Having Your First Kid At 22 And A Portfolio Management Approach To Parenting | Matt Wensing (father of 4, founder/CEO Summit)

Matt: To do a startup, you're choosing to climb Everest and something else.

Okay. If that doesn't sound good to you, like don't do it. Right. But I'm not going to sit here and say like, oh yeah, I got eight hours of sleep, I exercise, I ate great. You know, kids love me. My wife thought I was fulfilling every possible need. Like, no, that's not how it works. So, you know, finite resources, right? Allocate them wisely.

Adam: Welcome to Startup Dad, the podcast where we dive deep in the lives of dads who are also leaders in the world of startups and business. I'm your host, Adam Fishman. In today's episode, I sat down with Matt Wensing. For nearly 20 years, Matt has been a founder and CEO. Starting with founding a company called Risk Pulse, where he now sits on the board.

To today, where he is the founder and CEO of Summit, a no code platform for building tools and workflow automations. He's a loving husband and the father of four teenagers. In our conversation today, we spoke at length about getting married and having kids in your very early 20s. How little he knew, and how amazing it is to be a young dad with children now in their teens.

We talked about how you have to eliminate the excess from your life if you want to prioritize work and family, and he uses a powerful metaphor around points allocation to describe it. We ended with two deep topics. Helping teens navigate a tech first world successfully, including a growing awareness of the impact of social media on teenage girls, and how losing one of his own parents to cancer unlocked some truths he didn't know before.

Matt's stories were amazing, and I hope you enjoy them.

Adam: I would like to welcome Matt Wensing to the Startup Dad podcast. Matt, it is a pleasure having you here. Thank you so much for joining me today.

Matt: Thanks for having me, Adam.

Adam: Let's dive in. You are the founder and CEO of a company called Summit. I am very curious about this company. It is an AI company as many companies are these days, but it seems like maybe you've always been an AI company. So tell me a little bit about Summit. Cause I'm so curious about it.

Matt: Yeah. Well, thank you. So Summit is a no code platform, but compared to others, what we're focused on is not necessarily moving data from one place to the other. Think of like your Zapiers, your Makes, et cetera. We're focused on the interesting parts in between and the AI era, if you will, makes this incredibly interesting because a lot of folks want to use AI within a workflow that they already have.

You know, have this workflow, it's automated, it's great, but now they have all these AI powers are like, how can I bring those in? You know, how do I just bring in a little, we call it like a little surgical strike of AI, if you will, into this workflow, which is going to make it like five times better.

And what we're enabling is it just becomes much easier to leverage AI within your Zaps, within your HubSpot workflows, et cetera. And it's a no code platform. So you don't have to be a developer to build it. So if you know how to build automations and those. You can now use us to enhance your automations.

And that's what we do.

Adam: I love that. Probably helping a ton of companies out there and you've been in business for four plus years?

Matt: Four years. Yeah. Yeah. These are never short journeys.

Adam: No, no. And you, I saw that you were at like a very long term founder before that. So we're going to get into all of this stuff. All right. So that is probably the last work topic that we're going to talk about on the show, because this is a parenting podcast.

So I'm going to go all the way back in the timeline here and ask you about your life growing up. What was Matt like as a kid? 

Matt: Oh man. Uh, I'll say very introverted growing up probably resonates with a lot of other folks listening, perhaps. I was, you know, consumed with, I love to draw. I loved art. I was the kid in elementary school that when art class happened, kids would kind of come around my desk and see what I was doing and making and drawing.

I was blessed with with the gift of kind of art and drawing. My dad gave me that, he's an architect and really always loved art and engineering, I think as a result, I kind of always saw things and things that were made as like a combination of aesthetics and design and real physics. And so my dad was really influential in that.

And then I say, my mom gave me the gift, she's a hundred percent Hungarian and gave me the gift of. You know what? You got to actually put yourself out there in life and talk and engage and travel and all these things. So from her side, I got the, well, things don't just happen on their own. You actually have to come out of your shell, you know, stop playing video games for a while and go tell somebody what you made. Right. So kind of a very otherwise typical. Suburban 80s and 90s kid latchkey kid came home to an empty house and had to figure out what to do. Do my chores, ride my bike around the neighborhood until it got dark. Kind of miss those days.

Adam: Yeah, yeah, that is a foregone era, I think for a lot of parents. So, you grew up in the U.S. what part of the country did you grow up in?

Matt: I grew up in South Florida, so I was like, say, about an hour north of Miami, West Palm Beach area. Yeah, a lot of family down there.

Adam: All right. Awesome. Did you have any siblings or any, anybody to beat up on when you got home from school?

Matt: I was the youngest, so,

Adam: So you got the beating up on.

Matt: I did. I did. My brother was four years older and I feel like he was, we would definitely have our spats. We were more different than similar. And so I think that actually was like a pressure release valve where he was great at the things I wasn't.

We would do stuff together. We'd hang out all summer at the grandparents house, build forts, do fun stuff like that in the Carolinas and Georgia, made great memories, my siblings, we fought a little bit but mostly we were just friends. And I think having that gap relieved some of that.

Like competition, if you will. It was never really competition. I'll say that, that's probably the best description. It was, he can drive now, cool, you know, he could take me somewhere or, you know, we would do things together, but we were never competing. Which I think was a good thing.

Adam: Yeah, and does your brother have a family and does he live near you or..?

Matt: he does. Yeah. So, brother and sister. So my sister's eight years older than me, actually. My brother's four years older. So my sister is a doctor in South Florida. So she lives across the street from where my parents lived for a while. And so she's practicing there. And then my brother is a firefighter paramedic.

He's actually about to get his, what they call, “retirement drop.” So he's actually about to be done with his service. Yeah, he started really young, right out of college, 19 years old, and he will have had 20, what is it? 25 years of service or something like that or whatever it is coming up here. So full pension, all that good stuff, but well deserved and well earned.

And he has a daughter and a wife down there in Florida. So we go visit.

Adam: Okay. Well, you have a partner and four kids, which is double the number of children that I have. They're all teenagers, which is also fun. So you've got like a house full of teenagers I'm curious how did you and your wife meet each other?

Matt: So this answer is, used to be weird. So back in 2001, two and three, so we met in 2001 and in 2001 or more like 2002 when we were dating basically. And I told people, Hey, how'd you meet? I say we met on the internet and people thought that was the weirdest thing in the world because you don't meet serious lifelong friends and partners on the internet.

Like, you know, there was no dating apps or anything, but we met on a message board, believe it or not. It was like, Sleepless in Seattle, practically like the last era of that shows how old I am and yeah we didn't actually meet each other in person until we had sent back a bunch of like, You know, correspondence and chat messages and that whole thing.

And yeah, then we met in person and we got married young. So I think three years later we got married and that was that.

Adam: Okay. So that is one of the reasons that I reached out. I saw you talking about having kids at a very young age, which also implied, I think for you that you got married at a really young age. So how old were you when you had your now 19 year old daughter?

Matt: So she was born in July of 2004 and I turned 23 in November of 04. So I was 22 years old when she was born.

Adam: Wow. And you and your wife had gotten married a year or two before that, or?

Matt: I think we were 21.

Adam: Wow. Okay. I don't think I had the mental and emotional capacity to be married at the age of 21.

Matt: I know that I did either. I mean, if my wife were in the room, she'd say we didn't know what we were doing either. And I think it's so true. It's so true. We didn't. I think we were like, we were two trees that had barely started to grow and we just got planted next to each other, almost. And it was like well, we're either going to like blend together here or not, you know, and we changed a lot, but that was what it was more like that than like, a lot of other metaphors you could use, but you know, we were very malleable still ourselves.

Adam: What was the decision at 21 to get married and then a year later to start a family like is there something about something in your background or in your wife's background that was just like, yeah, this is normal and this is what we're going to do at 21. You know, it's time. 

Matt: I wouldn’t say it was in my background so much. A little bit my wife's. I mean, we both ended up in a pretty, I'd say like conservative culture by the time we were in our late teens and early twenties. And, you know, just the whole mindset towards dating and relationships and all that. It's a lot of like, and I think it's changed now, but like 20 years ago, it was pretty extreme in that sense of like, you know, it just, there just wasn't that like, hey, you know, date a bunch of people, experiment, see who you like.

