Tax-Efficient Strategies for Maximizing Investor Returns with Martin Cowley

Jack Sharry: Everyone, thanks for joining us on WealthTech on Deck. Each week I speak with leaders about issues, opportunities, strategies that move the wealth and asset management, annuity retirement and fintech industry forward. We often talk about the innovations and disruptions that occur around building comprehensive advice platforms. Our guest developed capabilities and strategies to help advisors, investors and firms enjoy better financial outcomes enabled by digital and human advice. Today, I have the pleasure of speaking with a person who has innovated and contributed to the build of more comprehensive advice platforms than just about anyone I know. My friend and colleague, Martin Cowley has been immersed in working with clients day to day for the past 25 years and building better platforms. And today we’re going to discuss the five ways to achieve tax alpha, through a comprehensive advice platform. Martin, welcome to WealthTech on Deck again.

Martin Cowley: Thank you, Jack, it’s nice to be back.

Jack Sharry: So Martin, let’s start with you telling our audience about the work you do each day and the kind of clients and issues you deal with. So maybe a high level of who you worked with what you do, and how that all turns out each day.

Martin Cowley: Sure. So as Head of Product Management, I sit in the middle of several groups at LifeYield. So oftentimes, I’m working directly with my team figuring out new product features. Other times, we’re working with our development and QA groups, to just chart progress as we’re building something out. That’s kind of the internal side of it, along with our research team led by Paul Samuelson. So there’s a lot of internal stuff that happens. And then there’s the outward facing part where I’m often involved in sales opportunities with new clients, existing clients. And as our clients are going to implement some of the LifeYield functionality that I’m working very closely with them to help advise and help make sure that our software is being made the best use of as part of their system.

Jack Sharry: So basically, you’re working with folks that are building platforms, they’re ticking and tying all the different elements and pieces. So rattle off a few. So audience understands, you’re somewhere in between data aggregation, planning, proposal, ongoing portfolio management, rebalancing, all that kind of stuff, talk a little bit about sort of the role you play because the firm’s are have a lot of these capabilities. But a lot of what you’re doing isn’t really is about coordinating all those various aspects and elements and then adding our own secret sauce to make things better, right.

Martin Cowley: Yeah, so a lot of it is in understanding the setup that our clients have, because everybody’s different. There’s a lot of proprietary systems that have been built over the years. Sometimes they’ve come together as part of acquisitions. So all of our clients are completely different from each other, there may be some common themes. But the actual systems that they have, and the combination of systems that they have is very different. I’d say even that combination of functions that are trying to provide for their advisors is different. Some firms put more emphasis on planning than others, for example, others may be more keen on managed products that are run in house, as opposed to letting advisors customize. We see a lot of different situations there with a lot of different tools. So I think a lot of what I have to do. And what my team has to do is figure out in each unique client circumstance, what’s the best place to put LifeYield? We have so many different functions. Now, we have to figure out where’s the best place to start to get something up and running quickly? Where’s the best place to start for a client that’s implementing LifeYield? And where should they go next? It’s like a roadmap in its own right.

Jack Sharry: Gotcha. We’ve been hearing this term hyper personalization become the new buzzword. And we’ll get into taxes in a moment. Often it’s referring to that but beyond and is you in particular, have worked with various firms on putting it all together, issues of cost, risk, tax, social security, all come together. And so in a lot of ways, you’re coordinating those various aspects and elements of the ecosystem. I know your favorite word there, Martin, but the the idea is that you’re pulling it all together and ultimately trying to improve outcomes for clients. Is that basically what you do each day?

Martin Cowley: Yes, absolutely. There’s an end state that people might be looking for which way you’ve got all of the LifeYield functionality turned on. Everything’s tightly coordinated. Everything’s being run at the household level. But then there’s the reality of the fact that so many systems have been in existence for quite a while and they’re pretty entrenched. There’s some very mature workflows and processes that people have around managing in the vigil accounts. So we have to respect that we don’t assume we can’t assume that we can replace any of those things, really, we’re trying to build the connective tissue between these various systems to help them coordinate, as best they can.

