The Brilliance of Failure, In the Words of a Self-Made Billionaire E-commerce mogul Michael Rubin plays fast and hard and has lost a lot along the way. But to hear him tell it, that's exactly why he is winning now.

By Catherine Clifford

Opinions expressed by Entrepreneur contributors are their own.

Michael Rubin became friends with the lady who served his debt collection notices when he was in high school. That's because by the time he was 16, Rubin was $200,000 in the hole.

Being there -- being down that far, that early on in his career -- is exactly what he says made him the ever-hungry, ever-restless business man he is today. Rubin sits at the head of Kynetic, an umbrella company for three e-commerce businesses that collectively employ more than 2,000 people full-time and thousands of seasonal part-time employees.

Rubin's entrepreneurial career started early, and by the time he was 14, he had opened his own ski equipment retail store. At the end of a snowless ski season when Rubin was 16, Rubin was left with $200,000 worth of debt to vendors and not enough inventory to cover it, even if there were demand from snow-bound skiers.

"I was essentially bankrupt at the age of 16," says Rubin. "That almost near-death experience kind of built the next success for me in business."

Related: How Michael Rubin Went From Bankrupt to Billionaire

With the debt collector showing up daily, Rubin needed a clever out -- and fast. He realized that if his ski shop was unable to sell the ski gear, then neither were other nearby ski shop owners. Rubin came across $200,000 worth of ski equipment being auctioned off at a fire-sale price for a bit over $12,000.

The problem? Rubin didn't have $12,000.

His father refused to lend him money because he wanted Rubin to go to college, and he knew that there would be a smaller chance of that happening if his son had an existing business to run. Rubin went to a family neighbor and borrowed the cash. It came at a very steep price -- approximately $1,000 a week.

In going around his parents and taking the very expensive loan from his neighbor, Rubin was able to buy the ski inventory on clearance. He then turned around and sold the inventory on the wholesale market, which enabled to pay off his debts. This was a whole new business model for Rubin -- buying and selling closeouts -- and it worked.

By the time Rubin was in his 20s, he had built a closeout business that was generating more than $100 million a year in revenue.

Related: Self-Made Billionaire Michael Rubin: E-Commerce Is Rapidly Changing (Video)

Rubin learned the business model because he had to. He was pressed against the wall. That's how Rubin has learned most of what he knows about business.

Here are his best tips.

1. Fail without fear. "I am such a big believer in this. I could give you a long list of things I have done wrong," says Rubin. Of particular note was being more than $200,000 bankrupt at 16. "That was a big failure, by the way," he says.

Rubin says that he often hears from aspiring entrepreneurs about their great ideas, but they are consistently blocked by some variety of fear.

2. Learn from failure. In the same breath that Rubin encourages would-be entrepreneurs that failure is ok and good, he also says that you have to be able to learn from it to make it productive. To be able to fail forward, you need to learn from each mistake.

"I like to fail," he says. "I have had so many failures and each time I have failed, I have figured out how to grow."

3. Don't go it alone. If you are going to build a company, you have to bring on smart people to help you. Rubin, the ever sports aficionado, says it's all about having a solid team. "If you have a big idea and you go after it, you have to get the right team together," says Rubin.

4. Stay focused. Entrepreneurs are often easily excitable. But to build a great business, you must stay focused. "Many times I have gotten distracted," says Rubin. "That has hurt or impeded success." Rubin says that with his early sports gear business, GSI Commerce, he got distracted too easily. But with Kynetic, the business he currently leads, Rubin is "laser focused."

5. Love what you do. For Rubin, retirement is not on the horizon because he loves what he does. He always has loved building businesses, and that means the motivation comes easily. "Some kids are good at sports, some are good at school work. I just always loved business, from the time I was a little kid. It was always something that I really enjoyed," Rubin says.

Related: 10 Trends for 2014: We Seek Imperfect, Human Moments. With Our Smartphones at the Ready.

Catherine Clifford

Senior Entrepreneurship Writer at CNBC

Catherine Clifford is senior entrepreneurship writer at CNBC. She was formerly a senior writer at, the small business reporter at CNNMoney and an assistant in the New York bureau for CNN. Clifford attended Columbia University where she earned a bachelor's degree. She lives in Brooklyn, N.Y. You can follow her on Twitter at @CatClifford.

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