Greetings from Charleston.

It's prom night at our house. I just got back from taking pre-prom photos of our 17-year-old and her friends — the weather is perfect, friends are in town, and tomorrow we're headed to see My Morning Jacket with Alabama Shakes. Should be one of those weekends you don't forget.

This week, we launched Relay at Milemarker. We've been building it and rolling it out with customers for a while now, and as of Tuesday, it's live for all of them. The team is stoked. The early results are even better than we hoped. More on that below.

Next week I'm on the road — New York, Tampa, Atlanta, and Chicago. If you're in any of those cities and want to grab coffee, reply, and let's get something on the calendar.

On Wednesday, we launch the first in a new webinar series with SignatureFD called How I AI. It's a behind-the-scenes look at how firms are actually adopting AI to transform the way they work — less theory, less hype, more "here's exactly how we're using this on a Tuesday morning." Laura Hubbell kicks it off. Worth having on your radar.

How I AI: with Laura Hubbell, CFA | SignatureFD · Luma

Every RIA has AI tools now. Almost none of them are actually using them. Advisors and ops teams signed up, ran a few prompts, and quietly went back to doing…

luma.com/kjsaeybz

Without further ado, I'm going to break down the state of automation in the industry as I see it. I think it matters, and I think it's time.

Our team at Milemarker has also been shipping some of the most transformative updates we've ever released, and it's a delight to see the immediate impact on how firms run their businesses.

Here's this week's Rising Tide.

1. A Letter from the Office of Automation

2. Podcast: Serving Clients in Life's Most Difficult Moments 🎧

3. Milemarker Relay Launch

4. Milemarker On the Road ✈️

A Letter from the Office of Automation

I want to tell you something I don't talk about much.

In my past, one of my most fruitful marketing expenses has been in the category of automation.

Not on marketing. On the automation of it. Marketo. Salesforce clouds stacked on Salesforce clouds. A custom data warehouse. Zapier Enterprise. Segment. A team of people whose full-time job was keeping the plumbing working.

I'm proud of the work we did. It was ahead of its time for our category, and a lot of what we built still compares well with what most firms in our industry are doing today.

But here's the honest reckoning. It was expensive. And it was not nimble.

Every new campaign was a month of integration work. Every pivot was a small army reconfiguring plumbing. The stack could do almost anything — eventually. What it couldn't do was turn on a dime.

MarTech moves four or five times faster than anything we see in fintech or wealthtech. Running a billion-dollar marketing operation on Salesforce-era architecture was like trying to run a Formula 1 team with a diesel truck. You could do it. You wouldn't win the championship.

Here's a fun fact, though. The automation I put into place with some of today's largest wealthtechs back in 2013? Still doing its job. Quieter now. Older. But a house built on a rock.

That matters to you. If you start investing now — particularly by getting real control over your data — what you build is going to outlast almost everything else in your stack. Automation done on a strong foundation compounds. It doesn't decay the way most software does.

On Tuesday, we launched Relay. This letter is everything the press release didn't have room for.

Data is the fuel. Automation is the scale.

Every company is becoming a technology company. Not in the "we have an app" sense — in the deeper sense. How work flows. How decisions get made. How customers get served. All of it is becoming a software problem.

A software problem needs two things: clean fuel and a way to turn that fuel into motion without a human pushing every step. The fuel is data — unified, trustworthy, and real-time. The scale is automation — the thin layer on top that turns data into action.

Without both, you don't have a technology business. You have a service business dressing up as one. And the market will figure that out.

The numbers back this up:

• Automation can reduce costs by as much as 30% across enterprise processes (Bain & Company, "Most Automation Transformations Fall Short").

• Leaders cut process costs by 22% — versus 8% for laggards, and the gap is widening (Bain & Company, "Automation Scorecard 2024").

• Data-driven organizations see EBITDA increases of 15 to 25% (Böringer et al.).

• AI and automation can absorb 60 to 70% of the activities currently filling employees' time (Chui et al.). Not eliminate the jobs. Free the people inside them.

Translate those numbers into a mid-size wealth firm running at a 25% margin and the math isn't subtle. A 10% reduction in operating expenses is an enterprise-value story, not an efficiency story.

Most of wealth management hasn't picked up on this yet — especially mid-size and large firms. Automation in those firms is atrophied. Not because leaders don't care. Because the muscle hasn't been used. Because every attempt got stuck on the same thing: the data.

I used to spend a lot of money each year building bridges between systems. We should have been building ground.

The ground finally exists. The thing we were simulating a decade ago with integrations and duct tape is a product you can buy today. The excuse is gone.

A few years ago, somebody floated the idea of a Chief Automation Officer. I got the impulse, but it's the wrong instinct. Automation isn't a department. It's everybody's job, same as AI. The advisor is automating client review prep. The ops lead is automating morning recon. The CCO automating attestations. Everybody.

The firms that win this decade won't be the ones with the fanciest strategy. They'll be the ones where everybody is automating the repetitive stuff.

So here's what I hope for you.

Make this the year you automate everything you can. Not because we launched a product on Tuesday, but because the cost of not doing it keeps rising and the cost of doing it keeps falling. Those two lines are about to cross.

If you're a Milemarker customer, Relay is in your hands. Thin automation layer on your unified data. Included in what you already pay.

If you're not, automate anyway. Find one thing that eats an hour of your week and give that hour back. Then find another. Look around at what we're building for the firms we partner with. Get curious about what's possible now that wasn't six months ago.

Every business is becoming a technology business — whether its leaders have accepted that yet. A technology business needs data as fuel and automation as scale.

Two of those we can sell you.

The third — the conviction that your firm is, in fact, a technology business now — is on you.

Have a great weekend.

References

Bain & Company. "Automation Scorecard 2024: Lessons Learned Can Inform Deployment of Generative AI." Bain & Company, 2024, www.bain.com/insights/automation-scorecard-2024-lessons-learned-can-inform-deployment-of-generative-ai/.

Bain & Company. "Most Automation Transformations Fall Short, Despite Opportunity to Reduce Costs by as Much as 30%." Bain & Company, 13 Mar. 2023, www.bain.com/about/media-center/press-releases/2023/most-automation-transformations-fall-short-despite-opportunity-to-reduce-costs-by-as-much-as-30/.

Böringer, Jan, et al. "Insights to Impact: Creating and Sustaining Data-Driven Commercial Growth." McKinsey & Company, 18 Jan. 2022, www.mckinsey.com/capabilities/growth-marketing-and-sales/our-insights/insights-to-impact-creating-and-sustaining-data-driven-commercial-growth.

Chui, Michael, et al. "The Economic Potential of Generative AI: The Next Productivity Frontier." McKinsey & Company, 14 June 2023, www.mckinsey.com/capabilities/mckinsey-digital/our-insights/the-economic-potential-of-generative-ai-the-next-productivity-frontier.

On the Pod: Serving Clients in Life's Most Difficult Moments

Episode 140: On this week’s episode, Kyle Van Pelt sits down with Anne McPhail, Managing Director at Novare Capital Management. With more than 30 years of experience across corporate banking and wealth management, Anne brings deep experience in wealth management, with a focus on guiding clients through major life transitions and building advisory relationships rooted in trust, empathy, and long-term perspective. 

Anne talks with Kyle about what it truly means to serve clients through life's most important and often most difficult moments. She shares how genuine empathy and thoughtful financial strategy come together to create meaningful client relationships, how leading advisory firms deliver a consistent, high-touch experience at scale, and how Novare develops the next generation of advisors without compromising trust.

In this episode:

(00:00) - Intro

(01:43) - Anne's money moment

(04:18) - Novare's life transition playbook

(07:13) - Scaling personalized service across the firm

(09:06) - Anne's advice for young wealth professionals

(11:19) - Developing the next generation of advisors

(18:28) - Staying current in a changing industry

(21:17) - Integrating planning into every aspect of clients’ lives

(25:00) - Building trust that lasts through life's uncertainties

(25:56) - Philanthropy, community, and relationship building

(30:37) - Anne's outlook on the future of financial services

(33:50) - Anne's Milemarker Minute

Milemarker Launches Relay: No-Code Automation Built on a Unified Wealth Management Data Lake

Unlike generic API-based tools, Milemarker Relay runs on top of data already normalized across 130+ wealth management systems—so workflows understand accounts, advisors, sleeves, and compliance rules out of the box.

Milemarker Launches Relay

Milemarker launches Relay, a no-code automation tool that connects unified data lakes to 400+ systems, streamlining workflows for wealth management firms.

www.milemarker.co/articles/globenewswire-milemarker-launches-relay

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

1. New York, NY - April 20

2. Tampa, FL — April 21-22

3. Chicago, IL — April 23-25

4. Omaha, NE — May 4

5. Nashville, TN — May 7

6. Indianapolis, IN — May 11-13

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

Jud Mackrill

Greetings from New York.

I'm up here for a quick spring break trip with the family while my oldest daughter kicks off her college exploration tour. The trees and plants are in full bloom, but there's still enough nip in the air to remind you that winter isn't that far gone.

We're all coming out of March Madness this week. I watched more college basketball this season than I have in years — I'll blame the Nebraska men's run for pulling me in — and it was a fun one to get lost in.

Speaking of getting practical: our next How I AI session is coming up, and if you missed the first one with Laura Hubbell and my business partner, Kailash Duriaswami, this series is worth having on your radar. Less theory, less hype, more "here's exactly how we're using this on a Tuesday morning."

How I AI: with Laura Hubbell, CFA | SignatureFD

Every RIA has AI tools now. Almost none of them are actually using them. Advisors and ops teams signed up, ran a few prompts, and quietly went back to doing…

luma.com/kjsaeybz

Our team at Milemarker has also been shipping some of the most transformative updates we've ever put out, and it's a delight to watch the immediate impact on how firms run their businesses.

This week, I want to focus on a comment from UCLA women's basketball head coach Cori Close as she recapped her championship season. The principles she laid out are massively applicable to today's talent game — a game that's too often short on virtue, grit, and character.

Here's this week's dollar-slice-pizza-fueled Rising Tide.

Now, on to this week's article.

1. Talent Is Your Floor

2. Podcast: The Hidden Cost of Fragmented Data 🎧

3. Milemarker On the Road ✈️

Talent Is Your Floor

Sunday afternoon. Post-lunch. Remote in hand.

I turned on the women’s national championship game. South Carolina vs. UCLA.

I’ve lived in South Carolina long enough to appreciate what Dawn Staley has built. Six straight Final Fours. Three national titles. A third consecutive championship game appearance. This year’s team wasn’t supposed to get here — they had the youth, the transfers, the question marks. But they showed up anyway. That’s what Staley’s program does.

They ran into a buzz saw.

UCLA led from the opening tip and never let up. South Carolina shot 29% from the field. The Bruins won 79-51 — the third-largest margin of victory in championship game history. It was pretty obvious by halftime, but truly over by the third quarter. South Carolina could not find an answer.

I almost turned it off. I usually do when a game gets that lopsided.

But I stayed.

I watched the final buzzer. The confetti. The celebration. The postgame interviews.

And then UCLA head coach Cori Close said something that stopped me cold.

Close had been at UCLA for 15 seasons. Mentored by John Wooden himself. Never won a national championship. This was her program’s first — ever — in NCAA women’s basketball. And in the biggest moment of her career, standing on the court with confetti falling around her, she said this:

“The talent is our floor, but our character will determine our ceiling.”

She’d been telling her team that all year. Not just in the locker room before the title game. All season long. It was their operating principle.

Read it again: talent is the floor. Character is the ceiling.

Think about how counterintuitive that is. We live in an era obsessed with talent. We recruit for it. We pay premiums for it. We build entire strategies around acquiring the most talented people we can find.

And we should. Talent matters. UCLA had five seniors score in double figures. Gabriela Jaquez put up 21 points, 10 rebounds, and 5 assists. Lauren Betts — the Most Outstanding Player — had 14 and 11. That’s not a fluke. That’s elite talent performing at the highest level.

But here’s what Close understood: talent got them on the court. Character is what made them play the way they played. The connectivity. The attention to detail. The composure under pressure on a stage they’d never been on before.

Talent assembled the roster and helped them win before the pressure got turned up. Character won the championship.

I think this has real implications for all of us.

Wealth management is full of talented people. Smart people. Credentialed people. People who can analyze a portfolio, build a financial plan, and articulate a market thesis incredibly well.

But talent alone won’t build a great firm. It can’t create a culture that retains people for decades if all that talent isn’t backed by character that stands up to pressure. It doesn’t produce the kind of client relationships that survive bear markets and generational transitions.

Character is the ceiling.

Character is the advisor who calls a client before the client calls them — not because there’s an alert in the CRM, but because they actually care. Character is the ops team that stays late to fix a data issue nobody would have noticed for weeks. Character is the leader who gives credit publicly and takes blame privately. Character stays curious when something seems wrong. It doesn’t flash to anger reflexively. It doesn’t celebrate when something goes wrong for someone. It takes care. It perseveres.

Character is what shows up when the pressure is on.

Dawn Staley demonstrated character too on Sunday. After getting blown out in the championship game for a second straight year, she stood at the podium and acknowledged her team’s effort wasn’t enough that day. She gave UCLA credit. She kept the focus on her players. She handled it with grace.

That’s character when the ceiling caves in.

We’re in a talent arms race in this industry right now. Firms are fighting over advisors, technologists, and operators. NIL deals for financial services professionals might as well exist given the way recruiting has evolved. And I get it — you need talented people to compete.

But talent without character is a team that looks great on paper and falls apart when it matters.

Character without talent is a team that overachieves but eventually hits a wall.

The magic — and Close figured this out over 15 years — is when talent becomes the baseline expectation and character becomes the differentiator. When the people on your team are both excellent at what they do and excellent at who they are. When those young women walked in to her gym in LA, she didn’t expect them to be fully formed. She taught them skills on the court and for life.

I’m thankful to be surrounded by people like that. At Milemarker. With our clients. With the partners and advisors I get to work alongside every week. People whose character consistently exceeds their talent — and their talent is already remarkable.

That’s the ceiling worth chasing.

“The talent is our floor, but our character will determine our ceiling.”

Fifteen years of coaching. One quote. One championship. And a lesson that applies far beyond basketball.

Build talented teams. Absolutely. But never stop measuring what actually matters.

The floor gets you in the game. The ceiling determines how high you go.

On the Pod: Best Of — The Hidden Cost of Fragmented Data

Episode 139: On this week’s episode, Kyle Van Pelt sits down with Kailash Duraiswami, Chief Technology Officer at Milemarker, where he leads the development of data infrastructure and AI-powered solutions for modern advisory firms.

In this episode, Kyle Van Pelt talks with Kailash about his unconventional path from launching an RIA straight out of college to building tech that transformed data operations for financial firms. They unpack the challenges firms face with fragmented data, the importance of centralized infrastructure, and how AI will reshape wealth management. They discuss why firms need to reclaim ownership of their data, how to avoid becoming an “accidental CTO,” and how Milemarker is building scalable, simplified tech solutions for advisors navigating a multi-platform, AI-enabled world.

In this episode:

(00:00) - Intro

(03:17) - Kailash's money moment

(08:20) - What is Pantenix?

(11:34) - The value of a data warehouse

(13:55) - Kailash's thoughts on cloud-based infrastructure

(15:40) - The importance of data platforms

(19:53) - Why becoming a CTO should be intentional

(23:54) - AI in wealth management

(26:10) - The advantage of building your own language models

(33:15) - Why CTOs in RIAs need to understand wealth management

(37:26) - Why all-in-one platforms limit user experiences

(40:27) - Kailash's Milemarker Minute

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

1. Nashville, TN - April 13-14

2. New York, NY - April 20

3. Tampa, FL — April 21-22

4. Chicago, IL — April 23-25

5. Omaha, NE — May 5

6. Nashville, TN — May 7

7. Indianapolis, IN — May 11-13

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

Jud Mackrill

Happy holiday weekend, everyone. Hope you're getting some time to slow down with your people.

