One lunch changed Aaron Watson’s life. What followed was a rapid rise from senior accountant to CFO IQmetrix and several high-growth SaaS businesses.In this episode, Aaron breaks down the exact systems they used to expand into new verticals, evolve from SMB clients to enterprise carriers, manage capital with discipline, and operate multiple companies under one unified structure.If you're scaling a SaaS business, a founder running multiple entities, or a finance leader building a stronger operating model, this episode delivers practical, battle-tested insight.Chapters:00:00 Intro01:20 Aaron’s journey from accountant to CFO07:45 When the wireless market shifted13:10 Moving upstream to enterprise18:35 Launching new verticals24:50 How they run multi-entity P&Ls30:25 Capital allocation without VC38:40 Building shared ownership culture46:55 Aaron’s rapid-fire insightsWatch the full interview and subscribe for more conversations with the operators behind the world’s most resilient businesses.

What does it really take to lead in a world reshaped by AI, hybrid work, and constant change? Dessalen Wood has some answers – and they start with people. As Chief People Officer at Syntax, Dess is helping shape how leaders navigate the biggest shifts in today’s workplace: hybrid work, AI, and the evolving expectations of employees everywhere. Tune in for a refreshingly human perspective on the future of leadership.

Michael Edelman’s career has spanned chemistry labs, high-growth tech, billion-dollar licensing deals, and now leading a Canadian semiconductor materials company through rapid global expansion. In this episode, Michael shares how he’s built businesses at the intersection of science and strategy. From hiring people smarter than himself, to navigating high-stakes patent battles, to scaling Polar’s team and culture, Michael brings candid insights on leadership, resilience, and turning big ideas into thriving companies.

Brendan White’s path from Big 4 accounting to leading finance and ops at a high-growth fintech was shaped by curiousity, adaptability, and a willingness to take leaps. In this episode, Brendan sits down with Joe to talk about what it takes to succeed in founder-led, fast-moving environments. From building credibility in new industries, to scaling processes without losing agility, to how AI is changing the operator’s toolkit, Brendan shares practical lessons on leadership, trust, and asking the right questions.

Jimmy Tristovski’s journey from pursuing engineering to people analytics is anything but typical, and that’s what makes his perspective so interesting. In this episode, Jimmy breaks down how data, culture, and systems thinking come together to build high-performing teams. From scaling culture at The Score to rethinking capacity models at PolicyMe, he shares lessons on hiring, employee experience, and why role players often win over superstars.

Trish Saltys’ career is a masterclass in leadership through complexity. From stabilizing crisis-stage companies to scaling founder- and PE-led organizations, Trish has built a reputation as the go-to operator for high-stakes transformation. In this episode, she shares lessons from her journey, including how she’s led teams through chaos, built trust in turnaround environments, and learned to grow into roles that felt just beyond reach.

Rob Cherun’s journey from finance to entrepreneurship is a masterclass in scaling, leadership, and strategic growth. As the former CEO of Stealth Monitoring, he transformed a $5M company into a $150M industry leader. In this episode, Rob shares insights on search fund investing, building high-performing teams, and the key decisions that drive business success.

Alex Kaju’s journey from aspiring CFL athlete to behavioural scientist reveals how psychology shapes hiring, business, and everyday choices. Now an Assistant Professor at HEC Montréal, he explores how decision-making biases impact recruitment, corporate strategy, and consumer behaviour.

AI experts John Stroud and Jen Schellinck from AI Guides discuss how businesses can prepare for AI’s rapid evolution. They talk about the rise of AI "agents," the importance of in-house AI expertise, and how leaders can foster AI adoption strategically. With real-world examples and actionable insights, this is a must-listen for anyone looking to harness AI’s potential and stay ahead of the curve.

Cyriac Alappat, Principal @ Cross-Border Impact Ventures talks about his inspiring journey from public accounting to venture capital, sharing insights on on leveraging risks, resilience, and a global mindset to succeed in finance and venture capital.