Dustin Parker: Connecting the Dots of a Life - Fire, Failure, Discipline, and Risk

For those who aren't familiar, there's this really famous Steve Jobs quote. The idea was that you can't connect the dots of your life, what led you to where you are looking forward. You can only do it when you look backward.

And she gathers us up quickly and we all head home. Our house is on fire. When you grow up in a small town, everyone kind of knows everyone. I couldn't continue just being a goof-off. The school resource officer recommended to me a state police boot camp. I became somewhat obsessed, I think, with that progress. Some things look far more risky than they are. I've been somewhat conservative. Throughout our lives financially. And so downsizing our expectations around what it meant to live. Take the risk and be willing to fail and just know that you're going to be able to get back up and do it all again.

So here we are, Dot by Dot, episode 0 or episode 1, depending on how we're counting. And you were brave enough to let me interview you. And I thought it would be helpful to get started with just the name Dot by Dot and where the idea comes from. And so for those who aren't familiar, there's this really famous Steve Jobs quote that he gave in a commencement speech. And the idea was that you can't connect the dots of your life, what led you to where you are looking forward. You can only do it when you look backward. And life is full of these serendipitous little moments that lead us to an outcome that we never could have predicted at the time. And we carry life lessons with us. We carry skills with us that we accumulate through these series of dots. And the benefit to me with interviewing you is that I know a lot of the dots that I want to focus on. And rather than starting all the way back at the beginning, I thought I'd like to start with something that would be a really big dot in anyone's life that I know was big in your life when you were a child. And I'm just going to give you the cue and let you jump in and explain what it was, but a house fire.

Yeah, so, uh, I can remember, uh, it was my 13th birthday, to be exact. And we were out celebrating. My mom had taken me and some friends to the movies to watch a movie. And while we're sitting in the theater, we're probably halfway through the movie at this point, uh, she gets a phone call and I can hear panic and confusion. And she gathers us up quickly and we all hop into our minivan and head home as we learn that our house is on fire. Um, it's probably 8:30 or 9 o'clock at night when we arrive back home. And of course the fire company is there. There's lots of lights. It's dark out. Uh, my dad was actually, I think, out of town, uh, that, that evening with my brother. And my house was completely inflamed. Uh, and I remember very specifically, um, that my mom was concerned about all of the family photos that we had hanging on the wall. This was before we had such a digital inventory of everything. And the firefighters were very thoughtful. And actually, before things became too inflamed, and they were able to actually grab a lot of those photos off of the walls in our living room at the time. And she was very appreciative of that. But in a moment, we went from happy celebration birthday party to not having a home. Uh, and it was quite a surprise. My parents had lived in that home, I think, for 30 years at that point. All my siblings grew up in that home. I was the youngest, and it was the only home that I ever knew. So it was, uh, it was a big shock.

So you're 13 years old, you lose your house on your birthday, which is obviously a dot that anyone would remember. But one of the things you just said really stuck with me, and that was that the firefighters were thoughtful enough to take down the family pictures and For me, that brought up a couple things. One, the importance of family, and I think in your life, that would be something that you would say has been really instrumental to your growth, but also the importance of community. And so those same firefighters that helped your family with that, you later went on, I think, to serve in the same volunteer fire company. And that's really just a demonstration of the tight-knit, small-town community of Bridgeville that you grew up in. And so would you mind talking a little bit about just just what community means to you and what it's meant over the course of your life to live somewhere that's not New York City or London, but a tiny town.

Yeah, I think when you grow up in a small town, um, everyone kind of knows everyone, and there's, there's certainly pros and cons to that. But I remember when we, we got back to our home and the scene of, of everything that was going on, that, um, we, we knew everyone there. You know, my family knew all the firefighters. My grandfather was in the fire company. My dad had previously served in the volunteer fire company as well. And so it was our community, our friends that were helping us through this challenge, which I don't know, felt a little bit more comforting maybe than it would have otherwise. These weren't strangers. They were people that we went to church with, that we saw in the grocery store. And, you know, I think that that just made it a little bit easier to kind of navigate through that. And then just having family locally that could help support us through that. We moved in with my grandparents, which they live just down the street, and that gave some stability. And in many cases, people don't have, you know, that opportunity to do that. And I think we lived there for a couple years while my parents fought with the insurance company, and eventually they rebuilt a home a little further out in the country. But it was a disruptive time in life. And when we moved in with my grandparents, my grandmother was struggling with Alzheimer's at that time. My grandfather was having some lung and breathing issues, and his health was poor as well. And so there was just kind of a lot of chaos at the same time. I'm navigating high school and puberty and all of these different things that was quite disrupting, I think, for a young boy at that time.

If you have to go back and imagine how your life might have been different had you not lived in a small-town community, what, what do you think that growing up experience gave you that maybe someone that doesn't live in that world wouldn't understand?

I think there was always like an underlying sense of safety and just that no matter where you are in your community, that someone has your back and someone's going to protect you. And I can remember getting on my bike sometimes at 7 or 8 o'clock in the morning in the summer or on the weekends and not coming home until dinnertime and riding all through town, riding through the graveyard, meeting my grandfather at the local diner where he would, uh, buying me lunch or breakfast and just kind of having that neighborhood feel and that sense of community where you felt like you belonged and you understood the other people that were there and they understood you. I think it just made it a safer, more comforting experience. And, and there's so many things that I love about cities and the amenities that they provide and the experiences that they provide and the culture. And there's just so many incredible things about cities, but I, I don't think that I would ever trade my childhood for where I lived. I think it really kind of shaped who I am today, and it was a great place to grow up.

Yeah, well, and it's basically where we're raising our kids, so trying to give them a little piece of that as well while also showing them the world. So there's definitely, there's definitely something about just living in a place where if someone's child is diagnosed with cancer, the whole community comes out and throws fundraisers and starts GoFundMes. And I mean, there's something really special when the high school football team wins, there's a parade in the town and the church is participating, and it's just something really special about that that I think would be hard to replicate in a bigger city.

