🎙️ Episode #14

Love, Marriage & Bootstrapping: Kim & Jason Coleman on Building a Software Company With Your Spouse

Love, Marriage & Bootstrapping: Kim & Jason Coleman on Building a Software Company With Your Spouse podcast cover

Show Notes

Kim Coleman and Jason Coleman are two entrepreneurs who have shared the journey of building a software company. However, their mission has been much more than a professional partnership. They’re a married couple with two kids who’ve built a successful company and several software products together: it’s safe to say they bring a unique perspective to the world of bootstrapping. 

In 2006, they launched Stranger Studios, a web design and software development studio. In 2011 they launched their now flagship product Paid Memberships Pro. The big success followed in 2015 when they started building the team.       

For most folks,  logging off or commuting home at the end of the day is enough to separate your work life and your personal life. But for Kim and Jason, the lines are not as clear cut. In this episode, they discuss navigating personal and professional challenges, that range from compromising (or not) on hard decisions to facilitating a healthy work environment that encourages team morale, all while maintaining a harmonious marriage.


Thanks to Kim and Jason for joining us and providing such valuable advice about building successful distributed companies. Join us next week with Chris Badgett, the co-founder and CEO of LifterLMS and one of the leading voices in open-source eLearning and educational technology.

plugin.fm is brought to you by Freemius, your all-in-one payments, subscriptions, and taxes platform for selling software, plugins, themes, and SaaS. If you enjoyed this episode, head over to plugin.fm to check out previous episodes.

Chapters & Episode Notes

0:00 – Intro

1:12 – The Journey into Software Entrepreneurship: Kim and Jason’s Story

6:00 – From Consulting to Product: The Evolution of Paid Memberships Pro

13:16 – Navigating Decision-Making as a Couple in Business

21:25 – Balancing Business and Personal Life in Partner-Led Ventures

26:00 – Managing Disagreements in a Joint Venture

28:44 – Creating Boundaries: Separate Workspaces for a Harmonious Marriage

36:45 – Strength Through Adversity: Overcoming Hardship Together

39:28 – Navigating Entrepreneurship as a Couple: Key Lessons and Advice

44:44 – Outro


Kim: A lot of people, when they hear that we work together, the immediate thing they say is, “I could never do that.”

Patrick: Today, I’m joined by two entrepreneurs. Successful software journey is a side-by-side endeavor that goes far deeper than a professional partnership.

Jason: We doubled the prices, and people kind of didn’t blink. Like new people were paying twice as much and twice as often, and kind of overnight in one month, we went from $5,000 a month to $20,000 a month. Then we made it full-time products.

Patrick: As a married couple who built a successful company with several software products, Kim and Jason Coleman bring a unique perspective to the world of bootstrapping.

Hello everyone, and welcome to another episode of plugin.fm. In this episode, we’re going to explore how Kim and Jason navigate personal and professional challenges, from compromising or not on hard decisions, all the way to facilitating a healthy work environment that encourages both team buy-in, all the while maintaining a harmonious marriage.

In 2006, they launched Stranger Studios, a web design and software development studio. In 2011, they launched their now flagship product, Paid Memberships Pro, and they really saw success in 2015 once they started building the team. Kim and Jason, welcome to the show.

Jason: Hey, Patrick.

Kim: Hello, thank you, thank you for having us.

Patrick: Yes, and thank you for joining us. I am excited to chat with you. It’s been a little bit since we’ve chatted in person, I guess on a podcast. I want to start with what inspired you two to venture into software and why start your own company.

Kim: For us, we’ve been high school sweethearts. We started dating in, actually, 1999, so really a long time. We followed each other through college and when I graduated college, I just thought, you know, I could keep freelancing. We were doing side work through college to make extra money, and I thought, why not keep doing this? I had a lot of freedom of my time. I was living very well. I think we’re both people who like to live well, so we saw that as kind of the clearest path to keeping up the lifestyle we wanted, the balance of work and fun, and more time to spend together.

Patrick: That sounds, go ahead, Jason, tell me your thoughts.

Jason: Oh yeah, totally, like I guess just to piggyback on that. I see Kim and I as high agency people, like we like to have control over our life and what we’re doing, and really one of the best ways to do that is to start your own business and schedule your own time, and like at this time of year, who knows when this podcast goes live but you know it’s almost December and yep when like working from home, we would do our Christmas shopping at like one in the afternoon on a Tuesday, so that’s like a small thing but then raising kids you know from the home working from home being able to take off when we want to and owning the stuff that we’re building so we benefit more from the you know the business itself was all super important to both of us so it made perfect sense.

Patrick: Yeah, there’s a lot of agency working for yourself, and I think if you do it right, it’s maybe the most secure feeling you can have is when you work for yourself. And actually, especially since you two run a subscription company, that is even more reliable on top of a regular business. So you really have really high agency and really predictable revenue, and also awesome time management over your own life. So I love hearing that.

Let me ask a little follow-up there, but did you think about going into tech versus going into any other industries, or was it always, “I’m interested in web development” or something like that?

