Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Founder of Tilled)

[00:00:00] Caleb Avery: You have to be honest with yourself about what the trade offs are going to be and whether or not you can accept those. And so there’s a limited amount of time that you have in your day. And if you look at what your day looks like today, no kids, it’s going to look real different when you start the business and when you start having kids and you have to be honest with yourself about whether that’s something that you want to sign up for because if you don’t, then you’re setting yourself up for a pretty dangerous situation where you’re either going to be unhappy with the kids, unhappy with the business or unhappy with both.
[00:00:29] 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. Caleb Avery founded his first company when he was 19 years old and has been hooked on the founder journey ever since. Over seven years ago, he founded Tilled, then subsequently went on to have three kids with his wife, Kelsey, while continuing to grow the company. Today, he joined me to talk about parental leave regrets, why it’s hard to make friends as a parent, his third job as T-ball coach to a five year old, what his boundaries and non-negotiables are as a dad, and why spending time with his kids at bedtime is his top parenting priority. He also told me an incredibly hilarious story about the worst experience he’s ever had assembling a kid’s toy. You don’t want to miss it in the lightning round.
[00:01:24] Adam Fishman: If you like what you hear, please subscribe to Startup Dad on YouTube or Spotify so you never miss an episode. You’ll find it everywhere you get your podcasts. I hope you enjoy today’s conversation with Caleb Avery. Welcome, Caleb Avery, to Startup Dad, Caleb. It’s my absolute pleasure to have you on the show today. Thanks for joining me.
[00:01:43] Caleb Avery: Yeah, thanks so much for having me on. I’m excited.
[00:01:45] Adam Fishman: First question, you have a very cool neon background. What is going on over your head and behind you at the moment?
[00:01:52] Caleb Avery: This is the shameless plug that I set up for my business. So this is Tilled, PayFac-as-a-service. I set up this podcast studio probably, I’d guess three years ago at this point. And at the time I would come in, record podcasts and I’d go back out to my desk and then I’m spending seven, eight hours a day on Zoom. And so I’m out at my desk and my Zoom background sucks. And so probably two years ago, I finally just caved and brought all my monitors in here and set everything up where now I just spend my entire day in a soundproof closet and I love it, but there’s times where it’s like maybe a little natural light would be good.
[00:02:32] Adam Fishman: I love that. Well, cool. It’s a very cool neon sign. Especially
[00:02:37] Caleb Avery: For
[00:02:37] Adam Fishman: Those listening, highly recommend you check this out on YouTube because you ain’t ever seen a neon sign like this before.
[00:02:42] Caleb Avery: Etsy and like three or 400 bucks and YouTube could have a really cool neon sign. So honestly would like highly recommend it.
[00:02:48] Adam Fishman: Okay. I dig it. All right. Let’s get to the topic of the day, which is parenthood and fatherhood and building companies. So you’ve got three kids, two and a half to seven. You founded this company Tilled about seven years ago, a little more than seven years ago. Was your oldest kid born when you started Tilled?
[00:03:08] Caleb Avery: No. So she’s about to turn eight. And so she was probably just under one at the time when I really started the business. But for the first couple of years, it was really just myself trying to figure out some of the early components. And so it wasn’t really until COVID that the business really started to take off, which was conveniently right around the time when my second was born.
[00:03:35] Adam Fishman: Okay. What was the conversation like between you and your wife, your wife’s name’s Kelsey, about starting a family and simultaneously a company. Did she think you were Looney Tunes or was a lot of conversation, a little conversation, you just yo-lowed it? How’d that go?
[00:03:53] Caleb Avery: Yeah. In the very beginning, there wasn’t much of a conversation. She was fully supportive like, “Let’s go do this.” I’ve been an entrepreneur ever since she’s known me. So I started my first company when I was 19, which was like literally just after I had met her. And so she’s watched me build the first business and is my biggest supporter building that company Tilled and just in life. The big conversation came when COVID hit. So early days, she’s like, “Yeah, go build your thing.” Life’s good. I had some mailbox money that was coming in from the first business. All was well. And then COVID hit and small businesses were shut down. So my first company was an ISO going door to door selling to small business owners where we’re making money every time they process payments.
[00:04:38] Adam Fishman: Yeah, that’s not happening.
[00:04:40] Caleb Avery: For decades was a very stable business. And then all of a sudden COVID hits and small businesses are closed, volumes are down, revenue’s down. And then she’s looking at me like, “Hey, what are we doing here? You’re starting another company. We’ve just had a second kid. What are we doing here?” And so that was definitely more of a conversation at that point in time. But ultimately her question was like, “Do you believe in what you’re building?” And the answer was yes. And so it wasn’t the longest conversation, but there was definitely a conversation to be had there.
[00:05:12] Adam Fishman: Raising young kids and being an active parent is tough. It’s pretty exhausting. Building a company, also really tough and exhausting. Were you worried that you’d have enough energy to do both of these things or what was the calculus in your head around this?
[00:05:30] Caleb Avery: For me, the calculus was really recognizing that something was going to have to give in this. And so as all parents know, you’re just tired all the time. Kids, all they do is suck the energy out of you. And then startups, basically the same thing, just sucks the energy and the life out of you. And so I think for me, the trade off going in was knowing that I was going to have less time for myself. You have to set aside a certain amount of time for the business. You have to set aside a certain amount of time for the family. And so the sacrifice, at least in my mind, is, okay, well, I am going to have less time for me, Caleb. Is that worth the sacrifice of building the business and having the family? And in my mind, that was a no-brainer. I’ll do that deal all day long.
[00:06:14] Adam Fishman: And less time for Caleb meant what? You weren’t going out and playing 18 holes on the weekend or running a marathon or something?
[00:06:23] Caleb Avery: For me, golf and skiing are my two passions. And so skiing is funny because I have this app called Ski Tracks. And when I go out and ski, turn it on, records vertical feed, speed, all that good stuff, but it also has season over season stats. And so I’ve lived in Colorado for 10 years. My oldest is about to turn eight. If you look back, hey, nine, 10 years ago, I skied a lot. Stable business, working for myself. I skied a ton. Golfed a ton, life was great. The skiing has just completely fallen off a cliff since having kids where it’s like going from 20, 25 days a year on the mountain to if I get three or four days on the mountain, I’ve done great. And you have to realize one or two of those days is skiing with a five or a seven year old.
[00:07:09] Caleb Avery: So we’re not going to the back bowls of Vail, we’re ripping down the magic carpet. Golf for me, that is my favorite thing on the planet. I am so happy when I’m on a golf course. And basically where I’ve gotten to is I don’t really golf in Colorado. So when I’m at home, very rarely am I golfing. So the vast majority of my golf is traveling for work. And so taking out clients, taking out customers, playing in tournaments at trade shows, and that’s just kind of what I know I’m signing up for at the moment.
[00:07:40] Adam Fishman: Cool. As someone who just recently went skiing this weekend with my kids, I can fully appreciate. We’re past the magic carpet, but I can fully appreciate that time, that season of life. Okay. I wanted to ask you about your first kid and taking paternity leave. I’m putting this in air quotes
[00:08:00] Caleb Avery: For those who kids. Yeah. Air quotes is definitely good for this.
