Stewardship Leadership with David York

Reading Time: 15 Minutes

In today’s podcast, we’re joined by David York as we discuss the power of stewardship leadership.

After the Interview:

About David York

David R. York is an estate planning attorney and CPA with more than 20 years of experience. He’s worked with 7,000 clients, including billionaires, business owners, celebrities, and entrepreneurs of all shapes and sizes.

He has represented first generation wealth creators, fifth generation wealth maintainers, and everything in between. He has also worked with individuals, couples and families across the wealth spectrum and countless non-profits looking to make a difference.

Early on, David recognized the characteristics of those who make positive impacts on the next generation and those who fail to do so.

Read the Transcript

Allison: Welcome back to the deliberate leaders podcast. I am your host and executive coach Allison Dunn. I am excited to introduce our guest today. We have with us David York.

He is the author of the Gift of Lift, Harnessing the Power of Stewardship to Elevate the World. He is not only an estate planning attorney, but he is also a CPA, which is an awesome combination, with more than 20 years’ experience with over 7000 clients, including billionaires, business owners, entrepreneurs, celebrities, and sports figures, and everyone in between.

He deals with 1st generation wealth creators to 5th generation wealth maintainers. He works with individuals, couples, families and nonprofits looking to make a difference in an all too broken worlds. Early on, David began to see a common traits and characteristic of those who make positive impacts in the world, and those who successfully transfer wealth with intentionality and purpose to the next generation. Sadly, those who fail to do so often with tragic results. David, thank you so much for joining us here today.

David: Yes, thank you so much, Alison, really been looking forward to this.

Allison: Me too. I love to kick these off with a deliberate conversation.

David, what would be your number one leadership tip for our listeners?

David: I would say to approach leadership as a steward and to me that is a person who’s fully invested in something bigger than themselves.

Allison: OK, so thank you for defining that. That is like a very much of the highlight of our podcast today. Let’s get started. We’re going to title this episode: Stewardship Leadership, which I’m actually going to ask David to maybe define a little bit further. It’s around the concept of harnessing the power of stewardship to elevate the world, which I think is a very beautiful admission.

What is the actual definition of steward leadership to you?

David: Yes, well, let me give you maybe the experience to kind of kick this off, and then how I see steward leader. Several years ago, I was working with Gail Miller. She’s the owner of the Utah Jazz. One of the wealthiest women in the United States, credibly smart, generous, wise person. We were working on a trust to keep the team in the state of Utah. We’re one team state, right? It means a lot to our state. So she was working to make sure that it stayed in our community.


David: We were working on a trust to accomplish that and in the midst of going over the trust, I just happen to ask her, I said,

“How will it feel to no longer own the Jazz?”

She just kind of casually looked up at me and she said, “Well, I don’t own the Jazz.”

I just kind of pause because, here I am. I’m an estate planning lawyer. She was, at the time running 70 different operating businesses. She knew the details of all of them. She’s very smart person but I had that lawyer moment where I just kind of paused and I said,

“No, actually you do own the Jazz.”

I’ll never forget, she stopped what she was doing. She looked at me and she said,

“No, I’m a steward of the Jazz.”

It was such a powerful moment, because I saw someone who had transcended ownership and here most of us, especially in a capitalist economy, we think of ownership as kind of the pinnacle and yet she had something that was beyond that and she just exemplified to me that notion, and again, I’ve spent the last 6 years thinking about this, researching it, studying it, writing about it and the conclusion I came to was, what I said, is a steward is someone who’s fully invested in something bigger than themselves and so she was all in, there’s no question, the time, the effort, the resources, but it wasn’t about her and that’s what I think makes steward leaders so unique is that they’re all in, but it’s not about them.

Allison: I think that’s a great definition and like example of someone who has transcended that. What a beautiful thing since, it’s a team sport, right? You can’t really own that.

David: Yes, exactly.

Allison: Even though you can, it’s difficult to look at it that way.

David: Yes.

Allison: Can you give me some other examples of what you would consider to be some of the world’s best leadership stewards?

David: Yes. I think about some of the characteristics of them.

The number 1 characteristic: is that they have a, what I call: a because-therefore, model for leadership. So most of us engage in what I call: an if-then relationship with the world. If I do this, then this will happen or if I invest in this, then this is the return I’ll get, and it’s very transactional.

If I do this for my employees, then they will do this and its very expectation based, it’s contractual, whether people know they’re engaged in that contract or not, right? And at the end of the day, it tends to be fairly unfulfilling, because you either get what you thought you were going to get anyway, or you don’t, and you end up frustrated or upset.

