What 7 Kids Taught Me About Letting Go | Nate Quigley (Dad of 7, Co-founder/CEO of Chatbooks)

[00:00:00] Nate Quigley: If there’s one big lesson of my life that’s been beaten into me, I’m still trying to resist half the time and then every now and then remembering, “Oh no, you have to learn this one. Let go of that,” is I’m just not in control of a whole lot of things. Specifically what choices other human beings make, I don’t have a remote controller. I’m guiding people where I want them to go.
[00:00:24] Adam Fishman: Welcome to Startup Dad. The podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I’m your host, Adam Fishman. Today I’m joined by Nate Quigley, co-founder of Chatbooks, the photo book company that helps families preserve their memories. Nate has had quite the journey. He started the company after being overwhelmed by nostalgia, watching his oldest child approach leaving their house, struggled for years with a product nobody wanted until his wife, Vanessa, staged an intervention and suggested they just print Instagram. That simple pivot transformed everything and now she’s the co-founder of Chatbooks with him. Nate is also the father of seven children ranging from 18 to 30 years old along with two grandchildren, which makes him a startup dad record holder, the first with seven kids and the first startup granddad. In our conversation today, we talked about the unique dynamics of co-founding a company with your spouse and how Vanessa became the accidental co-founder who saved the business.
[00:01:32] Adam Fishman: His philosophy of work-life integration rather than balance and treating their company like a family farm where all the kids contributed, how his parenting evolved dramatically from child one to child seven, and what he learned about letting go of control, the challenge of allowing your kids to grow up and make their own mistakes, how technology has changed parenting and his approach to screen time with seven different personalities. And of course, the family rituals and traditions that kept their household of nine running smoothly. If you like what you hear, please subscribe to Startup Dad on YouTube or Spotify so you never miss an episode. You’ll also find it everywhere you get your podcasts. I hope you enjoy today’s conversation with Nate Quigley. Welcome Nate Quigley to Startup Dad. Nate, it’s my absolute pleasure having you on the show today. Thanks for joining me.
[00:02:22] Nate Quigley: Thank you, Adam. Great to be here.
[00:02:23] Adam Fishman: We were talking a little about this in the green room, so to speak, but you do hold the startup dad record for most number of children and that’s seven kids. And so to help ground everybody on this discussion, sort of some of the topical things we’re going to discuss, what’s the range? What kind of age range are we dealing with here with your kids?
[00:02:43] Nate Quigley: Adam, we are almost empty nesters over here. Our oldest is 30 years old. It’s crazy. I mean, that really will make you feel old when you say you have a child who’s 30 and our youngest is 18. Our youngest was theoretically graduating from high school in like a month.
[00:03:00] Adam Fishman: Wow. But there was a time where all of these kids lived under your roof in your house, all seven of them at once.
[00:03:08] Nate Quigley: When I hear people say, “Oh yeah, we have four kids.” I think, “Oh man, how four kids.” I have to remind myself like, “Wait, we had seven.” It does absolutely sound crazy and at times I’m sure it looked really, really crazy from the outside, but because they kind of come one at a time and they’re spaced out a little bit, you’re like the frog that’s getting bored, you don’t really realize what’s happening and all of a sudden you’re like, “Oh, there are a lot of us here.” Okay.
[00:03:31] Adam Fishman: Yeah, you and your wife get pretty tasty when you’re at 215 degrees after that seventh kid. Well, that’s cool. I’m excited to get into this and all the things you’ve learned.
[00:03:41] Nate Quigley: Am I your first startup granddad too?
[00:03:44] Adam Fishman: That’s a good question. You might be. It’s been pitched to me before
[00:03:49] Nate Quigley: Startup granddad.
[00:03:49] Adam Fishman: But you may be … Yeah. I’ve had somebody pitch their own dad. They’re like, “I have an 85-year-old great-grandfather who’d be awesome on the show.” And I’m like, “Okay, that’s not quite the vibe I’m going for.” But no, this is great. Startup granddad.
[00:04:03] Nate Quigley: I’m a 53-year-old startup granddad.
[00:04:05] Adam Fishman: Okay, wow. I love that. Well, maybe we’ll get into what you’re doing differently with your grandkids than you did with your own kids. That could be an interesting topic of discussion. So the other thing I learned about you is your wife is also the co-founder of your company and the two of you have been running it for 15 years. The first question I have for you is, can you tell me about co-founding a company with your spouse? What was that like?
[00:04:28] Nate Quigley: Well, she would say I had absolutely no inclination at all that I was going to start a company with you and I absolutely did not want to do that, but she had become Rescue the foundering flailing startup that I had started.
[00:04:40] Adam Fishman: Wow.
[00:04:41] Nate Quigley: No, it’s a true story. I was kind of in peak dad of seven mode and I just had this massive wave of nostalgia start buffing me around. Our oldest was 16 at the time and I could just kind of all of a sudden get this little vision ahead of the kids leaving the house and just sort of this life that we’d built together that was obviously our whole world was just going to peak and end and sort of start ending or at least start changing in a really big way. I think that led to where are we putting all our photos? Where are we putting all our videos? And the thing that’s become Chatbooks was this sort of response to this weird wave of nostalgia pain. Don Draper described nostalgia. I had some quote, like a famous Kodak carousel thing. Nostalgia is basically pain. And I was feeling it.
[00:05:31] Nate Quigley: So I was like, we have to build a thing that doesn’t exist yet that sort of gives us a place to put our family stories. It means so much to us. So that’s great. That’s a fun founding story. But the company we started, I was calling it Folk Story. No one was using it. It was too hard, too complicated, all the things you’re not supposed to do in a startup. I was just building the thing for myself and not talking to any customers and just sort of toiling away in the cave. And then with my CTO technical co-founder, we built another version of the thing that still no one was using. It was even more complicated. It had even more features and bells and whistles and platforms that supported and no users like mom and my sister were the only people who were using that other than me.
[00:06:13] Nate Quigley: And so that went on for two and a half years actually, believe it or not. I mean, I’m sure some of your listeners have read The Lean Startup. We were like the absolutely unlean startup. It was just sort of every chapter we did the opposite and had just sort of hired five or six people. Vanessa and I were paying everybody out of our checking account and continuing to transfer from savings and various other pieces and small piles of money we could find. And eventually Vanessa came downstairs one day and she said, “Hey, what are you doing? Are we ever going to get paid again? Have you looked at our finances? Do you know what’s happening here? Have you kind of lost your mind? Nobody wants to use this thing that you’ve built and you’re not paying attention.” And she had actually just been with our youngest son who at the time, he’s now 18 at the time he was like five or six or something like that.