So, yeah, I totally agree. And I think about the utility of that to some extent. I think, um, we can't necessarily feel the pain to the same extent when, you know, there's a bombing that happens in another part of the world, or there's some sort of disease or, or natural disaster or something. As much as we, you know, may want to care about those things and, and do what we can to support those people, when it's your own neighbors and when you know your neighbors and you know their parents and grandparents and those grandparents and parents are friends with each other, then I think there's just a different sense of belonging and a different sense of meaning to that community. And you're right, I think when, when things happen, both good and bad, people show up for each other. And while people may have different political beliefs or just walk different paths in life in general, all of that goes away. When, when you need each other. And I've seen that so many times. I've seen it through natural disasters, a tornado that came through town, just so many different things that have come up in our community where they just rally around each other. And any divides that may occur at normal times seem to fade pretty quickly. I mean, it's similar to like when 9/11, you know, I know, remember being kids when that took effect. And, you know, the country just kind of rallied around each other. And suddenly all of the things that made us feel so different or so at odds with each other just didn't matter so much anymore. I think that that's even more so true on a pretty consistent basis in a small town.

Yeah, totally. It reminds me a lot of— anthropologists always say that our brains evolved for tribal living, you know, and we just have a certain amount of people that we are able to really hold in our heads at one time. And when you are in close contact with those people all the time, it just really doubles down on the relationships. And it's, it's something that's been really special to me to see, you know, moving in from— not from a big town, but just to an even smaller one, an even tighter-knit community. And, um, you know, just being able to raise our kids in it, it's, it's been a cool experience. So it's not something I would trade. Well, speaking of your childhood, I always like to think a lot about, um, the seeds of what led to your path today. And I see it in our kids too. I like watching the things that excite them. You know, Avery, our daughter, likes to set up little pretend stores, like usually Ulta Beauty, or she had fake library in her room, a pet store. But when she has free time, she likes to perform, or she likes to create a retail environment, or things like that. Our son Ford, what he likes to do for fun is to look at bugs or watch YouTube videos about coconut crab facts, and he's always just been fascinated by animals and insects and has the scientific mind. For you, I would love to hear your earliest entrepreneurship experiences, and I think you probably have a couple that we could dive into.

I can remember, uh, being a kid and not knowing it completely at the time, but just being fascinated with the idea of having my own agency and being able to make my own decisions. Uh, and I think a lot of kids, you know, dream, fantasize about the idea of becoming an adult so that they don't have a boss and they can buy and do their own things. I probably had a little bit of a stronger sense of that maybe than a lot of my peers did at the time. And Uh, one way that I found to get a little bit more agency in my life as a 5, 6, 7-year-old, however old I was at the time, was to have yard sales. Because if I, uh, could find a way to make money, then I could buy the things that I want without having to ask my parents to buy those things for me because I wanted to take control of my own destiny. And so, uh, it was a, it was a pretty, uh, pretty good Ponzi scheme that I had going because I would, uh, find things around the house that, uh, no one wanted or that were in our junk drawer that everyone seemed to have. Or occasionally I would find, you know, my old toys and things that I didn't want anymore. And I would invite my grandparents over and any family and friends that would be willing to, uh, to participate in this nonsense. And I would have these little yard sales first inside the house. I would set up a TV tray with these little items on it that, uh, people could purchase from me to make a little bit of money. And then, uh, eventually it moved to the yard, uh, the front yard. We lived on a pretty busy street. And so when, uh, my parents had a yard sale, it seemed like that was something that people did somewhat frequently in those days. I would, uh, very much be an active participant in that. And I would be out selling all day, uh, trying to earn a few bucks so that I could buy whatever it is that was interesting to me at the time and kind of take control of my own destiny.

That's so great. I can just picture your parents shelling out dollar bills to buy their own things back from them.

Yes, they were very kind and played along with this, uh, this Ponzi scheme.

And then as you got a little bit older, even before you could drive, you started an actual business out and about in the world.

Yeah, I, uh, my brother, uh, is 20 years older than me and he's always been very entrepreneurial and, uh, he kind of has been a mentor in that sense, uh, for me throughout my life. And he, uh, worked, uh, in construction, but he also had a lawn care business. And that lawn care business grew to be pretty successful. And, um, I, uh, I first started, uh, kind of just emulating what it was that he was doing and borrowed my grandfather's mower and would cut people's grass on his street that would allow me to. And then eventually I, I joined him in that business, and I spent some summers working for him in that business. And, uh, I think I was Fired 2 or 3 times, um, for, for not, uh, participating as actively as I should have. But eventually, uh, I think probably the time I was 14 or 15, he had moved on to other things or was ready to move on to other things at that point. And I purchased the business from him. I'm sure it was a very generous offer, but, um, I did. I purchased the equipment and, and the trailer and everything, and I took over the business that that he had initially established. And that business really helped me pay for college. It helped me create that agency that I sought so deeply and helped me buy my first car and all of the things that a teenager would do with money at that time. It taught me about accounting and bookkeeping. I had employees because I couldn't drive, and so I had to hire people that were older than me to drive me to the various places that I had to cut grass. Two of the bigger contracts that I had were, um, uh, the Delaware State Fairgrounds, which was pretty significant. That was probably enough to keep a lawn care company in business by itself. It was a big job. By the time we finished, uh, cutting, uh, that, those grounds, it was time almost to start again. Uh, and then I had, um, some, some home builders and of course a ton of residential properties as well. I learned about marketing at that time. I learned about sales. It was just a, a really, I think, formative experience for me that, uh, I'm really glad that I had the opportunity to have. And, uh, it certainly gave me a sense of freedom and agency for a teenager at that time that I don't know that I would've learned otherwise.

