The WealthTech Podcast Episode Transcript

Guest: Ray DiNunzio, Partner TOS Advisors

Host: Mark Wickersham

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Mark Wickersham: Ray, welcome to the wealth tech, podcast I'm excited for this conversation. Can you give a quick introduction of yourself and Tos advisors.

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Raymond DiNunzio | TOS: Sure. Hey, Mark? Thanks for having me on Ray DiNunzio.

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Raymond DiNunzio | TOS: based in Houston, Texas, and TOS started originally started about 12 years ago. It was a De Novo single family office that was a family that held a holding company. 9 operating businesses sold their largest business

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Raymond DiNunzio | TOS: for about 3.5 billion dollars.

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Raymond DiNunzio | TOS: and it was a cross border transaction. Lots of complexity, lots of things to track over the years it evolved and the family office came out and became more complicated and more complicated. In 2,018

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Raymond DiNunzio | TOS: my friends there asked for permission to sort of spin out of the family office. And we kept the name of the organization from that point forward we just saw an opportunity in the marketplace. Mark so many people are frustrated with sort of the family office experience, the operation technology, solving problems, the administrative burden grows way faster than its ability to manage it.

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Raymond DiNunzio | TOS: And honestly, I got intrigued by this concept of an exponential organization which is done out of Singularity University with salaam. Ismael and a good friend of mine ran a company in Houston called Arctic and Arctic, is a big, cooler company, people know Yeti really well. Arctic is a very similar company, and Jim and his brother John built this company.

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Raymond DiNunzio | TOS: evolving it and calling it

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Raymond DiNunzio | TOS: fast followers, and where Yeti had 650 employees, they had 23,

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Raymond DiNunzio | TOS: and this really rung into me. They did the same volume, did the same thing, and I started looking at this singularity university stuff, and I was of the opinion like, could you apply this concept

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Raymond DiNunzio | TOS: to a family office because I had had a traditional career in finance work for a large global

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Raymond DiNunzio | TOS: bank and ended up on the executive team for their private wealth, management, division and their family office practice, and everyone struggles in these family offices, and

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Raymond DiNunzio | TOS: the punchline here is in an exponential organization. You can do things 20 times better or faster.

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Raymond DiNunzio | TOS: And you know, should be significantly cheaper than somebody else doing it. And it's embracing technology. Leasing don't owning. It's creating dashboards. And if you look up this concept, it's really fascinating to me. And we just had this idea that maybe there was time for a different way to approach the administrative burden of a family office, and rather than everybody inside the office trying to do it, could you outsource that, and could you outsource it with all the best technologies being operated on your behalf?

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Raymond DiNunzio | TOS: So we started that off. We were early in this idea of outsourcing this. And

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Raymond DiNunzio | TOS: people didn't really understand what we're talking about in 2,019 people very much understand it today. And we're really fortunate to be having the success that we are.

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Mark Wickersham: Well, your timing must have been great with the you know, the Virtual family office. And then, with the advent of covid and firms having to embrace that anyways. Tell me a little bit about your tech stack and how

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Mark Wickersham: you've developed your tech stack your tech stack. And what can family offices learn from that particular process.

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Raymond DiNunzio | TOS: Yeah. So

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Raymond DiNunzio | TOS: I mean the dilemma that we all face. And my friends certainly did, too, is, I think, fundamentally, technology is sold. It's not purchased. And we tend to buy technology off demonstrations calling up people that we know. Hey, Mark, what do you use? Why do you use it?

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Raymond DiNunzio | TOS: That's sort of the general way that people go about this, and my friends in the family office, my partners in an 8 year period they were rewiring the family office for the 3rd time.

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Raymond DiNunzio | TOS: and they spent good money. They hired consultants, they hired professionals. I think the divide between the consultant business and the client. Experience is that oftentimes the consultants don't operate the technology and never operated it.

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Raymond DiNunzio | TOS: And so they don't really know what the outcome is. And the salespeople can sell you. Here's this experience, Mark, in a perfect world. But your world's not perfect in your family office, right? And so it doesn't necessarily line up as well as it could. What we did at the time when they were facing this dilemma.

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Raymond DiNunzio | TOS: and we instituted it for the family office that they were working in

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Raymond DiNunzio | TOS: was. I had had this time at this big bank, and we spent a lot of time with a major consulting firm Boston Consulting Group.

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Raymond DiNunzio | TOS: When I was at the firm at the bank. And so I went to them first.st And I said, You know, you guys, we spent a lot of time together like over the 18 years I was at this bank. Help me understand, if you have a high performing family office, what's going on there? Why is it high performing. What's the experience? And there's a distinction between high performing investment management which everybody wants and ascribes to be a great investor. But a high performing family office is operating like a business.

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Raymond DiNunzio | TOS: and you are measuring everything. You understand sources and uses of capital. There's no surprises on closing the books every month from a tax construct.

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Raymond DiNunzio | TOS: You understand how to manage the artwork collection and the risk around the art, your insurances, your loans, what you should have onshore offshore, what the legal structures look like for everything where you want to express your next dollar and alternative investments or private equity or direct investments. You know why you're doing it. You're not just buying it because someone's presenting it to you. Then, very much like run the family office like a high performing business.

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Raymond DiNunzio | TOS: which was interesting, and at the time they suggested that the budget was 5 56 basis points on a billion dollars to have a high point family office.

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Raymond DiNunzio | TOS: not including any investments. And so

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Raymond DiNunzio | TOS: you know, what we looked at was the activities that go on in a family office, and we wanted to minimize the burden, and the dilemma that my teammates were faced with was.

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Raymond DiNunzio | TOS: they had a very good family that they worked for. Principals were on top of everything, wanted to measure everything, didn't trust everybody, but they were very, very focused on not a lot of headcount. They were a very private family. They did not want people knowing their business.

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Raymond DiNunzio | TOS: but they're willing to pay for everything and anything. So that's why they kept trying and looking for this unicorn technology.

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Raymond DiNunzio | TOS: We spent a lot of time visiting with many, many family offices in my career. I've met with thousands, some of the largest in the world. Those were our clients. When I was at the bank, the family offices that looked like professional investors. We were balance sheet partners, largest client. When I was there we had about 12.5 billion dollars worth of balance sheet exposure. So I came calling to these folks and asked if I could come and go visit with them.

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Raymond DiNunzio | TOS: and we were long time friends, and I've known most of the patriarchs, and we're like, sure. Come visit. We'll have dinner, and I'm like, well, I'd like to spend a day and a half or so with the family office. And really, Mark, just spending time interviewing everybody in the family office, understanding what everybody did.

