to see the idea as part of an assignment, gave him a C+, saying it was an imaginative idea but a logistical nightmare.

His fellow students laughed at him. Others in his industry didn’t take him seriously.

It was starting to look like all those people were right.

So Fred, with no one else to turn to and nowhere else to go, withdrew his last 5k on a Friday afternoon and flew to Las Vegas.

As he fingered his bankroll at the blackjack table he had second thoughts.

“What am I doing? This will never work,” he muttered to himself.

But then he thought about his situation. How the fuel bill needed to be paid. And without access to fuel, he’d be out of business.

So he handed the cash over to the dealer who exchanged it for chips and he started betting.

Small bets at first but as he started winning he felt more emboldened and pushed more and more chips into the circle.

Fred caught a hot streak and found himself in the zone. Pushing more and more money onto the table and winning more and more hands.

He was so focused that he didn’t even realize a crowd had formed behind him, cheering as he was now literally winning thousands of dollars per hand.

When he finally snapped out of his trance, Fred counted his chips and realized he had $27,000 worth in front of him - a bit more than he needed. He cashed out, headed to the airport and flew back to Memphis. He never gambled again.

There is a fine line between courage and desperation.

But, honestly, the source of motivation doesn’t really matter. There is just something remarkably powerful about going all in on something.

We’ve probably all been mostly in or somewhat in or half in on many things.

I know I have. It’s probably our default state.

But, quite honestly, it’s the most frustrating place to be. Because you are putting in effort, you are hoping for an outcome, but you probably aren’t getting enough things right to get what you want.

Two things can happen here.

The first is that you quit. Which, honestly, isn’t always a bad decision. Unless it leads to a disastrous outcome or deep regret. Then, perhaps, it’s the worst decision.

The second is you push all in.

This happened to me with our business.

It was six months after COVID had shut us down. We were not doing well. We had to lay off nearly our entire staff. We had a gym full of people who had been nice enough to prepay for sessions back in March. But now we were in the process of fulfilling those sessions with no money in our account (we had, clearly stupidly, used that money to pay our staff through the pandemic so they could stay afloat and, incorrectly assumed, that would solidify their loyalty. It did not.)

I remember checking our spreadsheets and realizing we only had 4 clients who would have bills due anytime soon. It was just about the lowest I’ve ever felt.

I told Kyle who was diligently changing light bulbs in the basement (Kyle is finatical about light bulbs) and we decided in that moment that, whatever we needed to do to keep things going, we would do it. We’d die on the turf if that was what was necessary.

And I realize that sounds remarkably dramatic but it did feel like life or death at that moment.

Even my own fitness has gone through an evolution of dedication. At first, all I would commit to was cardio. First three days per week. Then five. It wasn’t until later that I added in strength training and then figured out my nutrition and then added supplements until I was all in on reaching my goals.

There is something remarkably liberating about going all in. Because it takes thought and second-guessing out of the equation.

Sure, there is still pain involved. You can feel isolated. You can get tagged with being obsessed. Loved ones will worry about you. You will lose some of the things you’ve had before.

But, in so many ways and for so many things, it’s the only thing that works.

So if something feels important to you I implore you to ask yourself if you are all in. To ask yourself what else you can be doing to get yourself where you want to go. I bet you there is something.

And then, take a leap of faith. It’s the only good fight there is.

The Fred I mentioned earlier is Fred Smith.

He founded a small company called Fed Ex.

Seems like things worked out for him.

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