Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"
Episode - 40
Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished”
Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars.
Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized.
Scott is a natural creative who sees building a business as an artistic endeavor. It was this intrinsic need to create that sustained him through the grueling journey of building his business.
Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created.
In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children.
What We Discussed:
00:00:00: Introduction and welcome to Scott
00:00:11: Reflections on selling the company
00:01:22: Feelings post-sale and personal identity
00:04:01: Comparing business to art
00:04:58: Transition from attorney to entrepreneur
00:06:57: Founding and growing Levelset
00:10:15: Key roles and talents in the company
00:12:21: Starting a new business and family considerations
00:18:00: Debating the reasons to start another business
00:21:02: Seeking purpose and fulfillment
00:23:21: The necessity of creativity and purpose
00:24:06: The challenges of balancing personal and professional life
00:25:01: The paradox of purpose
00:26:31: Rebuilding life and purpose post-exit
00:27:56: Adjustments and surprises after exiting a company
00:30:02: Facing mortality and existential reflections post-exit
00:32:36: Managing personal expectations and regrets
00:35:07: Reflecting on unfinished business and the non-finality of accomplishments
00:40:03: The journey and appetite for creative endeavors
00:42:44: Exploring new experiments and hobbies post-exit
00:44:28: Writing and reflecting on vision after business exit
00:45:32: Building and helping companies after the exit
00:47:08: Structuring the company's vision
00:47:48: Financial exit and its impact
00:50:25: Managing newfound wealth
00:52:58: Becoming a cautious investor
00:56:00: The hedgehog concept
01:01:53: The influence of entrepreneurial family upbringing
01:04:42: Wishing entrepreneurial experiences for children
01:07:32: The importance of self-reliance and vision for entrepreneurs
01:09:22: Strategy Development and Investment Philosophy
01:11:07: Changes in Motivation Over Time
01:14:40: Current Motivation and Challenges
01:17:36: Inspiration and Choosing People to Surround Yourself With
01:18:21: Building a Network Organically
01:20:33: The Importance of Purpose and Motivation
01:24:49: Reflections on Authenticity and Meeting New People
01:25:04: Legacy and How to be Remembered
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Anastasia Koroleva: [00:00:00 - 00:00:03]
Hi, Scott. Thank you so much for joining me today.
Scott Wolfe: [00:00:03 - 00:00:05]
It's my pleasure.
Anastasia Koroleva: [00:00:06 - 00:00:18]
So you had a big exit three years ago. Can we go back to that moment and tell me how you felt when the company was sold?
Scott Wolfe: [00:00:21 - 00:01:20]
Yeah, the, I mean, well, one thing is, it's a lot of mixed feelings. Everybody probably experiences a lot of mixed feelings with that. I was really proud of the company when it was sold. I was very happy. I thought that I had a lot of, I guess, high highs in that moment. It was a whirlwind. It was fun, but also a little bit of anxiety around, like, well, something's leaving your hands. That was in your hands, and there's a little bit of anxiety about that. Optimistic about it, but a little anxious. But for the most part, I mean, it was a really high, high. It was the culmination of a lot of work. And I kind of remember, remember, or I remember noticing that it was the top of the mountain for this particular asset, this particular journey, and appreciated. And I had fun. I loved it.
Anastasia Koroleva: [00:01:21 - 00:01:26]
Yeah. How did that feeling change over the past three years?
Scott Wolfe: [00:01:29 - 00:02:44]
In different ways. I think there was probably some anxiety afterwards feeling changed in the shorter term, like in maybe the twelve month term after it, into more of. More of the feeling of loss that maybe I was predicting or worrying that I might have. So then you start to feel the loss of what you had before. There's a lot of identity wrapped up in that. So I was starting to question where I belong in that company and in the world. But I don't know if the, and what's funny is even though you have a little bit of loss, a little bit of grief, a little bit of identity complex, a little bit of sadness and frustration at times, a lot of frustration with something that you had a vision for and that you are, that you were the author of Kind of going in directions that maybe can frustrate you. Kind of like, it was like a child going to college and, you know, starting to wear clothes, you don't like them to wear a, and go out later than you like them to go out.
Anastasia Koroleva: [00:02:46 - 00:02:56]
But would you say it's a loss of control that bothered you, that you could no longer have a say on what happened to your company after the sale?
Scott Wolfe: [00:02:57 - 00:03:58]
No. I mean, maybe there was a degree of that. I think that with respect to that question, it was more about authorship. It's like if you're a, to me, and I guess every founder, every CEO, every leader is a little bit different. But to me, I felt, in retrospect, like I was very much an author of a work. I was like a painter painting a painting. And I had all this control in a way. It wasn't like I could control what we did in a day, but I was the author of the direction. It was my piece of. And then after that, it isn't the control of a team or the control of a plan or the control of an objective. It's more about you just, you're not the author anymore, and that's, you can't write what you want to write. Exactly. You can't paint what you want to paint. Exactly.
Anastasia Koroleva: [00:03:58 - 00:04:05]
Yeah, no, no, I completely understand. Would you generally say that business is a form of art?
Scott Wolfe: [00:04:06 - 00:04:35]
I think so. Personally, yeah, I think. And when I think about what I enjoy doing, what I enjoyed about the process of building the company, it was a lot. A lot of it was. A lot of it was design. It was a design job. You know, it was an art job. And more than it was corporate work.
Anastasia Koroleva: [00:04:36 - 00:05:07]
To me, I very much can relate to it. We both started as attorneys, but then in my business, I also definitely loved the creativity and saw it as a channel for my creativity, and then very much missed exactly that. So I know what you're talking about. So going back to your being an attorney first, how did that transition go for you through business building and to today?
Scott Wolfe: [00:05:09 - 00:06:56]
It was really smooth. I was a weird attorney in the sense that I wasn't exactly expecting to become an attorney. I went to law school, so I knew I was going to get a law license, but I was doing it sort of in connection with a family business that my parents had. And so I wasn't necessarily gonna go practice. But when I got my law license, a month after I took the bar exam, Hurricane Katrina came and hit New Orleans and sort of flipped the family business on its head. And I found myself opening a law firm that focused on construction law and insurance law and helping a lot of the contractors and property owners in New Orleans with the volume of construction. So I was running a firm that I wasn't. I wasn't like, all of a sudden, I was practicing, but then I was almost. It was my own firm. Right out of law school, I hung my shingle. And so before I knew it, I had two or three attorneys working in my office, and I was kind of running a business, and I had some other businesses I started on the side of that business, one of them being level set. And so it was like I was juggling a lot of balls. Everything was everything. There was a lot of activity, and I wasn't an attorney. You know, I didn't get that, like, traditional sense of an attorney. So the transition to level set was fairly smooth because it was kind of one of. I was always having three or four things in my that I was juggling any time, and level set just started to consume more attention. And so it was pretty smooth.
Anastasia Koroleva: [00:06:57 - 00:07:02]
So let's talk about level set. How long did it take you to get to an exit?
Scott Wolfe: [00:07:04 - 00:07:06]
Depends on how you count.
Anastasia Koroleva: [00:07:08 - 00:07:09]
How do you cut?
Scott Wolfe: [00:07:10 - 00:09:23]
I say that Levelset had three beginnings, three foundings. The first founding was around 2008, when I was two or three years out of law, three years out of law school. It was in the throes of post Katrina New Orleans. And I had three or four different things that I was doing, the law firm being one, my parents restoration company being another. And I had a. I had a software development company where I was building little software products, and I built this idea for levelset as kind of like a turbotax slash legal zoom process for construction liens. And so that's when it was originally founded, but it lived on the side of my desk for like five years. So from 2008 through 2012, it did fun, but it was just a really, it was a very pet project with the main show being a lot of the other stuff I was doing. It was in 2012 that I had my first child, and this little side project was just like, it just called me, and it was working in a way that I just felt. I felt it working. And so level set had its second beginning, which is that I shut off my attention to all the other projects and I focused exclusively on it. And I raised. I started raising. I raised a small family, friends, angel, kind of round of financing. And I ran that like that for three years. Cash flow positive, very, like mature, very conservative growth. And then it got a third and final founding in 20, 12, 15, when I started raising venture capital for the company. Then it went through a few rounds of venture capital and sold in 2021. So six years from our first venture capital round, nine years or ten years from me going exclusively and starting to work on it. And maybe, I don't know. What's that, 14 years, 15 years from its true origination?
