$100M-Net-Worth Retired Founder: Chasing Energy Instead of Money
Episode - 24
$100M-Net-Worth Retired Founder: Chasing Energy Instead of Money
Today's guest has chosen to remain anonymous to ensure the utmost authenticity and vulnerability in sharing his story. Four years ago, he fully exited his business and now describes his life as post-economic. He realized he had a money addiction his entire life and took a radical step to address it—he avoids any money-making activities, focusing instead on activities that increase his energy. In this episode, we focus on how to know what we truly want and whether we have enough.
What We Discussed:
00:00:10: Introduction of the guest
00:00:23: Understanding the guest's journey of addressing his money addiction
00:00:33: The episode focus: What we truly want and whether it's enough
00:00:42: Reflections on personal addiction and happiness
00:01:05: Daily reflections and life assessment
00:01:11: Existential questions about 'rewinding' life
00:01:21: Introduction of the host
00:01:31: Discussion on the guest's anonymity and privacy concerns
00:02:09: Reasons behind the guest’s anonymity
00:03:34: Transition into personal story of the anonymous guest
00:03:50: Guest’s journey after selling their business
00:04:50: Post-exit experiences and behaviors
00:06:15: Shift in lifestyle post-exit
00:08:06: Encouragement to follow genuine personal desires
00:08:11: The journey towards self-understanding
00:10:01: Working with a life coach for personal growth
00:13:27: Identifying and understanding habitual patterns
00:14:01: The struggle with subroutines in the brain that were once successful
00:17:20: Further exploration into habitual tendencies
00:17:35: Understanding the pursuit of money.
00:19:21: Discussing the concept of having enough money
00:20:47: Admitting a money addiction
00:21:14: Finding support in a group post-business exit
00:22:10: Dealing with the aftermath of selling a business
00:24:48: Helping other business founders without seeking financial gain
00:26:10: The role of the "Beyond the Finish Line" group
00:28:07: Reflecting on selling the second business
00:32:57: Finding fulfillment after the business exit
00:35:14: Seeking balance between disengagement and involvement
00:36:55: Learning about patience and setting oneself for success post exit
00:40:30: Discussion about the concept of happiness
00:42:54: Importance of feeling relatable and not alone
00:46:36: Discussion about addiction to money
00:52:58: Living life based on energy chase
00:57:59: Understanding of freedom after financial stability
01:01:20: The fulfillment and energy from contributing and purpose.
01:01:48: Personal growth and self-improvement
01:03:44: Conversations about energy and decision-making
01:04:15: Legacy and inheritance discussion
01:06:36: Talk about providing for children without spoiling them
01:07:03: Personal mental health check-in and progress
01:08:05: Reflections on learning, activation and spiritual journeys
01:09:45: Vision about the four false gods
01:11:01: Giving advice to fellow exited founders.
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Anonymous Guest: [00:00:00 - 00:00:09]
I actively try to avoid things that are taking my energy and if I find myself I'm in a situation where my energy is being sucked from me, I leave.
Anastasia Koroleva: [00:00:10 - 00:00:39]
Today's guest has chosen to remain anonymous to ensure the utmost authenticity and vulnerability in sharing his story. Four years ago, he fully exited his business and now describes his life as post economic. He realized he had money addiction his entire life and took a radical step to address it. He avoids any money making activities, focusing instead on activities that increase his energy. In this episode, we focus on how to know what we truly want and whether we have enough.
Anonymous Guest: [00:00:39 - 00:01:09]
If you can't figure out what you want, you'll just want more. If I would have had the ability to send a tweet to myself right before I exited, it would be, you will miss pursuing an important objective with people you like, respect and trust. Money and sex are the are the two addictions where everyone seems to envy the addiction. You can give your kids too much and ruin them, or you can give them nothing and they'll hate you. When my head hits the pillow at night, I just ask myself, is today a day I would want to relive?
Anonymous Guest: [00:01:09 - 00:01:15]
At some point in the future in my life? Would I rewind this day, or is this a day I would just as soon skip?
Anastasia Koroleva: [00:01:21 - 00:01:22]
Hello, Jeff.
Anonymous Guest: [00:01:22 - 00:01:23]
Hello.
Anastasia Koroleva: [00:01:23 - 00:01:25]
Very happy to see you here.
Anonymous Guest: [00:01:25 - 00:01:31]
Thank you. Thanks for having me and thanks for shining a light on this strange little corner of the world.
Anastasia Koroleva: [00:01:31 - 00:01:46]
You are my first anonymous guest and you and I agreed that you will explain to my audience why you chose to be anonymous and we are not mentioning any businesses you were involved in. We are talking only about you anonymously.
Anonymous Guest: [00:01:46 - 00:01:56]
Yeah, well, the obvious answer would be this guy's a fraud or he's hiding from someone. So feel free to draw your own conclusion. My truth is that.
Anastasia Koroleva: [00:01:56 - 00:01:58]
I know you are not. For what it's worth.
Anonymous Guest: [00:01:58 - 00:02:19]
Yeah, I go by a twitter handle for an account I opened just about three months ago, which is retired founder and a website, retiredfounder.com dot. The reason I'm anonymous is a few things. One is I don't have anything to sell. I am post exit, I am post economic. I'm not chasing money.
Anonymous Guest: [00:02:20 - 00:02:29]
So I don't have any. I don't have a newsletter. I don't do coaching. I don't take equity. I don't take any that I have nothing to sell and I really value my privacy.
Anonymous Guest: [00:02:29 - 00:02:50]
I am someone who I will introduce myself to to anyone who reaches out and meets. I'm not hiding. I can guarantee I'm not anyone you've heard of anyone that's terribly interesting, anyone that was on the front page of any magazines. And I like it that way. The other two things are it allows me to be extremely authentic.
Anonymous Guest: [00:02:51 - 00:03:13]
I'm going to tell you things today my parents don't know. I'm going to tell you things today my kids don't know. And I've just found for my own purpose, I can be more authentic when I'm retired founder than if I'm Jeff, which you feel free to call me. And then the last thing I mentioned is it protects the innocent and the guilty. So I might talk about my old company.
Anonymous Guest: [00:03:13 - 00:03:33]
I might talk about a private equity firm that was the second firm that bought my company. I might talk about someone I know who has a money habit. And I just want to protect those people that are in my life to the extent that I might be sharing something about them that may be flattering or less than flattering. So thanks for accommodating that.
Anastasia Koroleva: [00:03:33 - 00:03:49]
Absolutely. I think it's exciting, especially the part that you'll be authentic and telling us secrets nobody knows. So let's jump right into it. Can you tell me when you sold your business and how you felt right after?
Anonymous Guest: [00:03:50 - 00:04:12]
Sure. I had two exits, and I'll go through the first one quickly. I had a.com business. If any of your watchers are old enough to remember that era that we sold for a million and a half dollars, I netted about a million on that one. And I felt great because I had some money in my pocket.
Anonymous Guest: [00:04:12 - 00:04:40]
And I proceeded to spend a lot of it in bad ways and invest a lot of it in bad ways. Took the remaining chips I had left after making some bad decisions and started a software company in 2003 that we exited in 2017. And to get back to your question on the bigger outcome, it was fantastic. For six months after, after selling, I was really worn out. I needed a rest.
Anonymous Guest: [00:04:40 - 00:04:57]
I spent six months after retiring. I sold the company, majority recap in 17, and I retired in 18. So those first six months were just like heaven. I skied 65 days that year. I spent time doing things that I just never had time to do.
Anonymous Guest: [00:04:57 - 00:05:03]
I listened to music. Anastasia, have you ever listened to music? Like, just listen to music where you weren't doing something else?
Anastasia Koroleva: [00:05:04 - 00:05:42]
Of course. Actually, I talked to a psychiatrist, a friend of mine, just a couple of days ago, and he told me that the reason we feel so happy listening to music is because the music engages our old brain, our reptile brain from millennias ago, and allows our front brain to rest. And that makes us happy. And actually, he was saying, we were discussing post exit journeys, and he said, if anything tells people to do anything that has rhythm in it, music or, you know, breath work or yoga, because as soon as there is rhythm in it, we feel happy. So it's very interesting that you mentioned it.
Anonymous Guest: [00:05:42 - 00:06:06]
Yeah. And music has been a part of my life as a background, but I had never actually sat down and listened. I remember listening to Fleetwood Mac Rumors album, top to bottom, not doing anything else, just sitting there in my, you know, my speaker in front of me and listening to it. It was a really interesting experience. So I had a great six months after my exit.