[00:07:05] Nate Quigley: And this kindergarten teacher had given him this little four or five, six photos that came out of the school year and he was looking at him and crying. She heard him crying, goes into his rooms, “Hey, what’s wrong, Decky?” And he was like, “Mama, I don’t want to grow up.” He was feeling that same nostalgia pain that got me to start the company, but then she realized this kid has five photos printed of him, period, that the sum total of documentation of his life of these five pictures is his kindergarten teacher gave him. So she came downstairs with that, with a little bit of a head of steam fired up thinking, “I got to run the intervention on this out of control sounder.” And she said, “Hey, this isn’t working. I don’t want to use it. My sisters don’t want to use it. My friends don’t want to use it.
[00:07:53] Nate Quigley: Nobody wants to use it, but if you could just print my Instagram, that would be a lot of what you’re getting at. I would actually have it in my hands.” And so at that moment, I mean, some startup founders get to this point, maybe the smart ones don’t have to go through this sort of process that I did, but I was finally humble enough to really listen to who should have been my core customer, my wife. I said, “Print your Instagram. That actually is a really good idea.
[00:08:22] Nate Quigley: I think we could maybe do that.” So anyway, next day we went into the office, we kind of shoved all the old code to the side that we’ve been barnackling up for two and a half years and just sort of started fresh in a little hackweek kind of mentality. And the Instagram API was wide open. I had a buddy who had a print shop, one thing led to another and a couple weeks later we had a big stack of books, handed them to Vanessa and she’s like, “Yeah, that’s it.” And then her friends were like, “Hey, how do I get mine?” And that was how Chatbooks was born.
[00:08:50] Adam Fishman: Oh, that’s cool. And I imagine sort of starts to spread a little virally or word of mouth because you can keep them in a bag and you’re like, “Hey, let me show you this thing.” And then your friend’s like, “How did you make that?” “Well, Chatbooks.” Very cool. Oh, love the growth strategy. Well, congrats. And like they say, behind every successful founder is a partner who made them successful.
[00:09:12] Nate Quigley: And she wanted to give the idea and then leave again. And I’m like, me and five other dudes. And clearly what we were missing was in the family, the mom spends all the money in general, that’s pretty well known research of mom controls so much of the discretionary spending in the household and we didn’t have any insight into what was in her head and what she cared about. We were digitizing everything and putting everything in the cloud and building all these other apps and Vanessa just had the insight, no, I want to print it and have it in my house and off we went.
[00:09:46] Adam Fishman: Yeah. Sounds like you were busy solving the kind of technical problem and not necessarily the human problem, which your wife was like, this is the problem to solve.
[00:09:56] Nate Quigley: Exactly. So anyway, unfortunately for her, she’s the accidental co-founder. We never let it go. We had a lot of fun together. Thank goodness.
[00:10:04] Adam Fishman: That’s good. That’s good. And then your kids, obviously this is 15 years ago, your oldest was probably around 15, 16, something like that. So your kids got to watch the two of you build this company together for much of their youth. What was that like? Did that come into the dinner table conversations or anything like that? Were you debating strategy with your wife at the breakfast table or how’d that work?
[00:10:31] Nate Quigley: It’s funny. In the family, we call it Chatbooks our little family farm. And maybe that’s just an excuse of we did not separate at all work and personal life. It just all went into the pot together. And the kids have at various times, all of them been on the payroll in some form or fashion, even if it’s like a quick internship. Even our 18-year-old was just with another buddy at our office last week setting up and taking down tables for an event at 10 o’clock at night. We were paying them hourly. Yeah, the kids have all been part of the story and we just decided early on, my dad had this saying of like, don’t worry about work-life balance. You’ll never get there. It’ll just drive you crazy. It’s work-life integration and that’s how it is. And I latched onto this idea that I had an uncle and an aunt who were dairy farmers and I doubt they were talking about work-life balance.
[00:11:23] Nate Quigley: They were just on the farm. Every time I went down to visit them, my cousin Lucas would be driving a tractor and he was like 14. So we just embraced the idea of we’re all just going to work in this together and this is our life. It’s not work-life and personal life, it’s just our life and we’re building this thing together.
[00:11:40] Adam Fishman: Cool. Very cool. So you had a lot of reps at this, obviously parenting and starting a company, but if you think across your universe of memories of kids and raising kids, what’s the earliest memory that you have of becoming a dad?
[00:11:59] Nate Quigley: This is pretty easy to remember because our oldest son, our 30-year-old was born on my birthday.
[00:12:05] Adam Fishman: Oh, okay.
[00:12:06] Nate Quigley: I turned 23 at midnight and he was born like an hour later. So that’s my earliest memory was kind of the first diaper situation at like five o’clock in the morning and I’m a 23-year-old kid. My wife was 22 and we have a baby now.
[00:12:20] Adam Fishman: Wow. But I guess for the rest of your life, your birthday takes second fiddle to his, right forever.
[00:12:26] Nate Quigley: Yeah. It’s gotten a lot more fun now that he’s also kind of a grown man and we’re just like, we’re just having a birthday together. I think it’s actually good that we are on May 9th because now everybody remembers that both of us have a birthday.
[00:12:38] Adam Fishman: Awesome. Awesome. Well, happy almost birthday. This episode, I think it’s going to come out a couple weeks after your birthday. So I’m sure you’re going to do something really fun for it. Okay. So because you’ve had so many reps and you parented so many kids, I’m wondering, I imagine that how you parent kid number seven, your 18-year-old now, is much different than you parented kid number one or two. And so I’m wondering if you’ve found that you’ve learned something or you’ve shifted your approach to parenting as you’ve gotten more reps.
[00:13:11] Nate Quigley: Yeah. I mean, as you say that, I’m just thinking it is different for sure. And I think this is the classic, the older kids look at mom and dad and they’re like, “What are you doing? You never want to let us get away with that.” And it’s true. I’m sure that’s very true. You just prepare the facts of Calvin’s 16-year-old life and Declan’s 16-year-old life, super different because Vanessa and I are older and tireder and more worn down. But maybe the thing that comes to mind the most is, and this is a little cliche, but yeah, we have seven Quigley kids. They’re all so different. They’re just their own individual human beings that just arrived on the scene and Vanessa and I get to be the stewards of the whole thing with a lot of responsibility, but they’re not like mini Nate and mini Vanessa.