Anastasia Koroleva: [00:09:24 - 00:09:41]
Yeah, yeah. Makes a lot of sense. So. But you had to still grow quite fast because you raised, what, 46 million and you exited for half a billion. So that from a little side project on the side of your desk is quite a jump.
Scott Wolfe: [00:09:42 - 00:10:12]
And, yeah, we grew, it grew very little until 2012. From 2012 to 2015, it grew like, it grew, let's say, from 150,000 to like $2 million of revenue. Good growth, good, good fast growth in three years on very little farming. But then it really took the turbo fuel. I mean, we raised 46 of the 46 million between 2015 and 2019. Right. So we were really blowing in those four years.
Anastasia Koroleva: [00:10:15 - 00:10:32]
So for you, when you look back, what do you think your key role was in the company? Like, what it is you brought to the table that made a difference from the standpoint of your personality, your talents?
Scott Wolfe: [00:10:34 - 00:12:20]
I never thought about it like that. I mean, if you look at it from pure corporate talent, I think I was talented in marketing and in product roles. And specifically, I have a very, I have a knack around, like demand generation and creating a position and creating brands and content marketing and blending the, like I like to say, blending differences between product and marketing. A phrase I would use all the time is everything is marketing. And so the product, I like looking at companies like Zillow and saying, hey, whose product? And who's marketing at Zillow? And it's really hard to tell because they're so overlapping. Right. The product itself creates the marketing. So I think from a corporate talent standpoint, it's somewhere in those things. When I think about what I brought as a leader, I think I brought a lot of enthusiasm for this particular point of view. I brought a point of view, a strong point of view, and a lot of enthusiasm behind it in a category that I really understood well. And I think so in that regard, my enthusiasm and point of view was super important to everything, kind of finding its way to the accomplishments that we had.
Anastasia Koroleva: [00:12:20 - 00:12:35]
Yeah. So the reason I asked you this question, Scott, is because I'm trying to understand how your understanding of your role in the first business then translated into your current business because you already started another one, right?
Scott Wolfe: [00:12:35 - 00:12:38]
Yeah. I don't know about that. Yeah. I mean, yes.
Anastasia Koroleva: [00:12:39 - 00:12:39]
Okay.
Scott Wolfe: [00:12:39 - 00:12:56]
And technically, but it's living on the side of my desk a lot like, a lot like level set did for five years back in the day. Yeah. So it's technically, there's another business there.
Anastasia Koroleva: [00:12:56 - 00:12:58]
Why are you dragging your feet?
Scott Wolfe: [00:13:00 - 00:15:18]
I'm dragging my feet for a few reasons. One, and since I have a few reasons that's making me want to drag my feet more. One reason is I'm not sure I want to do it again. I remember how hard it was to build levelset and I'm not sure I want to do it again at all. And I think about, what if I did it and I spent 15 years doing it, or ten, and I had a great outcome. Oh, they give me another ribbon. I put the ribbon right here. Be like, hey, he did it again. You know, like, what's the point? That's one reason I'm not sure if I want to do it. The other thing is I've been very. Maybe. Maybe it's a little bit of my own fear of, like, sticking my neck out again. Maybe it is the pressure of having such a successful outcome the first time and not necessarily knowing how to re enter the world at a ground zero again. But I see I have, like, three kids. They're non eleven and 13. Very freshly non eleven and 13. And I think, what if I didn't do anything until my nine year old was twelve or 13? That's like three or four years from now, I'd still be able to do something. I'd still be young. But if I did work for the next three or four years on this new business and, like, threw everything I had into it, I think there's a pretty significant chance of me maybe regretting that I didn't take those four years and just like, breathe. Yeah, right? So I'm apprehensive about getting too far into something in while I have a young family at home. In a time when I'm like, I got the. I have the opportunity to not go work that hard on something. I mean, not everybody has to work that hard all the time, right?
Anastasia Koroleva: [00:15:22 - 00:16:26]
Absolutely. I think you're very wise because three years is a very short period of time. You need to go through that process. And frankly, I am very happy to hear that you're not rushing into big commitments yet. Because what I see a lot, if you zoom out, actually, and you look at stories of exited founders, what I see again and again is that people rush into something very quickly because they just can't tolerate the discomfort of not having a business or not being busy or having to actually introspect, God forbid, and they rush into something very quickly, and then a few years later, they regret it, and it's very hard to undo. So what I found is that it actually takes a decade for people to just adjust to new reality, which is fascinating because nobody expects that. People think, oh, you know, in a few months I'll be fine. But it's not actually true. If you commit to something in a few months, most likely you'll spend years.
Scott Wolfe: [00:16:26 - 00:17:06]
Undoing it and you don't know what you want. Like, I don't know. I really don't know what I want. I don't know if I want to start another company. I think I know how to start another company, and I think I can. But maybe a joke I like to say is, maybe I want to be a stand up comic. Like, I don't know. I don't know if I don't want to be, like, I don't know. I have the opportunity, which is unique, to do anything that I want, which makes it a little harder. I read somewhere about Peyton Mannon, who, you may know because you're in London, you may know Peyton Manning. You know who that is.
Anastasia Koroleva: [00:17:06 - 00:17:08]
Yeah, of course.
Scott Wolfe: [00:17:10 - 00:18:00]
I don't know. So, he was a. He retired when he retired from football. And I always think it's fascinating how people retire from professional sports because they always retire very young, and they literally been doing it since they're, like, you know, five years old. So I always think it's fascinating. What do they do when that just goes away? And Peyton Manning's old coach told them to spend the year not doing anything and just to figure out what he doesn't. What he doesn't want to do. Right. Like, figure out the things you don't want to do, and. But it's definitely a challenge. And so I found that to be kind of wise, and I've been trying to make sure I don't jump into anything, but it is definitely challenging. Okay.
Anastasia Koroleva: [00:18:00 - 00:18:27]
So, yeah, so, you described why you wouldn't start a business. It's because you already know how hard it is. You know how much pain and sacrifice that requires. It takes a long time. It takes you away from the family, and you want to be there for your kids in the next few years. Now, can you try to be a devil's advocate and actually tell me why you would do it?
Scott Wolfe: [00:18:28 - 00:21:20]
Yeah. So, there's a lot of reasons. One is that you don't really get. You don't really accomplish anything or discover anything by sitting on your back porch on a rocking chair. I didn't start level set from a rocking chair thinking, hmm, what kind of business? What kind of things could I do with my life? What kind of business could I start? Life kind of got thrust onto me, right? I had hurricane Katrina. My house was flooded. I had businesses popping up all over the place. I was active. I was in the stream. And so, being introspective and thinking is fun in ways, but it's not in the stream, and I'm not going to discover what I'm not gonna discover, like, a calling or a mission or a purpose or I'm not gonna discover, like, healthy, fulfilling work by sitting on my porch on my rocking chair. Yeah. So, one reason to start a business, or to get, is to get in the stream and just start plugging away at something that. Some little crack in the universe that you think you see some art, you wanna some, some art, you wanna create. Like put painting, you need it. You need a paint, you write and you need to write. So that's one reason. The other reason is that I do have like, an impulse to create. That's what I, as far as I really remember, I created little businesses and created little concepts, and I have impulse to. To do it. That's why this other thing exists. It's like I. And that other thing, if you, if you looked into it at all, it. It relates very much to my background. It is not, it's not like I sat around thinking about what would be a good business. This is a something that I kind of. It was. It's one of the threads of my life that I keep pulling on. And I have an impulse to work on it. So I, that's another reason to start, is because that is my, my impulse. And the third, the other reason is just to have the. Just to. Just to hear the gunfire. Just to hear the sound of the gunfire, of going do something else. Whereas otherwise, you're kind of in like this paralysis of not doing something. And then the longer you don't do anything, the more foreign it becomes.
