Legacy, Loss, and Living With Passion with Elliott Kallen

Introduction and episode preview

00:00Bill Gallagher: Have you ever had a week when you're completely slammed, but somehow nothing actually moved? Is this one of those weeks? That's not really a time problem. It's a busyness habit problem. My new book, Busy Is Broken: Do Less, Scale More, is all about growing by doing less, not more. Read or listen to a sample chapter over at busyisbroken.com. That's busyisbroken.com. It's also on Amazon and other booksellers.

00:35Bill Gallagher: All right. At the end of the day, what really matters? At the end of our life, what matters? I've been struck by this thing for a long time. At the end of our life, right after our life, there are two things among many, but two things that contrast: your eulogy and your obituary. Right? And the obituary talks about what you did. The eulogy talks about who you are for people. Both are interesting. We're going to talk about your legacy and what really matters with Elliott Kallen. Hang in there.

01:13Bill Gallagher: Hey everybody, I'm Bill Gallagher, Scaling Coach and host of the Scaling Up podcast. Our show comes to you every week. More than 650 now at scalingcoach.com or wherever you're getting this right now: YouTube, LinkedIn, Apple Podcasts, Spotify. Like it, subscribe, notify, don't miss one, right? You can always skip it if it's not for you. But we've got an awful lot there. And if you'd like to come and do a workshop, put your hand up, say, let's see what you got for me. Let's test it. Step up. I know you're ambitious. If you watch, if you listen to this show, you should talk to me. You should reach out. So go to scalingcoach.com, join me for a workshop. I will alter the way you think about your business in just a couple of hours.

02:03Bill Gallagher: All right, listen. My friend is Elliott Kallen. And Elliott is founder and CEO of Prosperity Financial Group. We were in a business forum for CEOs some years ago and he's just a huge-hearted man who runs a great business, really helps a lot of people. So Prosperity Financial Group is financial management for folks. They help people figure out and create their future for their business, right? But it's not just about the money, it's about everything that you leave behind. He's also the president and co-founder of A Brighter Day charity that he launched after the suicide of his youngest son. And he's a bestselling author. He hosts his own show and he runs this charity. So, Elliott, welcome to the show. Thanks for joining us today.

02:50Elliott Kallen: Great to be here, Bill. Thanks for having me on.

02:56Bill Gallagher: Yeah. So the growth of your business and the loss of your son were really closely aligned events in your life. Talk about the contrast to that and tell us the story of whatever you think is important for people to know there.

Buying out a partner and losing a son

03:15Elliott Kallen: Great. Well, thank you again for having me on, Bill. Let me tell you first about Prosperity Financial Group. That's company number three that I've started. Now I'm at four and five. Obviously I'm some form of an entrepreneur, not necessarily a serial entrepreneur. I don't know what exactly that means, but I love entrepreneurship and I love starting things. And I started Prosperity Financial Group almost 30 years ago with a partner and it was time to buy him out. It was time to retire his number, so to speak. He had gone the distance and was done. And so in December 2014, we signed a five-year deal for a million plus taxes, $1.5 million basically. And that was the buyout. And three weeks later, my youngest son walked, jumped in front of a truck at the University of Montana and took his life. And so that little euphoria was a really short-lived program.

04:09Elliott Kallen: And then I came back to work after burying him in Lafayette, California. And I'm sure every parent can imagine it's a horror story. I don't need to go into every detail of it, but it's a horror story: identifying a body being hit by a truck and transporting back. And so it's just a horror story. And I couldn't even work for the next two months. I'd stare at my computer screen because that was my screensaver, my kids. I had two other kids. And like you, you're a father, you can't even imagine it. You'd be, it wipes you out. No one can. No one should either. So, it's not meant to make anybody else cry, but I just had to deal with this.

04:46Elliott Kallen: And so we went on this journey and I realized I needed to sink into work, but I also needed to do something, not in memory of my son, but to prevent other families from going through this tragedy again. We wanted to prevent teen suicide. And since I'm a charitably inclined person anyway, we started now business number five, a foundation called A Brighter Day or abrighterday.info, which creates resources on stress and depression. And now it's touching 3,000 families a month. So here we have $500 million in individual wealth, $500 million from another company I own in individual wealth and a foundation. Don't think I think 40 hours a week is a part-time job.

05:30Bill Gallagher: I know you're a hardworking guy. He's like, I've got to get in the office. I'm like, Elliott, let's have breakfast or something sometime. He's like, no, it has to be before like, I don't know, a too early time for me. I'm like, let's just need…

05:43Elliott Kallen: I get up at 4:45. I go to the gym. It's the only time I can work out. I'm in my office by 7:30 and I try not to be the last one to leave, but invariably once or twice a week, I'm out of here at 5:30, 6:00. These are long days, but I'm still not accomplishing everything I want to do. And I'm trying to start a new business coming up for 2026. So, there's that plate is always falling. I love it.

