Preston Rutherford. Missed 10-Digit Exit
Episode - 29
Preston Rutherford. Missed 10-Digit Exit
Preston Rutherford. His company was sold in a 9-figure exit 5 years ago.
A couple of years later, the combined company had a 10-digit IPO. But Preston wasn't there to experience it.
While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth journey.
In this episode, Preston shares how he learned to appreciate what he had, communicate more vulnerably and understand the compounding effect of experience, skills, and relationships.
What We Discussed:
00:01:11: Welcome and introduction of Preston
00:01:19: Discussion about Chubbies founding and Preston's departure
00:02:34: Reasons for leaving: Burnout and mismanagement
00:03:50: Emotional intelligence and conflict management
00:06:12: Reflections on exiting and the value of shared experiences
00:08:33: Journey back to Preston's zone of genius
00:09:16: Overcoming burnout and the importance of perspective
00:10:46: Mismanagement of emotions and communication
00:12:19: Self-worth and financial concerns
00:13:22: Learning to value what Preston loves
00:15:48: Realization of misalignment with new ventures
00:17:16: Misconceptions about challenge and difficulty
00:18:04: Support systems: Wife and co-founders
00:21:13: Search for self-worth and effective therapy
00:24:10: Building self-awareness and understanding feelings
00:25:39: Redefining success and life’s work
00:28:07: Goals for personal fulfillment and family life
00:29:14: Cultivating Relationships and Focusing on Family
00:33:02: Balancing Work and Self-Worth
00:35:08: The Struggle to Relax and Seeking Therapy
00:36:03: Redefining Freedom
00:40:01: Leaving Chubbies: Financial and Personal Struggles
00:44:02: Building a New Business
00:47:02: Achieving Clarity for the Next Venture
00:48:02: Reflecting on Fatherhood
00:48:47: Legacy and Never Giving Up
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Preston Rutherford: [00:00:00 - 00:00:04]
In terms of my leaving the business, I wish I didn't leave at that time.
Anastasia Koroleva: [00:00:04 - 00:00:35]
Preston Rutherford. His company was sold in a nine figure exit five years ago. A couple of years later, the combined company had a ten digit IPO, but Preston wasn't there to experience it. While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth journey. In this episode, Preston shares how he learned to appreciate what he had, communicate more vulnerably, and understand the compounding effect of experience. Skills and relationships.
Preston Rutherford: [00:00:35 - 00:01:05]
Don't have feelings, don't be able to articulate them, just focus on the work and just do it. Probably also just skewed views of emotion from my upbringing. I did let the burnout get to me and the lesson was that the grass isn't greener and the importance of compounding my self worth was tied up in how much money I was making. And because I wasn't making a lot of money, my self worth was diminished and I felt like I was letting my family down.
Anastasia Koroleva: [00:01:11 - 00:01:17]
Hi, Preston. Thank you so much for joining me today. Very excited about our conversation.
Preston Rutherford: [00:01:17 - 00:01:19]
Yes, I am, too. Thank you for having me.
Anastasia Koroleva: [00:01:19 - 00:01:40]
So you exited Chubbies in 2019, which makes it five years ago. That's long enough time for you to have processed at least some of the consequences of that decision, and I hope we can dig deeper into that today. If you don't mind. Let's start with why you started Chubbies and why you left.
Preston Rutherford: [00:01:40 - 00:04:13]
Sure started it because I think there were a combination of reasons coming together around that time. One was so there were four co founders who also happened to be four of my best friends in the world, and four of the people, or three others of the people who I sort of love and respect and look up to more than anyone else in the world. In terms of why I left, I'd say a mix of reasons, many of them I regret, to be honest. And so I'd say, number one was feeling burnt out, not appreciating, losing appreciation for how blessed and lucky I was to be able to be doing what I was doing. I'd say two, Washington, a little bit of mismanagement with the, I don't know what you would say, the familial communications around. Just the general idea being you start the business with no significant other, no marriage, no kids, no mortgage, and then you add those things as you go along. So your burn rate changes and fixed cost change. And I think there were some areas of mismanagement on my end around that, which I've learned a lot from, and I'd say interpersonally as well with the other founders and broadly my sort of personal and professional learning arc, I'd say there were some areas of improvement where I allowed there to be some continuing rifts or conflict that went with sort of like myself, but then also other founders that I just didn't manage well. Emotional intelligence, low. Yeah, so I'd say those were the three things. And then maybe a certain extent, shiny object syndrome where I thought, oh, the grass is greener over there, I just have to go over there. And so I'd say that was an additional error. So I'm sure there are many more, but I could focus on those three or four.
