Ep 45 | A Surprisingly Easy Solution to Estate Planning in Your 30s

Estate planning isn’t just for the ultra-wealthy. Priya and David Meister (CEO of Steward) break down a practical, values-first plan for your 30s: why a revocable trust plus pour-over will beats a will-only setup, how to pick trustees when family dynamics are messy, and the power of updating beneficiaries, granting trustee discretion, “cross-naming” trusted friends, and giving while living.

Takeaways:

• Get the core four in place: revocable living trust, pour-over will, durable power of attorney, and healthcare directive.

• Update beneficiaries across every account (401(k), brokerage, bank, insurance) and consider naming the trust.

• Separate “kid care” from “money care.” Guardians ≠ Trustees.

• Revisit your plan after major life events. Perfection isn’t required. Execution is.

Guest Bio:

David Meister is the cofounder and CEO of Steward, a technology-forward estate planning platform pursuing trust company licensure so it can serve as a regulated, fiduciary trustee. A two-time founder (previously at Sidecar), David focuses on helping modern families create and administer customizable, attorney-backed estate plans that prioritize privacy, clarity, and better outcomes across generations.

Follow Priya Malani:

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Transcription

I don't think a lot of people think about going outside of their family for their will, for their estate plan. But beyond naming Stewart as a trustee, you can actually think about naming other people in your network, maybe close friends, and maybe, like you said, what was the word you use? Like cross? Cross naming. I call it cross naming. I won't say mutually assured destruction, but the idea is that both people truly understand what they're getting themselves into because this is an important aspect.

And you know, what I don't like to do is fear monger. I don't like to talk about the bad probate stories. I don't like to talk about 401ks that have been locked up for years. I want to talk about what do you care about in terms of your values and who do you trust with that process.

Who the fuck am I to tell you what to do with your money? My name is Priya Malani, currently managing millions of hard working dollars. Enough for play, let's talk. Welcome to the F Word Smart Money.

David Meister, welcome to the F Word.

Thank you so much for having me, it's a pleasure. I'm really pumped. So you're a two time founder, This is Stewart is your second company. Tell us a little bit about what prompted you to build Stewart, who it's for, and the problem you're trying to solve. When you transition from a company, you start to ask yourself a lot of questions. And after my first company Sidecar, I took some time and really started to reflect on life and children and family and succession planning and my parents getting older, things that a lot of us probably think about. And I start to get enamored a couple of concepts and really start to think about two concepts. One is a radical concept called Die with Zero, and the second is a slightly more abbreviated version of that, which is give while living.

And it's a less extreme version. And so for me, that's where the concept Stewart really started, which is how do I start to facilitate those concepts in my own life? And I started by going to a few estate planning attorneys here in California. And I felt like they were great professionals and they offered great perspective, but they didn't have the same frameworks that we built at Sidecar in fund administration and investment vehicle administration in estate planning. And some of the concepts with respect to documentation and administration were similar. And so I started to think, wow, maybe I'm on to something here. Our mission is better outcomes for families. And that doesn't mean that you have to be married or have children. It just means that broadly as a generational planning exercise, we want to help you have better outcomes.

And so it's really for anyone who needs to create an estate plan and also eventually administer that estate plan. So we are working to become a licensed Trust Company. And what that means is that we can actually step in as your trustee legally and regulators hold us accountable as a fiduciary.

Gotcha. OK, so we have to back the F up for people who have no clue what estate planning actually involves. What is it? And I think a better question is like, what do most people get wrong about it? I think most people think that estate planning is about death and huge houses, right? And the answer is estate planning has nothing to do with either of those things. The way I think about it is estate planning is about whom or what do you care about. So if you're looking to save money on estate taxes or income tax at the state level, you can use trusts. If you're looking to donate to your alma mater or a soup kitchen or help put a bench in a local park, that's also an important part of estate planning. And so for me, you first have to start with the question, who and what do you care about?

For most people, that starts with their children and then branch out from there. And if you, obviously most of us, hopefully all of us care about our children, then you back up and you say, OK, how do I create an estate plan just for the basics? A will, which is probably what you are all familiar with, are some light instructions for a court of law to figure out what to do with your stuff. A trust is a slightly more advanced document that hopefully takes all of the stuff that was in your will and got poured over or that you put into the trust and does it a bit more privately and hopefully in a more streamlined way.

