Episode title: Don’t Leave A Mess – How to Disaster-Proof Your Family Legacy - with Sandy Pollack
Hosted by: Chris Raper (Baby Boomer)
Guest: Sandra Pollack, Author of Don’t Leave a Mess, Founder of Trimaran Advisory Group Ltd. Also a Family Enterprise Advisor, Certified Financial Planner, Chartered Life Underwriter, and Trust and Estate Practitioner.
Description:
This episode of From Generation to Generation features a masterclass in thoughtful wealth transfer from two seasoned professionals. Chris Raper and author Sandy Pollack unravel the psychological and relational layers of estate planning, from money scripts and family dynamics to the silent pressures between generations. Listeners will gain practical tools and heartfelt perspective to transform financial planning into a legacy of clarity and compassion. Sandy’s insights come from decades of working with business families, culminating in her bestselling book Don't Leave a Mess. Chris, a baby boomer dad and seasoned wealth advisor, adds his own lens—personal, professional, and deeply reflective. Don't Leave a Mess: How to Disaster-Proof Your Family Legacy is available in print and audiobook for those looking to go deeper. Visit dontleaveamess.ca to learn more.
As always, if you have any questions or feedback, we would love to hear from you: chris.raper@raymondjames.ca. Or you can find us at www.aspirawealth.com.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.
Sandy Pollack 00:00
We feel that there is a big gap in the planning industry where we're spending too much time focusing on strategies, tactics, and tools, and not enough time on discovery and helping our clients uncover their values, their vision, and their goals. Because they have them, they just haven't documented it or expressed it.
Chris Raper 00:05
Every right implies a responsibility, every opportunity an obligation, every possession a duty – the Rockefeller family motto.
Welcome to From Generation to Generation, the podcast that looks at wealth transfer in three distinct forms. Wealth of character, the who you are, wealth of intellect, the skills you contribute to the world, and finally, the money. And it is my belief that if we don't pass the character and the intellect to the next generation, the money's never going to last. For those of you that do not know me, I am Chris Raper, a baby boomer dad and co-founder and wealth advisor of Aspira Wealth of Raymond James Limited. And for those that do know me, you will note that I am without my champion podcast leader, my Gen Z daughter, Brittany. And Brittany has moved on to pursue her ambitions. And while I confess feeling like an inexperienced co-pilot being asked to take full control, I do want Brittany to pursue her dreams, and she has chosen a fresh path. And I congratulate her on that. On with the show. And maybe in Brittany's terms, the show must go on. I am super excited to introduce my guest today, hailing from Ottawa, Ontario, Sandy Pollack, best selling author of the book, Don't Leave a Mess, How to Disasterproof Your Family Legacy, and founder of Trimoran Advisory Group. Welcome to the show, Sandy.
Sandy Pollack 01:44
Thank you, Chris. It is a pleasure to be here.
Chris Raper 01:47
So Sandy, I'm going to put you on the spot. You recently did a five-minute TED talk for Family Enterprise Canada. Can you share that with us?
Sandy Pollack 01:55
Oh, you are putting me on the spot, aren't you? Oh, my goodness. I could give you the talk in five minutes. We're eating time. That's okay. It really started with, there I sat, quietly sipping a cup of coffee prepared for me by my gracious host. It was a quiet moment, yet heavy, across sat Joanne, eyes swollen, voice trembling. A month ago, she said, we were in Europe, laughing, reconnecting, sipping wine. Mark said he had a headache. He went to go lie down. He never woke up. The ambulance, check. The hospital, check. The funeral, check. The flowers, check. The hugs, check. The condolences, check. And then the silence. And the questions. Where's the will? Who's running the business? Why are the bank accounts frozen? Where's the paycheck? Papers and papers, some still missing, some unclear. Confusion, chaos, grief. Joanne looked at me with sadness. I don't understand. We had an agreement. I took care of the family. And he took care of the finances. I never expected to be thrown from the kitchen table to the boardroom table overnight. Why did he leave me this mess? You know, she said, we always kept talking about that we had to get our planning, and our wills updated. But you know, we just got too busy. Time at the cottage, kids, family weddings, celebrations, just seem to always put it off. She sadly admitted. This isn't just Joanne's story. This is the story of countless family business owners, families who never took the time to update their wills, who never took the time to secure appropriate life insurance, who never took the time to have those hard conversations. Because we're busy. Because we're afraid. Because we think we have time. But death doesn't wait for a convenient moment. It doesn't care about your vacation plans, or your business deals, or your daughter’s wedding. There is a price for silence. Close businesses, broken families, conflicts, a legacy of lawyers, instead of a legacy of love. So, let's flip the script. Let's stop looking at estate planning as something morbid. And let's look at it as something aspirational. Ask yourself, what are your hopes and dreams for your family? What values do you want to pass on? What legacy do you want to share? Because planning isn't about death. It's about life. It's about protecting the people you love. It's about giving them clarity, not chaos. You have the power to write a different story ending. So why don't you start today? Speak to your spouse. Speak to your lawyer. Speak to your financial advisor. Teach your children not just how to inherit wealth, but how to steward it. Because they're counting on you. Your employees are counting on you. Your family is counting on you. Your community is counting on you. And you do have the power to write a different ending. Leave a map. Don't leave a mess.
