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Jeff Wills: “Leave nothing to uncertainty”

I just want more people to ride bikes — especially kids. It doesn’t need to be hardcore racing in lycra shorts; riding to the park, to your friend’s house, to school, to work; it’s all riding. Bikes enable people to get outside, feel better physically, explore new places, spend time with others, affordably get where they need […]


I just want more people to ride bikes — especially kids. It doesn’t need to be hardcore racing in lycra shorts; riding to the park, to your friend’s house, to school, to work; it’s all riding. Bikes enable people to get outside, feel better physically, explore new places, spend time with others, affordably get where they need to go…so much!


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing…Jeff Wills who is the founder of REGGIE. Jeff is a life-long cycling enthusiast and has been riding and racing all styles of bikes since he was a teenager. He’s also had a successful career in advertising where he’s worked with many of the biggest marketers in the world. He has brought his passion and experience together to build a fun new brand in cycling.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

REGGIE is really a partnership with my sister Laura. I bring the cycling passion and Laura brings the design expertise.

My background is cycling and advertising. I started riding when I was 13 and joined my local club (Oshawa CC). I continued to race on the road and mountain bikes into my mid 20s. I had wanted to be a pro and went to Belgium in 1991 to see if I could make it if I focused only on riding my bike. I learned within a few weeks that I wasn’t good enough and after finishing the season I came back and got a job at an ad agency in Toronto. I have continued to work in advertising ever since. Aside from REGGIE and being a keen observer of brands in cycling (and everywhere else), I have never done anything specific in the category.

Laura’s been a designer since she was about 5 years old and our mom gave her a box of fabric scraps and a sewing needle. She was hell-bent on being a fashion designer until the end of high school, when she suddenly switched directions and went to university for a Fine Arts degree instead, and started studying graphic design. She’s been working in graphic design and branding ever since. She’s always had a bicycle too, but she’d say she’s the Wills Kid with the slower bike… she was mostly a city commuter until picking up a luxury cycling travel company as a client, and then she started riding bikes all over Europe while art directing their photo shoots. She loves to ride her bike too, but just not the racing type.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah-ha” moment with us?

It was more of a life changing experience that took it from a hobby to a business.

Originally, REGGIE was born on a ride with friends. We were making fun of B&W videos on rainy mountain sides by one of the big brands. They were so serious and quickly becoming a bad stereotype. How we would mock these videos made for fun conversation on the ride.

A couple of years later, I was preparing for a big mountain bike race. I was one of the founding members of the Rapha Cycling Club (a big brand from London) and they didn’t want me wearing their jersey in a mountain bike race. I needed something so we designed our first Classy Camo jersey and it included the big REGGIE chest banner. For the next couple of years, I just made a handful of jerseys for friends and it continued as a fun hobby that we all enjoyed.

In September 2016, I had a bad crash while riding in the Pyrenees on a Cent Cols Challenge tour — arguably the toughest amateur cycling tour in the world. I broke my neck in 3 places but was lucky to not be paralyzed — and this made me realize that I needed to prioritize things in my life for pure enjoyment. So while I was recovering, we decided to turn our hobby into a little business to extend the fun to other riders.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

The cycling apparel category is overloaded with competitors doing the same old thing. Our business is based on a unique brand rather than just the product we produce and sell. We follow a few core pillars to ensure our brand and business are successful: our brand is about fun and standing apart from everyone else, and our pieces deliver stand out designs, top quality and high performance, exclusive fit options, and good value. Nothing happens that doesn’t make people smile.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Be realistic and objective about the business opportunity. Friends and family will say they ‘love it’ and ‘go for it’ but that enthusiasm has very little connection to business success. Ask any business owner: lots of people say they’re going to buy something but very few actually do. Before anyone makes the big jump, they should crunch the numbers really hard and then assume it’s probably going to be very challenging to get things off the ground let alone be successful.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I have a rule: if the business gets in the way of my riding, something is wrong. If I can keep my personal passion around riding strong, it’s super easy to connect that to the business and everyone else that loves to ride bikes.

And then we stick to our brand that we love. It would be so easy to compromise on our designs or anything core to the brand to broaden the appeal and increase sales, but it’s empowering to fight for something you love.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Our brand is about having fun and riding bikes. We run the business under the same premise and after three years it’s still super fun. But it’s a business and it requires work and time to keep it going and sometimes we can get jammed with deadlines and workloads. At first, we started to do too much, like introduce a number of designs at the same time, but now we build on what we’ve already done and put limitations on doing too many new things. This takes some pressure off our time and lets us focus on doing fewer things better.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

You’re responsible for EVERYTHING! This means you get to do the stuff you love AND a whole bunch of things you will hate. For me, that’s stuff like banking, accounting, taxes, inventory management. I knew this would be the case but takes way more time than you think and while it’s all critical to keeping the business going successfully, it’s not much fun.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Our return rates are extremely low for our category but probably half of them make me want to give up on the digital model. Despite lots of tools to help shoppers figure out their correct sizing, sometimes they will be way off when they should know better. It’s like they put no thought into it. Most returns are understandable and I’m happy to help but it costs us a lot of time and money to do returns so the added annoying factor for these few makes me want to quit sometimes. I just have to keep it in perspective. We had one of these super annoying returns recently and after dealing with it, the customer sent us one of the most encouraging notes we’d ever received.

Who has inspired or continues to inspire you to be a great leader? Why?

While our business sells cycling apparel and gear, the brand is about riding and having fun. For me, being around other cyclists pushes me to live the REGGIE brand. I need to keep it fun, ride lots, and look good as an ambassador for the brand and an example for other riders.

How have you used your success to make the world a better place?

While I like to think every time a rider pull on a REGGIE jersey, it makes them smile and want to ride, we have also been able to contribute directly to getting more kids on bikes. Through a cycling event in Europe, we leveraged our brand, design, and online channel to raise money for a cycling centre for kids in London.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

We’ve done this before in completely different businesses so we knew what we were getting into for the most part.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I just want more people to ride bikes — especially kids. It doesn’t need to be hardcore racing in lycra shorts; riding to the park, to your friend’s house, to school, to work; it’s all riding. Bikes enable people to get outside, feel better physically, explore new places, spend time with others, affordably get where they need to go…so much!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Leave nothing to uncertainty.”

I never assume there’s one answer to anything. I want to find the best answer to everything. Whenever I try to figure something out I will keep digging until I’m satisfied I understand all the options and able to make the best decision. It allows me to take chances or play it safe.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Actually, I wouldn’t want to do breakfast or lunch, I would want to go for a ride with them. It’s a great way to get to know someone. I’m sure there are plenty of big names that ride bikes but the one I know of and am a fan of is Reggie Miller. He loves to ride and gets that it’s fun. I think our brand matches up well with his name!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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