Keith Roberts built a successful agency but his talent for generating revenue masked a spending problem that nearly destroyed it. A $100,000 deal backfired, foreclosure notices piled up in his office, and the business stopped being fun. He learned that the skill making him rich was killing his company.
When was the moment when you said, holy shit, this isn't working?
It was hard to realize this is not going to be the fruitful life that I had envisioned. As the company grew, it created this machine that ate money.
Keith Roberts is a transformational leadership speaker and founder of Zenman, where he spent 24 years creating digital solutions for major brands like Frontier Airlines, RE/MAX, and the Lumineers. Author of The Zen of Business, he blends ancient wisdom with modern leadership strategies, delivering powerful, story-driven keynotes that help leaders navigate change with intention, clarity, and purpose. What was your first big break, man?
First big break ended up being the biggest backfire. It was over $100,000 to walk away. I realized, like, man, when you get that shot, you can't fuck it up. I mean, I just can't imagine the emotions getting a big shot and then having that rug pull. I disappeared off the planet, and that was probably the moment when it actually stopped being fun. What were those early entrepreneurial experiences like? Failed tremendously. Yeah. My initial relationship with money wasn't the healthiest relationship. I've always been great at making money, but I've always been slightly better at spending money. No matter what you have going on. I mean, I had foreclosure notices that were on my office that I was taking off the door before an employee saw it. So they didn't know how bad things really were. But there was somebody in a hospital that would cut off their left arm to trade problems with me. Now we'll go back to the question that you stole from me. What would you go back and tell the version of yourself that was in the thick of it in the agency?
I think, um,
