Teaching Kids Business Skills: A Father's Story

Ever wonder what your kids might learn from watching you run your business? Scott Dillingham, owner of LendCity Mortgages, sat down with his two children, Isaiah and Aubrey, for a candid chat about business, life, and yes, Pokémon cards.

What started as a fun family podcast episode turned into real lessons about how kids pick up business skills just by being around you.

The Daily Negotiator

Isaiah has a serious passion for Pokémon cards. And by serious, we mean he negotiates with his dad almost every single day to get new ones.

Scott noticed something interesting: his son doesn’t just ask once and give up. Every day brings a new angle, a fresh approach, a different strategy. Sound familiar? That’s exactly what good business negotiation looks like.

The best part? Isaiah doesn’t even realize he’s building a valuable skill. He’s just really into Pokémon cards.

When Customer Service Gets Real

Here’s where things got funny. When asked what he’d do with the family business, Isaiah had plans to turn it into a Pokémon store. His idea? Challenge customers to battles. If he wins, he gets their card. If they win, they get one of his.

But when Scott asked what happens if someone wants his rare Charizard card, Isaiah said they’d never get it and could never come back.

That’s when dad had to step in with a gentle business lesson: if you want customers to come back, you can’t tell them to leave. It was a perfect real-world moment about customer service and why protecting your business sometimes means making sacrifices.

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The Emotional Intelligence Advantage

Isaiah does something else that caught our attention. When his mom feels sick or sad, he draws pictures to cheer her up.

This matters more than you might think. In a service business like mortgages, understanding how people feel and wanting to help them matters just as much as knowing the numbers.

Empathy isn’t something you can easily teach in a classroom. But kids who naturally want to help others feel better? They’re learning something valuable without even trying.

Learning to Overcome Fear

Aubrey, Scott’s nine-year-old daughter, had her own business lessons to share. She visits the office regularly and has formed close bonds with the staff.

Her favorite thing? Playing pranks with the team. They’ve hidden coworkers’ belongings, shared funny videos, and created a workplace atmosphere that feels more like family than corporate office space.

But the real lesson came from something unexpected. Aubrey was scared of Harry Potter at first. Really scared. But she gave it a chance anyway, and now she loves it so much she’s redecorating her entire bedroom with a Platform 9¾ theme.

Why This Matters for Business

Trying something that scares you and pushing through? That’s exactly what business owners do every day. Whether it’s making that first cold call, hiring your first employee, or taking on a bigger loan than feels comfortable.

Aubrey also taught herself to beat a challenging Harry Potter video game through pure persistence. No one made her do it. She decided she wanted to learn and stuck with it until she figured it out.

The Bike Riding Method Every Parent Should Know

Scott shared a parenting tip that’s too good not to mention. When teaching Isaiah to ride a bike without training wheels, they found a YouTube method that actually worked.

Here’s the trick: take off both the training wheels AND the pedals. Let your kid push themselves along with their feet while sitting on the seat. This forces them to learn balance first, without the complication of pedaling.

Once they’ve got the balance down, put the pedals back on. Keep the training wheels off.

Isaiah mastered it quickly using this approach. Sometimes the best way to learn something complex is to break it into smaller, simpler parts.

Building Confidence Through Activities

Both kids are learning physical skills that build confidence. Isaiah claims he can run at “supersonic speed” and even beat a car in a race. That childhood confidence matters.

Aubrey practices karate and recently got featured on her karate school’s website. But what she values most isn’t the recognition. It’s learning how to defend herself if she’s ever in a bad situation.

She even practices defensive moves at home, occasionally catching her dad off guard with random judo chops and kicks.

What This Means for Your Business

The real story here isn’t about kids taking over a mortgage company someday. It’s about how business owners can involve their families in what they do without pressure or expectations.

Your kids don’t need formal business training to learn valuable skills. They pick up things just by watching you work, visiting your office, and seeing how you interact with people.

The staff at LendCity clearly love having the kids around. They bring them gifts, play with them, and treat them like family. That kind of workplace culture doesn’t happen by accident. It happens when the owner values personal connections over corporate formality.

The Bottom Line

Scott’s kids might not actually take over LendCity someday. Isaiah might end up running that Pokémon store after all. Aubrey might become an actress.

But the skills they’re learning now—negotiation, empathy, persistence, confidence, overcoming fear—those skills will serve them well no matter what path they choose.

And that’s really what good parenting and good business have in common. You create an environment where people can learn, grow, make mistakes, and figure things out on their own.

Whether you’re raising kids or building a team, the same principles apply. Give them space to explore. Let them try things their way. Be there to guide them when they need it. And celebrate their wins, even if those wins involve rare Pokémon cards.

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Frequently Asked Questions

How can I teach my kids about business without pressuring them?

Let them visit your workplace and interact with your team naturally. Kids pick up business skills like negotiation, customer service, and problem-solving just by watching you work. Focus on exposing them to your world rather than teaching formal lessons.

What business skills do kids learn naturally?

Kids develop negotiation skills when they ask for things they want. They learn empathy by comforting others. They build persistence through hobbies and challenges. These soft skills matter just as much as technical knowledge in business.

Should I expect my kids to take over my business?

No. Expose them to your business and let them explore their own interests. The skills they learn from being around your work will help them succeed in whatever career they choose, whether that's taking over your business or pursuing something completely different.

How do I create a family-friendly workplace culture?

Welcome family members into your office space. Encourage your team to build personal relationships. Allow room for humor and playfulness alongside professional work. When your team treats each other like family, that warmth extends to your clients too.

What's the best way to teach kids to ride a bike?

Remove both the training wheels and the pedals. Let your child push themselves along with their feet while sitting on the seat. This teaches balance first. Once they master balance, put the pedals back on and keep the training wheels off.

How can I help my child overcome fears?

Encourage them to give scary things a chance in a safe environment. Celebrate when they push through initial fear. Whether it's trying a new activity or watching a movie that seems scary at first, overcoming small fears builds confidence for bigger challenges.

Why does emotional intelligence matter in business?

In service businesses especially, understanding how people feel and wanting to help them matters as much as technical knowledge. Kids who naturally want to make others feel better are developing skills that will serve them well in any customer-facing role.

How do kids learn persistence?

Through activities they choose themselves. When kids decide they want to master something—whether it's a video game, a sport, or a hobby—they learn to stick with difficult tasks until they succeed. This self-directed learning builds stronger persistence than forced activities.

Disclaimer: LendCity Mortgages is a licensed mortgage brokerage, and our team includes experienced real estate investors. While we are qualified to provide mortgage-related guidance, the broader financial, tax, and legal information in this article is provided for educational purposes only and does not constitute financial planning, tax, or legal advice. For matters outside mortgage financing, we recommend consulting a Chartered Professional Accountant (CPA), licensed financial planner, or qualified legal advisor.

Written by

LendCity

Published

December 22, 2025

Teaching Kids Business Skills: A Father's Story | LendCity