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Today’s episode features an inspiring conversation with Karishma Ismail
, an expert in helping high-achieving entrepreneurs and families create meaningful connections and lasting legacies. Joining host Dave Wolcott, Karishma Ismail brings her personal journey as a first-generation immigrant and successful entrepreneur, highlighting the struggles and lessons learned along the way—from witnessing her father’s tireless work ethic to navigating her own path through burnout, success, and ultimately, clarity about what matters most.
Throughout this episode, Karishma Ismail peels back the layers of what legacy really means, moving beyond dollars in the bank to focus on the importance of family unity, intentional connection, and self-awareness. She offers simple, practical strategies for fostering connection and harmony within families, especially for those managing wealth across generations. Karishma Ismail and Dave Wolcott also explore why family conversations can be challenging, particularly during the holidays, and how breaking old patterns and roles can spark new, authentic relationships.
Whether you’re an entrepreneur, a family leader, or someone seeking deeper fulfillment and connection, this episode is packed with valuable lessons for building a legacy that isn’t just inherited, but truly lived every day.
In This Episode
- Why disconnect happens in families—especially among high achievers and across generations
- How to create intentional connections and safe spaces for family conversations
- Practical strategies to break old patterns and foster ongoing family harmony
- The power of living your legacy today, not just planning for the future
I want to show up here because this is really what matters. So I’m just taking that approach of like, we don’t need to waste the next 30, 40, 50 years of living life disconnected. Let’s create that connection today so we can really enjoy those pieces today.
Karishma, welcome to the show. Really excited to really talk to you today about one of the most important things about wealth building, and it’s actually legacy. And legacy is one of those, you know, one of those things that’s really hard to put your finger on. And, and I think, you know, we all kind of talk about it as if it’s something very meaningful and important. But as you start to kind of drill down, we don’t necessarily have strategies or tactics on what that legacy means beyond a certain number in a bank account or a portfolio. Right. So really appreciate your time today and coming in to help really dispel and create some clarity around how we can create some strategies around, you know, creating a bigger legacy. Legacy for those out there.
Beautiful. Well, thank you so much for having me.
Yeah. Awesome. So why don’t we begin and, you know, tell us a bit about your journey, your journey and how you really got here in terms of legacy, because obviously you must have gone through some transformation yourself to really start to embody this work that you do.
Yes. Beautiful. And it’s true, I believe all of us entrepreneurs, it’s our own stories that shape our journey and our paths in service, servicing others, especially when it comes to coaching, consultant type roles like myself. You know, it’s interesting because I come from a first generation, I’m first generation Indian. My dad, we came to America when I was 5 years old, and my parents built, they lived the American dream. You know, they built a business from scratch. And I saw my parents, especially my dad, working seven days a week, you know, really creating the business that allowed us to have a great life and a great lifestyle. And, you know, it was interesting.
I remember just as a kid watching him and saying, is this what business is supposed to look like? You know, that sacrifice? And I didn’t have the words for it as a little girl. I just remember the feeling of not having my dad, you know, there, except for Sundays, which was our family days together. And I think for me, a lot of that, seeing that created a lot of resistance in me, especially as I became a mom, that I never wanted to have something that would take me away from my children because that was really important to me. And I always had this inner yo yo.
Until, of course, you know, six, seven years ago, in my training and development journey, I was climbing up the ladder. I’m a global training manager. I’m coaching executives and helping them with productivity and business and conflict and all these, like, HR issues and all these things. And I hit my own burnout.
And I realized that the only way that I could actually have the time, freedom that I really wanted was to become an entrepreneur. And it was interesting because my, I came into my business and I found myself doing the very thing that I told myself I would never do, which would be, which was sacrificing the time with the family for time with business. And in fact, I was very lucky. A lot of synchronicities, life happened, and I believe when you align to your purpose, beautiful things happen.
My business, you know, took off. I’m hitting, you know, almost six. I hit my first six figure month just a few months into my own coaching business, and I found myself completely burned out, and I couldn’t get myself out of bed.
And I created this new glass ceiling for myself where, because I’d hit this great number and I’d quote, unquote, made it, now I had to surpass those goals for myself and work even harder. And I found myself becoming the very thing I hated, which was resentful, angry, overwhelmed, and not the mom that I wanted to be.
