The WealthTech Podcast

Modernizing Family Offices: Data, AI & the Path Forward | Chris Dickson, RSM US LLP Family Office Advisory

• Mark Wickersham • Season 2 • Episode 10

In this episode of The WealthTech Podcast, host Mark Wickersham talks with Chris Dickson, National Senior Manager at RSM Family Office Enterprise Advisory. We dive deep into how family offices can evolve their data, technology, and operating models for the modern age.

🎯 Chris shares a front-line perspective on:

  • Why family offices must treat data as infrastructure, not just reporting
  • How to modernize legacy systems without losing institutional knowledge
  • Where AI fits into the data conversation—and where it doesn’t
  • Why selecting the right source systems is more important than ever
  • The critical role of data governance and ownership in tech-driven offices

💡 Whether you're navigating a digital transformation, selecting a new reporting platform, or just trying to make sense of your firm's data ecosystem, this episode delivers real-world advice from someone who’s helped family offices get it right.

📈 Tune in for a clear, actionable discussion on modernization, AI, and building technology that works for the complexity of family wealth.

🎥 Watch on YouTube: https://youtu.be/XOHlEtUDQH0

About Chris Dickson

Chris is a nationally-aligned senior manager within RSM’s Family Office Enterprise practice, where he plays a pivotal role in supporting the expansion, execution, and go-to-market strategy for family office advisory services. Known for critical thinking, Chris is passionate about innovation and collaboration. He believes that integrating multiple perspectives into any conversation is essential for crafting the best solutions.

About RSM US LLP

RSM US LLP empowers family offices with trusted advisors and scalable solutions—built for complexity, guided by legacy, and designed to thrive across generations. RSM US LLP is the U.S. member of RSM International, a global network of independent assurance, tax and consulting firms with 65,000 people in 120 countries.

About The WealthTech Podcast:
The WealthTech Podcast is a bi-monthly interview series hosted by Mark Wickersham. Each month we present conversations with various industry leaders that focuses on the challenges family wealth firms face with technology, people and process. The podcast is produced by Brad Oliver.

The WealthTech Podcast is brought to you by the generous support of Risclarity. Risclarity fills the technology gaps family wealth firms face when serving the complex needs of ultra-high net worth families.

Transcript – The WealthTech Podcast: Host Mark Wickersham, Guest Chris Dickson, Family Office Head, RSM

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Mark Wickersham: All right. Chris, welcome to the wealth tech. Podcast. I am happy to have you on. This is gonna be a great show. We got a lot to dig into. Wonder if we could just kind of do a quick introduction about

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Mark Wickersham: who you are and who you work for.

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Chris Dickson: Absolutely. Thank you, Mark, and before I dive into that, just want to thank you for having me here, it's always a pleasure to reconnect and chat with you. So for everybody listening. I am Chris Dixon. I lead Rsm's family office advisory practice. I have been working in the family office space for my entire career. About 14 years

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Chris Dickson: I started as an auditor. So I'm a CPA. By trade, and I got hired out of school to work at a regional accounting firm in the Philly suburbs, focused on the wealth and asset management industry, and I was lucky enough to have a few family office clients, and then, because I had a few family office clients

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Chris Dickson: got recruited to join Ernst, and, young as they were building out their family office advisory practice spent about 6 to 7 years there, and then got recruited to join RSM. About a year and a half ago, and really focused on building out their family office, advisory capabilities and enhancing their broader family office offering. So it's a pleasure to be here and happy to dive into the details.

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Mark Wickersham: Great, I mean, that's

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Mark Wickersham: Look, John Carroll. Paul Mckibben. Couple couple of legends there that sure

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Mark Wickersham: you're working with tell me, tell me about your journey within the family office space. How did that begin? And then, you know, obviously, you've kept your whole career within the family office space. What do you love about the space.

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Chris Dickson: Absolutely so. I'm not going to lie. I really didn't even know what a family office was growing up or going through college. It's not like. There's a family office, 101 in most universities that they teach you about. So my real 1st foray into it was when I was at that regional accounting firm, and I just happened to have a few family office clients, and

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Chris Dickson: I just thought everything they were doing was awesome. I mean family offices can do amazing things in areas where they focus from a venture capital, broader investment, philanthropy and an impact on the community. So when I had the opportunity to join. Ey, I really leapt at that opportunity. One I also audit really wasn't for me. I didn't really want to spend my whole career there. So I jumped at the opportunity to go more on the advisory consulting side.

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Chris Dickson: And then I just double down. I mean, like I said, family offices can do amazing things, and what I love most about them is every day is something new. I mean, there's that old adage, right? If you've seen one family office. You've seen one family office, and like that's partially true and untrue at the same time, because if it was fully true, then consultants wouldn't exist because consultants require some kind of mega trends or some commonalities to exist. So consultants do exist because there are mega trends.

 

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Chris Dickson: but it's the family, their dynamics, their behaviors, their personalities, what they're trying to achieve in the family office, and how they want to go about doing that is so vastly different. So while there might be common activities. The way in which those get applied in the family office is unique, family office to family office. So every day is something new, and that's what I love most about it.

 

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Mark Wickersham: Yeah, I I would agree with all that. I think they're they're unique. I think also that the complexity that

 

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Mark Wickersham: family offices have to deal with as part of their operating environment. Given that, they're small businesses, right? Even a large family office is 40 50 people. Typical family office is much smaller than that. And and given what they're, they're managing and giving the the breadth and depth of services that they're managing. It's really

 

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Mark Wickersham: complex. I would also agree with you on that. Not every family office is is a unique snowflake. Right? There are different commonalities across them, though you know, obviously one of the reasons people have family offices is, for a certain degree of customization

 

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Mark Wickersham: given that they manage a complex portfolio and and have

 

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Mark Wickersham: a lot on their plate. How should family offices think about outsourcing? Where should they look to outsource? Obviously they can't do it all. What?

 

 

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Mark Wickersham: Where? Where do you advise? And what's what's your take on? How family offices should approach outsourcing.

