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

Posted on December 23, 2025 by Dan Pascone

Answer in Plain English (TL;DR)

No, AI is not about to replace great financial advisors—but it is already changing how they work. In this episode, Dan talks with Rob Burgess of Financial Planning Magazine about where AI and wealth-tech can automate tasks, where it can’t replicate human judgment, and how smart advisors are redesigning their tech stack around client conversations, not just back-office efficiency.

If you’re a high-earner wondering whether you’ll “just use an app,” this conversation shows how AI can handle notes, data, and drafts in the background while your advisor leans harder into strategy, behavior, and helping you make better decisions with real money at stake.

Key Takeaways

AI is already everywhere in wealth management—mostly behind the scenes. From CRM integrations to note-taking, planning tools, and prospecting software, more and more advisor tech quietly runs on AI and automation.
The tech stack is becoming as important as the investment lineup. CRMs, planning software, reporting tools, and “glue” platforms like Zapier or Make all influence how responsive, organized, and proactive your advisor can be.
Clients still want humans front and center. Research and real-world behavior both show that when clients feel like they’re interacting with a bot instead of a person—especially in emails or advice—they quickly question the value they’re paying for.
The goal isn’t to pay someone “just to use AI.” The value is in working with a professional who knows how to combine planning, judgment, and technology to deliver a more comprehensive, coordinated, and efficient experience.
Done right, AI lets advisors offer more services under one roof. Tax planning, estate coordination, document storage, meeting prep, and follow-up can all be streamlined so your financial life feels like one integrated system, not a stack of disconnected accounts.

Key Moments

[mm:ss TBD] – Rob’s path from local newspapers to covering tech and AI for financial advisors.
[mm:ss TBD] – How B2B publications like Financial Planning help advisors navigate new tools and trends.
[mm:ss TBD] – The three “pillars” of advisor tech: CRM, planning software, and portfolio/reporting tools.
[mm:ss TBD] – Where AI already shines: note-taking, summarizing meetings, and integrating with CRMs.
[mm:ss TBD] – Why clients feel shortchanged when they learn an advisor’s emails are AI-written.
[mm:ss TBD] – The difference between “using AI to do your job” and “using AI to do more for clients.”
[mm:ss TBD] – Lightning round: tacos, guitar, history buff, and the advice Rob would give his younger self.

Episode Summary

In this episode, Dan sits down with Rob Burgess, a reporter at Financial Planning Magazine, to unpack the question on a lot of people’s minds: will AI replace financial advisors? Rob shares how his beat shifted almost overnight from general wealth-tech coverage to an almost non-stop stream of AI stories once tools like ChatGPT arrived. He explains what it means to write for a B2B publication that speaks directly to advisors, not the general public, and why that vantage point gives him a front-row seat to how the industry is actually changing.

The conversation zooms in on the “tech stack” that sits behind every modern advisory firm—CRMs, planning platforms, portfolio tools, and the integrations that connect them. Dan and Rob talk about why Salesforce, Redtail, Wealthbox, RightCapital, eMoney, MoneyGuidePro, and others are more than logos; they shape how quickly an advisor can respond, how well information is captured, and how cohesive the client experience feels. They also explore where AI is already adding value: note-takers that capture meetings accurately, automated summaries, and tools that reduce manual data entry so advisors can stay present with clients.

From there, they tackle the trust question: if clients sense that every email or plan was machine-generated, what are they really paying for? Rob shares examples of research showing that perceived overuse of AI can lower the value clients assign to professional services, while Dan explains how thoughtful integration of AI has helped Tailored Wealth expand services and centralize a client’s financial life under one secure, coordinated system. The big takeaway: the advisors who win in an AI world won’t be the ones who ignore it—or the ones who outsource everything to it—but those who use it to deepen relationships and deliver better, more holistic advice.

Transcript

Dan: (00:00) 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: (00:27) 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.

Narrator: >> Brought to you by Tailored Wealth, helping business leaders live their version of a rich life. >> 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, competent money decisions.

Dan: (00:58) 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. Yeah, this is going to be fun. You’re you’re going to be very much a uh unique and and different guest than we’ve had in the past and uh I’m excited to get into what you do and and your expertise and your experience and all that.

