Will AI Replace Financial Advisors? | Dan Pascone with Rob Burgess | EP #45

Posted on December 23, 2025 by Dan Pascone

Answer Box: TL;DR

AI won’t replace great financial advisors—but it will absolutely replace parts of what they do. In this episode, Dan talks with Rob Burgess, a reporter at Financial Planning (formerly WealthManagement) who covers advisor technology, AI, and investment strategies. They unpack how AI and modern tech stacks are reshaping wealth management—from CRMs and planning software to note-taking tools and autonomous “AI advisor” experiments. Rob explains where AI is already adding real value (note-taking, summarizing, data stitching, faster planning) and where it risks undermining client trust (robotic emails, fully automated advice with no human judgment). The bottom line: advisors who use AI as a force multiplier to deepen relationships, expand services, and simplify client experience will thrive; advisors who try to automate away their humanity will struggle to justify their fees.

Key Takeaways

Who Rob is & what he covers:
- Rob Burgess is a reporter at Financial Planning Magazine who covers investment strategies and technology, with a heavy focus on AI in wealth management since ChatGPT launched.
- He previously worked at Wealth Management Magazine, and before that in local newspapers and legal media. He came into the advisor world from outside the industry, which gives him a fresh lens.
B2B, not mainstream media: Financial Planning and WealthManagement are B2B (business-to-business) publications—written primarily for:
- Financial advisors, RIAs, broker-dealers
- Firm leaders & decision-makers (especially around tech and strategy)
- Vendors and platforms serving the wealth management space
The content is niche—highly relevant if you’re in the industry, easy to ignore if you’re not.
Major trend #1: Advisors expanding services (“light family office”).
- More RIAs are layering on services beyond traditional investment management—things that historically lived in family offices.
- Examples Rob sees:
  - Estate planning coordination
  - Tax planning (not tax prep, but strategy)
  - Helping clients with big life decisions—even unusual ones like buying cars through concierge-style services
- Tech, including AI, makes it easier to operate as a “one-stop shop” or at least a “quarterback” coordinating these services.
Major trend #2: Tech stacks & integration headaches.
- Rob runs a recurring series called “Show Me Your Stack”, where advisors walk through:
  - Their CRM (often the core hub)
  - Planning tools (eMoney, MoneyGuidePro, RightCapital, etc.)
  - Portfolio management & reporting tools
  - Other apps: scheduling, marketing, automation, AI tools, etc.
- Advisors want all this tech to talk to each other smoothly, but true, seamless integration is still rare.
- Tools like Salesforce can integrate deeply but require heavy customization and governance; some smaller RIAs choose lighter CRMs or even non-industry tools like monday.com.
Major trend #3: AI everywhere (visible & invisible).
- Almost every tool in the advisor stack now has some form of AI baked in—sometimes helpful, sometimes just marketing.
- Early high-value use cases were mostly back office:
  - Meeting note-takers that summarize calls and push key points into the CRM
  - Internal summaries, research, and analysis
  - Prospecting tools to find or prioritize leads
- More recently, Rob is seeing AI move into the front-of-house:
  - AI-assisted financial planning (faster what-ifs, scenario modeling)
  - AI in investment tools and client-facing portals
Planning & CRM are beginning to blur.
- Core tools advisors rely on:
  - CRMs: Salesforce, Redtail, Wealthbox, HubSpot, Go High Level, monday.com, etc.
  - Planning software: eMoney, MoneyGuidePro, RightCapital, emerging players like Labretto
  - Portfolio & reporting platforms for performance, billing, and client portals
- Dan notes: planning tools are adding more workflow, document storage, and meeting management features—traditionally CRM territory.
- Everyone wants one coherent experience instead of five disconnected logins; AI may eventually stitch these pieces together more naturally.
Will AI replace advisors—or just parts of their job?
- Most AI vendors and platforms tell advisors: “We’re here to help, not replace you.” They position AI as a copilot, not a competitor.
- But Rob points out not everyone is shy about automation:
  - He highlights a CEO whose company, Range, openly aims to build a fully autonomous “Waymo for financial planning”—a direct attempt to replace advisors for some consumers.
- Real risk: if clients feel their advisor is just pressing buttons in AI tools, they’ll ask, “Why am I paying you?”
- The advisors who win will be those who use AI to:
  - Do deeper planning and analysis
  - Free up time for conversations, empathy, and judgment
  - Bring tax, estate, and planning pieces together in one coherent strategy
Client perception really matters.
- Rob cites a Morningstar study he wrote about: when clients are told an email from their advisor was written by AI, they immediately value the advisor’s time less.
- People are generally okay with AI working behind the scenes, but react negatively when it feels like:
  - They’re talking to a robot
  - The advisor “couldn’t be bothered” to write something personal
- Example: McDonald’s ran an AI-generated ad that was obviously machine-made; public backlash forced them to pull it.
Where AI genuinely shines for advisors:
- AI note-taking & transcription.
  - Dan and Rob both rave about tools like Otter for recording, transcribing, and summarizing meetings.
  - Great for:
    - Capturing every detail without scribbling notes
    - Auto-pushing key points into the CRM
    - Generating accurate follow-up emails and tasks
- Freeing up attention in meetings: Advisors can actually look clients in the eye instead of staring at a notepad or keyboard.
- Rob’s own workflow: as a journalist, automated transcription turned 25–30 minutes of audio (which used to mean 1.5–2 hours of manual transcription) into a quick review task. He still edits the transcript, but the time savings are huge and the quality for readers is higher.
Dan’s view as an advisor & firm owner:
- AI lets advisors:
  - Offer more comprehensive services (planning, tax-aware strategy, estate coordination, investment management) under one umbrella.
  - Centralize client information in one secure vault and portal—making life simpler for clients.
  - Spend less time on manual grunt work and more on high-value conversations.
- But he’s clear: humans are still needed to:
  - Interpret goals and values
  - Explain tradeoffs and risks
  - Guide behavior and decision-making over time
Lightning round highlights:
- One meal for life: Rob picks tacos (Dan enthusiastically agrees).
- Non-phone/PC tech he can’t live without: His electric guitar.
- Bucket list item checked off: Visiting the Sixth Floor Museum at Dealey Plaza (JFK site), interviewing their curator, and donating original 1963 newspapers from his paper.
- Advice to younger self: “Buy Bitcoin…and don’t just write about it.”
How to connect with Rob:
- Read his work at Financial Planning (financial-planning.com).
- Connect with him on LinkedIn.
- Find him on Bluesky as ROBABURG and on Facebook.
- Dan will also tag him when sharing this episode on LinkedIn.

