Episode #63 - Work 100 Hours a Week at Apple… or Build Systems That Work for You? Jon Chose Both

In the latest episode of The Queen of Automation, I sat down with Jon Weiskopf, a brilliant former Apple engineer turned real estate investor who’s building an empire by rethinking everything we thought we knew about the industry. His journey from racing lawnmowers in Pennsylvania to running global engineering projects for Apple is wild enough. But what’s even more powerful is how he walked away from all of it to reclaim his time, rebuild his purpose, and build a business on his terms.

We talked about burnout, ambition, and the myth of work-life balance, especially when you're used to high-performance environments like Silicon Valley. Jon got brutally honest about the toll of 100-hour workweeks, parenting during a pandemic, and the shift that happened when he realized he’d spent 20 years building real estate but never owning any of it. That moment changed everything.

What really stood out in our conversation was Jon’s ability to blend hardcore engineering thinking with practical entrepreneurship. He’s building systems and processes for his real estate business that pull directly from his time leading projects at Apple. Except now, he’s the boss. We dug into why owning your time is the real currency, and how automation, operational clarity, and delegation are the tools every entrepreneur needs to build sustainably.

This episode is a must-listen if you’ve ever found yourself stuck in a “successful” career that no longer fits. Jon’s story is proof that it’s never too late to pivot. Sometimes your biggest leap comes right after you burn it all down and start again, smarter, simpler, and on your own damn terms.

Connect with Jon on LinkedIn to follow his journey and get inspired by the systems he's building from the ground up.