Dan: (01:18) So, why don’t you start by just giving our audience a quick highle overview 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 uh cover investment strategies and technology, the latter of which, as you might imagine, involves AI a fair amount.

Rob: (01:38) So, uh that’s that’s been part of uh my coverage area since uh well, ever since Chat GPT came out, basically that’s most of what I’ve been writing about. So, uh yeah, I’ve been here about a year and a half. And uh uh before I uh started in this field, I was a local newspaper editor in uh northern Indiana.

Rob: (01:58) Never really had heard of I mean I I knew I guess what a financial adviser was roughly, but I certainly hadn’t thought that much about the industry. But uh then I got a job at Wealth Management Magazine as a reporter kind of also covering technology. And uh yeah, like I said, that was uh well, let’s see, I started that in October 2022.

Rob: Chat GPT came out in October or yeah, November of 2022. >> So, I 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: (02:47) All right. Very cool. I’m 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 uh 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, you know, I I certainly am, but for those that aren’t, tell us a little bit about the type of audience that uh that that that you’re you’re covering and also who’s reading it, the types of topics in general.

Dan: (03:10) But 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 that are following.

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

Rob: (03:29) 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. Uh 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. I I do narrow cast for a pretty specific audience. As you know, I also previously had worked for a legal publication here in Indiana, the Indiana lawyer, uh, where I was managing editor of that publication.

Rob: (03:52) And yeah, that was focused on the state’s legal community. And and once again, I don’t know why you would read that publication if you weren’t an lawyer in Indiana. So it’s a little bit different than like I said I most of my background before all this was uh kind of local newspaper you know local journalism general interest you know not not really any specific audience other than where you might be happen to live and and care about the doings of you know that that area um but yeah this is a pretty uh unique uh field in that yeah I am kind of focused very

Rob: (04:24) specifically on the wealth management industry advisors people that decisions within firms, especially regarding around technology and things like that. But luckily, there’s a lot to say. It never I never run out of things to to write about. So,

Dan: >> yeah, I’ve uh I’ve I’ve seen plenty of your articles and uh I’ve been lucky enough to be featured in a couple.

Dan: (04:44) So, I appreciate that. But let’s 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 and and and influencing and impacting most industries. What are the general trends you’re seeing in financial planning and wealth management?

Rob: >> Yeah.

Rob: (05:07) So, I mean there’s a lot of them, but uh one that I’ve been focused on, you know, here recently is uh kind of advisers expanding their services beyond what you might normally expect just a regular RAIA to offer. you know there’s these family office style I mean at least in the past services that you know people didn’t really consider that uh you know just a regular adviser would be offering but you know as as time goes on uh adding more and more of these things that can look like a lot of things estate planning tax you know not not preparation necessarily because you

Rob: (05:41) would have to be a CPA for that but you know tax planning is of course an important element and you know even even down to helping people buy cars I went do a presentation at the last T3 conference about, you know, somebody that their whole business is just helping advisers help clients, you know, buy cars.

Rob: (05:59) And that’s, you know, kind of a concierge service that you might not expect from a regular adviser. So, that’s one thing. Gosh, there’s so many. I do a series called Show Me Your Stack where, you know, we talk about people’s uh tech stacks and uh you know, how things do and don’t talk to each other. Uh integration is always a big topic.

Rob: (06:17) People always want the pieces of their tech stack to talk to each other better. Of course, you mentioned AI. That’s that’s been a huge uh game changer with the especially the notetakers >> and some prospecting tools that have come online that have people have found value in. So yeah, and also everything else in your tech stack probably has AI injected into it whether you want it or not.

Rob: (06:39) So it’s like everything, you know, this little popped up, you know, whatever. I I’ve seen it in my own, you know, programs I use it. It’s just it’s it’s embedded now.

Dan: >> Yeah. Very cool. Uh you said a bunch of stuff there that uh that’s really interesting to me. Tell me more about the show me your stack segment. Uh that’s that’s very very interesting because I spend a lot of time as a business owner and sort of running an RAIA 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

Dan: (07:09) actually run the business dayto day and then more the client engagement level. So this the uh the technology facing with the the clients to make the client experience better. 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 I mean I can think in the last just the last year I can think of five different services that we’ve added to to our local suite that we didn’t offer in the past.