 

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Chris Dickson: It is hard because it's going to be more art than science. Like I said, family offices do amazing things in areas that they want to specialize in areas that they want to focus. And for the most part the areas that they want to focus are really on the investment side, the philanthropy side. So they build in-house teams to really sort of manage those aspects. They might co-source and have outsource partners that they leverage from an investment due diligence standpoint.

 

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Chris Dickson: but for the most part they like to build the investment function or the philanthropy aspects of what they're doing in house where they don't necessarily like the focus is on the business of the business, and what I mean by that is building out a really robust accounting and finance team. Some family offices do that. Others prefer to kind of outsource those aspects to 3rd party firms that have maybe already made the capital investments and technology that they have

 

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Chris Dickson: most don't like to build a full it department within their family office. They may have done that at their operating company, and they may not want to replicate that necessarily at the family office.

 

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Chris Dickson: Hr. Is also another area where they might have somebody. That's the chief human resource officer. They've been deputized in that capacity, but they don't necessarily want to be doing the day to day payroll processing or the benefits administration. So where we tend to see the most where most family offices tend to outsource is really what we would consider to be those back office operations.

 

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Chris Dickson: those accounting Finance bill pay services, the tax compliance, to a certain extent they'll keep the tax planning in house, and they might keep a few tax directors in house. But leverage 3rd party firms like Rsm. Or the Big 4 to really do the tax work paper preparation

 

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Chris Dickson: and then also outsource their it, cyber security and their Hr services so that way they could really focus their dollars and their people on really making the greatest impact that the family wants to make, whether that be investments, philanthropy, or really, whether they just want to build an in-house team that's focused on really client service so focused on servicing the family. Whether that be their travel, planning their events. The next Gen. Education. So, keeping more of that front office client facing roles in house.

 

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Mark Wickersham: Yeah, I think that makes sense. Right? What's the mission of the family office? Focus at that core in house and then outsource some of the

 

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Mark Wickersham: other capabilities the business of the business I love that. I think obviously one of the things that that every family office should be thinking about outsourcing is cyber. Right? Don't don't assume that it is taking care of it. That it's such a unique specialized just to stay on top of it that you probably should have a specialized firm that focuses with nothing but cyber.

 

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Mark Wickersham: what about Rsm runs an annual survey on operational excellence

 

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Mark Wickersham: operational like alpha is really important. Anything family offices at times can struggle around that, especially when it comes to

 

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Mark Wickersham: technology management and some of the the more

 

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Mark Wickersham: capabilities. What does the survey show, and and what separates kind of the high performing family offices from some of the others?

 

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Chris Dickson: So I think I love that question 1st and foremost, because often people hear operational excellence, and they say, Well, what should I be doing, and how should I be doing it? And that's not really what operational excellence is all about.

 

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Chris Dickson: So our former fearless leader, who unfortunately, is no longer with us. Tony Wood used to say that operational excellence is really about the effective use of people process and technology. And that's what I think is really important I want to focus on is the effective use, because there's not a 1 size fits all. There's not going to be a silver bullet that says this is the way you need to do it, or how you should do it. It's really more about the mindset. Right? So how do you define?

 

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Chris Dickson: Find your policies, procedures? Are you applying those consistently? Are they clear? And do your people understand them?

 

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Chris Dickson: Is there confidence and execution? So I like to always go back to that patient capital and that operational confidence mindset. So in order for the family to want to keep their capital together and invest together, yes, there needs to be harmony amongst the family. But there also needs to be operational confidence that when they are relying on this family office to do the things they're trying to achieve that the family

 

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Chris Dickson: office is going to do that effectively. It's going to be doing it efficiently. And when a member of the rising Gen. Wants to see a financial statement or they want to see an investment performance report. If it takes that family office 2 to 3 weeks to pull that information together, that rising Gen. Member is going to be wondering. Well, why do I have this family office? Why are we funding this? Why are we spending this money. I can go on to my.

 

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Chris Dickson: put my applications on my phone log into Td bank or city, and sort of see what my cash statement is, or see what my investment portfolio is via fidelity. So they want more access to real time information, and not every family office is ready to do that yet, and that's where operational excellence comes into play. It's more of the mindset. It's that continuous improvement. It's that moving forward and not looking back and staying in the past.

 

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Chris Dickson: It's doing that next best thing. What's that one thing we can do to shore up our operations? What's that next hire? Can we start thinking about succession? Should we outsource certain things, it's more of a mindset around continuous improvement. And I think the firms that do it and do it. Well are those that have defined their vision for the family office? What are the services it's going to provide? How is it going to provide those?

 

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Chris Dickson: And then what's the people, the process and the technology that we're going to need not only today, but in the future to be able to do that.

 

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Chris Dickson: And it's just moving in that direction. So every year, every few years is an opportunity to rethink that vision most don't do it until there's a generational transition. And at that point you're leaving it up to the next generation. And those owners to really set that stage. And if they haven't had to participate or engage in the family office to that extent in the past, it can create some uncertainty for those both within the office and outside.

 

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Mark Wickersham: I mean a lot of times. You don't see the family offices really surviving right to the next generation. And there's a variety of reasons for that. It's not all around operational excellence, but I think certainly, you know, putting a report out 60 days after quarter end, and in a kind of a you know, thick Pdf binder, those days are are kind of gone, and I love this approach. You know this Kaizen approach where you just try to get better every day is a is a worthy goal

 

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Mark Wickersham: when it comes to tech stack. Obviously, family offices really struggle with technology and getting their technology line up with their their operational profile. How can family offices make better decisions when it comes to technology? And how can I get better results from technology.

 

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Chris Dickson: So I think technology is always going to be a challenge to a certain extent within the family office space. It's been a challenge. I think it'll continue to be a challenge. And that's because the nature of technologies and the nature of what it needs to solve, for in the family office space is complex at any given time. There's 5 different types of accounting that needs to be performed within a family office, your traditional financial accounting, your double entry, accounting your accounts payable.