Chris Raper 06:45
wow, I have never been able to communicate it in such an eloquent manner as you just did. So thank you so much for that. Can you fill in the backstory for us? Tell us a little bit about who you are and how you got into the financial services industry.
Sandy Pollack 07:02
Oh, okay. So I'm originally from Montreal, Chris, as I think we've chatted about before, I'm a graduate of McGill University. And it was actually a 72-year-old man that was coaching me in squash that at McGill that it suggested… 72 years old, he could have been 42. Sandy, and I was either going to go into labor law, or I wasn't sure, because labor relations was my major. And he said, No, I think you'd really like, you know, financial services and insurance. And his name was Harold. And I said, Harold, you gotta be crazy. I don't want to talk about death and families and picket fences. And I had this whole vision. And he said, No, the industry is really going through a transformation. And I think you would really find it interesting. So I interviewed people from the insurance industry, what they liked, what they didn't like, and had offers. But there was one particular firm that I had to go through 11 or 12 interviews before they really looked at me differently. And I had a different take on planning more in terms of entire planning, not just strategy planning, because strategy planning often backfires, and started building my practice in Montreal, fell in love, my husband convinced me that Ottawa was, you know, more opportunities, and he's very persuasive, he's a surgeon. And so after a couple of years did take compliance, we didn't I didn’t move to Ottawa, and had to restart my practice and again, pivoted more towards what we do. And so we work with a lot of family business owners on areas such as family business, succession and transition planning. So we have a consultative practice, we are very strong in the estate planning. And we believe in working collaboratively with our clients, whether it’s investment advisors, lawyers, accountants, but we always start with the wealth builder and the wealth holder, to give them an opportunity to unpack their story, and understand their values. And sometimes they don't even know why they make decisions until we go really deep into how they grew up. And did they grow up with money without money? How did they build and learn about some of their failures and doubts and and also their family dynamics, because the best estate plans and we've done some very rigorous estate planning, using, you know, insurance and having all the professionals at the table. It's not because you've saved taxes, the best tax strategies aren't.. don't end up being perfect. It's the qualitative issues that end up creating conflicts, litigation. And it's very sad because the person that built it up did not intend it to end that way. But people are so busy with their biases and their different professions that they forget to take a step out and look at the whole picture. And what is it that the client really wants to achieve? And sometimes they don't want to, because they don’t connect with their wealth. I mean, I had a client we, you know, has been my client for the last 10 years, and he's worth $90 million. And he says, that's not me. And I said, I didn't say that was you. This is what you've built.
Sandy Pollack 10:12
And I really feel that there is a big gap in the planning industry, where we're spending too much time focusing on strategies, tactics and tools and not enough time on discovery and helping our clients uncover their values, their vision and their goals, because they have them, they just haven't documented it or expressed it.
Chris Raper 10:36
Yeah, they haven't unpacked it. And I found your book extremely helpful in that. And I recognize that, you know, one out of three learners across their population is an audio learner. So this podcast is super helpful for them because I'm hopeful that we'll draw enough out of you today that it'll make them go read the book.
Sandy Pollack 10:59
I'm just going to say this. It's also available in Audible, in audiobook.
Chris Raper 11:04
Perfect. So Sandy, I wanna dive in on the family dynamics because that's where I got the most out of the book. You talked about a couple of things, understanding as an entrepreneur, what are we running from? And that certainly resonated in my life. And so I'd like you to unpack that. And then if you can move from there to, like you said in the book, not everybody got the e-gene, the entrepreneurial gene in their DNA. So if you're a gen two, participator of privilege, you didn't create the privilege, how do those two generations interact with one another? Take it away.
