Keith Smith: Exited Founder + Single Dad Talks About Mental Health, Purpose & Creator Economy

26:28What can I do to avoid it? What sort of tasks can I pile on myself to feel like I'm, you know, like I'm just too busy? There's no way I can invest this time in myself. You know, like all of those things would start to come up and I would, you know, probably half the time bail. And now I view my, when I go to my analyst twice a week, I view it like how I hear oftentimes some people talk about going and getting a mani or pedi. You know, it's like it's a moment of pamphlet. It's a I get to get a little massage. I get to get treated, you know, et cetera. It's like I get to go and sit and somebody who is an expert who went to Columbia gets to sit and listen to me for 45 minutes, drone on about all my shit.

27:06Like, how fucking great is that? And so I just view it as a moment where I get to go to the brain spa and enjoy some time, some downtime for Keith. And so that shift in mentality has made it very different. I've been going for a year and a half. I've never missed one appointment. And so I enjoy that process now. And it's not like eating broccoli. It's a really enjoyable process. flow so besides enjoyment what else did you get out of it I've learned some shit about myself and I think they they say that the the thing about about psychoanalysis is that in particular as a form of talk talk therapy it's very Freudian is is that I it's not necessarily about you know discovering things about yourself or anything like that really at the heart of it it's about being okay with what you will find out about yourself.

27:54And that, it took me a while to kind of internalize that. I think I still am probably internalizing it, but it's, as I started to learn stuff about myself, probably a year and a half ago, I would have been a little bit freaked out. And as I've, you know, kind of gone through this process and it's been a very good, healthy process for me, I learned a lot of stuff about myself, a lot of things that I didn't think actually existed, but actually do. And I've generally been okay with those things as I uncovered them along the way. And that's been a real game changer for me. Fantastic. So it's self-knowledge that you get.

28:25Self-knowledge. And I think, and why do I do this? Why do I do this thing? Or why does this thing keep happening to me? That's probably a better example of it. I think until we fully understand our unconscious self, we think that destiny probably has a lot more to do with our life than maybe it really does. And in retrospect, some of the things that I would have chalked up to destiny or bad luck were probably me self-sabotaging, you know, and me just like unconscious, you know, frankly, fucking with my conscious self. And so being able to better understand those things about yourself so that you can walk around in this, you know, in this wonderful meat sack that we all get that, you know, that we can say, okay, I actually have a little bit better understanding of what's going on here.

29:11I don't fully crock at all, but I'm getting better, and I'm starting to understand it a little bit better. I feel like that is a progress that, for me, has been really, really valuable. So for someone who started their, I guess, career focusing on biblical literature, how do you balance that psychoanalysis and spirituality in your plan for your own personal development and growth? So without getting too much into, because this will be a really controversial topic, so I will steer well clear of it, but I was raised in a very religious household. And I would say I've spent the last 30 years pulling those barbs out of myself and trying to better understand the programming and to deprogram myself to a large degree and so that I can get back to some basics.

30:05And so that's been a big part of it for me is just understanding my relationship to my theology, which is very substantial, and my relationship to religious organizations, which is to say that we're like oil and water probably is probably the best way to say it. And so I'm not a big fan of religious organizations as a whole for myself personally. And so trying to figure out how to be able to still have my beliefs and my theology separate from those religious structures that I think have probably, you know, tainted the real underlying message pretty significantly. And so a lot of it for that is, you know, the time and analysis for me has been just good to be able to assess that, understand it better, and take some of the stuff that I was doing kind of on my own to be able to better understand and to learn and have an expert opinion to be able to help guide me through that process, which has been extremely helpful.

31:12And I think, by the way, I think this is part of a larger topic that I'm so happy you're getting into because I think the idea of mental health and treating mental health proactively and reactively, especially for founders, is something we don't talk nearly enough about. And there is a stigma still, oddly, about it, part of a CEO group that happens to be all men. So I think that's part of what was going on in this particular dynamic. But I'm part of the CEO group where we all talk about our business challenges and that sort of thing. And we get together once a month. And when I first started going to analysis, I brought this up and I said, you know, we need to de-stigmatize, you know, this idea of treating mental health and crickets all around the room.

31:57People looked at me like I had three fucking ads. Like, what the hell is this guy even talking about? And I went, all right. So that's, I guess, my answer there. We're very uncomfortable when we start talking about their mental health. And I think some of that is men. Some of that is middle age. Some of that is the entrepreneurial journey. We've convinced ourselves we have to have all the right answers and we can't show weakness. Whatever it is, it's not healthy for us and it's good if we can shine a bright light on this stuff and start to talk about it. No, absolutely. If you look back at the history of humanity, spirituality and mental health were the same thing.

32:26They disconnected recently. But if you look at the basics, if you go to first principles of both, all religions, they teach us the same thing essentially. They just have different packages depending, I guess, on the particular culture, whatever works for that particular culture. But also if you look at the basics of psychology at the end of the day, it's very similar. So to me, for example, what was talking again about less is more, I think if you strip everything down to basics, whether you go from psychology or from spirituality, the basic values are still the same. The basic rules, the basic wisdoms.

33:09So that's why I was fascinated by the fact that you had this religious understanding, you had this experience with psychotherapy, and then you have this amazing experience with entrepreneurship and how you think about all of it to come up with your own wisdoms. It's beautiful. I really enjoy listening to you. Okay, so let's go back to more practical things. So were your repeat businesses, your sequels, different from your first one in terms of the industry and your focus? Or you tried to do rinse and repeat? I didn't do rinse and repeat, but I would say that the first company that I started after my exit was, at least they rhymed with the prior one.

