In This Episode
In this episode, Rory Holland sits down with David Benskin, the founder and CEO of Wealth Access, to explore the grit required to change the way financial institutions use their data. David reflects on his 13-year journey as CEO, from his early days at Merrill Lynch to navigating the global financial crisis and launching a platform to solve the fragmented data problem plaguing financial institutions, wealth advisors, and clients alike.
They discuss the decision to rebrand from a data aggregator to a connected intelligence platform, the vital role of clean data as a foundation for AI, and why technology should empower—not replace—the human element of financial advice. Beyond the boardroom, David shares how coaching his kids in wakeboarding mirrors the responsibilities of a CEO.
Key Takeaways
- Solving the Right Problem: David didn’t set out to build a tech company; he set out to fix the fragmented data problem that wasted 50% of his time as an advisor.
- Data as the AI Foundation: For AI to be effective in finance without hallucinating, it must be built on a secure, organized foundation of both structured and unstructured data.
- The “Connected Intelligence” Pivot: Rebranding wasn’t just a visual change; it was about moving from simple data unification to providing actionable intelligence for financial institutions.
- The Power of Small Language Models: Wealth Access focuses on small language models in secure environments rather than broad, public LLMs to protect sensitive financial data.
- Scaling the Human Element: The goal of modern fintech is to automate the boring parts—like gathering 401k data—so advisors can focus on high-value human conversations.
- Leadership and Accountability: Drawing a parallel to boating, David notes that as a CEO, you are the driver; if the wave isn’t right for your team, the responsibility ultimately rests with you.
- Institutional DIY Competition: The biggest competitor for fintech firms is often the bank’s own internal build vs. buy indecision or the need to organize their data first.
Hook
David Benskin: …and I was with one of our clients in North Carolina and it was the one of the family members that owns the bank and he’s like, “You know, we’ve been working together for about five years, and I’d love to just hear from you what you guys do.” And I said, “You know, we’re a data unification platform that unifies your existing books and records to create hyper-personalized experiences.” And we’re actually sitting on the dock on the water and he’s like, “Do you want a beer?” And I was like, “Yeah,” so he brings back a beer and he’s like, “Tell me what you really do.”
Intro
Rory Holland: Hi, I’m Rory Holland, CEO of CSTMR and the host of Mighty Finsights. Every year I talk with hundreds of financial leaders and innovators. We unpack the highs and lows of working in financial services and FinTech. Today, I’ve invited the founder and CEO of Wealth Access, David Benskin.
A little background on Wealth Access. They’re an intelligence layer that unifies data across every line of business so financial institutions and wealth managers can operate as one. They’re creating clarity and connection in a world clouded by fragmented data.
Rory Holland: In this conversation, we’re going to discuss why entrepreneurs need to be problem solvers who are okay with everything being their fault, the reason small language models may be more helpful than massive LLMs, and how category design helped Wealth Access establish authority in the marketplace. Join me as we dive beneath the brand to learn what’s really happening.
Shared Love of Boating and Water Sports
Rory Holland: Well hey, David, welcome to the show.
David Benskin: Thanks for having me, good to see you Rory.
Rory Holland: You too, man. I was just commenting how nice you look, good to see you in a sport coat.
David Benskin: I got dressed—got dressed up for today, man.
Rory Holland: Well, appreciate that. There’s lots of stuff I want to get into about Wealth Access and your background, but one thing that we have in common and we talked a bit when we first started talking before we were, it was really hot, I remember. I don’t remember what time of year it was, probably summertime. And we both love boating. So tell me a little bit about that and also like your kids? I think your whole family wake surfs, is that right?
David Benskin: They do, they do. And we’ve actually been down to Austin to do a little wake surfing down there. Yeah, I, you know, one of the things that in getting out of the office and really charging the batteries, obviously spending time with family is a big part of that. But we got into boating. Nashville’s a city that, you know, we have lakes here. And so finding things to do, and wake surfing’s been kind of our go-to thing to go enjoy with the kids. And I think one of like my missions is what, our kids who bring their friends, I want to get them all up on a wakeboard. It’s kind of a coachable moment but fun thing to do.
Rory Holland: Yeah, and do, so have you been doing boating your whole life? Like have you back in the day when double ankle high wraps, I don’t know if you go back to that, was slalom skiing and all that?