Anastasia Koroleva: [00:21:20 - 00:21:58]
Yeah. Yeah. Our skills can atrophy and it's, of course, a concern. Okay, so you basically feel you want to have the sense of fulfillment, which I assume running a business used to give you, and sense of purpose, and you have this creativity and this inner need that needs to be realized. It needs to be channeled and needs to become something. Right. It's inside of you. So would you say you're lacking a sense of purpose? Would that be the right description of it?
Scott Wolfe: [00:21:59 - 00:23:16]
I hate to say it because, like, I have, like, I have a lot of. I have. I have a lot of family to deal with. Right. Like, I have things. I have. I have a. I have purpose. So you hate to say that you lack purpose, but the answer, I think, is yes. Like, I lack a. I lack a. I think it's. Maybe it's not that there is something around identity and purpose and these terms, but the other thing that I feel like, that I quite don't have my hand around is that I don't feel like I'm building anything or I don't feel like I'm creating anything. And so, and I think about. I've thought about this a good bit where if you have a person like, like Stephen King, who's written so much, and, like, what could possibly be the purpose of him writing another book, right? I mean, he has so many things he's written. He's probably fine just not writing anything. Like, it isn't, doesn't make a difference.
Anastasia Koroleva: [00:23:17 - 00:23:19]
Except that he needs to.
Scott Wolfe: [00:23:20 - 00:23:31]
Except he needs to do it. He needs to write the book because he needs. So there's something in that that I think I'm missing.
Anastasia Koroleva: [00:23:32 - 00:23:54]
But to me, it would be part of your purpose, because the purpose is the reason we're here. Right. It's our biggest desire. That probably stems from the very reason we're here. And if that creativity is inside of you, then that's exactly what it is. Like, Stephen King is probably here to write those books.
Scott Wolfe: [00:23:55 - 00:24:36]
Yeah, but he could stop. He could also, he could also switch and do. He could get into movies or he can get into. He could start a business, you know? And, like, there is a lot of purpose to, like to raising children. Right. There's a lot there. And if I fast forward my life ten years from now, if I. If I would, if I could spring forward ten years, it's much more important that those three children and my family be in a. In a good position than me to write another book.
Anastasia Koroleva: [00:24:36 - 00:24:37]
Yeah.
Scott Wolfe: [00:24:37 - 00:25:09]
Right. And maybe I can find a creative outlet in writing a book or something else besides building a company. Maybe there's another craft that I want to hone in on. But I understand what you're saying. This is the struggle. This is the struggle. What is the tug of war?
Anastasia Koroleva: [00:25:09 - 00:25:59]
You know, I actually, I hear it a lot, and I was there as well myself. And I call it the paradox of purpose. Because you want purpose without the pain, right? You don't want that pain anymore, but you want this rewarding feeling that you are self realizing, for the lack of better word, but you're doing that creative thing that you love doing. Right? So it's not easy, and it's very personal. But I think, first of all, nobody said that there should be just one purpose or definitely one purpose in life. And I don't think there is anything wrong with you accepting your parenting as a purpose for this period in your.
Scott Wolfe: [00:25:59 - 00:26:23]
Life while I am getting a lot of fulfillment out of parenting, so to speak, or just being there more. A lot more than I was before. Um. That still doesn't change. It doesn't. It still leaves a lot of, like, anxiety and yearning in. In the. There's a lot. You have a lot of time in the day. I used to think I had no time in the day.
Anastasia Koroleva: [00:26:23 - 00:26:24]
Exactly.
Scott Wolfe: [00:26:24 - 00:26:27]
And now I feel like there's a lot of time in the day.
Anastasia Koroleva: [00:26:27 - 00:27:41]
Yeah, yeah. It's a difficult adjustment. But also what I realized over time for myself and other people is that when we build our business, we essentially build it to satisfy our own needs. Like for example, what you were talking about, your creativity. But there are also other things. For example, our business actually satisfied our love and belonging and all other levels of the Maslow pyramid beautifully. And we just got used to it and didn't fully appreciate until we exited. And then what happens is that the whole pyramid gets shattered. So there are so many conflicting motivations inside of us. There's so much going on. There is so much that needs to be understood and actually fixed and satisfied. And for example, love and belonging that we were getting from the employees and partners. And all of it now needs to be satisfied in the family. And it's very unfair and difficult, actually, to expect. So I totally understand what you're going through. And I think it's great that you're taking the time because you now need to rebuild that pyramid around something else. And family alone will not do it.
Scott Wolfe: [00:27:42 - 00:28:42]
That's right. And I think it's the other thing that's interesting about a company. Having your own company that you build is not only do you build it to satisfy all those other things, but you build it. The suite, it's actually. It's actually like perfectly. It starts to fit like a glove in other ways. You can go work somewhere else, but you don't have the ability to make that other place that you work no fit all your needs like a glove. Everything gets to fit perfectly for you. So it is. And then the other thing that I was. A few things I was surprised about, about exiting. And one of them you just said was that it shuts you down to zero. It doesn't. It isn't like you lose. It isn't like a subtle descent. It's just everything just shuts off like a switch.
Anastasia Koroleva: [00:28:42 - 00:28:42]
Yeah.
Scott Wolfe: [00:28:43 - 00:29:58]
And that is a little disconcerting. And the other thing that you don't really appreciate when you're at the top and even at the moment of exit, when everything feels good, you don't appreciate that. It's that the day of. It's like when you're born. It's like I'm born November 6, 1980. And then my death day is blank. Right. No one tells you necessarily your death day. And it's sort of like that business too. Don't quite. You always know it's going to end. In some way, quite know it's going to end on November 2, which is when ours. And even though I knew I was, I didn't choose to sell it directly. I wasn't looking to sell it on November 2. It just happened that way. If you would have asked me on February 2 whether of that year, whether my whole journey at levelset was going to end on November 2, I would have thought that that wasn't the case. Like I would have been. I wasn't expecting it.
Anastasia Koroleva: [00:29:58 - 00:30:32]
Yeah. In that way, of course. So, talking about death, an interesting topic. What I hear every now and then is that some people, after they sell a business, especially after many years, they have this fear of death because they actually face their own mortality as well. When we're busy, we don't think about it. When we're not busy, suddenly all these scary thoughts come to our head. Did you experience that?
Scott Wolfe: [00:30:34 - 00:32:00]
No, but maybe an analog to that is that when you are in the throes of running a business at the level that I was running it, it's not that I'm not thinking about death. It's just that I feel like so much of the world is spinning with me. And when you sell and you exit and you're gone, it's kind of like you shot into outer space and you're just floating up there, and you watch everything still turn, and it's not turning with you anymore. And it didn't make me think about death, so to speak. But it did make me reorient my place in life. Like in the world where, you know, after death, the world's gonna be just fine and the world's gonna. And the world's gonna go on. And I think you get a glimpse of that when you exit a company, because you, in a way, the world and business and the market you were in, that you were really, you know, plugged into, it all goes on, and you're just floating out there in sort of irrelevance.
Anastasia Koroleva: [00:32:00 - 00:32:00]
Mm hmm.
Scott Wolfe: [00:32:00 - 00:32:13]
And that's why I think I can see the analogy. I never did feel it in a, like, in a, in you see it.
Anastasia Koroleva: [00:32:13 - 00:32:24]
More as a humility lesson. It sounds like that the world goes on without you, and that teaches you, you know, the laws of the universe in a way.
