Escape From Corporate Prison Seems Like a Good Idea, Until You Get Into the Details

In most cases, the individual doesn't really want to be an entrepreneur; they are unhappy with their job and just want to fantasize about doing something different.

The process usually comes to a screeching halt because of this paradox: the business that fits the parameters of the escapee does not fit their parameters.

While expectations vary depending on their age and current income, the average target compensation I hear is around $300,000 per year.

How much a bank will finance obviously depends on the strength of the business and amount of collateral the buyer can offer.

Suddenly, the escapee realizes they will be investing a ton of their own cash yet the business will still not give them near the $300,000 compensation they need.

So when I get a question about buying a business, I reply “How much cash can you invest and what’s the least you and your family can live on for five years?”

In most cases, when confronted with the reality of investing a large amount of cash while having to adjust their personal lifestyle to make the numbers work, the escapee suddenly seems ok with their life inside the corporate prison.

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March 01, 2025

Escape From Corporate Prison Seems Like a Good Idea, Until You Get Into the Details

Jim Cumbee

“I’m tired of my corporate job at ______, I want to be an entrepreneur, be my own boss, how do I buy a business?” I hear this question about once a week, at least. The ensuing conversation often feels more like a counseling session than a business conversation. In most cases, the individual doesn't really want to be an entrepreneur; they are unhappy with their job and just want to fantasize about doing something different.

I know that sounds harsh, but the process to escape from corporate employment to business ownership is long and windy. The process usually comes to a screeching halt because of this paradox: the business that fits the parameters of the escapee does not fit their parameters.

Huh? Let me explain.

The escapee first tells me they want a business that will replace their current corporate compensation. They usually forget to include the value of their employer’s 401K match and health care cost, so once we’ve done all that math, the escapee now has their target compensation. While expectations vary depending on their age and current income, the average target compensation I hear is around $300,000 per year.

Then I hear, “OK, Jim, find me a business that has cash flow of $300,000.” Though every situation is different, as a general rule, a business with cash flow of $300,000 would sell today for $1.2 million (maybe more, maybe less -- but stay with me, I’m trying to make a point). Does the corporate escapee have $1.2 million in his/her bank account? Usually not, so they need to get bank financing to support the deal. How much a bank will finance obviously depends on the strength of the business and amount of collateral the buyer can offer. Normally, a bank will loan slightly more than two times cash flow, or in this case around $700,000. The buyer, therefore, needs to bring around $500,000 cash to the closing table.

So assume the bank loans $700,000 on a seven-year term at a rate of 8%; that’s an annual payment of about $56,000. This means the owner’s actual cash flow will be approximately $240,000 per year. Suddenly, the escapee realizes they will be investing a ton of their own cash yet the business will still not give them near the $300,000 compensation they need. So instead of saying “My family and I can make this work, we’ll tighten our belts,” they will usually say, “this business doesn’t work for me.”

Therein lies the paradox, they say they want a “good opportunity” but when they see it, they don’t want it because the opportunity doesn't meet their current income expectations. So when I get a question about buying a business, I reply “How much cash can you invest and what’s the least you and your family can live on for five years?”

In most cases, when confronted with the reality of investing a large amount of cash while having to adjust their personal lifestyle to make the numbers work, the escapee suddenly seems ok with their life inside the corporate prison.

 

Meet Jim

Tennessee Valley Group

Jim is an attorney (non-resident status with the Missouri Bar) and though he no longer practices law, he has read and negotiated enough legal documents to fill a cargo tanker. He has an MBA from Harvard Business School and knows how Wall Street and private equity operates. Jim is a Tennessee Supreme Court Rule 31 listed general civil mediator with tons of experience helping business owners (large and small) work through sensitive problems to achieve winning results. He is the author of "Home Run, A Pro's Guide to Selling Your Business, Seven Principles to Make Your Company Irresistible."

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