I grew up in a house with four brothers, no sisters, on a lake in Indiana.
And as a Gen-Xer, people like me aren’t supposed to cry. We’re supposed to stuff it down and power through. So I was shocked when business brought me to my knees while I was building my agency.
Left to right: Chris, Ken, James, Jeff, me.
The First Cry
Not sure if this one even counts, but before I started my agency, I was stuck enduring round after round of layoffs at Fox knowing that eventually I would be let go along with everyone else in our department. The stress was brutal. I was job hunting, but in the 2002 economy, nothing was coming. That era forced a few tears out of me. Even now, 23 years later, I still feel a pang of anxiety when I think about it.
The Second Cry
I lasted six years until the next cry. In 2008, my agency was thriving—seven figures in revenue, a second studio space, everything clicking. And then, October hit. The Great Recession wiped out most of my personal net worth.
I had money in the business bank accounts, so I decided to keep my team employed, hoping things would turn around. By February 2009, I was out of financial runway and had to lay off half my team in one scary, sad afternoon. It was a gut-wrenching day. Driving home, I broke down and sobbed, feeling like a massive failure. I’m sure my team members shed their fair share of tears too.
The client logo wall in my second studio space.
The Third Cry
Another six years passed. (Is this a pattern?) In 2014, I tried to step back from my agency. We had 20 employees. I had my dream studio. My first book, Burn Your Portfolio, had been released. But stepping away didn’t work—revenue and profits tanked fast.
I had to jump back in, make some tough staffing changes, and clean up a mess of client projects. One in particular was a total nightmare—manipulative, constantly shifting scope, and costing us hundreds of thousands. It got so bad I ended up waiving $70,000 in outstanding invoices just to be done with them.
This wasn’t just “the third cry.” This was months of stress and breakdowns. It felt like everything I had built over 12 years was slipping away. That’s when I started thinking, What’s next for me? A year later, I sold my agency.
My agency team at the time my book, Burn Your Portfolio, was released.
The Fourth Cry
By August 2015, the sale was complete. My team of 20 merged into an agency of 60, moving into their office about 15 minutes south of ours. A few days later, I went back to our old studio to cancel the internet and phone service.
My studio space was lifeless. Dark. Silent. No music, no hustle, no laughter—just an empty scene that had once been filled with creative energy. I sat at my office manager’s desk, made the call to cancel service, hung up, and then cried.
I’m still not sure if they were happy tears—because I had successfully exited—or sad ones for the exact same reason. Probably both. But for the first time in a long time, I let the emotions come out.
The Riser lobby sign in the dumpster after we cleaned up the studio and prepared it for lease. Before we left, I grabbed the R out of the trash and it now hangs in my home office. I wish I would have kept all the letters.
How Often Should People Cry?
I still struggle with crying. My nephew started dating a great girl who has a master’s in psychology. During our first conversation, I jokingly asked her to psychoanalyze me. (I love asking educated people to do that. Haha.)
She was spot on with her assessment. During the conversation I asked, “How often should people cry?”
She answered, “Probably about once a week.”
Oof. My once-every-six-years streak needs some work.
How often do you cry?
Has business ever brought you to tears?
Me with my head down on vacation trying to manage the trauma of building an agency.