Like, you know, feel yourself out, that kind of thing. It was very like, everything's so serious and everything's, you know, this is either something big or it's not. And so we kind of went into it with that mindset. And so it was just like, yeah, it’s weird to say that out loud now looking back, but that's just where our heads were at.

It was very like we took it really seriously. And I think that can be really, so we were in a friend group at the time and sadly I'd say the majority, I don't know if it's actually majority. I hate to say statistical words that aren't true, nerd, but I would say a lot of the friends that we had in our group growing up, they took the same approach.

They didn't, it didn't end up well. Like two years later, three years, five, 10 years, it didn't end up well. So like, that is not a recipe for success. That is not like a advice, you know, it's what we did and we made it, you know, I wouldn't give that advice now. I'm not giving that advice to my kids now.

Adam: Yeah. Yeah.

Matt: And my parents didn't give it to me, but you know, did I listen? No. Did it work out? Yeah. But, you know, I feel very fortunate that it did.

Adam: Yeah. So your wife and you get married, and by the way, your wife's name is Skye, right? I don't want to refer to her as your wife. So Skye and you get married pretty young, barely able to legally drink alcohol at your wedding. And then you decided to start a family pretty shortly thereafter.

What was that decision like?

Matt: Well, well, remember we just got done saying that our, you know, intellectual mental faculties weren't all there yet. So decision is a strong word. we always told her oldest, like you weren't an accident, but you weren't like by design either. I think it was sort of a, like, we're married now and we're not really afraid of anything.

And so let's just let life happen kind of thing. So yeah, I think at the time I had a part time job. I remember I was making $10 an hour at one job, $12 an hour at another. No benefits. She had also a similar situation. So yeah, we were just living in a little apartment in the suburbs of Chicago and quote unquote made that decision.

But again, it was more of a, you know, what can life do to us? We're invincible, right? We'll be fine. We're going to be fine. That was our mantra. It still is. It's going to be fine. So, so not the types to worry too much in that sense.

Adam: So you're barely out of college when you have your first kid, you're in your early twenties. And this is, you know, I had kids relatively early by Bay Area standards, but I was still in my late 20s when our daughter was born. And so I'm curious you now have a 19 year old, a 15 year old and two twin 13 year olds?

Matt: 13 year old, right.

Adam: So you've got a full house in all senses of…when you think back on the last, like 20 years and having kids at a really young age, what are some of the reflections that you have on that decision and kind of like what it means to be a young dad? I mean, your kids are not too far away from being out of the house and you're still a pretty young guy.

Matt: Yea. So I took my son to my second drive now he's got a car he's got a summertime job coming up. He needed to go for a drug test for that mandatory thing. So we need to go to this clinic. So I'm like, you're driving. So I get in the car, eating my snack.

He's driving us to his thing. He's gonna, he's yeah, 15 this year. This is what happens actually. You start like, he just turned six. He just turned 16 actually. So I screwed up the dock. This is what happens when you're, so he turned 16 in February, it rolled by and I just like went right through it.

Adam: Yeah. It's just another birthday of among many.

Matt: Yeah, yeah, exactly. So he turned 16 a couple months ago, and so he's that's why he has his license. Now he's driving. Anyway, we get there. We go to the front thing. The guy goes I said, since he's a minor, you know, do I go back there with him when they call his name kind of thing? Because, like, as a parent, that's kind of a new experience.

And he goes what's your relation? And I was like father, he's, and he goes, oh, seriously, sir I thought maybe you were his like older brother or something like that. And I go, well, okay. Taking a step back. He plays varsity football. He's like 5’11, 175. He's a big kid. It does not look like he could possibly descend from me at this point.

And I'm like, no, this is actually my son. So, so those things are happening now. It's fun. It's always been a lot of fun. I would say having the energy to live through twins was really nice.

I couldn't obviously life finds a way, but doing that now would be harder. Keeping up with them is fun. but from their perspective, I think one really nice thing is our kids, when they were born, were all born into circumstances that were not as comfortable as they are now. And so you can't go back and I'm not saying this is a requirement or anything, but just like, encouragement for people who maybe are thinking about it or have kids young.

It tends to be the case, especially if you work in tech or elsewhere, that like you earn more as you go, like you become more senior, life gets easier. You know, you can buy them the car now kind of thing. But when our twins were born, we were in a two bedroom apartment. We were sort of stepping over things and there were a lot of things we just couldn't do. A lot. You know, our first family vacations were not, you know, Whistler ski trips. They were, let's go to the state park in the minivan and, you know, put up a tent, and like bike around and, you know, figure out what's fun about the bugs that are crawling around or the creek.

And so you'd like, get that experience as a kid. And I think some of those experiences, frankly, are more challenging, might be the wrong word, but just like we said at the intro to my life, it's the, I have to kind of make do with less things around me. And, you know, especially in a larger family, when you sort of have less to go around, I just think they got that experience and I'm glad. So like the oldest one, especially, she's 19, she remembers how life was, you know, years ago and I'm glad she got to experience that. You know, she's now getting her first apartment. She's in college now. She's lived in a place before that, where she just had a little electric stove and whatever, and not the fancy Samsung refrigerator. So she's not like, not used to life, you know, as that. So that's one fun thing.

And otherwise I would say, yeah, just having the energy has been good kind of being with it. There's all those silver linings, you know, and then yes, there's all the downsides too, but those are the upsides.

Adam: When you look at other people who are sort of similarly aged to you, do many of them have, you know, multiple teenage children or they have younger kids or…?

Matt: So this is what happens. It's funny that you say this and this affects us, right? Because our friends as parents of kids are often our kids, friends, parents. I

got that right, right?

Adam: I followed you.

Matt: yeah, yeah, yeah. And we all know inevitably sometimes, or, you know, you'll learn I'm not really friends with her anymore.

And you're like, oh, that's kind of awkward. Like, I actually kind of emotionally invested in that or, you know, or we are friends or we're going to different high schools because we're zoned differently. So I don't even really see them anymore. And so you're almost like in this washing machine of your own, of like your social group, as you said, like just based on where your kids are sort of attaching, but here's what happened on that.

It's funny. So when our oldest was doing her first things, we would show up to things and we were like in our early twenties. And you know, we would regularly be with parents who were like, sometimes like 10, 15, 20 years older than us, like sitting around a jimboree or whatever, a play date. And we're like, we're just not even in the same generation. This is funny.

Adam:  The parentsare waiting for you to jump in the ball pit!

Matt: Exactly, they're like you must be the nanny or the oldest. Are you like, is this the young, do you have like 11 kids and this is the youngest one and you're the oldest one? Like what is going on? You're the oldest cousin, I guess. And so then as they grew up, by the time we get to the youngest now, you know, the 13 year olds, their parents are a little bit older than us, but what we basically find is that might be their oldest or middle kid. You know, and so we've the ladders have kind of shifted and aligned where we're getting closer in age to them, but then you find out that like, oh, this is our youngest, this is your oldest, or this is your whatever, but we're closer in age now. And that's kind of fun too, because those were, those are, I would realize those, they go out and hang out with some of those guys or whatever, and they're sitting there talking and like my favorite music, if I'm being nostalgic, it's like, oh yeah, like Pearl Jams, Stone Temple Pilots, like, you know, there's a few that are maybe earlier. They're sitting there dropping like the Led Zeppelin references, and the this, and I'm like, I know they're hits, but like, I don't know they're deep cuts. Like, we're obviously not the same generation here.

But it's fine, it's fine, like, I have those conversations with anybody, so,

Adam: Yeah, you're like, can we go talk about Soundgarden for a bit or Stone Temple Pilots.

Matt: Yeah, exactly. Like, like, they're like, oh yeah, they were, I went to, I saw them live when I was 23 and you're like, huh? You're like, hmm. Yeah I exactly. Like, I have, I borrowed my brother's CD. Yeah, exactly. When I was 12.

So yeah, a little different.

Adam: Yeah. So if you were, if you can think back to you know, you're an early twenties parent and a lot of dads don't talk about or think about the kind of emotions that come up when you're a father for the first time or the second time, or in your case, the third and fourth time.

What sort of emotions arose for you as an early twenties parent where you completely freaked out because you were yourself so young, or were you like. You know, you've mentioned before, like, hey, we got this. We'll just roll with it. But like, how do you think, you know, that went for you as a young parent?

