Back-to-school prep is in full swing in our house.

In the same way, many of our businesses are gearing up for the last push of the year. The last four months to finish strong and lock in for the next year in terms of planning, budgets and vision.

As we approach this change of season, here’s what is on the docket for this week’s Connected.

  1. AI’s Over/Under: How AI Will Practically Impact Wealth Management
  2. Elevating WealthTech Marketing Strategies – Diana Cabrices 🎧
  3. Last Chance: Forging the Future of Financial Advice 📍
  4. LPL Adds Direct Indexing. Is anyone left to add DI and Is anyone Actually Using It?
  5. Barstool Goes Independent. What does this mean for mixing media and finance?
  6. Steve Martin Walks You Through the Evil Banjo Forest

In the words of late Michael Brezatto, let’s let it rip.

AI’s Over/Under: How AI Will Practically Impact Wealth Management

Today, we can’t visit any news source without hearing about AI and its larger-than-life applications.

TV and movies have touched on AI and similar ideas forever. Heck, I’ve talked about it a lot in Connected, in the press and on a bunch of podcasts.

In fact, I kicked off my week with my friends Jack Sharry and Matt Nollman talking AI on the WealthTech on Deck podcast. Produced by the Turncast team, Jack’s show is arguably the best podcast out there on the reality that is wealth technology that is truly powering the future of wealth management.

Jack Sharry - Lifeyield

On a topic that gets a lot of buzz, its often difficult to separate the signal from the noise.

Jack and I ran through a lot of ideas around AI and cut to the clear facts on where its overrated and where its truly practical.

To me, AI is becoming increasingly practical. We are seeing it analyze complex data and simplify lots of situations. We are seeing it transform functions that used to require teams of people and create instant scale inside of RIA’s and BDs.

Depending on who you are, what you have to deal with in terms of technology support, compliance overloads and general time, you have a varied experience on where AI has relevance for you now and tomorrow.

Let me break down a few things that Jack and I discussed as they are really relevant to the decision-makers who read Connected.

Why AI is Overhyped

Simply put, AI is overhyped.

Media outlets, shows and movies love to depict AI as a highly advanced and autonomous technology that can mimic human intelligence perfectly.

But this couldn’t be further from the truth. AI is effectively in its infancy, and the need for human intelligence, especially when it comes to financial advice, will not be going anywhere anytime soon.

Here are just a few of the most prominent limitations AI has when it comes to replacing financial advisors:

Lack of Contextual Understanding: Financial decisions are influenced by individual circumstances, family dynamics, and life goals. Humans can better understand a client’s situation’s broader context and nuances, leading to more tailored and relevant advice.

Complex Decision-Making: Financial advice often involves intricate decisions that require weighing various options, considering long-term implications, and understanding each client’s unique needs. Human advisors can engage in nuanced discussions to help clients make informed choices.

The Broader Scope: Financial decisions are often intertwined with non-financial goals such as philanthropy, legacy planning, and personal values. Human advisors can help clients align their financial decisions with these broader aspirations.

AI cannot yet replicate the unique qualities that human financial advisors bring to the table—such as empathy, emotional intelligence, personalization, and a holistic understanding. The personalization element of having a financial advisor is invaluable.

Notice I said, yet.

Why AI is Underhyped

While AI isn’t the end-all-be-all, it certainly has its place in all of our businesses.

It’s about knowing what AI to implement and where to implement it in your business to optimize processes and enhance decision-making.

Here are a couple of my favorite AI tools that I use every single day:

Loom AI

Loom AI is a video messaging tool that allows you to easily record yourself, your screen or both simultaneously to efficiently share ideas. Simply hit record and share the link to the video (which anyone can view without having to make a Loom account) with team members, business partners, clients or prospective clients.

Loom also automatically creates a written transcript of each video as well as creates a customized title.

Fathom AI

Fathom is an AI virtual meeting assistant to record, transcribe, highlight, and summarize your virtual meetings via Zoom, Microsoft Teams, or Google Meet.

It is also integrates with your CRM (Salesforce, HubSpot, etc.) to sync your highlights & notes to any matching Contacts, Accounts, & Opportunities, as well as auto-generates call & action item summaries that can be dropped into Notion, Google Docs, Asana, Todoist and Gmail with a single click.

My favorite part about both of these tools: all you have to do is just hit record, and AI does the rest.

The New 80/20

I believe that with AI, there’s a new 80/20 emerging.

80% AI-driven analysis, 20% subjective assessment.

80% AI may seem like a lot, but hear me out.

As AI handles routine tasks, data analysis, and algorithmic trading – real life advisors can focus on high-value activities like personalized advisory, emotional support, ethical considerations, and complex decision-making.

The operational aspects of our businesses that AI has the potential to effectively and efficiently navigate often require the most attention throughout the day. AI enables you to automate the routine, time-consuming things in your business so you can spend your time on what matters most—spending time with your clients.

Taking a balanced perspective is usually the best way to go with most things in life, and AI/human intelligence is no different.