Anastasia Koroleva: [00:06:06 - 00:06:17]
It does sound like ultimate luxury, doesn't it? Because you have the time and the mood to do that. Beautiful. Okay, what happened next? After six months.
Anonymous Guest: [00:06:17 - 00:06:39]
I did all the things I wanted to do, and I did all the things the world tells you you're supposed to do when you retire. And I could step through these, I'll step through these quickly and feel free to circle back to any of them. The first thing the world at aggregate says, what are you going to do next? What's your next big thing? And it's sort of expected of you, perhaps, to do that.
Anonymous Guest: [00:06:39 - 00:06:55]
And I knew I wasn't going to pursue the next big thing, so I didn't spend too much time with that one. I was an angel investor, an advisor. Hated it. I did nonprofit work, or tried to engage in nonprofit work. Hated it.
Anonymous Guest: [00:06:58 - 00:07:14]
I played a lot of golf. It was okay. But it's not the thing that I want to get up and do every day. And I bought just a whole bunch of stuff, which made me pretty unhappy overall. The things that it seemed like I was supposed to do.
Anonymous Guest: [00:07:14 - 00:07:27]
Oh, and I said, on boards, by the way, for any founders, and I found this across the board, and feel free to be the one that breaks this streak. It was miserable. I'm a founder. I like to do things. I hate to watch other people do things.
Anonymous Guest: [00:07:27 - 00:07:38]
And when you're on a board, you get in a room every three months and watch 6 hours of PowerPoint, and it's just miserable for me. Did any of those sound true to you?
Anastasia Koroleva: [00:07:39 - 00:08:03]
Absolutely. Sounds very familiar. And I regret I wasted so much time and valuable resources, like energy chasing those ideas other people have. It took me years to really start developing the sense of what is genuinely my desire and what is. I'm just copying from others subconsciously.
Anastasia Koroleva: [00:08:03 - 00:08:05]
So I can relate to that.
Anonymous Guest: [00:08:05 - 00:08:06]
Absolutely.
Anastasia Koroleva: [00:08:06 - 00:08:11]
Tell me about your journey, how you got from there to where you are.
Anonymous Guest: [00:08:11 - 00:08:35]
Now, the period where I was accumulating things and trying different things on. Lasted about three and a half, four years. And I have this weird quirk. I have a lot of quirks. One of the ones that I have is I have a hard time being happy because I'm really good at preparing to be happy.
Anonymous Guest: [00:08:36 - 00:09:07]
So we had four houses, and I bought an airplane, a jet. And I was going to be really happy, but I couldn't be really happy because the jet had, you know, this burl wood mahogany, you know, finish in it, and I had to have, you know, titanium to be happy. And we had this great house right on the beach. And so I was certainly going to be happy with that as soon as I got the theater seating done. The theater seating was not right, so I had to get that done, and then I'd be happy.
Anonymous Guest: [00:09:07 - 00:09:24]
And summer of 22, I had finished all of the projects. By then, we had sold the airplane. And I was just thoroughly unhappy. I was thoroughly unhappy and I was bewildered and I was lost and I was frustrated. I was a little mad at the world.
Anonymous Guest: [00:09:24 - 00:09:50]
I was a little mad at myself that I had done all the things that I thought I was supposed to do. I had this moronic vision that somehow I would be, I don't know, jetting around, doing cool things with awesome people every day in the winner's circle of life. And it didn't happen. It was isolating, it was lonely, and it was frustrating. So that was when I hit the ball.
Anonymous Guest: [00:09:50 - 00:09:52]
Summer of 22, and now you're writing.
Anastasia Koroleva: [00:09:53 - 00:10:07]
As a retired founder because you want to share ideas of how to retire. As a founder. Do you mind sharing some of the ideas you think would be the most helpful for my audience?
Anonymous Guest: [00:10:08 - 00:10:36]
Yeah, if your audience are post exit or soon to be post exit founders, I would point them to a paper I assume you have, like, show notes or something you can link to. There's a great paper that's written by a guy named Ag Wasserstein. He'd be a great guest for your show, if you can get him. He's a. Have you read his paper on the entrepreneurs epilogue?
Anastasia Koroleva: [00:10:36 - 00:10:40]
And I know exactly what you're talking about, but do talk about it.
Anonymous Guest: [00:10:40 - 00:11:10]
Yeah. So I guess I wanted to say I didn't become enlightened overnight. I went down a rabbit hole, and I found that paper as a starter. And from that, one of the co authors is a guy named Rick Eigenbrode, who wrote a book called what happens when you get what you want? And I spent a good year and a half just trying to get my head straight about what went wrong and what to do about it.
Anonymous Guest: [00:11:10 - 00:11:37]
Just this bewildering state, like, what happened? This wasn't supposed to happen. So I guess the first thing I would say for your listeners would be, don't fall into the trap of doing the things that the world expects you to do, and don't go buy a bunch of stuff. It isn't going to make you happy. And you may have to just get it out of your system.
Anonymous Guest: [00:11:38 - 00:12:02]
Buy a house, buy a plane, buy a car, buy whatever you want to buy. I've yet to come across someone, and I've had a lot of conversations, I've yet to come across someone who said, you know, what really made me happy was just having a bunch of shit laying around that I have to take care of. Not one. Not a single one. And I'll tell you, I've yet to come across someone who said, you know, I did a bunch of angel investing, and I sure love tracking down those k one s to get a subpar market return.
Anonymous Guest: [00:12:03 - 00:12:05]
And, you know.
Anastasia Koroleva: [00:12:05 - 00:12:07]
Usually for a couple of years, people enjoy it.
Anonymous Guest: [00:12:08 - 00:12:27]
And I should stress as well, run your own race. Run your own race. For others, this may be completely rewarding. I haven't seen any signal from the conversations I've had that that makes you happy. If you find a nonprofit that you want to support and work with, go for it.
Anonymous Guest: [00:12:27 - 00:12:43]
That's. That's great. But if you find as a founder, they move at a pace that is too slow for you, or you have a feeling that you are not making a big enough impact, it's okay. You're not special. If you.
Anonymous Guest: [00:12:43 - 00:13:07]
If you run into this situation, you're not special. You are in the same path that I took, and I believe you took, and some of your other guests have taken that. Where you wind up a little lost and a little confused. And if you're not one of those, I have friends that have retired, and they play golf every day. They play golf in the morning, they have lunch.
Anonymous Guest: [00:13:07 - 00:13:25]
They talk about golf while they're playing golf. They talk about golf at lunch, and then they go play golf again, and then they'll have a cocktail, and they'll talk about the next round of golf. And that's great. I'm super happy for them. Please shoot me in the face if that's what I'm doing for the rest of my life.
Anonymous Guest: [00:13:25 - 00:13:34]
It's just not how I'm wired. So that's what I'd say. Figure out who you are and be that person.
Anastasia Koroleva: [00:13:34 - 00:13:36]
Well, easier said than done, don't you think?
Anonymous Guest: [00:13:36 - 00:13:37]
Oh, yeah.
Anastasia Koroleva: [00:13:37 - 00:13:41]
So if we dig a bit deeper, what helped you understand yourself better?
Anonymous Guest: [00:13:41 - 00:13:43]
I'm still working on it.
Anastasia Koroleva: [00:13:43 - 00:13:50]
I'm sure that's a lifelong journey, but if there's something already that helped you make progress, that would be very helpful.
Anonymous Guest: [00:13:50 - 00:14:03]
Yeah. I think the most progress I made was working with my coach, Rick Eigenbrode. And I have probably 30 or 40 pages of notes from my time with him. And I love that man. He did so much for me.
Anonymous Guest: [00:14:03 - 00:14:20]
And I go back to our first conversation and see the guy that was just. I was angry. I mean, I was really frustrated. I was bitter, resentful. So working through the process with him, and he's an expert in this field, was really helpful.
Anonymous Guest: [00:14:20 - 00:14:51]
And I can give you a couple of takeaway points, because I don't mind just giving the answers to the test, if you want to know the answers to the test, at least for me. And the first one was recognizing the subroutines that my brain was running that made me very successful as a CEO of a software company that were killing me in retirement. And these may sound familiar to you. You may have them, you may not. I think we made a list of ten or twelve of these.
Anonymous Guest: [00:14:51 - 00:15:26]
So, for example, accumulating versus decumulating was a habit. Optimizing was a habit. I don't need to drive across the street to park to save $10 anymore. Being in control versus letting go was a bad habit. My desire to finish whatever I'm doing, whether I'm eating a meal or having an interaction with my kids, to finish what I'm doing, and then get to the next thing, as opposed to living and being in the moment, was a bad one.