Dan: (07:40) and it is creating more of like a one-stop shop experience. I haven’t gotten to the level of helping clients buy cars yet, although I guess we we we could probably >> not many people have. I think it’s a up and coming segment, but yeah, >> that’s definitely really a high net worth family office type of service. We we can come back to that.

Dan: (07:58) But let’s talk about show me your stack. What has surprised you the most if you as you’ve gone through those segments and and has it been more focused on the client-f facing technology or the businessfacing technology?

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

Rob: (08:21) So even if pieces of the test tech stack that I talk to people about have a client-f facing part sometimes they don’t turn that on or they don’t you know that’s not the part they show them they might have to get another portal or or kind of tailor it to that but I think that is uh becoming more of a thing.

Rob: (08:38) Also AI is 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 but you know most of the applications I saw were back office things initially things that the client wouldn’t necessarily see because if you know it makes sense if if AI makes a mistake you want to be there to to clean it up before someone else sees it.

Rob: (08:56) So you’re not might not ready to you know unleash that. But I’ve started to cover uh certain uh pieces of tech stacks that are, you know, involved in financial planning, involved in investment management. They’re starting to come online and people are starting to to bring that to the front of the house. So that’s been interesting to see.

Rob: (09:14) You know, in terms of the the rest of the tech stack though, um you know, one thing I I always ask about first when I when I do that series is what’s your CRM? Because that’s usually the main kind of piece that that holds it all together. A lot of people have said Salesforce because that’s the biggest one, but that does take a lot of customization.

Rob: (09:34) It can do a lot and uh it can also get kind of out of control if you don’t have somebody there managing it and tailoring it for for your specific needs. So, some people have gone different directions even looking outside the wealth management industry because maybe they’re, you know, a solo RAIA that doesn’t need all the bells and the whistles of something, you know, massive like that.

Rob: (09:55) So they might even, you know, look at something outside the industry for for that. So that’s been that’s been really interesting to see just the ways that people kind of just depending on whatever their niche or their specialty or the client base they serve or how big or small they are, they might be like, you know, this can do a lot. There’s a lot of tools here.

Rob: (10:13) I don’t necessarily need all these tools and I might just be better off getting something all a cart that might be out of left field for most people. 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 forms, right? So Salesforce is sort of industry agnostic, but to your point, you you you

Dan: (10:43) typically, especially in our business, want to have it customized to your interface. So, we actually, I don’t mind telling you, we actually just made a migration to Salesforce. So, we just went through migration, a custom build, customization. Um, and >> while it’s early on, I’m very much liking it.

Dan: (11:01) And the thing I like about Salesforce is the ability to connect to other places, right? >> Yes. So, you know, for those that don’t know as much about our industry, you have sort of some big players like Red Tail and Wealthbox, which I would say are probably the two biggest players that are specific to financial adviserss and financial planners, with Salesforce being the gorilla that is sort of industry agnostic, and there’s a couple of others out there.

Dan: (11:26) I’ve seen go High Level is is is a little more of a marketing platform, but has a uh has a CRM experience. I’ve used that in the past. and uh HubSpot, you know, has has has crept its way into the financial services industry. So many folks that might be in tech or in other businesses are familiar with those. And you know, it’s interesting to see how that that has made its way into into financial services and financial planning.

Dan: (11:49) What other ones are you seeing uh in your coverage, Rob, other than the ones that maybe I’ve mentioned >> of CRM, you mean? >> Yeah. >> Gosh. Well, there was one guy who used something called monday.com, which I had never heard anyone say, and that’s that’s not one 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 when he talked about that.

Rob: (12:12) So, that was that was one example. I I do hear people talking and maybe this is something I need to to cover more in the future, but will we need a CRM going forward with all these advancements in AI and things becoming integrated? We we kind of think of that as the the bedrock of everything.

