Live From New York: A Special Episode on Fintech Innovation



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Jan 5, 2023

Live From New York: A Special Episode on Fintech Innovation

This special episode of Crafted was recorded live at Rise, Created by Barclays, an incubator for fintech startups. In this fireside chat, we speak with Ainslie Simmonds, President of PershingX at Bank of New York Mellon, and D. Orlando Keise, head of Banking Foundational Platform at UBS. Ainslie is building a modern wealth management platform and D. Orlando is building a digital bank from the ground up.  We’ll discuss what it takes to innovate at big financial institutions and hear their advice for fintech startup founders.

Here’s D. Orlando Keise and Ainslie Simmonds on Crafted, Artium’s new podcast.

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D. Orlando Keise: It’s not often that at a bank you get the opportunity to really look at things greenfield, and that’s what we’re doing. We’re looking at the question of how do you build digital banking solutions, and you’re almost 2023, and saying if we were going to do that the way that you would want to do it from scratch, what would that look like?

Ainslie Simmonds: So four months later, they came out with, “Daaaa,” this architecture diagram, and I sat there, and I was like, “Are you freaking kidding me? It just takes these three things to make this whole thing work?” And they’re like, “Yeah, we think so.”

Dan Blumberg: Welcome to a special episode of Crafted, recorded live from New York at Rise, created by Barclays. Rise is an incubator for FinTech startups and hosts amazing events, including the one you are about to hear from Artium.

So joining us now are Ainslie Simmonds and D. Orlando Keise. Ainslie is the president of Pershing X at Bank of New York Mellon. Pershing X is an innovative new wealth management platform for BNY Mellon’s clients, including broker dealers, registered investment advisors, and trust companies. Previously, Ainslie was the global head of digital at PIMCO, and she’s held top product and marketing roles at major financial institutions and startups, including LearnVest, which we’re going to talk about. And she started in the CPG space at Campbell’s Soup and Molson Coors. Please join me in welcoming Ainslie Simmons.

Ainslie Simmonds: Thanks.

Dan Blumberg: And D. Orlando Keise has spent his career leading technology teams in FinTech. He’s built everything from marketing experimentation platforms to trading systems with billions of dollars in transaction value. He’s got extensive experience at large financial institutions and startups, again, including LearnVest, as well as proptech startup, TheGuarantors, and insurance startup, Wellthie. Today, D. Orlando is the head of Banking Foundational Platform at UBS, where he is building really cool stuff, some of which he might maybe be allowed to talk about. D. Orlando, thank you so much for being with us.

D. Orlando Keise:  Absolutely.

Dan Blumberg: So I’m really excited to have you both on stage. You’re both building very ambitious things at very big financial institutions. You both have startup experience, big company experience, and startup at a big company experience. And in this session, I’d love to discuss what it means to work and innovate in those contexts. Before I get there, I wanted to start with a little warmup question. Ainslie, this is for you to start. It’s a bit of an odd setup. It’s one that listeners of Crafted may recognize from our very first episode. It goes like this. You game?

Ainslie Simmonds: Ready.

Dan Blumberg: All right. So I love how blog posts always have these really grandiose titles that always have a little bit of a switch in the headline. So I’m going to give you the title of a blog post that you’ve written, and then you can write it for us. Don’t worry. You got this. Here. You wrote this. “Everything I needed to know about building financial products I learned selling Campbell’s Soup.”

Ainslie Simmonds: Oh, that’s not even hard. So it’s been a really interesting wild ride over the last number of years in my career, because when I started at Campbell’s Soup Company, I worked in product management. That was what it was called. And you thought about building PnLs, and you thought about product definition, and you did a lot of customer intimacy, and a lot of data and analytics. Does any of that sound familiar? So it was sort of the OG product management happening in the real world.

And then when digital happened, what was so fascinating and why it was so fun to just make the jump, everyone asked me, “How did you make that jump?” It was literally the same job except better, because now you can measure everything. So I remember Campbell’s Soup days, you used to have to pay for data that was six months old, blah blah blah. And now the Internet, you get it in four hot seconds. So it’s the same stuff, it’s the same skills. It was a super easy switch. I think if you’re ever looking to hire product managers, it’s a good place to go find people still.

Dan Blumberg: Orlando, how has not selling Campbell’s Soup held you back? 

D. Orlando Keise: Well, I didn’t know before now, but now I realize.

Ainslie Simmonds: Did you not know that about me?