Anonymous Guest: [00:15:27 - 00:15:44]
And my personal favorite. My personal favorite from this list is my ability, my uncanny ability to find something that's wrong and fix it right away. And when you're running a software company, you know, we did security, and that's pretty. That's pretty valuable, right? Find.
Anonymous Guest: [00:15:44 - 00:15:55]
Find something that's wrong and fix it. Great. Now go on vacation with that person. And my wife is down the hall. She probably wants to come in, and she'll take over the microphone here for an hour.
Anonymous Guest: [00:15:56 - 00:16:09]
But imagine a guy who's checking into his suite at the four seasons, and I'm on my hands and knees because there's a little fray in the rug somewhere or something. Just something. Just something absolutely ridiculous. And it's like, did you see the ocean? Did you?
Anonymous Guest: [00:16:10 - 00:16:25]
Did you see the ocean? And those things are deep seated. And it's funny. I'm glad to make fun of myself and others. But those things are burrowed in there, and they're hard to undo.
Anonymous Guest: [00:16:25 - 00:16:41]
It's hard to stop chasing money. It's hard to stop chasing the things you're chasing and doing the things that helped you in that. In that pursuit. So I say I'm a work in progress. I would say I'm at the stage now where I can identify when those things are happening.
Anonymous Guest: [00:16:41 - 00:16:56]
I can't cease them yet, but I can see them when they're happening. So that was the first one. And there's one other big answer. I pause because I'm conscious that I've been talking for too long. Do you want to pick at that one, or do you want to get up on the.
Anastasia Koroleva: [00:16:56 - 00:16:58]
No, I absolutely love what you said.
Anonymous Guest: [00:16:58 - 00:16:59]
Okay.
Anastasia Koroleva: [00:16:59 - 00:17:09]
I love what you're saying. If anything, I want you to go deeper and give me even more specific examples, if you don't mind. I think it's fascinating and super helpful.
Anonymous Guest: [00:17:10 - 00:17:11]
Of the routines, like the habits I'm.
Anastasia Koroleva: [00:17:12 - 00:17:34]
Trying to break, for example, other habits that you noticed that were not helpful, give me as many as you remember. And if you succeeded in reversing any of them, or if you maybe decided that you can accept some of them because they can fit into your new life and be helpful in some other ways, I'd love to hear that.
Anonymous Guest: [00:17:35 - 00:17:55]
Yeah. Interesting. So some of these maybe are me and could be leaned into as opposed to push to gets. Probably depends on the situation. I think the one that's most interesting to me is the pursuit of money.
Anonymous Guest: [00:17:56 - 00:18:29]
I have always been chasing money. My entire life, I've been chasing money. And I didn't do this with my therapist, Rick, but I think if I got on a psychologist couch and, and talked about my childhood, I would say that my dad used to go to work really early in the morning before anyone was up. And he'd come home right at dinnertime for 15 minutes, and then he'd go into the basement and work on his office papers. And if I had to guess, it's that my dad worked so much.
Anonymous Guest: [00:18:29 - 00:18:46]
And I love my dad. He's a great man. But it must have been modeled to me that money must be really important if dad spends all of his energy on this and not, you know, playing catch with me. Right. Is this the part where I cry?
Anonymous Guest: [00:18:46 - 00:18:48]
Is it too early to. Is it too early to cry?
Anastasia Koroleva: [00:18:50 - 00:18:51]
Makes a lot of sense.
Anonymous Guest: [00:18:51 - 00:18:53]
So, yeah. And. Sorry. That's just about. That's just about me.
Anonymous Guest: [00:18:53 - 00:19:05]
I'm. I'm a person that's always been about money. I had a paper route when I was ten, deliver newspapers at 430 in the morning for $26 a week. I sacked groceries. I sold things door to door.
Anonymous Guest: [00:19:05 - 00:19:17]
I was a kid that would, like, knock on the door with a flyer like, you know, can I cut your grass? Can I shovel your snow? I was a telemarketer, a survey taker. I was an umpire. I sacked groceries.
Anonymous Guest: [00:19:17 - 00:19:31]
I did anything I could for money. I've always been, always been about the money. And I'm trying to stop that because I have the perfect amount of money. Do you have a view on what the perfect amount of money is as a number?
Anastasia Koroleva: [00:19:31 - 00:19:32]
Do you have a number?
Anonymous Guest: [00:19:33 - 00:19:34]
Nope, it's not a number.
Anastasia Koroleva: [00:19:34 - 00:19:37]
Or how do you define it for yourself?
Anonymous Guest: [00:19:37 - 00:19:38]
It's enough.
Anastasia Koroleva: [00:19:38 - 00:19:55]
Yeah, agreed. But it requires a bit of work to understand what enough is. Not only not only with money, but with many other things, even in relationships. What's enough in terms of expectations from your spouse? Right.
Anastasia Koroleva: [00:19:55 - 00:20:19]
What's enough in terms of your expectations from your children? The concept of enough is extremely important for anyone. But for people in our situation is critical. It defines whether we are going up or we are sort of just staying where we are even going down. In terms of the level of fulfillment in our lives.
Anonymous Guest: [00:20:20 - 00:20:56]
Absolutely. And I've spoken with people who have one 10th of what I have or less that have enough, and they're very happy. And I know people that have more than ten times what I have who seem miserable. So the key back to the point we're on is finding a way to cease that thirst for more money. I say money and sex are the two addictions where everyone seems to envy the addiction.
Anonymous Guest: [00:20:57 - 00:21:08]
And I have a money addiction. I really do. I've always been in pursuit of it, and I'm working hard to cease that by recognizing that I have enough.
Anastasia Koroleva: [00:21:08 - 00:21:13]
Did you find an anonymous group of people with the same problem to support you?
Anonymous Guest: [00:21:14 - 00:21:34]
I have formed an anonymous group of people who I wouldn't want to package it as, you know, money anonymous or something like that. It's not that bad where it's all hell. There are groups all people talk about. But yes, I have a group. It's called beyond the finish line.
Anonymous Guest: [00:21:35 - 00:22:23]
And it's a group of post exit founders who have enough. And they want to talk to other founders who are post exit, post economic. Not about how much money they have, not about how they're going to get the next 10 million, the next hundred million, but to talk about how to maximize the benefit of what we already have for ourselves and for the world and try to connect with the things that are our new purpose and passion. When you have that great big hole in your heart from selling your business and your, you have lost your structure and you have lost your purpose and you have lost your identity. So that's what that group is.
Anonymous Guest: [00:22:23 - 00:22:34]
That's what it talks about. Btfl.org comma, beyond the finish line.org thanks for the, thanks for the plug on that. Small group. Small group. It's very rare.
Anastasia Koroleva: [00:22:34 - 00:22:35]
It has to be small.
Anonymous Guest: [00:22:35 - 00:22:55]
Yeah. It's rare to find someone who has done really well that is willing to shut it off. In my experience, that's the most rare thing. It's not the dollar volume. I guess the group probably ranges from 25 30 million in assets to a couple hundred million in assets.
Anonymous Guest: [00:22:55 - 00:23:11]
It's a wide range, but it's enough. And my coach says I'm going to keep plugging my coach as well. If you can't figure out what you want, you'll just want more. So the point of the group is to figure out what you really want.
Anastasia Koroleva: [00:23:12 - 00:23:13]
Have you?
Anonymous Guest: [00:23:13 - 00:23:37]
I'm working on it. I think the two things that really give me energy and thank you for putting me on the spot and holding me accountable to my own nonsense. The two things that I'm doing, and I use energy as my scoreboard. So not what's going to make me another buck, what's going to give me energy. And I'm happy to be talking to you today, for example.
Anonymous Guest: [00:23:37 - 00:23:45]
Thank you for having me. I have great energy right now. I'm going to have great energy when we finish. I had great energy. Looking forward to having this conversation today.
Anonymous Guest: [00:23:45 - 00:24:10]
So thank you for the energy. It's my scoreboard. The two things I've found that give me energy are working with founders. I think we have a certain wiring or communicate on a particular frequency that's difficult to reach with other people that are not founders. I don't have any science behind that, but I just find, I find all my best friends to be founders.
Anonymous Guest: [00:24:11 - 00:24:42]
And that's along the spectrum of a college kid thinking of dropping out because he or she has a business idea all the way through the beyond the finish line, people who have sold their business and are trying to figure out what's next. I talked to people who are selling their business. I talked to people who were having problems with their business. I talk to people who are, you know, going straight up or going straight down. And the key is I do it for nothing.
