Be Gentle On Your Own Self-Criticism | Matt Martin (Dad of 3, co-founder and CEO, Clockwise)

[00:00:00] Matt: I do think it's really, really important through the arc of the whole relationship, but especially when people are tired, it's just like take a beat and communicate how you're feeling, communicate what the ask is and also give your spouse some leeway that they're probably making the same mistakes is like they're assuming things, you know, maybe they're getting short with you. They're probably sleeping less than you are if you're the dad. So like, I think it's really, really important.

I don't know that I have a special angle on it other than just like, can't assume that people know what you want.

[00:00:31] Adam: 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. In today's conversation, I sat down with Matt Martin. Matt is the co-founder and CEO of Clockwise, an amazing product that optimizes your team's schedules to create more time in everyone's day.

Prior to that, he was an engineer, and a lawyer. In addition to being an incredible founder, he's also a husband and the father of three kids, including a set of identical twins. In our conversation today, we spoke about the change in working style that's required when you become a parent, the importance of clear communication, both at work and with your spouse and partner, including the most important aspects of communication to get right, and the need to both focus and be gentle on your own self criticism and the demands or expectations you have for yourself. We also talked about the support structures that have been really critical for his dual working parent household. I hope you enjoy today's conversation with Matt Martin.

[00:01:42] Adam: I would like to welcome Matt Martin to the Startup Dad podcast. Matt, it is amazing to have you with me on the show today. Thanks so much for joining me.

[00:01:52] Matt: Thanks for having me. I'm stoked to be here.

[00:01:54] Adam: For those folks who are not familiar with Matt Martin, tell me a bit about your professional background.

You are a founder of a company that is a very cool company. So let's hear about it.

[00:02:04] Matt: So I, too many years ago now, founded the company clockwise. We provide an AI powered scheduling assistant. So if you need help cleaning up your calendar, and I think if you have a pulse, you probably do. We can help you do that pretty quickly, easily, and with low effort. You can sign up at getclockwise.com. Anybody can get up and running. You get a free 30 day trial, and then you even have a free plan thereafter. We work with some insanely great companies like Netflix, Uber, Atlassian, Pinterest, the list goes on, to help make sure that everybody has a schedule that's not only productive, but sane.

[00:02:39] Adam: Cool. Productive and sane. That is a great topic for this parenting podcast.

[00:02:45] Matt: If you're a parent, you only get one of those.

[00:02:47] Adam: Right. You don't get both. We can't have all the nice things. What'd you do before clockwise? Were you in a different line of work or different career path

[00:02:56] Matt: Yea my background is kind of funky. So right before Clockwise, I was at a different startup named Relateiq that was acquired by Salesforce. So immediately proceeding clockwise, I was managing our front end engineering team. Inside our little subdivision inside Salesforce. And then prior to that, I was at a number of little startups.

And prior to that, I was an attorney. And so that's, the weird path that I took. college, I was really into politics. I was kind of tinkering with software engineering on the side, but I thought, you know, maybe I want to go to public policy. So I went to law school and practice as an attorney for a little bit.

Decided it was not for me, which was a very expensive lesson to learn. And bailed and went into software.

[00:03:36] Adam: You follow that well worn path of a attorney to startup founder.

[00:03:40] Matt: That's right. That's right. Yeah. It's the most linear path you can find. It's a good process.

[00:03:45] Adam: Oh, that's funny. So tell me a little bit about what life was like growing up. What were you Matt? Like as a kid?

[00:03:52] Matt: I grew up in Minnesota uh, I grew up in the suburbs of Minneapolis so in a lot of ways, kind of like a standard suburban upbringing, you know, riding bikes around. I was a weird combination of a little, I won't swear

[00:04:07] Adam: it's an explicit language allowed podcast.

[00:04:09] Matt: Alright, I'll let her rip, I was kind of a little shit and not in like the typical ways I said, I've always had kind of a problem with authority and that really shone when I was like eight, nine, 10, 11, 12.

But yeah, I mean, I just, you know, biking around, playing video games, reading comic books, kind of pretty standard suburban kid in Minnesota stuff.

[00:04:29] Adam: Yeah. Sounds a lot like me. I grew up in a Detroit suburb, so a very similar Midwestern upbringing. Tell me about your family now. You have a wife and you have three kids, if I'm not mistaken.

[00:04:44] Matt: You are not mistaken. The wrinkles show it. Yeah, no, we have three kids. So my wife is a doctor. Actually my best tip for anybody listening who is also a dad or a parent, try to marry somebody who is a pediatrician. Uh, It's kind of an unfair hack on having kids. We've avoided many trips to hospitals that I probably would have brought them in for.

And she's like, nah, it's just a rash. But my wife works as a pediatrician here in Minneapolis. And I have twin girls who are four years old, identical twins. That was a surprise. And despite having identical twins, we were nuts enough to go for number three, and I now have a six month old boy.

[00:05:24] Adam: Wow. So your wife is a doctor, a pediatrician. That's a pretty intense job. And you are a startup founder. Also an intense job. How do the two of you manage having two like dual track careers? And, you know, a cadre of children with all the needs and time suck that goes on with that.

Like, do you have certain support structures in your family or flexible work arrangements? How have you two set it up so that you can kind of make all this stuff work?

[00:05:57] Matt: Well, at the end of the day, we both allocate about 30 minutes for each other just to cry into a pillow. We find that's helpful. No, I mean, look like we have a pretty balanced partnership. I think you should probably ask my wife if that's accurate.

[00:06:09] Adam: I'll check in with her after the show.

[00:06:11] Matt: Thank you. Yeah, that's good. Report back with what she says.

I'll be interested. It starts with just being pragmatic, honestly. I mean, I find there's a certain brand of type a parents and both my wife and I are very type a, but I think we've avoided this trap where you're trying to do everything quote unquote right. I mean, there's so much information out there.

There's so much stuff that can be consumed on everything from the web to Tik Tok. And I think that we ground this a little bit and just straight up pragmatism to start, which is we do have dual track careers. You know, it's not a matter of. making the best balance or making the best decision in the moment, but actually making the decision that gets us through.

