Sherry and Rob reveal their plans for their first course (FounderFamily: Date Night Bootcamp) and talk about some of the ups/downs and unique challenges entrepreneurial couples face.

Support ZenFounder

Episode Transcript

Rob:So the book The Entrepreneurs Guide to Keeping Your [beep] Together currently in the process of being converted to Kindle and we already obviously the manuscript’s finish. We got a proof of the book printed out, or you know, a full print copy. Cover looks great. Kindle is in the works. We already recorded the audio version. We can’t upload that until Amazon had … this and that, so it just seems to be one more week waiting on something.
 During that time we are prepping our first course. It’s called Founder Family Date Night Bootcamp. I know you’re putting a ton of time into research and writing. We don’t have a landing page yet but if you’re interested in what is essentially gonna be a video course with other materials of Sherry and I talking through how to stay connected with your spouse, your significant other, through date nights and through being deliberate because as founders, if we’re not deliberate we can go months just thinking about our business, and not paying attention to the people around us, the people that matter. So, it’s gonna be a look at how to stay connected through date nights. We will send updates via the mailing list. If you’re not on it, zenfounder.com and you’ll see the cool little Drip widget in the upper right.
Sherry:Yeah, you can tell I’m in deep work because my desk is a mess.
Rob:It’s a train wreck.
Sherry:I have piles of books. I have Hold Me Tight by Sue Johnson. The Five Love Languages, of course. Seven Principles for Making Marriage Work. I have like, 10 books on my desk and then I have four mugs, three water glasses, one martini glass, four takeaway coffee cups. It’s like a bar/library all on my desk.
Rob:I was cleaning up the office this week and … this weekend and tidying mine up, and I turned and looked at yours, and it was like a scene in a movie. The record skipped, and I just pretty much just backed out of the office. Just-
Sherry:Just walk away, walk away man.
Rob:Not gonna touch that.
Sherry:I have read some people post things on social media that say that studies show that messy people are smart. Or like, messiness is correlated with intelligence, but I have not read the original research, so I probably should not be spreading pop culture lies.
Rob:Right, you’re quoting the internet as your source.
Sherry:I did that. I did that. Let the record reflect that I did that.
 So anyway, all these books and drinking glasses have meant that I’ve been thinking a lot about couple life. Particularly trying to think about the unique experiences that entrepreneurial couples face, and some of the unique challenges that make family life trickier for those of us who are starting and running our own businesses. I think, we know that there are some mental health uniqueness’s and some value and existential differences in the way that entrepreneur’s view their lives, and I do think there are also some significant defenses in family life.
 That’s where I’m trying to think through, and iron out, and I’m going back and listening to old interviews with couples that I’ve interviewed on the podcast and interviewed for other products. Of course, digging out the old books from graduate school and trying to really put together a course that is helpful. I thought maybe we would talk through some of these ideas today just as a good practice for us getting ourselves on the same page to do the course together.
 I think, as I’m sitting down, I think through this there’s a couple of different unique challenges that I think entrepreneurial couples face. One is that higher than average number of ups and downs that I think go along with entrepreneurial life. Financial ups and downs. Emotional ups and downs. The pressure of ramping up to where to launch the aftermath of that. The ups and downs that go along with the sale. There’s just a lot of life shift and change that I think goes along with entrepreneurship that’s a little bit different than my friends that work at law practices or hospitals, and have more stable career trajectories or more predictable career trajectories. Does that ring true for you?
Rob:It does, it feels like there’s probably more resting on our shoulders as founders. Any job can be stressful and if you do work at a law practice you can think about work all the time, it’s totally possible. Or if you work as project manager or something, you can take that weight on but as a founder I feel like owning the company and feeling responsible for everyone’s well being, and feeling the weight of every customer that gets angry and feeling the weight of just all the … there’s employee stuff, there’s co-founder stuff, there’s growing the business, there’s can I make payroll, there’s financial. There’s so much there that is not just thinking about work, but it truly is this weight on you that I think I hadn’t experienced. I certainly hadn’t experienced it until I ran my own companies, so it is a different … certainly a different weight on me, and then that translates into it being so much harder to be as engaged with you as I would like to be.
Sherry:Yeah, I think that’s the other piece that I’m really thinking a lot about is that entrepreneur’s have this emotional engagement with their business and that I think has some significant implications for the emotional engagement they have with their family.
 Sometimes it feels like … Drip, for example was this other entity that you loved that I was like sometimes jealous of. Not very often, but there’s this sense that because a business is sort of an extension of you. There’s some messy overlap between your identity and the business that you run, and that can get a little bit tricky in the emotional life of a family.