It can also kind of be controlling, because-therefore model is different. It’s the ‘because’ is your why, right? It’s, what is that thing that is bigger than you? And then what is your response to that and so because-therefore, model is just fundamentally different, I think of Nelson Mandela. Obviously, people know him and he was the face of the anti-apartheid movement.

What a lot of people don’t realize is, during his 27 years of imprisonment, in a harsh, terrible conditions, he was actually offered his freedom 6 times but each time it was conditional, he either had to leave the country, or he could never engage in politics, he could never speak in public and every time they offered him his conditional freedom. He refused it, because what he believed was that no one is fully free, no one is truly free, unless they’re fully free and so for him his ‘because’ was freedom. So therefore he couldn’t accept anything less than a full expression of that freedom and so that’s an example of a steward. He was all in, but it wasn’t about himself.

Allison: Thank you, those are two really fantastic examples, David.

Can you help kind of explain and or talk about the steps to foster a stewardship type of mentality for our business owners?

David: Yes, to me, it starts with knowing who you are, what you value and what you believe.

I think that clarity of purpose is so critical and it’s so valuable. It gives us direction and honestly, one of the things I find about stewards is they care more about direction than destination. In other words, so many of us were focused on, once I get to this point, then I’ll be happy again, right? If I get a million dollars in the bank, then I’ll be happy. If I can sell my business at an 8 multiple, then I’ll be happy.

It’s about reaching a destination. Stewardship to me is ultimately about a direction and that’s a draw that comes from that clarity and invariably, and I see this in estate planning, I see this in successful wealth transfer with successful business leaders. They know their ‘why’ and then their ‘why’ drives everything else but it’s interesting, because we live in information age, right? We have access to all of this information at our fingertips, and yet, so many of us struggle with knowing who we are, what we value and what we believe. I think it all started, that’s kind of the wellspring that everything else comes from.

Allison: David, obviously, my company’s name is Deliberate Directions. Deliberate leaders is about setting a direction so very much resonates with what you just said.

Do you find that when you’re working with your clients, that they have a sense of what their core purpose in their ‘why’ and what they value because that drives so much of that direction?

David: Yes, it’s interesting, I see that in their business life. I mean, you cannot be successful in business without having clarity. In fact, it was funny. I was talking with a group of really successful business owners and I asked them, I said, 

How many of you would credit the success of your business to your articles of incorporation?

They all just laugh. They all laugh, they were like 0%. We credited 0%. I said,

Why are you successful?

They said,

We knew the problem that existed in the world. We knew how we wanted to solve it and we surrounded ourselves with great people.

They knew their ‘why’ they knew their ‘who’ and that drove everything else and I say that to say we focus so much on strategy and structure, when it’s really about clarity of purpose but that said, I see so many clients, they know how to become wealthy, they don’t know how to be wealthy and they don’t know how to take what they do so well at work, where it’s all about intentionality, and purpose and clarity.

They have their elevator speech for their job, and ask them what the elevator speech is for their life or their family and they stumble, because it’s the tyranny of the urgent, right? You’re so intentional at work, and then you go home, and it’s about getting dinner made, and getting the kids off to lessons, and homework, and chores, and other activities and so, I find a lot of clients who struggle with finding that intentionality in life, because we just don’t think of it in those terms, like we should and yet, the same principles of a successful business are the same in life, when it comes to wealth planning, all of those things.

Allison: Yes. It’s not uncommon to sit in front in front of someone, and they have a very clear idea of what their business or their financial goals are, but not necessarily those of their partner and or for their family.

David: Yes, absolutely.

Allison: That very much resonates with me and as you say, it’s out of balance, if you don’t have it. For the long term plan, for sure.

David: Yes.

Allison: You kind of identified 4 pillars for building company culture and how steward mindset can strengthen that. Can you outline those for us?

David: Yes. To me, one of the areas that stewards can have such a positive impact is when it comes to culture. If purpose is your direction, culture, to me is the current that it swims in, right? It can either be a current that helps push you towards your goal, or it can be an impediment.

My wife and I, we love bicycling. There’s nothing more empowering than a tailwind, you have that tailwind behind you just going and yet, there’s nothing more discouraging than a headwind. One of the things that I realized is not only do my clients who are most impactful, both in business and in their communities and their families, not only do they know where they’re going, but they have great culture, and I see 4 pillars of that. First is communication. That involves both sharing and listening.

