I Told a Kid to Start a Podcast. His First Episode Made Me Rethink What We Tell Our Teenagers.

In September of 2024 I was in Austin waiting to try a VR headset that, two years later, still hasn’t become a real product.

While I waited, I ended up talking with a kid who was volunteering at the venue. He was a high school senior. We talked for a while about what might come next for him, and what struck me wasn’t his ambition, plenty of seniors have that. It was that he could actually hold a conversation. He had his finger on the pulse of what his generation was going through and he could articulate it in a way that made you want to keep listening.

Near the end I told him he should start a podcast.

Then nothing. No follow-up. I didn’t put him in a system or set a reminder to check in. I said one true thing to a kid I’d met an hour earlier and went back to my life.

Two years later, a text. He’d just dropped his first episode.

I listened to it that day. Max interviewed a twenty-year-old named Tony who’s building a startup that uses AI to analyze athletes’ form and help them train without paying for a personal trainer he couldn’t afford in high school. They talked about a lot of things. But the thing that stuck with me was Tony’s answer at the very end, when Max asked what he’d tell an eighteen-year-old about to walk across the graduation stage.

He said: you have so much more time than you think.

I’ve been chewing on that statement, because I’ve lived the argument he was making, and I don’t think it’s the argument most people hear when it gets made.

I could write the easy version of this. I’m a guy who skipped college, started a business at nineteen, and has been self-employed for twenty-seven years. I could tell you college is overpriced, that it delays the start of your actual life, that it hands a nineteen-year-old a pile of debt before he’s earned a dollar, and that nobody knows which of these degrees AI is going to hollow out in the next decade anyway.

All of that is true. And it’s also not helpful, because there are already a hundred people saying it louder than I ever would, and none of them are talking to the parent who’s actually scared.

Here’s what I think is more honest.

At eighteen, you have a very small window into what’s out there.

You only know what you’ve been exposed to. Your parents’ jobs. Your teachers’ jobs. Whatever your town does for work. A handful of professions that show up on TV. That’s the menu. And it feels like the whole menu, because you have no way to know what isn’t on it.

Then we take that kid, with a worldview built from maybe a dozen data points, and ask him to make a decision worth four years and six figures. And we act surprised when it doesn’t hold.

That’s the actual problem. It was never which path you pick at eighteen. You’re not choosing. You’re guessing.

Here’s the part I want to be careful about, because I felt it while I was listening.

To be clear, this isn’t what Tony was selling. His actual answer was that you have more time than you think, and to be patient, which is the same thing I’m arguing. But scroll social media for ten minutes and there’s a new prescribed path taking shape: start a company. Be a founder at nineteen. Take the gap year, do the bootcamp, ship the startup. It looks like rebellion against the college default, and it’s dressed up like freedom.

It’s the same disease in a different costume. It’s still a narrow default, handed to the same kid, with the same tiny window. For some people it fits perfectly. For most it’s just a different flavor of somebody else’s answer.

I’m not telling anyone’s kid to skip college and go build a startup. That’s just trading one blind guess for another.

When I was nineteen I opened a skateboard shop. Online first, then a physical store about a year later. My friends were going to college. I was pretty sure the worst thing that could happen was I’d end up back at my mom’s house digging out of debt, and that seemed survivable, so I went.

I ran that shop until I was twenty-five. Then it ended.

And I want to be precise about this, because the way that story usually gets told is wrong. It’s not “I started a company at nineteen and won.” I didn’t win. The shop ran its course. But running it taught me how a business actually works — inventory, margins, customers, marketing, all of it — from the inside, at an age when my friends were reading about it. When the shop ended, I started building websites for small businesses, a skill I’d taught myself while running the store.

The photo at the top of this post is that desk. Twenty-five, shop closed, teaching myself to build websites. A door I wouldn’t have known existed if I hadn’t spent six years running a store.

Then photography took off. Then, when the housing market collapsed in 2008 and I was newly married and didn’t want to spend every weekend shooting weddings, I pivoted again into marketing.