[00:08:03] Adam Fishman: Because you told me this, and you and I have actually a very similar set of regrets from our first kid, which is just the abysmal decisions around paternity leave and taking time off. And so I’m really curious, tell me about those regrets from your first kid.
[00:08:22] Caleb Avery: Yeah. So my daughter, almost eight, I just felt like for me, I didn’t have the time to take off. So I was working on a different startup that I was an investor in. They were raising capital at the time. And literally I am at the hospital. She was probably two or three hours old and I am writing documents to send out to these investors for this financing round. And so it just felt like we were in this crunch time in the business. I still remember at the hospital, I’d sent out the docs to one of these investors. I get a call and the guy’s like, “Hey, there’s a typo in one of these docs.” And I’m like, “Dude, I’m looking at a four hour old baby at the hospital. Is this a problem?” And I just remember the guy apologizing profusely. He was so embarrassed. He’s like, “My bad.”
[00:09:09] Caleb Avery: “I’ll sign the documents. I’ll wire the money. Don’t worry about it.” So probably low key a good fundraising hack is make people feel bad because you’re at the hospital. But in all seriousness, a lot of regrets for me in that time, because I wasn’t present, I wasn’t spending that time with her. And I basically went immediately back to work because I felt like that’s what I needed to do at the time.
[00:09:33] Adam Fishman: Yeah. Yeah. I don’t want to get too much into family dynamics. Was that a tough thing for you and your wife for you to kind of immediately jump back into the fray?
[00:09:43] Caleb Avery: I think she knows me just as a human being and as a person. And so that was probably her expectation. And so I don’t think that she was honestly disappointed all that much. And we had a lot of support with my parents, her mom, we had nanny. So there was a lot of support for her. And so that was like, I had told myself, “Oh, well, I’m setting her up and our daughter up for success, so I don’t need to be there,” which in hindsight is the furthest thing from the truth, but at the time that was the rationale.
[00:10:16] Adam Fishman: Yeah. So you barely took any time off with your first kid a day, you’re hammering out bank terms and funding documents at the hospital, which by the way, is not an uncommon story that we’ve had on this podcast. So I don’t know if I would say in good company, but you’re in common company, but with your second kid, you did something very differently. I want to ask you two things. One is, what’d you do differently with your next kid? And then how have both of those experiences really influenced your thoughts on the importance of parental leave and taking time off when you start a family? Yeah.
[00:10:54] Caleb Avery: So second time around, my now five year old was born in February of 2020, which is important as we get into the story. And so I started to have regrets leading up to him being born, just thinking back to the experience I had with my first. And so I told myself, “Hey, I’ve got to take a week off. I can’t just be next day going back into the office.” And I took the week and it was an incredible experience. I absolutely loved every minute of having that time with him. And I went back into the office for exactly one day. And that one day I show up and I think we have two or three employees at the time and you’re starting to hear these news stories of, “Oh, what’s coming over from China? COVID’s happening.” And one of the employees in the office just looks terrible.
[00:11:41] Caleb Avery: He just looks sick. We’re watching the news, reading these stories, I’m looking at him and I’ve got a one week old baby at home, which anything you read at the time was like, “This is deadly for babies.” And so I’m like, “All right, we’re calling it everybody go home. We’re getting out of the office. We’re going home.” And so we probably actually shut down before other companies were just because at the time I had a one week old baby. And that’s when I went from five days a week working in office to five days a week working from home and did that for years. But I got to spend another couple of weeks because at that point in time, we had no idea what was really going on with the business and we were just waiting to see what was going to happen with COVID.
[00:12:24] Caleb Avery: And those couple of weeks still to this day are some of the best memories that I have of any of the kids early on in their childhood. And so it’s really influenced how I think about the concept of parental leave, but also almost more specifically paternal leave. Because I think, especially in the US as a society, we have this stigma, at least in my opinion, where it’s much more accepted for women to take off time around a baby being born. That’s just generally expected. There’s physical recovery and breastfeeding or whatever it is that they’re going through. Whereas I think for dads, it’s almost this macho, “Oh, well, I can’t miss work to hang out with the baby. I need to get back into the office.” And for me, having had both experiences and living both of those, I’ve been really insistent for the folks on my team, both men and women that have had kids, that they take the time.
[00:13:24] Caleb Avery: We’ve had guys on the team that have taken eight, 10 weeks to go spend that time with their kids. And I’ve talked to each of them after the fact, and they never would’ve done it if me, the CEO of the company wasn’t calling them saying, “I will be upset if you don’t take this time off,” which I don’t know if that’s HR appropriate, but I think for me, I just shared my experience, “Hey, I lived both of these lives and I would never regret that time for a second.” And they took the time, they loved it. And it’s just one of those impactful things that I’ll never forget.
[00:14:01] Adam Fishman: Yeah. Okay. Wow. Well, I’m glad that you had both ends of the barbell experience there to help you develop your perspective on this. And it sounds like it’s made you a more, I don’t know, empathetic founder and CEO when it comes to other people starting families. So kudos. Glad that that could happen. I wanted to ask you about something that you mentioned as we were talking through this show, but it’s actually something really interesting that I haven’t heard a lot of dads on this show express. Maybe no one, even though I believe this to be true, it’s just something that’s never come up. And that is, you told me that it’s really hard to make friends. Because I hadn’t heard a lot of other parents say this out loud, I just wanted to sit with that for a second and ask you, what do you mean by that?
[00:14:50] Adam Fishman: What’s hard about making friends when you’re a parent? Yeah.
[00:14:55] Caleb Avery: So I’ll take the probably unpopular opinion, but I think there’s a lot of people that share this point of view that it is difficult as a parent with little kids to find families that you enjoy spending time with. And what I mean by that is for kids, they make friends everywhere. I mean, my five year old can’t go to a playground without finding a kid that he wants to play with for the hour or two that we’re there. And so for the kids, there’s no problem whatsoever making friends. But from my point of view as the parent, thing one is I want to find kids that I actually think are a good influence on my kids. And so some of the times the kids that they want to hang out with are not kids that I think are a good influence on them. And so for me, I’m not wanting to encourage them to spend time with a kid that I think is a bad influence on them.
[00:15:43] Caleb Avery: And so that filters down the children that my children want to hang out with that I want them to hang out with. And then the second part of the equation is finding parents that I actually want to hang out with. And so the way that I think about it is like you’ve got these two Venn diagrams of the kids that my kids want to hang out with and the parents that I want to hang out with. And it can be really difficult to find the overlap in those two circles where we have some really, really good friends that are parents and the kids seem like they want nothing to do with each other. They have nothing in common. They don’t want to play together. And you’re like, can we just be friends so we can travel and go on trips together? And then vice versa.
