Bill Flagg. Five Exits Later: Pursuit of Inspiration

Episode - 36

Bill Flagg. Five Exits Later: Pursuit of Inspiration

 
 
 

Bill Flagg. He spent 20 years building five incredibly successful tech businesses, then unexpectedly sold them all.

To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life.

Two years ago, Bill moved with his family from Colorado to Portugal with no plans of returning anytime soon.

Today we discuss this transformation, his craving for inspiration, creativity, simplicity, and soul-nourishing experiences.

What We Discussed:

00:00:12: Introduction of Bill Flagg and his career

00:00:22: Bill's transition from business building to seeking simplicity

00:00:45: Bill's move to Portugal

00:00:53: Overview of the episode's discussion topics

00:01:06: Interview begins with Bill Flagg

00:01:30: Bill's background in creating businesses

00:02:05: Bill's involvement with Reg Online and its growth

00:02:28: Bill helping other entrepreneurs grow their companies

00:03:08: Bill's final company and shift to a new chapter

00:03:39: Bill's life decision to stay in Europe

00:04:43: Bill's recognition of needing a new chapter

00:05:02: Bill's motivations beyond financial gain

00:06:31: Bill's current creative pause

00:07:06: Importance of taking a pause for discovering inner creativity

00:08:18: Bill's new adventures and learning experiences

00:09:00: Rediscovering joy and midlife awakenings

00:09:30: Inspiration from the book Siddhartha

00:10:19: Rediscovering different aspects of self

00:11:21: Embracing a new cycle of creativity and exploration

00:12:02: Bill's joy in creating things others haven't seen

00:12:15: Transition to life in Europe for better work-life balance

 

00:13:22: Bill's fears and emotional state after stepping away from business

00:14:34: Enjoying the simple pleasures of life in Europe

00:16:09: Acceptance of moving on from the startup ecosystem

00:16:28: Planting seeds for discovering new creativity

00:17:13: Excitement about collaborating and creating in community

00:18:22: Inspiration from the documentary "We Are the World"

00:19:11: Exploration of creativity in a non-transactional context

00:20:16: Pausing philanthropic activities for true inspiration

00:21:42: Realizing the importance of sincere giving

00:22:27: Discoveries about post-exit emotional and financial challenges

00:23:07: Psychological recovery after a significant business exit

00:23:49: Reasons for common mistakes and their impact

00:24:10: Early career struggles and finding focus

00:25:20: Personal struggles with relocation and possessions

00:26:27: Adjusting after selling a business

00:27:57: Redefining retirement and identity

00:29:00: Thoughts on identity and discovery

00:30:32: Concerns from exited founders about family perceptions

00:31:20: Final thoughts and conclusion


  • Bill Flagg: [00:00:00 - 00:00:12]

    You start a new cycle that goes back to zero again, in a way. And I think that's what midlife awakenings are about. And sometimes it feels like a crisis because everything is changing. 


    Anastasia Koroleva: [00:00:12 - 00:00:31]

    Bill Flagg, he spent 20 years building five incredibly successful tech businesses, then unexpectedly sold them all. To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. 


    Bill Flagg: [00:00:31 - 00:00:45]

    So passionate about what I was doing for so many years, and that passion was dying out. And the conversations were feeling repetitive, and I wasn't finding creative joy in it anymore. 


    Anastasia Koroleva: [00:00:45 - 00:01:09]

    Two years ago, Bill moved with his family from Colorado to Portugal, with no plans of returning anytime soon. Today, we discuss his transformation, his craving for inspiration, creativity, simplicity, and soul nourishing experiences. Bill, thank you so much for joining me today. 


    Bill Flagg: [00:01:09 - 00:01:10]

    Great to be here. 


    Anastasia Koroleva: [00:01:11 - 00:01:17]

    So your current LinkedIn profile has exactly one sentence on sabbatical in Europe. 


    Bill Flagg: [00:01:17 - 00:01:18]

    That's right. 


