Windows are open in Charleston today.

The wine and food festival is in midstream, and the Lowcountry is beautiful.

Tomorrow I'm headed to Future Proof's East Coast event — sand, sun, and meetings over the next few days. If you're going to be there, let me know.

I'm writing this fresh off our monthly all-hands. Every month, we gather the whole team, walk through what we accomplished, welcome new customers, preview what's coming, and take a minute to actually celebrate each other. It's one of my favorite hours of the month.

Today's meeting had some extra energy. That's just what happens when you work with extraordinary people.

This week's newsletter is about something I introduced this quarter that has quietly become one of the highlights of my work life — something that's unlocked a level of creative output from our team I didn't see coming.

Here's this week's Rising Tide.

1. What's Your Clauduary?

2. Building Resilient Firms in the Age of AI with Chip Kispert 🎧

3. Milemarker Compliance Webinar Replay

4. Milemarker On the Road ✈️

What's Your Clauduary?

January 2nd.

Most people were still recovering from New Year's Eve. I was standing in front of our team announcing a new company mandate.

I called it Clauduary.

The idea was simple: every week in January, each person on our team—ops, sales, marketing, design, engineering—had to share something they'd built or figured out using Claude. Not just "I tried it." Something real. Something that changed how they worked.

No exceptions. No observers.

Why it mattered

We were already in a partnership with Snowflake. We'd built our own AI-powered product. AI was core to what we sold.

But I was watching my team—smart, capable people—and was filled with deep curiosity of what they could unlock if they dug deeper.

The tools were there. The access was there. The habit wasn't.

Clauduary was about forcing the habit. Publicly. Together.

What happened

Something shifted fast.

Within a week, people were showing each other things none of us had thought to try. Automations. Prompts. Entire workflows that didn't exist before. One person figured out how to compress a two-hour research task into 20 minutes. Another built something in Claude Code that our team had been talking about for months.

We moved everyone onto Claude's Team plan. We set up Projects. We built Skills.

The rapid iteration was real. The ROI was obvious. Worth every cent—by a long shot.

The bigger thing

Here's what Clauduary reminded me.

Education has never mattered more—and it's never been harder to keep up.

We can't rely on what we learned five years ago. The floor is rising. The clients we serve are getting smarter. The questions they're asking are getting harder.

Years ago, Jamie Hopkins and I were at Carson together. We pushed a mandate: every client-facing advisor had to earn their CFP. It wasn't popular at first. But it worked. It raised the floor. It created a culture where learning wasn't optional.

I think that bar only goes higher from here.

Clients don't just want someone who passed an exam. They want someone who understands the current landscape—tax, markets, technology, planning—and can apply it to their life. That requires people who are genuinely curious. People who are building new skills, not defending old ones.

Where we are now

Clauduary was supposed to end January 31st.

It didn't.

I wouldn’t let it.

The momentum was too good to stop. So we extended it through February—because no one said Claudary only had 31 days. Same principle. Keep sharing. Keep building. Keep surprising each other.

Now it's March. We're calling it the Ides of Claude. And yes, I'm already thinking about what April looks like.

The point is: what started as a one-month experiment has turned into something more durable. A rhythm. A culture. A standing expectation that we're all moving forward together—not at the speed of the most enthusiastic person on the team, but as a collective.

New things keep showing up. New use cases. New ideas from people I wouldn't have expected.

That's the thing about cultures of learning. They compound.

The question for you

What's your Clauduary?

Not AI specifically—though I do think you should be using it. I mean: how are you, as a leader, creating the conditions for your team to learn together?

Is there a shared challenge? A shared goal? A weekly ritual that forces the habit?

Because the firms that figure this out aren't just going to be better at technology. They're going to be better at everything. Better at serving clients. Better at retaining talent. Better at adapting when the next thing shows up—and it will.

A healthy brain loves to learn. I genuinely believe that. I hope it's true for you too.

— Jud

What are you building with AI at your firm? Hit reply. I read every response.

On the Pod: Building Resilient Firms in the Age of AI

Episode 134: On this week’s episode, Kyle Van Pelt sits down with Chip Kispert, Founder & Managing Partner at Beacon Strategies. Chip has spent decades building and leading one of the country’s most trusted wealth management partners, helping shape its national footprint through intentional M&A, strong partner alignment, and disciplined operational systems.

Kyle and Chip explore what it takes to build durable advisory businesses while embracing innovation. They discuss the power of structured peer roundtables, how firms can move beyond legacy technology assumptions, and why operational rigor becomes more important as firms grow. The conversation also dives into AI adoption—distinguishing native versus enabled tools, addressing internal fear, and establishing formal AI policies—highlighting how thoughtful leadership can turn disruption into long-term enterprise value.

In this episode:

(00:00) - Intro

(01:45) - Chip's money moment

(04:23) - What Beacon Strategies does and who it serves

(08:03) - Why structured roundtables outperform traditional conferences

(11:39) - Why firms are reassessing legacy technology providers

(15:19) - Native AI vs. AI-enabled tools

(17:27) - Managing fear and uncertainty around AI

(22:48) - Avoiding AI overload and creating a formal policy

(27:29) - Introducing the Beacon Provider Network (BPN)

(31:20) - One area financial services must improve

(35:08) - Chip's Milemarker Minute

Milemarker Compliance Webinar Replay

Earlier this week, we hosted a workshop featuring Dr. Jordan Hutchison of RFG Advisory. We walk through how his team has built an AI-driven compliance solution that provides scale, clarity, and real operational impact — and what's actually stopping most firms from getting there. If you're thinking about AI for operations or compliance, this is worth 45 minutes of your time.

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

1. Miami, FL — March 8-11

2. New Orleans, LA — March 9-12

3. Sarasota, FL — March 24

4. Tampa, FL — March 28-29

5. San Francisco, CA — April 14-15

If you would like to arrange a meeting time, please reply to this email, and we’ll schedule something on the calendar.

Jud Mackrill