So at a practical level, that means we spend way too much on childcare. I joke, but it’s insane privilege to be able to do that. Just with both of us working full time jobs, there's probably no way to balance this without help of a nanny. And not everybody can do that. And we can, and it's a tremendous assistance.

We have a daycare that we love that the twins do really well at. And then evenings, you know, just kind of all hands on deck. You know, right now we're in that phase where the six month old is still breastfeeding. So it's kind of my wife on deck for the six month old and I'm on deck for the twins.

And that's more or less the default, but then we have a shared family calendar that we put anything on that might disrupt that rhythm so that we have advanced notice about it. We can kind of block and tackle around it.

[00:07:29] Adam: That makes a ton of sense. Calendaring all hands on deck. Love that. At least you have like one hand for each of the twins. You can you know, keep stiff arm them while your wife's trying to do her thing. Yeah, I think I appreciate that you mentioned with two working parents, like without childcare, without daycare, nanny, like it's pretty difficult to make all that work.

[00:07:52] Matt: Well, here's another thing, Adam. I mean, we lived in the Bay Area. We lived in downtown San Francisco for the last 12 years and only recently moved to the Twin Cities. Clockwise, fortunately, it's completely remote distributed. I have a lot of employees across the U. S. And it was a really tough call. I love San Francisco.

It is still the epicenter of tech and startups despite what somebody from New York might tell you. Or Miami. I mean, that's just a joke. I'm going to get hate mail now. But with a third on the way, both of our parents are here. So that was another just pragmatic decision, tough one. Cause it has career implications in terms of how close I can be to some stuff.

But really like, I think makes me a better CEO and co-founder because I can devote more time and attention and still wake up pseudo in a state of sanity. That was a big one as well.

[00:08:45] Adam: So you founded Clockwise, you mentioned the beginning a little over eight years ago. Your twins are four. So you had them about halfway through this clockwise journey. I guess I have a couple of questions about that for you. One is You know, what was that conversation like, or that, that discussion or process with your wife when you're like, Hey, we're two working parents, I'm working as a founder to start up, like that's a big responsibility.

I've got a lot of children that all work at the startup with me. And then she's a doctor. So I guess what was that conversation like around starting a family? And then how have you found that your working style has changed or your approach to work has changed as you've become a parent?

[00:09:32] Matt: So for us I started this company with two other co-founders who at the time of founding were dads. And so entered with it in a lot of ways, really fortunate to be able to see an example of them deciding to jump into it, even with kids.

For me uh, having kids was a journey. So at the time that we found this, I was in my early thirties. I just turned 40 last month. 

Adam:Happy Birthday.

Matt:Yeah, thank you. Thank you. And my wife and I kind of decided that we're ready to have a kid. Yes, that was the target.

We decided that we're finally ready. We've been married for several years. And it just felt like, okay, let's, you know, let's do it. There's no good time. And we'll figure it out. But then it took a lot to have a kid. We went through IVF multiple rounds of banking and it won't bore you with the full process, but really quite a journey in order to have a kid.

And at times thinking that maybe we couldn't have any at all. So give you all that context because by the time that we were at the point where Ashley was pregnant, it was just like, we were in it and we had been in it for a while. And so I don't know that we ever really had that substantive conversation about what is this going to mean?

Because it had been such a challenge that now we're just determined to make it happen. But I will never forget that first ultrasound when the doctor said, Oh, there are two in here. Because one thing that happens actually with IVF is a lot of the clinics will implant two embryos at a time, because it increases the odds of success.

And implantation isn't super fun anyways, so you may as well increase the odds of success with each round. And for the clinics, it allows them to put better stats on their website, so they like to do it. And we had specifically said, no, thank you. Because A we didn't have that many embryos to spare and B we just wanted to have a single kid.

We didn't want to risk twins, but then the embryo split uh, someone had different plans for us. So, but yeah, that was the journey. I mean, we really didn't have that conscious conversation just because of the way that we got into it. And then my style changed quite a bit.

[00:11:35] Adam: Tell me about it.

[00:11:36] Matt: Yeah. So first let me acknowledge that it kind of scared the shit out of me. like, even though we had jumped into this process of trying to have a kid, we're determined to make it happen. I hadn't had that period of process, what that would really mean for me. And so once it became a reality that Ashley was pregnant it was really pretty intimidating to think I have to lead this company while taking on twin kids and there's before you have kids or I shouldn't say you at least for me before I had kids. I could brute force issues. You know, it's just like I'm gonna work later. I'm gonna put in more hours. I'm gonna work over the weekends and God knows I did a lot. After kids, I learned that I just couldn't do that anymore.

And I tried for a little bit, honestly not consciously. I just fell into the same patterns. And fortunately I had an investor and mentor who I was expressing this to. He said, no, no, no, no, this is going to make you a better CEO. It's going to make you more disciplined. And I remember at the time being like, Oh yeah, that sounds great on paper.

How does it actually work? And it unfortunately didn't give me a playbook, but I did figure it out, which is I have to set boundaries and more structure in my day. And I have to be more diligent about spending my time on stuff that actually is high leverage and being better about delegating the stuff that doesn't, and these are kind of classic techniques that aren't even related to being a dad.

They're just related to, as your workload increases dramatically, how are you going to continue the throughput? One way that your workload increases is by squeezing the amount of time that you can actually spend on it. So I put structure into my day, you know, put an end time on and one tip for any working parent out there, if you can get away with it in your job is to put on 30 minutes to an hour before the end of your workday on your calendar every day as a recurring meeting that's blocked. It allows me before I have to switch gears and go prep dinner or go help with the kids, it allows me to kind of clear out my inboxes. And a lot of the times I still have to come on after bedtime, you know, at eight o'clock, but then for that in between period, say between 5:30 and 8, I have clarity.

I'm not juggling all those loose threads in my head. I know either that I need to come back on eight and knock out these three things or not. And so that's just one very specific tactical example of the ways that you have to bake in more structure and be more diligent about how you're spending your time.