Quick note before we get to this week's article.

I've been in daily conversations with firms about AI for months now. And the same gap keeps showing up. There's no shortage of excitement about what AI could do. But there's a real shortage of clarity on what it actually looks like on a Tuesday morning when your ops team is drowning.

So we're launching a new webinar series: How I AI.

The idea is simple. Less theory. Less hype. More "here's exactly how we're using this in real practice, every day."

The first session features Laura Hubbell, CFA and our CTO Kailash Duraiswami, and we're going to get as practical and specific as we can — real workflows, real tools, real results. The kind of stuff you can take back to your team the same week.

Sign up to join us here:

How I AI: with Laura Hubbell, CFA | SignatureFD · Luma

Every RIA has AI tools now. Almost none of them are actually using them. Advisors and ops teams signed up, ran a few prompts, and quietly went back to doing…

luma.com/kjsaeybz

Now, on to this week's article.

1. What the Romans Meant by Best

2. How to Build Deep Client Relationships at Scale 🎧

3. Milemarker On the Road ✈️

What the Romans Meant by Best

I’ve been a marketer since fifth grade.

I sold stuff to my classmates between classes. Little arbitrage plays. Buy low at the store, sell high in the hallway. Everybody won.

Until the school created a new “non-solicitation” policy. My first cease and desist. They didn’t name me. They didn’t have to.

I didn’t necessarily “stop”. I just pivoted into different verticals.

That instinct — take what exists and make it better — has a name. It’s over 2,000 years old:

Optimus.

Most people think “opti-” is one root. It isn’t.

It comes from two ancient ideas that merged.

First: Latin ops — power, wealth, abundance.
Originally, it meant to produce, to create plenty. Over time, it evolved into optimus — “the best.” Not through talent, but through output and resources.

“Best” once meant something closer to most resourceful.

Second: Greek opsis — sight, appearance, the act of seeing.
From it came optikos — anything related to vision.

Two different meanings:

• Abundance and performance

• Perception and appearance

Both ended up in “opti.”

That’s why we get words like:

• From Latin: optimal, optimize, optimism

• From Greek: optic, optics

Even today, when people say “the optics look bad,” they mean appearance — not performance.

That distinction matters.

We treat “optimize” like one thing.

It isn’t. It depends on what you’re trying to improve — output, or perception.

Some things optimize through time. Great wine doesn’t come from working harder at the crush. It comes from waiting. Barrel aging. Patience. The winemaker’s hardest job is resisting the urge to do.

Some things optimize through intensity. Surgery. A product launch. A compliance audit. These demand everything you’ve got inside a narrow window. You can’t casually optimize a scalpel.

Some things optimize through repetition. Your golf swing. Your sales pitch. Your morning routine. Not one heroic effort. Ten thousand small ones, each a little better than the last.

Some things optimize through subtraction. The best writing is rewriting — cutting what doesn’t belong. The best portfolios aren’t built by adding positions. The best tech stacks aren’t the ones with the most tools.

And some things optimize through sight. You can’t fix what you can’t see. Dashboards. Data. Transparency. Before you produce abundance, you need clear eyes.

That’s the Greek root earning its keep.

Here’s where it gets dangerous.

My favorite plant in Charleston is the bottlebrush. Bright red blossoms. Hummingbirds love them. They bloom throughout the year.

The other day, my father-in-law was about to trim his way back. Thankfully, someone stopped him.

A bottlebrush can handle a prune of up to a third — and it’ll come back stronger. More blossoms, more life. But push much past that line and it may never recover.

Optimization has a threshold. Most people don’t know where it is until they’ve crossed it.

Because optimization takes so many forms, it’s easy to apply the wrong kind. Or the right kind in the wrong dose.

Bringing intensity to something that needs patience. Adding repetition where subtraction would serve. Obsessing over optics — how it looks — when the real problem is ops — how it performs.

In wealth management, the most common version? Optimizing for activity instead of outcome. More reports. More meetings. More tools. More data. Pruning past the line.

The Romans would call that a corruption of ops. The appearance of work without the abundance it’s supposed to produce.

Real optimization starts with one question the Romans would’ve understood:

What are you actually trying to produce in abundance?

Time? Optimize by subtracting.

Scale? Optimize by systematizing.

Clarity? Optimize by seeing.

Value? Optimize by compounding.

One more thing.

Voltaire said “the perfect is the enemy of the good.”

But optimus never meant perfect. It meant the best you can do with what you’ve got.

The Latin superlative wasn’t aspirational. It was practical. The optimates — Rome’s ruling class — took their name from it. Not the dreamers. The doers with resources.

That fifth-grader didn’t have a business license. No capital. No permission from the administration.

But he had a product, a market, and a hallway.

That was optimus for a ten-year-old.

What’s yours?

On the Pod: How to Build Deep Client Relationships at Scale

Episode 138: On this week’s episode, Kyle Van Pelt sits down with Michael Vedders, Senior Vice President of Marketing & Enterprise Resources at NorthRock Partners. With more than a decade of experience in marketing and leading complex organizational projects, Michael has helped build teams, launch major branding initiatives, produce compelling creative, develop multi-channel planning, and use insights to inform strategy.

Michael talks with Kyle about how wealth management firms can build deep client relationships at scale. He discusses the importance of storytelling in creating a strong brand narrative, how NorthRock's personal office business model works, and why the future belongs to firms that use data and automation to serve more people and build deeper human connections.

In this episode:

(00:00) - Intro

(02:38) - Michael's money moment

(04:58) - Michael's frustration with traditional wealth management

(07:24) - What marketing really means in wealth management

(10:02) - How to build trust and deeper client relationships

(12:48) - The "quarterback" model of financial advice

(16:42) - How NorthRock manages deep relationships at scale

(21:52) - NorthRock's personal office business model

(22:54) - Michael's outlook on the future of financial advice

(29:03) - Redefining performance beyond returns

(30:57) - Michael's Milemarker Minute

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

1. New York, NY — April 9-10

2. Tampa, FL — April 21-22

3. Chicago, IL — April 23-25

4. Omaha, NE — May 5

5. Nashville, TN — May 7

6. Indianapolis, IN — May 11-13

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

Jud Mackrill

Good morning.

Writing this from Tampa. My youngest has a tournament today — second trip down here this week, and I'm not complaining once.

Bermuda grass. Warm air. 7am. There are worse ways to start a day.

This week I'm pulling back the curtain on a routine we run at Milemarker that's quietly become one of our most important cultural anchors. I'll also sneak in some college football, because I can't help myself.

Here's this week's Rising Tide.

1. From Transactional to Transformational

2. How Financial Advisors Can Turn Messy Data into Actionable Results 🎧

3. Building Workflows Webinar Recap

4. Milemarker Announces Integration with SmartX

5. Milemarker On the Road ✈️

From Transactional to Transformational

I’m back in Tampa for the second time this month. And I’m not complaining.

This city has something going for it. The energy is good. The food is better. If you haven’t had the chef’s burrito at Green Lemon on South Howard, fix that. It’s one of those spots that keeps pulling me back.

But that’s not what this week is about.

This week is end-of-month. And at Milemarker, end-of-month means something specific.

We get together as a team. We walk through the business — the mission, the product, the customers, the numbers. We talk about where we are. We look back first. Then we look forward. And then we go forward together.

It’s not complicated, but it is phenomenal.

Here’s why: The last section of every one of these meetings is the part I care about most. It’s the part where we acknowledge each other.

In 22 years of doing this work, I have never experienced anything more rewarding than this practice. Full stop.

When you take time — real, intentional time — to acknowledge the people you go to battle with every day? The people who bring their best to your company, your customers, your culture? There is nothing like it.

And the more I do it, the more I wish everyone did it. But I know most places think there too busy to make time for it. I’ve worked at enough companies to know that acknowledgment is rare. Most people go years without hearing it from the people they work alongside.

Here’s what I’ve learned: this practice changes you as a leader.

When you understand your people deeply — not just from your own interactions, but from the collective, from what everyone on the team sees in each other — it changes everything. It changes how you value them. It changes how you think about the work. And suddenly, the whole thing stops being transactional. It becomes something far greater.

A person who has had a huge influence on my life is Tom Osborne. Most people know him as the legendary Nebraska football coach. 255 wins. Three national championships. A record of 255-49-3 across 25 seasons. The College Football Hall of Fame waived its three-year waiting period to get him in.

But what most people don’t know is that Tom Osborne holds a PhD in educational psychology from the University of Nebraska. He earned it in 1965 — before he ever became a head coach. He went on to write multiple books, including More Than Winning and Faith in the Game, that had nothing to do with X’s and O’s. They had everything to do with people.

Osborne talked extensively about the shift from transactional leadership to transformational leadership. He described how, early in his career, everything was about outcomes — beat Oklahoma, win a national championship, meet the expectations. And for the first 10 to 15 years, he operated in that transactional mode.

But over time, something changed. He stopped chasing the scoreboard and started investing in the people. He put players at the center. He built a culture where the staff served the athletes, not the other way around. He believed the best way to change behavior was to catch someone doing something right and reinforce it.

And when he made that shift? That’s when the championships came. The three titles — in 1994, 1995, and 1997 — all came after he moved from transactional to transformational.

I think about this a lot.

In our industry — wealth management, fintech, whatever you want to call it — we’re surrounded by transactions. Integrations. Data feeds. Contracts. Migrations. Basis points. It’s easy to let the whole thing become mechanical.

But the companies that win aren’t the ones optimizing for transactions. They’re the ones building cultures where people feel seen, valued, and invested in. Where acknowledgment isn’t a quarterly HR exercise. It’s woven into the rhythm of how the team operates.

When you come together at the end of the month and someone says something about a colleague that reveals a depth of understanding you didn’t expect — that’s transformational. When a team member who’s been grinding on a complex integration hears, from someone in a completely different function, that their work mattered — that’s transformational. When people feel like the work they do connects to something bigger than a deliverable — that’s the whole game.

Osborne built one of the greatest dynasties in college football history. But he didn’t do it by running better plays. He did it by caring about people more deeply than anyone else in the building.

That’s the model. That’s what I’m chasing.

If you’re leading a team — of any size, in any industry — I’d challenge you to try this. End your next team meeting with acknowledgment. Not performance reviews. Not KPIs. Just one simple question: Who on this team do you want to acknowledge, and why?

You might be surprised what happens next.

Have a great weekend. Go acknowledge somebody.

On the Pod: How Financial Advisors Can Turn Messy Data into Actionable Results

Episode 137: On this week’s episode of Next Mile, I sit down with Verity Larsen, Founder & CEO of Versoft Consulting. Versoft partners with RIAs to help navigate complex technology decisions, system conversions, and data strategy.

Verity talks with Kyle about the realities behind data lakes in wealth management and why maintaining clean, accurate data is harder than it looks for RIAs. From the myth of "clean data" to the hidden costs of data lakes, Verity shares a behind-the-scenes look at why so many firms struggle to turn data into actionable insights. She also explores the limitations of AI, the operational disconnects that quietly slow firms down, and what it truly takes to make data work for growth and better decision-making.

In this episode:

(00:00) - Intro

(02:00) - Verity's money moment

(04:33) - The challenge of validating data in system conversions

(08:40) - What it takes for an RIA to maintain clean data

(13:28) - The disconnect between management and staff workflow

(16:43) - Common reasons people hire Versoft

(20:53) - How people can make the most of their current technology

(26:27) - Why systems calculate the same metrics differently

(32:01) - The limits of AI in data and system management

(37:43) - The truth about data lakes: adoption vs. actual results

(40:11) - What firms should be doing with their data lakes

(42:28) - The next best step after centralizing data

(44:47) - Verity's Milemarker Minute

Building Workflows Webinar Replay

If you missed our webinar earlier this week, be sure to check it out here.

Building Workflows that actually work

Discover how Milemarker leveraged Automation and data-driven strategies to optimize revenue and streamline business growth.

www.milemarker.co/case-studies/building-workflows-that-actually-work

SmartX Announces Integration with Milemarker

We are pleased to have announced our integration with SmartX earlier this week. This is only the beginning and we are excited about how we can dramatically enrich the experience of advisors looking to have deeper control and insight across their asset management.

SMArtX + Milemarker | AI-Powered Dashboards & Automation

Take your SMArtX data to the next level. AI agents, custom dashboards, and smart automation — all inside your firm's branded console. Live in days.

lp.milemarker.co/smartx

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

1. Tampa, FL — March 28-29

2. Baltimore, MD — March 31

3. New York, NY — April 9-10

4. San Francisco, CA — April 14-15

5. Tampa, FL — April 21-22

6. Chicago, IL — April 23-25

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

Jud Mackrill

Good morning.

Thursday afternoon, Nebraska won its first NCAA Tournament game in program history. 129 years of basketball. Nine trips to the tournament. Zero wins — until now.

It got me thinking about the places and moments that stick — the ones that are impossible to replicate and easy to overlook. This week's main piece is about that.

Also this week: a new podcast episode on bringing consumer fintech into wealth management with our friends at Wealth.com, our upcoming webinar on building workflows that actually work (March 25th — register if you haven't), and where you can find the Milemarker team on the road.

Here's the Rising Tide. Have a great weekend.

1. There Is No Place Like

2. Bringing Consumer Fintech and Wealth Management Together 🎧

3. Webinar: Building Workflows That Actually Work

4. Milemarker On the Road ✈️

There Is No Place Like

It’s a beautiful Thursday afternoon here in Charleston. I just wrapped up a marketing summit with my team — we held it at my house — and we finished just in time to flip on the 11:40 Central tip.

Nebraska vs. Troy. First round. NCAA Tournament.

Quick context if you’re not a college basketball person: Nebraska men’s basketball has been one of the least successful programs in NCAA history. Going into today, they were 0-8 all-time in the tournament. The only power conference program to have never won a first-round game. Not once.

This year was different. The Huskers came in 26-6. No. 4 seed. Best in program history. A team that opened the season 20-0. And today they didn’t just win — they dominated. Nebraska 76, Troy 47. Pryce Sandfort hit seven threes and scored 23. The defense held a team averaging 80+ points to 47. It was the largest margin of victory for any program’s first-ever NCAA Tournament win.

My oldest son Gideon is a freshman at Nebraska. He was home with us — he’s part of our marketing team, so he was at the retreat. And I got to watch this historic game sitting right next to him.

Now here’s the thing about being a Nebraska fan. The good, the bad, sometimes the ugly — there’s this pervading part of your identity that at the end of the day, there’s just something special about that place. Something special about the people. How it all works. There’s a saying: there’s no place like Nebraska. I was born there and spent a lot of my years all over the country and I fundamentally believe it. It’s deep in me. It’ll never go away.

Sorry, this isn’t really a Nebraska tourism newsletter. Thanks for making it this far.

The chances are, if I asked you, there are parts of your life — subcultures, communities, experiences — that are just distinct. Different. Maybe it’s how you grew up in whatever part of the world. Maybe it’s a moment in time when you were building something. Maybe it’s the instant you all of a sudden hit that inflection point and everything changed.

There’s no place like it.

And I’m afraid that in the way the world goes — rapid building, consolidation, scale at all costs — this idea of uniqueness gets lost. It gets underappreciated. Because it’s not monetary. Usually it’s actually far from that. Sometimes money can even be a distraction to the thing that matters. But it’s something that’s really important to everyone there. It’s palpable.

I’ve been fortunate to experience a few of these.

There’s no place like seeing At the Drive-In play to 150 of your community in an underground club — the last time before they headed off on a 17-year hiatus.

There’s no place like seeing Rage Against the Machine play their second-to-last live performance at MSG.

