Life After the Exit: Why So Many Founders Struggle with Anastasia Koroleva – EP 239

Justin Donald: Hey, Anastasia. So good to have you on the show.

Anastasia Koroleva: Hi, Justin. Really good to see you too. Very exciting.

Justin Donald: Well, yeah, this has been a long time coming. This has been over a year that we have talked about doing this, maybe closer to a year and a half. Maybe it could be even two years.

Anastasia Koroleva: No, two. Of course.

Justin Donald: Oh, my goodness. So, I'm so glad we finally got it on the books because you and I, we share some communities together. We're part of TIGER 21 together. We're entrepreneurs together. We're in a post-exit founder group together. I mean, we're in all kinds of groups. We're in some other entrepreneurs' circles. So, I'm so glad that we get to have you on the show and tell your story because you really are an expert in the world of exits. You're an educator. You're truly a foremost expert because you're a four-time exiting entrepreneur, which is super rare, right? That's unicorn status. And then you have your own podcast, the Exit Paradox. And so, I can't wait to dig in and figure out how you got to where you are.

But one of the things that before we even dive in that I think is so important, a lot of people think that once you have an exit or once you make a lot of money, it's like, "Hey, life is good. All problems are solved. Money solves every problem that you could have ever had.” And by the way, money solves a lot of financial problems, and it takes care of a lot of things. But I would love to just hear from you to just dispel this fallacy that once you make it, all is good and you just coast the rest of your life.

Anastasia Koroleva: Well, I definitely learned that lesson the hard way, and we can talk about it for days, but basically, I realized that I never even questioned before my exit what would happen afterwards. And I certainly did this expectation that somehow life will definitely be easy and not harder. And what I found is that so many new challenges come to our lives that we didn't expect. We are not equipped to deal with them, and that causes a lot of anxiety and stress. And that stress and anxiety poison what should be a celebration of our success. And it takes people, on average, 10 years to go through this if they do it through natural trial and error.

But of course, I had no idea. I wasn't prepared for it and, again, learned it the hard way. But at the same time, there are so many incredible gifts that we get from an exit, and it's so easy to forget about them just because we are so shocked by things being different from what we expected.

Justin Donald: Yeah. What would you say some of the greatest gifts are? Again, I feel like a lot of people might say that it's money, and maybe that's one of them. Maybe that's a top five or a top 10. For me, there are so many other gifts, much greater than the financial rewards that have happened through exits.

Anastasia Koroleva: Yeah. I think money is definitely an amazing gift, and if anything, I only appreciated it more over time. I think one of my problems actually was that I did not fully appreciate its power, and I made quite a lot of really stupid, very common decisions, poor investment decisions exactly because I did not have a full appreciation for the power of money, for the power of financial freedom. I also didn't realize that just getting a lot of money doesn't mean you're financially free. Obviously, you are an expert in this, and I learn from you all the time that you need to take certain steps before you can actually be financially free. So, wealth is for sure a gift that needs to be appreciated and protected properly.

And I often come across people who, especially with very large exits, they kind of make my mistake. They say, "Oh, I used to chase money for such a long time. I don't want to do it ever again. I have enough.” So, they start ignoring their money and making stupid decisions, which actually, later they regret. And one of the things I'm trying to do is say, "No, don't be ashamed that you respect your wealth. It's perfectly healthy. It's good.” Because I think what happens is that the first stage after we get our wealth as an exit founder is turning it into financial freedom, which is by itself very hard, as you very well know. We need to change our mindset. We actually need to learn a lot. We need to meet other people who can teach us how to do it properly.

But then even after that, I think our job adjusting to wealth is not done. Because for me, the final kind of highest level of thinking of wealth is thinking of wealth as leverage for the life we want to have, but also that contribution we want to give to the world. So, it took me so long to understand that, "Oh, actually, this wealth is not just something that's for me. It's also something to multiply my positive impact on the world.” And then suddenly it doesn't sound that selfish and smallish as it did for me before.

Justin Donald: Right. Yeah. I love that.

Anastasia Koroleva: And then some people have the opposite problem. They actually just can't stop chasing money, and that's another kind of tragedy, and it takes a lot of time to get out of our systems.

Justin Donald: Well, culturally, I think we have built a society around chasing that, which is not as important. You find out later on that chasing money and people spend their whole lives doing it. They do it to the extent of relationships and their health, and they find out later that it's not what it was cracked up to be. And really, financial freedom trumps whatever the net worth number is. I don't even care what the net worth number is, but to be financially free, it opens up the playbook for so many other decisions.

Anastasia Koroleva: Absolutely. Yeah.

Justin Donald: Personally, professionally, right? We talk a lot in the Lifestyle Investor community and mastermind. We just did an event this last week, and I like talking about how most people aren't even good at making money, but the ones that are good at making money rarely are good at managing money. The ones who are good at managing money are rarely good at multiplying money. That's a very small percentage of the population that's actually good at that. Most money managers have no ability or no real understanding of how to multiply money, but what's the whole purpose of making money, managing money, multiplying money? It's to make money matter. It's to have the impact. It’s to do the things. It's to support friends, family, loved ones, strangers, people going through tough times, people that didn't get the hand that you were dealt.