    Anastasia Koroleva: [00:01:19 - 00:01:36]

    You also look great, and I know you're quite happy to be in Europe, but I also happen to know that you've sold five companies before you deserved your sabbatical. So I would love to hear that story. If you can briefly tell me about those businesses, how you exited them and when, and then we'll focus on what happened afterwards. 


    Bill Flagg: [00:01:36 - 00:03:43]

    So I've been creating and building businesses, I mean, since middle school, basically. And so it's been a lifelong dream and passion, and I thought I would do it until the day I died. But I started getting involved with mostly tech companies. Software as a service primarily. And in 2007, I got. Well, in 2003, I got involved with a company called Reg Online. It was really my first real tech company. And online registration for conferences and events. We grew it. My partner had started the company a couple years earlier. We grew it ten x and in 2007 we sold it. I took the money from that and started getting involved with other entrepreneurs, primarily self funded companies that didn't raise outside money and help those entrepreneurs grow those companies. 1020 30 x. When I got involved, and in the last couple of years, for varying reasons, with each company, my goal was to continue growing them indefinitely. And for various reasons, for each one, we sold each of the companies. I only have one company left. It's a kids adventure camp company. So it's more of a social good business. But I came to realize that I was ready for a new chapter, an entirely new chapter. And one of my lifelong dreams was to live in Europe. We decided as a family to come do that for a year. And I got bit by the bug. And I said, I don't want to go back to the US. And so now we're living sort of more longer term here in Europe and Canada. 


    Anastasia Koroleva: [00:03:43 - 00:03:46]

    So when did it start your sabbatical? Officially? 


    Bill Flagg: [00:03:46 - 00:04:00]

    I'd say after the completion of the sale of my biggest company survey. Gizmo Elkomer was the name. And we completed that transaction two years ago. 


    Anastasia Koroleva: [00:04:00 - 00:04:01]

    Two years? 


    Bill Flagg: [00:04:01 - 00:04:10]

    Yeah. And so, yeah, I'd say that was really before that. It was sort of the run up. As my other company, we were selling my other companies. 


    Anastasia Koroleva: [00:04:10 - 00:04:18]

    So you said you were ready for the next chapter. What did it mean for you at the time? How did you recognize you were ready for the next chapter? 


    Bill Flagg: [00:04:18 - 00:04:38]

    I was so passionate about what I was doing for so many years, and that passion was dying out, and the conversations were feeling repetitive and very repetitive. Like, I wasn't. I wasn't finding creative joy in it anymore. 


    Anastasia Koroleva: [00:04:39 - 00:04:43]

    So essentially, it was no longer inspiring for you. 


    Bill Flagg: [00:04:43 - 00:04:43]

    Correct. 


    Anastasia Koroleva: [00:04:43 - 00:05:01]

    Which is actually really interesting, because most people just say I got burnt out sometimes. Some people say my motivation has changed because I no longer wanted to chase money, financial freedom, all these goals were gone. But for you, it was more about inspiration. 


    Bill Flagg: [00:05:01 - 00:05:06]

    Yes. I never did any of it for the money. 


    Anastasia Koroleva: [00:05:06 - 00:05:07]

    Okay. 


    Bill Flagg: [00:05:07 - 00:05:08]

    It was. 


    Anastasia Koroleva: [00:05:08 - 00:05:09]

    What did you do it for? 


    Bill Flagg: [00:05:10 - 00:06:31]

    I loved using business building as a creative platform as a way to engage my creativity on how to best serve customers and how to inspire employees and I, and how to create great cultures and organizations. And it became more and more. I became further and further away from the process of doing that as the companies grew and as we had, you know, bigger executive teams and as I had less ability, you know, real ability to engage in the way that I originally did as a hands on entrepreneur, I did it more so. And it was. It was for a while, I was engaged with my partners in helping inspire them to do that, the original founders of the businesses. And so that was inspiring to pass on what I had done hands on operationally, and to do that with them. But then they started handing it off to hired executive teams, and so then became another part removed. And that's the part where I just didn't feel I had. I was solving problems, but not, didn't have the creative inspiration. 