There’s no place like when I was at Orion, when we hit the moment and implemented the tweaks that let our inbound marketing flood in. We became the brand. We changed the game.

There’s no place like when we unified all those brands at a national RIA and built a far more modern infrastructure — and all of a sudden transformed the lives of our advisors.

There’s no place like hitting product-market fit on an idea that is deeply ingrained in what you believe in and what you know will reshape the industry.

There’s no place like working alongside a team that you love more than yourself and would do anything to take care of.

There’s no place like working with that team late into the evenings, through the weekends, and building something from nothing.

That’s zero to one. And honestly, for me, zero to one is where the magic happens. It’s heads down. Doing the work. Getting through differences and finding consensus. Creating something from nothing. It’s this crazy thing that allows you to create a world that is completely its own.

I’m so thankful for every opportunity I’ve had to be part of that. And I believe I’m part of it right now.

There’s no place like it.

I hope you have those places you can recall. Or better yet — I hope you’re making them right now. Because this isn’t something that happens to you. It’s a place you create.

There’s no place like it.

Have a great weekend.

— Jud

On the Pod: Bringing Consumer Fintech and Wealth Management Together

Episode 136: On this week’s episode, Kyle Van Pelt sits down with Nicole McMullin, Senior Vice President of Product at Wealth.com. Nicole is a seasoned product leader with a proven track record of building and scaling high-performing product organizations. She brings deep experience in product strategy, cross-functional leadership, and translates customer needs into meaningful outcomes. 

Nicole talks with Kyle about the intersection of consumer fintech and advisory technology and how modern fintech principles can transform the advisor-client experience. She explores how new tools, AI workflows, and integrated platforms are helping advisors move away from manual processes and toward more proactive, emotionally intelligent conversations with clients.

In this episode:

(00:00) - Intro

(03:09) - Nicole's money moment

(09:42) - What advisory firms can learn from consumer fintech

(12:58) - Nicole's 'aha' moment at Wealth.com

(13:37) - Wealth's new tax planning strategy

(14:44) - Addressing fragmentation in wealth management

(16:26) - What attracted Nicole to join Wealth.com

(21:46) - How advisors should evaluate new technology

(23:33) - Nicole's outlook on the future of wealth management

(27:56) - How Wealth.com provides the best wealth management experience

(30:16) - Nicole's Milemarker Minute

Webinar: Building Workflows That Actually Work

Workflow automation promises better processes, smoother handoffs, and more efficient teams. But in many firms, even well-designed workflows end up being ignored.

Join us in this upcoming webinar to explore why that happens—and what it actually takes to build workflows that teams will actually use.

Register here:

Building Workflows that actually work · Luma

Workflow automation is having a moment in wealth management. Better process design. Smarter handoffs. Systems that promise to eliminate the back-and-forth that…

luma.com/90c6xqjp

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

1. Tampa, FL — March 24

2. Scottsdale, AZ — March 24-26

3. Tampa, FL — March 28-29

4. Baltimore, MD — March 31

5. New York, NY — April 9-10

6. San Francisco, CA — April 14-15

7. Tampa, FL — April 21-22

8. Chicago, IL — April 23-25

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

Jud Mackrill

Mid-March. The best time on the sports calendar.

Conference tournaments are wrapping up. Selection Sunday is tomorrow. Brackets are about to consume every group chat, office Slack channel, and family dinner for the next three weeks.

I'm coming off a few days in South Florida — good conversations, good weather, team scattered all over the map doing their thing. Now I'm back in Charleston, settling into the weekend, and very much looking forward to watching it all unfold.

But before the brackets take over, something from this week's Big 12 tournament caught my attention. They debuted a full LED glass court in Kansas City — the entire floor is a screen — and the players’ reactions were fascinating. Not because they were surprising, but because they mirror something I see in wealth management every single day.

This week: what a basketball court can teach us about change management.

Here's the Rising Tide. Enjoy your weekend.

1. Playing on Glass

2. Relentless, Relevant, and Ready: Orion Ascent Recap 🎧

3. Webinar: Building Workflows That Actually Work

4. Milemarker On the Road ✈️

Playing on Glass

March Madness is almost here.

Conference tournaments are happening this week. Sunday, the bracket drops. If you’re lucky, your team stays relevant for a week. Maybe two. If you’re really blessed, three.

This is one of the best stretches in sports. It’s also one of the worst for productivity. At previous wealthtechs and RIAs, we’d do a chili cook-off. Brackets printed. Focus is on the 5-12 match-ups and less on whatever your version of TPS reports may be. 

But this week, something bigger than a bracket caught my eye.

The Big 12 tournament in Kansas City debuted a full LED glass floor. The entire court is a screen. Controlled from an iPad. Team logos morph during intros. A shattered-glass animation fires after dunks. Sponsorships rotate in real time beneath the players’ feet.

It looks like the future.

It also gave a guy a migraine.

After Kansas State’s loss to BYU on Tuesday, forward Taj Manning was blunt. He called the floor slippery. Said his teammate Khamari McGriff got a migraine from the flashing lights mid-game. Called it an eyesore. Said nobody wants to play on it.

He wasn’t alone. BYU’s AJ Dybantsa — a likely top pick in this year’s NBA draft — said he liked the concept but the glass was slick. Arizona State’s Allen Mukeba said the shoes and the surface just didn’t match. Iowa State’s Killyan Toure said the flashing colors were disturbing. Kansas coach Bill Self brought his team to KC a day early just to practice on it. His review: functional, but different.

Here’s an unexpected wrinkle: McGriff — the guy who got the migraine — said he actually thought the floor was cool. He noted he gets seasonal migraines anyway. Even the refs said the spring-action frame was easier on their knees than hardwood.

Same floor. Wildly different experiences.

So will they scrap it? I don’t think so. They totally did.

Twitter tweet

The floor was built by a German company called ASB GlassFloor. The technology has been used in Europe since 2008. The NBA All-Star Game has featured it. This was just its first sanctioned appearance in American college basketball.

Fast forward three years. Major arenas across the country will have some version of this. The economics are too obvious: dynamic sponsorships, multi-sport flexibility, broadcast-ready visuals that change on the fly. That’s not a toy. That’s a business model.

But the technology has to improve. The traction needs work. The lighting effects need to account for players sensitive to rapid visual changes. The grip coating needs another generation of refinement.

Version 1.0 always has problems. That doesn’t mean the concept is wrong.

Sound familiar?

I just got back from the Future Proof conference in Miami. And I keep hearing the same conversation: firms trying new technology — AI tools, note-taking assistants, workflow automation, new planning software — and getting mixed results. Some of it feels great. Some feels hard. Some feels like it’s giving everyone a headache.

There’s a growing awareness of what firms should be doing. But there’s a widening gap between awareness and execution. Everyone knows AI is changing how people work. Fewer people know what to do with it on a Tuesday morning.

And all along the way, there’s a gravitational pull toward the naysayers. The person who got the migraine. The advisor who tried the new CRM for a week and hated it. The ops person who says the old way was fine.

Listen to them. Respect them. Be empathetic.

But don’t let them drive.

The future isn’t binary. It’s not “this works perfectly” or “burn it down.” It’s progressive. The LED floor will get better. The AI tools will get better. The integrations will get smoother. But only if we keep playing on them.

What’s the glass floor at your firm right now? What’s the thing that’s clearly the future — but isn’t quite there yet?

Have a great weekend. Enjoy the games.

On the Pod: Relentless, Relevant, and Ready: Orion Ascent Recap

Episode 135: On this week’s episode, Kyle Van Pelt sits down with Jessica Perez, VP of Growth at Milemarker. Jessica brings a boots-on-the-ground perspective to the wealth management technology space, working directly with advisory firms to help them unlock the full potential of their data. 

Kyle and Jessica recap key lessons from the Orion Ascent conference, where the central theme was “Relentless”—a mindset focused on continuous improvement across technology, client experience, and firm operations. They discuss how advisors can avoid the overwhelm that often follows large industry events and instead identify one or two meaningful priorities to pursue. Jessica also shares her perspective on evaluating technology partners, embracing innovation like AI without chasing every trend, and focusing on the changes that truly move an advisory firm forward.

In this episode:

(00:00) - Intro

(01:28) - Orion Ascent recap

(03:15) - How advisors can apply a relentless mindset without getting distracted

(07:29) - The "AI frenzy" and improving client experience through smarter technology

(10:29) - How AI conversations are shaping advisor technology strategy

(13:24) - From tinkering to transformation

(15:02) - Evaluating whether technology vendors are true partners

(20:11) - Why data sharing and integration matter more than ever

(25:08) - Turning conference inspiration into real firm improvements

(38:43) - Jessica's Milemarker Minute

Webinar: Building Workflows That Actually Work

Workflow automation promises better processes, smoother handoffs, and more efficient teams. But in many firms, even well-designed workflows end up being ignored.

Join us in this upcoming webinar to explore why that happens—and what it actually takes to build workflows that teams will actually use.

Register here:

Building Workflows that actually work · Luma

Workflow automation is having a moment in wealth management. Better process design. Smarter handoffs. Systems that promise to eliminate the back-and-forth that…

luma.com/90c6xqjp

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

1. Sarasota, FL — March 24

2. Tampa, FL — March 28-29

3. 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

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.

Using Data Automation To Optimize Revenue

Discover how Milemarker leveraged Automation and data-driven strategies to optimize revenue and streamline business growth.

www.milemarker.co/case-studies/ai-compliance

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

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 Appoints Adrienne Paulsen as Vice President of Operations

Wealth Management Data Infrastructure Leader Adds Veteran Orion Executive to Drive Operational Excellence and Client Success...

www.globenewswire.com/news-release/2026/02/23/3242596/0/en/Milemarker-Appoints-Adrienne-Paulsen-as-Vice-President-of-Operations.html

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

I hope you’re doing great.

Earlier this week I did a day trip to New York and back. Clients, prospects, partners, friends. Dense schedule. Long day. Worth it.

On the flight home, my brain wandered back to grad school. Specifically, to one of my favorite things from studying ancient languages: the difference between the present active tense and the aorist tense in Koine Greek.

I know. You didn’t open this newsletter for a grammar lesson.

But I think this one matters. It shows up in how we lead our teams, position our firms, and talk about what we’re building. I want to break it down.

Here’s this week’s Rising Tide.

1. What Are We Building?

2. How Creativity Fuels Better Financial Leadership with Andrew Evans 🎧

3. Milemarker On the Road ✈️

What Are We Building?

When you talk to technology companies, you’re often met with quick, rhythmic statements. We are building a better mousetrap. We are redefining cloud compression. We are launching a new way to wear shoes.

Big ideas. Competitive ideas. The kind that help you quickly get the gist while aligning a team of builders and problem solvers around a shared direction.

When you speak with most RIAs, you hear things packaged quite differently. “We help families enjoy their wealth.” “We guide clients toward financial independence.” “We provide holistic planning for retirees.”

Noble, true—and almost always past-tense in their posture. The mission is declared. The identity is established. The sentence is complete.

I’m sure you can spot the difference, and it matters more than you might think.

In Koine Greek—the language the New Testament of the Bible was written in—verbs carry something English often obscures: aspect. Specifically, the present active indicative tense communicates action that is continuous, ongoing, and in process. Not something that happened. Not something that will happen. Something that is happening right now, with the subject actively doing it.

The aorist tense, by contrast, is like a snapshot. It says something occurred. Full stop. No texture. No duration.

The present active is kind of like a video that puts you inside the action while it’s unfolding versus the aorist tense this more akin to a narrator telling you what occurred.

One Greek grammarian described it this way: the aorist views an action from the outside, as a completed whole. The present tense pulls you inside the action—up close, ongoing, in motion.

Of course, you didn’t come here to get a grammar lesson. Maybe you were hoping for something like a leadership framework. That’s where the application of our grammar knowledge comes into play.

Technology companies—the best ones, at least—instinctively operate in the present active state. They describe what they are in the process of building. The verb hasn’t resolved. The work is not done. And that’s the point. The unfinished nature of the statement is what creates energy. It’s what attracts builders, investors, and early adopters. It signals that there is still meaningful work to do and that the people doing it are actively in motion.

“We are building the data infrastructure that will power the next generation of wealth management.”

That sentence is alive. It’s happening. You can join it.

“We built a great data platform for advisors.”

That sentence is a plaque on the wall. It’s finished. There’s nothing left for you to do but admire it.

Most RIAs don’t have a building problem. They have a tense problem.

When everything about how you describe your firm lives in the completed state—we are a fiduciary, we serve high-net-worth families, we provide comprehensive planning—you’ve created an identity, but not a trajectory. Identity is obviously important. But identity without trajectory is a firm that might feel static, even when it isn’t.

The firms that are winning right now—the ones attracting next-gen talent, scaling past $1B without doubling headcount, commanding premium valuations at exit—they talk differently. Not because they hired a better marketing agency, but because they think differently about what they’re doing.

They are building something. Present tense. Active voice. In process.

Here’s what happens when you shift from the aorist to the present active in how you talk about your firm:

Your team leans in. People want to be part of something being built, not something that’s already been built. The present active state tells your team there is still meaningful contribution to be made; that their fingerprints will be on what comes next. This is especially true for the next generation of talent you’re trying to recruit—they are not looking for a seat on a finished train. They want to help lay the track.

Your clients feel it. When a client hears “we are building a planning experience that adapts to how your life actually works,” they hear something different than “we provide comprehensive financial planning.” One is alive and moving toward them. The other is a brochure.

Your competitors can’t copy it. A static identity can be replicated. A firm in active motion—building, iterating, improving—is a moving target. It’s the difference between a fortress and a fleet.

Acquirers pay more for it. Enterprise value is a bet on the future. If your language, your culture, and your operations all communicate the completed state, an acquirer sees a business that has peaked. If everything about your firm communicates the present active state—we are building, we are scaling, we are deploying—an acquirer sees a business with unrealized upside. That’s what commands a premium multiple.

I think about this a lot in how we talk about Milemarker. We are building data infrastructure for wealth management. Not “we built” it. Not “we have” it. We are building it. Every day. The present active indicative. Continuous. Ongoing. In motion.

That’s not spin—it’s how good companies actually work. The product is never done. The integrations are always expanding. The platform is always evolving. Describing it any other way would be dishonest.

The question for you is simple: when you talk about your firm, are you inviting the listener into the story or are you just narrating the past?

Are you describing who you are—or what you are in the process of becoming?

The present active state doesn’t just change your language. It changes your posture. It changes your hiring. It changes what your team believes is possible.

And the firms that figure this out? They aren’t the ones that built something great.

They’re the ones that are still building.

On the Pod: How Creativity Fuels Better Financial Leadership

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Episode 132: On this week’s episode, Kyle Van Pelt sits down with Andrew Evans, Chief Executive Officer of Rossby. Before Rossby, Andrew served as Executive Vice President at TAG Advisors and as a Securities Principal at Cambridge Investment Research. 

Andrew talks with Kyle about entrepreneurship, growth, and designing better businesses. With a background in musical theater and a career that spans mortgage brokerage and financial advising, Andrew shares the parallels between creative careers and financial services, why repeatable processes beat flashy marketing plans, and how thoughtful design can transform the advisor experience. 

In this episode:

(00:00) - Intro

(01:39) - Andrew's money moment

(04:55) - Parallels between mortgage brokerage and financial advising

(07:07) - How Andrew built his early book of business

(11:50) - The financial-planning version of a closing credit

(13:07) - Redefining traditional conferences with The Unconference

(16:41) - How The Unconference generates the best business ideas

(19:43) - What it means to drive business forward

(25:04) - The concept of "less but better" in business and technology

(28:39) - Designing intuitive systems and reducing operational friction

(32:22) - Creativity, patience, and building differently

(35:16) - Andrew's outlook on the future of the financial services industry

(44:13) - Andrew's Milemarker Minute

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

1. San Diego, CA — February 22-27

2. New York, NY — February 28

3. Miami, FL — March 8-11

4. New Orleans, LA — March 9-12

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

Jud Mackrill

Wednesday I pointed the car toward Orlando, Florida. This morning I'm in a Jacksonville hotel lobby between client meetings, trying to get back to Charleston in time for my daughter's 14th birthday party tonight.

