3 Entrepreneurs Who Lost Before They Won

Matt Henderson
Mission.org
Published in
5 min readJan 12, 2016

Colonel Sanders didn’t open KFC until he was 62. Sony started with electric rice cookers.

The American Dream comes with a lot of assumptions and promises. That, if you work hard, your dream will be fulfilled; if you are relentless, you will win. It isn’t that black and white, and most understand that.

People understand that jumping into the pursuit of happiness comes with a lot of potential dangers. Happiness is binary. After you jump into the chase, you either end up happy, or you don’t; and that’s frightening enough to keep people from jumping in at all. It’s much safer to stick with the narrative of “well, if I did jump in, I would’ve won.”

The American Dream is binary on a macro-level. You either win or lose. On a micro-level, though, you can’t treat it with the same logic. If you ‘jump in’ and lose a month later, you haven’t really failed. The pursuit of happiness is a “journey of a thousand miles,” a month of effort is merely a few steps.

A marathon runner can stumble coming out of the gate and still win the race.

It’s important to understand that a micro-loss is good. “Hustle” does not promise you victories, it promises you quicker losses. The more things you start, (generally) the higher your chances of victory become. For many of our society’s most romanticized, most successful people, if they hadn’t lost, they wouldn’t have won. For many, their losses were the main ingredients they used to cook up their wins.

Colonel Sanders

At age 22, Harland Sanders got fired from his job at a railway after getting into a fistfight with a colleague. At 24, he became a lawyer, only to get fired after getting in a fistfight with his client in the courtroom. At 26, after getting a job as an insurance salesman, he got fired for refusing to follow management’s directions. At 30 he started running a ferry boat company. It went fine until a bridge was built near his route. At 33 he started a gas lamp company, only to be run out of business by the electric light. At 34, after getting fired from a job selling tires, he began running his first gas station. Until, of course, the Great Depression wiped it out when he was 37. At age 40, he found another gas station to run. While running this gas station, he started developing his secret fried chicken recipe. When Sanders was 45, his primary competition closed down after the owner was convicted of murdering Sanders’ district manager. At 49, he started another gas station with a restaurant and motel. The same year, his restaurant completely burned down, but the state of Kentucky recognized his “contributions to state cuisine,” giving him the honorary title of ‘Colonel.’ Three years later, at age 52, his second gas station went out of business due to the lack of tourism (and other factors) caused by World War II. Ten years later, at 62, Colonel Sanders opened the first Kentucky Fried Chicken in Utah. After running out of money seven years later, he was forced to sell his original gas station. Within five years, 600 restaurants sold Kentucky Fried Chicken. Colonel Sanders sold KFC for just over $15,000,000 (in today’s money).

“[Colonel Sanders] only had two rules: Do all you can and do it the best you can. It’s the only way you ever get that feeling of accomplishing something.”

It took Colonel Sanders 52 years to ‘make it.’ He had zero wins before he actually won. If Sanders never got into that courtroom brawl, he would’ve been a subpar lawyer for the rest of his life.

Rowland Macy

Rowland got a job as a whaler when he was 15, only to quit when he was 19 because he wasn’t getting paid enough. At 22, he started a thread-and-needle shop in Boston. It went bankrupt. At 24, he opened a dry goods store. It went bankrupt. With hopes of striking it rich in the Gold Rush, he went to California at 27. He found no gold. He started Macy’s in Massachusetts at 29. It went okay, it was a modest success. Seven years later, at 36, he moved Macy’s to its flagship location in New York. He made just $12 the first day. By the end of that year, though, Macy’s was a success, making $90,000. 19 years later, Macy’s became a ‘department store.’

It took Macy 14 years to succeed in retail. After succeeding in retail, it took him 19 years to create the department store we know today as Macy’s. If he found gold in California, he likely would have never established Macy’s. He would have made a few million dollars from gold, but would’ve never grown his $3.5 billion share of Macy’s.

Masaru Ibuka

After serving in the Imperial Japanese Navy during World War II at 37, Ibuka started a shop that produced a variety of products. His first big product was an electric rice cooker, but he scrapped it because he couldn’t develop something that cooked the rice perfectly. A year later, his next big product, an electrically heated cushion, failed because it would get too hot, burn things, and start fires. Other products like radio adapters and voltameters he produced at this time became somewhat successful. During the next four years, he was able to secure the rights to sell tapecorders. The company changed its name to Sony to have greater success in America; and, during Ibuka’s 49th year, Sony sold over 100,000 transistor radios in the U.S.

Even after getting a late start, Ibuka was able to fail fast and, eventually, win.

These three people created great, successful, dynamic organizations that have bettered the world in many different ways. After losing a ridiculous amount of times, they became successful.

They leveraged nearly every single one of their losses to give themselves a better chance to win on their next venture.

Success and failure is not synonymous with winning and losing. Failure is merely the absence of success. If you don’t succeed, you fail. If you don’t jump into the pursuit, you’ve already failed. No one starts life in a state of success (it’s relative), everyone starts in the field of failure.

Both winning and losing create success. The only thing that creates failure is a lack of winning and losing, a lack of trying. The best way to create one great product is to create one hundred poor products.

A little bonus: Colonel Sanders on “What’s My Line?” in 1963.

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Matt Henderson
Mission.org

Building things like @vonhughesnyc @rumblrapp @nova_ventures in NYC