082 | Former Goldman Sachs Insider Reveals the Smart Way to Use Insurance with Wallis Wilkinson Tsai

Patrick: [00:00:00] Have you ever felt like the world of insurance is designed to confuse more than to clarify pushing products instead of delivering real solutions? Welcome back to another episode of the Vital Wealth Strategies Podcast. I’m your host, Patrick Lonergan, and today we’re pulling back the curtain on a part of financial planning that’s often misunderstood and massively under leveraged by high income entrepreneurs.
My guest is Wallace Wilkinson, Sai, former Goldman Sachs investment banker, hedge fund investor during the 2008 financial crisis and now co-founder of Above Board Financial, where she helps clients turn insurance into a powerful tool for protection, tax strategy, and legacy planning. In this episode, we tackle the uncomfortable truths about how insurance is usually sold and why that outdated model leaves so many business owners, underprotected and misinformed.
Wallace breaks down the real role insurance should play in your overall wealth strategy from shielding against [00:01:00] catastrophic risks like disability and long-term care to using life insurance for tax-free retirement income, buy sell agreements, executive benefits, and even estate tax reduction. If you’ve ever wondered whether you’re truly using your insurance to its fullest advantage, or if you’ve been pitched a policy that made your stomach turn, this conversation will give you the clarity and confidence to take control.
Stay with us to the end as Wallace explains how high net worth families are using tools like irrevocable life insurance trusts, survivor life insurance policies and private placement life insurance to build wealth tax efficiently and preserve it across generations. And if you’re ready to stop guessing and start strategically designing your own tax savings roadmap, head over to vital strategies.com/tax.
That’s where we help entrepreneurs like you build smarter plans with clarity. Confidence and powerful savings baked in. Let’s dive in. I’m excited about this conversation today. We are going to talk about [00:02:00] insurance, and, uh, sometimes that’s not a, a very exciting topic, but we’re gonna dig into the nitty gritty.
And today we’ve got Wallace Wilkinson si with us, and we are going to, uh, get into all of the, the insurance opportunities out there. And the cool thing is, is Wallace is a former Goldman Sachs investment banker, uh, also teaches at Harvard Business School. And so I’m excited about this analytical approach to insurance and how it, uh, is going to apply to, to you as the listener.
So Wallace, thank you so much for joining us here today.
Wallis: Thank you for having me.
Patrick: Yeah, I am, I’m thinking about the listener and they’re looking to build a financial strategy and they know there’s, there’s potential catastrophic risks out there. Right. You know, I. I could pass away unexpectedly. You know, unfortunately, I had two college roommates that passed away when they were 30 years old, within six months of each other, like unexpectedly.
And it was like, it sort of reset me as the, the risks that were out there. Um, it could be disability, it could be, [00:03:00] you know, uh, any number of factors. And so I’m, I’m looking forward to, uh, to, to getting into this, uh, discussion about insurance and your approach. ’cause I personally feel, and we’re in the industry, um, that when you start talking to an insurance salesperson, it feels, it doesn’t feel good.
I don’t like the way it works today. They’re financial interests seem like they’re in opposition to mine. So thank you so much for, uh, uh, being a part of the conversation today. So I’m, I’m thinking about the, the problems of insurance as, as a consumer. Okay. I think there’s this external problem of, I know there’s these risks out there.
I’m not sure how to evaluate those risks. And you know, I’ve always got this tension between, we’ll call it Dave Ramsey, who says, you know, buy term and invest the rest. And I think there’s probably some truth to that in the right situation, but there’s also, um, there’s also the financial aspect of life insurance or insurance products in general that, uh, the [00:04:00] math just works and it makes sense to have insurance in the right scenarios.
Then philosophically, I, I touched on this, but buying insurance, the process just doesn’t feel good. You know, it, it feels like there should be a better way, and I, I feel like you do a great job of bringing that to the marketplace. So I’m looking forward to getting into that here today. So. Before we do that, can you give us a little bit of your background and, and how you, you went from Goldman Sachs and, uh, to being in the, the insurance marketplace?
Wallis: Sure. So as you mentioned, I started out as an investment banker at Goldman Sachs, and I was in the financial institutions group, so our clients were insurance companies, banks, asset managers, and the like. And then I became a hedge fund investor focused on those spaces. And I was actually investing in those types of companies throughout the 2008 financial crisis.
And so saw a lot of volatility and learned a lot about risk management. But while I was at Goldman, I would get a lot of colleagues and friends who had come to me and ask for advice about [00:05:00] personal financial matters that they were considering. And I noticed that the advice being given in insurance especially, was often just frankly, really bad.
Like a lot of sales lines that weren’t backed up by any sort of sound analysis. Mm-hmm. As you mentioned, like just interactions that often don’t feel very good. And so when I started above board, we initially were, you know, thinking about different areas we might focus and we ended, my co-founder and I ended up focusing on insurance because it is such an kind of yucky corner of the financial services world in some ways.
But also when the products are used correctly, it can be awesome, right? It can deliver amazing outcomes for people and their loved ones if you’re making good choices. And that ability to make a good choice starts with accurate, honest analysis.
Patrick: Yeah, I love that. So can we get into. How you you [00:06:00] go about that, that analysis?
Uh, because I, I think about when we’re looking at these things, there’s so many factors, right? It would be great if it was just sort of like an ab scenario, like we’re gonna do this or this. But when we, we look at the, um, the complexity of the client’s lives, right? There’s lots of different factors that need to come in.
And we’ve even found sometimes doing some of our analysis that, um, in this scenario, the insurance makes sense and this other scenario, it maybe doesn’t, with all of the factors remaining the same. So how do you go about doing that, that analysis in a complex scenario?
Wallis: Yeah, sure thing. So it varies a bit by product and then obviously by client as well.
But when we have a client come to us and they’re thinking broadly about all the different product areas that we handle, which includes life insurance, disability insurance, and long-term care, we start with a general framework that first we wanna make sure that we’ve hedged the risk of disaster. And so that involves things like looking at.
Is the client at a [00:07:00] place where they could just stop working and be comfortable and happy with the lifestyle they have? And if the answer is no, then that suggests that they probably need to think about disability insurance. And we’ll look at both any workplace coverage they already have, as well as options they could get in the market.