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Raymond DiNunzio | TOS: what they created from a work product, what technology they use where the work product went. Why, that person wanted it. What did they do with it? Right? What was their work burden like 3 years ago 5 years ago? What's it like today? What staff look like then? What does it look like today? What technology they use? What's the budget look like? Really wanted to

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Raymond DiNunzio | TOS: count almost every keystroke of activity going on in that family office, right. And we all hear this idea that

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Raymond DiNunzio | TOS: if you've been to one family office, you've been to one family office, and I guess that's interesting

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Raymond DiNunzio | TOS: the way we look at family offices is they're way more similar than they are different now. You could have a professional capital markets, team trading equities, derivatives doing whatever. That's fine, that's unique. And you can be an allocator. And that's fine, and that's unique. You could do direct investments. But the operation and the operational burden is very similar. So we in in one of our big offices here in Houston, like we have big whiteboard app, we just really whiteboarded out all the activities in a family office. And our approach was

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Raymond DiNunzio | TOS: to create a very digital environment to operate the family office from. We didn't want humans touching data.

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Raymond DiNunzio | TOS: And that's how we kind of got to designing the technology that we use and thinking about those pieces. It's the outcome of the pieces. It's not the pieces right? It's the outcome that you desire. It's not the user interface of the technology. And I think, I think potentially, that was unique approach to looking at the problem when we were doing and going through that exercise in 2,018 and 19.

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Mark Wickersham: Yeah, I think the that saying, you know, we've seen one family office. You see in one family that they're not necessarily snowflakes, right. The a capital call can only be processed so many ways right? And that there's

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Mark Wickersham: certain steps that that need to take place for that capital call to be, you know, efficiently and timely and accurately

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Mark Wickersham: executed. So if you can kind of map that out and apply technology to it, I think I think that makes

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Mark Wickersham: a lot of sense. You had a a recent blog post you were mentioning. I thought it was really interesting perspective, because when I look at family offices or office, they're often really over relying on excel and and like retail software and part of your perspective on that was that there is a lack of intentionality in design, because they come out of an embedded operating company. Can you speak to that a little bit more.

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Raymond DiNunzio | TOS: Yeah, it's really interesting, because you'll have a very successful entrepreneur or family or family business

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Raymond DiNunzio | TOS: and then they and this happens more than it doesn't happen right. They remember what it was like to start the company that created this windfall of wealth.

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Raymond DiNunzio | TOS: And then they they go and start the family office the same way, and the difference is, when they started the business they had 10,000 50,000, 100,000, whatever it was to start the business. And now they have hundreds of millions, if not billions. And they're creating an environment with almost no oversight, with intention. Right? It's really interesting and

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Raymond DiNunzio | TOS: and it happens

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Raymond DiNunzio | TOS: in every corner of the family office world that we see, we see big private equity guys, billions of dollars, 4 billion dollar one that we know well, and he's telling all the analysts. All they need is excel. Because when he came out of Stanford and started this private equity firm. That's all he needed, right? Right? But there's there's so much to look at.

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Raymond DiNunzio | TOS: That it's difficult to get their arms around. And and in that piece. I also address what one of the interesting things that happens is when they move from the business, and oftentimes they're forced to move the employees out right? There's a change of control. There's something happening. There's going to be a change of control. And so they take the team that they know and trust and move them into working with them in the family office.

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Raymond DiNunzio | TOS: And then you've got a Cfo and a Treasury person. These people that are very bright and talented, and certainly loyal and trustworthy, but they don't know anything about managing assets in this way.

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Raymond DiNunzio | TOS: right? So they're really not prepared to even think about

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Raymond DiNunzio | TOS: how to go about setting up a family office. There's a good expression that we picked up upon. I am not the author of it. I can't remember who told it to me might have been Peter Braxton in Vail. There's no blueprint for running a high performing family office. There's a blueprint for almost every other business. There isn't 1 for running a family office. Well.

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Mark Wickersham: It is. It is interesting. Obviously, these people are hired, you know, trusted Cfo, the treasurer. They've they've done that particular job. Well, they're they're

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Mark Wickersham: the the family's comfortable with and trust them with them. But then you have these. You know other disciplines that you need to incorporate, and

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Mark Wickersham: I think the part of part of the problem with the, you know, you see, Excel and this retail software, it's just quick to stand up and they need something right away. And they need the okay, let's just start tracking this information and get excel going. So

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Mark Wickersham: and then, you know, a year later they got this massive spreadsheet, with probably 5 or 6 significant errors in it. And it's it's a beast unwind. Wait, let's talk about

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Mark Wickersham: There's a couple of different approaches when when family offices can look at technology, there, basically 2 camps. And I, obviously, there's no one right answer for every single family office. But there is a right answer for every family office around. Best of breed versus all in one or comprehensive solutions.

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Mark Wickersham: Can you talk to me a little bit about that. What are what are the pros and cons in these approaches like? What? What's your take on on it.

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Raymond DiNunzio | TOS: Yeah,

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Raymond DiNunzio | TOS: so we we test all technology before we buy it right? And we would love to find the unicorn that could solve all the problems life.

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Mark Wickersham: Silver bullet.

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Raymond DiNunzio | TOS: Right if you could do everything from one place. I mean, it certainly sounds elegant.

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Raymond DiNunzio | TOS: From a practical application. We knew what we were solving. For when we went and started down the path.

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Raymond DiNunzio | TOS: and so we could quickly say that this is not going to work for us

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Raymond DiNunzio | TOS: right? And one of the problems with a few of the problems, with the all in one solutions, and especially now in 2025,

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Raymond DiNunzio | TOS: is technology is moving really fast, really fast. We've never seen it move this fast, and

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Raymond DiNunzio | TOS: the the ability for you to compete when you have as a closed architected system, and try and be the best at everything I think is gosh, darn impossible.

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Raymond DiNunzio | TOS: And what you're gonna get stuck with is a system that

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Raymond DiNunzio | TOS: is difficult to upgrade. It's difficult to manage. It's difficult on the companies, too, right? Because you have a finite amount of resources. And let's just be honest with ourselves, like 25 years of my career has been spent on family offices from some of the biggest in the world at a big bank to doing what we're doing now.

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Raymond DiNunzio | TOS: family offices, as much fun as they are to talk about, and the wealth that they have

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Raymond DiNunzio | TOS: and the things that they manage. I mean, we're pretty unique people that are in the family offices. We're not very commercial. Oftentimes

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Raymond DiNunzio | TOS: we don't oftentimes have legitimate budgets to do things.

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Raymond DiNunzio | TOS: We don't necessarily make rational decisions. And we can't move things forward. So if you're a software provider, do you really want to build software for us like, let's be honest, like, should.

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Mark Wickersham: It's not a rational buying behavior either, right?

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Raymond DiNunzio | TOS: No, it's.

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Mark Wickersham: Market.

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Raymond DiNunzio | TOS: Did terribly. And so and and so when you, when those companies transition and they take in private equity money or different things happen, and we see this a lot, right? Technologies get old very quick, because you have to continue to put a ferocious amount of money into R. And D, if you're going to stay ahead. And newer technologies today

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Raymond DiNunzio | TOS: make technologies even 5 years ago. Very obsolete, right? And the evolution of large language models. And what can be done, and how these things move forward. There's just so much more you can do with agents than you do with humans, or that you can do with software. And you can't

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Raymond DiNunzio | TOS: out software your way out of bad processes. Right? You just can't and so I think the difficulty from the All in one solution. It may, it may work well for a very modest operation, or something that you're comfortable with things not necessarily being at your fingertips.