Matt: Yeah, yeah, yeah. It reminds me of that Jurassic Park quote, it's like, it always sounds fun at first, but then like, what does he say, like, then the screaming and the yelling and the whatever yeah, yeah, like, it always starts fun. I think the naivety allowed me, and I'll just speak for myself, to like, jump into that pool pretty ignorantly. I think my wife, being a woman and being more mature in many ways, like, kind of realized what it was going to take before I did, honestly. I think I was still living a little bit of a college guy's mentality life, not in the partying sense. I already said, like, I went to a nerd school.

I was a geek. I'm not about that. It was just like, oh, I have free time. I can do stuff or whatever I have this, right? I think the biggest thing that hit me the soonest was just realizing that just a lot of the free time I had was gone. It was, It was still there, but it was going to be replaced by this life that needed me every 11 seconds it felt like, five minutes, 11 minutes, whatever it was, but there was no time for me to like, you know, goodbye Madden 2004, you know, , see ya in the future, maybe kind of thing. That was hard, you know, like, oh yeah, I'm not going to see another live show again for a long time. I'm not going to, you know, just the few outlets I had in that sense.

And my wife was extremely supportive. I supported her if we needed to get out. Like we did that for each other for sure. But you know, that's like a rarity. That's not like, that's not every day, pretty much every day you're in the trenches with each other. And you know, if you can read it on your Kindle while you're wearing the ergo or something good for you.

But like, You're not going to see that movie. The 11 o'clock showing that is not happening. So that was hard. And I think the other emotional thing was more like, accepting or realizing that a lot of the advice that I was getting was only going to work some of the time.

And we had kids that were very I'm sure a lot of people say this, but like, let me just say shout out to the parents who have the kids who are not like staring up into space and just kind of waiting for the next thing. The ones who were like, you can see it in their eyes that they're like, they're analyzing everything.

They're three steps ahead of everything, you know, and they know what's about to happen before it happens somehow, even though it shouldn't be the case and they're testing you every moment,

That's a different experience. And I would talk to friends, especially friends who had, you know, a lot of children and you're like, oh, you had a lot of children cause yours are kind of just waiting around for the next thing. Like, it's just a different thing. And you're handing me this book that says how easy it is to sleep train and do this and do that. And I'm going, why am I at my wits end? And eventually over enough time, I met other parents who go oh yeah our kids are like that too.

Like we understand, you know, and like they have that glimmer in their eye at a very early age and you're like, okay, so I'm not just a failure. And I'm not just not able to follow the advice. It just turns out that nobody wants to read or write a book about certain kinds of challenges because you couldn't make a lot of money by saying like and actually I don't know how to do this. It's going to come down to whatever play you got to call in the huddle as it's happening. Godspeed, right?

Like what? Like I want a refund. Yeah.

So that was hard. I would say that was difficult. It feels like that's basically seven years of emotions in seven minutes.

Adam: So you, you've been building companies and growing a family since, by my calculations, like 2006 or so from some LinkedIn sleuthing that I did about you. What advice do you have for people who are trying to do both?

Matt: I like to think of it as like, character points. Okay. So you have this, like you get to design your character and you have like a 100, 10 points to allocate. Let's keep it simple. You've got your categories of like, hobbies, spouse, career, kids.

You can only allocate 10 points across all four of those, and like anything less than a six and you're probably not even going to be able to make like, you're going to be able to tread water with like a four, maybe anything less than that, like it's gone. That's the reality. Your time is a zero sum game basically. And I think I had to let go of something like basically like people were like, oh yeah. Oh my gosh. That movie, like the whatever, whatever.

I'm like, why is this not resonate? When did this come out? And they're like, I look it up. Oh, 2011. Okay. That explains why I've like never heard of it. I've never seen it. I have no idea what you're talking about because like there was no time for that. Like I chose two things. I chose career. It was just building the business and I chose kids.

I would say spouse was a treading water thing for a long time. And hobbies and whatever else you went with her. That was basically a zero, right? I had to be a zero. There wasn't enough points left. Right. what would I say my breakdown was, is actually a real talk.

It's like, I was probably. I always tried to maintain at least a six or greater for the business that left me with four points to spread across kids and spouse and hobbies. So, you know, hobbies had to be zero. I mean, I was borrowing from categories like sleep, you know, which isn't… health is probably another category, you know, I mean, God bless you if you can get up at 4 am and do that as well, but that's what I ended up doing. So I will say my schedule ended up being pretty insane. Like. was a while where I'd actually get up at 4 30 in the morning, code, I would actually, I was always an early riser mentally. I was like, I'm sharp in the morning.

So like, if you're not, I get it, but I would get up at 4 30. I would code from 5 to 7 or 5 to 8 when breakfast family breakfast was, I would get my core work done before family breakfast even happened.

Adam: Wow.

Matt: Which left me free to like be an involved dad. I worked from home before that was very popular either.

So then from like, so 8 AM, you know, the Cheerios thing, the high chairs, all that stuff, we got to go to Costco. She's not going to go alone. I'm going to go and help out. You know, that let me basically be free to at least be physically present from eight to two, nap time, basically. And then nap time was another session of email and coding and whatever.

And then if they went to bed and all things went well, and you know, I was free again by nine or 10, I could do, you know, I, maybe I could do 30 minutes of work then, or sometimes I would work, I hate to say it. I worked till 12 o'clock or one in the morning. I'd get maybe five hours of sleep. You know, you can't sustain that, but like to do a startup, you're choosing to climb Everest and something else.

Okay. If that doesn't sound good to you, like don't do it. Right. But I'm not going to sit here and say like, Oh yeah, I got eight hours of sleep, I exercise, I ate great. You know, kids love me. My wife thought I was fulfilling every possible need. Like, no, that's not how it works. So, you know, finite resources, right?

Allocate them wisely.

Adam: I love the real talk because that's the truth that people need to hear,

Matt: Yeah. And I think like occasionally I would shift gears and say like, you know, I really need to focus on my sleep. So I'm going to give up this part or I'm going to take that. I'm going to take that nap in the afternoon when they nap because I'm freaking at the wall. Like I call it hit the wall. I tell my wife I've hit a wall.

That means like I got to sleep some to catch up. But you know, part of that was being 23 and having infinity energy too. So, you know, I wouldn't do the same thing now. I don't think I could.

Adam: Right. I was going to ask, if you think about this points allocation, How would you say your points allocation has changed as the kids have gotten older and you've matured and also gotten older and, or just learned about your limits or what works and doesn't work?

Matt: It was definitely, you know, health and sleep was like a zero category for a long time. Thankfully I was able to do that without like terrible consequences. I'll say this. Like. The kids doesn't have to be a seven or a six or, you know, any more because, it's funny, you say a full house. Yes and no. Actually, the thing about teenagers that is really surprising is how absent they are compared to before. So, you know, we talk a lot and we dramatize the conflicts, the emotional things and all of that. But don't forget when you watch the sitcoms or the shows as movies, that's happening in the five minutes of interaction that the parents have with the kid, as they're grabbing their car keys to go out the door, as they're showing up late, cause they were at a friend's house as they don't want to talk about their day and going and hiding in their room so that you're not physically engaged or present with them as much, even though they're still there, right. And I think that's a healthy thing. It's a great thing. And my son's like, hey, I'm going to, you know, I'm going to go over to my friend's house and do this tonight. I'm not looking for a reason to say no, you know, I'm like, awesome. Sounds great. Like I'm secure. I don't need you to be home for any reason.

So what I'm trying to say is that freedom has allowed me to say, like, going to take a nap, I'm going to sleep in if I need to, I'm going to go use the rower for half an hour and I'm not needed. Right. And I was able to, I would say, shift some back to the health piece there.

I'd say you Also, just that freedom of attention means that, you know, if my wife and I want to go out during the day or spend time together or do whatever, travel together those are all available to us now and they just literally aren't, you know, and that's normal, I guess that's what I'm trying to say too, is like, it's normal that they're not, but you do get to play with that equalizer, if you will, and shift those things around later.

Because the pressure comes off of one of them where they're like, dad, I just need, I need this now. This is what I need out of you. And you're like, okay, you know, I can do that. It takes me 15 minutes. But also I'd say like the ability to pull someone aside sounds wrong, but say like, hey, do you want to go out to eat?