Anastasia Koroleva: No, absolutely, and this is exactly why wealth is a gift and it should be respected and we should spend time learning how to manage it. And talking about other gifts, obviously, we get our energy released from the business, and we get our focus released. But the problem with those two is that they often get trapped in all these psychological issues. And because we are so emotionally disturbed and intellectually confused that we can't actually direct our focus and energy where it should be going. It takes a long time for exited founders to actually start channeling energy in the right place. And in many of our communities, you hear it a lot when people say, "Oh, I have such low drive. I have low energy. Maybe I'm sick. But I checked myself everywhere. I tried every longevity trick, and I'm still not driven.”

But people are not driven because they don't have that sense of purpose or that sense of direction for a very long time. So, we do get that gift of energy and release focus from the business, but we don't know how to actually use them. So, for a while, they don't also, obviously, another super amazing gift is our freedom. But then again, we get all this freedom and then soon enough, we end up in decision paralysis because it's too much freedom. And again, we just don't know how to use our freedom. Turns out that this incredible thing we wanted also requires some skills and understanding in mindset shifts.

Justin Donald: I had a really good friend and mentor once tell me, "Too much of a good thing isn't always a good thing,” and it has just stuck with me through life. And it is so true because whatever the thing is, you get too much of it. Man, it can be the end of you.

Anastasia Koroleva: Yeah. And of course, post-exit, we have to go through this period of just learning basic life skills because most of us, when we build a business, we create a whole world right around our own personality, which is usually quite quirky and doesn't really fit naturally into the world, right? That's the reason why we often go into entrepreneurship. We don't quite fit into the world. So, we've created this beautiful world and we thought, "This is the reality,” and then we sell that world, we lose it, and it turns out that we still don't fit. Actually, oftentimes we fit even less than we did before. And these are just some of the challenges that people don't expect.

Justin Donald: Well, let's get into some of your earlier companies. So, there are four companies that you started and exited, and I'd love to hear just what that looked like each step of the way, what may be. You learn to get better the next time. Maybe what lessons were learned in a way that you had to learn them the hard way to figure out the next iteration. Anything you want to share?

Anastasia Koroleva: How much time do you have?

Justin Donald: Right? Yeah. We could do this all day.

Anastasia Koroleva: Exactly. So, let me try to be brief. First of all, the first company I joined early on, I didn't start it. So, I was very lucky to be able to join a company and then kind of see what entrepreneurship actually is because at that time, I was an M&A lawyer in New York.

Justin Donald: Yeah. You went to NYU law school, I saw.

Anastasia Koroleva: I went to NYU and then I worked at Skadden, Arps for five years. And that's actually when I first got fascinated by what happens when people sell their businesses. Because when I represented the buyer, these were usually companies, they’re very pragmatic, and they were very sort of intellectual about it. But whenever I represented a founder, it was a completely different story. It was so personal. It was so wonderful in a way, but so challenging. So, anyway, I was a lawyer, and then I met the man who became my husband. And he had a startup, and he persuaded me to leave the law firm and join him in his young startup, which we basically then…

Justin Donald: Nice move. That was a good play right there.

Anastasia Koroleva: Well, it wasn't obvious at the time. All my friends were thinking I was totally nuts to live my legal career for a small startup.

Justin Donald: High-paying, comfortable job. You can move up the corporate ladder, but it's what everyone wants. It's what we're trained from get-go to desire, right? So, you buck the trend early on.

Anastasia Koroleva: Well, I was absolutely charmed by the Silicon Valley, right? I lived in New York. I didn't know California. I hadn't been there. I only knew New York. And then I met him and he introduced me to this completely different world, and I felt, "Oh my God, finally.” I feel like a fish in the water. My people, the energy, everything, just fell in love with the whole package. So, in that sense, I was extremely lucky. And I started learning the basics in an environment which is more comfortable than many founders face because somebody already started that company. But then a few years in, I started feeling that I really wanted to also have my own company. And I wanted, like, the first company was B2B, software as a service, but I wanted to have something for people, a B2C company.

So, the second one was very different. It was, basically, we came up with a different way to connect phone calls, which really benefited immigrants. So, that was very relevant for me personally, and that's exactly what I was looking for, something that I could personally relate to. And it was the time when I really learned how important product market fit is because we created this very experimental technology. We put it out there in the world. We created the world's ugliest website. We didn't do any marketing. Justin, we literally did not spend either effort or money on marketing. And a year later, we had 15 million in revenue, and we were still three people.

Justin Donald: Oh, my goodness.

Anastasia Koroleva: And all we wanted to know is like, who are these idiots who are buying this service? Like, we couldn't even understand why because, again, luck was definitely a big part of it. But the product market fit was my biggest lesson. You asked me about the lessons. I think once you experience it once, like this real product market fit, when people are just grabbing your product before you can even create it, it's very hard to ever again settle for not having it. So, my other businesses, that's all I cared about. I'm like, "Can I get to a product market fit quickly?” If not, I don't want this because I know how amazing it fits, how easy it becomes when you create something people actually want.

