Keith Smith. Money + Time = Existential Crisis

Written By Anastasia Koroleva

Episode - 22

Keith Smith. Money + Time = Existential Crisis

 
 
 

Keith Smith. This exited founder has spent 2 decades building 5 companies and raising 2 children as a single dad. A deep and original thinker, he chose to confront his post-exit mental health issues head on. In this episode, Keith openly shares his insights, therapy takeaways and how he found his latest mission in empowering creators with his innovative AI tools.

What We Discussed:

00:01:27: Welcome

00:01:58: Keith's Personal Background and Experiences

00:03:13: The Impact of Wealth on Keith's Life

00:05:12: Personal Growth and Changes in Priorities

00:07:20: Changing Perspective on Equity Distribution

00:11:39: Starting A Business with A New Co-Founder

00:13:00: Motivation to Start the First Company

00:14:20: What Wealth Means

00:15:24: Balancing Entrepreneurship as a Single Dad

00:19:45: Current Status of Keith's Children

00:20:20: Reflecting on Business Experiences

00:26:04: The Role of Psychoanalysis in Personal Growth

00:28:26: Unravelling Patterns through Understanding the Unconscious Self

00:29:42: Balancing Spirituality and Religiosity in Personal Growth

00:35:30: The Intersection of AI and the Creator Economy

00:38:38: The Allure of Creativity for Tech Entrepreneurs

00:40:07: Addressing the Loneliness Epidemic through Connection

00:42:20: Solution for loneliness through AI

00:43:52: Potential use cases for AI

00:45:15: The advantage of AI clones for teaching and sharing experiences

 

00:46:58: Future of the AI project and its potential impacts

00:53:03: Reflection on identity evolution and imposter syndrome

00:55:07: Concept of success and how it has changed over time

00:58:15: Recognizing and overcoming the imposter syndrome

01:00:02: Discussing systemic biases in the startup world

01:01:19: Self-sabotage and Unconscious Desires

01:03:07: An Example of Self-sabotage?

01:03:28: Choosing The Right People

01:06:55: Relationship and Breakups

01:08:48: Dating Strategy

01:09:20: Sense of Purpose

01:10:57: Level of Fulfillment

01:12:59: On Being Alone and Joy

01:14:54: Relationship with Children

01:17:37: Identity as a Single Dad

01:18:05: New Hobby - One Wheeling

01:19:14: Lessons Learned Since First Life

01:21:22: Impact of His Children on His Perspective

01:23:06: How He Wants to be Remembered

01:24:40: Thoughts on the Future of Aging

  • Keith Smith: [00:00:00 - 00:00:09]

    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. 


    Anastasia Koroleva: [00:00:09 - 00:00:36]

    Keith Smith, he is exited founder, has spent two decades building five companies and raising two children as a single dad. A deep and original thinker, he chose to confront his post exit mental health issues head on. In this episode, Keith openly shares his insights, therapy takeaways, and how he found his latest mission in empowering creators with his innovative AI tools. 


    Keith Smith: [00:00:36 - 00:01:21]

    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. I view myself like a software package. Whenever you're going to come up with a new version, you're very thoughtful about what are the features that we need to add? What are the features that we need to deprecate? What are the things that are no longer useful to us? What are the things that are getting in the way? One of the biggest, 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. 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. The advice that I would give to my younger self if I was to do it over again is, dude, start therapy at least three months before you exit. 


    Anastasia Koroleva: [00:01:27 - 00:01:28]

    Hey, Keith. Good morning. 


    Keith Smith: [00:01:28 - 00:01:29]

    Hi, Anastasia. Good morning. 


    Anastasia Koroleva: [00:01:29 - 00:01:38]

    Thank you so much, Keith, for joining me. I'm very much looking forward to digging deeper into your amazing and very diverse experience. 


    Keith Smith: [00:01:38 - 00:01:40]

    Thank you. I'm excited to talk about it. 


    Anastasia Koroleva: [00:01:40 - 00:01:58]

    So, I know you've had quite a lot of exits, quite a lot of interesting failures, and I would love you to share the wisdom that you acquired along the way with us today. So can we go back to that moment in 2009 when you had that life change and exit and talk about how you sell it right after? 


    Keith Smith: [00:01:58 - 00:03:13]

    Yes, and I should clarify, too, I had kind of a two part exit for that company, the first part being in 2004, where I, for the first time, got what I certainly considered to be life changing money at that point in time. And for context, I grew up in a middle class home. My father was a schoolteacher. My mother was the secretary at the local church. From a socioeconomic standpoint, that is what I was used to. And where I had grown up and grew up in Oregon, which isn't exactly a wealthy state, necessarily or not necessarily viewed that way. And in a small, formerly logging town that had suffered from lots of industrial decline. And so that was kind of my background and my experience. And so when I was able to take eight figures off the table, it was all of a sudden very, very significant, and it fundamentally changed things. And what it didn't do for me, interestingly enough, is it didn't give me security, at least not emotional security. 


    Keith Smith: [00:03:13 - 00:04:30]

    If anything, when I look back on that period of time, what it did for me was it changed my mindset from a building to a protecting mindset, which ended up being a pretty dangerous mindset, I think. And it took me a couple of years to kind of work my way through that and get back to a building mindset. And so I wasn't prepared for that. I wasn't prepared for that shift. I also wasn't prepared for just the little silly things that you don't expect. Like your friends and family suddenly think you're a lot smarter than you used to be, and you're really not. You're not any smarter than you used to be. You're still the same idiot that they knew and when you were poor, but suddenly they give you deference and they defer to you. And if you aren't careful, suddenly you'll find out that every time you start talking, everybody else stops and you can start to interrupt people. And that's not a healthy thing or a healthy habit to be in. And so there are just little subtle things like that that are weird that you aren't expecting, and then nobody really told you would happen. And they are good for us as humans, generally speaking, and unfettered, they create bad personality traits, and people with resources and bad personality traits is not a great combination. So it's not a good thing for humanity generally. 