Scott Wolfe: [00:32:25 - 00:32:29]
Right, right. And I knew it before, but I never felt it before.
Anastasia Koroleva: [00:32:29 - 00:32:49]
Yeah. It's a huge difference between, it's a huge difference between knowing something and actually experiencing it, isn't it? Like if you take about. Take the whole post exit experience, maybe you heard before from your friends that it's not that easy, but until you actually experienced it, you don't know. It's like having kids are falling in love, isn't it?
Scott Wolfe: [00:32:50 - 00:33:05]
Yeah, that's right. And. And that makes you wonder, man. Wow. Do I. Do I even. Was it a good idea to do. Was it a good idea to die like this?
Anastasia Koroleva: [00:33:06 - 00:33:08]
Do you ever regret it?
Scott Wolfe: [00:33:08 - 00:35:07]
Versus. Or would you rather live in. Would you rather, would you rather live in the ignorance of bliss? The bliss of ignorance because you don't know that it's over yet? I don't. I regret selling it in different ways, but I also don't regret selling it in different ways, so I can't tell. Maybe. Maybe my regret is more appropriately described as just grief of it being, like, over and being gone. But it had to. I mean, that, that grief was going to come at some point, in some form. And. And the. The decision to sell was so sound. I think the information that I had, I did. I do. And what I would, I wish. There's a lot of things that I wish would be different. There's things about the. Things about the. The fate of the. Of the assets after the acquisition. You know, it's not, it's not my art piece. I don't necessarily like who's. I don't necessarily like where it is on the wall. Right. I don't like, I don't like the placement. I think a few inches higher. If you just. So. Those things are troublesome. They're aggravating, but it's hard to conflate. I don't want to conflate regret with it. It's this too much positive that came out of the transaction. It was too good of a decision financially for not just me, but for lots of people, and career wise, for so many people. It's so hard to regret it, but there's a lot of other feelings of, you know, there's a lot of other feelings that can simulate regret.
Anastasia Koroleva: [00:35:07 - 00:35:09]
No, of course. What do you miss most?
Scott Wolfe: [00:35:11 - 00:35:12]
What? Say again?
Anastasia Koroleva: [00:35:12 - 00:35:20]
What do you miss most? Maybe besides your ability to channel your creativity? Because we talked about that.
Scott Wolfe: [00:35:22 - 00:36:09]
Yeah. I don't know. I don't know if this is challenging creativity, but one thing I definitely miss is that I feel like I have unfinished business in the space, and that's probably. That aggravates me the most. I don't know if that's missing it the most, but with the. We built, we made so much progress toward a vision that I had. You heard that? So we made so much progress toward a vision that I had. What's going on is somehow my sonos speakers just turned on. Do you hear the music?
Anastasia Koroleva: [00:36:10 - 00:36:12]
I heard a little bit just now. Yeah.
Scott Wolfe: [00:36:14 - 00:37:13]
That's weird. All right. So I was making so much progress on the vision that I had, and I. I knew where it was going. Right. I still know where I would take it and what I would do with it, and it just got taken out of my hands, and I feel unfinished business there. Like, part of that, it makes me want to jump back into it in some way. But it's like you can't quite get those ingredients together again. Like, I'm have to do a new dish now. I can't do that dish because. So I feel a lot of frustration with that because it's not going to happen now. Interesting. It's interesting about how much. How somebody can make a little bit of an impact in the world because I can watch it and, like, it's not going to happen now.
Anastasia Koroleva: [00:37:14 - 00:37:14]
Okay.
Scott Wolfe: [00:37:14 - 00:37:18]
And that's. That's in that way. That's frustrating.
Anastasia Koroleva: [00:37:18 - 00:37:32]
Yeah, I can see that. Because as an artist, you basically see your piece not being ever finished and somebody else playing with it in ways you don't approve. Yeah.
Scott Wolfe: [00:37:32 - 00:37:34]
Right, right.
Anastasia Koroleva: [00:37:34 - 00:37:36]
That must be super frustrating.
Scott Wolfe: [00:37:37 - 00:39:16]
Yeah, it's very frustrating. I miss the rhythm of the work that level set gave me. I miss being challenged in a way. I like not being challenged now in some ways. There's a lot of peace in my way of life now, but. But I. But I definitely feel a different pace of, like, of growth in the. I was growing and getting better at this job. Right. I miss that feeling, but I miss the people the most, probably. I miss, like, the people that we were working together with the most. When I really reflect on it, it's like I read a good book, an okay book called the Monk and the riddle about starting companies and the companies. He said that when he sold his company, the true downside of the deal hit him, which was that they were never going to be like, this group of people were not going to be able to work together anymore, build that thing. And I think that when I bring all. When I start going through my mind and thinking about what do I miss? I guess I come probably to that, which is I really miss the group that we built and we were working together as a great team, and now that team doesn't get to work together again ever.
Anastasia Koroleva: [00:39:16 - 00:39:22]
Yeah. So how do you think that can be replaced?
Scott Wolfe: [00:39:28 - 00:40:25]
I don't know if it can. I mean. Well, it can be. It can be. There's a few. There's a few versions of it being replaced. You can. You can really replace it in that you can get. Build another team. Right? Like, you can. You can go build another team and have another experience and another journey, and it won't ever. I mean, it'll never be that, that team. It will never be that journey that's gone. Right? I mean, that's completely gone and never to be assembled again. And so you can do it again. And that gets back to kind of, like, the very beginning of our conversation of a reason to do it again. But then that one's gonna be gone, too, you know? You know, like. Like, that one's gonna disappear as well.
Anastasia Koroleva: [00:40:25 - 00:40:25]
Yeah.
Scott Wolfe: [00:40:26 - 00:41:50]
So I can do it three times. I can do it four times. Let's say I'm lucky enough to do it twice or three times. I will appreciate. I can't. I can't quite figure out to myself whether the journey is the thing that is worth it. Is it, like, if I need it, that I need it to do, if I need to do it again? Because I want to replace that. Not replace it. I want to have it again. You know, I have a. Like Jerry Seinfeld said. He said, I don't know why people are arguing. I don't know why people are so worried about spoiling your appetite. I keep getting new appetites. I'm never going to run out of appetites. I'll never run out of the appetite to have the journey again and again and again and again. I can keep, like, sharpening my tools, and I can keep going to work and carrying my little lunchbox and doing it. Or maybe I can find another journey in another. In another in another medium. I think about people like Steve Martin, who, you know, he's a stand up comic for. He reaches the mountaintop of stand up comedy, he goes, man, I don't want to do that anymore. I'm gonna go write novels, and now I'm gonna go play the banjo, and then I'm gonna go work on this. Like, yeah, maybe. Maybe that is.
Anastasia Koroleva: [00:41:50 - 00:42:43]
Yeah, as long as you're ready for the learning curve, to learn something brand new from the start. Sure. But it's a tricky decision. So are you experimenting with anything? Because one thing I often talk about with other executive founders is that we find ourselves with very narrow experiences in life when we've spent so much time going very deep, very narrowly on our business. And there is this desire to catch up, but also to see what else is out there and experiment and explore. It's hard when you have kids of your age so you can't just start running around exploring life. But I'm still curious if you are doing something in that direction.
Scott Wolfe: [00:42:44 - 00:44:24]
Yeah. And I think the kids do make it hard. Like, this particular age bracket of my children, there's just so many activities that it's like a constant. They're interruption machines. So it does make it hard to have a lot of uninterrupted space, which is part. And. And the other thing that is different about my founding of level set and some of the other things is when I founded level set, I was in the stream, I was doing five or six different things in the stream of an industry, of industries, and now I'm not in any stream. Right. Because you're just throwing out, like, you're throwing out, like, like, like an old western film where they throw you out of the bar and you land. You just land on the outside and you're like, all right, now what do I do? I'm playing with another company concept. Right. So I've been to playing with that. That gets me. That is a little experimentation. I've been experimenting with, like, writing. I did a lot of writing during level set in a different way, so I've been experimenting with that. And the rest of things that I've been playing with has been more maybe, like hobby ish style, spending more time than spending time with, like, spend a lot of. I've been saying yes, as much as I can with the family.