It's been that kind of week. I’ve had five conversations that each could've been their own newsletter.

There was one idea that kept creeping into every discussion: the AI-driven arms race and how it's hitting wealth management firms at every level. Then a piece called "Something Big Is Happening" went viral this week — 75 million views — and said out loud what a lot of us in the industry have been thinking but softly.

I think it’s time to stop softening the blow.

Here's this week's Rising Tide.

1. The Custodial Arms Race

2. Why the Future of Advice Is Less About Tech and More About People 🎧

3. Milemarker On the Road ✈️

The Custodial Arms Race

Why it's good — and why everyone needs to keep their head on a swivel.

Wednesday morning I was driving into Orlando when I got a call from an industry reporter looking for a scoop on an AI and a custodian working together.

This was coming off of Altruist's announcement of their Hazel-driven agentic solution that immediately turned heads and dropped share prices at the establishment custodians.

Even if I had a scoop, I’m careful to never comment when the news isn’t mine to share. I do, however, always enjoy catching up.

That phone call confirmed something I've been feeling for months.

This week, Matt Shumer, CEO of HyperWrite, published "Something Big Is Happening". It went viral — 75 million views in days. His argument is simple: the gap between what AI can actually do right now and what most people think it can do has gotten dangerously wide.

He put it perfectly: "I keep giving them the polite version. The cocktail-party version. Because the honest version sounds like I've lost my mind."

I felt that in my bones. I've been doing the same thing — speaking carefully about it at every conference, every call, every dinner. So let me stop.

The Polite Version Is Over

If your firm doesn't have a clear path to operating with AI in your workflow by the end of this year, you will spend 2027 feeling like you can't catch up.

That's not hyperbole. That's the trajectory.

Altruist didn't just launch a feature. They made a statement. The establishment custodians felt it immediately — not in their product roadmaps, but in their stock price. That kind of wake-up call gets boardrooms moving.

Shumer used a COVID analogy that's hard to shake. Think back to February 2020. Everything was normal. Stock market humming. Kids in school. Then three weeks later, the entire world rearranged itself. He writes: "I think we're in the 'this seems overblown' phase of something much, much bigger than Covid."

That's the speed we're operating at now. And this time, we know that it won’t be a temporary change.

Before you say "I tried AI and it wasn't that great" — Shumer addresses that head on. Judging AI based on a free-tier experience from 2024 is like evaluating smartphones by using a flip phone. The models today are unrecognizable from six months ago. The gap between public perception and current reality is actually enormous.

In our industry, that gap is where firms are going to get blindsided.

Here's what this looks like in wealth management right now:

• An advisor feeds a messy household portfolio into AI and gets a rebalancing recommendation — with tax-loss harvesting flagged — in minutes instead of days.

• A compliance team runs AI across their ADV filings and catches inconsistencies that would've taken a junior analyst more than a week to unearth.

• A firm surfaces patterns across their entire book and identifies cross-selling opportunities they've not been able to see before.

None of this is theoretical. It's happening today at firms that stopped waiting.

But AI Is Only as Good as the Data Underneath It

Here's what most people are missing: this isn't just about AI. It's about putting the technology you already have to work.

Most firms are sitting on a mountain of tools and data they barely use. The AI layer is powerful — but it's only as good as the infrastructure underneath it. Fragmented data across fifteen systems with no connective tissue? An AI copilot isn't going to save you. It's going to hallucinate on bad data and make you feel productive while you're standing still.

The firms that win in 2026 aren't the ones that bolt on the flashiest AI feature. They're the ones that get their data house in order first.

The Security Problem Nobody's Talking About

Here's the part nobody in the AI hype cycle is addressing.

Most advisors can't do what Shumer describes. Not yet. Not safely.

He tells people to feed AI a messy spreadsheet. Paste in quarterly data. Let it find the story. Great advice — if you're a tech founder working with your own data.

But if you're an RIA with a fiduciary obligation and client PII everywhere? You can't just drop a client portfolio into ChatGPT and hope for the best. Your compliance team would — and should — lose their minds.

Most off-the-shelf AI tools aren't built for regulated industries. When you type a prompt into a general-purpose chatbot, that data leaves your environment. It goes somewhere. For an advisor handling sensitive client information, "somewhere" isn't good enough.

This is the gap keeping most firms on the sideline. Not a lack of interest in AI. A lack of trust that it can be deployed securely.

That's why my team built what we built. Our AI sits on top of your data lake environment. The data is already there. Already governed. Already within your security perimeter. It doesn't leave. It doesn't get trained on for broader use. It doesn't go beyond the container it operates in.

This containerization gives your compliance team what they actually need to greenlight AI adoption. Not as an experiment. As infrastructure.

Because the goal isn't just to use AI. It's to use it in a way where you can look your clients and your regulators in the eye and say: this is secure, this is compliant, and this is how we deliver better outcomes.

Competition Makes Us All Better

Before anyone reads this as doom and gloom for the incumbents — this arms race is a good thing.

Custodians compete on technology. Advisors win. Platforms race to deliver better integrations. Firms win. Clients win.

That's the whole game.

Schwab, Fidelity, and Pershing aren't going to sit still while Altruist grabs headlines. They're going to respond. They're going to invest. They're going to ship. Every one of those moves benefits the advisor in the chair trying to serve their clients better.

The worst thing that could happen to wealth management technology is a comfortable oligopoly where nobody feels pressure to innovate. We had that for years. It wasn't great.

Shumer tells a story about a managing partner at a major law firm who spends hours every day using AI. Says it's like having a team of associates available instantly. He's not using it because it's a toy. He's using it because it works. And he expects it'll do most of what he does before long. That's a managing partner with decades of experience.

Now apply that same lens to our industry.

When I see Altruist swing big with Hazel, I don't see a threat. I see a spark. The custodians that lean in will come out stronger. The ones that dismiss it will get left behind. The advisors in the middle become the beneficiaries of a technology war where the real winner is the end client.

Is Your Tech Stack Bound for Extinction?

Every firm leader should be asking: is the technology I'm building on going somewhere — or slowly dying in plain sight?

Not every platform makes it through this next cycle. Some of the tools you rely on today are already on life support. You just can't see it yet.

Three questions to find out.

Is it being updated regularly? Not a press release twice a year announcing a "refreshed UI." Real updates. New capabilities. New integrations. A consistent shipping cadence. If your platform's release notes look like a ghost town, that's your signal. A platform going somewhere builds. A platform going nowhere maintains. If the last meaningful update was six months ago, you have your answer.

Is it being actively led? Does the team have a vision or are they just keeping the lights on? Is there someone out front casting vision and making bets? Or has it gone quiet — multiple ownership changes, no clear direction, nobody you can point to who's driving the ship? Pay attention to the silence.

Does it have its head in the ground on integration, automation, or AI? This is a big one. If your vendors don’t value integration outside of themselves forcing manual workarounds for things that should be automated — you have a problem. A platform going somewhere connects to everything and automates the repetitive stuff. A platform that’s going extinct wants you to export a CSV and upload it somewhere else.

The hard truth: switching costs feel high until you realize the cost of staying is higher.

What to Do This Week

Shumer's piece resonated because he didn't just sound the alarm. He told people what to do. Same energy:

1. Audit your integrations. Map every system. Find where data flows automatically versus where someone is manually moving it between platforms. Every manual handoff is a liability. Know where they are.

2. Put AI on a real problem. Not a toy problem. A real one. A portfolio review. A compliance question. A client communication. Use the paid model — not the free version, not a quick Google-style question. Give it context and data. See what comes back. As Shumer writes: "The people who are getting ahead aren't using AI casually. They're actively looking for ways to automate parts of their job that used to take hours."

   And check your ego. The managing partner at that law firm isn't too proud to use AI. He's doing it because he's senior enough to understand what's at stake.

3. Ask your vendors the hard questions. What's on their AI roadmap? When was their last major integration release? What are they shipping in the next 90 days? Vague answers tell you everything.

4. Get your team in the room. Block one hour. Show them what's possible. The biggest barrier to AI adoption isn't the technology. It's that the team hasn't seen what it can do on their actual work. One hour of hands-on exposure beats a year of reading about it.

5. Set a 90-day checkpoint. The pace of change means quarterly reviews aren't enough. Set a date. Reassess your stack, your AI adoption, your competitive position. If you're not materially further along, something needs to change.

Keep Your Head on a Swivel

New partnerships. New product launches. New competitive dynamics. Weekly, not quarterly.

Shumer's piece compared this moment to the early days of COVID — not because AI is a virus, but because the speed at which everything is about to rearrange itself will catch most people off guard.

He closes with something every wealth management leader needs to hear: "The single biggest advantage you can have right now is simply being early. Early to understand it. Early to use it. Early to adapt."

The people who move early don't just survive. They win.

The custodial arms race is here. It's the best thing that's happened to wealth management in a long time.

But only if you're paying attention.

If this resonated — share it with someone on your team who needs to read it. Most people won't hear this until it's too late.

On the Pod: Why the Future of Advice Is Less About Tech and More About People

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Episode 131: On this week’s episode, Kyle Van Pelt sits down with Joe Moss, Founder at AdvisorTechBook. With a background in real estate and data analysis, Joe has become a go-to resource for financial advisors looking to optimize their tech stacks. 

Joe talks with Kyle about the rapidly evolving world of advisor technology, AI, and personal branding in wealth management. He discusses how financial advisors can simplify their technology, leverage AI effectively, build meaningful personal brands, attract top talent, and grow organically in an industry where relationships matter most.

In this episode:

(00:00) - Intro

(01:26) – Joe’s money moment

(02:34) – Joe’s winding path to fintech

(05:47) – How people should evaluate AI in the future

(10:16) – The Zero Basis Points theory

(12:29) – The importance of data lakes in connecting AI capabilities

(18:49) – Why advisors need to tell their own stories

(20:41) – Strategies for attracting and retaining the best next-gen advisors

(27:35) – The difference between an audience and a community

(28:22) – Joe’s thoughts about the future of the financial services industry

(32:27) – Joe’s Milemarker Minute

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

1. New York, NY — February 18

2. San Diego, CA — February 22-27

3. New York, NY — February 28

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

Jud Mackrill

I'm in an unseasonably not-snowy Park City this week. Despite the warmth and lack of powder, it's still a hard place to beat.

Park City, February 5, 2026

I've been listening to a different live album every day. There's something about the uniqueness of each performance—the risk, the imperfection—that I keep coming back to. Maybe it stands out more now after watching lip-synced performances at the Grammys and hearing auto-tune become the default rather than the exception.

This week, I'm thinking about what it means to go live—and why that matters more than ever.

Here's this week's Rising Tide.

1. Going Live

2. Forging a Path to Freedom and Independence with Adam Spiegelman 🎧

3. Milemarker On the Road ✈️

Going Live

I accidentally took a Waymo in Atlanta a few weeks ago.

My Atlanta Waymo

Here's what happened: I ordered an Uber while on a highly detailed call and didn't really pay much attention to the Waymo notice, hopped in, and slowly crept to my destination. Just sensors, screens, and an empty front seat staring back at me like a confession of the future.

It was one of my top 10 worst Uber rides I've ever had.

The car was overly cautious at every intersection, hesitating at stop signs like a teenager with a learner's permit. It made routing decisions that made no sense—taking three right turns instead of one left. When another car wanted to merge, the Waymo just... stopped. Waited. Let itself get bullied by Atlanta traffic, which is not a city that rewards politeness.

But here's the thing I kept thinking about: this is temporary. The hesitation, the awkwardness, the inhuman rhythm of it—all of that will get optimized away. Eventually, Waymo will drive better than any human driver. Statistically, it probably already does.

Note that I wrote this article prior to seeing the news that people are still very actively involved in remotely controlling Waymo cars.

And that's the real problem.

When it works—really works—it'll be sterile. Safe. Optimized. The adventure gets automated out.

The Assembly Line Comes for Everything

We're watching automation accelerate in ways that felt theoretical six months ago.

If you've been paying attention to the AI agent space, you've probably heard of OpenClaw—the open-source AI agent that went from a weekend project to 100,000 GitHub stars in a week. People are buying Mac Minis specifically to run these things 24/7. They call it the "new team member." Not metaphorically. Literally: an autonomous system that checks your email, manages your files, and executes tasks while you sleep.

The assembly line was introduced in manufacturing a century ago. Now it's coming for everything else. Knowledge work. Creative work. The stuff we thought was safe because it required judgment.

And mostly, we're talking about this wrong. The conversation is always about what gets replaced. What I find more interesting is what becomes more valuable.

The Live Album Test

I've had live albums on repeat all week, and I think there's something useful in the comparison.

A studio can produce the perfect album. Every note precisely placed, every frequency balanced, every mistake erased. It's the Waymo of music—optimized, consistent, safe.

But there's something irreplaceable about real people playing real instruments in real time with real stakes.

Years ago, I spent time with Mike Mogis in his Lincoln, Nebraska studio, where we worked on an album for one of my friends at Presto!. Mike has built a career as a member of Bright Eyes and as a producer of several celebrated indie albums, including a couple by Phoebe Bridgers that won Grammys in recent years.

In the studio, the process of recording, editing, and refining is a grind. Hours adjusting tuning, adding layers, retaking riffs. Mike plays pretty much every instrument, has perfect pitch, and can understand what the artist is trying to achieve. He works in the moment to create something that will stand the test of time.

But it's art with an undo button.

Live recordings don't get that luxury.

Think about Nirvana's MTV Unplugged in New York. Kurt Cobain is clearly struggling. The performance is raw, vulnerable, and occasionally messy. He forgets lyrics. He changes arrangements on the fly. And it's devastating in a way that Nevermind can't touch—not because it's better produced, but because you're watching someone be human under pressure.

Or Rage Against the Machine's The Battle of Mexico City. There's no safety net. They're feeding off a crowd of 50,000 people, adjusting in real-time, channeling energy that can't be rehearsed. The studio version of "Killing in the Name" is precise. The live version is a confrontation.

Radiohead's In Rainbows: From the Basement is the inverse—controlled, deliberate, but with a tension that comes from knowing there's no second take. They're reinventing songs in real-time, trusting each other without a conductor.

The imperfections are proof of life.

What "Going Live" Actually Means

So what makes live performance work?

Improvisation—when the plan breaks down (and it always does), you adapt in the moment. Not with a pre-programmed backup plan, but with genuine creative response to something unexpected.

Collaboration—reading your bandmates, trusting without conducting, knowing when to lead and when to follow. This is different from coordination, which is just sequencing. Collaboration is anticipation.

Thinking on your feet—no undo button, no second take, no editing pass. The constraints create focus.

Reading the room—adjusting to the audience, the energy, the moment. The same song plays differently at a funeral than at a celebration. Context changes everything.

Presence—the stakes create a quality of attention that can't be faked. When failure is public and immediate, something sharpens.

These are the same skills that matter in work and life as automation handles the routine. The meeting where the slide deck doesn't matter as much as how you respond to the question that wasn't in your notes. The negotiation where the script breaks down. The presentation to the board where someone challenges your assumptions.

The live moments.

The Waymo Future

The Waymo will get better. The AI agents will get better. The studio will keep producing ever-more-perfect albums.

None of that makes the live skills less valuable. If anything, it makes them more valuable. When polished outputs become cheap, the ability to improvise becomes expensive. When consistency is automated, presence becomes rare.