[00:14:00] Nate Quigley: It’s really been wild to see how different they all are. And so of course we’re doing it differently for each kid because man, they are all different.
[00:14:10] Adam Fishman: Did your older kids try to parent the younger kids a little bit as they were coming into the world?
[00:14:17] Nate Quigley: We would’ve loved to share the load a little bit. What I do really love, and this is a great blessing of our life, is that our kids do love each other. There’s nothing more amazing or rewarding to watch than watching our kids together and they’re there for each other when hard things come. And we’ve had some hard things in our family and watching the kids rally around each other has been amazing.
[00:14:37] Adam Fishman: Oh, that’s great. The other thing I’m wondering about the evolution of you as a parent is have you found that as you’ve gotten more reps at parenting or you’ve learned what works and what doesn’t work, or you’ve kind of evolved, become more tired, as you said, has that shifted how you manage people too? I mean, you’ve had the company for tracks many years of the growth of your kids.
[00:15:01] Nate Quigley: No, it’s true. I mean, the 15 years is not wrong, but we printed, again, we had that three-year wilderness period that I hold responsibility for. We’ve been printing books and actually growing the team for 12 years or so. Yeah, I think so. I mean, if there’s one big lesson of my life that’s been beaten into me, I’m still trying to resist half the time and then every now and then remembering, “Oh no, you have learned this one, let go of that,” is I’m just not in control of a whole lot of things. Specifically what choices other human beings make, I don’t have a remote controller, I’m guiding people where I want them to go. That’s really been the big difficult and painful discovery. I mean, it shouldn’t be painful, it shouldn’t be difficult, it’s just be celebrated, but it is tricky when you’re raising little kids and you’re like 1000% responsible for how they make it through the day, like their basic safety, their basic nourishment, their basic teaching about how the world works and what’s dangerous, what’s not, you feel that so heavily, so intensely as a parent, but then somehow, slowly, they become fully autonomous human beings that you’re just not going to nudge them here, nudge them there.
[00:16:18] Nate Quigley: Maybe you’re going to try to inspire them a little bit or influence them some by how you behave or what you do, but just the whole letting go thing is I think really, really hard to do, at least it’s been really hard for me as a type A dad to figure out, but you kind of just get forced to figure that out. And so I think that’s definitely got to play into how I think about work too. These are my team members. These are not things I’m steering, things I’m kind of leading and inspiring and setting up, but again, we get to drive our own cars. This is great. That’s how it should be, but that was a hard lesson for me.
[00:16:58] Adam Fishman: Yeah. I think related to that, and I’ve heard people say this, and this is something you shared with me too, is there’s a single right way to be a parent or a founder. A lot of different parents, you can have people who objectively you would look at them and be like, “Oh, that’s not a great parent.” And yet their kids turn out fine. Or the other way around, great parent, kids turn out maybe less fine. Same with founders. You’ve got all kinds of stories of what makes a fantastic founder and everyone’s got their canonical truth. But I think one of the things that you believe is that you have to play to your strengths as an individual, as a leader, as a dad. And so I’m curious what your strengths are, what you consider your strengths as a dad.
[00:17:41] Nate Quigley: Oh, man. Yeah, I can list a bunch of weaknesses really easily. It’s funny, that thought, I do remember talking to Vanessa early on because she was a vocal performance major, an opera singer.
[00:17:53] Adam Fishman: Cool.
[00:17:53] Nate Quigley: Actually on stage performing and stuff and raising her seven kids. And so all of a sudden she’s kind of in the business. She’s like, “I don’t know what I’m doing. I don’t know how to be a founder. I don’t know how to be a marketing person. I don’t know any of this stuff.” And I would say to her, “Hey, V, there’s no one way to be a founder. Just be you. You’re a storyteller. Be that kind of founder. Go tell our story everywhere you can.” And she did an amazing job of that. So yeah, I think the same thing does true apply to this. There’s no one right way to be a parent and I do believe in playing to your strengths. I guess if there’s any one thing that I would think I’m sort of strong at, I do feel pretty deeply. I really love my kids and that can show up in bad ways too. That can also be toxic because you’re overhelping and guilty of having done plenty of overhelping over the years and I can be a little emotional because I feel it so much that … But I think that that is probably if there’s anything I’m just incredibly dedicated to my kids and I won’t quit.
[00:18:54] Nate Quigley: And I think they know that. I think they know that dad’s going to be there. When push comes to shove, I’m in there with them.
[00:19:01] Adam Fishman: You mentioned, oh, I could name all the weaknesses that I have. We tend to think about that first. Where would you say as a dad you’ve sort of stumbled and have had to learn or evolve?
[00:19:14] Nate Quigley: I think it is this thing where I’m 53. I am on lap seven of this be your dad deck and I have these things we’ve done before and they seem to work. So we’re going to do those things and Declan’s just not having it. I really did, I think with my youngest son in particular, who just has a different personality. He’s incredibly strong-willed. And if I’m saying, “Let’s go left,” he’s like, “Well, we’re definitely not going left.” And when I say, “Well, hey, Deck, this is just how we do it in our family.” He’s like, “Well, not with me, you’re not going to do it that way.” Maybe just that need to keep being humble and keep remembering, okay, well yeah, maybe that was helpful for our first couple of kids. That was a totally different time, almost like a different planet. I think back to what was life like in the early 2000s, you know what I mean?
[00:20:06] Nate Quigley: It’s just we’re in a different world. So if there’s one thing I’ve figured out, it says I’ve got to stop thinking I know how this is going to work and just sort of accept what’s in front of us and try to make the best decision and then just try to keep supporting and loving my kids even when my youngest is pushing every single button on the console, I’m still his dad.
[00:20:27] Adam Fishman: Yeah. That gets to the point that you made earlier, which is everybody’s driving their own car. As much as you want to have your hand on all the wheels at once, you can’t. And even if you could, they’re going to take it from you and they’re going to drive it the way they want to drive it. So you just got to support them and care for them.
