Episode 76: The Family Side of A Startup Acquisition: Part 2

Rob and Sherry continue their conversation about the struggles faced during Rob’s company’s acquisition. They talk about all the different elements that impacted them and the family and discuss what may lie ahead.

Episode Transcript

Rob Walling: This week Sherry and I continue a two part series where we talk about the mental side and the psychological struggle and the impact on the family of my start-up trip being acquired. So if you haven’t listened to part one, which was last week’s episode, I highly recommend you go back and listen to that because in this episode we basically continue with that conversation and look at all elements that impacted me and my spouse and the family, and then where we’re headed next.

Sherry Walling: I think one of the low points for me was there was moment when you were feeling really stressed out and you kind of made this giant, scary statement. “If I don’t do such and such by August, I’m gonna lose a million dollars!” I just stopped and looked at you and was like, “That is not true. It’s not true at all.”

I realized at that moment that the stress of this experience had just gotten so inflated that it was kind of messing with your sense of reality. And that was one moment and it was, like, the low point. But I think it was really representative of how hard this was, that there were so many moments when it felt like the world could fall apart, our lives could fall apart. Maybe I’m being a little bit dramatic, but the stress sort of felt very dramatic, every now and then, here and there.

Rob Walling: Yeah, to be honest, I don’t even know what that even means. I don’t know what I … I seem to vaguely remember saying that in this cloud of stuff, but it doesn’t even make sense in terms of the reality of things, so yeah, I was like really … I must have been really out of it.

Sherry Walling: You don’t remember that? I think you were talking about like … we were having a conversation about whether we were gonna drive or fly to Minnesota. I was like, “Let’s drive, we can, you know, see the Grand Canyon and Mount Rushmore and blah, blah, blah,” and you were like, basically, “I can’t. I have to work. I need to get things done.”

Rob Walling: Oh, yeah.

Sherry Walling: You were being super dramatic.

Rob Walling: That’s in essence was it was. So I was being dramatic of like, “I’m gonna lose a million dollars.” Like throwing this thing out, yeah.

Instead of just saying, “You know, I really can’t do that.” I mean, right? That’s the logical thing is to say, “You know, I can’t take two or three weeks and drive. I just have to work, especially in this early period as we’re transitioning, blah, blah, blah,” and instead I just throw out kind of this drama. It’s just the best way to describe that, right?

Sherry Walling: Yeah, and it was, like, almost funny, and I remember just looking at you and being like, “That’s not true.” And you looked sort of wounded and hurt and like you wanted to defend yourself and come back at me and explain how it was true, but you couldn’t because you knew it wasn’t true and you know you were being very [crosstalk 00:03:16] dramatic.

Rob Walling: It happens. Stress does things to people, you know?

Sherry Walling: Indeed.

So now the deal is finalized and today is the fourteenth of July and we are getting on a plane in three days to make our way to Minneapolis.

Our car is there, our stuff is en route, our second car ships tomorrow, and the deal is done and it’s finalized, and we’re all in on this, kind of, next phase of this start-up life adventure.

We’ve obviously told the children. They were the last to the table. We wanted things to be very final and clear before we told them. So I actually picked and rented a house and then I told them after I could show them pictures of their new room and the lake that they will live near and talk to them about their neighborhood and schools, cause I think that has helped them with a sense of what they’re looking forward to. I overhear them having these funny conversations about whether or not the Trader Joe’s in Minneapolis will have the mango lemonade that they like this summer, and whether or not there’ll be good ice cream, and, you know, they’re sort of thinking about what life is going to be like and talking about it together.

Rob Walling: Yeah, and, I mean, just to chime in, we’re moving to Minneapolis. Some of the Drip employees, the Drip employees were given the option whether they wanted to or not. Some are and some … we are keeping an office open in Fresno … and some folks are staying there as well. That’s the cool part. It’s like, I’m now at the point where it’s really exciting to think about moving to a new city and Minneapolis is a pretty sweet city. If you haven’t been you should go check it out. There’s lakes within the city limits. Our house is a block from a lake. It’s just a really neat, nice place to live and I’m geared up and excited about … cause we are good at adventures. That’s something our family does pretty well, and that’s how I’m thinking about this, kind of starting a new chapter.