I'm not arguing against automation. Progress is real.

But I'm increasingly convinced that the people who will thrive aren't the ones racing to automate their own capabilities. They're the ones doubling down on the live skills—improvisation, collaboration, thinking on their feet, reading rooms, and being present.

The future belongs to people who can go live.

On the Pod: Forging a Path to Freedom and Independence

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Episode 130: On this week’s episode, Kyle Van Pelt sits down with Adam Spiegelman, Founder and Wealth Advisor at Spiegelman Wealth Management, a firm that offers investment and wealth management programs and services for high-net-worth clients. The company’s mission is to develop enduring relationships with clients by providing professional guidance for a lifetime of financial security. 

Adam talks with Kyle about what it really means to go independent and why freedom, service, and intentional scale matter more in financial services. He shares why he left large firms to build a boutique RIA, the emotional weight of the transition, and how he maintains a human-centric approach in an automated world.

In this episode:

(00:00) - Intro

(01:32) - Adam's money moment

(03:18) - Navigating the LPL acquisition of Commonwealth

(06:07) - What Adam learned after going independent

(08:41) - The reality of independence

(10:09) - The challenges and rewards of building a custom technology ecosystem

(13:03) - What made Commonwealth technology user-friendly

(17:53) - Adam's vision for Spiegelman Wealth Management

(20:20) - What great service actually looks like in practice

(22:31) - Adam's growth strategies

(26:04) - Adam's outlook on the future of the wealth management industry

(28:30) - Adam's Milemarker Minute

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

1. Orlando, FL - February 11-13

2. Jacksonville, FL - February 13

3. New York, NY — February 17

4. San Diego, CA — February 22-28

5. New York, NY — February 28

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

Jud Mackrill

Greetings from a hopefully-soon-to-be snowy Charleston.

This week I've been in the trenches—new product rollouts, back-to-back meetings with firms across the country, the usual crunch. And somewhere in the middle of it all, I found myself thinking about MacGyver.

Stay with me.

There's something about constraints that either breaks teams or makes them wildly creative. This week's piece digs into why—and what AI is about to change about that equation.

Here's this week's Rising Tide.

1. MacGyver, Swiss Army Knives and Your AI-Driven Advisory Firm

2. The Real Alpha Inside Modern Advisory Work with Mitch Hamer  🎧

3. Milemarker On the Road ✈️

MacGyver, Swiss Army Knives and Your AI-Driven Advisory Firm

There's a reason MacGyver became a verb.

The show was ridiculous, of course. (Unless you were 10 years old in 1992).

A guy defusing bombs with chewing gum and a Swiss Army knife, escaping locked rooms with nothing but duct tape and sheer determination. Week after week, the same formula: impossible situation, no resources, ticking clock—and somehow he'd pull it off without all the hype of Walker, Texas Ranger’s need for unnecessary roundhouse kicks.

It was pure fiction. But the concept lodged itself in our cultural vocabulary because it captured something true about how creativity actually works.

We don't say "let's MacGyver this" because we believe we can literally build a radio transmitter out of a paper clip. We say it because we recognize the principle: sometimes the best solutions come when you're forced to work with what you've got.

The Comfort Trap

In wealth management—and honestly, across most of financial services—we've gotten comfortable. Not comfortable in the sense that business is easy, but comfortable in how we approach problems. We've built processes. We've established "the way things are done." We've created enough padding around our operations that we rarely feel the sharp eyes of true constraint anymore.

And that comfort is quietly killing our creativity.

When you're not fighting for survival, when you're not improvising your way through each day, something gets lost. The grit fades. The spontaneity disappears. The muscle memory for creative problem-solving atrophies because you simply don't need it anymore.

I see it in firms all the time. They have resources. They have technology. They have teams. But they've lost the scrappy energy that built them in the first place. They've traded the paper clip mindset for a procurement process.

The Fixers Without a Voice

Here's the thing—most firms actually have their own MacGyvers. They're the people in operations who've rigged together workarounds to keep things running. They're the advisors who've figured out how to make three incompatible systems talk to each other. They're the ones who see problems before anyone else and quietly fix them.

But too often, these people aren't given strategic influence. They're stuck in tactical mode, patching holes rather than shaping direction. The firm benefits from their creativity but never elevates it. Never asks them what they're seeing. Never brings them into the room where decisions get made.

This is especially missed in the maze of consolidation.

That's a massive missed opportunity. The people closest to the friction are usually the ones who understand best where the real problems live.

Why Constraints Actually Work

The reason MacGyver resonated—the reason it became cultural shorthand—is that it reflects something real about human cognition.

Give people unlimited options, and they freeze. Give them boundaries—tight ones—and they start innovating. Constraints force your brain to make connections it would never make otherwise. You start seeing potential in things you'd normally overlook.

This isn't just folk wisdom. A 2019 Harvard Business Review article reviewed 145 empirical studies on the effects of constraints on creativity and innovation. The finding? Individuals, teams, and organizations alike benefit from a healthy dose of constraints. It's only when constraints become too extreme that they stifle creativity.

The show was exaggerated, but the underlying truth wasn't: limitation breeds invention. Every entrepreneur who's bootstrapped a company knows this. Every small team that's outmaneuvered a bigger competitor knows this. Every person who's had to figure it out because there was no other option knows this.

AI May Be Your New Swiss Army Knife

Here's where this gets practical.

Think about what your best problem-solvers actually do. They connect dots. They remember that client situation from three years ago that's relevant to today. They spot patterns others miss. They know where to look.

Now imagine giving them a tool that can do all of that instantly, across every piece of data your firm has ever touched.

When your data is organized and accessible, AI can help your team answer questions in seconds that used to take hours. Which clients are approaching a life event that might trigger a planning conversation? What's our exposure to a specific sector across all portfolios? Where are we bleeding time in onboarding?

The fixer who used to spend half their day pulling reports can now spend that time actually solving problems. The advisor with a hunch about a client opportunity can validate it with real data in minutes.

But here's the catch: AI is only as useful as the data you feed it. If your information is scattered across disconnected systems, if your client data lives in six different places with six different formats, AI becomes just another tool that promises more than it delivers.

The firms getting real value right now aren't the ones with the biggest budgets. They're the ones who've done the unglamorous work of getting their data house in order.

What's Coming

Where we are going is about to get a lot faster.

The next few years won't reward firms that are best at improvising with duct tape and paper clips. They'll reward firms that have their data in order—the ones who've built the foundation to drive meaningful change rather than just react to it.

When the pace accelerates, the gap between firms that are prepared and those still patching things together will widen quickly.

Getting Ready

This requires intentionality. Elevate your fixers. Bring them into strategic conversations. Ask them what's broken that nobody's talking about.

Get your data house in order—not as a someday project, but as an urgent priority.

And honestly assess whether your firm is building capability or just buying time.

A cheesy 80s TV show understood something we keep forgetting: the magic happens when you've got nothing but your wits and whatever's within arm's reach. But the next chapter isn't about making do with less. It's about being ready for more.

On the Pod: The Real Alpha Inside Modern Advisory Work

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Episode 129: On this week’s episode, Kyle Van Pelt sits down with Mitch Hamer. Mitch is the Founder & Lead Advisor at Intersecting Wealth, where he partners with families to navigate their financial lives with clarity and intention. With an approach rooted more in psychology and behavior, Mitch helps clients step back from the things that get far too much attention and focus on the priorities that are often overlooked. 

Kyle and Mitch unpack the real alpha inside modern advisory work. They also discuss the challenges of scaling a highly personalized service, the importance of building a multi-generational firm to serve multi-generational clients, and the self-aware entrepreneurial path that focuses on alignment, work-life balance, and finding your own unique way in the industry.

In this episode:

(00:00) - Intro

(01:55) - Mitch's money moment

(03:32) - Mitch's journey from options trading to wealth advisory

(09:16) - Why advisors say planning is everything

(12:08) - The challenges of scaling highly personalized service

(15:38) - What it takes to start an RIA without an established book of business

(22:03) - The difference between a strategist and a technician

(25:40) - How Intersecting Wealth builds a multi-generational firm

(29:35) - The future of Intersecting Wealth

(31:26) - Mitch's take on the future of the financial services industry

(34:27) - Intersecting Wealth's tech stack

(35:34) - Mitch's Milemarker Minute

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

1. Park City, UT — February 5-6

2. Orlando, FL - February 11-13

3. Jacksonville, FL - February 13

4. New York, NY — February 17

5. San Diego, CA — February 22-28

6. New York, NY — February 28

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

Jud Mackrill

Good morning. I hope you had a great week.

As a large portion of the country gears up for winter weather—or maybe by the time you're reading this, you're already in the middle of it—I'm sitting here with a cup of coffee and my dog behind me, who is missing my wife. In an effort to comfort him, I went down a wormhole of dog-specific YouTube programming, which is keeping him company for now.

Nacho

This week I'm talking about adaptation. I can't seem to keep myself away from college football, so I'm using the season finale as a jumping-off point. There's a story here I found genuinely interesting—one with some cool parallels to how we run our businesses and live our lives.

I hope you're staying warm.

Here's this week's Rising Tide.

1. The Rematch: Why Adaptation Beats Adoption Every Time

2. How to Build a Firm That Outlasts You with Tyson Ray 🎧

3. Milemarker On the Road ✈️

The Rematch: Why Adaptation Beats Adoption Every Time

This past week, like many people, I turned on the college football national championship game in Miami between the Hurricanes and Hoosiers. I had just seen Indiana play in person at the Peach Bowl in Atlanta, and in my mind, the difference between them and everybody else was pretty massive. I was expecting them to dominate, but the Hurricanes came to play in their home stadium. It was a great game all the way down to the end—probably one of the best finishes to the college football season anyone could have hoped for.

At the center of this story was the storybook unfolding of Indiana football and Fernando Mendoza. Mendoza carries himself with such professionalism and kindness; it's truly refreshing to see a person bring that to their day-to-day.

But here's the part of the story that I found remarkable.

Same Player. Same Number. Different Outcome.

Go back in time with me to the previous season. On October 5, 2024, Mendoza was playing for another team - Cal. As their quarterback, he was facing Miami's Wesley Bissainthe—number 31—who delivered a hit that helped complete the Hurricanes' comeback win. Bissainthe’s tackle of Mendoza wasn't just a play; it was a punctuation mark on a difficult loss.

Fast forward to this year. Mendoza went to Indiana through the transfer portal and was marching his new team through every game to a win. The only game left to play was the national championship and on the other side of the field, stood that same defender - Bissainthe. Same number on his jersey from the previous year. A similar opportunity to punctuate a game, but this time, Mendoza didn’t go down. Instead, he trucked through Bissainthe on a touchdown run that has become one of the defining moments of the game.

Everyone Talks About Adoption. Almost Nobody Talks About Adaptation.

The tech industry and financial services too, love the word "adoption." We measure it. We build onboarding programs around it. We celebrate when a firm "adopts" a new platform, a new CRM, a new reporting tool.

But adoption is just the beginning. Adoption is the next step after signing the contract. It's sitting through the implementation. It's changing rhythms and finding new steps. It’s much more than checking the box that says yes, we have this now.

Adaptation goes even further.

Adaptation is what Mendoza did between October and January. He didn't just join a new team and follow their patterns—he transformed how he played too. He studied film. He understood what went wrong. And this time, when number 31 came at him, he didn't try the same thing and hope for a different result. He lowered his shoulder and kept his feet moving forward.

The Bissainthe Principle

Here's what I'd call the Bissainthe Principle: your biggest obstacles have a habit of showing up again.

The market correction that rattled your client's confidence will return in a different year. The estate planning conversation they avoided will resurface when it's more urgent. The emotional decision-making that cost them money in 2022 will await them in the next downturn.

And here's the hard truth: those obstacles can become definitional. They can either perpetually limit your clients, or your clients can learn from them and overcome. There's no third option where the obstacle just goes away. Because even if it were to never occur again, that obstacle has in some way made its mark.

The same is true for you and your firm. The technology implementation that went sideways. The key employee who left and took clients with them. The merger conversation that fell apart. The growth plateau you couldn't break through. Those moments don't just disappear from the rearview mirror—they shape how you make decisions today, whether you realize it or not.

The question isn't whether you or your clients will face number 31 again. The question is whether you'll have done the work to meet that moment differently.

Your Clients Already Know What Got Them Knocked Down

It’s so common for your client relationships to exist precisely because someone got hit by their own number 31.

Maybe it was a portfolio that wasn't built for the volatility they actually experienced; a tax strategy that looked good on paper until it didn't; a previous advisor who stopped returning calls when the market got hard; an inheritance handled poorly; a business sale where they left money on the table because nobody was quarterbacking the complexity.

They learned a hard lesson, and that lesson is part of why they're sitting across from you now.

The question is: are you helping them just adopt a new advisor, or are you helping them adapt from what they learned?

Because if all you're offering is adoption—new accounts, new allocation, new quarterly reports—you're asking them to believe that this time will be different without showing them why.

Adaptation means something more. It means asking: what broke last time? What did you learn about your own risk tolerance, your own decision-making under pressure, your own blind spots? And how does the plan we're building together specifically address that—not in theory, but in practice?

The clients who thrive with you long-term won't be the ones who simply adopted you as their new advisor. They'll be the ones you helped adapt into better stewards of their own wealth.

The Transformation Test

Here's a simple way to know if you're helping a client adopt or adapt:

If they could swap you out for another advisor and nothing would change about how they make financial decisions, you've helped them adopt.

If working with you has fundamentally changed how they see their own wealth—how they respond to volatility, how they think about risk, how they prepare for the next disruption—you've helped them adapt.

Mendoza didn't just adopt Indiana's playbook. He adapted everything he'd learned from getting knocked down into a version of himself that could truck through the same defender on the biggest stage.

Number 31 Is Coming Back

Whatever knocked your clients down before—the panic selling in a downturn, the advisor who disappeared, the estate plan that fell apart—it's on it’s way. That challenge will show up again, maybe even wearing the same jersey. The next bear market. The next health scare. The next family transition. The next moment where fear tells them to do something they'll regret.

The clients who thrive won't be the ones who adopted the best advisor. They'll be the ones who adapted from what they learned.

Your job isn't just to manage their wealth. It's to help them become the kind of people who are ready for the rematch.

What's your clients' number 31? And what are you doing to make sure they're ready when it comes back around?

On the Pod: How to Build a Firm That Outlasts You

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Episode 128: On this week’s episode, Kyle Van Pelt sits down with Tyson Ray, CEO, Founding Partner, and Senior Wealth Advisor at FORM Wealth Advisors. Tyson helps financial advisors exit their businesses with clarity, confidence, and no regrets. He's been recognized as a Forbes Best-in-State Wealth Advisor, AdvisorHub Advisors to Watch, and Barron's Top 1200 Advisor.

Kyle and Tyson discuss what it takes to build a successful wealth advisory practice that balances growth, client care, and community impact. Tyson shares the strategies, leadership mindset, and values that have guided his career to success. He also discusses his SPACE (See, Prepare, Act, Commit, Exit) framework, which reveals how advisors can exit their practice confidently and fully compensated, while keeping their clients' interests first and foremost.

In this episode:

(00:00) - Intro

(02:12) - Tyson's money moment

(05:48) - Valuable lessons Tyson learned during the early stages of his career

(07:26) - How to build a career that lasts a lifetime

(10:23) - The power of structure, boundaries, and accountability in scaling a firm

(13:51) - The SPACE framework

(21:29) - The importance of building a multi-generational team

(30:07) - How Tyson finds and trains his team members 

(32:52) - Why you should “never enter data twice”

(34:59) - Tyson's outlook on the future of the industry

(40:36) - Tyson's Milemarker Minute

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

1. Phoenix, AZ —January 26-28

2. Charleston, SC — January 26-28

3. Park City, UT — February 5-6

4. Orlando, FL - February 11-13

5. New York, NY — February 17

6. San Diego, CA — February 22-28

7. New York, NY — February 28

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

Jud Mackrill

I started my week in Lincoln, Nebraska.