Kim: I would kind of… Or I did personally. And I have a love of baking and cooking, and I worked at a cool café growing up. So part of me was like, “Let’s open a bakery or café.” And Jason would joke about running a sandwich truck or some other kind of food truck. But really, we couldn’t beat the lifestyle of sitting and working in your pajamas, you know, in your living room, and having your kitchen nearby. And for many years, the pain-free not having a team to manage or other people involved, that it was just the two of us. So for the first few years, there was a lot of takeout and chilling and video games and good life balance.

Patrick: That sounds really magical, to be totally honest. It sounds great.

Jason: No, I remember, like, was it like the first or second month that I left my job and started working with Kim. We binged like The Sopranos. That’s like our work-life balance. Like software is so scalable and programming development when people ask about it, it’s like, is that a good job? And I’m like, it’s kind of like the most valuable skill on the planet right now, so it’s not so bad. Like, it’s in high demand, and so it really just, you know, we had those skills, we enjoyed the work, I think anyway, so it makes a lot of sense to stay into that field, yeah, even though we’ve kind of, and we still do every once in a while, like, consider and start to venture out into side projects, but the core business is in software, and that’s where it’s at.

Patrick: And that’s also, you know, I think that’s also maybe because this is weird, but I think your business has made it, right? Paid Memberships Pro is so sustainable and so predictable and is at such a high level where you can employ a full team of people and yourselves, that you have the opportunity to experiment with new businesses. I don’t want to say for fun, but you could. You could try something for three months and see if it works for you and then go back to Paid Memberships Pro and reinvest your time there.

Kim: Yeah, we’re very careful about that. We do brainstorm it a lot. I think that’s being an entrepreneur. You can’t not step into that zone. You, like, see a cool storefront for sale, you’re like, “That would be my bakery,” you know, consider it. But then, you know, reality check, that’s why Jason’s there to say, like, “Let’s do the numbers, let’s make the spreadsheet,” and then you’re like, “Oh my God, no, I have to wake up at 3 a.m. No.”

Jason: We have to keep our eye on the ball, but we do every once in a while venture out, and just the best opportunity when we come down to it is just always to kind of grow the thing that we have already working.

Patrick: Not enough businesses forecast what would happen if they do X or what would happen if they don’t do X. Jason has a really great insight coming up, knowing how much revenue they’d have to give up to experiment with Paid Membership Pro.

Okay, so you started in 2006 and up until 2015, it was just you two, and then you launched, and that’s when you started developing the team on Paid Memberships Pro. Maybe even give us a little bit of the explanation of some of the gaps in between those dates, and Jason, I’ll start with you this time, but you know, it wasn’t, “Oh, we know we need to build a subscription software, there’s a gap in the market, we’ll make a killing.” Like, there you had it was an evolution, so how did you go from 2006 to 2011, 2015 to today, yeah?

Jason: Yeah, like the quick story. I’ve gone through it in detail on some other podcasts, but like, we were doing any old web development contracts for anything, SharePoint website. Was it Photo Crank? Who knows? They were trying to build like Instagram in 2006, which was way too early. I think the guy that we worked for had patents, and he sold them to Facebook and made a bunch of money or something. But his weird flip phone Instagram we helped develop like didn’t, so whatever it was, like all kinds of random stuff. And then we slowly narrowed in on WordPress as like a focus, and then e-commerce as a focus within WordPress, and then memberships as a focus within e-commerce space. And that’s when we started building, you know, the software on top of WordPress to manage membership sites for a few of our customers. We were just contracting one-off projects at that time. But then once we built it, we took another year after that to kind of generalize it so we could release it open source. And we really, we were motivated to like be close to the money. Through 2008, we realized like our clients who just had like fun blogs on the side or doing like, you know, they’re trying to do kind of unsustainable stuff with their website like they’re like, “Oh, I need money, I can’t spend you know on this anymore.” But the people whose websites were making them money, they were like, “You’re now the most important.” I lost my job, but my side project that was bringing in money is now the most important thing in the world to me. So we wanted to be close to the money. And we also saw the success back then of like WP eCommerce as like an open source project that people were, you know, and there was like the Thesis vs. Matt Mullenweg kind of battle, and we were like, “Oh, we’re on team open source.” So we wanted to share the code that we had built and really build a platform.

So from like 2011 then to 2015, we were like straddling consulting and products. Like PM Pro was kind of ramping up, but we made most of our money consulting, and it was always like taking time. We could bill hundreds of dollars an hour for clients, but we, like, for like $20 a month, answer your support. We were spending way too much time on Pay Mers Pro, not getting paid the same. And then around 2015, we made that jump. We’re like, “Hey, for these next three months, we’re going to turn away all the consulting work. We were making an investment at that point.” So we’re like, “Hey, for the next three months, I, you know, we’re making like $20,000 to $30,000 a month consulting.” So it was like, “Oh, we’re going to make like a $60 to $90,000 investment to see if we can make Paid Memberships Pro work.” And it, and it did. Like, luckily, we, you know, we spent three months doing stuff and luckily it worked out. We started asking for money more often. We doubled our prices, and people were, we, we had already built up the, it took a bunch of years to, like, build up the user base of the free Pay Mers Pro product. So then when we started giving, you know, saying, “Hey, you should maybe pay us for this add-ons or this other thing,” people are like, “Sure, we love you,” and, and we’re like, “Oh, okay, we then we made it full-time products and we stopped all the consulting.”

