Building Better Business Exits, with Jessica Craig

Are you preparing your clients for a successful exit, or just responding when they call, desperate to sell? What vital steps might you be overlooking that could turn “the deal that got away” into your next big win?

Too often, business brokers and advisors find themselves on the back foot, reacting to urgent sellers rather than guiding owners through a strategic exit process years in advance. This episode challenges you to shift from transactional thinking toward building value, clarity, and trust with business owners, transforming disappointment into opportunity and long-term success.

Guest Jessica Craig, founder of Exit Welle and President of IBBA Canada, shares her journey from corporate banking to entrepreneurship, revealing why “education-first” exit planning is critical in a market where most business owners aren’t thinking about their eventual transition until it’s too late. Jessica dives deep into common obstacles like owner dependence, messy financials, and the impact of market realities on valuation. She opens up about lessons learned from deals that fell apart and offers actionable strategies for pipeline growth, including referral networks, educational outreach, and the power of consistent marketing. The episode delivers practical advice on approaching tough conversations, leveraging Canadian-specific exit structures, and balancing long-game efforts with direct outreach.

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