Anonymous Guest: [00:24:42 - 00:24:48]
I do it for love. I won't take a dollar. I won't take an option. I won't take a war. I want nothing.
Anonymous Guest: [00:24:48 - 00:25:04]
And so that's helped me separate from that money quest. If, like, there's such a thing as an alcoholic that can't have booze in the house, so I can't have money involved. As I'm, as I'm trying to mentor founders, I'm just not capable of doing it.
Anastasia Koroleva: [00:25:04 - 00:25:13]
It's quite radical, but very clean that you separate yourself from any money making endeavor.
Anonymous Guest: [00:25:14 - 00:25:26]
Yeah, it's a hard habit to break. I think I'm on the right setting. I'm not always. Sometimes discoveries I make are not durable. I hope this is one.
Anonymous Guest: [00:25:26 - 00:25:53]
I feel like this is one that's durable. So I do that@retiredfounder.com. Dot I do that on twittertiredfounder, and I felt nothing but I've received nothing but good response and love from people. It was, I was in Austin last week, week before, and I met a dozen or so people that just follow me on Twitter. And, you know, most people don't speak up or say anything.
Anonymous Guest: [00:25:53 - 00:26:04]
They use their own names. Another reason it's good to be anonymous. And, you know, it was great. It was great to be able to, to connect with live human beings. And I didn't get murdered, which was nice.
Anonymous Guest: [00:26:04 - 00:26:50]
And I have people say, like, oh, you wrote this thing, and it was really, really helpful. So that's been good for me. And then the other thing is the beyond the finish line group, which is currently just post exit, post economic founders, but I believe has a broader application of being a resource and a platform and a place, a community for people who have finished something and are now lost. Imagine being maybe youre an Olympic swimmer or something like that, and you spend ten years to, you have all the structure in the world of your training. You have all the purpose that youre a swimmer and youre trying to win a medal for the United States of America or your home country.
Anonymous Guest: [00:26:50 - 00:26:59]
And you have this identity when you look in the mirror. Im a swimmer. Its what I do. And then it happens. You win your battle, maybe, or maybe you don't, and it's gone.
Anonymous Guest: [00:26:59 - 00:27:49]
And I can speak to this as an entrepreneur where some of the things I wanted to get away from, like that structure, like, oh, man, it's the weekly finance meeting or it's the quarterly board deck or it's the daily sales stand up. I want to get rid of that in my life. And it turned out to be kind of the scaffolding holding things up. And so I think there's a, I think there is a, I may have some purpose in helping. I can't help a swimmer or, you know, could be a police officer or an astronaut or someone who's, you know, completed their task or finished, you know, running a marathon to help understand why you got the thing you wanted and now you're feeling lost.
Anastasia Koroleva: [00:27:50 - 00:28:06]
Yeah. I know that you did not build your at least second business specifically to sell, and the offer to buy the company came to you as opposed to you looking for it. Do you ever regret selling?
Anonymous Guest: [00:28:07 - 00:28:09]
Never. Never for a second.
Anastasia Koroleva: [00:28:10 - 00:28:11]
Why is that?
Anonymous Guest: [00:28:11 - 00:28:26]
I was in it for the money, and I got it. It's an ugly thing to say, but it's true. Here comes authentication. I was in it for the money, and I got it. Do I wish I would have stuck around another year or so?
Anonymous Guest: [00:28:26 - 00:28:43]
Probably. But I was shot, I was tired, and I had the first chunk of money. Then I got hit with a second chunk of money, which was twice as big as the first chunk of money, and then a third chunk of money. But no, I don't regret it one bit.
Anastasia Koroleva: [00:28:43 - 00:28:55]
So would it be correct to say that you achieved your closure by realizing that you were in it for the money, you got the money, and then you want something else, and then that's why you regret it? Would that be correct?
Anonymous Guest: [00:28:55 - 00:29:13]
It would be rational and logical to say that it wouldn't be completely true. What I find, talking to post exit entrepreneurs, it's. I don't know, maybe in some ways it's like a dog, you know, sniffing each other, like, okay, I exited. Yeah, I made this much money. I'm good, I'm here.
Anonymous Guest: [00:29:13 - 00:29:44]
But most of the conversation is about the feelings where most don't make a pristine exit. Most have feelings. Maybe they didn't get treated as well as they thought they would be treated by the acquirer or the private equity firm. Maybe somebody didn't get treated right, or maybe somebody got too much or too little or something that happened. There's a lot of feelings that come along with it that end up, I think, haunting the post exit founders.
Anonymous Guest: [00:29:44 - 00:30:14]
And some of them go back and do it again, even though they have all the money they need. Like, I'm going to go do it again, and this time I'm not going to have this part of the outcome that I didn't like. So, yeah, partially true. The financial. The financial aspect was solved and then solve again times a few, but the feelings persist.
Anonymous Guest: [00:30:14 - 00:30:38]
I didn't get treated very well by the second private equity firm that bought my company. So we exited in 17 and then again in 20, and that company said they were really excited to have the founder involved with the business and then later asked me to not talk in the board meetings. So. And that's fine. It was their company, and they did quite well with it.
Anonymous Guest: [00:30:38 - 00:30:50]
So using my wallet, which was my key metric, they did fine. But how hard is that for a founder to sit in a board meeting?
Anastasia Koroleva: [00:30:50 - 00:30:58]
Maths have hurt quite a bit. It's like seeing your baby abused by someone else, in a way.
Anonymous Guest: [00:30:58 - 00:31:12]
Yeah. I use the analogy of, like, someone that's been on a particular battlefield for 13 years, and a new person comes in and says, you know what we're going to do? We're going to go take that hill. And you say, you know what? That hill looks really good.
Anonymous Guest: [00:31:13 - 00:31:23]
I've. I've seen that hill, and I've. We tried to take that hill five times, but here's what you don't know. There's a machine gun nest. Uh, there are snipers, there are landmines and tanks.
Anonymous Guest: [00:31:23 - 00:31:33]
And by the way, there's nothing up on top of the hill. And they say, be quiet. And that was. That was just me. And that look, that's.
Anonymous Guest: [00:31:33 - 00:31:41]
That's just ego, right? I mean, I sold it. It wasn't mine anymore. That's just ego. But, yeah, absolutely, absolutely hurt.
Anonymous Guest: [00:31:42 - 00:31:57]
It hurts when I go back to my old office building, which, which I own, and I was in. I was in last week, and I'm watching people shuffle around, kind of like, is it Friday yet? And, you know, hurts my heart. Hurts my heart. Because it was a special place that had.
Anonymous Guest: [00:31:57 - 00:32:00]
It had great energy, and now it feels like.
Anastasia Koroleva: [00:32:00 - 00:32:03]
So, Jeff, it wasn't just about money. It sounds like.
Anonymous Guest: [00:32:03 - 00:32:05]
Yeah, yeah. As it turns out. Yeah.
Anastasia Koroleva: [00:32:05 - 00:32:11]
Good catch, if anything, it actually sounds like your closure hasn't quite happened.
Anonymous Guest: [00:32:11 - 00:32:13]
I'm getting closer. I'm closing in on closure.
Anastasia Koroleva: [00:32:14 - 00:32:37]
Closure is a big topic in my conversations, I'm sure in your postex founder community as well. And I found that there are two extremes. There are people who take this radical disengagement approach, and they just completely disconnect from the old business. They don't want to hear about it. They block any communications.
Anastasia Koroleva: [00:32:38 - 00:33:00]
And then there are completely different people who are actually trying to keep the relationships, and they make an effort to continue the relationships with employees and co founders and all of that. Where do you fall on that spectrum in terms of social engagements? With your previous company.
Anonymous Guest: [00:33:00 - 00:33:24]
In the first phase, with the first private equity buyer who is outstanding, will recommend to anyone who's thinking about partnering with a private equity in tech, contact me. I'll tell you all about it. I had a good relationship. I did expect to probably be more involved or more needed or more called upon than I was. I was treated with great respect.
Anonymous Guest: [00:33:24 - 00:33:47]
I could walk into any meeting at any time and be and feel welcome, but I wasn't called in. Maybe quite as much. Maybe I wasn't as important as I'd hoped I would be. So in that case, I was kind of in the middle between radical disengagement and still being involved. And then by the end, I was completely removed.
Anonymous Guest: [00:33:47 - 00:34:01]
And today I'm completely removed from the operation. And I've also sold all of my stock as of 2022. So, yeah, I guess I'm maybe just tethered emotionally some.
