The Art of Raising Leaders

Watching the Next Generation Take the Lead

(Photo: With my oldest son at his St Andrews Graduation)

If you want to raise a leader (regardless of career path) who can walk through fire, you have to stop protecting them from the world and start preparing them for it.

As you know from my writing, I’ve always been a proponent of the Puddle Jumper mindset.

It is that “ordinary magic” of being allowed to fail, get dirty, and realize you are the one who can get yourself back up.

I watched this evolution with all my kids.

They are all doers and developing leaders.

True leadership isn’t just about being smart; it is about seeing a void in the world and having the absolute audacity to fill it.

It’s also about being a good person. How many of us have had run-ins with brilliant jerks?

I see it all the time.

The talented painter who can’t find financial success because he can’t work with a gallery owner and is arrogant to clients.

The SEAL who thinks he’s too talented to get kicked off the team, only to be kicked off for talking back to his leadership (seen this personally).

None of us is as smart as all of us.

I’m an investor in my oldest son’s tech start-up, LandLord.

I just read through his Q1 2026 investor update, and frankly, it hit me right in the chest.

He isn’t messing around!

He’s leading a full-scale disruption of the real estate market.

Here’s an excerpt:

“Many People, One Purpose”

Property managers are careless and mercenary. It’s not their property and a modest revenue satisfies their commission.

This is why Landlord is building the world’s first AI property manager–starting with the most profitable real-estate type in the world, self-storage. With this technology, anyone can use our AI to invest in property as easily as buying a stock.

In 1979, a small company called Graphics Group built the world’s best computer for making computer-animated films. However, every animation studio passed.

The studios were hiring huge teams of artists to draw every frame by hand, and they didn’t believe computers could ever compete. But the Graphics Group team knew they were right and that their computers would change the film industry forever.

So, they did something radical.

They decided to make the computer-animated film that every studio didn’t believe was possible to force the hand of the film industry. The movie was Toy Story, and this company is now called Pixar.

Over the past 6 months while selling we learned 3 things:

1. 95% of self-storage owners are older and don’t believe AI can run their property

2. 5% of self-storage owners are younger but only want to vibe-code their own tools

3. The 5% are dominating the 95%

The path to complete disruption of the self-storage market is devouring the 95% with our AI.

In the past four weeks:

• Week 1: AI scans thousands of deals, finds the best one, and negotiates the purchase

• Week 2-3: We raised $275,000 to acquire property #1

• Week 4: Working with our AI we complete due diligence and are now under contract.

Our team will be forced to evolve our AI from top to bottom management.

The pain for huge storage funds and small retail owners is going to be competing with us.

The pain-relief will be paying a monthly subscription for our AI to run their property too.

What impressed me most wasn’t just the tech, but his leadership philosophy. His update mentioned a “Many People, One Purpose” mantra and a set of design commandments that favor simplicity and rigorous testing over bloated tradition. One of his rules is: “If your mom can’t use a feature, it doesn’t exist.” That is the kind of clarity and focus that defines a real leader.

The Return on Investment

We often think of parenting as a game of control, but it is actually about trust.

I gave Jackson real-world responsibility early, like having him manage one of my own self-storage investments as a college freshman.

He didn’t just maintain it; he modernized it, found the friction points, and used that frustration to build a superior software solution while he was still in college. He didn’t wait for permission to innovate.

As parents, our mission is to clear the runway so purpose can land. When I see my son leading a team to dismantle an outdated industry, I know the mindset his mom and I cultivated worked.

So, let your kids break things. Let them face the cold wind of a difficult day. When they stumble, don’t swoop in to fix the problem. Stand beside them and remind them that falling is just the tuition for becoming an independent leader.

Thx for listening. Brandon