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Off The Wall

Jun 12, 2023

Are you a founder/business owner looking to exit your business? Do you want to better understand the exit process and the types of advisors you need on your exit team? You’re in the right place. This is Part 1 of our series, Business Exit Planning is a Team Sport. 

In this discussion, our guest reframes exit planning in a whole new light, to illustrate how exit planning is just great business strategy. Listen in as hosts David Armstrong and Jessica Gibbs welcome Greg Maddox, a Senior Business & Exit Advisor at Cultivate Advisors, to talk about why you need to run your business with an exit in mind and the three key advisors you need by your side. 

You’ll also learn three common challenges business owners face and how exit planning can solve them. You’ll gain insights on how to figure out your “freedom point” in business, the exit plan action steps you should take while actively running your business, and how to build an exit team that will actually increase your ROI and make your exit process smoother and easier. 

We’re all going to exit at some point. Hopefully, it’s on our terms and timeline.” 

  Greg Maddox 

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Episode Timeline/Key Highlights: 

[00:41] Introducing Greg Maddox & the topic of today’s episode. 

[02:19] The difference between exit planning and leaving your business. 

[07:10] Why 75% of business owners regret selling their business. 

[11:36] The mindset shift you go through after exiting your business. 

[12:27] Why you need a business exit team & Types of advisors you need. 

[20:47] Why do you need a wealth manager for an exit, not just a financial advisor? 

[29:00] Why you need to run your business with an exit in mind. 

[36:09] Stay tuned for Part 2! 

Resources Mentioned: 

Learn more about Cultivate Advisors: 

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