Rob: (12:31) But what is that always going to be true? I don’t know. I mean, maybe in the future some people might find that they can do without it and they can kind of amalgamate other tools into that. >> Well, it’s an interesting discussion because um and this is my next question for you is how much coverage have you done or topics have you covered related to the financial planning softwares? Right? I look at it as like I think there’s really like three core softwares that most financial advisors and planners are utilizing or have some form of access to through a broker dealer or

Dan: (13:07) an RAIA or you know whatever the a wirehouse whatever their structure is they’re typically using if they’re doing financial planning which has become more and more prominent in the space I think most folks see value in that today I certainly do our our the foundation of our is this is built on the financial plan, but there’s the financial planning software, there’s the CRM, and then there’s typically some form of either portfolio management andor reporting softwares.

Dan: (13:34) So, I’m I’m interested to hear your your thoughts and your take on the financial planning softwares and how much coverage have you have you done in that space? >> Oh, yeah. Well, I always ask about financial planning and you’re right. I feel like more and more that is people kind of feel like that’s something to have to have.

Rob: (13:48) It’s not really optional anymore. you know, e-money is obviously one uh that a lot of people use. Money Guide Pro, those are some of the main ones. So, yeah, I mean, there there’s a lot of lot of different ones there. There’s a few upstarts coming. Uh I just profiled a company called Labretto and they do a lot kind of an interesting take on that and they’re they’re an upand cominging one, but but yeah, those are like you mentioned there’s there’s a few big players that most people uh bounce and so >> yeah, no doubt about it. You mentioned

Dan: (14:18) two of the big ones. I would add Right Capital into that mix as a as a really big player. That’s who we’re currently using. And you know 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 right 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 if you’ve got it integrated properly even do

Dan: (14:51) >> to some degree they’re offering starting to add on some level of um like meeting management or meeting rhythm and cadence for reviews and stuff like that. Previously really really managed at the uh the CRM level. And then there’s like the portfolio management which is if you’re doing sort of full scale comprehensive wealth management which we do you want to have something that’s tied to where the client’s accounts are actually housed and you know the integration is the key.

Dan: (15:20) So that’s my next question for you is how much do you get into integration and like how complex have you found this stuff to be because I find that uh integration is just like I spent a lot of time thinking about and looking at how all of our systems kind of talk to each other. So I’m interested to hear any lessons that you’ve learned or insights that you’ve gained on that topic. Well, yeah.

Rob: (15:41) I mean, like you you mentioned with uh Salesforce, that’s one of the big selling points for Salesforce is how integrated they are with so many things and, you know, how deeply embedded they are already. So, it’s like you don’t have to worry about, you know, double entry or or losing things in the in the translation in the shuffle there.

Rob: (16:00) So, that is a constant problem for people. I always ask them that’s a question I always ask in the show me your stack when I do those. It’s like, how is how are things talking to each other? how much and some things don’t talk to each other very well but it’s like how how much uh you know value do you get out of the software even though you know the integrations are are kind of difficult but yeah you’re right it’s it’s definitely something in the in the industry it’s an ongoing issue of those lack of total integration you know I

Rob: (16:25) think people definitely kind of dream of that one you know smooth interface between everything but I don’t think we’re quite there yet >> 100% you know you you see softwares like uh like make uh and zapier or zap year I don’t know which one it is zapier zapier I was going to mention that those are those are those have become very very popular to sort of connect your your your tech together all right so the elephant in the room when it comes to AI I think in any industry not just ours is you know this this this perspective of

Dan: (16:59) how am I using it to help what I do versus am I afraid that it’s going to replace what I do so give me like any insights or information you’ve gleaned from the people that you’ve chatted with and the stories that you’ve covered around where that sits for financial services, financial planning, wealth management, etc.

Rob: (17:18) >> Yeah. So, it’s been really I mean that’s a constant topic that I’m that I’m covering is because you know people that are boosters of AI, people that want to get this in advisor’s 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: (17:36) this is, you know, helping, this is an assistant, this is something, this is something you can bounce ideas off of. This is something that’ll make you faster and save you time. 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: (17:55) He wants to make it like the Whimo model of the driverless car, but for financial planning, basically. Like, that’s that’s his goal. He says it out loud and he doesn’t care who knows it. And there are other people on that tip like I was saying uh you know before about you know this going into financial planning investment management.

Rob: (18:12) 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. 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? I can go out and 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.