David Benskin: I did. Grew up in Memphis, Tennessee, so we hada ccess to the very clean Mississippi River to do a very stable current.
Rory Holland: That was a really kind way of saying it.
David Benskin: Yeah, no. But yeah, we’ve, you know, have always gotten out on been around water and gotten out there and had a good time doing it and certainly, you know, spending time being able to go do that has been a fun experience for really the whole family. But it’s different now, right? Like it’s different. You go a lot slower wake surfing. You’re going 10 miles an hour and it’s really a lot easier at my age today.
Rory Holland: Yeah, I was going to ask you about that. So going from slalom skiing and I remember being sore back in the day. I was also a lot younger when I was doing that. But going a lot faster, crashing a lot harder, you know trying to like drag, like drag your hip on the water as you make the turns. The transition to wake surfing, did you wakeboard then transition to wake surfing when that came out? Was there like a, did that phase in or did you just jump right into wake surfing?
David Benskin: We just jumped right in. So I think maybe it’s like as to your point as you get older. I, whether it’s like getting out on the water or in the mountains snow skiing, one of my missions is like not to get injured. So it’s maybe part of that. But yeah, we just started doing it, saw, you know, it was a popular thing to do and had some friends that had boats and we just started doing it. And then our kids started also at a young age too. And so like seeing them progress as they’re going through it’s a fun thing.
Rory Holland: Can you guys all do it without the rope?
David Benskin: Yes, although I try to encourage my kids to use the rope.
When You’re the CEO Everything Is Your Fault
David Benskin: You know, one of the things that I’ve also learned about getting out on the water and driving the boat is everything’s your fault, right? If the wave’s not right or another boat’s coming and so it’s kind of like trying to keep them up to go you know, as long, they do compete, so all three kids will try to go without a rope and really be able to like who can stay up the longest? And I think one of the other things not to ramble about this, but it’s like as kids grow and they get taller, it becomes like more challenging as they’re like lanky. So it’s just a fun little—little project to—to do.
Rory Holland: Yeah, wake surfing’s something that my son with his sport, with Motocross, when we had time, we loved getting out on the water because it’s, you know, we raced up near you, outside of Nashville, in the summertime, usually end of July, first of August. And so getting out on the water—not that we had a boat in Tennessee because we didn’t, but I’m not saying that—but getting out on the water was great. And he’s the one that introduced me to wake surfing because I had wakeboarded and we mentioned—I mentioned the slalom skiing and all that. But man, it was really hard, but I asked you about doing without the rope, I finally figured that out last summer. So and he coached me into it, which was really wonderful.
So I want to shift gears a little bit but staying on the coaching front—or actually let me back that up. Before we get into the coaching, I wanted to say one thing that you said which is—which just made me think of a variety of different things, but I’m going to talk about “it’s always your fault.” And it sounds like one, it’s like being the founder and CEO of a company; two, being married. You know, thinking about that, like how has that translated, like when you think about your work as a founder—and we’re going to get into Wealth Access in a minute here—but like when you think about that and the responsibility that you have in coaching your kids, taking care of your family on the lake, like how does that translate for you into the work that you do as a founder and CEO?
The Origin Story of Wealth Access
David Benskin: Well, I think part of that is I didn’t really, you know, as a founder and CEO of Wealth Access, you know, set out—I wasn’t set out to build a technology company, I was really set out to fix a problem. And when you bring that into coaching or teaching kids how to wakeboard, I would compare it to the challenges that as an advisor that I saw for our clients that really couldn’t get a clear picture of their financial situation. And for them communicating with us, you know, we had 50 families my team did in terms of us helping them make these financial decisions and kind of coaching them to achieve their goals, it kind of ties into that.
Rory Holland: Yeah, I love that. And probably—describe for me—I’m going to get into Wealth Access a little bit, but we can move back and forth between this because your history in the space—and you and I both lived through the global financial crisis in 2008 and like what that did to a lot of people financially and companies too. So there’s a lot of history I think that you have in deciding, you know, I think 13 years ago, is that how old Wealth Access is?
David Benskin: That’s right, that’s right.
Deciding It Was Time to Start a Company
Rory Holland: Yeah, so 13 years ago, making that decision to start Wealth Access, what was that decision point? And it sounded like you wanted to help people and coach people and you ultimately solve a problem. What led you to start Wealth Access and—what it’s pretty courageous to start a tech firm in—in finance.