So, what happened was we sold the first company with my husband and it didn't go very well. So, both of us didn't take it well at all because both of us didn't have any experience, any understanding of money. The company was bootstrapped. So, we had this nine-figure exit and suddenly all this cash, no idea what to do with it. And we reacted to it very differently and it actually broke our marriage. It's one of the reasons why I got so interested in the phenomena because I thought, "Why? It makes zero sense.” This is when we should be having the time of our lives, but didn't happen. Now, we are very good friends, no problem. But for a while, it was really tough emotionally and then in all possible sense. And then it took me four years to remarry and start a new family.

And that was four years when I also tried to build new businesses. And the first one, which I started after the second one was sold, actually didn't work at all. It didn't work because I didn't appreciate what happens to our motivation. I just really wanted to escape all my worries, including the divorce and the whole shock that the exit wasn't what I expected. So, I wanted to go back to my comfort zone, which was, paradoxically, a startup environment. So, I started this new company for wrong reasons. It wasn't the right thing to do, but it took about two years before my motivation changed dramatically, and I just found myself in this space. I'm like, "What am I doing?”

I have two little kids, I'm going through this really difficult divorce, and here I am hiding in an office trying to build a business. And I felt guilty all the time being in the office. And then I felt guilty being at home because neither, like, I wish I knew you at the time, because I really could use an expert in the whole lifestyle and investing situation. And I made so many silly investments at the time. So, this four-year period was a bit difficult. But then, of course, once I've created stability and safety, I could get my mind off all those worries. And then this kind of natural flow of energy and creativity just showed me the direction. But it took a while.

Justin Donald: Yeah, no kidding. And so, it's interesting to hear this, and I'm curious on like the progression of exits. Is this one where you kind of stair-stepped up each time? Did multiples change? Were multiples the same? By the way, you can be as vague or as detailed as you want. I'm just always curious in all the metrics on exits and take-home. And by the way, congratulations first and foremost because in your first exit, you're set for life as long as you don't do anything crazy, right? I mean, it is tough to hear that it was through that that your first marriage ended. But I know your husband now and he's wonderful and I'm glad you have found him and I feel like he is just a grand slam. So, it all worked out. But I am curious on some of the details, like did you kind of have some ups and downs in it, or did they progress up, or what did that look like?

Anastasia Koroleva: No, absolutely. All my four exits were completely different. And it's so interesting. It's almost like having several kids in the family, right? They just have to be different. Maybe somebody is more stable and they do what, as you mentioned, kind of you stack them up and you get wiser every time. In some ways, I definitely did, but what I found is that all my subsequent exits, after that first one when I was set for life, they were in different ways affected by my own evolution as a person who has to deal with wealth and whose motivations changed.

So, for example, my business number three, I know I sold way too early in its story. I actually had a product market fit. Things were going really well, and I was at the point when I needed to scale it. And from the business standpoint, I was very happy with how I was approaching it. I felt, "Oh, I was building on that knowledge I've acquired before.” The team was fantastic like everything was good. But what happened was that's exactly when I got really affected by the divorce and the fact that the kids were suffering. And I had to make a very tough decision. I had two little kids who were suffering, and then I had a startup baby who also felt like a baby. And I had this super tough choice, like, which baby I sacrifice.

And obviously, I sacrificed my corporate baby. I cried for two months, but I never regretted it. I never regretted it. Sometimes I get this feeling like an unfinished creative project like I was painting a beautiful painting. I had the vision in my head, and then I had to walk away from it. And there was some dissatisfaction about it. I also know that I could have sold it for much more. But you know what, it's fine. Because also, again, my motivation was changing, and it wasn't that important anymore. Other things were more important, and that's fine. And now I think I am at a very different moment when I really just genuinely feel that my life is so aligned with my sense of purpose and what I want to contribute to the world.

And it would be completely impossible for me to even think of sitting down and saying, "Oh, which business I’m going to start now so I can exit it as quickly as possible?” I could do it intellectually, but I'm not driven at all to do that. And that's okay.

Justin Donald: Yeah. It is.

Anastasia Koroleva: It's a stage in a natural evolution. My first exit was 14 years ago. So, it took a while.

Justin Donald: Yeah. Well, I had a friend and mentor once tell me that you're basically always holding these two balls. One happens to be a glass ball and one happens to be a rubber ball. You don't ever want to mix them up. The glass ball is your family, and the rubber ball is your business. And your business is so darn resilient. You can drop it a million times. You can drop it to the point that it stops bouncing. You can always pick it back up. You can always recreate it. You can always start a new one. It has resiliency through and through, right? Your family is the glass ball. And you drop it once and it shatters. There's no picking it back up. There's no catching up on the things that you missed. And that just screams to me that you made the right choice.

And you know what? You still got an exit, which is great. I get the unfinished business part of it. But, I mean, you still sold it, you still made a profit, and could you have made more? Sure. But could you have made more, and it may have been at the detriment of your kids? Yeah. And so, my wife is so good at saying if you're saying yes to something over here, then by default you're saying no to something over here. And you've got to be very intentional about what you're saying yes to because of what you're ultimately by default saying no to. And that's really gotten me to shift a lot more of my yeses being family and not the business because the business will figure it out and if it doesn't, if the team doesn't, if I don't, if the systems don't work, like, if it just doesn't work out, I would still rather lose the business than my family.

