Exit Planning

Business lawyer Rachel Wasserman joins Jason to discuss the realities of selling to private equity. Listeners learn how PE segments differ in intentions and time horizons, why a buyer's motivation matters before entertaining a sale, and how a deal can reshape staff, culture, and operations long after closing.

Jason compares the two main ways to exit a business: a share sale versus an asset sale. This solo episode explains the tax and liability differences between the two structures, why sellers usually prefer one and buyers the other, and how the final structure and price are often settled through negotiation.

Jon Shell of Social Capital Partners introduces employee ownership trusts, a structure that lets an owner sell a business to employees through a trust. The discussion compares EOTs with ESOPs and co-operatives, reviews the UK's experience since 2014, and explains where Canada's own version stands.

Exit planning specialist Jeff Cullen of Basecamp4 joins the show to discuss successfully exiting a business. He explains why exit planning is largely just good business planning, how gap analysis shows owners what separates a 2x valuation multiple from a 4x, and how owners react when told their baby is not pretty.

Jason Watt shares a first-hand account of selling his family business, ups, downs, and unexpected turns included. Listeners will hear how working capital adjustments and shareholder loans caught him off guard, and why specialist lawyers and experienced advisors matter in a sale.

Kim Moody breaks down Bill C-208, the law aimed at easing intergenerational transfers of small businesses, family farms, and fishing corporations. Listeners will learn what the bill changed in the Income Tax Act, why its drafting raises concerns, and what may still need fixing.

Dane ZoBell of Felesky Flynn discusses succession and tax planning for the family farm. Topics include which assets can qualify for the capital gains deduction, why rising land values have outpaced that shelter, and how gifted property affects the next generation's tax options.

Transition coach Dave Sinclair joins Jason to explore the emotional side of selling a business. Learn why owners often feel lost after an exit, how defining an ideal life and breaking it into a day-to-day journey helps, and why a growth mindset makes major life shifts easier to navigate.

Jason talks with Peter Merrick, author of The King of Main Street, about mentorship and grooming the next generation of business leaders. The discussion covers what makes a true mentor, why an aging population makes succession pressing, and how owners can find life beyond working on and at their business.

Dr. Tom Deans, author of Every Family's Business, joins Jason to talk about exit planning when family succession is on the table. The conversation covers why a willing buyer matters as much as a willing seller, why a smooth transition rests on the owner rather than the children, and how treating kids like valued employees shapes long-term outcomes.