Cultivating Great Leaders Takes Something More Than Hard Work
Entrepreneur Office Hours - Issue #298
What I’m about to write isn’t going to surprise anyone reading this, but I’ll share it anyway: I’m not exactly the most traditional educator on the planet. I’ve heard my classroom leadership style called both innovative and chaotic, and I’d argue both descriptions have their merits.
Either way, I usually justify my approach as being better than some imagined “normal” alternative (whatever that might look like). Still, if I’m being honest with myself, I sometimes wonder if my methods are really as good as I claim… or if I’m just really good at telling stories.
Recently, though, I had an experience that reminded me there might be some genuine merit to leading young people in a way that sometimes borders a bit too far toward out-of-control.
This semester, I’ve got two students helping me teach a class. I’ve known both of them since they were freshmen. Now, as upperclassmen, they’re co-leading a few sessions. On the second day of class, I walked in with absolutely nothing prepared because it was their day to run things. Honestly, I was nervous. In the back of my mind, I was already preparing for the inevitable moment when their presentation would end after 30 minutes and I’d need to “fill” the next 45 with whatever random teaching scraps I could cobble together.
But that moment never came.
Instead, they were amazing. Passionate. Energetic. Confident. They didn’t just present; they taught. They led discussions. They sparked curiosity. They had become subject-matter experts in their own right. And as I watched them, I couldn’t help but think about how far they’d come — and how, if I’d done things the “normal” way, I’d never have gotten to see it.
The truth is, if they’d been doing “just another class assignment,” they would’ve phoned it in. They’d have asked for a rubric and gone on to deliver a competent but forgettable presentation. Instead, because I’d given them space over the years to experiment, fail, and try again, they stepped up and treated the class as their own.
And that’s when it clicked for me: leadership is a long game.
You don’t grow leaders by dictating every detail or demanding perfection right away. You grow leaders by investing in them early, giving them space to try, letting them stumble, and encouraging them to keep going. You don’t always see results immediately — in fact, you usually won’t. But if you stay patient and consistent, one day you’ll look up and realize the people around you have grown into something extraordinary.
Whether in the classroom or in a startup, that’s what leadership is about. It’s not about control. It’s about cultivation. And if you’re willing to play the long game, the payoff is worth it.
-Aaron
This week’s new articles…
Nobody Actually Wants Your Startup to Succeed (and That’s a Good Thing)
What if all the people you think are cheering you on are actually cheering for something else?
How Experienced Founders Know if Their Startups Are Going to Succeed
From the inside, your startup is never going to feel as successful as you want, so good founders look for certain kinds of metrics.
Office Hours Q&A
QUESTION:
Hi Dr. Dinin,
First off, thank you for all the content you share. I’m a senior at a small liberal arts college, and your posts always give me a mix of motivation and existential dread — which I think means they’re working 😅
I’ve been thinking seriously about launching a podcast. I already have a concept, I’ve recorded a few test episodes, and I even have some friends who’ve offered to help me produce it. But I can’t help feeling like maybe there are already too many podcasts out there. I’m wondering if it’s even worth the time and energy to add another one into the mix.
My question is… how do you know when something is worth starting even if the market seems totally saturated?
Thanks again! And if you ever guest on student podcasts, I’d love to have you!
-Rachel
You’re right. There are too many podcasts out there.
Just like there are too many blogs.
Too many YouTube channels.
Too many Instagram accounts.
Too many startups.
Too many coffee shops.
Too many books.
Too many job applicants.
Too many everything.
If the existence of “too many” were a valid reason not to try, I suppose nobody would ever start anything. So instead of worrying about “too many,” let’s reframe the question…
Rather than asking:
“Is it worth starting another podcast?”
Try asking:
“Is it worth starting my podcast?”
That’s a better question because, no, people don’t need another generic podcast. But they might need yours. And it changes the important issue from whether or not the world needs another podcast to whether or not you can give them something no one else is giving them, and, by doing so, create meaningful value.
By the way, none of this means you have to develop some revolutionary concept. It could just mean your point of view is valuable. Or your energy. Your curiosity. Your honesty. Your weird obsession with vintage ketchup ads from the 1970s. (Okay, maybe not that last one. Or maybe especially that one. Who knows?)
In other words, yes, the podcast market is saturated. But markets always look saturated, and yet people still manage to come along and do something better, smarter, funnier, more honest, more relatable, more useful — or, simply put, more valuable.
That’s what makes the difference… value
So don’t ask whether podcasts are “worth doing.” Ask whether you’re willing to keep showing up with something only you can do that creates meaningful value in the world.
If the answer is “yes,” hit record.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.