And I’m so grateful for that, looking back, you know, five years ago, because a lot of that shaped how I do business today, which is about really having that balance, being proud of who I am. So even my brand kind of was birthed from that concept of living my legacy, of being proud of who I am as a person, as a mom, as a partner, as a friend, as a coach, like as a human being, while I leave and create and build that legacy that I desire to leave behind for the children.
And it’s been such a fascinating journey because in the last five years, supporting 150 plus clients, it’s been the exact same struggle that I’ve seen, where a lot of us high achievers are so great at creating something, building something, having something, and our identities are so enmeshed in our businesses that we’re so proud of. But we don’t like the way we feel when we’re not working, and our marriages are in a state of disarray. Our kids are disconnected.
And for me, there was a really a big desire, and kind of having gone through it, to really support my clients to embody that freedom while they also leave the thing behind, and not to have nothing but regret facing them in the last few years of their life.
So for me, there’s like a deep, deep mission of helping facilitate that inner freedom, if you will, that legacy of love, connection, and joy while we leave something behind for the people that we love.
Yeah, that’s awesome. You are really running a meta business, which is really one of the best expressions of a business, right. It’s really an expression of your consciousness. And to be trying to solve the same problem for yourself that you’re bringing to other clients is really a great way to operate because, you know, who knows it better than you? Right? Coming for sure. So that’s fantastic. Well, I find it fascinating again, if we kind of think about some of the statistics around legacy, you know, most wealth, it’s over 70% is lost by G2, and by the time it hits G3, it’s actually closer to 90% that’s lost. But how can, you know, people start to think about legacy, right, so that they don’t become one of those statistics. And not only really just about wealth, right, because that’s just financial capital, but some of these other important things and legacy. How can people start preparing? What are some of the strategies that you recommend?
Legacy isn’t a destination in the future – it’s how you live today.
Yeah, that’s a great question. And you know, it’s interesting because even this, I’ll call it niche of this problem that came to me, you know, as a coach, it actually was a need that was identified from wealth advisors that supported high net worth individuals, founders, as well as family offices, where, you know, they’re supporting clients that are at the table and they’ve got all the wealth strategies in place. Yet there’s a fundamental inability to move the needle, a fundamental inability to kind of establish those financial principles and do what needs to be done to grow the wealth, sustain the wealth, preserve the wealth, transfer the wealth.
And kind of going deeper into those dynamics, it was really about disconnection, the disconnection within the family unit. Disconnection could be between partners, between spouses, between siblings, between founders, you know, first gen founders, next gen kin. And there was a lack of, like, basically a disconnection that was happening that was preventing those conversations from taking place, which prevented the financial pieces to take place.
And so essentially when it comes down to it, so if the problem, kind of the root problem, kind of what I see is disconnection, then thereby the solution is fostering deeper connection. And you know, when you think about, like, you know, when you think about, and I’ll use like a partnership example with two partners, when there’s disarray. A lot of disarray in companies is because of disarray or lack of alignment of values.
And a lot of times, you know, especially when it comes to very interesting dynamics and you have a lot of wealth at the table, the founders that created the wealth may have very different values than the values of their children. And now we go two, three, four generations forward, you know, fourth gen, those values may look completely different. And a lot of times, you know, the third, fourth gen may never have even had the opportunity of being asked, like, what’s important to you, or even feel like their opinions counted.
And thereby, like, you know, having a safe place. And you know, I’ve been blessed to be a part of those interesting and complex conversations. But having a neutral person to help facilitate those conversations and really give everyone a safe place to express who they are, what they care about, what they want, really allows those conversations to happen, thereby allowing the financial advisors to do what they’re best versed to do.
So if someone is listening and they’re in that state of disarray, I would really encourage them first and foremost to just bring everyone to the table and say, hey guys, what’s important to you? And just allow those conversations to happen. Because it’s the unsaid conversations that often create those rifts.
And all we can usually see is just the tide is, you know, the tides are rising and there’s a lot of conflict, but we have no idea what’s happening. So just even having that safe, neutral environment to start having those conversations can make such a big difference because now everyone really has a chance to express what they care about, express who they are, express like what matters to them, not what is supposed to matter to them based on what they were born into.