To me, the sharing is that investment, but the listening is that transcendence, because a lot of us want to speak and not many of us want to listen, and it’s just inherently other centered. In fact, I think that’s more than anything else. Our society has a dearth of asking questions and I think asking questions is one of the most relational things you can do.

The second, its cohesion, the families, the organizations that we see the most successful. They have a strong sense of cohesion or commonality and that’s an interesting one, because for so long, we relied on social cohesion, where we all thought the same, look the same, voted the same, believe the same and diversity is such a great powerful tool, but it can actually be sometimes a hindrance to cohesion and so I think it’s important to embrace the diversity and the uniqueness, but also realize well are there sociology or psychologists call it: Task Cohesion. Let’s not try to all be the same, but what can we accomplish together. Cohesion to me is having that clarity of direction and then engaging in that.

Third is identity, knowing who you are, but then knowing that about everyone else, and then last is impact. That’s when you combine both purpose and investment and that, one of the things about impact, and I tell this with especially my high net worth clients, but really everyone. Impacts not optional. You can’t choose whether or not you’re going to impact others and the more wealth you have, the more impact it’s going to make. So, if it’s not optional, it’s at least be intentional but to me, culture is built on those 4 pillars of communication, cohesion, identity and impact.

Allison: Thank you for wrapping those up. I was like, going to repeat them back so that everyone caught them but those are fantastic pillars. Thank you very much.

You talk about the eight-ness and realities of money, meaning and happiness in the book. Can you just kind of give us some insight into that?

David: Yes, it’s interesting and this is drawing from 25 years of doing estate planning and wealth transfer and I always tell people, if there’s one thing that I’ve learned, it’s that we value things based on what they cost us.

When something doesn’t cost us anything, we just simply can’t value it like something that comes with cost. That’s why I think the average American inheritance is spent in 18 months. So what people accumulate over the course of their lifetime, is on average consumed by the next generation and 18 months and you say, ‘OK, well, that’s the average American’ that’s not true of the wealthiest.

Studies have shown even among the wealthiest Americans, the half-life of wealth is 8 years. You take someone who inherits $20 million, statistically speaking in 24 years, so basically, one generation, on average, they have 2 and a half million dollars left and it’s because there’s no cost associated with it and there’s no transcendence. In other words, I’m going to give you something that costs you nothing, I’m going to give no meaning or purpose behind it and then we wonder why it’s just consumed.

Allison: That’s an incredible statistic.

David: One of the myths, I would say when we think about cost is that $1=$1. The reality is, it’s just not the case. They did this really fascinating study, bunch of college students where they sold them, these mugs that were worth $7 and they sold them to the kids for $2. Half the kids they sold it to with a credit card. The other half, they made them pay $2 of cash and as you may know, there’s been studies out there that show, if you pay cash, you have pain receptors that actually go off in your brain, you experienced loss and pain, even though it’s just a minute that you don’t experience with a credit card, which is why in general, we spend more on credit card but that wasn’t the experiment. They then went back to the kids and they said,

“Hey, we’re sorry, we actually oversold these mugs. We want to buy them back from you but you can set whatever the price is.”

 There were $7, you bought them for $2. What would you sell them back for? Well, the half that bought it with credit card, were much more willing to resell the mugs and in general asked $3.83 for them, the half that paid the same $2 but they paid with cash and they felt that tiny bit of pain, were on average, much less willing to resell the mugs and on average, asked $6.71 for the mugs.

They showed that with other things as well when it came to charitable giving and so we tend to think that we try to make things as costless and as simple and as easy as possible on people and we don’t realize we’re actually undercutting value when we do that. There’s actually a few brands that have been looking at ways to make it harder for people to buy their products, use their services, because of that, that value [Phonetic] proposition that comes with that cost and so I think it’s really important to understand the importance of cost in relationship to value.

Allison: When you’re kind of highlighting that concept with the transition of wealth that is in massive proportion happening at this point in the world, I think just in general, like the largest it’s ever happened.

What are things that we should be thinking about, as wealth creators and wealth maintainers that has that value and the impact that we’re looking for?

David: Yes, it’s a great question and just to emphasize the point, in July of 2019, researchers, the statistician said that at that moment in time, there actually became more millennials than baby boomers because the baby boomers are slowly shrinking but right now we have about 70 million baby boomers, who collectively have about $60 trillion.

They’re in the process of beginning to transfer that to 70 million millennials, who currently have $5 trillion. It’s going to be the largest wealth transfer in the history of the world and for the most part, it’s undirected and unintentional and it’s being transferred to kids who are unprepared and uninformed but I think what I experienced and what I see is that, again, if we value things based on what we cost us, a lot of my clients, especially higher net worth, they are focusing far more on opportunity transfer, as opposed to wealth transfer, and other words.