Jack Sharry: Gotcha. So the platform is you work on at some of the biggest firms in the world, literally, the wealth management firms. And we also do a lot of work with insurance companies, we work with asset managers, we work with a variety of different types of firms, they each come at it from a slightly different angle, based on where they are in the marketplace. But ultimately, about helping the advisors be more productive and effective, and also helping clients improve their financial results. That’s fundamentally what you work on day in and day out, as we just discussed, that’s around reducing taxes, managing risk, minimizing taxes, and maximizing Social Security. So for today, we’re going to focus on taxes. And let’s start by identifying the five ways to improve tax alpha at a high level, and then we’ll get into the detail a little bit.

Martin Cowley: Sure. So the way we look at it, we’ve divided it up into five different buckets as far as how you can improve tax alpha. And any one of these can be implemented by itself. But as you implement more of them, they kind of play off each other and you get to enhance benefit. So the whole is greater than the sum of the parts, when we put these five pieces of tax alpha in place. And some of them are very widely used already, in certain respects. So one is very widely used is tax harvesting. So loss harvesting, to offset gain realization later on the taxes that will be due on realized gains. But if you look at that, historically, it would often be something that was a specific request from a client to an advisor at the end of the year, because they know at the end of the year, how their taxes have played out from trading earlier in the year. So there becomes that kind of reconciliation at the end of the year to try and negate any tax impact, and tax harvesting was used to do that still is today. Now what’s common, is doing tax harvesting on an individual account, which is definitely a valuable thing. If you do it across accounts, multiple taxable account, then you’ve got a larger pool of tax lots to pick from. So that, by definition ends up giving you more freedom, more leeway, you can be more efficient when you look at it across account. And the other aspect of it is that it needn’t be a end of year process. This can be something that happens all the way through the year, we often refer to some of the work that we do, whether it’s in tax harvesting, or an asset location, we refer to certain things as opportunistic, you’re just looking for an opportunity to arise when the market moves in a certain way. Or if a client has a cash inflow or a cash outflow, or they bring a new account across. All of those are opportunities to refine that client’s household and make improvements through tax. So we do tax harvesting, but we’d like to think of it as broader than just one account running on a clock.

Jack Sharry: Yeah, let’s talk about that a little bit. Because what are things that you deal with every day, I certainly am fond of myself and conversations. The industry is founded over the past 40 years for decades around individual accounts and individual tech products, that everything was sort of bought in a serial fashion, not terribly well coordinated a little bit of asset allocation. But often because they have two or three custodians, it’s not very well coordinated, to be honest, as you also use the everyday because you see lots of client households. So talk a little bit about the distinction between single account management in a serial fashion versus coordinated multi account. I mean, it’s a huge difference, which most people don’t fully understand or appreciate. So maybe talk about that single account management versus multi-cam management.

Martin Cowley: Sure. So in terms of single account that style Everybody’s used to, you’re working on an individual account with a set of holdings, and some people might be picking stocks. More likely these days, people are running it to some kind of model, some form of pre-selected security weights, they’re trying to rebalance to, or at least a category level asset class level weights that they have to try and adhere to. So that in itself is a product that’s a very well established and beneficial product in helping the control risk and give certain opportunities for tax harvesting. But they’re limited because it’s a silo. The single account is a silo. Now, when you think about an advisor, as soon as an advisor has more than one client account, then traditionally what they’ve really had to do was set up two separate accounts or however many separate accounts it is. They can manage those accounts in whichever way they can put different products in those accounts. So having multiple accounts says something that every client has, and a lot of advisors are already having to deal with. But there’s some opportunities there that not everybody’s taking advantage of. So I mentioned, from the most straightforward tax harvesting view, the fact that you can see multiple tax lots across more than one account gives you more room for efficiency, it gives you more tax lots to pick from putting it simply. So you can be more selective about what you pick, you can do a better job in harvesting losses and avoiding gains. But it’s not limited to that by any means. Tax harvesting, can be considered alongside asset location. And we really put a lot of emphasis on asset location we have done over the years. Asset location for the most part is, by definition, a multi account exercise, where rather than managing an account, one at a time, to some asset allocation that’s specific to that account, if you elevate the allocation are a level so that it spans multiple accounts. So if you elevate some of these asset allocation up so that it runs across the various accounts that they have, then that’s another opportunity for tax efficiency, this time through avoiding the taxes moving tax inefficient asset classes out of the way of the taxes by moving them out of taxable accounts. So we’ve put a lot of emphasis on location over the years to try and improve the after tax return on the portfolio, not just look at the pre-tax return.

