Syama Bunten
Wealth doesn’t break families, but what happens around wealth often does. Amy Castoro has spent her career working inside of those moments.

Women don’t talk about money the way we should. Not honestly, not openly, and not with each other. But that’s changing. I’m Syama Bunten, founder of Wealth Catalyst. And getting rich together is where the conversation lives. Every week, a different woman, a different path, and a conversation that will change how you think about your own financial power. This community is growing and you belong in it.

Please subscribe so you never miss an episode and leave us a five-star review so more women can find their way here. Now, let’s get rich together.

I am here today with the incredible Amy Castoro, the CEO of the Williams Group. Amy, your work sits at the intersection of wealth, trust, and what it really means to build a legacy that lasts, especially in today’s longevity conversations, what it looks like to be living with family legacy and dynasty. Everyone needs an Amy Castoro to be able to talk to.

I am so thrilled to be able to have you here on today’s show, not only to be able to share your story and, but through sharing your story to give our listeners an opportunity to see how you do take big and difficult topics and make them feel accessible and grounded in real family life. It was such a gift to have gotten to meet you earlier this year. And I’m so thrilled to be able to welcome you today on Getting Rich Together.

Thank you for being here.

Amy Castoro
Thank you so much for having me. I love the vision that you have for this program and the message you’re sending out. It’s an honor to be a part of it.

Syama Bunten
So Amy, obviously, anyone who meets you today sees you as a total powerhouse. are someone who walks into a room, lights it up. You speak with ease, with grace, with a lot of comfort. But obviously, this wise woman in front of me was a little girl at one point in her life. And maybe she was always wise. Maybe not. You’re going to tell me, but let’s go back.

to a young girl somewhere between the ages of 10 and 12 years old. Where were you in this beautiful world of ours? Where were you living? What was life like? And Amy, what was money like around you?

Amy Castoro
Well, what a fascinating question. So I’m one of four. I’m number three. We, there were four kids, so two boys and two girls. I was the oldest girl. And we lived in an exquisite home. It was built in the 1800s and had a raccoon porch. Yeah, it was really exquisite. I have to credit my mom on that. She walked up to the house one day, knocked on the door and she said to the lady, you ever decide to sell this house, give me a call.

And that woman called about two years later and we all moved in. It was amazing. Yeah. But you know, that’s, that’s women taking care of women. just, always hats off to moms who have that kind of foresight. So I was the oldest daughter and I was an athlete. I was more like a tomboy out running around the neighborhood. used to play something called kick the can.

And that was my favorite because we would get out there and all the kids would come running and our house was kind of the Mecca that everybody hung out at. And I just loved everyone around us. We had a house that was very open. The kitchen had a potbelly stove. And so kids would come or adults would come and we would just strike up unusual conversations. I think we had a knack for attracting the folks that didn’t feel like they belonged anywhere else. And yet they were the most interesting.

They would bring food or not. Maybe they’d show up because they needed food. But the door was always open. One time, when I was around 10 or 12, we came home from being up at the lake and people were having a party on the porch and we weren’t even there. it turned out to be a great party. But it was that kind of place. The door was always open or there was a window that was open.

Syama Bunten
Was that driven by your mom, your dad, both of them? Were they both on the same page with like, it sounds like a really sort of generous way to be raised, right? With this feeling of let’s give and welcome and be in community. Where did that come from, do you think?

Amy Castoro
Honestly, I think it was both of them. My dad passed away at 57. He was a police officer and he died of a disease that was really very rare, but his heart was very full. He taught bicycle safety and everybody knew him in the community as exactly that, a very kind and generous guy who cared a lot about young people. He always had some kind of project going on and people would come and they’d learn woodworking from him or.

how to fix a bike. Yeah, he was just that kind of a guy. And then my mom was always welcoming. mean, the other day, an 89 year old woman asked my mom, who’s also 89, to walk the dog just before she was walking out the door. And she’s like, ⁓ we gotta do it. It’s just kindness. We just gotta help her out. And she was forever bringing home a stray animal or a stray person. ⁓

Yeah, that’s really what life is like. I think around that time, my dad started to get sick. And so we knew there were bigger issues in the world than things that most people would be concerned about. And so we just made space for people. And one time, somebody’s son got locked out of the house because he’d been out too late. And he climbed the tree and in the window of my mom’s bedroom, and he woke her up and he said, don’t worry, Mrs. Z.