34:03It was kind of tangentially in a similar space. and it evolved over time to be probably very distinctly different than the prior company, but at least it started in a kind of relatively similar category. My next startup after that was in a completely different field. It was in fintech, so I went from ad tech to fintech, and so it was very different. But I had started my career with a fintech company. It was before there was the word fintech because this was back in the early 90s. But so it was a little bit of a full circle for me. And there was a lot that I had learned and done and that was kind of foundational through my various startups that led me to the place where I could actually credibly run and build a fintech company.

34:55But, yeah, they were different. And then now my new startup is – it has very similar business model and strategy to the business that I exited in 2004 and later in 2009. But it's with a very different market and a very, very different underlying technology set, which is, of course, driven by AI, which is just fundamentally a whole new thing anyway. So what made you make this decision every time to go to quite a different space? So the thing that got me off the dime at this map from my last company, so when I left my fintech company, I'd been there for nine years, had built this company, was comfortable, knew all the levers, all the dials, all the switches.

35:46It wasn't exactly stretching me as an entrepreneur. And so I remember I had this moment of self-reflection and I asked myself the question, Keith, if you continue to build this company and you get better at being able to transfer money a little bit faster from point A to point B and get slightly better at being able to take a couple more basis points on those monies when you transfer them back and forth, are you really going to be happy with the contribution you've made to society as an entrepreneur? And I didn't like the answer that I got back. And so that was the thing that drove for me. And this was part of my iterative process of this.

36:22This all kind of happened around a new birthday and me questioning, okay, what is this version of Keith going to look like? What pieces do I need to deprecate? What pieces do I need to add? And I realized that I wanted to pour my entrepreneurial energies into things that were going to have a positive impact on society. and I knew that I wanted to lean in very, very hard into AI, knowing that that was going to just be this fundamental technology shift, unlike anything that we've seen since the Internet itself came along. And so those things drove me. And then the other piece that drove me really was that I've had this love and this infatuation with the creator economy.

36:57I've been working with creators for, in some form or fashion, for the last 14 years, and I just am absolutely fascinated by the fact that there's this group of small businesses that is very similar to most small businesses, but very different in other ways. The most significant way is that they're the most influential small businesses the world has ever seen. They influence like 60 % of buying decisions in the world at this point in time. And so they are a fascinating group of people and it's a delight to serve and build tools and build pot. Absolutely. I'm very happy you brought us to this subject because it's one of the reasons I was so eager to talk to you.

37:33So I've been studying post-exit journeys for 13 years now, and I've seen this trend recently, and it's a very strong trend, that more and more successful executive founders go into creative economy. And when you ask them about why they do that, it's where they see the most impact. I mean, part of it is probably understanding that they want to channel their creativity in a way that's very independent. But another part is this is the most impactful thing I can do. So now when I came across me for you and you, I thought, oh, my God, this is perfect. Because essentially, correct me if I'm wrong, but what you're doing, you're leveraging AI to help people multiply this impact, amplify this impact and make it even easier for them to achieve that very goal to maximize their impact.

38:29So please talk to me about that. And if you can help me understand whether I'm correct thinking that for an exited founder, it's a particularly interesting product. Yeah, I think that's a really interesting observation. I'm happy to hear that I'm very unique and special, just like everybody else. So that's good. It's funny when you find your behavior is very predictable, or at least fits a particular pattern. So it's like, oh, I'm on a special, unique journey. And oh, yeah, everybody else ended up at the same exact place. So that makes sense. And I think it's for a lot of the reasons that you cite.

39:01It's this, you know, this sense of like, you know, you spend I think as an entrepreneur, oftentimes, especially as a technology entrepreneur, you spend a lot of your time in the spreadsheet. You know, and I say that, you know, as a broad term where you're building product, you're coding, you're thinking about numbers. It's all very quantifiable. So there's always something that is attractive about the thing that wasn't quite there in the last thing that you did. And so being drawn to a creative environment and to customers that are steeped in creativity is something that makes sense to me and is certainly a part of what attracted me to this customer base.

39:40And I also don't view them as customers. I view them as partners. We aren't looking for creators to pull out their credit card and to pay for things from us. We want to partner with them. We want to be able to allow them to leverage their content, to be able to be able to have a bigger voice, to be able to have more impact, and to be able to make money while they sleep. And that's something that generally has not been available to them previously. So that's how we think about it. But let me back up just a little bit. And I'll say that the problem that we are trying to solve for, and so after I had this talk with myself, didn't like the answer that I got about the impact that I was going to have on the world, I said, okay, what impact do I want to affect?

40:16You know, what are the things that I see that are going on in the world? And I think one of the biggest things that is a negative for society that we see in America, but we see all around the developed world in particular, is the loneliness epidemic. And I think we all are aware of what's going on here, but most of us don't necessarily feel it because we now live in a world that is more connected than it has ever been before. but we are all aware that there are significant cohorts of us and of folks in our society that feel more connected than they ever have at any time before. And that is a disparity that we are setting out to try to figure out how to be able to at least collapse a bit.

40:56And so it's a big aspirational goal to say that we're going to solve loneliness. I'd like to say that we're probably going to put a dent in loneliness first before we start to get so greedy as to think that we can actually solve it. But I think one of the things that drives loneliness, and as we started looking at this and really trying to better understand the problem, is that the world is so connected, why are we, why are there that are less connected now? And part of that is because the behavior that a lot of folks are exhibiting online is they're either doom scrolling or watching endless porn.