Anastasia Koroleva: No, absolutely. Absolutely. You see, you're very wise. You're wiser than me. I had to lose my first marriage to get to that. But that's life. Sometimes it needs to teach us.

Justin Donald: Don't you worry. I made plenty of mistakes along the way. I mean, I am the master of making poor choices and learning from myself when I could have and should have been learning from other people. So, I'm right there with you. I was thinking about our conversation. So, two years ago, and it was actually, what, two years and three months ago, we had a conversation, and was this in Scottsdale? No, this would've been in Florida again.

Anastasia Koroleva: It was in Florida. Yeah, I remember it very well.

Justin Donald: And this was such a fun conversation because you had asked me some questions about Lifestyle Investor. You had asked me some questions about my passions and what I want out of life, and you are really looking for kind of your next project, something that is your masterpiece. And it didn't necessarily have to be another business per se, but it had to do with the thing you're most passionate about, which is people, relationships, teaching. You're an expert on exits and so it's like creating a community with people that have exited and just doing epic stuff together. And I had such a fun breakfast with you kind of walking through in my mind how I see it. Not that it has to be that way, but it was just kind of fun iterating with you.

Anastasia Koroleva: Well, Justin, I'm sure I got much more out of that conversation because it was your clarity and your confidence and the certainty about what you are doing that inspired me so much because I walked out of that conversation just so energized and also thinking, "Oh, my God, like, everything's possible. Look what Justin achieved. And my dream is possible.” Because I was very certain about my dream at the time. Like, I felt that I had this mission to help other exited founders not make all these horrible mistakes. And I felt I had clarity that would be very useful for others, but I wasn't quite sure how to deliver it to others so that it's actually helpful.

Because all that knowledge is completely useless if you can't package it and deliver it in a way that helps people. And that conversation was really life-changing for me, to be honest, just to understand how you do it and why you do it. I'm very grateful.

Justin Donald: Well, thank you. I'd love to hear more, like share all the cool things that you're up to inside of this community.

Anastasia Koroleva: Well, my biggest passion right now is my Post-Exit Academy because I realize that what's missing out there is, again, well-packaged insights. There are communities that are absolutely amazing. Your community is a great example of it, and some of the other ones that we are both members of. And most communities try to help members on their journeys. And I think what I can actually give to the world are these dynamic insights from my experience, but also from my experience in interviewing hundreds of other exited founders. Because for me, the patterns are very clear. And I think that the patterns most people are talking about post-exit are not actually necessarily correct.

Like, for example, lots of people are imagining this very simple arc. We go up emotionally, then we go down for a while, and then we figure out what we want to do next, and then we are fine. And then we kind of plateau because then hedonic adaptation kicks in. And then we are back more or less emotionally where we were before an exit. And I found to my great surprise, actually after I looked at hundreds and hundreds of stories, is that it's not what actually happens at all. What actually happens is we do spend about 10 years going through this sort of wave after wave after wave because that first arc, which ends with us finding something new to do, is usually a mistake.

So, if you talk to someone who just usually it's like maybe a year after an exit, they just found something new and exciting to do, I was there too, they will tell you, "Oh, I'm in such a good place.” I figured it all out. Right? Talk to them five years later because year five or year six is when most people pay for their early mistakes, right? This is when they realize all that angel investing was stupid.

Justin Donald: Right. So true.

Anastasia Koroleva: Exactly.

Justin Donald: Hopefully, you learn it that early, right? Some people you don't even know for 10 or 15 years so hopefully you figure it out in the shorter timeframe that really is the wealthiest people in the world only put 1% of their net worth in those deals.

Anastasia Koroleva: Yep, exactly. But you know what I'm talking about. Like, so many exits happened in 2021, right? We had this huge sort of wave of exits.

Justin Donald: Yeah. We had a ton in our community. This is so crazy. We had 24 exits that year with 12 of them inside a Lifestyle Investor, 12 of them being inside of a six-week period of time.

Anastasia Koroleva: No way. That is crazy.

Justin Donald: It was crazy. So, I mean, we're well over 50 exits as a community, and it's probably closer to a hundred now. And we keep our community quite small. And so, actually, we just did an event last week. It was buying and selling businesses. And so, we brought some experts in from all across the board that just do a great job buying and then some world-class experts to help on exiting. A lot of people that I featured on this podcast, and then we brought in Andrew Howell with York Howell on estate planning.

Anastasia Koroleva: Yeah. But you see these people extremely lucky to be in the community, right? Because they could rely on others to support them through this first crazy sort of wave in the rollercoaster. Because I think in the beginning it's just so important to simply normalize your situation, to understand, "Oh, there are 50 more people in my community that are going through the same thing.” So, it's wonderful.

Justin Donald: Yeah. Totally. Yeah. You need to have people around you, period, that you can do life with, that you can learn from, that have been through what you are going through and/or are going through it at the same time you are.