David Benskin: Yeah, so, I know that there were two moments that really led me to convince my wife that it made sense to leave a stable recurring revenue business to get into a software company. But, you know, the global financial crisis was challenging and, you know, I was at Merrill Lynch and, you know, the firm itself was going under, right? And so it was super challenging and you had clients literally calling saying, “Am I okay?” right? “What’s my balance sheet?” you know, “What’s the FDIC or SPIC, am I going to be okay?” And it was really challenging to gather all of their information, their balance sheet and communicate with them. And so that was obviously an important time. And then, you know, the other was COVID, right? And I think, you know, my wife is a banker and hearing her on the phone with her small business clients that had to shut down their business and they’re kind of trying to figure out what to do there. And I think a lot of that is around, you know, communication, you know, really connecting people with their data.
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Rory’s Commentary
Rory Holland: We have access to more data than any humans at any point in history. The entire internet is accessible from the palm of our hands. But David experienced it a different way. People were desperate to understand what was happening with their wealth, but they couldn’t. We can’t predict the next crisis or when it will hit. What we can do is be prepared. Wealth Access helps institutions by creating a cohesive data ecosystem so they can tackle whatever comes next, be it chaos or opportunity.
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David Benskin: And so understanding those two events and how difficult it was for advisors and for clients to understand what they were, you know, what decisions they had to make and how they could really get through those challenging times and everybody ended up doing that there’s just a better way to do it. And I think if we can solve the fragmented, you know, problem of information and data and not have advisors or clients having to scramble to figure that out, then I think people can really get connected and have real conversations about, you know, what’s going on and make really informed decisions.
Rory Holland: And so that was—that sounds like your experience through that whole process was part of the formation of Wealth Access. Is that accurate to say?
David Benskin: Absolutely. Yeah, I—mean, go ahead.
Rory Holland: I was just going to say, it sounds like you started building it almost on spreadsheets, like in how it would all work before tech—became—you introduced the technology side and development, is that accurate?
David Benskin: Yes, I would actually go back a little further. So when I first started at Merrill, it was, you know, financial planning and wealth management, you know, back then and again, this is like late 90s, so this has been a while. But it was the way that the firm was doing financial planning and like straight-line analysis, it was kind of everything was boilerplate. And so literally in my first couple of years, I was like, this, you know, returns don’t go in a straight line and started to leverage technology and actually found a few startups that were doing more Monte Carlo simulations and probability analysis and really understanding like the sequence of returns matters and part of that also was putting data into it. So I think it started at least my interest in technology really early on and then navigated that through a large financial institution to figure it out.
Rory Holland: What was that—take me back in time that moment when you decided, “You know what, I’m going to step away from this,” and the conversation with your wife, “I’m going to step—I’m going to start a company.”
David Benskin: So she knew I had the entrepreneurial bug and actually saw a few companies come through Nashville in financial technology that I was familiar with. And part of it, you know, the aha moment specifically was I was at my office at 7:00 at night with a spreadsheet in front of me and putting all this information, you know, to prepare for a meeting that I had with a client the next day. And I was—the data that I was putting even into the spreadsheet that I had built, you know, you would call a client and say, “Hey, what’s in your 401(k)?” They’d say “stocks.” You know, “how much is there?” They’d say “$400,000.” And then you get the statement and it’s like an energy ETF 100% invested and it’s a completely different level. So I started to look at it, Rory, in a way of like, this is not the best use of time. And it’s important to be able to, you know, have conversations with clients. And I actually identified in my role as an advisor there were really three primary things that I should be focused on. One is know your clients, right? If you think about the human element of, you know, having a real conversation with a client about, you know, is your family still intact? Are you selling your business? What’s going on, are you healthy? And part of that is bogged down because you’re at the office building a spreadsheet and then they—you have to ask them the questions of “what do you have” and it’s an awkward conversation anyway. The other issue was, you know, we’re responsible for managing money, so that takes a little bit of time. And the third was really you need to be able to grow a business. And I found that all three of those things were diluted by about 50% of my time trying to gather this fragmented data and back to the being determined to find a better way that was that evening I came home and told my wife, I was like, there’s an opportunity here, there’s a real need for this. And it’s really, you know, been an extension of what we do to really do that at scale at financial institutions to enable them to really have these conversations. They’re the trusted advisors with their clients and so it’s great, you know, being able to build that and deliver that at scale.
