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15: From Nearly Bankrupt to a $50M Acquisition with Brian Will

Episode 15 . 51:15

Brian Will was on the verge of personal bankruptcy when his partner told him he would be investing another $66k into their insurance business. They had already dropped $500k into it and had made zero revenue since they started a year prior.

Almost ready to quit, Brian decided to hold on a little longer, and within 18 months their company was acquired for $50M.

Brian went on to become a serial entrepreneur. Over the past 35 years, he has created or co-created six very successful companies in four different industries, had four successful exits, and consulted on projects for both private and public companies in sales and management training. He also owns a growing chain of restaurants in the Atlanta area.

In this episode, you’ll hear about two online health insurance companies that Brian built from the ground up and eventually sold to venture capital firms.

He shares why most successful companies are made up of a progression of ideas that lead to greater success, the importance of being able to adapt as you go, and some simple tactics that your sales team can use to better connect with prospects.


“Sometimes you need to rely on other people’s experience, knowledge and ability. Take your ego out of it and listen to somebody who’s actually done this before. When I made that decision, my whole life changed.” – Brian Will

“You need to take care of yourself first because a nonfunctional YOU can’t be an effective CEO or entrepreneur. If your life is in such a wreck that you don’t know which way is up, your business is probably also a wreck.” – Brian Will

“If Tim Cook needs a board of directors to help him make decisions, what makes you think you can do it all by yourself?” – Brian Will

“Find somebody who is five or six steps ahead of you and take their advice.” – Brian Will


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