And usually the answer ends up being that they need both. Now in life insurance, if somebody has people who depend on their income and those dependents are, you know, reliant on that income for the standard of living that the family enjoys, then they absolutely need life insurance to address the risk of premature death.
And life insurance can be used to address the risk of premature death. And there are also a lot of really smart, interesting things you can do with it with respect to supplemental retirement planning and estate planning. I know you work with a number of clients on tax optimization strategies and it can be super helpful there, but our first order of business is always making [00:08:00] sure that we’ve taken the risk of disaster off the table right before we go look at those optimizations.
Patrick: I love that. Thank you. And so you touched on one of my, my favorite topics. We love tax optimization. Can you talk to us a little bit about how life insurance can fit into a tax strategy?
Wallis: Yeah, absolutely. So there’s using life insurance for the purpose of building cash value, which is the value that a policy holder or say like beneficiaries of a trust, depending on how you’re structuring it, can use while the insured person is still alive.
And in those cases, we’re often analyzing, well, how does this cash value grow inside the insurance policy versus if the client did something else with the money. And oftentimes that’s something else is putting the money into a taxable brokerage account. And I think one of the things that we do really well is we run that analysis in a very thoughtful, [00:09:00] personalized way.
And you mentioned earlier the Dave Ramsey adage of buy term, invest the difference. And the way that we analyze it, we, it actually is possible to reach that conclusion. I think one of the hallmarks of intellectually honest analysis is that it is possible to get an answer that is in your favor and also possible to get an answer that’s not in your favor.
And so when we do this analysis for clients, like there is an objective, clear answer about whether insurance is actually a good tool for this job. And, you know, we take into account things like this, client’s personal tax rate, both based on their income as well as the state they’re in. Um, and when working with clients, other advisors such as yourself, we love that collaboration ’cause it allows us to really dial in those assumptions and make sure that the, the conclusion is valid.
Patrick: Yeah, I love that. And one thing that we’ve seen with life insurance that I think is, um, and this is where my bias can come in, I think about, um, oftentimes we, we look at [00:10:00] the, we’ll call the best upside potential, okay? And when we’re going to do the comparison between, you know, an investment portfolio and the life insurance, the investment portfolio potentially has more upside potential.
Now, there’s times where I see if a client, their, their goal might not be upside. It might be, what is the likelihood I’m going to get to my outcome, right? Like, I want a higher likelihood than I do more upside. And so oftentimes it’s interesting to see how life insurance, you know, we might not have as much upside.
We might have a more narrow band of likely outcomes, but the fact that we’re gonna get to the, the desired goal is up. And it’s, it’s interesting when you start looking at all of those different factors that it can make a tremendous impact. We’ve just seen, uh, clients’ likelihood of success for their financial plan happening go up when they add some life insurance into the mix versus, you know, uh, an investment portfolio.
And it was just an aha moment for me to go, oh, [00:11:00] this is so interesting when you start factoring in all these, these pieces and some of the guarantees that can come with life insurance policy that, uh, uh, you’re gonna get to where you want to get to. So, um, good. So can we talk a little bit about disability insurance?
I, I think that’s one of the, uh, the areas of, um, planning that, that seems to get neglected. You know, I think a lot of people will have life insurance policies like, yep, I understand. I need a term policy to make sure if something happens to me, my people I love and care for are taken care of. But I think that same exact statement, you know, if something happens to me, I need my loved ones to be taken care of, can apply to disability, but it doesn’t seem to get the, the same attention.
Um, can you talk to us a little bit about how to, how to analyze some of those, those needs and what, uh, you’re typically looking at there for, uh, for clients?
Wallis: Sure thing. So with disability insurance, the way that we think about it is that if a client is not yet at a place where they’re truly only working for fun, mm-hmm.
Then [00:12:00] looking at disability options really makes sense. And I think sometimes people view disability insurance as being kind of like a tangential, like maybe you get it, maybe you don’t, type of thing. And I think that unless you’re really at a place where you are ready to retire in the standard of living that you would be happy about, then you can’t think of it that way.
You really need to think of it more the same way that you do with homeowner’s insurance, where if you buy a home, like it would be a big mistake to not carry homeowner’s insurance. Right. And so I think that there’s that mindset shift that needs to take place where there needs to be an honest reflection on.
Are you ready to retire? And if the answer innocent standard of living you’re happy about. And if the answer is no, like you need something that gets you there. And so once the client kind of reaches a point where they’re like, no, actually for the standard of living that I enjoy, my continuing to work at least for a few years is important, then we can start to explore options.
And one of the nice things about disability insurance too is that there’s a range of choices you can make about the type of [00:13:00] product that you’re getting. And so if you’re somebody where the answer to that question is, as long as I can make it through the next five years, I should be good. You know, you can get a disability insurance policy that only would cover five years of benefit and it’s less expensive than one that would cover you until age 65.
And so there are different ways that we can help a client tailor what they’re getting to actually address the risk that they have.
Patrick: Yeah, I love that. And, and I think I. Especially when we start talking about disability policies, there’s some nuance to those that really matters, right? Like, okay, if I’m disabled, what is the definition of disability?
Right? Does it mean I can do any kind of work, uh, if I can go be a Walmart reader, does my my policy pay? Or is it if I can’t do my specific line of work? And, and so I think, I think those things are, are critically important, and having somebody that understands the insurance world and all the options available to, as [00:14:00] clients and consumers of, of insurance is, is, um, critically important.
So I, I also wanna talk about business owners. I think there’s, um, there’s this thought process of like, oh, I’ve got enough assets, right? And this goes back to our disability conversation. Um, and long term insurance can fit in the, this equation too. Like, I’ve got enough assets. If something happens to me, my, my family will be okay.
But I think there’s levels where. We need insurance and even if our financial lives are taken care of. Uh, and I, I think of two sort of main pieces there. The first one is we’ve got, uh, business partners. Uh, something happens to me, um, the business, they may not wanna be in business with my wife. Uh, they, they might just, my wife might just wanna check and they just own the business.
And so I think that’s maybe an option. And then I, there’s also the, I’ll call it the estate planning side of the equation. You know, sometimes our clients [00:15:00] have a hundred million dollar valuations that they haven’t done any, any business planning for. And so there’s an estate tax problem out there. Uh, the cool thing about the estate tax is, um, if you have enough long runway, you can usually get rid of the estate tax, but you need a long runway.