Key Moments

00:00 – Episode setup. Dan introduces himself as CEO and host of Making Sense of Your Money and previews the topic: how AI and wealth-tech are changing advice, where automation helps, and where human judgment still matters.
00:27 – Show intro & sponsor. Tailored Wealth is introduced as the sponsor, and the podcast mission—cut through financial noise and help business leaders make smart decisions—is restated.
00:58 – Meet Rob Burgess. Dan welcomes Rob, who shares his role as a tech and investment strategies reporter at Financial Planning and how he “fell into” the advisor world after a career in local journalism.
02:20 – The ChatGPT tipping point. Rob explains how ChatGPT’s launch in late 2022 made AI an unavoidable part of his beat, quickly dominating his coverage.
03:10 – What is a B2B publication? Rob explains the business-to-business nature of Financial Planning and WealthManagement, and how they narrowly target advisors and firms rather than the general public.
05:07 – Trend: expanding beyond investments. Rob describes advisors adding “family office-style” services: estate planning, tax planning, and even concierge help like buying cars—services not traditionally associated with a typical RIA.
05:59 – “Show Me Your Stack.” Rob shares his recurring series where advisors walk through their tech stacks, exposing the realities of integration (and lack thereof), and the constant desire for tools to talk to each other.
06:39 – AI is injected everywhere. Rob notes most tools now have some AI in them—especially meeting note-takers and prospecting tools—and that AI is increasingly present whether advisors explicitly chose it or not.
07:40 – Business tech vs. client-facing tech. Dan points out the difference between tech that helps run the business and tech that shapes the client experience, noting his own focus on both sides at Tailored Wealth.
08:38 – CRM as the hub…for now. Rob explains why he always asks advisors which CRM they use (Salesforce, Redtail, Wealthbox, etc.), and how that often defines the rest of their stack. He also questions whether CRMs will be as central in a future dominated by AI and tighter integration.
11:01 – Dan’s move to Salesforce. Dan shares Tailored Wealth’s recent migration to Salesforce, highlighting its integration advantages and how it connects to other tools and systems.
12:12 – Alternative CRMs & monday.com. Rob describes advisors using general-purpose tools like monday.com as CRMs when they don’t need all the complexity of enterprise platforms.
13:07 – Planning tools and convergence. They discuss key financial planning systems—eMoney, MoneyGuidePro, RightCapital—and how planning platforms are adding CRM-like features (document storage, meeting workflows).
14:18 – Integration: still the pain point. Both talk about tech stack complexity and tools like Zapier and Make that help connect systems; full integration remains more ideal than reality.
16:59 – Will AI replace advisors? Dan asks the big question. Rob explains that most vendors frame AI as a copilot, but some companies, like Range, explicitly want to build advisor-less planning engines.
18:38 – Client perception & AI-generated communication. Rob describes research showing clients devalue advisors when they know AI wrote their messages—and why visible, front-of-house AI can backfire.
19:52 – The McDonald’s AI ad backlash. Rob references McDonald’s fully AI-generated ad that drew public criticism and was eventually pulled, illustrating how audiences react to “lazy” AI use.
20:59 – Dan’s framework: AI + human = better. Dan argues clients are fine (and often thrilled) when professionals use AI to enhance service—not replace their thinking. The key is using tech to deepen advice, not hollow it out.
21:48 – Advisors as one-stop shops. Dan ties AI and tech back to the advisor value proposition: combining planning, investments, tax, and estate under one coordinated structure with a single secure vault and portal.
23:38 – AI note-takers & the human moment. Rob and Dan discuss note-taking tools like Otter; clients often prefer having a recorder in the room so the advisor can focus entirely on the conversation.
26:10 – Rob’s own AI “must-have.” As a journalist, automated transcription has been life-changing for Rob. It doesn’t replace his judgment; it frees him up to do more meaningful reporting.
27:14 – Lightning round begins. Dan kicks off quick questions to learn more about Rob personally.
27:28 – Tacos for life. Rob chooses tacos as the one meal he’d eat forever.
27:45 – Favorite non-phone/PC tech. Rob picks his electric guitar as his essential piece of hardware.
28:45 – Bucket list moment. Rob shares his experience visiting the Sixth Floor Museum at Dealey Plaza, donating historic newspapers, and interviewing the curator.
29:24 – Advice to younger self. Rob jokes—but also half-seriously says—“Buy Bitcoin. Don’t just write about it.”
29:38 – How to connect. Rob gives his contact points: financial-planning.com, LinkedIn, Bluesky (ROBABURG), and Facebook.
30:15 – Dan’s close. Dan thanks Rob, reminds listeners they can find more content at makingsenseofyourmoney.com, and encourages them to keep focusing on their version of a rich life.