[00:20:47] Nate Quigley: And they should. Yeah. So this is kind of a weird thing. This is very grandpa old dad thing. I’m into birding. I’ve got a life list. It’s like Pokemon for adults finding different species of birds. So I’m really into that. When I’m doing well with my kids, it’s when I’m thinking about them like they’re a rare bird and I’m taking field notes and are like observing and like, “Oh, isn’t that interesting? That’s how they’re doing that, huh? Oh, cool.” When I’m looking at birds out in the marsh where it’s some binoculars, I’m like, “Oh, that’s really rad how they walk and there’s like tail bobs.” And when I think when I’m doing my best as a dad, I’m just looking at my kids that way instead of saying, “Why are they not soaring in that direction to where I think they should go?” I’m kind of doing the natural history of Declan Quigley instead of, “Declan, wait a minute, you got to be kidding me.
[00:21:36] Nate Quigley: Why that?
[00:21:37] Adam Fishman: “Yeah. Approaching it maybe more from a point of observation and curiosity than like, why can’t you be doing it this way?
[00:21:43] Nate Quigley: When I’m doing well, I’m being curious.
[00:21:46] Adam Fishman: Awesome. I love that quote. That’s a good one. We’re going to turn that one into a clip I’m sure of it. You probably talk to other founders, younger founders, people who are up and coming and they’re thinking about starting a family as sort of many do or you’re talking to a younger dad who’s thinking maybe I should go start a company. What advice do you offer those folks? What do you tell them about the Venn diagram of those two things?
[00:22:12] Nate Quigley: Yeah, this is funny. I actually, when some younger person from my alma mater or whatever reaches out to me and I always try to respond when we have some kind of connection like that saying, “Hey, I want to start a company. This is my idea.” I actually usually spend like 10 or 15 minutes trying to talk them out of it mostly because I think if one old random dude can talk you out of it, you really shouldn’t do it because it is going to be such a bumpy long road that I just do that little quick acid test like, “Can I convince this person to just get a normal job?” And if so, I probably help them in some ways. But then if we get through all that, then I kind of do say as many of the sort of don’t do what I did, things I can pull out of my hat, because I do think that you should do a lot of idea validation.
[00:22:59] Nate Quigley: You should do a lot of how can you de-risk this before you’re all in? And all the lean startup stuff is right in my humble opinion and it’s easy for people to miss it just like I missed it. You get hot to trot on your idea and away you go. So I do a little bit of that. And then my boiled down startup advice is don’t quit, don’t run out of money. You kind of must be present to win. You have to be on the field. And the only thing that takes off field is if you say, “Forget it, I’m done,” and you walk off or you run out of money and you’re just forcibly removed from the field. Yeah, I would say those two things apply to dad life as well. You do need to be able to provide for your family that said don’t run a money part.
[00:23:39] Nate Quigley: And I’ve been dangerously close to the edge on that a few times in my startup career, but the don’t quit thing I think is the most valid point. Stuff is going to happen that’s going to be tough and yeah, your kids are going to push your buttons a bunch and they’re going to do stuff that you just kind of scratch your head at and it makes you sad. Watching your kids get hurt and specifically hurt themselves is really painful, really hard to watch. But the don’t quit thing I think is that’s what I would love to have on my tombstone. This guy didn’t quit.
[00:24:12] Adam Fishman: You mentioned that it’s hard. You got to let your kids stumble a little bit and you want to be there as the backstop for them so that they know. You mentioned that you want your kids to know you love them always. That’s like job number one. And so then they know that they’ve got this backstop that they’re like, “I’m going to go out and do what I do in the world and probably make some mistakes, but dad’s always going to be there. He’s got my back.”
[00:24:34] Nate Quigley: I hope my kids always know that I want them to feel like we’re going to leave the car analogy for a second, but there’s a while where we’re both in the boat together, but I’m kind of driving the boat and then you’re driving the boat but I’m still kind of in the boat. And then now you’re just in your own boat and you’re just going on adventures and I want you to know that I am this pier you can come back to. I’m a harbor that when things get gnarly, you can come back here and there’s always going to be this harbor and this pier. I hope you always know you can come back here when you need to.
[00:25:04] Adam Fishman: Yeah. Awesome. I want to talk about some frameworks and household rituals that you have. You shared a bunch of fun ones with me. So the first one is tell me about family night. What is and what was family night?
[00:25:16] Nate Quigley: So family night for the longest time growing up we’re members of the Church of Jesus Christ of Latter-day Saints. And family home evening was like a thing for everyone who was a member of our church. And you just kind of blocked off Monday night as untouchable. Monday night was the untouchable family night and then eventually moved to Sunday night because it was just too hard to get it to happen during the week. But it was awesome. We had this awesome little ritual for our family where the kids looked forward to it and one of the kids was going to conduct our little 45 minutes together and they would organize who was going to be in charge of the treat, who was in charge of the game, who was going to do this, who’s going to do that. And there was like this whole routine went through with a song at the beginning that everybody knew and a song at the end that we would sing together.
[00:26:01] Nate Quigley: Both of the songs had like hand motions and there’s some unbelievable video from that era. And this is kind of like when the peak of this was when all seven kids were there and the was like two or three and starting to participate. I think that’s when I was all of a sudden like, “I got to quit my job and start a family memory company.” Yeah, it was great. We’d do the song, someone would say a prayer. There was Talent Corner so some kid would get up and do something on this little stand in front of our fireplace. We had the Quigley Creed. The Quigley Creed was a very important part of the family maybe in ritual where the kids would do Quigleys are respectful, responsible, considerate, and kind. They would go through that. We would line them up from oldest to youngest and this little descending line of Quigley kids.
[00:26:49] Nate Quigley: And the end was we would kneel and hold hands in a little circle and say a family prayer. And it was a really amazing long period of our life growing up as a family. That’s what we did once a week. That holding hands, kneeling thing, I was like, in my mind, I’m like, “We’re going to have this little wall that’s going to protect the kids from all the scary, bad things that are going to come try to get them in the world.” And I distinctly remember thinking if we can just keep the kids holding hands, keeping the scary things at bay, we’re going to be okay as a family. And of course that doesn’t work. I mean, the scary stuff gets in. Unfortunately, we could not prevent all of the skin knees of life from happening to our kids as they work through this high wire act of going from a kid to an adult.
