Sherry and Rob open up about some of the events that have happened with their family in the last couple months. They talk about how the power of entrepreneurship has helped them tackle hard things and how important it can be to have supportive people in your life.
| Sherry Walling: | So one of the highlights of my fall was giving a talk at Business of Software in Boston at the middle of September. It was a great talk. I had a lot of fun, went to the speakers’ dinner, stayed up way too late, drank way too much, hanging out with friends and fellow speakers. |
| And I took a really early flight the next day because there was a hurricane supposedly coming in towards Boston. And I was really tired. I hadn’t slept much. But I’m sitting on the plane. I’ve got my laptop open. And I’m sitting next to this woman who’s going on vacation to Las Vegas. And so she’s chit-chatty, and she’s like, “Have you been to Las Vegas?” And I’m like “Yeah, I have. Like every year.” And at some point I just put my headphones on and stopped engaging with her. | |
| And I started crying on the plane, pretty hard. Which was very embarrassing and not really my normal MO, but I was crying because I was writing this document, writing about our family. And writing about all of the things that I love about you and our two boys. And writing about all the things that we would change, or we would lose if I made a decision that I had to make, or that we had to make together. | |
| So I’m on the plane, I’ve just given this great talk. And I’m descending into this mess of tears and fear and worry about the future. That was, I think, a Tuesday. I came home on Tuesday, and I turned around, and on Friday I got on a plane, and I flew to California with a question in my mind of whether or not I would return home with two more children. | |
| And I think the plane ride after BOS, the plane ride home from Boston, crying on the plane, writing, trying to just put everything out into words, get it out on a piece of paper, so I could sort of sort through how I felt about this decision. That was one of the most sort of pivotal moments for me in the last couple of months. | |
| Rob Walling: | And so today we wanted to talk through what that experience has been like. And I wanted to frame it and structure it around a talk. Actually really a non-talk. It was more of a conversation that I had from the stage of MicroConf Europe that was in Lisbon a few weeks ago and kind of want to talk through, not only that process, but just dive into the power that we have as entrepreneurs and I think a lot of things that we take for granted, and things that we don’t talk about in our space, are things like once you’ve achieved freedom and you run a business, what next? |
| Like that’s the goal for so many people, but what else is there, and what other moral imperative should we feel, both for our families and colleagues, friends, and to the broader world. | |
| Sherry Walling: | I think when I say also that today episode’s sort of intensely personal. You used the term moral imperative, and I think that’s a good term to use. But it’s also one that is personal, like one that really reflects one’s own individual values and approach to life. So we’re going to talk about what has happened in us and in our family in the last couple of months. But this is us talking about this family situation and how it’s shaped our businesses and how our businesses have shaped the decisions that we’ve made. It’s definitely a personal one. It’s about us. |
| Rob Walling: | Right. And I don’t want to come across as preachy, nor as we owe the world this as entrepreneurs or anything like that, but I do think these are the things we’ve been mulling over for a while. |
| Sherry Walling: | We got this phone call on a Sunday night from a social worker letting us know that some kids, two children who are in our family, one of them we haven’t seen for nine years, one of them we’ve never met, and we got this call from the social worker saying that these kids were gonna go into foster care unless we were willing to be sort of an emergency custody home for them. |
| Rob Walling: | And this is the kind of news that is really, it’s kind of hard to absorb, and it’s hard to imagine that it’s real. I think the original timeline that was given was four days or something. Like you have 72 hours, 96 hours to do this. That didn’t turn out to be reality, but I think it was someone kinda trying to speed the process along. |
| But this is insanely … I mean it’s like dropping a bomb in the middle of your life because you have a very short amount of time to decide. Do we turn our lives upside down? Put a lot of things on the line that we have carefully, carefully crafted? Alright, we have been very deliberate about the decisions that we’ve made. When we had kids. How many kids we had. Our house is set up for the number of people in there. | |
| We still fit in a sedan. We still fit in one hotel room. We travel a lot, and it’s just the perfect amount of people. So there’s just so many things that we had crafted about our lives that, if you say yes to this, that you could potentially just break it and spill it all out. | |
| But then how do you say no to it? That’s the hard part. It feels like the right choice to do this, but at what cost? | |