    Anastasia Koroleva: [00:04:30 - 00:05:12]

    I absolutely agree with you, and it's beautiful to see how you had the time to process these thoughts and look at that change in yourself from a different perspective now. Okay, so that was your life changing event, and I can see how it changed emotionally and intellectually, and not just financially. It took you two years, you said, to go back to the building mode. This is something I'm very, very interested in. So what it is that helped you come back to who you are, which is a serial builder, what helped you make this transition? Was it just natural progression over time or something triggered it? 


    Keith Smith: [00:05:12 - 00:07:17]

    So there were a number of things in my journey in particular that I think make it unique. So it's probably not the kind of lessons that I can apply more broadly or generally to the entrepreneurial community at large, but I think that's probably true for each of us. We all have very unique circumstances in each of our stories. So some of it was that my company ended up having challenges, and so I started reinvesting dollars back into the business and took a big risk. And so that put me into a build mindset. Some of it was that I started going through just my own kind of worldview shift and change, which had a lot of characteristics to it. But I think the through line, or if you were just to kind of summarize it, is that I started to, for the first time, which is kind of a scary comment, by the way, that I started to for the first time as an adult, at the age of 40, started to have empathy for people who were not like me. And that was something new. And that started a shift as well for me. That kind of led me down a path of saying, you know what, let me think differently about how wealth should impact me. Let me think differently about how wealth should impact my family. Let me think differently about how I should raise my children and the values that I should be instilling in them, because it becomes very easy, once you have resources, to be able to neglect the things that are the most important things for us to do. For me, very specifically, that was to raise my children. I was a single dad, I was raising my two kids on my own. And to a large degree, I had taken my eye off that ball.So I got back into the, you know, got my priorities straight, started, you know, thinking straight about things. And this was not a, there was not a particular moment where this all shifted. It was, it was a progression, and I'm still on that journey, and I'm still trying to be a better dad, even though my kids are now grown and out of the house. But yes, it's been, that's started a shift and it's been an ongoing journey since then. 


    Anastasia Koroleva: [00:07:17 - 00:07:20]

    So how exactly did your priorities change? 


    Keith Smith: [00:07:20 - 00:10:05]

    I started to think differently about the various people that help you first off on your entrepreneurial journey. And I think there's a, in my first couple of businesses, I think that the shift in values maybe is reflected by my equity stinginess. That was a kind of a barometer for how I viewed the value of the people around me on my journey. And in the first couple of startups, I was very equity stingy. And it was like I had created this company. I formed it out of nowhere. My idea, I'm going to hang on to as much equity as I possibly can, and there's some value in that that's not necessarily a bad instinct. It means that you value your company. It means that you place a high value on this thing that you think will be worth a lot down the road at some point in time. But it's very important to make sure that there is a shared incentive. So that's just going to give you a lot higher likelihood of being able to be successful and have better outcomes. But it's also, I think, just as we see our economic structures in our modern societies, where we have owners and we have workers and we have haves and we have have nots, that the best way to make sure that we get rid of the wealth disparity that we have that's growing at this point in time is to make sure that more people are owners and more of the workers who are actually doing the productive day to day work have a vested interest in the outcome of these companies. And the reality is, especially in America, and I think this is true for generally, for any modern capitalist society, is that unless you have an ownership stake, you will never achieve wealth. You may have high income, but you won't achieve wealth. And so making sure that we individually, as entrepreneurs, spread that equity around, but I think hopefully that starts to have a larger impact where we can start to spread equity around to workers generally, so that we can start to have a better participation from an overall societal perspective into the wealth creation that's happening. You could see that shift in my cap table stinginess. And I wouldn't necessarily probably say that I'm generous with the cap table at this point in time, but I have a very different view of it. And I like to reward those folks. And part of that is informed, by the way, by one of the most rewarding moments I ever had in my entrepreneurial journey, which was the moment I sat around with six of my co founders. And we cheers because all of them had been become millionaires that day. And it was a day that we took money off the table and seeing those folks and the life changing money for them ended up being far more rewarding and far more emotional for me than receiving that for myself. 


    Anastasia Koroleva: [00:10:05 - 00:10:15]

    And would you say that now it motivates you to create more businesses, to share that newly created value and wealth with other people, your co founders? 


    Keith Smith: [00:10:15 - 00:10:28]

    Definitely. Most definitely. Yeah. It has fundamentally shifted how I talk about it, the language I use, the amount of equity that the folks that are around me get, et cetera. So yes, it's informed a lot of those pieces. 


    Anastasia Koroleva: [00:10:28 - 00:10:46]

    So if you start a business today and you invite a new co-founder with whom you haven't had experience before, I'm sure you would be concerned whether that person would continue doing the work and actually invest in their time and effort. How do you make sure, how do you incentivize those people? 


    Keith Smith: [00:10:46 - 00:11:39]

    I had this situation with my current company. My co-founder, I've never worked with before. He's much younger than I am, much smarter and much more ambitious, and much more energy as well. So those are all good things. And he had startup experience and he's our CTO, but we hadn't worked together before, and I'd known him for years, so I knew his integrity and I knew his character. And so those things were not questions for me. And I knew he had a high work ethic, but I didn't know the quality of his work. And so what we did is we just vested his equity. And so it creates this great incentive because there's a wonderful potential outcome. But the equity itself is probably very little risk to me, because if we decide six months in or nine months in, that it's just not a fit, then the equity portion itself, because of the vesting structure, is not going to have an impact. 