The Early Days of Wealth Access
Rory Holland: So what were the—staying kind of in the beginning days of Wealth Access, what were those first couple of years like?
David Benskin: We actually had a functional prototype within the first, I think 11 months of the business and we actually had revenues. So we had paying customers. But, you know, the proof of concept that I decided was, hey, we’ve always been a business-to-business, we are a software-as-a-service working with financial institutions or financial enterprises. But I also thought about it from the client first. And went around to a few people that I know and said, “Would you pay $100 for a dashboard just to see all your stuff on your smartphone?” And so they did that. That was a very short three-month timeframe to really get the proof of concept out. And then in terms of the first two years I decided in coming from a big, you know, wirehouse, obviously the RIA market,the independent wealth advisory space has continued to grow. And I viewed it as there’s less red tape and so we could probably get them to license this solution. And they had a real problem. They were probably, the clients were usually sole practitioner, smaller RIAs, but they were using multiple custodians, and custodians are Schwab, Fidelity, Pershing. And they didn’t really have a way to unify that data and engage their customers and so that’s what we had built and we’ve always been really good at continuing to integrate data from these disparate sources to be able to enable them to better communicate, engage with their clients. And we started to integrate with a bunch of different platforms and so we grew really fast, I think, you know, going past the first couple of years, but, you know, at our peak, I think we had something like 200 RIA firms and were growing at a pretty rapid pace. So it was a fun time and, you know, my wife told me I had two years to get after that get after this and now we’re 13 years into it. So it was certainly challenging but had a great team around me and we’re able to build a solution that, you know, solved really the same problem that I had as an advisor to help them do the things that they needed to do.
Would David Found Another Company?
Rory Holland: Yeah, I love that. Thanks for sharing all that. Just a question that comes to mind is as a founder myself, and I’ve done it a handful of times now, had you founded a company before or was Wealth Access your first one?
David Benskin: It was the first one.
Rory Holland: In hindsight, would you do it again?
David Benskin: Oh, that’s a good question. I was not ready for that question. You know, starting a company has its challenges, right? Putting people together, building the right team and we’ve certainly had, you know, our challenges, but it’s been a great journey. So I think would I do it again? I would respond by saying that, you know, every couple of years I still think that Wealth Access is just starting. And, you know, we’ve continued to evolve the business, you know, going from, you know, sole practitioner RIAs, now we, you know, have 65 financial enterprises, banks ranging from, you know, half a billion in bank assets to close to 300 billion and so we’re doing it at scale. And so it’s still exciting in terms of what we’re doing and building out a team to solve some of these challenges. So I actually view Wealth Access as kind of an evolution to continue to scale it.
Category Design and the Decision to Rebrand
Rory Holland: Yeah, it’s a journey, right? Just like life running a company, things change. Clearly technology changes, we’re in just this hyper—particularly with AI now coming out—this hyper evolution. But you used to be, if you recall back when we were younger, things would change over decades. Remember the 60s, the 70s, the 80s, the 90s? Now it’s—like feels like monthly or every year, the acceleration is crazy. So you had mentioned it’s kind of like every two years like you’re like a startup. Well, tell me a little bit about this rebrand, like you guys made a big decision to rebrand the business, reposition yourself, you’ve got some new technology out there. Tell me a little bit about the experience—the decision point that you made to do that and then what is the process felt like and what’s the experience been for you going through a rebrand and kind of relaunching the business?
David Benskin: So one of the challenges actually, what actually drove this, I read a great book called Play Bigger and it was around category design, right? So which category is your company going to be in and, you know, what do you do? And what I found over the years, Rory, is like the industry has put us in these different categories and, you know, I think initially we were an award-winning PFM digital experience, and then we were considered a data aggregator. I think somebody called us a CRM, like we’ve been in all these different categories. And so I think part of that created challenges for us in terms of where do you fit in and when you’re working with financial—with enterprises, you know, it’s like which bucket do you actually do? And we made—I made the decision that we were either going to design our own category in terms of where we’re going to fit in, but does that really matter versus, you know, what is the perception of the market?
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Rory’s Commentary
Rory Holland: David’s realization is shaping the future of his company. The decision to rebrand Wealth Access and to design their own category was a bold move that many business owners wouldn’t have made. It’s a tough marketing challenge because you can’t rely on comparisons with other products or companies. You have to teach the market why you’re a different animal altogether. Not every company even gets an opportunity to shape a new category, but that’s exactly what Wealth Access is doing.
