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March 4, 2026

How I Teach My Kids to Think Like Entrepreneurs

Some of the most valuable business lessons don’t happen in a boardroom, they happen in everyday life.

In this short video, Rory shares how a simple snow-shoveling job turned into a powerful lesson for his kids about service, reputation, client selection, and referrals. What seemed like a small moment quickly revealed the same principles that drive long-term business success and financial prosperity.

Entrepreneurial thinking doesn’t have to start in a classroom or a corporate setting. It often begins with hands-on experience, real responsibility, and understanding how effort creates value.

Watch the video to see how everyday experiences can shape a lasting business mindset.


Transcript:

The Best Business Lesson Started with a Shovel

The best business lesson I’ve ever taught my kids started with a shovel. Hi, I’m Rory O’Hara, founder of Ausperity Private Wealth in Moorestown, New Jersey. Today I want to share a short story about my son because it captures some of the most important business lessons I’ve learned over the years—and how I teach my kids to think like entrepreneurs through real-life experiences.

A Snowstorm, a Driveway, and a First Dollar Earned

It happened in real time in the middle of a snowstorm, when my son earned his first dollars on his own by shoveling a neighbor’s driveway. What stood out to me wasn’t just the money—it was how quickly the fundamentals of business showed up: service, pricing, client choice, reputation, and referrals, all wrapped into one experience.

Why Great Service Gets Rewarded

The first driveway took longer than he anticipated. It was a big space and the snow was heavy, but he did the job carefully. He cleared the whole thing, shoveled close to the edges, and knocked on the door afterward to make sure they were happy.

When the neighbor paid him, they didn’t just give him what he asked for—they gave him extra. That was the moment the lesson clicked.

When you provide great service, people notice. They’re often willing to pay more than the minimum. Whether you’re shoveling snow, running a business, or managing complex financial decisions for clients, effort shows.

You Don’t Have to Say Yes to Every Client

After that first driveway, word spread. A few more neighbors waved him over. By the last job, he was exhausted and frustrated.

He asked, “Do I have to say yes to everyone?”

That’s a powerful question. The answer is no. Not every client is the right client. Some take more time than they’re worth. Some drain energy. Some don’t respect the value of good work.

Learning to choose where to spend your effort is a critical business skill—and one of the most important ways to teach kids to think like entrepreneurs early on. Whether you’re a kid with a shovel or an executive managing high-stakes decisions, saying yes to everything usually leads to burnout.

How Referrals Actually Work

Here’s where it got interesting. That first neighbor told someone else. Then another person said, “I heard you did a great job down the street.”

That’s referrals in action.

Happy customers lower the cost of acquiring the next client. In business, referrals rarely come from flashy marketing. They come from consistently doing what you said you would do—and doing it well.

How Reputation and Effort Compound Over Time

That afternoon went far beyond shoveling snow. It revealed how work creates value, how reputation compounds, and how effort today sets up tomorrow.

These same principles apply when managing client relationships, navigating stock compensation, handling a lump sum payout, or planning for retirement income.

Entrepreneurship at its core is about creating experiences that make clients want to come back—and tell others.

Passing Down Mindset, Not Just Money

If you’re thinking about how to pass down not just money but mindset, these lessons don’t have to be complicated.

At Ausperity Private Wealth, we spend a lot of time helping families think intentionally about decisions, values, and long-term impact.

If that’s a conversation you’d like to explore, we’re always open to it. Thank you for listening.