Anastasia Koroleva: [00:44:24 - 00:44:25]
Yeah.
Scott Wolfe: [00:44:25 - 00:44:28]
And then that takes a lot of time.
Anastasia Koroleva: [00:44:28 - 00:45:02]
So talking about your writing. Talking about your writing, that article of yours that I love about vision, you wrote it about a year after your exit, so I assume you were in the process of processing your experience of building a business. And I think it's brilliant. And you talk about how to form vision for a company. Could we quickly talk about that? And then I want to see how that translated for your own into your own vision for yourself.
Scott Wolfe: [00:45:05 - 00:47:37]
Well, I don't know if it translates to my vision to myself, but the reason why I wrote that and which gets into the reason why I write a lot of things is I was. I had a particular person I was working with who's frustrating me, because there was something about the. I mean, when I built levelset and built the vision out, I didn't exactly, like, construct it according to a framework that I had in mind, but when I was helping, and that's one thing that I've been spending a decent chunk of time on since the exit is kind of helping other companies and various, like, arm's length roles of advisor or board member or helper. And I don't like when I find people that are doing it differently or wrong, and I can't tell which one it is right? Is it wrong or is it different? And so I get frustrated. And so that particular article that I wrote was born out of being frustrated with how I saw someone else failing at setting a vision, which had me reflect on, what does vision even mean and how do you put it together in a company? And then I kind of assembled that article, and I have a few things I've written in article wise that kind of run that same course, like noticing something, getting frustrated, and then reflected on, well, how did I do it? And how does this make sense? I. With, like, the company that this little company toy that I'm playing with now, very naturally, if I were to take that little framework that I put together and start looking at it with this toye, it matches perfectly because it's kind of like my. It's just the way that I. The way that I build something follows the way that I think about this company the moment that it hatches from the egg. I think about it in this way, these segments, this way of thinking about the vision. I should. Maybe I'll go read that article now and bring it up and think about it with respect to my life, because I didn't apply it that way.
Anastasia Koroleva: [00:47:37 - 00:47:38]
Yeah.
Scott Wolfe: [00:47:39 - 00:47:41]
But there may be something there.
Anastasia Koroleva: [00:47:44 - 00:47:56]
So let's talk about a few practical things. So when you had your exit from the financial standpoint, was it a life changing event for you?
Scott Wolfe: [00:47:58 - 00:47:59]
Yes.
Anastasia Koroleva: [00:48:00 - 00:48:19]
How did you react to it? Because there is quite a well known phenomena called sudden wealth syndrome, when people go quite crazy when they suddenly become wealthy and have extreme fear of losing money and all of that. Did you experience any of that?
Scott Wolfe: [00:48:20 - 00:49:48]
Unfortunately, no. It sounds like a lot more fun. I might had a great time. That's what I should have done. No, I. For, in retrospect, I'm happy. I feel like I was wise. I had talked to a few people who had a similar event, and my instinct was to be slow and to make sure that I went slow. So one thing that was interesting, on the one hand, it didn't feel like anything at all. From the standpoint of one day you have not that much money, and then the other day you have a whole lot of money. And I didn't. That. That particular feeling was very dull to me. I did not feel much there. On the other side, I. My instinct was to do nothing. I don't know why, but my instinct was that I wanted it all have time. I didn't want to go invest in things. I was very, I was very cautious about making any decisions at all.
Anastasia Koroleva: [00:49:48 - 00:49:55]
Did it cause people, did it cause you stress? Were you calmly cautious or you were just very scared?
Scott Wolfe: [00:49:56 - 00:50:59]
No, I wasn't scared. I was calmly cautious. I was intellectually cautious. I knew that it was a different thing having that much money. I knew that I didn't know what to do with it necessarily. And I knew that I had to learn more before I just started shooting from the hip and saying, I'm going to do this and this and this. And I did. I learned a lot about wealth in that twelve or 24 month period. I very slowly dragged my feet with applying any of the money to any investments, and I found my way into, I think, like advisors that I trusted. I found my way into investments that I understood and have, like, a pretty conservative approach to it that has worked. And I also didn't go and do, I didn't buy anything. I don't think I bought anything.
Anastasia Koroleva: [00:51:01 - 00:51:33]
Scott, I'm so impressed. I never hear things like that. I'm really impressed because most of the people I interviewed, they say, oh, yeah, absolutely. You go down before you go up financially after an exit, because you make all these mistakes. And I'm one of those people. I made lots of mistakes. I angel invested for fun, to get my identity back for all their own reasons, and made an impulsive thing. So I'm very impressed you had the wisdom to not do that.
Scott Wolfe: [00:51:34 - 00:52:04]
I did, yeah. I feel good about that. I don't feel like I went down. I don't feel like I made mistakes. I won't say I didn't make mistakes. I feel like I didn't make anything, that I don't have regrets there. I did still. There's still a few, like, things that I did to. You mentioned angel investments. I didn't make a lot of. I knew from the beginning I didn't want to be an angel investor.
Anastasia Koroleva: [00:52:04 - 00:52:05]
Mm hmm.
Scott Wolfe: [00:52:06 - 00:52:40]
Because I'm not an investor. I'm very like, I'm not an investor. Why would I go, people spend their career trying to be investors. Why would I take my money, which I put all this risk behind, to go risk it? I don't need to risk it. I can go put it into. I don't need to risk it. So I had that feeling, but still, the number of people right after that exit, that, the number of groups and whatever that kept knocking on the door, of course, it was hard to say no to them all.
Anastasia Koroleva: [00:52:40 - 00:52:43]
Yeah. How did you go about that. How did you go about that?
Scott Wolfe: [00:52:44 - 00:53:18]
I dragged my feet, and that's kind of been, like, my best friend is dragging my feet. And then I did, like, get sucked into a few of them at very small level. So when I, when I would get, like, forced, I almost felt like it was charity. I treated it like charity, actually. So the one ones that I invested in that actually thought of it kind of like I felt like I was almost having to do it as charity.
Anastasia Koroleva: [00:53:18 - 00:53:19]
Yeah.
Scott Wolfe: [00:53:19 - 00:54:25]
A lot of local stuff, like New Orleans based stuff and things in the ecosystem that did a lot for me. Mm hmm. I looked at it as charity, and. And then eventually I learned how to even not do that. Yeah. Like, how to just say no. And ways that I say no now is I invest in a few funds that I have relationships with and that are in my categories. And now it's very easy for me to, like, you know, take a lot of that inbound in all those inputs and direct them into. All right, well, look, I think that you'd be a match for this fund, go to the investors and. But that's a very sen, that's, like, a very tricky area, I think, for people who exit. It was tricky for me, and I had a pretty firm point of view about it. It was still hard.
Anastasia Koroleva: [00:54:25 - 00:55:14]
Yeah. You know, our mutual friend who introduced us, who was also your investor, Ho Nam, prefers to invest in hedgehogs. Right. Hedgehogs are people who are very good at something, one thing, and they do it very well. Also, as he explained it to me a couple of weeks ago, there's another side. When a hedgehog sells a company, that person can still be a hedgehog as long as the next thing they do, they don't do for money. So I now understand why he considers you a hedgehog. Otherwise he wouldn't invest into you, because you do have this amazing, rare ability to really understand what you're good at and not try to chase all these other goals and things.
Scott Wolfe: [00:55:16 - 00:55:28]
Yeah. For, for whatever reason. That's probably true. And. And I like what ho ho is always such a wise investor.
Anastasia Koroleva: [00:55:28 - 00:55:29]
Yeah.