[00:14:06] Adam: Yea, so it sounds like you build in that kind of like an off ramp to your day where you have that point of transition. I like this idea of, you know, I can clear out some of the stuff that might be jumbling out of my head or like that one email that I'm thinking about that I know I saw a couple hours ago and like, want to get to it.

And if you don't get to it, you'll just be thinking about it all the time when you're trying to like, you know, catch the food that your four year olds are throwing around or something.

[00:14:33] Matt: Well, or the worst. I mean, I found, I think there's a little bit personal, but I think most people have this, which is, you might be trying to read it after you've transitioned, you know, you have to leave the office, you know, you have to get home, you know, you have to help cook dinner or help take care of the kids, but you still have your phone on you. And so, you know, you're trying to read it and it just, I know that A, what I'm doing on my phone at that point for work is going to be really low leverage because it's going to be very distracted. It's not going to be good work, even if it's just an email, I'm not going to be thinking about it clearly.

And it's going to really add to my stress while I'm with my kids. It's not gonna allow me to focus on that. And so, you know, just having that, I like how you phrased that having an off ramp for the day. A lot of the times when I go through, you know, I go through all my inboxes, I go through email, Slack, my to do list, any open docs, sometimes I don't get all of it, but then I try to move it all into my to do list and sometimes when I look at that email, That I would have been thinking about or looking at my phone.

It's actually something where like, because I take a moment to off ramp, I can either knock it out right there or it's really clear that it doesn't need a response tonight. Like I can do it tomorrow morning. And it's just like the amount of clarity that adds is just, it's huge. It's huge.

[00:15:52] Adam: I wanted to ask you touched on this with your twins that you remember the sonogram and then going, Oh, there's two. And you were like, Oh, okay. Is that the earliest memory that you have of becoming a dad? Or is there another one that Oh, you know, maybe right after the kids were born or one of those early late nights or something like that.

I'm always curious to hear about people's earliest memories of fatherhood.

[00:16:14] Matt: That is the earliest because that was literally the time that we heard that there were kids, you know, and we had, haven't gone through the ups and downs of all of it. You kind of learn to be skeptical about earlier signals. And so I didn't really embrace that. We're going to be, you know, and it's still, there's still odds even at that point, but that it was likely that I was going to be a dad until we saw it sign up.

So that one really sticks in my head. Another one that really sticks in my head is, you put up your registry and you start to get stuff that comes in and we had a group of friends actually from law school. I did get something from law school. I got some friends. That were nice enough to get one of the strollers on our list.

And it came and it's this double stroller. You know, side by side, cause I have two kids and it hit me for the first time, just like how much my life is about to change. Cause there's like this physical manifestation, as the dad, you know, you don't biologically carry the kid. So, seeing that stroller, I was just like, Ooh, crap.

[00:17:18] Adam: Yeah. And those double strollers are heavy too.

[00:17:22] Matt: Yeah. And this was like a light, secondary one and it was as lightweight as it could be like, you know, like this is like, we're not talking like the tank, the huge one, but just like seeing the physical size of it. I was like, oh man. But one thing that I think is really common and I always like to reiterate, even though probably most dads these days hear it, they just think it's so important to know.

I didn't feel like a close connection, really like a close emotional connection to my kids until I don't know what the point was, maybe call it six months, you know, like, like when they start smiling that happens a bit but their personality doesn't really start to show until a little bit later.

And even then it's early, and for some dads and I don't doubt them. I mean, I think these people are really out there, like they have this, you know, pseudo religious moment when they first see their child. And I'll never forget it. I will never forget that moment because it was a very emotional moment, but it was emotional because of the birth and seeing my biological child for the first time.

That connection wasn't there in the same way and it almost felt like I was not doing something right. But it just took a little bit because when they're first born, they're kind of like little blobs. You know, if you like, you just had to keep them alive.

[00:18:35] Adam: Yes. I like to say that kids look a lot like Winston Churchill when they're born. They're just like, not a lot of neck, no hair, a lot of wrinkles, you know? It's interesting. You mentioned like, hey, a lot of dads probably know this instinctively or have heard this. But I think, you know, many dads have brought that up on the show.

And I think it's important because I think it's important for dads to hear this, that like, You know, you're not broken if you don't feel this immediate, like emotional pull to your kids. And it sounds based on the number of people who've been on the show and talked about it pretty common. You also feel a little bit useless as a dad in the early days.

Like there's fewer things that you can do. You're not necessarily responsible for that kid eating, for example. so I totally get it. and I appreciate you bringing it up because the more times we talk about it the more people will understand.

So I wanted to ask you a little bit of one of the topics we talked about sort of in the prep was this idea of communication.

And I think this one's really interesting because you can probably appreciate this as a CEO, but in companies. Most of the problems as you get bigger, end up originating with communication. A lot of problems are ones of communication. People don't know something you're not on the same page, you're out of alignment. And especially in a fully remote company, I imagine communication super important. Would you say that the same is also true in parenting and those lines of communication with your spouse and how do you manage that?

[00:20:04] Matt: Not as well as I should. I mean, I think that the answer to your question is yes. And I think that especially it's really important in any relationship to have clear communication, but also to acknowledge. that people can't read your mind, you know, and I, I'm bad at this at times.

And I think that especially in the early months of having a kid, you're most prone to this, because what's going on, you're tired, you're not sleeping, you're kind of stressed out, you know, it's a new view on your relationship with your spouse that you've never had before. And as you noted, the division of labor is inherently unequal.

And so like you're trying to help out where you can. And I have personally gotten into bad habits of, you know, just assuming that the other person knows what I want or assuming that they're going to communicate. And I do think it's really, really important through the arc of the whole relationship, but especially when people are tired, it's just like take a beat.

And communicate how you're feeling, communicate what the ask is, and also give your spouse some leeway that they're probably making the same mistakes is like they're assuming things, you know, maybe they're getting short with you. They're probably sleeping less than you are if you're the dad. So like, I think it's really, really important.

I don't know that I have a special angle on it other than just like, you can't assume that people know what you want.