Rob: (18:38) And so I think people need to see that connection. And I think any time savings that people get from this, the successful people that I’ve seen have have put that back into client engagement and, you know, connecting with their clients and having that that one-on-one uh piece, not like, oh great, I don’t have to talk to my clients anymore.

Rob: (18:59) click you know those people are going to lose out because you know there’s been studies done if if a client thinks that you are and this is from a morning star uh study that I wrote about if a client knows that an email that you sent them was generated by AI they instantly think you’re worth like many dollars less per hour because they’re like okay you can’t even talk to me like like that’s you can’t even like write your own email to me what am I paying you for you know so um yeah if if people sense and and I have seen this even beyond wealth management. This is just

Rob: (19:31) kind of a societal thing. I don’t think people mind it like working in the background where they can’t see. But if they know that just the whole thing is just you you put a prompt in, you got a thing out and it’s like here look at this. McDonald’s had a AI ad that they took down after people were outraged about it because it was completely created by AI.

Rob: (19:52) It looked like it was created by AI. everyone knew it was and nobody liked it and they eventually took it down because they’re like you can’t even be bothered to like you know put your own ad together why am I watching you know what I mean so and I think that’s true in every industry like that’s the value I try to bring as a journalist is like you know I’m talking to people you know I’m out there you know actually connecting I’m not just going to put a prompt in be like write a story about this and then be like here read this there you go I wouldn’t read

Rob: (20:19) that and I wouldn’t expect anybody in my audience to read that either you know what I mean 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 like fool people that we’re not using AI.

Dan: (20:35) It’s like AI to show you that we’re not using AI, right? I mean, that’s that’s that’s become you’re you’re right. We we as humans have become like sensitized to searching for is this done by a machine or was this done by a human. And I totally agree with you. And it’s interesting because if you think about I think about like the different services that I use as a consumer.

Dan: (20:59) I frankly you’re right you you you wouldn’t want to there’s like a negative perception to I’m paying someone just to use AI. But if the idea is I’m paying a professional to and that professional is really good at using systems and technology and artificial intelligence to provide me a better service.

Dan: (21:19) Well, to me like I’m all in on that, right? And so I think it’s an interesting um almost tie back to what you said at the beginning of our conversation which is what I think AI has allowed I know what has allowed us to do in our business is provide more services to the client. So I think today if you’re just going around and using AI and saying I help you to manage your investments well I mean you know that that that has become a commoditized service. It really has.

Dan: (21:48) 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 really still requires like a human element to like understand stuff like goals and what you’re looking to achieve because I found any time that I’ve given a new client sort of like reigns to like run with the financial planning software it doesn’t end well so I I do find that there very much need to be humans still involved but I’ll say this from our perspective I think that it’s allowed folks in my space to provide more of a

Dan: (22:21) 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 and trust and wills person. 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 that 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, which is

Dan: (23:00) what I really, really preach as a value that we try to bring to our clients is 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 sort of technology suite. You don’t necessarily need to know all of the buttons that are being pushed.

Dan: (23:19) You just need to know that I’ve got one secure vault that I upload documents into and that I be able to view my financial life in one place. And I think that creates a high higher level of service. >> Oh yeah, absolutely. And kind of going back to, you know, what I said earlier about notetakers being one of the main applications.

Rob: (23:38) I think that’s a perfect example of that because, you know, 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 and you’re more interested in taking the notes. Whereas, if you know that it’s being recorded, you know that 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.

Rob: (24:04) You don’t have to take your attention away in the moment. You can actually have a more meaningful This is a topic that I discussed as a at a panel at our Advise AI conference here a month or two ago. Um, you know, and that’s that’s really allowed people to I think that the people see that value and that is a way that you know, people find more connection through using that that kind of AI. For sure.

Dan: (24:27) >> Yeah, it’s amazing. This would be an interesting story for you to cover especially on the financial side would be like what are the pieces of AI that consumers want their financial partner to utilize, right? Because to your point the the notetakers for the most part um you know while in some cases depending on your compliance infrastructure you need to get authorization to be able to use them but let’s take compliance out of it for a second.

