5 CEOs That Turned Million Dollar Losses into Huge Wins For Their Company

The tale of the self-made millionaire is one that captures the imagination of the masses. Yet the story of "overnight success" almost never accurately demonstrates the struggles and losses encountered on the way.

As any entrepreneur will know, the path to success is never as smooth or as a glamorous as the movies depict. When faced with adversity and tough times, the following five millionaires didn't let failure hold them back - and instead came back stronger and more successful than ever.

1. Bill Bartmann

Bill Bartmann

This success-story-turned-failure turned back into success and resulted in riches much earlier than most. Bartmann became a millionaire thanks to his debt-collection firm, Commercial Financial Services (CFS). However, this debt-collector found himself in debt personally when his company was pulled out from under him by the US government and forced into bankruptcy due to alleged accounting fraud.

While Bill Bartmann was found to be innocent, his partner wasn’t and was convicted. Bartmann was left as a free man but a business failure. However, rather than letting that be the end of his career and his millions, he wrote a book that shared his story and secrets to earning the big bucks. Using this as a stepping stone, he eventually opened a second edition of his first firm. Appropriately named CFS II, this firm made over $10 million in a single year, and Bartmann learned from his mistakes – he keeps a closer eye on the on-goings of his employees now.

2. Steve Jobs

Steve Jobs

Being fired from any job can make you feel like a failure. But nothing really brands that title on you quite like building a wildly successful company from the ground up, then hiring the person who will eventually fire you from your own creation. Steve Jobs is the poster boy for being kicked to the bottom of the barrel but persevering anyways. Having created Apple at just 21, by 23, Jobs was already a multi-millionaire. It was only three years after Jobs hired a CEO for his company that the new CEO decided Jobs was his own weakest link – and fired him.

Twelve years later, while Jobs spent his time creating a second company, Apple found itself straying away from success and instead teetering on the edge of bankruptcy. The skills, inventions, and experience Jobs had gained in the interim made him a valuable asset; so much so that the company ended up hiring Jobs back in 1997. Within a year, the iMac was born and Microsoft had invested $150 million to get the company back on its feet. Jobs was CEO of his own creation again, and his technology is likely in your pocket right now.

3. Dorothy Hamill

Dorothy Hamill

For Dorothy Hamill, winning Olympic gold wasn’t enough. With her success in the Olympic rink, and her reputation as a wildly successful skater, her popularity and bank account alike grew thanks to her performances in prime-time TV specials. These alone netted Hamill over $1 million a year. However, she had little luck off the rink and she made some poor business decisions, including her investment in Ice Capades. She was also known to overspend her earnings on jewelry and other luxuries. All this led her to extreme debt and eventually bankruptcy.

Rather than taking that as the end of her career, Hamill used this publicity to her advantage. People remembered her face and her story, so she continued to star in NBC specials and toured skating circuits around the world. She also took her potential as a TV personality to the next level, hitting the big screen with the movie Blades of Glory, becoming a contestant on Dancing With the Stars, and eventually writing an autobiography that rose to the top of the charts. These efforts not only eliminated her debt, but grew her current net worth to $5 million.

4. Donald Trump

Donald Trump

Political opinions aside, it’s hard to deny that when it comes to losing it all and coming back more successful, Donald Trump has the trump card. When Trump Entertainment Resorts was at the top of its game, hundreds of casinos and hotels spanned the world – all with Trump’s name brandished on the front of them. These businesses not only raked in money for those who played their cards right, but also for the multi-millionaire chairman and CEO himself. Things seemed like smooth sailing until the recession of the 80s hit his business particularly hard, and the entire business went into bankruptcy.

It was a considerable failure, one that nearly dragged Trump down with it. He avoided personal bankruptcy by the skin of his teeth, and spent the next few years crawling out of personal debt while also trying to rebuild his business. He managed to overcome the colossal failure by not only getting his business back on its feet, but launching a successful career as a reality TV star that put him beyond the millionaire category and into the billionaire playground. From bankruptcy to President, Donald Trump never let the bumpy road hold him back.

5. Martha Stewart

Martha Stewart

Pop culture has poked a lot of fun at Martha Stewart, whose name has become synonymous with stardom turned jailbird; that’s proof enough that failure came for this TV personality fast and hard. The home and fashion authority for most, Martha Stewart was at the height of her career with a range of cookbooks, magazines, and TV shows to her name. With her magazine, Martha Stewart Living, selling like hotcakes, she was rolling in both money and success.

That is until Stewart received five months in prison for lying to investigators about insider trading. That very well could have ended her career, as many speculated it would, since greater success stories had gone down in flames for less. However, Stewart didn’t miss a beat and immediately revamped her TV show to draw in more attention, unveiled new home furnishings and interior paint lines, and released a book that rose high in the charts. With a current net worth of $300 million, her failure became merely a bump in the road.

A huge part of taking the leap and becoming a full-time entrepreneur is about having the faith, passion and commitment to proceed despite perceived obstacles. As our five millionaire failure survives show, there's really nothing you can't bounce back from.

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