Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"

38:26I'll never run out of the appetite to have the journey again and again and again and again. And 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 medium. I think about people like Steve Martin, who, you know, he's a standup comic for, reaches the mountaintop of standup comedy. He goes, man, I don't want to do that anymore. I'm going to go write novels. Yeah, as long as you're ready for the learning curve to learn something brand new from the start. Sure. So are you experimenting with anything?

39:13because one thing I often talk about with other exited 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 you know start running around exploring life but i'm still curious if you are doing something in that direction this particular age bracket of my children they there's just so many activities that they it's like it's like a constant they're interruption machines you know 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 street 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 right and you and you land you just land on the outside and you're like all right now what do I to do um i'm playing with another company concept right so i've been touring with that that gets me um that that is a little experimentation um i've been i've been experimenting with like writing um i did a lot of writing during level set in a different way um so i've been experimenting with that um and the rest of things that i've been playing with has been more maybe like hobby-ish style um spending more time than spending time with like spending like spend a lot i've been i've been saying yes as much as i can with the family yeah so talking about your writing talking about your writing that that article of yours that i love about the vision you wrote it about a year after your exit so i assume you you were in the in the process of processing your your experience of building a business and i think it's brilliant and you talk about how to form vision for for a company could we quickly talk about that and then i want to see how that translated for your own, uh, into your own vision for yourself?

42:02Which gets into the reason why I write a lot of things is I was, I had a particular person I was working with who was frustrated me. Um, because there was something about the, um, I mean, when I built level set 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.

42:52Right. 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 hadn't reflect on, you know, 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 reflecting on, well, how did I do it? And how does this make sense?

43:33I, with like the company that I, this little company toy that I'm playing with now, I very naturally, if I were to take that little framework that I put together and start looking at it with this toy, 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 will read that article now and bring it up and think about it with respect to my life because I don't I didn't apply it that way.

44:22Let'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? Yes. 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 money and all of that did you did you experience any of that unfortunately no it sounds like a lot more fun

45:01i might have i might have had a great time that's what i should have done 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, 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 to have time.

45:55I didn't want to go invest in things. I was very cautious about making any decisions at all. Did it cause you stress? Were you calmly cautious or you were just very scared? 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 say, and I'm going to do this and this and this. And I did. I learned a lot about wealth in that 12 or 24 month period. I very slowly dragged my feet with applying any of the money to any investments.

46:55And 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. Scott, I'm so impressed. I never hear things like that. I'm really impressed because most of the people I interview, 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 and to get my identity back for all their own reasons and made an impulsive thing.

47:45So I'm very impressed you had the wisdom to not do that. 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 because I'm not an investor. I'm not very, I'm very like, I'm not, I'm not an investor. Why would I go? People spend their career trying to be investors. Yeah. Why would I take my money, which I put all this risk behind to go risk it?

48:34I 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 to it was it was it was it was hard to say no to them all. Yeah. How did you go about that? Dragged my feet. And that's kind of been like my, my, my best friend is dragging my feet. And then I did like get sucked into a few of them at very small levels. 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 the 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 yeah a lot of local stuff like new orleans based stuff and things in the ecosystem that did a lot for me um i looked at it as charity and um And then eventually I learned how to even not do that.

49:46How 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 um 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 be a match for this fund go to the investors um and but that's a very that's like a very tricky area i think for people who exit it. It was tricky for me and I had a pretty firm point of view about it. You know, our mutual friend who introduced us, who was also your investor, Honam, prefers to invest in hedgehogs.

50:43Hedgehogs 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, So 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. Ho is always such a wise investor and a wise counsel on the board. And whether I probably even honed my hedgehog-iness further with Ho there as a nice echo to be on it.

51:43But I definitely do. I feel I have a lot of perspective overlap with Ho around that, which is you can't even even at Levelset, besides me personally, at Levelset, I really wanted to focus the company on what it was, its hedgehog concept. Yes. And I got I got a lot of this from being such a big fan of this book that I read when I was like 12 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 not and and digging into that. and um i don't i i get turned off when i when i see it's interesting because after an exit that's an interesting thing to put like an 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 to expect you that one wants 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.

53:05And 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, 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 um they can go become an investor they can go into charity and philanthropy um they could go into um you know there's all there's all these different lanes of second purpose but it's an interesting thought 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 which is that you it's like the old city slickers movie the secret to life is one thing are you remember that from city slickers yeah yeah yeah 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.

54:37No, but I think that's not, I don't know that's true. I think Steve Martin is a proud hedgehog. Okay. If you, if you, if you study him, He just hedgehogs into different things. And all of them were art. Okay. You know, they're all art. But he was a stand-up comic and he like dug that hole and he reached the top. And 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 he never did them all at the same time. He would go really deep. Given that for you business is art, all the other arts are open for consideration. Why not? And you can still be a proud hedgehog and Ho will be happy.

55:25Right, Ho will 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, too, which is teaching, philanthropy. A lot of people go into expression, right? Into different types of artistic expression. Yeah. And yeah, I think that that's a, it's possible.

56:02In, in 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 that teacher lane a lot of times I was um in expression lane I was writing a lot as a CEO and I was um creating a lot

56:34so it's 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, 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. And, and you keep going back to the idea of a vision in our interview, which for me also signals that there is something there that brings you back to that. Can we talk about kids? Sure. So you grew up in a family of entrepreneurs who had a family business.

