Jay Leno: how to survive long bouts of unemployment

Ms Julia Meech had stumbled upon a mystery. She was a curator of Japanese art at New York’s Metropolitan Museum. While going through historical records of how the museum had acquired Japanese prints over the years, she found something very surprising. 400 index card records showed that Japanese Shunsho prints that the museum had acquired were sold to them by a certain “F. L. Wright.” 

She dug in further and found that their Japanese arts dealer was none other than the famed architect Frank Lloyd Wright! Wright had made a fortune selling 400 Japanese prints to the museum between 1918 and 1922!

But before we continue his story, let’s jump to the future and see a struggling comedian.

Jay Leno and his early struggles

Jay Leno always knew that he wanted to be a comedian. He started a comedy club in the college he was studying at. He was good. But it was hard to make money with comedy.

He was 37 years old when he became a regular substitute host for the Tonight Show. In other words, Leno was 37 years old till his comedy gig started bringing in enough money consistently. So then how did he survive?

“Follow your passion and success will follow” was true for Leno. But not for a very very long time. Leno could follow his passion and continue as a comedian only because he had a hobby that earned him money. A side hustle.

Leno bought old classic cars, fixed them, and resold them. That’s what allowed him to stay in the game long enough to eventually succeed.

Side hustles for the win

Side hustles are important. They create a safety net. Leno bought his first car when he couldn’t even drive it himself. Leno was 14 years old when he and his father saw a 1934 Ford pickup truck that did not work. Leno bought the car for $350 and his father taught him how to fix it over the next two years. 

Leno traded the pickup truck he had fixed for the Datsun 1600 sports car when he got his own driving licence. And since then he has always had a thing for fixing classic cars. And thankfully, it was a skill that paid well.

But it was still him selling his time. Classic cars are a niche market that paid well. But if Leno didn’t invest his time, he wouldn’t earn.

Are there better side hustles?

Frank Lloyd Wright’s side hustle

Frank Lloyd Wright is considered one of the best architects of modern times. But he lived a very extravagant life. There was no way consulting as an architect would pay for Wright’s luxuries. And so, he started selling Japanese art prints to his clients for their homes as well as their art collections.

Japanese art had always influenced Wright. When he visited Japan in 1905, he met a few art dealers there and bought Japanese art for himself. But soon realised that he would be able to sell them to his clients as well.

In 1912, he expanded his small side business and started selling art prints to people beyond his clients. He started selling them to art collectors as well as museums. Within a year, he had a big commission from William and John Spaulding – art collectors from Boston. They bought 1400 Japanese ukiyo-e print blocks from Wright for $100,000! Wright earned a cool $25,000 out of the trade!

That was a ridiculous amount because it was 10 times more than what his last architecture project had earned him!

It was the perfect side hustle. Because it fulfilled two criteria:

  1. It could be done anytime. Which allows you to focus on your passion work as your main gig.
  2. The effort put in is not correlated to the returns. It’s not constrained by the hours you put in – just by how many people you can sell to. So it can scale up as a solo business. 

For years, Wright earned more selling Japanese prints than from his architectural practice! It’s what allowed him to have a devil may care attitude, take more risk in his work, and break the trends.

Action Summary:

  • Side hustles are good safety nets. What can you buy and sell?
  • Put in the effort to do two things. But one of them being a side hustle – something that you spend minimal time on.

Quote Unquote

“Everyone should have 3 hobbies:

  • One to make you money
  • One to keep you in shape
  • One to be creative”
    – Naval Ravikant