Navigating Divorce and Co-parenting Relationships | Sol Kennedy (Dad of 2, founder BestInterest)

 Startup Dad Sol Kennedy Final Edited Transcript

[00:00:00] Sol Kennedy: Especially the court system can get you drawn into the conflict. This desire to win, the desire to make right. You know, your attorney might even say, well, you can go after this and this, and you should do this, and you'll, you'll win.

And you know, at the end of the day, there is no winning. And just if you remind yourself of that, that sometimes it's okay to let the other side win if it meant that you could spend an extra set of weeks with your kids, right. Just in presence rather than in the court system.

[00:00:31] 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. Parenting can be hard enough, but navigating divorce and separation. Then co-parenting is something people usually don't want to discuss. To talk about life as a co-parent, I sat down with Sol Kennedy.

Saul is the founder of Best Interest. A product he's built to help co-parents navigate the messiness of that relationship. He was inspired by his own challenges with co-parenting. Sol is a serial founder who is built and sold multiple companies. He's also been a head of product at Dropcam, a product manager at Google, and an angel investor in companies like Coinbase, GitLab, and Instacart.

In addition to being a serial entrepreneur, he's also a single halftime dad of two kids and a co-parent. In our conversation, we spoke about navigating divorce and co-parenting, important lessons that Sol has learned from that experience. The emotional rollercoaster of halftime parenting as a single dad and his experience taking time off to be a full-time dad when his daughter was very young.

Sol shared a mistake he made as a parent and how that experience has helped him grow into the dad he is today. I hope you enjoy today's conversation with Sol Kennedy.

[00:01:55] Adam: Welcome, Sol Kennedy to startup Dad, Sol, it's a pleasure having you here with me today. Thanks for joining me.

[00:02:03] Sol Kennedy: Thank you, Adam. It's great to be here.

[00:02:06] Adam: So for folks who don't know much about you professionally, we're obviously gonna get into your parenting journey, but tell me a little bit about you and what you do for work and what you've been doing for the last couple of decades.

[00:02:18] Sol Kennedy: Yeah, I've always been an entrepreneur. And that's how I identify is, I start companies. And I started my first company when I was 15. Kind of did that whole thing and I've always been attracted to creating software. So, my first app was a popup on your Windows or Mac computer way back in the old days on startup.

And it would be an inspirational message that would pop up. And that's my career as I love starting companies. I love starting from scratch, learning how to do it all myself, and then growing a team out of that. And so yeah, that's what's brought me to today, being a dad and also running Best Interest.

[00:03:00] Adam: Cool. I can't wait to talk about Best Interest. This is gonna be really, really fun and a unique conversation we've never had on this show before. So, tell me about your family now. You are a single dad. 

[00:03:15] Sol Kennedy: I am, yeah, I have two kids. They're six and eight great little kiddos. We live in Northern California. And yeah, I am a halftime dad. So I have custody, joint custody with their mother and I have them half the time. And typically during the weeks we split it 2, 2 5, which means they're kind of shifting back and forth during the week.

And then in the summertime we do week on, week off. That's how we split up the custody. And I have a, a wonderful partner, Louise, who's really actively involved in the kids and helping out. And yeah that's, the family.

[00:03:52] Adam: How old were your kids when you went through the divorce process? And tell me a little bit about that experience.

[00:04:00] Sol Kennedy: Yeah. So, the process of our marriage unraveling started pre covid

and fortunately in hindsight, actually a week before the lockdowns of Covid was when we decided to separate. And it was definitely a challenging time to be shifting from being married to then being single and not being able to meet anyone, not really being able to socialize, having lockdowns, negotiating, how do you manage kids when there are lockdowns?

That sort of thing. It was definitely an intense time to be learning the ropes of co-parenting.

[00:04:39] Adam: Yeah. And your kids were, I mean, pretty young then, right? Like if I've, if I'm thinking about back like five years ago, they were like one or two and

[00:04:49] Sol Kennedy: one and a half. And three and a half.

[00:04:50] Adam: Yeah. So how do you have that conversation with kids at that age? Like, they understand so little it would seem, so I'm curious, like, what is that, like, how do you approach that with like, really little kids or how did you, I guess?

[00:05:08] Sol Kennedy: Yeah. That's a really good question. And yeah, I don't have all the answers for sure. You know? But what's interesting when they're getting started on this journey themselves so young, it just becomes their normal, you know?

And we kept it really simple. Daddy's getting a new house. Mommy's getting a new house and we're moving and then we're gonna each have houses and you're gonna go back.

