What happens when the business exit is not the only exit happening?

In this episode of Your NEXT, Jerome Myers sits down with Brian Roeder, founder of Bee Oak Partners and Managing Agent for Transworld Business Advisors’ Monterey office.

Brian shares the story of building Barrel Oak Winery from raw land into one of Virginia’s busiest wineries, welcoming up to 1,500 guests on busy Saturdays, growing a committed team, raising more than $2 million through nonprofit events, and ultimately selling the business in 2022.

But this conversation is not just about selling a winery.

It is about navigating a double exit.

Brian built the business with his former wife, and as the marriage came apart, the business had to be protected, investors had to be considered, and the dream they had built had to be carefully unwound.

He describes the moment after the wire hit as a physical release, like a load had been lifted from his shoulders. But relief did not automatically create clarity.

After the sale, Brian moved back to California for what he thought would be his next chapter in the family business. When that path did not unfold as expected, he faced another transition and another question:

Who am I now?

In this episode, Jerome and Brian explore:

The emotional weight of selling a business

Why the team is often what founders miss most

How divorce, investors, employees, family, and identity can collide during an exit

Why relief is real, but not the same as purpose

What Brian calls “the hollow place” after success

The difference between connectors and extractors

Why the right advisor starts with the owner’s story, not just the numbers

How Brian now uses his experience to help other owners avoid the mistakes he had to learn the hard way

A successful transaction can close the deal.

An excellent exit protects the person on the other side of it.