Anastasia Koroleva: [00:04:13 - 00:04:18]
So overall, do you regret exiting?
Preston Rutherford: [00:04:19 - 00:06:16]
Well, to define exiting, I guess there are two. There's my leaving the business and then there's going through a transaction where the business was acquired in terms of my leaving the business. Pros and cons, mixed feelings. I mean, I wish I didn't leave at that time. I mean, I think if I were to be perfectly transparent, I wish I had stayed with my other co founders and stayed through the acquisition, stayed through the joining of solo brands, because I think shared experiences mean something and I kind of put those relationships totally on pause, but they continued to develop, whereas I kind of felt like in some ways I was, in some ways I had to go out and learn these sorts of things so that I could be so resolute in where I stand now. Meaning I had to learn these lessons myself rather than a theoretical way. But I think from that perspective, I wish I didn't leave the business at that time in terms of exiting, there being able to be an exit transaction, acquisition, no regrets, feel so blessed and lucky that that happened and all a testament to, sure, I maybe played a little bit of a role, but the other founders, everyone else, whole team, who really made this happen. And so I just have so much respect and admiration for all of them for truly putting the business in a position where it was so valuable to the degree that other folks wanted to own it and multiple folks wanted to own it. A fantastic gift and blessing that that acquisition happened.
Anastasia Koroleva: [00:06:16 - 00:06:31]
So you basically mentioned that you stopped appreciating what the business was giving you when you made the decision to leave, and also you thought that the grass would be greener the other side. So did you find it being greener?
Preston Rutherford: [00:06:31 - 00:08:33]
No. No. I mean, I guess it depends how you define greener, but maybe from the perspective of being massively humbled and having to learn some brand new things, accelerating rate of mistake making in a variety of realms. Learning some other fields like enterprise software, real estate, two things that I was at least theoretically interested in from those perspectives. The grass was greener in that I learned other things. But I think the lesson, I want to be careful with the word regret. So let's just change. Every time I mentioned regret earlier in the conversation, let's just change it to a lesson or a learning the lesson was a, that the grass isn't greener and b the importance of compounding in life, compounding relationships, compounding lessons, expertise. Not to say that you can't start over or that you can't reinvent yourself, but take into account that starting over is not just starting over. Watch a few YouTube videos, and there's a reality to all of this. Compounding reputation, compounding all of these things, I really learned the value of. So my exiting the business and trying these other new things maybe helped me appreciate that much more. The value of that experience, that expertise that was gained to where now what I'm doing is effectively coming back to that world that I loved at the beginning, but maybe soured on a little bit, but now just realizing, oh, my gosh, this is my home and I'm so grateful to be back.
Anastasia Koroleva: [00:08:33 - 00:08:39]
How long did it take you to complete that journey back to your zone of genius?
Preston Rutherford: [00:08:40 - 00:09:16]
Zone of genius is a very nice way to put it, and I know that's a broader term, but again, I just want to call out that. I'm not sure if it's. Maybe it's my zone of genius, but to the extent it's objectively genius, I can't claim that, but it took me. So, 2019 and what is it, 2024? And I've been working on this new business now for about a year. So that is four years. So basically it's a second college, if you will. So I went back to a four year university of lessons and then, yeah, came back home.
Anastasia Koroleva: [00:09:16 - 00:09:34]
So you mentioned you were also burnt out, and that was part of the decision. What did you do to overcome that? To heal that? I don't know if you can call it trauma, but to heal whatever your health suffered during the years while you were building the business.