Hanging out with my oldest son, Gideon. Seeing old friends. Experiencing the kindness and vitality of Middle America.

It reminded me of one of the last times I'd been in Lincoln. My wife and I walked into a hotel lobby and the young man behind the desk knew my name before I could even get to the front.

I didn't remember his.

"Are you Jud?"

"Yes. How do I know you?"

"I was in your home years ago. When I first moved to the United States. I was part of a small group at your church."

And then I remembered him. His story. His life. And as I remembered, nothing else mattered very much. I caught up with him, this person who remembered my family and me (who now live 1,084 miles away). A moment of grace that made my whole day better.

There's been a heaviness lately. Maybe you've felt it too.

I've been thinking about how easy it is—for me, certainly—to let systems, partisanship, and tribal loyalties create distance between people. How can I chase scorecards that won't matter in the end?

And I keep coming back to this: when we get to the end of our lives, most of those scorecards will have faded.

What remains is the everyday.

The interactions.

The times we opened our doors and welcomed others.

That young man in Lincoln remembered being welcomed. Years later, across a thousand miles, it still meant something to him. It meant something to me, too.

This week, I'm resharing something I wrote in 2024. It was based on something Chance the Rapper published about his experience chasing metrics.

I hope it's useful.

I hope it reminds you of moments when you've been touched by grace.

Here's this week's Rising Tide.

1. 3,333 Reasons to Make Your Own Metrics & Master Your Impact

2. The Operating System Behind Scalable Advisory Firms 🎧

3. Milemarker On the Road ✈️

A Throwback from 2024: 3,333 Reasons to Make Your Own Metrics & Master Your Impact

Chance the Rapper has become one of my favorite recording artists over the past 7+ years.

As owning your music catalog has become increasingly important, Chance began his career independently, absent from outside labels or management.

Chance’s career began with an album titled 10 Day, recorded during a 10 Day suspension from high school in 2012. With an introspective, unique delivery, listeners hear someone who openly shares insecurities, challenges, and doubts, in a mixtape style that keeps you on your toes with each new song.

Chance has never signed with a record label and has been able to release his music for free to listeners – relying on touring, streaming royalties, and uniquely branded partnerships (Kit Kat, the White Sox, and 3M) for income.

In the summer of 2024, Chance was announced as the headliner for the Minnesota State Fair. As the day of his performance approached, his brother, who manages his work, received confirmation that the fair had sold only 3,333 tickets for a venue seating 14,000.

In a world where crowd size has become more important than ever, the natural reaction to only selling 24% of your tickets is to call in sick. No one wants to be the guy with empty seats.

Chance looked at it differently and wrote a new song about it.

What Matters & Why

It’s easy for so many of us to look at the same metrics everyone else is to decide if our work or our life is worthy. It’s easy to look around and gauge our own ‘crowd size’ to decide whether to play or not.

Or we could look for the metrics that matter most to us.

We can choose to define our own metrics.

Make Your Own Metrics & Mastering Your Impact

Each day, year, month, and moment brings us an opportunity. An opportunity to be honest, refocus, and keep our eyes on our own paper.

The statement that comparing is the thief of joy has so much truth to it.

Can we learn from observing others? Absolutely.

But we shouldn’t let it define us.

How do we go about leading businesses more focused on our unique purpose?

Identifying Impact Metrics

If we go to the root of what we do, it’s important to highlight key indicators of our impact.

1. Start with How Our Clients Define Success
   The chances are that your clients couldn't care less about your AUM. They do care about how you help them and how well you understand them.
   

2. Identify Unique Market Metrics

   If you serve a niche, lean into it with the metrics that you focus on. If you serve doctors, consider the factors in their lives that can ultimately speak to your impact (e.g., helping them pay off college debt or get it written off).

   Work with small business owners and see how you can help them extend the value you provide to the people who work for them, and get focused on how many jobs you are influencing through financially solid leaders who now have the confidence to lead well and invest with clarity.
   

3. Identify Your Adoption Metrics

   Real change comes through adopting new practices and behaviors. If you look at all the things you can do for your clients, start identifying how many of them have adopted each of them. If this makes your clients' lives better, consider this as a new start for how your team works to serve the rest of your clients.

What are the metrics that matter to you?

What are the metrics that matter to those who love you?

On the Pod: The Operating System Behind Scalable Advisory Firms

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Episode 127: On this week’s episode, Kyle Van Pelt sits down with Matt Regan, President at Wealthcare. With more than two decades in the financial services industry, Matt has helped build several transformative business models, including launching the retail brokerage and OpenIPO system at WR Hambrecht+Co. His work has consistently focused on scaling world-class organizations with a strong commitment to the client experience.

Kyle talks with Matt about building scalable, sustainable advisory businesses at the intersection of technology and operations. Matt shares his journey into wealth management, the evolution of Wealthcare from planning software to a full-service platform, and how standardized systems drive organic growth and enterprise value. They dive into affiliation models, M&A strategy, talent challenges, and the future of advice in an AI-driven world—especially for emerging advisors and smaller clients.

In this episode:

(00:00) - Intro

(02:44) - Matt's money moment 0.

(03:58) - Wealthcare's origin story

(06:20) - Wealthcare's affiliation model

(12:24) - Common pitfalls in M&A

(14:04) - The talent gap and finding Gen 2 successors

(15:33) - Matt's thoughts about the future of M&A

(19:34) - What it takes to build a firm from $0 to $100M in today's market

(22:47) - The role of AI in serving HENRYs (High Earners, Not Rich Yet)

(26:50) - Why soft skills are the new hard currency

(28:27) - Matt's outlook on the future of the industry

(32:37) - Matt's Milemarker Minute

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

1. Phoenix, AZ —January 26-28

2. Charleston, SC — January 26-28

3. Tysons Corner, VA — February 3

4. Park City, UT — February 5-6

5. San Diego, CA — February 22-28

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

Jud Mackrill

It's Friday night, and I’m sitting next to some of my friends in Atlanta — watching Indiana shellack Oregon in the Peach Bowl.

best mascot in college sports

This week, I’m focused on growing my team at Milemarker with the right leader for the next stage of our onboarding. The major challenge here is that what you can and should do to lead in a technology company is radically different than it even was six months ago.

No one can afford to be recruiting static talent. We have to build a team that can keep up, constantly think differently, and leverage technology to constantly challenge the status quo.

In many respects, adding talent and investing in your talent is completely new territory in 2026.

With this, I’m writing about the new war for talent and what this really means today.

Here’s this week’s Rising Tide.

1. The New War for Talent

2. Scaling White-Glove Client Experiences with Sarah Simmer🎧

3. Indiana’s Curt Cignetti on the Keys to Leading in 2026

4. Milemarker On the Road ✈️

The New War for Talent

Getting the right talent is everything.

If you run a wealth management firm or a wealthtech company, you know exactly what I'm talking about. Finding people who fit your culture. Who can execute. Who see the vision and carry it forward. People who help you build something far greater than yourself.

It's some of the hardest work there is. We're all spinning a lot of plates right now.

But here's the thing—there's a new war for talent happening, and this battle is more within than without.

Things are moving simply too fast.

The real differentiator isn't who you can poach from a competitor. That game's been going on for as long as there have been RIAs. Musical chairs. It never stops.

That's not the war I'm talking about.

The new war for talent is about AI adoption. The day-to-day practice of thinking about your work differently. Transforming how things get done at an exponential pace.

This is what's going to separate firms going forward.

If you're not leaning in as a leader right now, you're missing what I believe to be one of the most meaningful waves of change to sweep our industry. A real chance to do better for our clients. To build better products and solutions. To go deeper in the detail and help we can provide.

This is such an interesting time.

Look at the data: 95% of wealth and asset management firms have scaled AI adoption to multiple use cases. 78% are exploring agentic AI.¹ Family offices leveraging AI to improve operations? Three times more this year than last.²

The technology is here. It's everywhere.

And yet—only 29% of firms are seeing substantial impact.¹

That's the gap. Not the technology. The adoption.

McKinsey found that AI high performers—the firms actually seeing meaningful results—are three times more likely to have senior leaders who demonstrate ownership and commitment to AI initiatives.³ Leadership here isn't just setting strategy. It's role-modeling the behavior. Getting hands-on. Being the champion.

Here's what stops me in my tracks: only 6% of employees feel very comfortable using AI in their roles.⁴

We have the tools. We don't have the adoption.

And here's the uncomfortable truth—there's no pool of talent out there that's really good at this stuff. That's not how it works. You're not going to find them waiting on the sidelines.

The talent you need is most likely the talent you already have.

Your leaders. Your team members. Getting their hands in managing data with AI. Using it to do more with what they have. Building processes and skills on top of it.

This is the new war for talent. The war is within.

Here's what the numbers say: 87% of companies worldwide already experience or anticipate a significant skills gap.⁵ IDC estimates these shortages could cost the global economy $5.5 trillion by 2026.⁶ AI-exposed roles are evolving 66% faster than other positions and command a 56% wage premium.⁷

The gap widens every day you wait.

The question isn't whether someone has a great résumé or came from the right firm. It's whether they can transcend this change. Maybe they're amazing relationally—and they always will be. But behind the scenes, you're going to need bots and agents and skills executing the deep work.

That combination is what drives value now.

I don't think you're going to hire as many people this year. I don't think you need to.

What I do think? You can make your team wholly more efficient if you embrace this. It'll save you money. You'll have a team that's far more empowered to do meaningful work.

But it requires something from you.

Question everything with your IT department. Challenge them—help me have the tooling I need. Same with compliance. It can all be accomplished.

Don't take no for an answer. Push in. Get clearer.

Your people want this. 51% of workers say enhanced training is their top priority for improving AI outcomes.⁸ And here's the kicker—36% of employees planning to resign cite inadequate training as a driving factor.⁴

Invest in your people or lose them to someone who will.

This is the new era. It's going to be an adventure. Truly exciting—and probably a little scary for your team.

But if you can understand this, adopt it in your mind, and be the champion it requires? You can transform how work happens. You can make your business far better.

Go change the way you work today.

Good luck out there.

Footnotes:

¹ EY, "GenAI in Wealth & Asset Management Survey 2025" (September 2025)

² RBC and Campden Wealth, "The North America Family Office Report 2025" (October 2025)

³ McKinsey & Company, "The State of AI in 2025: Agents, Innovation, and Transformation" (November 2025)

⁴ Universum, "Talent Outlook 2025"

⁵ McKinsey, as cited in TalentGuard, "From Skills Gaps to AI-Powered Career Growth" (March 2025)

⁶ IDC Analyst Brief, "Closing the Gap: Verifying AI Skills in the Enterprise" (2025)

⁷ PwC, "2025 AI Jobs Barometer"

⁸ SHRM, "From Adoption to Empowerment: Shaping the AI-Driven Workforce of Tomorrow" (July 2025)

On the Pod: Scaling White-Glove Client Experiences

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Episode 126: On this week’s episode, Kyle Van Pelt sits down with Sarah Simmer, Partner and Senior Wealth Advisor at Heritage Wealth Advisors. Sarah delivers customized wealth management and tax planning services to individuals and families, with a special focus on multi-generational households.

Sarah and Kyle discuss what world-class client experience truly requires, especially for ultra-high-net-worth families. She shares the tactical side of scaling a white-glove firm, highlighting the importance of rigorous client segmentation, the courage to have difficult fee conversations, and and how data can be used to determine exactly who you should and shouldn't be serving. 

In this episode:

(00:00) – Intro

(03:10) - Sarah's money moment

(06:11) - How Sarah's mother influenced her career in wealth management

(09:13) - How an auditor's mindset translates to serving high-net-worth families

(10:30) - What client experience means for ultra-high-net-worth families

(13:16) - How Sarah uncovers and manages client expectations

(17:55) - Why proactively discussing fees can reinforce value

(22:46) - How Heritage scales white-glove service to ultra-high-net-worth clients

(30:03) - How a scaled white-glove service feels personalized

(34:08) - Sarah's outlook on the future of the financial services industry

(36:22) - Sarah's Milemarker Minute

⚡️Bookmarks

Indiana’s Curt Cignetti on the Keys to Leading in 2026

Its nearing the end of college football season and I will definately ease up on all my college football mentions at some point. This quote by Curt Cignetti was really relevant in what it looks like to lead and build today.

In short, we need to be attacking at all times.

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

1. Phoenix, AZ —January 26-28

2. Charleston, SC — January 26-28

3. Tysons Corner, VA — February 3

4. Park City, UT — February 5-6

5. San Diego, CA — February 26-28

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

Jud Mackrill

Good morning. Happy New Year.

You've got five more days to say that before that expires.

I hope the holidays treated you well. Now that the new year is here, there’s a fresh clock ticking. Resolutions, goals and plans have been made. Now it's time to focus on execution.

Will you carry momentum forward? Or start from scratch?

I've been thinking about this a lot. College football helped me figure it out.

Here's this week's Rising Tide.

1. You're the Spark - Keys to Making Momentum Contagious

2. Next Mile: Why Wealth Tech Still Feels Broken 🎧

3. Elevation Point on Laying the Foundation for AI-Driven Growth

4. Milemarker On the Road ✈️

You're the Spark - Keys to Making Momentum Contagious

It's New Year's Eve and I'm texting with my friends who pull for the Miami Hurricanes. Normally, I can't root for the Canes under any circumstances, but Ohio State is due.

The Buckeyes had been sitting since the Big Ten Championship Game, while Miami had to fight through a first-round slugfest with Texas A&M. You'd think that extra rest would be an advantage. Instead, Miami took ten days to heal up and proceeded to punch a cold Ohio State team in the mouth.

Turns out, rest doesn’t always lead to readiness.

College football is about momentum. Teams that stay sharp, stay aggressive, and keep moving tend to win. The ones that sit back and wait for the next thing to happen? They often find themselves on their heels.

The same is true in business.

As we head into 2026, plenty of things are uncertain; markets, regulations, the political landscape, you name it. But your momentum doesn't have to be. There are things you can control. Rhythms you can establish. Energy you can create.

Here's the thing about momentum that's easy to miss: it's tied directly to influence.

And as much as you hope that someday, someone else is going to be that spark for your firm, you already know the answer.

You're the spark.

Your energy, your focus, your drive toward something is the catalyst.

This isn't just motivational talk. Researcher Sigal Barsade spent her career at Wharton studying something called emotional contagion, the phenomenon where emotions spread through groups like viruses. Her findings were clear: leaders' moods are disproportionately contagious. Your team is watching you, reading you, taking cues from you whether you realize it or not. If you walk in defeated, that spreads. If you walk in lit up, that spreads too.

Maybe you're fortunate enough to have other leaders in your firm who carry that fire. I'm thankful I do. But even then, if you're a wet blanket on motivation, you've got to find a way to change. Find the something that got you fired up in the beginning. Remember why you wanted to do all of this in the first place.

Because momentum isn't just about attitude, it's about physics.

In Good to Great, Jim Collins describes what he calls the flywheel effect. Picture a massive metal disc mounted on an axle. Getting it to move takes enormous effort. You push, and nothing happens. You keep pushing, and it inches forward. You push again and again, and eventually, the flywheel starts to turn. Then it builds. Each push compounds on the last until the thing is spinning with its own force.

That's momentum.

No single push gets credit for the breakthrough. It's the accumulation of consistent effort in one direction. And here's what matters for you heading into this year: the flywheel doesn't care about calendar years. If you built momentum in 2025, you don't have to start over. You get to keep pushing.

But if you stop? If you sit back and wait like Ohio State did? The flywheel slows. And you're back to pushing from a dead stop.