    Anastasia Koroleva: [00:06:31 - 00:06:33]

    So how do you channel your creativity now? 


    Bill Flagg: [00:06:33 - 00:06:50]

    I'm in a relative pause to create the space to discover what's next creatively. 


    Anastasia Koroleva: [00:06:50 - 00:07:16]

    You have no idea how happy I am to hear that, because I actually think most of the problems I see come from people not doing that and jumping straight into a new activity or trying to become the world's best investors, but never taking that pause. And then years later, they realize that they're just miserable because this inner creativity never found the right channel. 


    Bill Flagg: [00:07:16 - 00:07:17]

    Yeah. 


    Anastasia Koroleva: [00:07:17 - 00:07:18]

    And it's cool you're doing that. 


    Bill Flagg: [00:07:18 - 00:07:40]

    Thank you. It's not easy. It's uncomfortable at times because being so passionate, driven, focused, and having so much activity with so many companies really gets me up, gets me going in the morning, and to wake up in the morning and kind of feel the blankness is scary at times. 


    Anastasia Koroleva: [00:07:41 - 00:07:42]

    Do you feel bored? 


    Bill Flagg: [00:07:42 - 00:07:51]

    I don't feel bored. I would say the word is sometimes anxious. Yeah. I'd say it's uncomfortable at times. 


    Anastasia Koroleva: [00:07:51 - 00:07:54]

    So why are you doing it if it's uncomfortable? 


    Bill Flagg: [00:07:54 - 00:08:59]

    Because I feel like it's part of the unwinding process to let. It's not entirely just about that. There's also something that shifted in me in terms of connection with others and being able to play in a different way, in a non transactional way, in a non value generation way, in a. Going on adventures around Europe with. With my family and with. With friends and. And learning, becoming a beginner again at sports like surfing and sail racing and paddle and to. And to end. And so I feel. I do feel like I've sort of reverted. I just. I'm turning 54 this year. I do feel like. And I heard from someone that once you turn 50, you sort of revert to your, um, to being, uh, zero. Like being one years old again. Like you sort of revert. So, in a way, I feel like I'm a bit of a, you know, five or six year old kind of discovery. 


    Anastasia Koroleva: [00:08:59 - 00:09:01]

    In a child. You're connected. 


    Bill Flagg: [00:09:01 - 00:10:45]

    Yeah. My inner child is kind of you. You start a new cycle that goes back to zero again, in a way. And I think that's what midlife awakenings are about. And sometimes it feels like a crisis because everything is changing. There's discomfort, but there's also joy in that. Discovering again. Discovering. As a complete novice, I see your statue over there, and it reminds me of. Of the book Siddhartha by Herman Hess. And that book has been a really great inspiration for me this year, so much so, I hosted a dinner with a whole group of friends with that as the topic, where we each spoke to what came out of reading that book together. And for me, Siddhartha is a book about chapters in life and how we can be so many different things in the course of our life, and then stepping into something that we don't know and that we don't know who we are in it, and rediscovering a different aspect of ourselves. And so that's what I'm excited about now, just sort of rediscovering myself so much so that I keep trying to shed, like, when things pop up from the past or I have to, you know, deal with even investments or estate planning or things like that, I'm just like, ugh, this is not what I. Yeah, like, I don't even. I don't even want to, you know, that. That, that's like this old energy in a way. 


    Anastasia Koroleva: [00:10:46 - 00:10:46]

    Yeah. 


    Bill Flagg: [00:10:46 - 00:10:51]

    That I don't really want to play in, but I have to, have to be an adult at times because. 


    Anastasia Koroleva: [00:10:51 - 00:10:59]

    Yeah, well, I guess you could embrace it as a duty, which is a positive source of motivation. 


    Bill Flagg: [00:10:59 - 00:11:01]

    Duty, that's an interesting word. 