06:05Bill Gallagher: You know, I don't want to brush over… You say you can't think about it. You don't want to think about it. It's unimaginable, right? The most horrifying thing is to think about losing… And you're like, I don't want to make people cry. And I'm like, it's okay if people cry a little bit. Look, what you cry about if you're touched by this thing is your love for your own child or for a parent or for someone, right? The idea of losing someone you love, the thing that's there for you is the love and that's okay. Like, it's okay to be emotional about that. Right? And it's okay to let that propel you into saying, no, this shouldn't happen to anyone else. I want to support that charity. I want to take a part of that because I know someone who it happened to, because I know someone else, because it almost happened to me, because we've all felt it. Right? Because I have a friend like you who it happened to, because someone somewhere… Like, reach out. So we'll just put it up there again. abrighterday.info. As the… Wanda, if you'd throw it… Yeah. And we'll put it in the show notes a couple times and at the end, right? It's so, so important. And look, let's say they just prevent one.

07:22Elliott Kallen: It's amazing. Let me tell you something we do that I'm really excited about. Yeah, I mean, obviously, we're touching a lot of families every month. Yeah. We created a teen… We know that teens don't read our website. We get it. They're not readers. They've got 20-second TikTok attention spans. That's just the reality of it. I didn't create that. I'm sure you've had psychologists on here, business psychologists. They could talk about that all day because it's bigger than the two of us. Yeah. What we did is we know that teens love their phones. They love texting. Every truth that they know is on their telephone or it's not truth to them. It's what they do.

Creating a teen crisis texting hotline

08:05Elliott Kallen: And we created a teen crisis texting hotline that's 24/7, all 50 states. So now it's in three countries. All 50 states, basically. They could text and in under about a minute, they will have someone text back to them and they can have a texting conversation for the next 45 minutes, hang up, do it again all day, middle of the night, Christmas Eve, January 1st, their birthday, whatever the day that they're falling apart. And we did that because we wanted teens to talk. Well, we get about 50 to 150 new teens every single month that use that texting crisis hotline. And in five minutes, Bill, they ask the same question, all of them. Am I the only one feeling this way? They're totally isolated. You could blame it on social media. You could blame it on poor parenting. You could blame it on too much homework. You could blame it on we keep our kids too active. Whatever you want to use as an excuse, because they're all valid reasons. All of them are. But the fact is, we have created an environment of isolation of our teens with a break in social fabric that if we don't figure it out, it's going to get worse.

09:19Bill Gallagher: You know, the fascinating thing to me as you say that is, one, I know it's true, but I also know that we're never more connected, right? When I was growing up, we were like, where's the party at? We don't know. We heard a rumor from somebody and we'd drive around in the hills till we saw some cars and we'd look and see if we saw some young kids. And we're like, okay, that's where the party's at. We didn't know where everybody was and what they were doing because we hadn't talked to them. And phones were associated with locations, not people. So you couldn't text anybody. You couldn't find their location. You couldn't, like, you had no idea what was going on anywhere all the time, and you were just guessing and driving around in the dark, right? And now we're more connected than ever, and yet people feel alone. Why is that? What is that all about? And people are like, oh, I'm going to keep texting this thing. Call them, talk to them, hear a voice. Like, and you say, no, I can't do that. Like, oh, I can't. Whatever. Just go talk to people. Pick up the phone. Go to voice.

10:21Elliott Kallen: Well, you're right. They should talk to them, but here's an interesting statistic I give to people, or an interesting factoid on that statistic. Imagine this: we have the loneliest, most isolated generation in history in the United States. There are a lot of psychologists that would agree on that, so I don't, it's not my idea. I want you to think about the 1930s, being a late teen in the 1930s, the greatest depression the U.S., most of the world, had ever seen up until that point, right? 25% unemployment. Japan was on the march in taking over countries like the Philippines and eastern China. They were getting ready, they were having conversations about Pearl Harbor, you know that. The Germans were getting ready for war and what they were going to do in Poland and Czechoslovakia. 50 million people were going to die in the next six, seven years around the world because of World War II, and we have a lonelier, more unhappy generation of young kids. And that's hard to imagine, but we've done it. We've managed to do it and pull out all the stops to create poor communications.