Scott Wolfe: [00:55:29 - 00:56:12]
And a wide counsel on the board and whether I probably even honed my hedgehog enos further with, with ho there as a nice echo beyond it. But I definitely do. I feel I have a lot of perspective overlap with ho around that, which is you can't. And even at level set, besides me personally, what at level set, I really wanted to focus the company on what it was, its hedgehog concept.
Anastasia Koroleva: [00:56:12 - 00:56:13]
Yes.
Scott Wolfe: [00:56:13 - 00:58:20]
And I got a lot of this from being such a big fan of this book that I read when I was like twelve years old around positioning. And I think there's so much whether the success of a company, the success of a person around understanding who you are, who you're nothing and digging into that and I don't, I get turned off when I see, it's interesting because after an exit, that's an interesting thing to put, like interesting thing to bring up around hedgehogs because after the exit I think there is a lot of pressure that comes to do for people that expect you, that one want you to do a lot of things. Yeah, right. They expect you to. In my case, there was all these expectations or things being thrown at you about all the things that I could do. And I still feel this way, like there's a lot of things I can do. And it's a lot of strange pressure around like all the paradox of choice, to use the term paradox again. Right. When you have all these choices, it's paralyzing. And when you look at what people do after an exit or when you look at what people do after they like, after they really make it, there's a, there's only so many categories. Like they could become a coach, they could be a mentor. They can become, they can go become an investor. They can go into charity and philanthropy. They could go into, you know, there's all these different lanes of second purpose. But it's an interesting thought from Ho that any of these lanes. Oh, you can go do another business again. You can do it. You can run the, you can run the tape again. Whatever you do, just go, just remember what it was that made you successful to begin with. It's like the old mini Slickers movie. The secret to life is one thing. You remember that from city slickers?
Anastasia Koroleva: [00:58:20 - 00:58:21]
Yeah, yeah, yeah.
Scott Wolfe: [00:58:22 - 00:58:29]
The secret to life is one thing. And I'll tell you what, that is one thing.
Anastasia Koroleva: [00:58:31 - 00:58:52]
Exactly. But Scott, there is a reason I asked you before about sort of options that you are looking at, because maybe that whole Steve Martin's path of switching between very different activities are not, is not for you. Because maybe you're a proud hedgehog.
Scott Wolfe: [00:58:54 - 00:58:58]
No, but I think that's not, I don't know. That's true. I think Steve Martin is a proud hedgehog.
Anastasia Koroleva: [00:58:58 - 00:58:59]
Okay.
Scott Wolfe: [00:58:59 - 00:59:05]
If you, if you, if you study him, he just hedgehogs into different things. And all of them were art.
Anastasia Koroleva: [00:59:06 - 00:59:06]
Okay?
Scott Wolfe: [00:59:06 - 00:59:30]
You know, they're all arthem. But he was a stand up comic and he, and he like dug that hole and he was. Reached the top and then he's. Then he went into writing, and then he went into music, and they're all, like, similar. They're all in the same category, but. But he never did them all at the same time. He went. He would go really deep.
Anastasia Koroleva: [00:59:30 - 00:59:46]
Okay, I understand. So, given that for you, business is arthem, all the other arts are open for consideration, and you can still be a proud hedgehog and who will be happy, right?
Scott Wolfe: [00:59:46 - 01:01:31]
I would be happy. Yeah, that's right. In a way, I think that's correct. I don't think I'm an art. I don't think art is necessarily the exact place, but a lot of people go into. I was mentioning the things that people go into, which is teaching philanthropy. A lot of people go into expression, right. Into different types of artistic expression. And, yeah, I think that it's possible. And a lot of what I did as CEO and found in the company, a lot of times I was a teacher and a coach. Right. Which is in that teacher, Lane. A lot of times I was in expression lane. I was writing a lot as CEO, and I was creating a lot. So a lot of times, I was investing in a different way. So all those things can be done again in the context of, I'm going to take a company and do it, or is there one that I'm drawn to that I said, you know, I was really good at getting other people to see a vision and to believe a vision and to work around a vision. And I did that through articulation. What else can I articulate? Right?
Anastasia Koroleva: [01:01:32 - 01:01:33]
That's brilliant. I love it.
Scott Wolfe: [01:01:33 - 01:01:34]
Yeah.
Anastasia Koroleva: [01:01:34 - 01:01:51]
And you keep going back to the idea of vision in our interview, which, for me, also signals that there is something there that brings you back to that. Brilliant.
Scott Wolfe: [01:01:51 - 01:01:52]
Maybe.
Anastasia Koroleva: [01:01:53 - 01:01:54]
Can we talk about kids?
Scott Wolfe: [01:01:56 - 01:01:57]
Sure.
Anastasia Koroleva: [01:01:57 - 01:02:09]
So you grew up in the family of entrepreneurs who had family business. How much that affected your desire to be an entrepreneur?
Scott Wolfe: [01:02:12 - 01:03:04]
I think it did a lot. I know that as some examples of how that affected me is that I don't know anybody in my family who wasn't an entrepreneur. I don't know anybody in my family, to my uncles and my aunts and my grandparents, who ever filled out a job application somewhere. I've never filled out a job application ever. I don't even know what it feels like to work on my resume, to, like, go work. I don't even. So it's. So when you say, does it. Did it affect you? It's like, it had to. I don't even know what it's like to be in a different paradigm.
Anastasia Koroleva: [01:03:05 - 01:03:08]
So do you wish that for your kids.
Scott Wolfe: [01:03:10 - 01:04:52]
Yeah, it's a problem. And I've noticed. And it's one of the, if I do have a regret about selling, that is one regret I have about selling, which is, again, it's hard to use that term, regret. But still, I do wish that what they, my kids, what they saw when I was, when I was working at levelset and building at levelset is they saw me really enjoying what I was doing, me really putting together something, building something, and being an entrepreneur. And now they don't see that. And I don't like that they don't see it. And the other thing, when I was growing up, I was actually working in the grocery stores, I was working in the business, and I got a lot of, I got a lot out of that. And my kids don't have that at all now. And so it does bother me in a way. I wish that that were different. It is. It's tricky, though. It's, it's, it, it is. I was fortunate. I do want them to have it. I am at a little bit of a loss of how to precisely give it to them. I definitely mean, I can't go buy a grocery store just to have a place for them to go work after school. And so it is something that I think about often don't have a real solution for it.
Anastasia Koroleva: [01:04:52 - 01:05:52]
Two of my kids are a bit older than yours, and then one of them is younger. And with the older ones, I actually really wanted them to be entrepreneurial as well. I thought it's the right path. I actually had a corporate career in a law firm, unlike you, when I was a lawyer. And I always thought that I don't want my kids to go there. So what I did, I actually raise them unemployable. And we'll see if it's a good idea or not. But they do both have a business. The older one is already very successful in his business. It's not easy, especially when your child becomes completely financially independent at 15. It's actually very, very scary. So I'm not trying to say that this is what parents should do. What I'm trying to say is that shaping their mindset and just letting them see that the entrepreneurial path may be fun and full of freedom, maybe perfectly enough, and they don't need to work in a store.
Scott Wolfe: [01:05:54 - 01:07:21]
What I think is something that it isn't. There's nothing specific. There's 8 billion ways to raise a child. There's nothing specific about working in a store or whatever. What I think was given to me, by having an entrepreneur, having a family of entrepreneurs, is. I watched these young people, my parents were very young when they had me. My mom 16, my dad was 18. So I watched these young people who had no business doing what, like, they had no rights to do the. No credentials, no rights to do what they did. Right. And then, but, but was able to just do it. And what I think the lesson that kind of like, that I think that I got and that. That I think. I think my kids get got when I was doing level set, or at least even now, in retrospect, doing livestock, is that this entrepreneur mindset is just. That you can just. You can just do things. You can build things. You can. You can. You can see something and work on it and produce it. There's ways to get fed and to succeed and to feel good out of your own hands.
