The Curiosity Advantage: Transforming Family Wealth Through Strategic Learning

In our latest episode, we sit down with Torri Hawley, a dynamic voice in family enterprise education who brings both professional expertise and lived experience to her role as Director of Client Learning Experience at Tamarind Learning. Drawing from her journey as a seventh-generation member of a 150-year-old family enterprise, Torri shares insights about finding one’s place within a family business legacy. Named among Family Business Magazine’s “25 Under 35: Next-Gen Members to Watch,” she embodies the bridge between traditional family enterprise values and next-generation perspectives.

In this conversation, Torri explores the importance of patience, relationship building, and the unexpected ways our early career experiences shape our journey. Through personal stories and professional observations, she offers fresh perspectives on developing next-gen leadership and navigating the complexities of family enterprise dynamics. Her unique vantage point – as both a next-gen family member and an educator – brings depth and authenticity to discussions about growth, learning, and intergenerational collaboration.

About Torri Hawley

Torri Hawley serves as the Director of Client Learning Experience for Tamarind Learning, bringing a decade of experience working with enterprising families. As a seventh-generation member of a family with a 150-year-old operating company, she has been actively involved in governance from an early age, helping establish a family council and promoting next-gen education. She currently serves on her family office and operating companies’ boards and her personal experience drives her passion for helping next-generation members build confidence and credibility.

With a BBA in Family Enterprise Management from Stetson University and a master’s in strategic human resources from the University of Denver, Torri has earned certificates in family business and wealth advising from the Family Firm Institute. She has spoken at numerous prestigious conferences and was named one of Family Business Magazine’s “25 Under 35: Next-Gen Members to Watch.” Based in the Philadelphia suburbs with her husband Charlie and dog Murray, she remains committed to community service, particularly focusing on addressing childhood hunger locally.

Resources discussed in this episode:

Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd. 

Contact Torri Hawley | Tamarind Learning 

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at Assante Financial Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. And on this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.

Today, we welcome Torri Hawley, Director of Client Learning Experience at Tamarind Learning. As a seventh-generation member of a 150-year-old family enterprise, Torri brings unique firsthand experience in family governance and next-generation leadership. She serves on her family office and operating companies’ boards, while holding advanced certifications from the Family Firm Institute. Recognized as one of Family Business Magazine’s 25 Under 35: Next-Gen Members to Watch, Torri combines her academic background in Family Enterprise Management with a passion for empowering next-generation family business leaders through education and engagement.

My goal is to be the most curious person in today’s conversation with Torri, where we’ll explore the delicate art of educating next-gen wealth inheritors. Through her work at Tamarind Learning, Torri brings both professional expertise and personal experience to our discussion of patient capital, relationship building, and navigating family wealth conversations. Drawing from her own journey as a family enterprise owner, she’ll share insights on how small actions today shape tomorrow’s opportunities.

Now, let’s dive in!

Cory:  Well, welcome, Torri. We’re excited to have you here today to share your wealth of knowledge and experiences with us. Let’s dive in, shall we?

Torri:  Yeah. Let’s do it.

Cory: Torri, imagine you’re delivering the commencement speech to the graduating class of 2024, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Torri: This is a really fun question, and I actually went back and listened to a couple of your other guests for a little inspiration, and my advice is threefold, and sort of how my career has played out.

First of all, don’t underestimate the power of small connections. So this actually comes from Adam Grant’s Give and Take. I read this in college, and I’ve thought about it a lot since. I want to make connections with people in the world and be good and kind. and all of these things, and it comes back to you. So I will say this happened in my own career. I met Kirby, probably close to 15 years ago. That’s Kirby Rosplock for those of you who don’t know. I did not say a single word to her in that entire duration, and then one day she reached out to me, and here I am. So that’s the first one.

The second one is the power of doing things you don’t want to do. My career has been full of things, and I had to get a job, so I started working in accounting. But I learned so much. and it ended up being in a multigenerational family business. So I learned so much about the industry and working in a multigenerational business and governance with them.

And the last one is give things time, especially if you are a young person, a young next-gen, and you want that career yesterday. I cannot state enough that patient capital also applies to your career. So don’t worry if you are not the executive, or you’re not whatever you want to be right now. It has taken a long time for me to land where I have, and I’m deeply happy, and I couldn’t have been here without all of this other trajectory along the way.