    Keith Smith: [00:11:39 - 00:12:05]

    What will have an impact is the momentum and the lack of momentum and the detraction for momentum that would happen if we had to separate as co founders. I'm happy to report that this is one of the best co founder partnerships that I've had in my entrepreneurial career. So it's going swimmingly so far. But that's the exact. I mean, the vesting structure is ideal for this kind of thing, and making sure that we mitigate our risks to the company. 


    Anastasia Koroleva: [00:12:05 - 00:12:12]

    Okay, so if we go back to when you just started your first company, what motivated you to do that? 


    Keith Smith: [00:12:12 - 00:13:00]

    So there were two things. I think, as I look back, they were probably pretty simplistic. But initially it was that, you know, I. I guess the summary, if I was to just take away one thing, is that I realized at an early age that I don't do well toiling within somebody else's vision. So that's my flowery way of what my parents used to say, which is that I have a problem with authority. And I think that's probably a pretty consistent personality trait. Most of us who are irrational enough to go off and start our own company, I had no pedigree to start companies. I had no business degree. I had just finished school to Bible college to get a biblical literature degree. And as they say, the things. 


    Keith Smith: [00:13:00 - 00:13:24]

    What you can do with a biblical literature degree is anything you can do without a biblical literature degree is what the answer is, it wasn't exactly the bedrock foundation that you need to start a company. And I had no business starting a company. It was a very irrational event on my part, but it was really about making sure that I could create a vision that I could work within that I can be passionate about and pour my energies into. 


    Anastasia Koroleva: [00:13:24 - 00:13:26]

    Was financial freedom part of it? 


    Keith Smith: [00:13:26 - 00:14:09]

    Yeah. I think there was a moment in my early twenties where I realized that what money does is it buys you freedom and it buys you optionality. And I value optionality immensely. And so the idea that you are beholden to other people, especially in a capitalist society, we, you know, unless we're born into money, we are born into being beholden to the capitalist society, and we're going to have to create value if we're going to survive in this, in this system. And you can buy your freedom with, you know, with a few million bucks. And so if you can, if you can figure out how to be able to squirrel away a few million bucks, you can then put your energies into whatever you want to do, not into what you have to do or just what you're good at. 


    Anastasia Koroleva: [00:14:09 - 00:14:20]

    So is it what wealth means for you today, something that buys optionality and freedom, or are there other aspects that you're thinking about? 


    Keith Smith: [00:14:20 - 00:15:10]

    Yeah, I think it's freedom for myself and for my family and for those around me to be able to focus on the things that they want to do rather than things that they have to do. So that's kind of thing. One. I think the second piece is to enact the change that I want to see in society. You know, that that is one of the things about America, like it or hate it, is that if you have capital, it gives you a platform and a voice.Maybe not necessarily just as a, you know, from a, from a publicity perspective, but just in terms of being able to influence things. And so I think that's, that's, that's a trailing next piece of it as well. But I think the, you know, my view also is that the amount of wealth you have to do it in order to do that significantly is, is, you know, it's pretty substantial. So, so that's limited at this point in time, but that's a future goal for sure. 


    Anastasia Koroleva: [00:15:10 - 00:15:24]

    Okay, so your priorities when it comes to your business and financial activities changed after you exit over time? Not right away, but it took some time. They evolved. How about your priorities with respect to your personal life? 


    Keith Smith: [00:15:24 - 00:16:53]

    Yes, it certainly did, but I think this was part of a larger journey for me that probably had nothing to do with wealth accumulation. And I had wealth accumulation and wealth loss and wealth accumulation again. And so I had kind of a, a bit of a rocky kind of experience in relationship with wealth accumulation. And that's oftentimes part of the entrepreneurial journey. But I think kind of separate from that, I was going through a longer term kind of life shift. And this is consistent with my overall view on my life and how I want to operate my life, which is that I view myself like a software package and as you, as you work on a software package. For those of us who've been in the software world, and I've been developing software packages or software tools in one form or another, or working with my developers to do so my entire career. Whenever you're going to come up with a new version, you're very thoughtful about what are the features that we need to add, what are the features that we need to deprecate, what are the things that are no longer useful to us, what are the things that are getting in the way. And I really like viewing myself through that same exact lens. And it allows me to be able to think of myself as iterating and improving. And a lot of what that's about, especially I found this in my thirties and forties, is that a lot of my software iterations were more about deprecating features than they were about adding features. And so it was getting rid of shit that I had accumulated along the way and getting rid of that rather than just adding new things. 


    Anastasia Koroleva: [00:16:53 - 00:17:46]

    Yeah, I totally agree with you. For me it's quite similar. I realized that I started really making progress in my personal growth once I started thinking that way. What it is I can remove from my life that doesn't serve me anymore, as opposed to keep adding more. And generally this is how I think we come to that distilled wisdom that is very ours, very helpful practically because we produce it. So I'm absolutely on the same page with you on that one. What about your children? Because of course it's very unusual that you've been a single dad while building these five startups. And I had a period in my life when I was a single mother. So I have lots of empathy and compassion and understanding of this situation. I would love to hear a bit more about that experience. 