Sherry Walling: I have a list of activities that we’re gonna do and places we’re gonna visit. When we did visit, we got to spend an afternoon with Clay Collins from Leadpages and we had a lovely time together. He was talking up the ice cream selection in Minneapolis, so we have a list of ice cream places to try. There’s some great museums and the theater and the kids are gonna do a little summer camp at the children’s theater. So there’s some cool things to look forward to.

One of the other low points for me was needing to close down my practice and saying goodbye to most of my patients and to my colleagues. One of the things that got really complicated was that I have, had, two post-doctoral fellows who work under me. I’m their supervisor. Their jobs are tied to me, basically. So that has left a lot of upheaval, and one of them has to find a new position, because there’s only one other person who is able to supervise in our clinic and he can only supervise one of them. It’s a little bit technical, but that has been really hard, is kind of the way that this transition has kind of adversely affected other people. You know, the people that I care about and work with.

So I think everything is gonna be okay and obviously in the long run this the right decision for Drip, it’s the right decision for our family, but it certainly has not come without some pain, and I have not done as well as I thought I would, given I’m the one who was like, “Yeah, let’s move, let’s go on an adventure. This will be great.”

The goodbye process has been harder for me emotionally and logistically than I thought it would be.

Rob Walling: Yeah, and I think for me, since there was so much time and energy put into the deal, and selling the house was such a challenge … I mean, there were so many challenges were going on and so many of them have wrapped up. By the time it had ended, I had to say goodbye to a few people. That’s always bittersweet. But having come from such low … low point may not be the right word, but just such a hard time, and to now be done with that? I feel, just very, excited, and like everything’s going up into the right. But it has been hard to watch you deal with the transition, because you typically are much better at transitions. You tend to get excited about new adventures, and so to see you be impacted as strongly as you have been, it says a lot. It’s an indicator of how hard this actually is for you to have said these goodbyes.

And so to think about wrapping this up, there’s so much that we learned from this process, that in retrospect, is helpful for us to think about and might be helpful for someone else to think about as they’re entering into a similar process.

One is that negotiation in general, in this type of stressful time period, is probably gonna be hard on the founder and it’s gonna be hard on the whole family. I think negotiating in specific is important to do well.

Sherry Walling: Yeah, I think it’s another opportunity to be really good at the swifts between work and family life. As much as you and I in particular like to have our work and home life somewhat integrated, I think once there’s this, that level of negotiation and the tension and the stress that go into that, separating work and family life becomes much more important. Making those shifts between who you are at home and being nice, generous kind dad and husband, and who you are in the midst of the negotiation, which is someone who is very, very careful, and very attentive to details, and needs to take a hard line sometimes. So that’s one thing I kind of wish we’d done a little bit better, is having these more significant breaks between the work process and the family process. But you know that’s not perfectly realistic in this scenario.

Rob Walling: Yeah, I mean, I remember during this time thinking how can we make this better, and the chaos that was going on with the selling the house and the septic issues and moving across versus moving to Minneapolis versus selling a company. It was like there was more going on in this three month period than perhaps we’ve had going on in ten years. It was nuts. And that was … I think if you can at all … I mean, we’ve talked about this on the podcast, that if you can take hard things and do them one at a time and space them out, that is the best way to do it. As soon as you have two, or three, or four that you’re attacking at once, that’s when it tanks you, and that’s when you get decision fatigue. You get frustrated. You get stressed, and that’s when things start coming apart.

