In this episode, we sit down with Steven Maxted to talk about what it really means to fail forward and how that concept has played out in both his career and his life. Steve shares the story of losing his job during a corporate merger and the surprising opportunities that followed once he allowed himself to embrace uncertainty. He talks about the mental rollercoaster of being laid off, the panic that followed, and why that moment ultimately became the push he needed to build something of his own.

We explore how resilience plays a key role in both entrepreneurship and endurance sports, two areas Steve is deeply committed to. He reflects on how marathon and triathlon training helps him stay grounded and build mental toughness that directly translates into his approach to business. Whether it’s getting through a brutal swim during a race or navigating a failed startup, Steve shares the tools and habits he uses to keep showing up, even when things don’t go to plan.

The conversation also covers his transition from corporate agriculture to starting multiple ventures under the Type A brand. We unpack how Steve’s mindset shifted as he began building a company that reflected both his identity and values. From launching a bike rental business to starting a podcast, Steve shares how each experiment—successful or not—taught him something that shaped the next move.

We also dig into the importance of instinct in spotting business opportunities. Steve shares how trusting his gut has helped him make high-impact decisions, like flying to Vegas on a few days' notice to meet a potential client. That choice led to lasting business relationships and validated his belief that being proactive and showing up matters more than having a perfect plan.

Later, we talk about data, reflection, and learning to zoom out. Steve discusses the importance of taking time each month to assess what’s working, what’s not, and how to pivot. He emphasizes how vital it is to check in with your own risk tolerance, ignore outside pressure, and trust your own judgment when you’re building something from scratch.

We wrap up the episode talking about what it means to grow something in a place like Winnipeg. Steve reflects on the strong sense of community that makes the city feel more like a big village. He shares how growing up there shaped his worldview, and how his brand continues to be proudly Canadian in its voice and values.

Whether you’re a new entrepreneur, a seasoned founder, or someone navigating a big life transition, this conversation offers an honest look at what it takes to build something meaningful and keep moving forward.

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