41:31And these are both sit back and receive kinds of behaviors. You're not volunteering anything into this transaction, you are just sitting there and just swiping up, swiping up, swiping up, or just viewing, and you're not actually participating in this behavior at all, and that creates further isolation. So I equate it to having cotton candy for dinner every night, and I love cotton candy, but if I ate it for dinner every single night, I'd get no nutrients, and I'd eventually end up with cavities and diabetes, and so it's just not a healthy dinner, And so in moderation, you may be fine to have at the fair every once in a while, but it's not the kind of thing we should be having for dinner every night.

42:07And that's effectively what we've done to a large segment of Americans and folks across the world is that their media consumption now consists of a bunch of really tasty cotton candy that is giving them cavities and diabetes. And so our solution to this is to leverage AI to be able to create personas that folks can actually interact with and develop real relationships with. And I know that sounds weird. And a lot of people, when they hear us say, hey, we're going to have, you know, these synthetic, authentic relationships, they go, oh, you're just going to exacerbate the loneliness problem. And we'll see that, you know, I'm open to that criticism and I hear that criticism and we try to make sure that we take that into account.

42:47But our view is that the behavior that we are replacing is this behavior that is cotton candy-like behavior. And we aren't trying to be the Brussels sprouts on the dinner plate in terms of the healthy meal of media that we consume. Probably the mashed potatoes and gravy. We're not the kind of thing that you want to have for dinner every single night and solely just mashed potatoes and gravy. That's also not going to be healthy. But it's a lot healthier than cotton candy. And it brings folks closer to the kinds of interactions that they would have with real people. And it becomes an on-ramp to real-life human interaction again.

43:23And so that is our hope and that is our goal is that by creating synthetic relationships for folks that are disconnected and lonely. And these relationships are based on real people because they are personas that are trained on the actual full corpus of content of these really genius creative creators. and so now all of a sudden these personas, these AI personas can be developing relationships with this very lonely set of folks and be able to bring them out of some of this disconnected world that they live in. Yeah, it's so interesting that you focus on loneliness. When I first came across me for you, actually I thought about education because I thought, okay, how cool is that if there is an amazing educator who created this AI persona, and then other people can actually learn from that person by asking questions.

44:15Because for most of us, this is the best way to learn. If we can all have access to the best professors in the world any time of the day by just asking them a question and getting an answer as if we're chatting with them, isn't it amazing isn't that how we intuitively learn so i didn't even think of loneliness and another thing i think i thought about was my uh you know exited founders because i see as i mentioned there is a trend for these people to want to teach and share their experiences and um i can just imagine someone who who built a very successful company and i've interviewed so many of these people who really, really want to help young entrepreneurs to learn from them.

44:58And they work extremely hard recording videos, writing books, doing all these things, like really trying to share their wisdom with the world. But wouldn't it be amazing if they could create this AI clone for themselves who would be there for these people whom they want to help all the time answering their questions. So do I understand correctly that this is how MeForYou could be also used? Yes, absolutely. And these are our future use cases. You explained some of them beautifully. I think about the use case where I could be standing in front of my computer a year from now, and because it has computer vision, it can see me and the AI can see me.

45:44I'm standing in front of the AI persona of my favorite stylist, and I'm saying, hey, hey, I'm going to an event tomorrow night. Do these shoes match these pants? And, you know, is this the right outfit? Should I change? You know, those are really interesting use cases. Propping up my iPad on the kitchen counter and cooking with my favorite celebrity chef. And so they can see what I'm cooking and see how I'm presenting it and how I'm plating it and tell me what wine I should be pairing it with. Those are really interesting use cases. The reality is, is that when we started, we were a text-based chat and that's all we were.

46:15And so none of those really sexy, really cool use cases and educational use cases were available to us. We've now added voice. We will be adding video shortly. So what we want to be enabling is really what feels like a FaceTime call where you're just having a real human interaction video call with the AI persona. And the other piece of it, though, is not just about feature sets because we need to have those additional feature sets built in, but it's also about where do you start? You know, what vertical do you... And this is one of the questions that I don't know about the rest of the entrepreneur set, But it plagues me significantly.

46:49Where do I start? I almost always am building a platform that has a million use cases in my mind in terms of where it can eventually go. Where do I start in order to be able to get my initial traction, get my initial momentum, rather than trying to just boil the ocean? And so we started with an entertainment use case and a relationship, companionship-based use case. We think that eventually the idea that you have access to all of these great folks that will educate you, give you insights, train you. If I want to be an entrepreneur, I can learn from the best entrepreneurs. If I want to be able to be an amazing chef, I can learn from the best chefs.

47:28If I want to be able to have the best golf swing, I can learn from the best pro golfers. Those are all things that are use cases that we think will be available to us at some point down the road. For now, we're very focused on let's make it really entertaining. Let's make it really interesting. Let's make it feel like a companion. And we will build out all the rest of the feature sets. And likely those other use cases will come under a different brand heading, but very similar kind of underlying feature set. You know what would be fun? One day when you have your own virtual clone, I'll interview that clone instead of you and we'll compare how well you trained it on your own personality.

48:04Let's come back in six months or so. And I think that would be a lot of fun. Because we do have what we refer to as KeithBot, and we have a couple versions of KeithBot for various different things. But he's just text-based chat and audio at this point in time, and so he wouldn't be nearly as interesting. Well, I say that maybe before far more interesting. I don't know. But, yes, I think that's a great idea, and I would love to do that down the road. Fantastic. So besides me for you, what's next for you? What are your plans for the future? Would you love to achieve change or do? You know, I think I'm very civic-minded, and I care a lot about our country, and I care a lot about the direction that we're headed.

48:52And so while I – God forbid I will ever get directly into politics, I think I want to be more involved as time goes on, at least from the sidelines. I care a lot about this, you know, this this democratic experiment that we are, you know, a little more than a couple hundred years into now. And I'd like to see it continue. And I think self-government is is one of the greatest gifts that humanity has ever given itself. And I'd like to see it continue. And so I think, you know, that's that's probably is I think about kind of that that the larger impacts that I would like to have. That's probably where I would where I would like to focus is making sure that we have a self-governing democracy that is fair and equitable for all.