Preston Rutherford: [00:09:34 - 00:14:21]
Yeah, I think I just really learned the power of perspective and of gratitude, but not superficial gratitude, which is something that, at least for me, was more of what I demonstrated in my life, was just sort of like, man, I'm so lucky to get to do this. I love. I love xYz, but it didn't permeate my being. So what do I mean, by that or what's a little bit more clear, my so to be clear, in Chubbies I did let the burnout get to me and it completely tainted my, not completely, but heavily impacted my decision making, my perspective on timelines, the things that I thought were important. And so I wasnt too pleased with that. So im again trying to apply those learnings to and basically for me it comes down to just trying to think longer term, optimize for the right things. And what helped me, let's say, come to terms or repair or get back in touch with the or get away from this notion of burnout and then come back to the place maybe where there was burnout was just truly, I guess, learning for myself that burnout came from my mind being effectively mismanaging emotions and communication with myself, with my wife, with my co founders around where I was in life at that time, where I thought I should have been at that time. What I had to show for it, a lot of it comes down to money and being in a startup. A lot of your theoretical money or net worth is tied up in the theoretical equity value of your business, and getting into your mid thirties and not really having a lot of cash. If you mismanage that, which I think I did, in terms of what's important and I what I connect to my self worth and my identity, you know, it can take you on the wrong path. So I think a lot of that and then just being afraid to have humble conversations with people and be honest and be able to be open to someone telling me, hey, you really messed up here, and then being able to vulnerably say, hey, this is what I feel. I could be crazy, but this is what I'm feeling, rather than you are doing this or whatever. And then the third thing is getting clear, and then standing strong in my foundation and who I am and what my self worth is and that it's not and what I love. And if it doesn't make a lot of cash in the short term, that doesn't mean it's bad, because a binary exit may or may not happen. I think that's the reality with a lot of things, that you start from scratch, or the exit or the acquisition may not be the dream that you always thought it would be, and that might have been the reason you started in the first place. But just knowing if I love this and I feel like it makes the world a better place, I need to own that and be strong and confident in that, and then be able to be more adept at managing all these other things that I've kind of talked about that I feel I let get in the way of and block the reality that I was the luckiest person in the world to be doing what I was doing, working with people I love, creating something that other people loved, and that if it didn't exist, our customers world wouldn't have been as good as it existing, and we wouldn't have been able to provide these great jobs and wouldn't have been able to do all of these things that were truly a gift. So I think that's the way that I was able to get past the burnout or deal with or rationalize or come back to this world of zone of genius, if you will.
Anastasia Koroleva: [00:14:21 - 00:14:24]
How did you go through that process of finding out who you are?
Preston Rutherford: [00:14:24 - 00:16:33]
Probably by learning that these other things did not align with who I am, if that makes sense. So, meaning you don't know, what are the other things? So, when I left Chevy's, I did real estate investing. I joined a real estate investment company, and then after that, I joined an enterprise software company. And so I got those two areas of experience. And so doing both of those things, it was hard to tease out whether this is just the agitation associated with doing something new, or is it just purely not wherever I am at home or in my zone of genius, or aligned with who I am as a person. So that was difficult. But I think it's sort of like the classic situation of you don't appreciate your health until you're extremely sick. And so I wasn't able to appreciate what I had until it was just so clear that I was sick or that I didn't, that I wasn't in the realm of an area that I felt alive or at home, or that I was fully actualizing, or whatever term you want to use. That was the way that I found that it wasn't a fit for me, because in a lot of ways, I devalued the feeling of, not that something was easy, but just that it was something that I loved. I had this weird thought in my mind that things always had to feel super hard, or because I really loved it, that for some reason it was selfish or these weird things where it was a distortion of the reality that was. This is something that truly is something that I love and is aligned with who I am.