Cory: Love it! And, I love that you mentioned Adam Grant’s give and take, because I only recently read the book because one of my previous guests sent me a copy. I love the small connections. I think that there are so many deposits that we make along our life into things that we have no idea if they’ll ever come back around, if it’ll be a payoff to us or others.

So tell me, Torri, in your experience now and the work that you do, where do you see that apply to the people that you support?

Torri: That’s a great question. So I work with adult next gens at Tamarind Learning. These are people who are earlier in their career. They are building their life.

I think even the way that young people actually interact with me, you know, showing up, being timely, being positive, communicative, all these different things. And I don’t necessarily care so much about me, but I think about myself as a young person, especially as a young inheritor, as a young owner of my own family enterprise, and how important those things are. So I see that as a great reflection of knowing how they’re going to interact with learning and personal development and skill development. 

Cory: That’s awesome. And so those adult next gens, you know, they’re showing up. What does that look like in other parts of their world? If you see that they’re showing up, they’re on time, and they’re respecting you, what other places do you think that comes out in their world?

Torri: That’s a good question. So you had Joshua Nacht, and he does research on family champions. And I think that is such a good example of the sort of people who, who are showing up and who are really living out sort of that, like, values, empowered, stance. Certainly, with young people in their own careers, how they’re interacting with people who, you know, shareholders, stakeholders, and also if we’re going to refer back to “Give and Take”, all kinds of different people.

I don’t have the best answer for you because I’m not in their day-to-day walks of life, but how I see it play out in their personal development. One thing that’s really interesting to me is someone does some pure learning with our curriculum and our platform, and they said one of the coolest things for these groups coming out of it is that they work so much better with advisors. They are empowered, informed and they’re not afraid, and that’s part of why we do the work that we do is because we want to empower the next-gen.

Cory: You mentioned stakeholders and then advisers. I want to kind of get into some of those relationships that maybe it is a direct result of the learning that somebody does at Tamarind, or maybe it could be an auxiliary benefit, or just learning that’s done afterwards or outside of what they do at Tamarind. And I think that, again, it might be that a conversation like this is a catalyst. It might be one of those components of the education, they’re going through a lesson and it clicks for them. But I’m thinking about those stakeholders that you mentioned and yourself having some of those experiences as a family enterprises owner, where do you see some of those relationships with those stakeholders where maybe, again, a small deposit could pay off, for that next-gen?

Torri: I’ll speak generally, and then I’ll speak personally.

I see these kinds of things playing out with next-gens in their own careers, where they had a positive interaction with an adviser, and maybe the next summer they get an internship or something like that. A lot of the people we work with, and this was partially the story and the narrative that I was told, is especially as a woman, don’t worry about it, you’re taken care of. So never really interfacing with people, advisers, and management,, you’re taken care of. Don’t worry about it. And then you are unfortunately an adult at a later stage in life and the responsibilities are so much bigger, and you haven’t been getting all of these reps along the way. So you’re not working with a tax accountant or you’re only interfacing with the family office, for example. So it’s a really safe and insulated way of doing this.

Something for me that if you are a parent with young adults in your life, one of the things that built this skill in me and my siblings, was we were despite the “you’re taken care of,” we were always invited to board dinners, and meeting with executive leadership from a young age.

I remember being 10 or 12 and sitting at a table with executives and important people, not ever being told that I couldn’t have a voice at those tables. So as a result, in some ways it’s backfired because I have maybe a little bit too much confidence, but not being intimidated by talking about business topics or, wealth management topics, money taboos, all those kinds of things.

So from a personal perspective, that’s where that has shown up for me, the ability to not be intimidated and afraid of encountering those kinds of scenarios as well as people.

Cory: I love that! And just even the idea, you made the comment of becoming an adult and those responsibilities become harder. And there’s those little things that parents can do, or grandparents too, or advisers even, to suggest that that that rising-gen, be it even in childhood, maybe not young childhood, but, you know, those later years of practicing to become an adult in a safe environment, can be so impactful. So how do you see it in other areas that, and you said that a lot of the work that you do is with adult next-gens, but just helping people get those reps, understand some of the complexities of their wealth and the decisions that maybe have been made for them, but maybe they can be empowered to participate in some of that. How do you see some of those happening?