Episode Summary

In this episode of Making Sense of Your Money, Dan sits down with Rob Burgess, a tech and investment strategies reporter at Financial Planning Magazine, to tackle one of the biggest questions in modern wealth management: Will AI replace financial advisors?

Rob’s background is unusual for the industry. He started in local newspapers and later edited a legal publication in Indiana before joining Wealth Management Magazine and eventually Financial Planning. That outsider’s perspective gives him a clear view of how rapidly AI and technology are transforming the advisor landscape.

They start by defining the playing field. Financial Planning and its sibling outlets are B2B publications, written for advisors, firm leaders, and vendors, not the general public. Rob’s beat is at the intersection of strategy and technology—and since late 2022, that’s meant a heavy focus on AI.

Rob describes two big shifts in how advisors work:

First, advisors are expanding their service menus beyond traditional investment management—adding estate planning coordination, tax strategy, and even concierge-style help like assisting clients in buying cars. What used to be the domain of family offices is starting to show up in more mainstream RIAs.
Second, the average advisor’s tech stack has become both more powerful and more complicated. CRMs like Salesforce, Redtail, Wealthbox, and even non-industry tools like monday.com sit alongside planning platforms such as eMoney, MoneyGuidePro, RightCapital, portfolio management systems, client portals, and a growing wave of AI tools.

Dan and Rob spend time on integration, one of the industry’s perennial headaches. Advisors dream of a seamless world where data flows perfectly between systems—but in reality, they often rely on patchwork solutions (including connectors like Zapier or Make) and manual workarounds. As more functionality gets built into planning tools and CRMs, the lines between these categories are starting to blur.

The conversation then zeroes in on AI. Rob notes that early high-impact use cases were largely back office: AI-powered note-taking, transcription, and summarization, along with prospecting and some data analysis. That made sense because if AI makes a mistake, you want a human to catch it before it hits the client. Over time, AI has crept closer to the client-facing side—assisting in planning scenarios, helping generate materials, and even appearing in some client portals.

Dan asks the big question: Are these tools going to replace advisors?

Rob explains that most vendors frame AI as a copilot: a way to save time, improve accuracy, and enable advisors to focus on higher-value work. But he also highlights outliers like the CEO of Range, whose explicit goal is to build a driverless financial planning system, akin to a Waymo for your money. Whether that vision succeeds or not, it shows there are serious efforts underway to automate large parts of the advisory process.

Both agree that the real risk isn’t just what AI can do, but how it’s perceived by clients. Rob cites research showing that when clients find out an email from their advisor was written by AI, they immediately value the advisor’s expertise and time less. People don’t generally mind if AI operates behind the scenes to make things smoother. But when AI is front-and-center—like a fully AI-written ad from McDonald’s that had to be pulled after backlash—there’s a sense that the company or advisor didn’t care enough to show up personally.

Dan connects this to his own practice at Tailored Wealth. He’s a big believer in using AI and technology as force multipliers—to expand services, bring more of a “one-stop shop” feel to planning, and centralize clients’ financial lives in one secure vault and dashboard. But he’s equally clear that humans are indispensable for understanding values and goals, explaining tradeoffs, and guiding behavior over decades.

They highlight one area where AI is an unambiguous win: meeting note-taking and transcription. Tools like Otter allow advisors (and journalists like Rob) to record conversations, auto-transcribe them, and push key points into the CRM or follow-up templates. That change means advisors can give clients their full attention in meetings instead of trying to scribble down notes—and then follow up with far more accurate and complete summaries.

Rob shares how this has transformed his own work as a reporter. Transcribing interviews used to be one of his least favorite tasks; now AI handles the heavy lifting, and he simply reviews and corrects. The result: more time for actual reporting and better outcomes for readers.

Throughout, Dan keeps bringing the conversation back to the core value of a great advisor: turning complex tools into simple, human, coordinated plans. AI might help calculate scenarios faster, stitch data together more neatly, or generate polished documents. But it can’t sit across from a person in a tough life moment and help them weigh the tradeoffs between retiring early, supporting aging parents, paying for kids’ education, or handling the psychological side of risk.

The episode closes with a lighthearted lightning round. Rob chooses tacos as his forever meal, names his electric guitar as the non-phone/PC tech he can’t live without, recounts a bucket-list visit to the Sixth Floor Museum at Dealey Plaza—where he donated 1963 newspapers from his old paper—and gives his younger self the cheeky but honest advice to “buy Bitcoin—don’t just write about it.”

For listeners wondering whether AI will make advisors obsolete, this conversation offers a more nuanced answer: AI will change what advisors do, and how they do it—but the advisors who lean into emotional intelligence, judgment, and human connection will be more valuable than ever.

Full Transcript

Dan: I’m Dan Pascone, CEO and host of the Making Sense of Your Money podcast. Real conversations to help high earners make sharper decisions so their money works as hard as they do. This is episode number 45 and my guest today is Rob Burgess of Financial Planning Magazine, and we discuss how AI and wealth management technology are reshaping financial advice, where automation helps, and why human judgment still matters.

Dan: Before we dive in, make sure you’re subscribed on your favorite platform. And if you find the show valuable, I’d really appreciate you leaving a quick review. Thanks so much and enjoy.

Announcer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Announcer: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: All right, Rob, thanks for joining the Making Sense of Your Money podcast. Really excited to have you today.

Rob: Yeah, thank you for having me. I’m really excited to be here.

Dan: Yeah, this is going to be fun. You’re going to be very much a unique and different guest than we’ve had in the past, and I’m excited to get into what you do and your expertise and your experience and all that.

Dan: So why don’t you start by just giving our audience a quick high-level overview of who you are, what you do, and how you got into your field.