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Raymond DiNunzio | TOS: We designed everything for an environment where everything is at your fingertips all the time. The data should be live, or very close to live all the time, and the most important thing that we looked at. And it was sort of our our true North was. And this is this was really unique in 2019, not sure how unique it is today. But we wanted to create an environment that was 100 digital.

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Raymond DiNunzio | TOS: And we didn't want humans touching data or moving data around, right? A lot of problems with the the all in one solution sets is while the user interfaces look lovely and they're nice and they're attractive. How the data gets in and the limitations to it, or where your problems are like, how do you get artwork in right? How do you get currencies in. How do you get bank accounts in Riyadh Saudi Arabia, in like the bigger families, have all this stuff.

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Raymond DiNunzio | TOS: and what ends up happening? I think oftentimes with a lot of families. And another inherent problem with the best of breed breed approach is

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Raymond DiNunzio | TOS: they're not. They don't know necessarily where they're going

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Raymond DiNunzio | TOS: as they move along. And they they end up with this technology debt. They keep buying things, they become obsolete. And they're moving data from place to place to place all the time with humans. We worked a lot with the folks at vain on some research.

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Raymond DiNunzio | TOS: and they've created this trend to swivel right? And somebody's taking data from one place and swiveling it and moving it into another place. And and unfortunately,

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Raymond DiNunzio | TOS: that's what most people experience with the.

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Mark Wickersham: Think you're not right.

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Raymond DiNunzio | TOS: Right.

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Mark Wickersham: I think you know, for some family offices.

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Mark Wickersham: you know. I think it's somewhat their tech personality in terms of if they don't want to manage multiple vendors they want, and maybe it's a smaller operation and want some a simpler approach they can be a good good take. I do think that. You know those all in ones

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Mark Wickersham: depending on the amount of tech debt that those firms have

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Mark Wickersham: are are set up well for AI, then that you have one unified closed in platform.

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Mark Wickersham: You do have the the where you spoke about, though there are making choices on their roadmap, and there's limitations. You can't do everything well. So you need to make sure that the choices that they're making the approach that they're making to their R&D's in line with where you want the product to go. Cause. If you have a particular feature or function

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Mark Wickersham: that's important to you, that may not be important to them. Then that's just gonna languish a little bit. The the other thing is around, regardless of whether you're comprehensive solution or whether you're a a standalone is, you need to have Api connectivity. There's no longer. You can just do everything yourself. Even the most comprehensive systems still need to be able to to plug into

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Mark Wickersham: the tech stacks. Can you talk to me a little bit about you know how how you've taken approach to integrating different pieces of software and getting a unified approach with with different vendors.

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Raymond DiNunzio | TOS: Yeah, I mean that that was really right in the very beginning for us. And we knew what we were trying to solve for.

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Raymond DiNunzio | TOS: And so again, we would. We would eliminate technologies because we run data through them. We test them. We talk with the people big part of what we think about when we think about technology companies we want to embrace is, what are they spending on? R&D, like, that's a big thing identifying the gaps. That's a big thing. When we started down this path we, we

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Raymond DiNunzio | TOS: some reason or other, we're able to start speaking with people in the engineering departments, and we convinced one very large company that we all know

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Raymond DiNunzio | TOS: that we'd like their technology a lot. We thought it was really elegant the way things could be visualized, and it was almost limitless with visualization. Whether it's artwork. We want to visualize automobile collection. We want to visualize that you name it. You can bend it this thing around. But we thought it would be a lot better if we could have the data connected from

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Raymond DiNunzio | TOS: basic example. But alternatives at the time. And so for them. That was like the 1st Api connectivity that they had built.

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Raymond DiNunzio | TOS: and we had to have it that way because we were literally staffing a very complex situation with 2 people sitting in a family office. Right? And so you have all of these entities, all of this real estate tons of alternatives, 7 different big banks around the world. All this stuff had to come into one place

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Raymond DiNunzio | TOS: so the principal could see it, but he didn't want a lot of people. And so that that was paramount to us and thinking about that. And there's there's a concept called a canonical data structured environment

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Raymond DiNunzio | TOS: that I, I learned from one of the guys from 2 Sigma, the the hedge fund firm.

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Raymond DiNunzio | TOS: one of the computer scientists. And and we thought about that a lot we thought about. Not only do we want the things to be connected.

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Raymond DiNunzio | TOS: but we actually want the data to go live everywhere where it's supposed to live.

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Raymond DiNunzio | TOS: So it's 1 thing to connect it from A to B,

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Raymond DiNunzio | TOS: but what about A to B, to C, to DEF, and G, and so, like, we wanted the system to be able to have interconnectivity upstream downstream and move things everywhere that they should go and route that data without a human being touching it. Right? And

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Raymond DiNunzio | TOS: that's, I think, pretty still unique. Today. We've learned a lot in 5 years. And

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Raymond DiNunzio | TOS: the evolution of this stuff is really interesting. And what's happening now is happening so rapidly in the ability to do these different things. And I'll tell you another thing that's that's really important that we learned along the way is data, reconciliation and audit.

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Raymond DiNunzio | TOS: And that's a beautiful case for AI, and where you can put agents on things that are continuously learning and identifying problems, what it ends up doing for us and for most of the technology firms that we work with. We were either early access partners meaning they were new, they were evolving. They came out of a venture firm, and we helped interconnect them in the ecosystem and build relationships and bring

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Raymond DiNunzio | TOS: 4 or 5 engineering departments together from different firms. And go. You guys are all related. You didn't know it, but you are.

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Mark Wickersham: Figure it out, yeah.

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Raymond DiNunzio | TOS: Let's be aware of each other, and how we can make these things move

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Raymond DiNunzio | TOS: and so, sitting this artificial intelligence on top of other people's technologies to mine for erroneous data and do different things. We can show them where the majority of their errors are coming from

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Raymond DiNunzio | TOS: right. And so we have stuff where you've got missing data, and no technology is perfect. It probably never will be perfect. But we we want to get it as is close to sort of.

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Raymond DiNunzio | TOS: you know, 98, 99% as much as we can in in the beginning, when we started looking at this, if we couldn't like rationalize 85% or better data quality. We would say, we cannot use this technology because we we don't want humans in here.

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Raymond DiNunzio | TOS: And so adding this technology on top of other people's technology. And the way we've created this using AI, it literally will identify. Here's an example, Mark, you're expecting 6 different private capital statements, same same fund, private equity fund. But you own it. And all these different things for a whole host of different reasons, and everybody did their job. But there was a glitch at the Administrator, and for some reason only 6 were telegraphed through the system, and so there's 1 missing.

