Justin Donald: The Post‑Wealth Work‑Life Balance
Episode - 58
Justin Donald: The Post‑Wealth Work‑Life Balance
One of the hardest parts of life after an exit is striking that balance.
On the one hand, enjoying the incredible lifestyle we've earned. On the other, protecting and growing the wealth it took so much to build.
My friend Justin Donald has lived that tension and he wrote a best selling book about it and created a community called Lifestyle Investor to help others walk the same path. It's easy to dismiss the drive for more financial success once we've already had an exit. But Justin shows us it doesn't have to be a choice and fulfillment can live side by side.
Today he shares his story, his hard earned insights and the way he's chosen to live his own life.
What We Discussed:
00:00 – The shift from “have to work” to “get to work”
00:20 – Anastasia introduces Justin Donald and the idea of ambition vs fulfilment after exit
01:12 – Why work when you don’t have to? Finding meaning and fulfilment
02:17 – Introduction and greetings
03:10 – Justin’s early beginnings and first entrepreneurial experiences
04:25 – The gift of learning self-reliance
04:44 – From door-to-door sales to early business ventures
07:33 – First exits and lessons from building and selling small companies
09:21 – Transition from trading time for money to investing for freedom
09:31 – Defining financial freedom before becoming a millionaire
13:03 – Writing The Lifestyle Investor — from passion project to bestseller
14:10 – Donating profits to fight human trafficking and the book’s viral success
16:10 – Building the Lifestyle Investor community and its strict values
16:27 – Launching programs for young adults and future investors
16:35 – What financial freedom really means
18:58 – The balance between hard work and fulfilment
19:31 – Justin’s year-long sabbatical — lessons from doing “nothing”
23:17 – The true luxury: working because you want to
23:38 – Building life around values — faith, family, health and business
26:38 – Managing time and boundaries: the schedule that reflects priorities
27:36 – Breaking free from the rat race and the myth of “more money”
30:40 – The power of asking higher quality questions
32:50 – The exited founder’s dilemma: work or retire?
33:40 – Why taking time off after exit is essential
36:05 – Knowing when not to rush into what’s next
37:27 – Retirement vs sabbatical: doing things in the right sequence
38:35 – The fallacy of retirement — why people need purpose
40:00 – Pivoting from “have to work” to “get to work”
41:20 – Reinvention and second acts: From Strength to Strength
42:57 – Learning new skills after success — and why “ikigai” isn’t always right
44:02 – Staying a student: the joy of being a beginner again
45:06 – Teaching as the most fulfilling next chapter
46:20 – The story of Justin’s aptitude test and rediscovering his destiny to teach
50:51 – Purpose and profit: resolving the moral tension
51:14 – Why wealth creation and impact can coexist
54:24 – Giving, purpose, and the meaning of fulfilment
55:11 – Teaching financial wisdom to his daughter
57:33 – Legacy: how Justin wants to be remembered
58:25 – Closing thoughts and invitation to Lifestyle Investor community
59:32 – Where to find Justin online
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Justin: [00:00:00 - 00:00:20]
It's that pivoting from have to work to get to work. And if you get to work on the schedule that you want with the people you want, what would you do? What does that look like? How many hours would you work? What days would you work? Which people would you work with? What would you do? What would your actual role be? What would the greater impact be? And it doesn't even have to be for money.
Anastasia: [00:00:20 - 00:01:12]
One of the hardest parts of life after an exit is striking that balance. On the one hand, enjoying the incredible lifestyle we've earned. On the other, protecting and growing the wealth it took so much to build. My friend Justin Donald has lived that tension and he wrote a best selling book about it and created a community called Lifestyle Investor to help others walk the same path. It's easy to dismiss the drive for more financial success once we've already had an exit. But Justin shows us it doesn't have to be a choice and fulfillment can live side by side. Today he shares his story, his hard earned insights and the way he's chosen to live his own life.
Justin: [00:01:12 - 00:01:42]
Why work if I don't have to work? Well, I can't sit around doing nothing. I learned that. I love to learn that. I'm curious and I'm an eternal student and every single day I learned something because I wanted to learn it. Now that I don't need to work for money. Well, what if I just work because I show up better and that's it? I have to have meaning to my life and I have to have some sort of impact for me to feel fulfillment.
Anastasia: [00:01:42 - 00:02:17]
My friends, we're here to help each other make better decisions post exit with our time, energy, wealth and relationships. If what we share here resonates, let us know by subscribing or following. It helps us bring on incredible guests and reach more exited founders who need these conversations. Do me a favor, hit that subscribe or follow button. We're in this together. Hi Justin. So good to see you.
Justin: [00:02:18 - 00:02:26]
Thanks, you too Anastasia. It's always a pleasure getting time with you. And you know I've been looking forward to this time. It's been a couple years coming here.
Anastasia: [00:02:27 - 00:02:33]
That's so true. That's so true. Way overdue. But we are finally here.
Justin: [00:02:33 - 00:02:34]
Yes.
Anastasia: [00:02:34 - 00:02:58]
So Justin, for me you are not just a friend and not just an exceptionally successful man, but you are someone who figured out something that everyone wants to figure out, which is not only how to get to the financial freedom, but also how to get the most out of it. So I will try to get as much of your wisdom today as I possibly can out of you.
Justin: [00:03:01 - 00:03:09]
Well, I'm happy to share. I'm an open book as always, and I feel like I've learned from a lot of great people over the years and I just want to pay it forward.
Anastasia: [00:03:10 - 00:03:19]
So can we start with you just telling me briefly, how did you get to where you are today and where you are today? So my audience knows.