Why today's teens are the loneliest generation

11:29Bill Gallagher: You know, I told a family member recently, I said, what will make a big difference for you in going through a challenge is for you to take a walk. And I'm going to show you, let's go take a walk. Here's how to take your walk. And I took him out for a walk and I taught him to be aware. Like, get out of your head. Now look around you, smell the air, feel the breeze on your face. Look up in the trees, notice that bird, watch the people go by. Like, open yourself up and be connected to. And then I took him into a clump of trees and I had him look up into the thing. And I said, allow yourself to be awed by what you see there, right? Like, what's going on up there? And I had him alter his perspective because what we do is we go in our own brain and our thoughts start to cycle up and we have that internal conversation, the internal voice that is running in our head at every moment, right? If you're listening now, you got that. It's the voice that just said, what voice? Right? And that voice is often not on your side, right? That voice is telling you to be more afraid, to worry that people don't love you, that you're not good enough. Like, that voice is, if you're in a bad way, that voice isn't helping. So if that voice isn't helping, talk to somebody else. Get out of your head, open up your eyes, talk to somebody else, text the thing, call a friend, walk outside, right? That makes the difference. I know after September 11th, right, it's like ancient history now, right? I remember being like, oh my God, everything just changed. We watched the towers get hit on TV and that kind of thing. Thousands of people killed in a matter of a very short amount of time. And I remember the coming days, I looked outside and I'm like, the trees are still growing, the sun is still rising. You know, the tide goes in, the tide goes out. Like, life didn't end. Some events happened. It's going to have an impact on us, profound. But like, get connected to something other than that crazy thing that's going on inside your head, right?

13:46Bill Gallagher: Well, you're 100% correct. How to translate that to teens is a challenge.

13:50Elliott Kallen: You think about parents, so many single parents have no time. They've got one or two jobs. They're just trying to get through the day. The idea of taking a walk, turning off the cell phones, taking earbuds out, sitting down for dinner for an hour just to have a conversation, the good old-fashioned way, cell phone free. So important to do. That's what we teach, and it's hard to do.

14:10Bill Gallagher: You look at, like, you open your cell phone and you flick through videos and Reels and TikTok, this and that and whatever, like YouTube Shorts and everything, like these little bites. And everybody that you flick past, you flick past so many people who are more attractive than you, who appear happier, appear more confident, appear richer than you. They've got a better car. They're on a private jet. It's all just crap. And you can flick through it and be amused and be entertained and come from a different place, right? It's not inherently, but it's very, it's too easy to look at all that and just feel like you are worthless.

14:57Elliott Kallen: Right. Like, you don't believe, you're 100% right, but your thoughts are not getting shared very easily with teens. And I have to tell you, my teens came home. It was their, my twins' freshman year and my youngest guy, senior year in high school. And they were home and they said, this is the world of heavy duty Facebook and they were even on shorter things. We're still Facebook. And they said, Dad, are we the only people in Lafayette that don't go to Tahoe or Hawaii for Christmas vacation? Yes. That's what it felt like.

15:32Bill Gallagher: I've taken my kids to Tahoe and Hawaii.

15:36Elliott Kallen: You're a bad dad. Okay. Thank you.

15:42Bill Gallagher: So, but not enough, right? Like, not enough. Did I take them? Did you take them? It is remarkable that a certain amount of money can help you deal with life. And, but it isn't the only way to solve a problem. You can have a lot of money and you can live in a nice house and you can be miserable and you can be happy and you can hate your spouse and hate your friends, or feel unloved and unappreciated and unseen.

The six-sided box metaphor for mental health

16:13Bill Gallagher: Right? All of those things can happen. Teens have this thing and they get in a whole weird place somewhere around middle school often, and then they close the door and then they retreat into their own thinking and they flick through things that leave them feeling even worse about themselves. Right? And I know we have listeners right now. My kids are grown and they're through that little moment, but they both had it.

16:37Elliott Kallen: Well, I want you to think of a teen's life as kind of a box. It's a six-sided box. It's got four walls, a top and a bottom. And you have the same box, Bill. And that box is generally for you, because I know you, it's generally the color green or blue, whatever means go or positive for you. That's how you view the box. But for somebody that's feeling really bad about themselves, that box is turning gray and then it's turning black on the inside. And so if all six walls eventually turn black, then the teen begins to reconcile because they've already withdrawn socially in this process. And they begin to say, well, life sucks. Yesterday was bad. Today was really bad. Tomorrow is going to be horrible. No one's going to miss me anyway. And there it is. The suicide part. No one's going to miss me anyway. It sucks. I'm probably ruining other people's lives. And that's where suicide. That's suicide. What we've got to do and what we do as a charity and what we have to do as a society is get that box, not that it needs to be green all the time or blue, whatever you see as positive, but to know that the colors change throughout the day. There are moments, Bill. And if you think about, you've had kids and marriage, you're still married, that your marriage sometimes is not really very blue or green. It's very gray. And you're not in a good space with each other. And sometimes that leads to divorce and sometimes that leads to something where you need to reinspire, reinvigorate and reengage to get it back to a green or blue color, whatever that is. Teens can't reconcile that. You can because of life experience, not just maturity, but life experience has taught you that you have good days and bad days. And that sometimes after a good day is a crappy day, sometimes after a crappy day is a spectacular day. You just got to hang in there for both.