[00:27:38] Nate Quigley: That’s a really tricky sort of ridge for them to cross. But I have to hope that somehow programmed deep into their brains, like what were these kind of moments, these rituals where we’re like, “No, I’m part of something. I’m part of the Quigley family. I’m not by myself. No matter how I feel right in this moment, I was hoping that that would be a little bit of a foundation for them, get them through some hard times.” And to get Vanessa and I through some hard times as we watched the buffetings start to happen.
[00:28:08] Adam Fishman: Yeah. Well, and that relates back to what you said about, I mean, we talked about the car analogy, but then you talked about the idea of being the pier, it’s a place they can always come back to. And it’s almost like one of the outcomes of that, and you mentioned your kids all have really good relationships with each other. One of the outcomes of that, the Quigley Creed and Family Night is you’ve created this group that they know that they can come back to in a storm or whenever and a bunch of people have their backs, which is pretty great. Again, you can’t control what happens out in the world, but you can create the safe place that people can return to the pier and the storm, I guess. So I think that’s great. So there’s another ritual you have, which is called Family Fandangos.
[00:28:55] Adam Fishman: So tell me about what Family Fandangos are. I came across this name in our prep and I was like, oh, that’s going to be fun. I got to ask him about this.
[00:29:03] Nate Quigley: One of the elements of family and I, you do announcements and there’s like a little announcement song, you have to have decent stuff on the calendar or the announcements is boring. So we would try to have on weekend a month where you camp out or go to Cooperstown. We used to live in the Northeast and it didn’t ever have to be very dramatic because the kids were really young, but having a family fandango on the calendar that gets mentioned at announcements, I think it was just fun for us. And we’re just trying to like some kind of a memory and often it did involve camping when the kids were younger. We did have one glorious mega fandango where we did a house swap with a family in the south of France for five or six weeks. I did know in the time as much as it’s made me sad and I’m starting the company at the same time as we started the company, we did this little break between companies and I’m like, “This is like the apotheosis.
[00:29:57] Nate Quigley: It’s never going to get better than this.” And that was the Meanful realization to be watching my little three-year-old and five-year-old girl with a bag out under their arm going in this little alley, realizing it’s never going to get better than this. This is it. This is peak Quigley right now. But yeah, that was the mega fandango that I’m really glad we took the time and the money to go do that because it was a magical moment for us.
[00:30:21] Adam Fishman: Having been to the south of France once, I can say that sounds like a magical time. That would’ve been really fun. Is that the most memorable family fandango for you?
[00:30:31] Nate Quigley: I mean, you probably can’t even call that a fandango because it was just so over the top awesome. We had another one that was just drive to Niagara Falls and mini golf along the way and just a normal camp out in some normal little campground. But there were some good moments like that.
[00:30:49] Adam Fishman: Related to the fandango, but maybe slightly split up a little bit, what’s the 15-year-old adventure? This is another thing you have.
[00:30:57] Nate Quigley: Yeah, we did do this all seven times and it’s just as simple as the boys and I went when our son Calvin turned 15, we went to Costa Rica for a four-day, three-night thing with actually one of my buddies. So it was like Calvin, me and one of my pals. And it was good because Calvin and I were having that look sort of Calvin was leaving. I’m a kid and dad’s cool. I’m a teenager and I’m not really sure I want to talk to my dad. And my friend that came with us was the classic ultra extrovert jibber jabber. So he was just talking the entire time and Calvin and I didn’t have to fully talk to each other. That would’ve been actually probably hard for us. But we had this extra third wheel who just sort of made the whole machine work a little better for us and it was a great trip for us.
[00:31:44] Nate Quigley: And then Vanessa’s done the same thing with the other girls, but they just pick what they want to do and we cook up an adventure and go do it together.
[00:31:51] Adam Fishman: Cool. Now you’ve given me something to think about because my kids are not too far away from 15 and I’m kind of like, “Oh, now I need a 15-year-old adventure. That’s got to be fun.”
[00:32:01] Nate Quigley: For us, it was the perfect time. Another one, I went mountain biking with our second son and he was a competitive mountain biker and I was just barely trying to keep up. And he was absolutely getting me through all insane rides in Moab. He was the guy feeding me like the gummy bear like, “Dad, you can make it.” And it was all blasted at the end of the second ride that I couldn’t drive. He didn’t have his driver’s license. I’m like, “Henry, you’re going to have to drive.” All the way back, I was trying to stretch my legs out that were totally crampy. And I’m like, “Get us down the road. Keep it in the middle of the road. You’re going to be
[00:32:39] Adam Fishman: Fine.” Take the wheel. I’m useless.
[00:32:42] Nate Quigley: 15-year-old took the wheel.
[00:32:43] Adam Fishman: Yeah. Well, you made it. I mean, you’re talking to me, must have turned out. The legs are still recovering, but your body is here. Okay. I wanted to change gears. So those are amazing. The 15-year-old adventure, the Family Fandango, even just family night. Love all of those. I think there’s a lot in there that people who are listening to this show can take away as little nuggets that they might want to introduce in their own families. I wanted to come back to something that you mentioned earlier. One of the things that you told me, and you said it a couple times on this show already, is that the hardest thing about being a parent is to let your kids grow up, go out and live their lives without you and just have that happen. And I want to hear a little bit more from you about why that’s so tough.
[00:33:33] Adam Fishman: As a dad who’s kind of seen this happen now seven-ish times and you mentioned you’re about to be full on empty nester. So you’ve seen this six times, almost seven, and I’m sure it doesn’t get any easier. Probably gets harder with each one. Why is it so tough?
[00:33:49] Nate Quigley: Man, it is almost like this cruel trick of nature that the infant and those of you listening, you’ve held the baby in the hospital right after the baby’s born, you’re just immediately imprinted like, “I love you forever. I’ll do anything for you no matter what for the rest of our lives.” In an instant. I don’t know how that happens, but it’s just so powerful. You can describe it, but when you actually experience it, you’re like,
[00:34:15] Adam Fishman: “Okay,
[00:34:15] Nate Quigley: Wow, something crazy just happened to us through this process of the birth and then you’re holding the baby and you can’t believe how incredible your wife is and the world’s just different.” And then their heads are bigger than they’re supposed to be and their eyes are bigger. They’re like Disney characters blanking at you and they just for the next year, two years, three years, they’re saying these little cute things and it’s just like, okay, this child owns me forever. And then you do have to be like, “And now I’m going to just let them go and hope for the best.” And I think I talked about birding before. My wife and I have talked about this and even to the kids sometimes, this idea of the Merganser, no one’s going to know what a Merganser is. It’s a really cool duck.
