by MR Magazine Staff

By Christopher Blomquist and Karen Alberg Grossman

Although we rarely realize it at the time, lapses in judgment and bad business decisions ultimately can prove to be fantastic learning experiences. We asked industry insiders to share their biggest work-related blunders—and what the resulting sting taught them in the end.

Christopher Bossola, CEO, NSTO (parent company of Need Supply Co. and Totokaelo), Richmond, Virginia

I’ve made hundreds if not thousands of mistakes in my career. Identifying the worst is beyond my quantitative skills. But a general theme does come to mind. I’ve learned to trust my gut and act more quickly to exit projects, brands and even people that are not moving us forward in a positive way.

Oliver Spencer, designer/founder, Oliver Spencer, London, England

The worst business decision I ever made took place in Paris where I sacked my store manager on the spot. He was managing another store as well as mine at the same time so he had two jobs without informing us when we were paying him full time. It was a bad decision to sack him on the spot because I got taken to a tribunal, and hundreds of thousands of euros later I lost because of the employment laws in France, which are shocking.

Eliot Rabin, owner, Peter Elliot, New York

My biggest career mistake, clearly, was not buying the building—1535 Second Ave., corner of 80th Street—that my landlord offered to sell me for $375,000 back in 1985. (I had a 750-square-foot store that I was renting for $2,000 month; I was doing $800,000 a year and making money!) He called me when he decided to retire and encouraged me to buy the building. I made the mistake of discussing it with various friends and advisors who discouraged me, saying the building was worth only $275,000. But my instinct was to go for it so three weeks later I called the landlord and told him I wanted to buy it; by that time, he’d sold it to an Arab doctor for $450,000. (Its most recent selling price was $36 million.)

So, this new landlord immediately raised my rent to $4,000, then $6,000, then $8,000. And that was back then! (If you wonder why so many storefronts on the Upper East Side are empty, it’s because rents are ridiculous! No one can afford to do business here. It’s a very sad situation.)

My other big career mistake was opening five stores with insufficient capital.

Daniel Leppo, executive vice president of menswear, Bloomingdale’s, New York

The biggest mistakes I make seem to center around soft-pedaling feedback. It does the person receiving it no good in the long run and leaves your team with the same knowledge gaps to repeat their mistakes.

Jim Murray, president, A.K. Rikk’s, Grand Rapids, Michigan

My biggest mistake was our venture into streetwear. The category was getting so much press, and everyone predicted it would bring in millennials so I thought we should give it a try. That was a mistake. We lost sight of our DNA, of who we are, of who pays our bills, of who buys the Zegna and Cucinelli and Isaia that make up 70 percent of our volume. We thought maybe the children of our core customers would buy the streetwear brands but they didn’t. So now we offer streetwear influences from within our core brands—Alessandro Sartori is doing a wonderful job incorporating current trends into the overall Zegna and Z Zegna collections. Our customers know and trust our core brands, so as long as these designers keep bringing in fresh looks, we’ll focus on these.

Geoff Schneiderman, president, Eleventy North America, New York

As far as mistakes in this business, how does one even count them all? In all fairness, I truly do not believe in “mistakes” simply because each decision or event is a setup for what is meant to come next. Certainly, I’ve made decisions that might have seemed bad at the time; however, I believe that without these missteps, I might not be where I am today.

I do recall one mistake very vividly—it was Eleventy’s first holiday delivery in the USA, and I was offered an opportunity to make an exclusive gift-giving sweater program for one of the major department stores. I was so excited because it was a huge order and it was going to raise tremendous awareness for the brand. Let’s just say we’re still looking for that awareness opportunity, and all of our cousins, nephews, uncles, and mailmen will be receiving these sweaters as gifts for the next several years. Live and learn!

Ed Boas, president, Lanes, Miami, Florida

I’ve made so many mistakes in my career that I can’t begin to list them. And I still make mistakes: my wife points this out to me every day! But I try to correct them, not dwell on them, and move on. And apparently, I’ve done more things right than wrong because I’m still in business, doing what I love: buying and selling beautiful clothes, helping guys look great and making fabulous friends among my customers and vendors. That’s what still gives me tremendous joy.

Simon Kristoph, director of wholesale, Groupe, New York

This is an interesting question because I’ve made so many mistakes, ha! I would have to say overall my biggest mistake was being young with an attitude that I knew better than anyone else in this business. The way I rectified it was to spend time with great mentors (I was lucky to have had several) and to pay close attention to how they managed their business. That’s not to say I stopped making mistakes, I just got better at managing them. We are always learning after all.

Wally Naymon, owner, Kilgore Trout, Cleveland, Ohio

Having never made a mistake, that’s a difficult question to answer. But seriously, I could probably fill a book with my mistakes. For me, my biggest errors have been trying to be conciliatory when confronting incompetence, being too concerned about hurting the feelings of the incompetent ones. I’ve since learned that it’s best not to massage the message since it could lead to a learning opportunity and possibly personal growth from their previous level. It happens both at the store level and in relationships with vendors. Obviously, after 42 years, I’m speaking about previous situations since with our current team and vendor partners, it’s all sunshine and roses.

Leo Tropeano, founder, Mugsy Jeans, Chicago, Illinois

My biggest mistake was going to market too soon. I thought the product was perfect when we launched but I didn’t realize at the time that what I think isn’t what’s important. At the end of the day, what the customers think about the product is the only thing that matters. It’s a double-edged sword here because trying to sell an imperfect product in those early days allowed me to get the feedback I needed to tweak and perfect our jeans. But I could’ve saved a lot of time and money if I’d spent more time developing before going into that first production run.