It’s Brian, I’ll be okay. I’m just gonna sleep on the sofa. can’t get in the house. And so she said, just call your mother.

Thanks for us.

Syama Bunten
I love that. And what was like, what was your high school life like? Was it, you know, getting into athletics and spending your time sort of after school that way? Were you knee deep in your books? Were you like, hey, I need some independence. I’m going to get a job. Like, how did you think about high school and what was it that you knew of yourself at that young age?

Amy Castoro
Yeah, I was an athlete. So I did gymnastics and I was a cheerleader and I was very social. So in the middle of everything and I had friends in all camps. Some of the friends that were not athletic, probably cutting class, they were my friends as much as the ones that had their noses in the books and did really well. So I figured out early on.

that people were just people and they were all super interesting. I had an assignment once where I went around to all the neighbors’ houses and I pretended that the assignment was I needed to learn about their life and who they were and what they had to teach me. And then it was such a fascinating exercise. I did it again six months later and they said, wow, you got that homework assignment again? And I forgot that I had already gone to their house. But it was then that I started to realize that there was something to learn from everybody.

That was a big part of the world.

Syama Bunten
What informed you? What were some of the stories or the feelings, I guess, from these stories? What do you think you were so connected or attracted to?

Amy Castoro
In high school, I had a teacher who taught sociology and he talked about the human condition a lot and that on the other side of violence was kindness and that if we could learn to feel and not just judge that there would be less violence in the world. And sure enough, in my adult years, I studied with a guy named Dr. Richard Strozzi-Heckler and he holds the same philosophy.

that there’s good in all of us. And it’s just a matter of working with somebody long enough to discover that. But I will say that in high school, we really didn’t have much money. The money story was that we didn’t have any. And so we had to get really resourceful on that. My dad stopped working and somewhere around high school, mom went to work and she took a job at what was called the Stadler, a hotel.

in New York City. And I remember watching her put her boots on every morning and get out the door in New York and fight through the cold and the freezing and go to work and then come home and cook dinner and keep everything going. And I saw the strength. I saw the strength of women and the resourcefulness and the determination and that we can’t do it alone. We really can’t do it alone. So I think we all, all four of us learned resourcefulness.

We, my brother, one of my brothers was really handy with mechanics and we all needed cars cause we had to work and he, my mom went to the junkyard with them and they came back with a Volkswagen and the Volkswagen didn’t have any seats. So it, we put an egg crate there and we could actually drive the car sitting on an egg crate. So we didn’t do that for very long, but what we did do was get four or five other Volkswagens.

So in the morning when you would go to work, you wanted to be the first one out the door because then you could drive one of the Volkswagen’s that worked. Because if you waited too long, you’re going to get the one that was used for parts. So it was pretty funny. We did really well. I have to acknowledge my mom and setting a role model of what it means to be a woman in those years. For her, it would have meant staying home. But for us, it was no, this is a powerful woman who knows

how to generate wealth, how to raise a family, how to take care of an ailing spouse. were pretty powerful years for me. Yeah, I learned a lot.

Syama Bunten
Go mom!

That’s powerful. So when it came time to prelaunch yourself in the world and head off to university with such a fierce female role model, like what, you know, what sort of stuck with you as you were deciding to choose what you wanted to study, where you wanted to go, how close to home you wanted to be sort of, it sounds like there was the strong inner connectivity within the family and certainly

loss and trauma can either break a family or bring them closer. And it sounds like I’m inferring here, but that things became close. it sounds like things really, the value of our precious human life and the impact that we could make in this world. It’s like it all, things become really simple, right? When those things happen. So how did you sort of

moving into university, how did you know what you wanted to study? Were you like, at that point, yeah, of course I’m going to end up running the world and impacting all these lives. How did you sort of context yourself and what did you want to do at that time?