    Keith Smith: [00:17:46 - 00:19:45]

    Yes, thank you for asking about that. I love talking about this experience and it is interesting. I don't run across a lot of other male entrepreneurs that were single dads. I do run across a number of women who figured out how to be able to both start a family and start a company and figure out how to be able to do that at the same time and oftentimes by themselves, I'm always just amazed at hearing those kinds of stories because I think they're incredible and I think they're very hard. I have a couple observations about it. I think the first off is that I think it was hard on my children. I don't think it was probably fair, because with the entrepreneurial journey comes an implicit agreement that you are going to be a bit of a workaholic, and you are. This is not a nine to five job that you just clock out of, and then you don't think about until the next day you are on. You're always thinking about it, and that robs your family of a lot of things. And if you don't have a two partner system where, you know, and, and I would joke a lot that, that at least, you know, if it was like, you know, two parents and two kids, you can, you can play man to man defense. You know, when you're, when you're one parent and you have two kids, you got to play zone defense and that's all you got. And, and you got to try to figure out how to be able to cover both of them at the same time. You're still trying to figure out how to knock out the rent and make some money and build this business. And so those are things that I think we as entrepreneurs can do, but it does rob our children of a certain level of joy and probably peace that they would have otherwise gotten. My kids version of that is they like to joke now that they're adults, that they were raised by Wolf. And I think that kind of sums up perfectly kind of what their upbringing is like. I'm happy to report that they are both wonderful, well adjusted adults at this point in time. They're both making their dent in the universe. My daughter is actually one of my co founders at my latest startup, which is not something I would have imagined would have been happening or that I would have pursued, but it is one of the great joys of my career so far, and I really, really thoroughly enjoyed that. 


    Anastasia Koroleva: [00:19:45 - 00:19:47]

    Amazing. What does your son do? 


    Keith Smith: [00:19:47 - 00:20:20]

    My son is we're kind of also a little bit in business together. So we have a family home out in Seattle. I live in New York City. My daughter lives in Brooklyn. That's where my company is founded. We moved from Seattle, though, about ten years ago. And so after my son graduated from high school, he went back to the west coast to go to college. And so then he started caretaking our second home that was out there. And so it's on, it's on property and it has a couple of buildings. And so he has to maintain those, keep them up, and he loves to work with his hands and he is extremely handy. 


    Keith Smith: [00:20:20 - 00:20:46]

    And anything that is mechanical or that he can use a wrench to fix, he is all about it. So he and I, we do not have any of the same characteristics that way, but in terms of needing to operate within our own vision, that is a very consistent trait between the two of us. And so he manages that property, lives in one of the buildings, and keeps that cash flowing, and just got done with school, and so now he's looking for his next full time gig. 


    Anastasia Koroleva: [00:20:46 - 00:21:34]

    Brilliant. So going back to your business story, so you sold one company in 2009. How did you start the other ones? I also know not all of them, you would call successful exits, and I'm sure you've learned a lot from them. And I would love to dig into that because I have been a victim of this illusion that after my first exit, I thought, oh my God, now I'm going to do it all over again. And my next exits will all be bigger than my previous ones, and I can do two at the same time. And I see lots of other people making the same mistake, which I think is a mistake because it comes from being disconnected from reality and not having processed your own experience. But I would love to hear your journey. 


    Keith Smith: [00:21:34 - 00:23:40]

    Yeah. So a couple of comments about that. I think you're exactly right. I so resonate with those comments. And I characterize my prior five startups as three exits and two lessons. And I think that when we fail, we tend to learn more, we tend to get more out of those lessons. I think those were incredibly, incredibly valuable to me. And I agree. I think one of the things that we forget very, very quickly when we have a successful exit is how much luck played a part in getting us to that particular moment in time. The bullishness on our capabilities, which is probably way overblown at that point in time, goes up significantly. And we start to think, oh, yeah, we're invincible. We can go and start another company and it'll definitely be a success. Maybe we'll start two or three at the same time. And we see a lot of repeat founders doing that, and some are incredibly successful at that. And those folks I absolutely marvel at, they are astounding to me. The reality, my reality has been that it's, while there's a lot of lessons that I know and there's a lot of obstacles that I can avoid this time around. I can't just be lazy and just assume that because I've seen this movie before, I know what the outcome is going to be, because the pattern matching oftentimes goes away in the next generation of a company. There's new tools, there's new mediums, there's no new realities, there's new economic realities, et cetera. So we have to be just as adaptive and work just as tirelessly as we did previously and get the luck to go our way just as we did previously. And getting all those things to line up nicely together is very, very hard to do. Certainly there are some friction points that get taken out of the startup and company formation process and building when you've had a successful exit. But in many ways, I think we bring our own new obstacles to bear, just because sometimes that experience can sometimes be a detriment as much as it is an asset to us. 


    Anastasia Koroleva: [00:23:40 - 00:23:47]

    So in your case, tell me about these obstacles that you now realize were obstacles caused by the first success. 


    Keith Smith: [00:23:48 - 00:25:15]

    So I think there's a lot of it had to do with that mindset that I referenced earlier, which is that if we go from a, from a building mindset to a protecting mindset, that by itself is just very different. And it's nearly impossible to be in a protecting mindset when you have nothing to protect. From a financial perspective, when you start out at the lower end of the socioeconomic scale, you don't have to worry about protecting anything. All you can think about, and all you have to think about is if you're ambitious and you want to move forward, is how do I rise and how do I come up and how do I get to the next rung? And so it's all about forward, forward, forward momentum. And then all of a sudden you realize that you have this bag of money that you need to protect, and that just shifts your thinking dramatically, and it makes you sometimes more paranoid. It can bring about new anxieties that you didn't even realize that you had. So the advice that I would give to my younger self if I was to do it over again is, dude, start therapy at least three months before you exit, because you're going to need some context, you're going to need some grounding, you're going to need some perspective, you're going to need a third party who's going to be able to see your emotional state going like this and be able to hopefully give you some sort of baseline to be able to ground you and bring you back to reality. And so that's super important. And I didn't do that. And as a result, it caused a lot more heartache, probably, than I needed to cause for myself. 