Justin: [00:03:20 - 00:04:21]
Yeah, sure. So I guess, you know, to be on point with your podcast. You know, I did start as an entrepreneur. I started a, you know, a few different businesses when I was younger. I don't, I mean, they were true businesses. I don't want to call them necessarily, you know, type of exit that your guests have had. But you know, even in high school, when I was, well, actually I started in middle school, I started selling newspaper subscriptions door to door and I was horrible at it at first, just awful. And I finally like developed the courage and the confidence to do well there. And so I did that for years. And so that's, you know, I paid for a lot of my college by doing that. Saving up the money I had. My parents basically said in seventh grade, you know, if you want to have money, go do stuff, go get a job. Like there's, we don't have the money to support you doing all the things you want to do, going out with your friends, you know, and that stunk for me because all my friends, their parents just gave them money, you know.
Anastasia: [00:04:21 - 00:04:24]
Wow. And so that must have been very hard for you.
Justin: [00:04:25 - 00:04:44]
Yes. But today I would say that was the greatest gift I was ever given is that I had to, early on in my life figure things out. And so by the time I was in high school, I was running my own crew of kids going to neighborhoods, selling newspaper subscriptions and coupon books.
Anastasia: [00:04:44 - 00:04:44]
Oh, awesome.
Justin: [00:04:44 - 00:07:32]
And so that was really, you know, besides small little knick knacky businesses as a kid, like that was my first decent sized business. Now that wasn't one that I had an exit on though. I didn't package that up and sell it. It probably wasn't sellable. Maybe someone in the industry would have bought it. But I just eventually shut that down and ended up going to college. And then periodically I might roll it back up and head out. I really only saw it as a mechanism to make money and to sharpen my skills in training and teaching and developing people. From there, I ended up working for a period of time with a direct sales company and I helped build out a lot of their programs, their sales training, their leadership Development, their kind of retention tools, that sort of thing. And so during my time of kind of building that out and kind of building my own company to support that, I created a consulting company that then went out to all these other businesses and did the same thing. And so with some companies I was an advisor. With some companies I was a consultant. So sometimes I would take advisory shares and that's it. Sometimes I would take advisor, you know, some sort of a retainer or some sort of, you know, payment over a period of time, maybe, you know, annual contracts or different things like that. It just always depended on the company. And so at a certain point I was able to sell that company. So that was my first exit. I don't even want to call it a big exit. I mean, we're talking, you know, around seven figures. Nothing, nothing crazy, but that kind of gave me my first real taste of what it was like to see, you know, kind of a first influx of cash. And I was able to use some of those dollars to start buying real estate. You know, I got into real estate really early on and, and so I remember, you know, buying and selling some, some different, you know, whether it be mobile home parks or single family homes. There were a bunch of those that I had done over, over time, which were all. I did pretty well on each of those. And I remember one year I had bought a mobile home park and I sold it at a year and a month later and I made more money on that single transaction that I probably only put 5 to 10 hours a week towards than I was making annually with my consulting company.
Anastasia: [00:07:33 - 00:07:33]
Oh, wow.
Justin: [00:07:33 - 00:07:50]
And so that was the impetus to say, hey, I've got to let the consulting company go because that's trading time for money and I really need to be focused on allowing money or assets produce my return.
Anastasia: [00:07:51 - 00:07:51]
Yeah.
Justin: [00:07:51 - 00:09:21]
And so that was a big aha for me, you know. And so I've bought and sold other companies. I started another, you know, handful of businesses. I've had a few other smaller exits. I had, you know, another dog training company that I had some operating partners come in and run. And in a year and a day, we were able to create about 11x on our money, 11.2x on our money, just by doing the right SEO and opening up the window and, you know, really putting more revenue on the books. I started a single family home maintenance company that really took off and the VCs got interested early. We built our own proprietary layer of technology over it so that we could be, you know, more of a tech company than a services company when we went to raise from the VCs, and that was a really, really smart move. And that allowed us to raise it at a higher valuation. Made our business obviously more, you know, worth a lot more since we could value it based on revenue and not based on ebitda. Right, Makes sense. So, yeah, I mean, that's just kind of how it got started. So along the way, I bought and sold, you know, a handful of things I've never had. You know, a crazy monster exit like many of your guests have had. But what I like to say is I've had a lot of singles and doubles and then a few triples and maybe a small handful of, you know, little in the park home runs.
Anastasia: [00:09:21 - 00:09:29]
So let's talk about what you're doing today because I think it's very exciting and I think it's relevant for many people in my audience.
Justin: [00:09:31 - 00:13:03]
Yeah, well, you know, it was interesting because we talked about this on my podcast when you were a guest, which is trying to figure out what's next, what's the next chapter? I mean, at this point in life, I don't need to make more money. Years ago, I mean, I created. So maybe the best way to enter into this is I figured out financial freedom well before I was ever a millionaire. So all the expenses that it cost me to live the life that I lived, I had covered in passive income. Right. I had assets producing that income. I wasn't even a millionaire yet. In short order, I did kind of eclipse that number. And then we've just kind of grown and scaled. And as I have scaled my passive income by default, the natural byproduct is my net worth has grown. But I've always looked at financial freedom being way more important than any net worth number. And so I started realizing I wanted to teach this methodology. I wanted to teach people how to buy their time back, how to not be, you know, doing something that you don't love, or owning a business that really owns you, or, you know, in a corporate gig where, you know, you've put all this time in and you feel pot committed but you hate what you do. Right? It's like, how do we help people buy their time back? How do we help people make smart investment decisions? Most entrepreneurs are horrible investors, and if you give them enough time, they will blow through all the money that they made in their exit. I mean, it's crazy, but it's two different skill sets. And so I wanted to teach people the way to do it, where you can create cash flow and you can do it in a. In a low risk way. And so I built this brand called the Lifestyle Investor. And I didn't think it was gonna go anywhere. It was a passion project through and through. I dumped some capital into it and I was like, well, I don't know exactly what to do. I just know I wanna teach people. I had friends for years telling me I had to write a book and teach people, coach people, just that they wanted to learn the things that I've been doing for all these years. And I was like, after hearing it enough times, one of my buddies gave me a real hard time and he's. We were on a walk here in Austin and we were going around town, lake here, and he goes, hey man, I've been asking you for a decade to write a book and you keep kind of like kicking the can down the road. So I got a tough question for you. What if you die and your daughter never learns all these great things that you have figured out about investing money and building relationships and creating and multiplying net worth? And it was a real punch to the gut. And so the next day I started writing that book. Back then, I didn't have a following. No one knew who I was. I didn't have an email list. I was not very present on social media. And so I had a friend say, hey, if you can sell 10,000 books in like the life of this book, right, then you have truly been successful because only 5% of people who write a book ever sell 10,000 copies. So I said, that's my lifelong goal. I'm going to hit 10,000 copies. And I really was thinking I might have a few hundred people buy it and then just kind of add up over time. But when we launched it, by day two, we had 10,000 people that had bought the book.
