The Kingdom Investor

54 - Generational Generosity: Passing Down a Legacy of Giving | Crosland Stuart

March 07, 2023 Daniel White Episode 54
The Kingdom Investor
54 - Generational Generosity: Passing Down a Legacy of Giving | Crosland Stuart
Show Notes Transcript

Do you make a positive impact in your community through your generosity? Would you like to cultivate a legacy of generosity to pass down to your descendants? Join us as we sit down with Crosland Stuart, founder of Crosland & Company to discuss the importance of generational generosity. 

In this episode, Crosland shares how her family instilled in her a commitment to stewardship and generosity emphasizing the importance of integrating faith into daily life. She talks about the challenges of passing down generosity to the next generation while highlighting the importance of educating and involving children early on. She reflects on her personal journey of generosity and how investing time in people's lives through discipleship and mentoring can have a greater impact than just monetary donations. Listen to the inspiring conversation now as you continue to enrich your journey through stewardship and generosity. 

Key Points From This Episode: 

  • What is one thing that Crosland is passionate about or excited about right now?
  • Crosland gives snapshots of her background and upbringing.
  • Crosland discusses generosity across generations as lived out within her own family.
  • Crosland talks about how other foundations succeeded at passing generosity down to the next generation.
  • Crosland reflects on past failures of not practicing generosity well and the lessons learned from them.
  • What are the ways that we can practice generosity outside of the typical money-giving?
  • Crosland discusses the idea of good citizenship which stems from faith and generosity to the local community and has been passed down by Crosland’s grandfather to the succeeding generation. 
  • An example of acts of generosity that were passed down as a legacy to the younger generation.
  • Crosland’s thoughts on the great wealth transfer and how we can turn it to be a blessing.
  • Crosland answers the mentor-minute questions.


“Generosity is not a function of wealth; it is a function of the heart.”

“It's not our dollars that are going to make the difference, it's our time. It doesn't matter how big your checks are, you need to be investing in people's lives.”

“Practice humility, generosity, gratitude, and joy. They're like muscles, if you don't use them, they atrophy.”

Links Mentioned in Today’s Episode:

<a href="">Nuance Podcast</a>

Legacy, LLC website

Crosland Stuart on LinkedIn

Perception Ministries

"Knowing God" by J I Packer

"Humility" by Andrew Murray

"Gentle and Lowly" by Dane Ortlund

The Kingdom Investor Podcast on LinkedIn 

About Crosland Stuart

Crosland Stuart is the founder of Crosland & Company, LLC which is engaged in multiple business lines that includes communications, literary representation, foundation consulting, and family business interests. She is also a literary agent and project development specialist with Legacy, LLC. She also serves as chairperson of the E.B. Kennedy Scholarship Program Board of Directors of the E.C. Stuart Foundation which has partnered with Erskine College to annually award full scholarships for the past sixty years. 



ANNOUNCER: Imagine taking your generosity to the next level, impacting more lives, and leaving a godly legacy for generations to come. Get ideas and strategies to do just that when you listen to these personal stories from high-level Kingdom champions.

The Kingdom Investor Podcast showcases business leaders who have moved from success to significance, sharing how they use worldly wealth for kingdom impact. Discover how they grew in generosity, impacted more lives, and built godly legacies. You'll find motivation, inspiration, and practical steps to grow as a Kingdom Investor.


Daniel White (DW): Hello and welcome to The Kingdom Investor Podcast. This is your host Daniel White. Today we interview Crosland Stuart. Crosland is the founder of Crosland & Company. She is a farmer at heart, utilizing a leadership style of cultivating, preparing and planting. In this episode, we talk about generosity across generations. 

If you have enjoyed the show, help us reach more listeners by sharing with your friends and writing a review. And now without further ado, let's jump right into the show.


DW:  Crosland Stuart, welcome to The Kingdom Investor Podcast. How are you doing today? 

Crosland Stuart (CS): I'm doing great, Daniel, thanks so much for having me.

DW:  Absolutely. I'm excited about our conversation today, to hear a little bit about your story and talk about what generosity means to you and kind of how you've seen it modeled in your life, in your family. 

CS:  Well, generosity is one of my favorite topics. And so I love talking about that. Looking forward to today.


DW:  So, what is one thing that you are passionate about, or maybe one project that you're excited about right now?