| Sherry Walling: | Yeah, how do we say no in the sense that we have abundant resources? We have more money than we need. I have more shoes than I need. I’ll say it out loud. We have resources, both financially but also emotionally, personally. We have energy. We have passion. We have community. We have support. We have all of the things in place that you need to do hard things, which is why we’ve been able to do hard things. |
| And so, to be asked to do, yet another hard thing, it’s sort of like, hey this is what we do. We do hard things because we can, and because we’re well suited for it and well resourced for it. | |
| Rob Walling: | And it’s also hard to think about all the things that we have planned in terms of our businesses, and the growth that’s happening with you and your brand right now. Getting the book out. All the stuff that we’ve been thinking about, and trips we had planned to Europe and there was one to New England, tickets that have already been bought. |
| Some of that stuff is short term, but you can tell that adding two more members of a family, going from four to six … Two of our cars at the time wouldn’t even hold that many people. It just instantly calls a lot of stuff into question. We don’t have that many bedrooms in the house, and we have to be in the house until sometime next year. | |
| There was a lot of deliberation. You and I went back and forth, neither with such a strong opinion. It wasn’t so much a discussion, a back and forth, you and I, one person saying yes, one person saying no. It was both of us saying I don’t know, let’s keep processing it, for days on end. | |
| Sherry Walling: | The con list is tremendous, and then there’s an unknown list that’s even longer. All the things about how. What kind of shape are these kids in? They’ve had a really hard go of it. What’s their situation? What’s their mental health? What’s their physical health? How do they interact with other kids and then our kids, and what it does to them to have their relationship disrupted, have our family dynamic disrupted? |
| There’s so many unknowns, and that’s the hardest thing for me. I can kinda play pro/con really well. I can do math with everybody else, but the list of unknowns is just impossible to calculate or answer those questions, is what makes a decision like this very, very difficult. | |
| Rob Walling: | Right, and then the pros list was basically one bullet, and it was because it’s the right thing to do. Right? In our opinion, because it’s the right thing do. That was a hard thing to keep coming back to that. |
| Sherry Walling: | So we decided no, and I said no to you. I said no to some of the people involved, and then you came back that night and said, “I don’t know if you’re playing reverse psychology on me, but when you said no, it made me feel like we should say yes.” I was like, “Okay, well I’m not playing reverse psychology, but I’m just trying to make a decision cause I have to get on a plane.” |
| Rob Walling: | Yeah, when you said no it was such a relief. I gotta be honest, but then there’s just that thing in the back of your head kinda gnawing, you know? Isn’t this what we do? Isn’t this who we are? Like we can do this because we’re entrepreneurs. |
| You know, it’s cause we’re people who … Like probably most people listening, we do hard things. You take on things that are highly uncertain, that you know are gonna be hard, that are not gonna have a short term payback, that are gonna require you to get out of your comfort zone. | |
| All this is starting a business. That’s what those things describe, and it also describes this decision. And so, it’s odd for you and I not to want to lean in to things like this, but obviously the potential negative ramifications of it are so substantial that it required a lot of processing. | |
| Sherry Walling: | And the reality is, you can’t lean in on all fronts at all times. And we know that. We’ve learned that lesson before. We can’t lean in on two businesses, 2.5 businesses … I mean, we can’t lean in on everything. That’s not the nature of what it means to lean. Leaning is one direction. That’s the physics of it. I think that was the difficulty of like, this will cost something. It will cost so much. |
| Do we do that for people we don’t know who are in a bad situation, but that we didn’t cause? We have no responsibility here, other than responsibility that we choose. | |
| Rob Walling: | Yep, and so, I think it was somewhere between two and three weeks after that first call, you flew out and you came back with two more kids. And it was … Yeah, it was really a challenge. It’s been a challenge for the past couple months, just a lot of ups and downs. |
| Sherry Walling: | The logistics. |
| Rob Walling: | Yeah, the logistics. |
| Sherry Walling: | Have been challenging. I didn’t even think through all of it, but our coat closet was a nightmare. There were two people’s things in there. Now there were four kids. Well there were four, and now we need six. It’s just been … Where do everyone’s socks go? And the kids arrived with nothing, like clothes on their back. Nothing. |
| So the first day we’re going to Target and getting socks and underwear and clothes for everybody. The logistics turned out to be really challenging and time intensive at the beginning. We were organizing the bedrooms, getting dressers, getting everybody situated so they had a little corner to sleep in. | |