 

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Chris Dickson: But most family offices live and breathe on tax. So there's tax basis accounting that needs to be done. Then you're throwing the portfolio, accounting in place for their marketable securities and their liquids, and you had a very fantastic conversation with the folks from Arch just a couple of weeks ago that talked about the complexity with alternatives and accounting for that and data management around that. So you've got financial accounting. You've got tax accounting. You got portfolio, accounting both liquid.

 

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Mark Wickersham: Partnership accounting right there.

 

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Chris Dickson: Accounting. Everything exists in tiered ownership structures, so to be able to flow everything up and then do the allocations, particularly if they've got a lender profits, profits, interest, model in place can be highly complex.

 

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Chris Dickson: And then, for those that you know might have a private trust company, or might have family members serving as trustees or the family office executive serving that capacity you might have trust, accounting that needs to be done. Fiduciary accounting. So at any given time 5 different types of accounting. Then you throw the performance reporting across a multi asset class portfolio and the risk analytics around that

 

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Chris Dickson: 5 different types of accounting, and then the performance and risk. So it's always going to be challenging. So when we when we like to focus on setting up a family office de novo. We really focus on what are the services you want that family office to be doing, and that gets tied into? Really, what is the purpose of the family office. And then what is your investment? Philosophy? How are you trying to deploy this capital that you have, and we can connect them, and they can have conversations, and we'll loop in their investment advisors because we're not an Ria. We can't provide those services.

 

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Chris Dickson: But we begin to have those conversations because depending upon their asset class and how they want to deploy it. Certain technology is better than others. If you're in alternatives, right? Do you need an arch. Do you need a canoe to support on that data aggregation? If you're heavy in privates? Does an Msci or the old Burgess Caesa make a little bit sense in terms of what it can do from a scenario planning and J. Curve analysis standpoint.

 

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Chris Dickson: Do you need an adapar which is going to be really kind of a leading platform from a multi asset class performance standpoint. So, depending upon your asset allocation and the asset classes you're willing to invest in that can inform the Investment Book of record decisions

 

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Chris Dickson: on the accounting side. It's

 

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Chris Dickson: how many entities you can have is multi entity accounting going to be important should you be thinking about? Maybe elevating out of a quickbooks and going into a multi-entity accounting system like a summit or an assetta, or sage intact, or Microsoft dynamics business Central. And if you're going that route now, you've got multiple systems. Is that really the path you want to go down to? Do you want to worry about the data flows and the integrations and the reconciliations that might need to occur.

 

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Chris Dickson: Are you comfortable? Kind of diversifying your vendor risk in that way. And is that something you're willing to do

 

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Chris Dickson: as a pro and and then manage the con of the data flow and the data integration between the systems. And if you're not, then do you maybe want to consider an all in one or comprehensive solution, like an archway, or an Eton or a fund count. So we spend a lot of time focused on not just what are the services?

 

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Chris Dickson: What are the asset allocation, and reporting requirements? But also, what is your risk? Philosophy? Do you prefer to diversify your vendors? Are you comfortable? Having vendor risk in just one vendor in place? That's responsible for all of this accounting and reporting.

 

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Chris Dickson: and then from there it's just the selection process based on their requirements. And and that's where I think hiring a consultant can be very beneficial

 

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Chris Dickson: because we've talked about it earlier. Family offices tend to be lean and mean in terms of their headcount.

 

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Chris Dickson: and if you're a family office executive. You may have been in another family office. You may have been in maybe 2 or 3, or maybe you just came out of the Mfo. World or the banking world. You may not have gone through a lot of technology selections and implementations. You may not have seen

 

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Chris Dickson: 1015, 100 family offices. So it's it's important to get in a consultant, at least in my mind. I know that's a little bit self serving, but we have requirements, databases. We've seen hundreds of family offices. We know what works, what doesn't work, what technology platforms. They leverage. So in sort of maybe shortcutting the vendor selection based on all that we can identify the 2, 3, or 4 systems that they should really evaluate, upfront, and and really accelerate that process a little bit more.

 

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Chris Dickson: So.

 

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Mark Wickersham: Yeah, I think that makes sense. One is, I thought that was a great breakdown of of

 

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Mark Wickersham: the considerations around best of breed versus comprehensive solutions. Like I said, there's there's no one right? Answer, right? There's it depends on the on the firm's technology personality. Are they comfortable with maybe going with one vendor, or you know, the vendor management risk. They want to diversify that. But then they're having to manage multiple vendors and and making sure those integrations are are working properly. I certainly think getting help getting a guide.

 

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Mark Wickersham: The family offices aren't doing this on a regular basis. If you can use a consultant that that is doing search selection, strategic planning on a regular basis for family offices. That's a great use of being able to try to leverage that expertise

 

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Mark Wickersham: when it comes to search and selection in particular. What are some of the common mistakes that you see firms make when it comes to selecting a vendor.

 

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Chris Dickson: So I tend to see 2. So the the real 2 mistakes that I tend to see is that they just go into it sort of

 

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Chris Dickson: demos like they just go in and they just start with that market scan. They haven't started with their requirements. They're looking at an at a par and comparing that to a sage intact, or they're looking at a sage intact and comparing that to a fund count. So it's sort of going into these demos, and looking at apples and oranges and bananas instead of apples to apples. Right? Maybe I want to take a look at that macintosh, and compare that to the.

 

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Mark Wickersham: I look at apples to bicycle, something.

 

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Chris Dickson: Example. Exactly.

 

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Chris Dickson: So. I think that's part of it is sort of without defining those requirements. And without that broad understanding of that technology landscape they tend to just go scattershot. They tend to just see the platforms that are out there and go directly to the Demos, and when you go directly to the Demos, the the Tech. The Fintech providers are putting their best foot forward. They're gonna show you what they want to show you. And you're gonna get a perception that this is what that system is.

 

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Chris Dickson: and what its capabilities are. And is that really what its capabilities are? What are the pros cons and challenges that those systems have.

 

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Chris Dickson: So I tend to like family offices, to take that step back, be a little bit more strategic, really define their requirements upfront, and then use that to funnel down on what? Their.