CS: Oh, gosh, I have my own company. And it really has three main business lines. I'm a literary agent, I do foundation consulting, and I do communications which primarily involve content creation, management, and strategy in there. And so I've got a lot of exciting projects on all fronts. But one that's really interesting is a new podcast that I've been asked to participate in. So, I'm usually on your side of the table. It's a little different to be on this side of the table.  But a client I work with, The Collaborative, has just launched a podcast called Nuance. And it's all about public theology and what that looks like in the public square. So, really, public theology is just our faith outside the church, and how it gets integrated into life. And there's no 12-step program. There's no manual. I mean, we certainly have the scriptures. But a lot of life is lived in the gray, in the nuance. And so we're trying to have a dialogue and a conversation about that. And that's a lot of fun for me.

DW:  Yeah, I'm excited about that. And, I've added it to my list of podcasts to listen to. So I'm looking forward to it. So, would you give us maybe just a little bit of background and context around your life and maybe recap your background?

CS: Sure. I am a fifth-generation native Floridian and probably go back that far in terms of Christian commitment as well, which is just an amazing thing. And so I have greatly benefited from generational faith. And we'll talk later about generational generosity as well. There's just been a beautiful legacy at both of those things. I've had my own business for a number of years, and there's a lot of the day-to-day grind I don't love but I love having my hand in a lot of different pots. And really the thing that kind of ties all of this together is I love coming alongside people and helping them realize their dreams or goals or expectations, whether that's in bringing a book to market or getting, you know, content out where it needs to be so I just love doing all that.

DW:  Yeah, that's really neat. So, can you share maybe a little bit about what that generosity across generations looked like for you and, maybe talk a little bit about that?


CS: Sure, I've been really blessed to be born into a family where generosity was really at the top of the list. It was not uncommon to have discussions about stewardship and giving, and the church around our dinner table. I think one of the greatest things my family gave me is their sincere commitment to the church. The church was a part of our life. And the week really revolved around church. But my parents and my grandparents, and then what I know about my ancestors before me, did not stop there with their faith. This idea that their faith was siloed off for Sunday activities, or Bible studies, or whatever we want to put in that silo like we see so much now was not part of their world. And they would never have thought about it like that.

CS: I mean, my great-grandfather was integral in starting communities in the Central Florida area. And he would look at a community and go, okay, well, what does a community need? It needs a Methodist church, or Presbyterian Church, a Baptist church, an Episcopal Church. And so, he helped start all of those. Because a vibrant community that's flourishing has to have churches. So both my father and my grandparents, and my mother as well, but we're really invested in the community. And that may be easier when you're in a smaller community like I grew up in, but I do think, I live in Orlando, or greater Orlando, and you have options all the time about making contributions. 

CS: And so, there was this idea that we are to be good citizens, not just good stewards, not just good church men, but we are to be good citizens. And that comes out of our faith. Not some, I don't know, some kind of false civic duty, but it was rooted in their faith. And there was a lot about looking at a community and saying, what do you need? And so I saw that in action in a number of different ways, in both my grandparents' lives as well as my parents. It left a huge impact on me.

DW:  So, you do a lot of work with different foundations and consulting with foundations. How have you seen other foundations succeed at passing generosity down? Or, well, I guess, yeah, passing generosity down to the next generation?

CS: Well, nowadays, we have all kinds of foundations. So, lots go beyond just family foundations, which is primarily what I'm most familiar with. But I'll tell you when I go to conferences, that's a big question, the one you just asked. How do we bring in the next generation? And it's not easy. You know, the next generation has lots of other opportunities. Foundations are not the only means by which you can give. There are lots of other tools in the toolbox, so to speak, in this day and age than there were a number of years ago. Nowadays, you wouldn't necessarily start a foundation unless there was a huge purpose you are going to put in because I think other concerns have been raised as well, like, what is your sunset plan? You know, what if the next generation doesn't want to carry on your vision? And that's a really important thing. Just look at Harvard and Princeton. You know, they're having huge issues. They've got enormous endowments, but they have gone way beyond, and not necessarily in a good way, what their original founders intended.