Anastasia: [00:13:03 - 00:13:03]
No way.
Justin: [00:13:04 - 00:13:13]
It went viral on social media, became a number one Wall Street Journal bestseller in USA Today best sell, and really had a mind of its own.
Anastasia: [00:13:14 - 00:13:20]
Yeah, obviously knew about the bestseller thing, but you never mentioned how fast you got there. That's incredible.
Justin: [00:13:21 - 00:14:10]
Yeah. And part of me, I think with this book, I donated all the proceeds to fight human trafficking from day one. So I was never gonna touch a penny of it. I wanted it to be for something bigger and more important. And I really think that choice, like, that was it like, because I don't benefit, I really think the, like, had I done it with me in mind, I actually don't think it would have the success that it's had today. And as of 2023, it's the top 1% of all books ever sold. So by volume, the lifestyle investor has sold more copies than 99% of the books that have ever been sold, which is so mind boggling to me because I could have never in a million years dreamed that. And the podcast followed suit. A top 1% of all podcasts based on monthly downloads.
Anastasia: [00:14:11 - 00:14:16]
You must have felt it's a sign that you should go and you should teach people.
Justin: [00:14:17 - 00:16:10]
I can see that 100%. Like, this was just fuel to the fire. It was motivation. It was. I feel like I had some liftoff and I started hosting these live events and building communities and all the stuff you and I have talked about where I wanted to build this epic group of individuals that we just want to do life and business together, and we have each other's back and we learn and grow together. And everyone's humble and everyone's kind. People are hungry to learn, eager to give of what they know and their expertise. And you and I are part of a lot of groups and there are amazing people in those groups, but there are also a lot of people that are misaligned in values and intentions. And it's like, you gotta wade through all these different people to get to the ones where you're like, you, Anastasia, you are my people. Right? Like, I felt that immediately when we met. And so I was like, well, what if I just built a community that 100% of those people are that way? Like, there's no wading through to find people with the right same values and, you know, framework for life that it's just like every person you meet, you're like this. This person's amazing. And so that was it. We figured, why not be as strict as humanly possible on who gets in. We capped it at 100 for like six years. And then we just opened it up as of January 1st this year. We just bumped it up. And we'll probably go to 125 this year. And then Tribe of Investors is kind of like the next tier down. And I think they're at like 60 or 70 members now. That's the newer one. And we technically started our young adults program in the fall called Lifestyle investor foundations for 18 to 35 year olds. And that one has taken off too, which.
Anastasia: [00:16:11 - 00:16:25]
That one is so needed. It's so needed. Especially now for the generation that has all these incredible tools at their disposal to create that life of financial freedom and get the most out of it.
Justin: [00:16:26 - 00:16:26]
Yes.
Anastasia: [00:16:27 - 00:16:35]
Justin, going deeper into that, how do you define financial freedom? What is it for you?
Justin: [00:16:36 - 00:18:58]
Well, Yeah, I think for me, I mean, the technical definition, the way that I teach it, is that you have more money coming in in passive income than your expenses in life, what it costs you to live. And I think there's a few levels in there. So there's like survival income. So it's just enough to get by, right? You don't have to work, but you're not living your current lifestyle. It's like you're paying all your bills, you're able to provide food, groceries, utilities, all that. And then from there you go to your current lifestyle. And then from there you might go to your ideal lifestyle, or you just continue to harvest surplus income, everything above and beyond what it costs you to live. And then what I like about those dollars is, you know, on, on the money that you've worked so hard early on, it's like you're saving 5, 10, 15, 20, maybe up to 25% so that you can retire at some point or have financial freedom or have some good investments. But with the surplus income, 100% of that can go to wealth creation to impact. And that's powerful, you know, and so I look at these different levels of financial freedom. So, like, from a technical standpoint, passive income exceeds lifestyle expenses. You're a lifestyle investor, you have passive, you know, you're financially free. What does it really mean, though? Well, it means that now you don't have to work. You get to work. You get to work on what inspires you, what fulfills you, being around people that light you up, working a timeframe that makes sense, building boundaries that serve family and friends first and faith and whatever else is important to you first. Because it's amazing what happens when you have a schedule that you love. And by the way, I wouldn't say that I'm static ever. I mean, I've got a pretty. I've got a lot of boundaries around when I work and when I don't work. But when I get into something, like, I'm all in, like I can pour in for a long time. It's not like I'm trying to get.
Anastasia: [00:18:58 - 00:19:06]
Away from working hard. You work hard. So you make it sound as if, as if it's always pleasure first, but it's not. You work hard.
Justin: [00:19:07 - 00:19:11]
You've got to have things that you're passionate about and that fulfill you. Right.
Anastasia: [00:19:12 - 00:19:30]
Because I wanted to ask you, you really don't have to work. And unlike many people in my audience who are not quite sure yet how to actually convert their exit wealth into financial freedom, you know exactly how to do it. So why do you keep working?