[00:34:59] Adam Fishman: I am familiar with that duck, believe it or not, but I bet most people listening to this show are not. So it’s a duck.
[00:35:05] Nate Quigley: We won’t get into why this duck is so cool, except to say this, the mother Mergansers are the very beginning and dad, the chinks will be on mom’s back. She’s swimming down the river with three or four chicks on her back and then the chicks start to fall off and they’re trying to keep up and then eventually they just are swimming behind mom and then they start to swim off a little bit on their own. And then lo and behold, mom and dad are just kind of by themselves again and they actually do breed for life, which is really cool. But how does that process happen? It seems to work for Mergansers. Eventually they just realize, okay, I’m big enough and I can get my own food and I’m out of here. I have not figured out yet how to be like that dad Merganser who’s like, “Oh good, they’re not on my back anymore.
[00:35:48] Nate Quigley: Great. They’re off doing their thing.” I think it’s because you’re so programmed early to protect and take care of this child. Our process is a lot longer than the Merganser process. So you’re really helping these young children avoid peril for so long and then just slowly you got to figure out and now’s when you let them go. I don’t know. It’s a hard trick.
[00:36:12] Adam Fishman: Yeah. Wow. Well, I will forever now think of this as the Merganser story. You want happy,
[00:36:19] Nate Quigley: Healthy Mergansers on the pond, but how you get from like they’re on my back to they’re doing their own thing is a stunt.
[00:36:26] Adam Fishman: Yeah, it is funny. And just about every species in the natural world has something like this, but ours kind of goes the slowest it feels like. And the longest, it’s probably why it’s the most painful and difficult.
[00:36:38] Nate Quigley: And I guess we don’t have claws or wings. We have this ability to tell each other stories, this ability to really bond with one another and work together. And so maybe ours is just like the hardest version of this where what makes us humans and what makes us capable is actually part of the same secret sauce that bonds us to our children so tightly.
[00:37:00] Adam Fishman: Yeah. So a couple more questions for you. The first one I want to talk about, you will have an interesting perspective on this because you’ve seen 30 years of kids in technology. Your oldest is 30 and so cell phones were not a thing when he was born. Social media was not a thing. The internet was like fledgling if at all. It was a dial-up modem probably. And so how have you handled technology in the household as your kids have grown up throughout the years and it’s become much more front and center for your younger kids lives?
[00:37:39] Nate Quigley: Man, this is obviously not an exciting insight, but it is so hard to be a teenage boy or girl in 2026 because you’ve just got all the super geniuses of Meta, Google and TikTok just coming at you wanting all your attention. You have all of the insecurities and foibles of a 13, 14, 15-year-old person. It’s really not a fair fight. I don’t think all for the 13, 14, 15-year-old kid. I mean, I really do believe that Jonathan Haidt’s kind of got some stuff right in his book. If you’re a kid who’s got a propensity toward anxiety or maybe you’re OCD at risk, this is going to be a lot harder to get through than it was in 1850 and make sure you’ve got the cows in at night or something like that. We’ve done a thousand different things and they’ve all failed in different ways.
[00:38:36] Nate Quigley: I definitely think that parents should be involved and we’ve tried to be involved with how your kids are using these mobile and algorithmic feeds early. We’ve experimented with a lot of different technology. We’re actually small investors in a company called Bark, which I think has-
[00:38:54] Adam Fishman: I know that company. Yeah.
[00:38:56] Nate Quigley: An amazing company, great products to try to control some of the wifi access in the house, try to provide some guardrails, but their approach I think is really excellent. We have such a small investment. This is not me pitching Bark, but what I love about it is it just prompts conversations. So your kid still has, they’re still texting their friends, but if something comes in that triggers one of the sort of bark alarms, it just sends you a note saying, “Hey, you should talk to your kid about this.” Versus trying to block everything, you can’t block everything. You can hold hands in your little circle kneeling down family prayer all you want and you’re not going to keep everything out. And so can you just give parents enough information that we can hopefully have these curious type question conversations where we can let the kids know like, “Hey, I’m here to help you with this thing that sounds a lot like self-harm.
[00:39:50] Nate Quigley: Can you tell me more about that?” So I like that. I also think sometimes it’s good to just brick the stupid phones. There’s another great company called Analog that is sort of creating these time and location based using Beacon technology just to sort of turn your phone into a dumb phone for the whole family. We’ve also used this company called Brick where you tap the thing and brick your phone. So Analog’s kind of like the brick that you don’t have to tap, just like a certain time all the phones brick. I think we do have to kind of fight back. It is sort of like small rebel force versus the galactic empire. I mean, it’s not a fair fight and it’s going to be really hard, but those are some things we’ve tried. I would say we also had a hard and fast rule back to like, we’ve done it this way forever.
[00:40:34] Nate Quigley: And then the seventh kid’s like, “Well, I’m not doing that.” Plug your phone in the hallway at night. That’s just a generally speaking really good practice for all of us. And so we can talk about why that’s so smart until we’re blue in the face. And our youngest kid’s like, “I’m not doing it.” And so then you’re like, “Well, I’m going to take your phone away.” He’s like, “Okay, well, I’ll just get another phone.” And so depending on the strength of will of your various children, you’ll run into these boundaries pretty fast and pretty hard. But I did notice this is one small mini smile as I walked down the hallway, I noticed my son’s phone plugged out in the hallway. I gave up trying to enforce that boundary a long time ago or he must have realized, “Man, I got to get some sleep.
[00:41:19] Nate Quigley: This isn’t helping me.” And maybe he remembered that mom and I had really felt strongly about that and just did it on his own.
[00:41:26] Adam Fishman: Or maybe he’s buttering you up for something.
[00:41:29] Nate Quigley: Or maybe he couldn’t find a charger and he happened to find one out here. I have no idea, but I told myself a little story there.
[00:41:35] Adam Fishman: Yeah, no, I think you should pat yourself on the back for that one. I think you’ve earned it. So maybe you’ve won this one.
[00:41:41] Nate Quigley: We’ll see.
[00:41:41] Adam Fishman: Well, I love those. I’m obviously familiar with Bark. I’ve heard of Brick. I’ve never used it myself.
