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The Hollow Place After an Exit with Brian Roeder
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.
Connect with Brian Roeder:
https://beeoak.com
[email protected]
Take the Exit Readiness Assessment:
https://www.exittoexcellence.com/era
Schedule a conversation with Jerome:
https://calendly.com/yournext/30-minute-1-on-1
Learn more about your ad choices. Visit megaphone.fm/adchoices
View all episodes
By Jerome Myers - Advisor to exiting founders
5
6464 ratings
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.
Connect with Brian Roeder:
https://beeoak.com
[email protected]
Take the Exit Readiness Assessment:
https://www.exittoexcellence.com/era
Schedule a conversation with Jerome:
https://calendly.com/yournext/30-minute-1-on-1
Learn more about your ad choices. Visit megaphone.fm/adchoices