Amy Castoro
There was a lot of pressure to study one of the sciences or to come out with some sort of skill set. So I started to study accounting and then Dr. Silverstein looked at me about a month into the course and said, this is not for you. Which, you know, as a young girl, I remember having a math class and Dr. Brown was, I think a World War II veteran and he would just

pat me on the head and say, you know what, you don’t have to worry about this. I’ll pass you anyway. And boy, did that hurt. Yeah, that was, I never really did get through my academic years, a solid grasp of math. And it was really challenging because there was that stereotype out there. So I wasn’t surprised when Dr. Silverstein said, yeah, you’re, this is not for you. But I did come home in tears and I said to my mom, I really don’t know what to do. I’m really upset. I’ll never make anything of my life. And she said, well, what do you love?

And I said, I love the ballet. She said, well, why don’t you study ballet for a little while and let’s see what happens. And sure enough in the ballet class, I met someone who was studying organizational psychology. And from there, my career took off. My first position was in retained executive search, which was really looking at how people spend their time at work and why some women would excel and men would excel and why women didn’t.

how men made decisions versus how women made decisions. And it was fascinating. I was so enthralled by that. And then shortly after that, I got picked up into another career. But yeah, I remember the moment I came home and she said, yeah, follow your heart. It will never lead you astray.

Syama Bunten
True words have never been spoken. What a beautiful and life-affirming thing to hear as a young woman who’s like, holy shit, I’ve just been told by my professor that ⁓ I’m not going to make it into the thing that I think. And what an abundant mindset your mom had in terms of following your heart and your dreams.

And who would have thought, you know, ballet could lead to organizational psychology.

Amy Castoro
Yeah, I would have thought it’s so true. You know, I see that in the families today. There’s so many wealthy next gen family members. They’re in that question of what do I do with my life and how do I make those decisions? And there’s a lot of pressure on them, pressure to do certain shoulds in the world. So holding that place of possibility that you don’t know, but if you follow what you’re really interested in, you’ll end up in the right place.

Yeah, that abundance mindset is really, we didn’t come from much and we all came with a really hardcore work ethic that if you’re gonna make anything in the world, it’s from your own effort. It would have been easy to follow a scarcity mindset. But there was a moment where I remember my mom saying, the bills are due. I don’t know where the money’s gonna come from, but something will turn up. And then a week later,

she gets a check in the mail and we all go on vacation.

Syama Bunten
I’m like, we need to next like have a conversation with mom. That’s hard. How wonderful. So okay, you are getting ready to graduate college now have an understanding of, let’s call it phase one of purpose. I want to exercise the skill set into the world. When it came to securing and finding a job, was your mindset

you know, I’m going to find the right thing. Were there lots of opportunities? You know, was it more like, ⁓ crap, I really need to get a job right now. And like, how am I going to, you know, navigate this? How did you secure the first job? And, you know, at that time, obviously, no one’s really, I’m sure talking about salary and negotiation and, you know, money, it’s like, you kind of get what you get, right? And so you till you know any better. But what was that first job?

search like how did you land on your first home base?

Amy Castoro
So I had gone to an alumni meeting at the school and somebody stood up and said that they were a headhunter. And I thought, well, if nothing else, that’s a cool title. So I’m going to look it out. And sure enough, I put an objective. In those days, we had resumes with objectives and it said headhunter. And I sent it to, I don’t know, maybe 15 different firms in Manhattan. And one guy called me up and he said, no one’s ever put headhunter on the resume for that reason alone. Come on in, I want to find out what you’re all about.

And that was an all-male firm. They were a Hasidic firm. And my last name was Zygorski at the time. So I think they thought I was Jewish. But on my way out, I tried to straighten the mezuzah, which is an angled decorative piece. And they looked at me and they said, you’re not Jewish, are you? And I said, no, I’m not Jewish. But I really love what you guys have going on here. And I know I could learn a lot. And sure enough, they hired me.

And it was by far one of the most impressive positions I had because I learned a lot about business. learned a lot about why people tick, what lights them up at work. I learned how to hold people to their promise and their commitment in the 11th hour when they have to move across the country and they’re waffling on the job. I was able to be a contribution in their lives that took their income.

significantly higher so they could now put their kids through a better school. It was really a fascinating role and one that I’m forever grateful for.