So we all come into this notion that this is all about wills. I like to focus more on trust because I like privacy and I like not paying a lot of court fees. What do you mean by poured over? Most people don't wake up every morning and think about how do I put every single one of my prized possessions into a trust. And because of that fact, lawyers designed a concept called a pour over will, which is where you take all items that did not make their way into the trust, which is usually most, as most people don't think about this on a daily basis. And it then pours those assets into the trust.

There's a lot of complexity that we can go into probably another time with a detailed estate planning attorney. But I think the basic concept is that a will is public. It's in the public view, and probate is about opening your life up to the world so they can contest it and figure out who gets what. And a trust is meant to be a vessel that's private to you, and it's a place where you can share your values with your family.

OK, still a lot to unpack there. But you know, for those listening, Stewart is not a free tool. And you've said that your clients aren't necessarily interested in using free tools. They're interested in something maybe more robust, which is the point of Stewart. Why would someone pay for this if you can do this online for free? Like what makes the Stewart approach different from free or low cost options?

I think first of all, all of the options in the market are doing a tremendous service because in most cases something is better than nothing. So going to one of the free services is better than having nothing, especially if you have a simple situation, you don't have a ton of assets, but you want to make sure that your wishes are honored. The low cost options that offer basic trusts are also doing a service to our market. They're also spending a lot of time educating the public and we are woefully behind on estate planning and trust broadly as a country.

The reason why folks come to Stewart is because they want the best in technology in terms of customization paired with a partner attorney that's going to make sure that this document reflects the situation of their family. That complexity usually comes from assets, so sizable assets, complex assets like multiple residences or private assets, so assets that are not public equities. It also could come from having a special needs child. Maybe they are expecting a large inheritance, but they're not quite sure how much. I think ultimately the comfort of knowing that you can truly customize the documentation to your family's situation and also meet with, in every instance, a licensed attorney that is a partner to us. So they're not part of our company, but they are ones that we've worked with previously and that we stand behind. That's really the differentiation.

But that's not to say that you shouldn't go to one of the other services and get an estate plan if that's what's right for your situation. Just get like you said, something's better than nothing. In almost all cases, I'm sure there are trusts that are not drafted the way you intend them and we can get, we won't get into that, but I think in most cases something is better than nothing.

Yeah, it's good to have a professional though on your side. So you've mentioned special needs, you've mentioned inheritance, all these hot button or slightly messier topics. It feels like one of the reasons that people avoid estate planning is because maybe they have a messy family dynamic or maybe they don't even know who to name in their will or as their trustee. It can feel like that would be a blocker to entry to like, OK, I can't think about this right now because I don't know how I would go about it. What do you suggest in those cases?

You know, there's a lot of reasons to not estate plan, not tax optimize, not do a lot of things in broad financial services that we should be doing. And so I appreciate that and I come from that world. I think ultimately this should be a positive exercise where you're sitting with yourself or with your partner and you're going through basic questions like who do I want to benefit if I'm no longer around? Who do I want to take care of my kids? What values do I hold dear?

And so one of the ways that we're solving that at Stewart is that we are in the process of creating this Trust Company in which we can be named and we can have guidance from you frameworks, maybe tech enabled frameworks, using the buzzword AI to help you get comfortable knowing that maybe your family member or friend can cover some of the tasks, we can cover the others. And so I think that's a big unlock and something that we saw as we started to talk to our customers is they get to this trustee screen, as you mentioned, and they're like, I don't know who to name. And we don't want that to be a blocker, but I think that it's one that is a blocker.

And so that's one of the ways we're solving it. I think the other way is to maybe cross name a friend so they agree to take on the responsibility for you, you agree to take on the responsibility for them, and that way there's this kind of maybe fabric that's created this stronger bond between you. I actually called a good friend of mine and asked him to serve as a role in my trust not that long ago. And he was truly honored. And I think he was really excited would be the wrong word, but I think he was. I think it's a bigger honor than being asked to be in someone's wedding. So I think you just have to make it positive. You have to say this is a part of life and go from there.

That's great advice. I don't think a lot of people think about going outside of their family for their will, for their estate plan. But beyond naming Stewart as a trustee, you can actually think about naming other people in your network, maybe close friends, and maybe, like you said, like cross naming. I call it cross naming, so I won't say mutually assured destruction, but the idea is that both people truly understand what they're getting themselves into because this is an important aspect.