Rob: Great, yeah. So my name is Rob Burgess. I’m a reporter at Financial Planning Magazine. I cover investment strategies and technology, the latter of which, as you might imagine, involves AI a fair amount.

Rob: So that’s been part of my coverage area since—well, ever since ChatGPT came out, basically that’s most of what I’ve been writing about.

Rob: I’ve been here about a year and a half. And before I started in this field, I was a local newspaper editor in northern Indiana. Never really had heard of—I mean, I knew what a financial adviser was roughly, but I certainly hadn’t thought that much about the industry.

Rob: But then I got a job at Wealth Management Magazine as a reporter kind of also covering technology. And, yeah, like I said, that was—let’s see, I started that in October 2022. ChatGPT came out in November of 2022.

Rob: So the next month I was off to the races and like I said, pretty much been writing about AI and how it relates to the wealth management industry ever since.

Dan: All right, very cool. I’m pumped to unpack that with you because that’s a fascinating topic. Obviously, AI is everywhere these days, but I’m really excited to talk about how it impacts my industry and financial services in general.

Dan: Before we do that, tell our audience a little bit about Wealth Management Magazine and now Financial Planning. Tell us a little bit about the outlets that you report for. For those that aren’t familiar with them—and I certainly am—but for those that aren’t, tell us a little bit about the type of audience that you’re covering and who’s reading it, the types of topics in general.

Dan: We’re going to dig in a little bit deeper as to what you cover, but just tell us a little bit about the two outlets that you’ve worked for and the types of folks that are following.

Rob: Sure. Well, just for people that don’t know, these are called B2B, business-to-business publications, meaning it’s not a general interest category.

Rob: You know, people will ask me what I do and what I write about, and I’m like, you might be interested in what I write about, but if you’re not a financial adviser, you might not be. I don’t know. And I won’t be upset if that’s true.

Rob: I do narrowcast for a pretty specific audience. As you know, I also previously had worked for a legal publication here in Indiana—the Indiana Lawyer—where I was managing editor of that publication. And yeah, that was focused on the state’s legal community. And once again, I don’t know why you would read that publication if you weren’t a lawyer in Indiana.

Rob: So it’s a little bit different than, like I said, most of my background before all this was kind of local newspaper—local journalism, general interest, not really any specific audience other than where you might happen to live and care about the doings of that area.

Rob: But yeah, this is a pretty unique field in that I am kind of focused very specifically on the wealth management industry, advisers, people that make decisions within firms—especially regarding technology and things like that.

Rob: But luckily, there’s a lot to say. I never run out of things to write about.

Dan: Yeah, I’ve seen plenty of your articles and I’ve been lucky enough to be featured in a couple, so I appreciate that.

Dan: But let’s talk a little bit about technology, because I think this is a really interesting topic. So tell us, generally speaking, the trends that you’ve seen as of late. We know AI is taking over and influencing and impacting most industries. What are the general trends you’re seeing in financial planning and wealth management?

Rob: Yeah, so, I mean, there’s a lot of them, but one that I’ve been focused on here recently is advisers expanding their services beyond what you might normally expect just a regular RIA to offer.

Rob: There are these family office-style—at least in the past—services that people didn’t really consider that just a regular adviser would be offering. But as time goes on, they’re adding more and more of these things.

Rob: That can look like a lot of things: estate planning, tax—not preparation necessarily because you would have to be a CPA for that—but tax planning is of course an important element. And even down to helping people buy cars.

Rob: I went to a presentation at the last T3 conference about somebody whose whole business is just helping advisers help clients buy cars. And that’s kind of a concierge service that you might not expect from a regular adviser. So that’s one thing.

Rob: Gosh, there’s so many. I do a series called Show Me Your Stack where we talk about people’s tech stacks and how things do and don’t talk to each other. Integration is always a big topic.

Rob: People always want the pieces of their tech stack to talk to each other better. Of course, you mentioned AI. That’s been a huge game changer—especially with the note-takers and some prospecting tools that have come online that people have found value in.

Rob: And also, everything else in your tech stack probably has AI injected into it whether you want it or not. So it’s like everything—you know, this little pop-up, whatever. I’ve seen it in my own programs I use. It’s just embedded now.

Dan: Yeah, very cool. You said a bunch of stuff there that’s really interesting to me.

Dan: Tell me more about the Show Me Your Stack segment. That’s very, very interesting because I spend a lot of time as a business owner and running an RIA understanding what is the right tech stack for us—both at the business level, right? I almost look at it in twofold: the business level, like how you actually run the business day-to-day, and then the client engagement level—the technology facing the clients to make the client experience better.

Dan: I completely agree with you. It has become a lot more prominent today. I think this is a good thing for the consumer—that folks like me are… I mean, I can think in just the last year of five different services we’ve added to our local suite that we didn’t offer in the past.

Dan: And it is creating more of a one-stop shop experience. I haven’t gotten to the level of helping clients buy cars yet, although I guess we probably could.

Rob: Not many people have. I think it’s an up-and-coming segment, but yeah.

Dan: That’s definitely really a high net worth family office type of service. We can come back to that.

Dan: But let’s talk about Show Me Your Stack. What has surprised you the most as you’ve gone through those segments, and has it been more focused on the client-facing technology or the business-facing technology?

Rob: Well, that’s a good point too because a lot of things might look good on your end, on the advisor end, and might not be intuitive on the client end.

Rob: So even if pieces of the tech stack that I talk to people about have a client-facing part, sometimes they don’t turn that on or that’s not the part they show clients. They might get another portal or tailor it to that.

Rob: But I think that is becoming more of a thing. Also, AI is, I think, entering into that picture as well. So with—you know, I hate to keep going back to AI, but I write about it all the time—most of the applications I saw were back-office things initially, things that the client wouldn’t necessarily see.