D. Orlando Keise: Well, I didn’t know how it would‘ve helped me to … Yeah.

Ainslie Simmonds: Oh, how it applied. Gotcha, gotcha.

Dan Blumberg: So these two know each other well, because they worked together at LearnVest. We did not plan this. This was a surprise.

Ainslie Simmonds: It was a total surprise. I was like, “Wait. That guy?”

Dan Blumberg: And so they were both at LearnVest, both before and after its acquisition by Northwestern Mutual. D. Orlando joined just as the acquisition was sort of in the works. And so the acquisition was a big deal in the FinTech world, a big deal in the New York startup world. And I’d love to get to what you all are building today in a moment, but first, I would love to go back to around 2015 and the years just before and after the LearnVest acquisition. And just for those who don’t recall, LearnVest’s mission was to democratize financial planning, especially to make wealth management more accessible and approachable to women. Northwestern Mutual bought it for $250 million in 2015. About three years later, though, it effectively shut LearnVest down and later relaunched it, but it’s mostly a small content site today.

And D. Orlando, I wonder if you could start just by sharing one story from pre and post. I guess you joined just as the acquisition closed, so maybe as the culture was changing, one story that felt more like the original and one as it was changing, and Northwestern Mutual was making its presence known. And more importantly, if you could share how those stories impact how you think about innovating at your own large financial institution today.

D. Orlando Keise: Yeah, for sure. A big part of any time you’ve got an acquisition like that where there’s a larger company and a smaller, more nimble, faster moving company, a big part of the motivation behind that is people and the way that the people work. In LearnVest, we had what you’d imagine as a New York tech startup, we moved fast, we were agile, small-a agile, we lived it, breathed it. A large company that acquires a company like that is trying to be that. There’s a thing where larger companies are trying to become nimble and agile, and smaller companies are trying to be more process-oriented and grow up. So in the early days, again, I landed just as it had happened, but nothing had really changed yet. We were exactly that breed of animal where we were able to get people around a desk and solve some problems, innovate organically.

And I think as the acquisition became more and more real and we started to interact with more and more of our counterparts from Milwaukee and get to know our new partners more, a big part of it was teaching our partners how to operate in the same way. There were a lot of opportunities to educate a new way of doing things. You’ll find some folks that are naturally acclimated to that and some folks, it’s a little harder to make that shift, but that’s a big part of what the change really is, teaching folks how to work in that agile way.

Dan Blumberg: You want to take that as well?

Ainslie Simmonds: Sure. I was at LearnVest really early days, I think right after we raised the A, maybe right around the B. I can’t remember. I think it was like 12 people. So when Northwestern Mutual acquired us, we were probably about a hundred, and that’s a very small team in the sort of behemoth of Northwestern Mutual. It’s a very, very large company. I think stories to tell is you have to start to really understand, I think it’s really important if your company ever gets acquired, hopefully it does, if that’s what you want, it’s really important to understand what’s their business, how do they make money, because you’re going to get pulled in that direction, period, no matter what it is. So if you don’t know that, please do know that, because your company’s going to go there.

And for us, Northwestern Mutual is one of the biggest providers of what’s called permanent life insurance. It’s sort of a product where it has an investment component and a life insurance component, and that was a massive cultural change for LearnVest, because LearnVest was trying to help people democratize finance, and so the best insurance product is a much cheaper version called term insurance. It was the craziest, at the heart of the company belief that term insurance was the answer for everybody, and at the heart belief for Northwestern Mutual that permanent life insurance was the answer for everybody. So there were a lot of conversations about that, and it took a lot of time and energy and effort to educate on both sides and kind of find the middle ground. But I would just say the gravitational pull is always going to go to where the acquirer makes money.

Dan Blumberg: So I’d love to talk more about what you’re building today, and I imagine there is education that you’re doing today with your colleagues in different areas. So maybe you could start, Ainslie. Tell us more about Pershing X and what you’re building.

Ainslie Simmonds: So if you don’t know much about how financial advisors work today, they essentially use about 8 to 12 tools to be able to give you what you need. So they have to fire up a financial planning tool and a portfolio construction tool and a trading and rebalance tool. I can go on. There’s 8 to 10 of them, and with all the FinTech money that’s coming into the space, they keep acquiring more tools, number 11, number 12, number 13, and it’s really become a massive problem, because nothing connects. You, as a client, you need it to see the full you, and they needed to see the full you.