Torri: Yeah, I’m actually going to go back to, I got a family enterprise degree at Stetson University through the head honcho at that program, Greg McCann. He had developed the family enterprise program around really showing up as a young inheritor and a young family enterprise member in some pretty structured ways.

For example, anytime that a guest speaker came to our classes, we were required to send them an email and say thank you so much for coming. Here’s one thing I learned, and here’s how I’m going to apply it to my life. And that’s kind of a parenting thing, but something that was really impactful to me. Now when I meet people out in the world, if I have a job interview, and even if I don’t get the job, I send a little email or a note, and I thank them. That was one of the really cool things about the Stetson program.

Another was actually setting up sort of like quick lunch dates with executives in the community. So you have the opportunity to just sit and have a casual lunch with someone, and I’ll go back to actually, if I have a commencement speech thing, shoot your shot, reach out to people, introduce yourself, say, “Hey, will you be on my podcast? Will you have a conversation? I want to pick your brain.” Especially as a young person, the worst answer you can get is, “Sorry no. I’m too busy and important.” And then you know whether they’re a giver or a taker as well.

Cory: I love that! That’s exactly what I was thinking, as you were mentioning, you know, reaching out to the executive is, again, that deposit in that relationship. And so, connecting the, you know, you’re sending the email after an interaction. It is one of those things that is small, but it builds character for the person who’s doing it, but also is amazing for that relationship. Again, you mentioned that some of those things pay off in ways that you wouldn’t have otherwise thought.

Let’s go back to your meeting of Kirby, because you mentioned how it was a gap between when you met her and when she reached back out. How did that play in your world? Because I’m sure if she offered you the job when you first met, if there even was a job, maybe you weren’t ready.

Torri: Yeah, 100%. And that goes back to that patient capital thing. So I’ll start before I talk about Kirby and sort of our journey.

I desperately wanted to work with the next-gens coming out of college. As a 21-year-old, all I wanted to do was coach and develop the next-gens, and it took 10 or 12 years for me to circle back to that.

So my mentor in college works in the industry and works in the field, and we’re still good friends now. But the advice that he gave me, and to be clear, he doesn’t remember this advice, was to get older, get some life experience, get some chops, and do some different things. And that was hugely important. I needed to hear that, and my pithy line now is who wants to pay a 21-year-old to do anything, but certainly to coach a 19-year-old, and I definitely needed some adult perspective because I feel way more positioned to do that now.

So going back to my relationship with Kirby, she and I actually met when I was in undergrad. She and I, this was an opportunity that I got through Stetson because I had built relationships with Greg McCann and Dennis Jaffe, and the people in the program, and they saw me sort of as this family champion rising general.

So I was talking to Family Enterprise USA (FEUSA). They’re sort of a lobbying governmental group now, but at the time, they were doing a lot of family enterprise research. And so, Kirby is further into her career than I am by about a decade or so, she’s basically where I am now today, and she and I were both sort of positioning for a junior board seat at FEUSA. And for me, it was such a long shot.

This also goes back to “show up, go to the meeting, get the reps, do the thing, get the rejection,” all that, and we didn’t really interact again for close to a decade. But I remember sitting on the pool deck, talking to her, having a conversation, building the relationship, and then 10 years later, she invited me to follow Tamarind Learning on LinkedIn, and I accepted. And I said, “not only do I accept this LinkedIn invitation, but will you hire me?” And about a week later, I was at Tamarind.

Cory: That’s so cool, I love that!

Torri: Really, really fun! It was a cool connection, and she didn’t actually super well remember, and then I was like, “But that’s how you know me!”

Cory: And, Torri, your comment from your mentor of “get older,” that could be received in a very negative way. It could be motivating the way you speak of it, or it could really take a lot of the wind out of the sails of, you know, “will I ever be good enough or ready or or whatnot?” How did you receive that yourself, and what do you think, if somebody was receiving that advice, they could do to use it to be empowered rather than discouraged?

Torri: That’s a multilayered question.

