In 2024, veteran footwear executive Rick Blackshaw founded STOKE Shoes, a performance-lifestyle brand engineered for the 65 million American men with wider feet overlooked by traditional athletic footwear. STOKE combines wider, anatomically accurate fits, high-rebound cushioning, and practical designs for real-world wear, translating decades of footwear leadership into sneakers built for comfort, simplicity, and everyday utility.
Blackshaw has transformed iconic brands and built category-defining businesses across the industry. Across senior leadership roles, he has driven growth, revitalized heritage brands, and led complex organizations through periods of scale and change. Most recently, he served as President of HEYDUDE, where he led the integration of Crocs’ largest acquisition and helped evolve Crocs from a single-brand company into a multi-brand organization. Earlier in his career, Rick grew Chuck Taylor All Star global wholesale revenue by 400%, revitalized Keds through the Brave Girl Movement and a landmark Taylor Swift collaboration, and led successful turnarounds at Sperry and CCM through product innovation and modernized marketing.
What is your typical day, and how do you make it productive?
My days are usually somewhere around 7 a.m. to 7 p.m., with breaks in between, and I’m usually checking communications one more time before I go to bed. Startup life doesn’t really respect a traditional 9-to-5 schedule, so I’ve learned to embrace that reality while still trying to create some structure.
I try to schedule my day in blocks and use the time between meetings to drive specific tasks to completion. I’m a big believer in short bursts of focused execution rather than letting things sit on a never-ending to-do list. If I have 30 minutes, I want to know what I can actually get done in those 30 minutes.
And when I feel myself fading, I’ll do some push-ups or pull-ups. It sounds pretty simple, but changing your physical state can change your mental state pretty quickly. Sometimes five minutes of exercise is more productive than staring at a screen for another hour.
How do you bring ideas to life?
The first step is having enough time to think. That’s a luxury in a startup, and a lot of my thinking happens during off hours—or sometimes in the middle of the night when I wake up and my brain decides it’s time to solve a business problem.
Once I have an idea, I try to communicate it as succinctly as possible. If you can’t explain an idea clearly, there’s a good chance you haven’t really figured it out yet. Then comes the less glamorous part: grinding it into existence. Ideas are easy. Execution is where the work is.
What’s one trend that excites you?
The obvious trend that excites me right now is AI. The analytical power of tools like Claude is wild.
We’re still very early in understanding what these tools can actually do. I don’t view AI as a replacement for judgment or creativity, but as a force multiplier. It can help you get from a blank page to a thoughtful starting point incredibly quickly and, if you challenge it rigorously, it can help you pressure-test your thinking as well.
What is one habit that helps you be productive?
Time blocking. I try to create defined windows where I’m focused on getting something done rather than constantly reacting to whatever comes into my inbox.
The other habit is physical movement. When my energy or focus starts to drop, I’ll exercise rather than trying to force myself through it. Sometimes the best productivity hack is simply getting away from the computer for 10 minutes.
What advice would you give your younger self?
I’d tell my younger self not to worry so much about the meandering.
Early in your career, you can feel like you need to have everything mapped out. I don’t think that’s true. The early career detours, experiments and seemingly unrelated experiences tend to work out just fine. What’s important is not settling for something you know isn’t right simply because you think you’re supposed to have a straight-line career.
Tell us something you believe almost nobody agrees with you.
Have a conscious path, but understand that you’re going to get knocked off it. That’s normal. You can have a plan and still end up somewhere completely different. In my experience, things have always worked out for the better—even when, in the moment, they didn’t feel like they would.
What is the one thing you repeatedly do and recommend everyone else do?
Exercise. It’s probably the most consistently useful thing I do for both my physical and mental health.
I’d also recommend learning how to disconnect. I’m not particularly good at this myself, which is ironic given that I’m recommending it. With consumer brands, there’s always another competitor to watch, another piece of social content to see, another trend developing. You can fall down that rabbit hole very easily.
At some point, you have to put the phone down and let your brain work on something other than your business.
When you feel overwhelmed or unfocused, what do you do?
Exercise.
It sounds almost too simple, but it works. When you’re overwhelmed, continuing to sit there and process more information isn’t always the answer. Getting up, moving your body and stepping away from the problem for a little while can reset your perspective.
What is one strategy that has helped you grow your business or advance in your career?
I’ll give you four:
1. Find the real gap, and size it honestly.
STOKE didn’t start with a product. It started with a number.
Seventy-five percent of American men have wide feet, but only about a quarter of them are actually buying wide shoes. That’s a roughly 65-million-man gap that the traditional footwear industry wasn’t really pricing for.
You have to figure out the total market, but then go one step further and find the portion that’s genuinely underserved for a structural reason—not simply because somebody hasn’t marketed to them correctly. Structural gaps tend to stick around. Marketing-driven gaps usually don’t.
For me, part of that insight also came from simple observation. Walk through any airport and look at the 25-to-54-year-old guys. You see a lot of men with big feet who probably don’t want to spend $160 on a running shoe that is likely too narrow for their “big dogs.” That was an obvious consumer problem hiding in plain sight.