And so it’s like, okay, in the short term, if something happens to us, uh, how are we going to pay this estate tax bill that’s coming, coming down the line? And, um, I’d like to spend a minute talking about, you know. How insurance can solve that problem too. So, uh, I, I’ve, I’ve highlighted two things. You know, we’ve got business owners and we’ve got estate tax, um, estate planning, uh, issues.
So can we start with the business owner side and how we go about just evaluating, um, whether a, a business owner’s going to need insurance and what kind of scenarios that would make sense?
Wallis: Yeah, absolutely. So a number of our clients are business owners and, um, the framework of, you know, thinking about whether you could comfortably retire is very much something in the personal sphere [00:16:00] to answer.
Mm-hmm. But you’re absolutely right that when somebody is an owner of a business, you also wanna think about it from the perspective of orderly operations of the business and transferring the business in the event of either disability or premi of death. And so thinking about how that would work, because it can be tremendously disruptive if that happens and the company is unprepared.
So absolutely there are. Business planning use cases for both disability insurance and life insurance. And we help clients put those in place to make sure that if any owner or key contributor at the firm either died or were disabled, that that would not be a financially catastrophic event for the business.
And interestingly, for business owners, we found that it can often be advantageous to do their personal coverage for disability insurance, especially, although we’ve done it at life for life insurance sometimes as well. Um, but for disability insurance [00:17:00] especially, you can have meaningful discounts on exactly the same policy that you would’ve gotten as an individual if you set it up to go through the business.
But then it’s also portable. So if life takes you to a different venture or a different role, you can take the policy with you. So there’s some really smart things you can do. If the client is a business owner or even a key executive right there, sometimes the implementation of these policies comes from a valued team member raising their hand and saying like, Hey, like I have this idea for executive benefits, or like, I’d love for us to add this, and it can be a great chance for business owners and HR professionals to put something in place that really comes off as thoughtful and forward thinking and making the employees better off.
Patrick: Yeah, I, I love that. And if it’s okay, can we talk a little bit more about the executive benefit piece? Because I, I think there’s so many ways to structure that and, and I think there’s, you know, the business can be protected if I lose a key person, but then there’s [00:18:00] also the opportunity to, um. For the employee to have some tremendous benefit to, for their contribution to the business.
And so can you just walk us through, uh, a few of those, maybe like a, a simplified structure that you’ve seen and, and it can be as complex as you wanna make it, but, uh, you know, it can be hard to, to outline these things, um, uh, in the, the framework we’ve got here with the podcast, but yeah. Do, do you wanna just talk a little bit about how executive benefits can work with, with life insurance policies?
Wallis: Sure thing. Sure thing. So with life insurance, um, some of the advantages that I mentioned earlier about the tax free growth of cash value, um, that works if you’re thinking about it in your personal planning. And it can also work if you’re thinking about it in the context of executive benefits and giving some additional upside through, um, the individual’s employment.
Um, and then there’s another angle on this that I’ll just flag in case it’s relevant to any of your listeners that. We’ve had some clients in the past where they’re not insurable in the [00:19:00] individual market, but they definitely need life insurance. And sometimes these executive plans can actually create an opportunity to get that life insurance because you’re doing it with limited or you know, practically no underwriting and it’s completely above board.
To do it this way, you just have to find the right program designed to be able to implement this. But it can be a total lifesaver for, you know, an executive or an owner who for any number of reasons can’t qualify at this moment in time for private coverage. Yeah. Um, but in terms of the benefits of doing it at the company level, you can structure it so that you’re basically offering additional tax advantaged.
Upside that you can use to fund benefits to the employees and incentivize them even to, you know, commit to being with the company. And there are a lot of different structural choices you can make depending on what your goals are and what your constraints are. ’cause oftentimes at the business planning level, [00:20:00] different businesses have different goals and constraints around mm-hmm.
What they were trying to provide to their employee and how much they’re willing to pay. And there are a lot of levers you can pull to dial in the plan that optimizes for what you’re going for.
Patrick: Yeah. I, I love that. And so, just maybe a few things that you can feel free to correct me on. Um, the nice thing about using, I’ll say life insurance as an executive compensation plan is, uh, I can.
I don’t have the same ERISA rules that I do with the 401k. I don’t have maybe necessarily testing limits and that type of thing. I can go, I’m gonna carve out my executive team and they’re gonna get this benefit and I don’t need to worry about some of the other employees in that, that mix. Is that a, is that an accurate statement or, or not?
Wallis: Um, so we generally like to make sure we’re working with the HR professional because, you know, we’re not lawyers ourselves and we wanna make sure that the company is comfortable with how it’s being set up. There are things you need to consider with respect [00:21:00] to fairness and how the plan is structured.
There are some bright lines, but things you cannot do. But the general idea that it’s okay to offer an executive benefits plan where you might have some benefits that are available to say like the top 20 executives that aren’t available to the other like, you know, 800 people like sure. That is definitely like a well established thing That’s okay to consider.
But then yes, when we’re implementing, we wanna make sure that the way that we’re doing this is absolutely comfortable for the, the HR folks who need to ultimately sign off on it.
Patrick: Sure. Yeah. No, that’s, that’s good. And I, I’ve seen a, I saw this in the context of a bank, uh, that we were, uh, working with. They had this, this strategy already in place, but what they would do is they would, um, you know, fund these life policies and then they would gross up some additional, ’cause it was effectively a taxable benefit to the, the employee.
So they would gross up some of the, the tax that the employee would have to recognize for [00:22:00] this, this, uh, benefit. Um, and then they got this like, asset that was accumulating tax free cash value for retirement. And, you know, I’m not exactly sure how the death benefit worked out. If the, uh, you know, family received some of the death benefit, the business received some, uh, can you give us a little bit of.
Um, maybe just clarity on how those pieces come together. Am I, am I on track where generally the, you know, the business will help with some of the, uh, the tax side and then how does the death benefit play out? Is that owned by the employees? It owned by the business? What happens there?
Wallis: Yeah, so with all these, uh, company or business use case insurance plans, I would say that you have some different design choices and whether, whether or not it makes sense to have individual ownership or company ownership depends in part on the size of the company and what you’re trying to do.
Um, but typically what you’ll see is that the company, uh, is the [00:23:00] owner. Um, but also with insurance policies, you do have the ability to transfer these assets in the future. And so there are some scenarios where down the road you might choose to transfer ownership of a life insurance asset. Um, but generally you.
