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.

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.

Some entrepreneurs plan every step before they take it. Others build the path as they go. Geoff Bell is one of the latter. From oil rigs in northern B.C. to multiple tech exits, his story proves that success rarely follows a straight line but persistence always pays off.

Every owner knows that transformation is hard. But few realize that hesitation, not competition, is what quietly erodes company value. That’s the insight Rocky Ozaki, Founder and CEO of The NoW of Work, shared when we spoke ahead of BTF Vancouver 2025.

Every founder dreams of building a business worth millions, few expect the emotional roller coaster that comes after they do. For Kevin Michaluk, better known as CrackBerry Kevin, the journey from a $15,000 bet to a $115 million exit was both exhilarating and disorienting.

For many business owners, selling a company is the most significant financial and emotional transaction of their life. Yet too often, preparation begins only when the decision to sell has already been made. Mike Milani, Executive Managing Director & Principal at Baker Tilly Capital, LLC and Chair of BTF SoCal 2025, has spent nearly four decades advising owners through M&A transactions.

Debby has advised countless executives through acquisitions, turnarounds, and restructuring. In every case, the first question is the same: do people believe what you say? “The leader needs to be trustworthy. Without that, no matter what you do, your organization’s not going to be successful because the people… they’re not going to believe your strategy.”

Every entrepreneur faces moments when survival feels uncertain. For Mike and his team at Manitoba Harvest, that moment lasted more than two years. The company was in negative equity (its liabilities outweighed its assets) and it was relying heavily on trade credit to keep operations alive.

Ari Pandes, Associate Professor of Finance and Associate Dean of Professional Graduate Programs at the Haskayne School of Business, University of Calgary, is sounding the alarm on a troubling trend in Canada’s economy: the steady decline of operating companies listed on public markets, and the broader failure to scale up domestic businesses.