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3 Surefire Ways for Successful Entrepreneurs to Lose It All Entrepreneurs rushing to reach the proverbial next level often end up broke instead.

By Howard S. Dvorkin Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.


More than two decades ago, I began creating businesses that help Americans get out of debt, from a credit counseling agency to a factoring firm. While many of these businesses focus on subprime clients or struggling small business owners, I've met many well-capitalized entrepreneurs with solid business plans and a fierce work ethic who, by the time I'm introduced to them, are on the brink of failure.

Sometimes they reach out to me themselves. Other times, my friends ask me to consult with these once-successful, now-struggling business creators. Almost always, I can distill their problem into three categories.

Related: How 10 Billionaires Faced Failure (Infographic)

1. Believing your own hype.

I admired a 29-year-old entrepreneur who began launching his own businesses as a teenager, when he opened a lawn-cutting service and hired his friends. When I met him he was a moderately successful owner of a handful of small companies that all related to landscaping and home repair.

In a few years, I told him, he'd be financially secure. That wasn't good enough for him. He'd been telling himself -- and worse, others -- that he'd be a millionaire by the time he was 30. So he made hasty and risky decisions based on ego rather than sound business judgment.

I see variations of this all the time: Entrepreneurs who have a personal timeline for success that doesn't mesh with the reality on the ground and in their books. I've met 40-year-olds who were adamant they'd retire at 50. Sadly, they tried to build up their companies too quickly, overexposed themselves and were left needing to work until well into their 70s.

I live in South Florida, where you really can't judge a book by its cover. Everyone in business, regardless of whether they are up to their necks in debt and have $5 in their savings account, puts on an image of success. Time and time again, I meet people who have the appearance of financial success, but later find out it's just a facade.

What about the 29-year-old? In his haste to become a millionaire by 30 he alienated his employees and clients until he almost lost his business. Thankfully, he was young enough to learn from his mistakes and recover. Now, a decade later, his net worth is over $1 million.

Related: 8 Traits Common to Millionaires Under 30

2. Surviving your midlife crisis.

I need to be vague with the details here, for reasons that will become clear.

An entrepreneur in his late 40s led and expanded a successful family business with his brothers and sisters. After years of hard work expanding the business, he went through a midlife crisis. He cheated on his wife, got another woman pregnant, got divorced, broke up with the pregnant woman, then ran into the arms of another woman for solace. She also happened to be an employee.

Now he's paying for three children by two women and his work has, unsurprisingly, suffered. His brothers and sisters are angry at him for destroying multiple relationships. They no longer trust him to lead the business, which has stagnated at precisely the moment when he needs more money.

You might think, Anyone can make these terrible decisions, not just an entrepreneur. However, I've seen entrepreneurs suffer midlife crises more extreme than other people. My theory: Entrepreneurs pour so much of themselves into their work when they're young, they struggle to pace themselves as they get older. They took risks in the past that paid off, so they think nothing of personal risks that could devastate the people around them.

Of course, this isn't every entrepreneur or even most of them. Unfortunately, though, it's some of them.

Related: Midlife: Time for a New Start, Not a Crisis

3. Believing you're a genius.

I can't count the entrepreneurs who have asked me to invest in their latest venture. More likely than not, I pass. This shocks them. "You've started many businesses," they tell me, "so why can't you see the opportunity here?"

Many times I do indeed see the opportunity, just not with them driving the bus. I simply don't trust them to make it profitable. The reason is simple: They've been successful in one business, but now they're overreaching. They want to venture into a field they know nothing about using someone else's money.

"But I made lots of money over here!" They protest to me. "Surely I can make a lot of money over there!"

I've made this mistake more than once in my life, but that's often what it takes to learn a lesson. I've seen so many friends lose their shirts when they became convinced they're geniuses about everything, forgetting that their original success resulted from their work ethic and specific knowledge of the needs of one industry.

This is number three on my list, but it's the number one way I've witnessed successful entrepreneurs become failures. Yet all three of these scenarios have one thing in common: They're all desperate acts of successful entrepreneurs who could have been gradually more successful simply by not doing anything crazy.

Sure, we all took risks to get where we are today, but at some point successful entrepreneurs must swap the excitement of risk-taking with the mundane matters of steady growth, efficient management and gradual improvement. Of course, many entrepreneurs -- including myself -- launch new ventures so we can once again take risks. However, those risks are measured. We never risk it all because now we have much more to lose.

Don't start thinking you have the Midas touch because you were successful at one business. One success doesn't mean that you are going to be successful at everything you touch. Before the recession I invested in a bunch of business opportunities and did quite well. When the recession hit I had at least 30 investments in various businesses. Half of them went bad and I took a beating. However, I was able to invest fresh cash into businesses that, from a timing perspective, were great opportunities coming out of the recession. That more than made up for any losses that we incurred from prior investment failures.

Lesson learned: Just because everything you touched turned to gold before doesn't necessarily mean everything you do will be successful in the future.

Howard S. Dvorkin

Entrepreneur, investor, personal finance advisor and author

Howard Dvorkin, CPA is the chairman of, an entrepreneur, personal finance adviser, and author. He focuses his endeavors in consumer finance, technology, media and real estate industries. Money cannot buy happiness, but going into debt always buys misery. That’s why I launched

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