None of that was a plan. Every one of those pivots was possible because the last thing had shown me a door I didn’t know existed.

The shop wasn’t the destination. It was the window opening.

That’s the case for taking some time. Not “startups are better than school.” Just: you can’t choose from a menu you’ve never seen, and the fastest way to see more of it is to go do something real.

A gap year gets a bad rap because it sounds like uncertainty, like you couldn’t figure it out, so you’re stalling. I don’t see it that way at all. Taking a year to widen the window before you spend four years and six figures is what a mature person does. And if you do end up going, having a year of real context underneath you doesn’t waste the education. It amplifies it. You’ll know what the questions are for.

I had tight years in my twenties. Genuinely hard ones. There were nights I wondered if I’d made a mistake, and I’d think that if I just had a degree hanging on the wall, I’d feel more at ease.

Then I’d talk to my friends who went. Some were doing well. Others were struggling to find any real fit in the corporate world, and a few were walking away entirely from the thing they’d spent their early adult years learning to do.

Now, at forty-six, I’m grateful. Not conflicted about it. Grateful.

But there’s one thing I wish I’d understood back then, and it has nothing to do with a degree.

Surround yourself with people who genuinely want to see you improve and aren’t afraid to tell you when you’re not living up to your own expectations.

I had people around me who were willing to tell me what I was doing wrong. That wasn’t the shortage. The shortage was in me, because of some voices I’d grown up with, I was resistant to that kind of feedback. And I never found the people who could see through that resistance and push me anyway.

Somehow I slipped through. Most people are either anti-authority or they follow it blindly. I was anti-authority and somehow still willing to listen to wisdom, and I don’t think I earned that. I think I got lucky.

That’s the thing I’d go back and fix. Not the college part. The people part.

Which brings me back to that podcast.

Tony’s got four older brothers and five older cousins. All of them entrepreneurial. One brother’s company is worth more than a billion dollars. He grew up in a house where excellence wasn’t a goal, it was the baseline.

He didn’t coast in on that, and I want to be fair to him here. He got rejected from every school he actually wanted. He took a gap year when nobody else at his school was taking one, and lost some friendships over it. He taught himself to code. He cold-messages strangers on LinkedIn every week until he runs out of connection requests, and one of those messages sat unanswered for three months before it put him in a room with an NFL team. He does the work.

But he does it with a room full of people who are further down the road and who don’t flinch about telling him the truth. And he knows it. At twenty he’s already saying out loud that he doesn’t want yes-men around him, he wants the person who’ll tell him not to do the thing.

He has, at twenty, the exact thing I say I wish I’d had at nineteen. And it isn’t a degree.

That’s what a mentor actually is: somebody else’s worldview on loan until yours catches up. People who are ahead of you have seen more of the menu than you have. That’s the whole value. And it’s the thing that makes the difference between wandering and moving, so pick your mentors wisely.

College is one way to buy that proximity. It’s an expensive, indirect, four-year way to buy it, and it frequently doesn’t even deliver. But it is a way. And if your kid skips it, you have to solve for that deliberately, because it will not happen by accident. It didn’t for me.

If you’re a parent right now looking at a teenager who has no idea what he wants, I understand why college feels like the safe answer. It’s a plan. It’s something to point at. It buys four more years before anyone has to know.

But I don’t think safe is what it is. I think it’s just the default with the best marketing.

What I’d want for my kids, and I’m saying this as someone whose oldest is closing in on this decision, so I’m not writing from a comfortable distance, is a wider window before they choose, and people around them who’ve already seen more of it than they have.

Everything else is guessing. And we should at least be honest that that’s what we’re asking them to do.

If you took a non-traditional path, or you’re staring down this decision with your own kid right now, I’d like to hear where you landed and whether you’d do it again. Reply and tell me. I read every one.

Max’s first episode is here:

Max is twenty and he’s already better at this than most people twice his age. Two years ago I told him he should start a podcast. I’m glad he did. Good work Max!

- Jerad