Rob: Because it makes sense: if AI makes a mistake, you want to be there to clean it up before someone else sees it. So you might not be ready to unleash that on clients.

Rob: But I’ve started to cover certain pieces of tech stacks that are involved in financial planning, involved in investment management. They’re starting to come online and people are starting to bring that to the front of the house. So that’s been interesting to see.

Rob: In terms of the rest of the tech stack though, one thing I always ask about first when I do that series is: what’s your CRM? Because that’s usually the main kind of piece that holds it all together.

Rob: A lot of people have said Salesforce because that’s the biggest one, but that does take a lot of customization. It can do a lot, and it can also get kind of out of control if you don’t have somebody there managing it and tailoring it for your specific needs.

Rob: So some people have gone different directions, even looking outside the wealth management industry. Maybe they’re a solo RIA that doesn’t need all the bells and whistles of something massive like that.

Rob: They might look at something outside the industry for that. So that’s been really interesting to see—the ways that people, depending on their niche or specialty or the client base they serve or how big or small they are, might say, “You know, this can do a lot. There are a lot of tools here. I don’t necessarily need all these tools, and I might be better off getting something a la carte that might be out of left field for most people.”

Dan: Yeah, it’s a really interesting topic. And to frame it from a perspective of our audience, I think we’ve got a piece of our audience that might be financial advisors or in this business, and then we’ve got others that frankly are in different industries but deal very much with CRM in some way, shape or form.

Dan: Salesforce is sort of industry agnostic, but to your point, you typically—especially in our business—want to have it customized to your interface. We actually, I don’t mind telling you, just made a migration to Salesforce. So we just went through migration, a custom build, customization.

Dan: While it’s early on, I’m very much liking it. And the thing I like about Salesforce is the ability to connect to other places, right?

Dan: So for those that don’t know as much about our industry, you have some big players like Redtail and Wealthbox, which are probably the two biggest players that are specific to financial advisers and financial planners—with Salesforce being the gorilla that is industry agnostic. And there are a couple of others out there.

Dan: I’ve seen Go High Level, which is a little more of a marketing platform but has a CRM experience; I’ve used that in the past. And HubSpot has crept its way into the financial services industry.

Dan: So many folks that might be in tech or other businesses are familiar with those, and it’s interesting to see how that has made its way into financial services and financial planning.

Dan: What other ones are you seeing in your coverage, Rob, other than the ones that maybe I’ve mentioned?

Rob: Of CRM, you mean?

Dan: Yeah.

Rob: Gosh. Well, there was one guy who used something called monday.com, which I had never heard anyone say. That’s one of those ones that’s kind of out of the industry that I hadn’t really heard anyone mention before, and I had to look into that when he talked about that.

Rob: So that was one example. I do hear people talking—and maybe this is something I need to cover more in the future—but will we need a CRM going forward with all these advancements in AI and things becoming integrated?

Rob: We kind of think of that as the bedrock of everything. But is that always going to be true? I don’t know. Maybe in the future some people might find they can do without it and can amalgamate other tools into that.

Dan: Well, it’s an interesting discussion because—and this is my next question for you—how much coverage have you done or topics have you covered related to the financial planning softwares?

Dan: I look at it as: there are really three core softwares that most financial advisors and planners are utilizing or have some form of access to through a broker-dealer, an RIA, or a wirehouse—whatever their structure is.

Dan: They’re typically using, if they’re doing financial planning—which has become more prominent; I think most folks see value in that today, I certainly do—the foundation of our business is built on the financial plan.

Dan: But there’s the financial planning software, there’s the CRM, and then there’s typically some form of either portfolio management and/or reporting software.

Dan: So I’m interested to hear your thoughts and your take on the financial planning softwares and how much coverage you’ve done in that space.

Rob: Oh yeah. Well, I always ask about financial planning, and you’re right. I feel like, more and more, people kind of feel like that’s something you have to have. It’s not really optional anymore.

Rob: You know, eMoney is obviously one that a lot of people use. MoneyGuidePro—those are some of the main ones. There are a lot of different ones. There are a few upstarts coming. I just profiled a company called Labretto, and they do a lot—kind of an interesting take on that—and they’re an up-and-coming one.

Rob: But yeah, those are—like you mentioned—there are a few big players that most people bounce between.

Dan: Yeah, no doubt about it. You mentioned two of the big ones. I would add RightCapital into that mix as a really big player. That’s who we’re currently using.

Dan: And what I would tell you on that front is it’s interesting to see how CRM and financial planning softwares are either integrating or, at times, to some degree overlapping. Because a lot of what you can do, at least on the client side, with a CRM, you can also do in a financial planning software today—like house documents, keep communications.

Dan: If you’ve got it integrated properly, even do—

Dan: To some degree they’re starting to add on some level of meeting management or meeting rhythm and cadence for reviews and stuff like that, which previously were really managed at the CRM level.

Dan: And then there’s the portfolio management, which is if you’re doing full-scale comprehensive wealth management—which we do—you want something that’s tied to where the client’s accounts are actually housed. And integration is the key.

Dan: So that’s my next question for you: how much do you get into integration and how complex have you found this stuff to be? Because I find that integration is—I spend a lot of time thinking about and looking at how all of our systems talk to each other.

Dan: So I’m interested to hear any lessons that you’ve learned or insights you’ve gained on that topic.

Rob: Well, yeah. I mean, like you mentioned with Salesforce, that’s one of the big selling points for Salesforce—how integrated they are with so many things and how deeply embedded they are already.

