Op-Ed: Leadership lessons from the trenches

When we started Resly five years ago, I had no experience running a business or managing large teams. I didn’t have a grand master plan or decades of leadership experience under my belt. All I knew was the type of boss—and the kind of business—I didn’t want to be. But one thing was certain: we had a killer product.

Fast forward to today, and Resly has grown into a company making a huge impact in the hospitality industry. Along the way, I’ve made plenty of mistakes, learned from trial and error, and discovered what really matters when building a business and leading a team.

This article was originally published in the latest edition of Resort News. Read it HERE.

As we hit this milestone birthday, I’ve been reflecting on some of the biggest lessons I’ve learned—things I wish I’d known when I started—and insights that might help other business owners and managers navigating their own challenges.

Here are five key lessons from the past five years in the trenches.

Lesson 1: The bigger the company, the harder alignment becomes—vision is everything

When Resly was starting out, alignment was easy. Everyone knew what we were building, why we were building it, and how we wanted to get there. But as we grew, I quickly realised that the bigger the company gets, the harder it is to keep everyone moving in the same direction.

It’s not enough to have a vision—you need to constantly reinforce it. It must be more than a statement on a slide deck; it has to be something people see, hear, and feel every day in the decisions we make, the way we work, and how we interact with customers.

That’s why we recently took the time to redefine our vision and ensure everything we do—our goals, strategies, and even how we measure success—is aligned with it. It was a necessary reset, and it’s already made a huge difference in how we operate as a team.

For anyone leading a growing business, my biggest takeaway is this: alignment doesn’t happen naturally—it requires effort and commitment. If your team isn’t clear on the bigger picture, or if they don’t see how their work contributes to it, motivation and momentum start to fade. Repeating the vision, embedding it in decision-making, and making sure it’s more than just words is what keeps everyone moving in the same direction.

Lesson 2: People truly are your greatest asset

It’s a phrase that gets thrown around all the time—“people are your greatest asset.” But when you’re scaling a business, it’s something you must actively prioritise. Growth brings change, and change isn’t always easy. Not everyone will adapt at the same pace, and not every decision will be perfect. But managing with compassion and treating people genuinely makes all the difference.

One of the simplest yet most powerful things you can do as a leader is to tell people when they’re doing a great job. Recognition—whether it’s a quick message, a public shout-out, or celebrating a company milestone—helps people feel valued and motivated. At the same time, creating a culture where feedback flows both ways ensure your team feels heard and engaged. If feedback is encouraged, actioned, and seen as a tool for growth rather than criticism, it builds trust and accountability.

As Resly has grown, we’ve made it a priority to celebrate team wins, not just individual achievements. When the company succeeds, it’s because of everyone’s effort, and it’s important to acknowledge that. Prioritising face time, team activities, and moments to connect—whether through structured events or casual catch-ups—keeps the culture strong, even as we scale.

At the end of the day, a business doesn’t grow unless its people do. Investing in them isn’t just the right thing to do—it’s essential for long-term success.

Lesson 3: Adaptability is the real superpower

Coming into a well-established industry as a new business was always going to be a challenge. Competitors had been around for decades, and we were the fresh-faced newcomers. At one point, a competitor tried to discredit us by calling Resly a “fly-by-night” operator. Instead of going on the defensive and trying to prove we belonged, we leaned into being new.

We embraced our fresh perspective, our willingness to challenge the status quo, and our ability to move fast. That mindset has shaped who we are today.

Adaptability has been one of our greatest strengths. While larger companies are often weighed down by legacy systems and slow decision-making, we’ve been able to pivot quickly, experiment, and evolve. Whether it’s responding to industry shifts, customer feedback, or new regulations, being agile has helped us stay ahead. It’s not about chasing trends—it’s about recognising when change is needed and having the courage to act on it.

For any leader, uncertainty is inevitable. But rather than fearing it, embracing change as an opportunity rather than a threat is what separates businesses that thrive from those that fade. The ability to stay open-minded, challenge old ways of thinking, and move with confidence—rather than hesitation—is a real superpower. And in an industry that’s constantly evolving, it’s what keeps us ahead of the curve.

Lesson 4: You can’t do it all—and that’s okay

In the early days of Resly, Rico and I were the go-to for everything—sales, support, product decisions, operations. If something needed doing, one of us took it on. At the time, it felt like the only way to keep things moving. But we learned the hard way that without boundaries, burnout is inevitable. No matter how passionate or driven you are, you simply can’t do it all.

One of the biggest shifts I had to make as a leader was learning to delegate and trust my team. Letting go isn’t easy, but it’s necessary—not just for your own sanity, but for the growth of the business.

When you empower the right people and give them ownership, things don’t just get done—they often get done better. And it frees you up to focus on where you add the most value.

For business owners struggling to let go, start small. Hand off tasks that don’t require your direct involvement. Set clear expectations, but resist the urge to micromanage. And most importantly, build a team you genuinely trust. The sooner you realise the business doesn’t rely on you alone, the sooner you’ll create something that can scale, evolve, and thrive—without running yourself into the ground.

Lesson 5: Don’t be afraid to make mistakes (just don’t make the same one twice)

Mistakes in business are inevitable. No matter how experienced you are or how well you plan, you’re going to get things wrong. The key is not fearing mistakes but learning from them.

One of the more painful lessons I learned was when we hired an HR consultancy. They had a sleek sales pitch and seemed like the perfect fit. We didn’t do our due diligence, didn’t ask the hard questions, and didn’t even do a basic Google search. Given HR is one of the most important functions in a business—responsible for looking after your people—it’s shocking to think I made this decision with so little care.

That mistake taught me two things: first, due diligence matters, no matter how good something looks on the surface. And second, owning mistakes and moving forward is more important than trying to avoid them altogether.

Keep learning, keep growing

Five years in, I can confidently say that running a business is never about having all the answers—it’s about staying adaptable, learning from every challenge, and surrounding yourself with the right people.

Of course, none of this would have been possible without the incredible people who have been part of the journey. A huge thank you to Rico, my co-founder and partner, for being there every step of the way. To our fabulous clients, who continue to trust us and inspire us to do better every day. And to our beyond amazing team—Resly wouldn’t be Resly without you.

Stay true to your purpose, back your people, and keep pushing forward—you’ll build something that lasts. Here’s to the next five years and beyond!

In 2025, Resort News, the monthly print magazine for the management rights industry, is celebrating its 30th anniversary!