Anastasia Koroleva: [00:34:01 - 00:34:09]
So being important was important for you. How do you find satisfaction for that need these days?
Anonymous Guest: [00:34:09 - 00:34:21]
Yeah, a couple of. A couple things come to mind. One is just being useful feels good. Having load to carry feels really good. Spending yourself in worthy cause feels good.
Anonymous Guest: [00:34:24 - 00:34:47]
And the other thing, if I would have had the ability to send a tweet to myself right before I exited, or just had ability to send a ten second message, it would be you. You will miss pursuing an important objective with people you like, respect and trust. That's hard to replace.
Anastasia Koroleva: [00:34:47 - 00:34:47]
Absolutely.
Anonymous Guest: [00:34:47 - 00:34:49]
Yeah, absolutely. It's hard to replace.
Anastasia Koroleva: [00:34:49 - 00:34:52]
So you didn't replace it yet?
Anonymous Guest: [00:34:53 - 00:35:31]
I'm working on it. The my retired founder bit has opened doors for me where I can find that comfortable place where I can do some good and hopefully do some good and feel useful while not getting so overwhelmed that I want to quit. And I talk about spectrums a lot. There's a spectrum in retirement where on one end I could just live this life of luxury and comfort and safety and accomplish nothing. And I think that would be thoroughly dissatisfying to me.
Anonymous Guest: [00:35:32 - 00:36:00]
But I could do it. Sounds pretty good when I say it out loud. And then on the other end of the spectrum is going and doing something really hard again, like starting another company or deciding I'm going to take on climate or homelessness or healthcare, education, something like that. And I'm pretty scared of that side, if I'm being honest. I've observed when failure is an option, it's probably going to happen.
Anonymous Guest: [00:36:00 - 00:36:18]
So I'm trying to find something that's closer to the middle, where I can feel like I can be challenged and be useful, but also have success. And I don't mean to criticize again, run your own race. I don't mean to criticize anyone. My friends that play golf every day, good for you. If you fall into that slot.
Anonymous Guest: [00:36:18 - 00:36:41]
Count yourself, I think is lucky. And for my friends who have retired with vast sums of money and they're going at it again or they're taking on some intractable problem, pat on the back, you know, just happy for you. That's just not me. Do you ever think about your, you know, using my spectrum as an example? Like, hey, that's, I want to do that.
Anonymous Guest: [00:36:41 - 00:36:45]
And it's challenging, but not so hard. It's going to break my spirit, you know.
Anastasia Koroleva: [00:36:45 - 00:37:15]
I'm completely with you. And what you just said now is very similar to what I tell people when they ask me the question. So I'm exactly in that place. But I also do see people who spend some time in the space where you and I are right now. And this podcast is for me a way to be helpful and useful and get that satisfaction without making it as hard as it was building companies before.
Anastasia Koroleva: [00:37:16 - 00:37:53]
But I also met people who spent some time in this space and then they do find usually very naturally, something very difficult to do, but they're so motivated by that time that it actually seems still quite comfortable. And that's what fascinates me. I love meeting these people. I love to understand why and how they got there. And I'm kind of playing with my own reactions to emotional reactions to what they're saying to see, oh, maybe actually that's where I going to be.
Anastasia Koroleva: [00:37:53 - 00:38:41]
But if I learned anything in my 13 years since my first exit, is that letting go and giving things time is extremely important. And for me, for example, my lifestyle is much more about setting myself up for good things to come into my life, as opposed to cheating them like crazy like I did before. But setting yourself up for good things to come is also quite hard work. It's all about those habits you mentioned and making sure that you have the right habits, you have the right attitudes, you have the right mindset. It's a lot of work, a lot of internal work, and then some external work as well, because you have to be very discerning with respect to the people around you because they influence you without you fully realizing it.
Anastasia Koroleva: [00:38:41 - 00:38:56]
So for me that's the whole, that's work in a way, pleasant work, but it's work. But I'm very curious about the future and where it takes me as I'm getting better at creating the system to invite good things into my life.
Anonymous Guest: [00:38:56 - 00:39:19]
Yeah, that's an enlightened, does it make sense? It makes perfect sense. It's a very enlightened view. And I wonder if you would have been able to record that and beam it back to your first exit if you would have listened or not. In some ways, it feels like you have to go through it to get that enlightenment that you have.
Anonymous Guest: [00:39:22 - 00:39:40]
When I talk about the post exit blues, which is the world's smallest violin, it's a tough thing to talk about. It's embarrassing in some way. It's a combination of and embarrassing, which is. There's probably a german word for that, but it's. But it's right in there.
Anonymous Guest: [00:39:42 - 00:40:01]
If. If anyone listening. Let me speak directly to the audience. If anyone listening is thinking, this guy is the biggest moron I've ever heard in my life, and I share. I don't mind sharing because I'm anonymous.
Anonymous Guest: [00:40:01 - 00:40:22]
I have $100 million. If someone were to tell me ten years ago that there's a person out there, he's on a podcast for some reason, today, he has $100 million, and he hasn't found happiness, I can guarantee. Guarantee 100%. I would have said, idiot, get out of the way. Hand me the money.
Anonymous Guest: [00:40:23 - 00:40:29]
Let me show you how this is done. And I just think you got to go through it.
Anastasia Koroleva: [00:40:30 - 00:40:39]
And they would be very naive, because once they get that hundred million, they'll realize that happiness is still a lot of work away.
Anonymous Guest: [00:40:39 - 00:40:58]
It is. Yeah. I was having a conversation yesterday, and we kind of stumbled into this idea that maybe everyone has a comfortable amount of. Let's call it expenses rather than. Than assets, like a comfortable amount of expenses.
Anonymous Guest: [00:40:59 - 00:41:23]
I go back to the last four years or so running the company, where things were going pretty well. I was getting paid well, and we were taking the kids on nice vacations, and we paid off our house, and it just felt pretty good. Right? And so that was, like, the sweet spot. And when you're below that sweet spot and you're scrambling and you're not quite sure if.
Anonymous Guest: [00:41:23 - 00:41:43]
Am I gonna have to sell the house? Can we afford the. To go to the dentist? Whatever that thing is, it's really uncomfortable. The part that is surprising is the discomfort that comes from the gap on the high side, where, you know, so maybe I'm just using numbers as an example.
Anonymous Guest: [00:41:43 - 00:42:18]
So maybe my comfort zone was when I could spend $400,000 a year, a, you know, that's a good amount of expense. And now if I use, you know, the portfolio, you know, Monte Carlo, I need to be spending $2 million a year or $3 million a year if I don't want that number to run away, need to spend it or give it away, and it creates a different kind of discomfort that I can hear myself talk. I can hear people, like, slamming their laptops closed. So if you're still. If you're still here, if you haven't slammed your laptop closed.
Anonymous Guest: [00:42:20 - 00:42:25]
Thank you. But it creates a different kind of, honestly, an unexpected discomfort.
Anastasia Koroleva: [00:42:25 - 00:42:33]
Yeah, absolutely. Absolutely. And I think if. If anyone is still listening, it means that they can relate to that.
Anonymous Guest: [00:42:34 - 00:42:55]
I hope so. And as we talked about recall, I think this is a really important conversation, and I think you have a really important podcast here, and I would love for you to have five listeners that make it to the end of this, or, you know, whatever it is, one listener that makes it to the end and says, I'm not alone. I'm not the only one.
Anastasia Koroleva: [00:42:55 - 00:43:31]
Yeah, no, absolutely. And we talked about it before that. We, both of us, met so many people who have comparable amount of money to you, and then they're still chasing more and going back to that beautiful idea of addiction to money. So many people are not yet at the point where they can say, here I am. I am an addict to money, because the society actually considers it as a good thing that you keep running for it.
Anastasia Koroleva: [00:43:31 - 00:43:39]
And I am so happy for you that you recognize this problem and that you are dealing with it. You're definitely not alone.
Anonymous Guest: [00:43:39 - 00:44:11]
Thank you. Yeah, I won't name the name of the organization. Sounds like you had a different experience with the organization of high net worth people. But I find it sad, disheartening. Maybe I'm projecting my own self, but when you're in a room with someone who has so much resource and they're spending and giving away very little of it, and they're putting their energy to just getting more that they can't.
Anonymous Guest: [00:44:11 - 00:44:19]
Like you can't spend this much. So I guess I better go back and get more. For some reason, not judging, but I just don't understand it.