So what we are building is a platform to connect financial tools for advisors, so we’re calling it an operating system. And what that requires in finance is a data layer that normalizes all the various ways in which financial data gets expressed in the market, and there’s many different ways. You’re talking about crypto and digital assets, just one asset class, you’ve got bonds, you’ve got stocks, you’ve got ETFs, you’ve got mutual funds, yada yada. Everybody does everything a little bit differently, so you have to do this sort of normalized data layer. We have to have an operating system, which is what we’re building. We’re also building the data layer.

And then to really make money, we’re talking about the little dirty secret in finance, you also have to provide the applications and the investment products that go in it. So if you sort of think about it as layers of a cake, you’ve got the data layer, you’ve got the operating system layer, you’ve got the application layer, and then you have the financial products layer. You mentioned ambitious. I don’t think this could be done if we didn’t have the kind of long-term funding and commitment we have from the Bank of New York Mellon, because to simultaneously hit all of those things and have them all be orchestrated is near impossible. It’s some pretty fancy footwork. So that is what we’re working on. We’re about a year in. We have about 500 people already working on it.

Dan Blumberg: Orlando, the foundational layer, foundational is in your title at UBS, can you talk more about what you’re doing there and how you think about building platforms?

D. Orlando Keise: Sure, yeah. I can talk a bit about that. So obviously, not breaking news. UBS, we have high and ultra-high net worth clients as our wheelhouse. So in short, what I’m doing is I’m part of a team that’s building a digital bank for those clients. Now, as the Foundational platform, the part that I’m responsible for is really the central nervous system of that digital bank. All of the parts of that system talk through the piece that I’m responsible for. You asked about how do you that, how do I approach building solutions there at a large organization like this, and interestingly, it’s the same game when it comes to actually building good software. At the end of the day, no matter where you are or what the context is, it always comes down to building an appropriately representative model of something in the real world. That’s a big part of what it means to build a foundational platform correctly.

It’s modeling the domain, all of the things that our clients need to do, making sure that that model is, again, sufficiently accurate so that we’re able to just reduce friction in what those clients are trying to do. I think a big part of what we’re solving for today in FinTech is what we were doing yesterday and what we’re going to want to do tomorrow. The path that we’ve been on is about reducing friction. The technology, if you do it right, it should seep into the background. It’s about getting out of the way of what they want to do and make sure that we’re providing those experiences.

Dan Blumberg: That echoes back to the conversation Jamiel and I just had. I imagine both of you are building on COBOL, right?

Ainslie Simmonds: Yeah, absolutely.

D. Orlando Keise: Yeah.

Dan Blumberg: And I mention that, because banks, the post office, they all run on this code from the 1970s, and I’m curious. I imagine you’re not building on COBOL, but I imagine it’s related, it’s there, you deal with it in some cases, I’m sure. Can you talk about how those legacy systems, whether they’re on COBOL or whatever the legacy system is, how they’re holding us back? I’ll start with you D. Orlando. As you’re thinking about building a digital bank, how that underlying infrastructure, what’s really important as you build that?

D. Orlando Keise: So that’s a helpful question, because it’s teeing up an opportunity for me to say we are not doing that. It’s not often that at a bank you get the opportunity to really look at things greenfield, and that’s what we’re doing. We’re looking at the question of how do you build digital banking solutions in, well, almost 2023, and saying if we were going to do that the way that you know would want to do it from scratch, what would that look like? And then let’s solve that problem, instead of being constrained by any sort of limitations of the past. We are famously tightlipped about what we’re doing, so it makes it hard to talk about that. But anyone who’s interested in solving that kind of problem, please find me and talk to me, because we are doing something that you don’t often get a chance to do in the industry, and it’s very exciting.

Dan Blumberg: Can you talk more about the interoperability. I know it’s one of your favorite words. Maybe you can talk about how the platform infrastructure leads to that, what you were talking about a second ago, the financial advisor has 8 or 12 different apps that need to talk to each other, need to have a singular view of the customer, and how the foundational layer is so critical to that.

Ainslie Simmonds: You can imagine as you’re trying to get really complex financial applications that have to cover someone of modest means to folks that you cater to, ultra-high net worth, the ways they think about it and view and what they need in their money are very, very different. So I would echo what a lot of D said. You have to really map it and you have to really think about it. I used to say I was embarrassed to say, but now I’m kind of proud to say we hired a few really smart data architects and put them in a room for four months, four months, four months. And you think about that burn, and you’re like, “You’re still in there, right? Oh, Jesus.”