Patrick: So, I always love the transition from consulting to product because it’s such a, it’s such a, it feels like every hour you’re consulting, you’re like, “I’m making money.” It feels really good and it’s really hard to go to software and especially like open source where like random people can submit really edge case bugs or like really your plugin doesn’t work when I’ve installed these 30 specific plugins. Well, okay. You like lots of edge cases that you don’t necessarily get paid for. Okay. So you, you talked about how much you made consulting. Can I ask how much you were making roughly that time with Paid Memberships Pro? Like, you know, was it a thousand dollars a month, $5,000, 10? Any idea?

Jason: No, I can look at the stats, but my feeling is it was like $5,000 a month on Pay Memberships Pro, and then we kind of, we doubled the prices and we doubled the number of places we were asking for money. So like, we used to be able to use our add-ons for free, and now we’re like, “Hey, you have to pay for the add-ons,” and, and people kind of didn’t blink. Like, old users, we always like grandfathered them into like that people still are paying $47 a year for access to our $600 plan, but new people were paying twice as much and twice as often, and it just like kind of overnight in one month we went from $5,000 a month to $20,000 a month, which was enough to, like, wow, cover most of the consulting and pay our bills, and we could make a living on it, and then we’re like, “Hey, let’s let we grow it from there.”

Patrick: Wow, it’s really incredible to double your prices and double all the things that you’re asking when you’re asking money. That’s really incredible to go from five to 20 to double.

Jason: Yeah, it’s crazy, and I mean, I guess we paid our dues like the four years before, like really grinding it, but I think sometimes other entrepreneurs are in the same situation where they’re kind of nervous to raise their prices, to ask for money in certain situations, or sell it a certain way, and you’re like, just take one of these tried and true business models and try it out a month and see if it works on your business, and you might be surprised like we were. But the other important thing is to make an investment, so we to do that because we were making money consulting like we had to, it’s easy to say double-double but actually took a lot of updates to the website and building a license server and all this stuff so we had to like hey that’s going to take a month or three for us to do that we had to make that investment and and luckily it paid off.

Patrick: The more I talk with Jason and Kim, the more I realize that you have to be aligned on three things: one, your business values; two, the priority of the business in your life; and three, you just need to have exceptional communication. We’re going to get into all of these in the rest of the episode.

Kim: I’ll share what our life did during that window because this is about partners and you know what was our life doing in that same time frame. We got married in 2007, we had our first child in 2008, our second child in 2011. So when you know 2015 came around we had two kids, you know one was what seven years old St in kindergarten one was still a tiny you know three four year old child so life didn’t slow down during that window it wasn’t, let’s not also make progress in these other things that are important to us as a couple.

Patrick: I can only imagine that I only have one kid who’s very young and I cannot imagine. I  guess I have a hard time imagining launching a business with two young kids so I give you both of you kudos on that.

Kim: We have a very cute video of Jason preparing to record like a video for membership Pro with Isaac on his lap and Isaac saying you know what’s this daddy what’s this so it was really cute because they were so little at that time of our life maybe for a good reason they were little they don’t remember how much we worked how much we handed them off between the two of us but you know it was a cool time.

Patrick: Fascinating. Okay, so I think my so I’ve my second job after college I worked at the small advertising agency and it was also a husband and wife Duo and they broke up the labor and what I think what makes the most sense to me is one person does all the creative and one person does all the admin and I think that’s probably one way of doing it but I don’t I don’t know if that’s your way so I guess my question is how much do you overlap on skills and responsibilities and how much do you balance each other versus I’ll just handle this and you just handle that. I’ll start with you Kim.

Kim: Yeah, so when we were consulting we operated where one client was mine one client was Jason’s so it was less about skills and more about like who was the decision-maker who was the owner of this project m I did always do more operations type things like paying the bills but Jason always us kept us in like a vision and projection and cash flow orientation so it’s interesting how we’ve we overlap in all those areas I don’t come from a computer science background Jason does so for the first years he was like the developer I was the designer of things and over time I learned the development things out of necessity and he learned some of the basic he’ll tell you he doesn’t have the design like the CSS coding skills but he has the eye to know a website’s usability and things like that so I think we crossed for a long time and did each other’s roles kind of here and there and I think more lately we’ve diverged from that and specialized more out of necessity because you know our team needs us in different ways as we’ve grown different people need more focused time with Kim for this these purposes and more focused time with Jason so it’s interesting how that shifted over time yeah definitely not a I’m an admin and Jason’s an operator at this team.

Patrick: I like hearing that you you shifted a little bit it’s it’s probably good for both of you to have done this almost the same job like you know I’m thinking of a vent diagram where like 90% of is is overlapping it’s probably good because then you totally understand the role and and you’ve both done the job and then to separate a little bit more and specialize a little bit more when you when you have a team that needs it would you ever go back to kind of doing maybe in a magical world where the team was smaller would you ever go back to kind of doing almost the same thing.

