Fly Your Flag Early

Why a small farm in Wisconsin might have more to teach us about running a great business than any conference ever could. Sometimes, it’s important to Fly Your Flag Early to showcase what sets you apart.

Every year for the past five, I’ve taken a week or two to work off the grid—though “off” might be a stretch. I’m still taking meetings. Still talking to clients. Still doing the work. But my headquarters shift from airports and offices to the Northwoods of Wisconsin.

The change in scenery clears the mental clutter. The noise of back-to-back calls and nonstop travel gets replaced by something quieter—and much more useful: perspective.

One of our favorite traditions up here is Pizza and Pint Night at a local farm called Stoney Acres, tucked into the countryside near Athens, Wisconsin.

Tony runs the place, and he’s exactly what you hope a guy named Tony running a pizza farm would be: passionate, grounded, and magnetic in the best way. He’s tossing dough, cracking jokes, pulling pies from a wood oven while people gather around tables in the middle of a field. It’s honest, unpretentious, and deeply good.

Everything in the pizza is made on the farm—except for salt, olive oil, and cheese. And the cheese is local. The beer? Brewed on-site with local grain and hops. And there’s a returning favorite: a rhubarb sour called simply “Fhubarb.” (Yes, it’s as refreshing as it sounds.)

But what’s more powerful than the pizza or the pint is the presence of this place. Tony and the Stoney Acres crew have built something that’s become a staple in the region. They’re more than a business. They’re a cause.

And that is what sticks with me.

Fly Your Flag—And Fly It Early

One principle my wife and I have leaned into while running our businesses—whether embedded inside a national RIA or running our own firms—is this:

Fly your flag. And fly it early.

If you care about something, make it obvious. Don’t bury it in jargon. Don’t hide behind “best practices.” If you believe in it—own it. Put it front and center.

Stoney Acres isn’t shy. They care about sustainable farming. About community. About fun. It’s not marketing. It’s just who they are.

And it raises an honest question for all of us:

When people work with you, what do they get right away?

What do your clients feel before you ever tell them?

What does your team know without needing to read the handbook?

These values might be hard to put into words—but they should be easy to spot.

We’ve got too much sameness in our industry. Too many firms trying to be everything to everyone. Too many advisors afraid to stand for something.

But the truth is, people are drawn to conviction.

To clarity.

To originality.

Maybe you need your own “off-the-grid” week to figure it out. Maybe the time around this holiday is enough. But whatever space you can carve out, use it to reconnect with who you really are—and then start building from there.

Here’s to being the best version of ourselves.

To not hiding.

And to building things that matter.

Because we’ve got enough homogenous junk already.

Let’s make something better.

—Jud