Anastasia Koroleva: But, Justin, at the same time, I found that as wonderful as it is, there is also a big danger when you are going through this in a big wave with other people because we tend to amplify and multiply our mistakes. So, this early stage is always so full of stupidity, simply because our emotional state is not good. The quality of our decisions cannot possibly be good when we are dealing with so much emotional disturbance. So, when people are all looking for answers, but everyone around you, those who go through the same stage, that's I think why we see so many like venture studios or angel investing right now. These things make no sense financially. Also, the chance of them succeeding is so low like a venture studio means that…

Justin Donald: Less than 1% on these one-off deals.

Anastasia Koroleva: Of course, because your focus cannot be on one thing. You are taking so much risk with your money and your time and everything, but it's just incredible how many people are jumping into venture studios and then they find themselves working very hard, draining their money, their energy. And usually what I noticed is like if you think about it, 2021, right, when we had all these exits. It's 2025 now. So, most people are now in year four. In my experience, year five, year six is when they start seeing those early mistakes. So, we may have these two years now when there will be lots of unfortunate stories. And most people will not tell anyone unless they're in a community like yours, when they can trust each other. But for those who are out there alone or too proud to share, they may find it very difficult to go through this year five and six.

Justin Donald: Yeah. I agree with you completely. When you learn how the billionaires invest, it is wildly different than the way that we have all been taught, the way that people in our circles and peer groups and our parents invested or learned to invest, or the way that Wall Street has taught and conditioned us to invest. It is night and day, just night and day. I mean, when you study the single-family office investment data and asset allocation, it is so different than what most people have ever seen, have ever thought about. And it's like, "Oh, it makes sense. There are patterns. There are rhythms.”

Like, all of these wealthy people are doing the same thing like go across the board and check every major bank. Go to Goldman, go to JP Morgan, go to UBS, go to even look at like the private equity giants like Apollo and KKR. Like, look at their numbers, their high net worth people, and they literally match across the board. It is uncanny.

Anastasia Koroleva: But do you agree that so many of us after an exit just have this incredible confidence that it's just really based on an illusion. We may be good value creators. It does not make us good investors. Quite the opposite, right? The mindset, the personalities are the opposite of what the best investors have.

Justin Donald: Yeah. We try and teach people in our community this all the time, "Do not rush into investing. Learn how to invest.” I mean, take a year off if you have to, at least six months, and don't do a darn thing because the mindsets and temperaments are 100% different between entrepreneur and investor. An entrepreneur is a silver-lining type of person. They're very positive. They're very optimistic. Against all odds, they're going to find a way. But if you go into investing with that, you're going to lose all your money. You have to go into it saying that everything's a bad deal unless you can prove otherwise.

So, as an entrepreneur, you go into everything as, “Yes, it's possible.” As an investor, you have to go in as, "No, this is a horrible deal.” It's two completely different mindsets, skillsets, and it is so challenging to me when these exited founders have so much confidence that because they exited their business, now they know how to invest in all these other businesses and then invest in all the high-risk, one-off, or early-stage. Even if it's VC, that's still super risky. I mean, still a good VC like the top tier one, best VCs in the world are still only getting it right three out of 10 times, 30%. And that's really good. If you're bad, it's like 10% or less.

Anastasia Koroleva: No, absolutely. Absolutely. And this overconfidence lasts until people start losing a lot of money, right? But again, sometimes it takes years because you talk to someone, even in year five, if they haven't seen the results from the angel investing yet, they may be very optimistic.

Justin Donald: That's right.

Anastasia Koroleva: But I'm actually curious what you think about the reasons also, some kind of deeper reasons why people behave like that. Because I found in my own experience, but with other people as well, that sometimes we just miss the action, but we don't actually want to work full time, right? We want this balance, lifestyle investing, work-life balance. We don't know how to find it, and we think, "Oh, okay, you know what? I'll invest into someone. I'll mentor them whenever I want to. I don't have to run a business. Perfect.” Right? And then you talk to them several years later, and they're like, "Oh, this is boring. It was such a waste of time. They didn't listen to me. They only wanted my money. They never cared about me anyway.” And because I didn't have control of the business, I couldn't actually realize that entrepreneurial itch that I had. Is it what you see as well in your community?

Justin Donald: Oh, yeah. We see it all the time. So, there's the danger that a lot of entrepreneurs is going to face is that their ego and their identity is tied up in their business. You sell your business, now, boo. Like, poof, it's gone. You now don't exist like who you are, who you were. And people like, I mean, I am smiling as I say it and I don't mean it in jest, but I mean, people lose themselves. They literally go through a straight-up crisis of identity. And so, we see that all the time. Then we see the overconfidence like, “I was so successful over here. I'm going to be so successful in anything I do.” And there are situations and seasons where that can help. I think overall, it probably lends to more disaster than success.

I think humility and curiosity, to me, are the two things that are going to help people really thrive in this world and in the next chapter, scaling the next mountain. So, I think a lot of entrepreneurs have a hard time with that. I think that their meaning in life is often wrapped in business. And that maybe isn't the healthiest place to have the most meaning. I think people with strong faith, with very strong family values and family ties and strong relationships, and friendships will prioritize those three things over a business, which I think is a lot healthier in general.

