Fail Brilliantly: Seven Years Later

[NOTE: I recently hit the seven-year anniversary of being laid off for the second time and starting this journey. Following is my reflection.]

Seven years ago.

Seven years ago, I had just been laid off for the second time in two years.

Seven years ago, my best guess about what I’d be doing today would be nowhere near reality. Give me the time to list every possible scenario, and I’d shoot off a combination of optimism and realism…

Work for a non-profit.

Work in marketing.

Work in sports.

Work in game development.

It’s gotta be one of those four. And who knows where I’d be. Seven years ago, we were in Colorado. But where would we be now? East coast? West coast? Midwest?

One thing would be certain: I’d have an employer. And if my career trends continued, I likely had two or three employers during those seven years. And I may have even been laid off again.

I had never worked for a single company or done one thing for five years. Why would the next seven years be any different?

As I compiled that hypothetical list, I’d likely reserve the most optimistic guess for last. It would be last because it would be so unlikely…


Sounds amazing. Find more time with my family. Watch my kids grow up. Participate in their lives. Coach their baseball teams. Have control over my schedule. Own my time.

Just so unlikely. I wasn’t trained to start a business. I was a freaking philosophy major, after all. And I had never shown the initiative or drive to not only start a business but succeed at it.

Okay, maybe I’d try it. Maybe I’d throw something at the wall. I had long thought of creating a fantasy games product. Maybe I’d do that. But succeed? Still ticking without a boss seven years later, and it’s not because I’d hit rock bottom?

Maybe others could have believed it. But following two layoffs in two years and confidence in the toilet, there’s no way that I believed it.

It’s difficult to explain. But I guess I should put that college major to good use and get philosophical about it.

It’s been an amazing, fulfilling, eye-opening ride. I’ve learned so much about myself along the way. Most importantly, I’ve learned how I was my own worst enemy — that my own beliefs about myself and my capabilities prevented me from doing what I wanted.

So… Why am I still doing this today? Why am I my own boss, and not answering to someone else?


I could have never done this alone. Others can. But I was not in a place where it would have been possible for me.

It started with my wife, Lisa. She was insanely patient with me as I blew through our savings while waiting for the perfect job opportunity that would never come. She embraced the idea of risking it all to do something different. And now, she’s my business partner.

But there have been so many more whose support has been critical to my own sanity and growth. John Robinson started as a friendly voice of emotional support as I navigated this new world. Today, he is an official part of the team.

Local business owners and friends kept me busy in the early days. They encouraged me. They provided ideas and contacts to keep me experimenting.

Dozens and dozens of marketers — from those who reached high levels to those who were still struggling like I was — were there to help with kind words, provide connections, and give needed constructive criticism.

A growing and evolving team surrounded me to keep this crazy business buzzing and moving forward. Their patience with my quirks and uncomfortable leadership, their willingness to help and contribute throughout the chaos are sincerely appreciated.

Andrew Foxwell reached out to me during a time when I was much more likely to read and respond to my emails (I’m terrible at that now). But he caught my eye early as someone who was selfless and smart and funny. His friendship and contributions to my communities, training, and content have been a huge boost.

And I can’t ignore the support from my reading audience. While I don’t always respond, your feedback and kind words keep me going. Passion and motivation are so much easier to find when you know that you’re making a difference in people’s lives.

There’s a long, long list of people I could name individually here. Ultimately, I’d forget or not have the room for too many important names. I haven’t forgotten.


After that second layoff, I could physically feel the pressure of having to provide. My ability or inability to make a living would determine whether we could stay in our house, would need to find a new school and neighborhood, or whether my wife would need to go back into the workforce.

With each passing day without a paycheck, the pressure increased. While I attempted to keep a positive outward appearance, I was truly desperate.

I HAD to make this work. I had to make SOMETHING work. I can’t sit around the house forever. Eventually, things will be taken from us. Our lives will need to change dramatically.

