Business Transition – Transition Talks

The Emotional Side of Selling Your Business (Ep. 10)

By Transition Talks | March 21, 2025

How do you plan for life after selling your business?

Join Josh Ackerman as he explores the emotional and psychological journey many business owners face after selling their enterprises.

This isn’t just about the numbers; it’s about understanding the push and pull factors that influence your decision to exit, from health changes and market shifts to personal aspirations like political involvement.

Josh explores different exit strategies, from outright sales to retaining partial ownership and consultancy roles, and illustrates the importance of maintaining a vibrant social circle and identity outside of work. With valuable insights into aligning your financial and personal goals, this episode is a must-listen for anyone considering a business transition.

Key discussion points include:

The push and pull factors affecting business exits [00:03:43]
Emotional readiness for life post-sale [00:08:43]
The importance of social connections beyond business [00:14:00]
Different types of business exit strategies [00:10:30]
Encouragement to think strategically about life’s next chapter [00:16:39]
And more!

Connect with Josh Ackerman:

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Inside Context Financial: Guiding Family Businesses Through Change (Ep. 2)

By Transition Talks | June 6, 2024

What makes Context Financial uniquely equipped to handle family business transitions?

In this episode of Transition Talks, Josh Ackerman talks about what makes Context Financial uniquely equipped to guide family businesses through significant transitions. He shares the company’s history, founded by his father in 2000, and emphasizes the importance of understanding client context. Josh explains the focus on helping family businesses navigate ownership transitions, whether to the next generation or external buyers. He also highlights the team’s dedication to building trust and understanding client goals from the first meeting.

Josh discusses:

The company origins of Context Financial
Context Financial’s focus on helping family businesses prepare for a transition, whether internal or external
Why Context Financial’s approach to understanding your business’s unique context can make all the difference
The importance of understanding client goals and maintaining trust
How clients’ first meeting with Context Financial is a no-pressure, exploratory conversation about your needs and our services
And more