Hey, the house is free. It's just us tonight. You know, do you want to hang out? Like, you know, we'll go to the wings place. So we'll go here. We'll do this. That's really cool. You know? And to know that like. It's not because your spouse is like at home, you know, holding it down with the rest. It's just like, actually everyone's kind of doing their own thing.

Except for us, you know, do you want to hang out for a bit? And they say yes. And you're like, best feeling in the world. Right.

Adam: Yeah. That's awesome. That's awesome. So I wanted to ask you about advice. You know, when you're a parent or when you're becoming a parent, you get a lot of advice some of it is good. Most of it is bad. But if you could rewind the clock and you're just getting peppered with advice by people and maybe this didn't happen to you.

But I do find that it happens a lot. Or maybe you're being bombarded by Instagram advice and TikTok videos about how to be a better parent, stuff like that. What advice that you got, would you tell yourself to completely ignore?

Matt: So I was seeking out a lot of advice then. Because, you know, being the A plus student types. You know, it's like we want to ace this. This is a new classroom rolled in called parenting. I want to get an A. And so you're like, voracious. you know, So you're taking the stuff in and you're like, a lot of times people are dropping knowledge and you're like, this is amazing.

This person has all the success of these kids is going great. I think though, what's really dangerous though, is that man, until the score settles out, right, until the game is like over, if you will, you don't really know who's won in this game. And so when you get advice from people and you like, look and you're like, oh yeah, everyone's just sort of in order and locks, everyone's, the kids are smiling, everything seems so put together.

Like it's working. They're winning. Right,

Adam: Yeah.

Matt: Man. Like don't judge yet. Like don't assume that it's working actually, because humans are extremely complex. Kids are still developing that relationship that the parent has, the kid is changing, I saw enough people sort of run with advice that I got early and like stick with it.

Adam: Mmhmm

Matt: The results weren't great. And they were actually like the opposite of what I was going for. And so, I saw, you know, oh, they're three years older, five years older, 10 years older. Like that's the next wave. It's talking to somebody who's along the path, but I would say like, if those kids aren't like adults yet and they're not thriving and they don't have a good relationship with their parents, still, like let the jury sort of wait it out, right? Because what you're really going for as a parent isn't obedient looking teenagers on the outside or little toddlers that, you know, never fuss or whatever you're looking for. Like, I want to be in a situation when I'm in my forties, fifties, sixties or whatever, where my kids want me to help take care of their kids.

If that's a thing where my kids are like calling me and we're having good, like, I want that. Right.

Adam: Yeah.

Matt: But those people, like, honestly they're even more rare. And I think like, that is so rare that you don't even necessarily find them available for advice. Cause just most people don't have that experience.

And so I would tell myself, Matt is like, don't assume that it's working yet, just cause it looks like it's working would be one thing. And I think that that would cut across a lot of advice. And then I would also say being a little bit more, I was pretty strict. I would say I got less strict.

Obviously time goes by. I think that's natural.

I think that's natural because I think we realize that actually it kind of works as well in many cases. I'm not saying no boundaries, please don't misunderstand, but I'm saying like, there's a difference between boundaries and strict, and I think like strict is easier to actually do than boundaries, you know, a very strict leadership style.

We all know companies are the same way. You know, it's sort of like the boss that like everyone has to listen to. But like, do you want to talk to them? Do you want to like go out to eat? Do you actually want a relationship with them?

Adam: Yeah.

Matt: You know, it really does come down to the heart.

And I think fortunately, I feel like we realized that in time, but I still think we started out like way too like we're gonna nail this and obviously the answer is to be really disciplined about all this stuff and like 10 years from now. You'll probably think that was all just like hilarious naivety.

Adam: Yep.

Matt: And like, maybe you can't learn any other way. So that's fine too. Like you're not going to listen to me saying this out loud and also learn, like you kind of maybe have to learn, but I remember a little story. We were doing sleep training with one cause we were told that that was like the way to do it.

And so our oldest, Again, like first one. Yeah, we're going to do this right. I feel like we, we like do that thing. We're like, okay, we're just gonna let them cry. Cause you know that's not love. You know, it's okay. You know, we, every need's met. Like they should just go to sleep. We read the book and it was like, oh yeah, it's normal like if they cry for some amount of time, but then they'll, whatever, a little bit, go to sleep. So our oldest. She's in there crying like, okay, it's gone on a little bit longer than the book says, but then there's quiet. I’m lik oh, yeah. Yeah. I literally remember the movie. We were watching the Russell Crowe movie, Master and Commander.

Okay. I remember the movie that was even on, right? We're watching this thing. We're having our, like, us time, like, which is super rare because the kids are in bed. It was like 11 minutes later, or the next scene, suddenly, boom, just eruption, like, back at it, full force, not, and we're like, but that's not what the book said, like, the book said, but the book said, like, that this wasn't gonna happen, and, by the way, this wasn't like the first night we tried it, or the second night, this is like weeks of trying this stuff, and we just went like, maybe this book isn't a fit for her.

Like this is maybe just not the answer. And then you're like, but this person has four kids. That's fine. That's how random works. Guys. Do you realize it's bunchy? They could have four where it all works. You can have four where it doesn't work. And this poor person over here has the first one where it works.

And then the next one where it doesn't just to gaslight them into thinking that they know something. Right. And then they get the second one. So, you know, those were things where sure, if it works great, but like, if it's not working, what do you know, what are we doing here?

Right. It's, we're not trying to like. Be the, you know, greatest number of successes with this method. You only get four shots or two shots or one shot. Like your goal is to do what works for each. And when you have older kids, they will look and go, wait a minute, you're parenting them different.

Adam: Yeah.

Matt: Yes, leadership styles actually have to be about.

And that's something I learned at work. I remember early on in my career as a manager I had a mentor and I said, you know, I just want to send this email out. Everyone just opens the email and reads it. And these people open the email and read it and they actually do the thing. And then like these people don't do it and he goes, well, they used to report to me and they did stuff and it's like, okay, well, what's your secret?

He's like, well, for that person to do it, you actually need to have a conversation. You need to like talk to them. It might take five minutes. It might take 10 minutes, maybe it's a phone call or whatever. And I go, okay, that's not scalable though. And that's not like, that's not as efficient. And I don't want to do that or whatever.

And then it comes down to like, but are you trying to lead these individuals? Are you trying to just do what works for you?

Adam: Yeah.

Matt: What is your goal here? And I really, parenting is like the ultimate version of that. We were like, there's no swapping this employee out. There's no corporate organization, reshuffling is going to happen.

Adam: We're going to re-org you.

Matt: This is who you're working with. Yeah. You're going to be reorgs

Adam: Twins. You're being reorg. You're now reporting to mom.

Matt: Yeah, actually auntie and uncle. Yeah. You're going to be with them for a while. But So yeah, you got to do what works for each one. And so it's like, well, how come you did this? It's like, well, if I did that with you, would it work?

No. Okay. If I did this with you, would it work? Nope. So you understand, I have to approach this differently. Right. And like, oh, okay. You know, it's a blast.

Adam: You mentioned a lot in that, last thing we were talking about, about the parallels between work and professional life and family life and like working with employees, working with kids, do you think that being a parent has made you a better CEO and founder?

Matt: Hmm.

Adam: I know you don't have a controlled ab test here because you've basically been a parent as long as you've been a founder.

Matt: I don't know. Yeah. And part of me wants to do that. What's that? That awesome response. Yochich when he was asked the NBA, are you a better basketball player because of of your family life? And he just goes, no,

Adam: Mm-Hmm.

Matt: And everyone was like, you do realize that the NBA is trying to turn you into a superstar.

Right. would say that the honest answer is I don't know. However, the parallels would be things like I think that I have had to, through the crucible of parenting, and I mean that in the nicest way possible, it's got its joys, don't get me wrong, you really do learn about, let's say you have a family of two, okay you could argue there's one relationship, which is, you know, me to her, or her to me, or whatever, I actually look at it as there's more relationships than that, there's myself and what I think of myself, there's myself and what I think of her, And then there's what I think of our relationship and then vice versa, right?

So you have all these mappings, right? All, all these complexities. And it explodes. And I think family life has sort of showed me that, oh wow, I am in a, you know, again, I use all these words, inescapable experiment, or social experiment in a way of going, this person just said these words, I'm in the same room, I heard them, and I know what I took away. That does not at all mean that person over there, the kid, or the parent, took it the same way. Right. Because I have all this history and context that neither of them have. And I even have my own perception of, oh, my goodness, their relationship. Right. And that has taught me is that when I say something at work, the assumption of clarity is almost always presumptuous, right?

