Bill Flagg. 5 Exits Later: Pursuit of Inspiration

0:00Welcome to the Exit Paradox Podcast, where we discuss how to build a fulfilling and meaningful life after selling a business. I'm Anastasia Koroleva, an exited founder who spent the last 13 years researching and collecting stories about life after a successful business sale. 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. 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.

0:49I 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 he wasn't finding creative joy in it anymore. 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.

1:24Bill, thank you so much for joining me today. Great to be here. So your current LinkedIn profile has exactly one sentence on sabbatical in Europe. That's right. 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. So I've been creating and building businesses since middle school, basically. And so it's been a lifelong dream and passion.

2:09And I thought I would do it until the day I die. 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 10x 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 helped those entrepreneurs grow those companies 10, 20, 30x when I got involved.

3:06and in the last couple years um for various varying reasons with each company um my goal was to continue growing them definitely um and for various reasons for each one we we sold each of the companies um i only have one company left it's 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 U.S. And so now we're living sort of more longer term here.

4:00in Europe and Portugal. So when did it start, your sabbatical, officially? I'd say after the completion of the sale of my biggest company, Survey Gizmo, Alcomer is the name, and we completed that transaction two years ago. Two years. Yeah, and so, yeah, I'd say that was really, before that it was sort of the run-up as we were selling my other companies. 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? 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.

4:48Like I wasn't finding creative joy in it anymore. so essentially it was no longer inspiring for you correct which is which is actually really interesting because most people just say i got burnt out yeah 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 yes i never did any of it for the money. Okay. What did you do it for? 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 how to create great cultures and organizations.

5:47and 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 as a hands-on entrepreneur I did it more so and it was it was um for a while I was engaged with my partners and 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 off to you know yeah hired executive teams and um and then so then became another part removed and that's the part where I just didn't feel I had, I was solving problems but didn't have the creative inspiration.

6:48So how do you channel your creativity now? I'm in a relative pause to create the space to discover what's next creatively. 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. Right. 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. Yeah. It's cool you're doing that. 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.

7:52And to wake up in the morning and kind of feel the blankness is scary at times. Do you feel bored? I don't feel bored. I would say the word is sometimes anxious. yeah I'd say it's uncomfortable at times so why are you doing it if it's uncomfortable because I feel like it's part of part of the unwinding process to let it's not entirely just about that there's also something that's shifted in me in terms of connection with 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 uh friends and and and learning becoming a beginner again at sports like surfing and sail racing and paddle and and and and and 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 discovering in the child you're connected yeah my inner child is just kind of you you start a new cycle that goes back to zero again in a way and i think that's what you know midlife awakenings are about and um sometimes it feels like a crisis because everything is changing.

9:35There'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 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 you 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. Yeah. And then stepping into something that we don't know

10:30and 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 deal with even investments or estate planning or things like that, I'm just like, this is not what I, I don't even want to, it's like this old energy in a way that I don't really want to play in, but I have to be an adult at times. Well, I guess you could embrace it as duty, which is a positive source of motivation. Duty, that's an interesting word.

11:19So 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. I don't know if I'm doing it faster. I tend to be in an instigation phase. You're exploring what else is out there besides building businesses, which you really enjoyed, but now ready to move on. Is that correct? Yeah, I've moved on, and I don't know what is next. I'm being an entrepreneur in business. is 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 and delighted people.

12:22Which 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 ready for the next chapter.

13:04Independent of price or value. 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. Yeah. 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 Portable, where you live, inspiring enough? Like you mentioned, you decided to stay longer than a year. New cultures, and I love discovering.

13:50I mean, Europe is just such a mix. It's obviously so many different cultures and languages, and there's something about it that's, you know, I'm really enjoying being in the discovery. mode and the and also a sense of 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 yeah 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 um business wise and um and i always had a dream of coming to returning to europe after i made it in the u.s because of the the prioritization around um life over work and um and that involves you know just the simplicity of sitting down for dinner with friends regularly and making and having two hour three hour lunches with wine and just simple things like that that really um right now is really feeding my soul and helping me to slow down in um how I'm you know And before it was just all about, okay, how much more can I create?

15:27And 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 U.S. It was my experience. Whereas, like, I'm almost returning back to my roots. Because my fathers 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 business owners in Frankfurt. So it feels like coming home for you, being in Europe. Yeah, it does. 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?

16:27No, I don't have that fear because as of now, I don't feel like I want to go back. So you really feel you're done with that part of your life and something completely different is likely to emerge from your experience now? 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 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 that, the best things that have come into my life. and so what I'm the seeds that I'm planting to discover is how can I be creative and how can I be creative in community because I'm realizing 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 I just watched the documentary on the plane right here on the creation of We Are the World have you seen it?