And you know, what I don't like to do is fear monger. I don't like to talk about the bad probate stories. I don't like to talk about 401ks that have been locked up for years. I want to talk about what do you care about in terms of your values and who do you trust with that process.

Oh but now I need to know. Give me like one story where things just all went to hell in a handbasket. Give me a really crazy story that you've seen. So there's someone that works in our office that's at a company that's just next to us and his dad passed a few years ago and his parents were separated and he actually had a trust that was drafted that sat at the attorney's office for years, several years and it never got signed and never got approved and never got notarized. I'm not sure who is at fault, the attorney or I assume that they were pings from the paralegal to get this thing signed. I think this estate was close to 8 to 10 million dollars and they still haven't gotten access to it.

Certain states do have easier probates. And this is someone who is an entrepreneur. It's someone who I think that money could change how he thinks about his life, how he, whether he can buy a house, whether he could have taken a bigger chance as an entrepreneur versus selling his business to a larger competitor. These are life-changing fact patterns. And so I think you never know what's going to happen. And what you want to know is even if you take a long time to update it, at least know that the core principles and building blocks were there. That was just one example I heard recently.

The other one was I was at a founder event a while ago and I spoke to a founder and I was telling him what we did. And he's like, Oh yeah, my wife passed last year and we still don't have access to our 401k. Something as simple. And he's probably a little bit older than I am. But look, these things happen and you just want to take some small steps to make sure things are done well and positively.

Yeah. And so that's sort of the drawback of going with like a less tech enabled and just a brick and mortar type service is that paperwork ends up on the desk and it doesn't get signed, it doesn't get pushed through. And now at the time of someone's death, it's already a stressful time on your friends and family. And now you've just put all this additional burden, paperwork, figuring out the ins and outs when you leave some of those T's not crossed and I's not dotted. And so getting it done can be make or break in those stressful situations.

It doesn't have to be complicated. It doesn't have to be hard. There are solutions for every family, whether that's an expensive law firm that is the right firm for you. If that's your situation, Stewart is the right solution for a large chunk of the market. And then there's other options that you mentioned. The key is to get it done. And I think a lot of attorneys will say, look at it every year. If you had an event that year, you bought another home, you had a large exit as a business, you had your third child, you've had a family member get a diagnosis. Sure, look at it every year. But I think at the very least get it done the first time and look at it every once in a while. But I think that looking at it every 5 minutes is not necessarily what's important. We're too busy for that.

So the listeners of the F Word are in their 30s, they're in their wealth accumulation years or not the ultra wealthy yet. What are some of the things that you would say have changed in the estate planning landscape that might be pertinent to people who are high earners, not rich yet versus ultra wealthy? I'm going to nerd out a little bit on distribution standards for a second, but it used to be the two distribution standards were very popular. The first was either a stagger distribution where you make, you see in the movies at 30, they get their inheritance or at 35, or it's staggered half at 30, half at 35. I think that's becoming less popular for folks in your demographic because their assets could grow to a point where you might not want to hand all of your assets to someone at 30 or 35 for a variety of reasons, including tax or your kids are just different than you expected or they have challenges that you weren't anticipating.

So I think that's one thing to think about is we want to be a little more thoughtful, especially if you don't reach for that estate plan that's stuck in a drawer. You don't want to have a gotcha situation down the road. It's very difficult from what I've understood from attorneys to having a trustee not distribute if it's in black letter that it has to be done at 30.

The other thing I think is that folks are giving a lot more discretion to trustees to avoid lawsuits. And so if you're someone who's growing your wealth, having a full discretionary standard in the right context, for me personally, that makes sense because you don't know what's going to happen down the road. You don't know what court cases are going to do to define standards. And so just giving the trustee discretion for a variety of reasons, including protecting your assets is interesting.

Those are developments that I think as you see folks who are growing their wealth and their wealth could change from when their documents are signed to when they're active. Those are some interesting things. The other thing we've seen is that the estate tax and the gift tax has drastically changed. So in the new bill that was signed by Congress this summer, you may all know it's now at 15 million per person or 30 million per married couple that's exempt from lifetime gift or estate tax. So I think that's just something I think people think, oh, there's an estate tax, but they don't quite know the actual facts.