Syama Bunten
Wow. you know, launching and I mean, obviously launching yourself anywhere in the country, it’s challenging, but certainly New York is not cheap. You know, it’s like, it’s difficult to sort of, you know, land and figure things out. At what point in your in your career in this early stage was it like, all right, I’m ready to like,

get my apartment and like do the thing and you know, when did you start to have that first anchoring sense of like, all right, I’m ready. And like, here’s here’s what it’s gonna look like.

Amy Castoro
Do know, I think it was in the second year of that position, I was earning six figures and I thought, okay, my income is worth more than the house right now. It’s time for me to go find my own feet. And I took a job. mean, I took an apartment with two other roommates and it was phenomenal. We were not in the best part of town, but in a great family oriented part of town. It was me, a blonde, a brunette.

and a redhead. And underneath our apartment was a bar. And so the guys would climb a telephone pole out in front to try to look in the window. It was really a fun time in our lives. It was really neat. And it was really fun. And then I had a couple more apartments and then I got married. And then we moved out to California. took a job with the Walt Disney Company as part of their Disney University.

Syama Bunten
⁓ my god! ⁓

Amy Castoro
Wow.

Syama Bunten
So before, back, you know, earning six figures in your 20s is a big deal, right? It’s like, you know, there’s, there’s so much you can, could have and did do, I imagine with your money. How did you, how did you organize it in your mind? You know, obviously, there’s that moment where you’re like, my God, you know, I make more than my parents do, or I’m making, you know, more and, then and how you spend it, and do I save it? And do I buy the shoes? Do I want

the thing, like how did you, with these early sort of notions of identity, the money, what did you do with it? Like, how did you sort of organize, was it like, hey, there’s this great bar downstairs, drinks on me, you know, like, how did you start to think about this money that you were making at a young age?

Amy Castoro
You know, I saved it. I didn’t do much more than that. We didn’t grow up with this concept around investing. I did pay off a lot of debts for me or my sister or my mom. We just pitched it in and everybody took care of everybody else. wasn’t, I never felt like it was my money. I felt like it was, ⁓ I landed in this great job and now I can help in a more meaningful way. That’s really what I did. And then my mom sold the house and everybody kind of

moved into their own roles and I moved across the country. had a brother out there. So it just saved it really. I paid off whatever debts I could. I remember my sister wanted to go to camp and we didn’t have a sleeping bag for her so I bought one on a credit card and it took me about seven years to pay off the sleeping bag. So yeah, we did that kind of thing with it.

Syama Bunten
Real quick, I want to tell you about something I built for you. May 14th, New York City, the Wealth Catalyst Summit. One day, 140 women who were serious about what they do with their money. Executives, founders, investors in the same room having the kinds of conversations that just don’t happen anywhere else. Private markets, real estate, how to get on boards, how to buy a business, how to make your capital actually reflect what you believe.

If you’ve been listening to the show, you already know that this is your room. Seats are limited and we are coming up on this event May 14th. So register today at wealthcatalyst.com. Link is in the show notes. Now back to the conversation. Being great at what you do affords you a lot of opportunity, right? And sort of like being able to identify and see yourself and

moving up and then certainly you got married, which is very exciting, and then deciding to move across the country. So what were some of the inflection points that led you to being like, all right, I’m getting out of the East Coast. I am going to plant myself somewhere where it sounds like you had some family, but it’s always hard. Having had moved across the country myself, San Francisco, New York, New York, LA, LA back to San Francisco.

I know it’s like you might know people, but it’s not always easy, right? Like it is, it can be challenging. What were some of the inflection points that led you to saying this is the right opportunity for me? I feel like we’re in a good spot to do this and we’re gonna make this move. And was it something that you had to, was it like a family decision? Like, did you talk to your husband and was it, know, let’s make this decision together and triangulate how this works? Or was it like, baby, we gotta go to California.

Amy Castoro
I’m

Syama Bunten
What was it like?

