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Off The Wall

Jun 21, 2023

If you want to keep yourself, your family, and your assets safe throughout your business exit, tune in to this episode. This is Part 2 of our series, Business Exit Planning is a Team Sport.  

Tune in as hosts David Armstrong and Jessica Gibbs continue their discussion with Greg Maddox of Cultivate Advisors. In this episode, they’re talking about the importance of prioritizing your personal wealth throughout a business exit (separate from business wealth) and why you need an experienced wealth advisor on your advisory team while planning your exit. Greg also teaches you how to identify, address, and manage risks in your business so you can have a smoother exit and post-exit experience. He also breaks down the tax strategies and tips you can use to save money now and set yourself up for success in the future. 

That’s what the freedom point is about, it’s about how do I sustain my life without my business, or make working in the business optional? That’s the freedom that we would eventually have.” 

  Greg Maddox 

Episode Timeline/Key Highlights: 

[00:44] Introducing Greg Maddox & the topic of today’s episode. 

[01:35] Why you should consult a wealth advisor during business exit planning.  

[07:18] What’s your freedom point? 

[13:03] Why do entrepreneurs need a wealth advisor that has experience with business ownership? 

[17:01] Separating your personal wealth from your business wealth. 

[24:36] How to identify the risks in your business. 

[28:46] How to address/manage risks in your organization. 

[36:23] The importance of business continuity planning. 

[41:05] Tax strategies and tips for business owners who want to exit. 

[47:18] Stay tuned for Part 3! 


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About Greg Maddox: 

Greg is a Senior Business & Exit Advisor at Cultivate Advisors in Chicago, IL. As a serial entrepreneur, Greg Maddox provides his clients with the same long-term planning he used to make his own businesses successful. From owning a mortgage company that went through the housing bubble crisis to a financial services company during the ’08 financial crash, Greg steered his businesses with clear foresight no matter the turbulent environment. Now, as an advisor, Greg brings exit planning into the present and helps his clients live their Ultimate ExitLifestyle—even if they never sell! And for those ready to move on to the next chapter in their lives, he ensures they are mentally and financially prepared to fund their next step and live an amazing life. 


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About “Off the Wall”: 

OFF THE WALL is a podcast for business professionals and high-net-worth investors who want to build wealth with purpose. A little bit Wall Street, a little bit off-the-wall; it's your go-to for straightforward, unfiltered wealth advice on topics that founders, business owners, and executives care about. Learn more about our hosts, Dave and Jessica on our website at