Sherry Walling: I think the other part of it is that this is not a process that happens neatly in a nine-to-five time frame. You need to have conversations with Clay when you and Clay could have conversations. Those ended up being in the evening. Sometimes they ended up being on the weekends, and it just didn’t sort of neatly fit in to this nice, controllable, “here’s my work time and here’s my family time.” Again, that was stressful and difficult, but obviously it’s sort of worth it and it was warranted in this case.

Rob Walling: Yeah, I mean that’s an interesting point you bring up, because a lot of us, especially if you’re a bootstrap founder, and you’ve gained control of your schedule where you maybe work and you don’t work on the weekends, you don’t work evenings, whatever, wherever phase you’re at … in something that’s this challenging, it may very well wind up that you’re gonna need to kind of expand your working hours and your expectations. That can have an impact on both the founder themselves, who’s used to not doing that, he’s used to not thinking about work on the weekends or in the evening anymore, or it can certainly have an impact on the spouse or significant other.

I think another thing I took away from this is in terms of the negotiation, it’s definitely good to be in a position where you don’t have to sell when you are running a profitable company, and growth is happening. It feels great and it feels like you don’t need to sell at all.

But counterintuitively, that very well may be the very best time to sell, because it’s when you’re the best negotiating position. I guess that doesn’t necessarily translate to kind of the entire family experience, but it is something that I took away from it.

I think that’s a good way to put it. I think, “options,” is the emphasis there. It isn’t like I’m some master negotiator or some person who knows who to pull these levers and do these things, but it’s just that I always knew that there was an option to keep going on the path that we were going, because both family life and business life and professional career were doing fine. Nothing was gonna crash and burn if this deal didn’t go through. Although the whole time it was something I wanted to happen, but it didn’t have to happen. I think that’s probably a good position to be in if you find yourself thinking about this type of exit.

Sherry Walling: Yeah, I think you always felt like you had a lot of choice, which was important. I mean, this kind of process is really, really stressful, and I think all the more stressful if you feel like you’re going into it with very limited options, or that this is something that you have to do.

I think one of things that I have reflected on throughout the course of this process is that it was definitely much harder on me than I thought it would be.

In the context of this podcast, as well as the general organization of our lives, I’m generally very supportive of Rob and feel a lot of flexibility and freedom and kind of, like, “Hey, do what you wanna do. We’ll make it work. I’ll do whatever I can to support you. I feel very flexible and up for an adventure.” And that has definitely been my stance on one level throughout the entirety of this process.

But I think as embedded as I have become in my own career and in my own work in Fresno, it definitely became much more difficult to say goodbye and to pick up roots than I thought it would be.

Certainly, if the outside of this conversation and, I mentioned briefly, but someone in my clinic has to find a new job because I’m not gonna be there to supervise them, and many of my patients who have been long term people who have significant trauma experiences, and it’s been my role and my privilege and my responsibility to sort of take care of them as a psychologist. And so to shift all of that has been much, much harder than I thought.

As I’ve said over and over, I think it’s a good thing. I’m happy about the move. I’m happy for this part of Rob’s life, but I think it’s come at significant sacrifice for me and for my career. To be honest, I don’t know that you fully know that or have acknowledged that or have maybe appreciated that, and you don’t need to or have to, but I guess it’s just another place in which those of us who are involved in this kind of entrepreneurial journey, at least in this case, it feels like there are some really significant sacrifices that I made willingly, but have been very hard and painful, nonetheless.

Rob Walling: Yeah, and that’s interesting, because that all comes out of moving, right? And that was the one thing I didn’t want to do. And that upfront you said, “this is on the table.” Because there were other factors in play, and you love adventure and wanted to get out and explore other things.

Sherry Walling: Yeah, and that’s really interesting because there’s the catch-22 really. Because you’ll say, “Oh, well you wanted to do it this way,” and then I feel like I don’t get much compassion or support for how hard it has ended up being.

Rob Walling: You don’t tend to get hung up on emotional things, and that the fact that this had struck you so hard made me realize how much of a challenge it was for you. But I totally get it.

It seems that you had stronger ties than either of us realized in the place where we were living.

