Entrepreneur
Let me take you way back to 2005.
Technologically, it’s a different world. The iPod rules — and with the iPhone two years away, flipping open a Motorola Razr wins you cool points. Facebook is an obscure startup. For most people, the cloud is still just a thing in the sky. And AI? Mostly sci-fi.
It might sound like ancient history, but that was the reality when I started my point-of-sale company. Back then, POS terminals were glorified cash registers — clunky black boxes with limited powers. That’s where we came in, bringing retailers iMac-based systems that simplified checkout and yielded insights into their business.
Twenty years later — in the age of AI, 5G and 24/7 social media — we’re still going strong.
How can company founders and leaders adapt in the face of relentless change? What are the principles that help your business survive — and thrive? Today, that kind of adaptability is more important than ever, given economic uncertainty, geopolitical turmoil and accelerating tech change.
Here are four lessons I’ve learned along the way.
Related: How to Reinvent Yourself and Your Business in This Moment of Opportunity
1. Throw away your job description every year
Keeping the business relevant means being willing to take on new roles.
When we started, I was the main software developer, and I loved it. But I soon learned that entrepreneurs sometimes need to “kill their darlings,” as a great writer once said. Although I’d been coding since age 13, I had to step away so we could grow our engineering team and scale the business. The same went for another passion of mine, user interface design.
I’ve seen so many founders bottleneck their business because they cling to what they know. As a company grows and changes, it’s essential to absorb new skills. For example, when we took the business public, I learned everything I could about finance. Lately, I’ve been tackling a whole new challenge as we exit the startup phase and focus on profitable growth.
2. Focus on culture. It matters way more than you might think
For many companies, culture is an afterthought or window dressing. Today, we see how quickly businesses are jettisoning their DEI policies in response to political pressure. But culture is anything but superficial.
When I launched our company in Montreal’s Gay Village, the entire core team of four was from the LGBTQ community. As the business grew to encompass people from all walks of life, we encouraged everyone to be their authentic selves.
It doesn’t matter what you look like or what your background is. Everyone gets a fair shot based on their contributions. In our latest annual diversity, equity, inclusion and engagement survey, more than 85% of team members said they can be their authentic self at work.
The upside of a truly welcoming culture? Companies attract and keep quality people who want to build their careers. When employees feel a sense of ownership and know they can make an impact, they’re more invested in the business.
3. Keep falling in love with your customers
I still fondly remember working side-by-side with our first handful of customers — a Mac dealership, a furniture store and a spa and wellness business. They told me what features they dreamed of — creative ways to check out, track customers and reward them — and I coded them into our product on the spot.
In the early days, building that kind of camaraderie with clients is easy. The trick is sustaining it as you grow. The bigger a company gets, the less time employees spend with the people who use its products or services. The fallout from losing touch with customers can include falling sales, brand damage and reduced loyalty.
So, for founders and their companies, staying close to customers is well worth it. One big benefit: intel on the ground. Rather than telling customers what they need, you’re asking what matters to them and what their pain points are. This, in my experience, is one of the most powerful ways to sustain product-market fit over time and avoid drifting away from your customers’ needs.
We still do that today. For example, I regularly hold Table Talks that bring our customers together over dinner. At one recent event, a vintage-store owner grilled me about the effectiveness of social media ads in getting shoppers through her door. She wanted a way to track the ROI of her social media investment, and that got our gears turning in terms of new features.
Putting customers front and center drives the bottom line. In one study, companies that were leaders in customer experience grew their revenue more than twice as much as CX laggards.
4. Look outside the company for inspiration
As much as I love being an entrepreneur, it’s not enough. I’ve realized that to sustain energy and focus, I need to feed other sides of my life. For me, things like visual art and environmental conservation are just as important.
I think too many leaders neglect this dynamic. The business becomes their alpha and omega, and they actually feel guilty having a life outside work. While this might deliver returns in the short term, it’s not sustainable. Building a business that endures decades, not just a few years, is a marathon. Seeking sustenance outside of work isn’t a luxury; it’s a necessity.
And, to be clear, it’s a two-way street: By giving back and expressing my passions, I’m able to bring new insights, skills and energy to the business.
Environmental conservation, for example, has given me a new lens on work literally and figuratively. To raise awareness about threats in places like the Amazon, I decided to start making films, with zero knowledge of the industry. Producing documentaries such as the Emmy Award–winning Wildcat, about threatened ocelots in the Amazon, turned out to be a masterclass in beginner’s mindset, adaptability and humility.
All of this enriched me as a leader. Besides making me more confident by testing my abilities in a new arena, it showed me the power of thinking big and how much a small group of determined people could accomplish. No matter what your passion is outside of work, finding an outlet can be equally energizing and restorative.
For any founder, staying in business for 20 years is a long time. There’s no magic formula for going the distance, especially as the pace of change keeps quickening. But if I’ve learned anything on my two-decade journey from flip phone to AI, it’s that the fundamentals really don’t change. While tech trends come and go, the same basic principles that served me well as a founder back in 2005 still hold true in 2025 — and beyond.
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