Rob:Yeah, and that’s the thing is … I don’t know, I think something like an adaptive quality is with running business, or maybe even being just good at your job in general, but I think some founders specifically face is focus, and the ability to have a one track mind and drive towards an end goal and relentlessly do that over the course of days, weeks, months and years.
 That’s what’s gonna bring you success in business and with your own company. There’s weight on you to do that, so you feel pressure. But that emotional engagement with your work it has a tendency, a real tendency to cause emotional disengagement at home because you’re sidetracked, you’re focused on work on your business when you should be hanging out with your kids or thinking about, what does my spouse need help with tonight, as an example. Can I offer to do that? So you can show up and have a conversation and feel like you’re present, but still not be as engaged as you would if you didn’t have your business on your mind at all times.
Sherry:I think people can feel when you’re there but not there. I think that’s a really … it’s like a low grade constant stressor on a lot of entrepreneurial families. I’m kind of thinking of the example of families where one person in the couple-ship is an entrepreneur, and the other one isn’t or has a more traditional job. Of course, there’s lots of different family constellations we could think about but in that case, that emotional disengagement or emotional preoccupation with the business, it’s your thought life but it’s also your feeling life.
 That creates this, again this low grade kind of constant, I think, stress on the emotional quality of the relationship because the thing that we are asking ourselves in the context of relationships is, “Will you be there when I need you?” It’s a really simple question, but it’s a really profound question and it’s the basis of what we call in my field of psychology, what we call attachment. Can we really be fully attached to someone, and the answer is that we can be attached when we believe that they’re gonna be there.
 Sometimes it can feel, I think, in an entrepreneurial life like there’s a lot of … there can be a lot of upheaval and transition and you’re hoping that your little business will thrive and will be something that outlasts you. That it will be there for a long time. But you can have this insecure or fragile attachment to your business because it’s so fragile. But the quality of the emotional relationship with your partner, you obviously want to not to be fragile. You want to feel like despite the chaos, and the ups and downs, and the successes and the failures, that your partner is going to be stable and emotionally present in a stable way.
Rob:Right and you and I have experienced both having the other one show up and not being able to show up for one another. If you … in the first chapter or I guess the intro of the book that’s coming out in a couple weeks you tell the story of our New Haven year and how neither of us had the kind of mental bandwidth, or the full bucket, or just the ability to show up for the other, and it really wreaked havoc on our lives for that year.
 I think of the example of a time when you really showed up for me and it was in 2014 when I was having all kinds of … it was really Drip was having financial issues basically, and I had hired out a head of revenue because I wanted to try to get to product market fit sooner, and I hired three developer … well, Derrick and two other developers and we started just burning through cash and I had this big cash cushion of, I forget what the number was exactly, it was like maybe $120,000. It was more money than I’d ever seen in a bank account.
 This was all from businesses I had built up over a decade putting money into this account. It was just … it was my, I’ll say my businesses life savings, in essence. I was like, I can handle this burn because I have all this money, and within 45 days I had almost $100,000 of expenses that I just wasn’t counting on come through. I had a tax bill come. I had some expenses for a conference that I was throwing that I had forgotten about, it was like 20 grand. It was just these things all came through at once and I was super stressed, and I remember thinking I don’t know if I’m gonna be able to payroll. I started looking up borrowing from my 401K, which is something I never do. I never did that but I was evaluating all the options. Can I sell an app? ‘Cause I still owned other apps.
 That year from about March until really October, November was pretty damn stressful. I was stressed about the money and you weren’t. You never … you talked with me a lot and helped me process it and said things like, “You’re gonna figure this out” and it’s not that it’s not that big of deal but it’s that it’s like, we’re gonna come out of this the other side. Even if everything had gone south, we wouldn’t have lost the house. We would not have been bankrupt. We would … it wasn’t like I mortgaged everything. You were the reality check for me. To constantly say, “What’s the worst that could happen?” It was like, “Well, I have to lay somebody off that I just hired.” And you’re like, “Yeah, that’s a bummer, but that’s not the end of the world. You’re way more stressed about this than you should be.”
 You were my sounding board, my sanity check and you had … you were seriously engaged listening to me angst out over this for what was in retrospect way too long.