Amy Castoro
You know, in Manhattan, I think it’s on Lexington, maybe 53rd, there’s a really long escalator. And I was going down that escalator on my way and a woman in front of me tripped. She was not hurt, but I jumped over her and I pulled her foot out because I was afraid it was going to get stuck in the escalator. And I saw that her shoe had come off, but she still had five toes. And then I jumped on my train and I thought, my gosh, I’ve become this hardened person.

where I’m just here taking care of somebody, but I’m still not gonna miss my train. And that was one of the moments where I said, yeah, I don’t know. think I’m looking for a little more depth of relationship than what the busy city was affording me at that time. So that was definitely a moment to say, yeah, I’m gonna go check out the West Coast. And I loved it. I couldn’t have loved it more actually. I was in Hermosa beach with my brother for a little while and…

That was before Hermosa was really built up. And I was working for Disney. It was just an unbelievable opportunity that was new, not just for me, but no one in my family had never ever worked in a place like that. As a matter of fact, in the interview, they said, what’s your favorite land? And I said, ⁓ I’d have to say Africa. And they’d say, no, no, no, we mean in the park. And I said, ⁓ I’ve never been, because we couldn’t afford to go to Disney. It was clear across the country.

And I said, but that bush cut in the shape of Mickey Mouse knocked my socks off. So I’m all in. then I said, but any company that’s willing to fly that many disabled folks from across the world to the park so they can enjoy this kind of equipment I want to be a part of. And so I quickly signed up and I knew I was in the right place. Wow.

Syama Bunten
and what was the role that you took there?

Amy Castoro
I had a few different roles. I was part of Disney University where we would teach classes on leadership, on management. We would hire the professional people. We all train in the park position. So I got to train as Chip and Dale. So I got to be a character for a little while. That was really fun. How cute!

Syama Bunten
I love that. I’m having great visuals.

Amy Castoro
And you know, it’s amazing how that costume can bring so much joy to everyone’s face, whether it’s a two year old to a hundred year old. And so to be able to just do that for, you know, maybe four hours was really rewarding. And I knew that bringing that kind of joy to people is what really lights me up.

Syama Bunten
Mmm, that is so powerful.

Amy Castoro
Yeah, it was, it’s pretty powerful. And then after Disney, I took a job with Grant Thornton as part of their management consulting group. And there I started to learn about family businesses and my experience of working with people in key positions and understanding their why and understanding whether or not they should keep a business or sell a business and how that speaks to a legacy just all made sense in my background. It was

less about the what should we do, more about the why. And that just made perfect sense. So I took that position and really loved it. I loved the opportunity of getting to know people on a personal level, not just from a spreadsheet.

Syama Bunten
I mean, it’s really your education and proclivities into psychology and how people operate is such a powerful through line throughout your life. While you were sort of progressing and obviously you mentioned you were at the first beginning, it was all about saving, know, and like, let’s pay things off. When did you start to feel in your life a sense of, let’s call it financial security? You know, I think that there’s a moment where you’re like,

You know, I feel and you can and you’re very well open to say I still don’t feel this way. And you know, I’m still I’m still getting there. But was there in this early part, right? As you’re I feel like as we’re as we’re getting this external validation in the world, right, it’s supposed to indicate for us certain things. It’s supposed to indicate that you’re making it. You know, there’s the prerequisite. I buy the house. I, you know, do the this. got my 401k or my

pension, you know, it’s like the things sort of start to the boxes get ticked off. When did those boxes start to get ticked off? And did they correlate, I guess, to a sense of security for you? How did you start to navigate?

Amy Castoro
Yeah, you know, I wish I could say I’m there. I’m really not there. And I don’t think that will surprise you. And a lot of my clients also come from humble beginnings. there’s a drive, there’s a determination, in my case, to just keep generating wealth, not necessarily for my sake, but for future generations, so that we can share it, so that we can

afford more opportunities for people. When I was leaving New York, I remember taking the coat off my back and giving it to a homeless woman. And in that moment, I felt like, ⁓ actually, I can actually give something up for someone else. And that, so I had a resourcefulness that I could continue to generate and less about, I’ve got this much and I’m good now. So if anything,

I would say that I have deepened trust in myself to be resourceful, to keep generating. That happened probably in my 30s, when I could see I could be successful at things.

Syama Bunten
Yeah, it goes back to your, if I’m going to make it in this world, like, I know I can do it. And here you have been for decades now proving out to yourself, you know, that young thesis of like, I got this and over and over again, getting it, you know, and sort of catching yourself, you know, your career and the places where you found yourself while different.

have this underlying sort of feeling around them. Were there any inflection points within your career progression that sort of gave you this feeling of stepping more and more into your power? you’re starting, because today, obviously, are, I mean, there’s so much more to come. We’re obviously living so much longer now than ever before. And I know you deal with this with your clients.