Sherry Walling: I have really significant responsibilities. I also feel like, for you, you’re going to gain. Your team is mostly going with you. Your team is gonna grow. You’re gonna benefit from these relationships with Clay and with other people who can be … people to bounce ideas off of and to learn from and to learn with. And I’m going to empty space. I don’t know. And, so, a little bit of that excitement is tampered by the fact that, like, I have some ideas of what’s next for me, but in general, I think I have more trepidation about my own professional future than you do at this point.

Rob Walling: Well, sure. I mean this is much similar to us moving down to L.A. for grad school or moving to Connecticut for post-doc where you had, or I guess it was internship, where you had stuff lined up, and I was wondering, like, “how is this going to look for me?” And I totally get it. I’m not trying to compare it, or say one-to-one. “I did this for you so you have to do this for me.” But I do know how that feels, to be moving into a place where it’s like, “wow, I don’t know anyone. I’m gonna have zero work colleagues.” Cause that’s how Connecticut was, right? That’s how L.A. was, as well. Like, I’m gonna know no one and you’re gonna have a cohort of people. You’re gonna have your classmates or your other interns. So yeah, I understand, and we have two kids, right? So it makes it even more complicated.

I mean, I guess it’s an interesting conversation. Like do you wish that it was different at this point?

Sherry Walling: I don’t. I feel like one should reinvent one’s self a few times before forty, so I have a couple more years before that deadline.

No, in all honesty, I think it was time for us to leave Fresno, and I was very, very comfortable in my job. But I’m not sure I was pushing myself or learning many new things. So, it was time, but it’s hard.

It’s good, but it’s hard. That’s, like, the summary. That’s all I can say about it. I don’t regret it. I’m not afraid of it. At this point, I’m really excited. But it’s hard.

I’m also really, really sad to leave the ocean, which sounds shallow, maybe, but I’m really sad to leave the ocean. That’s become my happy place and my home.

Rob Walling: Yeah, you have a real link to that. I feel like a lot of times the right decision is the harder one. I do feel … I didn’t want to move. You and I were both comfortable where we were, but I know that it was very likely stunting both of our, kind of personal growth and personal expansion of where we could be.

Sherry Walling: I think I’m a little fearful about what’s ahead. I think I’m not sure how we’re gonna transition back into some sanity after the level of stress and anxiety that you’ve been under. I’m a little afraid that that’s gonna be the new status quo, the new normal.

Rob Walling: What are you talking about? I’m totally lounging.

Sherry Walling: Yeah, okay.

Rob Walling: Last couple weeks have been [crosstalk 00:17:42] different.

Sherry Walling: Yeah, you’ve chilled out a bit.

Rob Walling: Yeah, little bit. The electric chair is little scary sister. I mean, hopefully, I’ve been conveying this, but I can feel it. You know, I have enough kind of self reflection as this point to look at myself and think, “oh my gosh. You are a completely different person that I was three weeks ago.”

Sherry Walling: Yeah. Yeah. Better. Better.

Rob Walling: Don’t say maybe! How about the kids? Are they more flexible than we thought?

So we’ve been without a home for about five weeks now, and it will be another four weeks before we’re settled in our new house. They’ve lived with friends, they’ve lived in a dormitory, they’re now in an apartment. We’re getting ready to move in with friends in Minnesota for a couple of weeks, and then we’re gonna move into our new house while you’re at MicroConf Europe and I’m like, handling the move.

Rob Walling: That’s gonna be terrible. Yep.

Sherry Walling: So, but the kids are doing fine. We basically have a huge … each of us has a suitcase, a small suitcase full of clothes, and a backpack with our computer and iPad and whatever, books and stuff. And then the boys have an extra duffle bag that’s essentially full of Legos and art supplies and origami paper. That’s been key, they’ve actually been pretty fine in all of these different environments because they have their selected activities to go and have fun with.

