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15: From Nearly Bankrupt to a $50M Acquisition with Brian Will
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Show Notes
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.
Tweetables
“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
Key Takeaways
✔️Creating and selling the very first health insurance call center.
✔️Why it’s so important to be able to roll with the punches and adapt as you go.
✔️From nearly bankrupt, to being acquired for $50M 18 months later.
✔️Why you will never be an effective entrepreneur if you don’t take care of yourself first.
✔️The story of Brian’s first $100k week as a consultant.
✔️Why everything should be taught at a 5th grade level when training your staff.
✔️Learn how prospects retain information. HINT: your sales team better find out what the “chicken” is!
✔️The personal filters that are subconsciously driving every decision you make—and why ego is your enemy when building a business.
✔️What is The Dropout Multi-Millionaire all about?
Full Transcript
Brian Will
“Brian Will is a serial entrepreneur and sales consultant with over 35 years of experience. He has built and exited six successful companies across four industries, including two major online health insurance businesses acquired by Silicon Valley venture firms—now among the largest platforms in the U.S.
Brian’s journey began with a landscaping business at age 20 and led to four major exits, followed by consulting roles with private and public companies in sales and management. Today, he owns a growing restaurant chain in Atlanta and splits his time between Georgia and Florida. A proud father and adventure-seeker, Brian is known for turning near-bankruptcy into multimillion-dollar success through grit and adaptability.”
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15: From Nearly Bankrupt to a $50M Acquisition with Brian Will
Episode 15
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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.
Tweetables
“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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