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The Real Semi-Charmed Kind of Life: Building a Persistent Wealth Management Company

Future Proof Recap, Milemarker a Luminary Finalist & Larry Ellison on the Race for GPUs

It feels great to be back on the West Coast.

Me with Kim, Kyle and Jessica from the Milemarker and Mammoth teams.

A number of our team were at the Future Proof Festival in Huntington Beach. It was our third year attending, and each year, Matt, Nyle, and the team that runs the conference continually raise the bar and redefine experiences for our industry.

If you weren’t among the +4,200 people who attended this year, I highly recommend you circle it for next year.

Here’s this week’s Connected Advisor.

  1. The Real Semi-Charmed Kind of Life: Building a Persistent Wealth Management Company

  2. Financial Planning for Wealth Creators with Craig Robson 🎧

  3. Bookmarks

    • Larry Ellison on the Race for GPUs

    • Milemarker is a Finalist for the Luminaries

  4. Milemarker On the Road ✈️

Let’s kick this off. 🦵🏈

The Real Semi-Charmed Kind of Life: Building a Persistent Wealth Management Company

Earlier this week, I found myself at a Third Eye Blind concert in Orange County as part of the Future Proof Festival.

It's not exactly the music I usually gravitate to, but there’s no denying their impact.

As I stood there, watching the crowd sing along to every word, I did what most of us do these days: I pulled out my phone and started digging into their story - starting with Wikipedia.

The band has been around since 1993, when Stephan Jenkins and Kevin Cadogan formed it. Today, only Jenkins remains, but the band and the brand are still here. Twelve million records have been sold, and songs have appeared in over 30 movies and TV shows.

Third Eye Blind didn’t stop when the lineup changed.

They didn’t quit when the music industry shifted.

They didn’t fade away when things got tough.

They kept showing up. They kept writing, recording, and touring (averaging at least 50 shows a year).

They kept going.

And that’s what it takes to build something great.

An Industry Always In Transition

At the same time I was listening to Jenkins sing “How It's Going to Be,” I was surrounded by advisors at the largest conference in Wealth Management. Some were friends, some were clients and some were people I’d never met before. But as I listened to their stories, I couldn’t help but notice the same theme: persistence.

I met people who are in the thick of acquisitions. Others are growing their practices, creating real value, and spend most days heads down, doing meaningful work for their clients. But here’s the thing—none of it is easy. It’s lonely. It’s hard. It’s late nights and early mornings. It’s wondering if anyone else cares as much as you do.

Sometimes, you even start to question yourself: Am I crazy for wanting this so badly? Wouldn’t life be easier if I just work a 9 to 5?

But here’s the truth: Building something from nothing is always worth it.

I was talking with a friend on the way to the airport. He’s with Mercer Advisors now. I remember when I was first introduced to Mercer. In 2011, they were at $3.6 billion in AUM when I helped them move from Schwab to TD Ameritrade, from TechFi to Orion, and onto Salesforce as their CRM.

Today? They’re over $45 billion in AUM. The scale is different, but the philosophies of their advisors are largely the same. The secret? Persistence.

That’s how they got here.

James Clear does a nice job of describing persistence.  

The most useful form of patience is persistence. Patience implies waiting for things to improve on their own. Persistence implies keeping your head down and continuing to work when things take longer than you expect

Compound Persistence

As part of Future Proof, Josh Brown and Michael Batnick interviewed Peter Mallouk of Creative Planning. Today, Creative Planning is a powerhouse, but it started just like any other firm—small, scrappy, trying to get off the ground. Peter and his team kept showing up. Every day. Writing the songs. Practicing. Delivering.

And now? Creative Planning is a juggernaut.

This post is for you—the advisor feeling like your legs are about to give out. The one wondering if anyone cares as much as you do. Guess what? It doesn’t matter if they care. What matters is that you care. What matters is that you keep showing up.

As a builder, I’m here for you. We need more great advisors doing great work, serving clients in their own way. And let me tell you, I’ve never been more excited about this industry’s future. We’re getting smarter, more self-aware, more tech-savvy.

The future is bright.

And if you’re out there, working late, grinding it out, and pushing the needle forward for your clients—I see you. Keep going.

Just like the successful founders of the brands you admire kept showing up, do the same.

The world needs what you’re building.

________________________

On the Pod: Financial Planning for Wealth Creators with Craig Robson

In this episode, Kyle sits down with Craig Robson, Founding Principal and Managing Director at Regent Peak Wealth Advisors, to explore the art of financial planning for wealth creators.

Key discussion points include the importance of using a tailored tech stack that meets a firm’s specific needs rather than a one-size-fits-all approach and how involving the next generation in family wealth discussions ensures a smooth wealth transfer. Craig also highlights his approach to solving complex financial challenges and the value of being an independent advisor.

Key Takeaways:

  1. Choosing the right technology solutions differentiates independent advisors from larger firms.

  2. Engaging the next generation in family wealth discussions fosters financial understanding and a sustainable legacy.

  3. Successful financial advisory services go beyond asset management, incorporating life coaching and consulting for holistic client support.

Episode Breakdown:

• 01:24 - Craig’s hockey story

• 02:56 - Craig’s money moment

• 08:56 - Why Craig left one of the world’s largest wirehouses

• 15:06 - Why Craig serves wealth creators

• 22:01 - Thoughts on being a fiduciary

• 26:54 - Helping the next generation of investors

• 36:21 - Growing organically

• 42:21 - Craig’s Milemarker Minute

This episode sheds light on what it means to build a legacy, manage generational wealth, and use the best tools to serve clients at the highest level.

Bookmarks

The Race for GPU’s is Like F1

Larry Ellison recently shared his perspective on why Nvidia is the most important company in the world today. I thought it was a very interesting perspective on how global competition will become increasingly intense.

Milemarker is a Finalist for the Luminaries

We are proud to announce that Milemarker is named a finalist for the Luminaries awards — which will be announced December 11 in Las Vegas.


Milemarker on the Road

Catch our team on the road at the following events or cities:

  1. October 6-7 - Arlington, TX

  2. October 8-10 - Birmingham, AL

  3. October 23-24 - Nashville, TN

  4. October 25 - Charleston, SC

  5. October 28-30 - San Francisco, CA

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

Jud Mackrill