    Anastasia Koroleva: [00:11:01 - 00:11:24]

    So someone I interviewed a couple of weeks ago called it a rebirth when he went through it, and it took him, I believe, 13 years of lots of mistakes and kind of going down and then going back up and then looking back, he calls it a rebirth. But you seem to be doing it faster. 


    Bill Flagg: [00:11:24 - 00:11:31]

    I don't know if I'm doing it faster. I tend to be in an instigation phase. 


    Anastasia Koroleva: [00:11:31 - 00:11:44]

    You're exploring what else is out there besides building businesses, which you really enjoyed, but now ready to move on. Is that correct? Which makes a lot of. 


    Bill Flagg: [00:11:44 - 00:12:02]

    I've moved on, and I don't know what's, you know, what is next. You know, is it being an entrepreneur in business, it's like getting creative. Thinking unconventionally was really where I got. I think most of my joy was creating things that others hadn't seen before. 


    Anastasia Koroleva: [00:12:02 - 00:12:44]

    And delighted people, which is the essence of creativity. Right. Artists do that, but also entrepreneurs do that. Just a different form of art in a way. Right, right. Fantastic. You know, I moved to Europe for a very similar reason, too. I ran out of motivations in the middle of building my third and fourth business. I decided to sell them, which was way too early in terms of their cycle. Definitely not the best decision financially, but never regretted it, because, like you, I just felt I need to move on. That's why I was really curious how it felt for you that you were ready. I also just knew that I was. 


    Bill Flagg: [00:12:44 - 00:12:49]

    Ready for the next chapter, independent of price or value. 


    Anastasia Koroleva: [00:12:49 - 00:13:10]

    And it's not necessarily age. I was way younger than 50 at that time, like 38, 39, something like that. So I don't think it's necessarily always your age, but maybe it's enough intensity in your previous experience that you're ready to do something else. 


    Bill Flagg: [00:13:10 - 00:13:11]

    Yeah. 


    Anastasia Koroleva: [00:13:12 - 00:13:29]

    So I absolutely relate to that. And I'm absolutely sure you'll find that new form of creativity that you're looking for. But do you find for now, Europe and particularly Portugal, where you live, inspiring enough? Like you mentioned, you decided to stay. 


    Bill Flagg: [00:13:29 - 00:15:50]

    Longer than a year, new cultures, and I love discovering. I mean, Europe is just such a mix of, obviously, so many different cultures and languages, and there's something about it that's. I'm really enjoying being in the discovery mode and also a sense around life where growing up as an american, I took great pride. And it was an amazing place to build businesses. Amazingly easy place in the world to build businesses and an amazing ecosystem, particularly in Boulder, Colorado, where there was a ton of our entrepreneurs that I was surrounded by. So that was a great place to create business wise. And I always had a dream of coming to, returning to Europe after I made it in the US because of the prioritization around life over work. And that involves just the simplicity of sitting down for dinner with friends regularly and having two hour, three hour lunches with wine, just simple things like that. That really, right now is really feeding my soul and helping me to slow down in how I'm, you know, before, it was just all about, okay, how much more can I create and how much more value can I create, and who can I, you know, do it? You know, create with? And who can I? It was very, very transactional in the US, it. My experience, whereas, like, I'm almost returning back to my roots because my. My father's came from Frankfurt just before being here in London, and where there was a dedication in front of the apartment that my dad was born in, in Frankfurt, and to him and his brother and my grandparents, his parents. And so there was. And they were. They were business owners in Frankfurt. 


    Anastasia Koroleva: [00:15:50 - 00:15:54]

    So it feels like coming home for you, being in Europe a bit. 


    Bill Flagg: [00:15:54 - 00:15:55]

    It does. 


    Anastasia Koroleva: [00:15:55 - 00:16:09]

    Great. So do you ever have this fear that you are now out of that startup creative system and you may slow down too much and not be able to ever go back? 


    Bill Flagg: [00:16:09 - 00:16:15]

    No, I don't have that fear because as of now, I don't feel like I want to go back. 


    Anastasia Koroleva: [00:16:15 - 00:16:21]

    So you really feel you're done with that part of your life and something completely different is likely to emerge? 