Sure. So you had your first acquisition by the age of 15. It's pretty impressive for the resume. But it's funny, you keep using the word freedom and agency, and I think definitely that's true. But what I keep thinking is, as a teenager, we are so self-conscious and worried about looking silly and putting ourselves out there. And it makes me really curious how you had the courage to go do something like that. Where do you think you got the, just the courage to take a risk like that?

Again, I think I had, um, I had a good example with my brother before me. In many ways, I just kind of followed in his footsteps in, in business. But also, I felt like there was some areas of my life that I almost felt like I had no agency in. And so I wanted to control the things that I felt like I could control. I was, as a teenager, more than 100 pounds overweight. And while I now understand how to control that, I didn't at the time. And so my school experience was not as great maybe as others had, you know, dealt with bullying and just being uncomfortable all the time in my own skin and. And so I felt like if I can't solve this problem, then what problem can I solve? And it seemed somewhat natural to me in business to find ways to, to market, to sell, to make money, um, to serve customers. And so I think I leaned pretty hard into that, uh, far more than my peers did and had some success in business at a, at a pretty early age and, and just kind of fell in love also with just marketing and sales in general. I always joke with our teams today, like, in some ways I wouldn't care if we were selling toothbrushes. You know, I just— I love the idea of building a brand, marketing that brand, and finding differentiated ways to sell whatever that product or service is. And I think I fell in love with that at a pretty early age.

Yeah. And it's funny, the idea of control and agency does come up a lot, and I would imagine feeling that lack of control when something like a house fire happens, or when something like, you know, the social dynamics of being a teenager feel out of your control, that it makes sense to me that finding an area and an arena where it was your kingdom to, you know, kind of lay out the way that you want to, it makes a lot of sense to me. So interesting. Well, from there, you know, then we go off to college, right? You lost 100 pounds sometime in that timeframe. And so, you know, speaking of control and taking control of a different area of your life, what sparked that and what lessons do you carry forward from that life experience?

Yeah, I mean, I think, I mean, there's no justification for it, but I think I was kind of a knucklehead in high school in part because I was overweight. And I wanted to find my place in the universe somehow, some way. Uh, and, uh, and so I was attempting to be a class clown, um, just kind of disruptive in the classroom. And, and ultimately, um, that led to, uh, me getting in a fight in school. Um, and I think as high school fights often are, it was with one of my friends, uh, but Unfortunately, sorry, Nick. Unfortunately, the, uh, the school administration had a zero tolerance policy, and, uh, and so I was suspended. But also with that fight came an arrest, and it wasn't like I was handcuffed away and taken to prison, but there's a formality to that, I think, when you have a zero tolerance policy around violence in schools, which is understandable. And so that was my senior year, and it was kind of a wake-up call for me. I knew that I couldn't continue just being a goof-off, and I needed to take things a little bit more seriously. And one of the things that the school resource officer recommended to me at the time was to go to something called Trooper Youth Week, which was basically a 1-week-long state police boot camp so that you could learn what it would be like to become a state police officer. And so there was a classroom session, but there was also a lot of physicality to it, similar to what you would think of as a traditional military boot camp. I can remember scrubbing the floors with toothbrushes and getting up early with the sound of a trumpet and, and running and just being forced into discipline that I probably hadn't yet learned at that point in my life. And so I went to this. It was, I think, a couple of weeks after I graduated from high school. Is when it started. And I think during that one week, I lost something like 20 or 30 pounds because you could only eat what they gave you to eat. There were no second helpings. There was no dessert, which I had become quite accustomed to. And we were exercising a lot and running a lot. And so it kind of pushed me to get into shape and have a little bit of discipline in my life. And so I was, um, I became somewhat obsessed, I think, with that progress. I saw like, wow, like in, in just a week's time, like I lost like 20 pounds, which is insane. I felt like a different person. They made me cut all my hair off like they do in, in boot camp. Uh, and at that time I had a pretty long hair. And so when my parents come to collect me from, from this camp, I literally looked and probably acted like a completely different person than, than the boy that showed up. And I continued those habits. I felt— it felt good to feel like I had control over those areas of my life. And so I remember coming back home and continuing to make my bed the same way that we were taught to while we were there. I kept my room quite a bit cleaner than I had previously. But I also continued the exercise and the eating habits that I learned there. For me, it was— I always struggled and still today struggle sometimes with portion control. And so what I learned was if I eat just 1 or 2 meals a day, then portion control isn't quite as important if you're eating 3 or 4 meals a day. And so that's what I did. I ran every single day, I think, for a 2-year period without missing a single day. It was typically a 1.5-mile loop around the development that was across the street from our home. Sometimes once a day, sometimes twice a day, but every day there was that routine that I did. I also worked a pretty physical job that summer at UPS, so I would get up at 3 in the morning and go load those trucks and come out a completely sweaty mess at 8 or 9 o'clock when I finished. I would go on that run and then take a little nap, and when I woke up, I would have my first meal for the day. And so I think from, uh, both restricting calories and just exponentially increasing the amount of exercise that I was doing, it allowed me to lose over 100 pounds before I started college, which was just a couple months away. And so by the time I, I started college, people that had been my friends for my whole life that hadn't seen me that summer didn't even recognize me. I was a completely different person in every way. Uh, and, uh, it was a transformative summer for sure in my life. And I felt like I stepped into much closer to the person that I am today over that summer than the person that I was prior to it beginning.

It's really an incredible story, especially when you consider it's only a couple month time span. And there were a couple things that you said there, and I'm just curious if you had to assign a weight as to, you know, what really was the factor that changed things for you. You said you kind of felt like you had hit a rock bottom, right, with a fight and being pushed in a direction. But the other thing that really struck me is this idea of how our habits become our identity. And it sounds like you really overhauled your habits. And now, you know, what, 20 years later, watching you, you are definitely a very disciplined person with your habits. So was there a lesson in terms of daily routine or habits that you feel like you took away that sticks with you today?