18:37Bill Gallagher: Well, I know that when I'm feeling really great that it won't last forever. So I really want to enjoy it. And I know that when I'm really dark, I know also this won't last forever. So I want to make sure I don't dwell in it. Right? I keep like, somebody said it. I forget who the quote is. If you're going through hell, keep going.

Suicide rates in wealthy versus poor communities

18:57Elliott Kallen: Yeah. You're dealing with, you're dealing with Scaling Up with CEOs primarily. And CEOs, that doesn't mean you have successful children, but you could because they have money and access. There's more suicide in the United States of teens who come from wealthy families than come from poor families, which means that, and that's the key that you should think about, means that Danville, California has and Campbell and Stanford area, Atherton, and that whole area has a higher suicide rate than Richmond and Oakland per capita and per person.

19:32Bill Gallagher: Right. Well, I mean, and also like a past guest on the show, former Vice Chair of the Joint Chiefs of Staff, was on, lost his son to a drug overdose. Right? The son had a habit he couldn't kick. Like, he was not a well kid, and they did all kinds of things to help him. Very accomplished, money, education, like good environment. And he didn't live. So, like, having access to that can create incredible pressure. I know in my own family, people have been like that. I had a dear friend who was very successful in his career, very accomplished. And then his area of business failed and he lost his job with a very large, well-known national company. And he put a gun in his mouth and he tried to kill himself and he lived. And it was incredibly traumatic for the family. And he went through years of reconstruction and that kind of thing. And then talking about it, right, depression and suicide became his life's work since then. And but like watching somebody get, like, choose their identity. My own father was highly successful, spoke more than a dozen languages, was a bestselling author, was a college professor and became a dysfunctional alcoholic, and he took his own life.

21:11Elliott Kallen: There you go. So there's an example, Bill, just to keep you together here. It's hard, but the money, the languages with your dad, the money, and some of these incredible CEOs that you deal with in your job, your business. And you've got maybe one of the most successful Scaling Up companies there. That's not everything. And that's what you learned the very hard way and your dad learned the worst possible way is that there's more to life. And my business, Prosperity Financial Group, talks about that all the time to people going into retirement or going near retirement. What really matters to you. And if your family really matters to you more than your job, more than your money, then let's get that as a focus.

21:57Bill Gallagher: Yeah, dive into that. So, you've had conversations with clients at the end and near the end of their life and that kind of thing. What actually matters do you say? What have you learned about this?

22:08Elliott Kallen: Yeah. So, I think a good example of what matters here is the conversation and a real story of what I did with my wife. So, with my wife, I'm on marriage number two. So, we're a blended family. I have two surviving children. She has two surviving children. One lives with us, her son who's now lived with us for ten straight years. He's 12. The other one doesn't live far away, has an autistic child, and my kids are around the world. And so we sat down and we said, let's talk about what's important to us. What do we love and what do we like? And what are we willing to give up if need be? And I try to put my clients through this exercise. So we take the material side of things. What do we love? Well, we love travel, food, wine, and entertainment. Cooking it, collecting it. I've got a thousand-bottle wine room. I travel around the world taking cooking lessons. I'm trying to improve. I'm married to my biggest critic. She's really hard on me with food to make sure I get it right, which is okay. Sometimes it's a little hard. But we work on it. And now we're starting a new business that involves that too. That we love. Those things we love. We play golf. We talked about it. I like golf. I'm not a lover of golf. I like golf. I've got to second golf, too, but I like golf. I could give it up if I had to. We like going to the gym, but if we couldn't go to the gym and we took walks every day and that was the only way to do this, we could survive in doing that. And then what do we want to do with our family? We have a 12-year-old that lives with us. We're his legal guardian and he's been with us for ten years and we just made a decision that we are going to allow he and his mom, I love having him. It's the mom. It's the adult in the house. That's tough. We're going to let them stay till he graduates, till he goes off to college. It's six more years instead of fighting about it because we love having him there and we want to do the right thing. But the day after he goes to college, she needs to move out. Mom needs to move out. Because that's not a love situation. Even though I love her, I don't love the situation. We talked about that. And those are some things we're in control of. But the average retiree in this country watches four to six hours a day