    Bill Flagg: [00:16:21 - 00:16:21]

    Yeah. 


    Anastasia Koroleva: [00:16:21 - 00:16:22]

    You experience now. 


    Bill Flagg: [00:16:22 - 00:17:22]

    Well, and what I'm. The seeds that I'm planting right now, because I don't believe, like, I don't. I don't believe I've. Anything has come into my life by seek, by necessarily seeking, but being open to discovering is where I have found things or found things of the best things that have come into my life. And so what I'm, the seats that I'm planting to discover is, how can I be creative and how can I be creative in community? Because I'm realizing, like, I love, I love the idea of collaborating and being in community. I think it's one of the great joys of being a human is that we get to connect with each other, you know, and create with each other. And, you know, I just watched the documentary on the plane right here, the creation of we are the world. Have you seen it? 


    Anastasia Koroleva: [00:17:22 - 00:17:23]

    No. 


    Bill Flagg: [00:17:23 - 00:18:16]

    Oh, it brought me to tears because here are all these amazing artists who created on their own, you know, and we're as big as, you know, as big could be. And then they brought together for one night into a room to create we are the world, where they co created together and saw each other's frailties and laughed with each other. And it was like a night, like the greatest night of pop is the name of the movie. And it's. I now understand why, because it was, it, it was just such a soul connecting thing for these artists to create this song together for the purpose of benefiting others in the world. Like, so beautiful. So it really inspired me to think more about, oh, it's not just my creativity, but wouldn't it be wonderful to be creative with others? 


    Anastasia Koroleva: [00:18:16 - 00:18:33]

    So you obviously experienced that in the business world. Well, business building business, I collaborated a lot in business. You just want to give it a different purpose. Right. You don't want it to be transactional anymore. You want it to be. How would you find? 


    Bill Flagg: [00:18:33 - 00:19:14]

    I think, okay, so the three aspects is using creativity, being in collaboration, and being of inspiration to others. I don't want to have a feeling like I owe anything to anyone or to the world or to, I kind of like. And at the same time, I know that there's great, great joy in that. And I've been. I've been. I've benefited from a lot, from a lot of success. And so that to pay it forward there is, and to share it is fulfilling in as well. But I'm not. I'm not quite there for it. 


    Anastasia Koroleva: [00:19:14 - 00:19:26]

    It wouldn't be genuine. It sounds like you, you're too busy figuring out things inside of you, so maybe you, you're just not quite ready to give any gift of yourself to the world because you're not ready. 


    Bill Flagg: [00:19:26 - 00:19:27]

    That's right. 


    Anastasia Koroleva: [00:19:27 - 00:19:39]

    It makes a lot of sense. Again, I love hearing it because I don't like when people just put this pressure on themselves and say, oh, I need to give to charity, even though they don't feel it. 


    Bill Flagg: [00:19:39 - 00:20:24]

    And I've actually pulled back from my. I had created a family foundation back in 2008 and gave to a lot, in a lot of different ways to a lot of causes, and I've pulled back a little bit so that I could create the space to go, okay, I don't. Where do I feel the energy? Where do I feel inspired? And because I. For years, I just continued to do what I was doing with it, and so giving myself permission to be go, okay, wait. Wait for it. Wait until I feel the real inspiration versus just doing it because it feels like I should be doing something. 


    Anastasia Koroleva: [00:20:24 - 00:21:16]

    I had this moment in my life as well when I realized that I really did not enjoy giving to charity, and I felt like such a horrible person, and I was beating myself up, and I had the bit of existential crisis, like, what's wrong with me and my values. And it was actually really, really painful until I found the place where you are. You seem to be wiser than me in this. In this sense. But then I just realized, no, I wanted to be genuine, to be sincere, to feel right. And like you, I stepped away from it. Then I came back with a completely different level of clarity and independence of thinking. It was no longer coming from the outside, because I imagined this pressure from the world that I need to give back. 