Sherry:I think that’s … not like I always do it perfectly but in that instance I did, or I showed up for you in a way that made you feel basically secure. You could work with this big problem that you were having without fear that your relationship, or your family was gonna fall apart. I basically said, “I’m here, and we are gonna be fine, and if Drip falls apart, so be it. But this part of your life is stable and secure and safe.” It’s a huge deal in human psychology so when we think about human attachment it really is the basis for human development. Without strong attachments as infants, infants will die. Even if they’re fed. Even if they have basic physical needs met. If they aren’t held, if they aren’t loved, if they aren’t cared for properly, if there’s not an emotional quality to the care taking that they experience, they can absolutely die. There’s been lots of cases of that documented in orphanages and institutional settings where this failure to thrive where infants haven’t grown properly.
 We have historically thought about that as a problem with child development but in the last 20 years we’re thinking about it a lot more with adult development too and the need for deeply emotionally connected relationships to really sustain us, especially in the midst of hard things.
 One of the terms that Dr. Sue Johnson uses for this kind of a relationship is secure dependence. I gotta say, as a feisty feminist I don’t really like that term but I do think it’s an honest term. It’s the freedom to really depend on someone else to be there for you so that you don’t have to protect yourself on all fronts at one time. You can go fight your financial battles and solve your Drip problems and be secure in your dependence on me as your partner.
Rob:In my experience it’s such a big deal to know that someone has your back. That at least on one front of your life that someone is there to help you out because the worst times that I’ve had in my life are where stuff’s going wrong on one front and then it goes wrong in my personal life, and then in my business, and then my friendship, and then my relationship, and then my family. That’s when you just lose your mind. The fact that I could be having these work struggles, it’s like I can have a chaotic work life, but I can’t also have a chaotic family life or home life. If those two are crashing and burning it is catastrophic. It is so hard to stay sane for me personally, and I’d imagine for other founders as well.
Sherry:It’s a little bit nuanced to describe what this looks like and feels like. Although most of us kind of know the difference but when we talk about a secure attachment or this secure dependence it’s relationships where we feel like our partner is accessible. They’re available, they’re reachable, they’ll pick up our calls, they are … they have time for us. They’re physically, logistically accessible and they’re emotional responsive. They are moved by our situation. They are sensitive. They are … there’s an emotional quality. They don’t necessarily have to have all the same feelings that we have about everything but that they show that they are emotionally impacted or invested in what’s happening to us.
 Then the third piece of the secure attachment in adulthood is engagement. The sense of being present, of holding our hand, of rubbing our back, of being invested and right next to us, if that makes sense. So accessible, responsive and engaged.
Rob:Right and I think back to that 2014 story I was telling earlier, and I remember you and I were in Thailand with the boys, and it was, if I recall, it was October and you were certainly accessible because it was nice that we had a lot of time to talk it through but you and I were hanging out chatting while the kids were off doing other stuff or sleeping or whatever. That one’s probably the easy part, frankly, in our relationship. But it’s the being responsive and engaged. The responsive to the fact that the difference between the New Haven year and the 2007 versus 2014 was that you and I were not emotionally available for the others in the 2007 and you were in 2014 and you were able to sit and hear my, whatever you wanna call ’em, fears, frustrations, anxieties and not feel burdened or weighed down or too stressed out. I know it stressed you out at certain times, but not feel like it was draining you of life.
 When we were going through this tough year three, four months ago with … as our family makeup was changing and we had the two additional kids, you and I could feel like neither of us had the emotional responsiveness for other problems and I remember specifically not telling you certain … like, “I was frustrated at work today.” Didn’t come home during that time and say it, because I knew that you felt like I did at home. That we were both just right at the edge of our ropes basically.
 Luckily that time has passed and I think that being emotionally responsive it can be a challenge but it’s something that … know where you are with that. Just start to … I think it’s just about knowing yourself. I will detect it in myself when I start to get run down and I realize I need to fix this or at least need to communicate to you that, “Dude, I’m on the edge and I can’t be emotionally responsive right now and I’m gonna try to fix that.”
Sherry:I think in the deeper sense when someone doesn’t feel secure in their relationship … like if I wasn’t committed to you and I was like, “Oh my gosh, we’re gonna run out of money.” and “Maybe I need to look at what other opportunities are available for me.” Kind of like if I wasn’t all in then the emotional quality of the relationship certainly will feel that. There’s this one phrase that we use to describe this is an anxious attachment, which is marked by anxiety, and clinginess, and lots of anger and emotional upset. In the situation that you talked about I might be more upset than you about the financial problems of Drip, and I might be very … just very upset and worried about it constantly, and what are we gonna do? What are you gonna do? Are we gonna be okay? We’re not gonna be okay.
 That’s obviously a reaction to a stressful situation, but it can also be a marker of a partnership that is not very secure. People don’t feel secure together. I think the other way that that can go bad is what we call an avoidant attachment where emotional is suppressed, and it’s kind of cold. In this scenario I might have said something like, “Well, what are you gonna do? You gotta figure it out.”
