When Steve Belyea started BASE Engineering, he had little more than an idea and a single customer. Over the next three decades, he built the company into a global business serving customers in 28 countries, completed two successful exits, and learned some expensive lessons along the way.

Building a business often looks straightforward in hindsight. Growth milestones, new locations and successful exits tend to become the visible markers of progress. Justin John and Eric Velez-Chua know the view from the inside usually looks different.

Some industries force clarity. Energy is one of them. Cycles move quickly, capital is unforgiving and decisions have long consequences. For entrepreneurs operating in that environment, the margin for error is smaller and the feedback is immediate.

For many business owners, transition has traditionally been something left for later, tied to succession or a future moment when the timing felt right. That approach is shifting.

Some businesses are built in environments where conditions are predictable. Others are built where conditions are constantly shifting. For Geoff Gay, leading Athabasca Basin Development has meant operating in the latter. Northern geography, resource cycles and global forces all shape the outcome, often in ways that’re outside any single company’s control.

Leadership is often associated with control, decisiveness and having all the answers. Phil Jewell sees it differently. From leading soldiers early in his career to building leadership programs across North America, his perspective has been shaped by environments where clarity, trust and accountability aren’t optional.

Many business owners spend years waiting for the “right time” to make a major decision about their company. Whether that means investing further, bringing in partners or preparing for a sale, the instinct is often to wait for clearer market conditions. Christine Pound believes that moment rarely arrives.

For many prairie business owners, global instability can feel distant. Tariffs, geopolitical tensions, supply chain disruptions and social media activism can often seem like issues for multinational corporations, not local SMEs. Grant Kook sees it differently. As Founder, President, Chief Executive Officer, and Chair of Westcap Mgt. Ltd., and now Chair of BTF Saskatoon, Grant brings a broad perspective to prairie business.

Many owners spend years building a business, only to discover late in the process that deals don’t fall apart on price alone. They unravel on terms, trust and expectations that were never fully negotiated in the first place. That reality came through clearly in our conversation with William M. Donnellan, President and CEO of IRL Group of Companies.