Kim: I’ll say in some ways we romanticize and miss that because we work less together and it was such a fun when I talk about those like moments watching Sopranos and working like we were side by side on a sofa arms touching you know like working together talking and he would unblock me and I would unblock him and it was really fun I think and now we don’t do that as much but when we get moments too we really treasure them because it’s like the old days for us.

Jason: Yeah, totally. I’m trying to organize the team to have more of that. What’s coming on it’s funny like was like Kim one of Kim’s love languages it’s acts of service and like there’s no better Act of service than like helping someone debug some code like it but yeah so we we definitely but out of necessity we’ve had to like there’s so much work that like it’s kind of like you manage this I manage that.

Patrick: I can imagine how in some areas of a business that I would share with a partner I would be really good at this and I would want to have the decision-making ability and they’d be really good at that and want the decision-making ability and you know you always want the other person’s opinion and input but then you just you merge it into all of the data and knowledge that you have and then you spit out even if it goes against what they want my question is when someone is not the ultimate decision-maker when it’s sort of there’s no clear person who’s better qualified how do you handle those decisions I would that’s probably the most stressful part of maybe working with your with your spouse so I would love to know I’ll start with you Kim.

Kim: Yeah, we had to make a decision when the kids were small because I needed to be there for them more available to them so there were times where you know Jason was operating more in the business I was operating more in the home front and over time it was like we’re going to give Jason the CEO title and what does that mean that means ultimate decision-making power right I have to be okay with that at all corners you know there are moments where it gets really tense and I think we’re going in a direction that feels not right or I think Jason’s making a decision that’s going to impact my quality of life give me more work you know do something that shifts everything in the way that I get to work and the time that I’m going to have ahead of me and what I thought I was doing that day and I have to be okay with that you know I’ve never as an adult I’ve never had a boss and there’s tiny moments where Jason gets to be the boss in our business and you know it it shows me why I’m an entrepreneur and why I work for myself because it’s not a comfortable place for me but you know I think just for the health of the team and the company I accept that that’s the the title he carries and the weight he carries and you know the decision-making ultimately is his in those moments.

Patrick: So, would it be good advice then if there’s another couple listening to this to at some point have someone who is the 51% decision maker versus 49% decision maker?

Jason: Yeah, and I think that’s general business advice too, like for you know married couples and other partners that like someone needs to break the tie or you might just get this deadlock. And so you kind of have to have like when you get deadlocked you have to have someone who makes the decision but it really works because Kim and I have a good relationship so the same things that are good in a marriage like having respect trust and lots of communication help in that same situation so when we are deadlocked on something it’s like Kim has respect if I’m overriding her Kim has respect and trust and we’re communicating through it and I think what’s also is that you know we neither Kim nor I are the kind of person who like rehashes what happened in the past or or you know regret things or think too much in the past if man there was what was I saying at home oh we’re talking about like when to eat when when to eat dinner was it like two weeks ago I was like we should probably try to eat dinner earlier in the day I feel like it would work better for the kids schedules and then for it wasn’t even that big a deal Kim’s like no I don’t know like we’ve been eating at 6:30 all the time let’s just stick to it and then she said today was like she’s like I think we should eat earlier in the day because it’ll help you know the schedule and and I’m joking about it because we’re coming on this podcast so I did say something but I wouldn’t have said I wouldn’t have been like I told you so or like make a big deal out of it or make her feel bad I’m bringing it up on the podcast because I think it’s a good story but we’re not you know Kim’s not GNA get upset about so that same kind of thing in a more serious business really you’re like hey we made a mistake we’re just like okay what do we have to do now you know and I’m like okay I’ll make sure in the future that we we get where we want to go so I think it doesn’t work with every couple I think that could be a source of conflict if there was like spite invol or I was like overriding Kim For No Good Reason without communication and also I am the CEO but there’s tons that I have the saying that people here in the business in the at work where I’m like I trust your judgment like it comes up and I’m like I have to know enough to be able to talk about things and kind of understand what’s happening in the business but if Kim is closer to it has more experience understands better which happens all the time like Kim’s awesome so we you know I say hey I trust your judgment on it and it’s not just some flipping like go do this and I don’t care it’s really like I honestly trust your judgment over my feelings and I let Kim make the decisions on things that are important where she has better judgment on it so it goes both ways even though I’m like making the decision I’m not like enforcing like what I always think is best at least I think so Kim and then hopefully Kim puts me in check when I do become too much of a tyrant.

Patrick: So, I had a follow-up question which you I think I’m hearing two things here one you have excellent communication skills and that that helps with resolve any problem and two I think you’re also aligned on you both said you you don’t think about the past and if you because you both think about the future to the same level you’re both focused on learning and improving and and progress then you aren’t rehashing because of your shared values you aren’t rehashing the past so is that kind of the two critical ingredients is shared values and and really good communication with your partner.

Kim: Yeah, those check-ins we have to both when things are difficult, you have to both check in and say like business’s side, is this where we want to be today now together, and if that decision doesn’t include the business or it doesn’t include where the business is taking you, like Priority One is your family and your marriage, you know there are businesses in WordPress that were run by couples that are not together anymore, you know it doesn’t always work out that way. And the business still goes on so for us it’s, you know, that has to be secondary, that the relationship health has to be there first but an interesting piece of this oh we’ll let him go good.