The love, like, give up exercise

24:13Elliott Kallen: Of television. And this morning I was watching some TV network, probably it was Morning Fox, and she had somebody on with Maria Bartiromo. She had somebody on who's an expert on social media and said the average retiree watches 6.1 hours a day of TV. That was a new number I never heard before, 6.1. That means that people are bored in retirement. And so you can only see family so much without being overbearing, but you could stay in their lives. You could travel and bring that to your family and travel, invite them to travel occasionally with you, knowing that our generation probably has to pay for it if that's available for them, because that's the only way your kids would like to travel with you if you pay for it and things like that. But it's so important that you have a life that is admirable and that your next generation looks up to and says, I want to be part of that, instead of you going down saying, how can I be part of you? It's a little bit, a little different way of looking at it.

25:17Bill Gallagher: I think thinking about what you enjoy, right? What you love, what matters to you. Like I love to cook, and just the act of cooking is very calming. I love to do it at the end of the day. It's a thing to decompress, to separate the end of the day, the personal side from the work side, to put an end to it. But even more than that, I love when the family gathers and I love when my family, whoever's here, is seated around the table or sitting out on the deck and having a meal together. I also love if we just go to a restaurant together, right? I love connecting family, and food is such a fantastic way to connect, whether you go out to eat or whether you made it yourself. Like they're both powerful opportunities to connect, right? It's fun.

26:12Elliott Kallen: I wish we had a weekly family dinner where everyone wasn't so scattered away, but I can't seem to pull that off. But I admit I'm with you, same page. Yeah, I love to cook. I love to try new things. Now I've been working for the last couple of years on my plating, as an example, to make it attractive, to get artsy with my plating. I've got a thousand bottle wine room, so it's about pairing the right wine with what. It's very cool what we're doing. And now when we go on vacation to a lot of places, we take cooking classes. And then we make it a, okay, what can we go in there? We tell them what we can eat, allergic to, and all that stuff. And now it's so much, everybody accepts the fact that you don't eat everything. I go in there and say, I don't eat pork, as an example. Nobody's offended by that anymore. We're in a world where they ask you upfront, what do you like? What can't you do? But getting people together, that's great. I'm going to see my son. I wanted to go see him. He's at Washington, D.C. I said, want to come out there? He said, no, let's go to Charleston and meet there, an example of what you want to do. And my daughter just moved to Amsterdam, outside of Amsterdam, and we're going there for fourteen days, a little side trip to London, but we're going there because we want them to be part of this. So that's a really important thing.

27:28Bill Gallagher: I think figuring out what those things are, the shared experiences and that. Like, those are specific experiences in a company. Then there's what you're building in your business and what stays beyond you. And then there's the quality or the characteristic. Who do you want to be and how do you want to be remembered by that family? I think that's really important, right? I think it's super motivating and clarifying to me and for a lot of the CEOs that I and senior execs that I work with is this question like, okay, after you're a successful life, right, after you've lived a full long life, lived however long you wanted, who will be gathered around? Right? Who do you want to remember you? And what do you want them to say? And I think that is a fundamental kind of thing. Want them to say I was the life of the party? I want them to say I made everyone laugh? I want them to say that I made everything beautiful? I want them to say that whatever. What do you want them to say about you? That's the quality of you as a human being that you can bring into your work, to your family, to your relationship, like everything, right? That's your legacy planning. We do that as part of our job. We're constantly talking about your legacy.

28:39Elliott Kallen: Legacy doesn't mean I'm going to give money to charity all by itself. That's a good thing to do, or start a foundation. Those are really good things. Legacy has a lot to do with your children. How do you want them to remember you? I don't think my father and mother ever thought about that at all, even though I remember them incredibly fondly. I have great memories of both of them, but I don't think they did that consciously. But my dad, because I did have my mom in high school, most of high school, my dad intuitively asked me great questions. And that got me more involved into a leadership position with a youth group that changed my life around in high school completely. Not that I was a degenerate, but I was like a lion in a cage not knowing which direction to go in. He got me focused into that, and then sports helped. But without having formal training and never getting beyond eighth grade and no parental things and part of the Great Depression, he knew the right questions to ask. And we try to educate on a charity and in our business, ask better questions to get better answers. I don't know all the questions they ask, but I know if I was talking to you, Bill, and you're an avid outdoors guy, windsurfing, airfoil surfing, blow dryer surfing, whatever you do out there in the water, right, it's amazing what you do.

29:56Bill Gallagher: Wing foil, we call it.