Would set it up with company ownership. And you know, certainly if you’re doing something like a buy sell agreement, if there’s more than like a couple people involved, you’re almost always gonna see it as, um, you know, company owned and company as a beneficiary. But it really depends on what you’re trying to achieve, how big this team is that you’re covering, uh, in terms of what structure makes sense for that individual client.
Patrick: Now I’d like to just shift to estate planning if that’s, that’s okay. ’cause I, I think this is, um, uh, sort of the second piece of the, the discussion where, okay, I don’t need insurance for my, I’ll say lifestyle anymore. Now I’ve got a, a separate set of problems. I’ve got, you know, maybe some liquidity needs.
I’ve got a tax bill that could be coming due. Can [00:24:00] you just walk us through some use cases for life insurance when it comes to estate planning, just to get our, our listeners sort of minds thinking about how this could apply.
Wallis: Absolutely. So one of the benefits of using life insurance for estate planning is that when you work with a qualified attorney, you can put it inside of a trust and effectively remove it from your taxable estate.
And the value of that is that the future appreciation of that insurance asset happens outside of your own personal balance sheet and therefore is not subject to future taxation. And the other nice thing about life insurance is a tool for these trust owned estate planning strategies is that you don’t have an annual tax bill from the insurance policy.
I’d say if you just went out and bought the s and p 500, right? Say you go out in a trust and buy vu, the Vanguard s and p 500 ETF, that can be a pretty tax efficient asset, but you’re still gonna be getting a tax bill related to the [00:25:00] dividend dividends share. Those are gonna be qualified dividends, but if you’re in that highest long-term capital gains bracket.
You’re in a state that has meaningful income tax as well, um, that can end up being a pretty significant drag on the long-term growth. And again, that’s something that our analysis takes into account when we analyze well, is insurance really the right tool for the job, for this estate planning strategy?
And oftentimes the clients who are considering this type of strategy are in a very high tax bracket. And so the math works really beautifully where having the life insurance policy be owned by a trust is a great thing to do, both for moving the death benefit outside of the taxable estate, but also in some strategies creating cash value that beneficiaries can access during their lifetime and while the insured is still alive.
Mm-hmm. And so one of the, you know, great joys I think of, you know, parenthood or being grandparents is watching [00:26:00] these little people grow up. And so we have some clients who use insurance inside of a trust. Not only because they want that trust to be there after they’re gone, but they wanna structure it in a way where there’s meaningful cash value that beneficiaries have the ability to access under the terms of the trust, um, so that they can watch their loved ones access this value.
And so the insurance policy can be a really smart way, both to plan a legacy as well as be able to gift something to your loved ones that you can watch them enjoy during your own lives.
Patrick: I love that. And let’s just talk about estate tax for just a second. ’cause I think you, you highlighted some really important things and I want to give a little more context.
So, uh, the estate tax exemption right now is just under $14 million per person. So married couple gets about $28 million of, uh, exemption from their net worth. Okay? So if I, let’s say I’m worth [00:27:00] $20 million, uh, from my business and just my personal assets, and then I have a. $20 million life insurance policy, uh, that is a survivorship policy that’s gonna pay out at the, the second passing between me and my wife.
Okay, that’s $40 million. That puts me about 10 million over that exemption. And that 10 million would be subject to federal estate tax, which is 40%. And then if there’s any state estate tax would be, you know, um, sort of layered on top of that. And so that’s a problem. We think about all the layers of tax with property tax and payroll tax and income tax and capital gains tax.
To pay an estate tax after, you know, I’ve sort of paid all these taxes along the way is, is really frustrating. So you brought up putting it into a, an irrevocable, uh, life insurance trust, uh, putting it into a trust that’s gonna keep it away from that estate tax. Um, I think that’s, that’s a beautiful strategy and I think it’s something that people need to be aware of.
Uh, that, uh, you don’t wanna count on these dollars all coming into your, your plan and then all of a sudden, you know, the IRS has their hands on [00:28:00] 40% of maybe a big chunk of that. So, uh, anything to, to add to that, uh, before we sort of move on to some of the next pieces of estate planning?
Wallis: Yeah, so I would say in terms of the estate planning, it’s really important to try and look ahead because sometimes people, especially when they’re, you know, busy working hard on something that has created this major wealth event for them, you know, it’s just like there’s so much going on, right?
Maybe they’re getting ready for an IPO or they’re just growing their business or they just sold it and there’s a lot happening and it can sometimes be difficult to kinda step back and say, okay, well, like where, what is the range of reasonable places that we might be 20, 30, 40 years from now? And like, what does that look like?
And so one of the things we will do is we’ll actually model that out and take a look and. We work with other professionals in the client’s life to make sure that we’re considering all these angles because there are tools other than life insurance can be, that can be part of a successful strategy. So for example, in a couple, right, maybe before that, you know the 14 million you mentioned per [00:29:00] person, just slightly under 14 million that’s currently scheduled to sunset.
There’s no change in law, which there could be, but right now the law is that that will get cut in half on January 1st, 2026. And so what we’ve seen some clients doing is choosing to utilize a hundred percent of that gifting capacity now, because the idea is that, well, even if it still gets cut in half, you can legally use it right now and basically have more gifting capacity than you’ll be legally entitled to in the future if current law is not changed.
And so oftentimes in this scenarios. Insurance is still part of the strategy, but I think the ideal approach to this is for a multidisciplinary team to think about the client’s situation and come up with like, well, what is the right role for insurance? And what else are we doing to make sure that we really end up with the best solution for the client?
Patrick: Yeah, I I love that.
I wanna take a quick pause because if you’re listening to this [00:30:00] episode, I know you’re serious about protecting your business, preserving your wealth, and planning for a future that’s not only secure, but tax smart. Wallace and I have been talking about how these strategies can be used not just as protection, but is a strategic financial tool.
But here’s the thing, tax strategy is the foundation, and that’s exactly why we created vital strategies.com. Forward slash tax, a powerful resource to help entrepreneurs like you start building a personalized plan that’s legally, strategically, and compliantly designed to keep more of your hard earned money in your pocket.
And out of Uncle Sam’s, we’re talking real strategies used by high level business owners, no fluff, no gimmicks, just proven methods to help you minimize taxes, grow your wealth, and do it all with confidence. So if you’re tired of overpaying and ready to take control of your tax bill, head to vital strategies.com/tax and start building your plan today.