Yes, so just partying and encouraging things like education, entrepreneurism, matching funds for home ownership. Instead of simply just giving kids unearned or undirected money, which is typically consumed, providing opportunities that come with a cost element, and then maybe it’s time, maybe it’s them matching some dollar amount, maybe it’s matching charitable giving, those kinds of things but by focusing more on opportunity transfer, we don’t undercut the cost and we can actually maintain value and then what we do is we create opportunities for them to create their own wealth, and then value that wealth itself.

To me, it’s actually going back to what I see is the original roots of wealth transfer, which was more opportunity based than it was simply transfer for consumption.

Allison: I look back at examples. My parents choosing to say like, we’ll help you with your first two years, but the last two years are up to you and that made all of the difference.

David: Yes, absolutely and it made you focus it know. Nassim Taleb, wrote this great book called Skin in the Game. He talks about cost and the importance of costs, and one of those is that it makes us adapt, and it makes us work hard, right? Like, why did you finish in 4 years? Because you had to finish that, you were the one paying it. I had a friend who, he was on his parents time and he was 7 years into college, then all that money ran out and then he had to figure out what he wanted to do and he finished in like a year and a half when it was on him but it’s because it didn’t cost him so he just didn’t value it.

Allison: In your work with clients on either whether it’s estate planning or financial wealth accumulation, what are some of the tools that you are using to help them take stewardship into consideration or amplify it, assuming that they already had that in some way?

David: Yes, the mantra that we try to use, really, for anyone but it’s especially true in the high net worth and ultra-high net worth is this resource where you value. I think it’s a great way to live your life but to do that, you actually have to know what you value.

Part of what we do is we actually take clients through an experience, where we help them understand the individual core values of every person in the family and then the shared core values because, to me, strength comes from unity and diversity. It’s not about us all being the same or thinking the same and I think uniformity has been a big emphasis and families in the past and businesses and organizations, which I don’t think is actually ideal, but it’s in that Venn diagram of the uniqueness of a group, whether it’s a family or a business, where can we agree and then where can we each uniquely expressed those shared values.

We actually start with that and then we just simply resource those. We don’t say that we support education, what we say is we value determination, we value knowledge and wisdom, we value empathy and so this is how we use our resources in furtherance of that, so it’s not about charitable giving, it’s about empathy. It’s about compassion. It’s about generosity and then we drive from that. So that’s what we try to do is help clients understand that ‘why’, and then let that drive the ‘how’.

Allison: Fantastic. I love that. Congratulations on the release of your book.

David: Oh, thanks.

Allison: That is exciting stuff. Who did you write it for?

David: Well, I wrote it, I think every author a certain extent right for themselves. Right? I wrote to answer the question of who is a steward. It’s both the blessing and the curse of being an attorney and CPA is everybody thinks that when I use the word steward, I’m talking about money, taxes, and yes, those exists and I live that every day but I wrote it as a different mindset and as an alternative to consumerism because I think a consumer is the opposite of a steward, there’s no investment, and there’s nothing bigger than themselves.

Unfortunately, we see the effects of consumerism all over, but for a lot of my clients, they saw the problems of consumerism, so they’re like, ‘Well, I’m just going to give my kids less’ but the opposite of consumerism isn’t minimalism. The opposite of consumerism is stewardship and so that’s why I wrote.

I wrote it for people who want to have a different mindset and mentality, than just the typical consumer mentality that it doesn’t just exist in the marketplace. It exists in our schools, it exists in our organizations, it exists among employers and employees and so that’s who I wrote it for.

Allison: OK, thank you for writing that. I like the kind of the consumerism isn’t minimalism, but stewardship, that’s a really kind of a powerful statement and a great way to look at it as well.

What is the best way for folks to either connect or follow you or find your book?

David: Yes, so the book The Gift of Lift, it’s on all the usual sites, Amazon, Barnes and Noble. There’s a Kindle version but you can also go to I’ve got some articles there on culture and this wealth transfer, I’ve also got a link there to a talk I did on wealth. You can also just go to If you want to see an 11 minute presentation on maybe a different way of looking at wealth transfer.

Allison: I watched it. I highly recommend it for those who are TED Talk fans. It’s a good one.

David, thank you so much for joining us here today. I’ve appreciated our topic and viewpoint.

David: Yes, thank you very much.

I'm Allison Dunn,

Your Business Executive Coach

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