It was very simple and it just, like I said, it became their normal. And these kids are so flexible. You know, I think divorce is hard on kids for sure, but in the case of our kids, they're like very just okay with this dynamic. They don't complain about it and they just have their systems. And what's also really interesting is that their relationship is even closer than they are with each of their parents because they're always spending time together, transitioning.

And I really love that, that there are such good buddies in this process.

[00:06:09] Adam: Yeah, that's sort of interesting that the only constant for them is each other, right? So yeah. It really is. So you went through this divorce process and now you're co-parenting. And you mentioned to me that co-parenting and the reason you've built this company, Best Interest co-parenting has been more challenging more challenging even than the divorce process.

So tell me a little bit about that and what have you learned in navigating this process so far?

[00:06:39] Sol Kennedy: Yes. Yeah. You know, I never thought that I would get divorced, I don't think anyone ever does. Of course. And facing the idea of divorce and co-parenting, I was really terrified, you know, about starting over and the divorce process actually, in hindsight and now knowing what I know about what other people go through, ours was pretty simple.

Like you mentioned. It was fairly straightforward. We mediated most of it. And so I have a lot I think us both for being able to take the high road in that situation afterwards though, the co-parenting was the most challenging thing for us. And what ended up happening was that I noticed we were just constantly getting engaged with one another, especially around communication. This was actually when I started getting back into dating. My first girlfriend at the time made just this nice gentle acknowledgement and observation that I was texting my ex a lot. And, I, at that time thought that was normal, you know, to be texting five to 10 to 15 times a day. And then I realized actually that's not the right way. It's not the right way to move on. There's a certain amount of communication that's necessary, obviously as a co-parent and there's some that isn't. And a lot of times the messages were taking me outta the process of being a dad, you know, being present with my kids and also moving on with my life. And so that became the spark, as you mentioned, of the business that I'm building now, which is helping co-parents communicate with one another.

[00:08:18] Adam: Yeah. And you described to me just the, this sort of adversarial system that exists. Tell me what you meant by that?

[00:08:28] Sol Kennedy: Well, yeah, so the family court system, I'm not a big fan of it. As a co-parent, I have experienced what I would describe as the underbelly of the family court system, where a very, very simple matter became incredibly complex. I was on the stand for many hours in a situation that really could have just been solved with a simple conversation.

And the family court system it's rooted in the court systems of this country and that there are winners and losers and there's good and bad and we have to assign blame and we have to decide who is right. And, you know, when it comes to families and kids, honestly, there are no winners in this type of battle. And so I ended up walking away having won the decision, but feeling like I had lost because it was such a time consuming and awful process for everybody. And so some of the impetus and the desire and the prayer of my current company is that we can save other co-parents from going down that path and ending up in the arms of the family court system, which I don't think always protects people.

[00:09:44] Adam: Yeah. Oh, I hadn't even thought about that. That, you know, we have the system that's de, that's really designed for punishment and we're trying to figure out something that's supposed to be equitable and like you know, it's partnership even in separation. And so that's really challenging.

[00:10:02] Sol Kennedy: Yeah. And there are no criminals here, right? We're all trying to do the best we can. We're all trying to be the best parents we know how to be. And you know, really at the end of the day, a system like this takes people away from their kids.

 And in the court system, you hear the term best interest, always referring to what is in the best interest of the kids.

And so when I was coming up with the name for my business, I thought, oh, that would be a pretty good name to remind people that it's really about the kids.

[00:10:30] Adam: Yeah. Oh, that's really interesting. I was wondering how you came up with that name. That's good. If you had like one piece of advice having navigated the court system

and just generally with co-parenting kind of broadly, what would you tell someone who's like going into this journey themselves?

[00:10:50] Sol Kennedy: You know, learning how to take the high road and also specifically learning how to drop the rope. And I'm not always the best at this, but especially the court system can get you drawn into the conflict. This desire to win, the desire to make right. You know, your attorney might even say, well, you can go after this and this, and you should do this, and you'll, you'll win.

And you know, at the end of the day, there is no winning. And just if you remind yourself of that, that sometimes it's okay to let the other side win if it meant that you could spend an extra set of weeks with your kids, right. Just in, presence rather than in the court system.

So I think that that is the key, is just learning how to not win and to just allow and accept and move on.

[00:11:44] Adam: It sounds like just not even getting into the battle that the court system or the lawyers want you to have is a good piece of advice too.