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David Benskin: And I think I told you this story and so our the evolution of Wealth Access is we’re going from a data unification to really, you know, a connected intelligence platform. And I was with one of our clients in North Carolina and it was the one of the family members that owns the bank and he’s like, “You know, we’ve been working together for about five years, and I’d love to just hear from you what you guys do.” And you know, I was like, “We’re a data unification platform that unifies your existing books and records to create hyper-personalized experiences.” And we’re actually sitting on the dock on the water and he’s like, “Do you want a beer?” And I was like, “Yeah,” so he brings back a beer and he’s like, “Tell me what you really do.” And you know, I was like, “We integrate all of your data so you can have meaningful conversations with your clients.” And he’s like, “That’s a really big problem.” And then it started another conversation. So the rebranding was not just the brand, it was the messaging, it was the perception, it was how do we not have to have, you know, a five-minute conversation with somebody to know what we do because we’ve got great results. I mean, we’ve been able to work with some of the largest financial institutions that are very active in M&A and going through that and we are the solution that’s putting the architecture together to help them to solve some of those bigger challenges. But, you know, what does the market perceive you as and how do you want to be positioned?
The other part of this is we’ve grown the team quite a bit and I went through an exercise with the team and I was like, “I want to hear your elevator pitch, like what do we do? What do you do when you meet somebody at a cocktail party?” And there’s a lot of different responses and I was like, “It would be a really good exercise for us to go through this rebranding to get their feedback, not just mine, and what’s going on in the marketplace and how do we continue to position and grow the business but to get us aligned.” And so even going through like our core values and connecting people on what we’re doing, it’s been a great exercise to go through I’ll say we’re not, you know, all completely dialed in in terms of our messaging, but it’s been a great experience for my team, for the company and, you know, we’ve already started to have conversations with existing clients and they’re like, “We totally get this,” you know, “in terms of what you’re doing.”
How the Market Has Responded to the Rebrand and Where Wealth Access Is Headed
Rory Holland: What you described is a common problem. I talk to, you know, hundreds of financial and FinTech leaders every year and that is a common problem, particularly with as their brands and the industry and technology evolves. And then the team, as your team grows, it gets harder to keep your—you know this, right? Like harder to keep your culture intact and it takes more energy and effort. And then when your sales team and your marketing teams start to move away from the core messaging and you start to lose it, then it can become a wobbly thing that—like gets out of control. And when we, you know, we did the work with you guys on the rebrand and I’m really proud of what you guys did and what our team did and I think it’s what you described sitting on the dock and the guy going, “Okay, tell me what you really do.” Like we don’t have that luxury to sit on the dock and have a beer with every prospect, right? So how we nail it through the process and what it comes out the other side and then how we execute it with some discipline with agility too, right? Because things are going to change and that sort of thing. It makes a huge impact because there’s an authenticity to it, there’s a truth to it because your whole team was involved in putting it together. And so going back to that moment at the dock, knowing what you know now that you didn’t know then, what would you say to him now? Like, “What do you really do?” Now that you’ve been through the branding process, is it changed at all?
David Benskin: Yes, absolutely. You know, I would say it’s just simplified things and in terms of I think part of it is our culture, I think we can go back to that. I think that’s a really important part. But from the communication today, it’s we’re solving a very significant problem which is whether you’re an RIA, broker-dealer on the wealth side, whether you’re, you know, working on digital banking or digital transformation at the bank, you know, it’s all really around fragmented data. And so being able to simplify that in ways that they actually understand because it is a real problem for these financial institutions and to enable them to actually understand that they have great teams, right? I mean the banks that we work with and any of the wealth firms, like the relationships that they have with their clients they’re the trusted advisor, they’re the trusted financial institution. And so and we’re this middle layer that’s connecting that and so it’s a lot simpler in terms of understanding the problems that we’re solving and I think it is easier for them to understand what we’re doing.
Rory Holland: Yeah and how has the market responded to this? Because I there can at times be some apprehension, like because you’ve—you described how people try to categorize. And that happens all the time with brands and businesses and like where do we—you do it mentally and like psychologically in your own head when you see something or you speak to someone, like “Where do these guys fit?” But like how do you see now how is the market receiving you now and is that category creation still part of your mission here or did you find yourself in a new bucket?