And you hear this with people on their deathbed saying, “I worked too hard for money or I put too much time into my business. I neglected my family. I neglected the key relationships. I neglected my health.” So, I mean, you hear it over and over. So, this isn't just me emotionally feeling that this is true. This is just based on a lot of things I've read and learned over the years. So, I think these are all the things that a lot of highly successful entrepreneurs fall prey to. And then, of course, if you're not an expert, you're going to be taken very easily in the financial world. There are so many smooth talkers, so many confident individuals that either have a track record or can make you believe they have a track record.

And even if they had a track record, you've got to understand that every decade is a little bit different. So, someone had a track record that was great for one decade, I mean, we had a frothy decade where everyone seemed to do great, but now we're in a new season and most of them are failing miserably. And so, I just think that track record has to span out a lot more than just 10 years.

Anastasia Koroleva: Yeah. And I think many of us post-exit lack their appreciation for professional investing because I hear it all the time people saying, "Oh, I really dislike my wealth manager or my bank, or whatever,” and I understand why. I've been there. I also had my disappointments. But it's incorrect to be a snob towards people who actually know how to invest money. And lots of entrepreneurs have that, and that's just wrong. We need help and we need to actually trust someone. And it's so, so hard because you're totally right. There are all these sharks out there looking for us knowing that we are vulnerable, but at the same time, we need to find someone whom we trust.

Justin Donald: Yeah. The trust is huge, and I also think not over-allocating to anything too. If you look at the wealthiest people, generally, if they have a money manager that they outsource to, most of the single-family offices hire a money manager in that manages. But even for like the multifamily offices that hire out to people, it's generally only 15% to 25% of their net worth that a money manager has, right? The rest of it, I mean, the vast majority, 50% to 60% is in alternative investments outside of wealth managers. These are just connections that they have with other people that are experts in their industry, right? Where they're investing as an LP or a GP, most commonly an LP with some GP economics and things for the wealthiest families.

And so, it's making sure that diversification is correct because you'll hear a lot of wealthy people say, “Hey, it is really easy to make a lot of money. It is really hard to not lose it.” And that's where they're great is they diversify and they don't put too much. They're never overallocated in any asset class. They're never overallocated with any single wealth manager. And they just have a thoughtful process about it all and the way that they check in and they have quarterly investment statements that they're looking at, that they're making decisions and they're making these decisions on a regular basis.

Anastasia Koroleva: But how do you feel about the other school of thought that it's better to actually put most of our money into something we understand really well, and there are also lots of examples of people doing that. They pick two, three, four maximum things and invest into them.

Justin Donald: Yeah. I think that it has worked for some people, and I think that if you are truly the foremost expert at something, I mean, that's a great strategy. The issue is the economic times or the black swan events that are unanticipated, and if it wrecks your one thing, then you're dead in the water. And so, to me, I don't like it as much from that standpoint. And I would also say if you do look at the single-family offices, I mean, the diversification play is common across the board. This is the masses. So, you might have some outliers that have done well because they're an expert and they keep investing in the thing that they know. But that is by far the exception to the rule than the rule itself.

I mean, the number of billionaires that invest the way I'm talking about is probably in the 90% quartile, I mean, just based on how many billionaires there are in the percentage of family office data that I have.

Anastasia Koroleva: You mentioned before that you found that faith grounds exited founders and helps through the process. And this is exactly what I found. And it's interesting that even before I found it through interviewing others, I found it through books in autobiographies. I spent years basically reading autobiographies of people who sold businesses to figure out, actually, in their stories what happened to them. And I was fascinated because even people like, say, Steve Jobs, we don't appreciate that there was a lot of spiritual clarity in him even before he started Apple. And when I read his biographies, especially his very detailed biographies, to me, it becomes very clear that this is exactly what helped him later successfully go through one business to another business to another business because he didn't have to go through this horrible existential crisis where he had to question everything under the sun. He had that clarity.

But also, Peter Thiel, another example of somebody with faith and clarity, spiritual clarity, and philosophical clarity. It's really, really fascinating. And in the old days, you see sort of all the exited founders who were very successful with it but then later what I found through my own research and talking to exited founders who are alive, I found that people who come from societies that are still very spiritual, whether it's formal faith or just have a spiritual tradition, they go through their post-exit journeys so much easier.

Justin Donald: Oh, yeah. Yeah. I mean, I think there's a ton of data to support it. I've experienced it in my own life. I know a lot of exited founders as you do. And I know the ones with the strongest faith and when I say strongest faith, not just that they're spiritual, that they actually believe in God as their creator, like those individuals navigate it so much better, so much easier, because the bigger picture I think for a lot of people you have an exit, it's the biggest thing that ever happened to you in life. For people that have a true faith, it pales in comparison to the greatest gift that we've ever been given. And so, I think that just kind of puts it into perspective.

