The Hollow Place After an Exit with Brian Roeder
The Hollow Place After an Exit: Brian Roeder on Selling Barrel Oak Winery
YouTube Description
What happens after you sell the business, feel the weight lift, and realize the next chapter is not as clear as you thought?
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 most popular wineries, growing it into a thriving hospitality business, welcoming up to 1,500 guests on busy Saturdays, and ultimately selling the company in 2022.
But this conversation is not just about selling a winery.
It is about what the exit takes with it.
Brian opens up about building the business with his former wife, navigating the breakdown of that relationship, protecting investors, preserving the company, and making it to the other side without lawsuits or destruction.
Jerome calls this a double exit.
The business exit and the relationship exit happened in the same season. And while the transaction brought relief, it also forced Brian to confront deeper questions about identity, purpose, family, work, and what comes next.
Brian describes the minute after the wire hit as a physical release, like a load had been lifted from his shoulders. But relief did not answer every question.
After moving back to California for what was supposed to be a clear next chapter in the family business, Brian found himself facing another unexpected transition.
Who am I now?
That question became part of his path into business brokerage, exit planning, and helping other owners avoid the mistakes he had to learn through pain.
This episode is for founders, business owners, and advisors who understand that an exit is never just about the number.
A successful transaction can close the deal.
But an excellent exit helps protect the person on the other side of it.
In This Episode
We discuss:
How Brian built Barrel Oak Winery from raw land into a thriving Virginia winery
Why a winery is really several businesses operating at once
What Brian learned from selling without the right guidance
The emotional reality of a double exit
How divorce, investors, employees, property, and identity can collide during a sale
The physical relief Brian felt after the wire hit
Why relief is not the same as purpose
What happened when Brian’s planned next chapter did not unfold as expected
Why going from entrepreneur to employee can feel so disorienting
The difference between connectors and extractors
Why Brian now leads with heart when helping owners
Why founders need advisors who care about more than EBITDA
Featured Concepts
The Double Exit
When a business exit overlaps with another major life transition.
The Hollow Place
Brian’s phrase for the post-exit period where the founder can feel empty, disoriented, or unsure whether the best part of life is behind them.
The Founder’s Exit Paradox
The moment when a founder achieves the outcome they were chasing and still finds themselves asking deeper questions about purpose, meaning, and identity.
Connectors vs. Extractors
Brian’s distinction between people who genuinely seek connection and people who are primarily trying to extract value.
Take the Exit Readiness Assessment:
https://www.exittoexcellence.com/era
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https://calendly.com/yournext/30-minu...
Connect With Brian Roeder
Website: https://beeoak.com
Email: [email protected]