Fly Your Flag Early

Joe Duran's Next Bet, Warehousing Your Black Diamond, Wealthbox, and more

I hope you’re enjoying a fantastic Independence Day weekend.

Here in Charleston, we’re keeping our golden doodle, Nacho, from completely unraveling at the sound of fireworks, while the kids fill the house with laughter, friends, and plenty of summertime chaos.

Nacho loves headphones / hates fireworks

We just returned from our annual trek to the Northwoods of Wisconsin. It’s part family tradition, part spiritual reset, and part logistical rodeo. But it always pays off. This week, I’m sharing a glimpse into one of my favorite stops—Stoney Acres Farm—where pizza, pints, and purpose come together in the most unexpected and inspiring way.

Also, a quick milestone shoutout:

This week, Kyle Van Pelt dropped Episode 99 of The Milemarker Podcast featuring our friend Brian Shenson. And next week? Episode 100 goes live—with a very special guest who leads one of the most inspiring wealth management firms I’ve ever had the chance to serve.

So, whether you’re reading this lakeside, fireside, or with one eye on Nacho and one on your inbox, thanks for being here.

Let’s dive into this week’s Rising Tide.

  1. Fly Your Flag Early

  2. On the Pod: Solving the RIA Puzzle: Leadership, Platforms, and the Missing Layer 🎧

  3. Bookmarks

    1. The Power of Integration: A Live Webinar with Black Diamond

    2. Eliminate the Hidden Costs of Messy Data with Milemarker + Wealthbox

  4. Milemarker On the Road ✈️

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.

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

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On the Pod: Solving the RIA Puzzle: Leadership, Platforms, and the Missing Layer

Episode 099: On this week’s episode, Kyle Van Pelt sits down with  Brian Shenson, Managing Partner and COO at Rise Growth Partners. With more than two decades of experience working with financial professionals, Brian has developed a deep understanding of the business fundamentals and operational aspects of wealth management services.

Kyle and Brian explore the evolving landscape of advisor tech and the power of intentional growth. Shenson shares lessons from his journey through Schwab, consulting, and BCG, diving into the challenges firms face with tech sprawl, data integration, and delivering personalized client experiences. They discuss how Rise is helping mid-market RIAs scale with purpose, leverage data more effectively, and build modern platforms that prioritize human connection and operational clarity.

(00:00) - Intro

(02:09) - Brian's money moment

(05:35) - Brian’s journey from Schwab to Rise

(09:57) - What captive firms can learn from independents (and vice versa)

(13:43) - Why most RIAs don’t build their own platforms

(19:19) - What it really takes to build great fintech

(20:54) - The vision behind Rise Growth Partners

(23:54) - Accelerating growth with strategy and tech

(27:11) - Who Rise is built for

(33:20) - Bridging the gap between advice creation and advice execution 

(38:35) - The power behind platforms

(40:46) - Brian's thoughts on AI, data, and the future of advice

(46:20) - Brian's Milemarker Minute

⚡️Bookmarks

The Power of Integration: A Live Webinar with Black Diamond

Tired of your tech stack feeling more like a tangled mess than a growth engine?

Let’s fix that—together.

🗓️ Wednesday, July 16 | 12–1PM ET
📍 Virtual | Save Your Spot

Join Milemarker and Black Diamond for a live, fast-paced webinar on how the smartest firms are transforming their data chaos into clarity—and turning integration into their secret weapon for growth.

​This dynamic conversation will dive deep into:

  • Why data integration is critical for driving operational efficiency and scalable growth

  • Real-world examples of how leading firms are unifying their tech stacks to gain deeper insights

  • Best practices for leveraging integrated platforms like Black Diamond to create a seamless advisor and client experience

  • The strategic mindset forward-thinking firms adopt to turn data into decisions

If you’re ready to ditch the tech headaches and build a connected, high-performing firm…

This is the conversation you can’t afford to miss.

Eliminate the Hidden Costs of Messy Data with Milemarker + Wealthbox

Messy data isn’t just annoying—it’s expensive.

Join Milemarker and Wealthbox for a quick, tactical webinar on how poor data hygiene quietly drains your firm’s time, resources, and client trust—and what to do about it.

🗓️ Wednesday, July 23 | 2PM ET

Learn how to clean up your CRM, eliminate risk, and finally make your data work for you.

Milemarker on the Road
Catch my team on the road at the following events or cities:

  1. July 9 - Birmingham, AL

  2. July 10 - Nashville, TN

  3. July 23 - Atlanta, GA

  4. July 29-31 - Denver, CO

  5. September 7-10 - Los Angeles, CA

  6. September 10-12 - San Diego, CA

If you’re in any of those cities and want to arrange a meeting time, reply to this email, and we’ll get something on the calendar.

Jud Mackrill