 

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Chris Dickson: what, the, what, the solutions out there could be. So start requirements, then go to Demos, not, Demos, to kind of back into your your requirements. The second is, I tend to see I've got a pain point. I want to solve this pain point. So I'm going to put this this bill pay system into place or this expense management system into place, or I may have gone the All in one comprehensive route. But I'm not getting the reporting I need. So I'm going to layer in this other reporting tool.

 

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Chris Dickson: So I tend to still see those that are looking more for point solutions, and by looking just at the point solutions and not really taking a step back to be like, Well, what are we really trying to do from a technology standpoint? What family office are we trying to be 5, 10 years down the line

 

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Chris Dickson: you're getting themselves? They're getting themselves into situations where they've now got 5, 6, 7, 8 different accounting systems or reporting systems or expense management systems, and none of them are integrated. They're not talking. So now they've got a lot of disparate point solutions that

 

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Chris Dickson: there's no integration. They're just doing manual processes around that. So that's that's the second is sort of just solving for short term pain points and not considering the larger picture that the family offices and taking that more of a technology strategy approach.

 

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Mark Wickersham: Yeah, I think those are 2 great points. I think you know, if you do see that sometimes they they do want to drive right into the demo, and you get caught up in the the shiny object syndrome right where you know. Maybe if you're often because the vendor is gonna show you. You know their their best foot forward, as you said, and you'd be like, Oh, that's really cool. And next, you know the you're drifting on. Why you originally started the search process. I think one is having some sort of technology roadmap

 

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Mark Wickersham: to be able to define. You know. Where are you going in 3, 5 years. It doesn't have to be a detailed execution plan. It's it's more of a north star right directionally, this is where we're going, and you. You adjust that over time, and it's it's a living, breathing type of document.

 

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Chris Dickson: Definitely have to adjust it over time, because technology evolves so quickly. So and and we're not expecting when we do these roadmaps or these strategy sessions. We're not expecting the family office to pull the trigger on 4 or 5 different technology platforms right away. Right? It's it's a staged approach. It's sequence. So maybe focus on this system. And then you know what? Here's the system we're recommending now, based on your requirements. But a year from now, when you're going to be looking to implement this or deploy this, maybe rethink it a little bit. Have that conversation with that tech platform

 

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Chris Dickson: again. See if anything's changed. So it's more of that North Star, as you mentioned that you're constantly working towards. Because, look, if you want to implement a performance reporting risk analytics system.

 

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Chris Dickson: and you don't have a general ledger. Maybe. Implement the general ledger. First, st your financial institutions and your advisors may you may be able to leverage them for the performance, reporting they'll have their own instances of performance reports. You can get that granted. It's their instance. You have to rely on them to give you the report. You may not be able to highly customize it, but you can meet ends meet in the short term, as you're getting your ducks in a row on other solutions. So there's always workarounds that can be done. As you're moving towards that north star.

 

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Mark Wickersham: Yeah, it's a good point. There is a sequencing. Sometimes you need to get other building blocks in place before you can do

 

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Mark Wickersham: auxiliary systems or to your point. Maybe you need to get the financial, the the accounting in place 1st before you get the performance measurement in place.

 

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Mark Wickersham: I think when it comes to individual search and selection, to defining that problem. And what success looks like upfront before getting the vendors involved is really important. I mean, there's 2 things that you need to see through is one is that

 

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Mark Wickersham: is it? Is it a good sales process? But maybe not a good product fit right, though that can be tough to discern the the flip side. You see it once in a while, too, is that there can be a good product fit for your organization. Maybe the sales process wasn't as great. And how do you see through that? Certainly, I think it. You know. Again, a a consultant can help guide a firm through some of those those type of things. But having

 

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Mark Wickersham: defined upfront, what are the pain points you're trying to solve? What does success look like? How do you measure it? Have those things defined upfront before you get into those? Demos is so important, because once that happens and you know, you're going down a different path. Let's talk about data independence. This subjects been coming up

 

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Mark Wickersham: quite a bit, and I think ours is a leader in this area. But how can firms own their own data? Why is it important? And is it even possible.

 

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Chris Dickson: So I I definitely think it's possible. Is it easier said than done for sure. So I I think there's a few approaches that can be done. So right like, if you're if you in house the technology, it's a little bit easier to own that data. Granted, you still need to take a look at the contracts and see what's in place. Right? So if you do tend to switch platforms.

 

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Chris Dickson: how can you export that data? In what file format. To what extent? How do I want to migrate this over? So I do think, looking at sort of like your data, access rights within contracts, regardless of whether in sourcing or outsourcing your services to a 3rd party. Provider is important. So one, I always like to say, start at the contracts.

 

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Chris Dickson: The second way, I like to think, and where I'm seeing a lot of family offices begin to explore today is really around the concept of a data warehouse. And maybe it's more of a data warehouse light. So it's more about focusing on, hey? I might have these disparate systems, and some may be integrated. Some may not be integrated. But I've got these underlying source systems. Maybe I've got yardy because I'm heavily focused on real estate, but I've got a sage intact.

 

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Chris Dickson: and I've got an adapar, and maybe I've got knowledge in place to help move data between them. Maybe I don't. But they've got these underlying source systems, and they're doing what they're intended to do.

 

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Chris Dickson: But now I've got really good data in one. I've got really good data in a second and really good data in a 3.rd

 

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Chris Dickson: What if I want to swap one of those out like, what's going to happen? Am I going to lose that data? How am I going to migrate it? So we're seeing a lot of family offices begin to think about putting a data warehouse in place. So that way, they're getting data from these underlying source systems, normalizing it.

 

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Chris Dickson: putting it into a location and then being able to generate reporting on top of that. So to me, I think that's going to be the greatest way to own and have that data flexibility, because then you can unplug a source system right? You can swap that out and plug something in. But you've already migrated that data and normalized it into a data warehouse that supported your reporting. So it makes that data migration a little bit easier. Maybe when you put that next system in.