But they came out with an incredibly elegant solution, and the reason they were able to do that is they could go pull custody data, they could pull banking data, they could pull client data, and they could put it all together and then say, “How is it not talking to agile? How is it not working? Where is it broken? Where are the holes? Why can’t you mash this together? What are the things that stop it?”

And so as a sort of startup in the bank, we have access to just go pull any of that. We can go ask anybody, and just be like, “Oh, I want to see your liquidity data, I want to see your whatever.” You can just get it all, and you get it and you stick them in a room and you now say, “Okay, if we were to try and build this for scale, what are all these themes and problems, and how do you fix them?”

So four months later they came out with, “Daaa,” this architecture diagram, and I sat there and I was like, “Are you freaking kidding me? It just takes these three things to make this whole thing work?” And they’re like, “Yeah, we think so.” And I was like, “Okay.” So now, we’re validating all of that, and we’re really putting it to task and see if this really can happen. But I don’t think you have the opportunity, just like D said, to do that very often in your life, where everyone’s like, “What do you need? Call me. What kind of data do you need?” And then you get to shove people in a room and just let them burn cash and then come out with an answer.

Dan Blumberg: How’d you set that data team up for success? What did they go in … I imagine they understood from you the goals of Pershing X, did they have designs? How were they structuring their time?

Ainslie Simmonds: I just said, “If we wanted all this to talk to each other, what would you do? You’re smart.” And then they were like, “Well, let me think about it.” I was like, “Okay.” And they thought about it, they really thought about it, and they really, really thought about it. And I think those opportunities to really take a step back and go, “Wait, this whole industry has all these things doing all these things, crossing all these wires.” I describe it a lot like the industry’s grown up almost like you imagine a ’50s switchboard. People are connecting shit to shit, and it’s starting to cross over. If you just get a chance to step back and go, “If it wasn’t a switchboard, how would this sucker work?” I think those are fun. That’s fun. I find that fun.

Dan Blumberg: The switchboard, in this case, is a financial advisor sitting in a swivel chair going, “And this and this and that.”

Ainslie Simmonds: Yeah, and if you really get those moments to be able to step back and go, “Well, if it wasn’t like this, how might it be?” And then you can really pull all the use cases and pressure test it. We had a million, billion client conversations, “If we did it this way, if we did it that way,” and that’s fun. It was fun for them.

Dan Blumberg: Yeah, the singular view of the customer, as well. I was working most recently at Citi Ventures doing work in wealth management, that was a constant theme to not have the data and not be able to see they have this credit card and this account and this account and their kids have this and there’s this trust, et cetera. And one of the things that surprised me about working, my career was largely working in news and media and then more recently in finance and consulting now, and one of the first things that I experienced really deeply at Citi was working in a regulated industry for the first time and seeing how many parts of the bank were set up in a way that kind of make you go big.

Like the approval process, if it takes 15 approvals to get anything out the door, why would you bother with a small thing? If you’re going to go through 15 committees, you might as well go in with a big thing, because it’s still going to be 15. Or on the tech side, if there are not frequent deployments, why would you waste a small thing if you’re not going to get a chance to iterate on it quickly? I’m curious if that rings true, and if so, how you have dealt with that at your respective institutions. Maybe you could start, D. Orlando.

D. Orlando Keise: Yeah, it absolutely rings true. It must ring true to anyone who’s spent time in the bank, I’m sure. We are actually doing a pretty good job of changing that. We’ve undergone a shift to Agile at the bank, and this is actually one of the things that my experience in other environments is helpful, because I both know what it looks like when you do it correctly, as well as having been in a big bank before, even pre-Agile, before anyone was saying the word Agile. I also know what the natural state of being is for that organization. Trying to bridge the two is important.

We had a rollout process where we introduced it to people, who have been operating in a different way, and some of those folks have read the Agile Manifesto, and they’re looking at the Agile Manifesto, and it’s this short document, comparing it to what they’re hearing about how we are going to do Agile. And some of the folks, well, some embraced it, and then some are being a little bit less constructive by comparing the two and saying, “Oh, well, the Agile Manifesto is just this one little thing. Why do I need to have all of these steps and these prescriptions that you’re telling me about how we are going to do it?”