[00:21:26] Adam: Yeah. And would you, what would you say is sort of the most important aspects of communication and the things you need to get right? Clearly you mentioned the expectations, the, you know, tone and tenor of what you're talking about. Are there other things that come in, get into mind where you're like, man, as a parent, these are some of the things that you really got to nail.

[00:21:47] Matt: Yeah. I mean, there are a couple of things in terms of with my spouse. I think that the calendar for us helps and it's a form of expectation setting, you know, making sure that is the worst is like, surprises that you can't logistically plan around, you know, that's just going to create problems for the family and it might create tension.

And so having some mode to communicate who's taking what, when, whether that's a calendar or whether you're just messaging, but always staying ahead of it. I think that reduces the likelihood that you have like a real bad situation. And then the other, I think is giving grace, and I try to practice this, but like reminding myself that just because my spouse is making a certain face. You know, that might not be about me or maybe it is about me and that's okay for the moment. You know, like we're all having a, we're all having a time. With kids the thing that I try to practice the most is like especially when they're having a really hard time or they're blowing up or, you know, I'm having a morning where it's fight after fight after fight after fight. Sometimes I do lose my patience, but I try to remind myself that they are learning and growing and that like my reaction is the only thing that I can actually control. I can try to help them and I do, and I can try to coach them, but they may not have the capacity at the moment or capacity in terms of where they are physiologically to really process that.

But I'm an adult. And I do have the ability to control most of the time and it's practice for me to be able to mediate my response and think about it. And just having that beat to reflect on that is helpful. Just recognizing that, like, I do control something in this chaos and it's how I show up. That doesn't mean I'm always able to show up at my best. We're all human, but like, I find that that's important.

[00:23:34] Adam: Yeah. Do you have any stories about getting it wrong? There's maybe this is a humbling moment, but you know,

[00:23:43] Matt: Yeah. Too many to count.

[00:23:44] Adam: Any one that you would share that, you know, maybe other people could relate to while listening?

[00:23:48] Matt: My wife and I probably have different philosophies on potty training.

[00:23:53] Adam: Oh,

[00:23:54] Matt: Yeah. And again, she's a doctor, so I will take her lead. But again, I'm also right now, at least mostly the person on deck for the twins. And there's a certain point in the life cycle of your child, where the poops go from being like, baby, even toddler poops to be like, Oh, you're a full human. Um, This is like, you know, you just took a shit in your pants. I'm glad you had a diaper. But like, this is a different level and I am just like. They're so close on just being done with them.

And I'm so excited for that day, for the day when I go into my garage and it doesn't stink to high hell cause the garbage is full of dirty diapers. And this has been a case where I've lost patience because, you know, as she reminds me, like the one thing that they can control is their body. And we really want to help coach them to understand that they are in control of their body.

And so trying to force them to do something, especially force them to go use the toilet, is not necessarily going to be productive and I try to take her guidance on that, but sometimes I just, like,

[00:25:07] Adam: hm.

[00:25:08] Matt: I will paint this picture so that every parent can empathize with me, where, you know, I have two kids that are four years old.

They know how to use the toilet. They know how to use the toilet for all functions. And we're going to bed and you just want to get bedtime going. One of them decides to go use the toilet. And the other looks me in the eye and go, I'm going to poop in a diaper. And I'm just like, no, you're not, you know, like, I just want to like, it becomes a power struggle and then nobody's happy.

You know, nothing productive happens. I don't win even if the kid goes on the toilet because then they withhold. And that's kind of a microcosm of those moments where I'm prone to getting, triggered is a loaded word, to getting fired up when it becomes a power struggle.

[00:25:55] Adam: Yeah.

[00:25:55] Matt: And I, and again, it's about reminding myself, like, what am I in control of?

And what am I not? But sometimes you just want to win. It's like, I'm the full adult. I know better.

[00:26:05] Adam: Yeah. It's also, you know, I didn't have this appreciation thinking about it I remember potty training my kids and you know, my kids are not twins. And when a kid needed to go, it was like, it often was very urgent. It'd be like doing their thing, playing their toys.

Oh, I immediately have to go to the bathroom. When you have twins. You only have one, you know, toilet installed in a given bathroom. And so I don't know, how does that even work? Do you have like, send one down to a different level? Like, you know, what, I don't even know if that’d work.

[00:26:37] Matt: A lot of screaming, a lot of screaming

[00:26:39] Adam: A lot of…quick, quick!

[00:26:41] Matt: Yeah, no, I mean, it's the with twins. I'll go on a digression here, Adam. When we first had the twins, you get parents all the time being like, I don't know how you do it with two. And we didn't know any better. So I was like, Oh, you know, parenting stuff.

I'm sure like you guys had a go of it too. Like it just is what it is. You know, just muddling through. Now that I've had a single one. I want to look everybody in the eye and be like, you fucking amateur. Like, you don't know, I don't even know what pairs of triplets do. I mean, that's just a whole different circle of hell, but the problem with twins, and this is true of the potty, but it's true of a lot of things is that the behavior of one will often trigger behavior in the other and it can be a variety of different behaviors that might be competitive, it might be fairness, it might be anger, but all of those come into play with the potty, too, one of them will go, Oh, I need to use it. Sometimes no problem. That one is urgent for that one.

Other times it's no, I need to go first and then a whole meltdown over not

[00:27:46] Adam: Oh no.

[00:27:47] Matt: And then when you try to incentivize them, I don't know if there's a good practice or bad, but you know, they get a reward for using the potty. Less so now, but at the earlier stages and it.

That also inculcated this behavior where one would really need to go, but then the other one just wanted an award too. So they'd go sit and like do nothing. And now you're having a debate with a toddler about whether they really use the bathroom. So I don't know, long story short, patience, but there's no winning.

[00:28:17] Adam: Maybe we can move off of potty training, but I, this is, I love this conversation and I'm so glad that I'm not in this phase at this point. What are some of the most surprising things that you've discovered as a dad?

