“Be prepared, most of them won’t show up.”

That’s what my partner Tony told me as we launched a new online school for high schoolers, where the goal is to teach them how to build their own online business. Specifically, an online school.

Yes, I see the irony. Inception-style education.

We’re running a pilot program with five students, and today was Day One.

I was crossing my fingers for three to show up. Mentally, I braced myself to teach just one, because teenagers and commitment go together about as well as oil and water.

But then the call started. All five were there. On time. Eager. Engaged. (Well, one was five minutes late, but honestly, that’s early by teenage standards.)

How did that happen?

How did we get the most famously apathetic demographic in existence, high school students, to actually show up for something educational?

The process was pretty simple.

In the week leading up to the program, I sent them daily emails. One email per day had something actionable they had to do: fill out an onboarding form, complete a short task, things like that.

The second email each day was a bit more personal. A short story, something inspirational, or just a glimpse into my life. Not the “Here’s my resume” kind of personal, but more like “Here’s a funny thing my kid said” or “My wife hates my jokes, but I’m telling them anyway.” That kind of thing.

I wasn’t trying to impress them. I was trying to connect with them.

And I didn’t stop there.

I also sent every email to their parents. Ostensibly, this was to keep the family informed. Realistically, it was to get them involved too.

Because after nearly 20 years of building online schools, I’ve learned something important:

Learning is a team sport.

And for most students, especially younger ones, their first and most important team is their family.

So I pulled everyone in.

Which is how, on the first day of class, we had a full house. Cameras on. Minds open. Ready to roll.

But we weren’t done.

You can probably guess what the first class was about.

I called it “orientation,” but the real goal?

More connection.

Most of the activities weren’t academic at all. They were designed to get the students to know each other. To break the ice. To lay the groundwork for something deeper.

I told them, “This is your first mastermind.”

You’re not just learning how to build a business. You’re learning how to build a network. For some of you, this might be the first time you’re building professional relationships.

The students in this room? They’re your peers. They’re sharp, ambitious, and they’ll all end up at top-tier universities. If you build a real connection here, you might just have friends, colleagues, and collaborators for life.

I could see the lightbulbs turning on.

This wasn’t just another Zoom class.

There were no grades. No gold stars. No busywork.

They weren’t doing this for me. Or their parents. Or some random GPA boost.

They were doing it for each other. For their families who made it possible. For the classmates they were starting to connect with. Maybe even for the teacher who’d been dropping bad dad jokes into their inbox all week.

But most of all, once that light clicked on, they were doing it for the future version of themselves they could suddenly see a little more clearly.

So here’s my question to you:

Are you intentionally building connections in your online school?

Or are you just crossing your fingers and hoping it magically happens?