    Bill Flagg: [00:21:16 - 00:21:20]

    And what did you eventually discover? You were inspired. 


    Anastasia Koroleva: [00:21:20 - 00:22:26]

    You know, actually, I'm doing this. This is my way of giving back. But I could not imagine it back then, because I was thinking in a very predictable, traditional way that I should give money. And then I went, you know, searching. I talked to so many people who got a lot of fulfillment from philanthropy, which I didn't, trying to understand their formula, why it worked for them. And sincerity turned out to be the difference between how, you know, what I was doing before and what they did. So I took some time off, and I thought, okay, I'll just wait for that moment when I'm inspired to give something. And then, very unexpectedly, in a way, it turned out to be that my 13 years I spent trying to figure out why people are often unhappy after they sell their businesses was exactly that source of my new sense of giving and purpose, actually. 


    Bill Flagg: [00:22:26 - 00:22:29]

    And what are you discovering? Like, what is. What is. 


    Anastasia Koroleva: [00:22:29 - 00:24:00]

    Well, the most, I think, interesting, in a way, the biggest discovery I made is that there is a root cause to pretty much all mistakes and suffering, because there are lots of mistakes. People don't want to talk about it. But from emotional mental health suffering to incredible financial losses, people use hundreds of millions in a decade by just not being in the right place. So the root cause is actually not doing this introspective work, not taking that pose, not to connect in with who you are, not healing. That's why I got so excited that you're doing it right, because most people jump back into activity way too early, and then more often than nothing, ten years later, they're unhappier, poorer, and all of that. So they chase more money and end up losing the money, but also losing very, very precious time. You know, statistically, I was really shocked when I came across it. But statistically, it takes ten years to recover psychologically from a life changing exit. And my conclusion and observation is that it's simply because people go in a completely wrong direction from the very beginning. So the reason it takes ten years is because they make all these mistakes. They feel absolutely horrible, and then ten years later, they only start doing what they could have started doing much sooner. 


    Bill Flagg: [00:24:01 - 00:24:23]

    I remember feeling that when I sold my company in 2007, I was 37, and, oh, God, I had so much energy. I just wanted to run after things, and I bumped into some stuff. Eventually, I found my groove with helping, really focusing on just a handful of companies. And that ended up working. 


    Anastasia Koroleva: [00:24:23 - 00:25:05]

    No, no, I just wanted to say, I think if people just understand where the most common mistakes are, where the dangers are, and they're just aware of those places, they can charter their own course in whatever way they like, but at least they will not keep making the exact same mistake. So I figured at some point that I kind of owed it to the world in a good sense, because I really felt like I wanted to give it this idea that the mistakes are very predictable and very well known. And you don't. I'm not in a position to tell anyone what they should do, but I can show where the dangers are so they don't waste the precious time. 


    Bill Flagg: [00:25:05 - 00:25:06]

    Yeah. 


    Anastasia Koroleva: [00:25:06 - 00:25:10]

    And go to happier place in their own way much faster. 


    Bill Flagg: [00:25:10 - 00:26:25]

    Yeah. I'm definitely in a different place now than I was back then for sure, to do this and a different phase of life. Right. Something new that I'm noticing that I'm struggling with is because of the move. We've. We're in between a bunch of different houses, and each house has its own own problems. At the time, I was like, oh, I can solve for this relocation by being in part with money, in investing in, you know, more homes that. But what I found is that it. All these assets are actually owning me, and I become a servant to these possessions so much so that, like, I joke that I just want to get a tent, live with a family in a tent, and not have any. Anything to manage or deal with or anything. But it was. That was kind of unexpected, both how I got into that, but it also gave me a sense of understanding how people can get lost and trap ourselves. It's a trap in a way. 