Now, let’s get back to the episode.[00:31:00]
Can we just touch on some of the gifting ideas and, and feel free to correct any of this. So let, let’s say I, I have, I dunno, $5 million of liquid assets, okay? That, uh, I, I want to get out of my personal estate and I, I gift those into a trust. And then the trust goes and buys a and my leverage might not be perfect here, but a, a $15 million life insurance policy with that, for that $5 million worth of the, of assets, if I move that $5 million outta my estate.
And then, um, and let’s just, let’s pretend I’m right at that limit of, of 28 million. And so I move that out and then I buy a life insurance policy in the, the trust, which gives me an additional 10 million, you know, my 5 million of initial tens,
Wallis: 15, yeah.
Patrick: You know, contribution. And then, you know, the 10 million of additional, you know, life insurance benefit on top of that is that entire 10 million totally exempt from, [00:32:00] from the estate tax Then, excuse me, all of the assets inside of that trust would be, uh, exempt from the estate tax.
Wallis: Yes. If it’s structured, if you worked with a lawyer who helped you structure that correctly, then yes, that is how it works. And to get that initial 5 million in there, I. There are some different ways to do that. I’ll just share a couple things that we see and you know, I’m not an estate planning attorney myself, but we work with a lot of estate planning attorneys, so I’m just sort of a lay person in an informed lay person perspective.
Yeah. On what we see ha people doing. Um, one way is to utilize a portion of your lifetime exemption, right? Like you as an individual have a little bit less than 14 million, so you could just choose to use five of it for that theoretical insurance policy that you’re talking about. Another strategy that we see people doing sometimes is utilizing annual gifting power for a life insurance policy.
And there’s an interesting thing that is available and we always recommend that a client should discuss this with our estate planning attorney if it’s something that might be of [00:33:00] interest and if it frankly makes sense given the structure of their family. Um, but you don’t necessarily need to have prorata sharing of the benefits among the beneficiaries.
So for example, if you have three children, but also seven beloved cousins, you could potentially have 10 beneficiaries on that trust, and that opens up annual gifting capacity for 10 people. But you don’t necessarily have to say everyone gets 10% of the trust, you have the ability to name different percentages, so you could treat the children differently.
Then you treat the beloved cousins and lawyers will have opinions about what’s the minimum percentage you need to give the cousins. But what I’ve generally observed is that it’s like, you know, single digit percentage of the trust can make them valid beneficiaries. And so if you think about [00:34:00] that, right?
Say you choose 2% as your number, then you’re doing 2% times the seven cousins equals 14% going to the cousins. And the remaining 86 can be divided between the three children. So there are different ways to approach this. I’m just sharing one example of something people might wanna consider.
Patrick: Yeah, I love this.
And so I’m going to, what we’re talking about now is the annual gift tax exclusion, which I can give a $19,000 gift in 2025 to, um, my, I’ve got three daughters, I could give 19,000 to each one of them. They don’t have to claim it as income. I don’t get a tax deduction for it. But, um, and my wife can also do the same.
She can give 19,000 to each one of my daughters so they, they all can get, you know, $38,000. Um, and so what you’re talking about here is like, oh, I’m gonna add in some cousins and other family members, [00:35:00] and now I’m gonna start to lever that 19,000 up. If I’ve got 10 people involved, now I’m giving $190,000 and my wife’s doing the same, we just got $380,000 transferred tax free.
Um, and then if, if I want to add life insurance into the mix, right, I might take that three 80 and be able to buy a multimillion dollar death benefit, uh, with those, those same dollars. And, uh, every year, as long as I’m alive, I can keep funding that, that policy the exact same way. And I think the thing you were highlighting there is, okay, I’m getting $380,000 into this, this trust fund, this life insurance policy, but I don’t have to give 10% of this to the, the cousins, you know, if I’ve got, you know, it doesn’t have to be a proportionate share of, uh, the, the benefit.
And again, that share, you know, we can figure that out with the legal team. But, uh, I love the, the financial I. Uh, alchemy that I think we’re creating here, [00:36:00] using these strategies given to us by the government and figuring out by, you know, super sharp people that look at the code and, uh, um, figure out ways to do this.
So that’s, that’s a, I love that idea. I think that’s, uh, that’s fantastic.
Wallis: Yeah. And it aligns with how a lot of us think about our loved ones, right? Like, they’re like the really close, my family members, like children, and then there are other folks who are like, you love them, you support them, but in a way that’s maybe a little bit different from how you would think about your children.
So it’s nice that the trust structure can reflect that reality.
Patrick: Yeah, that’s, uh, that’s fantastic. I, I love that idea. I feel like there’s probably a million different ways we can go about, you know, talking about how to structure the, the estate planning. Um, so I, you know, we’re talking about utilizing these, these gifting options to, to maximize the, uh, the value of the, the estate.
Um, any other, anything else that comes to mind from a pure estate planning perspective that. Uh, you see put into place that, [00:37:00] uh, you think is kind of a, a unique strategy that life insurance solves versus, you know, using a different tool?
Wallis: Yeah. So a couple of things come to mind. One is being thoughtful about the state framework for estate taxes that you’re in.
Um, I’m based in New York City and my company above Ford Financial is licensed to do business in the vast majority of US states, but we see a lot of New York clients just ’cause we’re headquartered here. And New York does have a unique estate tax regime and there’s some planning that needs to take place if you’re doing planning in New York.
That’s different from what you would do if you were almost anywhere else. So I think being thoughtful about how you’re structuring those trusts to be compatible with the state you’re in is a really important consideration as well. And then the other thing that can be interesting with respect to estate planning and life insurance is thinking about what assets in your portfolio.
Might benefit from being inside of a life insurance policy and how you can achieve that outcome, um, [00:38:00] in a good way. Um, so you had mentioned earlier about investment portfolios and whether the returns are, you know, higher or, or lower than we can get within a life insurance policy. And there are actually some types of life insurance policies where a professional advisor who, you know, the client has chosen and feels, reflects like how they are comfortable thinking about their investments.
A professional advisor can actually manage the assets inside the life insurance policy. Um, that particular type of insurance is called private placement life insurance, PPLI. And it’s a type of variable product, um, meaning it’s not just insurance, it’s also a security. And that can be a really interesting vehicle for when somebody has like, types of assets that might not be readily available off the menu of what you could get from other insurance policies.