Anastasia Koroleva: [00:44:19 - 00:45:07]
Well, you know, the explanation I have for it for myself, because I agree with you, it's not necessarily rational if you look at it from the outside, but I think it's actually avoidance, because dealing with feelings and dealing with the problem, and even accepting is a problem is very hard. It's much easier to just follow the momentum to keep doing the same thing. In a way, it's so interesting for us founders, the comfort zone is the hard work of earning money. It is our comfort zone. Getting out of that comfort zone is letting go, relaxing, you know, allowing yourself, not having control, and facing your feelings without judgment.
Anastasia Koroleva: [00:45:08 - 00:45:12]
That's extremely uncomfortable hard work.
Anonymous Guest: [00:45:12 - 00:45:42]
It is indeed. It might be analogous to the human's discomfort with mastering the food supply, um, and which is possibly a reason for the. The obesity epidemic. Like, as a species, we weren't designed to have, like, control our food and, like, have ample food, and, um, the, you know, the. The.
Anonymous Guest: [00:45:42 - 00:46:09]
There's this idea, maybe, that the same thing happens with money, where we have a scarcity mindset. Another one of my habit loops, a scarcity mindset, and it's really, you know, that that's not. That's not. That's, like, low on the brainstem, right? That's way down there that you, as humans, we have a desire to build more, because as cave people or whatever, you know, there was.
Anonymous Guest: [00:46:10 - 00:46:32]
There was never any certainty beyond the. Beyond the day. But I would say, I'll borrow another one of my coach's quotes. You cannot fill a hole with the thing that created it. So if you're chasing that money and you think chasing more money is going to fill the hole, probably not going to work.
Anonymous Guest: [00:46:34 - 00:46:49]
I think you make a really good point. Again, we're in a no judgment zone. If that's someone's purpose, to make more money and they choose to use capitalism as their scorecard and their way of giving back, there's certainly good that comes with it. I just didn't fall in that camp personally.
Anastasia Koroleva: [00:46:49 - 00:47:17]
So if tomorrow you stumbled upon an amazing purpose and you would realize that to be the most efficient in your contribution towards that purpose, you would need to build a business, would that kill the idea for you? Or you would actually consider a business as a form of the most efficient way to achieve something really important, satisfying and fulfilling?
Anonymous Guest: [00:47:17 - 00:47:56]
That's a really good question, and I don't know. I don't know the answer. Like I said, I think I'm an alcoholic that can't have the booze in the house. So I think I would struggle with that, because at my core, I'm so certain that I know chasing more money isn't the thing, but just to not get stuck on that point in a situation where that was the only way would be to invest or have an opportunity to make money, if that were the only way that I could pursue a purpose, then that would have to be considered, right? I mean, how would you not consider that?
Anonymous Guest: [00:47:56 - 00:47:56]
Yeah.
Anastasia Koroleva: [00:47:56 - 00:48:41]
Because most of my guests. I like asking people this question, and most of my guests are saying that they think to realize their full potential and to give their very, very best to the world, they actually have to build another business, because this is where all their talents, all the experience, everything, that's the best that they can offer to the world comes together. But it's interesting, when I listen to you, I wonder if you have a fear of money in a way, because, you know, you're addicted, which may be restricting you in the future or. It's actually not that. It's not a fear.
Anonymous Guest: [00:48:42 - 00:49:12]
I have two different, two different viewpoints on that, and it's a really interesting thread. One is when, when you're, when you're riffing on that person who's saying, well, this is my way of, you know, giving back to the world and maximizing my purpose or whatever, doesn't that sound a little bit like an alcoholic to you or an addict to you? Like, I just, you know, I just need this one. You know, just, there's just this, you know, kind of, I gotta get through the day or I'm gonna be more, you know, socially viable or whatever. The thing is, it just sounds like an addict to me.
Anonymous Guest: [00:49:12 - 00:49:41]
So, you know, maybe a way to look at this is what's a scenario where I would not be able to pursue something because I didn't have an economic upside in it. I give money to, to things, you know, without any expectation. I'm working on a lot of things for founders that I believe is, is, you know, a big, big part of my purpose. What's a scenario where I would absolutely need to be a capitalist pig to pursue that purpose and passion, for example.
Anastasia Koroleva: [00:49:41 - 00:50:27]
To make something sustainable? Say you're trying to solve an important problem, but if you don't make it financially sustainable, then it means that when you're gone, the whole thing falls apart. And you may say, I have the responsibility to build it into an efficient mechanism which produces money to sustain itself, which also supports people who are the best possible people for this cause, right? And then you realize that this is the best way to solve the problem. Would you stop at that point and say, no, no, no, I'm not going there because my addiction will come back.
Anonymous Guest: [00:50:27 - 00:50:57]
I would still, but I'd still say, let's say we came up with an idea to fix the healthcare system today, which would be great. Would it not be possible to pursue it? Of course it's going to require money, but it may not require me taking any money out and say, well, here, let me write a check for a million dollars and I'll help raise more money and I'll help hire people and I'll help develop product and I'll help, you know, do all of the things to accomplish the objective, but I'll never, but I don't have any stock. I don't have any, I don't take a salary. Would that be the same?
Anonymous Guest: [00:50:57 - 00:51:14]
Because I'm not, like, a successful capitalist that's now declaring socialism is the right way. I get money, makes things happen. I think, for me personally, is just needing to detach from a financial outcome for myself, if that makes sense.
Anastasia Koroleva: [00:51:14 - 00:51:34]
Okay, so you're gonna draw the line at where you would take the money out personally. So it's more venture philanthropy, for example, would be a good structure for something like. Like that, right? That it produces money, but only to feed itself to become better and better and better in solving the problem until the problem is solved.
Anonymous Guest: [00:51:34 - 00:51:41]
In this hypothetical, that would be my. That would be my first answer. I have to think through that more, but, yeah, that sounds right to me.
Anastasia Koroleva: [00:51:41 - 00:51:53]
That's amazing. Okay, so your early motivation was money. Your motivation now is having a happy, fulfilling life. Or how would you define it?
Anonymous Guest: [00:51:53 - 00:51:56]
I would define it very simply as chasing energy.
Anastasia Koroleva: [00:51:57 - 00:51:58]
Okay.
Anonymous Guest: [00:51:58 - 00:52:05]
I am working on doing things that bring me energy, and I'm working really hard to avoid things that take my energy from me.
Anastasia Koroleva: [00:52:05 - 00:52:08]
You're turning into an energy addiction.
Anonymous Guest: [00:52:08 - 00:52:10]
Yeah, yeah. And sign me up.
Anastasia Koroleva: [00:52:10 - 00:52:13]
Really sign me up.
Anonymous Guest: [00:52:13 - 00:52:32]
I've been. Since I've been been working with founders and the beyond the finish line group, I've been waking up really early with a bunch of energy, and I only have things on my calendar I'm really looking forward to. I mean, look, we've all got to go to the DMV sometimes. We got to go to the dentist sometimes. It's not like I found some parallel universe, but.
Anonymous Guest: [00:52:32 - 00:52:47]
But I actively try to avoid things that are taking my energy. And if I find myself, I'm in a situation where my energy is being sucked from me, I leave. It turns out no one cares. Not that popular. So that's what I'm.
Anonymous Guest: [00:52:48 - 00:52:55]
That's the. That's the mindset that I have. It's not money that matters. It's energy. And what's better?
Anonymous Guest: [00:52:55 - 00:52:57]
What's better than energy? What's better?
Anastasia Koroleva: [00:52:57 - 00:53:05]
Yeah. Energy is everything, right? We're all made of energy. I'm with you. Absolutely.
Anastasia Koroleva: [00:53:05 - 00:53:28]
So let's talk about specifics. You mentioned that one energizing activity for you is spending time with other founders because we are on the same wavelength or whatever it is. What are other examples that you found for you personally that are energizing?
Anonymous Guest: [00:53:28 - 00:53:50]
I do like to a lot of recreational things. I do like to play golf. I do like to mountain bike. I do like to ski. I like to do things for fun and to be silly, I don't like to be overly serious about anything I do, as I've read some psychology books about reconnecting with the person you were at birth.
Anonymous Guest: [00:53:51 - 00:54:20]
And then society pulls you away from that particular individual and says, this is your, this is your job to go make money or to go, you know, solve crime or whatever. You know, whatever the thing is you're, you're called to do to try to get back to that silly kid. And so those are, those are things that give me energy as well. I have friends that I play golf with that we just have a great time because we could care, really care less about the golf. We're goofing and making fun of each other.
Anonymous Guest: [00:54:20 - 00:54:41]
And that, that gives me great energy, too. Having, having interesting conversations with smart people, like now is, is really, is very energetic for me. And then, and then I like the little things, too. I'm not, I'm not that complicated of a person. My wife and I eat lunch and dinner together almost every day.