Anastasia Koroleva: [00:16:33 - 00:17:33]
Yeah. Preston, for what it's worth, I can very much relate to that. And I hear similar ideas quite often from existed founders that we really don't realize until we have a chance to think through it properly, that we associate difficulty with meaning and worthiness of any cause. And if it's easy, then we shouldn't be doing it, right? It's almost like we are cheating. We are looking for easy ways, and that shouldn't. That's wrong. This love for challenge, it has a flip side, right? Then we pay with our happiness, fulfillment and joy for that. And I'm very blessed with my husband, who doesn't have that problem. And he's the one who helps me understand that easy is good. Actually, easy is brilliant.
Preston Rutherford: [00:17:33 - 00:17:34]
Right.
Anastasia Koroleva: [00:17:34 - 00:17:51]
Easy means that probably that's where we should go. So I'm very, very happy to hear that you also realize it for yourself. But, Preston, I still find it very difficult to police myself. As I said, I rely on my husband to do that. But how do you overcome that problem?
Preston Rutherford: [00:17:52 - 00:21:13]
I don't know if I have a great answer. That's probably an area where I think there's room for further thought. I think the initial answer I would give is the sort of pain associated with going away and realizing that wasn't the thing coming home. Maybe I'm still in this honeymoon period. I don't think so. But I just don't know if I have a great process in place for self policing other than the one, of course, my wife and we've had to go through a lot in terms of working on our relationship and where we view our own respective self worth and value and what it's tied to. And for us, that comes from a lot of therapy, both individual and as a couple. So I think that we are both able to do that for each other much better now than earlier in our relationship. So that was an arc, that was a journey separate from that is having a co founder. These things that I did on my, let's call it my post exit, pre return back to, let's call it brand building, whether it be on the consumer side or just building technology, which is what I'm working on now. They were done alone, largely. And that's what I realized is something that does not work for me, does not work for me, is not a fit for me in terms of what I've found works. So having a co founder, someone who can balance me out, I find that I need, that I am not the singular founder who, I don't know, has this clear view of the future, feels completely sure of it, and certain at all times, so mission driven that you never have these feelings or get off off path. That's not me. I really found that I need other people to especially in the professional side who really balance me out. I also don't think it would work having someone who is just like me to. I think that would just sort of like accelerate or amplify the things that maybe are where things can maybe go wrong if some of these things are not tempered or balanced. So someone who balances me out and my co founder Tom is absolutely that and my superior in so many other ways. And so, yeah, balance. So, yes, wife and co founders and learning that about myself, but again, only learning that through failure, which painful at the time, but helpful now looking back.
Anastasia Koroleva: [00:21:13 - 00:21:21]
So can we go back to your search for self worth? I find it fascinating. So what eventually helped, what worked?
Preston Rutherford: [00:21:21 - 00:25:39]
So at the theoretical level, of course, it's disassociating my self worth from dollars in bank account or dollars in salary or whatever. And that is probably the big thing. And then there's this whole idea. So that's one. And that's sort of like on the micro level, at the macro level, for me, it was quite a bit of therapy around, talking these things out. I mean, I am not the most, in my day to day life, I would say the most verbose or articulate with my feelings. It's very much just swallow it, don't actually, like, be numb to it so that you can work and work really hard and not get distracted. And probably also just skewed views of emotion from my upbringing, I don't know where they come from, but really just having this interesting perspective on life and work and success, that emotion or being in touch with feelings or vulnerability or things along those lines was a sign of weakness. And that I should just be what I viewed as success, or what I aspired to be or how I wanted to behave was more in this realm of don't have emotion, because that distracts you don't have feelings, don't be able to articulate them, just focus on the work and just do it. And other things will pull you away from that. And it took me a long time to learn that. That's not the approach that works for me. And I had to, I think, learn those lessons and also come in contact with this idea of what I like because I was, for some reason, again, I was just very much in this world of it's what I should do, it's the right thing to do. It gets you to this theoretical next step of what success looks like based on some made up definition that I had. So that was another piece, which is just get in contact with what you want, where you feel alive, just get in contact with feeling at all from a foundational level. So those were the things in the past that I think colored my view. And a lot of it, I shouldn't speak disparagingly about all of it, because it helped me, I think, work really hard and differentiate myself and find a lot of success. Again, depending on how you define it, but broadly defined, let's just say. But taking time to just sort of do what can be seen as maybe boring or weird or whatever work of therapy, and just talking with someone about these things and learning about myself and why do I feel this way and what do I like and what do I not like, and what does feeling alive even mean? Building some semblance of self awareness and then being able to articulate that to other people and to myself. Those things were extremely helpful in helping me find what I love. And I think it also just goes back to the thing of what are the things that are easy? The things that are easy aren't necessarily bad or less valuable or a sign that you're not a success. And reframing my view of those things, I'd say those three things helped me get in closer contact with who I am.
