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. He believes leaders here must widen their lens. The global economy is more interconnected than ever and a single political decision thousands of miles away can ripple directly into a Saskatchewan company.

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. Speaking from decades of experience across construction, hospitality and real estate, William offered a buyer’s-eye view of what actually makes deals work and why so many fail unnecessarily.

For many Alberta business owners, the challenge right now isn’t opportunity. It’s uncertainty. Geopolitical pressures, shifting trade relationships, labour constraints, and rising operating costs are creating decisions that feel harder to time and riskier to make. As Todd Millar, President and CEO of TEC Canada and Chair of BTF Alberta 2026, put it, owners are dealing with forces that sit well beyond tariffs alone, including “on again, off again discussions with current political entities” that make long-term planning difficult.

When George Armoyan, Executive Chairman of G2S2 Capital, sat down with Christine Pound for a BTF keynote conversation, he spoke less about growth curves and more about judgment. It was less about timing exits and more about surviving cycles. From immigrating to Canada as a teenager to building one of the country’s largest private investment companies, George’s perspective has been shaped by volatility. Whether it was high interest rates and ailed bids or unpopular sectors and family expectations, his approach remained grounded, direct and unapologetically long term, which is exactly why it resonated with so many business owners in the room.

Some enduring businesses are built far from the usual centres of capital and attention. They take shape in environments where resources are constrained, execution matters and results speak louder than reputation. That perspective came through clearly during a conversation at BTF Winnipeg with Joshua Simair, Co-Founder and former CEO of SkipTheDishes. His experience offers a grounded counterpoint to many common startup narratives and resonates deeply with business owners thinking about growth, transition and long-term value creation.

Selling a business is often imagined as a finish line. In reality, it’s a mirror. That’s what Josh Hotsenpiller, serial entrepreneur and founder of multiple venture-backed companies, learned through years of scaling and selling. From the outside, his trajectory looks textbook: fast growth, strong valuations, multiple exits. But as he told us in his conversation with BTF, the process revealed something few founders expect, how far most businesses are from being truly acquirable. Now an Operating Partner at Stone Canyon, Josh helps other entrepreneurs prepare for that same moment of truth, turning “profitable” companies into acquirable ones. His advice is as honest as it is actionable.