Wealth means different things to different people. Now we can have this beautiful conversation where there’s a safety in expressing self. There’s an ability to create and foster connection because people feel safe to express. Therefore, it releases a lot of that heat and the turmoil. And now we can, you know, when everyone has a chance to express who they are, now we can actually talk about what it looks like to really move forward.
And for me as a coach, I get to help them see what’s similar, what’s the same.
Because ultimately I believe what we all want as human beings is the same thing. We want to be loved, we want to be seen, we want to be valued, we want to be given a voice. And when everyone has the ability to have that voice shared, those conversations are amazing.
So the first step would be try to have those conversations by yourself, try to create those connections with the family unit and start creating little steps to create harmony in the family because we can’t even talk about business unless we have a harmonious kind of place to stand. And then we can talk about what it looks like to move forward.
Why do you think these conversations are so disconnected at the family level? We’re recording this at the time of the holidays, and a lot of the listeners just finished Thanksgiving. You know, we’re in Christmas. And again, coming back to statistics, right? The holidays can be some of the most stressful times that people have, yet it actually should be, you know, the biggest time for gratitude and appreciation, right, and connectedness. But yet it seems to be really challenging with a lot of families.
So what do you think is really the root cause of that?
And that’s a very loaded question because I could probably talk about that for hours. But you know, when it comes, the first thing that came to mind for me was, you know, we all have, in every single one of us, family office or not, we all have these roles that we think we need to play. You know, we all have these masks that we wear, right?
And you might be a first gen founder I’ve worked with, you know, and you know, there’s a lot of weight of responsibility. There’s a weight of like, I’m the problem solver, I’m the fixer, I’m the one who has led the forces, right? And there’s almost this sense of like being in control, being in control. That of course is great when it comes to business, but we as human beings actually resist being controlled.
So it creates a lot of resentment for those that are around them, but it also creates a lot of resentment for that founder of having to be the one that is carrying the weight in every area of life. So there’s like this false sense of responsibility and feels really real, but it’s like a mask that that person wears, right?
The founder may wear. The next gen, second, third, fourth gen may have this resentment of, well, no one even asks me ever, like what I care about, and almost feel like they’re the ones being controlled or their voices don’t matter or decisions are made without even being consulted or even feeling like an imposter because they were never part of this empire that was built outside of them.
So this almost like feeling of nonchalance or, you know, my opinion doesn’t matter, like why am I here. And what it looks like is it may be silence. What it looks like may be someone just showing through their actions that they’re disconnected. And it doesn’t really mean that they’re disconnected or they don’t care. It means they don’t feel like they’re a part of it.
So these roles and responsibilities that we all have, where we all play a mask, we all do in our family dynamics, create a lot of tension.
And therefore it’s so easy for a lot of us, again, high achievers, to go to business and work all the time. That’s easy. Now you’re facing your family where you’ve got all those masks that you have to wear. And now there’s a lot of emotion around it because you have that mask of like, I have to be in control. But you also have this expectation from others. And now you’re expecting others to play the mask that they’ve also.
And so it just gets exhausting because now we’re just walking around with these, the weight of these masks that we’ve put on.
It’s like we haven’t learned how to give ourselves permission to let go of those masks and just relax and just be. And I believe that’s why family dynamics are exhausting.
And now here we are, and now you have an expectation of your child and your child isn’t respecting you or he’s disconnected from you, or she’s disconnected from you. It creates a lot of angst because it’s almost a sense of, I’ve done so much to support you and this is what I get, right?
So there’s all these emotions that come up from the people that we care about the most because of our own, what we deem that we need to do, but also what we expect others to do, versus kind of like just everyone give each other a break and just be and be who we are without all of that.
And I know how I’ve heard a lot of clients and I’ve supported a lot of clients that this time of year especially, those emotions are sky high and really exhausting and debilitating on every level.
And it should be something else. But unfortunately, that’s not what it is for a lot of families during this time of year.
Yeah, great insights to that. I mean, you know, my experience has been, it’s interesting because I think everyone is at a different level of growth in their life, right? And then when you get back together, especially with the older generations, I think everyone pictures you how you were when you grew up in that same household. So if you’re a younger sibling or something like that, you’re still treated as that younger sibling regardless of what you’ve done, right?