Anastasia Koroleva: [00:25:39 - 00:26:00]
So you're basically saying that your definition of success included financial success and being laser focused on your work. So you would at that time, think that you're less successful if you allow yourself not to be focused, but be distracted by feelings and emotions.
Preston Rutherford: [00:26:00 - 00:26:05]
I'd say that is an accurate description, yes.
Anastasia Koroleva: [00:26:05 - 00:26:09]
How would you define success today after you've done all this internal work?
Preston Rutherford: [00:26:09 - 00:28:07]
Three things. One is doing work where you're completely devoted to it, where it feels like your life's work. Now, that's obviously like, oh, great, yeah, I would love to feel that way. But yeah, I mean that for me, number one. Number two, doing that with people you love and respect, even if it means, let's just use it in the context of a startup, even if it means you own less of the company or you don't, you don't always go with your decision or whatever that might be. So that's number two. And number three is truly feeling like what you're doing is adding net new value to the world, inventing something on behalf of, or to serve others and make them more successful or whatever. Those three things for me, in a professional context, or how I view success. And it really just comes back to the cliche of it's not about the destination, but it's about the journey. Sure, but those are the three components of the journey that for me, truly define success just fully into one thing, my life's work. And then two, with people I love and respect. And then three, truly feeling like I'm inventing something where just if I look back on my life from my deathbed, feeling those things about what I was doing, regardless of money or fame or whatever, I will be happy on my deathbed if I was able to at least aim for and focus on those three things.
Anastasia Koroleva: [00:28:07 - 00:28:33]
Yeah, makes a lot of sense. So that's very clear. On your work side, if we switch to your personal side, how would you like to feel about your life? Like going back to your deathbed example. So if you're on your deathbed, how would you want to look back at your life and remember what was really amazing and the right thing to do in your personal life?
Preston Rutherford: [00:28:33 - 00:32:25]
I want to be proud of what I gave to my wife and kids. Meaning I find that I am. One of the things I struggle with is focusing on more than one thing at one time. So in my personal life, it is all my wife and my kids. Other people are really good at having relationships with their parents, their in laws, those sorts of things, even a large group of friends. And while in theory all that stuff seems awesome and I'm working on cultivating relationships with other dad friends who are roughly my age, these are things that I'm working on, but focus on what I gave to my kids and my wife, just in terms of being there consistently and with loyalty. For me, it's not time because I spend so much time on my work and I love that. And I don't feel the, maybe the shame of if my daughter were to say, dad, you work a lot, because I do time box it, and then I do have quality time with my kids. And so I'm not going to check the box on spent most of all day with the kids, honestly. Yeah. I'm always going to be working on something that checks those three initial boxes for the rest of my life. I love it. It brings me the joy and it allows me to bring that joy to my wife and to my kids. So I think that's it the one way. And as you can tell, I'm sort of processing this because I haven't thought about that component of the question, the personal piece. So, yeah, I think it's just there's this idea of never giving up, never giving up on them and then giving them everything I have in my life outside of that. And what I mean by never giving up just to give one note is I feel like one of my parents kind of gave up on, not on his life, and there wasn't anything around suicide or anything like that, but just in terms of trying as hard as they could. And that made me very sad and I think didn't mess me up. I don't want to say that, but I'm still working through that. So I want to show my kids that I want to give them everything I can. Just all effort, like, not with whatever time I give them, and my wife with whatever time I give them. And obviously, this is an impossible standard, but aiming for it, I'm going to give them my full effort on engagement. And that doesn't necessarily mean doing things, but it does mean focus and attention, I think, as the aim. And then showing them in other portions of my life that I'm giving my all that I'm not giving up, because I tend to think that's one of the most important things a person can give to this world in terms of a one on one human example, is just things are gonna knock you down. You gotta get. That's the one thing I want people to know from me, that I just kept getting back up. And I think that's maybe the most beneficial thing I can give to my kids.
