The Talk I Wasn’t Ready For

Less than a year ago, I had to sit my kids down and tell them something I’d been avoiding.

“The project Dad’s been working on isn’t going to work out. I have to start over.”

Their faces dropped. They’d been hearing about it at dinner for months. They were excited. They were rooting for me.

And now I had to tell them it failed.

Here’s the thing nobody warns you about when you build something as an entrepreneur with a family: the hardest audience isn’t investors or customers. It’s your kids.

They don’t care about product-market fit. They just know Dad was working on an idea and they see him as the best at what he does. So naturally, this idea in their eyes could grow into something BIG. Like, you know, Mr. Beast league success.

But after the initial disappointment, something happened that I didn’t expect. It opened up one of the best conversations I’ve ever had with my kids. About failure. About what it actually means to try something hard.

We talk about failure a lot in our house. Not making a competitive team. Missing a soccer goal. Failing a test. Making a poor choice.

But this conversation was different. Instead of what might feel like a “lecture” from Dad, they got to see me in a deeper, more meaningful way.

I told them about all the things I got wrong before building Naked Apartments. The bad ideas. The false starts. The moments I was sure I wasn’t cut out for this.

And I told them the truth: every single one of those failures was necessary. Including this one.

Not in a motivational poster kind of way. In a real, practical way. Each one taught me something I couldn’t have learned any other way.

Starting over isn’t fun. But I’ve done it so many times. And I know something now that I didn’t know when I started down this path 25 years ago. The starting over IS the work. It’s what entrepreneurship is all about. It’s not a detour. It’s the path.

My kids will fail at something big in the future. And when they do, I want them to remember this conversation. Not because Dad had all the answers, but because he didn’t. And he kept going anyway.

“There’s a difference between knowing the path and walking the path.”