29:59Elliott Kallen: Yeah, wing foil. Whatever. It looks like a big blow dryer is what it looks like. Whatever it is that's so important to you, I would ask you if I was talking about your legacy, are you doing this for you because it's pure enjoyment, and that's not a bad thing? Or are you doing this because you're hoping to pass down to the next generation that it's okay to be a little bit of a risk taker and an outdoors person and enjoy life and bring your family in on that? Because I think it's a lot of fun. And you do it on your terms, not on my terms.

Who do you want gathered around you

30:28Bill Gallagher: So I've taken my kids on sailing trips. We've done a lot of family sailing trips. I've taken them to try and learn surfing, and I've offered to take them to do the wing foil surfing. But it's like, I don't need them to get that. What I need them to see, like the example that I want to set, is to just follow your bliss, follow your thing. So like be outside, I think is probably important to lots of us more than we realize, and finding excuses and play. Like play, be outside, follow your bliss, do what lights you up, find your flow. That's like a key thing that, you know, that I would, we've also taught our kids to enjoy coming together. We've always hosted family events. So be a host, be a great thing to create family events. We have a family dinner in the spring and we have the holidays in the fall and we have, you know, when people gather at our house, we have, when the kids were young, we had

31:30Bill Gallagher: A Friday night dinner always. And then we would have a Sunday afternoon barbecue. These are regular kinds of traditions. And now that I have a granddaughter, and the last two years in particular, we've brought back the Friday night dinner. And so we have this Friday night dinner, we light candles and we're together. And it's really, really important to create these moments of connection.

32:00Elliott Kallen: I think what you're talking about, Bill, the word that I like to see you use, because you exude every part of that, is your legacy with your children is live with passion. It's a great legacy. When you think about that, most people go through life with a job or career but they're not very passionate about life. I mean, you love your children, sometimes you don't like your children but you'll always love your children. My mother told me that lesson. They annoy you, but you love them. But my children will tell you my father is the most passionate person I know, because he lives life believing in what he does and does it because he believes in it, back and forth all the time. Charity, business, interpersonal relationships, friendships, loyalty. Sometimes I feel like a mafia don because I feel like I'm watching Blacklist when he says, above all, loyalty. And so I put friendships and loyalty and business loyalty and passions all together. That's a great way to live your life. When you're teaching what you do, which is scaling up your business with large companies, medium companies to get big, wow, imagine that CEO wakes up tomorrow, changes his life around and realizes I'm building one heck of a business, I'm going to do better because of Bill, and now I'm reconnecting my family because of the passion that Bill is teaching me.

33:20Bill Gallagher: You know, it's interesting. Passion, being playful, going for it. These are definitely things that are like example and things that I want to pass, not just to my friends and family, but to clients and so on. I next week, I go away for a month retreat to write. And I have done several attempts to write and put out a book and none of which I ended up putting out. One of which I actually sold and then didn't finish. And now several attempts at this. And I've been thinking for a long time about what is it that I need to say. And I've kind of settled on this, that you could actually have a great life and having a great life, a life of balance, could actually make your business better. That if you lived more playfully, didn't work so hard, didn't lean in so much, like loosely, you would have a stronger team. You could have a better business. You'd have better strategic thinking. And so that's what I'm finally going away to write about it. I hadn't thought about it till you said it in that way, like, okay, so I want people to say, I want my family and my friends to gather and to say that I was a contribution, that I was generous, that I made a difference for them. That's what I want them to say. But the example that I want to lead, I think, is also important. And that's being playful, being going for it, and that kind of thing. My daughter gave me a really thoughtful gift this last holiday season. She made a calendar of me. She took various images of me, and then she played with them with AI and some things like that. And she put me in all these funny situations. And it was the most touching thing that I've had in many years. And I laughed and cried as I flipped through the twelve months of this calendar with pictures of me because they were all so silly. But I love that who I was for her was playful and silly enough that she could make that and I would appreciate that.

35:28Elliott Kallen: You're doing great with that. I'll give you a hint on books because I have an Amazon bestseller over my left shoulder called Driven, is that I hired a woman in Texas somewhere outside of Houston and she became my editor. And we would once a week, usually Sunday morning or Saturday morning, I'd come in my office, I'd work for two and a half to three hours every Saturday morning for one year. I would either dictate the book or I would write the book and she would take my dictation, put it out there, send it back to me. I have to reread it, realize I didn't like any of it or I like two thirds of it or whatever. There's a lot of stuff I wrote that I didn't like and I thought, wow, you are just rambling into insanity here. But that editor thing working with me saying, no, Elliott, you told me to be here 09:00 California time. What time are you going to be there? And I said, 09:00 your time, I'm talking to you. And we'd write for three, four hours. And then I learned that, wow, I can be really unorganized. But what she did is she taught me that writing is a business. So you have to have the discipline just as you have the discipline in scaling up is the same discipline.

