Grit, Growth, and Great Boots: How Todd Stewardson Built a Business on Determination and Vision

To Todd Stewardson, cofounder and CEO of Duradero, success is built on grit, curiosity, and the willingness to admit when you don’t have all the answers. We sat down for a conversation about his roots in the footwear industry, his experience navigating major career challenges during the Great Recession, and the lessons he’s drawn from decades of experience in sales and leadership.?

Can you walk us through the path that led you to founding Duradero?

Todd: I’ve been blessed to work for some of the greatest companies in the world throughout my career, but I definitely didn’t take the “traditional” path to the C-suite. I’ve always been in what I call the “fashion footwear and home furnishing sector.” I started out at Nordstrom on the sales floor before moving into roles like buyer and merchandiser. Eventually I got into the wholesale business, working with brands like Ralph Lauren, Timberland, Bally of Switzerland, and Ariat—always as either a senior sales executive or VP of sales.?

Things were good until 2009, when the economic downturn hit. That was a major challenge for me. After a brief stint in consulting, I made the shift into e-commerce when I joined this online home retailer called Y Lighting. That was right around the time digital marketing was getting big. Let me tell you, I was absolutely fascinated—I was like, “You can run an ad and see where people are going? You can track consumer behavior and adapt in real time? How did I not know about this?!” That inspired me to get involved in a couple of other ventures: an early text messaging platform for retail stores and a Kickstarter campaign for magnetic shoe closures. We aimed to raise $36,000 and ended up making around $360,000. That was such an adventure, and it taught me some really important lessons about scaling and adapting quickly.?

This all culminated four years ago, when I reconnected with a long-time contact in the shoe industry, who runs the largest shoe repair facility in the world. We could see this market opportunity: customers were willing to pay premium prices to repair high-end boots, so why not leverage that? That was why we created Duradero, a premium work boot brand with built-in repair services. We launched in 2021, and even though we didn’t have product until 2022 thanks to the pandemic, we’ve had an incredible couple of years.?

You mentioned facing challenges during the Great Recession. How did that affect your career path??

Todd: That was one of the toughest periods of my career. The economy was terrible. I found myself unemployed, having to navigate a job market where I was often overqualified for the roles that were available, without any idea what was next. I eventually decided to try my hand at consulting, despite having no clue what a consultant even did. Thing was, I’d always been a sales guy, and up until that point, I’d always been moving up in my career. So that was really humbling. It took me about a year to finally swallow my pride and say, “You know, I think it’s time to find a ‘real’ J-O-B.”?

I started applying for jobs—including roles I was overqualified for. I didn’t want to scare anyone off, so I would always tell them, “Look, I might not be Mr. Right, but I can be Mr. Right now—here’s what I can do for you.” That approach eventually got me in the door at Y Lighting, so in a sense, that period, as tough as it was, was the catalyst for everything that came after. I’ve always believed that people learn more from failure than from success, and that ended up being really true in my case.?

It sounds like continuous learning has been a common denominator in your journey.

Todd: Definitely. I always try to seek out environments where I’m challenged and, frankly, ignorant. There was a recent Sidebar gathering where I joined a breakout session on product-led growth, which I knew nothing about. I was a shoe salesman surrounded by all these tech leaders. But those are the moments when you grow, right??

What role has mentorship played in your career, either as a mentor or a mentee??

Todd: In sales, every day feels like an opportunity to mentor someone who works for you, and I love helping people out. It’s a really rewarding experience. I’ve also had a lot of guidance from others. When I was first getting into consulting, I worked with someone who really helped me with goal-setting, accountability, and execution, and that led to all sorts of opportunities that I never would’ve had otherwise.?

What led you to Sidebar?

Todd: I discovered Sidebar through James Clear’s newsletter, which I read religiously. I was intrigued by the idea of having a group of people who could challenge my thinking and expose me to new perspectives. I wasn’t sure if it was the right fit at first, but after talking to Ha Nguyen about her vision for the platform, I decided to stick with it, and I’m so glad I did. I really, really love my group. We’ve got all these fascinating people doing amazing work at innovative companies, and it’s really motivating and inspiring to me. I’ve also been able to share my expertise in sales and fundraising to help others, which is really fulfilling.?

What’s the most important advice you would share with leaders or aspiring leaders?

Todd: “Grit, don’t quit.” That’s the motto by which I’ve navigated most of my career. There are going to be times when you want to give up, but if you do, you almost always end up feeling like you quit too soon. So stick it out, even when things get tough.?

Don’t forget to be vulnerable, too. I’ve always thought the real definition of CEO ought to be “imposter,” because there’s no way you can know how to do everything. You won’t always have the answers. That’s why you have to surround yourself with good people and empower them to help you make decisions on things you know less about. That’s what it means to be a leader: to not be afraid to say, “I don’t know, but I’m going to figure it out.”

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