49:33So I think, you know, when I think closer to home and I think about things that I can probably have more control over or at least have more impact on, they are things that have to do with me, my family, my close circle and my loved ones. And so that's an area that I'm very focused on. But the impact that comes there really is largely driven not by the resources that I can pour into that effort, but by the time that I can pour into that effort. and so I look forward to having more time available. You know, at some point in time, I'll probably have grandkids. I want to make sure that I have time to be able to go and spoil them and make them ridiculous as I hand them back to my children.

50:14Those will all be fun things down the road at some point in time, but yeah, as I think about, you know, I'm 52, or as I like to say, I'm Keith 5.2 at this point in time. When I'm Keith 6.0, those will probably be things that'll be coming close and I'll be excited about those at the time. Amazing. Let's talk about your evolution of identity from the time you started your first business till today. You know, there's a lot of change. And my closest friends will tell you that I've changed just dramatically in terms of my worldview. I think there's some core underlying values that probably have not changed.

50:49And so I'm happy to say that there's still a kind of a true north that probably existed and still exists. I think how that expresses itself has changed pretty dramatically, not least of which in terms of how I vote. I was raised in a very stopsly conservative home, and as I started to realize that the world was unfairly tipped towards me just purely because of the lack of melanin that I have in my skin, And that was a weird thing to me, and I didn't understand it because I grew up in a town that had no racial diversity or very little to speak of. And so I kind of started to understand the world really when I turned 18 and left home and went to move to a big city and moved to Seattle and went, oh, wow, this world is very different than I expected.

51:44And there's a lot of different kinds of people out there, and they have a lot of different worldviews. So that's been an evolution that really kind of began when I turned 18 and left home and has continued to this day. And it really is that through line that I mentioned earlier, which I think the underlying theme is me trying to, and I think trying is probably the right qualifier to put on it, trying to better understand and empathize with people who are not like me and don't have the same worldview and the same world experience that I do. and trying to figure out how do we create more opportunities and be able to distribute the potential for opportunity more widely in our society.

52:24And I think that is not only good for those who have missed out on those opportunities, but it is fantastic for society as a whole. And we will do well as a society if we open it up to all folks and don't just try to push certain groups to the edges. and we have too much right now of folks in the center trying to push other groups of folks to the edge just purely because of how they were born, what they look like, what their ethnicity might be, et cetera. And I think those are things that are tragic and that has been a big part of my evolution as a human in terms of my worldview and how I view others.

53:03Amazing. So if we zoom back into that moment when you just sold your company and you no longer could call yourself CEO and co-founder, how did it feel and how did you get over it? What helped you to get where you are now? You know, it's really interesting. I think there's a big difference between when you have a failure outcome versus when you have a successful outcome. For me, anyway, when I had a failure outcome as a company, I didn't reflect. I spent time probably a year or two later reflecting, and I reflected a lot on what were the entrepreneurial lessons that I learned in that process. Like I did spend a lot of time, you know, writing those down, processing them.

53:45I didn't spend any time thinking about what did this mean for Keith and what does this do for my emotional state, you know, and those sorts of things. Because I was just like dusting the, you know, I was just, you know, getting the dust off me and I was going again and I was moving forward. And so that was the order of the day. So I didn't get a lot of reflection time. What's interesting is that I think when you have the combination, when you have a successful exit, you get two things. You get resources and you get time. and oftentimes those are the key ingredients to an existential crisis. And I think we see this a lot with recently exited founders is they're like, what the fuck do I do?

54:20Who am I? What am I attached to? What's my platform? I don't even know what's my purpose. And you're like, well, dude, you have$100 million in the bank and you have beautiful kids and you have this wonderful partner. You know, it's not all bad. You can probably figure this out. But it's very disorienting for a lot of folks to find themselves in that situation. And so time plus resources often equals existential crisis. I think a lot of times that can be good for us because asking the question, why do I exist, is a good thing for us to be asking ourselves and trying to figure out what is our purpose.

54:50And so those can be good things, but they can also be anxiety-ridden. And I was no different. I experienced both sides of that when I had successful accidents and when I had unsuccessful accidents. So would you say you're now detached from this identity of a foundacy or is it meaningful? for you in any way. It is still, unfortunately, core to my identity. Yeah, it really is. It's, as much as I would like to be able to have this perspective, be able to say, oh, I'm so much bigger than that, or I'm so much, you know, I'm a separate person from that, et cetera. And I am, but I'm not. You know, it's, yeah, it's, I am wrapped around the founder CEO identity and it is wrapped around me.

55:27What I'm not wrapped around is any individual company. Like I, I view those as, as vehicles, important vehicles, you know, really crucial vehicles. You got to be thoughtful about which vehicle you're going to be in, but you can be in another vehicle again before too long. And so, you know, being tied to the idea that you can go out and in a capitalist society, just get a team of people to believe in your crazy story that you're telling them, gain some resources and go and act this out and start doing this is just a beautiful, beautiful thing. And so I love that. I love that formation. process.

56:07I love the process of the zero to one. And it definitely is a core part of my identity. And so when I'm 70, 80, 90, I have a view that longevity is going to continue to go. And so probably when I'm 150, I'm probably still going to be starting companies. And I enjoy it. I love it. And it's a lot of fun for me. Amazing. So Keith, how do you define success? It's changed. So I do have a financial definition of it, but I have a broader definition as well at this point in time. And I think if you'd asked me that when I was 20, I wouldn't have differentiated between those two because financial success would have been my definition of success.