I actually think there’s a reason for that. As you’re trying to make a big organization that hasn’t worked in that way, work in that way, there’s more to it than just the little Agile Manifesto. The example that I gave this person, I tried to coach them afterwards, is I said, “All right. Think of the US and all of the laws that we have. The Constitution is a very short document. You can carry the Constitution in your pocket. You can’t do that with any of the legislatures. You go to any given state, and it’s a very big book.”

So there’s the principles, and then there’s how do we establish some sort of processes and culture that lives those, that is still compatible with all the things you have to do in a regulated entity. And then I also try to provide guidance that just as an individual practitioner on the ground, use the fact that you understand the principle and just live that. You don’t have to leave your head at the door. There’s a way to do both.

Dan Blumberg: Ainslie, are there examples of how you’ve helped push through things or change processes that had more of a 10 years ago or farther ago mentality to them?

Ainslie Simmonds: Yeah, I just try and ask myself is this reasonable or is it stupid? So one of the things we did is move a division of the bank into Pershing X to get it seated. It was a data division, and it gave us a lot of what we needed to start. And there is a bank requirement that because it was a named division regulated by such and such an entity, we had to have a board. And I was like, “Cool, we have to have a board. How many people do you have to have on the board?” And they go, “What do you mean? There’s 15 people.” And I said, “No, the absolute bare minimum, the number. Is it one?” And they’re like, “No, it actually has to be two.” I’m like, “Cool. Two it is.” So we took a board from 15 people to 2 people, it’s me and the finance guy. We meet for about 15 minutes, we sign the documents, and we’re good to go.

I’m trying to respect the bank in that there’s a regulatory reason why this thing has to have a board. Cool. It doesn’t have to be what the bank thinks it is to hit the regulatory requirement, so let’s just size everything. Is it useful or is it stupid? Well, it’s useful, if we didn’t have that regulation. If we didn’t have that requirement, we didn’t have that regulation, then maybe I could get rid of the board, but you know what? We’re regulated into it, we have a requirement, we have a regulation, so let’s just live the rule, but let’s cheat it a little bit. Not really a cheat. We’re still a board, we might be three people now, but it’s that kind of …

I always tell my team to just try and hack it if you can. You don’t have to be dogmatic. You can find the hacks, and we’ve done it in procurement, we’ve done it in approvals, we do it in all kinds of places, and it’s sort of fun. It sort of brings the team together. People are like, “How can we hack this?” I was talking about we have to take all this education, obviously, as a regulated entity. I’m like, “Do you know if there’s a test-out option?” And everyone was like, “Yeah.” I’m like, “Oh, I’m testing out of all these things if I can.” And we do. We have a contest now on who can test out the fastest. So you still have to know the content, you’ve got to get the 80%, but you don’t have to sit through the whole training. I think it kind of brings us together as a little bit of hack-the-bank a little bit.

It’s still in a very respectful way. We do respect. Listen, we’ve seen the downside of things not being regulated. Hello? And we’ve seen it not just in crypto but in real world too. I look at the fines Robinhood has paid for acting a little to the side of the regulatory environment. They’re there for a reason. People do shit. And so I like having the safety of it wrapped around what we’re doing, and I like smart people saying, “You know what? When you hit scale, this is going to fall over.” And I like having that expertise. So anyways, it was a long story.

Dan Blumberg: I love how you use a door-in-the-face technique or the anchoring bias of if you say a number, people anchor on the number, even if the number means nothing. Like if I say $75 million, and then I ask you how much is your house worth, they’ll give me a higher number. Then [inaudible 00:27:17]

Ainslie Simmonds: I’ll say the board of one. Is one okay?

Dan Blumberg: Yeah. So you said one, and they said okay, how about two? And you said cool. Right on. You mentioned Robinhood just now, so I’ll go to this question. Democratizing finance or giving regular people the tools that the wealthy have long enjoyed is a very common mission among consumer FinTechs. I literally met someone today when I was working here at Rise who was working in that vein. It’s similar to what LearnVest was doing. These startups are often not profitable, and one reason is that delivering sophisticated financial advice is just expensive, especially when it involves humans. And so I’m curious if you could just give advice, we’re here at a FinTech incubator, if you could give advice to builders in the space on where you do see opportunities to democratize finance or bring the tools of the ultra-wealthy down to the rest of us, but also do so in a way that creates a sustainable business model. That’s a big question. Whichever one of you wants to take it first, go for it.