Our whole industry is built on compounding. That's the focus. We help clients compound, whether it's assets or, increasingly, experiences. The math works the same way inside your firm. Energy compounds. Momentum compounds. And so does apathy.

If I go back to this game between Ohio State and Miami, I have a high level of confidence that if it were five quarters long, Miami doesn't win. Miami carried momentum out of the gate. It was fast and it was transformative. It took Ohio State too long to find theirs. By then, it was too late.

So as you look at the year ahead, here's where I'd start:

Where do you have momentum right now coming out of 2025? Identify it. Protect it. Double down on what's working instead of getting distracted by what's not.

Where do you need it? Maybe it's a team that's gone flat. Maybe it's a service line that's stalled. Name it honestly but without blame.

Where are you at risk of losing it? Momentum is fragile. It requires continuous reinforcement. Don’t think you can bank it and walk away.

What's your first push? The flywheel starts with one. What's the push you can make this week; not this quarter, this week, that gets things moving on something new?

And finally: Who's carrying the spark? If it's you, own it. If it's not, find them and clear their path.

These aren't rhetorical questions. They're the work.

Happy 2026. I'd love to hear what you’re planning.

On the Pod: Why Wealth Tech Still Feels Broken  

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Episode 125: In this special New Year's 2025 episode, Kyle Van Pelt brings together four standout voices to explore why wealth technology still feels broken—and what actually fixes it.

Jeremy Nelson explains how rising client complexity demands centralized planning and operational tech that can truly scale. Art Ambarik shares how fragmented data and poor transitions create bottlenecks that distract advisors from clients. Kylie Felker shows how efficient systems make room for unreasonable hospitality and deeply human service. And Terry Parham Jr. outlines how impact, efficiency, and effectiveness improve when firms own and streamline their data.

Together, these conversations reveal how better integration, not more tools, is the path forward.

In this episode:

(00:00) – Intro

(00:30) – Jeremy Nelson on rising client complexity and why centralized tech is essential for scale

(03:25) – Art Ambarik on data bottlenecks, advisor transitions, and removing operational friction

(08:30) – Kylie Felker on using efficient systems to create unreasonable hospitality for clients

(15:30) – Terry Parham Jr on evaluating wealth tech through impact, efficiency, and effectiveness

⚡️Bookmarks

Elevation Point on Laying the Foundation for AI-Driven Growth

I recently spoke with Elevation Point CEO Jim Dickson about the future of RIAs and why proactive data management and AI-powered tools are becoming table stakes. We also discussed Elevation Point’s new partnership with Milemarker and how a unified data foundation is helping fuel long-term, aligned growth.

Below are a few highlights from our conversation.

At Elevation Point, Laying the Foundation for AI Growth

The recent partnership with Milemarker is a harbinger of what’s to come, execs Jud Mackrill and Jim Dickson say.

www.thinkadvisor.com/2025/12/23/at-elevation-point-laying-the-foundation-for-ai-growth

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

1. Atlanta, GA — January 9

2. Phoenix, AZ —January 26-28

3. Charleston, SC — January 26-28

4. Park City, UT — February 5-6

5. San Diego, CA — February 26-28

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

Jud Mackrill

70 degrees in Charleston. Christmas week. Feels like June.

Before the holiday, I had the same conversation three times.

Different people. Same reference: the Domino’s Pizza Tracker.

“I wish we had that for our clients.”

Domino’s launched that tracker in 2008. Seventeen years ago. And advisors still bring it up weekly.

A $14 pepperoni pizza has better status visibility than a $200 million portfolio rebalance. That’s absurd. And it’s still true.

This week: why we’re still talking about pizza, and what 2026 should finally change.

Happy holidays. Here’s the Rising Tide.

1. Have Your Pizza and Track It Too

2. Next Mile: What It Takes to Build the Next Generation of Talent 🎧

3. Elevation Point on Laying the Foundation for AI-Driven Growth

4. Milemarker On the Road ✈️

Have Your Pizza and Track It Too

Domino’s launched its Pizza Tracker in January 2008.

That’s seventeen years ago. The iPhone was six months old. Obama hadn’t been elected yet. Lehman Brothers was still a going concern.

And yet, almost every week, an advisor brings this up to me: “I wish we had something like Domino’s Pizza Tracker for our clients.” 

Every. Single. Week.

Think about that for a moment. A $14 pepperoni pizza has better status visibility than a $200 million portfolio rebalance. Your client can watch their Meat Lover’s journey from prep to oven to doorstep, but they have no idea where their rollover paperwork stands.

How is this still true?

Let’s talk pizza. Let’s talk data. And let’s talk about why 2026 should finally be the year you can track your calzones.

The Dirty Truth About the Pizza Tracker

Here’s the thing about that famous tracker: it’s not quite what you think it is.

The Pizza Tracker is real technology—Domino’s patented it (U.S. Patent 10,262,281)—but it’s also part theater. The system is connected to actual store operations through Domino’s Pulse computer system, accurate to within 40 seconds according to the company. When a team member finishes prepping your order, they press a button. When it goes in the oven, another button. When the driver leaves, they punch out.

But here’s where it gets interesting: former employees have revealed that the system can be “gamed.” Employees sometimes mark orders complete before they’re actually done. Drivers use dummy accounts to take more deliveries than the system thinks they’re running. The tracker might say “delivered” when your pizza is still three stops away.

Why do they game it? Because the tracker isn’t just for customers—it’s a performance management tool. Corporate uses that data to rate store locations. So when Friday night gets slammed and there aren’t enough drivers, employees find creative workarounds to keep their metrics looking good.

The tracker is only as honest as the people feeding it data. Sound familiar?

The Real Genius of the Pizza Tracker

Here’s what Domino’s actually solved: they eliminated the “where’s my order?” phone call.

A TikToker who read the entire patent put it perfectly: “They’re not out to fool us. It’s to reduce the amount of people who are calling and asking, ‘What status is my pizza at?’

Before the tracker, every anxious customer meant an interrupted kitchen. Someone had to stop making pizzas to answer the phone, look up the order, explain that yes, it’s in the oven, and get back to work. Multiply that by dozens of calls per shift and you’ve got a serious operational drag.

The tracker didn’t just improve customer experience—it freed up capacity. It turned reactive service into proactive communication.

Now imagine that applied to your practice.

Why Advisors Still Dream of Pizza Trackers

When advisors tell me they want a “pizza tracker,” they’re not really asking for a progress bar. They’re expressing a deeper frustration:

They can’t see where anything stands. 

• Where’s that account transfer?

• Did the ACAT go through?

• Has the client signed the documents?

• Is the model rebalance complete?

• When did we last reach out to this prospect?

These answers exist somewhere—scattered across your CRM, your custodian portal, your portfolio management system, your email, your task manager, maybe a spreadsheet or two. The data is there. It’s just not connected.

And here’s the kicker: your clients feel the same uncertainty you do. They submitted that rollover paperwork and now they’re waiting. Wondering. Maybe calling. Definitely anxious.

Domino’s understood something profound: visibility creates trust. Even imperfect visibility. Even a progress bar that’s occasionally off by a few minutes. The act of showing people what’s happening—giving them a window into the process—fundamentally changes how they experience the wait.

The Gap That Shouldn’t Still Exist

So why, in 2025, does a pizza chain have better process visibility than most wealth management firms?

Three reasons:

1. Fragmented systems. The average RIA uses 15+ different technology platforms. Each one holds a piece of the puzzle. None of them talk to each other in any meaningful way. Your CRM knows about the client relationship. Your custodian knows about the assets. Your financial planning tool knows about the goals. Your trading system knows about the models. But nothing knows everything.

2. Data lives in silos. Even when you can access information from multiple systems, it’s disconnected. You can pull a report from Schwab and a report from Redtail, but reconciling them requires manual effort. The data isn’t unified. There’s no single source of truth.

3. No process layer. Here’s the real problem: even if your data were connected, you’d still lack the workflow infrastructure to track multi-step processes. A pizza order has five stages: prep, bake, quality check, out for delivery, delivered. A client onboarding might have fifty steps across eight systems. Without a process layer sitting on top of your data, you can’t track anything meaningfully.

What It Actually Takes to Build a Pizza Tracker

Let me tell you what Domino’s had to do to make their tracker work.

First, they centralized their order data. Every order from every store flows into a unified system. They’re not checking eight different databases—they’re polling one.

Second, they created standardized stages. Prep. Oven. Quality check. Delivery. The same stages at every location, logged the same way, measured against the same timelines.

Third, they connected the humans to the data. Every button press, every login, every punch-out feeds the system. The tracker isn’t a guess—it’s a reflection of actual events happening in the store.

Fourth, they built a customer-facing layer on top. The tracker itself is just a visualization of the underlying data. The real infrastructure is invisible.

This is exactly what’s been missing in wealth management. Not the visualization—the infrastructure.

The Warehouse Changes Everything

At Milemarker, we’ve been obsessed with this problem for years.

Here’s what we’ve built: a data infrastructure layer that sits beneath your entire operation. Every system you use—your CRM, your custodian feeds, your financial planning software, your portfolio management tools, your document storage—all of it flows into a central warehouse.

But we didn’t stop at data aggregation. That’s table stakes.

We built the process layer.

When a request comes in—an account opening, a money movement, a rebalance—it doesn’t just live in your request system. It lives in the warehouse. It lives in the data lake. Every stage, every status change, every timestamp gets captured.

Why does this matter? Because now you can see it. Track it. Report on it. And—here’s where it gets exciting—you can automate it.

From Pizza Tracker to AI Agent

Here’s what 2026 looks like.

Imagine a client submits a rollover request through your portal. That request hits your CRM. But it also hits your data warehouse. An AI agent picks it up, recognizes the request type, and kicks off a workflow:

1. Generate the rollover paperwork

2. Send it for e-signature

3. Monitor for completion

4. Submit to the custodian

5. Track the ACAT status

6. Notify the advisor when assets land

7. Update the client along the way

At every stage, the client can see where things stand. Not because someone built a bespoke tracker, but because the underlying data infrastructure makes visibility automatic.

Your own pizza tracker. For any process. Any “pizza”—or calzone, or breadsticks, or whatever your firm’s version of a complex multi-step client request happens to be.

The Lesson From a $14 Pepperoni

Here’s what seventeen years of Pizza Tracker envy should teach us:

The visualization isn’t the innovation. The data infrastructure is. 

Domino’s didn’t build a pretty progress bar and call it a day. They rebuilt their entire operational data architecture so that real-time visibility became possible. The tracker is just what customers see. The transformation happened underneath.

Wealth management has been trying to solve this backwards—bolting dashboards onto disconnected systems, hoping visibility will emerge from complexity. It won’t.

You need the warehouse first. You need unified data. You need a process layer that captures every stage of every workflow. Then the “pizza tracker” becomes much simpler.

2026: Have Your Pizza and Track It Too

I’ve been having this same conversation with advisors for years. The longing for a pizza tracker. The frustration with opacity. The sense that this shouldn’t still be a problem.

It shouldn’t. And it doesn’t have to be. The infrastructure exists now. The AI capabilities to automate complex workflows exist now. The ability to surface real-time status to clients and advisors alike—that exists now.

2026 should be the year you finally stop envying a pizza chain.

Build the warehouse. Unify the data. Create the process layer. And then watch what becomes possible when you can finally see—and show your clients—exactly where their order stands.

Prep. Processing. Quality check. Complete.

Your pizza’s ready.

Have questions about building your firm’s data infrastructure? Let’s talk. Because nobody should have to wonder where their money is when they never have to wonder where their pizza is.

______________________

On the Pod: What It Takes to Build the Next Generation of Talent 

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Episode 124: In this special Christmas 2025 episode, Kyle Van Pelt brings together four standout voices to explore what it takes to identify, attract, develop, and retain the next generation of talent.

Daniel Spurgeon shares how firms can spot potential early and create intentional career pathways instead of reactive hires. Kristen Oziemkowski explains what today’s young professionals are really looking for—and how purpose, culture, and clarity drive attraction. Eric Kittner highlights the power of mentorship, in-person learning, and real responsibility in developing talent. And Matt Matrisian makes the case that long-term growth, trust, and investment are essential to retention.

Together, these conversations offer a practical roadmap for building teams that thrive well into the future.

00:00) - Intro

(00:54) – Daniel Spurgeon on identifying potential early and building intentional career pathways

(07:32) – Kristen Oziemkowski on attracting young professionals through purpose, culture, and clarity

(16:53) – Eric Kittner on developing the next generation through mentorship and real responsibility

(24:52) – Matt Matrisian on retaining talent by investing in growth, trust, and long-term vision

⚡️Bookmarks

Elevation Point on Laying the Foundation for AI-Driven Growth

I recently spoke with Elevation Point CEO Jim Dickson about the future of RIAs and why proactive data management and AI-powered tools are becoming table stakes. We also discussed Elevation Point’s new partnership with Milemarker and how a unified data foundation is helping fuel long-term, aligned growth.

Below are a few highlights from our conversation.

At Elevation Point, Laying the Foundation for AI Growth

The recent partnership with Milemarker is a harbinger of what’s to come, execs Jud Mackrill and Jim Dickson say.

www.thinkadvisor.com/2025/12/23/at-elevation-point-laying-the-foundation-for-ai-growth

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

1. Phoenix, AZ —January 26-28

2. Charleston, SC — January 26-28

3. San Diego, CA — February 26-28

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

Jud Mackrill

Hey everyone, hope you're doing great.

I had a fun number of interactions with various readers this week—it's always energizing to get feedback. I just wrapped up my 144th flight of the year, touching down from time with clients and partners in Indianapolis. As I landed, my Flighty app pinged me with all the stats: delays, miles flown, the whole merit badge routine.

But when I look at the time I've been out this year, it doesn't always feel meritorious. It's a journey—one I genuinely enjoy getting to be on. And I always look forward to popping open my laptop on a Friday to create The Rising Tide.

This week, I'm talking college football (once again) as I gear up to watch the playoff games this weekend. I am looking forward to wrapping up the year with loved ones over the holidays and hope you’ve carved out some time for the people that mean the most to you.

Here's this week's Rising Tide. Hope you have a great weekend.

1. Forget Spotify Wrapped. Try This Instead.

2. Next Mile: How Planning Drives Better Investment Decisions 🎧

3. Elevation Point Partners With Milemarker

4. Replay: Milemarker Navigator - AI on All Your Data

5. Milemarker On the Road ✈️

Forget Spotify Wrapped. Try This Instead.

This time of year is interesting. We are swimming in retrospectives. Your flight count for the year. Hotels stayed. LinkedIn interactions. Spotify Wrapped. There's a plethora of retros telling sometimes fun, sometimes depressing stories about how your year went.

One retrospective practice that caught my attention comes from Eugene, Oregon.

I've really enjoyed the culture Dan Lanning has built as the head coach of Oregon. Recently, I watched him break down something interesting about how they operate—and it ties directly into this season of self-reflection.

After every game, Oregon players write essays documenting areas where they could improve. Not just verbal debriefs—written self-assessments. They evaluate what they did well, where they fell short, and where they are mentally. Then they share these with their coaches. Lanning reads each one personally.

As he puts it: "Self-awareness is something I'm really big on. If you can identify a problem within yourself before a coach tells you, then you have a better chance of solving that problem."

This isn't just for players. Every coach. Every staff member. Everyone has an improvement plan. One thing they must get better at.

It struck me how relevant this is to what we do.

It's one thing to have someone else tell you facts about your reality. It's another thing entirely to critique yourself, look for areas to improve, and then share that with your support system—the people positioned to actually help you.

Our industry sits on a foundation of coaching and supporting people. Regular people walking through life who raise their hand seeking assistance, outsourcing some function of their lives.

As the value of financial advice continues to evolve, we have more opportunities for creative dialogue around the things in our clients' lives that could be improving.