56:46There would not have been another part to it. And now when you say that, the first thing that comes to my mind is, are my children happy? Are they healthy? Do we have a fantastic, productive relationship? And the answer to all that is yes, so I'm very successful. I think there's metrics that I think we all kind of have for ourselves in terms of financial success. All of mine revolve around kind of the two tiers of do I have personal freedom for myself and for my family? And we live in this capitalist society to be able to do what I want instead of what I have to do. And then the second milestone is, do I have the resources to be able to impact society around me, hopefully for the better, in order to be able to kind of shift it more towards something that I think is good for society?

57:32And so I think those are kind of the two metrics. And so I'm – good news is I have goals still that I'm working towards pursuing and achieving on the financial success side. Great. Great. Are you familiar with imposter syndrome? Very common problem for successful executive founders. Yes, very much so. And there's a good example of something that I realized about myself that I didn't want to know about myself, but I figured it out through analysis is that I would have told you I don't have imposter syndrome at all up until I started analysis a year and a half ago. And then I realized, oh, shit, I do have imposter syndrome.

58:09It does plague me in ways that I didn't even realize it plagues me. And so, you know, I think we all have it. I would have recognized that I had it at some level and I would just thought it was a very minor part of my, you know, my psyche previously. It's probably bigger than I would like it to be. But generally speaking, it's not something that I feel like is something that is, that plagues me or is a major obstacle to me or has been in my world. I do think that that is very different for other groups of folks. And this goes back to, you know, to my comment about spreading opportunities around in our society.

58:45And I think there are lots of groups and pockets of folks that as a class, they've been told, you are not cut out for entrepreneurship, and you should not pursue entrepreneurship, or it's not, the doors are not going to be open for you. And we are going to purposely, you know, the system is going to have more friction for you than it is going to be for somebody else. And so that is something that I think happens a lot, and I think that leads to imposter syndrome. And I don't think that's imposter syndrome. I think that's a different thing, but I think a lot of times it expresses itself as imposter syndrome.

59:17But that's a societal and systemic tilt against certain groups of folks, and that's something I think that we can rectify without them just having to look internally as to how they can get over that. Fascinating. So basically by discovering your own imposter syndrome, you started feeling more compassion and started recognizing other people's imposter syndrome and how it can be an obstacle in their personal development. Absolutely. Absolutely. And sometimes I think it's not imposter syndrome. If you are a woman, you're a person of color, you are going to have a harder time raising money for your startup in America.

59:57And that's just fucking bullshit. And that's so aggravating, and it doesn't make any sense. And there's gold in those hills there for investors to be able to go and say, hey, look, we have some amazingly talented people that are just not getting seen and not getting funded and not getting the resources to be able to carry out their vision, and we should solve for that. And I think a lot of times, you know, if I'm a person of color or, you know, or a woman or a minority in the sense of the, you know, the capitalist system that we have and the capital allocation system that we've developed, then you can start to think, oh, yeah, I don't belong here.

1:00:30You know, this is not right for me, et cetera. And those are all the things that we say to ourselves when we have imposter syndrome. That's not imposter syndrome. That's systemic biases against certain groups of people. And that's something that we should fix as a society and not look to women and people of color to say, hey, go and fix your imposter syndrome and just muscle your way through it. Yeah. Obviously, there are objective obstacles in the society that's different. So you've been doing therapy for a year and a half now, you said. So what are the demons you uncovered, the biggest ones that you're willing to share?

1:01:08Boy, the big ones, I don't know if I am willing to share. Um, that's okay. Think about that. You know, no, I think it's, uh, it's, it's, it's a, it's a fascinating, you know, and if I say we should destigmatize mental health, then I need to destigmatize mental health. So, uh, so I think it's a great question. Uh, you know, I, I think there is a, there's a, there's a level of self-sabotage that I figured out about myself that I would never have thought that I actually did. And so trying to square my, my unconscious desires with my conscious desires is something that I had never spent significant time trying to do and resolve the disparity between those two.

1:01:45I think we all have disparity between those two. And to a large degree, we don't have responsibility for what our unconscious wants. And a lot of times what we have is a direct reflection of what our unconscious desired and wanted. and coming to grips with that idea and making sure that I then am introspective enough to be able to deconstruct what's been going on in my life to say, okay, these are the behaviors that actually led to this outcome. It wasn't just bad luck. It wasn't just that the stars aligned against me. It was that I fucked up in these three ways, and I shouldn't have done that, and it's kind of inexplicable when I look back as to why I did those three things.

1:02:31Let me think about that so I will be conscious and aware of that when I get the opportunity to make those kinds of decisions again in the future. And hopefully I can undo those patterns and I can be thoughtful and purposeful about them as I go forward and not self-sabotage. And that would, I would say is probably, there's a lot of pieces to that and that applies in a lot of different areas of my life. That's probably the biggest one. And it's not, they weren't in big obvious ways where it's like, oh, Keith's a heroin addict and so therefore it's clear as to that he's self-sabotaging. It wasn't anything that obvious.

1:03:01It was much more subtle. And those are the ones that are harder to detect. But it's been a lot of fun uncovering that stuff. Can you give me an example of those subtle ones? I oftentimes will. No, it is the short answer. I could and I would get myself into potential trouble here. So I'll leave that for my analyst about that one. And that's all right. Fair enough. I was about to expose some really some dirty laundry there. But I was like, yeah, I'll think better about that. Fair enough. I just wondered if you have a good illustration. It always helps to deliver an idea if you have a good story behind it.