Rob: So you don’t have to worry about double entry or losing things in the translation, in the shuffle there. That is a constant problem for people. I always ask—that’s a question I always ask in Show Me Your Stack when I do those: how are things talking to each other?

Rob: How much is integrated and how much isn’t? Some things don’t talk to each other very well, but it’s like, how much value do you get out of the software even though the integrations are kind of difficult?

Rob: But yeah, you’re right. It’s definitely something in the industry—an ongoing issue—that there’s a lack of total integration. People definitely dream of that one smooth interface between everything, but I don’t think we’re quite there yet.

Dan: One hundred percent. You see softwares like Make and Zapier—or Zapier, I don’t know which one it is, Zapier, Zapier—I was going to mention that. Those have become very, very popular to connect your tech together.

Dan: All right, so the elephant in the room when it comes to AI in any industry, not just ours, is this perspective of: how am I using it to help what I do versus am I afraid that it’s going to replace what I do?

Dan: So give me any insights or information you’ve gleaned from the people you’ve chatted with and the stories you’ve covered around where that sits for financial services, financial planning, wealth management, etc.

Rob: Yeah. So it’s been really—I mean, that’s a constant topic that I’m covering. People that are boosters of AI, people that want to get this in advisors’ hands, their line 90% of the time, when they’re not trying to scare people, is, “This isn’t going to replace you. This is a help.”

Rob: “This is an assistant. This is something you can bounce ideas off of. This is something that’ll make you faster and save you time.”

Rob: And I do think, to a degree, that might be true. But then I interviewed this guy, CEO of a company named Range, and his stated goal—and I wrote a story about this—is to replace financial advisors.

Rob: He wants to make it like the Waymo model of the driverless car, but for financial planning, basically. That’s his goal. He says it out loud and he doesn’t care who knows it.

Rob: And there are other people on that tip. Like I was saying before about this going into financial planning and investment management, I think the people that are pushing it into that are probably less going to be reassuring people that, “No, this is just to help, we don’t want to replace you.”

Rob: But I do think the danger is that if you’re a client and you see your advisor automating every piece of their job, it’s like, “What am I paying you for?”

Rob: If you’re just using AI—if that’s all you’re doing—I can go out and use AI and figure this out myself. So I think people need to see that connection.

Rob: And I think any time savings people get from this, the successful people that I’ve seen have put that back into client engagement and connecting with their clients and having that one-on-one piece. Not like, “Oh great, I don’t have to talk to my clients anymore.”

Rob: Those people are going to lose out, because there’s been studies done: if a client thinks that you are—and this is from a Morningstar study that I wrote about—if a client knows that an email you sent them was generated by AI, they instantly think you’re worth many dollars less per hour.

Rob: They’re like, “Okay, you can’t even talk to me. You can’t even write your own email to me. What am I paying you for?” So yeah, if people sense—and I have seen this even beyond wealth management; this is just kind of a societal thing—I don’t think people mind it working in the background where they can’t see it.

Rob: But if they know that the whole thing is just you put a prompt in, you got a thing out, and it’s like, “Here, look at this…”

Rob: McDonald’s had an AI ad that they took down after people were outraged about it because it was completely created by AI. It looked like it was created by AI, everyone knew it was, and nobody liked it. They eventually took it down because they were like, “You can’t even be bothered to put your own ad together. Why am I watching this?”

Rob: And I think that’s true in every industry. That’s the value I try to bring as a journalist: I’m talking to people. I’m out there actually connecting. I’m not just going to put a prompt in, “Write a story about this,” and then be like, “Here, read this.” I wouldn’t read that, and I wouldn’t expect anybody in my audience to read that either.

Dan: It’s such a great point, and you’re right. This is not specific to wealth management by any stretch, but it’s almost like there’s going to be a new industry forming to fool people that we’re not using AI.

Dan: It’s like AI to show you that we’re not using AI, right? That’s become—you’re right, we as humans have become sensitized to searching for: was this done by a machine or was this done by a human?

Dan: And I totally agree with you. And it’s interesting because if you think about—I think about the different services that I use as a consumer. Frankly, you’re right: you wouldn’t want to, there’s a negative perception to “I’m paying someone just to use AI.”

Dan: But if the idea is, I’m paying a professional and that professional is really good at using systems and technology and artificial intelligence to provide me a better service—well, to me, I’m all in on that, right?

Dan: So I think it’s an interesting tie back to what you said at the beginning of our conversation, which is: what AI has allowed—I know what it has allowed us to do in our business—is provide more services to the client.

Dan: So I think today if you’re just going around and using AI and saying, “I help you manage your investments…” Well, I mean, that has become a commoditized service. It really has.

Dan: The financial planning I think a little bit less so, even though there’s a lot of AI built into the financial planning softwares. It still requires a human element to understand things like goals and what you’re looking to achieve.

Dan: Because I’ve found anytime I’ve given a new client reigns to run with the financial planning software, it doesn’t end well. So I do find that there very much needs to be humans still involved.

Dan: But I’ll say this from our perspective: I think it’s allowed folks in my space to provide more of a one-stop shop offering. So I don’t think you need to necessarily go out and hire a financial planner, a CPA, a money manager, an insurance person, an estate planner and trust-and-wills person.

Dan: Usually, those things can probably be done under one umbrella now. And then it goes back to the other discussion we had, which is: if you find someone who is able to offer that comprehensive service and they’ve got their systems integrated properly, well now all of your documents, all of your information can live in one secure place.

Dan: That’s what I really preach as a value that we try to bring to our clients: you can have your tax return done, you can have your estate plan done, you can have your financial plans done, and you can have all of your investments in one technology suite.

Dan: You don’t necessarily need to know all of the buttons that are being pushed. You just need to know that I’ve got one secure vault that I upload documents into and that I can view my financial life in one place. And I think that creates a higher level of service.