[00:16:22] Caleb Avery: It’s like some of their best friends were just looking at the parents and it’s like, we have nothing to talk about. We have nothing in common. And so I think that’s really where that point of view is rooted for me is I want to find those people, which we have some great, great friends that we’ve met over the years where the kids have a ball. We as parents love hanging out together, but it’s not a long list.
[00:16:46] Adam Fishman: Yeah. Just that Venn diagram of overlap is very narrow. It sounds like the bottom line is like the reason it’s hard is because either the kids suck or the parents suck and finding a group where that is not true for both people in the equation is difficult.
[00:17:04] Caleb Avery: And I don’t know if that’s saying more about me or my kids or the other parents. I don’t know who the problem is in this situation, but that’s been my experience.
[00:17:13] Adam Fishman: Yeah, no, I think it’s actually more common than you might think. And that’s why I was kind of surprised when you brought that up and no one else has. Maybe we just didn’t want to say the quiet part out loud or something. I don’t know. But hey, here on Startup Dad, that’s all we do is say that. So aside from the realization that… And by the way, you probably didn’t know this going into being a parent. You probably didn’t have this thought in your head that like, “Oh, it’s going to be hard to make friends because there’s a couple of vectors I got to figure out.” So aside from that, what would you say is the most surprising thing that you’ve discovered after becoming a dad?
[00:17:51] Caleb Avery: Yeah, I think for me, and this might be another controversial one, but the idea of nature versus nurture. So if you had asked me prior to having kids, how baked are the kids when they come out versus how much influence do you as a parent have on the kids? Prior to having kids, I would have said, “Hey, it’s all on the parents. If they screwed them up, it’s totally on them.” Versus now I got a sample size of three. I think it’s a decent sample size. And the personalities that each of them had when they were a month, two months old, a lot of that’s the same characteristics that I see in them at almost eight, almost six, going on three. And that’s kind of wild to me that, at least from my point of view, these kids are coming out 80% baked. They kind of are who they are as humans when they come into the world.
[00:18:41] Caleb Avery: And I think as parents, we still have a very important job. You’ve got to mold that final 20%, which can have a big impact on who they are and then also try and steer some of those bad tendencies, if you will, and help teach them and coach them on how to improve those elements of themselves. But that’s been something that’s been incredibly surprising to me just at how consistent they have been over the eight years that I’ve known these little guys. They’re the same people as when they came out. And that’s kind of crazy to me.
[00:19:14] Adam Fishman: And no one really prepared you for that realization coming into it. Yeah. You have another important job in addition to being dad and startup founder and CEO, and that is five year old T-ball coach. Why was that an important thing for you to do? Like you’re a busy guy, you got three kids, you got a company you’re building that you’re in charge of, the livelihoods of all these people, you got a spouse. Why take on the T-ball coach role?
[00:19:42] Caleb Avery: For being totally honest, it wasn’t on purpose. So my dad signed up to be the T-ball coach.
[00:19:50] Adam Fishman: Your dad. So grandpa.
[00:19:51] Caleb Avery: Yes. So hey G-Pa, would you be my T-ball coach? My parents are very involved in the kids’ life. And so G-Pa says, “Absolutely. I’d love to do that.” Come to find out, he’s leaving two weeks into the season to go on a road trip for a month. And so we have him as the head coach, the assistant coach tears his ACL, can’t help. So we’ve got a headless chicken for this T-ball team. I am reluctantly thrust into initially the assistant coach role for whatever it is, two weeks. And then I get the promotion of a lifetime to be the head coach.
[00:20:27] Adam Fishman: Your executive skills took over and you just became the CEO of the team. Yeah.
[00:20:32] Caleb Avery: I had to fill this power vacuum that emerged. And I’m a very competitive person. And honestly, when the kids were little, I was like, “I’m not going to coach them because I don’t want to be this super intense T-ball dad that’s yelling at all the kids.” This was an interesting experience for me because five year olds are terrible at baseball. Let’s just be honest, let’s call a spade a spade. They can’t throw, they can’t catch. Half of them can’t even hit off a tee. These are not coordinated athletes that you’re coaching. And I remember we go to the first game, I know nothing about what’s going on. I didn’t want to be in this position. And I’m like, “Hey, who’s keeping score?” And the other dad looks at me, I think he’s got three or four older kids, he’s done this a lot and he’s like, “Hey man, we don’t keep score.” I’m like, “What do you mean we don’t keep score?” And he’s like, “We can’t.” And to me, it’s just not registering.
[00:21:28] Caleb Avery: And he’s like, “Just watch the game.” After the game, I’m like, “Oh, we can’t keep score because no one ever gets out. No one can catch the ball, throw it to the first baseman, him catch it and touch the bag.” That concept doesn’t happen. So this game would go on for eternity if we’re trying to keep score and determine a winner. And so at that point, after that first game, I’m like, “Okay, this is not about winning and losing. There’s no competitive fire to be stoked here. My job is to help these kids have fun.” And that perspective shift, all of a sudden I went from frustrated that I’m even there having to basically babysit these kids as they suck at baseball to all of a sudden, “Okay, great. We’re going to have a great time. We’re literally here to have fun. Let’s go run around.”
[00:22:12] Caleb Avery: “If you want to chase butterflies, you do your thing. Kids are digging holes over there at shortstop. You do your thing and we had a great time.”
[00:22:20] Adam Fishman: Yeah. Your role is not to mold young men and women into baseball studs. It’s basically teach them how to high five their teammate when they’re coming to the dugout or something like that. Here’s
[00:22:32] Caleb Avery: Basic etiquette and loosely understand the rules of the game and we’ve won.
[00:22:38] Adam Fishman: Okay. Well, how do you fit this in as a founder? Because you’re busy, work’s demanding. When do you have time to peace out for a T-ball practice or I assume games and stuff are on weekends and things like that, but is there much practice? I don’t know.
[00:22:53] Caleb Avery: The games were the easiest for sure. So the games were always on Saturdays and so I was able to make the games and the practices, I did my best. And so I attended most of the practices. And then we had basically moms that stepped up and they ran some of the practices. I have no idea what happened in some of the practices that I wasn’t in attendance for, but the kids seemed to have a great time. And I think for me, I just didn’t hold myself to this perfect standard of I have to be at everything because that wasn’t realistic for me. But I made it to I think all the games but one. I think I was out of town for one game and I made it to most of the practices.
[00:23:34] Adam Fishman: Okay. And did you give your dad shit when he was like, “Peace out. I’m going to be the coach, just kidding. Now you have to be the coach.”
[00:23:41] Caleb Avery: I was not that happy about it, to be totally honest. He calls me, he’s like, “Hey, you know I’m leaving on this road trip.” I’m like, “I have no knowledge. If we’ve had this conversation, I don’t remember it.” What do you mean? What are we doing here? He wasn’t that apologetic, which also didn’t help in the conversation. He’s like, “You got it.” It’s like, “I didn’t want to be the T-ball coach.”