Um, but you know, sometimes the kind of regular whole life or registered variable product is the best tool for the job. If somebody’s [00:39:00] attitude is simply, I want to do, I’ll call it the Warren Buffet strategy ’cause he’s publicly said that he thinks this is a good strategy for long-term wealth creation.
But buying the s and p 500, I mean, you can actually do that. And if you pick the right carrier, many of the carriers offer a low cost index to s and b 500 strategy. So if anyone listening to this is thinking like, oh man, like all the insurance investment choices are these, like high fee, actively managed things, that’s really not true anymore.
There is variation between carriers, which we help clients navigate, but if your goal is to just get at, go out and get a low cost index portfolio, you can absolutely do that with a number of variable products. Um, so I think that being thoughtful about what type of assets you want exposure to for your long-term estate planning.
Is important and then we can help you think about, well, like which insurance vehicle might be the right tool for getting this tax advantaged [00:40:00] aspect on those assets? Yeah,
Patrick: I love that. And I think one thing we remind clients of regularly is life insurance is a tax wrapper. Okay? So if I own an asset inside of that tax wrapper, it’s gonna get different treatment than if I own it outside of it.
And, uh, and then you start thinking about, uh, the leverage of the death benefit. It’s like, okay, there, there can be some real benefit to, um, setting aside our preconceived notions of life insurance and, and just looking at this as a tool, you know, is it going to be the most effective tool to help me get to where, uh, we want to go?
And at above board. I love that what you’re doing there and taking that analytical approach and going, Hey, this is the best tool, or No, it’s not, you know, we’ll, we’ll give you an honest answer on that. So, um, I think that’s, that’s fantastic. Now I’d like to talk about the types of insurance and. You know, why whole life versus universal life versus variable universal life and you know, all of the variations.
And so, um, yeah. We’ll [00:41:00] I’ll ask that question. Alright. Um, whilst now if it’s okay, you touched on the different types of policies. Just a, a second ago. Uh, when do I know when the right policy, you know, what type of policy I could use? Because that, that also seems really confusing. Uh, I’ve got a whole life policy.
Um, and we could maybe get into defining what these different things are, but I’ve got a whole life policy, uh, as an option. I’ve got a universal life policy, which I think can have some variations underneath it. I could have a, uh, indexed universal life. I could have a variable universal life. I could just have a universal life that almost seems like it’s a, an interest based product.
So can you talk to us about, you know, when we should. Use. Again, these are all, I think, tools and they, they all have their, their appropriate use when we should consider these, these different tools and, uh, what, what scenarios they can make sense.
Wallis: Yeah, absolutely. That’s a great question. And I think that it also touches on something that’s [00:42:00] critically important, but often lacking, which is that it’s really important for clients to know what they own.
And we’ve met a lot of people who come to us with policies they got elsewhere, and that often happens because they’re surprised or disappointed by how the policy is performing. And it usually boils down to the fact that they were not advised bet what this thing really is and how it works over time.
And I’ll give a couple examples of that as well, but at a high level, the way that I think about putting insurance into different categories is that the first question is, is it term or is it permanent? Right? And so term is temporary. It’s designed to last for a certain period of time. Can you, very helpful.
If your goal is to hedge the risk of premature death. But it’s not designed to last your entire life. And within permanent insurance, that has a, a lot of different categories within it. And sometimes people use the term whole life to talk about any policy that’s designed to last your entire life. Um, but that’s actually technically incorrect.
Whole life is actually a [00:43:00] subset of permanent. So if you think that permanent insurance is ice cream, then whole life might be mint chocolate chip. Mm-hmm. And whole life is a very specific design of policy and it is characterized by having very strong guarantees. Now, I’ll caveat that when I speak in generalities here, there’s always this question of like, well, like, isn’t there this one small carrier that does it a little bit differently?
And like, yes, that’s absolutely true, but I’m talking about kind of like the major providers who generally and consistently have offered these products for decades, typically with whole life. What you’ll see is that it has very strong guarantees. With the opportunity for additional upside through dividends that are technically not guaranteed, but for most of these major carriers or really for all of the major carriers, have been consistently paid every year for over 150 years at this point.
Mm-hmm. And one of the things that I like to think about with permanent insurance is what is the risk return of this insurance policy? Right? Risk [00:44:00] being like, what could I lose? In what scenarios would I kind of feel like, oh wow, this thing is not going great. Whereas like return or reward is about like, well, what could I make?
What and what scenario would I look back and be like, wow, that policy is like knocking it out of the park in my portfolio. I’m really glad I have it. And with whole life insurance, I think of that product as being more of a fixed income like instrument. In terms of the risk return. You’re not gonna have, you know, 9% returns from that policy, but you’re also not gonna have a big down year.
There’s like a baseline of crediting growth that’s guaranteed, and then you get this dividend on top, which dividends can change over time with things like interest rates. But generally this thing is gonna behave like a fixed income like instrument, which interestingly though has some protections against interest rate shocks.
So if you think back to like the interest rate shock that, you know, like led to Silicon Valley Bank going under [00:45:00] mm-hmm. With a whole life policy, you are insulated from that in a way that you’re not from just straight out owning a bond portfolio.
Patrick: Yeah.
Wallis: That’s kind of an interesting thing, thing to think about with whole life.
Patrick: Yeah. I think you, you’re hitting on a fantastic point here. Uh, I’m gonna highlight a few things that, uh, I believe you just said. Uh, one of the great things about whole life is when I see an illustration, you know, when you show me an illustration when I’m buying it. 10, 15 years from now, it’s not going to be that different, you know, it, it’s going to perform pretty close.
The factor there is the dividend piece. Um, and then to, to highlight on a, a key financial thing you just mentioned is the cash value in a life insurance policy doesn’t have that interest rate risk, right? So it’s, it’s interesting in the context of, uh, interest rates are sort of like a teeter-totter, right?
When interest rates start going up, my bond value goes down. And so if we’re thinking of this as a, um, an interest rate, um, [00:46:00] sort of play, right, like it, it’s could be an alternative to my bond portfolio. As interest rates start to go up, my bond value comes down and the opposite’s true, right? When interest rates go down, my bond value comes up.
