The Bold Entrepreneurs

October 9, 2026

If you're a new subscriber Welcome! What you are reading today is a revisit to a previous article slightly retitled. This is week 7 of my 8 week break from writing so I can complete a new project I'm working on and hopefully give my brain a break so this newsletter doesn't become too stale. The following is an article from August 2, 2025.

We can always find amazing inspiring stories and lessons by studying the entrepreneurs who were the first to market with their inventions. I’m always fascinated to hear how new inventions were inspired. Take farm tractors.

Farm Tractors

Benjamin Holt built a steam engine tractor in 1890 (his company later became Caterpillar). It was a great idea destined to revolutionize farming. But his tractor had a problem. It was extremely heavy and had a tendency to sink and get stuck in soft dirt or mud.

Then along came John Froelich. He adapted a gasoline engine to his tractor design and the weight problem was solved. His company, the Waterloo Tractor Company was later sold to John Deere. Deere wanted to manufacture tractors but didn’t want to start from scratch. So they bought their way in. They already made other farm implements so they already had their distribution channels. Brilliant.

And there was Henry Ford. He grew up on a small farm and always dreamed of building tractors for the millions of small time farmers throughout the world. He built his tractor using components already in use in his cars. One day he made a bold statement to a newspaper that he could make a million tractors and sell them for $200 each. At the time he did not have the ability to do what he claimed. And yet…

One day World War 1 came along. Thousands of tractors were bought for the European war effort and the tractor companies all made millions, including Henry Ford. Making that claim to the newspaper was a bold move.

John Froelich’s bold move was to take a gasoline engine used to run an elevator and adapt it to a tractor frame and build the world’s first gasoline powered farm tractor.

John Deere’s bold move was to buy Froelich’s struggling company and turn it into the world’s largest manufacturer of tractors and other farm equipment.

It's A Sign

There’s a lesson here. There’s an old saying “Fortune favors the bold.” Now when someone says “You’re crazy” and “That will never work”, I take that as a good sign that I’m on the right track. These men were willing to be bold to be successful. We see this in every industry. Bold people create entire industries and change the world.

Being an entrepreneur takes a bold mindset. We have to be willing to be different, think different, and do different. As we move along through our business/entrepreneurial careers we can sometimes lose that bold mindset. We slip into that wretched comfort zone and we forget to be bold. We forget our different way of thinking.

Be honest with yourself about this: Have you forgotten how to be bold? I did. We have to get that back.

Consider doing something bold in your business or career. What could that be?

Thanks to all our readers and welcome to the new subscribers! I hope you enjoy the newsletter!

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