How to Raise Entrepreneurial Kids

Welcome back to The 2x2 - the ultimate newsletter for executive consultants!

We’re joined by Leslie Elliott, Poolie CEO and mom of four, to talk about the curse of entrepreneurship – and nurturing them in your children early on.

We also exchanged a few business ideas.

Maybe one of you here can give it a shot with your kid. 👀

Read on…

⏰ Today in 5 minutes or less:

Entrepreneurial skills reveals itself early. You need to know how to recognize it.
Look for kid arbitrage – some business ideas are a better fit for kids.
Nurturing means knowing your kid’s limits and teaching them the math.

How Leslie Elliott Raised a 12-Year-Old CEO

How old were you when you first started a business?

Leslie Elliott, Poolie CEO and mom of four, is a business builder. And it seems her son is also wired for it.

It started when she found a half-empty twelve-pack Sprite in her 6^th grader’s backpack. When she asked James about it, he said he goes to an H-E-B before school and sells soda to his friends.

He made $20/day and called it SchoolDash. This is when Leslie knew she has an entrepreneur in the house.

Now, James is onto his second business venture: Grove Flower – a flower delivery subscription service for assisted living residents.

In this episode, we talked about recognizing that your child is afflicted with the curse of entrepreneurship and nurturing it in a positive way.

We also exchanged business ideas that we think kids can start today.

Let’s dive in.

Almost every entrepreneur started with a paper route when they were a kid. I think it’s a trait that reveals itself very early. What was your story?

Leslie: My first business was in fourth grade, selling golf balls and sodas on the sidewalk of a golf course.

There was a creek behind our house where balls always landed, so I’d collect them, clean them, and sell them to golfers. The sidewalk was public property, so the course couldn’t stop me – though the old lady driving the drink cart absolutely hated me for stealing her sales.

I started charging fifty cents, then learned different balls had different values, so I updated my pricing model. I added candy and sodas, priced them cheaper than the clubhouse.

I eventually raised the price from 75 cents to 85 cents, and people would tell me to keep the change. I hauled everything in a bike trailer to Albertsons when I needed inventory.

I initially did it because I wanted to earn money for a school trip, but I decided I didn’t want to spend all my earnings on that. When I got too old to be “cute,” I trained my younger sisters and took a cut of their profits until we moved.

That was my first real business.

You and I have mothered seven kids between us, and we both know this entrepreneurial spirit is not for every child. But with James, you saw something early. Why him?

Leslie: James has always been the old soul of the group. He’s perceptive in this way where you feel like you're talking to a nine-year-old when he’s three. He’s also started two businesses on his own already.

One of them was called SchoolDash, where he’d sprint off the bus, buy donuts, gum, sodas – whatever kids wanted – and then resell them at school. I found out because I grabbed his backpack to unpack his lunch and pulled out a half-empty twelve-pack of Sprite.

Last summer, his friend tried to sell a BMX bike for $50. James told me, “It’s worth $250. I’m going to buy it and resell it.” And I’m there trying to insert some ethics like, “You cannot rip off your friend.”

That’s James. He has instinct, and he sees opportunities everywhere.

The drive is real. It’s innate. It’s not something I could’ve taught, and it’s not something that fits all kids.

Kevin and Sierra are competitive and would love to make money, but James is wired for this. He’s always been five years ahead of himself in that way.

That brings us to Grove Flowers, the new venture. I love this story because it started with empathy. Can you walk through how that first spark became a business idea?

Leslie: My father-in-law moved into assisted living earlier this year, and when we were getting him settled, James and I brought flowers to make his place feel nice. We also brought extras for his neighbor, Judy, and another resident, Joanne.

We knocked on Judy’s door, and she almost cried. Same reaction when James handed flowers to Joanne.

These women were genuinely touched – like the kind of reaction where you feel it in your chest. And James noticed it immediately.

On the drive home, he said, “We should do this more often. I wonder if we could turn this into a business.”

That was the moment.

Because the Grove has 250 residents, and they’re a captive audience with limited outside interaction. Their kids can afford to send them flowers. And we already had access to a wholesale flower market nearby.

So James and I sat down on a Friday night, and we built a website: groveflower.com. I thought maybe he’d lose interest, but he came home Monday with business cards he’d made in class because he was bored.

We pitched the director of the facility, and James asked if he could set up a demo table during social hours. He’s making mini arrangements for samples, he printed flyers, he recruited his twin sister because he thinks her presence will “draw attention.”

At the heart of it, though, is that moment: the look on someone’s face when they receive something beautiful.

That’s what he reacted to. That’s why this works.

It’s arbitrage, yes, but it’s also empathy. He saw a real emotional need, and he built something around it.

Let’s break down the business model. Because beyond being a cute kid business, it’s also a very real one. How does the economics of Grove Flowers actually work?

Leslie: Right now, James is offering two plans: $45 for monthly delivery and $80 for twice monthly. He didn’t want to do it weekly because he didn’t think he could commit to that rhythm.

Costs are minimal because Goodwill vases sell for 99 cents, and then we just need the wholesale flowers plus his time. The margin is around 45% net at the current scale.

But here’s where it gets interesting. There are 12 facilities in Austin similar to the Grove, each with about 250 residents. That’s a total addressable market (TAM) of about 3,000 people. If we converted 10–15%, then that’s 300–450 subscribers.

At the current $80 pricing, that’s roughly $16,000 a month.

And you can run that with one or two kids until you hit the point where labor becomes your constraint. At scale, you’d need to hire more help, but the early phase is highly profitable.

The residents light up when a kid brings flowers. Adults could do it, but it’s not the same product. You’re selling a feeling.

Whether James sticks with it long-term doesn’t even matter to me. He already built something empathetic, scalable, and structurally sound.

What We Can Learn from Leslie Elliott (and James):

Look for kid arbitrage. Some small opportunities are ignored because they aren’t worth it for adults – or because it won’t work if they did it. James’ business can potentially generate $16,000 a month. That's not big enough for any adult, but it’s a huge opportunity for a business run by a kid.
Deconstruct existing businesses into very small pockets. The floral industry is huge, but James deconstructed it to find a pocket with huge potential. The opportunity revealed itself when he was empathetic, but his entrepreneurial spirit unlocked how to make it work.
See if your kid can actually run the business. Part of nurturing an entrepreneurial kid is knowing their priorities and avoiding burnout. James only delivers flowers twice a month because it’s what he can commit to. If it takes too much time from school or rest, then it’s not worth it.
Teach them how to run the simple math. Check the market size, likely conversion, margins, and their time limits. If the numbers don’t work on a napkin, they won’t work in real life.

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