    Anastasia Koroleva: [00:25:15 - 00:25:17]

    Did you start therapy after your exit? 


    Keith Smith: [00:25:18 - 00:26:03]

    I did a lot of therapy in my twenties and thirties, in my early thirties. I then took some time off, and then I spent my entire forties preparing for and delaying starting therapy again. I had a decade of saying to myself, I'm going to start. I had a friend who was in psychoanalysis, and he kept saying, keith, psychoanalysis is an absolute competitive advantage. He was a fellow entrepreneur mentor of mine. He said, it's an absolute competitive advantage. It's like having, you know, it's like going to the, going to the Olympics to try to compete in a, you know, in a sport and not having a coach, like, how could you possibly even imagine doing that? We all need it. We all need that. And so, so I had had CEO coaches. I had had that sort of thing, but I didn't have a. I didn't go to analysis. You know, during that period of time, I didn't go to talk therapy. Now I back in. 


    Keith Smith: [00:26:04 - 00:27:26]

    I'm happy to report that my procrastination streak is over. And so I started that about a year and a half ago. And that has been life changing. And, and what's interesting about it is, and I don't know what kind of caused this shift exactly, but it shifted for me. I remember going to therapy in my early thirties, and about an hour or two before my therapy session, my brain would automatically start thinking about all the things I could do to get out of this therapy session. What can I do to avoid it? What sort of tasks can I pile on myself to feel like I'm just too busy? There's no way I can invest this time in myself. All of those things would start to come up, and I would 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 manny or petty, you know, it's like it's a moment of pampering. 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, like, 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. 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 for. 


    Anastasia Koroleva: [00:27:26 - 00:27:30]

    So besides enjoyment, what else did you get out of it? 


    Keith Smith: [00:27:30 - 00:28:22]

    I've learned some shit about myself. And I think they, they say that the thing about psychoanalysis is that in particular as a form of talk therapy, it's very freudian, is that it's not necessarily about 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. It took me a while to internalize that. I think I still am probably internalizing it 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 kind of gone through this process and it's been a very good, healthy process for me, 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've uncovered them along the way. And that's been a real game changer for me. 


    Anastasia Koroleva: [00:28:22 - 00:28:26]

    Fantastic. So it's self knowledge that you get. 


    Keith Smith: [00:28:26 - 00:29:20]

    Self knowledgeAnd I think, and why do I do this? Why do I do this thing? Or why does this thing keep happening, 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 and me just unconscious, frankly, fucking with my conscious self, being able to better understand those things about yourself so that you can walk around in this wonderful meat sack that we all get, that we can say, okay, I actually have a little bit better understanding of what's going on here. I don't fully grok it all, but I'm getting better and I'm starting to understand it a little bit better. And I feel like that is a progress that for me has been really, really valuable. 


    Anastasia Koroleva: [00:29:21 - 00:29:42]

    So for someone who started their, I guess, career focusing on biblical literature, how do you kind of, how do you balance that psychoanalysis and spirituality in your plan for your own personal development and growth? 


    KeithSmith: [00:29:42 - 00:32:19]

    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. And 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, 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 tainted the real underlying message pretty significantly. And so a lot of it for that is 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. And 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 into analysis, I brought this up and I said, we need to destigmatize this idea of treating mental health. And crickets all around the room, people looked at me like I had three fucking heads. Like, what the hell is this guy even talking about? 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 aged, 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 yet it's good if we can shine a bright light on this stuff and start to talk about it. 


    Anastasia Koroleva: [00:32:19 - 00:33:51]

    No, absolutely. You know, if you look back at the history of the humanity, spirituality and mental health were the same thing, right? They kind of disconnected recently. But if you look at the basics, if you like, 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. So that's why I was fascinated by the fact, 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 were you tried to do rinse and repeat? 


    Keith Smith: [00:33:51 - 00:35:23]

    I didnt do rinse and repeat, but I would say that the first company that I started after my exit was at least a rhymed with the prior one, 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. 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 nineties, 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 a, and build a fintech company. But 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 with a very different market and a very, very different underlying technology set, which is of course driven by AI, which is just fun. Fundamentally a whole new thing anyway. 


    Anastasia Koroleva: [00:35:23 - 00:35:30]

    So what made you make this decision every time to go to quite a different space? 


    Keith Smith: [00:35:30 - 00:37:28]

    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. It was comfortable. I knew all the levers, all the dials, all the switches. It 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 us 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. That was the thing that drove for me. And this was part of my me iterative process. This 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 a technology shift unlike anything that we've seen since the, since the, 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. I'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, 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 platforms. 


    Anastasia Koroleva: [00:37:28 - 00:38:38]

    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. So 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 creating 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, 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. So please talk to me about that and if you can help me understand whether I'm correct thinking that for, for an exited founder, it's a particularly interesting product. 


    Keith Smith: [00:38:38 - 00:40:07]

    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 this 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, it's this, this sense of, like you spend, I think as an entrepreneur, oftentimes, especially as a technology entrepreneur, you spend a lot of your time in the spreadsheet. And I say that 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 create customers that are steeped in creativity is something that makes sense to me. And it's certainly a part of what attracted me to this customer base. And 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, 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 the problem that we are trying to solve for. 