First of all, the role of a mentor is to give you feedback. So I set myself up for receiving that feedback. I am not always the best at receiving feedback. I can be pretty defensive, and I’m sure at the time, I was looking for more. Because he was working tangentially in a role that I wanted, I kind of expected him a little bit to open that door for me and say, “Oh! work with me, or, here’s a job, that kind of thing. So I don’t know that I’m sure I handled it gracefully face to face, but was a little bit salty about it at the time, but that’s just about the repetitions of learning to receive feedback.

I definitely have, early in my career, gotten negative feedback from a boss and cried, so you have to grow up a little bit, and if you can’t do those things, can’t receive and hear feedback and hear that you’re not ready, then you’re not ready. So it sort of answers its own question.

Cory: I want to connect that back to your comment in the commencement speech about the power of doing things that you don’t want to do. Those years and that period you talked about, the accounting job, how did you go from receiving that feedback of, “okay, I need to get older, get some adult perspective, and now I’m doing things I don’t want to do.” How do you stay motivated while doing that?

Torri: A little bit of resilience. I always end up talking about this. I got fired from my first job, in a pretty indelicate fashion. I mean, from a technical resume perspective, they just did not renew my contract. And I hate that I always talk about this, but it was really instrumental to me. I did something so unbelievably cringe. I ended up emailing the highest person in the company and saying it’s unfair, that you don’t have health insurance for your employees. And they were like, “so if it’s so unfair, why don’t you just not work with us?” And I was like, great. That’s how I actually ended up in this other job working in accounting. And then in that same firm, I did IT and HR. I was a personal assistant. I did all these different things. Along the way, it was all about hunger to grow even if it was lateral growth.

I really am a jack of many trades, and I had to get comfortable with this idea of who I wanted to be in my career, which was this coach and mentor to next-gens, and the fact that I was doing IT because I was pretty good at it, and taking the value that I could from working in this multi-gen business.

So, get rejected really hard. I needed to fail in those ways. It was really important for me to open my mouth and be like, I’ve always been the top of my class. I have always been, you know, this is going to sound horrible, the smartest person in the room, and I needed to get swatted down really hard. I did not come out of that and be like, “I learned a lot.” It took a while to sink in that your opinion is not the most important thing. Sit on emails for 24 hours, don’t send the risky text if it’s going to get you fired.

Cory: One of the things that you’re saying that really stood out for me is that you were adding tools to your toolbox. Maybe you weren’t doing the job that you wanted to do, but all the way through, you were building that skill set that one day, and today serves you extremely well. You’re not doing IT and HR and all those activities, but you know what needs to be done or at least at a level to be able to talk to those people and relay that information really well.

Torri: Yeah, who knew that my background in IT was going to help me get a job at a tech startup? It’s the things that you have no idea where your career is going to take you, and where you’re going to land.

Cory: Circling that around to patience. You talked about patience. The next-gens that you’ve been working with, how would you give them that perspective of, “You’re not going to be the executive today, but wait,” and how do you relay those in for bad information in a way that they can really understand and work with?

Torri: This came up, in real life for me, actually, and sort of how I thought about the power of doing things you don’t want to do actually came from a conversation with Adam Hoffman. I went to him and I said this next-gen came to me, and he said he doesn’t want to do any kind of behind-the-desk work, he just immediately wants to work with clients. And I was sort of looking for some outside thoughts to overcome my own biases on this, because I clearly believe in this idea of the patient capital, building your career and doing all these things.

It’s different when you’re a doctor, for example, where there’s a really linear skill set. But if you’re trying to work in the family enterprise space, it’s not usually super linear, like, you get a degree in family enterprise, which is kind of what I had been hoping, to then go into the field.

So the advice that I gave this young person was I have biases against this. I have reasons for why I think you should go into the world, but I am never going to tell you not to chase your passion and do something you feel conviction about, and did it softly, but basically said, I’m not the person to bring that to. I’ll be here when you kind of come out on the other side of it because I think this is, again, you’ve got to send the stupid email and learn the thing. Some life lessons you have to learn.

So I hope this individual is out in the world and thriving and doing exactly what they want to do. But, unfortunately, all we can do is deliver softly and with compassion in building that connection. Depositing that connection with this young person and hoping that a few years from now, they might come back to me and say, “Hey, maybe you had some perspective, let’s grow together in this.”

