Dave Ramsey | Crain's Toronto

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Dave Ramsey


In 1992, Dave Ramsey founded Ramsey Solutions, headquartered in Brentwood, Tenn., to help people take control of their finances, establish financial discipline and live debt-free. Since then, the business has flourished with more than 600 employees. The CEO also hosts a radio show, "The Dave Ramsey Show," which is heard on more than 585 stations in the U.S. and Canada, and has authored several books.  

The Mistake:

My whole career is a mistake. Everything I've done has been a mistake. We tell our team all the time that 90 percent of our ideas suck – but we just don't know which 90 percent.

We make all of our money, and help all the people we help, off of about 10 percent of our ideas. Most of the things we try don't work, and we're pretty convinced that success is really standing on a pile of failures. Philosophically, from a leadership perspective, I had an epiphany a few years back.

I really – for the first many years of my career and even running the business – kept thinking I would be discovered and that someone was going to come along and take the radio show big or make the publishing successful. But that never happened. I kept thinking if I could get this one big break, that I would be successful.

We were on "Oprah" and it didn't change our lives, but it helped. We were on "60 Minutes" and it didn't change our lives, but it helped. You think when you get a major New York publisher pick your book up, now you don't have to work as much. It turns out they didn't do everything they had to do and I had to do it all.

I remember the very first time that happened, there was a guy on Channel 5 News and Chris Clark, the evening anchor, called me that day after I had just started my radio show. I was driving home and my cell phone rang and he said, "Hey, this is Chris Clark, do you want to come on Channel 5's open line tonight and answer questions on the news?" I didn't believe him and thought it was one of my buddies punking me. He said to hang up and call Channel 5 and they'll put you through to me, and I called back and it was really him.

As soon as I hung up, I called my wife and told her we were going to be on Channel 5 and it was our big break and everyone would now know about our books. I went on Channel 5 and it was a wonderful evening and Chris was a great guy, but it didn't change my life.

Success is really standing on a pile of failures.

The Lesson:

What we've kind of figured out was there's not one singular event to cause success to be easy. Instead, it's a grind and it's everyday excellence in the ordinary. It's death by a thousand cuts. That's how you win.

When I finally surrendered to that, it was a lot easier emotionally.

I don't place as much emotional, financial or team weight on a single event or decision. Let's do it, and let's do it hard and with excellence – but if we lose that one thing or it doesn't work out, we'll be OK.

When you put your expectations on the wrong thing, you live with some disappointment. I instead place my expectations on the grind and the process and I'm not disappointed as much, and our team doesn't lose morale.

Follow Dave Ramsey on Twitter at @DaveRamsey

Photo courtesy of Jamie Ellis.

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