[00:24:03] Adam Fishman: How have your personal T-ball skills improved since you’ve been the coach? Are you cranking homers off the tee now or…
[00:24:13] Caleb Avery: I would say I am much, much better at teaching a five year old where to stand in the batter’s box to make contact with the ball. And so draw two circles for their feet, stand in the circles. And that wasn’t a skill that I knew I needed prior to being a T-ball coach. So I can’t say my actual ball skills have improved really at all. Maybe the only skill I could highlight is running away from a group of 10 children. I’m pretty good at juking out all of the kids because that was our warmup before all of the games was like, “Come tag me.” And then we run around the outfield until I’m out of breath and then the game is over.
[00:24:54] Adam Fishman: That’s a good creative warmup and they don’t really feel like they’re warming up, but they are. So cool. You described yourself to me as a big kid. How does that play out in your life?
[00:25:06] Caleb Avery: It honestly surprises a lot of people that only know me professionally because that’s not exactly my personality on the day to day in a work environment. But I think for me, thing one is I just enjoy playing with my kids, their friends, whatever. I just enjoy it. And so for me, if I have my kids alone on the weekend, I’m taking them to a trampoline park or a ninja place or some activity where we can just go run around, be goofy, burn off the crazy energy that these small children have and just have a good time. But I think part of it is also rooted in the fact that I do work a lot. I do travel a lot. I’m gone a lot. And so I don’t want to be the parent that’s like, “Oh, go play on the playground. I’m going to sit here on my phone and watch Netflix.” That’s not being engaged with them or being present with them in the time that I’m there.
[00:26:00] Caleb Avery: And so some of it is like, “Okay, we’re going to go play. What are we going to go play as a family?” But the second part of it is I also just kind of like it. And so if we’re going to a kid’s birthday party at the Ninja Park, I’m going to be doing the activities and flying down the stuff, jumping into the ball pit and jumping on the trampoline with all the kids instead of sitting there hanging out with the parents. It’s just kind of who I am.
[00:26:23] Adam Fishman: By the way, I’ve been to one of those Ninja Warrior parks and that stuff is hard.
[00:26:28] Caleb Avery: It really is.
[00:26:29] Adam Fishman: Some of those things are real difficult.
[00:26:31] Caleb Avery: You don’t realize how out of shape you are until you’re hanging from stuff. You think you’re doing good. And I look over, my seven year old daughter’s just over there doing pull-ups. Her upper body strength is unbelievable. She does a lot of gymnastics and I’m just like, “Man, I am really out of shape.” But I think it’s the strength to weight ratio isn’t working in my favor quite like the five and seven year olds.
[00:26:54] Adam Fishman: Yeah, we could call it that. Is Ninja Warrior Park or Trampoline Park your favorite big kid activity?
[00:27:01] Caleb Avery: I would say so. I think those are the two places that we just absolutely love going. The Ninja Park, especially the problem is you have to be five to go into at least our local ninja park. And so we
[00:27:14] Adam Fishman: It’s probably for good reason.
[00:27:15] Caleb Avery: Well, yeah, the two and a half year old would just… He’s a danger to himself and others if he was there. So totally fair rule, but there’s just less occasions where I can say, “Oh, I’m going to take the older two, honey, enjoy the baby.” And so normally we’re trying to do stuff as a family. And so the trampoline park becomes the go to activity, which you can do when it’s too hot outside, too cold outside, doesn’t matter. It’s great year round.
[00:27:38] Adam Fishman: For sure. Although sometimes the trampoline park becomes like Mad Max in the Thunderdome and it’s just like Lord of the Flies in there.
[00:27:46] Caleb Avery: It really can be. If you go at the wrong time, either a year or Saturday morning when it snowed, it can be a zoo.
[00:27:54] Adam Fishman: I went there for a birthday party recently and I had to step outside because it was so loud. It was like a Vegas casino. Maybe I’ll go back. We’ll see. So as a founder, you probably talk to a lot of founders, right? It’s kind of a thing that founders do because it’s kind of lonely to be founder CEO. You need to commiserate with somebody. And I’m wondering if you ever talk to other founders who are younger than you thinking about starting a family and what you tell them about your experience building a company and raising young kids at the same time.
[00:28:27] Caleb Avery: I have had this exact conversation with several founders. I’m pretty active and vocal on LinkedIn just in general about building the business, having the family, whatever. And so pretty regularly I get inbound from founders that I’ve never met, I’ve never talked to that just are looking for advice. Could be fundraising advice, could be startup advice, could be family advice. And when it comes to the topic of starting a family as a founder, the advice that I give them is you have to be honest with yourself about what the trade offs are going to be and whether or not you can accept those. And so there’s a limited amount of time that you have in your day. And if you look at what your day looks like today, no kids, it’s going to look real different when you start the business and when you start having kids and you have to be honest with yourself about whether that’s something that you want to sign up for, because if you don’t, then you’re setting yourself up for a pretty dangerous situation where you’re either going to be unhappy with the kids, unhappy with the business or unhappy with both.
[00:29:26] Caleb Avery: And that’s not fair to you. It’s not fair to your wife. It’s not fair to your kids. And that’s probably not advice that they’re getting from a lot of people because you kind of have to have walked a mile in these shoes to understand that there is that trade off. And back to what we talked about earlier, for me, that trade off was just less time for myself. And so I know I’m going to golf less. I know I’m going to ski less. And I know when I do some of these things that I enjoy, I’m going to have one, two, or three children in tow to do that. And that sounds like fun to you, go have kids. And if it doesn’t, don’t have kids and both of those things are okay.
[00:30:04] Adam Fishman: Yeah. Or maybe get it out of your system
[00:30:06] Caleb Avery: Before you start the company.
[00:30:08] Adam Fishman: Yeah, exactly. Exactly. Yeah. So it sounds like the main advice is just like be clear eyed and go into this just knowing that it’s hard and that you got to be into it or it’s not going to be good for you in either direction. So cool. Since you started the company when you had really young kids and you’ve gone through this like seven years, seven plus years of building the company, would you say that becoming a dad has made you a better founder and a CEO than… I mean, obviously maturity, like you’re different than you were when you were 19 and starting a company. But do you attribute anything to parenthood and the responsibilities or the changes that have happened to you since you’ve had kids?
[00:30:48] Caleb Avery: Yeah, definitely. I think probably two big areas. I think thing one is just from a point of empathy, just as a parent, you have to have a lot more patience and empathy just to get through your day as a parent. And if you bring that mindset, that attitude, those characteristics into business, I think that’s positive for building a culture, building a business. And then thing two is I feel like for me, just the added responsibility of I have kids at home that I have to support. I cannot afford for this to be a failure is just that extra little bit of motivation as a founder to put in the extra time, to put in the extra hours. But I think it does change how you approach things a little bit where like when I was building my first company, 19, 20 years old, I was working around the clock.
[00:31:39] Caleb Avery: And that’s just the way that I operated was always on my phone, always on calls, always doing deals, doing business, whatever. And I think now having kids, you have to be a little bit more intentional about your time every day, assuming that you want to get home to the kids, which is certainly something that’s a priority for me. And so there ends up being this kind of forced prioritization exercise of like, I have X amount of hours today that I have to get 10 hours to get 13 hours of work done, how do we do it? And I think that concept of focusing in and drilling in on what’s important is actually really, really good overall for the business.