[00:41:47] Nate Quigley: Go Analog. Google Go Analog. I really love that one as a decide together as a family how we want it to work and then it just happens.
[00:41:56] Adam Fishman: I love that. Love that. I need to check out all those things now. So the other thing that’s new, even more so new than social media is AI. And I imagine also this is really interesting for you and your kids and your grownup kids. And I realized that probably over the last couple years is when AI has really gone bananas, but how has that worked its way into your family life? How are you engaging with your kids on that around AI?
[00:42:24] Nate Quigley: I think the first thing that comes to mind is just sort of talking them through what are people saying about AI, helping us all just sort of think through what is this, what’s good about it? What are we worried about? What do we want to try to protect ourselves from? And also in some ways, how do we just get ourselves comfortable with it’s here That’s just a fact because there’s some kind of temptation to say, and these are all valid concerns depending on where you get your news and your opinions and what your peers are saying, none of this is not right about, I’m worried about energy usage. Okay, well I get that. Me too. Let’s talk about how it’s all evolving. I’m worried about the fact that it’s built on the work of people who didn’t get compensated for all the training data that just got sucked into it that now can do this incredible design on the backs of a bunch of hardworking designers that weren’t asked if they should … I think validating all those very real concerns that I think specifically a younger generation of kids might in a college dorm room might talk about and be tempted to sort of just get on a barricade and die gloriously not accepting AI.
[00:43:36] Nate Quigley: And so part of what I thought my job was was just sort of listen and hear in Ballet’s real concerns and also try to think about, and therefore, what are we going to do? Because I don’t think sitting this one out is really a good idea. This is like the wheel got invented and we should start using the wheel. As it turns out carrying bricks versus wheeling them down is we should wheel the bricks, not carry them anymore. So I think some of it is just like being a thought partner for our kids to confront this insanely world changing technology and also help them think about what does it mean for their future? What do they have to be good at in a world that’s just … And we’re all just figuring it out as we go here. But I think maybe the most important thing was going back to really old stories like Prometheus and Pandora and these are useful analogies here and it’s not going back in the box.
[00:44:30] Adam Fishman: And I think you mentioned that you and your boys are working on a bit of a passion project with AI. So tell me about that one, because I found this to be really interesting.
[00:44:40] Nate Quigley: Oh, that one’s been really fun. So we live in Utah. Utah’s the high desert, there’s no water. But like in every other state of the union, other than like Arizona and Nevada that are ahead of us, there’s Kentucky bluegrass everywhere and it’s great to have some Kentucky bluegrass in the backyard where you can play cornhole or have your grandkids run around, but it’s pretty pointless on the park strip between the road and the sidewalk. There’s like three or four feet of grass that gets overhead sprinklered and most of your watering sidewalk and road and then it evaporates and goes away. And we’ve got the Great Salt Lake at the terminal basin of the watersheds in Utah and it’s at historically low levels that creates all kinds of environmental challenges for us. And again, we like birds so it’s bad for the birds too. We’ve got our family history, great grandpa was a forest stranger, my grandpa was a forest ranger, my uncle’s forest ranger, my dad worked for forest service.
[00:45:36] Nate Quigley: So we’ve got this sort of like western conservation thread running through our family that it matters a lot to us. And so we just started thinking to ourselves, how do we get more people to want to rip out the bluegrass and the park strip and replace it with localscaping? There’s more waterwise plants and other features and better smart controllers and their irrigation systems. So we just water the road and sidewalk less. Anyway, we decided let’s cook up some kind of a way to get the word out on this, do before and after pictures of what everyone’s sidewalk would look like before with the bluegrass and after with the localscaping, thinking that maybe the challenge is, I don’t even know what that means, what’s zero scaping, that’s rock. I don’t want just rock, but you can make a really beautiful park strip that’s way more water friendly.
[00:46:26] Nate Quigley: And so anyway, we’ve got this little project, we’re making 10,000 things we’re going to stick indoors of before and after pictures. And my sons who are, it’s amazing how quickly they’re catching on. They didn’t train as software developers, but with Cursor and Claude Code, all of a sudden you’re just building these things that make your 10,000 before and after cards and look amazing. We haven’t yet gotten the 10,000 run printed, but it’s been really fun to watch to see what my boys have been able to build with AI to go after this problem that we all kind of care about. But just having like a project to work on together has been amazing a dad and son thing and also as just another way to push yourself to use AI in a new way every week is I think just good practice right now.
[00:47:13] Adam Fishman: That’s great. Sounds like a great project. And I’ll bet you know a printer who can help with this too.
[00:47:17] Nate Quigley: We can get them printed. Yeah.
[00:47:20] Adam Fishman: It helps. It’s the intersection of professional life and personal. All right, well that does it for the regular portion of the interview before lightning round. But last thing I’d love to ask people is how can folks follow along or be helpful to you?
[00:47:37] Nate Quigley: I know you might have dads in startups on this podcast, but if they could all just talk to their partners and say, “Go follow Chatbooks on Instagram,” the best way to follow along with what we’re doing.
[00:47:47] Adam Fishman: Well, I may go tell my own wife about this.
[00:47:50] Nate Quigley: It’s not that I don’t want dads to show up. We just know having surveyed our custody for 10 years, it’s not the dads.
[00:47:55] Adam Fishman: Yeah, I would say my activity level on Instagram is pretty thin.
[00:48:00] Nate Quigley: As it turns out, you’re probably not going to be a great Chatbooks customer.
[00:48:03] Adam Fishman: Probably not.
[00:48:04] Nate Quigley: 95% of our customers are women, and it’s always been that way.
[00:48:07] Adam Fishman: Yeah. Well, I get it. I see how people use Instagram, so I totally understand. Okay. So we’ll put that in the show notes. We’ll make sure everybody goes and checks it out. All right, let’s do a quick lightning round before we adjourn for the day. Here we go. What is the most indispensable parenting product that you’ve ever purchased?
[00:48:26] Nate Quigley: Oh man, indispensable parenting product. I mean, it might be Bark or Analog or Brick.
[00:48:34] Adam Fishman: Okay.
[00:48:34] Nate Quigley: It’s helping us fight back.
[00:48:36] Adam Fishman: Strong endorsement. What is the most useless parenting product you’ve ever purchased?
