Stephen Dubner

Her idea was kind of like Airbnb, connecting people who have a spare bedroom with someone who needs a bedroom. Or like Uber, connecting people who have a car with someone who needs a ride. Simple, right? In her case, she was connecting people who wanted to learn to fly with flight schools in their area.

Her idea was kind of like Airbnb, connecting people who have a spare bedroom with someone who needs a bedroom. Or like Uber, connecting people who have a car with someone who needs a ride. Simple, right? In her case, she was connecting people who wanted to learn to fly with flight schools in their area.

She would list locations, prices, availability, and then you would use her app to schedule lessons. That was the idea. Now she just had to build it.

She would list locations, prices, availability, and then you would use her app to schedule lessons. That was the idea. Now she just had to build it.

She would list locations, prices, availability, and then you would use her app to schedule lessons. That was the idea. Now she just had to build it.

So she hired a web developer.

So she hired a web developer.

So she hired a web developer.

Oshkosh is a massive air show held every year in Oshkosh, Wisconsin. And when I say massive, think of Lollapalooza and Burning Man combined, but for aviation.

Oshkosh is a massive air show held every year in Oshkosh, Wisconsin. And when I say massive, think of Lollapalooza and Burning Man combined, but for aviation.

Oshkosh is a massive air show held every year in Oshkosh, Wisconsin. And when I say massive, think of Lollapalooza and Burning Man combined, but for aviation.

The debut turned out to be a disaster. Flight schools weren't interested. They were skeptical of Hoffman and her product. Most of them weren't interested in digitizing their systems anyway. It was a terrible experience, but she didn't give up.

The debut turned out to be a disaster. Flight schools weren't interested. They were skeptical of Hoffman and her product. Most of them weren't interested in digitizing their systems anyway. It was a terrible experience, but she didn't give up.

The debut turned out to be a disaster. Flight schools weren't interested. They were skeptical of Hoffman and her product. Most of them weren't interested in digitizing their systems anyway. It was a terrible experience, but she didn't give up.

That was Jill Hoffman. Now on to John Boykin, who lives in Belmont, California, between San Francisco and Silicon Valley.

That was Jill Hoffman. Now on to John Boykin, who lives in Belmont, California, between San Francisco and Silicon Valley.

That was Jill Hoffman. Now on to John Boykin, who lives in Belmont, California, between San Francisco and Silicon Valley.

This was about 10 years ago.

This was about 10 years ago.

This was about 10 years ago.