[00:32:21] Adam Fishman: Awesome. I want to stay on this topic of things that you have to be intentional about because one of the things that you told me is that the most important thing for you is bedtime with your kids. Why did you decide that bedtime’s going to be your thing? And how does that, as the number one priority with your kids, how does that affect or influence your behaviors, your work behaviors and sort of other things that you do?
[00:32:46] Caleb Avery: It started around this idea of like, when can I spend time with my kids, knowing that I’m going to be busy in the office. I travel a lot for work, and so there’s going to be a lot of time that I’m away. And so what is a time that I can set aside that I can be 100% present? I’m not thinking about work. I’m not half on my email, half paying attention to the kids. And also that they’re fully present with me. They’ve got a lot going on. They’ve got school, they’ve got homework, they’ve got friends, they’ve got their iPads, whatever’s going on. And I feel like it’s that fun time for me where they’re kind of goofy, they’re tired, they’re getting that last little bit of crazy energy out. They want to snuggle, they want stories. It’s a really fun time for me in the day.
[00:33:35] Caleb Avery: And so it’s something that I just decided early on was going to be this non-negotiable for me that like I’m going to do everything I can to be home for as many bedtimes as I can. And so that’s actually how my kids count how long my trip is. It’s like, how many times is daddy missing bedtime? And so what that manifests itself in terms of changes for me, if I’ve got work dinners, I schedule them at like five o’clock. So I’m doing the senior special dinner hour, which in general having little kids, you eat early or at least we do. And so that’s also my preferred dinner time. But if I have people flying in for business meetings, I schedule a five o’clock dinner. So I can be home by 7:30 to put the kids to bed. And then the other is it changes the flight times.
[00:34:20] Caleb Avery: And so for me, when I’m thinking about trying to schedule my trips, a lot of times I do make changes to the schedule to try and get home for that 7:30, 8:00 window to be able to put the kids to bed. And it’s just something that I’ve gotten used to being intentional about. And so now that’s the routine.
[00:34:40] Adam Fishman: Cool. Related to this, on this show, we’ve talked a lot about work-life balance, work-life integration, this concept that balance doesn’t exist. We’ve had a lot of different takes on this. Everyone’s got a slightly different take. There’s themes, but very different. One of the things that I learned about you is that you don’t really think about work-life balance. You focus more on boundaries and non-negotiables. And so I’m curious, first, what are boundaries and non-negotiables? What does that mean?
[00:35:14] Caleb Avery: It’s the idea of what is family time versus what is work time, and then what does family time look like? And so if I am at the Ninja Gym with the kids, what does that look like for me? And so the boundary is, okay, I’m not on my phone, I’m not doing emails, I’m not doing calls, I’m hanging out and playing with the kids, because you can spend the same amount of time, the same amount of hours with them, but not be present. You’re not actually getting any quality time with them. And so what I try, and not saying I’m perfect, my wife would be the first to say I fail at this at times, but what I try to do is to be intentional about setting that boundary. And for me, one of the things that I’ve actually found helpful is going into the office and having that separation of the drive home to finish up the calls.
[00:36:04] Caleb Avery: And if I have to stay an extra hour or two, I stay the extra hour or two to get stuff done and then get home and set that boundary of like, okay, well, now I’m paying attention to what’s going on at home. And for me, I feel like if I don’t set that boundary, if I don’t establish those non-negotiables like bedtime, it’s very easy to work later. It’s very easy to take that later flight home because you’re tired or you’ve got to fit in that extra meeting. And so it’s easy to let those things slip versus if you’re conscious about saying, “This is what’s important to me and this is the plan for how I’m going to accomplish this thing that’s important to me,” then your brain changes that decision. When you’re looking at flights, if you don’t have that boundary or that non-negotiable in your head, okay, well, for me, this is easier.
[00:36:55] Caleb Avery: I can have dinner, I’ll get home at this time. It’s fine for me, I’ll go to bed, but I take that earlier flight because I know I have to be there.
[00:37:03] Adam Fishman: It’s also by setting those, and again, you’re not perfect, no one is. I have yet to meet a perfect dad on this show, by the way.
[00:37:13] Caleb Avery: Doesn’t exist. Or they’re a liar.
[00:37:15] Adam Fishman: Yeah. Right, right. At least you can say, “Well, I’m holding up my end of the bargain. So even if I have to skew my time a lot more towards work, I’m not going to fall down on the commitments that I’ve made because that’s the important thing. I’ll have to work really hard, but bedtime’s bedtime. Getting home early is the bar that I’m holding myself to.” So that’s good. I think you described it as you get to feel like you’re winning even if you’re skewed a little bit more towards work.
[00:37:47] Caleb Avery: Yeah. To me, that whole concept of balance is an unrealistic standard. And so I liked the way that you put that as this is the standard that I’m holding myself to. It’s not realistic for me, at least in this time in my life building the high growth business that I am. I can’t work 10:00 to 3:00 and go pick up the kids and go grab ice cream every day. And that’s not what I signed up for in the job that I’m in right now, but I do have my own standard that I do my best to hold myself to. And yeah, I love the way you put that.
[00:38:19] Adam Fishman: I always love asking this question to people. What is something that you and your wife, Kelsey, don’t agree on when it comes to parenting?
[00:38:29] Caleb Avery: I would say probably the number one thing that comes up the most is the idea of cursing in front of the kids. She’s like hard boundary. We don’t do it. It should never happen. I’m not exactly the other end of the spectrum. There’s relative spectrum in this conversation. I’m somewhere in the middle where that is a part of my natural vocabulary. There’s just times where that comes out. And I think my philosophy with the kids is it’s unrealistic to expect that they’re going to grow up and be adults that don’t curse. That’s probably not the standard that we’re setting ourselves up for. If they choose that, God bless them, but that’s not my expectation of them as kids. And so I would rather set the expectation of like, “Hey, here’s when and what is appropriate, and here is when and what is not appropriate.” And introduce them to the idea that this is a word in vocabulary, but you can’t use it at school, you can’t use it with your friends, you can’t use it here and establish that idea of appropriate etiquette around the topic versus avoiding it altogether, which I’m never going to win this argument with my wife.
[00:39:40] Caleb Avery: I’ve resigned myself to that, but that is my point of view on the topic.
[00:39:45] Adam Fishman: That does seem like an unwinnable one for me, but maybe we’ll see. But I think what’s interesting about that, especially with swearing, and it happens. The older your kids get, the more they are exposed to other kids who have various spectrum of language that is allowed in their household. And it may almost be better to just establish kind of like what we were saying, a boundary and a non-negotiable. You’re going to hear this word at some point and your friend’s going to say it in school and that’s not a good place to say that word and here’s why. But you can’t just kind of put your head in the sand and assume that they’re never going to hear it. So maybe learning it from you is not the end of the world, but don’t tell your wife I said that because then she’ll be mad at me.