2. Be obsessed with the consumer.
Understand what’s in your consumer’s heart, mind and wallet better than anyone else.
That’s a Nike maxim that has stuck with me because it’s so important. Consumer obsession isn’t just a marketing philosophy; it’s a potential source of durable competitive advantage. If you understand your customer better than your competitors do, you can make better product decisions, better marketing decisions and better business decisions.
The consumer ultimately decides whether your idea works. You have to be willing to listen to what they’re telling you—even when it’s different from what you want to hear.
3. Build a platform, then let iteration do the work.
We grew Chuck Taylor from roughly $340 million to $1.8 billion in global wholesale revenue without launching some completely new franchise. We kept iterating on one iconic silhouette that had incredible visual DNA.
The lesson is to find a platform that’s strong enough to extend for a decade and then put your energy into extending it rather than constantly reinventing it.
Sometimes that platform is a product. Sometimes it’s a marketing idea.
At Keds, for example, we were facing irrelevance in a surging vulcanized footwear category dominated by Chuck Taylor and Vans, both of which had strong male-centric platforms built around rock ‘n’ roll, skate and surf. We decided to build something different: a “brave girl” movement. And we found the ultimate brave girl in Taylor Swift.
The point is that the platform gives you something to build on. You don’t have to start from zero every time.
4. Protect gross margin like it’s oxygen.
Almost every turnaround I’ve run—including Sperry, Keds and CCM—involved moving gross margin by 500 to 1,000-plus basis points before the revenue really moved.
That’s not a coincidence. Margin is what gives you the room to reinvest in product, marketing, people and growth. If you chase top-line growth without paying attention to the economics underneath it, you can scale yourself directly into a cash crisis.
Revenue gets the headlines. Margin gives you the oxygen to keep going.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
I’ve been knocked off a couple of perches in my career. When you’re in leadership, it’s easy to assume that if something changes, it must be a direct reflection of your performance. I’ve learned that’s not always the case.
When those things happen, I try to catalog the great things the team accomplished and the things we did that translated into real business success. I think about how we took a brand from Point A to Point B and what we learned along the way.
You also have to maintain some perspective. A career isn’t one job or one title. It’s a collection of experiences, successes, failures and relationships.
And, as I’ve said before, things tend to work out for the better. Sometimes you just don’t know that until later.
What is one business idea you’re willing to give away to our readers?
Broccoli chips.
I think there’s an opportunity to take something that people know is good for them but don’t necessarily crave and turn it into a genuinely addictive snack. Make broccoli crunchy, flavorful and legitimately delicious rather than trying to convince people that they should enjoy eating steamed vegetables.
What is one piece of software that helps you be productive? How do you use it?
Claude.
I use it for just about everything—brainstorming, organizing thoughts, pressure-testing ideas, researching questions, working through problems and turning a rough thought into something more structured.
It’s definitely not an end-to-end solution, and you still need judgment. But it’s remarkably good at taking a pile of ideas and helping you make sense of them.
The key is to challenge it. Don’t just accept the first answer. Push back, ask it to find holes in its thinking, give it a different perspective and make it defend its conclusions. Used that way, it’s less of an answer machine and more of a thinking partner.
What is the best $100 you recently spent?
Corporately, we bought Dickies work shirts and personalized them for the team.
I really like the idea of putting them on and going to work. There’s something about a uniform that creates a little bit of identity and camaraderie. It also makes me laugh because you can wear one to a party, restaurant or Starbucks and suddenly people make assumptions about you.
There’s a fun psychology to that. What people see influences what they think you do, and sometimes it’s interesting to play with that.
Do you have a favorite book or podcast from which you’ve received much value?
The All-In Podcast gives me a lot of value. I like that the hosts cover technology, business, politics and the broader forces shaping the economy.
You have to screen out some of the bluster, but that’s part of the entertainment. I don’t necessarily agree with everything they say, but I like hearing smart people argue different sides of complicated issues. It forces you to think.
What’s a movie or series you recently enjoyed and why?
I’ve really enjoyed Sundae Conversations with Caleb Pressley. It’s funny, irreverent and different from the typical interview format.
For the family, Ransom Canyon with Josh Duhamel has been a favorite. It’s one of those shows that’s easy to get into together, which is increasingly rare.
Key learnings:
- Life is a fight for your attention. The challenge is to control where you put that attention and use it to advance rather than simply letting it get consumed by things that pass the time.
- Things work out for the best. Your career won’t follow a straight line, and setbacks don’t necessarily mean you’re going backward.
- Have a plan and work it. Be intentional about where you’re going, but recognize that you’ll inevitably get knocked off course. Adjust and keep moving.
- Find the real gap. The best businesses often begin by identifying a structural problem that an existing industry has overlooked or underserved.
- Protect the economics. Growth matters, but gross margin and the ability to reinvest are what give a business the oxygen to sustain that growth.