| Rob Walling: | And then within … I think it was probably a week after that … I mean, you and I weren’t sleeping very much because there was a time change going on, and the kids were stressed out. Everybody including our kids were stressed out. A few too many people to be in the house all at once, and within a week of that, I sent an email to Mike and Xander, who I cohost MicroConf with Mike, and then Xander is the coordinator who helps us run it. And I said, “I have some news that may impact my ability to attend MicroConf Europe this year”, which is a big thing to say cause I’ve attended and really run every MicroConf with Mike, and more recently with Xander. |
| So it was a very hard thing to come to, but it was something that you and I talked about it. We just can’t do everything. We’re gonna break apart here. Somethings gotta give, and it was kinda a tough thing to do, but it really was this … It brought me to start to think about his thing that I’ve noticed in certain people. And the people I get along with, and the people I admire in life and in business, are the people that value people over results. | |
| You could say relationships over results. I like to say people over results. And what I mean by that is, I’ve worked with, for and around people who, the results are what matters. You think about Steve Jobs, or you think about Henry Ford. You think about Benjamin Franklin. You think about these great inventors and artists and stuff and business people, and they sacrificed and completely nuked all the relationships they had. Their kids disowned them. They didn’t stay married. They had multiple marriages. They really were just tough people to deal with, but they got results because the results were the most important thing to them. | |
| And most types of industry have this exact thing, and there are few exceptions to it. But what I’ve noticed is in our community and the people who I tend to be around, and who I tend to enjoy being around, are those who value people over results. It’s not that we don’t want results. We still want to ship stuff. We still wanna write the book. We still wanna grow your business by two or three x each year, but you’re not willing to do that at the sacrifice of yourself, your sanity, of your family, of your close friends, of your colleagues, of the people that you love and trust. | |
| And that’s something that has occurred to me as we’ve gone through this process is, this is a hard thing to do because we all want results and we’re all seeking that as founders, but I feel like the bootstrap founder ethos and even if you’re not bootstrapped. If you’ve taken a bunch of intra funding, then yes, results over people. That’s how they do it in that space, and that’s one of the reasons it doesn’t jive with me personally, very well. | |
| Sherry Walling: | That’s what you sign on for if you do that. If you do it that way. That’s what you’re committing to. |
| Rob Walling: | Yeah, exactly. It’s growth over any individual. You won’t hear me talk smack about venture capital very much. I mean I believe that in certain instances, you should do it. It’s great to have growth capital, but the one thing that has always bothered me in all cases is that raising venture capital, in almost every case, means you care less about your people than about growth because the imperative on the investors and on the board, and then on the CEO, and then passed down, is that you have to grow. If you have to sacrifice people along the way, then that’s what happens. |
| And that’s the way a lot of businesses … I mean, this is one the critiques of just business in general. This is not some anticapitalist rant. That’s what I’m trying to say. It’s not all or nothing, right. It’s not only people and no results, but it’s, when push comes to shove, who are you gonna back? And maybe to you people is, maybe it’s just your spouse for now. Maybe it’s your little family, you’re a unit. Maybe it’s your colleagues. Maybe you have three or four folks who you’ve hired and who work with you. Maybe it’s a 50% company you’ve grown, but that deep down, you know that you are willing to take care of those people as much as you can within reason and not just always go after results over the people. | |
| And so, I sent this email to Mike and Xander and basically said, “I don’t think I can speak, and I may not even show up.” This is like four weeks, maybe five weeks before the conference. So I was devastated to send this. This was very hard for me to send it, and I actually procrastinated on it. And you can imagine, if you’re working with a team of people who value results over people, then it’s like, forget it. Get outta here. We don’t like you. | |
| Sherry Walling: | Get your crap together dude. Get here anyway. We don’t care about your sobbing heart story. |
| Rob Walling: | Yeah. |
| Sherry Walling: | You made a commitment, follow through. |
| Rob Walling: | Right. And that’s the responses from Mike and Xander. My next response was, I’m gonna read from his email. He says, “If you can’t make it, then we need to find another speaker or cohost. In the grand scheme of things, that feels like a rather trivial problem to solve. It’s not as if the sprinkler system blew in the middle of the conference. Oh yeah, we made it through that too.” |
| And that got a good laugh when I actually said that at MicroConf, but he said, “The short of it is this, don’t worry about MicroConf. We’ve got your back. If you need anything lifted off your plate, please don’t hesitate to ask for help.” And Xander said, “Well, darn it.” It actually was a four letter word, star, star, star, star. “That’s really tough, not only do I understand how rough this must be for all of you, but I know how incredibly important it is for the kids. Completely understand about MicroConf. Your things will go on.” | |