Rob Walling: I wish I had an entire bag full of Legos and art supplies. This is where you and I went wrong.

Sherry Walling: True. It’s true.

Rob Walling: Yeah, the kids have done well. In the past, one of our kids has had more struggles with the moving around, and it seemed like whether it’s age or whether we’ve just indoctrinated him into the chaos of this, things have been much, much easier this time around.

Rob Walling: And so, I guess to wrap us up, what’s next for everybody? For you, it’s consulting and a remote therapy practice.

Sherry Walling: Yeah, it’s been interesting, because I don’t know if you can hear it in this larger conversation, but I’ve been feeling just a little bit bored or a little bit sad about not being totally sure about what’s gonna be next for me. It just, in the last week, I’ve had three founders reach out and make connections with me about consulting, which is sort of the direction I would like to take, to do more consulting with founders and their families and then to maintain a small, more traditional therapy practice that’s a remote practice.

And so, it’s been cool, but you know, a few people have reached out and said, “Hey, we need you! We like you. We want to work with you.”

In a time when I’m really question like, “What am I doing in the world? What is my calling or my job right now?”

Rob Walling: And so, if you’ve listened to a few episodes and you feel like you’re a founder, or you’re a founder’s significant other or both, and you find that you might need to talk through some of this stuff with someone like Sherry who has experienced dealing, obviously married to a crazy founder who’s lived a crazy founder life, as well as has a PhD in psychology and still has the professional experience to deal with this kind of thing, email sherry@sherrywalling.com. That’ll go directly to Sherry, and you can sort out if this might be something Sherry has offers, packages, where you can do three sessions at a time. Longer if you need, but it isn’t some big time commitment. Folks who have gone through this with her have gotten a lot of value out of it.

Sherry Walling: So what’s next for you?

Rob Walling: I gotta be honest. I’ve been trying not to sugar coat this as I’ve talked about it, but I’m genuinely, really excited for the transition. I’m excited about Minneapolis. I know it’s gonna be cold in the winter. You and I have done cold before in Boston and Connecticut. I’m excited to be part of the broader team at Leadpages. So far everybody I’ve met has been super cool. I’m pretty interested to learn, I mean, there’s a lot for me and my team to learn from the Leadpages folks. They started within, think it was maybe six months earlier than us, and they’re a massive company. They had massive growth, and so their marketing channels and marketing expertise are formidable. They are some of the best, probably the best in this space at potentially in the BDV SAS space at all at marketing. So just excited and interested to learn, cause that’s a big part of what keeps me interested, right, is learning new things and kinda connecting with interesting people. I think that’s what’s on my radar for the coming months.

Sherry Walling: I’m really excited about their swings. They have all these swings in their office and they’re really cool swings.

Rob Walling: Yep. And so we’re gonna swing in the office and drink cappuccino and Soylent.

Sherry Walling: Soylent green is people.

Rob Walling: And then the family’s all gonna have a Minneapolis adventure and there’s gonna be snow involved and snowmen and snow forts and snow fights and I guarantee you our oldest son is gonna build at least one of the snow scenes from Calvin and Hobbes.

Sherry Walling: He is quite a student of Calvin and Hobbes.

Rob Walling: Yep, there will be photographs of that. Keep your eyes on Facebook, people. And then after that, it’s living somewhere without state income taxes. Is that right? You feel me? Yeah, that’s a lesson.

Sherry Walling: How’s Hawaii?

Rob Walling: How’s Hawaii? I dunno, I need to google that. Cause living in California and receiving a single chunk of money, and then paying an enormous amount to the state just makes you feel like, “you know, if I were smarter, then three months ago we would’ve moved to Washington state, where there’s zero percent income tax.”

PODCAST

Subscribe to Podcast

Sherry has a unique combination of experience and education that results in an ability to completely understand what founders go through generally, crossed with their personal foibles specifically. The result is truly helpful, not regurgitated pop psychology or the “coaches” who haven’t been there before themselves.