You’re Watching the Field, But Are You Watching the Score?

Helium Advisors, Creative Planning Raises, & Brian Chesky on Launching

Certain weeks drag on and some fly by. This one has flown.

Despite having many things on our calendar, Kim and I were able to sneak away to catch Ray LaMontagne with Gregory Alan Isakov in Charleston on Tuesday. It was a perfect evening to listen to music under the stars.

If you haven’t been to the Lowcountry during this time of the year, you are missing an exceptional setting.

Sunday afternoons fishing with my 10-year-old son.

This week, I’m watching my 17-year-old son coach his little brother’s football team and plan their offense for Saturday morning's matchup between the Ravens and the Texans. The whole family plans our weekends around the games the kids are playing and college football games.

My thoughts this week center on some key takeaways from last week’s top CFB matchup.

Here’s this week’s Connected Advisor.

  1. You’re Watching the Field, But Are You Watching the Score?

  2. Helium Advisors — The Buddy System Develops Talent and Provides Robust Service for Clients 🎧

  3. Creative Planning Redefines Success for RIAs 

  4. Brian Chesky on the Benefits of Launching

  5. Milemarker On the Road ✈️

Let’s go.

You’re Watching the Field, But Are You Watching the Score?

Let’s talk about Alabama vs. Georgia, September 28, 2024. Sorry Georgia fans.

Alabama was rolling. Early in the game, it felt like they were unstoppable—picking up yards at will, moving the ball like a machine. But then, just like that, Georgia roared back. By the fourth quarter, it was tied up, and suddenly, all the early Alabama domination didn’t seem to matter anymore.

That is until Ryan Williams, a 17-year-old true freshman, stepped up. In the last minutes of the game, he made two ridiculous catches—think Michael Jordan in cleats—putting Alabama back on top in a game that moments before looked like it could slip away. Alabama found a way to win.

What does this have to do with your business?

The momentum of each day can swing, just like it can in a game. Being able to watch the scoreboard when the momentum is shifting will make or break your business.

Most of Us Only Check the Scoreboard When We Have To

In sports, the scoreboard is visible everywhere. But in business? You might only look at your key metrics once a month, once a quarter, or just before a board meeting. Frankly, that’s a problem.

When you’re on the field, running your business every day, it’s easy to focus on immediate tasks—the tyranny of the urgent demands you pay attention to burning questions and decisions. If you can’t check the score regularly, how do you know if all those seemingly urgent decisions you make are moving you toward a win? I don’t mean revenue alone—your true numbers like customer satisfaction, team happiness, profitability, and operational health are all important.

At Milemarker, we work with firms that struggle with exactly this. They know they’re on the field, but they’re flying blind without a clear scoreboard. What’s even more frustrating? They have the data—they just can’t see it synthesized or contextualized without a lot of manual work.

Here’s How Alabama Stayed Ahead

Alabama could’ve coasted, thinking they had the win locked up. But they could see the metrics, not just feel the momentum. They kept an eye on the clock, the score, the plays left. Their ability to focus on all of that data, gave them the direction to call the right plays. It’s what put Ryan Williams in position to step up and keep Alabama in control when it mattered most.

In your business, that’s what your scoreboard does—it keeps you focused on the things that matter. It gives you real-time data, not just a quarterly snapshot. Are your clients happy? Is your team motivated? How’s your cash flow today, not three months ago?

How to Build Your Scoreboard

Building a scoreboard that matters means integrating metrics into your day-to-day. Understanding the score isn’t just about celebrating wins after the fact—it’s about adjusting strategy in the moment to ensure you come out on top.

So, what’s your scoreboard telling you? If you need help to build one, let’s talk about how Milemarker can help you not just play the game, but win it.

Enjoy the weekend, and as always, keep your eye on the scoreboard.

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On the Pod: Helium Advisors — The Buddy System Develops Talent and Provides Robust Service for Clients

In this episode, Gary Russell, Partner and Co-Founder at Helium Advisors, discusses Helium's buddy system, how it works, and the benefits it provides.

Gary also talks about holistic planning and how using the right technology creates a unique client experience.

Key Takeaways:

  1. Helium's buddy system pairs advisors to enhance their skill sets and deliver more comprehensive client advice.

  2. Holistic planning considers all aspects of a client's financial life, including taxes, estate, and business planning.

  3. The future of financial planning involves more consolidation and integration of AI

Episode Breakdown:

  • 01:49 - Gary's money moment

  • 03:37 - What inspired Gary to become a financial advisor

  • 05:34 - What influenced Helium's culture

  • 07:39 - Helium's buddy system

  • 13:22 - Holistic planning defined

  • 18:19 - Leveraging technology for better client service

  • 23:40 - Technology in holistic planning

  • 26:02 - Gary's outlook on the future of the industry

  • 27:53- Gary's Milemarker Minute

This episode highlights the importance of collaboration and holistic approaches in financial planning. 

Creative Planning Redefines Success for RIAs

I worked with Creative Planning around 2010; at that time, you could tell how unique and differently wired they were. Of the top firms I’ve been able to serve, Creative has consistently focused on providing value to their clients. Congrats to Peter and his team.

Brian Chesky on the Benefits of Launching

I agree with Chesky that launching often has a greater impact on organizational alignment than nearly any other activity you can do. It has helps us align ambition, organize the normal business chaos into a reasoned methodical flow.


Milemarker on the Road

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

  1. October 6-10 - Arlington, TX

  2. October 23-24 - Nashville, TN

  3. October 25 - Charleston, SC

  4. October 28-30 - San Francisco, CA

  5. November 4-5 - New York, NY

  6. November 11-12 - Charleston, SC

  7. November 12-13 - San Diego, CA

  8. November 12-14 - Arlington, TX

  9. November 18-20 - San Francisco, CA

  10. November 21-22 - Omaha, NE

  11. December 4-5 - New York, NY

  12. December 9-11 - Las Vegas, NV

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