[00:28:28] Matt: Surprising is an interesting word I don't know that there were many huge surprises but I think that there are a few things that I didn't understand and wouldn't have seen with clarity one is just how much parenting is just going with the flow.

like, you don't change, like, there's not like a magical parent class. I mean, there are some parent classes, but like, you don't graduate and become a parent. You just have a kid one day and now you're a parent. And I think growing up, you look at your own parents to some degree, if not irreverence, at least.

Separation and the reality is one day you don't have a kid and the next day you do and you're still the same person and that's, I don't know, again, not surprising because I think you know, I would have said that, but just illuminating in the fact that there's not any magic here.

There's not like a playbook that you get. You know, you can read materials. Everybody gives you different advice, but a lot of it is kind of going according to your own judgment and your own values and trying to do the best job that you can. And I think that the lack of kind of a established system for how you do this is perhaps surprising.

And then another one is just. How much I can enjoy it at times, you know, I think it's really easy to talk about the burden of all this and, you know, it's really easy to talk about the burden because, you know, it, what can you do with a laugh at it? But, the joy of it is really true as well.

I like the thing that I reflected on when I first became a parent is I don't know how much this resonates for other people, but I often like before becoming a parent, I would think back and you have these memories that are ingrained in your mind of these perfect moments. You know, I think about one time when it was just me and a few of my friends at a campfire on the shore of Lake Superior.

And there are a bunch of those, like, I, I'm fortunate that I have a bunch of those, but they're fleeting. They, for some reason, they stick in your head and the frequency of those after kids just goes way, way up. And it's just like, it gives purpose in a way and gives emotional connection, it’s biological.

You know, we're made to do this, but it's just really rewarding at a level to see them grow, to experience life with them and to see the world through their eyes and sometimes it's joyous and rewarding. Sometimes it's really trying and rewarding, but it really gives purpose in a way that, again, I don't know if it's surprising, but I definitely couldn't have appreciated it.

[00:30:56] Adam: Love that. Those are a couple of really great points. Thank you. You mentioned advice. You got a lot of advice. And that is a thing a lot of parents get when they are expecting. So if you could rewind the clock no pun intended, by the way to the time, you know, four years ago, right before the twins were born and you bumped into, you know, four years ago, Matt, is there any particular piece of advice that you would give to Matt that really stuck with you that maybe somebody else gave to you or that you've learned in your four ish years as a parent?

[00:31:33] Matt: I would look that mad in the eyes and I would say sleep now and sleep much jokes aside. I mean, I think that it's difficult to prepare. Would have been difficult to prepare me for the reality of it. the type of person. You know, again, probably going back to problem with authority. It's difficult for me to get advice and really internalize it until I go through it. But if I could shake myself you know, and really get a message through, it's restructure your day and your expectations now.

One of the things that was really tough for me, actually tough I think psychologically, was that you're at a startup and it's so much work and it's so intense and I didn't do this consciously, but I realized in retrospect, I really used those moments of downtime as restorative, you know, whether that was the weekend or whether that was late in the evening and you just don't get as many of them.

It's just reality. They're taken up by your kids and family and you have to think much more tactically about how to get that. And so the advice that I would give to myself is both to try to get ahead of those expectations. The part that was tough for me was still no, like I knew, you know, I knew because of the reality I was living in as a new parent that I wasn't going to get them, but I was still, there's something that was still caught in that old world where I needed that rejuvenation.

I wasn't acknowledging that I wasn't going to get it through the normal means that I had previously and not getting it was leading me in a place where I was really upset about it. And resentful of not having that time. And that resentment could take aim at whoever caught it at the wrong moment, you know, whether it was my wife or the kids themselves, and I think that you know, helping myself get ahead of that and kind of restructure my expectations, but then also structuring in the time to have that restorative period, that would have been really, really helpful.

[00:33:33] Adam: Great. Was there any advice that you got that you would tell younger Matt to just completely ignore?

[00:33:42] Matt: I, I happen to not take much advice that comes from my parents. So there was already a pretty good filter on the source of information it was coming from. So I can't apologize. Not a great answer to your question, but I can't think of anything that sticks out as like, Ooh, I really wish that we had never done that.

In that vein, it's a little bit weaker sauce, but I think it's really easy to get amped up on the should nots as a parent, like, you shouldn't let your kid ride a scooter before his age, you shouldn't let your kid use a screen, you shouldn't let your kid, I mean, screen time is a huge source of guilt for a lot of people, and to some measure, those are correct, but I think that anything taken to extreme is suspect and re-anchoring in two things.

One is, like, A, what's practical? You know, like, what actually works with your lifestyle? Give yourself some grace to just, like, discard a rule every once in a while. And two, what brings your kid joy? I think one thing that gets too lost in the conversations around parenting is like, everything has to be educational, everything has to be productive, everything has to be in pursuit of something, everything has to be structured and like, I don't know, I don't want my kids watching Paw Patrol 24/7.

Like If they love that dumb show. And they want to watch it for 15 minutes or 20 minutes a day, like, great, whatever, you know, I do terribly dumb stuff as well. That just gives me some peace of mind.

[00:35:09] Adam: Sure. Okay. I love that. I wanted to ask a more lighthearted question, which is what's your favorite book to read to your kids? And do the twins like the same book or do they each have their favorite?

[00:35:24] Matt: Actually, this is one piece of advice that I'd give everybody is that you can find used books really easily, and especially used kids books. And like, we, I mean, my wife has maybe a borderline problem. We, we have many kids books but really it's kind of a delight. Cause like you get these books like as a new parent, they're going to come in your registry.

You're going to find them. You have some favorites from when you were a kid, which are really special. But there are only so many times you can read Goodnight Moon before you, before you just want to throw it out the window. And so finding a source where you can just like constantly scoop stuff up.

Local libraries are great too. I found that's really wonderful. Like we have rotational books that comes in and out now. That all said that right now, they're really into the Mercy Watson books.

[00:36:08] Adam: Oh, yeah the pig.

[00:36:11] Matt: Yeah. Yep. Mercy Watson, the pig. And for those who aren't familiar, it's kind of like a, it's a early reader chapter book.