So that's something I think people will be thinking about or not thinking about. And then the final thing is using your annual gift exemption, especially if you have small children to move small amounts of money is something that I think that people can do to do a little bit of what I call give while living. So those are some of the concepts that I think about in someone who's always growing their wealth over time and wants to kind of be future proof, but at the same time have this be appropriate for where they are today.

Can you give us a little crash course in how the annual gift exemption ties back to your estate plan? What is the tie there? Why do you bring that up? The annual gift exemption? A lot of families use custodial accounts where they are essentially controlling the account, but when the child turns the age of consent in the state, it's theirs with absolutely no guardrails. And I think there's some changes being done to that, but by and large that's how it is.

The estate plan is about your values and who and what you care about going back to that. And it might make sense to create a small trust where there's the guardrails around the assets where you can move your annual exemption. So when you're creating your estate plan, thinking about your beneficiaries, what are your guardrails? Who's going to enforce that? Starting to think about multi generational planning for those who are kind of maybe in the middle or the latter part of your segment, that's where it's connected because you're not going to come back to that when you're not estate planning, you're kind of trying to get everything done in one fell swoop.

And so a lot of times it's both cost effective and also efficient. And you're in the right head space to think about how you might start to slowly trickle dollars down if you're not ready to do these larger gifts.

OK. I think we're probably at a good point to talk about a revocable trust. So can you explain the concept a little bit and maybe why people should be thinking about that as an option? The beauty of revocable trusts is that they are able to be changed until you die, so nothing is set in stone and people situation changes and they can revise their revocable trust.

I think it's a very powerful tool for privacy, as I mentioned, to ensure that your wishes are honored in a more complex way than a basic will, and in the same way that a will is a snapshot in time where a judge makes a value judgement based on that document. A trust can be living or revocable and then change to be irrevocable upon death and continue to exist. Some wills create trusts, but ultimately a living trust can be a relatively basic document that can be changed.

And so the risk assuming you don't die, is that you can revise it over time as your situation changes. And my goal is to demystify this concept and make it very clear. This is not just for wealthy people, it's not just for old people. It's truly for everyone, whether you're getting a basic form from a low cost provider or a custom document from us or from a premium attorney. The Living Trust is a really great tool to make sure that everything you care about is protected, and it's done so in a very clean and private way.

I want to go to like a really easy to understand use case. So I am 35 years old. I work at Google, I make 220. I'm married and I have a kid on the way. You have a kid on the way. You have your second kid on the way. First kid, first, we're having a daughter, a daughter in February. I'm a February baby. That's so exciting. Oh my gosh. Congrats. OK, so what are the basic things that you want to be thinking about getting in place?

So I didn't talk about some of the other documents. I'm going to talk about them very briefly. One is who are you going to name as guardian of your children? That's the main catalyst for everyone to get in a state plan, right? Then that's it. It's not about your assets. It's who is going to take care of my children. And sometimes that's the same person as your trustee. Sometimes it's not. Maybe someone's really great with kids, not so great with money. So it doesn't have to be the same person, but it can be. Maybe you have two sisters and you want one sister to do one role and one do the other.

So I think starting there, so guardianship, then there's a power of attorney, which relates to making decisions when you're incapacitated as well, the healthcare directive, which has similar aspects for health and decisions around that. So I think you want to make these basic decisions. You want to take stock of what your assets are. And if you work at a large tech company, you've hopefully gotten some RSUs and stock and it's growing. You have a 401k.

The other thing that I think people can do, and it's completely free, is they can name a beneficiary in all of their accounts. So their bank accounts, their investment accounts, their 401k. You can actually just go in, login, pay no money, and name a person or multiple people. If you want to do it very cleanly, you can name a trust and then let the trust handle it. The main reason to do that is we have heard stories where folks have named their ex-girlfriend, ex-wife, ex-husband, family friend, and then they die and their spouse is a little confused as to why they're not getting the assets.

I think that most people make some of these decisions in their first kid, but they really make these decisions with their second child because it's less daunting. There's already so many things going on in their life after during their first child as I'm going through right now. That being said, you take stock of things. You come up with a basic trust, pour over will, you get it notarized. At Stewart, we send a mobile notary to your house or place of work, so you don't even have to go anywhere. You could also go to a local bank. A lot of law firms will also have you come to their office and they'll have multiple paralegals that are sitting there ready to be witnesses.