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Raymond DiNunzio | TOS: and it's not the end of the world. No one's going to lose their life. But how most people would figure that out is the Controller will eventually figure that out when they're looking at the numbers or the numbers will be wrong. And however you're visualizing that, and you may pick up on that, you may not

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Raymond DiNunzio | TOS: right. But as you're looking to express and make decisions, having live, accurate data makes a big difference. And so what we've got is on every morning we're running these system analysis. And it's saying, Hey, we got 6 X was supposed to equal 7. It identifies where it came from. We use process automation software. It generates an email back to the company automatically and tells it. There's a problem you're missing this

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Raymond DiNunzio | TOS: right? And it's fantastic way to improve the state of what's going on and what's happening in a family office and not have some poor soul have to go to data reconciliation because it's a it's not a fun job.

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Mark Wickersham: And the beauty of these agents, too, is that you know they don't sleep. They don't lay off that task until it's complete. Right? It's

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Mark Wickersham: you don't have that stuff that falls between the gaps. Oh, I thought you had that! Oh, you did, or oh, I did the follow up, but they never got back to me, and then I forgot about it, and then you don't catch it until you're closing the books, and and you've spent all this time trying to figure out why you're off here or there, you know. I think looking at those large data sets, do, AI is great for that. And hey, what's missing cost basis like you find that out when you

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Mark Wickersham: move it downstream to your.

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Mark Wickersham: you know, financial accounting system the hard way. But if you could have somebody early on in that part of that Acap process. Say, hey, that cost basis didn't come over when we open up that account at Schwab, you know that's can save everybody a lot of time that way.

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Mark Wickersham: before we get into the AI, because I know that we can't not have that conversation. Just talk to me a little bit about vendor management. In terms of how, when they come to selecting a a vendor, how can a family office better set themselves up for success when it comes to negotiating that contract. And what should that be thinking about in terms of putting in the actual contract.

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Raymond DiNunzio | TOS: Yeah.

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Raymond DiNunzio | TOS: So

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Raymond DiNunzio | TOS: there's a lot here, and there's a lot we've learned. And to be fair, I think all the companies are getting much better, too. Right?

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Raymond DiNunzio | TOS: But but I would build standards into my contract. And and one of the things that I would recommend to people

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Raymond DiNunzio | TOS: is

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Raymond DiNunzio | TOS: the technology firms are all gonna want you to come forward and say, Mark, you know, we're gonna give you really terms. If you sign a 3 year, we're gonna give you amazing terms if you sign a 5 year right? And and people that's where they forget that that's not where the negotiation ends. And I spoke with somebody recently a family office. He's like, Oh, man, the pricing so good. I'm I think we're gonna sign up for 5 years. I'm like, really 5 years. What happens if it doesn't work?

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Raymond DiNunzio | TOS: And

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Raymond DiNunzio | TOS: I mean, it's like what's very common nowadays. When people get married, there's a prenuptial agreement involved. Certainly there are for most people that

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Raymond DiNunzio | TOS: or relatives of the family office. And I would think about like, what do you do with technology if it doesn't work? And I would have milestones built in, I would have things done around. Implementation built in. It always seems like. And this was our experience. It may not be for everybody's but the sales. People come along, and they're all really nice, bright, shiny, happy people, and they're all fun and nice, and they're going to take you to lunch or for a drink, and all these different things. But then they're gone.

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Raymond DiNunzio | TOS: And once implementation happens, the thing that we think about a lot is, what does the 1st 90 days look like? And when are we done? When is implementation done?

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Raymond DiNunzio | TOS: And so

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Raymond DiNunzio | TOS: if the companies are really good and they are. They're almost all really good. But typically us as consumers of the technology, we hear things like out of scope. Mark, we didn't have this scoped out. And you're like, Well, how could that be? We gave you volume information about ourselves, and this is all you do. And yet we were led to believe this is going to be a 4 to 6 month process. We're in month 9.

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Raymond DiNunzio | TOS: And we've heard horror stories, people in month 15 and 18.

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Raymond DiNunzio | TOS: And with certain products. We're gonna need another $100,000, right? And so

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Raymond DiNunzio | TOS: there's a concept in the energy business since we're based in Texas called a 9 line, and you know you've got so much money into this. Well, you're just going to keep spending it until you get the oil out of it right? And so you know that that unfortunately, will happen with technology. So I think about what happens when it doesn't work.

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Raymond DiNunzio | TOS: And I'd have penalties built in both ways if you can. And they want to sell you the technology. They want to be flexible. And as long as they hit their milestones these things shouldn't be a problem for you, they should be able to execute it. But if they don't like, why shouldn't you have a reprieve?

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Raymond DiNunzio | TOS: Right? And if you sign a 2 year contract. What? What's really going on in the 1st 60 days?

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Raymond DiNunzio | TOS: Right? So don't pay for it. And if you're going into the system, if the implementation team can't start for 5 weeks. Why are you paying for it?

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Raymond DiNunzio | TOS: Right? So be mindful of that.

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Raymond DiNunzio | TOS: Be mindful of of how things are going to work with other things that you have. So when you're buying technology, there's this concept of technology, debt and technology deficit technology, debt is the things that we've already got on the books, and however they're working or not working, they are what they are.

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Raymond DiNunzio | TOS: But does the new pieces that you're adding in? Speak to those work with those. How are you going to move that data? You know, we have all these data silos like, how are we going to move this stuff around. Think about the outcome that this is going to provide. You think about how much training is going to be required and not just training required to get it up and running. But when you speak to your peers and your friends and the people in the industry, or on forge, or at conferences, or wherever

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Raymond DiNunzio | TOS: like. How much effort does it really take for you to get this thing moving? And at what level would you grade yourself that you have it at.

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Raymond DiNunzio | TOS: so you could very well say, you know, this is Ray. I love. Ay, ABC, software, it's done really well, Ray, Grade yourself.

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Raymond DiNunzio | TOS: based on what you think you can get out of the tool. Where are you? And I'd say it's analogous to a lot of other software out there, right? I mean.

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Raymond DiNunzio | TOS: Salesforce is a very famous one, and most of us have a love, hate relationship with it, right? And so. But I'm certain that there's

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Raymond DiNunzio | TOS: tens of thousands of people that have extraordinary relationships with it, and it makes their lives effortless and amazing.

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Raymond DiNunzio | TOS: live without it.

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Raymond DiNunzio | TOS: But the implementation really matters. And so, you know, even when you pick the right technology for you, there's a 50% chance. I think that you're not going to be happy with the outcome.

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Raymond DiNunzio | TOS: And so I would focus on that. What's it going to take? What level of competence do our people need? How much output are we going to get out of it. What's the adoption rate going to be? What's our real budget look like for this? Because it's not about the technology. There's the implementation, the service packages that go along with it. Do you need to keep somebody on retainer to help update with it? Because a lot of these technologies

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Raymond DiNunzio | TOS: can help solve a lot of problems. But the operator on it needs to be an expert. Right? It's you put a golf club in Tiger Woods hand. You give me the same club. It's gonna have a very different outcome.

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Mark Wickersham: Result, right.