[00:11:51] Sol Kennedy: Totally. And you know, that's, again, that's just really what I believe Best Interest’s purpose is, is that for me, it started with communication breakdowns and, you know, blaming each other and getting defensive. And then, you know, 30 texts later you're, you're up in arms, right? And, And that's not helpful for anyone. But learning how to communicate effectively with one another to ensure that your message gets across, that conflicts are deescalated, that can really help because in a co-parenting dynamic, It's such a weird relationship. If you've never been a co-parent, you don't really know how uniquely challenging this is.

Here is this person that you literally decided you don't wanna be in relationship with any longer for whatever reason. You know, there might have been something really traumatic too, in that there might even have been emotional abuse or whatnot, and yet now you're forced into a relationship with them that isn't any better.

You both are the same people and now you're having to navigate and make really important decisions, highly emotional decisions with one another. It's one of the most challenging human relationships that I think anyone can have.

[00:13:08] Adam: Yeah. Wow. That framing is really interesting. You, like, you've knowingly decided that we don't wanna spend time together anymore, and yet you have to. Right. You like, have to negotiate and navigate all this stuff. That's challenging.

So you're a si, you know, single dad, halftime parent.

 Tell me about that experience. What kind of feelings? Like What's that like? I.

[00:13:30] Sol Kennedy: Yeah, I appreciate that question. You know, it's a unique thing to be a halftime parent. You have this experience, or, I have this experience of when I'm with my kids, especially when it's just me and it's two on one. Honestly, that can be really challenging. The ages, my kids are like, it's getting a little bit better, but man, there's so many demands and it's overwhelming at times.

And so a lot of times I have this feeling like, oh, I need a breather. I need a break. I need some adult simulation. You know, especially during covid. It's like, where are my adults? I'm surrounded by kids, and gosh, I need a break. And then you get your break and you're like, oh, man, I really miss my kids. Oh, this is awful.

Like, I can't see them, I can't talk to them. I have to pretend like they don't exist in a way. That's hard. It's weird to go from this, it's like a black and white kind of experience of, okay, now you're, single, you're back to hanging out with adults. Oh no, you're back to being a dad, you know, and back and forth.

Oh, the kids are sick now. The schedule's adjusted. You

know? So it can be really, it can be really challenging. It can be really lonely to be doing that, you know, post covid obviously it's changing, but we live in a culture that we're not tribal. We're all living in our own homes and we're all doing the parenthood thing pretty much solo, unless we're making extra effort to get everyone together and do play dates. So it can be pretty isolating to have kids.

[00:15:07] Adam: Yeah. That what you described is like a rollercoaster ride of like, I'm on, oh, I'm off, I'm off, I'm off. I'm on. Uh, I'm off. What a wild feeling.

[00:15:17] Sol Kennedy: Yeah. There's like a splitting that happens too, where like, I almost feel myself putting on the daddy cap when it's like that day. I, I know that they're gonna come and my personality shifts subtly, you know, probably even hormones get ready, you know, like I'm ready to get in my daddy mode.

From being a single guy.

[00:15:35] Adam: Yeah. The thing too that you mentioned is, you know, six and eight, you know, it's not newborns. So, you know, you're not changing diapers and things like that, but six and eight year olds, and I think you have two boys, right?

[00:15:47] Sol Kennedy: No girl and a boy

[00:15:48] Adam: A girl and a boy, okay.

But still at that age.

You have to be on all the time when they're around, like they wanna do stuff, which is amazing. You know, I hear stories about like, the teenage years when they don't want to see you at all. But it's also like, I think it's okay to also admit, like, it's also exhausting,

[00:16:07] Sol Kennedy: Oh yeah, I wanna admit those sorts of things because, you know, I know it not normal to, you know, like a lot of people won't admit to being bored when they're around their kids. But honestly, it can be really boring to keep playing the same game over and over again. That can be really hard. You know, six and eight is a unique time where especially my 8-year-old, she's starting to be a lot more independent, you know, and like, she dresses herself now and that's been a while, but, you know, she'll get up on her own. She'll come in on her own, like there's kind of this independence. She'll be doing her art projects, she's a great artist and she has her own life that's developing. Whereas my son, he's still very much in, like, he wakes up, he comes to me, he wants to play a game, he wants, he's like, dictating what we're gonna do next. And as his dad I'm, learning, well, how do I set boundaries with him so that I ensure that I have my own time? And there's also this guilt of being a co-parent, knowing that, well actually, I will be getting my own time because you're going back to your mom's today. So then I feel guilty even setting those boundaries. So that's also an interesting aspect of being a co-parent, is how do you maintain those boundaries with your kids.

