Seeing the Bigger Picture: Lessons from a Tree Lighting

Your 2025 Data Strategy, Wealthbox & Milemarker Partner & Homrich Berg

Greetings from Manhattan.

New York during the Holidays is always a pretty great time.

I’m wrapping up some meetings and headed back to Charleston as we knock out a busy December calendar at work and home.

This week, I’m sharing a bit of my holiday decorating experience as it relates to how we think about our own business - especially as we stand on the crux of such a key time in technology, operations, and the future of advice.

Here’s the Connected Advisor:

  1. Seeing the Bigger Picture: Lessons from a Tree Lighting

  2. January Data & Tech Strategy Sessions Available

  3. Milemarker Partners with Wealthbox

  4. A 12-Year Succession Plan Designed To Launch A Firm Into The Future 🎧

  5. Bookmarks

    1. Available Data Strategy Sessions in Q1

    2. Milemarker Announces AI Enablement & Data Strategy Offer

  6. Milemarker On the Road ✈️

Let’s turn on the lights and grab some cider.

Seeing the Bigger Picture: Lessons from a Tree Lighting

I’m not sure how your post-Thanksgiving weekend went, but if it’s anything like mine, it probably involved gearing up for the next holiday. In my family, we celebrate Christmas, and the transition from turkey to tinsel happens fast.

It starts with hauling decorations out of storage and inevitably realizing that something needs replacing—thankfully, stores are stocked. Then comes the crowning task: setting up the Christmas tree.

This year, there was a moment when Kim, my partner, called me over to assess the tree’s progress. “What do you think?” she asked. “Where am I off? Does something look imbalanced?”

Her question struck me because it parallels something we all face in business. It’s easy to get immersed in the details, but sometimes, you need a fresh perspective to see what’s missing—or misaligned.

The Business “Tree”

Much like decorating a tree, running a business involves balancing different pieces to create a unified whole. You have a vision for where you want to be, but achieving it requires more than just effort; it requires strategy, alignment, and perspective.

We know the future will look drastically different from today. Businesses that adopt the right strategies will outpace their competitors. Some will lead as innovators, others will follow closely behind, and some will fall behind entirely.

The question becomes: How do you position your business to thrive in the midst of rapid change, especially with transformative forces like AI reshaping entire industries?

Finding Balance and Perspective

Just as Kim asked me to come in and assess the tree, business leaders need trusted partners and advisors to offer an outside perspective. These collaborators help ensure everything fits together in a balanced, purposeful way.

Understand the Future: We know AI will be a game-changer. But what does that look like for your business? Where do you need to prepare?

Plan Your Next Steps: Once you’ve identified gaps or areas for improvement, it’s time to plot your path. Write down the steps you need to take, working through them sequentially and break them down into manageable parts. Review your current resources - people, technology, budget and time. Are they all aligned to meet the path you’ve created?

Bring the Team Along: Success isn’t just about what the CEO envisions; it’s about engaging the entire team. A cohesive plan involves input and buy-in from everyone. Make sure that part of your plan includes internal communication, feedback and discussion to get the most momentum possible.

The Importance of Clarity

As the year draws to a close, there’s no better time to pause, assess, and plan. A clear strategy, much like a well-decorated tree, can be the centerpiece that sets the tone for the year ahead.

Personally, I enjoy helping businesses achieve this clarity. It’s something I prioritize for my own companies and something I’ve been fortunate to do for firms across the industry.

Let’s Tackle 2025 Together

If you’re ready to take a fresh look at your business “tree,” I’d love to help. I have a limited number of engagements available in January, February, and March to work with you on getting clear, building a plan, and setting the stage for success in the year ahead.

Let’s make this your best year yet.

Click the link below to schedule time with me, and let’s create something extraordinary together.

Until next time, have a great weekend, and thanks for being a part of the Connected Advisor community.

— Jud

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New Integrations: Wealthbox + Milemarker



On the Pod: A 12-Year Succession Plan Designed To Launch A Firm Into The Future

Episode 070: Succession planning and growth strategies are critical considerations for RIAs seeking long-term sustainability. As firms evolve and leadership transitions occur, a well-defined succession plan ensures smooth handover and business continuity. Succession plans, coupled with strategic growth initiatives and investing in the right technology, allow RIAs to deliver better client service, attract top talent and potential leaders, and provide more sophisticated services.

In this episode, Kyle Van Pelt talks with Thomas Carroll, CEO & President of Homrich Berg. Thomas has an extensive background in wealth management, both as an advisor to clients and as a leader of client service organizations. They discuss the importance of a well-defined succession plan and growth strategies, how RIAs can effectively plan succession, and how investing in technology improves client and advisor experiences. Thomas also shares insights on the trend of advisors and clients migrating to RIAs, and the value of maintaining a culture and service model while scaling.

In this episode:

[02:05] - Thomas' money moment

[07:05] - Homrich Berg's 12-year succession plan

[10:07] - How RIAs plan for succession

[13:39] - The emotional aspects of leadership transition

[16:03] - Why advisors and clients migrate to RIAs

[19:38] - The "Goldilocks" size for RIAs

[21:59] - Maintaining the "Goldilocks" phase while scaling

[25:10] - Technology investments at Homrich Berg

[28:35] - Homrich Berg's philosophy for growth

[30:20] - Trends in wealth management

[34:05] - Thomas' Milemarker Minute

Key Takeaways

  1. A well-defined succession plan is important for a smooth leadership and equity transition in RIAs.

  2. Clients are becoming more sophisticated and seeking fee-only advisors who prioritize their best interests—a trend that’s driving growth for independent RIAs.

  3. The "Goldilocks" size for RIAs balances scale and client service. It is big enough to offer scale, resources, and technology investments, yet nimble and client-centric.

  4. Strategic growth can enhance client experience when combined with technology investments. 

  5. Optimizing core technology systems is more effective than acquiring multiple-point solutions.

⚡️Bookmarks

Available Data Strategy Sessions in Q1

I have several available sessions in Q1 2025 to work with advisory firms to help define technology and data strategy. Spaces are limited, but I’d love to discuss whether this can help you make meaningful progress.

These sessions are built to align your team around technology, assess your current strategy, and design a path for you to break through barriers that may be hamstringing your scale.

Send me an email if you’re interested: [email protected] 

Milemarker Announces AI Enablement and Data Model

We were excited to announce the Milemarker Data Model and AI Enablement solution earlier this week. If you’re looking to leverage AI in the future, having clean data that is properly configured is key.

Milemarker on the Road

Our team in Chicago this week



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

  1. December 4-5 Chicago, IL

  2. December 4-5 - New York, NY

  3. December 9-11 - Las Vegas, NV

  4. December 17 - Birmingham, AL

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