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Raymond DiNunzio | TOS: Right.

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Raymond DiNunzio | TOS: And I think people need to really work hard at operating these softwares. This is not the Star Trek Trek enterprise, and you're not talking to this machine, and it's not doing it for you.

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Mark Wickersham: I think.

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Mark Wickersham: yeah, I think a lot of some. Sometimes with these implementations. There's, you know, you might have selected the right vendor, but some.

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Mark Wickersham: maybe the family office wasn't fully prepared for the implementation, either.

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Mark Wickersham: I think Doug Fritz had a good saying, like fences make good neighbors, and and good contracts make for good vendor relationships that.

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Raymond DiNunzio | TOS: Yeah.

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Mark Wickersham: There is something to that in terms of

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Mark Wickersham: laying out the expectations. Clearly, it's obviously an avenue of last resort. But if you are in a situation where you're not getting the expected results from it. Well, why is that? Well, you had a 90 day plan with the milestones laid out in the project, and it's clear that you know who was responsible for what I just thinks. It helps clear, you know. Put the expectations in black and white as clearly as possible, and I think that that kind of sets you up for

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Mark Wickersham: for success. What are some of the other factors that family offices should take a look at in terms of implementing new software. That kind of helps them better increases the odds of success.

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Raymond DiNunzio | TOS: Yeah, do a lot of work upfront to really understand your processes.

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Raymond DiNunzio | TOS: Right?

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Raymond DiNunzio | TOS: You can't out software yourself out of bad processes, right? You just can't, and so define your process inside the office. Understand every step to a capital call. Where does the data need to go? Where does it need to live.

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Raymond DiNunzio | TOS: Everything from how you get that information about the capital call. Think about the number of fingertips.

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Raymond DiNunzio | TOS: how many people are copied from a duplication standpoint to make sure to check the bank, that there's liquidity in the bank account that you need in the particular entity that you need to do this 3 days before, and then the day that it's due like, think about all those calories spent from end to end. And then, when you look at the technology that you're looking at.

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Raymond DiNunzio | TOS: What of that? Does it solve?

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Raymond DiNunzio | TOS: Because oftentimes, if not, the majority of times when we buy technology off user interfaces.

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Raymond DiNunzio | TOS: it'll help you go faster. But sometimes in the wrong direction. And you're gonna you're gonna have to throw more bodies at it. And the more technology that a lot of people adopt. Unfortunately, the more headcount that they're adding to. So something that was supposed to make our lives more simple

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Raymond DiNunzio | TOS: or better.

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Raymond DiNunzio | TOS: often doesn't feel that way, so we can't express loud enough that what is the outcome that we're looking for? How close does this bring us to the outcome that we want.

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Raymond DiNunzio | TOS: and let's be honest with each other about budgets. Right? I mean, that was the most helpful thing about working with Bcg, like I get it. We don't have limitless budgets. But when you pick technology based on price, you're generally making a mistake.

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Raymond DiNunzio | TOS: outcome, outcome, outcome all day.

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Raymond DiNunzio | TOS: And you, you know, if any, all of us in the family office industry in space, and that work in family offices probably should go back to university and become industrial psychologists. So we can explain to the principals why we need to spend this money right? Because we're trying to look after their capital.

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Raymond DiNunzio | TOS: We're trying to not have big tax surprises.

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Raymond DiNunzio | TOS: We're trying to not have bad trust and estates and surprises estate plan surprises right?

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Raymond DiNunzio | TOS: In order to do that. Let's go back to that benchmark that Bcg created, and I think it went up this year. Jp. Morgan came out with their inaugural

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Raymond DiNunzio | TOS: family office publication, and they said, It's 64 basis points now. And so you know, that's.

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Mark Wickersham: Spending on tech.

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Raymond DiNunzio | TOS: Well to be on the operations and the service of the family office, not on, not on the investment of capital, right? So no deployment of capital, no real estate, maybe the real estate of the office, which is what it is.

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Raymond DiNunzio | TOS: but not.

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Mark Wickersham: Do you? Do you have a tech spend like a benchmark or or guideline that you see for top performing family offices.

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Raymond DiNunzio | TOS: I've seen some stuff out there.

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Raymond DiNunzio | TOS: I think Cambridge put some. No, Camden put some stuff out last year on it, but that's really it's all over the map, right? You have some people. We have a family office that we know really. Well here in Houston. They own every piece of technology under the sun

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Raymond DiNunzio | TOS: every piece, because they keep trying to buy more thing. And it's going to magically solve their problems. And they magically always seem to have 3 open recs for more people.

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Raymond DiNunzio | TOS: but but but if at least you can go back and frame this with them, like what is our budget.

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Raymond DiNunzio | TOS: And by the way, the budget needs to grow like, what are we going to be able to get through with this year? Where do we want to be operationally in 3 years the workload is going to continue to grow. Had a conversation with a family we know really. Well, somebody I used to work with when I was back in the bank. This fellow ran the investment bank. Now it's a massive investment bank, probably top

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Raymond DiNunzio | TOS: 20 or 10 investment bankers in the world, and his daughter setting up the family office, and we had a discussion, and she's like Ray. I just came out of this family office in New York, and there's like 8 people working in admin in the family offices just on their real estate stuff. And I'm like, huh!

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Raymond DiNunzio | TOS: And she's like. Well, we don't want that. We only want to have smart investors. Her brother worked in a massive hedge fund. They're all graduates of an extraordinary business school.

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Raymond DiNunzio | TOS: and my commentary is like, you're going to end up here. You're not going to have a choice right? You're going to keep growing and keep investing more and keep having success. And the more success you have, the more stuff you're going to have to track, and the more things you're going to have to do. And the more bodies you're going to throw at things right? And the more technology and the way she's buying technology, she's falling in love with technology

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Raymond DiNunzio | TOS: and basing on the CEO and the demonstration. And she's a venture person. So it's not wrong. She's falling in love with these companies. But the more tech. She's adding the more people she's gonna need.

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Raymond DiNunzio | TOS: right.

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Mark Wickersham: Just the nature of the of the beast. Let's let's talk a little bit about data data management. I think. Certainly during the implementation process.

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Mark Wickersham: Family offices love. They want as much data as possible, backdated data.

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Raymond DiNunzio | TOS: Oh, yeah.

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Mark Wickersham: What's your perspective on that? It certainly can be expensive. I think it could be a way in which you can get an implementation to go sideways. But what are your thoughts on on historical backloading of historical data?

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Raymond DiNunzio | TOS: We have a new client coming on board and

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Raymond DiNunzio | TOS: in Austin. And they brought up this idea of going back with all their data. And I'm like, what's the rationale for it? Why do you want to do it?

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Raymond DiNunzio | TOS: And

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Raymond DiNunzio | TOS: well, you know, we want it like, you know, we have it. And we, we would like to move it over. I'm like, okay, so you have the data like.