Justin: [00:19:31 - 00:23:08]
Well, for a while I didn't. I mean, I did hit the pause button In 2017, we traveled the globe. I mean, we went on a year long worldwide trip, 13 countries, you know, me, my wife, my daughter, we just had a blast. We brought our babysitter for part of it, while we were in Italy for three weeks during part of that stint. And, and it was incredible. But I was intentional. I am not going to work for a year. And that was really hard. Anastasia it, I mean, I got five weeks in and I was getting shaky leg. Like I got, you know, I was kind of, you know, you know, getting amped up and, and I just remember, you know, having some wise people around me say, hey, one of the best things you can ever do, you know, after an exit and just at different periods in life, after working hard, is like taking a sabbatical and taking true time off and not shortcutting it and not, not shrinking it because all of a sudden you got the itch. So after five weeks, I just kept pushing. And then the next itch really came at about five months. Okay. And then really after that, it was kind of smooth sailing. I mean, maybe in a month, month 11, I started feeling like I gotta, I gotta do something. But it wasn't like I wasn't doing anything. I, I journaled every day during that, that year. And I love looking back and reflecting on all my takeaways because what, what did I take away? Well, I learned that I love to learn, that I'm curious and I'm an eternal student. And every single day I learned something because I wanted to learn it. Not for any other reason than that on all kinds of crazy topics. Number two, I learned that I love to teach. The more I learn, the more I want to teach people. Like, I love being, I love doing life with people, right? Real life, having real conversations, talking about real challenges, solving real problems. You know, number three, I really do enjoy investing and finding good deals that are wins for myself and now for our community. But back then, for that year, I would just periodically look at some stuff. And really it was like those three things led me to build the lifestyle investor. So that was an afterthought at that time. I mean, I read every single day. I mean, I read every day, period. So I read every day on that trip. I love to read. I feel like that's how I'm intellectually stimulated, is reading and podcasts and great conversations with people. And I just learned that I am on fire. I'm lit up when I'm doing those things. So why would I not do those things? Right. It's like now that I have the clarity and now that I don't need to work for money, well, what if I just work because I show up better for myself, for people that are around me, for my family and that's it. I have to have meaning to my life and I have to have some sort of impact for me to feel fulfillment. And so, you know, that's a long winded answer. Going back to your original question of why work if I don't have to work? Well, I can't sit around doing nothing. I just can't. I did it for a year and I didn't do nothing. But I just, you know, I was very strategic in what I did, and this is what lights me up the most. So it does not feel like work.
Anastasia: [00:23:09 - 00:23:15]
Yeah. Isn't that the ultimate luxury, to work because you want to and not have to?
Justin: [00:23:15 - 00:23:16]
That's right.
Anastasia: [00:23:17 - 00:23:36]
So, Justin, I know you well enough by now to know that you actually live what you preach. Can we go very personal and if you tell me some of the principles that help you keep this beautiful balance between work and life in your life?
Justin: [00:23:38 - 00:26:37]
Yeah. You know, I think for me personally, it's figuring out what matters most and then it's prioritizing those things. And so for me, you know, it'd be faith, family, other relationships. So like close friendships, non familial health. And then, you know, for me, business is kind of like under that. So it's all those other things first. And it's making sure that I'm grounded there and that I'm actually showing up the way that I intend to show up. And for example, I remember at one point in time I got challenged a little bit because I would tell people, hey, I'm a family man. I'm. I'm really working hard to put my family first. And, and so, like, and I'd made a lot of strides. I, you know, I think I, for a long time had put business first and then family second, and I kind of fit them in wherever I needed to fit them in. And I wanted to make a big shift. And I had a friend kind of call me on it and he goes, hey, you maybe are doing better, but I don't think you're where you want to be or need to be. And I'm like, what? I mean, what do you mean? Like, I, you know, and I want to play the comparison game. Like, look how good I'm doing compared to so, and so, you know. Yeah, because. Yeah, but. But if you play the comparison game, you got to compare yourself against the best, you know, fathers and family men out there as well, not just the ones that are not as good as you. And, and so he had said, well, your schedule is the truest reflection of, you know, how you're managing your time. So check your schedule. And I looked at my schedule. I'm like, oh, man, I'm still scheduling all my work stuff first. Like, it was a. I. It was like a punch to the gut because I. I was better, I was doing better, but I. I hadn't fully made the conversion that I wanted. And now if you look at my schedule, you'll see family first. You'll see family all intertwined throughout the day at even, odd times when a lot of people would be working. And that was a very meaningful conversation in the moment. I didn't like that he called me on it today. I'm really glad he called me on it, because I was able to build boundaries of what. Where does family time, time start and end? Where are the bound? When do I just never work? Like, I just don't work on the weekends. I just don't work in the evenings. I just don't do it. I like being around while my daughter is getting ready for school. Like, I just don't work at those times. And then I keep part of my schedule open for just, you know, creative time or personal things. I keep part of my schedule open for time with. With just friends. Like my Fridays, I. I don't work on Fridays. I. I really. I mean, the mornings, my wife and I do like, a date day. And then the afternoons, I hang out with friends. You know, it's a great time for building thriving relationships.
Anastasia: [00:26:38 - 00:26:42]
So how many hours a week on average, you think you work?
Justin: [00:26:42 - 00:27:17]
Yeah, I'm probably putting in 25 to 30 hours a week. Maybe 35 on a busy week. Um, you know, I. I really try to keep my work Tuesday to Thursday. Um, I like to keep long weekends and, and not feel like I have anything coming right out of the weekend on a Monday. And I like kind of wrapping everything up on a Thursday. So if I can, you know, put in five to seven hours those three days, I feel really good. And then every now and again, I put in a little bit of time on a Monday.
