Sam Edelman has made it, and lost it all, several times. He sold equestrian-inspired footwear to Ralph Lauren, co-founded Kenneth Cole Productions, and launched the shoe division at Esprit. He took his own shoe company, Sam & Libby, public in 1991, but sold it at a loss. That’s when he turned his attention full time to his horse farm and said goodbye to the shoe business. But a crippling riding accident made Edelman realize he wasn’t done with shoes, and shoes weren’t done with him, just yet.

--As told to Liz Welch

All in the Family

My father, Arthur, owned a leather tanning company that specialized in exotics. So when alligator, iguana, and python [lost popularity] in the 1970s, so did the idea that I’d take over the family business. I started buying and selling horses instead. My then-girlfriend thought equestrian-inspired footwear and accessories would do well. So my father and I started Horseshoes and became Ralph Lauren’s first shoe license. Then we lost our domestic factory and went out of business.

The Cole Years

I called Kenny Cole, who was at Candie’s, and went to work there. Then we started Kenneth Cole Productions. He did creative. I did licensing, legal, and selling, but the company felt too small for both of us. I went to Esprit to start their shoe line.

The Muse

I was 27 when I met my future wife, Libby. After I left Esprit, I said to her, “Let’s do our own line.” She agreed, and I said, “We may lose our house.” That’s one of three times I’ve said that. It was 1987. We sold our horse and raised money, but we didn’t have a lot, so we used our own story to sell our shoes. Our first ad was a photo of us on the beach. Our round-toe ballerina flats with bows were our first hit, and we had three of the biggest shoes in the history of the industry. I took my eye off the ball when we took Sam & Libby public. We sold the company in 1996.

Wake-Up Fall

In 2001, I got thrown from a horse, and my leg got twisted and broken badly. I was crippled for nine months. As I was lying in bed, reading magazines, I saw all these great affordable clothes paired with $800 shoes. I decided to start an affordable shoe line. I was rusty. Things had changed, and I made mistakes. Libby and I sold our new horse farm to finance our business. Then Brown Shoe Company, now Caleres, bought some, then all, of the company. Most founders are gone within six months of selling. But I’m still here. Caleres gave me an opportunity to realize my vision: to buy back Sam & Libby [which we did in 2012]. Edelman Shoes is a division of Caleres, but we run the company like it’s ours. If a shoe is late, it kills us. If it sells, we’re ecstatic. To this day, whenever I see someone wearing our shoes, I introduce myself. I still love that.