[00:40:26] Caleb Avery: I’m definitely going to go home and have that conversation.
[00:40:29] Adam Fishman: You show this exact clip.
[00:40:31] Caleb Avery: Adam
[00:40:31] Adam Fishman: Said. Adam, guy you’ve never met, but yeah. Okay, cool. All right. I want to ask you about technology. We’re getting kind of close to the end here and I really like to talk to, especially technology founders. How are you introducing and talking about technology with your kids? Obviously your two and a half year old, maybe a little bit young.
[00:40:53] Caleb Avery: He’s doing emails. He’s doing big deals.
[00:40:55] Adam Fishman: Vibe coding
[00:40:57] Caleb Avery: On the weekends and stuff. He’s building a startup.
[00:40:59] Adam Fishman: Yeah. I mean, we’re not too far off from that. If they can talk, it can happen. But you’ve got, like you said, almost six year old, you’ve got an almost eight year old. Have you introduced it? You mentioned iPads earlier in the conversation. How are you introducing it? How do you think about it? How do you think about the right balance and the relationship you want them to have with it as they continue to get older?
[00:41:20] Caleb Avery: This is another tough one. And this is one where I wouldn’t say my wife and I necessarily disagree, but there’s a lot of conversations where we’re trying to figure out what is that appropriate balance? When should they have it? What are the boundaries? What should they have access to? And at this point in time, they don’t have phones. They’re not on social media. So it is a little bit easier just because they are so young that it’s not even really realistic for us to even consider exposing them to certain things, but they do have iPads. They watch mostly Netflix or Disney Channel movies. They’ve got some games that we’ve downloaded for them, but we restrict it, one, based on what they can watch. So set up a profile for them that’s appropriate for them so that they’re not watching wild stuff that’s on Netflix and all the streaming shows these days.
[00:42:08] Caleb Avery: But I think the biggest thing is being intentional about the time restriction. When are they allowed to have it and when are they not allowed to have it? And making sure that that’s clear to them because what I hate is them, “Oh, can I have my iPad?” It’s like, no, it’s Thursday. You can’t have it. They get them on the weekends and they get them when we travel. And so for us, it gives them the ability to experience having that, but it’s not this tool that they have unlimited access to all of the time. There’s also times where it’s really helpful as a parent to just like, “Please go watch your iPad for 20 minutes. I need to do whatever.”
[00:42:45] Adam Fishman: Right. So your daughter, your oldest daughter is about almost eight, and I know she doesn’t have a cell phone yet, but there’s been a lot written about and talked about with, especially younger girls, teenagers especially. And she’s not a teenager. She’s five plus years away from that. It’s probably
[00:43:04] Caleb Avery: Terrible. Sometimes it feels like it. So I feel like we’re getting
[00:43:08] Adam Fishman: There. We’re approaching the tween years. Is that something that you’ve started to think about or talk about with your wife about what’s going to happen as she gets a little bit older or are you kind of punting on that conversation maybe just for a few more years?
[00:43:21] Caleb Avery: She’s not letting us punt on the conversation.
[00:43:24] Adam Fishman: Oh, she, your daughter?
[00:43:29] Caleb Avery: Yes, yes, yes. I don’t think any of her friends have one, so I’m not really sure what the push is at this point, but she’s got this idea in her head like, “I want to know when I’m going to have access to a phone.” And coincidentally, both my wife and I were 13 when we got access, a lovely flip phone. This is pre-iPhone, smartphone era, did almost nothing and it was great. And so arbitrarily, we’ve said that that’s the age right now, but it’s basically just to give her an answer today of just, sure, when you’re 13, you can definitely have a phone. But I think my wife and I know realistically, it’ll probably be before that. And I think for us, the way that we’ve thought about it is right now she’s not really doing much of anything on her own. We’re not leaving her at friends’ houses.
[00:44:19] Caleb Avery: She’s not staying home alone in part because she’s got a two and a half year old brother that we can’t leave him. So if you’re bringing a two and a half year old, almost eight year old’s the easy one. Please help us watch the other two. And so I think for us, that kind of paradigm shift will be whenever, okay, she needs to be at such and such place for an hour or two by herself, I want to know where she is. I want to be able to get ahold of her. And so it’s almost like we’ll cross that bridge when we as parents need it for our own sanity and her safety. And so that’s really the only way that we’ve thought about it thus far.
[00:44:58] Adam Fishman: Yeah. And I think there’s no judgment in any way, but that’s probably fine that you kind of really kicked the can on that decision for a bit. But it is funny that at eight, almost eight, she’s already bringing it up. She’s probably not the only one.
[00:45:11] Caleb Avery: No, no. I’m sure there’s some pod at school that they’ve got this idea that, “Oh, let’s ask. Let’s see what we can get.”
[00:45:19] Adam Fishman: So staying on the topic of technology, you’re a startup founder, you’ve probably heard about this AI thing.
[00:45:25] Caleb Avery: Never heard of it.
[00:45:26] Adam Fishman: Yeah, kind of a big deal. Has AI found its way into your parenting in any way yet? Are you doing anything with your kids? Are you doing anything for yourself that helps you with parenting?
[00:45:37] Caleb Avery: I would say for the most part, not really. The only thing that I can really think of is I wear an Apple Watch and especially at bedtime, the kids are funny. They just have a million questions all day long, all the time about a variety of topics. Some of them, educational, many of them, poop related. That’s just the nature of
[00:46:01] Adam Fishman: That checks out.
[00:46:01] Caleb Avery: Little kids. It does. And so most nights, if I’m still wearing my watch when I’m putting them to bed, they’re each two, three, four, five questions for Siri. “Hey, Siri,” which Siri’s probably going to start talking back to me here in a second, but they have all these questions that they have to get the answer to. What’s the tallest building in the world? What are the longest fingernails ever? Who had the first Guinness Book of World Records? How many teeth does a shark have? These are the things that when you’re five, you can’t go to sleep without the answer to this question.
[00:46:36] Adam Fishman: These are life’s critical questions.
[00:46:38] Caleb Avery: These are the most important questions in life. I don’t know the answer to them because half of them are ridiculous or trivia facts that I don’t even care to know the answer to. And so Siri gets a lot of action about eight o’clock in my household every night and it answers their burning questions and gets them in the mood to go to sleep.
[00:46:59] Adam Fishman: It is really funny how kids gravitate towards these Guinness Book of World Record type questions, the longest fingernails, the tallest building. There’s an age where they hit and it’s like that’s what they’re
[00:47:11] Caleb Avery: Obsessed with. You just need to know facts that you can go tell your friends, did you know the tallest wave in the world was 1700 feet tall or whatever it is? And it’s like, I didn’t know that. I don’t need to know that, but now I do.
[00:47:24] Adam Fishman: I sure didn’t know that either, but hey, I learned something new every time I do this show. Okay. We’re about to get to lightning round, but before we do, I wanted to ask, how can people follow along or be helpful to you in your journey?