But you go through a series of questions with your partner and I think it can be a really empowering kind of relationship strengthening exercise with questions maybe ignored previously. So I hope that's helpful.

Oh that's so helpful and we've seen that before. Ex-girlfriend still is the Benny, very awkward situation. So it's like the exercise actually cleans up some of your prior decisions as well that you may not have even remembered that you made because in your 30s, it feels a little bit like, why the hell would I need an estate plan? But there's actually quite a few good reasons.

And you touched a little bit on the living will or the POA, which comes into play. And we've also seen clients be like, yeah, you know what? I need one person to be the caretaker. I need the other person to handle finances. Would not give that same responsibility for my child to one human. So being able to articulate those kinds of things can bring a lot of peace of mind to a new parent and like you said, becomes even more pertinent upon that perhaps second child.

I also want to touch on inheritance because that's I think just a very when you're in your 30s to even think about approaching inheritance as a conversation can be so daunting. And yet, when you're putting together a financial plan, it is like a really, really integral piece to have information around. You need to talk to your parents about those kinds of things, when you would get the money, how much you might get. Maybe they want to die with nothing and use it all. But having that information is so, so important. How do you suggest people approach the conversation around inheritance, whether it's with their parent or their spouse's family, or just even thinking about it themselves?

So one of my favorite questions in our onboarding is do you expect inheritance? Because I think it triggers a lot more than meets the eye. To your point, just to clarify how Die with Zero works, because I think this is important, Die with Zero doesn't imply that the generation before is going to consume all of the assets. It assumes that they're going to go to one of three things. The first is your own experiences.

Historically we've had quite a run in the market going back 17 years, going back 100 years, we've had a good run. I won't give any investment advice here, but I do think that we've had some rigid rules that are like the 4% rule and other things that have been honored or enforced or followed that have been a little bit conservative historically. And that's a backward looking historical statement. What that means is that a lot of families die with more assets than expected.

And so the concept of Die with Zero for me is to invest in your own experiences, to invest in giving to charity and seeing the impact of that giving. And the third is to give to your children and grandchildren or other relatives or friends and see the impact of that giving. Die with Zero is a very relatively new concept. I'm not going to say it's controversial, but it's certainly not mainstream. I would love to make it mainstream, but I think it's the idea that if you don't have the conversation, you'll never know.

And so I think that ultimately, given where asset prices are today, the cost of a home, the cost of an investment property and education, I went back and looked at what does it cost to go to college now? What does it cost to go to Graduate School? That's part of the estate planning, right? A 529 plan, estate planning is not just about death. So I think you first have to come at it and say, I'm not trying to pry. I'm not trying to pierce this veil of whatever it is that you have mom and dad.

But I want to prove to you that I am someone who works hard, someone that contributes. If you work at a large tech company, if you're growing your wealth yourself, you're showing that you're responsible. If you start by demonstrating what you're doing with your estate planning, I think that then makes it a lot easier to make the case that you want this to be what I call generational planning as a team sport.

This comes up a bit more in terms of tax planning, but the idea is if you give a small portion to your children as they're being born at the age of zero and one and two, and your parents give a bit to you at the same time, you're starting to slowly create bridges across generations. And it means starting small. The other thing I've seen is what's called intergenerational gift. And what that is, it's actually not a gift, it's a loan. And the loan is at what's called the AFR rate, which is the minimum amount of interest that the IRS requires you to charge. So it's not just a gift.

And that does a couple of things. One, your parents don't feel like they've just given you something, but they've given you a friendly loan that you can use to buy a house. And I think that that's becoming a lot more popular. And I think that could be the starting point of starting to broach the inheritance question rather than kind of coming in guns blazing with what I'm getting.

Oh my gosh, I love that. I love what you said about using responsibility and forethought as the jumping off point for why you're even asking. I would even suggest that financial planning is an incredible impetus to begin that conversation, estate planning as part of that. And we've found that for clients who approach their parents by saying, listen, I'm putting together a financial plan, I want to not over or under calibrate what I'm planning for or what I need to plan for to sustain would be helpful to understand.

