He’s crashed three times in the real estate business and survived to develop again. At the same time he, and now his son Rick, have built Highland Bank into seven branches.

Now he’s also been through the University of Minnesota, graduating this May with a bachelor’s degree from the College of Continuing Education. He told Upsize what he’s learned along the way.

“My partner and I started on our own. Our first apartment building was at 34th and Emerson. We sold it to investors before it was done and I thought, “That’s pretty good.”

Then I talked with people I’d met in the Jaycees. They said they syndicated real estate. I didn’t know what that was. They said they raised money from lots of individuals. We sold a deal. It turned out to be our biggest commission to date. It was $100,000; we’d get it over three years, and split it between two people. It didn’t exactly put us on easy street, but when you’re broke, it looks good.

This was about 1965. My partner was traveling to Chicago. He saw all the offices being built around the airport. We went back to the syndicators to ask, “Can you raise money?” They said, “Sure.” It turned out later they couldn’t. We bought land from a farmer and Control Data, and built Metro Office Park. Control Data at the time was expanding; the freeway was going out to the airport.

When the syndicators fell through, five of us went to the bank and borrowed half a million dollars. Just three weeks earlier my partner and I were turned down for a thousand dollars. I remember walking out of the bank about four feet off the ground. I thought, “If they knew what I knew.”

At the beginning, as partners, we got along because we were all broke. Once we were making money we couldn’t get along. I started Wall Cos. I bought the land that’s now Normandale Office Park at 494 and Hwy. 100.

Meanwhile, a friend had bought a bank. He asked me to invest. I didn’t know you could buy a bank. In 1960 Alice and I were married. We had three kids. About 1965 we bought a little piece of the bank.

But the real estate business was my first business. Real estate is a risky business. In the early days, I thought this is the best thing since popcorn. But when it turns it’s like a stone rolling downhill. You can’t get out of the way. My world darn near came to a crash.

I bought my partners out. I knew it would be a bad ride. We decided to hunker down. I let everybody go except my secretary. Somewhere, somehow, it’s hard to remember exactly how, we got through. I had three kids, a wife, a house, a car, and no income.

One thing that was a surprise to me is how long it takes to start over again. Your own psyche is so beat up. You’re more risk-averse. Your credit is whacked.

I think having gone through some traumatic crashes, you develop a great deal of respect for people who’ve been through tough times.

The worst crash I had was in the late ’80s. We had owned the Foshay Tower; we ended up having to give that back. We had a big project in Florida, a retirement community. It took me 4 1/2 years to get out of business. I spent 4 1/2 years talking to people who didn’t like me. There’s fear every morning that you’ll lose everything you’ve got.

I’ve told my kids it isn’t so much that people fail in business, it’s that they quit. On the other hand, when you get into a lot of trouble you need to know when to get out.

The banking business is completely different. It’s regulated. It’s smoother to manage. It isn’t easy and we’ve proven that by screwing them up. I ended up buying Highland Bank from Irwin Jacobs, and added branches to those. The banks have been growing 10 percent a year. It’s allowed us to stay in the real estate business.

Back in the worst times, when I finally got out, it was about 1990. I said I have to get going, and I was looking at a mapping company. I was going to invest in it. The next day, I saw in the business section, that company had filed for bankruptcy. I said, “You’re like a quarterback who’d hit his head too many times.” I said, “I’m going to take a year off.”

I had this big boat in Florida, now I’m broke. I’m getting rid of all my toys. But I can’t get rid of the boat because I owe more than I could get for it. I said to Alice, “Let’s go live on the boat.”

I’m going to read great books, things I’ve never read. I said to the librarian, “I’d like a list of the world’s great books.” She opened up the card catalogs and said, “Here are the lists.” She said, “Make your own list.” So I did. I gave it to my secretary, and said, “Buy these books and ship them down.”

What happened in reading those philosophy books, I learned it’s not the answer it gives. It’s the question it asks. I went back to classes at the U. When I got into the degree plan, I wanted to name it, “Who makes the rules?” You get to a certain age, you look back and say, “Who made the rules? Why do I follow them?”

The last class I took was cultural anthropology. It turned out to be about culture, how it was formed, and culture is simply the set of rules and guidelines we follow.

Who makes the rules? We make them.”

— Interview by Beth Ewen, UpsizeMag.com