Sandy Pollack 11:47
Well, that's a really big, that's a huge question, Chris, and I'm not going to, I won't be able to answer it all, but I will say, we grow up, either with wealth or without, and we have what are called money scripts. I don't know if you're familiar with that. And so it could be the gentleman that I just was speaking to earlier was saying, you know, grew up very, very poor, but had that great uncle who was successful and would do things for the family and he decided that when he grew up, he never wanted to use thread born towels again, he wanted to grow up and be that uncle to help other people. So, we grew up with money scripts and more often than not, first-generation entrepreneurs, particularly if they were born in Canada or came to Canada as a young child, have a drive to build a bigger future and they're able to leave their history behind because all they see is possibilities and it's that idea of possibility thinking. So they build their business and build and build and build, and, you know, quite often they don't even look at their wealth, but I think that, you know, there are struggles along the way. And quite often Generation 2 doesn't see that side of their parents. They see their parents as, you know, superheroes, they do everything right, they're successful, and they've missed parts of those stories because as parents, we don't want to see our children see us in our most vulnerable position. So that's where Generation 1 and 2 have a different story and Generation 2 really feel like they're under this enormous shadow, this enormous, you know, oh my God, how am I ever going to meet that? How am I ever going to exceed that? And they feel that they have to exceed whatever their parents have done. They feel this deep sense of responsibility and the parents will say, don't, oh no, we just want you to be happy and I don't, but that's not acknowledging their feeling. And I think that this is where communication and having counseling comes in is to understand that well-being is another aspect, like that cultivation of human capital and that well-being and sense of purpose. Because you don't necessarily have to do better than your parents, you know, financially. And, you know, it's really the parents supporting and understanding that pressure that maybe they didn't realize they created, but unpacking that, discussing it, having open communications. Often it's a third person, a facilitator that can help so that.. that next generation, when they inherit wealth, they can be the best version of themselves, whether it's to be financially successful in, you know, whatever path they choose or not. Wealth can soften the edges of life to give your child that opportunity without feeling that sense of obligation. And I think with families, we have to be sensitive to that. And most aren't because they don't know. They don't know what they don't know.
Chris Raper 14:54
That shadow thing makes a lot of sense to me and I see that in my practice. I see it in my own family, my wife and I have been the wealth creator, but my kids grew up in a family of privilege. There's no denying that. And yet I'm sure they feel a certain amount of that, that shadow. And if I was your client coming to you for advice, what is my role to let them get out from underneath the shadow? How do I do that?
Sandy Pollack 15:23
First would be acknowledging that you need to have a family meeting to talk about the history of what you've built, the challenges and failures and what you've learned. To encourage your children to fail is really important when they have lived a life of comfort and to explain to them that you're either on the winning team or the learning team, there's no losing team. And that's really important. Failing is so key. I also think that equipping your children with some kind of financial fluency, understanding needs versus wants, having conversations is really important to connect the wealth to the history so that they become stewards. So if you can help both generations understand that if the values are the same, they're just looking at it through a different lens and be respectful of that lens, oh my God, you could create such amazing things to happen and impact in the world that one plus one communicating is like 10.
Chris Raper 16:30
You know, as you share that, Sandy, what's going through my mind is it's really important for both the wealth creator and that Gen 2, probably even Gen 3, Gen 4, Gen 5, to understand every individual in the family and the impact that they want to have on the world. Can the money support that? Family wealth support that, but is there a certain responsibility on Gen 2, Gen 3 to be able to provide for their own basic needs? How do you think about that?
Sandy Pollack 17:11
Oh, I think that it is imperative that the wealth builder, whether it's Gen 1 or Gen 2, understand that teaching things like saving, sharing, and spending, teaching those money skills and values and the difference between wants and needs and deferred gratification. Like, yes, you can get this. However, the choice is X and Y and having the struggle, having them work, what I would call, you know, regular jobs, whether it's at McDonald's or a summer camp or Tim Hortons. I think that that's really important because they get to, not just experience, there are some people that are living on this for their families, but they also learn the respect of the human effort to work. And I think parents, you know, our job is to protect our kids and to make them happy and to give them the best. Well, no, no, sometimes you know what? You don't have to give them the best. Sometimes a little something is okay. If they really want the best, let them earn it. Let, you know, put them on an allowance or shared ownership of their education because when they own something, when they put their own sweat equity into something, it's incredible how they take pride, they take care of it. And there's a sense of ownership. And I think as parents, there's a vast majority that fail to recognize that by doing everything for your children, you're disabling them and you're not enabling them to become the best version of themselves.