And also I've often found that when you suggest how much you're doing, they become more generous. You can say, no, I'm good. Like you thought you might have wanted to leave me that because I needed it. I don't need it. I want you to enjoy it. And what a cool statement to be able to make to your parents that you took such good care of me. I don't need that inheritance as much as you wanted to maybe leave and you can use it for your own experiences.

It's a very large, robust, deep can of worms conversation. It can be really a lot to tackle, but I like your approach. When it comes to the like, what happens in reality in estate planning and like real life scenarios or how should you think about this process in the context of the realities of your day-to-day life? And in that context, why is it important to have a full living trust and pour over will as opposed to just a will?

I think that's actually a really important question. I think that's actually the question that I would think your demographic should be thinking about. Like a lot, like that would be the misinformation that I think people are getting. So what's the answer? The answer is life happens and so you create this will that is very basic for where you are when you have your first child or before you have a child at 31, 32, 33, 34. And then life happens, your assets, you inherit some money, your big tech stock gets bigger, your friends start up that you angel invested goes big and you have a real asset grouping.

You have a real bag of assets and you have this basic will that you never addressed. And so for me getting a trust done now that's correct. And really what you're looking to do means that you don't have to do major surgery every year, every couple years. If you do forget about it, which most people do, you at least know that you got it done and you can kind of at least sleep at night knowing that you have a substantive plan as opposed to a basic will. And so for me, if you have a little bit more to spend on it versus some of the free options, it's always better to have something that could capture a future state rather than just the next year or two.

Forward-looking makes sense. This has been so great, David. So many amazing things that we've talked about just to get the conversation started around estate planning because it is not just for old wealthy people. We've talked about a lot of heavy stuff. So we always like to end the show with a segment that I call Best Bite. I'm a huge foodie. I love to eat out or cook at home. I just love good food, and so I would love it if you would leave us with a recommendation, maybe something you've eaten recently that just blew your mind.

You've been traveling a lot. You've been all over the place. You were in Vegas and Hawaii. Where have you been? Next week Hawaii. But yeah, I was in Las Vegas for 10 hours yesterday. Vegas has got good food. What have you eaten recently that you want to put on my list? I think Oprah might have beaten me to this, but there's a pizzeria in Los Angeles called Pizzeria Say and I'm from Brooklyn, NY originally, so I can say this with some conviction. Pizzeria Say is truly the best pizza I've ever had. And it's just remarkable. Location is kind of central LA. So wherever you are, you can get there. It is very tough to get a reservation. Sometimes it's hard on walkups. They are moving to a larger location in Palms, which is in West LA or West side of LA.

But Pizzeria Say is unbelievable. And if you're in Los Angeles, it's truly worth it. I think it was just named either second or fourth best pizza in the world. We have it probably every month or so. I try to eat too much pizza. But if you're in LA, check out Pizzeria Say. It's tremendous.

Pizzeria Say, that is such a great recommendation. Haven't gotten that one before. I was just in LA so now I have to go back to try it. Are you a Margarita kind of guy? Cheese, pepperoni? What's your style? So they have a special Margarita that's excellent. And then they also have this merguez pizza, lamb sausage pizza. That is, it's a lot. It's a lot of flavors coming together at once. So we try to split both of those and hopefully we have more than the two of us so we can manage. But yeah, I think Margarita is great. And then maybe one or two slices of the specialty is enough for me.

Oh my God, that sounds delicious. I have to get out there. Thank you again, David. If people want to find you, if they want to follow the Stewart journey, where do they go? You can go to usesteward.com, so USE Steward St e w a r d dot com. And if you want to shoot me a personal note, I am happy to reply to them. If they're legal questions, I may refer them to estate planning attorneys, but it's david@usesteward.com. We always love to hear what families are going through, what new parents are going through because it's important for us to learn how we can best serve you and help you get better outcomes. So my lines are always open for you all.

Incredibly generous. Thank you so much, David. And that's a wrap on today's episode. If this conversation got your wheels turning, David and the team at Stewart have made it super easy for you guys to take the next step. They've created a special page just for our listeners with everything you need to start thinking about your estate plan, no matter your age or your bank account. So head to usesteward.com backslash the F word and remember, estate planning isn't just for old rich people, it's for anyone who wants to take charge of building their life and making sure what's what doesn't get lost in translation.

Alright, see you next time.

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