Anastasia: [00:27:18 - 00:27:35]
So in your experience of teaching people for a long time now, what would you say is the most powerful argument for someone who just stuck and just keeps trying to earn more and more and more money and can't get out of that rat race.
Justin: [00:27:36 - 00:30:38]
Well, a lot of it's just conditioning. It's a pattern. A lot of entrepreneurs have been rewarded by that pattern. The thing that they will realize in time is that money is not the solve that they think that it is. For most people, they don't realize that based on regular intervals of earning because you're just wanting to accumulate more and more. Usually it takes a big exit for someone to actually get that it didn't feel as good as what they thought it would feel like. It didn't change their world the way that they thought it would change their world. Certainly can. It can help and it can. You can level up and, and by the way, sometimes it is a lifelong change, but it doesn't fill the hole or the void that you think it's going to fill, like spiritually and emotionally. I mean, it's almost like you get this biggest deposit you've ever had into your bank account and then it's only a matter of days or weeks until it's like, okay, that's it. What's next? Right. So, but people put all this hope into this big exit or into making more money. So some people are slow learners. There are a lot of things I'm slow learner, I'm a slow learner at. Luckily for me, it wasn't in, in money. You know, I just, I think that a lot of people, their life is ruled by either politics or money. And that's going to create quite a seesaw of emotions if that's the top of the fulcrum. Right. So I see it a lot, you know, how do you undo it? Well, I can assure you to, I mean, do this test if you're, if you're an entrepreneur. Most of most entrepreneurs make their decisions based on the fact that whether they have the money to do it or not, whether the business can afford it or not. But is that the highest quality question? Would you be making different questions and answers and creating different things if you didn't ever have to ask if you could afford it? You know, higher quality question is what's best for the business? What's best for the clients, what's best for the employees, what's best for your family alongside the business? Right. And, and so if we can answer some of those questions and take the financial part out of it, you'll see the value. You'll ask higher quality questions, you'll have higher quality, you know, creation solutions, experiments that you're willing to tackle and try because you're not worried about money. I just think it opens the door for better, like a better existence, for a better way to live, a better way to work.
Anastasia: [00:30:40 - 00:31:19]
At the last Tiger 21 annual meeting, you challenged all of us with lots of questions, basically asking us, did you do this, did you do that? And it was wonderful. I thought it was fantastic. So I can see how your method with asking people questions like this can shift something. You provoke thoughts and even inspire by those questions. It's probably what you usually do, isn't it?
Justin: [00:31:20 - 00:32:49]
I think so. I mean, to me the most thought provoking, commentary, ideas, intellectual stimulation all comes from high quality questions. I think the better quality of questions you can ask, the better quality of conversation you have. The more deep you can go, the more real you can go, the more impact you can have. So we can ask the surface level stuff. We can ask about, you know, or talk about weather or sports or whatever. That makes it just easy to talk about, you know, going shopping. Go. You know what, that's easy. What if we ask questions that are really penetrating, that are really like meaningful to life? What if we ask questions that people have never been asked before, they've never had to answer before, where they can't just rattle something off, they actually have to sit there for a moment, pause, internalize it, and then give a thoughtful response. And so often after sessions working with different people, I'll hear the comment of like, I've never told anyone this, I've never thought about this, I've never put this collection of ideas together. I mean, even when I wrote my book, I hired brilliant people that I thought were the best question askers out there to ask me questions, to elicit things that I felt like only a good quality question could unearth, Like I wasn't going to be able to do it on my own.
Anastasia: [00:32:50 - 00:33:39]
So Justin, you know how very soon after a big exit, and I'm sure you've seen it with people you talk to, we face this dilemma. Shall I work or shall I retire? I call it an exited founders dilemma. And I found actually that both paths have dangers and those dangers are hidden. It's not that simple. Neither path is necessarily right. But if you imagine someone standing on a table at that crossroads and you've been there, what kind of questions would you ask that person to help them choose for themselves which way they want to go?
Justin: [00:33:40 - 00:36:05]
You know, it's interesting. I mean, everyone's got their own journey and what was best for you may not be best for them. So that's why I like you even framing it this way. Like, what questions do you ask to help them come up with what's best for them? You know, I do believe deep down that everyone benefits from time off. If someone's been grinding, regardless of the size of the exit, that some time off will, will really bring restoration to everyone. Like, I really believe that. Now, how long of time may be different? What are you doing in that time? That may vary, but, you know, for me it would be less like, do you want to rush into your next thing or do you want to take time off? It's like, hey, how long do you think would make sense to take off? Like, it's, you're going to get to a point where you're going to have a lot of options and a lot of opportunities. When people know you're on the free market, more opportunities are going to just show up. And if you don't have a plan, you're going to say yes by default. And I think it's really important to know how you're going to respond and how long you're going to say no to buy your time, to buy yourself time and space to think, to plan, to create clarity. But it would be done through a series of questions. It would be done through a series of readings. Like, there's, there's a lot of content out there around exiting and what that looks like and the existential, you know, issues and, and you know, what comes from it. And I think that everyone is, I think everyone just benefits from not rushing into the next thing. The next thing could be huge. But that doesn't mean it's best for you or your family and just taking time to regroup and figure out what does a life of meaning really look like? What does fulfillment for you really look like? What does a good schedule look like? What does your involvement with your family need to look like? And it's like, answer all these questions. Actually, I have this list of questions that I have journaled answers to in different seasons of life, different transitions of life. And before I'm going to move on to that next transition, I just want clarity because that has made all the difference in the world.
Anastasia: [00:36:05 - 00:36:52]
But I heard something important in the beginning of your answer, which is early on, when we are at that crossroads, it may not be the best time to ask people what they want because it's actually too early. They may not know it quite yet. Right. There should be other questions and I think too many people are asking themselves, so what do I want to do now? And the problem is that a, they don't know themselves Enough. B, because they don't know, they're too vulnerable to other people's opinions. And we've seen so many people just rush into something because it's trendy or somebody else wants to do that and they think it's good for them as well. Happens all the time. It's very dangerous. So some questions asked at the wrong time may not be helpful.