But if we, we look back to your example of the, the interest rate sort of spike that caused Silicon Valley Valley Bank to fail, I. We could have, you know, interest rates start going up. I can pull my cash value, you know, if I want to, I can take a loan against my cash value at a potentially predetermined rate and then go reinvest if interest rates are 14%.
Uh, you know, and, uh, sort of take advantage of that. And I don’t have any, uh, concern about the, the value of my cash value going down because of those rising interest rates. When I think about the risks out there, we were talking about risk, right? That’s one risk that goes away. Uh, I don’t have interest rate risk with my, my whole life policy.
So I, I wanted to highlight those things, so thank you for for, for that. Yeah, yeah. No, it is a
Wallis: very cool instrument if you’re looking for that sort of like risk reward. And I think that the risk reward is very [00:47:00] compelling, but then, you know, sometimes clients are saying, you know, they’re looking more for like long-term equity upside.
And back to the point about making sure that we’re advising clients in the best tool for the job. If you’re somebody who’s looking for long-term equity upside. And you know, if you would be totally comfortable with say like a 50% draw down, like we saw in 2008, you know, the markets were down 50% roughly from peak to trough during the financial crisis.
If you’re somebody where you look at that and you’re like, you know what? I’m in this for the long term, either for my own retirement, which is decades away or for my children or grandchildren, and that type of volatility is okay and I just want leverage to the opportunity for higher upside from equities, then something like a variable policy can be a great fit there because mm-hmm.
With the structure of a variable policy, you basically have uncapped upside, right? You just get what the assets return. And with a lot of these policies, you can get a low cost indexed portfolio, but the flip side of [00:48:00] that is that you have volatility, right? So your policy could be down a lot. Um, and then there’s also a type of permanent life insurance, uh, universal life.
You mentioned it earlier, and you’re absolutely right that there are different flavors of universal life. Interestingly, the choices you make in policy design can result in policies that end up working pretty differently. But with indexed universal life, and I’ll be transparent that we handle this product too, but it’s also probably one of the top ones that I see where people got stuff elsewhere and didn’t know how it worked.
Patrick: Mm-hmm.
Wallis: With Index Universal Life, it is usually tied to an index. Oftentimes something that we’ve heard of, like the s and p 500 or the law of folks have heard of like the s and p 500. Um, sometimes it’s to a different index, but the idea is that there’s a credit. But then what people often don’t realize is that there are oftentimes ceilings or some other form of charge.
Mm-hmm. And that even if you have an uncapped [00:49:00] index, universal life policy, there might be some other form of charging you in there that could lead to a different result from what you are expecting. And I say this as somebody who’s gotten a number of outreaches where somebody’s like, the equity markets were up 18% last year, why is my policy up 4%?
Mm-hmm. And the answer is usually these kinda hidden clauses about what you’re actually credited and then what other charges get applied to your policy and people not understanding that dynamic.
Patrick: Yeah. This is a really important point because I, I think these, these financial instruments are complex and they’re, they’re oftentimes sold with a, an illustration that is, we talked about the whole life illustration.
The whole life illustration is going to do what the whole life policy is going to do. It’s going to look very similar. There’s not too many variables that can get that outta whack. An index universal life policy. There’s so many variables. You know, what [00:50:00] index I decide to choose? Um, you know, the fees that are applied, there’s so many factors.
And the way that’s sold to me oftentimes is, is rosy and it’s linear when the markets are not linear. And, uh, and so how do you go about really dissecting those policies and helping? ’cause, uh, I, I, the concern I see is trying to figure out as a consumer, which policy I should buy whilst we’re gonna spend an a year together meeting every month, and you’re gonna be informing me on all of the, you know, uh, the different options, right?
And the, the nuance in these policies. How do we go about actually without spending a year together, how do, how do we go about discerning which, which policies make the most sense, and how to avoid some of those potential? You know, risks that are out there with not fully understanding the, the policy we’re buying.
Wallis: Yeah, sure thing. I think this is where the advice [00:51:00] that we give it above board, and you know, how I think about risk management and how I advise clients really comes into play because when we think about it at a, a sort of simplified framework, right? ’cause you’re right, there’s a lot of complexity underlying these policies.
To me it comes down to a couple key questions, which is like, what type of risk reward are you looking for in terms of equities versus fixed income? And then what type of guarantees are essential to you and how much are you comfortable paying for those guarantees? Yeah. And so I think that’s sort of like the high level framework that we use.
And then we will go out and pull different illustrations that are in the range of what could make sense given the client. Stated goals. Mm-hmm. And we’ll look at things. So for example, I’ll give you an example of the client. There was, they were [00:52:00] looking at variable product and there was one product where the death benefit would be guaranteed out till age 120, even if equity markets returned 0% for the next 80 years.
Mm-hmm. Right? Like it would just be like literally this death benefit was guaranteed even if that horrible scenario played out. Yeah. Um, but the trade off there was that in a more, I’ll call it base case scenario, where the market returns say like, you know, somewhere between six and 8% over the long term, the, the cash value and the death benefit on that policy were lower than with a different policy where you could make a lot more in the six to 8% scenario.
But if markets returned 0% for, you know, 30 some years, the policy would lapse. Meaning you would have to put more money in or have it be [00:53:00] worthless. And so usually when we start to look at those illustrations, clients will gravitate towards one versus the other. How much do they want this thing to just be like an ironclad policy that is designed to make it through in even the most draconian scenarios?
Yeah. And how much do they view it as? Like, look, I mean, if my brokerage account returns 0% for the next 50 years, that would be horrible. And while it’s theoretically possible, that’s not the scenario I’m solving for. And I don’t really wanna pay an insurance company much money to protect me from that unlikely scenario.
Patrick: Yeah.
Wallis: And so we help people figure out choices like that.
Patrick: I love that and, and I think one other really important factor with. Uh, index universal life and, and oftentimes they’re using the s and p 500 as the index. If you look at the history of the s and p, this number could be off, but it’s not off by a ton.
About 50% of the s and p’s [00:54:00] return comes through dividends. When you, you’re in an index universal life, there’s no dividends that come in into that return. So it’s purely just the performance of the, um, the asset values, uh, over time. And so I think that’s an important factor too. ’cause, uh, you know, it’s, it’s not like owning, you know, the s and p in, in a life insurance wrapper.