 

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Chris Dickson: you don't need to worry. You just focus more on the opening balances. You don't have to necessarily worry about. Do I want to bring 2, 3, 5 years of data into that? Because you've already migrated and brought it into the data warehouse. And you're doing your reporting off of that. So it becomes your single source of truth for that historical data, and then can be used prospectively. So I think that is going to be the greatest way for family offices to get that data flexibility. And I know that's part of the value

 

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Chris Dickson: proposition of the all-in-ones as well as in one central location. And I think that's the right step. But there's always ancillary systems. There's payroll systems. There's sharepoint. There's other operational workflow systems. Data from there can be brought into that data warehouse as well. And you could do not only financial Kpis but operational Kpis.

 

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Chris Dickson: So I think that's.

 

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Mark Wickersham: I think that's a great point, I think. What is, you know, you talk about being able to minimize some risk

 

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Mark Wickersham: Consolidated Holistic reporting, I think you know, being able to put an AI layer on top of that versus having independent AI point, solutions can be able to give you a lot greater insights as well. Let's talk about AI

 

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Mark Wickersham: a little bit, I mean, how can you not? It's it's the biggest trend in in.

 

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Mark Wickersham: It's not even just family office. It's just one of the biggest technology trends period, AI hype and reality. How how should family offices be thinking about? AI?

 

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Mark Wickersham: What should they do to prepare for adopting AI. And you know, is it? Where are we at in the AI journey?

 

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Chris Dickson: So you and I have talked about this before, and at least throwing out the baseball metaphor. Right? So where are we? Are we in the 1st inning, are we in the 3rd inning? Are we in the 7th inning? When it comes to AI. I tend to like to think we're in batting practice. We're in the warm up. We're getting started, at least from a family office standpoint. And the reason why I say that is because it's going to happen. It's not a matter of if it's a matter of when

 

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Chris Dickson: you have Fintech providers that are already embedding AI into their platforms. It's happening. It's sort of like the cloud conversation back in the on-prem to cloud conversation. Back on the day a lot of family offices were focused on on Prem. That's where they thought the greatest security was.

 

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Chris Dickson: But they were already going to the cloud, because the Fintech providers were stopping supporting the on-prem versions. Nowadays. Not many are doing that, so they've sort of brought them there.

 

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Chris Dickson: I think the Fintech providers are going to bring the family offices to AI. It's just a matter. But it's going to be done, embedded within certain business applications. Right? So it's going to be embedded within your general ledger. It's going to be embedded within your alternatives, data aggregator. It's going to be embedded within your performance reporting solution. And you're going to be able to drive really great insights within the data that's in each of those systems.

 

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Chris Dickson: But it's not necessarily going to be pervasive across all business applications, unless maybe you do go the business or you go that data warehouse route.

 

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Chris Dickson: So why do I say that we are in batting practice? Because it's happening? But there's a lot of education that needs to be done. And there's a lot of cleanup that needs to be done prior to really being able to leverage

 

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Chris Dickson: that AI AI, just for business process improvement and efficiency purposes.

 

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Chris Dickson: So I think there's education that needs to be done not only to family members, but the family office executives in terms of really what is AI. How does it differ from robotics? Process automation? What are the different way? What are the different types of AI right? Are we talking about generative AI or something else. What are going to be the pros and cons and the challenges associated? That when is it safe to use it? Right like, if I'm in a family office. Can I use

 

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Chris Dickson: chat, gpt, maybe, but I wouldn't put my client information in there. I wouldn't put.

 

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Mark Wickersham: Yeah, I wouldn't be loading up the portfolio right.

 

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Chris Dickson: Yeah. So I think there's a lot of education that needs to be done in terms of what are the benefits? What are the challenges of AI. And then when should we be using it? I've heard instances of where family office executives prepare really good performance report. Send that to the family and to members of the rising Gen. And maybe they haven't necessarily engaged in conversations with the rising Gen. To really kind of assess their

 

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Chris Dickson: financial literacy, or sort of their sophistication. And you have the rising Gen. Members putting that into Chat gpt to better understand it, to ask the questions that they want to ask the family office staff. So the education goes both ways, not only educating the family office teams, but educating the family members on really what data is safe to put into AI platforms and what data is not safe.

 

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Chris Dickson: And then from there, I think there's work to be done on drafting, like, just like any good technology, use policy within a family office. AI use policies so that way those in the office really know what can be done and what the family's philosophy about AI data security data. Privacy is, and then they can go from there

 

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Chris Dickson: and then. I think.

 

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Mark Wickersham: I think that.

 

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Chris Dickson: Is going to be. I'm sorry. Go ahead.

 

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Mark Wickersham: That's a great point. They really should get some policies in place because people are gonna experiment with it right? They're gonna start.

 

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Mark Wickersham: I didn't

 

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Mark Wickersham: with it start playing with it, and they they may not be using it in the way that you would be the safest. That's the example of loading up the portfolio to get some insights on Chat Gbt. Right.

 

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Chris Dickson: Oh, for sure and shadow AI usage is is happening right? So like, even if you limit their ability to get access to like, chat, Gpt or other platforms on their work. Laptop people got phones. They got personal devices. People are using Chat, Gpt or other AI platforms one way or another. So I think really just trying to tackle that head on is going to be important for family offices, so that way their employees know what's expected of them. And and what's at risk? If if maybe they they tend not to follow that.

 

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Chris Dickson: The other, I think, is just data preparation, right? If you're going to be using AI to derive insights off of your data. You really need to make sure your data is clean. So I think there's a broader data strategy and data governance conversation that needs to happen prior to really deploying AI right? So how clean is our data? Who has access to our data? Where is our data stored? Where should our data be stored? Because, depending on where you're storing that and how clean it

 

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Chris Dickson: is? A may or may not be able to access it right, especially if it's only embedded in point solutions. So I think there's a broader conversation in terms of holistically taking a look at your data and going through that kind of data storage data, retention data, access rights and permissions management exercise prior to really wanting to deploy AI within your office.

 

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Mark Wickersham: Yeah, it's great point. I mean, they're they're 2 are related right? A AI is not gonna give you the results that you want. If you don't have your data clean and accessible and secure. I think

 

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Mark Wickersham: that in practice I like to think that you know that saying that the futures here is just not evenly distributed, that.