Yeah, all of us.
Yeah, the person that you are now, right? So I think sometimes maybe that’s where some of the friction lies. And then, of course, everyone grows at different levels. And so trying to create that harmony, I see, is challenging on the back end.
And that’s one of the things I’ve been working on. Our immediate family is, in fact, that was actually a big goal of mine this year, is to create harmonious family get-togethers. And so it was great, and I think we were really successful in architecting that environment very intentionally for this Thanksgiving. We had everyone in for that. But yeah, it takes a lot of thought.
Any comments there in terms of levels of growth and things like that?
I love what you said about intentionality because it doesn’t happen by accident. For a lot of us, I think that’s a facade. We don’t all live the Brady Bunch version of reality, right? But then the other part is, I think if you bring in a family that may see each other once a year, it takes time to acclimate and it takes time to create those bonds. So for me, I love the holidays and I don’t like the holidays because there’s a sense of forcedness, like having to come together for this.
But when you have regular touch points and those conversations, the dialogues, experiences are a recurring phenomenon. It takes the pressure off it being a certain way and it can just be. And now everyone has an opportunity to get in front of each other and simply connect for the purpose of connection, nothing else. And I think that’s the gold, right? Just allowing that to be a part of the norm, not the exception.
Because a lot of us, especially in America, the family get-togethers are the exception, not the norm. And then there’s an expectation of what it looks like or should look like that creates a lot of the angst for most.
Yeah, love that. Karishma, when we were speaking in the green room earlier, you were talking about really your branding and what it meant to you. Can you share that with the audience?
Yeah. So Live Your Legacy. I actually came into my journey as an entrepreneur, like I shared, and having supported 150-plus high net worth founders, family offices, clients over the last few years, what I’ve seen is just that angst of like, you’ve built everything and business is great, you have the dollars in the bank account, but then you come home and you feel disconnected. You come home and you feel lost. You don’t know who you are.
I’m supporting someone as we speak who is literally at the stage of retiring and selling his very successful business. But what does it look like to go from working for the last 30, 35 years to not working? And then you have to face the reality of everything else that isn’t work, and finding himself lost, disconnected, purposeless.
So what I’ve come to realize is that retirement or legacy or any of this isn’t about some destination in the future. It’s really about living that purpose, living that connection, living that joy today while you leave for the future. And when we think about family offices, high net worth, and anything that entails transfer of wealth, the only way that we’re able to even have those conversations about growing wealth, preserving wealth, transferring wealth, is if we have that connection in place. The conversations can only happen when connection is in place.
So even if you think about it from a business perspective or ROI perspective, living that legacy, being connected in the family, showing love in the family, being a part of the unit as a family, not the business part, but as a family, that is what makes all the difference on a human level, fulfillment level, purpose level, but also the business level and then the society level. Because when you’re happier on the inside and connected as a unit, everything you want to do to contribute to society reflects that love, that purpose, that joy. And it ripples into society, ripples into humanity. And that’s how important this work is.
Yeah, really love that. Really just changing up the timeframe. Because when we typically think about legacy, it’s all, okay, what are we going to leave when we’re gone? And we think about that in terms of assets, not only capital assets, but maybe a family constitution, or passing on values, or some type of philanthropic venture.
But I really love where you’re coming from with this whole approach of living your legacy today. It reminds me of one of the core leadership principles from the Marine Corps, which is lead by example. So living your legacy and those values that are very important to you allows your immediate family, your friends, and the people around you to experience that and understand what that is. And I think the ability to instantiate that in future generations has much more probability of success.
Absolutely. You’ve nailed it exactly. Because all we have is today.
Yeah.
And we think we have, you know, we really kind of look at life and say, okay, if I only had 24 hours to live, how would I live? It changes our discourse with everything. The things that we deem to be important, most 90% of it goes away. And then we look at our life, our families, what’s inside the household, and say, okay, I want to show up here because this is really what matters. So I’m just taking that approach of, like, we don’t need to waste the next 30, 40, 50 years of living life disconnected. Let’s create that connection today so we can really enjoy those pieces today and really focus on the human, focus on the relationships, focus on the things behind the scenes that are preventing that happy, joyous, free version of legacy.
Do you have a few strategies that people can start to use today?