You know, it is different. That’s absolutely
Wallis: right.
Patrick: Yeah. Good. Um, okay, so we, we’ve talked about whole life. We’ve talked about index universal life. What else do we have out there from a, a life insurance perspective that we can utilize.
Wallis: Yeah, so there’s also this question of individual versus survivorship, and that’s a really important one to consider when you’re doing long-term planning.
And it’s one that I think is often overlooked about, you know, whether or not the client’s goals are best served by choosing individual life insurance versus survivorship. And so the way that we approach that is that we’ll consider both scenarios if the client’s goal [00:55:00] could potentially be served by either.
So in an estate planning case, for example, where a client says, look, I’m not expecting to use this money in my lifetime. I only care about the death benefit. Um, oftentimes survivorship is a good thing to consider, but interestingly, if it’s also a client who says, my spouse and I want long-term equity upside in this trust owned policy strategy that we’re doing for the benefit of our grandchildren and beyond.
Yeah, then you might actually still be better served by individual policies because while there are survivorship variable policies available in the market, and sometimes those are great, sometimes you actually get better death benefit if you do two individual policies. And so we like to triage these different choices and really diligently think through the different options that exist.
And oftentimes there [00:56:00] are some trade-offs that clients will need to decide like, well, what feels more important to them? You know, are they optimizing for a scenario where they live kind of a normal to extended lifespan? Or do they wanna optimize for a scenario where maybe things don’t go so well and they are gone prematurely?
And so people have different feelings about that. Um, but sometimes the policy type that you choose can really make a big difference in what you get for your money and the return on investment.
Patrick: I love it. And, and I feel like this just fits so perfectly into your whole methodology at, at above forward financial round.
Like, we’re just going to look at your outcomes, what you’re trying to get to, and we’re gonna find the most efficient, uh, way to get you there. And we’re gonna, we’re gonna look at all of the scenarios, uh, from a financial point of view and, and figure out if it needs to be a survivorship policy, an individual policy.
And so I think that’s, uh, that’s, that’s fantastic. So, well, I feel like we could talk about this all day. Like, I, I feel like [00:57:00] insurance is, uh, an interesting topic and, um, I, I can already see future episodes where we’re gonna come back and sort of dive into to more of these, these things. But I’m just gonna highlight what we’ve talked about so far, and then you can, you can chime in on anything else we need to talk about before we, uh, before we start to wrap up.
But the first thing is like life insurance and insurance in general is. Is helping us eliminate risk, right? Um, if we think about the best use of insurance, uh, and this almost doesn’t matter which, which type of insurance we’re using, it’s to pay one premium and then file a claim, right? Like, that’s like the absolute leverage to use.
Um, and so that can, that can protect us on the immediate term if some catastrophic thing comes along and, and happens to us. Um, and then I think about some of the long-term, uh, benefits of, you know, the tax free nature, you know, start being tax efficient. Now I’m, now I’m excited. And so, uh, life insurance can be a fantastic tool to be, uh, tax efficient from [00:58:00] an estate tax perspective, from an income tax perspective, from a capital gains tax perspective.
It can be, uh, multifaceted there. So I think that’s, uh. Awesome. And you also touched on, um, what I’ll call financial alchemy too, you know, when we, uh, are able to fund some of these trusts with gifting strategies that, uh, are, are incredible. So, uh, I appreciate all of that insight. Is there anything else that we, we should touch on that, uh, is important before we, before we move to the next, next part of our discussion?
Wallis: Yeah, no, I think that summarizes it really well. I would just emphasize that, you know, the analysis really is different for each person and their goals. Mm-hmm. And so I think the approach that we take of like figuring out, well, how does the math look based on this person’s situation and what’s actually available to them, ensures that we find the right answer together with the client.
And that I would encourage listeners if they have sort of preconceived notions about different types of insurance to, you know, try to like lean into those questions or [00:59:00] preconceived notions and really like test them. Because sometimes what people think they’ve heard, or maybe even what they experienced with the past policy.
Is very specific to what they had and that there’s a way to do the insurance that is just different and better. Um, so in an industry where sometimes people end up in like suboptimal situations, I’d really encourage people to try to come into it with a, you know, blank slate. ’cause I think when you approach it in an intellectually honest way, there are a lot of really great opportunities that reveal themselves.
And for clients where that’s not the case, we’ll simply tell them, right? Yeah. Like, we don’t wanna sell an insurance policy that doesn’t make somebody better off.
Patrick: I love it. I love it. So, uh, Wallace, you’ve done something that I think is pretty cool if, uh, you’ve got a landing page for our listeners, if they go to aboveboard financial.com/vital strategies, uh, there, there’s a, a number of resources you can get on the email list.
You can get a quote, uh, you can just book a call. I think all of those things are, are tremendous. [01:00:00] Uh, and so if somebody feels like they have a, an insurance need that they need to be addressed, I think that’s a, a fantastic place to go. And we’ll have that in the show notes, but again, it’s above board financial.com/vital strategies.
And, uh, I think it, it’s a, a great place to start to just start to sort out, when we think about the, the, the entrepreneur that’s listening to this, you know, there’s risks out there and let’s take those risks off of, um, out of the equation, right? Uh, from a financial perspective. And so, uh, typically we can do that with, you know, repositioning some assets and using the leverage of, you know, the insurance products, whether it’s disability, life insurance, even long-term care insurance, if that’s, uh, something somebody wants to get into you, you help with all of those things.
So I, I, I think this conversation is, is fantastic and really can just take care of the people that you, you care about and your, your own, you know, success too. Just, uh, um, looking at, you know, how these tools can be used from a, a tax strategy perspective as well, I think is. [01:01:00] Fantastic. And then we think of the other side of that.
If I don’t take care of these things, you know, the potential downside, you know, the things that could happen to my family if this trajectory I’m on all of a sudden stops. And, uh, uh, that’s a little scary, you know, uh, as, as a husband and a father, it’s like, I, I worry about those things. And so, uh, we carry ’em pretty healthy amount of insurance and all the different categories just because, uh, uh, I don’t want, um, the people I care about, uh, to be left hanging.
So, uh, this has been fantastic. Thank you so much for tuning into this episode of the Vital Wealth Strategies Podcast. I truly hope you found this conversation with Wallace insightful and valuable, especially if you’re looking to build a stronger, more strategic foundation for your business and your legacy.
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