Rob: Oh yeah, absolutely. And kind of going back to what I said earlier about note-takers being one of the main applications, I think that’s a perfect example of that.

Rob: Because if you’re sitting there taking notes during a meeting, you might not be catching everything someone’s saying and you’re not really listening. You’re more interested in taking the notes.

Rob: Whereas if you know it’s being recorded, you know this is integrated with your CRM and your calendar, and you’ve already got a follow-up email scheduled with the key points or whatever—you don’t have to take your attention away in the moment. You can actually have a more meaningful conversation.

Rob: This is a topic that I discussed on a panel at our Advise AI conference a month or two ago. And that’s really allowed people to—I think people see that value, and that is a way that people find more connection through using that kind of AI.

Dan: For sure. Yeah, it’s amazing. This would be an interesting story for you to cover, especially on the financial side: what are the pieces of AI that consumers want their financial partner to utilize?

Dan: Because to your point, the note-takers—for the most part, while in some cases depending on your compliance infrastructure you need to get authorization to use them, but let’s take compliance out of it for a second—in most cases I find clients absolutely want the note-taker to be in the room.

Dan: Because you’re right, now we’re just having a conversation versus five years ago, if you’re sitting in my conference room and I’m trying to scribble down everything you said, am I really engaged in what we’re saying? That’s number one.

Dan: And B, I as a human might miss something that you said, but I can tell you my note-taker isn’t going to miss anything that you said. So for that information, to your point, you’re adding another layer, which is the integration between the note-taker and your CRM.

Dan: If now, as a client, I know that really everything I’ve ever said to my advisor is in my file in the CRM, to me as a consumer that’s an added level of comfort. That’s a value-added service versus, “My advisor used some form of AI to write me an email, he or she is too lazy to do that themselves.”

Dan: It’s a completely different dynamic, and the perception is really interesting: I really like this AI that you’re using, but this makes you look lazy. So that would be kind of an interesting topic for you to cover at some point.

Rob: Yeah. Well, I mean, in my own work, frankly years ago one of my least favorite parts of my job was transcribing interviews. I just—I’d get done with a great interview and I’d see that I had like 25 minutes to transcribe and I’m like, “Oh no, that’s another hour and a half.”

Rob: Right now I use Otter, which has AI built into it. And the rest of the day I’ll be all skeptical about AI, and then that happens and I’m like, “Yes, you can keep this part. I need this. I’m never going back to the other part.”

Rob: It doesn’t add value to me or my readers for me to sit here for an extra two hours. I still have to check it. It still spells things wrong. It still misses things. You can’t just rely on it blindly.

Rob: But man, it’s been such a time-saver and it allows me to get so much more work done that I think actually adds value. I don’t really think readers are being served any better by me listening to something at half speed and trying to catch every word.

Dan: Well said. Well said.

Dan: All right, I think that’s a great place to segue. That was a great conversation. You are officially entering, Rob, the lightning round now. So we’re going to get to know you a little bit more and talk a little bit more about you.

Dan: And what I tell every guest with the lightning round is: first thought that comes to your mind. Could be a one-word answer, could be a long drawn-out thought, or anywhere in between. You ready?

Rob: All right. Great. Let’s do it.

Dan: All right. One meal for the rest of your life. What is it?

Rob: Tacos.

Dan: You know what? I’m with you on that one. I think we would agree on that one. I like it. I’m with you.

Rob: Had tacos last night. My favorite.

Dan: So this is right in your wheelhouse. I’m very interested to hear your response on this. This one may take you a while to think about—or maybe it doesn’t. What’s one tool or piece of technology other than your computer or your phone that you can’t live without? Could be hardware, software, anywhere in between.

Rob: Oh my gosh, I would have to think about that. Let’s see. I would have said, about 10 years ago, my MP3 player, but I don’t have one of those—I just have a phone now. So I’ve got to think of something else.

Rob: Well, I play guitar—electric guitar. How about that?

Dan: All right. I like it. I like it. Very cool. All right, very good.

Dan: Do you have a personal routine or hack that you very much believe in that you could share with our audience?

Rob: Relating to work or just…?

Dan: Anything.

Rob: Oh gosh. Wow. A hack… let’s see. Well, uh, oh my gosh. I might have to think about this. I don’t know.

Rob: Gosh, what do I do? Can we come back to that one? I’ve got to think about that.

Dan: Sure, we can do that.

Dan: Do you have one bucket list item that you could share with us that you’ve already accomplished? Something you’ve already accomplished and checked off your bucket list?

Rob: A bucket list item… goodness gracious. Well, I got to go to—I’m a history buff, I love history—and I actually got to, when I went to the T3 conference this year, I went to the Sixth Floor Museum at Dealey Plaza and I got to interview the director, the curator there.

Rob: And I donated some newspapers from when I worked as a newspaper editor that somebody had brought from November 1963. I’m a big history buff, so that was a really surreal experience just from this year.

Dan: Very, very cool one. Thanks for sharing that.

Dan: If you could give one piece of advice to your younger self, what would it be?

Rob: Buy Bitcoin.

Dan: I love it. We’ve had that a couple times, actually. A couple people have said that on here. So that makes a lot of sense. That makes a lot of sense.

Rob: Don’t just write about it, Rob.

Dan: Yeah, don’t just write about it. Yeah, practice what you preach. I love it. And by the way, I could argue the same for me as well.

Dan: All right, very cool. And then finally, if our listeners want to connect with you, collaborate with you, check you out somewhere, what’s the best way to find you?

