To his coworkers at the Combined Insurance Company of America in Chicago, he was just Bob. A few months shy of his 24th birthday and newly married, Bob was ambitious, charming, and sincere—all qualities company president W. Clement Stone valued in his salesmen. To push high-volume, short-term disability insurance, customers needed to trust their words. Bob Knievel could look a man in the eyes and tell him that $3 worth of insurance was money well spent, and they'd believe him.

Years later, when Bob adopted the Evel Knievel persona and made breaking his bones a spectator sport, his former colleagues would stare at their televisions in amazement. There went Bob, clearing 10 or 14 or 20 cars on a motorcycle. There lies Bob, a heap of fractured limbs that needed to be scraped off the pavement like chewing gum.

In the span of just a few short years, the best insurance salesman in his assigned district had become the most famous daredevil in the world.

Getty Images

Born in Butte, Montana, in 1938, Robert Knievel stole his first motorcycle at the age of 13. Prone to delinquency and petty crime, he failed to get a high school diploma and instead entered the U.S. Army Reserves. By the time he was 19 years old, he was out of uniform and starting up a semi-pro hockey team, drawing crowds at local arenas and even playing Olympic hopefuls from the Czech Republic. (Knievel’s team lost 22-3.)

By 1960, any discernible skills beyond mediocre athleticism and amoral behavior weren’t quite ready to reveal themselves. Knievel struck upon the idea of becoming a merchant policeman in Butte, which was a fancy term for being a private security specialist. Knievel would approach businesses and promise he’d act as a kind of sentry, checking their locations for suspicious activity and thwarting any robbery or vandalism attempts.

What Knievel wouldn’t admit until much later was that he was frequently the perpetrator of that activity, breaking windows and robbing the registers of businesses that didn’t sign up for his services. It was his version of property insurance.

A few things conspired to redirect Knievel’s ambitions. He married Linda Bork in 1959, and the couple started a family. He also grew concerned that Butte authorities were close to catching up with his security monitoring scam. In the summer of 1962, Knievel decided to go straight and become a salesman for Combined Insurance.

The company’s district manager in Montana dispatched Knievel to Chicago, where he underwent a two-week training course in sales tactics endorsed by president W. Clement Stone. Stone had co-authored a book, Success Through a Positive Mental Attitude, and considered it his business gospel. The lessons were at the level of fortune cookies and free of cynicism (“Big doors swing on little hinges,” “Thinking will not overcome fear, but action will”) but Knievel never once rolled his eyes. He absorbed the strategies and hit the road back in his home state, prepared to sell the $3 policies and collect his 60 cents per signature.

Earning an honest living at that rate would require volume. So Knievel traveled to working-class towns and paid bars to allow him to set up an “office” in a booth, where he could catch the steady stream of farmers coming in for a drink. He stopped workers at a train repair station during lunch breaks, and preached the virtues of the payments Combined would offer in the event the insured had an accident. Sometimes he’d pass up the $3 and do barter trades, like when a rancher once offered to give him a lame horse.

If Knievel had a crowning moment in his gone-straight, suit-and-tie life, it was when he set a district record for the most policies sold in a single week. He had talked his way into a state mental hospital in Warm Springs, Montana, and sold coverage to the staff—and if company legend is to be believed, to many of the hospital's patients as well. Knievel logged 271 sign-ups that week.

For this, Knievel got an award and recognition; he was feted by company executives as an example of the can-do spirit their president endorsed. While he enjoyed the attention, what Bob really wanted was to occupy the office of the vice president. When Combined refused to promote him, he quit. Without advancement in sight, making a living out of a suitcase ceased to be appealing. Knievel wanted to do something else.

Getty Images

After leaving Combined, Knievel returned to his rudderless lifestyle. He found work at a motorcycle shop in Wyoming and thought a good way to drum up business would be to hop on a bike and try to jump over a pit infested with rattlesnakes.

It was.

That then gave him the idea to jump greater distances, which eventually led to him convincing the operators of Caesars Palace that he could make the 150-foot jump over the fountains near the front entrance of their Las Vegas resort and casino. He didn’t make it, but footage of the 1967 wipeout was absolutely mesmerizing: Airborne one minute and tumbling on the ground the next, Knievel looked like a crash test dummy. Convalescing in the hospital with multiple broken bones, Knievel’s popularity soared. He became one of the most famous men in America in the 1970s, rivaled only by Elvis Presley and Muhammad Ali.

Matt Tonning, one of Knievel’s former coworkers at Combined, was one of the millions of people who saw the footage. He was alarmed, but not because of the gruesome outcome. Over the years, Knievel had phoned Tonning to catch up and buy policies—10 in all, which was nine more than a salesperson was technically allowed to sell to any one person. Tonning liked Knievel so much that he usually just entered another salesman’s name to complete the transaction. The policies could not be canceled and covered any accident.

At no point did Knievel ever list his current occupation: daredevil.

Tonning was fired. When Knievel heard of his friend’s dismissal, he agreed to drop claims on nine of the policies.

If there were any hard feelings, Knievel never voiced them. He would later credit the unflinching optimism of Stone and his book as one of the key reasons he became a professional cheater of death. Staring up at the ramps that would launch him into the air, those sales lessons led him to believe he could make it—even when past experience proved otherwise.

Additional Sources: Evel: The High-Flying Life of Evel Knievel.