SkillJa is connecting athletes with coaches while delivering financial tools tailored to gig workers.
Built by Toronto-based athletes, SkillJa was founded by Vince and Mike, who met while working part-time and quickly bonded over their shared love for sports and drive to build something meaningful. Their friendship deepened through countless training sessions and honest conversations, many of which eventually sparked the idea for SkillJa. Vince sees Mike as a mentor, someone who challenged him to grow and take bold steps, both personally and professionally. Together, they created SkillJa to solve a problem they knew first-hand: the difficulty of finding great coaches and the lack of income support for those offering their time and talent. The result is a platform they would use themselves, one designed to connect athletes with quality coaching while supporting gig coaches with the financial tools they need to thrive.
They were selected across Canada to be part of Fintech Cadence’s 2025 Innovate Financial Health Cohort (The IFH Lab), a virtual program dedicated to founders who are on a mission to help improve the financial health of Canadians and Canadian businesses. Today, we sit with both founders Vince and Mike to learn more about SkillJa, their personal stories and what keeps them motivated in their entrepreneurial journeys.
Tell us about your startup and what inspired you to start it.
SkillJa is the easiest way for athletes to find local sports coaches. Whether you’re picking up a new sport or trying to level up your skills, we make the search process simple and transparent. The idea came from our own frustration, both Mike and I struggled to find quality coaches. That experience showed us how outdated and confusing the process was, so we set out to fix it.
What drew you to entrepreneurship and what energizes you to pursue SkillJa even when things aren't going as planned?
Vince was drawn to entrepreneurship because he didn’t want to just be a small part of someone else’s vision. He wanted to build something of his own, something meaningful that solves real problems and gives others the opportunity to grow with it. For Mike, he was drawn to entrepreneurship by the constant challenge and the chance to create opportunity, not just for himself, but for others. He thrives in environments where he can build, lead, and help people unlock their potential.
What keeps us going is knowing that setbacks are part of the process, and that the process itself is the reward. Building a startup challenges us to grow, think creatively, and constantly adapt. Whether it’s learning from users, designing new features, or tackling unexpected problems, there’s always something meaningful to work on, and that’s what makes it worth it.
How do you interpret your success? What about your failures?
Vince: I see success as reaching the goals I set out to achieve. It’s a chance to acknowledge the work that went in, but also a prompt to set the next goal and keep moving forward.
Failure, on the other hand, isn’t the opposite of success, it’s part of it. When things don’t go as planned, it’s an opportunity to reflect, adapt, and keep fighting.
What inspires you when it comes to finding a solution to help the financial health of Canadians? And to follow, what unique financial health challenges or opportunities do you see happening in the Canadian market?
What inspires us is the opportunity to help Canadians build a brighter, more secure financial future. Through things such as; access, education, and smarter financial tools. A major challenge in Canada is the rise of unstable income from gig and freelance work. It makes budgeting, saving, and planning for taxes difficult. But it also presents a big opportunity, fintech tools that help people manage irregular earnings can make a real difference for the growing number of Canadians working outside traditional jobs.
One of the biggest opportunities in fintech is helping Canadians navigate an increasingly financialized world. From buy-now-pay-later options to micro-investments, nearly every purchase now has a financial layer.
At the same time, the rise of the gig economy and side hustles has created demand for smarter tools to manage irregular income, taxes, and business expenses. The challenge, and opportunity, is building solutions that are flexible, transparent, and truly useful to Canadians.
What's the best career advice you've ever received?
The best advice we’ve received? “Why be a small part of someone else’s machine when you can build your own?” and: “Only take advice from people you’d actually trade places with.” Simple, but it keeps us grounded and focused on charting our own path.
How does SkillJa help coaches and athletes convert new skills into tangible financial improvement?
SkillJa empowers coaches to monetize their expertise by creating a competitive marketplace where they can set their own pricing, schedules, and client base. As they build a strong reputation, they can increase their rates and income over time. This structure turns coaching into a viable, self-directed career path, one that can support more stable employment and potentially unlock access to credit or financial tools through consistent earnings on the platform.
What partnerships are essential to SkillJa’s model and what excites you about them?
Local sports businesses are key partners for us. Collaborations with gear shops, training facilities, and event organizers allow us to offer real-world perks, like discounts or exclusive access, things that boost user engagement and retention. What excites us most is the potential for mutual growth: we drive high-intent traffic to local businesses, and in return, they help elevate the overall SkillJa experience. These partnerships lay the foundation for co-branded events, sponsorships, and a stronger, more connected sports community.
For all the aspiring entrepreneurs out there, what advice would you give to someone who is thinking about starting their own startup? What book(s), podcast(s) or movie(s) do you highly recommend?
If you’re thinking about starting something, just start. You don’t need all the answers right away, what matters most is taking that first step and sticking with it.
You have the power to create real change, but it takes conviction. Not everyone will see your vision early on, so you’ll need to believe in it, even when it feels unreasonable. That belief, paired with persistence, is what carries you through.
As per the reccomendations:
- Founders (Podcast) – Great podcast where the host David Senra talks about different biographies that he’s read on some of his favourite founders.
- Can’t Hurt Me by David Goggins (Book) – A great book detailing the levels of mental fortitude that can be achieved with discipline
- The Mountain is You by Brianna West (Book) – A great book about the struggle with self sabotage and how to overcome it.
- Icarus by Brian Fogel – A film that starts with sport and uncovers something much bigger, just like our journey with SkillJa.
What are you most proud of?
We’re most proud of bringing SkillJa to life. It might sound cliche, but turning an idea into something real, something that helps people, has been one of the most rewarding parts of this journey.
Finally, what’s next for SkillJa?
We’re focused on growing SkillJa’s user base and hitting our post-launch revenue goals. We’re also working on building a stronger personal brand to connect more directly with our audience and share the journey as we grow.
Where to find SkillJa:
Register to our upcoming IFH Lab Showcase here to listen to Vince and Mike pitch – taking place online on July 31st.