Anonymous Guest: [00:54:41 - 00:55:00]
We play backgammon. And if you're listening, my wife, who I will not name, I'm going to beat you at our lunch game, which is going to start here in an hour. So that gives me good energy as well. You know, sometimes it's the simple thing. Sometimes it's reading a book, sitting quietly, listening to music.
Anonymous Guest: [00:55:02 - 00:55:04]
I'm not. You don't need to make it too complicated.
Anastasia Koroleva: [00:55:05 - 00:55:24]
Did you find that you questioned, questioned some of the most foundational concepts in your life, like freedom or meaning, success as part of this process? And if so, how did you change your view on those concepts?
Anonymous Guest: [00:55:24 - 00:55:49]
The concept that turned out to be bunk for me was the happily ever after paradox, and they rode off into the sunset and lived happily ever after. And when you're a founder and you're in the grind, you're like, yeah, that's awesome. Riding off into the sunset. What could be better than that? But no one ever asks.
Anonymous Guest: [00:55:49 - 00:56:13]
But then what happened, let's say, three years later on a Thursday afternoon, what happened then? What happened when someone sprained their ankle? What happens when the smoke detector starts beeping at 02:00 in the morning? Is it still happily ever after? This is embarrassing as well, but in a way, I had this foggy vision that somehow the universe would treat me differently or I would be.
Anonymous Guest: [00:56:13 - 00:56:33]
I don't even know how to describe it, but it just felt like, well, certainly when I have all the money, the problems will, will be gone as well. And I guarantee my smoke detectors still go off at 02:00 in the morning. They never go off at two in the never go off at 02:00 in the afternoon. My smoke detectors and the person at the DMV could care less if I have a nickel or all the money in the world. So that was.
Anonymous Guest: [00:56:34 - 00:56:45]
That was one that. I'm not proud to say that, but it just, like, who knew you didn't just ride off into the sunset and live happily ever after every day for the rest of your life?
Anastasia Koroleva: [00:56:45 - 00:57:00]
So I'm sure that changed your definition of success, because it sounds like it was tied to money before, and then it's tied to energy. So your day is successful if you got more energy than you actually spent. Right? Would that be.
Anonymous Guest: [00:57:02 - 00:57:17]
Yeah, if I had to. If I had to pick one, I would. I would pick energy. I run this model I call the rewind day check, which is, my head hits the pillow at night. I just ask myself, is today a day I would want to relive at some point in the future in my life?
Anonymous Guest: [00:57:17 - 00:57:45]
Would I rewind this day, or is this a day I would just as soon skip? And I had a lot of skip days in the middle where just like, I felt like I was. I was preparing to be happy. I was trying to figure something out, and I haven't had any, anything but rewind days of late. And I would suggest to anyone, if you wanted to try that experiment, if you have too many skip days in a row, change gears, change gears, do something different.
Anastasia Koroleva: [00:57:45 - 00:57:59]
So let's talk about freedom. I assume you felt that you achieved freedom after your complete exit, after you finally left the company. What are your thoughts on freedom today?
Anonymous Guest: [00:57:59 - 00:58:15]
Freedom is the thing we all seek, financial freedom and independence and fu, money, or whatever you want to call it. And we're so fortunate. Gosh, I should just take a curve out here. Feel free to edit. But how fortunate we are.
Anonymous Guest: [00:58:15 - 00:58:44]
How fortunate I've been. I stood on the shoulders of my grandparents, who were farmers and factory workers, and my dad was a middle class office white collar worker. My mom stayed home, and my wife is loving all that. I'm just so lucky to have an opportunity to be in a capitalist free society. It's not a perfect world, but how lucky we were to have the fundamental freedom to pursue that ultimate freedom of, I'm going to wake up and do whatever I want to do today.
Anonymous Guest: [00:58:45 - 00:59:20]
When you get to the back half of that, where you have close to infinite options, there can be some drawback as well. Maybe you've experienced this. When you can have anything you can do, you know, within reason, you can kind of do whatever you want with your time and with your, your resources can, can also be a little vexing. You've probably read the paradox of choice, which, which was a, you know, ideally you just have, you know, one or two choices, and you pick that one. And when you have a thousand, you're more likely to be unhappy than if you just had the two.
Anonymous Guest: [00:59:21 - 00:59:24]
So it's a beautiful double edged sword.
Anastasia Koroleva: [00:59:24 - 00:59:58]
I found it took me years to master freedom management. I never expected it would even be an issue that it even existed, because I really was so motivated by freedom my whole life. And then I was overwhelmed and had no idea what to do with it and couldn't find direction and wasted a lot of energy chasing many goals all at the same time. And that's actually how I learned to appreciate energy. It was through struggling with too much freedom.
Anastasia Koroleva: [00:59:59 - 01:00:13]
And then I figured, okay, how about I take all this energy, I channel it somewhere? And this is when the question, what is it I actually want? Becomes very important. Because then you think, where do I channel it? Say, I can pull it all together.
Anastasia Koroleva: [01:00:13 - 01:00:23]
I can say no to many things, but where do I go? What is it I really want? I found that quite complicated.
Anonymous Guest: [01:00:23 - 01:00:32]
Yeah, well, you've proven beyond a reasonable doubt. You're the more interesting guest here. So tell me all about it. How did you. Is this a system?
Anonymous Guest: [01:00:32 - 01:00:39]
Have you written about this? Is this something that you could help describe your process for me and others?
Anastasia Koroleva: [01:00:40 - 01:00:56]
Well, I'm very much. I'm a big believer in what you're saying. Picking our activities based on their effect on our energy. And I'm religious about analyzing all the time. Is it energizing me or am I training energy?
Anastasia Koroleva: [01:00:57 - 01:01:33]
And it became so much of a habit that decisions became very easy over time. But in terms of channeling my energy, I think this brings us to purpose and the sense of purpose, because I only feel really fulfilled and deeply energized if I feel that I am contributing. So this is when I think there was a big growth for me. So, for example, this podcast gives me a lot of fulfillment because I feel I'm contributing. I can be helpful.
Anastasia Koroleva: [01:01:33 - 01:02:00]
I can bring people like you and give you platform to share your wisdom. Every time I'm done with an interview, I'm so energized. It's like it's early morning, so there's no question about that. And then growth, the sense of personal growth, becoming a better person as a direction, really energizes me. And understanding that I'm a better person than I was before.
Anastasia Koroleva: [01:02:01 - 01:02:13]
All these things I didn't understand earlier in my life, like working on virtues very intentionally, just to become a better person is actually extremely energizing.
Anonymous Guest: [01:02:13 - 01:02:33]
That's great. Thank you. Would you say that's become ingrained in you now, or do you still have to launch that mental process when you're. Maybe you're making a decision, someone invites you to lunch or to, I don't know, to do something. Is it natural to you now or do you have to stop yourself sometime?
Anonymous Guest: [01:02:33 - 01:02:37]
Like, well, that's chasing something. That doesn't bring me energy.
Anastasia Koroleva: [01:02:38 - 01:03:00]
It's becoming easier and easier. It's the power of a habit, right? Our brain also has this habit. Sometimes I like to make exceptions because sometimes it's very nice to just go with the flow and the feeling. I'm generally a very spontaneous person, so if anything, I actually need to restrict my spontaneously.
Anastasia Koroleva: [01:03:00 - 01:03:13]
But sometimes I feel, okay, I don't know this person, but I don't know what. I don't know. I'm curious enough. I'll go, I'll spend some time with the person, and then we'll see. And by now, more often than not, I'm pleasantly surprised.
Anonymous Guest: [01:03:13 - 01:03:16]
Oh, great. Are you good at walking out? Can you walk out?
Anastasia Koroleva: [01:03:16 - 01:03:27]
Well, if it's a big group, it's very easy for me. I just disappear. Yeah, I'm very good at that. My husband always laughs at me. I'm a master of disappearing.
Anonymous Guest: [01:03:27 - 01:03:31]
Yeah. Yeah. It's a gift. It's a gift. It's harder to do.
Anastasia Koroleva: [01:03:31 - 01:03:35]
The minute I'm not energized, I just disappear into the thing I am.
Anonymous Guest: [01:03:35 - 01:03:38]
Good for you. It sounds so simple. But it can be difficult to do.
Anastasia Koroleva: [01:03:39 - 01:03:42]
In a one on one. It's much harder, obviously, for all of us.
