Jill Hoffman

I don't think I've ever had just a basic conversation with Bert. And there's three cylinders that are working in his brain. And whenever you're talking to him, only one of those cylinders is spending time with you. The other two are thinking about building a new seaplane or trying to break a world record.

The goal was that you could find a local flight experience, book it, and pay for it all in just a few clicks from your phone.

I thought, how am I supposed to sell this platform? How am I going to show it to the aviation industry if it's not there? I just needed something to show them.

At first, it was wonderful because the web development team, they understood what I was trying to build and they added to it. And they said, you know, we solve problems. You know, what if a 14-year-old books a flight? What if it's canceled? How do we do that? I loved every second of it. And I thought we were on the same page because I was going to launch it at Oshkosh.

We invested money in ads, and I thought it was understood that I was going to pitch and show it, and it had to work. We were building a dummy site, and then they were going to make it live with some dummy profiles while we were building it in. And I get a call the day before we're supposed to launch, and the developer says, what did you mean by launch?

And it was the first time where I went, what do you, what? The communication, it shattered. And I just knew I was about to go into promoting this. I had everything on that with a dummy site. And ironically, I got a lot of people that wanted to fly. A lot of people signed up for it, but none of the flight schools saw any value with it. All they really saw was that it was glitchy.

I would talk to everybody I could. Two years of reaching out to everyone on LinkedIn I could find, trying to rebuild my reputation, just walking in, just feeling uncomfortable and trying to talk to the decision maker and show the product day in and day out across the country. So after getting no and no and no, and then one day I am at a flight school And it's set up like a Tesla showroom.

It's very modern, very excited. I've gotten to know this pilot very, very well. I was talking to him about the platform and our ideas of what we're doing to modernize. And he said to me, well, everybody did it. You know, I did it that way. Everybody needs to do it that way, too. And he just wouldn't sign in.

And that's the day I think I knew, if I can't get this young flight school owner that understands modernization, when he said, no, I did it that way, you can too. I think that was my tipping point. Or I just went, I'm done. I have no place else to go from here. And it broke me. You know, my grandfather lived through the Depression, and I think he gave me my earliest memories of money.

You pay for cars and cash, and, you know, you never waste. We were always very scrappy. We didn't grow up with money. Once I lost a $5 bill, and you'd think the world came to an end. But I lost over $100,000. And sometimes in the shower, I would physically just faint. get sick. And I felt like a complete failure, the shame of it. It took me a long time to figure out it was shame.

And it still hurts me. And it's very weird to have somebody ask me about it because I have the ability to clear a room. Nobody wants to hear about the failure when, in essence, that's all I needed at that time. I needed a story from somebody else that said... Yeah, I failed. Oh, and there's another guy over here and another lady over here that also failed. Oh, and, you know, my cousin also did.

And if I could have had those stories earlier on, I wouldn't have felt so incredibly alone like I was the only one.

If you fail as a woman, you had no business being there in the first place.

I thought the word failure was just something that you kind of said, and it really didn't apply to me.

I haven't really found that sweet spot of, oh, this is what I do very well, and it comes easily.

really a firm believer of, you know, perseverance. And if you build it, they will come. And the only way to fail is to quit. And you give it your full force and you will succeed. I mean, everybody else has.

Yes, my father is Dick Rutan. He was the first person to fly around the world nonstop, non-refuel, through bad weather and flying over hostile countries in a plane that if you threw a pencil at it, it would go right through the wing. He is part of the duo most people know of as the Rutan brothers. I like to call them the modern Wright brothers because his brother...

who's my uncle, Bert, is a revolutionary aircraft designer who has designed probably 50 different aircraft. So he's done crazy things like build experimental aircraft that look like they're flying backwards, using Volkswagen engines, all the way to a rocket, sending people to the edge of space.