That is a great question. I think the first thing I would say is, and it sounds so simple, but it’s what you mentioned a few minutes ago. It’s intentional connection. It’s intentional connection not for the purpose of going through documents together or talking about a business plan, but just showing up for the sake of showing up, right? And showing up because you want to and just enjoying the family. That’s the first piece.
The second piece is almost like a self-awareness thing of just observing yourself. Like, how am I showing up? We all get triggered by family. Every single one of us does. It’s a human thing. But noticing those triggers and noticing the parts that we play in those triggers. Am I being triggered because I want them to be a certain way? Is it my control that’s showing up? Is it me feeling resentful because someone expects me to be a certain way? Is it my rage? Is it my anger? Is it my powerlessness? Just starting to observe the self and observe the dynamics around self.
One of my mentors years ago used this expression. She would say, “Detach with love.” And I’ve shared this with so many clients. Again, it sounds so simple, but a lot of times those triggers come because we’re so emotionally involved in the situation. When you start noticing people like you’re watching a movie, especially during family gatherings, I still do this today. When all of us get together, there might be 10 or 12 of us in my house on Christmas. I watch the whole family like I’m watching a movie.
And then I can watch the crazy characters in my movie do what they do, but I don’t have to get wrapped up in it. I don’t have to lose my peace and get entangled in the drama. I can just watch it like a really interesting piece of entertainment. When we start holding our peace as the most sacred thing, that’s what allows us to enjoy that state of being. It allows us to let go of control.
It allows us to let go of all of the agenda items, because we all have them. Ego has all these agenda items. But having those opportunities to simply connect and be is super key.
And then the third piece is just noticing what’s happening. What is it that’s going on with that third, fourth gen that feels disconnected? Asking them the questions like, what do you care about? What’s important to you? What does wealth mean to you? If you could leave something to charity, what would that cause be? Just being curious about the people around you, even though they’re your family.
Even in networking they say it’s curiosity and asking questions that makes good conversations. So often we forget to do that with our families. We assume it should be this way or that it was what it was 10 years ago. But the person in front of us may be very different than they were five years ago or 10 years ago. I know I am.
Taking that stance of curiosity to start creating those bridges in the family makes such a difference. And not just from a peace, fulfillment, purpose, living-your-legacy standpoint, but now we’re talking about those hard conversations that happen in the boardroom. When there’s a sense of connection and feeling like you matter, you’re valued, and you’re heard, amazing things can actually happen when it comes to moving, growing, increasing wealth, transferring wealth, all the things that we started talking about today.
Intentional connection doesn’t happen by accident – it has to be designed.
Yeah, it seems like such a subtle change, but the impact is so powerful. And part of my vision statement is to be world-class, not only as a father, but also as a son, a brother, to all of my family around me. It’s been really interesting over the years because my parents are aging at the moment.
Certain things that would have triggered me in the past, I’ve paused and really thought about things from their perspective and tried to give a lot more grace to the situation. I don’t have to be right, and no one really has to be right. That self-awareness and coming at it from a different perspective can ease some of that dissonance, and then you can move into being in more harmony with the family.
Absolutely. And harmonious families are the ones that make it generationally. You can have a family in disarray, but when you ask that third or fourth gen if the values are the same, they’ll say no. And we’re all entitled to our own opinion. But ultimately, I believe we all want the same thing. We all want to matter, we all want to belong, we all want to feel loved.
If we create the space and the intention to have those conversations, to connect for the sake of connecting, to connect for the sake of loving, that’s the harmonious family. That’s the family that’s able to move together and bring a united front to everything they touch, the investments, the charities, all of it. And it makes such a difference. It makes such a difference.
Do you have any specific tactics people can do in terms of getting together on a regular basis, like an annual retreat, or anything else you can think of? My kids are in their 20s and live in different states across the country, and it’s even hard with immediate family to get together anymore. There’s a statistic Peter Attia shares about the number of hours you spend with your parents after you leave home at 18. It drops precipitously, and it’s really shocking. So how can we get back some of that time?
That’s a great question. Retreats are great. I think facilitated retreats can be even more powerful. You can be at an all-inclusive resort in Mexico, for example, and everyone can still be doing their own thing and having completely separate experiences. It comes back to intentionality around those retreats and gatherings.
