Preston Rutherford: Missed Exit

0:11In terms of my leaving the business, I wish I didn't leave at that time. Preston Rutherford. His company was sold in a nine-figure exit five years ago. A couple of years later, the combined company had a 10-digit IPL, 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. Don't have feelings, don't be able to articulate them, just focus on the work and just do it.

0:57Probably also just skewed views of emotion from my upbringing. I did let the burnout get to me and the lesson was A, that the grass isn't greener and B, 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.

1:27Hi, Preston. Thank you so much for joining me today. I was very excited about our conversation. Yes, I am too. Thank you for having me. So you exited Chubbies in 2019, which makes it five years ago. That's a 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. Sure. Started it because I think there were a combination of reasons coming together around that time one was uh 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 um i'd say a a mix of reasons many of them i regret to be honest and uh so i'd say number one was um feeling 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 was 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.

3:10And then you add those things as you go along. So your burn rate changes and fixed costs 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 like interpersonally as well with the other founders and, and broadly my sort of like personal and professional learning arc. I'd say there were from some areas of improvement where I allowed there to be some continuing rifts or conflict that 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.

4:11And 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. So overall, do you regret exiting? 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 stayed with my other co-founders and stayed through the acquisition, stayed through the joining of solo brands.

5:11because 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, I had to, 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, an acquisition, no regrets. Feel so blessed and lucky that that happened.

5:59I mean, 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. And so a fantastic gift and blessing that that acquisition happened. 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 on the other side.

6:45So did you find it being greener? 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, you know, rate of mistake making in a variety of realms learning some other fields um like enterprise software real estate two things that i was at least theoretically interested in you know from those perspectives the grass was greener in that i learned other things but the 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, um, starting over, watch a few YouTube videos and you, there's, there's a reality to all of this compound, compounding reputation, compounding real, all of these things I really learned the value of.

8:16So, um, you know, my, 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. How long did it take you to complete that journey back to your zone of genius? 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.

9:06But to the extent it's objectively genius, I can't I can't claim that. But it took me so 2019 and what is it 2024 so and I've been working on this new business now for about a year so that is four years so basically it's a it's a second college if you will so I went back to a four-year university of uh of lessons and then yeah came back home 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 built in the business.

9:50Yeah, 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 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, 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 wasn't too pleased with that.

10:51So I'm again trying to apply those learnings to and basically for me it comes down to just trying to think long term, 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 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.

12:00A 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-30s and not really having a lot of cash, if you mismanage that, which I think I did in terms of what's important and what I connect to my self-worth and my identity. You know, it can 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 with people and be honest and be able to be open to someone telling me, hey, you know, you really messed up here.

12:51And 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. Uh, and then the third thing, what is getting clear and then standing strong in my foundation and, and, and who I am and what my self-worth is and that it's not, and, and what I love. And, and, and if it doesn't make a lot of cash in the short term, that doesn't mean it's bad if, because a binary exit may or may not happen. I think that's the, 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.

13:36And 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 customer's world wouldn't have been as good as it existing.

14:15And 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, you know, 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. How did you go through that process of finding out who you are? 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 Chubby's, I did real estate investing. I joined a real estate investment company.

15:02And 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 where I am at home or in my zone of genius or aligned with you know who I am as a person. So that was difficult, but you know, I think it's sort of like the classic situation of you don't, you don't appreciate your health until you're extremely sick. And so I, 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, um, alive or at home or that I was fully, um, actualizing or whatever term you want to use.

16:04That was the way that I found that it, it wasn't a fit for me because in a lot of ways I devalued the feeling of not that something was easy, but this 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, um, or because I really loved it, that for some reason it was selfish or, you know, these weird things, um, where I was, it was, it was a distortion of this, the reality that was, this is something that truly is, is something that I love and is aligned with who I am. Yeah, Preston, for what it's worth, I can very much relate to that.

16:54And I hear similar ideas quite often from existing 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're cheating. Like we are looking for easy ways and that shouldn't, that just, 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.

17:47actually easy is brilliant right easy means that probably that's where we should go so I'm very very happy to hear that you also realized 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 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 like 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 following.

18:44One, 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.

19:51And that's what I realized is something that does not work for me. is not a, does not work for me. It's 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 on the, in the professional side who really balanced me out. I don't think I, 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

20:54where 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. So can we go back to your search for self-worth? I find it fascinating. So what eventually helped? What worked? So at the theoretical level, of course, it's disassociating my self-worth from, um, dollars in bank account or dollars in salary or, or whatever.

21:50And, um, and that is probably the, the big thing. And then there's, there's, um, 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 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.

23:28Don'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, and I, I, 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 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.

24:26So 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 you know why 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 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 what are the things that are easy the things that are easy aren't necessarily bad or less valuable or um a sign that you're not a success and reframing my view of those things.

25:48I'd say those three things helped me get in closer contact with who I am. So you're basically saying that your definition of success included financial success and being laser focused on your work, right? So you would at that time I think that you're less successful if you allow yourself not to be short, but be distracted by feelings and emotions. I'd say that is an accurate description. Yes. How would you define success today after you've done all this internal work? 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.

26:43Yeah, 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 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 are how I view success.

27:33And it really just comes back to the, 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, that for me truly define success, just fully into one thing, my life's work. And then two with, 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. Yeah, makes a lot of sense.

28:25So 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? I want to be proud of what I gave to my wife and kids.

29:00Meaning I find that I am. One of the things I struggle with is, is, um, 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, you know, dad friends who are roughly my age. These are things that I'm working on, but, um, focus on what I gave to my kids and my wife, just in terms of being there consistently and with loyalty.

29:59and doesn't 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 you work a lot because I 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.

30:53So, 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 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.

32:02And 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 going to knock you down you gotta that's the one thing I want people to 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 okay so focus on your family which makes a lot of sense given that you have little kids six and you know a year and a half one or so right so yeah 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?

33:03Yeah. 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? 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 ikigai or the toiling or just the work that we do as humans in this world to make it better in some way. So maybe I don't need to be too hard on myself.

33:58And I say I view that as a large component of my identity and my self-worth. um and and then it's yeah 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 um 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, um, something I view as extremely important. Now I still, and I'm still working through this in therapy.

34:46I still associate so much of my self-worth to things that I do. And I, yeah, I, 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, you know, transparently still working through. Yeah, I can see that.

35:35I can see that. And I love it. It's a process, isn't it? Yeah. 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? Great question. I think it comes back to the whole journey and destination thing and definition of freedom. So, and let me also say that I have so much gratitude to my wife.

36:26You 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, she's a phenomenal partner in that we very much balance each other out, which I am 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. um and it has allowed in in in that couples are families are 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 um being a part of a large organization finding ways to have massive impact in that context.

37:26Um, and so from a freedom perspective, if I'm checking those three boxes, at least professionally that I talk about, uh, 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, in a place to be able to create things that, 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 like binary theoretical event in the future that was very financially driven. And maybe after having experienced some tiny, tiny version of, you know, 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.