D. Orlando Keise: I’m definitely leaving that one to Ainslie.

Ainslie Simmonds: Oh, man. Thanks, man. Well, there’s two ways to make money at the core. You can save it, or you can earn money on your money. Or I guess you could start a startup and have a really lovely accent, but for most people there’s two ways to make money, you save it or you start making money on your money. What I would say is the financial services industry, the profit, the real money isn’t making money on your money, it’s investing. That’s where the money is.

The problem is when you don’t have enough money to invest, you’ve got to learn how to save, and that’s really hard. Consumers don’t like to save. We’re not really good at it. Nationally, our savings rate is terrible. We are essentially negative savings. The pandemic has actually made us savers. We were a 6% saving nation at that time, but not anymore. And so if you’re a FinTech trying to get people to save more, know that it’s really hard, and there’s not a lot of money.

So what I would say is if you can create a balanced product where you are probably losing money teaching people how to save, but you can get people to save enough that you can start making money in helping them make money on their money, you have a nice balanced product. What I see is people either end up in one or the other. They either end up in a saving app, “I know. Let’s make a budgeting app.” Okay, cool. Good luck with that. The budgeting world is really, really tough. It’s not fun to save money. It’s really freaking hard, and that’s where I think Robinhood actually had an insight and Acorns has an insight. They’re trying to micro-transact you into saving. And there’s other ideas there, too. I’m not trying to poo-poo all those savings.

But savings on its own is a very, very hard business to build. But if you can get people to save in their retirement first and then outside of their retirement second, you can actually build a really nice balanced business that can grow really, really well. After 20 years of watching this whole industry, you need a couple of hundred thousand dollars to make money in wealth as a wealth provider, and it takes a lot of work to get your first couple of hundred thousand dollars saved. So it’s that balance that’s really, really hard, and anyone who can crack that nut, I’d invest.

Dan Blumberg: Do you want to take this question, or you want to …

D. Orlando Keise: No notes.

Dan Blumberg: Okay. I think making college less expensive might be one major way to help people save, but that’s a whole separate issue.

Ainslie Simmonds: I said what people can do. I’m Canadian, so there’s a few things that I would potentially suggest that we would change, politely suggest with an A attached that we would change. It is a very different life for people that spend $10,000 to send their kids to college than $300,000. And that’s why the Swedens, the Canadas, I’m not going to even touch healthcare, because I know lots of people have lots of things to say about that, but sort of sponsored education is a big freaking deal, and it changes a lot of lives. It makes the nation smarter and people able to get there faster. But I’m not here to talk politics in the US. I just became a US citizen.

Dan Blumberg: Congratulations.

Ainslie Simmonds: Thanks, man.

Dan Blumberg: I’m curious where you see, you spoke a little bit about, you mentioned Acorns. They did really smart things around automation. They round up. You spend 62 cents, and they put 38 in your savings account, or you spend $3.62, and they rounded up to the nearest dollar. And I think there’s a lot of interesting things happening in automation. A very famous study is getting people to, when you start a new job, your 401K is automatically opted in. You have to opt out, and that’s had a massive impact.

Ainslie Simmonds: That is magic. That is magic. Amen to that.

Dan Blumberg: So I’m curious where you see more opportunity for automation, and you serve financial, you both work with companies that are really serving financial advisors, where you see the automation will never replace what the human financial advisor can do.

D. Orlando Keise: I guess my two reactions to that is that on the one hand, I think you’re right to highlight just the power of the automation. It’s not even just the automation, it’s the making you not have to think about it. That’s the part. How many people think that what they make is what they’re actually taking home in their paycheck, as opposed to actually looking at the gross and then looking at all the deductions and then doing calculations and decisions based on that. You just say, “All right. That’s already gone. I forgot about it, and now I just start from here.” So if you can do that to your entire economic strategy for bettering your financial security, then that’s huge.

I think in my personal experience, the challenge when you start talking about financial advisors and trying to apply it to that domain is that’s a different business. They actually are each bringing their own expertise and ideas and even specific things about the relationship between that specific advisor and that client, and it’s very meaningful. I don’t know how to intersect those. There may be a way, but it seems to me almost orthogonal in a way.

Ainslie Simmonds: Well, that’s where I might disagree with you, because I feel like I’ve seen a little bit of the future in … We just did a strategic partnership into an equity stake in the new financial planning company that hasn’t been in the US before, called Conquest Financial Planning, and this isn’t a commercial for them. But the reason I partnered with this one is because it’s the first financial planning application that I’ve ever seen that did that. What they do is they sort of take all of the possible things you could do with your money, and they use AI to serve them up to the advisor. Whatever your retirement goal is, the probability of you getting there would go up if you did these 20 things, and the AI just serves them up, right down the list, boom, boom, boom. And then what the advisor does is sit there with the client and go, “Would you do that one? Are you willing to do that one? What about that one?” And if the answer is yes, it goes on the right side, and then that now becomes the plan.