David Benskin: From a category I think what’s interesting about that is, you know, our biggest competition at Wealth Access is the bank themselves, them actually, you know, making the decision to look at the ROI, to look at the business case, to understand that. To answer your question, I don’t—I think it’s better—it’s been a great experience, it’s new, right? We’re relatively new in that. But from a business perspective, we’ve continued to grow at a very rapid pace and continued to expand with our existing clients but really excited since we’ve launched the brand we signed up a large financial institution based down in the Gulf that was a good win and I think, you know, the conversations have been great so far.
Rory Holland: It’s great to hear. Now that we’ve talked about some of the early days and this recent rebrand, what’s on the horizon for you guys?
Where AI Is Taking the Industry
David Benskin: Yeah, what’s on the horizon for us? So we started, today we support RIAs, independent trust companies, broker-dealers, private banks, some family office at banks and so we’ve really started on the wealth side overall with the business. And what we’ve also found is being connected and having the ability to help them integrate their own data, it’s expanded over to digital banking. And so we’re excited that regional and community banks can, we like to say, they can deliver a JP Morgan like experience to their clients without having Jamie Dimon’s $18 billion dollar tech budget. And so being able to expand that and increase like the conversations are real. And I, we’ve been tracking the ROI for our clients and so them being able to get a good return on their investment, the efficiencies that they’re gaining, being able to unblock some of these technology or data projects has been a great experience. And we’ve also integrated with some of their data centers in terms of, or their data warehouse, so Snowflake, Databricks, Azure, AWS, etc. And what we’ve found is that at Wealth Access, we’ve always been really good about unifying existing books and records and part of what we do is and our terminology we call it a universal customer record. If you think about it in simple terms how do you connect, you know, David Benskin has an account at the bank, Nancy Benskin, Wealth Access has a business account, my daughter has a credit card, whatever that is, how do you get that overarching you know, household at the bank and how do you integrate that in the digital experiences? And so we’ve gone to be really good at that.
Obviously AI is moving at a really rapid pace. We’ve been on that journey for a year plus in terms of doing that. And what we’ve actually found is we have both structured and unstructured data. And what was interesting when I was talking with one of our clients about AI, he’s like, “Well, that’s kind of a stretch in terms of what you guys do. Like you’re the digital experience with data.” And said, “It’s actually not, and it goes back to the Merrill Lynch days of adding productivity and efficiencies in terms of how you can actually, you know, leverage AI.” So imagine, you know, advisors being in a very secure—we call it the small language model, not the large language model—in a very secure environment of being able to have a conversation with data beyond just the financial data. Like looking at documents and statements and other sources of information to be able to unify that and make that very useful. And so that’s where we call that connected intelligence of—it’s my—our position that we don’t think that AI replaces advisors and those human relationships, but can we enable them to have more accurate data, more timely, to be more efficient, to do less with more, which is a common theme.
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Rory’s Commentary
Rory Holland: I’m not going to make dramatic predictions about which jobs are going to disappear because of AI. There’s too much noise and not enough signal. That’s also why I love what David is saying here. Wealth access isn’t trying to replace the wisdom, intelligence, and warmth of human advisors. They’re trying to create efficiencies so that advisors can spend more time on what matters. They’ve also seen how their platform can aid digital transformation across every department making everyone better at their job.
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David Benskin: We’ve been at replatforming Wealth Access for the last couple of years, we’re excited our first client actually goes live next week with that. So it’s been a big shift for us to replatform, to set up the architecture to really be able to scale the business and then obviously, you know, the next phase is to really be able to activate that data to bring a level of intelligence and productivity to the firms that we’re working with.
Rory Holland: Yeah, that’s exciting. Well, congratulations.
David Benskin: That’s really great to hear. It’s been another journey.
Rory Holland: Yeah, and we’re certainly on one with AI and where everything’s going. Like in your mind, where do you see it going from here? Like tech is—it the acceleration is crazy.