Yeah, I think probably some good and bad things around it. I think that one of the things that became apparent at that time, probably because I hadn't experienced so much of it before then was just an addiction to progress, which can become dangerous, you know, and, but I just felt like there was every day I would get on the scale and weigh myself and every day it would be an improvement, literally every single day. And you know, that, that, that can lead down all kinds of paths that can become dangerous for you. But I think that that was one lesson that I learned. And it goes back, I think, to that agency piece of it is you, you do have control over a lot of things in your life, uh, and there's, there's not often a hack. And that's what I had tried throughout high school. I tried all of the fads, you know, the Atkins diet, the Weight Watchers, and all of these things. And I was always the biggest, youngest person in the room when I was, you know, trying to do those things. And they would work for a little while. I might lose, you know, 10 or 15 or 20 pounds but ultimately I would revert to the same old habits that I had previously. And I probably just hadn't learned the level of discipline that I needed. And I also hadn't tasted the consistent progress that you could have. But once I began to taste that, then I think I understood it much better. And I've used that in several areas of my life. And I learn now that, you know, you can't— it's not realistic to have progress like with that weight loss journey where you're losing 10 or 15 or 20 pounds a week. And many doctors and health professionals would argue that's not the healthiest way to do it. And I would say, you know, it worked for me. It worked for me. And whether it was the best way to do it or not, that's, that's the only way that I was able to do that. And so I've learned to kind of celebrate a little bit more of the smaller wins, the ones that you don't notice maybe until you look up a month or 2 or 3 months later and you realize that you're a little bit better at this thing. Or you've achieved a little bit more of this thing. And I think it's Tony Robbins always talks about that he believes that progress equals happiness. And for me, for most of my adult life, I would say that that's likely true, that holds true for me. But again, I think there's some dark sides to that that are, that you have to be cognizant of too, because it can become an addiction, it can become problematic because it's not a straight line up. You know, and no matter what it is that we're doing, whether we're trying to lose weight or we're in business or whatever it is that we're, we're pursuing in life, there's always going to be times where you're not progressing. And maybe that progression is through the failure that you experience, that it just takes a while to kind of dissect and understand after it happens. But you have to get comfortable with that too.

Yeah, it reminds me, we've had a couple conversations float our way through podcasts and other things recently about just the discernment between when it's time to keep pushing through and when it's time to rest, or, or even just enjoy the gratitude for the things that you have accomplished. And I think, to me, from my perspective, that's something that you've been kind of implementing into life now, you know, 20 years later. But there is a time, a season of life, where maybe becoming a person that seeks progress, that has agency, was the right move for you. And, you know, I'm glad that you did, and I'm glad that you're not still losing 10-15 pounds a week because you'd be going back down to your birth weight at this point. But anyway, let's jump forward a little bit. So back, you know, you lost 100 pounds, you go off to college, and it's right around this time that we meet. And at that time, we were both in a completely different field that, to me, was another big dot when I look at your life history, which was working in politics and kind of what that meant to you and what your roles were, maybe giving an overview of what we did.

Yeah, so, uh, because I was a knucklehead in school, I, I didn't get into the big university. Uh, and so in many ways that was a blessing as well. So I, I was accepted into what, uh, Delaware had at the time, I guess they still do, called the SEED program. And so the first 2 years of my college was actually, um, to earn an associate's degree through the University of Delaware, but at the local community college. And so I could continue to live at home. They covered, um, most or all of the expenses related to that associate's degree, which kind of helped me ease into, uh, a college world that I probably wasn't ready for. And didn't have the maturity for at that point. But it also gave me an opportunity to work on political campaigns. And my best friend Justin had gotten offered a job to work for a guy that was running for governor at the time that eventually became our governor in Delaware. And it seemed exciting. It seemed fun. I was always kind of interested in politics. My grandfather was involved in politics. As a kid. And, and so I jumped at the opportunity to join Justin, not knowing completely what I was getting into. But I still think that that summer, which was 2008, was probably the greatest, craziest summer of my entire life. And working on a political campaign, regardless of your party affiliation or your beliefs about politics, I think is something that everyone should do at least one time. Because picking up the phone and cold calling people and selling them a candidate, selling them issues, knocking on their doors, coordinating volunteers, marketing, all of the things that go into that short period of time that you work on a political campaign are skills that transfer to just about anything you could ever imagine doing. And I think that a lot of the success that we've had in business comes from the experiences that we had working on political campaigns. And I, while I, I don't necessarily miss that part of our lives, can become jaded after a while and get a little bit burned out in that field, I'm very grateful for those experiences.

Absolutely. And just the, the tolerance to deal with rejection, I think, alone is, is something of going up to someone cold, not knowing how they're going to react, and having the courage just to approach over and over again and keep trying. Yeah.

And the thing I love about political campaigns, which is just really unique, is, is that it's a, it's a sprint. Yeah. There's a, it's a short period of defined time. You know, when the primary is, you know, when the general election is, you're not going to start that campaign, uh, full tilt, at least 2 or 3 or 4 years in advance, unless you're running for president. And so you have these several months, uh, where you're just, your entire life is consumed by this one project. And I think our, the human spirit can, can really dive deep on something and work 12, 13, 14, 15 hours a day and completely get lost in that experience if they know that there's an ending that is guaranteed. Uh, and that's what I loved in part about campaigns. You know, we, we worked 7 days a week. It was 12 hours a day, every single day.. And for the most part, we loved it. Uh, I got to do that with my best friend, which was really cool. And we got to meet so many people. I got to do things that my peers never did, you know, and, and experience the world in a way that, that I didn't know that I could. And so it was just such an incredible experience. And I, I, uh, I always think fondly about that summer.