Or wrong. It's like, hey, I, you know, we had to get in a private conversation. Hey, we had this, you know, a meeting today. I said this and this, like, what did you take away from that? Or what does that mean to you? Or was it clear when I said this, you know, the odds that they took away something completely different or didn't take away is high, you know?

And I think I, because I, enjoy thinking about these things. And I feel like it's just sort of a it's my role sort of in life and a lot of situations, even growing up, I'll say it this way, even growing up. I always felt like I was kind of the town translator or communicator. Like I was very often helping my brother understand what my mom meant.

Helped my mom understand what my dad, like. I guess I enjoyed it, but I also find it kind of fascinating and could also call it an undue burden as a kid to have to do that. As a parent I think it's more of your responsibility. And as a leader at work, it's more of your actual paid responsibility to be that translator and say, do we actually understand what each other is saying?

And why are we saying it? And I think the translatable thing here is good questions are the best, leadership 102 maybe is learn to ask good questions. What are you actually saying? Why why are you saying that? What are you worried is going to happen? Right. Is oftentimes the root cause because whether it's at work or home, it turns out feelings are actually really the driver of so much behavior.

I'm worried that the site won't launch in time. That's actually what's driving you going, hey, everyone, you know, this wasn't done by then and that's terrible. And we got to do this by then this is the most important priority or whatever. Oh, if you peel all that back, I'm worried the site won't launch in time because if it doesn't, then this terrible stuff will happen.

The leadership skill of going like, actually, that terrible stuff isn't going to happen, or we can mitigate that terrible stuff. Now, do you feel differently about priorities? Oh, yeah! Like, I wouldn't have even said we have to do that by then if that's the case or whatever. You're like, oh my goodness. So, with a kid, you know, like, why are you saying that?

Well, I'm just worried that if this is the case, then this. Wow. Okay. Guess what, like, that's not gonna happen, and it's not gonna happen because of this, but the words that are coming out are, like, stacked on, like, five assumptions, emotions at the bottom, assumptions stacked on top, and then verbal expression, like, this cantilevered off the top of this stack of cards.

And you're like, and then you listen to a conversation and this person only hears that part and they respond to just that little cantilever. That's just that verbal expression on top. And you're going, okay, it's my job to actually like unpack and unwind all of this. And I will say, man, this goes back to the hobbies.

You want a hobby. You want something that's going to consume an hour of your time. Talk to a 13 year old about what was their actual root cause of them saying what they said.

Adam: Try to navigate that.

Matt: Yeah. And like, I'm not saying that everybody has to, you know, therapy, sure, get help, like there's always an answer, but I think so much of that just gets like packed down and paved over. Right.

Adam: Mmhmm.

Matt: And you know, yes, it's like any other kind of debt that maybe it doesn't take an hour if you do it regularly, if you get in the habit of it, but like, there's a lot of times where that's your, I feel like that's the role of the parent in a large household and that's your role as a leader at work. If you want to keep these people, is to say like, why are these people saying this? Because everything else comes out of the mouth is pretty smart.

This one seems weird or off, you know, let me tease out what's really going on.

And you know, a lot of a lot of late nights, but now, you know, I would say, it’s a beautiful thing when like they're 17, 18, 19, and they reach out to you and say, like, I want to talk about something that's difficult.

Adam: Mm hmm. Yeah.

Matt: Was it worth all those hours? I think so. But like, there ain't, there's no shortcut right either.

And I'm also not saying, you know, if you can't do this, that's fine. Maybe your spouse can, one of you, if not get help, but like real talk, that's gotta happen. Right. I don't think you can like not do that?

I don't think you can not do that at work either. I think a lot of people don't do it at work and then their companies kind of become toxic, right?

Would be the takeaway.

Adam: Yeah. They don't get down into the root, the underlying root cause and root emotion there.

 Matt: It's too hard.

Adam: You and your wife your partner have been together for a couple of decades now, more, a little bit more than a couple of decades. And you've raised, or in the process of raising four kids.

Partnership is super important when you have kids and also you got married and sort of partnered up at a pretty young age. You change a lot over the course of your twenties and your thirties. And you change a lot after you have kids. It's impossible to agree a hundred percent of the time with your spouse.

What is something that you and Skye don't see eye to eye on when it comes to parenting?

Matt: Okay. So we have different fears, I would say, that drive us. And I have learned, we have learned to embrace that as a strength, meaning our powers combined, we're looking out for everything. So I am always worried about, especially when they're young, physical dangers. Now we do things, we do activities, go boating, skiing, you know, we're like, we play in the mud, we jump off of short enough cliffs kind of thing. Like we have a lot of fun. Don't get me wrong. We used to go to national parks all the time. I mean, we're adventurous, but I'm always like the one to say like, watch out, don't do this, whatever. Like I'm always afraid of people getting hurt. It's just my thing. And my, joke is you know, there's certain things that, you know, money or time can't fix.

Right. And I don't want one of those terrible things to happen. I worry about that stuff. My wife seems to like, just that's just doesn't worry her, right? She doesn't worry about those things. She's just more comfortable with, we did it, we're fine. You know, if they forget to wear their helmet or whatever, it's going to be fine.

And I'm like, okay, I know I survived my childhood and you did yours, but I think it's important for me to have that fear because it's needed, right? It's a good check. On the other hand, she's way more, and I'm gonna get to the disagree part. She is way more concerned about their emotional health, psychological health. She's more concerned about, you know, the stuff they're consuming, the amount of time on the devices, all of that, and going, are they being hurt non physically, but mentally, right? And I would say those are blind spots for each of us. And that would create decent amount of conflict about like, this is happening and I'm really scared and uncomfortable with it and you don't seem to be scared at all.

Adam: Mm.

Matt: What's going on and vice versa. Right? And so I think disagreeing on the appropriate level of like precautions to take on either of those was like a recurring theme for us. And I think rather than agree to disagree, I think I've learned to say like, okay, actually, I think that the safer thing is right to say like, okay, you're being overprotective but I'm going to meet you somewhere that's beyond my level because I know I'm self aware enough to know that I'm like blind to this. Right. So I'm probably like the wrong bar to set. You're probably also the wrong bar to set, but like, what's the downsides of that being the bar?

Adam: Right.

Matt: Probably not that bad. The kid doesn't want to wear the helmet. The kid doesn't want to get off their device, but like in the end, it's for their best, so we're going to do it. Right.

Adam: Mm hmm. Mm

Matt: But I'm not saying that like we came to that, like, I'm aware of myself. You're aware of yourself. We're aware of our different, all that, like, yeah, it turns out that takes like a long time to figure out.

Adam: Yeah. It takes a lot of conversations.

Matt: In the beginning you're both just at the beginning, you're both just saying the surface level stuff of like, this must happen and this must happen.

And the other one's like, I don't think that needs to happen. Right. And you're like how are you, how is that not terrifying you? Right. But I'd say part of the reason we've stayed together so long is we've kind of learned to actually find that synthesis, I like to call it.

And whether it's me or her, if we go to the root cause, we typically find out, oh, we can actually address like that danger and my danger concern. These aren't mutually exclusive. It turns out like, we're not even like, we're competing for air time and attention at this level, but like, we could actually have both.

Like we could make both better. But it's funny, like a lot, time is so scarce, right? And energy is so finite that a lot of the times the words we hear come out of our partner's mouths, we assume that's like the only thing they care about, or the most important thing they care about.

And it's just like, it's just their internal little siren going off saying like, somebody has got to care about this. Right.

Adam: Yeah.

Matt: And don't misread that as I don't care at all about the other thing. Right. And maybe they're just not scared of the other thing they care, but they're just not scared. Right. Just like that's been an interesting journey.

I would say the conflict then comes up what? It's not that we, oh, we're having this long mature conversation and we're arguing. No, the conflict comes when one of us doesn't actually voice our concern with their lack of concern and we just internalize it and we go like, oh my gosh, she's not even like, doesn't really care about that.

Now I'm arguing with like my own perception of her, right. And going like, how could you not care about that? It's so important. Like, what did, you know, it's a terrible person. Like, so then that breeds that like anger or resentment or conflict emerges, not because you're having this like wonderfully mature couch sofa conversation.