Things like that, the financial advisor could probably name 12 of those off the top of their head, but they probably can’t name all 25. They don’t know every single possible strategy that you could possibly pull off to do this thing, but the computer does, and it just goes, “Burp. Here they are.” And then the advisor sort of does that magic thing that is human that says, “Would you be willing to reinvest your tax return check or you buy-in some,” and you’re like, “I could do that. I’d reinvest my tax return check.” Cool, cool. That goes on the right side. I actually think that is where the future is. The computer sort of serves it up, and the advisor hits the ball with the client, and you get that agreement, you get that buy-in.

That’s always been I think what advisors have always wanted to do, but the financial world has gotten so complex. How can you know those 26 things? Good God, you can’t keep them all in your head, and especially for every different client type, you’re different, you’re different, you’re different. But surprisingly, your demographics do describe a lot of your life, sorry. So the computer just serves them up, and I think it’s possible. I think we’re getting there, I think AI is helping us get there.

Dan Blumberg: That actually leads right to my last question, which if you look at wealth and banking 10, 20 years in the future, what do you think is largely the same, similar to today, and what is going to be radically different?

Ainslie Simmonds: I’ll go first. I think what’s going to be the same is it’s a human business. I think what is going to be more different is the computer will help more. I think we’re just early days at what tech can do to make financial decisions easier. You talked about less friction. I just think there’s so much more to do. I think the industry’s really messy right now. We’re talking about eight apps to solve a problem. That’s crazy pants. So I think it’s going to move and it’s going to move fast, but humans are going to be there. I believed it my whole career. Everyone asked me, “Are the robots going to take over?” No, not a chance. Money is so human. Try and have a conversation with your spouse about money. It’s human.

Dan Blumberg: Orlando, I know you can’t talk in too much detail about it, but how are you building the platform that you’re building to be future-proof, so it’s ready for all the things that Ainslie’s talking about?

D. Orlando Keise: Yeah, yeah.

Ainslie Simmonds: You just did a mashup of us.

Dan Blumberg: You like that? It’s like a Benafer.

Ainslie Simmonds: That was great.

D. Orlando Keise: Great question. So I guess a couple things come to mind. The first is by just letting ourselves be untethered to a solution that’s dated and saying, “All right. How do you solve this problem that we’re trying to solve? How do you solve that today?” It means making very fundamentally different decisions at the core, at the foundation of the thing that we’re building then, which is why I’m glad to be at the part that I’m responsible for. And then, I think I actually agree with a lot of what Ainslie said.

Ainslie Simmonds: You know what? First time ever. Sorry. I was kidding.

D. Orlando Keise: No, I think there is a lot of opportunity to build technology that makes the thing that you were trying to do easier, and that reduces the time it takes to do that thing. I think a big part of what we’re doing when we’re trying to build software solutions at the bank, even in previous organizations, my previous FinTechs, it was literally the same game. We were making this thing that maybe took you a week to make it take a day. Right? So that’s a big part of it.

Dan Blumberg: Awesome. Thank you so much for joining us.

Ainslie Simmonds: Thank you, guys.

Dan Blumberg: That was Ainslie Simmonds, President of Pershing X at Bank of New York Mellon, and D. Orlando Keise, head of Banking Foundational Platform at UBS. Coming soon, we’ll bring you another great conversation from our live event at Rise, created by Barclay’s. We had a fascinating conversation with Jamiel Sheikh, who has founded three crypto companies, including Instamint, which he says will do for crypto tokens what Stripe has done for payments, that is make it incredibly easy.

Jamiel Sheikh: Doing tokens is complex, it’s complex work, it’s expensive. We just are focused on making it super easy.

Dan Blumberg: We’ll have more from Jamiel soon here on Crafted, a show about great products and the people who make them from Artium. At Artium, we build incredible products, recruit high-performing teams, and help you achieve the culture of craft you need to build great software long after we’re gone. We artisans love partnering with creative people to build their visions of the future. If you’ve got an opportunity you’d like to discuss or just want to learn more about us, check us out at or drop us a line at

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