The most successful entrepreneur I know is also a friend of mine. That’s a pretty good combination if you’re smart enough to shut up and listen.

Last week a group of friends traveled together for several days, and I got a little time with him on the side. Twenty-five years ago, I probably would’ve spent most of that time doing the talking. These days I ask questions.

At one point we were talking about Las Vegas. I love Las Vegas, though I don’t gamble. “Those massive hotels weren’t built because people are winning money,” I told him. 

My friend laughed and said, “I’m an entrepreneur. I gamble every day.”

That one stuck with me.

For most of my career I never thought of myself as an entrepreneur. The word seemed too lofty. Entrepreneurs were people who started tech companies, raised millions of dollars, rang bells on Wall Street, and used words like “scalability” before I even knew what scalability meant.

I was a restaurateur.

Before that, I was a waiter, then a cook. Eventually people started calling me a chef, though that title always felt a little above my pay grade, too. In those early days, I worked 90 hours a week in the kitchen of my first restaurant, which I opened with $25,000 from selling a piece of land I inherited from my grandfather.

At one point in my very early 20s, I was basically homeless, definitely addicted to drugs and alcohol, and headed nowhere fast. After getting clean and sober, I lived in one room above a garage and eventually opened that restaurant while paying myself $12,000 a year.

Still, entrepreneur wasn’t a word I would’ve used.

Over the years, other things found their way into my daily orbit. Books. Publishing. Television. Travel. Other restaurants. Other businesses. Some worked. Some didn’t. That’s business.

In less than two months I’ll turn 65. When I was a kid, 65 was the age when people retired. There was probably a gold watch involved.

At 64, retirement is nowhere on my radar. I work more hours today than I did 30 years ago and enjoy it more than I did then. One of my greatest hopes for my children is that, 45 years into their careers, they’ll still wake up excited about what they get to do that day.

Maybe that’s why I finally became comfortable with the word entrepreneur.

Not because of anything I’ve accomplished, but because I finally understand what the word means to me. An entrepreneur sees something that doesn’t exist, sketches it out on a cocktail napkin, and believes he can make it work. Then he puts his time, money, reputation, and a fair amount of sanity on the line to find out.

That sounds a lot like gambling.

Steve Wynn once said, “The only way to win in a casino is to own one.” Maybe there’s a business lesson in there. Entrepreneurs gamble every day, but at least we own the house. We put our money down, make the decisions, take the risk, and live with the consequences.

I’d rather make that bet than put my money on a pair of dice.

Failure comes with the territory. Alex Hormozi has written openly about his first nine businesses failing. His point is simple: “You only need to be right once.”

Failure used to embarrass me. Today I know it’s part of the deal.

I don’t need to borrow failure stories from Abraham Lincoln or Michael Jordan. I’ve got enough of my own. Restaurants that didn’t work. Bad hires. Bad decisions. Money lost. Opportunities missed.

Accept the loss. Learn from it. Move on.

Onward.

That word has become a guidepost in my life for a reason. Recovery taught me that long before business did. It’s taken me over four decades of active recovery and 12-step work to realize how much of what I learned there has guided the way I do business. Honesty. Accountability. Inventory. Making amends. Service to others. Admitting when I’m wrong. Asking for help. Taking things a day at a time.

I’ve started working on a book about it, though it’s a couple of years away. The basic premise is how principles from the world’s most successful recovery program can be applied to business and leadership.

No growth in my life ever happened during the easy stretches. The growth always came through adversity. No great novel exists without conflict. Apparently, neither does a career.

Another thing I’ve learned late is to buy as much knowledge and experience as I can afford.

At 26, I thought I knew everything. That’s especially impressive considering I was a terrible student and knew almost nothing. I was cocky, arrogant, egotistical, and had plenty of opinions backed by very little experience.

At 64, I hire executive coaches. I read. I seek out people who are better at things than I am and ask questions. After 45 years in the restaurant business and 38 years as an owner, one thing has become perfectly clear: I have no clue about a lot of things.

Had AI been available when I was 30, I might be writing this from my private island—or at least my yacht somewhere exotic. I hear plenty of people complaining about AI. They can complain all they want. It’s not going anywhere. What excites me is what some 26-year-old entrepreneur is going to do with tools I couldn’t have dreamed of when I opened my first restaurant.

The tools change, but business really doesn’t. Work hard. Keep your word. Treat people right. Own it when you screw up and get back to work. Next.

Someone told me early in my career that a person could make up for a lack of intelligence by outworking everyone else. I took that to heart. Competitiveness has always been part of my makeup, but business has never just been about winning. It’s about people. Relationships matter more to me today than they ever have.

That became clear again during my conversations last week.

My friend operates on a level far beyond mine, but the more we talked, the more familiar his priorities sounded. Eventually a large portion of our conversation turned to family. His love and dedication to his family were obvious. We may operate businesses at very different levels, but when it came to family, we spoke the same language.

If 64-year-old Robert could sit down with 26-year-old Robert before he opened that first restaurant, I’d have plenty to tell him. Ask more questions. Listen more. Find mentors. Hire people smarter than you. Buy knowledge. Don’t fear failure. Don’t confuse confidence with competence. Learn balance earlier. Stay curious. Never stop learning.

But there’s one thing I’d tell him not to change.

Family first.

My wife met me when I was 27 years old, making $12,000 a year and living in one room above a garage. I’m pretty sure I was still living there when we got engaged, so the prospects weren’t exactly dazzling. She signed on anyway.

For all these years she has supported every restaurant, book, trip, crazy idea, long day, early morning, and entrepreneurial gamble. She was a restaurant widow before we had children and the most devoted mother imaginable after they came along. There were times I put family ahead of business when the business probably suffered because of it.

No regrets there.

So, at almost 65, when someone asks what I do, maybe I finally have the answer.

I’m an entrepreneur.

And apparently, I gamble every day.

Just not in casinos.

Onward.

Corn Pudding

3 cups              Silverqueen corn (four to five ears)

2 cups              Heavy cream

1 cup               Half and Half

1 1 /2 Tbl        Sugar

2 tsp                Salt

3                      Eggs + 3 yolks

1 1 /2 tsp         Black pepper, freshly ground

1 tsp                Hot Sauce

2 tsp                Onion, minced

Preheat oven to 300 degrees. 

Combine all ingredients and mix well. Place in two-quart baking dish. Place two-quart dish into a larger dish and place in oven. Pour hot water into the larger dish so water comes up halfway on the sides of the corn pudding dish.  Bake 40 minutes. Remove from oven and allow pudding to cool 10-15 minutes before serving. Yield: 10-12 servings