But today you stand as someone who really is in her power, so it seems, right? Someone who’s able to open up the wings and hold people. And there’s a progression sometimes to get there. So, you know, what were some of the inflection points that had you look into the mirror and be like, okay, I have this and I know this because, fill in the blank, because something happened.

Amy Castoro
I have to track that back to early childhood again, where there was somebody whose life was going to be cut short in the next room. So how are we going to be resourceful for our own future? So I think you can go through that experience and come out many different ways. I came out, as I think my siblings did too, with a solid sense of can do. So regardless of the stereotypes for women, we really

Didn’t honor them the way that I think people expected us to I can remember one of that early positions where somebody made a comment to me that Would probably be considered derogatory and I just remember standing up and saying you can’t speak to me that way Whether I was trained to do that or not. It just felt so undignified that I wasn’t going to take it and and so I think that Being athletic. I think having two older brothers I think

there was just a place where a certain amount of dignity was instilled that said, yeah, I’m not taking that. So I think it’s just part of how I’m in that I’m in charge of my own future. You know, when we work with families and we work with these ultra high net worth women, it’s easy for them to see that someone else is pulling the strings of their lives.

And when we can give them the skills to say, you can advocate for your own future. You can make choices. Where do you need to stand in your dignity? Where do you need to step into your own power? What would you like that to look like? How do you set that unfolding? What are the conversations you need to have to move that? I remember working with one woman where her job was to move the rubber trees around in the car dealership. And she finally raised her hand after some

prompting and asked to attend a board meeting. And her father said, what are you going to do in the board meeting? She said, I don’t know. I just want to come and see. And finally, the board meeting happened. She raised her hand and she said, when are you guys going to design a car that women want to drive? So when she found her voice, A, to and B, to put a suggestion out there, it shifted the dramatic future of that business. Because now they had a whole car line committed to women.

So for me, what really lights me up is exactly that. It’s helping women find their power and we use it in a way that serves them, not on us. I think the numbers now is like $124 trillion is gonna transfer intergenerationally over the next 20 years. That’s a staggering amount. And when we look at what women are up to and how women think in terms of their

collaborative nature in terms of how they want to have a bigger impact in the world. I’m super excited about what’s possible because if women are slotted or projected to control $34 trillion by 2030, that’s according to the Ultra High Net Worth Institute, I say that’s a massive shift in financial power. So we just saw women stepping into really owning their resourcefulness, their

collaborative nature, their vision for how the world could be a better place.

Syama Bunten
Amen, Amy. mean, I am there with you. And it’s so wonderful to see how our lives become these mirrors of the visions of the world we want. For you, going from working for others to being the owner of a company is, that’s no small thing. It’s a big deal to be like, I’m no longer just going to…

be my best, optimal self within the constructs of organizations that already exist, but I have a vision and I want to be the owner of a company and I want to steward and lead something. What was the emotional transition for you like as you launched your first business and you sort of became the creator of destiny even more so than maybe what you had done in the past?

Amy Castoro
Well, so this business was started by an absolute visionary, Roy Williams. And when Roy started this business 60 years ago, he saw that all of the estate planning in the world is designed to take care of assets, not relationships. And so early on, he saw that wealth was not always a great contributor to the lives of others, and he wanted to shift that. So in doing his research, which was groundbreaking,

He learned that the biggest variable was actually trust and communication. So knowing that relationships are at the foundation of every legacy, I got really excited and invested in this company because of that and saw a way to say, this is considered a man’s business. We’re only using 50 % of the population and their wisdom. So for me, it was exciting to see how we could fold women’s voices in.

I remember one of the earliest meetings that Roy and I went to was with a family office group in Manhattan. And they did some of the biggest, most powerful deals that were done. Like their deals would move the stock market. And somewhere towards the end of the meeting, said, Hey guys, I, you know, I’d love to use the washroom on my way out. And they all kind of blanched and they said, we don’t have a ladies room. And I remember thinking like that was.