Jack Sharry: Want to talk a little bit about that. Because for those that are not familiar with asset allocation, or they’ve heard about it, and they’ve heard, it’s an important thing. Why is it so important? I know the answer, obviously, but I’m curious, as you might explain it to someone who’s a little less familiar, but essentially, all you’re doing is putting the most the appropriate assets in the appropriate accounts, using basically Roth or IRAs to protect more volatile assets or more taxable assets, and then taking the longer term equities as an example, in the qualify in the taxable account. So you’re really sort of leveraging that. But I know why, why that is, maybe you can explain why the big impact? And also how does that translate into a household portfolio versus a single account.

Martin Cowley: Okay, so hello, the time when somebody’s setting a target allocation, whether it’s for an individual account, or a portfolio, there’s a focus on the return on the anticipated return. And there’s mostly pre-tax return, that goes alongside an asset allocation. And that’s perfectly fine, we look at pre-tax return as well. As soon as you actually implement a target allocation across even just a single account. If it’s a taxable account, then you have some kind of tax footprint on that account, will sometimes refer to it as tax drag. We’ll also talk about after tax return. So putting the spotlight on the return of a portfolio after taxes are taken out rather than only looking at pre-tax. And that’s very highly customized to an individual client, because their tax situations are different. They’re split between their taxable assets and their qualified assets is different. They have different products with different tax characteristics. So there’s a lot of moving parts that all go together to managing a multi account portfolio. Now what asset location is all about is say I had some equity position, I had small cap equity, and I had an allocation to small cap equity, and I needed to figure out where’s the best place to put it. So if I would have hypothetically put that small cap equity, especially if it’s actively managed, and there’s a lot of turnover, meaning a lot of gain realization in a given year, then it’s going to be potentially quite tax inefficient, a certain amount of the return is going to go out straight out the doors and taxes. If it’s highly active, there’s potential short-term gain realization that’s going to get taxed at a client’s ordinary income tax rate. So that’s an example of a tax inefficient assets in a taxable account, were given the choice, you’d try and shelter it in a qualified account where all of the growth is tax free. So that’s one side of the location coin. And another one that’s kind of the opposite side of the coin, is if I were to think about municipal bonds, municipal bonds have no tax impact assuming the state minus and so they wouldn’t be a good choice. In a qualified account, you’d gain nothing by placing them in a qualified account. If it was a tax deferred account, you’re actually incurring taxes later when you make the withdrawal. So that’s an example of something that’s best placed in a taxable account. If you If you have room, and it’s the if you have room, that’s always the problem with asset location, there’s a lot of guidance in the industry about here’s an asset class, that’s a good fit for a qualified account. Here’s another asset class, that’s a good fit for a taxable account. But when you think about every client’s taxes being different, their tax situation is different. Everybody having different accounting capacities, then it’s not as simple as that there has to be. There’s some trade-offs, and we’re big on the trade-offs, implementing those trade-offs in the simple way.

Jack Sharry: Talk a little bit about how asset location can preclude or not prevent, but will make it so that from a tax loss harvesting standpoint, you may not have to do it as much if you do the asset location properly. Explain that dynamic that interplay?

Martin Cowley: Sure. So going back to that example, where we have the active, small cap, sheltered in a qualified account, because it was tax inefficient. That tax inefficiency is largely due to the turnover of an actively managed asset class. Now, if on the other hand, I move that into a taxable account, then there are some opportunities there because if it were more volatile, and there’s, it’s being sold and replaced more frequently, there’s more trading activity, then that also means there’s the potential for more tax loss harvesting opportunities. So it becomes a balancing act, the better off placing an asset class in a taxable account to be able to make use of that tax loss harvesting as the market moves up and down. Or are you better off hiding it in a qualified account so that it’s tax free? So question of which is the more valuable. And what we generally find on the tax harvesting front is that it is a very valuable exercise, especially early on. But some of the opportunities that tax loss harvesting dissipates over time, when you think about somebody who’s got a very mature portfolio, it doesn’t really matter if the market drops, they may still be out again. So they don’t have that opportunity to harvest the losses. Whereas placing it in the qualified account, we can do a couple of different things with that we can firstly sheltered from taxes and allow everything to grow tax free. But we can also do a little bit more with tax free versus tax deferred accounts, in that we can help grow the tax-free assets and help minimize RMDs on the tax deferred by correct asset location. Now, the fact that we tend to do that means that that opportunity for loss harvesting in the taxable account is reduced.