Anastasia Koroleva: [00:32:25 - 00:32:46]
Okay, so focus on your family, which makes a lot of sense given that you have little kids, six, and I, you know, a year and a half or so. Right. So you're in the very beginning of this exciting journey, and your identity as a father may be something that must be something that you are learning to have still. Right?
Preston Rutherford: [00:32:47 - 00:32:48]
Yeah.
Anastasia Koroleva: [00:32:48 - 00:33:02]
So you were saying before you found who you are, so. And we immediately started talking about work, but how do you think of yourself as a person and of your identity today?
Preston Rutherford: [00:33:02 - 00:35:17]
That is a work in progress, I would say. I think if I'm to be honest, I probably, and I don't know how to quantify this, but just to articulate, I probably put too much of my worth as a human in my work. However, at the same time, I do view there being a lot of value in the, whether you want to say icky guy or the toiling or just the work that we do as humans in this world to make it better in some way. Maybe I don't need to be too hard on myself. And I say I view that as a large component of my identity and my self worth. And then it's sort of like my family, who I am to my wife and who I am to my. My kids. And so, for instance, just showing up, going full out, I love being my daughter's. T ball coach, which is one of the things I just did. And I just absolutely loved that. And that wouldn't happen, I think, if I was just sort of. If I didn't view being a dad as an extremely, extremely important part of who I am as a. As a person. And that is something I view is extremely important. Now. I still, and I'm still working through this in therapy. I still associate so much of my self worth to things that I do. And, yeah, I don't know. I mean, I don't know if that's good or bad, but it's probably not in balance. And so maybe there's something more room for improvement there. But I just. I love doing, I love contributing, I love creating, and I think the world needs more of it. But I do tend to not be able to think that I am worthy or with worth if I'm not doing. And that can annoy my wife sometimes because I do tend to struggle to relax. So these are things that I'm transparently still working through.
Anastasia Koroleva: [00:35:17 - 00:35:22]
Yeah, I can see that. I can see that. And I love it. It's a process, isn't it?
Preston Rutherford: [00:35:22 - 00:35:22]
Yeah.
Anastasia Koroleva: [00:35:23 - 00:35:52]
Okay, so let's talk about freedom. So you left Chubbies and you had all the freedom in the world. And I assume when you started the company, as many of us, we would do it for financial freedom, for autonomy, whatever term we use for that. So how do you feel about it now? Did you achieve your freedom through the business? Do you want more of it? Do you want less of it?