Justin: [00:36:52 - 00:37:26]
Right, Totally agree. Yeah, I mean the goal is higher quality questions that lead to some sort of impact and, and sometimes you have to ask a question many times different ways to get to an answer. But sometimes people aren't ready to answer that question because they don't know and that's okay. But if someone doesn't know, it's that much more important to not go rush into something that busies up your time that may not be right. And now you have less clarity because you have less time to figure it out.
Anastasia: [00:37:27 - 00:38:34]
Yeah, I'm totally with you on this. And I actually came to the conclusion that the only reliably good solution for the exited founders dilemma is to do things in the right sense sequence. So instead of choosing either or, you say no, I'm not retiring yet, I'm taking a sabbatical. And then after that sabbatical I will work. Because actually retirement doesn't really work. I found it's not healthy. It's a strange concept when people retire too early when they are physically capable and then they have no purpose, no meaning. And yes they do all these things that they always want. Their heart is not in a happy place. Which is why I think what you are doing is so amazing because we need to integrate our life with our work and our friends and our families. Everything needs to be integrated. Not like I worked very hard and now I gonna go retire and do nothing. I think by the way. No, you wanted to say something? Go ahead.
Justin: [00:38:35 - 00:39:16]
Well, real quick, I just want to say this is a super morbid stat but I actually got it from a friend who's an actuary who has done the research and has that the average person who retires and does nothing has, has nothing that they're doing has a lifespan of four year. Just, just barely over four years. And so literally people die when they retire and they're not pouring into something someone, I mean that, that should be everything you need to know about the, you know, the fallacy of retirement is what I'll call it.
Anastasia: [00:39:16 - 00:40:00]
Yeah but you know, if you, if you look at us as humans from a very big picture perspective. Right. It's not, it's impossible to Explain why would Mother Nature or God create us to do nothing, to be retiring? Right. We are just, you know, cells in a living system. And cells, they take something and they give something, and if they function well, then Mother Nature wants us to live and thrive. And if we stop functioning well, like, we only take and we never give. Why on earth do we need to live? Right. From Mother Nature's perspective, that's how I see it. And then it says, you're useless, Go away.
Justin: [00:40:00 - 00:40:12]
That's right. By the way, I will also concede to say I do think some people should retire from the profession that they can't stand. So, like that retirement is worthy to me.
Anastasia: [00:40:14 - 00:40:18]
But that's a change, right? That's a change of what you do. It's not really retirement.
Justin: [00:40:18 - 00:41:19]
Yes. So it's that pivoting from have to work to get to work. And if you get to work on the schedule that you want with the people you want, what would you do? What does that look like? What would fill you up? How many hours would you work? What days would you work? Which people would you work with? What would you do? What would your actual role be? What would the greater impact be? And it doesn't even have to be for money. Like, think about it. Not even for money. And I think there's a lot of clarity that can come from answering that series of questions that I just, you know, tossed out there. But the. I think that there's something great in knowing that you can retire in having achieved a level of success, financial success, where you can say, hey, I could retire if I want to, but that doesn't mean you should retire. It actually probably means you should transition to the next thing that you probably should have been doing your whole life anyway. And now it's time to get started on that chapter.
Anastasia: [00:41:20 - 00:42:07]
Either that or maybe now is the time to do something else. Right? Because we also change over time, and maybe we did the right thing, but now it should be something else. It's like this brilliant book by Arthur Brooks, From Strength to Strength. Yeah, I think it has. I also love it, even though it's interesting that in our community, lots of people think it's depressing because it says, oh, you peak as an entrepreneur at like 38 or something like this. And people don't like that because they would. They want to keep going. But I don't think that's the message of the book. The message of the book is that now it's time to do something else. Right now it's your personalized intelligence. Maybe you should teach people what you've learned through your experience. And this will give the world more value.
Justin: [00:42:08 - 00:42:08]
That's right.
Anastasia: [00:42:08 - 00:42:10]
Not necessarily what you used to do before.
Justin: [00:42:11 - 00:42:57]
If you stop reading that book 25 to 33% in, you are going to be totally depressed. Because when I was reading that, I was like, man, this guy sure knows how to make a guy feel bad about himself. Like, I'm past my prime and virtually every profession that I could be in. Or I'm like, you know, at the tail end. But he does a great job of saying like, hey, but, but now your next chapter, the next iteration, your next mountain, has impact. There's meaning. It's going to be more meaningful than what you spent all your other years doing, because now you have more wisdom and you have, you know, clarity behind you and time is on your side from the standpoint of being more selective and picky with how you spend it. So it's a wonderful book.
Anastasia: [00:42:57 - 00:44:01]
But, you know, one thing I really loved about that book is that while it says all these things, it also says, but to jump on this next wave, you have to be ready to learn and acquire new skills. And the reason I love it so much is because in our post exit community, so many people are obsessed about the concept of ikigai. And there are different things I don't like about that concept for, for this particular group of people. I think it applies very well in some other context, but one of them is that it has this idea that to be fulfilled, you need to keep doing what you are good at. And I always felt, no, that's not what I find in real life. Like, the most successful, holistically successful people I've met who exited businesses with amazing wealth and then moved on to do something even more impactful and wonderful, they are eager to learn to do something different. Oftentimes, it's not necessarily the same thing.