Jack Sharry: Right, but a better impact for the client, ultimately?

Martin Cowley: Right, especially over the long term, you know, tax harvesting is good. It’s part of our our toolkit. But asset location does mitigate the need for tax loss harvesting, especially considering that it dissipates over time.

Jack Sharry: Let’s move on to talk about transitions, but keeping in mind, asset location and, and tax loss harvesting. Because there’s a dynamic nature to everything you’re describing. It’s not it’s no one thing that maybe asset location has more impact if you’re separated out. But ultimately, all this stuff works together. That’s really where the challenge and the complexity comes in.

Martin Cowley: Correct. When you’re looking at a transition. It’s another opportunity for tax efficiency, to be built into something that has the potential to be tax inefficient, liquidating a portfolio and then reinvesting from scratch is tax inefficient. Putting some controls on a transition from an existing set of assets over to a new model can be made a lot more efficient by putting controls on gain realization, and potentially breaking up the move from existing assets to a new set of assets over a year or more depending on what works for the clients and that their appetite for taxes.

Jack Sharry: Gotcha. Let’s talk a little bit about the last two rebalancing household level rebalancing and what we call retirement income sourcing. That’s really where you’re, again, you’re looking at the full portfolio. It’s not any one account of its own, but rather how they combine together. And they’re kind of two sides of the same coin terms of rebalancing and then also how that plays out in terms of income generation. But why don’t you talk a little bit about how those two come together?

Martin Cowley: Sure. So rebalancing is very well established. Obviously, what we focus on is household rebalancing. And household rebalancing can isn’t as simple as it sounds, either. It’s not just running and rebalance across a set of accounts as if they were one account. In practice with our clients, we often see an investment portfolio that comprises a lot of different accounts that are managed in different ways. We might have a hybrid portfolio that contains some You amaze it may have an SMA or two. It may have some advisor discretionary accounts. It could even have an account with the client managers. It’s a real mixed bag. So what we have done is we’ve allowed LifeYield to be used as a tax overlay across an existing set of accounts. And we can turn on as much control over those accounts as some of these somebody wants in a given scenario, we can work alongside managed accounts, were aware of the rules involved in rebalancing a managed account, we can take in the managed account models, we can even suggest models that get applied to a managed account. So downstream account, rebalancing systems don’t need to know that they’re being run as part of a household. So that’s kind of how we’ve thought about how we can add value to a set of accounts that have been managed together without disrupting things too much.

Jack Sharry: And really what you’re saying Martin is, it’s when you’re doing a household level rebalance, you’re factoring in things like tax loss, harvesting, and asset, location, and all of that. So you’re keeping the not only you’re meeting the risk profile, or the asset allocation, but you’re doing so in a tax efficient way, because markets go up and down every day. And so you’re always trying to keep it on balance, and take that to the next step. So when it comes time to start drawing an income, whether it’s an ad hoc withdrawal, or ongoing, systematic withdrawal, or your retirement income stream, talk a little bit about how that then translates to the income generation side of things.

