Senior Business Advisor

Chicago, IL

Greg Maddox

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Expertise Areas

  • Financials

  • Leadership

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.

Throughout his time building companies and advising leaders, Greg understands that the fundamentals of good business do not change. The same pillars that build a strong organization are the ones that are critical for success when transitioning or exiting from a company.

Many people who come to Greg feel like they own a job, not a business. But, with his help, his clients start to dream bigger and regain excitement in their work. Greg works with his clients to help them understand how valuable their businesses can be and see the real possibilities in their businesses and lives.

Greg Maddox
Because of Greg’s experience running a financial services company, he is uniquely qualified to collaborate with tax, legal, and wealth management professionals on the advanced planning successful entrepreneurs require. So often, entrepreneurs have all of their financial eggs in the “Business Basket” and are not fully protected from a tax reduction, asset protection, wealth transfer, and (eventual) exit perspective. Greg’s comprehensive roadmaps address all of these issues and accelerate the enterprise value of the business. Greg helps his clients think through these issues so nothing falls through the cracks.
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Greg provides his clients with fresh insights and enables them to take back control of their business. Too often, they feel chained to their business and sacrifice their families and outside lives to make their companies work. Greg helps them shift their perspective to create a business that can run without them, build multiple income streams, and have rich and meaningful personal lives.

Some of the clients that come to Greg have sold businesses or worked with consultants in the past but still struggle to create the life and business they want. His assessments, insights, and advice make exits more profitable and less stressful for even his experienced clients.

In 2021 alone, Greg helped seven owners prepare for and successfully sell their businesses despite the effects of the pandemic on the economy. It accounted for seven families who now have a level of financial security they never knew before that allows them to find new ways to create value and impact their communities.

Since joining Cultivate Advisors in 2018, Greg’s client promoter scores have been among the highest in the entire company because of the results he provides.

Greg is a proud veteran of the 101st Airborne Division. Being a part of the Army made his dad really proud, but when he walked away from a chance to attend West Point, his father jumped on an airplane to talk him out of that decision. After spending the weekend together, he understood why Greg was passing up on that amazing opportunity. It’s an interesting story—ask him about it.

Because of Greg’s experience running a financial services company, he is uniquely qualified to collaborate with tax, legal, and wealth management professionals on the advanced planning successful entrepreneurs require. So often, entrepreneurs have all of their financial eggs in the “Business Basket” and are not fully protected from a tax reduction, asset protection, wealth transfer, and (eventual) exit perspective. Greg’s comprehensive roadmaps address all of these issues and accelerate the enterprise value of the business. Greg helps his clients think through these issues so nothing falls through the cracks.Because of Greg’s experience running a financial services company, he is uniquely qualified to collaborate with tax, legal, and wealth management professionals on the advanced planning successful entrepreneurs require. So often, entrepreneurs have all of their financial eggs in the “Business Basket” and are not fully protected from a tax reduction, asset protection, wealth transfer, and (eventual) exit perspective. Greg’s comprehensive roadmaps address all of these issues and accelerate the enterprise value of the business. Greg helps his clients think through these issues so nothing falls through the cracks.

Posts by Greg Maddox

How to Value a Small Business
Book

Financials

Productivity

How to Value a Small Business

July 27, 2022

13 minRead

ByGreg Maddox