Jason: I was gonna say if we ever get like in a fight over business, like I’m often like I was like this is so dumb, like why are we fighting about a work thing, like our marriage is way more important than the business like and it it grounds us to, you know, get it over, get over ourselves and make a decision for the business so we can, you know, go on with our married life.

Patrick: Yeah, so I’m going to add a third thing there and that’s so it’s Val shared values really good communication and then also understanding that business is second to family and then I think that’s really easy to go oh Jason’s the CEO I might disagree with this decision but that’s his call and I’m just not not going to worry about it, not going to get into a fight about it in my personal life outside of work. I love hearing that. So are there any examples of where it did spell over and you had to like was there any anything that you might be able to pass on I’ll start with you Kim.

Kim: Yeah, I think knowing that running this is not for doing this is not for everyone is important to me and that’s maybe not the right answer to this question but I think it’s an important one because it can sound like it would be ideal you have complimentary skills you have overlapping skills and you both you know are sick of your day jobs let’s start a business together but just knowing that it’s not for everyone and that’s not a failure I think is a lot of people when they hear that we work together our friends our social life our family the immediate thing they say is I could never do that and it’s it they’re so convinced like I could never do that so if that is the first thing you hear when you listen to this podcast and you are hearing what we’re saying the first thing your mind tells you if I could never do that I would trust that instinct pretty strongly.

Patrick: Love it. Any thoughts from you Jason on this on the same thing, any potholes that another couple might step in?

Jason: Yeah, no good answer. I do think like that question you had about what work bleeding over into the personal life, it happens in reverse too, like some of the toughest moments are when personal life is bleeding over work, it’s tough. Like I mean, Kim and I have the perfect blissful marriage, it’s really good. I like it, I think it’s one of the best marriages, but there are times when we’re fighting about something at home or something going on and man, it’s really tough. We’re like, “We have the team meeting in 10 minutes.”

Kim: Stop crying and go to the meeting.

Jason: I don’t know, and we find a way. I think, I mean I think that comes up even in your personal life when you’re not going to work, sometimes you have to show up because your family is showing up and it almost forces you to, like, push, fight through things in a good way and like, “Hey, we have to figure this out.” But I mean, yeah, those times are tough too. But I like the part, like what Kim said, like we enjoy the work, we enjoy the work together, and it’s challenging but like that, that’s fun too. So like, it’s not like we fight through the challenges of that and because we get this, the benefit of the business, it’s really like we enjoy doing the work together, like that’s, and so that’s the primary thing. Like Kim said, if you don’t feel that, it doesn’t necessarily work for every every couple but it’s worth giving a shot, so like if you suspect you could do this like it’s kind of worth taking a month or two or three to like really try and and do it together because we have a ton of agency over controlling the destiny of our lives and our children’s lives and it’s pretty awesome so if you have a chance go for it.

Patrick: Agreed. So let me ask you a question about maybe dynamics and relationships. I think and let me give you an example outside of work for a second. So like when you’re playing board games with friends and there’s a married couple but sometimes married couples will like to work together to fight other people who are individuals so that’s just a dynamic I’ve seen at the board game table and I think there’s something about supporting your spouse. So when you do disagree with each other, do you show that to the team, you know? So Jason has made a decision. Kim, do you say I disagree with the decision, here’s why or do you kind of keep it private and maybe discuss it after work hours?

Kim: 100%, there are meetings where I have said, “I don’t agree with this, but you’re the CEO and it’s your decision to make.” I have said that in front of our team. There are times where Jason has said something on a team call or in a management meeting that I later tell him, you know, from my perspective, that read wrong or that that didn’t go over right and good feedback that felt harsh or you felt a little like unhinged.

Jason: Unhinged. And I think about this like it’s more important because we’re married. Like, Kim’s the most important person in my life, but I think we have these same issues with anyone on the team. Like, I don’t, you know, if I disagree with anyone else on the team, even the ones I’m not married to, we want that in the open. We don’t want to hide it. We kind of, but we, one of our values is being human and it’s like the work comes second, like we’re people first. So sometimes you have to put in the effort to take the rough edges off like feedback to make sure that you hear, you know, you’re hearing the employees’ ideas and respecting them and their time and stuff, and not just, you know, being mean or too quick or other things that can, you know, bossing people around. So sometimes the work is really hard and it’s like we’re moving fast or it’s like here’s a bunch of complicating we need to really quick like narrow down and I get into like, you know, scalpel mode like operation move really quick and it gets impersonal and sometimes that’s necessary but you don’t want to always be in that mode. Like, you know, we’re all human at work and we want to respect, you know, everyone we work with and it is, I think I’m a little bit more comfortable with Kim. I think that happens anytime, like you, a lot of times people are kind of meaner to the people that love them because they can kind of get away with it. Like it’s not like I’m doing this on purpose but it’s human nature and you know we a part of being a good spouse and marriage is recognizing that and trying not to slip into it so that you’re not making your wife cry all the time at work right at home.

Patrick: Good idea, good advice. I’m going to put that on.

Jason: Don’t make your wife cry. Yeah, that’ll be like the thumbnail. Don’t make your wife cry.

Kim: I think that’s a book title.