| Sherry Walling: | And I had to cancel. I did cancel a talk that I was scheduled to give in Seattle, and when I explained the situation, they were like, no problem. We’ll find someone else. We’ll still pay for your ticket. Just very gracious, and very okay to value the fact that this was something important in a couple of human’s lives. I appreciated that. It feels so different because you and I both have such … We value our commitments so strongly that to back out of something feels like such a big deal, and we have such trepidation about that. But when we’re on the receiving end of people over results, it’s pretty amazing to receive that kind of, hey it’s fine. Don’t worry about it. We’ve got you covered. |
| Rob Walling: | Yeah, and that’s something that I’ve just thought about a lot is this people over results, and the power that we have. Like I said earlier, as entrepreneurs, that we can … I hate it when startups say I wanna change the world. I’m gonna make a dent in the universe cause it’s so cliché, but you can change the world, but maybe for only five people. Or maybe it’s for 20. Maybe it’s for 50, but it’s your people. It’s that circle that you choose to have influence on. It’s like we have power as founders, let’s use it for good. |
| There are stages. I remember when I was scrambling, when I was employed, or when I was self employed, trying to keep my head above water. When I was employed making 15 bucks an hour, my second or third job. I guess my job out of college, I made 19 bucks an hour for some really pitiful thing. I really would have wanted to start higher, but that’s where I was in life. | |
| At that point, I couldn’t help the world. I couldn’t have taken on two kids. So that’s not what I’m saying here, but it’s like, your entrepreneur’s journey is, you tend to go from employed to maybe self employed, and then you become that entrepreneur where you’re actually running a business. | |
| And then eventually, if you make it past that, you become that investor, or that person whose able to just put money to work and not have to work day to day. And in the early stages, you’re scrambling trying to take care of you and your people, which may just be you. It may be you and your spouse, but as you progress past that, start to think about what does legacy look like. | |
| And it doesn’t have to be anything grandiose. It doesn’t have to impacting the whole world or sacrificing your comfort or feeling guilty about your success because I don’t think you need to do any of those things. But this experience really reminded me about how much power and influence that we have and that how we should use that power for good. And we should pass along, you know, use our resources, to the benefit of those around us as much as is feasible. | |
| Sherry Walling: | So we kinda went all in with the kids. We had new family photos taken. We bought furniture. We planned trips and worked hard to get passports, which we could never eventually get. And we went all in. We gave it our best and spent months talking … I should say spent hours, daily, for months talking with all of the kids about what was happening and what it meant and what it felt like. What family means and what it means to decide to make yourself less comfortable for the well being of somebody else. We’re sort of teaching our kids about power, all of the kids about power and the process of this. |
| One of the things that I did early on that was really important, at least for me, is I took that tearful document that I was working on, on that plane, on the way home from Boston, and I turned it into an email. A long email that I sent to our inner circle of friends and just let them know what was going on. And that I was scared. And that we were uncertain, but that we were gonna try. | |
| And that was very important because it mobilized our crew. So one of the things we got in the deal is a little girl. We have lots of boy clothes and boy things, but we haven’t had a daughter before. We haven’t had a girl in our home. So one friend sent an American Girl doll, and other friends sent boxes of beautiful hand-me-down clothes from their daughters. People sent letters to the kids. They sent packs of stickers, and other friends, local friends, came over and helped us take furniture apart and move it around. And spent hours with the stupid Ikea bunk beds, trying to figure things out. | |
| I think we both, but I’ll speak for myself, felt tremendously supported because we did decide to let people into the story. And not the version of the story that was, oh yeah, we decided to take on two kids, and now we have four. Hooray, but the version of the story that was like, we are scared. This is not easy. It’s not going well. We’re not … the real version of the story that wasn’t sugar coated, but that reflects what it feels like to have your life taken apart and redone right in front of your eyes. And it’s really important not to be alone in those kinds of moments. | |
| Rob Walling: | And so, as a listener, that might explain why I don’t think you and I have done an episode together in two months, maybe more. We had guest hosts. I did one or two solo episodes. You and I just couldn’t get into a room for 30 minutes, and since we certainly didn’t feel comfortable talking about it early on. It’s hard to talk or think about anything else when you and I get in a room. So the podcast is obviously been different and had to adjust over the past couple of months as we’ve tackled this challenge. |