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Raymond DiNunzio | TOS: what level of quality you think it is at? Is it 85% accurate? 95% accurate. Is it a hundred like if you lost your job? If it wasn't at, would it be 90 or better. And he goes.

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Raymond DiNunzio | TOS: I wouldn't bet my job on it. I'm like, okay, so why do we want to move it?

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Raymond DiNunzio | TOS: Curious like we can move it right? You can move this. It's historically done manually and historically inaccurate. And even when you're going and backfilling it in like, it's no different than excel logging people in. We work with a large accounting firm. Interesting. We help them automate and think about

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Raymond DiNunzio | TOS: doing quarterly estimated they had somebody downloading data data entry person. They had to check the data person. They had to check the checker and a managing director sign off on it because you're using for tax work. Well, if you're going to do a backfill, there's going to be a data entry person. That's it. So who's who's checking the accuracy of what they're putting in there.

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Raymond DiNunzio | TOS: They got to have 5 people involved to say how we categorizing this, you know, charts of accounts change all sorts of things, change in terms of

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Raymond DiNunzio | TOS: that being said.

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Raymond DiNunzio | TOS: we, we're looking at some really cool stuff. So we're very close to a couple of amazing venture firms that we we help sit inside the venture firms and look for new technologies and solve problems. One out of y combinator.

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Raymond DiNunzio | TOS: Like, it's it's data. It really comes down to this mark. Everything comes down to this

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Raymond DiNunzio | TOS: data, extraction data, structuring and data visualization. The technology is what it is, and it helps along the path. But those are the 3 things that we focus on all day every day.

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Raymond DiNunzio | TOS: So let's take backfill.

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Raymond DiNunzio | TOS: If we went backfill, let's just not move data. Let's take statement data.

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Raymond DiNunzio | TOS: because statement data out of your custodians or whatnot should be accurate, right?

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Raymond DiNunzio | TOS: And how far back can we go to get that? Well, the problem with that is, that's a that's manual, and somebody's got to get that off, and and then somebody's got to put that in a spreadsheet, and somebody has to do all these different things. But what if

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Raymond DiNunzio | TOS: we, in the advent of AI applications, we could train agents to go and ping that thing, capture that data. Read that information, move that data and automatically populate the upload for whatever technology that vendor that we're using and moving that through the system.

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Raymond DiNunzio | TOS: So our firm and a mutual friend of yours and mine are testing this with 3 companies right now

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Raymond DiNunzio | TOS: to see if that will give us the quality data that we want that we could do that without human beings touching it, and.

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Mark Wickersham: I think this is a great area where I can apply the the brokerage statements. I mean, we're talking about. Obviously, alternatives has been one of those areas. But

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Mark Wickersham: the brokerage, you know, firm is is the, you know, the books and records, and often the the data feeds that you get from these firms are are incomplete, especially around cost basis amortization. But it's on the statement. So if you can feed the statement in into the machine and they can convert it into structured data and do that all processes for you. I think there's a lot of value

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Mark Wickersham: in that for a lot of different applications. I I get excited about that particular use case. I think you guys overlooked because, you know, alternatives all day. Right? Let's talk about the impact of AI. And you know it wouldn't be a well tech podcast if we didn't talk about A. But how is AI impacted your particular business? What are you? What are you seeing, and how should family offices be thinking about adopting AI.

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Raymond DiNunzio | TOS: It's a good question. I mean, everybody's talking about AI, right? I saw a good piece out from

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Raymond DiNunzio | TOS: I think it was Bain.

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Raymond DiNunzio | TOS: and you like when you talk to the C-suite about like, you know, are they comfortable with their AI strategy? It's like 87%, like, yeah, we know what we're doing. We know we're going, we're doing this. But the people are actually doing the work and everything else are like, you know how confident with your firm strategy. It's like 37% right? And.

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Mark Wickersham: We have one, right?

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Raymond DiNunzio | TOS: Yeah, and and I, and I think everybody's talking about it and like, whether in asset management. And if you're thinking about well, tech, if you're thinking about like everybody's talking about it right?

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Raymond DiNunzio | TOS: They don't know what they're talking about, though, and like, you see, all these things written up about the applications for AI, and I certainly love Rebecca Gooch at Deloitte.

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Raymond DiNunzio | TOS: and the pieces that they come out with. But AI for AI sake is silly. What is or so, what applications are we empowering with AI and using agents to go solve other problems with?

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Raymond DiNunzio | TOS: Right? So for us, data, reconciliation makes sense. We're working on a couple new technologies right now.

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Raymond DiNunzio | TOS: We're not working on them. We're we're giving perspective on it as early access partners. So this is really interesting area mark where you can take this

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Raymond DiNunzio | TOS: connection and put it into a data room. And we have a family office that we're working with here in Houston to start up family office about 4.5 billion, and it'll help you do your deal analysis. So if you can actually have the the

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Raymond DiNunzio | TOS: agents go in, and they know what you're looking for as an investor. You can. You can mitigate certain things that you would never invest in. You can make all kinds of strategic and structural issues, and it can help you make those decisions. Omni was trying to do that out of Salt Lake a few years back they were backed by Svb and a bunch of different folks. We like them a lot. We we tested data with them. We wanted to help them build their product. And it it. The technology wasn't ready yet.

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Raymond DiNunzio | TOS: The technology is ready now, and that can really save you

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Raymond DiNunzio | TOS: 3 4 days worth of analyst work. And think of that! You could go look at hundreds of deals.

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Mark Wickersham: Right.

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Raymond DiNunzio | TOS: And then come back in. And it's gonna tell you it looked at a hundred deals, mark, here's 3

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Raymond DiNunzio | TOS: like, Oh.

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Mark Wickersham: On your particular profile that you have, you feel comfortable with that investment approach. You want founders that were operators that are in a particular.

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Raymond DiNunzio | TOS: Investor rights could be anything right? Yeah. Like, there's all kinds of different things that you could put in there from a direct investor standpoint, right? Dilution clauses, like all kinds of different things. If you're looking at venture or co-invest

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Raymond DiNunzio | TOS: right? That's fantastic, right? And so with the folks that we're working with at this really cool venture firm that we're close with. They're like, they're super optimistic that

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Raymond DiNunzio | TOS: in 6 months there's going to be so much more advancement than even where we are today. In these things, which is amazing, it's exciting. And it's frightening, because how obsolete are the companies that people have, that they've been working with that are 5 years old, and we all know how painful an implementation can be. My goodness.

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Mark Wickersham: Right right? And then they have to get off software that you barely have been on. I I think the agenic AI for the investment professionals in particular. I mean, they're that. Those are your expensive resources.

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Mark Wickersham: the the amount of deal flow that family offices see, they can't, even, you know, correctly kind of manage that kind of data tsunami. But if you could apply.

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Mark Wickersham: you know AI to that particular problem. So then you're really looking at the stuff that truly meets your criteria be able to to identify the outliers on that. I think that that's tremendous, even on the public side, like, send send these agents out to listen to all the analyst calls, and just just summarize all that information like you. You have a 10 x, or now of your investment professionals.