And then it's not about the money, right? If you know that you're loved no matter what, no matter who you are, no matter how you show up, and that you just belong, there is a different type of searching and seeking that you're doing than the person that doesn't have that. Obviously, they've lost their identity, meaning they don't belong, they don't know who they are, they don't feel loved. It was all these things that they did in their business to earn external accolades, and they felt love through that, but that's not real love, right? And so, maybe they're replacing love for connection or however you want to look at it, but I've just found that people with a strong faith really can weather all the storms, both good and bad, in a much more graceful fashion.

Anastasia Koroleva: Yeah. But also, the same is true for people who have very strong support from the family. So, for example, if we talk about ethnic groups, I found that Indians and Orthodox Jews are doing really, really well with their post-exit journeys. And one issue may be more obvious that these are societies that actually have a very strong understanding of what money is for and the tradition for managing money with respect and wisdom. But I think the two other things are very important. One is that spiritual clarity or faith, and the other one is this unshakeable family bonds, right, and having that, as you said, love and belonging, and support.

And those of us who are much more disturbed by the exit, usually at some point come to the conclusion that, “I really need to build a community of my own because, unfortunately, I'm not lucky enough to have that given to me by my family, but now I need to build that family.” And obviously, you and I know of a number of groups where people are trying to create exactly that, brothers and sisters by choice, right?

Justin Donald: By choice. Yeah. Not forced upon you, not a blood relationship, but a pure like these are the people I want. I always say I want to do business with people that I want to do life with. I want to do life with people I want to do business with. I just want it to be all intermingled. And so, that's it. I want to be intentional with who I spend my time with. And by the way, that doesn't mean it has to be the Lifestyle Investor Mastermind or the Tribe of Investor Mastermind. It doesn't have to be those. It doesn't have to be Exit Academy. It can be, but it needs to be something, something that aligns, people that align. We're not just a few people aligned. The majority of the members align in values, in morals and ethics.

Anastasia Koroleva: Yeah, but also in feeling that need and being very aware of that need. Because if we don't feel that need or not aware of it, we are not contributing to that community we're trying to build because I think that's one of the biggest problems with lots of peer groups that either failed or kind of half dead that I've encountered is that people don't contribute. And they don't contribute because they don't feel the need. And then over time, it just falls apart.

Justin Donald: Yeah. We always tell people, "If you want to get into the lifestyle investor, the things that we look for, number one, that you're hungry to learn and grow; number two, that you're eager to give and share of your expertise or things you've learned along the way; and three, that you have humility that you show up, that there's no showboating, no ego. And number four is that you're just kind. You're a kind, loving person.” And that's what we look for. And we have been very strict on that. We have turned away plenty of people. I mean, we have people that have made more money than most people could ever imagine, but they just were not the right fit. They just weren't.

And that it doesn't matter how much money someone has, that doesn't buy you into our community. I'm sure it doesn't for your community. It's got to be the right cultural fit, and those are the things that we look for.

Anastasia Koroleva: No, absolutely. Because you have someone who is there for your own reason, and it spoils the whole community. It's actually very dangerous. It's not worth it. You have to curate.

Justin Donald: Yeah. You have to curate. It's so important. We can't finish this podcast until we at least get to a couple of really key parenting things. What I want to let everyone know, you have just been a wealth of knowledge, an incredible resource on parenting, and I think any parent can say, “Hey, I did this really well and I messed this up.” I mean, I look at you as just a shining example of someone that has parented very well from an entrepreneurial standpoint, has raised a couple of great kids that are independent, highly successful, but have felt loved all the time through it. And it wasn't because you were easy on them. It wasn't because you had kid gloves on all the time. There were tough love moments. And I'd love to hear anything you can share for the parents out there that want to raise successful, loving kids.

Anastasia Koroleva: Well, I wouldn't give anyone advice on how to raise kids. And you heard my opinions because we discussed them in very safe closed groups. Because I think that some of the decisions I made are not for everyone. And for a while, I wasn't sure if I was right. Now, my oldest child is 18. We have three sons. So, they're 18, 16, and 6. And I think about it a lot because I feel the responsibility to raise my third one who is six with all the knowledge and all the experience I could get through from my raising the other two kids. But with the other two, with the older ones, there was a lot of risk-taking.

For example, at some point, I decided I am raising my kids unemployable full stop. And I don't care who says what. I tried employment. I tried financial freedom. I am absolutely sure that if you support a child, any child can find their own way to financial freedom if they just know that's the way. And the way I did it was very simple. I was basically going through the concept of freedom, especially because I have boys, and I think generally, for men, freedom means much more than for most women. That's sort of my personal observation. So, I thought to get to boys, freedom is a very good concept.

So, I was telling them that, yes, they can do whatever they want in life, but they need to make sure they're financially free because if they're not financially free, they're not free to self-realize in any possible way. And I was very determined to keep that position. And sometimes, I could see that schools didn't support that, and they didn't like that. And I needed to keep reiterating it. And at the end of the day, today, I'm very happy I did because my older kid has been financially independent since 13. And it did not stop him. There were tricky moments for me as a mother, because when your child is financially free at 13, when he's exposed to all sorts of temptations, and he's definitely not mature, I went through a period when I was really, really worried and concerned and thought that maybe I made really very bad mistakes there.