It's this pent up frustration with my perception of them. And then I go hot into a conversation with that as like my, like, that's my bogey, like, that's you know, yeah, that's where it comes from. So, yeah that's how we work very differently.

Adam: Love that. And it sounds like the main advice there is, you know, put it on the table and don't draw your own conclusions before you, you know, don't get kind of trapped inside your own head with the interpretation of what somebody else's position is. Like, put it out there. And talk about it.

Matt: Yeah. And it's so hard. It's so, that's so hard, right? Because you're like, I've lived with this person for insert years, months, whatever, decades. You can so easily spin up a avatar of them that you think is like, this is them. This is like, I know them, like, this is what they're going to do. This is what they would say- that is like, that is the enemy.

You know, somehow you've got to like, resist the temptation to spin up. What do they call them in AI now? Like they're deep fake, don't deep fake your partner, right? Like give them the freedom to surprise you or like delight you with the fact of like, no, I wasn't thinking that at all.

I'm just terrible with how I said it. Right. Okay. Well, we can work on that. Like, yeah, but that deep fake version of them spins up real fast, you know,

Adam: Yeah. So you mentioned that your wife thinks a lot about the emotional wellbeing and mental wellbeing of your, of your kids. Not to say that you do not, but that tends to be where she indexes a little bit higher than you. I have been reading a lot and there has been a lot of discussion, unless you're living under a rock.

If you work in technology, you're aware of topics around teenage girls or teenagers writ large and social media. And I've been reading this book, The Anxious Generation about that and the impact of a phone based childhood and things like that. So you have three teenage girls. One is like on the cusp of adulthood, right?

As a college student. What have you noticed about your teenagers relationship with technology? And what did you and or your wife do to prepare them for the tech first world that's unavoidable now that we live in?

Matt: Yeah. So I think there's two phases of this in a sense. It's like resist the tide. Right. You know, it's coming. You can put up your levies and your walls and your sandbags and everything. Like it's coming. So what we try to do at first is like, yes, you can play on the iPad. You can watch a show or whatever, but it's not yours.

So they didn't have, there was like this coming of age moment with electronics. I feel like it's actually like the car of today in that sense. Like, and I know people have used that analogy. It's like, when do I get my driver's license? Some kids, but these days, when do I get my phone? So that for us was a, they're in middle school.

Which I know it's also a dangerous time to get a device, but it was like, you're stuck. You didn't catch the bus. Like there's not a teacher there anymore. It's like, okay, Johnny, like get on the bus. You know, it's time to go home. Like you could literally just miss the bus and now you're standing there and you're like, you need to be able to communicate with us.

So pragmatic reason, it made sense, we're not going to like, have you be the kid who can't communicate with their parents who need to. But from there, can I just like set aside a moment to say, Apple has neglected the needs of parents in the electronics category in almost an unforgivable way, in my opinion, because screen time is a disaster.

All of the parental controls are a disaster. They spontaneously or weirdly stop working. They turn off, they turn on again. If you forget the password, goodness, help you. Like, like you have to jailbreak your phone practically, and I've got four kids, so I'm like literally trying to have to, and then like one of them finds out the password.

Adam: You're running tech support for the whole household, right? 

Matt: Oh my gosh.So, so I would say this, like first you resist the things coming in. Then you have them. Then there's obviously plenty of talk around like. There are bad people out there. This is what we're going to allow. It's not allowed. We had one of those, you know, I, I bought like a router for the house, like one of those Disney branded things, as opposed to like, looks at all the traffic, we locked out certain websites.

I stalled as much as I could, like, let's keep the crap out. But it is ultimately like, it is a porous wall. Like, I don't actually think parents should assume. Don't assume that you're going to be able to like, keep it all out forever. That is a bad assumption. And so we also, and I would say my wife, obviously like the irony is that I'm answering this question because she's so much better at this, but it's like the talking about the nasty stuff in a mature way, early, making sure they're aware of it, making sure they understand that exists, what's wrong with it, all that, like, don't have the world break the news to them of this stuff happening.

So like, just like a lot of generally good advice I feel like around this. Actually executing on it is way harder because it requires awkward conversations and uncomfortable things. You're like, is it actually time to talk to my nine year old about this? Like they're only nine, like it's very, you know, and that's, but then you're like, okay, but like they want to have their first sleepover and like, I don't know how, I don't know what's going to happen.

Like they have different rules. And so there's just really dangerous stuff, but I'll say this, the oldest is 19, 13, that's a six year gap. 19 year old has a very different relationship with social media than the 13 year old even. And the people who have kids who are really young now, I think it's going to be different than my 13 year olds.

So, you know, 13 year olds and even the 16 year old. Snapchat, Tik TOK, all that stuff. It's a thing, you know, we have the ability to log into their accounts anytime we want to. We have parental controls. We can talk about any time we will go through it and show them that we're going to go through it.

There's no real, like, we don't read their snap messages at some point, but we can't like, it's always like the, I don't just so you know, like we actually don't want to do this and we don't care about doing this and this isn't something we want to do, but like, don't ever put anything on there that you would not want us to read and know about.

And that requires what? That requires a foundation where they also know that like, they don't have a lot of secrets. Right. So it's not like, oh my gosh, I can't even talk to my friends then. Cause they don't realize how I talk to my friends. Like as a parent, you have to at least have that level of like, you know, Oh, that's great because I don't care because like, I literally, I'm just talking to my friends, like, and you know, how I talk to my friends.

Right. So it's almost like the first test comes earlier where if they don't have any secrets already, then asking for that transparency and trusting them there. You can install, if you will, like measures or safety measures that can work, have a chance of working, but they're not going to buck immediately because they're like, oh, you know, like, well, then I just can't use it at all.

You know? And they're like, well, why not? You know, like now we get now that's a really it's like, well, why can't you use it at all? Like if you're saying that I can and then they'll come up with some excuse or whatever. So like maybe what you should be doing at those younger years is just saying like, okay, yeah, my kids are gonna start talking to their friends differently than, you know, maybe I'm comfortable with or whatever.

If they say this or that, you're not trying to like bust them. That's not your job in life. But you're like, if I can't be allowed into the hall, I can't monitor the hall. So I need to be allowed into as much of their life as possible so that I can stay involved in those channels for as long as I need to, until I see like they're making good choices. They're healthy or whatever. So I mean, we've tried to use all the limits we can. I think that trust of like letting us be in there if we want to has been big. We don't actually, I think we've used it like every once in a while for like having those questions, like, is everything okay with them or whatever?

Like, maybe we'll do that. Typically it's funny, you know, like you have that fear and then you scroll through and you're like, oh yeah, like he's a big Seahawks fan. Like this is a bunch of highlights of their game this weekend. Like.

Adam: Right.

Matt: It's a really, it's the same way I use YouTube, right? It's like they're becoming like us, you know, that's okay.

That's actually the goal. But is it dangerous? Heck yes. And is it unhealthy? Yes, it can be. And I would say like teenagers and mental health and social media is a giant deal. There have definitely been times where we have installed like strict, this is the maximum, you know, I will say to its credit, strangely enough, whereas Apple has failed.

I think some of the individual apps at the app level have done a better job of adding parental controls than the device makers. So just a little, very practical tip. You'd be surprised. Go ahead and check those things actually work. And we've definitely used those. And I think like sometimes kids just need that healthy reminder too of like, oh yeah. I have been staring at my device for two and a half hours. Like that's enough for today. Like I need to like do something else and then they will, but is it a battle? For sure. You know?

And I would also have phases where it's like, okay, it's summer.

You don't have homework or whatever. I'm going to like actually do a little test here. We're going to have a week or two or a month where, and this is when they're teenagers, right? There is no limit on the time. I want to see how you self regulate yourself, like you claim that you can make good choices.

Let me actually see if you can. And then what does that do? It actually allows you to then collect a bunch of data and go back and have a much better conversation

Adam: Controlled experiment.

Matt: Oh boy. Yeah, actually that's kind of crazy. Yes. And then it's like, so you see how, like, this is why we have these guardrails.

Yeah, that makes sense. I'm not going to fight it as much. Cause like I made bad choices. It didn't kill them, but like if you let them spend those times and you can go back and look at it, it's just way more impactful than, you put up the wall. You can never touch the wall. Don't go over the wall. Don't leave the wall.

