Turning Passion into a Successful Business: Dean's Journey to Enrolmy
“Overnight success takes 15 years.” Dean Pendergrast, CEO at Enrolmy, smiles as he remembers his father reminding him of this when he was young. At the time, he didn’t quite understand it, but now, after nearly a few decades of hard work, setbacks, and successes, he sees the wisdom in those words. Success doesn’t just happen. It’s crafted, tested, refined, and pivoted, step by step, over time. And that’s the story behind Enrolmy, a journey built on hard work, goodwill, resilience, and a passion for making a difference.
Growing up, Dean was always drawn to helping and making a difference. He wasn’t the kind of kid to sit around with a game controller; instead, he spent his time gathering friends for projects, creating music, and finding innovative ways to bring people together. His passions revolved around creativity, problem-solving, and making an impact, not just for himself, but for those around him as well. This unique blend of connection, creativity, and a love for empowering others laid the foundation for what would eventually become Enrolmy.
When it came time to start Enrolmy, Dean being a parent himself, understood there was a real problem to solve. The platform was born from his desire to simplify the booking and enrolment process for children’s activity providers. But it was never just about the technology; it was about creating tools that Superpowered providers and parents. For Dean, it’s always been about enabling providers and parents to focus on what matters: the kids.
Dean’s vision for Enrolmy is deeply rooted in purpose.
“When I’m at the end,” he reflects, “I want to know I helped others grow. That’s success.”
And for him, that mission is what drives everything at Enrolmy. As Dean says,
“It’s the character that we inspire in others that we’ll carry with us.”
In the world of business, true fulfilment comes from knowing that what you do has a lasting, positive impact.
The Importance of Goodwill and Resilience
One of the core values Dean passionately advocates is the role of goodwill. This showcases that it’s not about being nice all the time, as being nice is often a cover for not asking the hard questions. Instead, it’s about creating an environment where people feel valued, tackle challenges honestly, and work toward the same goal above personal or political agendas.
“Goodwill is our core intention. It drives our activity for the good of all, our customers, each other and the good of the company.”
And that’s a principle that’s guided Enrolmy since day one.
Building a team with this mindset is essential. Dean credits his co-founders, Mike and Andrew, for helping to bring this vision to life. Their strengths balance each other perfectly, creating a team that isn’t afraid to challenge each other when necessary.
“We’re friends in business,” Dean says, “because we’re not afraid to call each other out, and the Lord knows, there’s been plenty of times that I’ve needed to be challenged, that’s for sure!”
This is a valuable lesson for anyone starting a business. It’s not about having a team that agrees on everything. It’s about finding people who share the vision and are committed to making it a reality, even when things get tough.
Seasons of Growth and Consolidation
Dean focuses on the importance of knowing what season your business is in. Enrolmy has been through its own cycles of growth and consolidation, each phase shaping Dean’s leadership and approach, teaching him to adapt, refine strategies, and recognise when to push forward and when to consolidate, ultimately contributing to him becoming a more resilient and thoughtful entrepreneur.
These seasons have brought their own challenges and valuable lessons. As the company moved into new markets, like the UK, Dean felt that the pieces were finally falling into place, creating the opportunity that they had been preparing for. He looks forward to the journey ahead, stating,
“We’re on the very cusp of what Enrolmy could be,”
For entrepreneurs, recognising the phases of growth and consolidation is crucial. There are times to push for expansion and times to refine, recalibrate, and prepare for the next big leap. Knowing where your business is on this journey helps you make the right decisions and use your resources wisely.
Building a Network of Support and Accountability
Dean has leaned on a strong network of mentors and advisors throughout his entrepreneurial journey. He compares it to a choir, where each person contributes their unique voice, making the harmony even richer. Having people who challenge you, encourage you, and ask the hard questions is invaluable.
“You can be successful alone,” he says, “but success with others is more rewarding.”
Dean believes entrepreneurs often feel like they need to go it alone, but building a solid support network can make the journey more fulfilling and sustainable. It’s likely to be a long road, so seek out people who will cheer you on and push you to achieve your maximum capability.
The Road Ahead: A Call to Action for Future Entrepreneurs
As Enrolmy looks ahead, Dean is filled with excitement for what’s next. With new acquisitions on the horizon and rapid expansion underway, the company is on track for an exciting period of growth and success. Yet, despite all the achievements, Dean remains grounded in his core values of goodwill, resilience, and purpose.
Dean’s journey serves as a testament to the power of patience, hard work, and a clear vision.
“Success isn’t an accident,” he says. “It’s the result of using your talents wisely and working together.”
So, whether you're starting a new business or looking to grow your existing one, remember this: stay committed, build a trustworthy team, and always work with a purpose. The road may be long, but as Dean says, it’s worth every step!
Dean is passionate about sharing his story and the lessons he's learned along the way. He’s available for speaking engagements and podcasts, offering valuable insights on entrepreneurship, growth and leadership. If you’re interested in having Dean speak at your next event, simply fill out this form to get in touch!
This blog is based on the podcast where host Tim Segedin sits down with Dean Pendergrast to discuss his inspiring journey from primary school teacher to the founder of Enrolmy.
If Dean’s journey has inspired you and you're ready to take your kids’ activity business to the next level, we’re here for you! That’s exactly what Enrolmy is all about; supporting entrepreneurs like you to succeed and make the next leap with ease. Let us handle the admin so you can focus on what really matters: growing your business and making an impact.