CS: So, you know, anytime you think about bringing up the next generation, it's a lot about education. It's a lot about bringing them into the conversation early, you don't want when they hit a family board for that to be the first time they thought about giving. And it becomes tricky. Because what if two of your four children are really responsible and the other two aren't? Do you leave two out or bring them on? You know, they're just all kinds of things. I think one of the best structures I've ever seen was sort of a quasi-foundation board that was created with the Gen three or Gen four groups. They had real decisions to be made so it wasn't just a shadow board. But it allowed them to practice, so to speak, and to begin thinking as a board member, because when you have a board hat on, you have to set aside your personal desires, and in some cases, your personal preferences, because you make a commitment to abide by what the board agrees to. So anyway, it can just get very complicated very quickly. But I think those are all really good conversations to have. 

CS:  The reality is, whether you have a foundation or not, those are the conversations we ought to be having with our children. And I don't have children. So the young people that I'm around, I ought to be engaging in those kinds of conversations, talking to my nieces and nephew about those kinds of things. And as parents, you need to be modeling it, for sure. And then having conversations with your own kids. I can remember being little, and given a little tiny allowance. But I was always brought into my dad's office, and there was a conversation about how much of my allowance is gonna go to the church. And that's where, you know, it was just a great picture, that generosity, I said this to you before, but generosity is not a function of wealth, it is a function of the heart. And as an adult, I have not learned that lesson well. And as I look back, I, you know, I've had to ask for forgiveness, because in certain stations in life, I have not done generosity well.

DW:  Yeah. So I guess, can I ask maybe some of those failures, or maybe lessons learned? What can we learn from that?

CS: Sure. There have been times when business was not good. There were times when I thought, okay, Lord, I just need to shut this down because I'm not making my bills, I can't keep doing this. And I was really frustrated in those years, that I couldn't give more. And I look back on that and think if generosity is not a function of wealth, which I don't believe it is, then I should have been content. I mean, Paul tells us in Philippians, to be content in plenty and want. And that's a really important thing. It's been a really important lesson for me. There are other places in scripture where scripture says we are to bloom where we are planted. And I think that includes the resources that we have at our disposal. And so the joy of my salvation, first of all, should be on display every day. And it should not be a function of what's in my checkbook.

CS: And so, and, you know, we certainly are all fallen. And so our motives are never pure, but we, when we give, we need to give out of joy. And I know a lot of people who give a lot of money and they don't necessarily, they're not very joyful, you know, and so it's a privilege to be able to give, um, it's a privilege if we give and get to see the fruit of that. We don't always get to see it. Sometimes we're called to be those cathedral builders, who are laying brick after brick and they would never see that church built in completion in their lifetime. And so there is a sense of contentment and peace about where God has made right now. And whether that's one zero behind a digit or three or four, whatever that season is. Give and give with great joy and thanksgiving. And God knows when we're faking it. So we need to pray that we have more joyful giving, you know.

DW:  Yeah, absolutely. So, can you maybe expound on some other ways that we, we should be generous, or can be generous, or get to be generous, that are outside of, you know, what we typically would think of as, you know, wealth, or giving money?

CS: You know, somebody told me years ago, and this man was quite wealthy, that for most of us, it's not our dollars that are going to make the difference, it's our time. And so I think, asking yourself - where am I giving my life away? And it doesn't always have to be a 501(c)3 organization. I think we get caught up in those kinds of things. Maybe there are people in your life who you need to be pouring yourself into. So, it's about doing that, making investments in people. As we, in fact, I would argue that it doesn't matter how big your checks are, you need to be doing the latter, you need to be investing in people's lives. One-on-one has nothing to do with a check. 

DW:  Yeah, so I, previous to this, I recorded an episode with John Rinehart from Gospel Patrons. I don't know if you know him or not. But one of the things that really stood out to me, that he said is that in his 20s, somebody invested, a pastor, I think, invested in his life. And what he said is, he basically deposited his life into mine, because the investment was over, you know, a series of years, on, you know, multiple times a week, you know, just doing life with him, taking him where he went, introducing him to all of you know, his mentors, and just pouring life into him. And now, you know, John's been able to impact so many more people through, you know, his books and his ministry and everything, and it's just so incredible how, you know, really, God can multiply that time that we've invested or deposited into other people's lives, you know, through discipleship, and, you know, just mentoring and investing in them. So yeah, I really like where you're going with this.