Chris Raper 18:47
You know, Sandy, one of the great lines in your book, and I remember reading this and circling it and highlighting it, was I would far sooner have somebody teach me something than give me something. Just well-chosen words, a lot of wisdom packed into that. Talk to me about the importance of generosity and passing that spirit of generosity from generation to generation.
Sandy Pollack 19:19
Well, there's a few ways that you can be generous. You know, you can give money, you can give time, right? Talent, treasures, and I can't remember what the other one is. Time, talent, treasures, and I think that, and I can tell you that I haven't been great at this because in our faith, we believe in giving quietly. So we, and I think that was a mistake. I can tell you right now, I think I somewhat blew it because although we gave time, you know, we volunteered in all different capacities, both community, school, religious, I think it would have been nicer, and now I'm coaching my clients to bring their kids in when they're giving money.
Chris Raper 20:09
I know that you and I share a Judeo-Christian faith background, and in Proverbs 13 it talks about a wise person leaves an inheritance for their children's children. How do you think about that?
Sandy Pollack 20:29
Define inheritance.
Chris Raper 20:32
That's where I was going, but so it's just not the money, right?
Sandy Pollack 20:37
that's why I asked you, what are you to find as inheritance? Everybody is different. And I think that it's not just the money, it's the values, it's the history, grandparents, stories of grandparents, you know, my grandmother, late grandmother immigrated from Poland, she met her husband in New York, they immigrated to Canada. And he built a very successful business when manufacturing in Montreal, Montreal, New York, where the big fashion, and Paris, Montreal, New York, anyways, he built this very successful business. And at 48, he actually passed away of a brain aneurysm. But he had two brothers in business, they had a shareholder agreement, they had a will, they had all their ducks in order. And it's funny, because it was with London Life, which is where I originally started my career. And they just built a house in a very affluent area in Montreal, mortgage was paid off, she got a cheque and that was able to sustain her till she was 95. Which was interesting, right? Even 50 years. I know, I know. And she still wanted to leave something behind, which was when we had to sell her house. And so here I got this inheritance, and it was $27,000. Now, I didn't need it, you know, but I remembered the stories. And so all we did was I said, you know what I'm doing with this money? I don't need it. I'm going to just top up the RESPs. Like for the next couple years, I don't have to do it. This is a gift from their grandmother. And that's connecting again. And I told that, that education was really important to your grandmother, it's important to me. And it doesn't matter whether you're educated as a plumber. Okay, you go to college for that. But it was connecting the story with the gift, which I thought was really impactful. And I will tell our listeners, if you have excess wealth, you can leave it to your family. call it a family legacy, you can leave it to the government, or you can leave it to charity. And if you plan your affairs accordingly, first of all, you must leave it to two of the three, okay, minimum, and most, but you can arrange your affairs in a way that you can leave it to your family, but not all of it and repurpose the taxes to a cause that's important to you, but have your kids involved in that.
Chris Raper 23:01
Well, if I circled that back to your children's children, what I'm really hearing and being a recent grandfather, twice over now and praying for many more, it really kind of imposes on me an obligation to invest time with those children. And because these stories don't get passed on if we don't invest the time. And so, I hope our listeners will take that away. Sandy, I wanna turn to the practical because your book is so good in the practical. And so, let's say we've sold the audience on, yeah, I finally have to do something, but where do I start? I've got an accountant, I've got a lawyer, I've got a financial advisor, a wealth advisor, however you wanna refer to it. I've got an insurance person, and in the book, you talk about this whole legacy planning being a multidisciplinary sport. But the importance of appointing a team lead. Unpack that one for me, please.
Sandy Pollack 24:16
Okay, so each profession, including my own because I'm a big risk and insurance, as well as we do advisory planning for fees, each have what I call our professional bias. You know, we have our biases, right? So, in that group, often there's one who is a little more curious, who is asking questions, who you go, geez, I think this person gets me or I can, I think I can trust this person. And first of all, they have to be competent in whatever they do. But I think finding one person that could be the lead advisor to say, okay, what is it that you want? And why? Planning is basically in a few very simple areas. It's about investment, tax, legal and risk. That's it for so get the people around. But before they start spouting off all that they can do in their strategies, one of those four needs to be the person to get deeper into what your real goals are, what your values are. So those can be honored in all your planning, because the best best tax plan is not the best estate plan is not the best family legacy plan. But I think working in collaboration, and asking questions and how is you know, have I missed something here? And more often than not, I will. But having that sense of humility to be of service to your clients or be a servant, what I call it servant leadership.
