When I was a teenager, our family went on a vacation where there was a gambling hall. My dad, while not much for gambling, asked if I wanted to put anything down. I was too young to enter, and so I asked him to bet $20 on black at the roulette table for me.

It would go one of two ways. I waited patiently.

When he came out, I was broke.

I used to think business and entrepreneurship was sort of that same way. A gamble of an idea took that course. One big risk. You throw it out, and it sticks and you are off to the races or it falls to the ground in shambles and you have nothing. 

A one decision kind of thing.

The more I learn, the more I think entrepreneurship is actually the opposite. That it is more like 10,000 choices over the course of that business idea’s life.

There are a few big steps on the front end, but just as many as you journey along.

Each choice requires decisions, and calculated risks examining the market, possibilities, consequences, over, and over, and over.  Each decisions changes as each day and plans unfold. 

As I look over the last 5 years. I see that. We have made literally thousands of little decisions. Color choices. Money choices. Style choices. Personnel choices. Manufacture, strategy, marketing, ad budget, etc. Honestly, it might be a million choices if you add them all up. Not all at once, but little by little.

One thing I learned and observed is you never want to bet on black. It's really a desperate move. And so often, leaves you... well... broke.

You want to move forward in a way, where you can learn from your choices, but NOT LOSE IT ALL and be out of the game.

So many folks I talk to who raised capital early, spent it, then when they were out of it, knew the game plan moving forward. But often, it was too late. So many of my mentors preached this to me, over and over. 

Mistakes, errors, risks. We need to live in a way, both personally and in business where we can all make them. But do you never want just one choice that is so big, you could lose it all.

Nothing is guaranteed in life, but entrepreneurship is about survival. And while a lot is spoken about the willingness to fail... I also think it should be about having the margin to fail, and still be in the game.

We made a choice a few months ago to sell wholesale. What it really means is selling to retail stores across the country, instead of being just an online brand. It’s an exciting opportunity as many of our customers have asked, and stores are calling and emailing us asking for our product. We have always wanted to be in stores, but we were too small to take the risk. We would have been betting Buffalo Jackson on black.

We decided to wait 5 years for that choice.

And as much as I wanted to get out there, as we watched other brands grow. It was through the help of good friends, that we listened to their advice.

We waited. And stuck to our plan. Growing our sales, our customers, making all those little choices.

Some of the store owner asked us, why did it take you so long? I think their concern was we were trying to work around them.

Dixie Pickers and Buffalo Jackson

(Dixie Pickers in Collierville, TN after placing an order for Fall '14 Line)

Well, we grew it through a risk of a few hundred dollars. So to get to a big choice, one that was risky, and had a lot of room for errors. It had to be a calculated one.

We were trying to make that choice when it was the right time. So we resisted the urge to gamble it all, when our company was not ready.

We wanted to do it when we had the interest and demand, the financial resources, people, product, and plan to pull it off. We had to crawl, before we walked. (As they say... crawl, walk, then run)

Maybe you could say, we are growing up. We are taking one more step.

We are so excited to bring our product into retail stores across the country. We have already signed up some amazing stores from Wyoming to Florida. It’s been so encouraging to see the interest.

Since we started with so little money. And grew it. It’s a big risk for me. We aren’t playing with someone else’s money. It’s the money that was created from selling tees and ties from plastic shelving units in my garage. 

I think about those two scenarios we are presented in life.

One requires our full engagement and over the long haul, the other… well… it’s why gambling is gambling. It could all change one way or the other in an instant.

I think it might be a good reflection for all of us... Are you living your life betting on black? Or the long haul with the 10,00 choices and risks along the path to one day get to your goal?

The overnight success? I think it's a myth. Just those gambling types talking.

The true story? It is the ten thousand risks and choices to get there.

Hope you are on that path.