It is. Yeah. And, uh, we met too. So that was cool.

Yes, we were, we were both working on, uh, campaigns and, uh, That was the summer we met, and it was at a picnic in Rehoboth.

That's right. Good job. But totally. And when I think about it too, I just think about getting a group of people that are really passionate about the same thing together, all rowing in the same direction, being caught up in that culture and that energy. And in a way, that reminds me a lot of what we still do today in our company.

Yeah. And I think, I think the nuance maybe, and maybe you could compare it to like a startup type environment. Is that there's almost like this brotherhood or sisterhood that comes from that campaign where you are so deeply embedded in that world with the people that you're doing it with that, you know, I still think about all the guys and gals that we worked with at that time. And there's just like a, there's a bond there, even though some of them I haven't spoken to in 10 or 15 years, that I feel like we could get back together and just return to those same conversations, return to that same work and just understand each other in a way that a lot of people don't. And, uh, I certainly would, you know, wouldn't want to compare this directly to like a military-type experience at all, but there's— I think there is that same sense of kind of brotherhood that you get from this because there's just— there's so few opportunities in life where you can spend 7 days a week, 12 hours a day, essentially living, you know, with this tight-knit family of people around a centralized goal and topic candidate, and it just kind of creates a different type of bond, I think, that is pretty cool.

That makes sense. I mean, working together as a team to overcome adversity, you know, and there's war adversity, but there's also, you know, just the adversity of long hours and a lot of nos and pushing through. And it shows. I remember visiting that office and delivering you guys coffee sometimes, and it was just like, it was like walking into the war room, and there's papers everywhere and phones ringing, and it was, it was a really cool experience.

And it was cool because I think in part because it was the most competitive gubernatorial race in the entire country, certainly as a primary. And Delaware was not used to that. You know, we— it's like a good old boy state where, you know, the next person in line kind of moves into place. And we had, you know, we were fighting hard in that race. And ultimately we ended up losing the primary. Right. Which was somewhat unexpected, but, um, we, we learned a lot of lessons. And, uh, I will, I will say that Justin and I won our county, so we, we did our part in that race. But it was a cool experience.

But I think that's a good point. That's where I was going to actually go next, is you ended up losing. And I think a lot of times, you know, one of the goals of this podcast is to show it's not all dots that are these shiny trophy success stories. Sometimes the dot is ultimately not the result that you wanted. And so what What do you think stuck with you about that, about putting in that much effort and still not getting the outcome that you hoped for?

Yeah, I mean, we were devastated. I mean, when you, when you commit that intensely to something for that period of time, it's, it's difficult to really know how you're going to feel if you don't come out victorious. And I know the other side, you know, would have those same thoughts and fears. Yeah, I remember primary night, us, being in Wilmington, hoping to celebrate victory because it was a very close race and getting the news and just, you know, the weight that fell upon all of us. It was tough. And, you know, I'm sure it was 10x as hard for the candidate and our campaign manager and the people that were more senior to me in that experience. But it hurt. It stung. And I think it probably took me— I don't know, a few months to really kind of move through that. And I continued to work in politics off and on for a number of years through college and post-college for a little while. But there was just something unique about that particular experience, I think, that was different than any other. You know, we— our campaign, because it was so competitive and it was fairly well-funded on both sides, was, was led by people that had worked at very senior levels in presidential campaigns. And so it was a tight ship. It was run, I think, uh, probably on, on both sides of that campaign. It was run as well as any campaign that I've ever seen. And, uh, I'm, I'm just really grateful to have that experience and to have learned from some of the best in the world at, at what they did.

Absolutely. Well, you mentioned, you know, you puttered around in politics for a little while longer after that, but then we took kind of a hard left turn. You and I both, and got into the field of teaching, which is completely different than politics, but still some really important lessons that I think we've carried through today. So talk about your time teaching and kind of what you draw from that life period.

After the campaign, um, I, I was entering, I guess, my sophomore or junior year of college at that point, and my degree program was international relations and foreign policy. And I, I thought that, you know, I would continue to pursue something in politics. And so again, like you said, I puttered around campaigns for a while. I ran a statewide, uh, campaign that was successful. We elected the first African American to statewide office at that time, which was something I was really excited to be a part of. We had a great team, uh, and, uh, and for a variety of reasons, I decided not to follow that candidate, um, into his office, but I didn't really know what I was going to do. Then. I just made a decision that I didn't want to do that. And so now what? And I wasn't necessarily qualified to do much else because that's really— that was my professional experience. My degree program was somewhat related to that experience. And so I decided to go back to school again, went back and got my master's degree in education. I think as a kid, I always— I had a lot of family members that were teachers involved in education.. And I always thought that that was— it felt like kind of a safe, normal trajectory of someone that they should pursue. And so that's what I did. And I had— I saw kind of the gamut of education. I started at an alternative school. Many of these kids were— had been in detention centers or had been expelled from their public schools, and they were sent here because it was somewhere else that they could be that wasn't there. And, uh, that was a, a really interesting experience. It's a great school and they do so much good for those students. My sister has, has worked at that school now for more than 20 years and now leads their administration. Uh, but it taught me a lot. It taught me a lot of things. And as a 20-year-old, or however old I was at the time, I had students that were 18 years old that were far bigger than me, that had seen a lot more of life than I had seen at that time.. And it was quite intimidating. And so I did that for a while. And while I was finishing up my graduate degree, and then I got a job at a public school that was a great school. It was a temporary position that I was able to get that unfortunately wasn't renewed, but that then led me to a charter school. And so I went from alternative school where these kids are, you know, in many times homeless, they're just dealing with really difficult situations. To a pretty standard public school, then to a charter school where most of these kids are coming from some wealth, from parents that have invested a lot of time and energy and money in them with high expectations. And the test scores at the school were some of the highest in the state. And so seeing the full gamut of education, I felt like I got to kind of sample it all and see what I liked and didn't like. And while I did enjoy spending time with kids, And I enjoy a lot of aspects of teaching. What I didn't like was that it felt like there was no real opportunity to progress financially. There was a tremendous amount of evaluations in that profession, and I didn't feel like that was who I was for the rest of my life. There was just something that just felt kind of off. I did it for 5 years. I enjoyed the time that I did it. I coached sports, I involved myself as much as I could, and, and I really tried to like it. And, uh, ultimately I, I just found that I didn't. I didn't like sitting in a classroom all day or standing in a classroom all day. I felt like I needed to be out in the world creating, building. And again, I think it goes back to agency. I felt like teachers have agency, of course, you know, they're, they're some of the most important jobs that we have in our society, but I didn't feel like I had as much agency over what I could teach, how I could teach, my own income, how I spent my time, all of these things, because it was so scripted, you know, and it had to be scripted based on, you know, regulations and state requirements and things. And so it became pretty apparent, I think, after about 4 years that this wasn't going to be for me.