Anonymous Guest: [01:03:43 - 01:03:48]
Thank you for sticking around. I appreciate you wanting to leave right now. Is your energy draining from your body as we're speaking?
Anastasia Koroleva: [01:03:48 - 01:03:52]
But can I become the host again? Can I keep asking you questions?
Anonymous Guest: [01:03:52 - 01:03:53]
Yeah, sorry. Sorry.
Anastasia Koroleva: [01:03:53 - 01:03:54]
I find it much more fascinating.
Anonymous Guest: [01:03:55 - 01:04:05]
I'm a teacher, I'm a student, and the only reason I know anything is having conversations. But, yes, please. I'll get back on the therapist sofa here.
Anastasia Koroleva: [01:04:06 - 01:04:16]
I'll let you go soon because I know I've been abusing you for too long, but there are a couple of questions I have to ask. How do you think about legacy?
Anonymous Guest: [01:04:17 - 01:04:20]
Well, it's fine that we're running short on time, because I don't.
Anastasia Koroleva: [01:04:22 - 01:04:23]
I thought you would say that.
Anonymous Guest: [01:04:24 - 01:04:53]
I like to think. And again, if that's important to someone, I don't need my name on a building. I don't need to be remembered across generations. I would like to think that the people that are in my life while I'm living would say I gave more than I took. I was honest, I was fair, and hopefully taught as much as I learned, and that's fine for me.
Anonymous Guest: [01:04:53 - 01:05:06]
I'd like to provide for my family within reason, not too much, not too little, and have a net positive effect on the universe. And I'm happy with that if I can achieve that.
Anastasia Koroleva: [01:05:06 - 01:05:08]
So you have three adult children?
Anonymous Guest: [01:05:09 - 01:05:10]
Yes, three adult children.
Anastasia Koroleva: [01:05:10 - 01:05:17]
How do you think of them and inheritance and giving wealth to them?
Anonymous Guest: [01:05:17 - 01:05:37]
Yeah. Well, step one is, I hope they don't find this podcast. So if you guys did, I was lying about the 100 million, okay? That was all a fraud. We're struggling with this, I think, like everyone else, because the choice is really two, you can give your kids too much and ruin them, or you can give them nothing and they'll hate you.
Anonymous Guest: [01:05:37 - 01:05:48]
I think that's a Charlie Munger line. So he chooses to ruin them. Charlie passed away recently, but a wise man. And I think if we. If I were to.
Anonymous Guest: [01:05:51 - 01:06:33]
If I were to come up with a structure today, I think that makes sense, would be to have some type of a facility that would provide absolute safety for them in the event when we're gone, but not so much that they're living a flush lifestyle. We also subscribe to the idea that once our kids show they have financial responsibility, we help them now, because if all goes well, my wife and I are going to live to be 90 or 100, probably. And what good does it do a 65 year old kid who's not a kid at 65 to get a big pile of money? So we do believe in always for you. Yeah.
Anonymous Guest: [01:06:33 - 01:06:47]
Yeah. So that's, that's it. I don't have a. I'm desperately wanting to turn the microphone around on you and ask if you've solved this. But that, that's my, my best answer is it does vary by kid right there.
Anonymous Guest: [01:06:47 - 01:07:03]
There are people who receive an awful lot and thrive and live, live beautiful lives, and then there are people that just have like a, you know, enough sustenance income that they fail to thrive at all. So I wish I had the answer.
Anastasia Koroleva: [01:07:03 - 01:07:12]
Have you had mental health diagnosis? Since you've been very honest and vulnerable, I figured I'd ask.
Anonymous Guest: [01:07:12 - 01:07:42]
Yeah, the only therapy I've ever done was Rick Eigenbrot, which I, who I hired in 2022. And I'm not sure if that was therapy or coaching or psychoanalysis or whatever it was, but he certainly helped me unpack those things that were jamming me up, but I don't currently go. Rick and I have become friends, so we do talk, but I don't have a therapist that I go to on a regular basis, if that's what you're asking.
Anastasia Koroleva: [01:07:42 - 01:07:51]
Is it because you ignored mental health for your whole life, or is it because you genuinely believe that you are healthy mentally and have always been?
Anonymous Guest: [01:07:51 - 01:08:11]
I've never thought about that. It's a good question. There's a voice I hear in my head sometimes that says, stop studying and analyzing and just go activate what you've already learned. Because I've come a long way. I've got a pretty clear view of what's in front of me.
Anonymous Guest: [01:08:11 - 01:08:42]
Do I really need to go on a ayahuasca voyage or to a spiritual retreat or sit in silence for a week? Maybe? I mean, maybe I would pick something new up, but I feel like I've got enough tools right now to go forward, and I feel like I'm on a good path. So part of me thinks maybe don't get confused with a new mantra or a new observation about who you are, what went wrong, what you should be doing, what's your purpose, what's your identity? So I don't know.
Anonymous Guest: [01:08:42 - 01:08:46]
Did that sound like I was avoiding something when you ask, that feels right to me?
Anastasia Koroleva: [01:08:46 - 01:08:57]
No. No. It's a beautiful answer. So does it mean that you haven't done any of these things? Silent retreats or psychedelics?
Anonymous Guest: [01:08:57 - 01:09:14]
I have not done a silent retreat. I have done, like every founder I know, I've done psilocybin twice, and it was great. It was great. It was very lightning. I don't know much time we have, but it was very useful to me.
Anastasia Koroleva: [01:09:14 - 01:09:15]
You'd recommend it?
Anonymous Guest: [01:09:15 - 01:09:27]
I wouldn't recommend it because it's illegal. Most places, including the place I did it, I had. Just. For what it's worth, I had. My wife was present, but not in the room.
Anonymous Guest: [01:09:27 - 01:09:45]
I said, hey, look, if I come down and tell you I'm gonna fly the helicopter across town, would you remind me? I don't have a helicopter, because I didn't know what would happen. And the, you know. So the first one was more of an experiment, and the second one was much more telling, revealing, I think, for me. And the short story of it, uh, if.
Anonymous Guest: [01:09:45 - 01:10:05]
If you want to hear it, is, uh, I had a vision of what's called the, uh, the four false gods. Are you familiar with this? It's a Thomas Aquinas concept recently surfaced by Arthur Brooks, where, as humans, we're. We're drawn to, uh, money, pleasure, power, and fame. And so I was.
Anonymous Guest: [01:10:05 - 01:10:16]
I wasn't thinking about this. I wasn't even aware that I had read about this. It just. It just manifested, and I felt these. These four dark forces that were pulling me and a light force above.
Anonymous Guest: [01:10:17 - 01:10:31]
Yeah, I was on magic mushroom, so take this for what it's worth, but the. The light that was above the. The water line was people and purpose and get away from these things that are. That are. Sorry, you don't need no more, you know, money, pleasure.
Anonymous Guest: [01:10:31 - 01:10:39]
I don't care at all about, uh, power or fame. Don't care. What I'm striving for is people and purpose.
Anastasia Koroleva: [01:10:39 - 01:11:01]
I think that is such a beautiful moment for us to finish this conversation, to wrap things up. I just want to ask you, is there any other piece of advice or idea that we haven't mentioned that you think would be helpful for fellow exited founders?
Anonymous Guest: [01:11:01 - 01:11:20]
I think we covered a lot of it. I think if you. If you wind up in a weird spot, you're probably not alone. It's a small community, but if any of this made any sense or some. Some version of it, there's a good chance you're not alone.
Anonymous Guest: [01:11:20 - 01:11:26]
That's the. That's the advice, I would say. You're not alone. And don't be, you know, don't be afraid. I mean, I'm putting myself out there, and I think that's why.
Anonymous Guest: [01:11:27 - 01:11:44]
That's why we're talking. Maybe people are drawn to the retired founder, Twitter account or website or whatever it is, is just. I'm authentic, and I was scared to death to put myself out there. Maybe I still am. And remaining anonymous, but the response I got was so great.
Anonymous Guest: [01:11:44 - 01:11:52]
It was just so great. Don't be. You know, your mileage may vary, but if something out there, put yourself out there, and there's a good chance you're not alone.
Anastasia Koroleva: [01:11:52 - 01:11:57]
Brilliant. Thank you so much, Jeff. I really, deeply enjoyed this conversation.
Anonymous Guest: [01:11:57 - 01:12:02]
It was great. Thanks for having me, and thanks for doing this work. Yeah, I really enjoy the podcast. Thank you.
Anastasia Koroleva: [01:12:02 - 01:12:04]
Thank you so much. Have a good day.
Anonymous Guest: [01:12:04 - 01:12:04]
You too.