Martin Cowley: So there’s even more moving parts when you get to that, what we look at. And we’ve done some of this for our own internal research to just prove how well asset location and tax harvesting and some of the other things that we do, how well they pan out over time. But it also is useful as a product in its own right through the API that we now offer. So income sourcing takes a portfolio, and it’s a multi account portfolio, which can have asset location turned on, it can be doing ongoing tax loss harvesting, household rebalancing can be doing all of those things. But in practice, when somebody’s running their household, they’re not just looking at their investment portfolio. They’ve got income from various sources, while they’re still working. They’ve got expenses while they’re still working. And after retirement, even after retirement, they’ve got Social Security benefits, and various other income streams from annuities and other places. So really, what we’ve done as part of income sourcing is we’ve got our core engine, which is responsible for rebalancing location tax harvesting. And then we’ve wrapped that in a process that’s able to run that portfolio over multiple years do a detailed job on tax calculations at the federal and state level, try out different strategies for Roth conversions. Look at different ways in which withdrawals can be made across the accounts. There’s all kinds of switches that you can turn on and off, then see how that pans out over time and potentially do some comparisons between different approaches.

Jack Sharry: And also RMDs, in terms of factoring that into the mix as to the timing both of for Roth conversion and RMD. What’s the timing? What makes sense, given what their income while you describe them, you know, far better than I.

Martin Cowley: Yeah. So as far as withdrawal, sequencing, none other aspects of that. And other aspects of that is Roth conversions. So Roth conversions are paying taxes. Now, ideally, in a in a low tax year, such as when you’re in that transitional period between finishing working and RMDs, kicking in on tax deferred accounts, or social security income kicking in assuming somebody’s delaying the Social Security benefits. So there’s that window where you can potentially make some cheap Roth conversions by a limited amount of tax up front, but then save big time on taxes later on, either for yourself, or to the eventual heirs of those Roth’s. So the other aspect of it is that RMDs get reduced if you’re doing Roth conversions. Even if you don’t convert the entire tax deferred account to Roth. The more you convert, the lower your RMDs are going to be an RMDs can kick somebody up into a higher tax bracket than they might want. They at least cause more tax liability than they want, whether they go into another bracket or not. So those are some examples of the kind of interdependencies between all of these topics when we’re running it as part of income sourcing over a long period of time. And one important thing that I just stressed with this. This follows the same theme that I mentioned the household rebalancing and tax all boosting asset location, we don’t assume that we’re taking over from existing systems, we were very careful in building our income sourcing product as an API, we’re very careful to design it in such a way that it plugs into planning. It helps replace planning, it becomes part of a workflow. And we like to think of it as a bridge between planning and implementation. There’s just an really natural flow. So you think of an advisor going through the planning exercise that’s pretty involved, it has certain inputs and outputs, there’s a lot of Monte Carlo simulation involved. The next step in the workflow, rather than jumping straight into implementation with product selection, is income sourcing, to then do a reduced analysis that tries out running that portfolio over some period of time. And then with different tactics turned on seeing what the outcome is for the client, the very first step of that analysis becomes the implementation step, the immediate implementation step for the advisor. So it becomes a pretty powerful story between planning and implementation.

Jack Sharry: So Martin, I’m gonna try to use a metaphor here, might be stretching a bit here, guys, Wizard of Oz, the wizard is back there moving all these dials, bells and whistles, and all that trying to help Dorothy get home, essentially, and I’m not gonna say you’re the wizard, but you’re close, you’re the closest thing we got right now. Anyway, the idea is that essentially, what you just described is Brian asset location by getting the right asset allocation in the right accounts, you can save on taxes. And as you accumulate assets over decades, hopefully, you’ll have more money, basically, you pay less in taxes, you have more money compounds to grow. So as the location was the first time you described, the second is, you’ve just mentioned it, well, we don’t do planning at LifeYield, we work with lots of planning tools. And basically we are the implementation side of what a planning tool will do. And as part of what we do at asset location, we also factor in tax harvesting. So to minimize the need for that, because it’s more efficient to do it through SSH at location. And then over time as assets are consolidated because that’s what happens as people get older, closer to retirement, they tend to want to have it in one place, largely because of administrative reasons. But also, frankly, they’ll benefit by having in one place in terms of after-tax returns. Basically, what kicks in next is the rebalancing, keep it in check, keep it the asset allocation in place while minimizing tax. So again, more tax alpha as you go, and then ultimately has to come out. And that’s when suddenly what you’ve developed and devised and implemented at many firms is an ability to look across the full house. So look across social security, look across issues around RMD, around issues of Roth conversion around all the multiple accounts that people accumulate over time. And again, your the bells and whistles and levers and dials and so forth. Essentially, what you’re looking to do is minimize tax at every step of the way. Maximize security benefits, because the government gives you raised between 62 and 70. So basically what you’re doing is looking at all the factors. And ultimately what happens is, it’s an API capability that maximizes retirement income, they capture that accurately.