    Keith Smith: [00:40:07 - 00:43:52]

    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? What are the things that I see that are going on in the world? And I think one of the biggest things that is, 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, you know, I think we, you know, we all are aware of what's going on here, but most of us don't necessarily feel it because we are, 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 disconnected 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. And 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 that are less connected now? And part of that is because the behavior that a lot of folks are exhibiting online is they are either doom scrolling or watching endless porn. And 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 once every once in a while, but it's not the kind of thing we should be having for dinner every night. And 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. But our view is, is that the behavior that we are replacing is this behavior that is cotton candy like behavior. And we aren't trying to be, you know, that the Brussels sprouts on the dinner plate in terms of the, you know, the healthy meal of media that we consume, probably the mashed potatoes and gravy, you know, we're not the kind of thing that you want to have for dinner every single night. And that, 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. And 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. 


    Anastasia Koroleva: [00:43:52 - 00:45:15]

    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, because 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 that amazing? Isn't that how we intuitively learn? So I didn't even think of loneliness. And another thing I thought about was my exited founders, because I see, as I mentioned, there is a trend for these people to want to teach and share their experiences. And I can just imagine someone 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, and 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? 


    Anastasia Koroleva: [00:45:15 - 00:45:27]

    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 mi for you could be also used? 


    Keith Smith: [00:45:27 - 00:46:58]

    Yes, absolutely. And these are our future use cases. You explain some of them beautifully. I think about the use case where I can 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. And I'm standing in front of the AI Persona of my favorite stylist, and I'm saying, hey, I'm going to an event tomorrow night. Do these shoes match these pants? And is this the right outfit? Should I change? 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 that when we started, we were a text based chat, and that's all we were. 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, it's not just about, about feature sets, because we need to have those additional feature sets built in, but it's also about where do you start? 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. Where 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? 


    Keith Smith: [00:46:58 - 00:47:51]

    In order to be able to get my initial traction, get my initial momentum, rather than trying to just boil the ocean. So we started with an entertainment use case. And in 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. If 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 in time 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. 


    Anastasia Koroleva: [00:47:51 - 00:48:04]

    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. 


    Keith Smith: [00:48:05 - 00:48:27]

    Let'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 Keith Bot, and we have a couple versions of Keith Bot 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 to. 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. 


    Anastasia Koroleva: [00:48:27 - 00:48:39]

    Fantastic. So besides me, for you, what's next for you? What are your plans for the future? What would you love to achieve? Change or do? 


    Keith Smith: [00:48:40 - 00:50:27]

    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. 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 democratic experiment that we are a little more than a couple hundred years into now, and I'd like to see it continue. And I think self government is one of the greatest gifts that humanity has ever given itself, and I'd like to see it continue. I think that's probably, as I think about that, the larger impacts that I would like to have, that's probably where I would like to focus, is making sure that we have a self governing democracy that is fair and equitable for all. I think 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, that's an area that I, 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. 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. Those will all be fun things down the road at some point in time. Yeah. As I think about, I'm 52. 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. 


    Anastasia Koroleva: [00:50:27 - 00:50:36]

    Amazing. Let's talk about your evolution of identity from the time you started your first business till today. 


    Keith Smith: [00:50:37 - 00:53:03]

    There's a lot of change, and my closest friends will tell you that I've changed just dramatically in terms of my, my worldview. I think there's some core underlying values that probably have not changed, and so I'm happy to say that there's still 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 staunchly 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, 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 started and moved to a big city, I moved to Seattle and went, oh, wow, this world is very different than I expected. And 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 be able to distribute the potential for opportunity more widely in our society, 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. 


    Anastasia Koroleva: [00:53:03 - 00:53:19]

    Amazing. 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? 


    Keith Smith: [00:53:19 - 00:54:59]

    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. I did spend a lot of time writing those down, processing them, thinking I didn't spend any time thinking about what did this mean for Keith and what does this do for my emotional state and those sorts of things, because I was just dusting. I was just getting the dust off me, and I was going again. I was moving forward. That was the order of the day. 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. I think we see this a lot with recently exited founders, is they're like, what the fuck do I do? Who 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. Like, 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 of why do I exist? Is a good thing for us to be asking ourselves and trying to figure out what is our purpose. And 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 exits and when I had unsuccessful exits. 


    Anastasia Koroleva: [00:54:59 - 00:55:07]

    So would you say you're now detached from this identity of a founder CEO? Is it meaningful for you in any way? 


    Keith Smith: [00:55:07 - 00:56:26]

    It is still, unfortunately, core to my identity. Yeah, it really is. 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. I'm a separate person from that, et cetera. And I am, but I'm not. I am wrapped around the founder CEO identity, and it is wrapped around me. What I'm not wrapped around is any individual company. I view those as vehicles, important vehicles, 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 being tied to the idea that you can go out 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 hack this out and start doing this, is just a beautiful, beautiful thing. And so I love that. I love that formation process. I 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. I enjoy it. I love it, and it's a lot of fun for me. 


    Anastasia Koroleva: [00:56:26 - 00:56:29]

    Amazing. So, Keith, how do you define success? 


    Keith Smith: [00:56:30 - 00:57:43]

    It's changed. 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. There would not have been another part to it. And now it's, you know, 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 shift it more towards something that I think is good for society? And so I think those are the two metrics. And so good news is I have goals still that I'm working towards pursuing and achieving on the financial success side. 


    Anastasia Koroleva: [00:57:44 - 00:57:52]

    Great. Are you familiar with imposter syndrome? Very common problem for successful exotic founders. 


    Keith Smith: [00:57:52 - 00:58:14]

    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. It does plague me in ways that I didn't even realize it plagues me. And so I think we all have it. 


    Keith Smith: [00:58:15 - 00:59:30]

    I would have recognized that I had it at some level, and I just thought it was a very minor part of 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 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 my comment about spreading opportunities around in our society. And 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 the doors are not going to be open for you, and we are going to purposely, 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 is. That's a different thing. But I think a lot of times it expresses itself as imposter syndrome, but 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. 


