Happy Saturday.

Writing this somewhere over Kansas — headed from San Diego to JFK after five days with my team and meetings with advisory firms that are hungry for change.

This week, we announced new leadership additions at Milemarker and rolled out a bunch of new features for our advisors. Lots of momentum.

But the thing I can't stop thinking about across these 2,400 miles isn't what's moving. It's what isn't. And more specifically, who's paying the price at the firms that are standing still?

Case in point: while I was writing this newsletter, news broke that Block — the payments company behind Square and Cash App — just cut 40% of its staff. Replaced by AI. That's not a think piece about what might happen. It's a headline about what already been done.

Forty percent. Let that satisfactorily sit for a second.

I'll unpack that in today's Rising Tide.

1. Someone Else Is Paying for Your Patience

2. How Great Operators Turn Complexity into Growth 🎧

3. Adrienne Paulsen Joins Milemarker

4. Milemarker On the Road ✈️

Someone Else Is Paying for Your Patience

I know. I've been beating this drum.

AI is moving fast. Firms need to act. The window is closing. You've heard me say it. You've heard a lot of people say it.

I'm going to keep saying it — but today I want to talk about something different. Not what's happening. You get that. The question I keep running into is why so many firms can't respond — and more importantly, who pays the price when they don't.

That second part matters. Because it's the part that keeps getting ignored.

The cost doesn't land where you think it does.

When a firm's leadership decides to "take a measured approach" to AI and data transformation — to form the committee, to study the landscape, to wait for the next board meeting — who actually bears the cost of that decision?

It's not the C-suite.

It's the advisor who spends three hours a week on manual data entry that should've been automated a year ago. It's the ops team drowning in reconciliation tasks because systems don't talk to each other. It's the client who gets a worse experience — slower responses, less personalized service, clunkier onboarding — because the infrastructure behind the scenes is held together with duct tape and spreadsheets.

It's the next-gen planner who takes one look at the tech stack, realizes the firm is stuck in 2015, and walks out the door to a competitor who's already running AI workflows.

The people who decide to wait are never the ones paying for it. And that should bother every leader reading this.

Your AI committee is not going to save you.

Here's how the delay takes shape in practice. A firm gets excited about AI. They form a committee. The committee meets monthly. They discuss "use cases." They assign someone to "research options." Six months later, they have a slide deck and zero implementation.

I need to say this directly: the committee isn't a strategy. It's a sedative. It gives leadership the feeling of progress without any of the actual movement.

Here's some perspective on pace: in the time it's taken most firms to form an AI committee, Anthropic has released Claude Opus 4.5 and 4.6 — two of the most advanced AI models ever built. Not incremental updates. Generational leaps. The technology your committee is "evaluating" has already been replaced twice by something dramatically better.

The AI landscape doesn't move on your meeting schedule. It moves on its own timeline. And that timeline makes your quarterly check-ins look like geological time.

While the committee meets, the advisor continues to do the manual work. The client is still experiencing subpar service. The cost keeps compounding — it just doesn't show up on the balance sheet. It shows up in attrition, in missed opportunities, in the slow bleed of competitive position that nobody notices until it's too late.

The elephant in the room.

When leadership decides to "do something about AI," they turn to IT. Makes sense on the surface. Technology problem, technology team.

But at most firms, IT is a small team whose primary job is to keep advisors logged in to their laptops and connected to the office network. They're troubleshooting VPN issues and resetting passwords. They're not AI automation experts. They're not data engineers. Asking them to suddenly become your firm's innovation engine isn't fair to them, and it isn't a strategy.

It's like asking your receptionist to design your financial planning process. Different skill set. Different mandate entirely.

The firms bumbling around right now aren't bumbling because they lack ambition. They're bumbling because they've delegated the most important strategic decision of the decade to people who were never hired to make it.

And who's paying? Not the person who made the decision to delegate.

Patience is a luxury. And it's not yours to spend.

Gradualism feels responsible. It feels measured. It feels like leadership.

It's not. It's a luxury that only the people at the top can afford. The advisor buried in manual workflows can't afford it. The client, comparing your experience to what a competitor just built, can't afford it. The young talent deciding where to build their career can't afford it.

If you're the one paying the cost of someone else's caution, send them this article. Because someone needs to say it plainly.

And if you're the one making the calls, stop letting other people pay for your patience.

If your firm isn't automating something new every week, you're behind. If your marketing is relying on an industry solution, you're in the stone ages. If you don't understand MCPs and don't have people actually working AI — not talking about it, not committee-ing it — you will be left behind at a level you've never experienced before.

I wish I were exaggerating. I'm not.

On the Pod: How Great Operators Turn Complexity into Growth

Episode 133: On this week’s episode, Kyle Van Pelt sits down with Jennifer Goldman, Founder and Strategic Operations Transformer and Integrator at My Virtual COO. Jen is an operations expert with 30 years of experience helping 1,000+ service businesses to thrive. 

Jen talks with Kyle about what it really takes to run a profitable, scalable advisory firm. From defining what makes a truly great operator to navigating the messy middle of firm growth, Jen shares practical insights on constellation thinking, building operational leaders, and making hard profitability decisions. She also dives into the emotional and structural crossroads firms face as they scale, the evolving role of technology and AI in operations, and why clean data and strong systems still require human ownership.

In this episode:

(00:00) - Intro

(03:33) - Jen's money moment

(06:39) - What it takes to be a great operator

(08:55) - How "constellation thinking" works

(12:19) - Balancing SOPs with creativity in operations

(14:42) - The profitability challenges in the growth process

(16:57) - What determines whether you should build or join a platform

(21:42) - How Jen utilizes AI in her work 

(23:01) - Why AI can't replace CRMs

(27:27) - Why it's important to have clean CRM data

(32:36) - What it takes to build a process for advisors and investors

(37:35) - What Jen looks for when engaging with advisors

(39:53) - Jen's outlook on the future of the financial services industry

(42:51) - Jen's Milemarker Minute

Adrienne Paulsen Joins Milemarker

Earlier this week, we announced that Adrienne Paulsen joined our team at Milemarker as VP of Operations. We are so excited for her to join the team and help us serve our growing roster of firms.

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. Tampa, FL — March 28-29

4. 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