Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies · Jason Swenk

#1 Overlooked Exit Strategy: Selling Your Agency to a Team Member with Natalie Henley | Ep #878

February 8, 2026·24 min·1 clip

Chuck told Natalie, "this company could be yours one day" before selling it to her.

Natalie Henley joins Jason Swank from the agency-owner side of the table. She runs a digital marketing agency headquartered in Denver, with a remote team spread across the U.S. The main topic is an overlooked exit: selling the agency to a team member. Jason keeps returning to the part most owners skip, which is how early planning changes both the value and the stress of the deal. Natalie is direct about the risk of waiting too long. Once an owner is already fried and pulling the rip cord, the thinking gets rushed and the value can take a hit. She argues that employee buyouts can be a very good outcome. They work better when the owner has enough patience to groom a successor before the exit becomes urgent. The conversation also draws a line between two very different reasons for leaving. If the owner just wants out of the day-to-day, someone else can be prepared to take that role over. If the owner is done with digital marketing altogether, that is a different decision. Natalie says some agency owners simply want a different business model and a different life. Jason and Natalie also talk about how punishing the agency model can be. It is a business that can push people to the edge if they do not actually like the work. The talk then gets into the mechanics of the buyout. Natalie explains that when Chuck came to her house, he had already called the bank Volume Nine uses and had an SBA loan priced out in advance. That kind of prep turns a frantic exit into something calmer and more workable. The episode keeps landing on the same lesson. Owners need to think about succession, money, and their next move before urgency takes over.

As heard by us

A practical look at selling an agency to someone already inside the business.

The episode takes up a familiar turning point for agency owners: when an employee-led exit starts to look like the right move. Natalie Henley and Jason Swenk keep the focus on timing, showing why a team-member buyout can work best before the business is already under strain, and…

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Why you'd press play

If you are thinking about an employee buyout, this gets practical fast.

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