Cory: I love that, because really what you said is you weren’t the right person for that job. They needed somebody else to give them whatever that message was, and hopefully, they did take that and go find what they needed at that point, keep growing, and hopefully, they do circle back. I think that’s wonderful in life when it does, but it doesn’t  always happen.

So, Torri, I want to talk about those reps, because somebody coming to you and saying, “I want to do this education.” It’s not exciting to say, “Hey, let’s go get knowledge in this area.” It’s exciting to say “I’m now an executive,” you know, like, going back to the patience and that status externally versus actually growing that knowledge internally. How do you work with people in that fashion to get that, call it validation that they’re looking for, for doing the work that they’re doing with you”

Torri: So you’ve been through our wealth education facilitator training, and so I’m hoping you might know where I’m going to go with this. But where do we start? Where do we start with any kind of these conversations?

Cory: Yes, it might be a leading question, Torri, but I’m not trying to put words in your mouth.

Torri: Yeah, so we start with why. It’s not super fun to learn about your role as a beneficiary. It’s not super fun to learn about what the responsibilities of wealth ownership are, certainly from a technical perspective. It’s super fun to spend money, but learning about investing, trust, and tax and estate planning, you have to think about why you want to understand it. Often what I bring to people is I have way too many worries about people in their forties and fifties, and I’ll come back to this, who were taken care of, “Don’t worry about it, you’re taken care of,” who now are tackling these big hairy monsters without their parents, without those emotional safety nets, and like this is hard. You have to unpack this in so many different ways from the parent perspective, the reveal versus conceal polarity.

What I really encourage young people to do, I feel like it’s a little unfair to call them young people. Young adults, rising gens, is think about what you might get out of this. Do you feel insecure in asking questions to your investment professionals? Do you wish that you knew what the heck was going on with your trust? Do you want to be on the family council? Finding what your driver is, is how we stay engaged. And that’s just an adult learning strategy. It has to apply to us. It has to be relevant to us, or we’re not going to do it.

Cory: Not that we want to drive motivation with fear, but the person in their forties or fifties who just lost their emotional safety net, how do we avoid that, maybe we are that person sitting there thinking, “I am protected.” You mentioned that the family office professionals just handle things, and mom and dad, they’ve just always taken care of what needs to be taken care of. And so somebody’s thinking about this now and saying, “Wow, maybe it won’t last forever; maybe I do need to start empowering myself with some of this knowledge.” You mentioned a whole bunch of terms there, trust, beneficiary basics, and all of that. How do they understand what they want? Maybe they don’t have a family council, but they know that they want to be involved. How do they get there?

Torri: Great question! Part of it is you don’t know what you don’t know, and that’s totally okay.

From the technical education perspective, I certainly have lots of resources, which I’d be happy to share. But take stock of the relationships and the assets in your life. If you own a home, you probably have a mortgage person or a banker or that kind of thing. So thinking about all these things you have in your life and the people that you have to work with, do you want to improve any of those relationships, and where do you start from if you’re going to do that? So that’s really general.

If you really don’t know what you don’t know, coming to something like Tamarind is great. I’ll also shout out that the 10 by 10 Learning Roadmap is really great for both personal and external skills, and that’s through all kinds of ages and stages, and they did a really great podcast with us that walks you through a lot of this because there are different things at age-appropriate times that we want to be prepared for.

So no shame in not knowing, but if you have an itch or you have a question, so personal example, I have gone through Tamarind’s investing coursework. I have a trust that is invested, and I wanted to overhaul all of my investments to be more in line with my values. First of all, I did a bunch of personal research. I use, you know, some of our collateral and our resources, but at the end of the day, I reached out to my investment person and said, “Hey, I don’t know a ton about this, can we just sit down and tell me the things that I don’t know?”

If you’re feeling activated in an area, don’t be afraid to be stupid. That’s actually my tagline. I don’t know anything. The more I learn, the less I know. So don’t be afraid to take stock. Chase your curiosity. Reach out to people. It’s a lot. I feel like I gave people too much homework.

