Happy Weekend.

I’m sitting here in the Delta lounge at O’Hare waiting to fly home from an awesome week on the road.

NYC, Tampa, Atlanta, and Chicago. Perfect weather and even better presentations and talks.

Jud on the left. Chris Horvath of Taiko on the right. 🙂

On Wednesday, we launched the first in a new webinar series with SignatureFD called How I AI — a behind-the-scenes look at how firms are actually adopting AI. Less theory, less hype, more practical application. Look for the next one soon.

And throughout the week, our team at Milemarker shipped some incredible new features — things I've wanted to launch for a very long time. More on that shortly.

Now, as I cruise back home, I wanted to share something I started writing on a flight out of LaGuardia earlier this week. It's about inspiration, succession, soul, and what happens when the songwriter is no longer at the helm.

Here's this week's Rising Tide.

  1. The Red Hot Chili Peppers Secret to Succession

  2. Podcast: How Advisors Can Beat the Biggest Retirement Risk 🎧

  3. Milemarker Relay Launch

  4. Milemarker On the Road ✈️

The Red Hot Chili Peppers Secret to Succession

It's 7:45 pm on Monday. Wheels up from LGA, en route to Tampa. Caught a perfect glimpse of Brooklyn and lower Manhattan as the plane climbed.

Foo Fighters' new album, Your Favorite Toy, dropped Friday. The opener, Caught in the Echo, came out as a preview a few weeks back, and it's in my earbuds right now (that's right — I’m using the always-tangled corded version again). It has everything you could want in a rock song.

I recently watched the Red Hot Chili Peppers documentary — part behind-the-music, part tribute to Hillel Slovak, their original guitarist, who died in 1988.

So much of music is about inspiration. And inspiration isn't an equal sport. It usually comes down to one or two people who actually propel things forward. If they stall, retire, or pass, success free-falls. Few people talk about it openly, but the absence is palpable — everyone in the room trying to pin down what's missing, when the real answer is that the spark is gone.

So where am I going with this?

The vast majority of you reading this is the spark. You’re the songwriters. The lead vocalists. The heart of the band at your various shops.

The trouble is, your inspiration is perishable. And so is mine.

If we don't professionalize ourselves as conductors — not just players — the music can fade. Your work gets reduced to earnings and metrics that are nowhere near the story any of us will be thankful for on our deathbeds.

Here's where it gets interesting. John Frusciante — the guitarist who replaced Slovak — didn't try to make the band his own. He went the other direction. He studied Slovak obsessively. Immersed himself in how Slovak played, composed, and thought about a song. He tried to think like him. Know him. Respect him. Channel him.

And that is why the Chili Peppers didn't just survive the loss — they became one of the defining bands of their generation.

The conventional wisdom on succession says the next person has to "make the role their own." And sure, eventually that happens — Frusciante became one of the most distinctive guitarists alive. But that came after. First came the immersion. First came the honoring.

Which brings me to something I've been chewing on, and I suspect many of you have too.

With all the consolidation in our industry — the PE rollups, the changing of the guard through corporate actions large and small — there's a whole new tranche of leaders sitting in chairs that used to be occupied by founders.

And it's not just me saying this. I hear it over and over across the industry: a lot of these companies are losing their soul.

The new leaders are doing their jobs. Running the P&L. Hitting the plan. But the reason the company came into being in the first place — the thing that made clients pick it, the thing that made talent show up — is quietly fading out of the room.

I know that's probably not the framing your PE team is going to offer you on the Monday all-hands. But for those of us taking the helm of the next stage of these companies, working to gain a deep empathy for the origin, the history, and the culture of what we're inheriting would do an enormous amount of good — not just for the business, but for the spirit of what we get to carry forward and lead.

That's the Frusciante move. Study it before you riff on it. Honor it before you evolve it. Know why the songs sound the way they sound before you start writing new ones.

Now, the honest flip side.

Sometimes the next generation isn't inheriting greatness.

Sometimes you're taking over from a bad leader. An unhealthy culture. A company three acquisitions deep into losing whatever soul it had to begin with. Not every founder left a legacy worth preserving — and not every "way we've always done it this way" deserves a standing ovation.

When that's the situation, the work is different. You're not excavating what was good and carrying it forward. You're finding the good — the pockets of it that still exist in the team, the clients, the original intent buried under a decade of drift — and helping the organization embody what it actually needs.

That's still honoring work. It's just harder because you have to separate what was truly the soul of the thing from what was just the baggage. And you have to do it without trashing the people who are still there, still believing, still showing up.

The Frusciante move isn't blind reverence. It's discernment. Know the songs well enough to tell which ones deserve to keep getting played — and which ones it's time to retire.

So the question for those of us who are the songwriters right now: have I made my playing legible enough that someone could actually study it? Have I made the music worth immersing in?

And for those stepping into a seat someone else built: have you done the work to understand the song before you decide to change the key — or, when the song wasn't worth saving, to find the good worth building on?

Because if we do our jobs right, the echo keeps going.

And if we don't, it fades.

On the Pod: How Advisors Can Beat the Biggest Retirement Risk

Episode 141: On this week’s episode, Kyle Van Pelt talks with Erik Brenner, CEO, President, and Founding Partner at Hilltop Wealth and Tax Solutions. With more than 30 years of experience, Erik has assisted thousands of individuals in integrating retirement, tax, and estate strategies. At Hilltop, he blends leadership and client advisory responsibilities, shaping the firm's future vision and strategies while providing personalized financial guidance to select clients.

Erik talks with Kyle about what happens when advisory firms stop treating tax and wealth management as separate conversations and start thinking holistically. He discusses the strategic decisions that helped transform Hilltop, including integrating in-house tax services, rethinking the client experience, and doubling down on education-driven growth. Erik also shares how to run great seminars and use technology to keep up with business complexities.

In this episode:

(00:00) - Intro

(01:06) - Erik's money moment

(03:30) - Hilltop's one-stop model: Integration of tax and wealth management

(07:13) - How Hilltop manages large wealth with tax problems

(09:35) - How the SECURE 2.0 Act impacts generational wealth

(16:37) - Using seminars as a modern growth engine

(20:28) - What makes a 5-star seminar experience

(23:39) - Managing tech across multiple business lines

(25:29) - Navigating the transition from being an advisor to a CEO

(27:33) - Erik's outlook on the future of the financial industry

(29:03) - Erik's Milemarker Minute

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

  1. Omaha, NE — May 4

  2. Lincoln, NE — May 5

  3. Nashville, TN — May 7

  4. Columbus, OH - May 12

  5. Indianapolis, IN — May 13-14

  6. Louisville, KY — May 15

  7. Phoenix, AZ - May 20-21

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

Jud Mackrill

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