Leadership Under 100

Most leaders believe that scaling a team is a linear path to success. Ian Kraskoff learned the hard way that it’s often a trap. In this episode, Ian Kraskoff (former leader at Uber and Loft ) shares the raw, unfiltered story of building a team to 60 people, watching it nearly collapse, and the "hellish" process of scaling back down to 15 to save the company. We dive deep into why "throwing people...

Bernardo Riveros co-founded ILAC—one of Canada's most successful English language schools—growing it from three small classrooms and a simple brochure into an institution welcoming thousands of international students every year. What started as an immigrant's dream in Toronto became a thriving business empire. Then, at its peak, he walked away. In this raw and honest conversation, Bernardo shares...

How does a 22-year-old from a small town in Brazil go from factory work to building and scaling a fintech company to over 100 people—and getting it acquired by one of Brazil's largest enterprises? In this powerful conversation, Mike Allan shares his unfiltered journey: starting with zero tech background, landing an innovation grant that forced him to incorporate his first company, pivoting from ha...

In this breakdown episode, I distill my conversation with leadership consultant Cameron McDonald into three practical lessons for teams under 100. We cover how to define leadership in a way you can actually use, why training values matter just as much as training tasks, and how simple one-liners shape culture more than long documents ever will. If you lead a small team and want clarity, consistenc...

How do you create and protect culture as your team grows? In this episode of Leadership Liftoff, I’m joined by Cam McDonald, leadership coach and former leader of a 100-person staff at a Leadership College, to talk about what founders need to know as they move from doing everything themselves to leading people. We unpack what leadership really is, why culture can’t just live on a wall, and how sma...

In this breakdown episode of Leadership Liftoff , we'll talk about three leadership lessons for teams under 100 drawn from a recent conversation with Luiz, one of the co-founders of the GigU App. This episode explores how rituals shape culture , why fun makes leadership stick , and how empathy creates responsibility inside growing teams. If you’re leading a small, scaling team and want leadership...

As teams grow, many founders and leaders unknowingly become the bottleneck—every decision, hire, and conversation flows through them. In this episode, Luiz Neves, co-founder of GigU, will share: Why founders and leaders often become the biggest constraint to scale How to move from “everyone follows the ball” to clear ownership and trust What empowered leadership actually looks like in teams under...

Welcome to Episode Zero of Leadership Lift Off. If you're finding this podcast and want to know what it's about, start here.