David Benskin: What do I think this week? So, I think it’s where’s it going? When I think about my experiences with AI, my journey with AI started—I looked at my schedule and it was like a Tetris game and I was like, “I need to figure out how I can better organize this,” and started down the journey of figuring it out. And then for the company, we made a decision at the leadership level that, let’s buy into this and let’s see how we’re going to actually leverage AI in the way that we’re doing things. And I would say, Rory, that the pace—I mean it’s continuing to evolve obviously with Anthropic and Claude, you know, in terms of seeing what’s going on there and some of the productivity gains it’s been amazing, right? And so for our company, we use Anthropic, we have enterprise OpenAI as well, and Copilot and Gemini, and they’re all kind of bringing different—those LLMs bring a different level of experience in terms of what you’re trying to do for different business lines.
And so in terms of where it’s going, I think it’s an amazing journey and I also think the most important part about AI is really the foundation of data. Like have you ever used AI and it hallucinates?
Rory Holland: Oh yeah.
How to Deploy AI in a Thoughtful Way
David Benskin: Yeah, and so if you view it as like a probability, it’s only as good as the data that you’re leveraging, right? And so where we sit in the space is we’ve helped these financial institutions integrate their data, so it’s a natural progression to be able to leverage that. The other thing that I would mention is we have an annual event where we had 25 financial institutions come to Nashville last year. We do have a bourbon tasting and I’m convinced that that is actually part of the incentive, but they do come to learn about technology and this was a big topic. And to answer your question about where it’s going, I think if you were to go back to the beginning of, you know, the end of ’24, beginning of ’25, and you were to talk to financial institutions, it was almost like, you know, we’re not there, we’re not considering it. Then you started to hear about some of them using Copilot, using it for various sources. And then the other third were saying CEO just came back from an event, he’s drinking the Kool-Aid, we’re all in on AI, it’s our largest strategic investment of 2026.
David Benskin: And then you ask them the question, “Well, how are you going to do it?” The first thing that they said is, “We’re going to get our data organized first, and then we’re going to go hire an AI person,” right? And how many AI people are out there and all due respect to banks, but like, you know, where are they going to land on that? And so what happened is that they decided—and we’ve kind of small group of our clients that are—we’re building it with them to figure out, you know, what are the things that we could gain. And we had five model or five issues that we went to them, I said we’re not talking about AI, the buzzword is AI, you can debate what is AI and what is not, but like tell me about what’s causing you challenges. And the things that were coming out is—like we have to put client reviews together, and we have 14,000 clients and we have to do it four times a year and it takes two people a week. It cost them $2 million dollars of labor to actually get that done. And so where I think it’s going is can you start to leverage technology starting with a foundation of data, obviously security is in front of all of that, to set it up in environment to where, you know, firms can really start to use that and have an outcome. You know, we’re going to pursue this to do these things and keep it very focused to be able to deliver that. So where it’s going, I think it’s going to be an amazing journey, who knows what’s going to happen next and we’re excited about where it’s heading though.
Rory Holland: Yeah, same. I’m both excited and a little bit concerned. Like who knows, right? I think of the movie War Games, I don’t know if you’re old enough to remember that way back when. I think it was Matthew Broderick, is that right?
David Benskin: That’s right. Would you like to play a game?
Rory Holland: Yeah, you unplug it and the computer doesn’t stop. But no, it is—I think it is exciting times though. I think there’s so much potential, so many problems to be solved, but to be solved strategically and well. I also have seen and I have a lot of folks in my, you know, in our respective networks, right? That are moving down paths and there’s lots of paths being pursued, but few conclusions being arrived at. So I think it’s easy to overdo it, but I think the focus groups like you’re describing, what are some of the core problems with your clients. The one you mentioned is a huge one, $2 million dollars a year to do 14,000 reviews. Like, yeah, you could streamline that.
David Benskin: Well you bring up a really valid point is how are you thoughtful about it? And how are you—like from a security perspective? And I think banks, and just any financial data, right? And like making sure that, you know, from a privacy, security, that you’re setting it up the right way and doing the right things with it I think is critical, right? In terms of how you’re leveraging that. But the value of being able to access—I mean you think about like note takers and all the communication, it’s like what are clients really saying? Or what’s their sentiment? And then, you know, I think in the financial industry, really having that information to then go back to have the connected conversation it really becomes meaningful. I think the challenge that financial institutions have today is now everybody’s coming at them from every different direction and there’s a widget that does this or this does that, and so they’ve got every vendor going to them saying “here’s these tools” and they all may be great, right? They all may solve a challenge. But, you know, one of the things with that is then how do you get the right information into it? How do you make sure that it’s secure? You know, what’s happening with that information? So I think, you know, taking a step back and being very thoughtful about it, because AI’s going to continue to evolve and as that does, it does create certainly opportunities for you know, productivity, for other gains that are going to be there. But you’ve got to be very thoughtful about how you actually do that and what you don’t do. And so we actually look at it in a way of as much offense as we’re playing, we need to also play as much defense and understanding, you know, what happens if and to go through that process.