Yeah, it's funny, my dad always used to say to me when I was in that life phase of trying to figure out what I wanted to do, that you need to figure out what you don't want to do before you can figure out what you do want to do. And in different different industries, different fields, there's usually some things you like, some things you don't like, and you're trying to find the right combination, the right balance. There's always, you know, no perfect fit, but it's clear to me that that wasn't the perfect fit for you. But that being said, I think there were some really valuable things that came out of us teaching, not least of which is I think we now have hired multiple of our former students, which makes me feel old, but also is really cool to see how you can follow a young person's trajectory from being in school 7th grade to being an adult that's, you know, married and in the professional world and all of those things. Um, but beyond that, I'm just curious from your perspective, as you reflect back, if there are any soft skills that you learned as a teacher that you think really inform the way you conduct business or think about things professionally today.

Yeah, I think anytime you're part of a, an organization, a bureaucracy, you know, a system that has been built for decades prior to you entering it, there's a lot of lessons to be learned there. Because there's always, you know, there's a negative connotation, I think, to the bureaucracy and these rigid structures, but there's some good that comes from that too. And I think it teaches you the things that if you were to have build your own organization, the things that you would take and the things that maybe that you would leave. And so I think that was one lesson. I think when anytime that you're working with kids in any capacity, I find that the kids end up teaching you far more than you teach them. And It's just fascinating to be around those, those minds, you know, and, and the curiosity that comes with it and the changes that are happening in their lives and then reflecting on your own life at that age and all the lessons that come from that. And I think it, I don't know, it makes you maybe be a little bit more present in life as well when you look at a child and you see the presence that they're living in while they, they may have hopes and dreams for their future. What happens right now is what's most important to them and what they're feeling most emotionally. And, uh, I try to remember that often, especially if we have kids now. I think that if Tony Robbins said that progress is happiness, which I do often agree with, I think that maybe the, the deeper lesson there is that presence is a part of that happiness. And I think that if we're always past-oriented or future-oriented, then we miss what's happening right in front of us and whatever that is that's happening in front of us might be the only thing that's real, you know. And I think the more that we can experience that completely, the more joy that we'll get from it.

Yeah, I completely agree. It's one of the great blessings of being around kids. And if it makes me a little emotional just thinking about being around young people, and especially those years where you and I were both teaching at schools where, you know, the children were dealing with a lot at home, and watching these, these kids that were 10, 12 years old coming in dealing with such tremendous baggage at home, and yet still having this light and curiosity and excitement about the world and dreams inside of them. It's just, it's really humbling, and it makes you look at adults differently too, because you realize a lot of the people around you, they were those kids, you know, that had to overcome tremendous adversity to get to where they are. And so it's, it's really an incredible gift to get to spend time with young people and see how they grow and develop.

Yeah, you and I always, uh, talk about that. I— whenever someone, an adult, does something really bad, you know, put whatever label it is on them, even as horrible as like murder, I, I try my best to think about them as a little child, you know, and think about what were they like as a baby, what were they like as a toddler, what circumstances led to the position that they're in today. And I think it allows us to be a little bit little bit more empathetic and to offer a little bit more grace for people, because I don't think anyone sets out in the world to say, I want to do bad things or be a bad person or be a villain. And I would argue that many of the people that are quite obviously doing bad things don't necessarily think that they're doing bad things. There's some justification. There's some experiences that led to the path that they're on today that seem right to them. And while we certainly shouldn't excuse bad things in any way, I just think it helps us be a little bit more human and understand that everyone's experiences kind of lead to, to where we are today and the things that we've, we've done, both, both good and bad. Um, and I think that empathy in that, that child is far easier when we think about it that way than it is as the big bad mean adult maybe that did something we don't like.

Yeah, and just like with everything in life, nothing's ever black and white or cut and dry. Just like life isn't always about progress, and it's also not always about resting in the present moment either. You know, it's always a push and pull, and people are very complicated. And you're right, when you think about them as children or get to spend time with young people, a lot of those threads kind of come together in a way that forms a picture, makes it a little bit clearer. Um, well, from there, I remember very clearly when we were both teachers, being pregnant with Avery and getting really close to my due date, and you saying, you know what, there's a real estate course starting, and We at that time had a tiny little rental house. I mean, I think we paid like about the price of a car for the house, and it was essentially a tiny house, even though it's not technically the cool tiny houses that people are building today. And we just kind of liked it a little bit, and we liked that, that field and thinking about housing and rentals and sales. And, uh, we went to sell our house at that time and felt like there were things that could have been done better. And so I remember you signing up for the real estate course, and almost to the day that Avery was born, is when your real estate license came in.