Anastasia Koroleva: [01:07:22 - 01:07:32]
Yeah. Yeah. Self reliance. Yeah. This kind of self reliance that. Yeah. And confidence. I agree.
Scott Wolfe: [01:07:32 - 01:08:42]
I think that is to go back to vision. The ability to trust some picture that you believe that you see and make it so is a trait that's important to an entrepreneur. And I think even important in editing any setting versus what I think is the bad, because corporate life doesn't have to be bad, but what I think makes it bad is that you feel like the world is being done to you, that the job is being done to you, that you're, you know, you're. You can't, you know, when. When, like, when a corporation is dying or it's. When it's. When it's dead inside is when the people who are working there are clock in and clocking out, and they're never taking anything out of their heads, and they're never seeing a future they want to build and go and work on it. They're just going, you know, work on whatever it is in the project spreadsheet for nine to five.
Anastasia Koroleva: [01:08:42 - 01:09:02]
Yeah, yeah. And that sometimes becomes a trap for those of us who, after an exit, become investors, and then we invest, and that can become just very soulless because there is no beautiful vision to build towards.
Scott Wolfe: [01:09:03 - 01:09:39]
Yeah, I think I thought about, and, like, I think that that's one of the things that I struggle with a lot with investing is that it's so out of your hands. And so if I wanted to become an investor, I would, and I thought about this. I would have to create a point of view. Like, what's my point of view about the impact in the. In the world or an industry or something that I would need to make. And then through that point, of view. I come up with a strategy and a thesis and I come up with, like, my own, and then I can start to invest to create that, like, to create that surge. Yeah, I think that would be interesting.
Anastasia Koroleva: [01:09:39 - 01:09:50]
Yeah, I can, I can see how that can become very exciting for you with your need for a vision and making it real.
Scott Wolfe: [01:09:51 - 01:10:06]
But if I'm just going to be an investor and I'm going to pull out the spreadsheet every month and be like, oh, look at this one. Went up in price and this one, I mean, that's like, I stab my eyeballs out. I don't even know why people do that. Yeah, but they have a vision. I love investors. They have a vision.
Anastasia Koroleva: [01:10:06 - 01:10:12]
Different people do need different things in life. Right. So as long as it makes them happy.
Scott Wolfe: [01:10:13 - 01:10:59]
Yeah. And the vision is a little bit more about, just more generically looking at the financial of the. You can have a vision for. I don't need to make an impact in an industry or in the world in that way. I can make an impact on all these portfolio companies lives and all the people within them. And there's some intriguing things when you, and maybe their vision is actually more wide than mine, you know, because they look at, they look at impact in a much wider, have a lot larger aperture than mine where I always want the impact to be like, on something very specific.
Anastasia Koroleva: [01:11:00 - 01:11:01]
Yeah.
Scott Wolfe: [01:11:01 - 01:11:03]
Which is a difference.
Anastasia Koroleva: [01:11:03 - 01:11:29]
Yeah. Yeah. So, Scott, how your motivation changed from the time you started a business until today, what do you think drives you most? Because you mentioned impact and it piqued my curiosity. When you first started the business, what was your motivation for it? If you're very honest.
Scott Wolfe: [01:11:34 - 01:15:24]
I don't even remember, because it was, it was so, there was so many different things that I was starting at the time. I don't even know what. I can't quite remember. What was the drive behind? It was an impulse. I had an impulse to just create little. When things popped in my head or I saw something, I'd create a brand for it, a website, and then I'd create a small product or service and I had a little portfolio of them. I had a collection of them. I don't know why. I can't quite remember why. Over time, I grew to become an expert in certain ones. And then I started to fall in love with the nuances of the ones that I understood well and so levels. I wasn't born with the pacifier being stuck in my mouth about construction payment challenges. Right. And a love for that. But as I worked more around it and kept coming up with more things with it. I started to understand it more deeply and then started to fall in love with the, with the nuances of it. And that made me care about the impact that I made with it. And so over time, I started to want that impact and want that vision to come to be of how I saw the nuances of this problem, how I saw them getting solved and I wanted to solve it. And that's kind of one of the challenges of resetting. And you say, well, how does that. Well, what is your motivation now? Now I don't have financial motivations. I'm not in the business of being. Trying to, you know, to be ten times wealthier than I am or ten times wealthier than somebody else. Like, I'm wealthy enough, and to a degree, my wealth is such that it's going to be hard for me to impact it. Right. Like, I can go get a job tomorrow that pays really well and it doesn't really matter. So that's not a motivation. All the, all the knowledge I have in the nuances that I fell in love with, I can go back to them, but I feel like I'm called to that sometimes. That little toy of a company that I have is connected to that in a way, but I don't have that. Motivation is lacking. I'm not locked into that. So it is challenging. What motivates me today is kind of a challenging thing because it's, it's. I don't, I haven't fallen into the motivation around any particular lane, and that makes it really hard to sit down and do anything. And if you don't do anything, you're never going to get motivated.
Anastasia Koroleva: [01:15:25 - 01:15:37]
Of course. Of course. It's this cognitive overload which leads to our decision paralysis, and then we just stuck then till we get out.
Scott Wolfe: [01:15:38 - 01:16:23]
And like I said earlier, you're not going to find motivation on a rocking chair. I'm not going to find level set thinking about what to do. I found level set because I started to, I started to dance with a problem that I started to get smarter about. So that is definitely, as I think about what I want to do with the next three years or five years or ten years, to the extent that I want to, where I need to feel that purpose, have that paradox of purpose and I need to fill it. I do know that I have to get my hands. I need to get pots on the stove.
Anastasia Koroleva: [01:16:23 - 01:16:24]
Yeah.
Scott Wolfe: [01:16:24 - 01:16:29]
If I don't have pots on the stove, I'm never going to find that purpose.
Anastasia Koroleva: [01:16:29 - 01:16:30]
Yeah.
Scott Wolfe: [01:16:30 - 01:16:32]
And I'm reluctant now to pots on.
Anastasia Koroleva: [01:16:32 - 01:17:44]
The stove, you know? You know, it's interesting. Yeah. It's interesting how you see it, because it kind of aligns with what I found for myself as a way to reignite my motivation, and that's inspiration. I like to think of inspiration as this tool that ignites my energy, because, essentially, what inspiration does, it creates desire. Right. We suddenly want something. We get inspired. We want something. We get all this dopamine rush. We have all this energy. And if it hits something inside of us, some need, like a need to create, for example, it can sustain itself for some time. If it doesn't, it doesn't. Then we just have a little bit of fun and joy around it. But inspiration is an interesting thing, because the most powerful inspiration we get from other people, which naturally leads us to think, okay, we need to be very careful about whom we allow to inspire us. It's like the social curation, in a way, which leads me to my next question, which is, how do you choose those people to surround yourself with?
Scott Wolfe: [01:17:51 - 01:20:29]
Well, I think you. I struggle with this, actually, because I was. For the first 40 years of my life, the people that I was surrounding myself with was very organically developed and with level set. You. You have this. You have something that is driving. Is the. It's driving the car to go find more people in the space, find investors, to find partners, to find a team members and leaders and partners. So when I had this thing in a variety of things that was driving people to me, I found myself, I guess, talented or good, or I found my magnet. Like, my compass worked to know which ones challenge me and pushed me and intellectually got me to new areas and made me grow. Now I feel like the assembly of who I am around a lot is very inorganic because I don't have anything driving me to find people to even like to connect with. And so there's nothing. I don't have a reason to see somebody once a week or three times a week. There's a very. So now, if I wanted to assemble a group of people to challenge me or to help me grow, it would be a very awkward assembly. I have nothing to assemble them to. What am I supposed to do, right? Like, have a dinner, like. Like, you know, like, what is it in the midnight in Paris movie where f. Scotts Fitzgerald and Ernest Hemingway and all these people get together, and what am I supposed to do? Like, put together little, like, intellectual parties? That would be very awkward. And so I have nothing to bring together these people to do. And so I think it's a challenge for me now, in a different way. And I don't know how to solve it without having some, like some. Some organizing principle.