 

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Mark Wickersham: as you said, that these there are vendors out there that are embedding AI capabilities into their solutions today, which is a great way to do it. It's a secure way, I think, especially around alternative investments around

 

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Mark Wickersham: unlocking unstructured data, converting that into structured information, almost eliminating that 1st low value. Low mile, 1st mile type of data Ag is happening today, which is great. It's too long. These family Ops spend too much time just trying to get data out of Pdf documents. And

 

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Mark Wickersham: AI seems great for for that, I think in the investment process, too, you're seeing with with a genic. AI. It's amazing. Some of the capabilities that are out there today that is not, you know.

 

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Mark Wickersham: something that's talk about a Futurist like these. These applications are in place today. They're providing real value today. And I think it's you know, family offices should should become educated on it. Right? What are the policies. How do I protect myself? But then, what are the capabilities? And how do I modernize?

 

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Mark Wickersham: Because I just think, like the the capabilities and the efficiencies are, they're just too great to be able to ignore. And I think you're

 

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Mark Wickersham: example of of cloud migration was a. It is that kind of wave, and and unfortunately, or fortunately, it took Covid to be able to really get those family offices to to migrate to the cloud. In this case I think it's 1 of those things where you're not gonna be replaced by AI, you're gonna be replaced by somebody that's using AI and I think it's imperative of family offices that to get educated.

 

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Mark Wickersham: to find ways in which they can even experiment with those capabilities in a secure way, because there's there's so much efficiency that's to be had. So what is next? With AI given that we're in batting practice? When do we take the field? And what do you? What do you see, as some of the developments that are out there.

 

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Chris Dickson: So you touch on. I think a genic. AI is probably next. And I said, batting practice like, that's a broad generalization, right? Like there are certainly some that are an inning 2, certainly some that are an inning 4. But I think broadly as an industry, we're still very much in that warm up stage, and it's rapidly approaching because the Fintech providers are bringing us there.

 

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Chris Dickson: I think immediate. Next up is is better leveraging. Gen. I. Gen. AI, right? So that's to derive the insights based on the underlying data, or even to use like copilot to record meeting minutes and meeting that are happening right now like, that's a great efficiency saver. Maybe I don't need my executive assistant. Maybe I don't need my business analyst on every single call, taking notes when I can use something like a copilot to really do that on my vendor diligence or

 

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Chris Dickson: my board meetings that I'm attending. It can really just streamline that. I think that's a good way to kind of dip your toes into the water and get that 1st at bat. I think that is a way to get people starting to be comfortable with it, but in terms of what do I think is is more broadly kind of next on the horizon. I do think it is that agentic? AI, because that's really where using AI to really kind of automate process and begin to make decisions.

 

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Chris Dickson: But I think when you begin to go that route. You really need to have trust in AI, and you really need to understand the process and the data that is going to be deriving those decisions.

 

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Chris Dickson: because at that point you're automating it. You might still have human in the loop to sort of review what's been done. But maybe you want to use that to really initiate the workflows around client onboarding. Or maybe you really want to use that to really go through the process of setting up your entities and the chart of accounts with those entities, and really maybe

 

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Chris Dickson: beginning to get that structure in place across your business applications. Maybe you want to do it. To accelerate the bank reconciliation process, which I mean realistically, is already sort of being done within systems nowadays from a automation standpoint. But there can certainly be improvement there in terms of matching unreconciled expenses to the banks. So I think there's a lot of benefits that Agentic AI can do in terms of just sort of

 

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Chris Dickson: automating workflows and beginning to make those lower level decisions. I think it's going to be a while before we're relying on a gentic AI to really make recommendations around, maybe portfolio rebalancing and then automatically deploy that. So maybe start small is what I would say when it comes to that type of AI.

 

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Mark Wickersham: Yeah, I think that those are all good points. I think Agentic AI is is the is the next frontier. I think you're seeing obviously that the note taking capabilities are are really good. I mean that that what it captures and how it captures it are are pretty spot on, and then, if you can have, if you have a meeting with a family member, and there are takeaways that that come from that family member. Obviously, that you know, those notes get automatically put into the Crm. The task can be automatically kicked off and initiated.

 

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Mark Wickersham: An AI agent isn't gonna have something fall for the cracks. It doesn't stop until that that task is completed where sometimes I think you know the human side, you get busy. Sometimes things can fall through the cracks. I do think to your point to that, the decision making. I think that the human in the loop it's gonna be a long time before. Really. You know, AI should be at the range when it comes to actually making decisions on portfolios or other matters. But

 

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Mark Wickersham: the other thing, I think, too, in terms of kind of condensing large amounts of information like, you know what happened with the portfolio over the quarter, like getting that 1st draft and be able to see that information that can make you remind me of things that you forgot about. That happened maybe earlier in the quarter, and to be able to kind of customize the

 

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Mark Wickersham: communication experiences per person or generation. A AI can be good at that, so it can actually even help with communication. So that there's yeah, there's a ton that there's happening on that front.

 

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Mark Wickersham: Do you think

 

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Mark Wickersham: you know, obviously, the bad guys have access to the AI as as well. What are what are some of the latest threats that you see? Family offices facing when it when it comes to cyber.

 

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Chris Dickson: Yeah. So I mean, AI is a double edged sword, right? So there's a lot of benefits that it can provide in terms of really boosting productivity and creating efficiency within family offices. Right? You mentioned its ability to digest large data sets and really drive insights right? Like, do I really want to read a 90 page legal agreement

 

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Chris Dickson: back to back? Probably not. Do I want to use AI to maybe summarize that, and then point out, like certain paragraphs that I should really focus on. Yeah. And then, if I really want to focus more broadly, I can as well, but at least gets it can accelerate that process. That's that's the benefit of AI, the the con, or the negative aspect of AI is bad. Guys have access to it as well. Right. So like everything it's doing in terms of really making strong, deep fakes like nowadays, it's so easy to just use AI to

 

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Chris Dickson: make a video about somebody, or to kind of copy their voice for a callback procedure. Right? So it really makes it challenging. Now it's much more sophisticated. It's much better, and it's much quicker to do these types of attacks. So I think family offices need to. And family members need to be educated on how AI can also enhance the bad guys processes right? And really make their

 

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Chris Dickson: attacks not only more targeted, more efficient and more realistic. I mean, social engineering is is it's really it's a whole new ballgame nowadays in terms of how they can basically type a message and then automatically tailor that to 10 different personalities or 150 different user profiles and really make targeted right? So like, say, I've got Chris Dixon family office, and Mark Wickersham is my key vendor. Right? AI can really make a really strong video of you. Copy your voice. And then.