Yeah, and, uh, it should be stated plainly that ever really since the time we were 18, we've, we've both kind of worked the same job, you know.

That thread hasn't been clear.

We were in politics together, became teachers eventually at the same school together, and there was a common thread there that I think, you know, we just really enjoyed spending time with each other and being together as much as we could. I think since, since we've been, or I've been 18 years old, there, there probably hasn't been more than 10 or 12 days in total that we've spent apart. And most of the days have been not just together, but together basically all day, which is, I think, somewhat unique. And so, yeah, I think that it became apparent that I wasn't loving teaching anymore at that at that time, you were expecting our first, which was kind of terrifying in and of itself and exciting and all of those things. And weddings are not cheap. And we knew it was going to be a little girl. And, and so we, we kind of talked about it. We saw that the real estate course was happening and I signed up for it kind of on a whim. And I fell in love with it. You know, I felt, I fell in love I think more with returning to kind of my business roots, even so, even more so than, than the real estate as an industry. As I think there's, there's a lot of challenges in, in real estate that, you know, we continue to try to solve. But I just love business. I love the idea again of building a brand, of marketing, of sales, of, of helping people and, and finding new ways of doing those things. And that was always important to me if we were going to enter I wanted to do it different than other people. And I think James Dyson, you know, talks about this in this book is like, if you look at a Dyson vacuum, it's purple and it's, it has a cylinder on top of it and it's oddly shaped and all of these things. And part of the reason with the colors specifically is because he specifically wanted to be different. And there is a value in that. And as we were kind of entering the real estate industry, I knew that I did not want to do things the same way that we had been served by, you know, people in that community through our selling process. And so we jumped in headfirst with a, with a baby arriving. My license came in, I think roughly that same day. And we spent that summer, you with a baby in your arms, cold calling and prospecting and trying to figure out what is our brand and, and all those things that you do as you enter a new field. And we fell in love with it, I think. I think we fell in love with building something together, of creating something together that would truly be our own. And I taught one more year, you taught half a year, and we left teaching. And our— everyone, our parents, everyone thought we were crazy. We had stability, we had benefits, we had wanted, you know, retirement, health insurance. And in order to make that happen, we sold our house, we sold our cars, we drove a 2001 rusted-out Pontiac Sunfire, moved in with my parents for a period of time until we could find something cheap that we could, you know, renovate ourselves. And so yeah, it was— it's a crazy formative time in life. And, you know, it's, it's amazing how quickly then the time goes by and you enter that field and And that's what we, we have been doing for 11 years. It's been a crazy wild ride, and it's been a lot of wins and challenges and losses and markets and everything that goes into that. But it's every day we're learning new things.

Yep. Yeah, absolutely. I mean, it's been, it's been a crazy decade-long ride at this point. And, um, you know, what it first brings to mind for me is just I always love this idea, and it seems to circle around in a lot of people's life stories where— and we already talked about it once in this conversation— but there are things that we just seem naturally drawn to as children, you know, before the world puts its imprint on us, before we feel pressure to be this way because of how our parents feel or our peers feel or our community feels. And for you, you started your, you know, play-work journey selling tchotchkes back to your parents in the living room, you know, and then you come full circle and go from a stable, you know, state benefit job right back into building a business again. And once again, you know, there have been a couple points on our journey, and I think that maybe you don't appreciate it as much as I do as an outsider, but of just the courage that it took to follow your own path at certain points. And certainly, you know, newly married, new baby, a stable job that you're giving up to jump into something completely unknown— I think a lot of people would say that took tremendous courage. And so what, what gave you the confidence to take a leap like that, especially at that moment in life when there were people that were saying, this is not a good idea, don't do this?

I was definitely scary. It was not without fear for sure. There's something in my nature, my DNA that is almost, I feel like, allergic to the stable path. I have like a negative reaction almost to that word. And it's a push and pull. Everybody wants stability and safety and security in their lives. But for me, I feel most alive when I'm taking a risk, when I'm trying something new, when I'm putting myself in a position to be uncomfortable and be humble through that experience. And how quickly can I learn to master this game? And what is the game? And all of those things that go into it. And so I started reading a lot of self-help books at that time and business books and different things. And I think the thing that probably gave me the confidence, other than, you know, having a brother that had succeeded prior to me in business, was reading Tim Ferriss' The 4-Hour Workweek. And, you know, whether he says it directly or not, I can't remember in the book, but there's almost like this— the real risk is not trying. The real risk is, is just accepting the easy path or the stable path. Now, there's nothing wrong with that if that's what you love, you know, if that's the thing that you love and that you want to do and that gives you meaning and fulfillment, then, then that's amazing. But it was clear for me that that was not the case. And so I could, you know, stay in that path and, and spend 20 or 30 years teaching and probably move into administration. And I felt like I could, I could imagine what my life was going to be for the next 30 years very easily. I could put it down on paper and it was very likely this is what's going to happen. And that made me very uncomfortable. I like adventure. I like journey. I like mystery. I like outsized returns on the risks that you take and the lessons that come from the failures in those risks. And so I don't know. I knew that some things look far more risky than they are. Believe the surface. I think I've been somewhat conservative throughout our lives financially, and so I don't think that I was comfortable taking that risk until I offloaded the financial responsibilities largely that we had, which was, you know, selling our house and our cars and just kind of downsizing our expectations around what it meant to live. And, and I'm thankful and know that, you know, not everyone has the opportunity to move back in with parents with a newborn baby and a dog and all the things that come with that. So that helped provide that sense of security and stability. But I knew I had to try. I knew I had to try it. And we were feeling a little bit of that early success. I think we weren't failing into something. We were kind of figuring it out. We were figuring that if you do these things, then here's the outcomes. And so we had kind of figured out the algorithm for success in real estate and through coaching and mentors and different people in the industry. And we knew that if we just if we just follow this formula, then these will be the results. And that's what we did. And we had confidence, I think, in our own abilities. We had confidence in, you know, that things just generally work out. And I think if you're going to be in, in business especially, you have to be an optimist. You have to assume that things are going to get better and that ultimately good things will happen. Because if you're not, you're not going to run a very successful business. And I think we've both always held that belief And I think a lot of it also comes from believing in each other. You know, I think if it's one thing for your parents to say, you know, that's crazy, don't, don't do it, or reconsider, it's another thing if that was your spouse. And I know a lot of people do contend with that and plow forward still. Um, but that's, that wasn't the case with us. I think, you know, you, you gave me tremendous confidence, and I think we kind of rallied around each other and That helped us launch into something that was scary, but we knew we— if we had each other, and we're going to figure it out. And we ultimately, we did, and we're still figuring it out.