Preston Rutherford: [00:35:52 - 00:40:01]
Great question. I think it comes back to the whole journey and destination thing and definition of freedom. And let me also say that I have so much gratitude to my wife. You were talking about your husband, but just in terms of our context, my family so grateful to my wife. She has provided so much stability for our family, both emotionally, financially, in any realm of life. And again, she's a phenomenal partner in that we very much balance each other out, which I'm just so grateful for. And I don't have the counterfactual to be able to imagine a world without that. But so much gratitude there, and it has allowed in that couples are families. There's a team component there. So she enabled me to live my fullest life, and I think she's living her fullest life and that she feels alive doing these things, being a part of a larger organization, finding ways to have massive impact in that context. And so from a freedom perspective, if I'm checking those three boxes, at least professionally, that I talk about of just doing this work with the people you love and respect and feeling like you're inventing something that new. Now, obviously, those are things that put a person in a place to be able to create things that I think matter in the world. So then all of the other things tend to take care of themselves. But I used to associate freedom with this sort of binary theoretical event in the future that was very financially driven. And maybe after having experienced some tiny, tiny version of financial freedom, even though in the Bay Area of California, it was not sort of like, I don't have to work sort of thing, because just prices and home values are insane. And as humans, we tend to, unless we're very disciplined, we tend to allow our burn rate to kind of grow to where you sort of never have that stress release. So that's a big learning, I guess, which is it takes discipline to even feel the financial freedom that is just way underrated, because you can be financially free at any number. It doesn't matter. It's just about managing the l component of your p and l. So, yeah, I think a redefinition of freedom certainly happening to where I can feel free in each moment, not if something happens and there's some theoretical financial result or whatever, that may or may not have some theoretical perceived impact. It's just sort of like embracing these inputs as freedom. So I feel the freedom that I didn't know I wanted, but now I know I want in this moment. But again, I feel so grateful that feeding the family, having a roof overhead, these sorts of basic things, are not a huge stressor, but even in the Bay Area, I don't want to say that, but I feel very grateful that those sorts of things are possible. It is a huge gift and luxury that sort of, like the basics are in a pretty good place to allow me to feel that freedom, but that's it. Less focused on sort of like theoretical binary, massive outcome, and more focused on just people I get to do my life with feeling like there's this semblance of life's work and something I can devote myself to. That's freedom.
Anastasia Koroleva: [00:40:01 - 00:40:16]
Let's talk about how you're leaving Chubbies has actually affected your relationship with your wife, if you don't mind. Like, what were the challenges? Because you keep mentioning that it was a difficult period for both of you.
Preston Rutherford: [00:40:16 - 00:44:04]
Yeah, I think my lesson, what I think other founders might share and resonate with experience wise, is just. It becomes challenging from a salary perspective. If as a founder in a business, you've been paying yourself the same pretty minimal number for 5678 years. And it can put a strain on the relationship if these conversations aren't being had pretty consistently, and if, if you're not able to approach them in a manner with sort of like vulnerability and being in touch with who you are and what you love and those sorts of things which have been themes I've discussed, and that's me. Like, I take that as my responsibility where I kind of fell short, which is I wasn't able, I really felt that my self worth was tied up in how much money I was making. And because I wasn't making a lot of money, my self worth was diminished and I felt like I was letting my family down, I was letting my wife down and letting, I don't know if I felt like I was letting myself down, but the people who I think were very, very, the most important to me. So whereas I could have reframed it and been able to talk more about, this is what I love, this is the theoretical equity value that we think we're building, it may or may not happen, but what truly is important, what truly do we care about? And I think we would have gotten past this sort of, you know, or I, I can only speak for myself, I would have gotten past this financial blocker or distortion of what success is, and I think that would have been extremely helpful. Now, my wife's not here, so I can't really speak for her, all of those obvious things, but yeah, I think that's what I would say is I just wasn't, I don't think I was emotionally equipped at the time to manage this very real component of being a founder, which is really coming to terms with the reality that, I mean, if you find a found a business that generates a ton of cash and you can pay yourself millions of dollars a year, different situation, but for where its an equity play and you need to be as lean as possible so you can invest everything back into the business or you feel like youre not doing your fiduciary to investors or to your co founders, then it can get difficult. And I think my other co founders probably struggled with it as well or dealt with it as well, but I just think they were better able to manage those conversations, maybe because they were more strong in who they were and what was valuable, what mattered in life. I don't know. Honestly, I haven't had this conversation with them, but those are just some of my reflections. I just look at these as lessons. I mean, I would call them personal failings in terms of how just not knowing who I was and what was valuable and thinking that I wasn't successful, and therefore I needed to just jump into some arena, like real estate investing or real estate private equity, that, well, there's a lot of rich people who do that, so I'll probably just go do that, completely underestimating the difficulties and the complexities and oversimplifying it. So I think those are my key points there.