Dan: (24:55) most cases I find clients absolutely want the notetaker to be in the room. Right? Because you’re right now we’re just having a conversation versus, you know, five years ago if you’re sitting in my conference room and I’m trying to scribble down everything that you wrote. Am I really engaged in what we’re saying? That’s number one.

Dan: (25:12) And B, >> yeah, >> I as a human might miss something that you said, but I can tell you my notetaker isn’t going to miss anything that you said, right? And so for that information to your point, you’re you’re adding another layer which is the integration between the noteaker and your CRM.

Dan: (25:28) If now as a client I know that really everything I’ve ever said to my advisor is now in my file in the CRM to me as a consumer that makes that that that’s an added level of comfort, right? Like that’s a value added service versus like my advisor use used a uh some form of AI to write me an email. he’s too he or she is too lazy to do that themselves.

Dan: (25:51) It’s a completely different dynamic and the perception is really interesting right as to you know 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 in time. >> Yeah. Well I mean in my own work like before you know frankly years ago one of my least favorite parts of my job was transcribing interviews.

Rob: (26:10) I absolutely 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.” Right now I I use Otter, >> you know, has AI built into it and, you know, I’ll I’ll 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.

Rob: (26:31) I’m never going back to the other part.” It doesn’t add value to me or my readers for me to sit here for an extra two hours, you know, I still have to check it. It still spells things wrong. It still misses things. You can’t just rely on it blindly. But man, it’s like been such a timesaver. And it allows me to get so much more work done that I think actually adds value to my I don’t really think they’re being served any better by me listening to something at half speed and and trying to catch every word. Well said.

Dan: (26:57) Well said. All right. I think that’s a great place to uh 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 and uh and uh what I tell every guest with the lightning round is first thought that comes to your mind.

Dan: (27:14) Could be a one-word answer, could be a long drawn out thought, or anywhere in between. You ready? >> All right. Great. Let’s do it. >> All right. One meal for the rest of your life. What is it? >> Tacos. >> You know what? I’m with you on that one. I think we would agree on on that one. I I like it. I’m with you.

Rob: (27:28) >> Hot tacos last night. My favorite. >> So, this is right in your wheelhouse. I’m very interested to hear hear your your response on this. This one may take you a while to think about or maybe it’s 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.

Dan: (27:45) >> 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, um, I got to think of something else. Well, I play guitar. Electric guitar. How about that? >> All right. I like it. I like it. Very cool. All right. Very good.

Rob: (28:02) Do you have a personal routine or hack that you very much believe in that you could share with our audience >> uh relating to work or just >> anything? >> Oh gosh. Wow. A hack. Let’s see. Well, uh oh my gosh. I might have to think about this. I don’t know. Um gosh, what do I I do uh can we come back to that one? I got to think about that.

Dan: (28:28) >> Sure, we can do that. >> All right. Um, 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? >> A bucket list item? Goodness gracious. Well, uh, I Well, I got to go to I’m a history buff. I love history.

Rob: (28:45) And I actually got to, uh, when I went to the T3 conference this year, I went to the, uh, um, sixth floor museum at Dy Plaza and I, uh, got to interview the director, the curator there. Um, and I donated some newspapers uh from when I worked as a newspaper editor that somebody had brought from November 1963. So, I’m a I’m a big history buff.

Rob: (29:08) So, that was that was a really surreal experience just from this year’s. >> Very, very cool one. Thanks for sharing that. Um, >> yeah. >> If you could give one piece of advice to your younger self, what would it be? >> Buy Bitcoin. >> I love it. We’ve had that a couple times actually.

Dan: (29:24) A couple people have said that on there. So, that makes a lot of sense. That makes a lot of sense. I think >> don’t just write about it, Rob. >> Yeah, don’t just write about it. Yeah, practice what you preach. I love it. And by the way, I’m I I I could argue the same for me as well. Um, all right. Very cool.

Dan: (29:38) And then, um, finally, if our listeners want to connect with you, collaborate with you, uh, check you out somewhere. What’s the best way to to find you? >> Great. Well, financial-l.com. Uh, you read all my stories there on LinkedIn. I hadn’t really before this year used it as a social uh platform, but I’ve I’ve taken to that this year and I’ve been getting more of an audience there.