Rob: Great. Well, financial-planning.com—you can read all my stories there. On LinkedIn—I hadn’t really before this year used it as a social platform, but I’ve taken to that this year and I’ve been getting more of an audience there.

Rob: I am on BlueSky as well if anyone’s on that. R-O-B-A-B-U-R-G is my handle. I’m also on Facebook—I don’t post there too often, but I am technically there.

Dan: Cool. All right, sounds cool. We’re going to tag you on LinkedIn because you and I have collaborated there a little bit. So we’re going to tag you in this episode on LinkedIn.

Dan: Well, amazing. Thank you so much for sharing your insights today, Rob. It’s been great having you.

Rob: Great. Thanks so much.

Dan: That’s it for the episode. As always, you can find our podcast, along with our newsletter, our YouTube channel, and this podcast at makingsenseofyourmoney.com.

Dan: As always, prioritize your version of a rich life.

Dan: Awesome, man. That was great. That was great.

Resources & Citations

Financial Planning Magazine: B2B publication covering wealth management, advisor tech, and investment strategies.
WealthManagement.com: Sister outlet focused on advisors and industry trends.
Key planning & CRM tools mentioned: eMoney, MoneyGuidePro, RightCapital, Salesforce, Redtail, Wealthbox, HubSpot, monday.com, Go High Level.
AI tools & concepts: ChatGPT, AI note-takers (e.g., Otter), Range (AI-first planning startup), integration tools like Zapier and Make.
Tailored Wealth: Dan’s advisory firm, integrating financial planning, investments, tax strategy, and technology into a coordinated client experience.

FAQs

Will AI actually replace financial advisors?

Rob’s view (which Dan shares) is that AI will replace tasks, not great advisors. Routine analysis, basic planning calculations, transcription, and some communication can be automated. But the core of advice—understanding human goals, handling emotions, and guiding behavior over time—still requires a person. That said, some companies are actively trying to build “driverless” planning tools, so advisors who don’t adapt may lose certain types of clients to lower-cost, AI-only platforms.

What are the most impactful AI tools for advisors right now?

The biggest wins today are largely back-office and workflow-related:

Meeting note-takers and transcription (e.g., Otter) that capture and summarize conversations.
Drafting summaries, follow-up emails, and internal memos (with human review).
Research and analysis helpers for quickly processing documents or data.
Prospecting tools that help identify or prioritize leads.

The advisors Rob sees thriving are using these tools to free up more time with clients, not to avoid clients.

How are planning software and CRMs evolving together?

Traditionally:

CRMs handled contact info, workflows, tasks, and communications.
Planning software handled cash-flow projections, retirement models, and what-if scenarios.

Increasingly, planning platforms are adding:

Document storage
Meeting management & tasking
Basic communication and client portals

Meanwhile, CRMs are integrating more tightly with planning and portfolio systems. Over time, these categories may feel more like one coordinated environment connected through AI and better integrations.

Is it okay for my advisor to use AI to communicate with me?

Most clients don’t mind AI being used to summarize or draft messages as long as:

The advisor reviews and personalizes what goes out.
The advisor is still clearly thinking about your situation, not just hitting “send” on auto-generated content.

Research suggests that if you know a message was written entirely by AI, you may unconsciously value that advisor’s time and expertise less. So it’s generally better when AI is a behind-the-scenes helper, not your primary point of contact.

As a client, should I care what CRM or planning tool my advisor uses?

You don’t need to know every product name, but you do want to know:

Whether your advisor has a coherent system or just a patchwork of tools.
How they store and protect your information (security and backups).
Whether you’ll have access to a clear, easy-to-use portal or vault for your documents and accounts.

The specific tools matter less than whether they’re used to give you a simple, secure, and transparent experience.

How can advisors talk about AI with their clients without spooking them?

Rob and Dan’s implicit playbook:

Be honest that you use technology to serve clients better.
Emphasize where AI helps: accuracy, documentation, time savings—not as a replacement for your thinking.
Show how the time saved is re-invested into more personal planning, proactive outreach, and strategy.
Avoid giving the impression that your job is just pressing buttons in AI tools; highlight where human judgment still drives decisions.

Disclaimer

This episode and written summary are for educational and informational purposes only. They do not constitute financial, legal, tax, or investment advice, and they do not create a client relationship with Tailored Wealth, Financial Planning Magazine, or any other entity mentioned.

Technology and AI tools discussed are examples, not endorsements or guarantees. Before implementing or relying on any technology, AI system, or financial strategy, you should consult with qualified professionals, including:

A licensed financial advisor or planner
A tax professional (CPA or EA)
An estate planning attorney
Your firm’s compliance team (if you’re an advisor)

Any views expressed by guests are their own and do not necessarily reflect those of Tailored Wealth or its affiliates. Past technology trends or investment outcomes do not guarantee future results.

Next Steps

If you’re a listener or client:

Ask your advisor how they use technology and AI in their practice.
Make sure you have:
- One clear view of your accounts and documents
- A sense of how your advisor coordinates planning, tax, and investments
- Confidence that your data is secure
If you don’t yet have a central vault or portal, consider consolidating your financial documents and asking for help building one.

If you’re an advisor or firm leader:

Map your current tech stack (CRM, planning, portfolio, vault, AI tools).
Identify where AI could remove friction (e.g., note-taking, summaries, data entry) without hurting the client experience.
Review how well your systems integrate; consider tools like Zapier or Make, or deeper integrations within Salesforce and similar platforms.
Experiment with AI in internal workflows first, then carefully expand to client-facing use where it clearly adds value.
Use time saved to expand real planning conversations and possibly your service menu (tax planning coordination, estate planning, etc.).

To explore how Tailored Wealth integrates planning, investments, and technology, visit the links above or reach out directly to discuss your situation.