Really like very short. But they like them a lot. And they're kind of fun. They allow me. And by they allow me, I mean, literally the twins will allow me to read it in a voice. Sometimes they tell me that the voice is awful. I need to stop. But I like them reasonably well. They have some narrative to them.

You get through them. Some of the favorites, one is actually kind of a surprise one. It came in off this used books that we're getting Paletero Man. They love Paletero Man. Yeah.

 Yeah. I hadn't either. If you look it up, it's about the Ice cream and popsicle vendors in LA.

and they just love that one. They got the chance to bring one to school that they got to read in their class. And that was the one that they liked.

[00:36:56] Adam: Cool, very cool. Paletero Man. We will look we'll look this up and link to it in the notes. So you you strike me as a high achieving guy. You mentioned you and your wife both pretty type A. It's hard to be a startup founder and then also a doctor and not be a type A person. And usually high achievers have a pretty vocal internal critic, kind of motivates them.

How have you navigated that internal critic as a parent and as a founder?

[00:37:27] Matt: Yeah. I think that the internal critic really gets loud for me when I'm worn down, you know, it's easier to put that critic into context when you have the energy to do it. uh, there are a variety of techniques for that. One that I really like is if I'm really stuck, just to write out voluminously, like not write for anyone, just like write out all my thoughts on paper and it helps get it out, which is a tactic I found it's useful for me.

I also sometimes use the tactic of getting out of the I voice. Internally, and trying to look at the situation as though I was advising a friend because often we're much tougher on ourselves than we would be on somebody else in the same situation, and you can't obviously completely get out of your head, but I found that it's helpful for me to reflect as though I were giving myself advice.

But it does really go back to making sure again that you get those moments that rejuvenate you and rest you however you can. I'm always a little bit tired. I don't get enough sleep. I try. But working out is really important for me. It just, it's a little bit of time that I hold sacred to clear my head.

I try to carve out time in the evenings just to, you know, maybe veg out and watch Netflix. Like none of this is rocket science, but I just think that critic gets really loud unless you take care of yourself. And so one of the things that's really easy as a parent is to focus all your energy on your kids and those around you, cause it feels a little bit selfish to take time for yourself. And again, check these notes with my wife, who you'll be talking to after this. But it feels a little bit selfish, but I think it's so essential. Like you got to budget out that time to make sure that you're your best.

Otherwise that voice just gets loud. You get irritable. It's just, it's not good for anyone.

[00:39:02] Adam: Yeah. We talked earlier about how being a dad has changed some of your relationship with work and your time management and things like that. I'm also curious how Becoming a parent has changed how you operate as a manager and a leader at your company. Would you say that's influenced who you are as a manager?

[00:39:29] Matt: Yeah, I think so. I mean, I think, you know, the first order stems from having to be more structured in my time. I really do think that I'm better at this now than before I had kids. I am more thoughtful, more structured. I am more diligent about how I'm using my time, about how I'm adding leverage, about where I interject and where I don't. I think those are all net positives that would have had to been learned sometime and being a parent and having limited time just forced it.

But the other perspective outside of kind of like being more deliberate that is structures for me as a manager is you realize how much conflict is just managing communication and how being able to spot the conflict and spot the emotional underpinnings of that conflict can really help you navigate it.

And it's not the same as kids, you know, I'm working with really talented adults, but I think that having it distilled down into a much rawer form with your kids, because they're developmentally so early, it is just raw emotion. And it sounds funny, but like seeing just raw emotional waves.

You realize like, there's nothing I can do with that. Like I just have to help coach them through it. And then he started to see a little bit like adults are way better at managing that raw emotional wave, but that's still there sometimes. And so, you know, there's often the phrase I'm going to butcher, but it's when somebody's complaining to you or brings an issue to you, are they asking you to solve it?

Are they asking you just to listen? Are they asking you to be a shoulder to cry on? Because the reality is they're not always asking you to solve it and trying to solve it when there's an emotional state or they're trying to work through something may be counterproductive. So I think it's influenced in a myriad ways, some more subtle than others.

[00:41:14] Adam: Yeah. I wanted to come back to communication a little bit, cause this has come up quite a few times in this conversation. You know, partnership is really important obviously in a co-founding relationship, but especially when you have kids with your spouse, I also think it's hard to agree a hundred percent of the time you mentioned some slightly different philosophies on potty training and things like that.

What's an area that you and your wife don't agree on when it comes to parenting?

[00:41:40] Matt: One that comes to mind is very talked about it is the potty training. Like, I think that setting just a firm rule and boundary like would have definitely done that absent her counsel. I think academically, I see that she's probably correct. The damn, you know, credential she has really is a trump card sometimes. But emotionally, it's really unsatisfying. And it's often at that boundary, honestly, like that's a fault of my own that I'm aware of is like when my emotional impulse is going one direction, but either her opinion or either the facts of what I read of the situation is going to another, it's really hard sometimes to modulate and navigate that even though like it should be a simple thing because I know, or at least have acknowledged that there's a different path that's better, the emotional impulse to like, I want this to go this way right now.

And again those are also points where communication can break down because I'm in a posture where. I'm not coming from a logical perspective. You know, I'm not coming from a perspective that's like grounded in any sort of fact or science. It just like, I feel this and I want this and that's not incredibly productive.

So I don't know that I'm the best example of how to communicate in those moments to be perfectly honest. But I have gotten better at just saying. And then walking away. If I can, sometimes I can't cause the kid, you know, kid needs help or something, but sometimes again, going back to those emotional waves, the best thing that I can do is just control my reaction and then like, let it cool down and give it some space.

[00:43:15] Adam: Love that. You have built an entire career in technology, or at least the last two thirds of your career. Something tells me you're not going back to being a lawyer. 

Matt: I don’t think so.

Adam: No, what is the relationship that you want your kids to have with technology as they get older?

[00:43:34] Matt: Oh man, this is like a really philosophical show. As humans were toolmakers and tool users like that is our big advantage that in language are big advantages over any other species on the planet. We have for our entire evolution figured out new and better tools and I see technology as really just another iteration of tools.