    Anastasia Koroleva: [00:59:30 - 00:59:44]

    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. 


    Keith Smith: [00:59:44 - 01:00:50]

    Absolutely, absolutely. And sometimes I think it's not imposter syndrome. If you are a, you know, 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. And 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 if I'm a person of color or a woman or a minority in the sense of 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, 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. 


    Anastasia Koroleva: [01:00:50 - 01:01:06]

    Yeah, these are 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? 


    Keith Smith: [01:01:08 - 01:01:19]

    Boy, the big ones. I don't know if I am willing to share. It's okay. No, I think it's a fascinating. And if I say we should destigmatize mental health, then I need to destigmatize mental health. 


    KeithSmith: [01:01:19 - 01:03:07]

    So I think it's a great question. I think 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 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. I 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 I think 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, uh. It wasn't just. Just that, uh, that the stars aligned against me. Uh, it was that, uh, that I fucked up in these three ways, and. 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, let 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 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. It 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. 


    Anastasia Koroleva: [01:03:07 - 01:03:09]

    Can you give me an example of those subtle ones? 


    Keith Smith: [01:03:09 - 01:03:21]

    I often times will. No is the short answer. I could, and I would get myself into potential trouble here, so I'll leave that for my analyst. How about that one? 


    Anastasia Koroleva: [01:03:21 - 01:03:24]

    And that's all right. Not enough. 


    Keith Smith: [01:03:24 - 01:03:28]

    I was about to expose some really. Some dirty laundry there, but I was like, I'll think better about that. 


    Anastasia Koroleva: [01:03:28 - 01:03:47]

    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. This takes me to your view on how you choose people you surround yourself with. 


    Keith Smith: [01:03:47 - 01:06:50]

    So there's 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 with my latest startup. There are four of us that are co founders. 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 if you have a breakfast of ham or bacon and eggs, there's two different animals that are participating in that breakfast. There's the chicken, and there's the pig. 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 you commit your entire self to it in the same way that the pig commits to the bacon. 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. But the way that I chose them was 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? What is the reaction? Because this is not a situation where it's just like, 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 we've all had those interactions where you go, I get done talking to this person, and, oh, my gosh, I feel like I just got drained. There was this big, soul sucking mosquito that was just sucking the energy out of my body at this point in time, or there's people that have the exact opposite effect on you. And so that's the first thing that I look for, is, is this person gonna drive me towards greatness? And am I gonna 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 compliment, as in praise me, compliment as in complete me and be able to say, okay, Keith is pretty good at this, but he's, you know, 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. That are really, well, you know, nailed down, and the things that they may be weakened. Keith has strength in. And so 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, so, but, but, but the two main ones is, what is, what do we do together? What is our energy level? And do they complement me, and do I compliment them? 


    Anastasia Koroleva: [01:06:50 - 01:06:54]

    Okay, that's clear. With respect to your business, how about your personal life? 


    Keith Smith: [01:06:55 - 01:08:47]

    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 I think about this in the context of choosing a partner as an example. And 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 creating a dynamic where, oh, my gosh, I feel so much more energized. I want to be in this person's presence. We really do come together and create more positivity together than we do separate 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, do they compliment me? One of the things that I don't bring into a relationship is fun and whimsy. And a relationship is not very fun without fun and whimsy in it. And so I want a partner who's going to bring fun and whimsy and lighten me up a little bit and let me see the fun in life and let me stop and smell the roses and encourage me to stop and smell the roses. 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. 


    Anastasia Koroleva: [01:08:48 - 01:08:56]

    Brilliant. I don't think I've ever seen such an eloquent description of your dating strategy. 


    Keith Smith: [01:08:56 - 01:09:20]

    It helps when you're in the middle of it. It's another biz dev deal, is what it is. You're trying to find the right partner, you're trying to find the right investor, trying to find the right partner. The outcomes are very different between all three of those. The 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 compliment each other well enough? 


    Anastasia Koroleva: [01:09:20 - 01:09:23]

    So do you have a sense of purpose? 


    Keith Smith: [01:09:23 - 01:10:57]

    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 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. They don't probably help me. They're just kind of. 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. One of the things. There's a lot of ways to be able to. To get out of those ruts. One of the ways that I found that is a very rewarding way is, and this is not advice, this is just me sharing my personal experience, but is 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. 


    Anastasia Koroleva: [01:10:57 - 01:11:08]

    Amazing. So if you had to rate your level of fulfillment from zero to ten, what would it be? 


    Keith Smith: [01:11:08 - 01:12:56]

    Oh, this is such a great question. So one of the things we do with our co founder team every week is we ask three one to ten questions, and they're not quite exactly this, but they force us to quantify it. And then we have this spreadsheet. We can track it all the way back and see how we're doing, and it's, you know, and we have it there for all to see. And we kind of give a little, you know, little anecdotes every week to each other as to why we're feeling this particular way. But it has to do with, you know, with personal, with health and with work is how we. How we rate our one to ten. And so in terms of fulfillment on a one to ten, I would say I'm a. I guess the narrative on that is that I am extremely happy, never fulfilled, and 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 still keep a motivation for myself by saying, okay, I want to be more fulfilled, or I want to be able to. To complete more and have more and have a particular purpose that I'm pushing for, but 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. 


    Anastasia Koroleva: [01:12:56 - 01:12:58]

    So what is it from zero to ten? 


    KeithSmith: [01:12:59 - 01:13:00]

    Oh, I didn't answer the question, did I? 


    Anastasia Koroleva: [01:13:00 - 01:13:05]

    No, you gave me a beautifully deep answer. I actually avoided answering the question. 


