The Operator
Practical thinking on ownership, building, growth and the decisions that become harder when the business is yours.
Revenue Is Up. So Where's the Money?
My son, Andrew, bought his first business at 25.
Two and a half years later, revenue is up nearly 50%. He's refining his marketing, building systems, and laying the groundwork for what he hopes will eventually become a multi-location business.
By most measures, he's making progress.
There's just ...
Oct 30, 2026
The Part of Success Nobody Shows You
We’ve become obsessed with the destination and forgotten what it takes to make the journey.
We love a good success story.
The entrepreneur who sells a company for millions. The founder who turns an idea into a thriving business. The executive who walks away from corporate life and builds somethin...
Oct 20, 2026
The One Problem I Couldn't Solve
**A Special Edition of The Operator**This post is different from what I usually write. It's not about business strategy, financial performance, or the mechanics of ownership. It's about a personal experience that fundamentally changed how I think about all three.It's the most personal story I've ...
Oct 12, 2026
You Probably Shouldn't Leave Corporate
Here's how to tell whether you're the exception.
I spend my time helping people leave corporate to build or buy a business. So take it seriously when I tell you most people shouldn't.
You have a solid corporate job with a steady paycheck and a 401K that's benefited from the stock market gravy tra...
Oct 05, 2026
Borrow Like an Owner
On my most recent SBA loan, rates had come down since we closed. So I called the loan officer who'd helped me get it started and asked whether we could revisit my rate.
She routed me to a loan servicing manager, who got on a call with me and ran through three modification scenarios, simply becaus...
Sep 28, 2026
Leave While It's Still Going Well
Almost everybody waits to be pushed. It's the worst possible condition to decide in.
Ask people why they left and you get a story that starts with something going wrong. A reorganization. A new boss. A promotion that went to somebody else. The role quietly changing into something they never signe...
Sep 23, 2026
I Bought a Company I Had Stopped Believing In
What my mentor said in week six of due diligence, and why I still repeat it.
Six weeks into due diligence I had a list, and the list was bad.
No product management to speak of. An org chart that made no sense when you followed it from the top down. Nobody inside the company could tell me what the...
Aug 29, 2026
You Don't Need More Motivation, You Need Less Shame
I saw it in ten minutes. She had been inside it for three years.
Three months ago I took a call from Megan, a former colleague and a good friend, and inside five minutes she told me she and her husband were thinking about selling the business or shutting it down.
I had to ask her to say it again!...
Aug 18, 2026
Retirement Is the Wrong Finish Line
I spent thirty years running toward a beach. Getting there is how I learned it was the wrong direction.
I came to this country with no money and paid my own way through school. I took my first job as a software engineer in 1988, earned an MBA, and moved into consulting for two reasons I was very ...
Aug 07, 2026
Cash Flow Beats Profit, and It's Not Close.
Profit is an opinion. Cash is a fact. And the day debt enters your business, bought or built, the two numbers split.
My son is 27, a licensed personal trainer who genuinely loves the work and is good at it. He studied sports management, minored in entrepreneurship, and has wanted to run his own f...
Jul 30, 2026
Runway Is a State of Mind Until It Isn't
The strength of your runway was decided long before the day you look up and see how little of it is left.
In December of 2020, a friend referred me into a startup in the Pacific Northwest doing genuinely exciting work in cloud security. Two ex-Microsoft product executives, Ivy League pedigrees, a...
Jul 30, 2026
What AI Made Cheap, and What It Made Priceless
Two years ago, I read Arthur Brooks's book “From Strength to Strength.” A friend had gifted it to me while I was considering launching a new online learning business. The last one I launched at 38, so doing it again at 56 was scary to say the least. The typical questions: What if I blow through a...
Jul 23, 2026
The Operator