But he went out of that period when he was just testing financial freedom in ways that made me uncomfortable. But once he was out, oh my God, everything changed because I talk to him now and he tells me things like, "Mom, I'm no longer driven by money at all. I'm driven by the fact that I know that I have the ability to help other talented people become financially successful because I can start a company. I can bring them as partners who bring some other knowledge, but I know how to make a company profitable. And that's my contribution to the world.” And I'm like, "Oh my God, that's great. I love that.”

Justin Donald: Wow. At 18. Imagine if we knew that at 18. That's incredible.

Anastasia Koroleva: So, with my third one, I'm absolutely determined to keep doing that even though, again, it's not for everyone. And the reason it's not for everyone is because you as a parent need to have absolute confidence in that concept, because you'll be challenged every day. Your kids will come and they'll say, "Mom, why are you so weird? Everybody else thinks I should be a banker.” And you have to know the answers to that.

Justin Donald: Well, I'll tell you, Anastasia, you had said something that just really stuck with me, and that was something to the fact of, I'm paraphrasing now, but something to the fact of with your oldest son, you never wanted him to feel like he's going to get bailed out early if he made a mistake or whatever, like he had to kind of pay for his mistakes. But at the end of the day, he would always have a place to sleep. He would never be out on the street. So, he always had a safety net of at least that, but that you weren't just going to bail out these financial situations that came by.

And I think from that standpoint, you now have the confidence and safety and assurance that worst case I can go live with mom and dad. Like, I've got a place like I'm not going to be homeless, but like, yeah, it is on me financially. I'm going to make these moves and I'm going to make it or break it, and mom and dad are not coming in to bail me out. And I think that is a powerful lesson.

Anastasia Koroleva: But it only works if every day you make sure they know there is limitless, unconditional love, which will always be there. So, for example, with my older kids, I was openly telling them that now is the time to take risks. Do take risks. I also told them, “I promise you, there will be moments you lose all your money. It's going to happen. And that's okay. Just expect it to happen. That's perfectly fine. It happens to every successful person I know,” which is not necessarily true, but sometimes you kind of have to give this reassurance and I love seeing that they're so not afraid of losing all the money, which by the way happened several times. It happened several times.

And I loved seeing that every new time. And you're right. They didn't have to hit the real bottom. There was always this safety. And I think it's great to help kids go through this early on when it feels natural that they can come home to their mom. If they start this process later and they have to do it when they're 35, it's still okay, but it's harder, right?

Justin Donald: Yeah. It'd be harder to come crawling back.

Anastasia Koroleva: Yeah. And then another thing, at about 11 or 12, my kids started asking me, "So, what's my inheritance?” Because you can't really fool them, right? They look at your lifestyle and they're like, you know. And they're like, "What?” And when I heard it for the first time, I was so shocked. I felt so unloved. I was like, "What are you talking about?” And then I realized that it's a fantastic opportunity for me to put the seeds in their head that will grow in the right direction. So, I told them, “I cannot promise you anything because the nature of money is to come and go, and I have no idea if there will be any money left by the time I'm gone. So, it would be very unfair and wrong of me as a mother to promise anything.”

“But what I can promise you,” I told them, “is that I will teach you the skills that will make it absolutely guaranteed that you will always climb out of any financial trouble. And that will be my inheritance. And that inheritance I will give you plenty of.” And I had to repeat it a few times before they completely lost interest in the topic because they realized they're not getting a number. But I think they internalized it. And that's very important to feel that money comes and goes like energy, right? And it's okay if it leaves as long as you know how to bring it back.

Justin Donald: That's beautiful. And by the way, even for adults listening to this, if you can get to the point that money just comes and goes, it is like energy, it is literally a tool to be used, and that's it. And don't put too much emotional baggage or neediness on it. When money can just be a tool and not the end-all, be-all, your life will change. Your life around money will change. So, such great words. Anastasia, where can people learn more about you and what you're up to?

Anastasia Koroleva: So, my academy is at PostExit.com. Easy to remember. And my podcast is called Exit Paradox. It's everywhere.

Justin Donald: Love it. Well, I've had a blast. I want to say we as a community, everyone listening in has had a blast because this was a great conversation. Such wisdom. So many cool things you've done and learned, and you're so open and willing to teach us. So, thank you. We appreciate it.

Anastasia Koroleva: Justin, talking to you is always such a great pleasure. Any excuse to talk to you.

Justin Donald: Well, I'm excited to join your show here.

Anastasia Koroleva: Absolutely. Yeah.

Justin Donald: So, hopefully, not only having people check you out here, but come check out my episode on your Exit Paradox. Well, I love to end the podcast with a question to our audience. So, if you're watching or listening, my question is the same every week. But what is one step that you can take today to move towards financial freedom and really just move towards living a life that you desire that's on your terms, so not by default like most people, but by design with intentionality? Pick one thing that you learned from Anastasia today and put it into practice. Thanks, and we'll catch you next week.

Anastasia Koroleva: Thank you. Thank you, Justin. This was so much fun.