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Peer Portraits: Samuel Bail, Troubadour

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Samuel Bail, Troubadour

You will soon find out that we are big fans of Samuel Bail. The Troubadour Co-founder and Oxford alumnus, has swam the English Channel, biked from Cairo to Cape Town, is an Ironman, a new father and a dear friend of HNDSM. We chatted with Samuel on a sunny afternoon in Toronto about his mindset in sport and entrepreneurship.

We’d love to know more about your background, upbringing and the road that brought you to where you are now, personally and professionally.

I grew up in a family of creatives – my mother is a potter – and I’ve always had an interest in design, so being in a business that involves product creation is very exciting for me.

When I was growing up, I spent a lot of time with my grandmother, who shared her passion for adventure and the outdoors with me. Since I was nine, we have gone on cycling and hiking trips together nearly every year (she’s now 88 and still up for nearly any adventure). This inspired in me a lifelong quest for adventures, whether it’s Alpine climbing, triathlons, or swimming the English Channel.

My love of endurance sports such as climbing, cycling, swimming and running is shared by my Troubadour co-founder, Abel Samet. We met when we worked together in finance. Our jobs involved a lot of travel and we became obsessed with finding the perfect overnight work bag. We wanted a bag that was refined enough for business, rugged enough for the great outdoors, and casually smart for weekends with friends. We couldn’t find it, so we decided to create it.

From the very first days of Troubadour, the performance of our products has always been extremely important. I think this is rooted in our participation in sports where it’s essential to have gear you can rely on, no matter what happens.

This means that every time we develop a new bag, I get to combine my athletic hobbies with my appreciation of product design and performance. I have the fantastic job of stress-testing new bags, to see how they perform in terms of function, comfort and ergonomics.

We have chatted previously about the role that endurance sports have played in your life. How does the mindset during training and competing translate to everyday life and business?

Building Troubadour has been similar to endurance sports in many ways. It has been a long road with lots of highs and plenty of challenges! :-)

Going into an endurance event, I know there will be moments when I’ll want to stop, but I just need to keep going. There are moments like that in my experience with Troubadour, too. Thinking about the bigger goal and working one step at a time has worked for me in endurance sports and also in business when things get tough. At the same time, I find both immensely fun and tremendously satisfying.

You completed the formidable feat of swimming the English Channel. Did that experience change how you see yourself? How so? What do you think differentiates you from others when it comes to committing and executing on such goals?

It didn't change how I see myself. It was a tough day and I'm glad I did it, but that's about it!

I like having goals like that because it gives me something to train for. When I have a goal that I'm excited about – and a little scared about – I'm motivated to train. I'm happiest when I incorporate some physical activity into my day and having a big goal pushes me to do that.

I always need a goal that's a little more challenging or different than the last to get excited about it and motivated to train for it.

When it comes to executing, I start by doing a lot of research on what I need to do to be successful. Usually that means finding people who can give me good advice. With that knowledge, I can create a plan and then I start chipping away at the plan, bit by bit, day by day.

Some days it feels like you're making quick progress, on other days slow progress, and on some days it seems like you have gone backwards. I try to maintain my belief in the plan and just keep building on the training.

When I decide I'm going to do something, I keep at it until it's done. I think tenacity helps me to achieve big goals.

Samuel Bail, Troubadour

What is something you believe everyone should experience in their life?

Whatever makes them happy! That’s something that’s very different for everyone, so it’s impossible to give one answer. I would only encourage people not to worry too much about failing.

What was your favorite moment today and do you have any favorite grounding rituals?

My wife and I became parents for the first time a month ago, and I love spending time together as a new family.

My grounding rituals are to get to bed early and try to move every day, ideally outside.

Work from home essentials? How are you coping with this new reality?

A good desk setup with a proper monitor makes a huge difference for me.

I find that getting out of the home/office every day, ideally to enjoy some sunshine, is super important. It's too easy to fall into a routine of staying indoors when you’re working from home. Getting outside for some sunshine and fresh air does wonders for my energy.

Any advice you can give to people just starting out in their fashion career (in and out of the current context of the virus).

Figure out what makes your business different. Make sure that whatever is unique about your business is something that people want, something they see value in.

It's also important to seek a lot of feedback and be brutally honest with yourself about what needs to change or improve in your product and communications. With these fundamental principles as a base, the sky's the limit!

Photography by Nunu Jamani

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