Chris Raper 25:49
servant leadership.
Sandy Pollack 25:51
So powerful, not for the advisors, it's powerful for the client and it's about being client-centric.
Chris Raper 26:00
So, picking up on that, Sandy, I've been in those meetings where, you know, we have the accountant, the lawyer, Gen 1, Gen 2. And I want to offer this as a note of encouragement to all listeners. It's really important that you, as the client, make sure that everybody in the room knows who the quarterback is or the champion. And because if that's not clear, things, egos, can get in the way. And so, I would just offer that as encouragement. Sandy, do you have any follow-up comment on that?
Sandy Pollack 26:46
Yeah, I would say that if I were a client, I'd want to know if I'm going into a meeting that there's a meeting plan. Because yet total mayhem. So, I would ask what's the purpose of the meeting? Why is it important? What are going to be the measurable results at the end of this meeting? And what are the next steps?
Chris Raper 27:06
Yeah. So I want to talk about, uh, in your book, bang, you're dead. Uh, and if you want to know what bang, you're dead is all about, you have to read the book, so you're going to have to buy it or buy the audio after somebody's dead, particularly on the second survivor or the last survivor. Things tend to come unraveled if there's not two things in order. Uh, and I only learned about the second thing from Sandy's book. There's a letter of wishes, which kind of deals with the, um, all the physical things, the chattels, if you will, the dining room table and, you know, and one of the things that happens as we age is, you know, we might promise things to one child or grandchild and we forget about that promise and then we turn around and promise it to somebody else. And this creates huge contention, uh, and destroys families. Talk to me about the importance of a letter of wishes with respect to personal effects, and then more importantly, maybe the legacy planning letter, the legacy letter you talked about, cause I found that super interesting and about doing that every 10 years or so.
Sandy Pollack 28:23
Letter of wishes could just be simple in terms of special effects that you have and who you want it to go to. And that could change, by the way. The legacy letter is more, some people call it an ethical will they're known as, which is things that you want to share with your family and lessons and values that you would like to pass on and also to share with your kids how you feel about them. And we don't say I'm proud of you and I love you enough. And what a legacy letter does is it's, it's beyond money. It's about helping your children not feel guilty whatever the gift is and give them something, a piece of you that's timeless that helps you as you navigate your own chapter in your own journey in life by putting in particular points. And it's something that the kids are going to have forever. I mean, my eyes are welling up as I'm thinking about it because you know, you never you know, you love your spouse, whether it's your first, second, third, whatever it is, and you love your kids. But to actually see it in writing, it's so overwhelming. And it's, you know, marriage, they leave their socks here, they don't put their dishes in the dishwasher properly. But this letter, you forget about all that stuff. And that's, that's the true meaning of having meaningful relationships. Just think about that and, and call an advisor advisor. And if it's the wrong one, then keep looking because there are many good advisors out there that can help make your your life journey and the wealth that you've built meaningful, purposeful, and empowering to many generations to come.
Chris Raper 30:19
Sandy Pollard, bestselling author of Don't Leave a Mess, How to Disaster Proof Your Family Legacy. And yes, you can and you should get the book on Amazon or Sandy's dedicated website, dontleaveamess.ca. Thank you so much for being a guest on the podcast and leaning in with us today.
Sandy Pollack 30:47
Thank you for inviting me Chris and you are most welcome and I hope this touches the heart and soul of many of your clients and listeners so that they can make a positive impact for many generations.
Chris Raper 31:01
To our listeners, thank you for taking the time today. I am sure that Sandy's conversation has spurred some great thinking, and there is a significant call to action. If that is resonating with you, I would encourage you to reach out. We can carry on the conversation. Feel free to go to AspiraWealth.com, where we are in the business of helping our clients live out their greatest aspirations. My name is Chris Raper. I am co-founder and wealth advisor at Raymond James Limited, bidding you good day and may God bless. Thank you to Nathan Clark for composing our music. Thank you to Jasmine Manhas, our new marketing director and now editor-in-chief for the podcast.
Jasmin 31:53
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