[00:47:36] Caleb Avery: Yeah. So LinkedIn is really where I’m most active. I don’t really have any other social medias. So if you want to find me, it’s either in person or LinkedIn. Those are your choices. But on LinkedIn, for good or bad, I share a lot about building the business, the dad life, the aspiring golf career, all of that on full display on LinkedIn. So if you want to learn more about all those topics, follow along. If not, great time to unfollow me because it’s probably downhill from here.
[00:48:06] Adam Fishman: Well, if you like this show, then you know exactly what you’re getting on LinkedIn. So no surprises. We’ll make sure we point people your way in the show notes. All right. Are you ready for lightning round?
[00:48:16] Caleb Avery: Maybe.
[00:48:17] Adam Fishman: I think that is the only appropriate answer.
[00:48:20] Caleb Avery: I think so.
[00:48:21] Adam Fishman: All right, here we go. What is the most indispensable parenting product you’ve ever purchased?
[00:48:27] Caleb Avery: The SNOO. Probably also among the most expensive. So if you don’t know what a SNOO is, it’s like this smart bassinet for kids to sleep in. And as a parent, anything that helps you sleep is a winner. So look up the SNOO. You will not regret it.
[00:48:40] Adam Fishman: Have you used it with all three kids or did
[00:48:43] Caleb Avery: You. Absolutely.
[00:48:44] Adam Fishman: Okay.
[00:48:44] Caleb Avery: Cool. Absolutely. And the resale value is incredible. So you can buy it and sell it. And if you buy it on Black Friday, it’s almost a free rental of the SNOO. So plan ahead, buy your SNOO on Black Friday, resell it unless you’re having more kids.
[00:49:01] Adam Fishman: Okay.
[00:49:01] Caleb Avery: It’s amazing.
[00:49:02] Adam Fishman: SNOO fan here. What is the most useless parenting product you’ve ever purchased?
[00:49:06] Caleb Avery: The little mirrors that rear facing child, you’re trying to attach this to the back of the seat. I don’t know if I just suck at installing them, but it’s either falling down at all times, in which case, I don’t think I’ve ever seen the baby in the mirror or it is an object for the baby to kick incessantly until it breaks. And so it’s like for me, it annoys the crap out of me and I’ve received zero value from it. And so if you want to light money on fire, buy the mirror for the car seat, but otherwise avoid it.
[00:49:41] Adam Fishman: That’s amazing. Also, what do you really need to see back there? The baby is strapped into a car seat. There’s not much going on. They’re not choking on anything because you’re not giving them anything to choke on.
[00:49:52] Caleb Avery: Unless they have older siblings. Oh, you’re very right actually. The curse of older siblings is like, they are there to like, “Hey, what’s going on with the baby?” But normally the question is like, what did you do to the baby is generally like something sounds amiss. What did you do?
[00:50:10] Adam Fishman: Yeah. Oh, I love that. We too owned the mirrors and I hadn’t thought about it until just now, but they were pretty useless for all the reasons that you mentioned. Okay. What’s the weirdest thing you found in your kids’ pockets or in the washing machine?
[00:50:25] Caleb Avery: I’ll go with what I found in my pocket. So as a dad, your kind of gear that you know you’re going to have, hand sanitizer, maybe some baby wipes, a Hot Wheels car. You kind of never know what you’re going to find in your pocket. But for me, when the kids were all wearing diapers, I carry dog poop bags. So if there’s ever an incident, you don’t want to just have a dirty diaper. What do you do with that? So carry the dog poop bags. Well, this was years ago. Thank God all the kids are out of diapers at this point, but I go to put on my big parka winter coat early on in the winter, reach in my pocket, dog poop bag, but it’s not empty. And so for many, many, many months, there was a dirty diaper riding shotgun in my favorite jacket.
[00:51:16] Caleb Avery: And it’s one of those totally my fault. Something happened, put it in there, put the jacket away, winter ended. So that was a startling find in my pocket that probably I’ve never told anyone about. So this is me admitting something that probably never should have seen the light of day today.
[00:51:36] Adam Fishman: Just incubating that for an entire summer in the closet.
[00:51:40] Caleb Avery: Love that. It was a good one.
[00:51:42] Adam Fishman: Okay. True or false, there’s only one correct way to load the dishwasher.
[00:51:47] Caleb Avery: Fun fact, probably my best performing LinkedIn post ever was this exact topic. I feel very strongly about this. My general opinion is if you don’t think that there’s only one way to load a dishwasher, you are the problem. And so I’ll leave it at that.
[00:52:05] Adam Fishman: I love that it was your best performing LinkedIn post. No one cares about my important business. PayFac as a service. Yeah, they don’t care about anything. What they care about is the dishwasher. I mean, clearly we’re asking the important questions on this show. What is your signature dad superpower?
[00:52:23] Caleb Avery: I think I got to go with snuggling. So we talked way too much probably about bedtime on this episode. And I’ve been told by three children in Boulder, Colorado that I am the best in the world at snuggling. My wife hates that they universally agree that I’m better at it, but these are the facts on the ground. Can’t dispute the facts.
[00:52:43] Adam Fishman: Okay. Well, three kids can’t be wrong. So I take that as a win. If those kids had to describe you in one word, what would it be?
[00:52:52] Caleb Avery: Silly.
[00:52:53] Adam Fishman: All right. What is, maybe in addition to finding the dog poop bag in your pocket with the diaper in it, what is the most frustrating thing that has ever happened to you as a dad?
[00:53:03] Caleb Avery: Let’s take it back to my first kid being born. So this might be a slightly longer story on this one, but so first kid’s born, I’m doing the documents for the funding round at the hospital. The backstory is we worked with the hospital to pick our insurance plan. So they told us this would be a good insurance plan for you to choose. Maybe 18 hours after our daughter was born, lady shows up in our room, “Hey, got some bad news. Your insurance plan doesn’t work at this hospital.” And I’m like, “That’s weird. Does Amy still work here?” Oh yeah, yeah. So Amy picked our insurance plan for us for this hospital and the lady starts to look pretty nervous. And I’ve been up for probably two days. I’m at like first kid, you don’t know what you’re doing. You’re tired. Labor always takes forever. I look at her, I am eerily calm.
[00:53:59] Caleb Avery: I’m like, “You have two choices here. You can work this out with our insurance company or you can get sued. Your choice. I’m good either way. Your choice.” We did not hear from anyone. She just leaves the room. She’s terrified. We don’t hear from anybody for probably 10 months about this. We get a bill that was like $1,500. It was the cheapest baby we had of any of the three. I think the hospital was like, “We’re pretty much just going to write this off total L.” But I was absolutely fuming in that moment. I don’t think I’ve been that mad because I probably haven’t been that tired in almost eight years.
[00:54:36] Adam Fishman: Yeah. I can say I would’ve not done very well in that situation. I’m impressed that you remained calm and just very clearly laid out almost in a, I don’t know, Liam Neeson way. Here are your options.
[00:54:50] Caleb Avery: What do you want to do?
[00:54:52] Adam Fishman: I could see that it’d be very frustrating. Okay, what’s the wildest thing that one of your kids has ever asked you to buy for them?