 

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Chris Dickson: you know, call me to say, Hey, can you initiate this wire, or Hey, I need you to sign this contract for the podcast that you're going to be on or something along those lines. And it's like, sure, if if I'm too busy focused on the work. And I just need to do this. I may not take that

 

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Chris Dickson: pause. To be like. Is this, is this real like? Am I aware of this and the threat? Enough that I'm going to slow down, and you know, maybe stop doing the Excel model that I'm doing right now to really kind of process. Whether or not this is a real request or a fake request, I might just push it through, and I think that is the biggest challenge is because, while you can do a lot from an infrastructure and a 3rd party security provider standpoint to really make sure your network.

 

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Chris Dickson: your infrastructure is solid. Humans are always going to be the weakest link from a cybersecurity perspective. And in the family office world

 

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Chris Dickson: often it's their lean machines. People are moving quickly, and sometimes people don't take that step back to really pause and be like. Is this a valid request, or should I just push it through, especially when they've got 50 different priorities that they're juggling. And it is a really good replication of maybe how Mark Wickersham communicates via email.

 

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Mark Wickersham: Yeah, I mean, it used to be phishing attacks that there were always kind of little quite off, we can tell. Maybe they weren't like a native English speaker, and the contacts or syntax was off even spelling mistakes. Now, this stuff is like it's within tone of the person that you're expecting to expect that the voice call back used to be the gold standard. Now that could be completely replicated with just a small snippet of actual

 

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Mark Wickersham: sound from a a person. Obviously, it goes to the point that 1 1 family offices being targeted. But 2 is, you gotta get professional help on this, and constant training, I think, is key to your point. That the human is the is the weak link on that they they need to be trained on on the latest

 

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Mark Wickersham: you know threats and and how to be able to the the spot. Them.

 

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Mark Wickersham: do you think? With the the promise of AI and the threat from cyber security that's gonna force. The the modernization of family offices, you know, so many family offices are are excel and and quickbooks stuck on kind of retail software, or even legacy products that vendors don't support anymore

 

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Mark Wickersham: is is that gonna get them off the slide? Or or is it. They're always gonna be a a subset of that family office population because they are cost center. That is is going to be resistant. The modernization.

 

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Chris Dickson: I mean, there's always going to be some resistance to change right? And I think that's going to just depend on the family members themselves and their personalities. Some people are much more open to change. Some people are much more willing to invest. The rising generation is demanding it. So I think not only is AI and Cyber threats going to really sort of

 

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Chris Dickson: bring family offices into the future. I think that the rising Gen. And the next generation. Family members are also going to bring family offices into the future. And I think in the absence of that modernization, I think we're going to see a lot of generational lift outs of family offices. We're already seeing that nowadays, in terms of maybe they're keeping the assets together from an investment standpoint. But the rising gens are creating their own family offices from

 

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Chris Dickson: tax planning a concierge service, and eventually an investment standpoint. Investments always do move over time, especially as they begin to disentangle them. You just don't want to take those capital losses right away. Right? So you have to really be strategic in how you begin to do that.

 

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Chris Dickson: But I think in the absence of modernization, there's going to be a lot of generational liftouts of family offices, and that's something that we're seeing. The other thing that I would mention around AI in particular is, I think it's going to lower the barrier to entry for ultra high net worth individuals into the family office. I mean.

 

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Chris Dickson: historically, I've always said 500 million dollars is the aum in terms of when a standalone single family office might make sense. Maybe you don't want to go the Mfo route. Maybe you want to stay embedded in your operating company. Maybe you want to go the virtual route. 500 million tends to be a good barometer in terms of when should I create a standalone, single family office, or when might it make sense from a cost benefit standpoint.

 

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Chris Dickson: Not always true, right? I've seen large family offices that are 400 350 million, but it tends to be good barometer. I do think AI is going to lower that barometer to 400 300 million, whatever it might be, because it's going to create so much efficiencies from an accounting and a personnel standpoint that your overhead cost your bips. Your cost as a percentage of aum is is just going to go down.

 

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Mark Wickersham: That's a good point like, yeah, that that minimum tier had been creeping up over time. 202 50 million 250 million that that was like the minimum. Minimum. And then it it seemed like, really for comprehensive family office. It almost seemed like you really needed a billion dollars for that to make sense. Obviously, Mfos can have provided

 

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Chris Dickson: For sure.

 

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Mark Wickersham: Revenue are are certainly a source for family office that are maybe smaller to get those those services, or to even partner with family offices. But I think that's a good point that actually AI might be a chance to be able to bring that that level back down again. Also, you know next, Gen. As you mentioned earlier, that the consumerization it right that what they experience in their day to day life

 

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Mark Wickersham: on their phone, you know you go to Fidelity. I can see real time what's happening with my portfolio, how much cash I have, and then you go to your family office, and the experience is a lot different. That that consumerization it, and what you experience with Amazon, these other things. And then you expect some sort of level of modernization with family offices. What I what I hope doesn't happen, and and unfortunately still does, I think to a certain extent, is that

 

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Mark Wickersham: they they modernized, due to some sort of event that some sort of key man had

 

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Mark Wickersham: key person risk, and that that person departed the firm, for whatever reason and they knew where all the bodies were buried, or there was a cyber attack, or there was a failure around being able to produce tax or whatever it might be. Unfortunately, you see a lot of family offices that get into, you know, a buying mode around technology because some sort of event happened, and I hope that

 

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Mark Wickersham: you know they use this as an example, that that to kind of be a little bit more, get in front of it before something happens, because it's not a big deal until it happens, and then it's a big deal when it does happen, as John Carroll would always say, so.