We know how those parables end, right? Person leaps over the wall, never to be seen again. Something terrible happens, right? This is sort of like, yeah, actually we're just going to put the wall down. And like, if you want to try it, like we're going to trust you. Right. And then you can kind of come back and like not letting them visit anything or do anything, but like in terms of certain dimensions, time or whatever, just like bedtimes, like, okay, yeah.

Why don't you decide what time you're going to bed tonight?

Adam: Mm hmm.

Matt: I've always found that to be like having a much better conversation than later about accountability and being like, so you're not good at this yet. Like you don't ebb and flow. You just flow.

Adam: Yep.

Matt: You're not like, well, I went to bed at eight the next night to make up for it.

It's like, no, actually you didn’t. you know, you just…

Adam: It was 2am every night.

Matt: It was two, you just kept abusing the privilege. And so, those are fun conversations to have though. Cause now I feel like the kid is going like, oh, this is how I earn. Liberties to like decide for myself is by showing that I can handle them responsibly versus like, I just can't ever go past a certain line.

Right. Because all of this is about knowing. I said earlier, it was about me knowing when I could give up. I could cross a line with my health. I could cross a line with this, temporarily, right. But then coming back and like, Just learning to regulate yourself. So that was our goal. We're still not there.

I'll take my own advice. Talk to me. And if the kids turn out like, okay. And well adjusted like in 10 years, great. But man, it's terrible. And I definitely have thoughts. Like, I think it will be not unsurprising if years from now, there's, there's more of a realization that like, okay, this is actually as dangerous as like smoking for the brain or whatever we need to do more than just what it is we're doing now. And I don't know what that is. You know, remove the nicotine, if you will, from the equation, right? Yeah, you know, that's gotta be the thing. And I'm guilty as charged, man. I was reading books. Reading those habit forming product design books. Right? Like, isn't that what we're supposed to be doing?

Adam: Nir Ayal, author of Hooked on the podcast last week.

Matt: Oh my gosh. Are there, that's the book. Yeah. And

Adam: Yeah,

Matt: I read it. I implemented some of that. I get it.

Adam: Yep.

Matt: I don’t know if we know, I got to listen to that now. I'm super curious.

Adam: We've now talked about the opposite of like how you stay focused, avoid distraction , and build healthy habits, which I think is important. I want, I wanted to end with one other question, which is the last topic that you had mentioned to me in our prep for this call, which is around aging parents and kind of managing parents and becoming a parent to your parents and things like that. You mentioned losing a parent and you also mentioned that there are kind of a bunch of truths that you discover or learn about when that happens. And so I'm curious to hear about what you meant by that?

Matt: Yeah. Yeah. So I lost my dad in 2017. So I was. I wasn't young, but I was 30. I wasn't old either. 30. About 35, 36, basically actually I think it's 35 long, long. Well, it was, he had cancer. So, it was losing him in a way that like, it was a surprise, but then it sort of unfolded over the course of months, you know, and like, just with him in particular, like I had, what was really amazing about that was, and the story gets to the truth, he spent over 50 days in the ICU.

Most of those days he could talk. And so, I mean, I say the greatest gift through all of that, as awful as it was like, being able to talk to him, I mean, you know, like, the gift is like, you kind of know what's coming, right, and so, like, you suddenly have no, a lot of those inhibitions and fears just disappear, right.

And melt away and let you get at those truths, right. Without that thing of like, oh, I'll ask him next Thanksgiving or I don't need to know that. Or what if he says this and then that really hurts, whatever. So like that was one part was just like nothing, no dumb question, no question, no, and then there's no time, like the present, literally there's only the present.

So that was part of it. And then the other part was just yeah, like you, you look back and sort of realize life is obviously extremely good. And our brains are really good at only remembering the good parts, you know? And I think the other truth I learned is that like, not everybody has the same relationship.

Not every kid has the same relationship with the parents that you do. Seems obvious. I've even said it a couple of times during this talk, but like, when you lose a parent, interesting how different siblings process it, interesting how. You know, their spouse processes it like that teaches you a lot of trues about, Oh my, you know, he was sort of a different, not that it was a different person to each of us, but he kind of was a different function and person and role for each of us.

And it doesn't mean that he did it right. Like in some of those cases, you know, maybe the role he played or the function he wasn't adequate, you know, definitely, but then you realize like, oh, but once you establish that, you're like, oh wow. But then there were these common things like, oh, with each of us, he was like this, oh, that's really interesting.

Like that's like a, that's a common way he interact with us. And then you sort of take that way and go like, oh, I didn't think of that as like potentially even unique, but now I realized that it's shared. Now we're getting at like the values that he must've had, right.

Because he bothered to do that with each of us, right, that was important enough for him to like, not forget for each of us to be that way. And so you learn a lot about a person. I tell you one funny story was I think this happened after the fact we were reminiscing and like growing up, sitting on the couch, he had a sweet tooth and so did I. And to this day I'll catch myself like putting some ice cream in a bowl at the end of the day or whatever. I'm like, this is like, just like, like, I'm like wearing practically the same like dad uniform that he did. I'm like, what? The white undershirt and the shorts?

I'm like, holy cow. This is crazy. But we always used to have like this candy jar next to the thing. And he loved the jujubes. Like they're like these chewable little gummy candies or whatever. They get stuck in your teeth. They're like, I guess it's just like fun to pick at them while you're watching a really long show.

Adam: A dentist nightmare.

Matt: Exactly. There's should be flossers right next to it. But I always, as a kid, obviously I love the orange ones and the orange ones and the red ones and the yellow ones, like those were delicious. And then they had a green flavor, which was like winter green mint or something and a black flavor, which is like licorice and I hated those of the passion and my dad would always like sit down and make he would always sit down. He'd open up the jar and like, you know, I'd take some obviously I would choose the ones I like and then he would always take the green and the black ones. And I was like, he's like, these are so good or whatever. He would say that. And I was like, man, he is so weird. Like, I can't, I don't know how he can like those or whatever, that's so strange. Come to find out, and I can't confirm this now because he's gone, but rumor has it that he didn't like him either, but two values at play. One is he was frugal and he hated to see things go to waste.

Two, what meant more to him than anything was us getting to have the good ones.

Adam: Ah,

Matt: Because he was a provider first and foremost. So he loved us getting to have the good ones more than he would have enjoyed the good ones for himself.

Adam: Wow.

Matt: And like, that's like a vignette of like, then you're like, oh my God, that fits right. That fits because like his whole life, you know, he's an imperfect person, but like, you then see that throughout the life of a person, you're like, oh my gosh that's why that's the same reason he did this. And that's the same reason he did it as the same reason that, you know, he ate the peanut butter and jelly sandwich so we could go off to college and do this, like,

Adam: Yep.

Matt: Those are like unlocks that you get sort of when you take the time to reflect back. And I think, you know, maybe you can do that. You know, hopefully we can do that with each other when we're still here, but you condense all that down to like, you know, a certain amount of time and you share those stories and you go, Oh my goodness, you know, I never knew that. And like, it actually says way more about life and him and anything than like flavors of, of gummies. So.

Adam: What an amazing story. And yet like such a simple story about jujubes to teach you so much about your dad. And like, I, what an amazing story.

Matt: And we don't know what, little story we're creating for ours right now.

Adam: yeah.

Matt: But we can, yeah, we can.

Adam: All right. Well, that's fantastic. Story is a great thing to end on. And so I wanted to ask you one final question that I ask everyone before we get to rapid fire. How can people follow along or be helpful to you?

Matt: I tweet a lot. So that's my, channel an addiction of choice. So Matt Wensing there. Yeah, I just tweet what comes to mind often and regularly. So love, follows there. And then If you happen to be interested in no code or automation, that's the company that I'm working on now.

I'd love for you to check it out, Summit. But yeah, in general, and I'm always looking for just, yeah, interesting folks, new perspectives. I try to make it a goal to follow people who disagree with me as well on the internet. It just provides that little bit of like, what is it that I'm missing? So, yeah, let me know what you think of my thoughts.

Adam: All right. Well, we will link to your Twitter slash X profile in the show notes along with your company. So, excited to send some people that way. All right. Are you ready for rapid fire?

Matt: Hit me.

Adam: What is the most indispensable parenting product that you have ever purchased?

Matt: The Ergo Baby Carrier.

Adam: Ah, what is the most useless parenting product that you have ever purchased?