Future Uses of AI in Your Advisory Firm

You will see AI rework how simulations work.

For years the 1000-scenario Monte Carlo simulation was the standard. AI allows for the injection of even more considerations to redefine how precise our probabilities of success truly are. This will augment your work vs. replace it. You will now be able to talk about more advanced nuances that may play into the success of a plan.

AI will Streamline Your Asset Location.

Advisors know that they should be better organizing their household structures to better optimize for taxes across asset location. AI will automate this work in a matter of years.

AI will Redefine Client Experience.

As AI becomes more normal to your clients, it will lead them to expect more from you quickly. Rather than talking to you, they want to be able to prompt information from you. Your job will be finding how to do this within your current systems and client experience, compliantly and securely.

AI will Help You Focus on Your Highest and Best Use of Your Time.

The reality is that much of what we deal with most days is administrative. Wealth Management, when in its perfect state, is a creative work — although many things tend to take away that feeling of creativity. AI will help us automate insight gathering so that you can better manage the creative orchestra powering the guidance for your clients and the advisors you may also serve.

A growing number of organizations are already running hard at this.

Don’t believe me?

Check Morgan Stanley’s Job boards.

Or Wells Fargo.


Where are you starting to see gains from AI in your own day-to-day?

When are you going to make an AI related hire or choose an AI related vendor?

Also, where are you seeing resistance to it?

On the Pod

Elevating WealthTech Marketing Strategies with Diana Cabrices

Listen to this week’s episode.

In this week’s Milemarker’s Connected Podcast episode, Kyle talks with Diana Cabrices, Founder and Fractional Chief Evangelist of Diana Cabrices Consulting. Diana shares strategies for building a standout brand as a financial advisor and practical tips on how firms can supercharge their growth.

The episode is available now on your favorite podcast platform. While there, please don’t forget to Download, Like, and Subscribe.

Last Call ATL – You’re Invited: Forging the Future of Wealth Management, August 16

This is your last chance to register for our in-person event next week. The event is designed specifically for RIAs, where we will walk through unlocking tangible success for your clients, business, and professional journey.

Connect with other advisors and industry leaders while you grab a pint and hear from Tim Maurer, Daniel Crosby, Ph.D., and me on the key issues rapidly shaping wealth management’s future.

Event Details:

When: Wednesday, August 16, 2023 at 4:30 pm EST

Where: Bold Monk Brewing, 1737 Ellsworth Industrial Blvd NW Suite D-1 Atlanta, GA 30318

We still have a few spots open and would love for you to join us. Save your seat here.

Highways and Byways. Quick Takes on Industry News & Relevant Content.

LPL Adds Direct Indexing. Is anyone left to add DI and Is Anyone Actually Using It?

Directing indexing has become the trendiest trading solution in recent years. With lots of solutions selling for high multiples to Blackrock, First Trust and others and many companies like Orion building their own, most advisors should have a Direct Indexing solution at their disposal.

The question now becomes, are you actually using it?

As a technologist in this industry for nearly 20 years, one of the biggest failures that exists is a lack of adoption.

If you have Direct Indexing today but are not making it a part of your solution, I’d love to hear what your barriers are? They often are very legit but often they are simply because you have too much going on already.

LPL Adds Direct Indexing Service for Financial Advisors

The nation’s largest independent broker-dealer is the latest to offer direct indexing capabilities for advisors and clients.


Barstool Goes Independent. What does this mean for mixing media and finance?

Barstool is a largely controversial, foul but very influential media brand that has recently gone independent to its original founder, Dave Portnoy.

Penn Gaming and Barstool were not able to work well together ultimately due to the heavily regulated gaming classification of Penn and he wildly unpredictable manner of Barstool.

The reason I even include this is that I fundamentally believe that every financial services company needs to be equal parts technology and media.

While this spin out could sort of be a case against this, I want to encourage you that there is so much great quality education that can come out of your company in the form of your own media brand.

To be clear, Penn didn’t get out of media. They just upgrade it to a professional partner.

Go for it. Say something that matters. Scale it to your audience and bring people into a clear and singular experience.

ESPN Shoves Barstool From Penn Sports-Betting Pact and Back to Founder Dave Portnoy

ESPN muscled aside the upstart Barstool Sports and struck a major sports-betting pact with operator Penn Entertainment that will put the Disney-owner sports giant into gaming and wagering in a majo…


Steve Martin Walks You Through the Evil Banjo Forest

Back-to-school time needs some nice mellow tunes to get you through the havoc. This week I found that with Steve Martin’s banjo duo.

This is what happens when you walk through evil Banjo Forest.  (Alison Brown and I playing Foggy Morning Breaking)


— Steve Martin (@SteveMartinToGo)
Aug 7, 2023



I’m on the road to Phoenix next week to find out what this 200 straight days of 400 degree heat thing is all about and then to meet up with our team in Atlanta. Hope to see some of you there.

Enjoy your weekend!

Written by Jud Mackrill

Edited by Amy Simpson