And I find it technology to be fascinating and really just irresistible to me because it's the intersection of tool making for other humans and playing off all of the innovation of the humans before me in a way that I get to stand on the shoulder of giants and just , that march of progress and being able to build something new for somebody, it's still exhilarating to me after years of doing it.

And so my hope would be that. I am able to educate my kids as the fact that these are just tools. You know, I don't have a real aversion. For example, we're not at this stage of their education yet, but I would have no aversion to them using chat GPT for homework. It, to me, it's another tool. And if the task at hand is to master how to craft your own prose, then it's the wrong tool.

But if it's to master your own prose and you want to have something to bad ideas off of, it's not a bad tool. And so for me, it's more about educating to understanding how and when to use technology and having curiosity about it so that it doesn't feel like a black box, it doesn't feel like a panacea, it just feels like, you know, another gadget or tool in your arsenal of things that you might use for whatever task you're endeavoring to accomplish.

[00:45:14] Adam: Have you started playing around with your daughters and chat GPT or anything like that, like the voice mode or anything?

[00:45:23] Matt: Yeah, not really. The closest we got to any of that is doing like the iPhone Animoji or Snapchat filters, which they get a huge kick out of. But we really haven't played with Chat GPT at all yet.

[00:45:34] Adam: I did talk to a dad on this podcast who is also an engineer and built an entire Paw Patrol, like interactive thing so you can ask it questions like you were in the Paw Patrol TV show. And yeah, apparently his kid is obsessed. So, you know, maybe someday you could do Mercy the pig.

 Matt:That'd be interesting.

 Adam:That's right. Last couple questions for you. What is a mistake that you've made as a dad?

[00:45:59] Matt: I think not knowing when to walk away from a situation, honestly, like, you know, whether it's my kids, like having. A big epic meltdown where I can't literally walk away, but I can just acknowledge that I don't have any role other than to help be there for them. Like, it's not about like fixing it.

It's not about, you know, stopping it. Just about being there. And then a more uh, tangible way, like walking away from a situation where like, you know, obviously like my wife and I are, not going to have a productive conversation and just like walking away from it. And I think there's a little bit of just knowing our own boundaries there that I always strive to be better about cause you know, again, type A personality like you always kind of want to get to the conclusion.

Like you want to get to the resolution and sometimes the resolution just isn't in your control. Especially with toddlers.

[00:46:48] Adam: Almost never in your control.

[00:46:51] Matt: Yeah, that's right.

[00:46:51] Adam: Can't put the crust back on the sandwich that you've cut off, for example.

[00:46:55] Matt: Yeah, yeah,

[00:46:56] Adam: Last question for you. How can people follow along with your journey or be helpful to you or clockwise in any way?

[00:47:05] Matt: There are a few things that, you know, I mean, first I have to pitch the product. I think it's an amazing product. You can go to getclockwise.com or clockwise.ai, they'll both give you the same place. Try it out and shoot me a note with what you think. I mean, our team is always available at support@getclockwise.com. You can find me at Matt@getclockwise.com ping me anytime if you have feedback about the product. And then if you just want to follow along, if, you know, I tend to talk a lot about time management, obviously, I talk a fair amount about startup building culture. I talk a little bit about being a dad.

I tend to do that mostly on LinkedIn these days. Other forums, I'm still experimenting with Blue Sky and with Threads a little bit, but the most reliable place to find me is on LinkedIn. And you can just search for me, Matt, Clockwise, you'll find me.

[00:47:49] Adam: Awesome. We will link to all those places in the show notes. That concludes the regular portion of our programming. Are you ready for our lightning round?

[00:48:00] Matt: All right, let's do it. I'll try to give not nuanced answers and just let it,

[00:48:04] Adam: Let it go. Whatever you can take the Frozen mantra. Okay. Here we go. What is the most indispensable parenting product that you've ever purchased?

[00:48:12] Matt: I think it's just the diaper pail, just having a pail that you can put the diapers in that doesn't stink. I mean, it will eventually, but being able to shut that lid, get a good one.

[00:48:21] Adam: What is the most useless parenting product you've ever purchased?

[00:48:24] Matt: We have so many baby carriers, I feel like we're collecting them at this point and I have yet to find one that's any better than the first one we purchased

[00:48:34] Adam: Awesome. The ideal day with your, probably your daughters involves this one activity?

[00:48:41] Matt: Getting out of the house. I know that's about as bland as it can be, but honestly, like if we can get out of the house, go to playground, go somewhere, go for lunch, like that is great in my eyes,

[00:48:50] Adam: Change of scenery. Love that. What is your go to dad wardrobe?

[00:48:55] Matt: jeans and a button down. I'm wearing it right now. You don't see the jeans, but throw the button down on, I mean, man, that is like very, very dad, dad. I'm starting to reflect in a way that I don't like. So…

[00:49:08] Adam: Now this may, actually may not be a fair question because you are married to a pediatrician, but how many parenting books do you have in your house?

[00:49:15] Matt: Oh my God, I, how like dozens, some of them are literally academic textbooks. I'll be a little bit more fair. How many parenting books have I read in our house?

[00:49:24] Adam: Yes. That's my next question.

How many have you read cover to cover?

[00:49:28] Matt: Cover to cover? One. I read one cover to cover that was about being a good husband to your spouse. But honestly, the only thing that got me through was guilt.

I was like, how can I be a good husband if I can't even read the book on how to be a good husband, like that was, otherwise it would be zero.

[00:49:47] Adam: Awesome. Awesome. If you're going to read a book about parenting and that seems like that'd be a good one. So.

[00:49:55] Matt: Yeah, it was okay.

[00:49:58] Adam: As many of them are, what is, or has been the favorite ages for your kids?

[00:50:03] Matt: All right. So keep in mind for the listener I'm only through four years old. But I would say, I have a real soft spot for two years old. Everybody talks about terrible twos. Mine at least didn't have that. They were just mobile enough that I could take them out on the go. And they're just like these adorable little like preformed humans but every age, this is so fucking corny, but every age has been amazing.