So that was maybe eight years ago. No, right. Not that long ago. And I remember thinking, how is it that some of the biggest deals in the world are being done? And there isn’t even a ladies room on the floor. So, you know, lucky for me, Roy played professional football and he stood out in front of the door. But still, it was kind of like that to me was astounding. And we just need more and more women to realize their power.

Syama Bunten
Look out!

Amy Castoro
speak up and trust their ability to navigate financial conversations or at least to ask the right questions.

Syama Bunten
I love them. know, it’s really, think sometimes, especially in our social constructs we’re in today, you know, sometimes people look to big decisions as being the decisions, but ultimately, sometimes it’s quiet decisions, it’s smaller things. It’s not that every woman needs to be a venture capitalist to change the world. Sometimes she just needs to redo her estate plan.

to be able to make sure that the right assets are moving in the right ways. I think that there’s a real hype culture around, especially in this moment now that more women are talking about the transfer. And I truly believe that there’s two things at stake here. It’s yes, there’s a transfer, but there’s also now been 50 years of women being able to sort of build wealth in these new ways, right? And being able to

to come to this sort of, know, coalescence of like transference of wealth, but also building it from our own ambition and our own ability to access capital. And so the changes that can be made are also very nuanced and varied. And I think that there’s something powerful about owning what is true to you, which may not be what is the most highly marketed truths.

that are out there for people to fall in line with. How have you sort of seen this coming to oneself? know, I mean, obviously in my own journey, I have found that there are heavily marketed conversations to women. Sometimes they are meant to instill fear or meant to make me feel like I’m not doing enough. You know, like there’s highly charged conversations that are marketed, but you get to be there in these most intimate spaces. So what have you sort of

scene or what have you been experiencing around that?

Amy Castoro
Well, I would say that, yes, women, when they meet with other women in these curated, high net worth populations where they can learn from each other, there’s more and more of a yearn for that. Where they’re sharing information, they want to get together. I can see it just in my work, more and more of these groups are popping up. And women are running them and they’re doing a phenomenal job. They’re freer with information. There’s a bigger conversation around support.

supporting each other. It’s really powerful. I’m also seeing them stepping into climate and ESG investing in a really powerful way. there’s a true values-based orientation there that to me gives me a lot of peace. I am seeing in my work, there’s two levels of trust. There’s the transactional trust. Can we trust someone to get something done that we ask them to?

And then there’s the relational piece. Do we have the kind of relationship that we can trust each other to do what we want to do? And so women just by nature seem to have more of an affinity or comfort or willingness to make the investment on the relational side. And I think that’s where we’re going to have more productive outcomes in philanthropy. That’s where we’re going to have more powerful women teaching their daughters about finance.

so that they’re growing up inside of the healthier system that way. So for me, in all of this chaos that’s happening in the world, it comes back to our neighbors, it comes back to our daughters, it comes back to each other supporting what each other cares about so that we can have a conversation that’s meaningful at the level of personal purpose. Then we can really move the needle. But if we’re out there just trying to make a buck,

and so ultimately the system will fail. So it’s really teaching people all the way back to my early beginning about kindness and care and how do we navigate a challenging conversation based on what the other person really cares about as opposed to what we’re going to do. And I see that in the political discourse where families can’t have a conversation about politics because it ends up being a fight over who’s right.

But when we shift the conversation to really wanting to understand what that person cares about, we can now have a conversation about that individual, not just about their beliefs. So this is a little bit different, but it’s a powerful way to go about that.

Syama Bunten
I love that. is, you know, it almost feels like a return to family values, you know, it’s like when we were raised, it was like you check things at the door to address the totality of a human and then things have become really perverted in ways, right? Like we’re looking for ways to separate ourselves rather than to realize how painfully similar we all are and you know, how much more, how much more in common.

everyone’s fears and sort of core emotions are, you know, as a result of sort of being in this work now, I imagine either your investing strategies or the ways that you think about your own money through the lens of now having experienced so many other people and guiding people has probably either been extremely reinforced in many ways and maybe also expanded, right, in terms of like what you see as possible.

Can you share a little bit of sort of your philosophy today for yourself on how your capital has changed? know, what has shifted for you in these last 10 years and how do you sort of take that introspective look for yourself?

Amy Castoro
You know, for me, it’s beyond my wildest dreams. And it’s a moment where I can look at the portfolio and then I have to look at it again and say, wow, how did that happen? And then… ⁓

Syama Bunten
You’re like, yeah, I’m doing it.