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Raymond DiNunzio | TOS: Yeah, there's

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Raymond DiNunzio | TOS: There's a company called Boosted AI. It's Canadian Company.

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Mark Wickersham: Right.

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Raymond DiNunzio | TOS: And.

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Mark Wickersham: I was blown away when I saw that demo. It's just like it's amazing.

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Raymond DiNunzio | TOS: Right, and you could think of the applications of that. So when we met with them.

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Raymond DiNunzio | TOS: like, you know, it's public market analysis scenario, you can say, you know, what 20 stocks do I want to have? If this is my thesis, or in this space? Right? It's going out to 175,000 different databases, and you can sit there and watch it like, build this thing for you. It's going to take 6 or 7 min, but it's compiling so much data and coming through and showing you that the analysis and why. And so I go to them. Okay, and we're working with

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Raymond DiNunzio | TOS: 3 other companies out of this venture firm to go pull in with with Agenda AI

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Raymond DiNunzio | TOS: Portfolio Company level detail on a private equity fund.

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Raymond DiNunzio | TOS: right? So that you can really know what you own.

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Raymond DiNunzio | TOS: and you can shock test the portfolio. So I go to the guys who boosted like, well, what if we have an energy shock. What happens if we go into a negative, more negative interest rate environment? Who knew? What if we have a tariff shock like you can have all this analysis, and you can run it against your publics, but you can also run it against all the holdings in the privates. And so now for the 1st time, I think well, maybe not for the 1st time ever, but maybe more readily available. People can go in and say, How do I hedge my private equity exposure

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Raymond DiNunzio | TOS: right

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Raymond DiNunzio | TOS: at the Portfolio Company, or where do I express my next dollar? Why do I do it this way? So you know most of us, most most family offices are buying things because they're presented to them, or they're connected to different people for deal flow. But if you really knew where you were underweight, and you wanted to have position in there, and maybe Ag. Tech or Lord knows whatever it could help. You identify those things, help you identify the gaps and then help you think about hedging it or leveraging it

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Raymond DiNunzio | TOS: right? If it's working really well, and you really like it like, what other things can I do to leverage what's going on in this particular space because of the success that it's having.

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Mark Wickersham: Yeah, I think it's the next frontier I mean, AI is especially on the private is kinda solve that kind of low value. 1st mile type of data, aggregation and conversion of unstructured to structured and and which is certainly a huge leap forward. Don't get me wrong.

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Mark Wickersham: because you know that that whole world stuck in 1996 in a Pdf. But now you can do these things that you're used to doing on the on the public side in terms of being able to do more dynamic analysis of your portfolio in the underlying companies. I think it's it's fascinating what AI is going to be able to do to the front office. Where? Where do you see AI impacting the back office? I know you talked about reconciliation a little bit. But

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Mark Wickersham: you talk a little bit more about that.

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Raymond DiNunzio | TOS: Yeah, I mean, we're we're seeing it happen. I mean for us. It's automated workflows for us. It's right doing that reconciliation. When we map things out and how we're moving data is we just create rules for these agents.

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Raymond DiNunzio | TOS: And then they're coming in and they're going and mapping the work and doing the work.

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Raymond DiNunzio | TOS: and they're moving things from one place to another.

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Raymond DiNunzio | TOS: And so this repetitive work, right? Bob Pasani at Atapar is always like, you know I love this expression eliminate undifferentiated, heavy lifting. Well, let's eliminate all lifting

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Raymond DiNunzio | TOS: right. And and you can do this, then, then, that helps you have so much more flexibility when you're adding technology that does have a canonical data, structured environment that is interoperated and doing these different things right? That's where we see really interesting applications for this stuff.

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Raymond DiNunzio | TOS: Fascinating work that can be done because it'll help us do. We're very proud of the work that we've done.

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Raymond DiNunzio | TOS: And but the the evolution of this is being able to retrieve and recall data anywhere in any format. Any way, you want to see it right, anyway, that you want to see it with the least amount of effort, like I think I

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Raymond DiNunzio | TOS: penned a piece a few months ago, and, you know, talked about return on effort like, how much effort does it take for you to get the result that you're looking for

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Raymond DiNunzio | TOS: right? How much of that can be automated? And in our opinion we want to automate everything that.

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Mark Wickersham: Good chunk of it, right? Right? So that the question is, does AI modernize the family office, I mean.

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Mark Wickersham: or do you still see kind of this bill curve where certain percentage of family offices, especially single family offices, are are

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Mark Wickersham: not gonna be legacy software excel? Or does AI really be like I, I have to.

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Mark Wickersham: I have to embrace technology. Now. It's just it's too much of a, of a of a game changer.

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Raymond DiNunzio | TOS: Well, I mean

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Raymond DiNunzio | TOS: it. It depends on so many things like, when we started the company we met with this

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Raymond DiNunzio | TOS: really amazing lady in Chicago worked for a very well-known family office, we would all know.

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Raymond DiNunzio | TOS: and she had a mutual friend, really good friend of mine from Kellogg, and we sat down and talked with her, and she was like.

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Raymond DiNunzio | TOS: I love what you're doing, Ray. But she goes. So many family officers are going to be afraid of you, I'm like, why'd they be afraid of me? And I mean I'm only 5 foot 6 on a good day, like 5, 6 and a half right like, and she's like, because the they have sold to the Patriarch that they're doing this already.

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Raymond DiNunzio | TOS: and they have their arms wrapped around this right. And so

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Raymond DiNunzio | TOS: is it is excel, going away no way.

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Raymond DiNunzio | TOS: no way, because you could more easily get an investment banker

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Raymond DiNunzio | TOS: to quit drinking and smoking. Then you could get them to quit using excel. And so when they build out their family office, they're hiring bright analysts that remind them of them on, excel.

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Mark Wickersham: Yeah, right, right.

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Raymond DiNunzio | TOS: Right? There's gonna be all kinds, too. And it's like, what's the ability to spend. And the problem is once bitten twice shy. So when you go in and say, we want to go get this technology. And I feel so sorry for these people in family offices like, I visit with people in New York in a major family office recently, top 5, guy from a major private equity firm.

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Raymond DiNunzio | TOS: And I know they're going down the wrong path with their technology architecture.

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Raymond DiNunzio | TOS: And I was just like dude. Let me help you like. Tell me what your organizational structure looked like. Show me the entities I don't care about what's in them. I don't care about anything else. Show me the sources, and I will map you a data architecture plan for you to move forward with that. At least, you can be comfortable with for 5 years, because the path you're going down now.

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Raymond DiNunzio | TOS: this technology that you're going down. I don't know who sold it to you, but it's going to be complicated. It's going to cost you more money. You're going to throw more bodies at it, and I suspect you're going to be rewiring in 3 years. And so you have to go back to the principal again, and they go.

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Raymond DiNunzio | TOS: We need some more money and like, Why do you need more money? Well, the system we have is not working right like that's that's hard to go.