[00:48:41] Nate Quigley: It might be those same things. Bark and Analog and Brick, but it’s just such a hard fight. And maybe the most indispensable thing is just some of the books that we’ve read that have taught me a little more about family therapy and how to actually, what validation actually means and what active listening means. I know that this is not a lightning round, so I’ll just zip it, but those are probably … If someone would’ve taught me what the word validation meant 20 years ago, it would’ve helped
[00:49:14] Adam Fishman: Me. Well, we’ll revisit the parenting book topic here in a moment, so don’t worry. What’s the weirdest thing you ever found in your kids’ pockets or in the washing machine?
[00:49:24] Nate Quigley: Oh my goodness. I mean, some of the things that are coming to mind, I don’t want to play out there.
[00:49:30] Adam Fishman: We’ll just leave it at that.
[00:49:32] Nate Quigley: We’ll
[00:49:32] Adam Fishman: Leave it at that. True or false, there’s only one correct way to load a dishwasher.
[00:49:38] Nate Quigley: The dishwasher for sure is just loaded. Yeah, there’s one way.
[00:49:42] Adam Fishman: Okay. All righ I’ll finally
[00:49:43] Nate Quigley: Give you a lightning right answer. There’s a correct way to load it.
[00:49:46] Adam Fishman: There’s a correct way. Okay. The ideal day with your kids, and I know they’re all different, but the ideal day with your kids involves what on activity
[00:49:56] Nate Quigley: With my youngest son who again, he’s forced me to grow so much. It’s fishing. He’s an incredible fly fisherman. He has tied a zillion flies that I’ve caught a zillion fish with, and I
[00:50:09] Adam Fishman: Love
[00:50:09] Nate Quigley: Being in the river with him.
[00:50:10] Adam Fishman: I recently last summer went fly fishing with my son who’s 11. And I mean, man, that may have been one of the hardest things I’ve ever done. If you don’t know how to do it, it is tough. I learned, but man, I was not good at it.
[00:50:24] Nate Quigley: We’ve had some great times on the river.
[00:50:27] Adam Fishman: That’s awesome. That’s awesome. It is a much more entertaining version of fishing, I find, because you’re constantly doing stuff. You’re
[00:50:34] Nate Quigley: Cloning knots and figuring stuff out.
[00:50:36] Adam Fishman: Yeah. If your kids had to describe you in one word, what would it be?
[00:50:41] Nate Quigley: Emotional.
[00:50:42] Adam Fishman: Okay. All right. Now I promise we’d revisit this topic. How many parenting books do you have in your house?
[00:50:49] Nate Quigley: Oh man. I mean, we have a lot. I would say bordering on 20.
[00:50:54] Adam Fishman: How many have you read cover to cover?
[00:50:56] Nate Quigley: Cover to cover, probably just for me, like two. I would
[00:50:59] Adam Fishman: Think
[00:51:00] Nate Quigley: Vanessa’s probably read all of them and she’s given me the Cliff Notes version knowing I’m not going to actually read them. All
[00:51:06] Adam Fishman: Right. Well, that’s good. That’s a pretty good ratio. What is the most absurd thing that one of your kids has ever asked you to buy for them?
[00:51:14] Nate Quigley: Oh man. The boys wanted the boat when we lived in Florida. Well, that sounded kind of ridiculous and then we did get them a boat.
[00:51:24] Adam Fishman: You broke down. All right. Was there a nostalgic movie that you just couldn’t wait to force your kids to watch with you when they got old enough?
[00:51:33] Nate Quigley: I mean, it’s funny that we just talked about fly fishing, but it was A River Runs Through It.
[00:51:37] Adam Fishman: Oh, yes. Yeah,
[00:51:39] Nate Quigley: Absolutely. It’s an incredible family story and I could not wait to watch that movie with my boys.
[00:51:45] Adam Fishman: Okay. Awesome. That is a great film. Two more for you. How often do you tell your kids back in my day stories?
[00:51:52] Nate Quigley: They would say every day when I’m being especially unbearable about why they can’t do X, Y, Z out, make it even worse by piling on it, just how uphill everything I did ever was.
[00:52:04] Adam Fishman: Yeah. Okay.
[00:52:06] Nate Quigley: A lot.
[00:52:06] Adam Fishman: A lot. Okay. And now last one, I’m not actually even sure how this would work logistically, but what is your take on minivans?
[00:52:15] Nate Quigley: I’m all in two thumbs way up on minivans.
[00:52:19] Adam Fishman: Okay.
[00:52:20] Nate Quigley: The two sliding doors.
[00:52:22] Adam Fishman: Oh yeah.
[00:52:22] Nate Quigley: You can unload a crowd. It’s like a Huey. It’s like you land and the platoon dumps out of the helicopter. The minivan is the most genius all American invention of all time. I love the minivan.
[00:52:33] Adam Fishman: Awesome. You did
[00:52:34] Nate Quigley: Unfortunately outgrow it eventually. But when we were five kids, minivan was life. Yeah.
[00:52:41] Adam Fishman: Do you know people who end up upgrading to a sprinter van because it holds even more. So that is a thing.
[00:52:47] Nate Quigley: We never had to go full maxivan. My wife was the oldest of 12 and
[00:52:54] Adam Fishman: They
[00:52:54] Nate Quigley: Were maxivan people.
[00:52:55] Adam Fishman: Wow. Yeah.
[00:52:58] Nate Quigley: We didn’t get there. We got to the front bench expedition.
[00:53:02] Adam Fishman: Oh yeah. Okay.
[00:53:04] Nate Quigley: That’s nine. Nessa, the smallest kid in the middle and then three, three.
[00:53:08] Adam Fishman: Wow.
[00:53:08] Nate Quigley: That was our peak.
[00:53:10] Adam Fishman: Wow. That’s awesome. All right. Well, on that note, thank you very much, Nate, for your time and for sharing all this great stuff and the lessons about being a dad of seven kids and building a company. All the best of your family. Congrats on almost becoming an empty nester. I wish you and the fam all the best for the rest of the year, so thank you. Thanks
[00:53:30] Nate Quigley: Very much, Adam. I really enjoyed the conversation. Thanks for having
[00:53:33] Adam Fishman: Me. Thank you for listening to today’s conversation with Nate Quigley. You can subscribe and watch the show on YouTube or wherever you get your podcasts. Visit www.startupdadpod.com to learn more and browse past episodes. Thanks for listening and see you next week.