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Off The Wall

Jun 28, 2023

Looking to grow your business’ value, maximize your exit results, and ensure financial freedom, even during a recession? To learn how, tune in to this episode! This is Part 3 of our series, Business Exit Planning is a Team Sport.

In this episode, hosts David Armstrong and Jessica Gibbs wrap up their three-part discussion with Greg Maddox of Cultivate Advisors by discussing how to maximize your business value and your exit results, all while prioritizing business freedom, financial freedom, and personal freedom.

Doubling down on the importance of hiring a wealth manager during exit planning, Greg talks about how to grow your business as an asset and diversify your income and wealth as a business owner. He then highlights what you should consider if you’re looking to maximize your exit options and sell your business during a recession. Finally, Greg addresses the 3 main problems business owners face in planning an exit and how to discern if an all-cash offer is right for you.

Greg is also offering a free resource to help evaluate the health and value of a business: Get Cultivate’s Business Health and Value Assessment here:

“Instead of chasing profit, if we focus on value first, revenue and profit come along for the ride. If you focus just on revenue and profit, you could probably make a lot of money, but whether or not you built an asset somebody else would pay you for, that’s less likely. So, I think it’s just a mental shift there.”   Greg Maddox


Episode Timeline/Key Highlights:

[00:22] Introducing Greg Maddox & the topic of today’s episode.

[01:51] Growing Your Business: The difference between multiplying value and adding revenue.

[03:44] How to multiply the value of your business.

[10:44] Separating Your Business from Your Personal Wealth: Ways to diversify income and wealth as a business owner.

[24:11] Maximizing your exit options during a recession: Evaluating buyers, deal structures, and future roles after exit.

[35:26] Is an all-cash offer worth it? How do you know if it’s enough?

[37:02] Greg’s final advice: Begin with the end in mind & Build a good exit team.

[42:12] How to connect with Greg.

Please see important podcast disclosure information at  

Resources Mentioned:

Listen to Part 1:

Listen to Part 2:

Learn more about Cultivate Advisors:

Business Health and Value Assessment (Free):

Listen to Best Practices for a Successful Business Exit with Kevin DeSanto:


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