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Mark Wickersham: Have to ask for money. You get that system. Then they have to go back and ask for.

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Raymond DiNunzio | TOS: We met a.

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Mark Wickersham: Fix the system.

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Raymond DiNunzio | TOS: We met another really, really big family officer. They're lovely people.

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Raymond DiNunzio | TOS: and they hired a consulting firm.

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Raymond DiNunzio | TOS: and the consulting firm came forward and gave them

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Raymond DiNunzio | TOS: their suggestion of technology softwares, which, by the way.

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Raymond DiNunzio | TOS: they may have been resellers of many of those pieces. And and we'd show them we did that same exercise map, the entities, map the ownership map where everything sits right. And then, you know, we we pre-engineer the outcome that we're looking at from the data structure.

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Raymond DiNunzio | TOS: and I showed it to her. And she's like this is amazing. She goes back to her consultant and hands it to her, and says, this is what I want you to put in the report.

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Raymond DiNunzio | TOS: and I go to her like we're having lunch, and I'm like.

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Raymond DiNunzio | TOS: why'd you hire the consultant? She goes. Oh, well, I don't want to deal with salespeople, and if it goes wrong I can blame the consultant right. She's like

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Raymond DiNunzio | TOS: like I was like.

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Mark Wickersham: Yeah, I mean, consultant should add more value than being a scapegoat, and they can help these family offices on these buying journeys. But sometimes you have consultants that are are there for consultants sake.

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Mark Wickersham: ray! This has been great. I like to wrap up these conversations a little bit on a personal note with 3 questions that have nothing to do with wealth. Wealth tech

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Mark Wickersham: what's a hobby or skill like a superpower? You might have that people don't know about.

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Raymond DiNunzio | TOS: Hobbies and skills. I love doing things fast boats, planes, racing boats.

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Raymond DiNunzio | TOS: love scuba diving, love skiing you and I, ski that we have that happen?

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Raymond DiNunzio | TOS: I love meeting people like one of the best parts of running that family office practice

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Raymond DiNunzio | TOS: for the big bank I was at was meeting all these founders and hearing their stories and doing different things, and a big part of what we do is trying to connect good people to other good people. It's not a superpower. My wife just says I talk too much, but I've never met a stranger like last week when we were in we were in aspen skiing and

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Raymond DiNunzio | TOS: sat down. This lady sits down next to us at at the bar we're having lunch at, and all of a sudden she's hanging out with 7 of us, and there's a huge wedding going on in Aspen last week from a well known family in Houston, and 25 private jets out there

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Raymond DiNunzio | TOS: like we. We became interconnected like immediately like, and my daughter says the same thing to me. Like, Dad, you go to London, you bump into a bunch of people, you know, right? Like.

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Mark Wickersham: Okay.

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Raymond DiNunzio | TOS: It's just fun meeting people, and, you know, makes life more enjoyable.

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Mark Wickersham: Well, that is a that is a superpower. So in terms of skiing, what's your what's your favorite place? What's your favorite resort?

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Raymond DiNunzio | TOS: Man, you know, that's that's a really tough one. If I'm gonna say North America

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Raymond DiNunzio | TOS: and you always create enemies when you do this, I lived in Colorado in the mid nineties, and nobody in Colorado who's a Colorado native likes Vail. I love Vail because of the back poles at Vail.

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Mark Wickersham: Feels amazing. It's like one of the best resorts in the country, but.

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Raymond DiNunzio | TOS: Yeah, but I mean every the you know the Colorado ends will tell you. They go to Winter Winter Park or Mary Jane.

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Mark Wickersham: Proper and right.

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Raymond DiNunzio | TOS: Right like they. They like the the technical ski hills.

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Mark Wickersham: Like a litmus test of how a hardcore a ski you are! But.

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Raymond DiNunzio | TOS: Yeah, on, on. I 70, right? Yeah.

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Raymond DiNunzio | TOS: And I'd say, like I would like when I lived on the East coast, we would when I was younger we'd we'd always go to Europe right and go to like Austria exam different places. And it's certainly in a completely different skiing experience.

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Raymond DiNunzio | TOS: Right? You go to Val d'isere. I think we need to like, get a couple of really fun technology people next year, and we'll put we'll put our own Mini Tech conference on with 12 or 24 technical skiers, and go to Val d'isere for 5 days, and ski across towns and eat great food.

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Mark Wickersham: That sounds great. Eat stinky cheese like. You know I got. I got a place up in a little cabin up in Maine, and there's sunny rivers

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Mark Wickersham: about a bigger resort. You can get up there, but I like the the family hill, Mount Abrams, especially when the snow is good, because I know where the little stashes are, and they don't get skied off by noon. So it's you know, everybody has their own thing, and they're different folks for different different skiing things in terms of business travel. Obviously you get to travel quite a bit. What's your favorite business destination?

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Raymond DiNunzio | TOS: Oh, man, I like them all like we. We travel a fair, much internationally at my household, and

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Raymond DiNunzio | TOS: had a great time in Istanbul last year. We spend usually about a month, a year in Africa, my wife from Kenya

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Raymond DiNunzio | TOS: and so we work with a venture firm out of Chicago quite a bit, and I spent a lot of time in Nairobi helping some of their venture portfolio companies and whatnot. That's more ag tech and things right has nothing to do with my day job.

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Mark Wickersham: Yeah.

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Raymond DiNunzio | TOS: Meeting people, building businesses and doing things around there.

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Raymond DiNunzio | TOS: Been spending way more a lot more time in Cayman than I've ever spent, because it's such an interesting international booking place. And we're working with a lot of folks down there. There's a lot of international activity down there. There's an amazing conference that happens down there every year, hosted by a very big family on the island.

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Raymond DiNunzio | TOS: probably the the most significant family office conference I've ever attended with over 125 family office represented over a billion dollars and world leaders hanging out there from Abu Dhabi Riyadh Dubai, the Uk.

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Raymond DiNunzio | TOS: It's extraordinary. It's like this miniature. Davos. Davos and Ted had a very immature child. Who's.

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Mark Wickersham: Had a baby.

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Raymond DiNunzio | TOS: Girl. That's their conference. It's spectacular.

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Mark Wickersham: Yeah, I

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Mark Wickersham: enjoy the travel aspect of it. I'll go anywhere once. But for me, I mean, it's it's close by, but it never gets old, is good. Old New York City man is like.

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Raymond DiNunzio | TOS: Yeah, Hong Kong and Singapore fun like we. I used to go there a lot when I was in San Francisco, working for the big bank like like those are just such great places to go

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Raymond DiNunzio | TOS: like fantastic everybody should go. Everybody should go hang out in Hong Kong and Singapore for a week at a time, and just take it in. It's it's unbelievable culture.

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Mark Wickersham: Sign me up alright, Ray. This has been fantastic. I could talk shop with you all day. I really appreciate the time and the insights.

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Raymond DiNunzio | TOS: Appreciate it. Mark thanks so much for having me.

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Mark Wickersham: Alright! Thanks.