CS: Well, I think in the business world, we think, a lot, particularly Christian business folks, we think a lot about this idea of compounding. And it tends to be more about, well, how am I going to strategically write that check? And I'm all for that, I'm the kind of person that I believe in investing in one direction for a long time. I'm not kind of, personally, I'm not a big shotgun approach. But that's a personal thing. But I think we forget that when we invest in people, there is a compound effect we can't even begin to imagine. I look at the people who have made a difference in my life. And the same thing in their lives, people poured into them. In some cases, in one of the cases, a gentleman told me years ago that somebody had paid for him to go to seminary. And he's having a huge impact on people. So I think, pouring ourselves into one another really ought to be a part of the warp and woof of our lives. And that ought to be as we think about what kind of legacy we are building or leaving, I would hope that that would be there. And that is true, even if you're the CEO of a big company. Because the reality is, you may have more free time than others do.

DW:  Right. Yeah. Yeah. And I know it's true in my own life. You know, there have been people that have really invested their lives into me. And I've drastically, you know, changed the trajectory of my life.

CS: Yeah. That's so amazing. That's great. What a wonderful testimony.

DW:  Absolutely. So, I want to go back to this idea of being a good citizen, what it means to be a good citizen, and how we can be generous in our local community. Can you talk a little bit more about that? I know you're talking about, I think, it was your grandfather, right?

CS: Yes, you know, every community is different. But I do think you can sort of sit back and ask yourself, what does my community need? What is lacking? Or what does my church need? How might my church serve its people, and the community better? My father was really involved in Rotary. And so the Rotary Club and Rotary International, you know, they serve the community in all kinds of ways. From service projects, they used to fund a home for kids who may have been in trouble but more often than not, it was their parents that were in trouble, to things like there was a very large county fair in my hometown. And Rotary really invested it well. The fair was all for kids who were either in 4HFFA, FHA, so it was all 18 and under. And there were hundreds and hundreds of kids and making an investment in that fair, that provided the opportunities that it did. I mean, was just fabulous. I say that as a participant.

DW: Yeah, that's really neat.

CS: So, you know, I think you can also invest in schools. Even public schools, they always need additional resources. I know someone who just, you know, went to a local school principal and said, what do you need? I've got about $20,000. And they said I need a computer cart with five computers on it. And so that investment was made. You know, or that number is probably off by more than $10,000. But, you know, so I think you can look at your school system. I think, also people ought to give where their passions are. Again, I think that goes to the joy of giving. Education is a big thing for me, it was a big thing in my family. And so I kind of lean towards education. But there are lots of different ways. And it's not always about investing in something that's got Christian in their tagline. Like, I know, in my hometown, there is a need for a women's shelter for abused women, it's sort of you go there for a temporary number of days, and then you move on. So, you can get the protection that you need.

CS:  So, I just think, and if you don't know, ask people who were involved in your community. It's just not that it's not that hard. I think the hard thing is, is that we don't tend to stop and ask ourselves those constant questions. I would go back and say, we need to ask ourselves that same question about who are you investing in? And if you're not, you need to survey your landscape and go to it. I have a friend of mine, and she says that she has the ministry of availability. And it's true. All of the whole time I have known her and I've known her now probably for 30 years. She makes herself available for young girls and young women who need counsel, need a shoulder to cry on, need to understand, you know, how God has them in this particular place. Anyway, I just think we need to think about how do we love one another well.

DW:  Do you have a particular story that stands out to you about generosity, whether that's from your family, or either even people that you know, or colleagues, or anybody?

CS: Well, one story I have, and I feel like I can tell it because I didn't have anything to do with it really. And it was my grandparents years ago in honor of a man who they just love, was actually kind of a great uncle for me, started a scholarship in his name. And I actually ended up running that program for about 19 years. But even before I got in the mix, my grandparents, were just trying to be faithful, and good stewards and generous. I mean, they were some of the most generous people. They were all that's good about being Southern, you know, they were gracious, they were warm, they were friendly. When you had a conversation with my grandfather, he made you feel like you were the most important person in the world and there was nowhere else he would rather be.

