Helicopter or Ground View? How Age Shapes the Way Business Owners See Their World

by Bill Gollan 17th of November, 2025

Helicopter or Ground View? How Age Shapes the Way Business Owners See Their World

The 100th edition of Bsale got me thinking about something that comes up in nearly every conversation I have: the way business owners of different generations think. Not just how they run things, but how they see the business itself.

After spending over 35 years running my own business and now working as a business broker, I’ve sat across the table from hundreds of owners. And there’s one thing I’ve noticed again and again: your age often defines how you see your business.

Some fly above it.

Others are right down in the thick of it.

It’s not about who’s better, it’s about perspective.

The View from Above

Many older business owners especially those in their 50s, 60s, and 70s operate from what I call the helicopter view. They’ve earned it. They’ve built long-term businesses, built trust, and built resilience through change.

From that vantage point, they’re thinking big-picture. How the business fits into their lifestyle. When to exit. Whether the next generation will take over. They’re strategic and selective with detail diving in only when the numbers or people tell them something needs their attention.

It’s a smart way to lead. But come sale time, the risk is that too much of the business is still in their head. Buyers want to see systems, structure, and succession not just experience.

The Ground-Level Operator

On the other hand, younger business owners those in their 30s and early 40s tend to be hands-on, boots-on-the-ground operators.

They’re in the data, the dashboards, the digital strategy. They track everything and optimise constantly. Many have built their business around automation and growth from day one often with the endgame of a future sale already in mind.

They come to the table with documented systems and scalable thinking. But sometimes they’re still proving the model. Or the business is so reliant on their energy and involvement that stepping away looks riskier to a buyer.

Different Views. Same Goal.

Both views, the helicopter and the ground level, bring strengths and blind spots.

Older owners bring consistency, client loyalty, and a calm confidence that comes from years of experience.

Younger owners bring innovation, data fluency, and scalable infrastructure.

What they share is this: both want to see the business succeed beyond them.

The challenge? Buyers don’t just buy your results they buy your systems, your transferability, and your ability to step back without it all falling over.

Final Thought

Whether you’re operating from 30,000 feet or knee-deep in daily ops, one thing’s clear: the way you see your business shapes how ready it is for sale. In a market full of owners now thinking about exit, especially the nearly 700,000 Australians aged 50–75, the timing and preparation matter more than ever.

There’s no right or wrong view, the helicopter or the ground level, only the importance of knowing which one you’re in. And knowing how to translate that view into something a buyer will understand, trust, and invest in.

That’s where the value is.

And that’s where I come in.

Tags: business owner small business tips business broker