Why I'm Starting Over in Business

It seems crazy to blow everything up and start over but it's definitely happening.

Why I'm Starting Over in Business
Photo by Riccardo Annandale / Unsplash

Can I let you in on a dirty little secret?

I’m a serial entrepreneur, who at the spunky age of 53, is completely starting over in business.

From scratch.

It seems crazy to think about, let alone do, but here I am with nothing more than a dozen ideas and the drive to make it happen.

Why in the hell am I doing this?

brown Converse high top shoes
Photo by Apostolos Vamvouras / Unsplash

In 1986 I launched my first creative venture called Dogman Designs. I customized Chuck Taylor Converse All-Stars and Levis 501s with Sharpie pens and an airbrush. I also designed psychedelic t-shirts.

And I fucking loved it!

It didn’t hurt that I made a lot of cash doing it either. When you make great money at the age of 16, it’s invigorating — though having a business was never my plan at all.

It just happened.

Fast forward thirty five years and I had mastered dozens of skills. Web design, graphic design, branding, screen-printing, mural and window painting, advertising, marketing, sign making, calligraphy and a lot more!

I’ve been fortunate to work with brands like HTC, Arnold Palmer, NASCAR, Disney, NCAA, Eskimo Joes, Michael Hyatt, BMW, and dozens of other high profile clients, in addition to small businesses all over the country.

None of this was planned either. It just happened.

But after a long career of doing projects for other people and helping them make millions of dollars, I was burned out. Done. Kaput. There was no interest continuing on.

Luckily in 2020 the stars finally aligned.

My wife and I sold almost everything we owned, including our home of 14 years, to live a life from the road. I blew up my marketing business and shut it all down.


After a year of traveling the country and dicking off by the pool while drinking beer, I landed several consulting projects for different businesses who paid me great money to turn their companies around.

I wasn’t looking for it. It just happened.

Everything I’ve ever made money from was never planned in advance.

A few of the best opportunities came from my uncanny ability to see a huge wave coming and then being able to surf it. The rest came from personal hardships like the economy changing or getting fired.

The hardships were always my favorite. That’s why I’m here.

Unless you’re extremely lucky or smart with your finances, or you have a sugar momma or daddy, money is not an endless supply. And now that I’m over the hump thinking about retirement, it’s time to get serious again.

Plus I spent too much money traveling. It just happened. 😜

Photo by Almos Bechtold on Unsplash

My life is like a phoenix — constantly being reborn from the ashes.

The fire and passion to overcome whatever challenge is in front of me has never been snuffed out. When I’m told something can’t be done, it motivates me even more.

My fourth grade teacher told me I’d never make anything of my life.

There are lots of people who doubted me back then and there still are today. But I’m determined to succeed. Even at my age.

My reasons for starting over are partly for survival, partly for embracing the challenge. I want to push myself to new heights, do the shit I’ve talked about for thirty years, and make a million dollars doing it.

I also want to come full circle, back to the beginning, my first creative love.

And it’s just happening.

wake up kick ass. be kind. repeat printed glass wall
Photo by Chris Curry on Unsplash

Besides achieving my goals, my objective is to show others it can be done, even when you’re over the hump.

I’ll document the entire process and openly share the results.

You’ll be able to see the good, the bad, and the ugly. You’ll also be invited to participate in the process by sharing your opinions and feedback.

Maybe we’ll all learn some cool shit together along the way!

Next up I’ll share how I plan on attacking my goals and achieving the objectives. It’s a definitely a work in progress but no business strategy is ever perfect.