As a postal letter-carrier, my father-in-law knew years in advance the exact date he would retire. He also knew that retirement wouldn't suit him.

So, a few years before his scheduled quitting time, he bought a defunct horse farm near his house. He figured people in his area would pay good money to board their horses and take riding lessons. He was sure he couldn't lose. He managed to blow his life savings on that disaster, plus far more money that he had borrowed. 

Then he bought an electric train, selling rides at the local mall on weekends and evenings. He didn't lose any money on it week to week, but he really didn't make any, either. It just wasn’t worth his time.

Finally, the week of his retirement, he met an older man who wanted to get off of a high-end stump grinder he owned. The fellow was "a good Christian guy," my trusting father-in-law claimed, as he always did about pretty much everyone he met. The man wanted just $50,000 for the stump grinder, "a steal."

When he told me about it, I felt like Jack's mom when she learned he had traded the family cow for some beans.

 Could he be this naïve? "You're not going to do it, are you? Are you really thinking about buying this guy's stump grinder?" I asked. 

"I already did," he said. 

I know a thing or two about losing everything and then, in desperation, clinging to the first hope that comes along. What I didn't know anything about was the stump grinding business, and neither did my father-in-law. Buying the machine, which he didn't even know how to operate, was a ridiculous gamble born of panic. His retirement loomed ahead like an unknown afterlife, and if someone had offered him a bull-milking business, he would have bought it. 

I knew my father-in-law was overly anxious to get his next chapter started, and he was probably running ahead of God. And I told him that. 

He ignored me, of course. Desperate people won't listen to reason.

A few years have passed, and a lesson has been learned.

 The stump grinding business was a huge win. My father-in-law will do over $2M in sales this year with healthy margins. He has two work crews and a pole barn full of stump grinders and bucket trucks. He's happier than he's ever been, and certainly more prosperous. The freedom he enjoys as an entrepreneur beats anything he experienced as a wage slave for the post office.

1 Don't listen to your son-in-law. He's not God. If you only start the business all your friends think will work, you'll never start anything. And if your friends do all agree your business idea is a winner, it won't keep you from failing. Unless they all want to become paying customers.

2. Be willing to spend some money. It turns out that landscapers are often cash-poor. Their basic equipment - mowers and trailers - is inexpensive, which makes for a lower barrier to entry, too much competition, and low margins. Many landscapers don't have the capital or the credit to buy their own stump grinders. But stumps have got to come out. Landscapers will often sub that work out to guys with grinders, like my father-in-law. The $50k equipment cost creates a barrier to entry for the stump grinding business, creating higher margins. If a business requires no investment, it generally means there will be too much competition.

Better businesses will require some capital, so don't be afraid to spend money to get started. "It takes money to make money," as they say.

3. Start small. Fifty grand is a lot of money, but it's not that much. Buying the horse farm was a mistake my father-in-law couldn't financially recover from. It took him years to dig out. The mall train cost him just $35k to buy. It was a dead-end, but not a disaster. In fact, he eventually he sold it for a small profit. Burning $50k on the stump grinder was survivable if it had been a mistake. Fortunately for him, it was far from a mistake.

4. “Start a business doing something you love doing” probably isn’t genius advice. Nobody loves grinding stumps. Stumps just need grinding. Most businesses are like that. “I want to grow up to be a professional stump grinder,” said no kid, ever. The market’s response to your idea is far more important than your enjoyment of the work involved. In fact, the market response is the only thing that matters, because without it, you won’t even have a business. What if turning your hobby into a business is something all the other people who love your hobby are already doing? Or what if customers don’t care that you love doing it?

5. Reinvention is naturally born of desperation. Xerox invented a ton of great products - the digital printer, the mouse, the graphic user interface, and the local area network - but did not go to market with any of them. Why not? They didn't have to. They were riding the dominance of their office copier business and didn't need to reinvent themselves. The companies that took Xerox's inventions to market are worth trillions; Xerox is almost worthless in comparison. The crisis you may be facing - a layoff, an impending retirement, a financial problem - is likely to be the genesis of your own reinvention. That doesn't make the nightmare you may be living any easier to handle, but don't be surprised if you look back at your current disaster as the start of a great new season. In life, there is no boom without a bust.

So should you start a stump grinding business? Don’t ask me. I’m not a paying customer. If I had a stump to grind, my father-in-law would take care of it. Instead, ask the market. Its verdict is the only one that matters.