I’ve been fortunate to facilitate workshops and retreats for families, and it’s about creating a safe, neutral place to have conversations. Everything doesn’t have to be heavy or about documents and ordinances. Sometimes we don’t even know how to break the ice with our family. They’re right there, but you feel like you can’t be yourself around them. We all have those feelings.
Having someone facilitate and bring structured activities can help everyone see each other from a different lens. It can be really beautiful and fulfilling. I think about children on summer break. Summer feels so long when you’re a child, but as adults, vacations feel like they’re gone in a blink. The difference is that children experience everything as new.
As adults, we get stuck doing the same things the same way, with the same behaviors, habits, and conversations. Even a family retreat can fall into that pattern. But having different experiences and stepping out of that comfort zone allows people to see each other differently.
When you come out feeling like you learned something about yourself and something about someone else, that’s the gold. Feeling like, I really enjoyed getting to know you, and I’ve never talked to you this way before. That’s the gold mine right there.
Yeah, 100%. And this is such a great time for this topic, right? We’re kind of coming into 2026. And there’s a great saying that you can really tell what someone’s life is like by looking at their calendar and their bank account. So if you can intentionally carve out time for your family and to be living your legacy, now is a great time to really do that. And I think that’s really cool.
Right. You were talking about architecting an environment in which people can express themselves and have fun. And I find that the environment is so much of it, right? So, like Thanksgiving, if you go back to your old house where you grew up, everyone kind of falls back into the same patterns. But if you go to, let’s say, a big Airbnb or some new environment, everything feels new and it changes.
So that could be one strategy. A friend of mine is doing something really neat where he takes his grandkids, once they turn, I think it’s age 13, and they get to pick their own trip anywhere in the world, whatever is interesting to them. And what an amazing bonding experience he creates with that next generation. I think there are some really neat ways to architect these experiences and create connection, but it must be done intentionally. And I think this is such a good time of year to really reflect on how we can improve that.
Absolutely, yeah.
Awesome. Well, if you could give just one piece of advice on how the audience could really accelerate their own legacy, what would it be?
I believe the biggest thing is to start allowing those hard conversations to happen. Unfortunately, I think sometimes pain is the driver for change for all of us. A lot of times, let’s say you’re trying to bring people into the boardroom from different generations and get the next financial piece in place, and you’re not able to. Instead of throwing your hands up and saying, “I’ll try again later,” it’s about looking at what’s happening and asking, what can I do proactively to change this?
Unfortunately, many of my clients come to me when some of the damage has already been done for a long time, but it doesn’t have to be that way. And it doesn’t mean everything is doomsday if it is. There are ways to start reversing that damage and creating greater harmony. Harmony is what facilitates growth. Harmony is what facilitates movement in a positive direction on every level, financial and otherwise.
So the biggest strategy I would say is going back to what I mentioned earlier: allowing a safe place of connection for the family to come together and asking, what’s important to you? What are the values that matter to you? Without judgment, without force, without “my prerogative, not yours,” but simply allowing those open conversations to happen. That can be truly pivotal.
It helps move the family closer together so they can co-create and do amazing things for the future, both within the family and externally in society. Sometimes it’s as simple as saying, “I’m concerned. I haven’t seen you in a while. What’s going on?” That’s very different from accusations or frustration. Asking from a place of curiosity and seeking to understand, not to control, makes a huge difference in connection and in preventing future conflict.
Yeah, totally love it. It’s been such a pleasure having you on the show. If people want to reach out, learn more, or connect with you, what’s the best place?
Thank you so much. I’m on LinkedIn, Karishma Ismail. You can look me up and send me a quick DM, just mention that you’d like to connect. My website is Live Your Legacy, and you’re welcome to book a free call. We can have a confidential conversation about what’s happening and what the next possible steps might be.
Awesome, Karishma. Thanks so much for your time and insights today. I really appreciate you.
Thank you, Dave. I appreciate it as well. Have a great one.
Thanks for listening to this episode of Wealth Strategy Secrets. If you’d like to get a free copy of the book, go to holisticwealthstrategy.com. That’s holisticwealthstrategy.com. If you’d like to learn more about upcoming opportunities at Pantheon, please visit pantheoninvest.com. That’s pantheoninvest.com.