1:03:38So this takes me to your view on how you choose people you surround yourself with. So there's kind of two major lenses that I guess I look through. I think about this as you're asking that question. I'm thinking about this in the context of my founding team. So with my latest startup, there are four of us that are co-founders. And that's not super typical, but it's not atypical. And the way that we came to that is that there were four of us that came together in the very beginning that we were the pigs at breakfast, not the chickens. And I don't know if your audience knows that metaphor. But, you know, if you if you have a breakfast of ham or bacon and eggs, there's there's two different animals that are participating in that breakfast.

1:04:31There's the chicken and there's the pig and the pig participates at a very different level than the chicken does. And that's what it's like to be a founder at a startup is that you're the pig at breakfast. You don't get to just lay an egg and then move on to the next thing. You're really involved in this thing. And and and you, you know, you commit your entire self to it in the same way that the pig commits to the bacon. And so – and it can be a little bit of a gross metaphor, but it kind of drives on the point that we are really invested in this thing. And so I found four people who, A, could really get that invested.

1:05:03But the way that I chose them was kind of two things. One is what happens to my energy level when I'm around this person? Do they detract from my energy? Do they spin me up? Do they propel me to greater things? Do they just make me comfortable and tell me what I want to hear? you know what is what is the reaction because this is not a a situation where it's just like I can I can judge them based on their isolated skill sets it's really how are they going to operate in this team and how are we going to operate together and are we going to have a situation where one plus one is going to equal more than two and and we've all you know had those those interactions where you go I get done talking to this person and oh my gosh I feel like I you know I just got drained like I like there was a there was this big soul-sucking mosquito that was just sucking you know, the energy out of my body at this point in time, or there's people that have the exact opposite, you know, effect on you.

1:05:55And so that's the first thing that I look for is, is this person going to drive me towards greatness? And am I going to be able to drive them towards greatness? And then the second thing is, are they going to be able to complement my abilities, my skills, my views, my background, my perspective, all of those kinds of things? And not complement as in praise me, compliment as in complete me, and be able to say, okay, Keith is pretty good at this, but he's terrible at these other three things, or not as good at these other three things, but he's now been able to build a team around him where he has these other three things that are really well nailed down, and the things that they may be weak in, Keith has strengthened.

1:06:34So if we can find those, and there's an ideal overlap, by the way, also, it has to match the jobs that you have open and the jobs that need to be done at that point in time in a company. So, but the two main ones is, what do we do together? What is our energy level? And do they complement me? And do I complement them? Okay. That's clear with respect to your business. How about your personal life? That's a harder one. I just went through a breakup. So that's one I've spent a lot of time thinking about. And yeah, I think there's an aspect of, so, you know, I think about this in the context of choosing a partner as an example.

1:07:10and so I'm on the dating apps right now and I'm going through this process and I'm borrowing a line from what the ladies use here in New York which is that I am dating with intention meaning I'm trying to find a partner I'm trying to find somebody who will compliment me in that same way and it's interesting if I boil it down I kind of use that same lens that I look through what is the energy level going to be between the two of us am I going to detract from her is she going to detract from me or are we going to end up you know, creating a dynamic where, oh my gosh, I feel so much more energized.

1:07:41I want to be in this person's presence. You know, we really do, you know, come together and create more positivity together than we do separate and, you know, away from each other. And that generally means that you have to start with two entirely old people on their own coming together before you can really have that sort of expectation. So that's kind of the foundational piece. And then the second piece is, you know, do they compliment me? One of the things that I don't bring into a relationship is fun and whimsy. And, and a relationship is not very fun without fun and whimsy in it. And so, and so I want a partner who's going to bring fun and whimsy, you know, and, and, and lighten me up a little bit and, and let me see the, the, you know, the, the fun in life and let me stop and smell the roses and, and encourage me to stop and smell the roses.

1:08:29And And those are things that I will oftentimes forget to do on my own. And having a partner who has a worldview that complements mine and is a little bit near-term optimistic more than I am is very, very valuable. So it's pretty similar, oddly, between picking a co-founder and picking a partner. Brilliant. I don't think I've ever seen such an eloquent description of your dating strategy. It helps when you're in the middle of it. It's another biz debt deal is what it is. You're trying to find the right partner. You're trying to find the right investor. You're trying to find the right partner. The outcomes are very different between all three of those.

1:09:10The underlying motions and mechanics are pretty similar oftentimes. It's about telling your story, making sure that you find somebody who's going to be a good fit. Do you have the right energy and do you guys complement each other well enough? So do you have a sense of purpose? I believe so. I think that's a fantastic question. But yes, if you would have asked me that question two years ago, I would have said no, at least if I was being honest. I do psychedelics a fair amount. This is a bit of a tangent here, but I mostly microdose mushrooms. And I would say, you know, any other intoxicant that I use, whether it's drinking or wheat smoking that I periodically might do, those are things that are just crutches.

1:09:52They don't probably help me. They're just kind of, you know, they serve to self-medicate the pain away a little bit for us. And we all kind of do that a little bit. I would say psychedelics are actually a net positive in my life and have been a significant competitive advantage to me. They are like a fresh snowfall. If you take the same ski run a thousand times, before you know it, you're going to be skiing in a rut. And you're going to be going down the same pattern and the same routine. And the snow is going to get worn down. And it's hard to get out of those ruts in our life when we do that.

1:10:27And one of the things, you know, there's a lot of ways to be able to get out of those ruts. One of the ways that I've found that is a very rewarding way is, and this is not advice. This is just me sharing my personal experience, but it's to do psychedelics, mushrooms in moderation and get a fresh snowfall and give my brain the ability to be able to pick a new route and a new path. And that is what that's been a big part of this journey over the course of the last couple of years that has allowed me to put myself into a place where my life does now have purpose. Amazing. So if you had to rate your level of fulfillment from zero to 10, what would it be?