Every moment of inactivity was accompanied by guilt. Rest? Relax? Sleep? How could I? What kind of parent and husband am I?

As awful as those first six to nine months were, I survived. And it was that desperation that forced me outside of my comfort zone to do things I wouldn’t normally do.

For years, I dreamed of starting some sort of business (nothing that ever would have worked, in all likelihood) when I had the comfort of employment. I truly believe that it was the desperation of unemployment that allowed it to happen.


I’m not going to lie to you and say that I was “hustling” and working 24 hours per day, eight days per week. That’s not what this “commitment” block is about.

It’s about doing — writing, creating, experimenting, and failing brilliantly — while there are few signs of progress. When there is every reason to wave the white flag and give up.

Looking back, my strengths and weaknesses allowed me to take a path that eventually led to success. I wrote and wrote and wrote and wrote. I wasn’t a comfortable salesman, so I didn’t create a product until near the end of the first year.

I firmly believe that this seemingly irrational commitment to content set the foundation for the business that still exists today. It laid the groundwork for building an email list and creating paid products. Without that content, I don’t know that I’d still be here.


On the surface, I may have seemed lazy in the initial months after being laid off. I rarely applied for a job. And when I did, I put very little effort behind following up and trying to make it happen.

Why? Deep down, I didn’t want it to work.

After years in the insurance industry doing crap that I hated (REALLY hated), I was spoiled for about five years doing a couple of pretty amazing jobs.

I managed fantasy games for the NBA for three seasons. Ridiculous. I worked as VP of Strategic Marketing for the American Cancer Society, following a cause that hits close to home (our oldest son is a cancer survivor).

So I didn’t want to settle for your typical, boring job. You know, the kind of job that 99.9% of people do. I was stubborn. Maybe a little crazy. But it’s a good thing.

Without this stubbornness, I’m sure I would have taken a job doing something that would have left me unsatisfied. I would have put dreams of doing my own thing on the back burner to simmer and eventually be forgotten.


I find that it’s common among entrepreneurs to allow ego to take full credit for success. “You create your own luck,” as the saying goes. But I find this to be complete trash.

I’d be an ignorant fool if I didn’t acknowledge the contribution of luck in my life. I’ve been extremely lucky.

That string of luck starts nearly 20 years ago…

As mentioned earlier, I started my career in the insurance industry. I was not a good employee. I did not enjoy my job. In that way, I was probably pretty normal.

So, what did I do? I wasted time on the clock doing things that made me happy. I was obsessed with fantasy games. I used company time to manage my teams and, ultimately, contribute to fantasy sports-related websites.

That deviance nearly got me fired (it should have). But it also got me noticed. It led to connections and likely the most amazing two and a half years of employment I’ll ever have while with the NBA. And it’s this experience and the contacts from it that forced others to take me seriously in the years following.

Most importantly? It was my first exposure to Facebook in 2007 (!). And while it was early, it was my first exposure to Facebook from a business perspective.

If I hadn’t been a horrible employee while working in insurance, I never would have worked for the NBA. If I had never worked for the NBA, I wouldn’t have had that first exposure to Facebook. If I hadn’t had that first exposure to Facebook…

What would I be doing today?


The bottom line is this: Don’t trap yourself with your own beliefs about limitations.

I had a belief that I was incapable of starting a business. I had a belief that I didn’t have what it took. I was wrong.

It’s not because there’s anything particularly special about me. I was wrong because I made incorrect assumptions about what it took and what I was capable of.

So, what will I be doing seven years from now? I don’t know. Given the crazy paths my life has taken so far, I’m an example of how we can do things that we think aren’t possible.

If you’re limiting yourself with your own self-doubts, stop. Those doing what you want to do don’t have it all figured out. They don’t necessarily have any magical skill or experience that you lack. They’ve likely benefitted from opportunities and luck and their own stubbornness.

Put your head down and create. Experiment, fail brilliantly, and discover your own potential for the first time.