Four year old has been really fun

[00:50:27] Adam: Okay. All right. But I, you know, I have to ask you, what has been your least favorite age?

[00:50:32] Matt: Zero to six months. Like, honestly, it's again, weird. It's so manageable, especially if you're the dad, because you're just kind of trying to survive because you're sleep deprived, but also like they're immobile, so they can't do much, but it's just like, it doesn't, it's not fun in the same way that later stages are fun.

[00:50:49] Adam: Yea. How many dad jokes do you tell on average in a given day?

[00:50:55] Matt: According to my metric or according to those around me. Don't know. I think I'm at like a solid three, three dad jokes. I need to work on that though. I think I can go higher.

[00:51:03] Adam: I think it only goes up as your kids become more aware and you become more willing to embarrass them.

[00:51:08] Matt: Well, but the, yeah, I mean the faces are what like dad jokes feed off of that embarrassed face or the eye roll. I mean, that's just gives me more power.

[00:51:17] Adam: Have you ever secretly thrown away a piece of your kid's artwork?

[00:51:21] Matt: Oh, yeah. Yeah. If you like, we drown in our artwork. Literally the teacher goes is like, your kids make like twice as much as the others. It's like, well, why don't you filter it before you put in their backpack?

[00:51:32] Adam: Just comes, it's just the crumpled ball of art that comes out of the backpack.

Yeah. I'm, I'm familiar. Yeah. What is the most absurd thing that one or both of your daughters have ever asked you to buy for them?

[00:51:46] Matt: They haven't asked for that much absurd things that, I caved because they don't ask that often I caved when I shouldn't have, they really wanted for their birthday. And of course, once one wanted one, the other one wanted the identical thing. A up unicorn. Little did I know, it also sings. Yeah. Bad choices were made. Really bad choices. And it sings in four different languages you can toggle. So, yeah it's wonderful. Those have gone missing, surprisingly. I don't know where they are.

[00:52:15] Adam: Strangely, we ran out of batteries. It's weird. What is the most difficult kids TV show that you've had to sit through?

[00:52:22] Matt: I found that Blippi was really rough. I, it's just like grading, but then I realized there's way worse stuff. Like Jules the other day found some, I don't even know what the name of it was, but it was just like barely animated cheapest production values of all time, just garbage. And I was like, where did you even find this?

So I say Blippi, I mean, Blippi, however, with the knowledge that it gets way worse.

[00:52:49] Adam: It does. It does. On the opposite side, what is your favorite kids movie?

[00:52:54] Matt: Favorite kids movie. Okay. Well, I don't know if it qualifies as a kid's movie. Wall E is my favorite.

[00:53:00] Adam: Totally a kids movie.

[00:53:01] Matt: Yeah. Okay. I don't, yeah, my, my daughters don't appreciate it yet. So like they won't, they don't agree, but I love Wall-E.

[00:53:08] Adam: I'm a huge Wall- E fan. What is the worst experience that you've ever had assembling a kids toy or a piece of furniture?

[00:53:17] Matt: Wow. We just moved to Minneapolis. I assembled a lot of pieces of furniture and you know, what drives me up a wall. Speaking of not having emotional patients, car seats, I hate installing car seats. It just like, there's something about the pressure of knowing that if you don't do it right, there's a potential risk associated with it and like being crammed in the back seat as you're trying to like maneuver these tanks of car seats we have these days. That's my least.

[00:53:43] Adam: Okay, the car seat. I get it. I get it. Have you ever accidentally mixed up your identical twins names?.

[00:53:50] Matt: Yes. Yes, I have. Yeah.

[00:53:52] Adam: Do you ever call them the name of your son?

[00:53:56] Matt: Yeah, that not yet. That will happen though. There's no doubt, but not yet.

[00:54:00] Adam: Okay. How long can a piece of food sit on the floor and your house and you will still eat it?

[00:54:06] Matt: I would say like maybe a minute, like I'm way past 15 seconds. If you ever want to see me at my most shameful just come to my house, like right after the kids have had their dinner and I'm just like eating little pieces of grilled cheese for no reason. Like they have no nutritional value. I don't need to eat them, but here we are.

[00:54:25] Adam: Human garbage disposal. That's the role of the dad. What nostalgic movie can you just not wait to force your kids to watch when they're old enough?

[00:54:35] Matt: Good one. So my mom loves White Christmas and we would watch White Christmas every Christmas. And I don't even know if it's good or not anymore. It just wormed its way into my being at a certain level. So, I look forward to that.

[00:54:49] Adam: Okay. All right. White Christmas. I might have to watch that now. Have you started telling your kids back in my day stories yet?

[00:54:59] Matt: I'm sure that I have, I, it doesn't come to mind right now, but there are many opportunities to do that.

[00:55:04] Adam: Okay. Now finally, you recently became a dad of a third kid and you live in the suburbs. What is your take on minivans?

[00:55:13] Matt: Ooh, I would say that they are the right choice for everyone. And I haven't yet allowed my identity to go into minivan territory. So it's really, it's like a personal journey, I think. And it's, you know, I'll figure it out one day and end up with the minivan because it's objectively the right choice.

[00:55:32] Adam: Yeah. It's the right tool for the job for you. Yeah.

[00:55:35] Matt: Yeah. I mean, you got three kids, you know, I've been like sliding doors. They're handy, but I couldn't do it. I couldn't do it.

[00:55:40] Adam: Yeah. Not yet. All right. Well, Matt, that concludes our lightning round. This has been really fun. Thank you so much for joining me on the pod today. And I wish you, your family, the best of times for the holiday season. And also uh, I hope everything goes well for you and Clockwise and your company.

[00:56:03] Matt: Thanks so much, Adam. It's been a lot of fun and I really appreciate you doing this. It's a great angle on a common subject.

[00:56:08] Adam: Thank you for listening to today's conversation with Matt Martin.

If you enjoyed the show, please subscribe, share, comment. 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 Harron. You can join a community of over 11,000 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, and see you next week.