Rob: (29:58) I am on Blue Sky as well if anyone’s on that. R O B A B U RG is my handle. I’m also on Facebook. I don’t post there too often, but I I am technically there. >> Cool. All right, sounds cool. We’re gonna tag you on LinkedIn because uh you and I have collaborated there a little bit. So, we’re gonna tag you in this episode on LinkedIn. Well, amazing.

Dan: (30:15) Thank you so much for sharing your insights today, Rob. It’s been great having you. >> Great. Thanks so much. >> That’s it for the episode. As always, you can find our podcast along with our newsletter, our YouTube channel, and this podcast at making senseofyoumoney.com. As always, prioritize your version of a rich life. Awesome, man. That was great.

Dan: (30:35) That was great.

Resources & Citations

Frequently Asked Questions

Will AI actually replace financial advisors?

AI is already replacing specific tasks—note-taking, data entry, basic reporting, and even some drafting—but not the advisor as a whole. The deeper value of an advisor lives in judgment, experience across cycles, behavior coaching, and stitching together taxes, investments, equity comp, and life decisions. For high-earning professionals, the likely future is not “no advisor” but “an advisor who is excellent at using AI to spend more time with you and less time on low-value admin.”

What parts of financial advice can AI handle well today?

AI and automation are particularly strong at summarizing meetings, organizing notes inside a CRM, drafting outlines of communications, and helping advisors explore different planning scenarios quickly. Many leading planning and portfolio tools now embed AI behind the scenes to surface insights and reduce manual work. The key is that a human advisor still needs to check, interpret, and apply those outputs to your specific facts and goals before anything becomes advice.

Where does human judgment still matter most in wealth management?

Human judgment matters most where the facts are messy, the stakes are high, and your emotions are involved—equity-comp decisions, when to exercise options, how much risk to take with concentrated positions, when to retire, and how to balance competing goals across a family. Advisors also bring pattern recognition from dozens or hundreds of client situations and can help you avoid mistakes that don’t show up in a dataset or a backtest. AI can inform those decisions but cannot own the accountability for them.

How should my advisor be using AI to help me as a client?

In an ideal setup, AI helps your advisor capture every detail in meetings, keep your records organized, coordinate across tax, legal, and investing tools, and prepare better for reviews. That means fewer dropped balls, smoother follow-up, and a more complete picture of your life in one place. If AI is being used primarily to write generic emails or canned advice without review, that’s a red flag; if it’s used to free your advisor to spend more time on strategy and conversation, that’s a positive sign.

Should advisors disclose when they’re using AI in their process?

Many clients are increasingly comfortable with AI as long as it’s used transparently and thoughtfully. In fact, some industry research suggests that trust can erode when clients discover AI is being used in “secret,” especially for communications that look human but aren’t. A good advisor will be clear about where AI shows up (for example, in note-taking or drafting) and where a human is still making the final judgment and recommendations.

What am I actually paying for if AI does more of the technical work?

You’re paying for a thinking partner who can design a plan you believe in, help you stick with it through volatility, and coordinate a complex financial life into something coherent and actionable. AI may help reduce errors and speed up the technical side, but it doesn’t sit with you when markets are rough, it doesn’t know your spouse or kids, and it doesn’t proactively push you to make hard but important decisions. The advisors who survive and thrive in an AI world are the ones who lean harder into those human roles, not away from them.

Disclaimer

The content in this episode and on this page is for educational and informational purposes only and is not intended as individualized investment, tax, or legal advice. Artificial intelligence tools and wealth management technologies discussed may not be appropriate for every firm or investor, and all strategies are subject to eligibility, changing laws, and market and technology risks. Before making decisions about your finances or technology stack, you should consult your own qualified financial, tax, and legal professionals.

Next Steps

If this episode raised questions about how your advisor—and your own plan—should be using AI, the next step is to look at your entire financial life in one place, not just your investment lineup.

Primary CTA – Talk with Tailored Wealth: Visit yourtailoredwealth.com to see how a Life-Driven plan can integrate technology, AI, and human advice so your money supports your version of a rich life.
Secondary CTA – Explore more AI & planning episodes: Head to the Making Sense of Your Money podcast archives to dive into more conversations on tax strategy, equity compensation, and investing in an AI-enabled world.