Justin: [00:44:02 - 00:45:05]
Yeah, I have a great desire and drive to constantly be a novice at something and then have the challenge of actually getting good at it. So that is me to a T. When I get very good at something, it becomes very boring to me and I do not want to keep doing it. I want to master something else or attempt to master something else or at least attempt to like, you know, find improvement in something else. Right. Like that part, you know, the whole saying of, like, it's not the destination, it's the journey. Like, that part I just really subscribe to because that is it for me. Like, I'm an eternal student. I want to learn stuff I know nothing about. I want to meet people and have conversations with you and others where it's like, I know nothing about so much of your expertise. Like, I want to learn, I want to get better. And, yeah, I'm not the guy that can just stay in the one thing. I mean, I get bored pretty fast when I feel like I know it and understand it and I'm on to the next thing.
Anastasia: [00:45:06 - 00:46:04]
But one of the things Arthur Brooks kind of recommends, if it's the right word for it, is for people who've had success in their first choice of professional activity to then go and share what they've learned. And you do that. Right. Justin, you are such a great example of somebody who does exactly that. And I think people who switch to teaching don't have to ever retire. And that's the beauty of it. In a way, it's great that we Peak at 38, because maybe it's great when we move to something that uses our crystallized intelligence earlier than we thought we could. Because, for example, entrepreneurs oftentimes learn at the very, very intense pace. Right. So by the time we're 38, we lived several lives by the average standard.
Justin: [00:46:05 - 00:46:05]
That's right.
Anastasia: [00:46:06 - 00:46:20]
Just because it's so intense. So there's nothing wrong if you, I don't know, sell a business at 38 and then you decide, now I'm going to write a book. I see that. It's actually a wonderful path, a very fulfilling path for lots.
Justin: [00:46:20 - 00:50:50]
Totally. And writing a book is very therapeutic. It's not an easy task. It's a big undertaking, but there's a lot of rewards to it. I got a really funny story. So my mom kind of made me do this aptitude test back when I was in high school. And I had done it a couple of times because I didn't like the results. And so, you know. Right. Yeah. Wrong answer. So the first time I did it, and I think this was my junior year of high school, it said, you know, Justin, you. You know, your skill set, your makeup, everything about you, like, you are destined to be. And I'm like, is it going to say entrepreneur? Is it going to say, like, you know, I don't know, like a stockbroker or, you know, you know, a. A financial analyst. What's it going to say? And it said, teacher. And I was like, oh, man, I don't want to be a teacher. All the teachers I know, like, they have, you know, these students are. Are just so disruptive. It's a hard gig. They don't make a lot. Their. Their schedule is Totally fixed. It's hard to, like, you know, inside the school year, go, go travel or do anything. So I'm like, that's horrible. We retake it my senior year. Sure. Be a teacher. And I'm like, no way. So I'm, I'm going to go chart my own path and I do all these different things. And all along the way, you know, I called it coaching people, you know, and then it's so funny, like, I had this epiphany, really, just like a couple years ago where I, I thought back to that and it was actually someone asking me a good question about it that brought it back up. And then I was like, like the craziest thing. Guess what I do for a living. I'm literally a teacher now. I figured out a way to get around the things that I didn't like because I'm a highly paid teacher and I can teach on my schedule and I can teach for a period of time or I could stop teaching. I can travel the globe. So it's like all the things that held me back from wanting to be a teacher have been removed or I figured out from my entrepreneurial background how to, you know, how to make them work for me, but that's it. But I do, I do think you have to be careful in today's day and age with teachers, especially those that are all over social media or especially those that, you know, they don't have a proven track record. Because today, I mean, I hear this all the time, you know, I'll say, oh, you know, what makes you think that, you know, this person is an expert at what they do? And they're like, well, they have, you know, 4 million social media, you know, 4 million followers on social media. I'm like, well, that, that means they're a good marketer. Like, you know, what, what do you, like I'm saying, like, what makes you think that they're good at what they do? Like, give me experience. And they're like, well, they have all these videos online. And I'm like, man, I cannot believe how many people substitute experience for large social media following where a lot of the people that are out there te these strategies make their money from these strategies they're not even an expert at. They didn't actually do them. So, you know, with you, Anastasia, you actually have run companies, you actually have exited four companies. You're an expert. You don't need the money from anyone doing anything today. That's exactly who I would want to spend money on to be in your ecosystem. Does that make sense? You know, for me, I make money on all my investments. I don't need the money from lifestyle investor. It's become a profitable business, but it's also become a business that does a lot of impact in the world, like, you know, just through various different measures of, of, you know, helping less fortunate and, and you know, serving those in, you know, that are, they're really, you know, damaged through human trafficking and whatnot. But I just want to say, like, I love to teach, but for those of you that are looking for experts, look for the track record, look for how many years they've done it. Look for the fact that they've made a lot of money doing it and that they don't make their money from teaching it and that they're not an expert, that they've only been in the, you know, in the coaching or social media space for a decade. Like, you can't, it's hard to become an expert inside of that, short of a time frame.
Anastasia: [00:50:51 - 00:51:13]
Yeah. That brings me to another question. Some people I talk to exited founders looking for what's next, feel there is something wrong, like morally wrong in pursuing something that will be profitable. Have you had those thoughts and how did you resolve those for yourself?