CS:  And they started this scholarship to honor basically the man who raised my grandmother and it ended up it was her actual paternal uncle because her father had died at an early age. And so they were just trying to be faithful. But over the decades, more resources became available, that scholarship grew. And as they were trying to be faithful, and then generous to say, to the institution, because it was, I won't go into the details, but it was privately endowed outside the institution. But they will go to the institution and say, can we design this, so it's a recruiting tool for you as well? Well, not only did it become the most successful recruiting tool they've ever had, it broke all the statistics on recruiting and how you invest your money and that kind of thing.

CS:  And by the time the program ended, while we were just awarding two scholarships, and they weren't full rods, but minimal compared to the next summer, I'm about to tell you. The institution was using that program to give away over a million dollars in scholarship money. We talked about a compound effect. Now, when they started that scholarship program, they weren't thinking about compounding. They were thinking about, we want to honor this man. We want to help this beloved institution. And we want to try to be faithful. And faithful they were. And by the time I got there, I'm the third generation and I just got to tweet things. It was a blast.

CS:  So, just to me, it's a picture of, I feel like, I feel like today, there's a sense in which we got to know what's on the horizon. Rather, let's just be faithful and see what God might do. Now, I'm a planner. So I'm all for vision and big ideas. But as somebody said to me recently, more often than not, God doesn't show us what's on the horizon. God shows us a breadcrumb that's right in front of us. And my grandparents and my father, they just kept making bread crumbs. And for me, I need to hear that and think about that more often. Because I skip over, I'm like, Okay, where do you want me to go? versus what's the next right thing to do? I don't know if that's what you were looking for but that's...

DW:  Absolutely, yeah, that's really helpful. And yeah, I really liked that. And just thinking about how like, you know, we always want to do something really great and really big for God. And it's like, well, just do be the steward of what I gave you first, and then we'll move on to something else.

CS: Yeah, that's exactly right.

DW:  Yeah, that's good. So, I want to ask you about your thoughts on the great wealth transfer that everybody's talking about. And, and just, I mean, there's probably a lot of danger to it. There are probably a lot of, you know, blessings that can come from it, but what are your thoughts around that and how can we maybe increase the odds of it being a blessing?


CS:  Well, I think for believers, I mean, secular non-believers need to think this too but we need to think about this is not ours. You know, we need to come at it with open hands. I think about that to him, nothing, nothing do I bring to the cross I claim. I have just butchered that verse. Sorry, that line, but nothing in my hands I bring but simply to the cross I claim. There's the line. You know, it's gonna happen, the great transfer. I do think you have some people giving more and more money away so that it doesn't transfer as much. Oh, also think we need to be thinking what's, what's the goal? You know, what am I going to do with the wealth? Am I going to get the second or third house? I mean, I don't have a problem with wealth. I'm all for capitalism and the success of that, but. And when I give, am I giving strategically? I probably shouldn't even use that word. But I don't know more and more I'm giving to people.

CS: I mean, they have organizations, but I've already I can see the fruit of what they're doing. And in most cases, they don't have much at all. So I don't know that I don't think this is a hard and fast rule. But somebody sent it to me a long time ago. And I've adopted it as part of my philosophy of giving. And that is, I love the institutions I have attended and have paid lots of tuition dollars but that's not where I'm going to invest. Now, none of them were Christian institutions. So I do invest in Christian institutions. But you know, the big public universities, they have lots of donors. And they have a lot more places where they can go get money, where the organizations that I give to whether it's the Geneva School, which is a Christian, classical school, or Mars Hill Audio, which is basically a Christian podcast before there were podcasts, with Ken Myers, or, you know, Kenny Crosswhite and Perception Ministries, whatever it is, their field of donors is much smaller than a public institution. And so, I do try to think about that and think, you know, maybe it's a better investment. Again, I'm not opposed to investing in public institutions. But for me, I do try to think about, who can I help that isn't going to automatically get it.

DW:  Yeah, yeah, that's good. All right, as we get to the end of this episode, before we enter the mentor minute, is there anything else, any other advice that you can give us or wisdom that you can share?

CS:  Oh, gosh, you know, I don't view myself as a dispenser of wisdom. But there are lessons I've learned on the path. And the biggest one is humility. And that's something that has to be practiced. Just like, generosity has to be practiced, gratitude, and joy. So, you know, they're like muscles, if you don't use them, they atrophy. 

DW:  All right, jumping into the mentor minute, who is the most influential person that you know, and how have they impacted you?