Try this: Ask your clients an open-ended question as they look ahead to 2026. "What are the areas of your life you wish would improve?"

The direction they take that question is only limited by their imagination. It'll speak volumes about where their minds and hearts are. And then you can figure out how to better lend advice in the framework of where they want to go.

I’m sure there will be answers that won’t have direct ties to financial planning, but the opportunity to state these things out loud? That's where transformation starts. We need to be facilitating that.

This works internally too. In one-on-ones with your team, ask them to write down the answer to this: "Who do you want to be at work this next year? Where do you think your department could be when 2027 comes around? What process do you want to improve?"

To create a culture where this works the best, you’ll have to withhold judgement about their ideas. Use their responses as a way to gain insight into what matters most to your team members.

It's important to not shame anyone for a bad performance during this process. If you can communicate that imperfection will always be a part of our lives in one hand and the concept that everyone's working to improve in the other, you can build a fundamentally healthier culture.

I'm seeing this at Oregon. If you’re already doing this, I’d love to hear about how it’s going. If not, maybe it’s time to start.

Consistency over time breeds excellence. Progress is transformative when it’s built day by day.

And here's my encouragement for you: consider doing this for your personal life. Write down your answers. Who do you want to be next year? What do you need to start doing now to become that? How do you want to grow? Then share it with someone who’s likeminded and can speak truth into your life.

We are in a process improvement business. We should always be working to get better—taking accountability for our performance on the field. Whether your field is client meetings, building technology, helping people get more out of what they've invested in, or navigating family, finances, and behavior.

If we become healthier versions of ourselves through increased self-awareness, think about the impact we can actually make.

This isn't a New Year's resolution list. It's way more practical. It’s a real way to improve your outcomes in the year ahead.

Have a great weekend.

- Jud

______________________

On the Pod: How Planning Drives Better Investment Decisions

Listen to Episode

Episode 123: On this week’s episode, Kyle Van Pelt sits down with Tim Thomas, Chief Investment Officer and Wealth Manager at Badgley Phelps Wealth Managers. Tim joined Badgley Phelps in 2008 and brings more than two decades of experience in financial planning and portfolio management. He specializes in security analysis and selection, portfolio construction, asset allocation, and alternative investments.

Tim shares with Kyle about the mechanics of modern portfolio construction. He discusses why the financial plan must be the north star for investment strategy, how to navigate the noisy and rapidly democratizing world of alternative investments, and how AI is changing the backend of advisory work without replacing the human connection.

(00:00) - Intro

(01:33) - Tim's money moment

(02:57) - Marrying financial planning with investment strategy

(03:56) - How investing has changed over time

(06:18) - The rise in alternative investments

(09:55) - Understanding alts as more than one asset class

(16:24) - How Badgley Phelps helps clients navigate the nuances of alts

(18:27) - Managing M&A and the acquisition of Marshall & Sullivan

(21:45) - How Badgley Phelps approaches holistic planning

(23:40) - Tim's thoughts about the future of the industry

(27:25) - Tim's Milemarker Minute

⚡️Bookmarks

Milemarker Partners With Elevation Point

Milemarker is proud to partner with Elevation Point as the firm scales its outsourced CIO (OCIO) business and growing network of independent RIAs. Through this partnership, Milemarker is powering a unified data infrastructure that connects portfolio, performance, and operational insights across multiple custodians and technology platforms—without disrupting what makes each partner firm unique. Together, we’re enabling Elevation Point to move beyond aggregation and toward true operational leverage at scale.

Read the full article below

Elevation Point Taps Milemarker to Grow Outsourced CIO Business

The RIA investor wants to better connect information across partner firms and its outsourced chief investment officer platform.

www.thinkadvisor.com/2025/12/18/elevation-point-taps-milemarker-to-grow-outsourced-cio-business

Replay: Milemarker Navigator — AI on All Your Data

Thank you to everyone who joined us for the launch of Milemarker Navigator — the natural language AI built for RIAs who are ready to operate differently in 2026 and beyond.

We introduced a new standard for data access in wealth management: instant answers, secure processing inside Snowflake, no SQL, and no exposure of client records. For firms tired of waiting on reports, juggling systems, or relying on external AI tools that require sending sensitive data out of their environment — Navigator is what comes next.

If you missed the session, you can watch the full walkthrough below:

Introducing Milemarker Navigator: Your Key to Being AI Powered in 2026

Introducing Milemarker Navigator learn how it supports RIAs in unifying data and overcoming challenges through innovative AI and automation

milemarker.co/introducing-milemarker-navigator-your-key-to-being-ai-powered-in-2026

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

1. Phoenix, AZ —January 26-28

2. Charleston, SC — January 26-28

3. San Diego, CA — February 26-28

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

Jud Mackrill

December is a stress test.

The inbox is full. The calendar is packed. Everything that "can wait until later" just arrived.

This is the moment that separates the organized from the overwhelmed.

I'm not going to tell you to slow down. You've got things to finish. Goals to hit. A year to close out strong.

But I will say this: don't forget to look up. The holidays are here. The people you care about are close. Both things can be true—the push and the pause.

Finish well. Rest well. They're not opposites.

Now.

I need to talk about Notre Dame football.

Not just because I love the game. Because what's happening with the Irish this season is a masterclass in how teams—and organizations—either rise together or fall apart.

The parallels are hard to ignore.

Here's this week's Rising Tide.

1. Take Your Ball and Go Home

2. Next Mile: Beyond Referrals — Transforming Advisor Growth 🎧

3. Replay: Milemarker Navigator - AI on All Your Data

4. Milemarker On the Road ✈️

Take Your Ball and Go Home

I spent last weekend at a kids’ flag football tournament in Tampa.

Watched a lot of football. Watched even more adults lose their minds.

Every bad call triggered the same sequence. Coach erupts. Parents follow. Kids stop playing and start feeling wronged.

The game shifts from “what do we do next” to “we’re being cheated.”

I drove home thinking about how early this starts. How quickly teams learn to blame instead of adapt.

Then I checked my phone.

Notre Dame—left out of the College Football Playoff after being ranked in the top 10 all season—announced they wouldn’t play in a bowl game at all.

Their athletic director called it a “farce.” Said the opportunity to compete was “stolen” from them.

The team’s official statement: they’re skipping the bowl and hoping to bring a national title to South Bend in 2026.

Translation: we’re taking our ball and going home.

This is the air we’re all breathing now.

Entitlement so thick you can taste it.

It shows up in youth sports. In college football. And it shows up in how we run our businesses.

The belief that your firm is the best and nothing can touch you.

The belief that you understand your clients while spending less and less time with them.

The belief that people are lucky to work with you.

These aren’t just blind spots. They’re the lies that prevent actual success from ever taking root.

Real success doesn’t get announced. It gets earned.

Every day. By showing up. By caring. By doing the work that makes you better.

Some firms try to buy championships. Throw money at the problem. Stack the roster with credentials. Build the brand before they build the substance.

But the best teams? They’re built by process and time. They’re the product of virtue and repetition. They taste different because they were made different.

If you’re running on the anabolic steroid version of success—pumping yourself up in the mirror, telling yourself you’ve arrived—deep down you know the truth.

You haven’t earned it yet.

The antidote is simple. Not easy, but simple.

Get grounded in reality. Your team should know your clients better than anyone. The more you learn, the more you realize how much you can improve. That’s not weakness. That’s the whole game.

Study the standard your clients actually expect. Not what your custodian allows. Sign up for Uber. Order food on DoorDash. That frictionless experience? That’s the bar. Your onboarding workflow held hostage by legacy systems isn’t impressive. It’s invisible friction your clients tolerate until they don’t.

Build a team that ships. We’ve entered the era of separation—people with ideas versus people who deliver. Find the ones who carry water. Who would do this work because they’re passionate about the problem. Who can actually reinvent how you operate.

And then show up. Every day. Wealth management is simple. Stay grounded in facts. Trust the process. Be in it.

Notre Dame could have played one more game. Proved something. Competed.

Instead, they went home.

Don’t leave early.

Play every down.

Earn the right to be a champion today.

______________________

On the Pod: Beyond Referrals — Transforming Advisor Growth

Listen to Episode

Episode 122: On this week’s episode, Kyle Van Pelt sits down with Eden Ovadia, Co-Founder of FINNY. Before FINNY, Eden worked on the private equity team at Boston Consulting Group, where she advised on major M&A deals across the wealth management space. Driven by her background in AI and engineering, and inspired by the wealthtech industry's shifting dynamics, Eden co-founded FINNY to help advisors build predictable, personalized, and tech-enabled organic growth engines.

Eden discusses why the wealth management industry is ripe for innovation and disruption. She also shares why referrals are no longer enough to drive organic growth, and how FINNY rewrites the marketing playbook using machine learning to create hyper-personalized, high-propensity matches between advisors and prospects.

(00:00) - Intro

(02:18) - Eden's money moment

(04:12) - Innovation in wealth management

(07:28) - Why referrals are no longer enough to grow organically

(09:25) - How FINNY rewrites the traditional marketing playbook

(16:16) - The power of niching and segmentation in organic growth

(18:14) - Introducing the F-score: FINNY's proprietary machine learning algorithm

(22:56) - What it takes to build an advisor-first tech stack

(24:18) - FINNY's future goals

(25:39) - FINNY's outlook on the future of the wealth management industry

(28:51) - Eden's Milemarker Minute

⚡️Bookmarks

Replay: Milemarker Navigator — AI on All Your Data

Thank you to everyone who joined us for the launch of Milemarker Navigator — the natural language AI built for RIAs who are ready to operate differently in 2026 and beyond.

We introduced a new standard for data access in wealth management: instant answers, secure processing inside Snowflake, no SQL, and no exposure of client records. For firms tired of waiting on reports, juggling systems, or relying on external AI tools that require sending sensitive data out of their environment — Navigator is what comes next.

If you missed the session, you can watch the full walkthrough below:

Introducing Milemarker Navigator: Your Key to Being AI Powered in 2026

Introducing Milemarker Navigator learn how it supports RIAs in unifying data and overcoming challenges through innovative AI and automation

milemarker.co/introducing-milemarker-navigator-your-key-to-being-ai-powered-in-2026

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

1. December 15-16 - Carmel, IN

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

Jud Mackrill

On Wednesday, we launched Navigator AI. From my vantage point, it’s our biggest and best product release yet.

Then my phone exploded.

Not with work.

With Spotify Wrapped.

This year’s Wrapped didn't just tell you your top artist or the song you played 143 times while insisting you "never overplay music."

No. This year, Spotify tried something new.

It guessed your age.

And let me tell you… it turned group chats into war zones.

Spotify guessed my age exactly.

My wife? Off by two decades.

One of our friends, 10 years younger than me, came in at 92.

Hilarious. But also revealing.

Because this is AI today. Sometimes eerily accurate. Sometimes as confident as it is wrong.

Everyone is trying to figure out what AI really knows. What it assumes and why. Where it helps. Where it hallucinates. And where the line is between magic and mess.

So this week, that's where we're going.

But first—a moment to celebrate.

Kyle Van Pelt won Thought Leader of the Year at the ThinkAdvisor Luminary Awards. Milemarker CTO, Kailash Duriaswami, won CTO of the Year.

Two Luminaries. One team.

Congrats guys. Proud to work alongside you.

All right. Let's dive in.

1. The Truth About AI and Wealth Management: We Have Learned the Words. Now What?

2. Next Mile: Connecting Advisors and Investors to the Innovation Economy 🎧

3. Want to see Navigator in action? Watch the replay

4. Milemarker On the Road ✈️

The Truth About AI and Wealth Management: We Have Learned the Words. Now What?

Three years of vocabulary lessons: Models. LLMs. GPTs. Claude. ChatGPT. Gemini. Version numbers that change every quarter.

You know the players. Your compliance team definitely does.

And if you're like most RIAs, you've started using the tools. The notetakers. The Zocks. The Jumps. The AI features quietly appearing in software you already pay for.

Congratulations. You're conversant.

But conversant isn't competitive.

And it's definitely not efficient. Not scalable.

Knowing the words doesn't mean you've changed how work gets done. Here's the uncomfortable truth: the learning curve isn't over, but it might be changing shape.

The first curve was about understanding what AI is.

The next curve is about understanding what AI can do—with your data, in your firm, under your control.

That's a steeper climb.

Most advisors are renting AI.

Someone else's model. Trained on someone else's data. Optimized for someone else's outcomes. That's fine for transcribing meetings. It's not fine for running your business.

The next frontier is ownership.

Not ownership of the AI itself. But ownership of how AI works with your data.

Your portfolio accounting. Your CRM. Your planning outputs. Your custodial feeds. Your compliance records.

Right now, that data lives in silos. You spend hours ferreting out conflicts, reconciling reports, building dashboards by hand.

AI can change that.

But only if the AI actually sees your data.

Here's what forward-thinking firms are doing:

Step one: Unify the data. Get everything into one place where it can actually be queried, analyzed, and acted upon.

Step two: Deploy AI on top of that unified data. Models that stay secure. Models that get smarter over time. Models you control.

Not one model for everything. Purpose-built models:

• An investment management model for research and analysis. Connected to portfolio accounting. Connected to market data. Connected to everything relevant.

• A business intelligence model for operations. One that actually understands how the firm works and helps leadership make decisions.

The firms that figure this out will have an unfair advantage.

They'll report faster. They'll see patterns earlier. They'll make decisions with confidence.

The firms that don't will keep doing what they've always done: manually pulling data from six systems to answer one question.

2026 is the year to move from AI user to AI operator.

Start with your data. Get it unified. Get it clean. Get it somewhere you can actually work with it.

Then start asking: What do I want to learn from this? What decisions could be faster? What patterns am I missing?

The vocabulary test is done.

The real learning starts now.

This is why we built Navigator.

At Milemarker, we've spent years helping firms unify their data. That work hasn't changed.

What's changed is what you can do once it's unified.

Navigator is our answer. AI that runs on top of your data—inside your environment. Not some generic model trained on the internet. A purpose-built system that actually understands your firm.

You get the power of AI without the risk of copying client data into ChatGPT.

Your compliance team sleeps at night.

And your firm starts operating differently. Faster answers. Cleaner reporting. Decisions backed by everything you know—not just what you can remember.

But here's the thing: Navigator might not be where you start.

Maybe you're still figuring out what unified data even looks like for your firm. Maybe you've got a bigger AI vision but no clear path to get there. Maybe you just want to talk through what's actually possible—and what's hype.

That's a conversation worth having.

We're deep in this every day. We'd love to hear what you're thinking about, what's working, what's not, and where you want to go.

No pitch. Just a real conversation about your plans for AI—and how to make them real.

Reply to this email. Happy to dig in.

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On the Pod: Connecting Advisors and Investors to the Innovation Economy

⚡️Bookmarks

Want to see Navigator in action?

Join us for a live walkthrough.

We'll show you how "Which clients grew AUM fastest this quarter?" gets answered in seconds—not days. No SQL. No IT tickets. No client data leaving your environment.

What you'll see:

• Live Navigator demo

• How AI runs entirely inside your Snowflake environment (zero data exposure)

• Self-service analytics for advisors and ops teams

• Real results: 75% reduction in reporting time, 90% fewer manual data requests

• Your 30-day roadmap to get started

Featuring Kailash Duraiswami (our CTO) and me, moderated by Jessica Perez.

Register here →

Catch the replay here.

Introducing Milemarker Navigator: Your Key to Being AI Powered in 2026

Introducing Milemarker Navigator learn how it supports RIAs in unifying data and overcoming challenges through innovative AI and automation

milemarker.co/introducing-milemarker-navigator-your-key-to-being-ai-powered-in-2026

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

1. December 15-16 - Carmel, IN

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

Jud Mackrill