    Keith Smith: [01:13:06 - 01:13:08]

    8.5. Yes. 


    Anastasia Koroleva: [01:13:08 - 01:13:11]

    Oh, wow. That is very high. Well done. 


    Keith Smith: [01:13:11 - 01:13:16]

    Yes, I would say that's an accurate assessment, and it might be different tomorrow. 


    Anastasia Koroleva: [01:13:18 - 01:13:20]

    Then maybe we're talking about levels of happiness. 


    Keith Smith: [01:13:20 - 01:13:26]

    Possibly. It's possible that I have a hard time differentiating between those two at any given moment. Yeah, it's possible. 


    Anastasia Koroleva: [01:13:26 - 01:13:58]

    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, you know, from somebody else. Can you tell me a bit more about that and how you balance joy and, I guess, fulfillment in your life, which would be the most serious thing. 


    Keith Smith: [01:13:58 - 01:14:54]

    Yeah. And I would say. I wouldn't 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 she's still good at it today and just has a way of making me smile, making me laugh. My son has the same impact on me. That wasn't the case five years ago. 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. 


    Keith Smith: [01:14:54 - 01:15:39]

    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 some of 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 doesn't qualify as fulfillment, but 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. 


    Anastasia Koroleva: [01:15:40 - 01:15:43]

    I can relate to that. You don't have time for hobbies. 


    Keith Smith: [01:15:43 - 01:17:37]

    Exactly. I'm like, I have a big to do list. Is that a hobby? I don't know. 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. I 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 where we are as parents. 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 going to 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. And that was received, you know, okay. At the time. Since then, it's. 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, look, it's been controversial, but I've told you before, I'm not your friend. I'm your dad. But now we get to reshape our relationship, and now maybe I'm your friend. We get to decide, 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? We get to define this. And I will respect your boundaries in whatever order and 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. That was so effective and so impactful to us that I did the same thing when my son turned 18. And it set just this foundation for this relationship with both of my adult children, which I had very high expectations for. 


    Keith Smith: [01:17:37 - 01:18:05]

    But this has been far more rewarding than I ever could have expected. It is. Every stage of my children's growth has been my new favorite stage, but this is 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. 


    Keith Smith: [01:18:05 - 01:19:03]

    I 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 a 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 6000 miles on my one wheel. It is 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 3 hp electric vehicle, I kind of don't want to go there. So Manhattan is great for me in that regard because most of the things I want to go to are within reach of my 3 hp 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 different. 


    Anastasia Koroleva: [01:19:03 - 01:19:06]

    Well, I'm sure it attracts a lot of attention in Manhattan. 


    Keith Smith: [01:19:06 - 01:19:14]

    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. 


    Anastasia Koroleva: [01:19:14 - 01:19:32]

    Brilliant. So you've given me so many golden nuggets in this interview. And to summarize this, I'd love you to tell me, what do you think are the most important lessons that you've learned since your first life? Change and exit. 


    Keith Smith: [01:19:32 - 01:21:22]

    I would say it's interesting. I'll give you two lessons that I actually learned for my children. There 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 upright of worldview, etcetera. And 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 home. And 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 rear view mirror and rolls down his window, reaches into his pocket, grabs the five dollar 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. 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. Took a while, but that lesson fostered. 


    Keith Smith: [01:21:22 - 01:22:46]

    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 CEO's 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, little being. And she made some comment that was a very feminist kind of comment. And I turned around to the person. I said, yep, see, I've raised a feminist, and my daughter just looks at me and she goes, dad, who raised the feminist? And 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 and 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 shake 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 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 are. Also, then training them as well. 


    Anastasia Koroleva: [01:22:47 - 01:22:58]

    I couldn't agree more. Also, they push you to be less selfish, whether you like it or not. It's probably the thought of it, no choice, making you a better person whether you like it or not. 


    Keith Smith: [01:22:59 - 01:23:02]

    Exactly, yes. So, well said. So well said. 


    Anastasia Koroleva: [01:23:02 - 01:23:06]

    So, Keith, my last question, how do you want to be remembered? 


    Keith Smith: [01:23:06 - 01:24:39]

    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. My group of people that I've helped do that is, is two of them, just my own, two children. Hopefully it's bigger, you know, a bigger audience than that. But I think if I can. 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 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. And by the way, I'll also point out that I don't think that's coming for another couple of centuries. I'll. 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. 


    Keith Smith: [01:24:40 - 01:24:46]

    We will see. But I think that day is probably a long way off. We'll see. Check back with me in 150 years and we'll see where we're at. 


    Anastasia Koroleva: [01:24:47 - 01:24:51]

    I am a big fan of that thought as well. I love thinking that way. 


    Keith Smith: [01:24:51 - 01:24:58]

    Good. I love finding other folks that are also of the same mindset because there's a lot of post exit founders that share this view. 


    Anastasia Koroleva: [01:24:59 - 01:25:04]

    Yeah, I guess most of us are optimistic by definition. Otherwise we wouldn't be where we are. 


    Keith Smith: [01:25:04 - 01:25:05]

    Yep. Or anybody that way. 


    Anastasia Koroleva: [01:25:05 - 01:25:22]

    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 say 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. 


    Keith Smith: [01:25:22 - 01:25:26]

    Thank you, Anastasia. This has been a delight. I enjoyed the conversation, the wide ranging topics. It was a lot of fun.


 
Anastasia Koroleva
Previous

Laurent Vernhes. Quality-Obsessed Exited Founder: "Business is a Form of Art"
Next

Connor Tomkies. Aftermath of an Exit: Healing, Reflecting, and Progressing Forward