Justin: [00:51:14 - 00:54:23]
Yeah, you know, it's interesting. I certainly have combated this a little bit because, and it's less from me, it's more from other people having their belief that if you've, if you've made it well now you, you shouldn't make any more money. Like, you should just like give everything. And I don't know that I subscribe to that. You know, I really believe it's also got to make sense for the people that are going to spend their time doing it. So for me personally, I have no problem if someone is an expert, has done very well in a certain thing and they create a new business and it's profitable. They, they are teaching what they're doing and it's profitable. I have zero issue with that. In fact, like, that's what I look for when I spend money. If I'm going to invest in myself, I'm going to those people. So not only do I not have an issue with it, I commend them for it. And I want to be around them and I want to be in their ecosystem. I also believe that, I mean, there's this world of haters that is, they're always going to exist and they're never going to be, they're always going to poke at you because you've had success or You've had a greater level of success than they've had, or you're doing things differently than they would do. And so they've got an ax to grind like that that world is just always going to exist. You see it on social media. Just look at all the naysayers to anything, any positive post. And so I try to not spend time, energy and attention there. And so you kind of have that world. You've got the world that is actually doing it. And then you probably have some people in the middle that are like, well, if you don't need the money, why are you doing it? You could just go do something else. If you're more maybe the cynical, skeptical people where it's like you, you know, why don't you go live on an island or whatever. And I think a lot of those people just don't quite understand the fulfillment that one can feel in doing work that they're, that they just love to do, where they believe that they're making a difference, where they, where they're seeing impact on a regular basis. And by the way, if I'm going to do that anyway, why not do it at a, at a large scale? Why not create more like I, you know, in my Lifestyle Investor Live event that we just did, we did our big spring event last week, one of the comments that I said is, you know, you want to create more wealth so you can have more impact. It's not just about you and consumerism. It's so that you can do better things in the world so you can have more influence, you can have more dollars, you can have more leverage. There's so many things that having more wealth can help you do. And it most certainly doesn't have to be you living a better lifestyle. And by the way, I have no problem with people that want to live a great lifestyle, but I also don't believe that all the money we make should go towards us. I do believe that those that have been blessed above and beyond the norm were called to be generous and we're called to help and we're called to give in a sacrificial way.
Anastasia: [00:54:24 - 00:54:47]
Yeah, but even from a very selfish standpoint, we cannot be fulfilled if we are not giving. Right. It doesn't mean we are giving money to charity like you are giving your knowledge to the world. Right. Your unique knowledge that you paid for with a lot of scars and time and energy.
Justin: [00:54:48 - 00:54:49]
That's right.
Anastasia: [00:54:49 - 00:55:09]
And you give it to the world and that gives you fulfillment. Can't be any other way. Right. 100% so, Justin, you have a daughter. How do you look at, you know, what you want her to think about? Wealth, success and lifestyle?
Justin: [00:55:11 - 00:57:33]
Well, I want her first and foremost to follow her dreams and passions. I don't want her to get lost in what makes the most money. I want her to know that she'll be equipped, equipped to make money, to manage money, to multiply money and to make money matter. You know, those are the things we talk a lot about in our community. She'll be equipped to do those things that. I'm going to work with her. I am working with her, but I'm going to continue to work with her there. So I want her to pursue her dreams, but I also want her to know that she will have and does have the skills to be able to compound wealth, to be able to multiply it, and to be able to do good work with it. I mean, we started at a young age with her, you know, kind of breaking up the buckets, you know, how young? Probably four or five. She started, you know, having spend money, save money, give money and invest money. And so it was like those four buckets of everything that she makes, even if it's money that people give to her for birthday or whatever it is, that to us has been hugely important. We see her heart growing for people in the process of that, where it becomes normal, it becomes, you know, if you do that at a young age, it's a lot easier to give money as you make a lot of money. But a lot of people don't give. They're. They don't have that conditioning. And then when they make a lot of money, it's that much harder because the habit isn't there, of course. But we also want her to, you know, I mean, we, we see the tendencies of like, I want to spend all this money, I want to get new stuff. And I get that. That's, you know, it's. These are things they need to experience. And like, part of me is, like, heartbroken when she spent all her money, but part of me is like, what a brilliant lesson, because she's asking for this and I'm saying no. And it's hard because I want her to be able to have it, but I'm like, you need, you know, you can use your own money. And she's like, but I don't have any. It's like, exactly. So that's why we need to save. That's why we need to invest. So, yeah, we're, you know, we're doing the best that, that we can with it and I think we're doing an even better job than our parents did. And we hope that she's able to do an even better job than we're able to do.
Anastasia: [00:57:33 - 00:57:35]
How do you want to be remembered?
Justin: [00:57:37 - 00:58:24]
You know, pretty simply just someone that wanted to serve the world in a great capacity. I just want to be remembered as a guy who gave of his gifts, gave of his time, gave of his money, gave of his resources, his network, his connections, and really helped people level up and, and take their lives to the next level. That's it. I don't need anything named after me. I don't need any buildings, I don't need any of that. I just want to be remembered as someone that helped others kind of level up and really live a life worth living.
Anastasia: [00:58:25 - 00:58:33]
Justin, this has been amazing. Thank you so much. And it's such a beautiful last answer. Thank you so much.
Justin: [00:58:33 - 00:58:52]
Well, thank you. It's wonderful being here. If people want to learn more about what we're up to, they can go to lifestyleinvestor.com for anyone that kind of wants next steps, we do these consultation calls, these strategy sessions that are usually 500 a person, but for anyone in your community, we'll just do a free one.
Anastasia: [00:58:53 - 00:58:53]
Thank you so much.
Justin: [00:58:54 - 00:59:31]
Yeah, if you go to lifestyleinvestor.com consultations, you'll learn all kinds of cool next steps. How to get from point A to point B more, you know, kind of broken down and catered to that person. So if you are interested in, you know, the book or the podcast or master classes or courses or masterminds, all that stuff's@lifestyleinvestor.com but if you want a hands on person on our team kind of walking you from point A to point B, creating, you know, financial freedom, becoming a lifestyle investor, what would be next? Go to go to lifestyleinvestor.com consultation.
Anastasia: [00:59:32 - 00:59:36]
What about social networks, which ones you regularly use?
Justin: [00:59:37 - 00:59:51]
We're on most of them, definitely Facebook, Instagram, LinkedIn, a little bit on Twitter. We may work a little bit more there.
Anastasia: [00:59:51 - 01:00:16]
So, Justin, thank you so much. I'll talk to you soon on this podcast. We're building a real post exit playbook together. If today helped hit follow or subscribe so you don't miss the next one and please share it with one exited founder you care about. Thank you.
