Chris Lamontagne is an entrepreneur & the CEO of Teespring, the world’s largest creator commerce platform. Teespring empowers people to create and sell their own customized products and focuses on reducing the friction between ideation and bringing the idea to market. 

Before Teespring, Chris created his first company when he was 19: RU, a sports-focused brand engagement platform that served top clients like ESPN and O2. Shortly after, he was recognized as the Entrepreneur of the Year by The Prince’s Trust. 

After successfully exiting the business when he was 23, Chris went on to help found Urban Electric Transport, an all electric car sharing program with a focus on green innovation, as well as Hiremarket, an online comparison marketplace for the construction industry. 

Chris has since continued to support young entrepreneurs looking to enter the modern tech and e-commerce space through scholarships to his hometown of Liverpool. He has expertise in crafting strategies for growth, customer acquisition, and go-to-market. 

Grace Tan (BT): What was your first business venture — the one you started when you were 19? 

Chris Lamontagne (CL): So when I was 19, I dropped out of university. I've realized that I'm a real kinesthetic learner — someone who learns by doing, in contrast to the traditional academic learner. So, I wanted to get out into the world, and I felt like it was time for me to supercharge my thinking and get some new ideas and innovation. 

At the time, I was really into sports. I played a lot of sports at school and university, and I kind of thought I was going to be a sports coach. … And then I kind of just as quickly realized that I didn't want to be a sports coach [laughs]. I had an idea to initially build a coaching business, but that idea would evolve a bit more from sports coaching to a marketing business for sports companies — and that became my first business. We were organizing and running engagement workshops and events for sports brands. We were a platform that specialized in connecting brands to younger audiences through sports, and our biggest client was ESPN, the American sports channel. We would deliver programs and marketing activations for clients like them. 

The business was around 30 people, and I ran it for about four years until I sold the business when I was 23, so I got very, very lucky in being able to exit the business. And that's how I started — how it all started.

BT: What were your most valuable lessons for your personal and professional life that you got from your entrepreneurial experience?

CL: One thing that I took from the experience was the concept of slowing down before speeding up again. 

I think that was probably the one of the best things I learned, and I think it’s critically important, particularly in more stressful work environments. You need to be able to stand back and look at where you’re going: understand your environment, where you are, and where your ideas, creativity, and energy come from. I think it's so easy to go into autopilot when it comes to thinking about your career and direction, but you need to be able to change the lens that you’re looking through, and consider things from different perspectives. Sometimes I’ve slowed down and been able to say, “I don't think I'm understanding the problem well enough,” or “I don't think I'm in the right mindset to solve this problem.” And trying to challenge your mindset starts with yourself first. I like to consider my physical environment — and this year’s been pretty bizarre for that, because you can't really go anywhere — but I’ll see if I’m trying to solve the same problem from the same place. 

That’s why traveling has always been a great way for me to unlock my creativity. I’ll get to be in different places, meet different people, and hear different ways of thinking. During COVID, though, I'll jump in the car to go for a drive instead, and that's how I'll try to come up with a solution to a problem — and then I can speed back up and really kick into action.

BT: What’s an example of a time where you challenged yourself to do something really difficult, or maybe do something you weren’t sure you could achieve?

CL: I don't believe that there are things I can’t do. It doesn't enter my mind, or I more likely don’t let it enter my mind. If I were told that something “isn’t possible,” my response is typically, “well, we'll see.” There's a ton of school of thought on this — the idea that you become what you think about. So you have to believe that no one's going to stop you. You set your own pace, and you are in charge of doing that stuff. 

BT: A lot of your work experience is in growth, specifically through go-to-market strategies for companies. How important is the go-to-market strategy for a company?

CL: I think it's super important, but I’ll give it some context as to why: in my career, I’ve found that when you run your own business — particularly if it’s a small business — it’s not an option if you grow or not: you either live or die. Your business has to grow very, very quickly, otherwise it's not going to survive. And I was young when I launched my first business — I was 19 or 20, with no money in the bank and with wages to pay, so not growing wasn't an option.

What I quickly recognized was that the concept of a ‘launch,’ and that launching new projects were just really good ways to drive growth in businesses. Those launches create momentum in the business for all stakeholders, internal and external. So my attention to the go-to-market part of business started very early in my career, and it really became prevalent. When I joined Gett, which is like an Uber competitor, my role was to expand our business across new territories. I was in charge of creating the playbook for new countries, and it was my job to go and launch Gett in 70 markets internationally. I would be the first guy on the ground: I would drop into their country, and set up the business.

From living that role for 3 years, I developed this approach of a ‘day one’ principle: I’d ask myself, if I just had one day to launch a business, how would I do it? And then you’d work backwards, and deconstruct the components. 

BT: What's one piece of advice you would give to people who might be looking to enter these sorts of super high-growth fields, as I think the general sentiment is that it is a fast-paced environment?

CL: So in terms of starting a company in a high-growth environment, you've got to realize that it doesn't start and grow straightaway, by itself.

You need to approach it with a flywheel mindset: how do you kick the flywheel? How do you inject some pace into the business? And that could be done with marketing activity, or growth hacking, or investments, or some mix of all those things, but you've got to be thinking about how to create and maintain momentum, and when it comes to joining a fast-growing company and being in a business that’s already growing, you’ve got to realize that there's a pace that's been set and you've got to keep up with that pace. 

One of our values at Teespring is to “embrace the pace,” and that motto actually came from our employees because at Teespring, we're never going to make apologies to our employees about how fast our business goes. In fact, it's probably only just going to speed up. And this sort of environment is really not for everybody and that's totally fine, but if you’re looking to enter a high-growth business, you need to understand that there’s really some speed involved, whether that's replying to emails faster, or better communication, or turning a workaround quicker.

I think where I've been really successful in working in fast-growth environments is that I didn't just take the pace that was already set — I’d even encourage us to speed up further. And so I’ve always been the sort of person to push and ask questions like “how do we get this out the door?” And people have kind of pushed back before, because they feel like they still need to improve things first before they launch. And my advice is that it’s actually more important to get things out the door, and then it will evolve and improve from there. It needs to become a thing first. Otherwise, it will just stay as an idea that we're talking about.