Anastasia Koroleva: [00:44:04 - 00:44:24]
So you're building a new business now, and you have reframed the purpose of your business from just chasing money into doing what you guys love. But how are you going to make sure the company is actually making money? Or do you have a firm belief that if you are doing something you love, money will come?
Preston Rutherford: [00:44:25 - 00:46:04]
Well, there's the third component. That is the notion that we are doing something that the world needs and that invents on behalf of a customer where there isn't something else solving this problem. So definitely feel like that box is checked. And we did raise. We raised a little bit of money from other people, people who know us. And raising money wasn't the easiest thing in the world. We went down the traditional venture capital route and didn't work for us. I don't know why I tend to rationalize as we're not an AI company, but I'm sure there were just other reasons why. But to people who knew us and love us and trust us, it was something that allowed us to make money, to raise money, to give us a little bit of Runway. Now we might not make money. I mean, we're pre revenue right now. We're building a technology product, and we might not make money, but the hope certainly is that based on the value that we create for our customers, that there will be financial remuneration. But still TBD, to be honest. And it's a little bit scary for sure. And yeah, I think that's just a reality. But the hope is that if it checks those three boxes, those are the right inputs where the outputs, I think will take care of themselves. But I'm sure it's going to get really hard soon because we're getting close to that time when it's like, okay, we'll start making money.
Anastasia Koroleva: [00:46:05 - 00:46:33]
It's always a challenge, isn't it, to balance what you want and your dream? We have these beautiful dreams. We're dreamers as entrepreneurs with something that is very practical, like our customers are telling us, oh, we actually don't want your dream, we want something else entirely. And then you make a decision whether it's you chase your dream or you make, or you sort of think about money and success of the business, right?
Preston Rutherford: [00:46:33 - 00:47:18]
Absolutely. I give all of the credit to, again, my wife for providing this stability. I mean, I can do what I do because of her. And then to my co founder, who is much more, while he's maybe the most brilliant and creative person in the world, he's also extremely practical and focused on the realities of having to generate value that someone would pay for. So, not that I'm just wobbling around and just being like, I don't care. I mean, I'm trying to. I'm clearly practical and I understand the realities of a business and that it's not just sort of like, let's just have a nonprofit. No, I do realize that there are components to that.
Anastasia Koroleva: [00:47:18 - 00:47:40]
So you went through this transition for five years after you exited Chubbies, and you made enough mistakes to learn from, and you did therapy. Was there anything else that you found helpful to achieve clarity and to be ready for your next business?
Preston Rutherford: [00:47:40 - 00:48:44]
For me, I'd say writing, whether you want to call it journaling or even the writing that I do on LinkedIn, where I just try to have a daily practice of trying to write something that can be helpful to the reader and bringing them value that they maybe wouldn't have gotten had they not read that post, writing has been extremely helpful, clarifying. And that's probably the main thing that I would call out, I guess, the other relatively obvious, but I didn't mention it, is just kids and seeing how, at least on my six year old, how fast it happens and how soon she will be saying, daddy, don't hug me. You're weird. Stay away. You know, those sorts of things that start to happen. So just hearing the advice is one thing, but seeing it happen is a completely different thing. So I'd say writing and then seeing the speed at which this kid thing just flies by.
Anastasia Koroleva: [00:48:44 - 00:48:47]
Okay, so my last question. How do you want to be remembered.
Preston Rutherford: [00:48:47 - 00:49:14]
As someone who never gave up? I think, and maybe that's a weird thing to say, but that's top of mind right now, just sort of gave every last bit for the work that he did for his wife and for his kids and never gave up, and ideally set that example for the people that I was closest to.
Anastasia Koroleva: [00:49:14 - 00:49:21]
I think that's such a beautiful end of our conversation. Thank you so much, Preston. I really, really enjoyed it.
Preston Rutherford: [00:49:21 - 00:49:24]
Thank you. This was a joy. I'm grateful for the chance to chat with you.
Anastasia Koroleva: [00:49:25 - 00:49:27]
Absolutely. Bye.