Cory: That’s awesome! And, a whole bunch of stuff that we will link to, because I think there are some great things there. And yes, that 10 by 10 Learning Roadmap, it really does give a great holistic perspective on life, and at different stages, and the way that they talk about it is focusing on really that one thing, that you can make the difference and improve on right now. So I think that’s a great tool.

Torri, I want to go back to the “reveal versus conceal,” because I think that that plays into, maybe it’s a family coming to you and saying we want to improve the knowledge of our next-gen, or maybe our whole family wants to do this together. Where does that play in? Maybe they are planning the reveal, maybe they’re getting ready, or they want to improve, get a base knowledge before they bring some of this information forward to the family.

Torri: Either end of the reveal or the conceal, you don’t want to do. You don’t want to withhold absolutely everything and shock them, and you don’t want to share absolutely everything and drown them in information.

Tamarind’s curriculum is a really nice incremental way to learn about your rights, responsibilities, and duties as a beneficiary, and then you learn about the role of the trustee and how you’re supposed to be interacting with them, literally how to set meetings with them and that kind of thing.

In terms of families coming to us and perhaps being a little bit afraid that “they’re going to tell our kids everything and they’re going to ask questions,” there’s nothing in our curriculum that says you must know how much is in your trust, how much you’re going to inherit, and what distributions are going to be. Instead, we’re really more focused around that beneficiary responsibility, stewardship mindset, that kind of thing, hopefully, preparing individuals and families to have that conversation in a graduated, and conscious way.

I will say, my mom came from “reveal land,” where my grandfather did not share really anything with her, and we went the opposite direction where my mom, basically the day my grandfather passed, she inherited. She said, “here’s how much you’re worth, here’s how much you’re going to get, here’s your valuation,” and just being like, “okay,” and then saying like, “but don’t turn around and buy a Lamborghini.”

We want to be a lot more structured and thoughtful, and this really lays the groundwork for actually also setting a degree of responsibility. If you can get through the Tamarind Learning Curriculum, you can pass the exam, you can engage in the homework, you’ve really shown some credibility and some responsibility. So that’s ways that we see it. And we have some families who say, “nope, we’re not going to touch any of this trust stuff, we’re just going to start with financial literacy and investing, and we’re only going to talk about that.” So it’s okay. You can take what you need for your family, given the age and stage.

Cory: And so with that, where the beneficiary now is is curious, that empowerment of knowledge helps, but there might be a point where the family or maybe the trustee, maybe they’re afraid of that. Have you seen situations where the family isn’t on board? Maybe the beneficiary’s really working, and comes to you and says, “I want to do this, but I don’t have the support of my family.”

Torri: Yeah, that’s tricky. I don’t know that I have an example necessarily. So often the decision-maker is the parent, grandparent, or trustee. So they’re going to gatekeep it, unfortunately. I’m not saying that we haven’t had any young individuals come to us and do this. We do have some people who have approached it in that way, but often they are in a position where they can make that investment.

I will say a lot of trusts have provisions for education, and so that’s one way to do it. And we’re always, on the Tamarind side, happy to have that conversation that we’re not revealing anything. I really empower beneficiaries to ask questions. You have the entitlement label either way, frankly. You may as well ask questions and be engaged so that no one can say you weren’t.

Cory: Absolutely! And I will make the plug that, for our Canadian listeners, because we do have many Canadian, but we do have many American and global listeners that the curriculum does cover, Canadian content, where it does need to be country specific. So that is amazing.

Torri: I now know so much about estate freezes, and that’s really exciting for me.

Cory: I love that! You can be an honorary tax lawyer in Canada. I’m sure Adam will bring you on and teach you everything he knows.

Torri: That’s perfect!

Cory: We’re nearing the end of our conversation today, and there are a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Torri: I’m ready!

Cory: What is one key strategy that you believe is most essential for building a successful family enterprise?

Torri I’ve been writing about this a lot myself, about the responsibility of ownership, and being a next-gen, and that being an owner isn’t just about shares.

I think the number one thing that we can do is be thoughtful about who is going to be a good multigenerational owner, and worry about developing the right skills after the fact. So look at character, look at values, look at how they interact with the world. Are they empowered, engaged, asking questions? And then worry about whether they have the technical expertise as something that can be built.

Cory: Love it! And what is one common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Torri: The biggest thing that I run into and I see, and I’ve experienced myself, is how to cultivate engagement over generations.