| Sherry Walling: | Yeah, that was part of asking for help too. My friend Carry Dils did two episodes, and Karim Marucchi did one. People showed up so that things could keep marching on. |
| Rob Walling: | People had your back. They had our back. |
| Sherry Walling: | Which is good. I think by way of maybe finishing up the story part of this, it didn’t go very well with one of the kids. Kids who’ve lived through a lot of trauma and upheaval and transition, it’s hard going for them, of course. |
| We had to make the very difficult decision about whether we could keep this kiddo once we had him with us, and we decided that we couldn’t. Largely because of the dynamics that were happening between him and our boys, or one of our boys in particular. We felt some safety concerns and blah, blah, blah. I won’t go in to detail, but that was this double whammy, difficult decision. | |
| I think that was probably the … That was the part of the story that is hardest, is that at least in part, we failed the experiment. That was the part of the story that, for me right now, is the hardest in that, it’s probably too strong to call it a failure, but the experiment didn’t fully work out. | |
| I had to stick a kid on a plane, and say, I love you. I’m sorry that it didn’t work. That kiddo is in a place where he is well loved. It’s an okay story, but I’m still working through what it felt like for all of us, I think. To try something hard, and for it to not work the way we wanted. Even with all of our effort and power and support and financial resources and our big hearts. It just couldn’t work. | |
| So that’s still a live topic for me, but the little girl is still with us. We’re hoping that that will be permanent, but even that, we don’t have full control over. So it’s the wild roller coaster that we all know as entrepreneurs of giving yourself to something and going all in and taking the risk and putting in the work and despite everything that’s within your power to do, it doesn’t always work out the way that you wish. That’s the story. Then you get up, and you do it again. And you just keep trying. | |
| Although, the analogy breaks down because let me just say, I’m not trying to bring any more kids into our family. | |
| Rob Walling: | Yeah, this … |
| Sherry Walling: | We’re done. We’re not gonna keep trying that at all. No, no, no, no. |
| Rob Walling: | I think we’re tapped out on that one, being particular. Yeah, no. I took it the same way as you did, and you and I both used the word … We said, “It’s not a failure, but it kinda feels like it” is how I’ve been phrasing it. It’s like we did the best we could, and we went all in. We couldn’t salvage it. I have no, at least I have no regrets because we were all in on it, and we tried everything. You and I were on the phone with each other, and it was like, things were just unraveling at the edges. |
| It was not a sustainable situation at all. To your credit, you went to bat big time and got stuff done. As you said, I feel like the situation now, is so much better for everyone involved. The kid you stuck on a plane is, as you said, in a very loving home and is in good hands, basically. So much better than what it would’ve looked like months ago if we had said no. Right? I mean there’s a net win here, and yet, you and I still carry this heavy weight and this burden of this is hard. This is the hard thing about hard things. | |
| Sherry Walling: | Yeah. I don’t regret doing it, and I don’t regret making the decision to call it either. I think we … |
| Rob Walling: | Yep. |
| Sherry Walling: | But it doesn’t make it hurt less. I mean, I think it will. I guess that’s, again, the hard thing about hard things. It’s just like objectively, we’ve done the cross benefit analysis, and we’ve made our decisions. We’ve taken our risks, and we have done, at every turn, the things that we thought were right and doable. |
| But it doesn’t save you from the emotional roller coaster of the ups and downs of it, which is why I guess I have job because that’s the nature of entrepreneurship too. The highs are high, and the lows are low. | |
| Rob Walling: | I feel like us talking about this here, serves two purposes. One is that, that’s why the podcast has been different for the last few months. Our lives have been in disarray, and that’s a logistical thing. The podcast had different hosts and all that, and that’s not necessarily our goal moving forward, but it is people coming to back us up when our back’s to the wall, which talks about again, people over results. It was friends who were willing to have our back. |
| I think another take away really comes back to that power that we have, individually as founders and entrepreneurs and people who get things done and are willing to try hard things and are willing to sometimes win. And the victories are great, and they feel amazing. And sometimes lose, and sometimes those failures can be devastating, but that we’re willing to embark on the journey, and we’re willing to get back up and try things again after … you know, no matter what the ending. | |
| Sherry Walling: | And all you founders out there, you’re just a bunch of beautiful badasses. You really are. Keep doing what you’re doing. |
| Rob Walling: | Cheers to that. |
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