Patrick: So this is actually a good transition. I would love to know, are there any habits or processes or top tips tactics that help you have a healthy harmonious marriage outside, you know, marriage and your personal lives outside of the business? And let’s start with you, Kim. Go ahead.

Kim: These are things that I’ve learned and I’m doing better at as I’ve gotten older in our marriage and in our business. When you see someone has like a grimace or a funny face or looks a little upset, you tend to go to your partner and say, “Is something wrong? What’s wrong? Your face looks sad.” And I try to do that less if I remember to, because it’s like people just make a face and then it creates this cycle of like, they think I’m upset, why do they think I’m upset, are they upset with me, and it’s just this like really sick, don’t do it thing. Like, if you actually want to unpack and sit down and care, you have to make the space to have that conversation, not just like a passing in the kitchen, like, “You know, why are you upset? You look a little upset right now.” We have to respect each other’s work boundaries and relaxation boundaries, and that’s a marriage thing. If you see your spouse needs to go sit and decompress on the recliner and read on their phone while you’re doing dishes, like, don’t carry resentment toward that, don’t interrupt their moment of transition time or like relaxation, and that’s something I’m doing better at as we’ve gotten older. Yeah, it’s interesting to work in the same environment and on the same project with your partner and not create some judgments about how much are they working, what are they working on, and as much as you wouldn’t do that if you weren’t working together, you know, why would you in a marriage, you would never ask your partner, “Are you working hard enough at your job that I’m not even a part of?” like, you wouldn’t.

Patrick: Kim and Jason purposefully work in different spaces in their home. The different spaces help them context switch from different tasks. We’re going to get into their separate physical spaces near the end so keep listening to learn more. That was kind of what I was getting at, Kim, that’s what I was thinking at the back of my mind is I’m definitely a morning person and my spouse is an evening person and so sometimes in the morning she’ll put on the TV at like 8 in the morning. I’m like, “What? Your day, it’s going to be wasted, it’s going to be gone.” That’s my paranoia, I guess I’ll call it. So I’ll follow up with you, Kim, and I’ll come to you, Jason, how do you respect each other’s boundaries when you may be different people, morning people, evening people, and some people can work in really long bursts and some people need quiet and there’s all these variables, how do you, how do you know when someone is in work mode versus personal mode, maybe that’s the right question to ask?

Kim: Yeah, Jason likes to say when he has headphones on, he’s working. He’s not great at always putting his headphones on. Sometimes he’ll sit at the while I’m cooking dinner. He’ll sit at the kitchen island and like start working and then I’ll say, “Oh,” and I’ll start talking to him and he’ll go, you know what the, the like, like I rolled really big for the people listening only here so I think then I have to say, like, “You’re sitting at my kitchen where I’m cooking dinner, you are in my space, you are in my zone right now.” So moving, creating separate space to work helps a lot and I think communicating, “I am working right now,” and then I will say, “This is the wrong place to be working right now,” you know.

Patrick: I like that, yeah.

Jason: It’s interesting how different Kim and I are. Kim is multitasking, doing lots of things at once. She can, you know, answer a question, go back to the work and stuff, and it’s not just the type of work I do, but I think it’s really my mindset. It’s like I have to be focused for an hour and you know, that it’s almost like a cliche about developers in particular. Like, you’re juggling balls and then someone asks you a question and you’re like, “Well, now I’m not,” you know? I dropped all the balls and you know, I’ve lost my momentum, I need that. And when we would work more closely together, Kim would interrupt, and it’s so dumb. It’s like, “Could you raise your hand before you ask?” “And could you Slack? I know I’m right across the desk from you, but could you Slack me?” Or if I have the headphones on, like, I’m trying to focus, don’t interrupt me. And it’s actually kind of like Kim’s walking around the house, like, talking to everyone as we, you know, as she talks to the dogs, which is beautiful, awesome, but anyway, and so this, like, talking at dinner, I would try to work at the table while you were cooking, but now I do that on purpose. I’m working on things that it’s okay to be interrupted, and actually, I’m here to answer Kim. I’m working on Kim’s stuff, usually, like, you know, little things that you need me to do or questions you have. And so I think we found that, too. Like, another kind of funny thing is I scheduled this, like, weekly check-in for the owners. I forget what you called it, but it was like Kim and I checking in about work. And in the same way where, like, I think about the future, Kim’s very much in the present tense. I would, during in that hour, I’m like, “This is my hour to think. Like, what do we want to do with this business? Do we want to expand? Do we want to hire? Do we want to make it smaller? Are we gonna, like, these kinds of big, big life question-type things in the business?” And Kim is like, “Oh, I thought that was our moment for you to help me, like, debug line 17,” or, like, “I know you have a to-do list that you haven’t done anything on for the past three days. Could we just check some things off the to-do list?” And I think there was a friction there, but then we were like, “Wait, we need both meetings.” So it’s like when I’m actually at the table and Kim’s cooking, I’m there, and I’m checking off the to-do list because that’s what she needs me to do. And when we’re walking the dogs and I bring up like, “Hey, like, I have this crazy idea about the business. It’s high, high level. Let’s talk about it,” she, you know, entertains me to talk about those things. So we find time for both, and we don’t try to do it at the same time.