Amy Castoro
Where there’s a moment, like if you’re in the stock market these days, it’s hard not to do well. So, knock on wood that continues. But at the same time, I do say, yeah, well, it’s been through some really selective investments that make the world a better place. And it’s things that I can really feel good about. There isn’t anything in my portfolio that I don’t feel good about in terms of its impact on the world and how it’s changing the lives of others.

and humanity for that sake. So I feel like through my wealth, I’m able to keep those engines of prosperity going, but also really have the impact over the next hundred years by funding these different sources. And for me, I also think about the kids. think about, have a son and a daughter and obviously a husband. And I think, well, if we could create enough wealth where they could stand on it

as a way to give to others. To me, that’s really powerful. And that’s, I feel like a responsibility we have.

Syama Bunten
That’s incredible. As you’re sort of, you know, thinking about legacy, right? Obviously children and their values and your whole work is around legacy. How do you sort of think about your work and let’s say at a young age of 105, you know, looking backwards and seeing sort of this core fundamental sense of purpose, you know, both in terms of

wanting to love humanity, which is very clear, and also in terms of your interests and how it sort of shaped this body of work, what might be some of the things you would be reflecting on? What does legacy look like for you at this young age, Amy, of 105?

Amy Castoro
You know, in my work, when we work with a family, I’m not only focused on the family in front of me. I’m thinking about the kids on the other side of the French doors and the life that they’re going to grow up inside of. When we look at the impact of AI on the world these days, it’s very hard to trust anything. You can’t trust what you see and you can’t always trust what you read. So my work and the work of our whole team is to really focus on

How do we build, manage, repair trust? So if we can lay down some skills that become the fabric of a family, then those kids grow up inside of a healthier system. So that even just by learning how to have a meaningful conversation in conflict without giving up their ground, they’re preserving their own dignity and the dignity of others. If we can teach that kind of level of communication so it spreads out at 105,

There’ll be countless people who have learned some new skills in a very fundamental aspect of life, which is trust. And to me, that would be really powerful.

Syama Bunten
So beautiful, Amy. we wind down our conversation, there are two of my most favorite questions to ask. The first is, what has been one of your most favorite recent ways of spending your money that has felt so fabulous?

Amy Castoro
let’s see. I think creating experiences for the family. I think it’s coming to this place in Naples that is so exquisitely beautiful so that we can enjoy each other and we can play tennis and golf and see the beauty of nature here. I would say that’s probably been my favorite way of spending money these days.

Syama Bunten
I love that. And then my final question, Amy, obviously you are standing here in the service of others and to shape this beautiful world that you’ve articulated. And yet we all still need something. What is it that you are calling in today? What does your heart want? What are you needing? And how can we, the audience, support you?

Amy Castoro
Yeah, you know, when I think about that, I think about creating more peace in families. When great families stay together, their wealth really can change the world. But when they divide over conflict, they lose that opportunity and we as a culture lose that opportunity. So for me, I think it’s for people to be able to say what they need.

in a moment for their own sake, for their own dignity, and to build the skill of navigating or co-designing a path forward so that both sides of a conversation are taken care of. They can have a conversation based on care, not on who’s right. I think that would serve the world, and I think it would create more peace in families.

Syama Bunten
Beautiful, Amy. It’s been an absolute pleasure to have you here today on Getting Rich Together. Thank you for sharing your life, your stories, your wisdom, your heart. It’s a gift to know you. Thank you.

Amy Castoro
Well, thank you for your time and your expert questions. I really felt seen and I’m grateful for that.

Syama Bunten
Thank you for listening. This is the conversation we come back to every single week. Real women, real wealth, and what becomes possible when we stop being silent about money. If today’s episode moved you, don’t let it stop here. Wealth Catalyst is where women go to take it further. Our Freedom Tour salons are gathering women in 32 cities this year. Intimate evenings in homes and private spaces where women talk honestly about money, risk, and what they’re building.

And if you’re ready to go even bigger, join us at the Wealth Catalyst Summit, a full-day event in New York City this May and San Francisco this October. Find your city and claim your seat at wealthcatalyst.com. We’ll see you there.