36:36Bill Gallagher: Well, I'll be telling the story of some CEOs that I admire and learn from, not perfect, but did interesting things and some others that I think were kind of less admirable. And I'll be telling the story of at least five, I don't know, maybe a few more of CEOs and what they did in their company. And then kind of the process that lets you shift into the more admirable one, and that's the intended story of the book. I will definitely need to find soon a new editor, but I'm going to get all the core stories done and the basics of the thing done in this month long retreat, and I'll do a little bit of writing every day.

37:16Elliott Kallen: And make sure your editor knows how their publisher knows how to market the book since that was one of the mistakes that we had is we had a publisher that wasn't comfortable in marketing. And so we took it over. And I'm not a book marketing person. So we could have had a lot more sold and things like that.

37:35Bill Gallagher: I think people that know that world, and I have often thought I would go with a traditional publisher, but I'm not sure. I may just self publish this time and hire a good marketing partner for it.

37:48Elliott Kallen: I love that. That's the right way to do it. You've got a lot to offer. Promise me that you'll put me as a footnote on page 267 or something like that.

37:57Bill Gallagher: Two sixty seven. I like the specificity of where that footnote's gonna go. Is your, there's what you love, right? There's who you are. How does this, like the family focus, the financial thing, pull it together for me in your world, or maybe it ties into Driven.

38:26Elliott Kallen: Well, Driven is the book, just to tell you something about Driven by Elliott Kallen, it's on Amazon. Can't just say Driven, I couldn't patent the word Driven. Too many Drivens. So Driven by Elliott Kallen. I wanted to write a book about my life. It's not really an autobiography, about the journeys of success and entrepreneurship. Because too many entrepreneurs in today's world think they're the next Mark Zuckerberg, that they're going to start a company and five years later, they're to sell it or take it public and they're going become a billionaire. And most entrepreneurial journeys, are anything but that. We have zigzags in our life. We go backwards, we go forward. I've had tragedy. A lot of families have a tragedy. Their spouse died, their parents died of horrible cancer. There's a lot of tragedy out there. And so I wanted to write a book giving acceptance and acknowledgement that life is not a straight line.

39:20Elliott Kallen: That was my goal of writing that book. It's not overly long, it's three and a half hours to read it. Amazon actually was one of our co-publishers on that, and I think you could buy for 99 cents the verbal version of it, the audiobook. I don't see any of that money, that all goes to charity, all of it goes to A Brighter Day charity. But 99 cents, how much does your charity make on 99 cents after Amazon is done? I have no idea. But we put that out there. For the business side of it, the funny part about this is what it did and what we talked about is, again, asking better questions. And if you're a family-centric person—and not everybody is, no matter what they say—but if you're family-centric, and you are, Bill, that means that you have to be more than just verbally family-centric. And you don't have to necessarily be the patriarch of your family. That's a personality thing that doesn't work for everybody. But you have to be an involved person in your family. And sometimes that means biting your tongue because I can't say that, or that's sharing my opinion in the right way at the right time. Like, if I was your father and I saw you on the blow dryer—like I said, on this foil thing on the water—and I see you on a bay and I find this to be a little bit disturbing because you could fall 15 feet on your head into a shallow bay. I'm making that up because these things happen, you know that. I might want to say to you, Bill, is there any way you could either create more self-preservation, or maybe not go up so high because I'm worried about you cracking your skull open? I can't just say that, because in your case, Bill, you'd be really defensive. Well, Dad, I love that, and this is what I do, and come on. You have to say it in a better way, and that means you might bite your tongue at one point to say, you know, Bill, one of the concerns I have is about such and such. But the timing of that is so important. And that's what you do as a parent and a family-centric person, is be the biggest cheerleader for your family, the biggest supporter of your family that you need to be. But timing is important because kids are defensive when you just attack them for what they're doing. So you need to bite that. You've been married a long time, Bill. I've been with my wife for 20 years, second marriage. Now, if I just go home tonight and said, you know, honey, you are the biggest crank at 5 in the morning I've ever met in my life. You know how that's going to go over. You don't even know my wife that well, and you know how that would go over. And everybody listening to this now, that goes over. But if we were out to dinner, I said, you know, sweetie, is there any way that you can work on, when I get you up too early—and I know I shouldn't do that, to put the TV on at 5 in the morning—but when I do, is there any way you could cuddle in so we can wake up in a better mood? That would go over so much better if I pick the right time and the right place to say that.