Matt: Those playmobiles are supposed to be in and be entertained for a long time? That are giant? And they don't use?

Adam:Yes. Yes. Most frustrating thing that has ever happened to you as a dad?

Matt: Just the inability to get a kid to go to sleep. I mean, that's just That to me was the peak of like, I don't know what I'm doing. I'm failing. I'm at my knees.

Adam: Yeah.

Matt: Yes.

Adam: I'm begging you.

Matt: Three hour bedtimes. Three hour bedtimes. Yes, exactly. Yes.

Adam: What are the favorite ages for your kids? 

Matt: Okay. I would say, I'm loving the teenage years, but I really miss the probably the nine, 10, 11, 12, the preteen, but grown up, you know, those go to the national parks and spend all day together kind of times. You can do that now as you're older, but They're just more like adults and that's different

Adam: How many dad jokes do you tell on average in a given day?

Matt: I'll go with one. I think that might be a little high. I try to, I mean, we're definitely at a multi week multiple per week basis. And some of the kids will even tell them to me now, which just feeds my, feeds my ego.

Adam: Yep. Because you have four teenagers, I am sure that you have embarrassed them a lot, even if you were not trying to, what is the most embarrassing thing that you've ever done in front of your kids or perhaps the thing that they told you was the most embarrassing thing?

Matt: Maybe when there's like a sleepover or something like that, actually there's sleepovers, something like that. And like, yeah, they're hanging out.

They're talking conversation, breakfast or whatever. I, you know, like I may be making breakfast or whatever. Maybe sometimes I'm like a little bit too present or involved or like, you know, am I like telling a joke or two, you know, like maybe my hovering skills aren't perfected yet. Like you got to know when to like swoop in, provide the sustenance and then like swoop out, you know, and like, you know, I don't want to be the guy with the skateboards, like, how's it going kids thing too much. So I think I've done that. I think I've done that, and I just, like, maybe, yeah, that, I know I've done that.

Adam: Okay. And you probably hear about it for many, many, many hours afterwards.

Matt: Yeah, yeah, exactly, or somebody points it out to me afterwards, like, you know, like, oh, oops, yeah.

Adam: Yep. What is the most absurd thing that one of your kids has ever asked you to buy for them?

Matt: Oh, okay, first answer, and she's gonna love this, our oldest, really, we just got a cat, she's still with us, amazingly. Old cat now, but she's a stray, came. We went to a pet store to get like the essentials. And there was like a, how to like raise your cat book or something on one of those like little racks or whatever it was like $14.95 or something like, honey, we don't need that.

We really don't need that. Like, I know it's cute, but it has a picture of a cat in the front. She's like a, she's like a five year old girl. She wants it desperately, you know, or whatever. And I'm like, she wanted it so bad. Yeah I later asked her how that felt, and she said she was pretty devastated that I didn't get it for her.

But the absurdity was just how badly she wanted it, and like, the ratio to the value, and just like, maybe it wasn't like the most absurd thing, but like, it was one of those things where you're like, I gotta put my foot down, right? Like, I can't just I can't just throw this in the shopping cart.

Like I can't do that. So, like there's a lot of cat information on the internet.

Adam: Okay. What is your favorite kids movie?

Matt: Oh, How To Train Your Dragon.

Adam: Good one.

Matt: Ah, wells me up. Good one.

Adam: What is the worst experience that you have ever had assembling a kid's toy or a piece of furniture?

Matt: Oh insert Ikea, probably bookshelf where I realized at the very end that piece A is actually reversible. And while you can screw in the things to the sawdust board on either side if you do it wrong, you're, you can't put the back on it. I mean,

Adam: That’s it. You're over.

Matt: Yes, I've actually rebuilt those things multiple times before and screwed up differently each time. Mmm, yes. 

Adam: But the instructions are just so good. 

Matt:I don't, they don't even have words on them. They're so clear.

Adam: Right. Okay. Have you ever accidentally mixed up your kids names and are you ever able to get your twins names correct?

Matt: Okay, so fortunately they're fraternal, so you'd think that I never would screw it up. But I mean, I have definitely done the blurt out the, you know, Jack, you know, whatever actually I meant you person. And they just look at me and they're like, okay, like with the girls, I have actually started at one end of the age spectrum and had to work my way down.

Adam: Just named all the names.

Matt: Exactly. I think as a parent, like, you know you're at the end when you just say, like, you just start using words like thing and the, do the, verb the thing as your, like, command. Cause you're just like, I can't come up with the words. Could you just fill them in, please? Yeah, it's like…

Adam: All right. You have a very hairy cow looking dog in the background. So this may influence your answer, but how long can a piece of food sit on your floor and you will still eat it?

Matt: Oh, yeah. So the, yeah the cow dog definitely messes this up because you can't, you just can't blow that stuff off. It doesn't work. You know, a piece of fruit or grape or something, you know, grapes have that like shell. And if you rinse it off…?

Adam: Mm hmm.

Matt: Come away unscathed. So like, there's, you know, there's definitely like the 10 second rule there.

I'll tell you a friend of mine once said, when the family was younger, kids would waste all this food. And it was like that frugal mentality were like, there's like half a burger on a plate. And so I'm like, sometimes I eat my burger and then like, I have another portion. Cause like, I eat the hamburger.

My friend goes like, wait, so you're eating trash. I'm like, it's not trash. He's like, you're about to scrape it into the trash. I'm like, it is not garbage until it goes into the trash can. Okay. Like, Before you do the scraping motion, it is completely edible food, right? Exactly. It's still food.

Adam: Uh, what is your absolute favorite nostalgic movie that you have forced your children to watch?

Matt: Well, I started to watch the Goonies with them. And then I realized that movie was actually not age appropriate yet. And I had no idea because I think 80s brain just like blots out so much of the stuff. Definitely forced them to watch a fair amount of Jurassic park.

I remember going through that trilogy a little bit older. The Matrix was a must, was must see. So that was probably with older. National Lampoon's Christmas Vacation is one that I finally got to introduce them to.

Like, this is what a dysfunctional family looks like. Now they're all teenagers now, so don't get me wrong. But those are some of the ones where they're like. Yeah, they wouldn't have chosen it themselves, but we now have a common vocabulary. Yes.

Adam: Awesome. That is a good, that is a good list. Alright, two final questions for you. How often do you tell your kids back in my day stories.

Matt: All the, all the time. All the time. And I kind of feel like there's a bit of a duty here where they kind of need to know. Like, I think that's good. I, If you start with that phrase, sure, you're just like the, you know, Grandpa Simpson at the cloud, but I think like I always enjoyed those stories because they put life in perspective.

When my dad would say them, I still share those stories. So, you know, yeah, they can be, they're tacky and they can be whatever, but it's useful anchoring, you know, and listen to me, I'm defending them. So I use them a lot. I'm sorry. Yes.

Adam: All right. And finally, four children plus a large dog and a spouse. What is your take on minivans?

Matt: Oh, get them. Get them. Yes. I mean, definitely like we had a little, we had a little Ford escape when we had our first, as soon as we had our second, we realized this was cute. But the stroller literally takes up all the cargo space alone. So we went Toyota Sienna 2005 Toyota Sienna. We had that until 2000 and I want to say 17. So we got to have her 12 years, 225, 000 miles in that bad boy. And all it needed was oil changes, you know, I mean, now that when I took it to the dealer and they said, we'll give you 500 bucks for it, they basically said this thing has a bright future hauling around, you know, some kind of produce in Mexico was sort of its final destination, but it was going to be used you cannot beat utility.

I mean, it's, it, minivans are the true, you know, utility vehicle.

Adam: Well, that is an incredibly strong endorsement to end on. So Matt, Thank you so much for coming on Startup Dad, for talking to me about your family and for telling some great stories, I super appreciate it. And I wish you the large family. It's the large teenage family, all of the best of luck in the world.

Matt: Thank you, Adam. Great to be here.

Adam: Thank you for listening to today's conversation with Matt Wensing. If you enjoyed the show, please subscribe, share, and leave me a review on Apple or Spotify. It'll help other people find this podcast. Startup Dad is a Fishman AF production with editing support from Tommy Heron.

You can join a community of over 10,000 subscribers and stay up to date on my thoughts on growth, product, and parenting by subscribing to the Fishman AF newsletter at www.fishmanafnewsletter.com. Thanks for listening. See you next week.