 

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Chris Dickson: Oh, for sure, and we do a lot of enterprise risk management for family offices as well. And I'm a big proponent of put a risk management framework in place at the get. Go be proactive about it, similar to cybersecurity. Right? Don't just do a punt test. Don't just do forensic remediation in when an event happens, right really be proactive about monitoring and managing, identifying, assessing.

 

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Chris Dickson: managing, and monitoring risk within your family office. But it's hard to get there. And and with some families, until an event happens, risk does tend to be more reactive. Risk management does tend to be more reactive than proactive. Exceptions are always the case. But I would say the same thing right. Don't just wait for AI to be brought to you. Don't just wait for that rising. Gen. To be asking that question

 

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Chris Dickson: because it's much harder to play catch up than it is to sort of plan for the inevitability and start making steps. Right? So that's why I like to focus on from an AI standpoint. Where should we be? We should be on a data, governance and data strategy standpoint, we should really be making sure we understand where the data is who has access to it and how we're going to use it. Do that first, st and then you're going to be better prepared for when AI is brought to you from the Fintech providers, or when you want to make that investment in AI yourself.

 

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Mark Wickersham: Makes sense all right. Chris. This has been great. I like to end the podcast on a personal note, 3 questions that have nothing to do with with well, tech or family office you recently were in at Disney. What what was your favorite ride at Disney?

 

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Chris Dickson: Favorite ride, so I think the the dad in me would say it was the Dumbo ride, or it was. It's a small world, because that's what my kids loved. But I think the the 36 year old guy that's sitting in front of you would say it was. It was most likely guardians of the Galaxy or Tron. Those were probably my favorite rides.

 

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Mark Wickersham: I got. We used to go to Story land every year, and I get sick on the teacups.

 

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Mark Wickersham: Let's do it again. I'm like.

 

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Chris Dickson: We did the teacups like 3 times.

 

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Mark Wickersham: What's 1 hobby or skill that you have, that people might not be aware of.

 

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Chris Dickson: So I love food, I mean, if you can't tell by looking at me. I love cooking food, even more especially barbecue. Come the summertime like made investments in the traegers have all of that. So you get me out there smoking a brisket over a Friday night into a Saturday. That's really where my passion is. My my children, my wife benefit from that as well.

 

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Chris Dickson: So I would say, cooking is probably what my secret hobby is. I also like baking as well. During Covid my wife got me into the great British baking show, so started doing my own breads and everything along those lines every Sunday make a loaf with my daughter, so she can have, like the fresh bread for Pb. And J. Sandwiches through the week. So kitchen is my passion.

 

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Mark Wickersham: Normally cooks are not good bakers and bakers.

 

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Chris Dickson: I didn't say I'm a good baker. I can do bread. I don't know if you'd trust me with a cake.

 

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Mark Wickersham: Cooking's an art baking's a science, as as they say. And then what's your favorite thing to smoke.

 

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Chris Dickson: I would say brisket ribs, wings, really anything I

 

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Chris Dickson: well, I mean, I've even done smoked salmon with an avocado salsa on top of that. So I'm all over the place. But I mean Brisket is sort of like that is the North Star. Am.

 

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Mark Wickersham: That's the super bowl right?

 

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Chris Dickson: Lot to go, but I would say I'm better at wings and ribs than than anything else.

 

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Mark Wickersham: I mean 8 h later, and you find out you messed it up. It's like.

 

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Chris Dickson: It's pretty unforgiving.

 

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Mark Wickersham: Good stuff. I do. I do like smoking the the chicken wings, though I think it. You know it's a quick hit right couple of hours.

 

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Chris Dickson: Oh, yeah.

 

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Mark Wickersham: Okay, I know you travel a lot for work best and worst airport.

 

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Chris Dickson: So I'm gonna say, the best and worst airport at the same time is probably the Philadelphia airport. It's my home airport, I mean, if you literally look at the rankings, I'm fairly positive it it ranks fairly low on the

 

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Chris Dickson: but I love it. It's just it's convenient. It's close by. There's good food options. So to me, like, it's just what I know best. So that's why it's the best. But it also gets a really bad rep. I think if I were to look more broadly than that

 

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Chris Dickson: I like Dfw, it's large. It's a little bit challenging to get across. But I mean really good barbecue there. So I enjoy that. Chicago. O'hare is also nice in terms of food options. So, as you can tell, I base a lot of my airports around food that's available. Less about how convenient is it.

 

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Mark Wickersham: I like Chicago because you could take the train into the city, and the train comes into the like so many airports.

 

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Chris Dickson: Otherwise.

 

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Mark Wickersham: Yeah, I, like.

 

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Chris Dickson: Right.

 

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Mark Wickersham: Like New York, some of these other airports like just get the train into the airport right? Just

 

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Mark Wickersham: my God, people! And obviously, I think, Newark, is it always sucked? And I know it's in the news, as as you know. For how much that is. But then some a couple of other airports, like the the New York airports, went from worse to first.st Laguardia and Jfk. Are both been modernized. Those they're pretty nice airports now, with lots of food options, you know.

 

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Chris Dickson: Oh, for sure!

 

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Mark Wickersham: Calls now.

 

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Mark Wickersham: So alright, Chris. Well, I'm looking forward to. Maybe you could do a maybe you could do like a book on on places to eat at in in airports that could.

 

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Chris Dickson: Be here, you know, and I'll add that to my to do list. My wife.

 

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Chris Dickson: She's in marketing, and she loves to write so she can always help me out with that.

 

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Mark Wickersham: There you go. This has been great, Chris. I really appreciate you being on the show, and thanks for sharing your insights.

 

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Chris Dickson: Of course. Thanks, Mark. It's always a pleasure being on here and appreciate the opportunity to not only connect with you, but to your audience. So thanks again.

 

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Mark Wickersham: That's great. Okay, let me see.

 

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