Martin Cowley: Yep, maximizes retirement income also helps minimize taxes, pre-retirement, we don’t think of ourselves as purely a retirement income. It’s not purely a retirement income play when it comes to income sourcing. Although that may seem kind of counterintuitive. A lot of what we’ve learned from our early days in doing retirement income, was the some of the techniques that we put in place during retirement to get extra tax efficiency, like asset location, really worked well pre-retirement as well. And they just helped set up the portfolio for an efficient drawdown.

Jack Sharry: Well, over time grows short, and with our audience, I’m sure in rapt attention to all the ways that we can help maximize retirement income, what to share with our audience in terms of what we’ve been discussing.

Martin Cowley: Sure. So one would be I think tax harvesting is well established. And it’s a valuable exercise, but it’s made more valuable when you spread it across multiple accounts, to the extent that you can. And the higher frequency is often better to rather than it being something that’s based on the client request. Running tax loss harvesting and an opportunistic way is a great way to do it. And that definitely builds tax efficiency. So that would be number one. Number two would be asset, location. Asset location is a tricky thing to implement. There are a lot of guidelines out there as to how to implement it and what a good asset classes to place in different account types. But as soon as you get into the weeds of a client portfolio, where they’ve got different tax rates, they’ve got different accounting capacities and potentially different investment preferences. is certainly different risk levels, then it becomes more difficult to put into practice. So it’s really powerful across multiple accounts, because of the ability to increase after tax return, really minimize those taxes, not just pre-retirement, but in retirement as well. So that’s the second point I would make. And then I guess the third one would be really what we were just talking about around putting it all together. So whether it’s tax harvesting, portfolio of or rebalancing, where I mean, across accounts, asset location, bringing accounts, bringing new assets across with a tax efficient transition, and then running income sourcing in an efficient way, where it’s thinking about different tactics to help save on taxes, and boost bequest goals and boost income goals. All of these things play off each other. And it is important, we think, certainly, I think, to have that income sourcing role is something that sits between planning, and execution, a lot of people have planning, a lot of people have execution. And that little bit in between the two is sometimes a bit fuzzy. So that’s really where we think there’s a lot of power in income sourcing. As an API.

Jack Sharry: We haven’t mentioned it explicitly, but I’ll just underscore the fact that taxes are the single biggest cost an investor incurs over the course of their lifetime, and more than all the rest combined. So taxes matter. I’m interested to hear what you’re gonna say this time around. You’re a man of many talents and many interests. So as we do each week, my favorite question, which is what is something you do outside of work that you’re excited or passionate about, that people might find interesting or surprising? Tell us about this.

Martin Cowley: I think about hobbies. Because I do have a lot of hobbies. One that I spent a lot of time on over the last 10 years or so, is karate. I did it for a couple of years at college in England and let it sit for 20 years, I think, before my daughter ended up getting invited to a friend’s birthday party that happened to be at a karate dojo, just north of where we now live. And so I got roped into it, got on the mailing list. And then I thought, okay, rather than taking my daughter to the class, I’ll participate in the class. So now 10 years later, I’m a second-degree black belt going for my third degree. And I do a lot of teaching. When you get to the more senior levels, it’s less about the technical aspects of karate for yourself. And it’s more about passing it on to other people, which is really satisfying thing when you you’re teaching somebody something that’s pretty precise. So yeah, that’s, that’s the other thing that nobody knows.

Jack Sharry: Well, I am not surprised. You are a man of many talents, certainly around what we’ve described here on the podcast, but also your classical baritone, and your black belt, karate. There’s probably five other things we haven’t covered. But again, it’s really been a pleasure to spend this time with you. Thanks for your insights and perspective for our audience. If you’ve enjoyed our podcast, please rate review, subscribe and share what we’re doing here at WealthTech on deck. We are available wherever you get your podcast. Thank you again, Martin. It’s been a lot of fun.

Martin Cowley: Thank you, Jack. I appreciate it.