Rob:Yep, which is … can sometimes be helpful, but can feel like someone’s bailing on you as well.
Sherry:It’s about the emotional quality not the words, right?
Rob:Yeah.
Sherry:There’s a way in which as a warm, caring wife I could be like, “Buck up little camper. You gotta figure it out.” But the coldness of, “This is your problem. It is not my problem. I’m not with you in this. You dug your own mess and you go figure it out and basically, don’t be bothering me.”
Rob:Right.
Sherry:It’s the emotional quality. That’s why sometimes these things are hard to talk about because there’s so much nuance. It’s almost … it’s never about the words it’s all about how it feels and what you communicate to your partner about your presence with them.
Rob:Yeah, that’s the thing is being aware that this stuff … a, that it’s been categorized, right? I mean, psychologists have studied it and really looked at all the ways these things can be done well and how they can be done poorly. That’s why I think it’s nice to have this taxonomy or this structure that you’ve just laid out of the different ways to do it, and then when you find yourself with your spouse or significant other telling you something that’s really stressing you out or that’s really stressing them out, to be aware of that in your own head of like, “Huh, am I getting overwhelmed by this? Because I need to figure out is it just that I don’t have the emotional availability right now. Is it that I never have the emotional availability and I need to get better at that in my life, or is this a temporary thing because I’m stressed here?”
 Just that process thinking of actually stepping back from the process and thinking, “Boy, this is why things are going south, how can I fix this?” Rather than because when you’re reacting emotionally and your lizard brains going crazy it’s not helpful. It’s not gonna just fix itself.
Sherry:Right. Fear and anxiety are the killers of connected attachment. Big fear, I’m afraid you’re not gonna show up for me. I’m afraid you’re not gonna be a good partner to me, that sort of like existential, our life together kind of fear. That is crazy making over the course of a relationship. That feels so much different than the ability to settle in and be like, “Hey, it’s not gonna be perfect all the time and there’s gonna be ups and downs and our life’s not always gonna be perfect, but I really do trust that you’re gonna show up.”
 That feels so different than “I live in fear that you aren’t gonna be the partner that I need or that you’re not gonna care when I’m hurt. Or you’re not gonna come comfort me when I’m sad.” That kind of fear and anxiety is really a killer to intimacy on every level. It’s a killer to great conversations. It’s a killer to feeling emotionally connected. It’s a killer to sexual responsiveness. It’s a killer to basically everything that a couple goes through in their day to day life.
 So having a handle on your level of anxiety about day to day stuff, and then anxiety about big picture relationship stuff is a really important way to begin to gauge how healthy your relationship is, and then to know what to do to make it feel more secure and healthier.
Rob:I like the way you’ve laid that out because it’s not only being aware of it and fixing it, it’s like what are the ramifications if you don’t? And laying out all the negatives and then the way that it can just undo a relationship.
Sherry:I think one thing I’ve really … I think is really important about this conversation, and maybe even going back to that term secure dependence is that a really strong, secure attachment, a relationship that’s interdependent is a fantastic foundation from which to really become the best version of your individual self. It’s not that you give over your emotional life to being part of a couple and you get lost in that, and this is why I think this conversation is super important for entrepreneurs.
 It’s kind of this … if you really want to kill it in your business, if you really wanna be the best programmer, marketer, product person, psychologist, lawyer, whatever, that you can be, that happens when you have a secure base. When you have this other person that you can trust and you depend on. That allows you the freedom to … in little kid infant terms, go explore the world. To go see how strong, and smart, and wise, and sassy you can be out there in the big world because you have a safe haven to come back to.
Rob:Yeah, that’s a good way to put it. It’s that someone has your back and that you always have this base to launch from. I know that even when … back in college before you and I were dating, and I was just flailing around, I was trying to start businesses, I was trying to do stuff, but I always had this underlying anxiety that I needed to care of this base need and it was to have, as you said, a base to with which to launch from, and I think that when I feel stressed about life or about our relationship I’m much less able to be creative and motivated on other things because all I wanna do is fix the underlying problem.
Sherry:We’ll be exploring this topic of attachment in some detail in the course. We also are gonna spend at least one of the episodes talking about sex and intimacy. We’ll spend one talking about big picture goals, and dreaming and planning together, and then we’ll spend one talking about day to day life and communicating well together. Then there’s some other topics I’m cooking up but I would love to hear from you if there are things that you wanna make sure we include in the course, or address, or talk about in terms of the life of an entrepreneur in the family. Please let us know.