57:32How much that affected your desire to be an entrepreneur? 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, my grandparents who ever like filled out a job application somewhere. I've never filled out a job application ever. So I don't even know what it feels like to work on my resume to like go work I don't even so it it's so when you say does it did it affect you I it's it's it's like it had to I don't even know what it's like to be in a different yeah um paradigm so do you wish wish that for your kids 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 my kids, what they saw 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.

59:09And 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.

59:34I wish that that were different. 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, I 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 it is it is a something that I think about often 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 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.

1:00:18So what I did, I actually raised 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. There's nothing specific.

1:00:59There's no, there's 8 billion ways, right, to raise a child. Because there's nothing specific about working in a store or whatever. What I think was given to me by having a family of entrepreneurs is I watched these young people. My parents were very young when they had me. My mom was 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 level set, 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.

1:02:09and work on it and produce it. There's ways to get fed and to succeed and to feel good out of your own hands, to go back to vision, the ability to trust some picture that you see and make it so is a trait that's important to an entrepreneur. And I think even important in 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 clocking in and clocking out and they're never taking anything.

1:03:15out 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 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 yeah to to build towards 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've come up with a strategy and a thesis and I'd come up with like my own and then I can start to invest to create that like to create that surge.

1:04:18And I think that would be interesting. Yeah, I can see how that can become very exciting for you with your need for a vision and making it real. 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 went down and down. That's 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. Different people need different things in life. Right. So as long as it makes them happy. Yeah. And the vision is a little bit more about just more generically looking at the financial.

1:05:04You can have a vision for, I don't need to make an impact in an industry or a 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 impact, you know, much wider. They have a lot larger aperture than mine, where I always want the impact to be like on something very specific. 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.

1:05:49When you first started the business, what was your motivation for it? 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. um it was an it was an impulse i i have 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 company website and then i'd create a small product or service and i had you know 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.

1:06:48And then I started to fall in love with the nuances of the ones that I understood well. And so I wasn't born with the pacifier being stuck in my mouth about construction payment challenges. right and 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 nuance of this problem, how I saw them getting solved, and I wanted to solve it.

1:07:44And 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 10 times wealthier than I am or 10 times wealthier than somebody else. Like I'm wealthy enough. The 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. 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.

1:08:39That little toy of a company that I have is connected to that in a way.

1:08:47But I don't have that motivation is lacking. I still don't, I'm not locked into that. So it is challenging. Like that, what motivates me today is kind of a challenging thing because it's, I don't, I haven't fallen into the motivation around any particular lane. This cognitive overload, which leads to our decision paralysis. And then we're just stuck there until we get out. 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 dance with a problem that I started to get smarter about.

1:09:42So that is definitely, as I think about what I want to do with the next three years or five years or 10 years, to the extent that I want to, where I need to fill 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. Yeah. If I don't have pots on the stove, I'm never going to find that purpose. 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?

1:10:38We 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?

1:11:25For the first 40 years of my life, the people that I was surrounding myself with was very organically developed. And with Levelset, you have something that is driving the car to go find more people in the space, find investors, to find partners, to find team members and leaders. in part. So when I had this thing and a variety of things that was driving people to me, I found myself, I guess, talented or good or, or I found my magnet, my, like my compass worked to know which ones challenged 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 connect with.

1:12:48I 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, you know, like what is it in the Midnight in Paris movie where F. Scott Fitzgerald and Ernest Hemingway and all these people get together. And what else does it 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.

1:13:37But 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 you can attract great minds without having something that is gravitational pull for them too yeah yeah um like they're not they're not there to do you a favor there you know you're finding a new 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 so without the something it's extremely hard have you tried joining any organizations i had some organizations i was a part of doing level set um doing certain moments of level set and they were okay and they were helpful in ways.

1:14:44I 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. Yeah. You have to be open to going and experiencing in them you have to go on those dates still yeah and i'm not opposed to like and my calendar gets filled in periodically by a variety of things and when i go like to a different city i i i dial you know i fill the calendar with different different folks that i've 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 yeah right i i remain i remain in that space um so i'm not a and i'm not opposed to to more i i i do not like um not feeling i do not like feeling i don't like i like it to be organic i don't like inorganic situations.

1:16:02Okay, 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? 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. It's okay. Right. It was complicated. It was more. It's got a bit of 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 this gets back to what we said earlier, where after you sell a company, you kind of like go into outer space.

1:16:41You look at the world and you say, oh, look at this. I'm not that I'm not that critical. And then who's going to remember me anyway? Right. 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. 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 and so. I've I don't really know, but I do.

1:17:36I have my family and I guess I care about that. They remember me and they remember, I guess, my point of view or like 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. You're going to get me into, I don't need to be in this existential quest about all this stuff. It's too much. And the more you try to solve it, you're never going to get to the end of this rainbow. And so all it's going to do is make it worse. It's a question that kind of reveals whom do you want to become in the foreseeable future.

1:18:45And what I can see is that you want to dig very deep into that existential crisis before you even consider thinking about it. I want to be in love with the things that I am. I like the feeling of being in love with things. and um 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?

1:19:29Like the dent can happen without you being remembered for it. That's good. Thank you so much. I could just talk to you forever. We just need to stop. A lot of fun. 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 hedgehog-y way. deep with nuances. Thank you so much.