Patrick: I love that. So I do have another follow-up here. I know you have this awesome RV garage space that you’ve converted into an office. So you have this really awesome separate built structure that is an office, and Jason, I believe you work there a lot, and I think Kim, you work in the house a lot. Is separate spaces like a key thing that you think a married couple probably needs?

Jason: Yeah, I think so. It’s awesome. It’s like, and then it’s aw when I come home for the day, you know, you still get like a little bit of that, like, “I’m home, honey,” type feeling. I think it’s good in general to have a separate space where you work. It puts you in the right mindset of like, this is the workspace. And, you know, the PC that I work at is also the one I play video games on, so that makes it tough. That’s like an antithesis of that, you know? But no, yeah, I think that’s really big that helped us a lot when we started doing that more.

Patrick: I’ve always wondered, so, per I’ll ask for myself personally here, so we have one office which I really like, but we don’t have a second one for my spouse, and part of me wonders like, is it worth either building a second space or one of us getting like a co-working space then we can swap out in this office? But it does let me ask you this question here, Jason, how high up the priority list would you put getting a second space in terms of, you know, you’re only making so much money every month? Where did, how, how important is that space?

Jason: Yeah, it’s a privilege to be able to afford a space or like going out. You can go to like, actually because I’m on a sabbatical now for a few weeks, I’ve been like going to outside to cafes to work again, and I realized like how well and how much, how much I can focus at a cafe and work, and so that’s like a lower-cost alternative. It’s like a few days a week, get out to Starbucks or the Panera, you know, type things to work.

Patrick: Love that.

Kim: I could never work outside of my little kitchen zone. It’s just, it’s exactly where I need to be to work, so I think that the check-in is if you both decide that you need distinct space from your home space, then yes, high priority, right? Because someone will always be fighting for that office, and you know, you’ll be rotating in and out, and you’ll be, “Oh, I have this call, and I need that privacy,” and that creates unnecessary conversation.

Jason: We kind of did that when we were sharing taking care of the kids, and yeah, it was like you scheduled a call, I have a call, you know what I mean? Like, we’re in the same, we can’t both be talking in the same place. What are we doing?

Patrick: Yeah, very cool. So I want to talk about some highlights. So, are there any memorable successes that the two of you have had that have strengthened your partnership, your romantic partnership, and brought you closer together? I’ll start with you, Kim.

Kim: For me, it was the idea of taking a sabbatical, so Jason’s on his first one right now. For myself, I took three weeks in September, and I traveled, and I took a sabbatical last summer. So I think those periods give you reflection on your own work and reflection on your relationship with work with your partner. When you are married and working together and have been doing it for us, it was 11 years before either of us took a distinct break from working together, which is a long time. When you work together and you take, you know, maybe you take a 10-day vacation with your family, you’re still working with the person you’re working with, and it’s impossible and not necessary to put a veto on speaking about work. You know, I think that you could say, “Oh, we’re not, we’re out to dinner tonight, we’re not going to talk about work,” like that’s unnecessary. You know, if you both want to talk about work, talk about work, if you both don’t want to, don’t do it. But the sabbaticals have been the distance that I’ve enjoyed. I think Jason is enjoying re-evaluating and checking in even with yourself as a human being and re-evaluating with yourself and how we work together and like what do we really want this to look like, you know? So I think those have been really important.

Patrick: Fantastic. I really like that example. What about you, Jason?

Jason: Yeah, I think about, I mean, it’s weird to frame it as a success, but I think of a story of something that Kim and I went through when our first son was born. He was in the hospital for a couple weeks and had to have surgery, and we were at, like, the Ronald McDonald House across from the hospital. And we, we were doing consulting work at the time, and we, you know, we would visit him in the hospital during the day, and then come back to the room, and we’d be programming for someone’s, you know, website, like doing work to make the money. And then those next few months were kind of tough. It was like the winter, plus we had medical bills, plus like we didn’t have time, you know, because of all the follow-up and stuff to do as much work. And we got really close to taking, like, real jobs. Like we had an offer for one of our side projects, like, “Hey, we’ll buy your side project and come work for us,” and we’re like, maybe we should do this because, you know, it’s like, and I think, like, the running our own business thing could have ended there, but we, we toughed it out and we stuck through it, and that was kind of like, you know, the bottom. And we, I think we learned a lot going through that, and I think we can always look back at it as time it’s like, hey, if we can get through that, we can get through anything, like nothing’s as hard as that.

Patrick: I like that. I mean, just a period of hardship that proved your relationship meets the metal.

Jason: Yeah.

Patrick: So I’ve been kind of talking about this the whole time as we’ve been going through this interview, but just to finish up here, what I guess what lessons would you share, what advice would you give to couples who are considering the same thing, and I’ll start with you, Kim?