Expressing concern without raising defenses

42:12Bill Gallagher: Oh, you know, that segues into so many things there. That's such a vivid picture about it. I've learned a couple of things around that. So my wife and I used to argue about the TV a great deal, until I learned the ideas that are embodied in Mark Goulston's book, Just Listen. And we teach it and we use it in our work with CEOs and that kind of thing. But it basically says, get over in the perspective and the brain of the other person. What's it like to be them? Right? And so my wife, in my argument about the TV, there was no timing, it always went nuclear whenever we talked about it, until I thought about, what's it like to be her living with me dealing with the TV?

43:03Elliott Kallen: Yeah. And you're probably like me. Most entrepreneurs, we don't sleep much past 3 or 4 in the morning. It's just horrible sleep patterns. Which means when you're bored, what do you do? You put the TV on. You could go to the other room and put the TV on and never think they'll go back to sleep, or you can just roll over and grab the remote, keep it low. You know, I can't. I've gone through that with my wife. We have constant conversations about what happens sometimes at 4 in the morning or 2:30 in the morning with the TV. Yep. It's hard.

43:31Bill Gallagher: I think thinking about what it's like for them is definitely a pathway to something. And then asking yourself, whatever you think you need to say, is it true? Does it need to be said? Does it need to be said by you? Does it need to be said now? Like, it's useful to ask those things that you alluded to there. A lot of times, it all comes down to, like, advice, opinion, and what you're not sharing is your fear. You know, if you said to me, using your original example, God, every time I see you out there, it looks intense and I just am so worried. I love you so much. I'm worried something will happen to you. And then you let me deal with that. That would be different than you telling me, would you please wear your helmet, right? Like a grandmother or somebody would do. Like, would you please—I do wear a helmet, right? And the sport I do is pretty dangerous. Right? I've cut myself before. The things we ride on are very sharp, these little hydrofoil wings that ride into the water, very sharp. It's dangerous for sure. Like, my wife's like, oh yeah, you could kill yourself out there. I worry that I'll get a call or you'll kill yourself, or even worse than kill yourself—because, you know, then we'd miss you and we'd love you, but we'd honor your legacy—but I worry that, like, you'd become an invalid of some kind and then I'd have to take care of you for the next 20 years.

45:00Elliott Kallen: Well, you buy a bigger disability policy or a life insurance policy and then you're covered. But it's not just when you say it, it's how you say it. And you're right, it's all about, I don't want to sound like your grandmother, I want to sound like your father or your friend on how I'm saying it. So the timing of it is so important, you know?

45:17Bill Gallagher: And it, yeah, I mean, you're 100% right. Talking about you than them. Like, I'm worried about this, I'm afraid of this, I love you. Like, that's different than here's what I want you to do, like advice, or like pleading and that kind of thing. So I try to ask my children questions.

45:38Elliott Kallen: So my daughter two months ago moved to Amsterdam. She uprooted her family, got sick of the United States, loved socialism, moved to a socialist country, high quality of life compared with the US. That's the Netherlands. Yeah. I have a million questions for her. And I have been a cheerleader, even though I fundamentally disagree with probably 98% of what she says. I have a fundamental need to be her cheerleader and I want to see my grandchildren. So when I have something I bring up to her about her marriage or how to make more friends, I find the right time and I just ask a question about it. You know, like, how would your life change if you had a couple more young moms?

46:20Elliott Kallen: That's the key. Yep.

46:22Bill Gallagher: Yep. Yep. Oh, there's a lot of gold here on the show. We've talked for a long time now, so we should probably wrap it up. But his book is Driven. Driven what? Say that full title.

46:34Elliott Kallen: Driven by Elliott Kallen.

46:38Bill Gallagher: Driven by Elliott Kallen, right? So the full thing. And you can find that on Amazon, 99 cents reportedly. But the idea for sure. And I think there's a lot of stuff in there, both his story and the example of all the people. So his company, Prosperity Financial Group, we'll put that in the show notes and on the screen there as well, helps people to build their portfolio and manage that so that the financial side of legacy is addressed. And as you could hear from Elliott, he takes a much bigger picture, not just what do the numbers say, but what do you actually care about in life? And then also A Brighter Day dot info is the charity that helps to prevent teen suicide. And if they can prevent even one more by adding your little effort, donation, participation in one of his events or that kind of thing, that would make a difference in sharing that and expanding what they do there. Elliott, thank you so much for joining us on the show today and sharing some of your stories and your wisdom with us.

47:40Elliott Kallen: Bill, thanks for having me. Great to be here.

47:44Bill Gallagher: Thanks to Anna and to Wanda for getting our show produced in and out every week. Thanks to my friend and mentor, Verne Harnish, who created the whole Scaling Up framework that's at the base of my business. And to all of you listening, watching, thank you again for tuning in. Until next week, keep scaling. Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken: Do Less, Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.