1:11:08Oh, this is such a great question. So one of the things we do with our co-founder team every week is we ask three 1 to 10 questions. And they're not quite exactly this, but they force us to quantify it. And then we have this spreadsheet, and we can track it all the way back and see how we're doing. And we have it there for all to see. We kind of give a little anecdotes every week to each other as to why we're feeling this particular way. But it has to do with personal, with health, and with work is how we rate our 1 to 10. And so in terms of fulfillment on a 1 to 10, I would say I'm a – I guess the narrative on that is that I am extremely happy never fulfilled.

1:11:52and that creates a dynamic for me where I'm pushing myself forward. But in the reality is, and that's been a nice anecdote that I've told myself for a long time, but the reality is that I would say, yes, I am very fulfilled because one of the things I realized is that fulfillment doesn't come at the end of your journey. It needs to be an integral part of the journey. And I think that's changed for me. And I've still managed to be able to kind of still keep a motivation for myself by saying, okay, I want to be more fulfilled or I want to be able to complete more and have a particular purpose that I'm pushing for.

1:12:25But I'll allow myself to be fulfilled, to be happy, to be even content, which is a word I used to be allergic to along the way and through this journey. And I think that makes A, the journey more enjoyable. B, very importantly, it makes you more tolerable of a person along the journey for all the people who are right alongside you. And I think it improves outcomes. More to come on that. Check back with me on five years, and I'll let you know if it improves outcomes, at least in my case. But I think it does. So what is it from zero to 10? Oh, I didn't answer the question, did I? You gave me a beautifully deep answer.

1:13:03I actually avoided answering the question. 8.5. It was that, yes. Oh, wow. That is very high. Well done. Yes. I would say that's an accurate assessment, and it might be different tomorrow. then maybe we're talking about levels of happiness. Possibly. It's possible that I have a hard time differentiating between those two at any given moment. Yeah, it's possible. So you said that you feel that you need someone else in your life to lighten you up. And yet, for me, you come across as a very kind of happy and almost bubbly person. So I was very surprised to hear that you need this from somebody else.

1:13:44Can you tell me a bit more about that and how you balance joy and, I guess, fulfillment in your life, which would be a more serious thing? Yeah, and I would say I wouldn't characterize it as, yeah, I probably use that word, but I should choose my words more carefully. But I wouldn't say I need that. I want that in a partner is what I want out of a partnership. And so the good news is, though, I have a lot of other relationships in my life that do bring whimsy, do bring joy, do lighten me up. Most notably, my daughter, she's been good at this since she was about three months old. And so and she's still good at it today and just as a way of making me smile, making me laugh.

1:14:30My son has the same impact on me. That wasn't the case five years ago. So both he and I, when we were in high school, we had challenging relationships, shall we say, with our fathers. And so he and I had our challenges, but we have a relationship now that is so rich and so fulfilling and so deeply important to me. And so both of my children, probably more than anybody else, bring me, kind of create that whimsy, get me to not look at life always so seriously and pull me away from those tendencies. So that's very positive. I think in terms of joy in particular, I think there's other things too I think that I would say – I don't know if this – this doesn't qualify as fulfillment.

1:15:20But having something outside of your family as a hobby is an important thing. And this is not something that – when you're starting companies and you're raising a family on your own and you're a single dad – I remember I was asked once when my kids were still in high school, somebody – I was at a party and they said, what are your hobbies? and I was like, fuck, I don't have a hobby. I can relate to that. You don't have to name for hobbies. Exactly. I'm like, I have a big to-do list. Is that a hobby? I don't know. And I have a bunch of things I feel guilty about that I haven't done today for my children that I wanted to do, but I don't think that qualifies as a hobby.

1:15:54I like to go to my daughter's cheer games and all my son's activities, but I guess that's a hobby, maybe. But that's kind of where we are as parents. And so the reshaping of our own identity is an opportunity when our kids leave the nest. And so my daughter moved back home shortly, just for a brief period of time after she graduated college. And I said, hey, I'm gonna give you the gift that most parents don't give their millennial children, which is the gift of independence. And so I'm going to invite you to move out the nest. So you have six months and then go out and start making your debt in the universe.

1:16:27And that was received okay at the time. Since then, in retrospect, it was the best move ever. She and I are both very happy that that was the case. But it allowed us to be able to develop a new stage of our relationship and to be purposeful about that new stage of our relationship. And that has been an absolute delight. So my daughter and I sat down. I remember when she turned 18 and we had this conversation. And I said, you know, look, it's been controversial. But, you know, I told you before, I'm not your friend. I'm your dad. But now we get to reshape our relationship. And, you know, now maybe I'm your friend.

1:17:00You know, we get to decide, you know, what are you going to call me? How are we going to interact with each other? How often are we going to talk? What does our relationship look like? Are we transparent with each other? Do we keep things back? Like we get to define this and I will respect your boundaries in whatever order, you know, in whatever way you communicate them to me because I want to make sure that I am respectful in this relationship. But I want to make sure that we are purposeful about this and we don't just let it accidentally happen to us. And so that was so effective and so impactful to us that I did the same thing when my son turned 18.

1:17:27And it set just this foundation for this relationship with both of my adult children, which I had very high expectations for. But this has been far more rewarding than I ever could have expected. Every stage of my children's growth has been my new favorite stage. But this is, you know, hands down my favorite stage by far. It's so much fun. It's so enjoyable watching them put their dent in the universe. And so I enjoy that a lot. And that's allowed me then to be able to give up the identity as caretaker. And so I still get to be dad. I still get to be friend. I get to be buddy. I get to be counselor.