As families get bigger, and they get further and further from the wealth creator and the legacy that they built, it can just kind of start to feel like a burden. So how can we keep connected to our community? That’s why my family does it is because we love the Sheboygan community and the people who live there, and we’ve been a part of that for a long time. So thinking about how we foster a love of the company and what it means.

Cory: I love that! And, yeah, that community, remembering what it is that that wealth is, what the impact is, is so important.

And, Torri, in your experience, what are the top three qualities that successful family enterprise leaders possess?

Torri: The first one that comes to mind is any good leader is someone who I think doesn’t see themselves as the main guy. So people who rely on their teams, people who know that they need help, and who can really cultivate a culture around them, is hugely helpful. And it deals with the key man issue, of what happens when that leader goes away.

Another one is being clear in your values. Every successful multi-generational family enterprise executive and leader that I know, it’s really clear about who they are, and that’s profound. It should be written on your forehead for everyone to know, and it makes doing business in life a lot easier.

The last one is being thoughtful, and conscientious, appreciating alternative approaches, and not thinking this goes back to resourcing other people, but not thinking you have all the answers.

Cory: Love that! Your second one there, not just having values that are written on the wall, but living those values is super important.

Torri: Important for the company, important for the leader. It’s an inverse relationship.

Cory: Yeah, absolutely! And, Torri, before we conclude our discussion, I’d like to highlight where our listeners can engage in more of the conversations you’re having. You mentioned some of the things you’ve been writing, as well as, maybe some of the content that you read and and listen to.

Torri: Yeah, definitely! So follow me on LinkedIn. I post about my dog, and that’s a lot of fun!

Also, follow us on Tamarind Learning. We really share a ton of fantastic resources that are outside of what we do. I’d actually highly recommend our newsletter. Once a month, we curate four articles that are the best, newest, and coolest research that is industry-relevant.

So those two things, I am getting my life together. I’m starting a substack. So, see me out in the world at some point. I think it’s going to be called Bad Beneficiary. Hopefully, by the time this is out, I’m going to have launched my initial series, and that’s all on Doug Gray pushing me there. So I’ll shout him out for saying “you need to write, Torri.” So, yeah, otherwise, check us out on tamarinlearning.com if you’re in the US, tamarindlearning.ca if you are in Canada, otherwise, I’ll see you on the Internet.

Cory:  Sounds great! And I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with our audience that we didn’t get a chance to touch on?

Torri: No, I’m just so grateful to be here. I will say you are actually a small connection that sort of has blossomed over time. You got interested in Tamarind. You were part of Tamarind’s facilitator training, and we keep connecting and talking to one another.

 So I’m really excited to see where this relationship goes.

Cory: Awesome! Well, thank you, Torri, for taking the time to share your sTorries, your experiences, and expertise with us. It’s been incredibly valuable for me. I know that our listeners will be grateful for your contribution to this episode. So, thank you!

Torri: Thanks so much for having me!

As we wrap up this episode, we invite you to reflect on Torri’s insights about the power of patience and small actions in building meaningful careers. 

Whether you are part of a family enterprise or provide consulting to them, remember Torri’s advice: don’t be afraid to ask questions, chase your curiosity, and trust that your investments in relationships and knowledge will pay off, even if the path isn’t clear today.

Throughout our discussion, we explored the multifaceted nature of next-generation development in family enterprises. We examined how small relationship deposits and embracing continuous learning can shape long-term success, and the critical balance between patience and proactive engagement. We also discussed the power of structured education in building confident, capable inheritors who can effectively engage with advisors, family members, and business stakeholders. These insights provide a practical framework for next-generation family members seeking to grow into their roles while building meaningful connections along their journey.

For families seeking guidance on next-generation development, Torri Hawley brings a decade of experience working with enterprising families. Through Tamarind Learning’s comprehensive curriculum and personalized approach, she helps next-generation family members build the knowledge and confidence needed for meaningful wealth stewardship and enterprise engagement. We’ve included her contact information and Tamarind’s resources in our show notes to help you begin your journey toward empowered family enterprise leadership.

Disclaimer: 

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This not an official program how Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those how Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at [email protected] or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.

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