[00:54:59] Caleb Avery: A pool. They were incessant that we must have a pool. And it turned into a good opportunity to talk about money. It was like, “Hey, I would have to work this long to buy a pool. Do you want to not see me for this long?” They’re like, “No, we don’t want that.”
[00:55:16] Adam Fishman: Yeah, good perspective. And you’re in Colorado, that pool’s not useful that long.
[00:55:22] Caleb Avery: It’s not. We have a hot tub and even that, I spend more time cleaning the hot tub than they spend swimming in the hot tub. And so I’m like, “You have not earned the pool. We’re good.”
[00:55:34] Adam Fishman: Okay. What is the most difficult kids’ TV show that you’ve had to sit through?
[00:55:39] Caleb Avery: It’s a long, long, long list, but the CoComelons, Baby Sharks of the world. Kids sing along TV just drives me crazy in a way that few things do. I’m a very even keel person, but I start hearing CoComelon and it’s like war flashbacks. I can’t do it. I’m not into it.
[00:56:02] Adam Fishman: All right. On the flip side, what’s your favorite kids’ movie?
[00:56:06] Caleb Avery: Sandlot. Grew up playing baseball, just epic movie. There’s language in there that you can’t get away with in kids’ movies these days. So it’s just a classic.
[00:56:18] Adam Fishman: Related, I was going to ask you what the nostalgic movie you can’t wait to force your kids to watch with you. Is Sandlot that movie or is there another one?
[00:56:26] Caleb Avery: I feel like I have forced them to watch most of the age appropriate nostalgic movies at this point. We’ve gone deep down the Disney classics rabbit hole. They’ve gotten to experience a lot of the classics. But I think for me, I love Die Hard. It’s just a great, great movie. And it’s not quite appropriate for any of them. Not quite yet. At this stage, that’s one of those five years from now or something, maybe the oldest one can watch it. I don’t know what that window is.
[00:57:00] Adam Fishman: It’s a Christmas movie, so you can do envelope at the holidays. Yeah. Okay. What’s the worst experience you’ve ever had assembling a kid’s toy or a piece of furniture?
[00:57:08] Caleb Avery: This Christmas, my mother-in-law ordered the kids a golf cart, 300 bucks on Amazon, definitely from China, full assembly required. I mean, this bad boy came in nine million pieces. Like a flat instruction golf cart, basically.
[00:57:25] Caleb Avery: Yeah. The instructions are like 10 photos. They’re like, “Good luck.” No YouTube video, just good luck. Probably five plus hours and not fun. This was tedious little screws or… It just horrible. Finally get the thing together. I’m not happy at this point. Turn it on, music’s playing. I’m like, “Okay, great. It works.” It’s got a remote. I go to press the gas, doesn’t go anywhere. And at this point I’m like, “I am going to throw this entire thing in a dumpster. I don’t want this. It’s terrible.” And honestly, it’s still a piece of crap, but I email the company and I’m like, “Hey, it doesn’t go.” And they’re like, “Oh yeah, this happens all the time.” And I’m like, “Not a good answer.” They’re like, “You have to replace…” I don’t even know what it was, this piece on it. And I’m like, “Oh, that sounds easy.” They’re like, “Oh, it’ll take you five minutes.” They send the replacement piece weeks later, because I’m sure it’s coming from China, open this bad boy back up, which takes 45 minutes because it’s horrible.
[00:58:32] Caleb Avery: And I look in there and this piece that I have to replace is super glued. All the wires are super glued in. It’s super glued to the golf cart base. And so I am chiseling with a screwdriver. At this point, I’m like, “I don’t care if I break this. I’m returning this. This is a piece of crap.” So I’m just stabbing this thing endlessly and eventually loosen it up, plug in all the wires, just throw it in there, put it back together. And it worked. I still hate this thing. I still kind of want to throw it in the trash even though it works just because my experience was just that visceral. And so don’t buy… Maybe we put the link in the comments to this golf cart and don’t buy this thing. It’s terrible.
[00:59:18] Adam Fishman: Well, not to poke the bear, but I feel like the icing on the cake would be if you did all this and your kids didn’t really like it. Do they at least like the golf cart?
[00:59:26] Caleb Avery: No.
[00:59:26] Adam Fishman: No.
[00:59:29] Caleb Avery: Nope. No. Which is just salt on the wound. Literally, it’s salt on the wound.
[00:59:35] Adam Fishman: Oh, that’s the best. No. Okay. Well, wow. I feel like this is a clip worthy answer to this question. I don’t know that I’ve ever had… In my being feel the pain of your situation here.
[00:59:49] Caleb Avery: I want to break it. All right. I need to do something.
[00:59:52] Adam Fishman: Okay. I got three more for you. How long can a piece of food sit on the floor and you will still eat it?
[00:59:58] Caleb Avery: It’s probably longer than I want to admit out loud. I think as a parent, you’re just kind of desensitized to food on the floor, half eaten. Oh, you took a bite out of this banana. Whatever. You ate half a sushi nigiri. I’ll still eat that. And so 15 minutes. I don’t know. What’s the appropriate… It’s a long time.
[01:00:21] Adam Fishman: I have a variety of answers. We’ll just leave it at 15 minutes. I think that’s a good one. What is your favorite dad hack for road trips or flights?
[01:00:30] Caleb Avery: I feel like the iPads feel like the cheat code now that the kids are old enough, but even still, we won’t let them have them until we’re on the airplane. And so it doesn’t matter if we get an hour drive to the airport, going through security, sitting at the gate, can’t have it. And then you get on that airplane and you finally unlock that iPad and they’re happy campers.
[01:00:55] Adam Fishman: Okay. All right. Final question. Three kids. Colorado. What’s your take on minivans?
[01:01:02] Caleb Avery: Hate them. Worst invention on the planet. My cars have gotten progressively bigger. So one kid, you can drive whatever you want. Two kids, lots and lots of options. Three kids, it’s like, do we buy a bus? At what point are we buying the Sprinter van? But I will never own a minivan. I think at this point, if I don’t have a minivan, you’re not going to buy a minivan. So I’ve got a Lincoln Navigator. I kind of want to get the extended version. We’re just going to keep getting bigger and bigger, but it’s never, never going to be a minivan. And you can mark my words on that.
[01:01:36] Adam Fishman: One quick follow up. Is your wife on the same page? Is she also no minivan or is she team minivan? Yes. Okay.
[01:01:42] Caleb Avery: No.
[01:01:42] Adam Fishman: Okay, good. A household undivided. This is possibly the most important decision. All right. Well, Caleb, this has been really fun. I especially love that story of assembling the golf cart and then performing open heart surgery on the golf cart. Thank you so much for all your candor and enthusiasm here, and I wish you and your three kids and your wife all the best for the rest of the year.
[01:02:07] Caleb Avery: Awesome. Adam, thanks so much for having me on the show. This was awesome.
[01:02:10] Adam Fishman: Thank you for listening to today’s conversation with Caleb Avery. 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. See you next week.