CS:  Oh, my goodness. I've got a handful. So if any of them are listening, don't be offended if I don't name you. But I'll tell you, I would say Kenny Crosswhite. He has a ministry called Perception Ministries. At the moment he is primarily serving as a personal coach and does a lot in the NASCAR community. So, when Tony Stewart was racing, Kenny was kind of NASCAR's answer for anger management, that kind of thing. But what I love about Kenny is, he's always learning. He's in the word and knows a word, maybe better than anybody I know. And he is as comfortable with a guy sweeping the hall, as he is with the owner of the race team. And he treats everybody the same. And I've seen it in action. I've known him for decades. His wife is just as lovely. And I mean, even to this day, when I have an issue, I call him and go, What am I gonna do with this? So? But I do have there there are others on that list, but he would have be a big one.

DW:  Yeah. And then what is a book or podcast that has changed the course of your life?

CS:  35:59

Two books, one would be “Knowing God” by J I Packer, it's a classic. It's been out for decades. Actually, three books, the second book would be “Humility” by Murray. I mean, it was written years and years ago. It's one of those books. While I don't, my desire is to read it every year. It's pretty short. But you don't have to believe everything he says. But man, it's really good. And then the second, the third one is a book I'm reading now and that's by Dane Ortlund book, "Gentle and Lowly". And it's all about who Christ is. Have you read that?

DW: Yeah, we did a study through it last summer. It was really good.

CS:  Somebody said to me the other day, they think that maybe one of the best sort of modern books or is and I would agree, the more I read, and I've been reading it, sort of devotionally. So I'm kind of marinating in it. And oh, it is great stuff.

DW:  So, Crosland, thank you so much for coming on the podcast and sharing your wisdom with us and your insight. Is there anything that we can be praying for you about?

CS:  Oh, yeah. I would love for you to pray for this new podcast, Nuance. It launched last fall. We're doing it seasonally. So there are six episodes a season. And we will start season two, I think, right at the beginning of March, and we're already recording for it, interviewing. And because it's on public theology, that first season was all about sort of laying the foundation. The second season, we wanted to do something that's really in front of people who are in the workplace. And so we're looking at gender identity issues. Well, we'll have the conversation around that. And just so people know, one of our goals is to kind of dial down the temperature so that we can have a conversation. We are not setting ourselves out as somebody who knows, people who know all the answers. We don't know the answers. Some of the people we've interviewed conflict on certain issues, which I think just shows they're complicated. I think for some of the issues, there's freedom to have differences. It's one of these things that if you're in business, it is staring you in the face, and I don't think the church is talking a lot about it. And there's some people would that would just assume, put their head in the sand. So we don't want to be doing that. And I think the big goal with it, people would come away from the podcasts with holy confidence, knowing that they can lean into what they already know and the truths of the Scripture. And then for the things that they don't know, the Holy Spirit and God is going to show up and provide the breadcrumb. 

DW:  Yeah. That's good. All right. Well, can I pray for you right now?

CS:  Oh, that would be great. And thank you so much. 

DW:  Absolutely. Let's pray. God, I thank you and praise you for just this time. And for Crosland and her family, her legacy of generosity. Lord, you have been faithful to her family for so long. And we just get to see the fruit from years of faithfully walking with you and pursuing you and putting you first in their lives and just how many people that's impacted, how many lives have changed. Lord, we just thank you for that. Lord, we pray for this new podcast, Nuance, that it would be a benefit to all the listeners and that they would be able to use that as a tool for ministry to advance your kingdom. We ask that your kingdom would come and your will be done on earth as it is in heaven. In Christ's name, I pray.  Amen.

CS:  Amen. Thank you again, Daniel. Really appreciate it.

DW:  Absolutely. Thanks for listening to this episode, and we'll catch you next time for another episode of The Kingdom Investor Podcast.




ANNNOUNCER: What if you could take your generosity to the next level, impacting more lives in your community and around the world, creating a godly legacy for generations to come?

Now you can. Your first step is crafting your kingdom investing thesis. Reserve your spot in our next online workshop where we guide you through the process of discovering your passions, create a strategic plan and connect you to opportunities that will help you fulfill your God-given calling as a kingdom investor. Register today by clicking the link in the show notes. 

Thanks for listening. Don't forget to subscribe and we'll see you next time for another episode of The Kingdom Investor Podcast.