1:18:05I get to be the person that they call for advice, which is so rewarding and so great. I don't have to be caretaker anymore. And that has freed me up to be able to have another identity. And so I have a new hobby. And so I took up the hobby of one-wheeling. I'd never really ridden a skateboard or any sort of board before. And so I started at age 50. and I've ridden almost 6 ,000 miles on my one wheel. It's my transportation, it's my hobby, and it's my exercise. I probably put 80 to 100 miles a week on it. And as I like to say, if I can't get there on my three-horsepower electric vehicle, I kind of don't want to go there.

1:18:43So Manhattan is great for me in that regard because most of the things I want to go to are within reach of my three-horsepower electric vehicle, and that's how I get there. and it's silly and it's ridiculous, but as I like to say, I used to have a car and it would bring me places and now I have a one wheel and it brings me joy. And that's very good. Well, I'm sure it attracts a lot of attention in Manhattan. I do get a lot of looks and a lot of stares and every once in a while people go, you know, get out of the road, what are you doing? So yeah, it's interesting. Brilliant. So you've given me so many golden nuggets in this interview.

1:19:19And to summarize this, I'd love you to tell me what you think are the most important lessons that you've learned since your first life-changing exit. I would say it's interesting. I'll give you two lessons that I actually learned from my children that were two absolutely just seminal moments for me. But I don't think I internalized them or really learned them until after my exit. So the seeds were planted and it didn't start to actually sprout until I think post-exit. And so the first was that my son, when he was about five or six years old, and keep in mind at the time, my mindset was very much this very conservative kind of worldview, et cetera.

1:20:13And so we stop at a stoplight. We're in Seattle. And my son is in the back, and he's very inquisitive, and he's always just observing and seeing everything that's going on. And there's an unhoused person that's sitting there with a sign, and they're asking for change. And Bennett says to me, he says, Dad, what does that sign say? He can't read yet. What does that sign say? And so I say, well, he's looking for money, son. He says, well, why is he looking for money? And I said, well, he's made some bad choices. And probably those bad choices led to more bad choices. And then that led to a bad circumstance until he probably lost his home.

1:20:43And so ultimately, you know, he just made a bunch of bad choices and that's where he ended up. My son listens to this and just kind of stares at me in the rearview mirror and rolls down his window, reaches into his pocket, grabs the$5 bill that he'd gotten for allowance for that week, reaches out and just hands it to the man. And doesn't say a word, just looks at me in the rearview mirror and rolled up his window and we went on. And there was a moment of like this empathy that I was lacking so badly at that moment that he just gave me at that moment. And it changed me. It didn't change me immediately.

1:21:20It took a while. But that lesson fostered. I had festered for a while. And it finally came to be a seedling. And then there was another similar situation with my daughter when she was about 14 years old. I was hosting a bunch of CEOs from the Seattle area at my home. and I was introducing my kids to them. And so I introduced my daughter and she's this tiny little thing and just this vibrant, packed with energy, a little bean. And she made some comment that was a very feminist kind of comment. And I turned around to the person and I said, yep, see, I raised a feminist. And my daughter just looks at me and she goes, dad, who raised a feminist?

1:22:01And it was this moment where I was like, oh, here's me taking credit for what she did. And it was, again, one of these seeds that got planted that didn't really start to sprout until later. But the underlying message in all of that was that when I had kids, it was something I looked forward to. I wanted to do since I was little. And so I was excited to be a dad. And I knew that I would impact my children greatly and I would shape them greatly. What I was not prepared for and what I did not know is how much they would impact and shape me. And that is the gift of, you know, So having children, raising them, being hands-on with them, and hopefully learning as much from them or maybe at least a significant portion from them as you were also then training them as well.

1:22:46I couldn't agree more. Also, they push you to be less selfish whether you like it or not. It's probably the choice. No choice. You have to be selfish. Making you a better person whether you like it or not. Exactly. Yes, so well said. So well said. So, Keith, my last question, how do you want to be remembered? You know, I want to be remembered as somebody who truly impacted and helped to be able to make society better and giving people more agency, more freedom, more autonomy, more liberties. and that may, you know, when my final chapter is written, that may mean that it's, you know, that's my group of people that I've helped do that is two of them, just my own two children.

1:23:38Hopefully it's bigger, you know, a bigger audience than that. But I think if I can give people the ability to be able to find their own freedom, to be able to have their own, you know, to be able to, you know, teach a person to fish rather than just giving them a fish, you know, kind of a concept so that they can come into their own and find the joy that comes with freedom within this kind of society and be able to have a society that is going to reward them and be able to allow that to happen. That's what I would like to leave behind, and I'd love to be remembered for being able to participate in helping that at least some level.

1:24:15And by the way, I'll also point out that I don't think that's coming for another couple of centuries. I know this is a controversial topic But I think that over the course of the next 20 years Humanity will likely solve old age And we will have the option if we choose it To be able to look like we are 40 years old For hopefully decades if not centuries And so we will see But I think that day is probably a long way off So we'll see Check back with me in 150 years and we'll see where we're at I'm a big fan of that thought as well I love thinking that way. Good, good. I love finding other folks that are also with the same mindset because there's a lot of post-exit founders that share this view.

1:24:59Yeah. I guess most of us are optimistic by definition. Otherwise, we wouldn't be where we are. Yeah, we're a little petty that way. Naively, irrationally optimistic, but still. Yes. It has been such a delight. And I have a million more questions for you, which I have to save for the next time because I have to let you go at some point today. thank you so very much for this for your time and your wisdom and opening up so beautifully. Thank you, Anastasia. This has been a delight. I enjoyed the conversation the wide-ranging topics. It was a lot of fun. So thank you.