    Anastasia Koroleva: [00:26:25 - 00:27:27]

    It's definitely a trap. And I think what happens to people who spend a decade or more building a business and then they sell it? What they realize very quickly is that so many of their very basic needs were satisfied by that business, and the business is sold, and suddenly none of those needs are satisfied. Like love and belonging actually came more from your team, then your family. For a lot of people, you know, your self esteem was. Was very much about the business and your identity, both internal, like your self respect, but also external from other people. So the business is gone, and then what do you have? You have money left instead of it. And then it's only natural to think, okay, now I have this resource, and I lost all of those source of sources of happiness, so I'm gonna buy them back. But you can't buy them. You can't buy love and belonging. You can't buy self esteem. You have to go through the journey of rebuilding them. 


    Bill Flagg: [00:27:27 - 00:28:28]

    Oh, well, my first round after I sold a company in 2007, people say, oh, how's retirement? I get so angry. I hated that. I'm never retiring, and now I've become comfortable with because I truly feel like I'm retired from being an entrepreneur. I used the past tense and saying, I was an entrepreneur and I don't feel that I am anymore. And so, in a way, I did retire from that, but am I retired as a whole person? I'm, you know, as you said, being, you know, being reborn in a way, becoming a beginner again at all kinds of different things. Maybe the term retired is I'm not working for a paycheck or making money, maybe that, you know, using my time to make more money. I don't know if that's the definition. 


    Anastasia Koroleva: [00:28:28 - 00:28:31]

    Of it, but post minus. Yeah, yeah. 


    Bill Flagg: [00:28:31 - 00:29:00]

    And it's interesting because there definitely is a. An old relationship that I am unwinding where I. I got a lot more joy out of earning money than spending it. And so not earning and spending, but spending a lot more than I ever have is a bit uncomfortable. It's a bit draining soul wise, for me. 


    Anastasia Koroleva: [00:29:00 - 00:29:09]

    Does it ever bother you that you don't have a clear identity or your identity? It refers to the past. Like past entrepreneur. Does it bother you? 


    Bill Flagg: [00:29:10 - 00:29:53]

    No, surprisingly, I thought, yeah, not being able to identify who I am and my, I have a buddhist coach that I talked to once a month who said, well, do you really know who you are? Like, well, sure. I mean, he's like, but really, do you ever really know who you are? And he said, and would you rather wake up every day and know exactly who you are or discover who you are each day you wake up? I was like, yeah, I love discovery. I love, ooh, can I try on what different hat I'm going to try on today. 


    Anastasia Koroleva: [00:29:54 - 00:29:57]

    Do you wish you started it earlier or you wouldn't be ready? 


    Bill Flagg: [00:29:58 - 00:30:33]

    Started retirement earlier, this discovery, discovery phase? Well, I've always been in this discovery phase. I'd say so. I don't, I mean, even when I was discovering new regrets. But I think discovery is, yeah, it's been one of my greatest joys in life and discovery through actual action. Right. There's discovery in reading books and thought and conversation. But discovery that involves action is a great joy in life for me. And it continues to be. 


    Anastasia Koroleva: [00:30:33 - 00:30:46]

    Another concern I hear from exited founders, retired founders, is about their children not seeing you working hard. Do you have that problem? 


    Bill Flagg: [00:30:49 - 00:31:20]

    A bit. I mean, I remind the kids of how hard I worked and for how long. And, you know, they, they remember some of my working, they're only right now 1012 and 14 years old. They're hard workers themselves most of the time. So, yeah, I don't, I don't think too much about, about, about that and about how it could necessarily affect them. 


    Anastasia Koroleva: [00:31:20 - 00:31:25]

    Bill, my traditional last question, how do you want to be remembered? 


    Bill Flagg: [00:31:26 - 00:31:30]

    First thing comes to mind is just passionate about life and living. 


    Anastasia Koroleva: [00:31:30 - 00:31:38]

    Beautiful. Thank you so much. I really enjoyed our conversation. Yeah, I love, I wish we had. 


    Bill Flagg: [00:31:38 - 00:31:42]

    More time exploring this topic with you. 


    Anastasia Koroleva: [00:31:42 - 00:31:44]

    Absolutely. To be continued. Yes, thank you so.


 
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Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance

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Tony Kula. Post-Exit Shift: From Workaholic to Ironman