We Just Wrapped Up Ascent. Here’s What I Keep Thinking About.

Most of this week was spent in Orlando at Orion’s user conference, Ascent.

Feels like yesterday that I was at Orion when the team realized we’d hit a tipping point—we needed an annual conference. So I got the job: brand it, bring it together, make it work.

That first year, I stumbled across Hilaree Nelson. Alpinist. Storyteller. Extraordinary athlete. She could capture your imagination like few others.

So we built the event around her. Brought her in. Launched Ascent.

Sadly, Hilaree passed away in a climbing accident in India in 2022. And standing in the middle of this year’s conference, I kept thinking about her story. About what she built. About what Orion was building.

And about the bigger question:

What are we climbing toward?

It’s the question that matters whether you’re scaling your RIA, choosing tech solutions, or just picking the right managed service provider for your printers.

So this week, let’s talk about that.

Here’s this week’s Connected Advisor newsletter.

1. What Are We Climbing Toward?

2. On the Pod: How Wealth Management Falls Short—And How to Fix It  🎧

3. Bookmarks

   1. Milemarker Names Kailash Duriaswami as Partner and CTO

   2. Plaid Tightens Its Brand

4. Milemarker On the Road ✈️

What Are We Climbing Toward? How We May Want to Refocus as We Build the Next Chapter of Wealth Management

This past week has been a lot of fun.

The company where I got my start in 2004 just hosted its largest-ever conference—1,800 advisors and attendees. A massive success for Orion.

Even more, it was a great moment to reconnect with so many people and companies I’ve spent significant parts of my life serving.

The market is compounding—not just financially, but structurally. Firms are jamming businesses into businesses, trying to make sense of it all.

It’s a cycle we see over and over:

✅ Advisors start at Morgan Stanley, Wells Fargo, LPL, et. al.

✅ They move toward independence.

✅ They join or launch their own RIA.

✅ Then they need help and ask—Do I build? Do I buy? Do I partner?

And in all of this, there are so many models:

• Lean and efficient firms.

• PE-backed aggregators.

• Hyper-specialized niche players.

• Independent, uniquely structured firms.

But beyond how firms are growing, I think there’s a bigger, more important question:

What are we actually climbing toward?

Are we just aggregating for the sake of growth and shareholder value?

Or are we creating something truly extraordinary—something that wouldn’t exist outside of this construct?

As the industry accelerates, three things should be top of mind:

1️⃣ Is what we’re building improving the client experience? Making it more future-proof, more valuable?

2️⃣ Is it giving us more time? To be present—with our clients, our teams, our families?

3️⃣ Are the solutions we are using increasing the value of our firms, or is it creating yet another mediocre feature that my advisors won’t use?

The industry will 3x in the next few years—just look at the research, the PowerPoints, the endless Cerulli name-drops.

We all know RIAs are the most exciting segment in wealth management.

But let’s not get caught up in the rush.

Let’s play with our cards up.

The more we define why we’re growing, the more we can align with the right partners, the right values, and the right vision.

So—what are we climbing toward?

Would love to hear your thoughts.

________________________

On the Pod: How Wealth Management Falls Short—And How to Fix It

Episode 079: In this episode of The Connected Advisor, Milemarker CMO and Cofounder Jud Mackrill speaks with Adrian Johnstone, CEO of Practifi, about his journey into wealth management and how Practifi helps RIAs streamline operations.

They discuss the evolving wealth management landscape, the challenge of balancing software customization with usability, and the future of AI in financial services. Adrian emphasizes the importance of thinking long-term when choosing technology and how RIAs can drive sustainable growth through better client relationships, rather than relying solely on acquisitions or market performance.

In this episode:

[02:05] - Adrian’s journey into wealth management

[03:34] - The origin of Practifi

[04:09] - Practifi's team, customer base, and market presence

[05:40] - Practifi’s unique position and connection with Salesforce

[08:51] - How Practifi combines service and software to deliver value

[13:12] - The importance of long-term planning when choosing a CRM

[16:36] - Practifi's design and user experience

[19:51] - The role of AI and the future of CRM technology

[22:09] - Practifi's ideal client profile

[23:28] - Data ownership and integration

⚡️Bookmarks

Milemarker Names Kailash Duriaswami as Partner and CTO

We are excited to officially name Kailash Duriaswami as a partner and CTO at Milemarker. His leadership and character have been a massive add to our team and I am thrilled to get to work alongside him.

Plaid Tightens It’s Brand

Kudos to the team at Plaid on their brand refresh. They are pushing further into being the fabric of financial services. Their product is a very effective tool we use to power unique solutions, and it's fun to see how they are continuing to reinvest in their identity.

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

1. February 12-13 - New York, NY

2. February 16-19 - Orlando, FL

3. March 1 - Anchorage, AK

4. March 10 - Charleston, SC (Closed Lecture at College of Charleston)

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