Whiskey, Bourbon, and Surfing
Rory Holland: Well financial leaders at the financial institution or RIAs, the different types of clients that you have, they’re all looking for help. Like solutions. Like you said, you could build a Frankenstein if you’re not careful with all the FinTech things that could plug in to your institution or to the work that you do. So I like that thoughtful approach. I wanted to just ask a question. So sounds like a lot of your folks that come to your event might be attracted to the whiskey tasting. Do you have a favorite whiskey?
David Benskin: I would have to say, so I am from Tennessee and our lake house is actually in Winchester, so if I say this, I’ve got to preface this by saying my wife’s from Kentucky, so there’s a difference between whiskey and bourbon. And so I would say Buffalo Trace, Pappy Van Winkle, you name which one, would be top on the list.
Rory Holland: Great choices. I’m going to throw out Basil Hayden and one more for my neighbor, Iron Wolf.
David Benskin: There you go.
Rory Holland: Our neighbor has a distillery, fantastic, award-winning bourbon. Very, very good. So when you come out, next time you come to Austin, open invite. We’ll go tasting.
David Benskin: Tasting and surfing.
Fantasy Heading Hunting and John Doerr
Rory Holland: So you had shared with me if you could hire anybody, if you could get a headhunter, find some top talent, you named someone I had not heard—I would did not have—would not have picked. Like who was it, like who would be your top pick as fantasy headhunting and why?
David Benskin: So it was a good question and I think for other, you know, executives or a lot of financial institutions, they may be very familiar with OKRs and objectives and key results. And so back to I read a book, but John Doerr is somebody, and I think for obvious reasons he’s probably, you know, one of the best in terms of venture capital—venture investing, he’s got pretty good results. But what I found is that, you know, you measure what matters. It’s setting objectives and having key results. And I think about it relative to Wealth Access, it’s easy to track, you know, financial accounts or balances. But, you know, how do you measure what really matters from a client’s perspective to them? And so I think it really ties into our business and what we’re really all about.
How to Connect with Wealth Access
Rory Holland: Yeah, awesome. That’s cool. Well it has been a pleasure, David. And before we go, how can folks learn more about Wealth Access, get connected with you?
David Benskin: Yeah, website is best, wealthaccess.com, and click to schedule a demo and connect with the team. So we’re really excited about the new website and that’s usually the best way to connect with us.
Rory Holland: Awesome. Man, it was a pleasure. So nice to chat with you. Thanks for the time.
David Benskin: Yeah, thanks Rory.
Outro
Rory Holland: Remember, at the beginning of the episode where David mentioned driving the boat so other people can wake surf? He described when something goes wrong on the lake, it’s always the driver’s fault.
Now you might feel like that’s an overstatement, but if you’ve ever wake-surfed, you know what a good driver can do – really it’s about shifting your perspective. In his 2015 book, Extreme Ownership, Jocko Willink teaches how this concept helped him navigate the unbelievable chaos and danger of wartime Iraq.
Obviously, wake-surfing and starting a fintech company aren’t the same thing as defying death in combat, but there’s a lot of important lessons that apply to both.
The truth is, we can’t control the challenges (or waves) life gives us but we can look at the situation and identify problems that we can solve. David looked at the technology and data gaps at Merrill Lynch and decided to own the problem and create a solution.
Wealth Access isn’t just helping institutions and investors make more money or cut expenses, although both of those things are true.
They’re creating an environment where everyone can see the same data and work toward common goals, strengthening outcomes for all.
If you can identify a problem and take ownership for the solution, then you and your company can wake-surf on the results too.
Thank you for listening to Mighty Finsights. You’ll find all of our episodes on our website cstmr.com, including more one-on-one interviews with fintech and financial leaders as well as deep-dive episodes on specific topics like branding and marketing. This show is produced and distributed by CSTMR, a financial marketing agency. All rights reserved. Our production team includes Zac Garver, Becky Dombrowski, Brad Jerger, Romina Gomez, and Belén Ancurio.