Yeah, well, I mean, and then here we are today, you know, what, 15-year wedding anniversary coming up. And so to me, I think we've covered a lot of ground, and I think we should probably start to bring it to a close. And so I want to look back and call out the dots that I see in your journey, and I'd love for you to, you know, flesh out, correct, tell me, tell me what you think is right or what maybe what's a little bit off. But when I look back at your earliest upbringings, I see a tremendous sense of community and of wanting to be integrated with people that support you, to give back to the community that gives to you. And I think that's always been incredibly important to us at the Parker Group and other companies. I see life lessons that pushed you towards discovering your own sense of agency when life felt out of control, when situations felt out of control. Then I see entrepreneurial experiences that gave you confidence that you could build something from nothing, whether that was lawn care, political campaigns, and then eventually real estate. And also just seeing the value of being able to carve your own path and make your own rewards in the world. What other dots do you think kind of contributed to that? Or tell me where I'm off base.

I think you nailed it. And, um, I think because, you know, we've spent 18 years together every day, almost 24 hours a day, I think we know each other really well and very intimately. And I think that, um, you know, I would say that maybe the biggest dot along the ride was me finding you, you know, because I think that you exposed me to a different world that I wasn't familiar with necessarily growing up in a really small town, a really tight community. You know, you had all kinds of world travels and things prior to me meeting you. Your parents kind of grew up in a bit more of a hippie generation than my parents did and just kind of a different perspective on life. And you were also far smarter and more academically successful than I ever was. And so It exposed me to a new way of thinking, a new community. I think I became maybe a little bit more cultured, you know, and, and I think that that's probably was, was the biggest thing that happened in my life. And, you know, many people say this and I wholeheartedly agree, the most important decision that you will ever make in your life is who you're going to spend your life with. And that starts, I think, with your, your partner or spouse in life. And, but it extends to your friends and, um, and your family. And while you can't necessarily choose your family, you can choose, you know, how much time you spend with your family. And you can certainly pull people into your family, maybe that aren't family by blood. And I just think that our, our, all of the dots in our, our lives in general are built around the people that are in it. And those people, whether we want to believe it or not, have tremendous influence on the things that we do and our own perspectives on life as a whole. And so choose those people wisely. And I'm grateful for all of the people in my life and even the ones that maybe I wasn't so grateful for at certain times in my life. I think it all led to a positive outcome in the end.

I didn't pay him to say that. Well, this is my last question, and I think to me it's the heart of what this podcast is meant to be about, which is when we see people that seem to have had success, it can feel inspiring, but it can also feel intimidating. And, you know, I know you mentioned a couple places along the path where you were out of politics, but you didn't know what the next thing was, and you were kind of searching. And I've seen now, at this phase of our lives, you know, almost 40 years old, that some younger people come to you and they say, you know, I look up to you, I want you to mentor me. And to those people that might be hearing this and be thinking, I'll never land there, or how do I figure out what my path is? Maybe I'm in something that just doesn't feel like the right fit right now, but I don't know what the right fit is. What advice would you have for someone that just feels a little lost right now?

Yeah, I'm still trying to figure it out myself, and, um, I, I'm probably uncomfortable even with the word success because I, you know, we're so fortunate that we get to spend time with, with billionaires and with some of the smartest and most incredible people on the planet. And when I, when I get into this like competitive mindset, sometimes it's like, well, I'm, I've done nothing with my life, absolutely nothing. And, uh, and then that's not a good way to think about, you know, the, the successes that we have had in life. But I, I, I think you have to really think about what, what doesn't feel like work to you. I mean, so many people talk about this, but what's play? What would you do for free? What would you pay to do, to have the opportunity to do. You know, for some people, maybe that's golf. For others, maybe it's music. Or there's so many things in the creative sense that that might be. Maybe it's business. You know, I, I don't know what that is, but I think that if we go back to our childhood and we begin to think about what were the things that we really enjoyed, enjoyed doing as a child, uh, that just felt right and, and felt like it gave us a presence in those moments that that we now have nostalgia about, there's probably some thread there that you could begin to pull that may lead you down the path of finding whatever that thing is. And if you're unhappy with what it is that you're doing, I think that's okay for a period of time. We often do things that we don't want to do for periods of time, but we shouldn't do that for our whole lives. And our lives happen much more quickly than what we like to admit. And so, um, if you're still in the same position a year from now that you're in today, and that position is not a place that you want to be, it's probably time to do something about it and to make a change. And I do think that we all have agency to make those changes, and there's plenty of people out there that would be happy to mentor everyone. And I think that people get filled up from mentoring. And so you just have to ask the questions, to take the chances, to, to go out on a limb, take the risk, and be willing to fail, and just know that You're going to be able to get back up and, and do it all again and maybe take a different path this time, but take the lessons that you learned to create something cool.

Love it. Well, thank you for answering my questions, for connecting those dots with me. It's a really fun conversation and really looking forward to future ones and just, you know, tracing life stories and learning the lessons we can from each other.

Thank you.