Anastasia Koroleva: [01:20:29 - 01:20:55]
Yeah, yeah. But we kind of have to do it. We cannot not do it because it would be similar to, you know, not dating ever, because we don't want to go through this initial period, which is not organic. Right. We have to do it. We have to rebuild our social circle around something else that we care about.
Scott Wolfe: [01:20:56 - 01:20:59]
Yeah. Yeah.
Anastasia Koroleva: [01:20:59 - 01:21:01]
It's a big challenge.
Scott Wolfe: [01:21:02 - 01:21:06]
And you have to. You're not going to attract the greatest minds.
Anastasia Koroleva: [01:21:06 - 01:21:07]
Why not?
Scott Wolfe: [01:21:07 - 01:21:20]
And you're not gonna. Unless you're not gonna be able to, in my opinion. I don't think you can attract great minds without having something that is gravitational pull for them.
Anastasia Koroleva: [01:21:20 - 01:21:21]
Yeah.
Scott Wolfe: [01:21:21 - 01:21:54]
Yeah. Like, they're not. They're not there to do you a favor there. You know, you're finding your room of five or ten people that. That challenge you and help you, but that's only because you're challenging them and helping them around something, of course. So without the something, it's extremely hard to get a real. To get. To get real group of people. And that brings you back to the first problem of finding something.
Anastasia Koroleva: [01:21:54 - 01:21:57]
Have you tried joining any organizations?
Scott Wolfe: [01:22:00 - 01:22:31]
I had some organizations I was a part of doing level set, doing certain moments of level set, and they were okay, and they were helpful in ways. I haven't done one after the exit, and maybe there are some out there that do this. I'm sure there are some out there for post exit founders and blah, blah, blah. I'm sure they have a bunch of different versions of it.
Anastasia Koroleva: [01:22:31 - 01:22:32]
Yeah, yeah.
Scott Wolfe: [01:22:32 - 01:22:33]
So possible.
Anastasia Koroleva: [01:22:34 - 01:22:48]
I can send you a whole list after the interview if you like, but you have to be open to going, and you have to be open to going and experiencing them. You have to go on those dates still.
Scott Wolfe: [01:22:50 - 01:23:19]
Yeah, I'm not opposed to, like, my calendar gets filled in periodically by a variety of things. And when I go, like, to a different city, I dial, you know, I fill the calendar with different. Different folks that I come across. I'm still involved with some old investors. I'm still involved on. I'm on the board of a few companies. Like, there's things that keep me. Keep the blood pumping in the space that I was in.
Anastasia Koroleva: [01:23:19 - 01:23:20]
Yeah.
Scott Wolfe: [01:23:20 - 01:23:41]
Right. I remain. I remain in that space. So I'm not a. And I'm not opposed to. To more. I do not like not feeling. I do not like feeling. I don't like. I like it to be organic. I don't like inorganic situation.
Anastasia Koroleva: [01:23:41 - 01:23:45]
Of course. It's easier. It's easier when it's organic.
Scott Wolfe: [01:23:46 - 01:23:46]
Right.
Anastasia Koroleva: [01:23:46 - 01:23:52]
But sometimes. Sometimes we have to get out of our comfort zone, reach out, meet other people.
Scott Wolfe: [01:23:53 - 01:23:58]
It's not be comfortable. It could be uncomfortable, but it's got. It's. It's not. It's not. It's not fake.
Anastasia Koroleva: [01:23:58 - 01:23:59]
Oh, yeah, that.
Scott Wolfe: [01:23:59 - 01:24:00]
Of course.
Anastasia Koroleva: [01:24:00 - 01:24:01]
Yeah.
Scott Wolfe: [01:24:01 - 01:24:05]
And to a degree, if I was going, like, trying to meet people.
Anastasia Koroleva: [01:24:07 - 01:24:07]
I.
Scott Wolfe: [01:24:07 - 01:24:14]
Just feel like there's a component of it that would feel fake if it was. I don't want to be forced.
Anastasia Koroleva: [01:24:14 - 01:25:00]
Well, I found if you open up yourself and you can actually be vulnerable, and authentic people tend to do that. It helps them. So one way to think about it is that you help others. You sometimes need a bit of patience, but they start responding in the same way, which is great, because it means that you have control over how genuine other people will be around you. Not always, but a lot of time. Okay, Scott, this has been absolutely amazing. I need to ask you my last question. I always ask the same question at the end of an interview, and that's, how do you want to be remembered?
Scott Wolfe: [01:25:04 - 01:25:15]
I mean, I thought about that when, you know, you know, what happens is, I think about that one sometimes, and then I think, I don't want to think about that. It's too complicated.
Anastasia Koroleva: [01:25:15 - 01:25:16]
It's okay.
Scott Wolfe: [01:25:17 - 01:28:09]
It was war. It's complicated. Warren Buffett said, oh, life is easy. You just write your eulogy, or you write your obituary, and then you spend your whole life trying to live up to that. And so, and this gets back to what we said earlier, where after you sell a company, you kind of, like, go into outer space. You look at the world and you say, oh, look at this. I'm not that critical. And then you say, who's going to remember me anyway, right? Like, no one remembers me, but, like, people don't remember level set anymore. And that was just three years ago. So I struggle intellectually with the. With the. Whenever I feel like someone is, I think. I think it's a lot easier. I think it's a lot worse to care a lot about that than it is to not care about that. In a way. Like, I think I see a lot of flaws in getting tripped up on. What do you want people to remember you by? And so I don't really know, but I do. I have my family, and I guess I care about that. They remember me, and they remember, I guess, my point of view, or, like, my. Be like, the way that I. The way that. The way that I would hope that their future behaviors and instincts are inspired by or instructed by my point of view, my instincts, and the way that I made decisions and was able to build things. I don't know if I need them. I don't know if I have a strong need to be remembered a certain way, but that there, yeah, it's. It's. I don't know what. And that gets me back. And I struggle with that. Like, well, then why did I. Why do I even do anything at all? Right, you're gonna get me into. I don't need to be in this existential quest about all this stuff. It's too, like, it's too much. And the more you try to solve it, the. You're never going to get to the end of this rainbow. And so all it's going to do is make it worse. So just, you know.
Anastasia Koroleva: [01:28:10 - 01:28:28]
Well, it's a very. It's a question that. It's a question that kind of reveals whom do you want to become in the foreseeable future? And what I can see is that you want to dig very deep into that existential crisis before you even consider suit of thinking about it, which is awesome.
Scott Wolfe: [01:28:29 - 01:29:36]
I love it. I just. I want to be in love with the things that I am. I like the feeling of being in love with things and. And I think that if you. What makes me happy is learning really deeply about certain things and getting very good at certain things and finding flow in certain things and having a point of view and trying to get that point of view expressed and out in the world and that dent made in some way, shape or form. I don't even need to be remembered for it. You know what I mean? Like, the dent can happen without you being remembered for it because, you know, I don't know who said it. Somebody said, it's like nobody thinks about you anyway and nobody. And they certainly don't think about you in 200 years. So don't get too tripped up on that. That's been okay.
Anastasia Koroleva: [01:29:36 - 01:29:45]
I love the open endedness of this. This is perfect. We are definitely doing it again in five years. I want to see where you.
Scott Wolfe: [01:29:46 - 01:29:48]
Everything's going to change.
Anastasia Koroleva: [01:29:49 - 01:30:09]
Thank you so much. I could just talk to you forever. We just need to stop. But it was a lot of fun. We went very deep and I'm very, very grateful for that. That's exactly how I like it. The hedgehoggy way deep with nuances. Thank you so much.