17:40no it brought me to tears because here are all these amazing artists who created on their own you know and were as big 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 the greatest night of pop is the name of the movie. And now I understand why, because 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. It was just 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 so you obviously experienced that uh in the business world well business yeah i collaborated a lot in business you just want to give it a different purpose right yeah you don't want it to be uh transactional anymore you want it to be how would you define i think 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 um great joy in that and i've been I've benefited from a lot of success.

19:21And so to pay it forward and to share it is fulfilling as well. But I'm not quite there. If you're not ready for it, it wouldn't be genuine. It sounds like you're too busy figuring out things inside of you. So maybe you're just not quite ready to give any gift of yourself to the world because you're not ready. That's right. 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. 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.

20:11and I've pulled back a little bit so that I could create the space to go, okay, where do I feel the energy? Where do I feel inspired? Because for years I'd just continued to do what I was doing with it. And so giving myself permission to go, okay, wait for it. Wait until I feel the real inspiration versus just doing it because it feels like I should be doing something. 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 a bit of existential crisis, like what's wrong with me and my values.

21:01It was actually really, really painful until I found the place where you are. you seem to be wiser than me 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. and what did you eventually discover that you were inspired you know actually i'm doing this for 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.

22:04And the sincerity turned out to be the difference between 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 and trying to figure out why people are often unhappy after they sell their businesses, was exactly that kind of source of my new sense of giving and purpose, actually. And what are you discovering? Like, what is... 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.

22:59Because there are lots of mistakes. People don't want to talk about it. But from emotional and 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 pause, not connecting 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 not, 10 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.

23:49You know, statistically, I was really shocked when I came across it. but statistically it takes 10 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 10 years is because they make all these mistakes. They feel absolutely horrible. And then 10 years later, they only start doing what they could have started doing much sooner. 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.

24:30And I bumped into some stuff, but eventually found my groove with helping really focusing on just a handful of companies. And that ended up working. 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.

25:14And 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 and go to a happier place in their own way much faster. 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're in between a bunch of different houses. And each house has its own problems. At the time, I was like, oh, I can solve for this relocation by being, in part with money, investing in more homes.

26:03But what I found is that all these assets are actually owning me. And I've become a servant to these possessions. so much so that I joke that I just want to get a tent, live with a family in a tent and not have anything to manage or deal with or anything. But 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. It's definitely a trap. And I think what happens to people who spend a decade or more building a business and they sell it, what they realize very quickly is that so many of their very basic needs were satisfied by that business.

26:59And the business is sold and suddenly none of those needs are satisfied. Like love and belonging actually came more from your team than your family for a lot of people. well, your self-esteem 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 sources of happiness. So I'm going to buy them back. But you can't buy them. You can't buy love and belonging.

27:39you can't buy self-esteem you have to go through the journey of rebuilding them oh well my first round after sold the company in 2007 it was like oh how's you know how's retirement and i get so angry you know i hated that i'm not i'm never retiring you know yeah and now i've become comfortable with um because i truly feel like i'm retired from being an entrepreneur I'm I I use the past tense and saying I was an entrepreneur and uh and I don't feel that I am anymore and so in a way I did retire from that um 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 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's you know using my time to make more money I don't know if that's the definition of it but post money yeah and it's interesting because there it 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.

29:03And 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. Does it ever bother you that you don't have a clear identity or your identity refers to the past, like past entrepreneur? Does it bother you? No. Surprisingly, I thought, not being able to identify who I am. And I have a Buddhist coach that I talk to once a month who said, well, do you really know who you are? I'm 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?

30:02I was like, yeah, I love discovery. I love, ooh, can I try on a different hat I'm going to try on today? Do you wish you started it earlier or you wouldn't be ready? Started retirement earlier? Yeah, this 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 things in business. So no regrets in this. 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 has been just a great joy in life for me.

30:50And it continues to be. Another concern I hear from exited founders, retired founders, is about the children not seeing you working hard. Yeah. Do you have that problem?

31:07A bit. I mean, I remind the kids of how hard I worked and for how long. And, you know, they remember some of my working. They're only right now 10, 12, and 14 years old. and they're hard workers themselves um most of the time um so yeah i don't i don't think too much about about about that and about how it could necessarily affect them um bill my traditional last question how do you want to be remembered the first thing comes to mind is just passionate about life and living beautiful thank you so much I really enjoyed our conversation I wish we had more time exploring this topic with you absolutely to be continued thank you so much