Kim: I would say that the harder part is the issues that will go on in your life and your children and your family and your parents and all of those things are infinitely harder than running a business together. So remember that, like we said, that’s the first and most important thing and make the business and the work the second thing and as much as possible be aligned with that because you could have someone who’s just driven to be an entrepreneur and you know they’re the one side they’re like, “I want to be a billionaire,” you know, and the other one’s like, “you know we just want to, you know, be comfortable, donate to charities we support, and pay our team well,” and if that’s like really out of alignment you know you’re in for a tumultuous situation. But I think also embrace that it’s going to be pretty crazy all the time almost every day and be okay with riding those crazy tumultuous seas. Jason’s gotten me into these ideas of, you know, being a bird flying above wavy water and a newer one he taught me was that if the sea is rocky your sailboat might go off course a little bit but that the direction of the sailboat is where you’re both headed so I think expect tumultuous seas expect going off course but as long as your sailboats are both aiming toward the same direction you know you’re in it for the right reasons.

Patrick: I like that, anything to add, Jason?

Jason: Is that Michael Singer podcast? Look that up.

Kim: I don’t even know the guy, I just know what Jason tells me.

Jason: The untethered life, yeah. I summarize business books and meditation books for Kim, but that, yeah, no, that’s a good one. That’s great. It’s like, you know, you can’t control the weather, you control the water, but you can control your sailboat, the steer, and but sometimes the wind’s just going against you and you have to take down the sails and ride out the storm. And that’s tough but you know if you, you just have faith that you, you’ll try to, you’ll have a chance to go back towards your targets. Yeah, I think I said earlier like give it a shot, like it really is such a great way to live life that it’s worth taking a shot for the people who think that they possibly could do it, like Kim said there’s a lot of, you know, partner-led businesses maybe it’s not as obvious from the outside how much influence, you know, like how much we’re working together on this thing so it’s worth taking a shot and you can always, you know, if it doesn’t work out you know kind of try, you know, it doesn’t mean your relationship is bad you know you just you know figure out you know what your relationship really needs maybe you don’t have as much fun as Kim and I do working together on things you and you can just you know find find different jobs to move on that one.

Patrick: Yeah, I think the last thing that I’m putting together here is to know yourself. That’s probably the key thing is just to know whether you individually and as a couple can make that happen.

Kim: I’ll add one thing if you have any hopes of your children becoming entrepreneurs like don’t do this because I think the example they’ve seen from us is like the furthest thing from life that they which is funny you would think the opposite but they’ve observed us yelling at each other about work things talking they’ve observed us very late at night you know they’ve observed us having frustration with things at work and issues at work and you know even though they’ve seen us celebrating big things we just got through Black Friday celebrating huge things you know they’re they’re very much like I don’t want to own my own business like I don’t want to no thanks so yeah like there’s a trade-off kids don’t want to do what you do most it’s TBD our kids are still kind of young as TBD I think like we’re still modeling some things and they might figure it out.

Patrick: And once they have that first real job where they have to show up at 8:00 a.m. or 3:00 a.m. for a bakery they may reconsider.

Jason: It’s almost a good thing, it’s funny, especially our son who’s older, like wants to get a job, and there’s nothing wrong with these jobs like, you know, working at the gas station, being, you know, the a cashier somewhere, or working in retail, and I’m like, you know, like your parents have, we have this business, like we’ve often offered them, like hey, we pay people online to do the same thing that you’re capable of. And as a kid I would love to have had these opportunities, in fact I did kind of work for my mom in in a certain capacity but like they’re not interested, like they’re not see it feels like easy to them so they’re like no I want like the more mundane job and it’s like Okay cool so it’s like it’s weird like they’re not following our footsteps to like work on the internet and take part in this Creator economy that we’re wrapped up in maybe someday, maybe someday I think they got to give it a go they get I think actually my our and maybe Kim feels this way too like the mundane jobs we had like in high school in college it really hammered home like oh I don’t want to do this I don’t want to work in a factory I want to you know and that kind of like led us to the way where we are now so maybe when our kids have that experience they’ll come back to entrepreneurship.

Patrick: That would be my guess but who knows, you just have to see where things go. Kim and Jason, thank you so much for sharing your thoughts and thank you for being on the show and I’d love to know where people can learn more about you, talk to you or reach out to you.

Kim: Our business’ website is strangerstudios.com and if you’re considering starting a business with your partner or having trouble with a partner you’re running a business with, I open myself to talking with you, you can reach out on our contact page there or email [email protected] we can set up a coffee talk and 20 minutes on Zoom to just hash out anything I can help unblock for you.

Patrick: That’s incredible. Thank you so much, anything to add, Jason?

Jason: No, that’s awesome, talk to Kim and help out too.

Patrick: Love it.

Jason: This has been great. I’ve really enjoyed this conversation. It has been fun to think and talk about these wonderful things.

Patrick: And thanks to our listeners for tuning in. If you enjoyed Kim and Jason’s interview, like and subscribe so that we can get more expert entrepreneurs onto the show to share their knowledge and experiences. Also, help us spread the word to entrepreneurs like you by sharing on your socials. If you want to know what we’ve got coming up before anyone else, visit plugin.fm’s website. Click on the Subscribe button to be in the know. plugin.fm is brought to you by Freemius, your all-in-one payment subscription and taxes platform for selling software plugins themes and software as a service. If you’re struggling to grow your software revenue,  send a note to [email protected] to get free advice from Freemius’ monetization experts. My name is Patrick Rauland and thanks for listening to plugin.fm.

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