[00:17:25] Adam: So it's hard enough to maintain boundaries with a 6-year-old. And then you know, he doesn't get to see you all the time. And so it's probably like very intensely, like, I wanna do all the things with you right now. have you developed any strategies for that or stumbled through figuring this out?

[00:17:40] Sol Kennedy: Stumbled through is a great way to put it. think, you know, in terms of being a dad, I. I like to just be really calm with them and I'm just, I'm generally a pretty grounded guy. That's just the way I show up in life and that extends to my kids.

And, you know, sometimes you have this experience as a co-parent that sometimes the other house is a black box. You don't really know what's going on per se, depending on the communication level. And then they just arrive and then they're just filled with energy and you hear a lot about like, oh, they come back so crazy from their dad's house or their mom's house and what's going on over there. Sometimes the kids are just really excited, you know, they're really excited to see you again after. And that's the way they're expressing their excitement is by being absolutely bonkers. And so for me it's about creating those rituals. So I, do a, a little ritual with them when they come back home where yeah, it's a little woo woo, but I'm a kind of a woo woo guy.

We do a little ritual where we gather and they each pick out a crystal in our object from, you know, the room. And we get together and we just talk a little bit about what happened and, you know, what we're gonna do the rest of that week. And as a way to just kind of ground into each other, welcome them back, and then, you know, say you're here now.

I think that's important to have that ritual so they are able to like say, okay, we're here now. We're all together.

[00:19:06] Adam: It sounds a little bit like the circle time that they do in school to kind of set their intentions for the day and like talk about what are we gonna do today? You're doing it, you know, what are we gonna do this week? Or what are we gonna do while you're here? But that seems to work pretty well in school, so.

[00:19:23] Sol Kennedy: Totally. Yeah. That's a very similar approach. And I also just, you know, when it comes to being with them, I just really like to be patient. You know, they might be going through a lot that I'm not even aware of. Right. And so it's about being patient with them and taking things slow and just listening to what they wanna do and, just being there with them.

That is one of the benefits of being a co-parent is that I do have the benefit of being able to be a little bit more on, because I've had sometimes a week off where I've been able to, you know, really focus on me time and renewing myself and then I can show up with my full energy and I'm not so worn down.

So that is another benefit of being a co-parent. I actually I wish that more married couples would give each other time off. I think that would be very beneficial to marriage to allow each individual to remain independent from their kids sometimes, because it can be a slog when it's the two of you all the time with the kids all the time.

[00:20:30] Adam: Yeah, I am curious. You were in the fairly fortunate position of being able to take some time off to be a full-time dad

[00:20:41] Sol Kennedy: Oh my gosh.

[00:20:42] Adam: A period of time.

And, then you went back and started a company, which is like the polar opposite. So I'm curious about both ends of that spectrum. Why did you decide to be a full-time dad or maybe that decision was made for you and then, you know, what made you take the leap back into company building?

[00:21:03] Sol Kennedy: Gosh, I mean, the company building first, just to say, I mean, it's a bit of a compulsion and we'll return to that, right? Um, Just to be honest here. But the taking the time off, you know, the way that my career had gone, I've always been a small startup guy. That's what I really like doing.

It's the most fun for me being able to put out the fires and put on the hats and not really worry about politics and stuff. Well, I ended up through an acquisition and then another acquisition at a big company at Google, and I thought going into it, this is my dream. I'm at big company, great healthcare, and sure enough, you know, great healthcare meant , kids and, and all that.

Like, it felt like the right time. And but I really didn't like the job. It wasn't my cup of tea. Like, it was very political. As a lot of companies are, you know, no dis in Google. They're a great company. But it was difficult for me to be in that environment. I was not being an entrepreneur in that moment in my career. And I've always known that I wanted to be a dad, always since I was a kid. I just had that dad vibe. Just always had that. So when I knew I wanted and I was ready to be a dad. I knew I wanted to jump in and have that experience and just do it wholeheartedly like I do all my other projects, like make that my startup basically was the idea. Yeah, so I decided to quit my job after my daughter was born, you know, eight and a half years ago now, and I thought that was gonna be maybe a year sabbatical and that I was gonna get back, get re-inspired, and that inspiration didn't come. You know, I , I was so focused on being a dad that was my inspiration and honestly, very overwhelming being a full-time dad.

I developed some very good empathy towards people that choose to do this, towards my mom who did this for my whole childhood. It's a lot of work. It's very demanding. And yet I wouldn't take it back. All the memories that I had just being with her during the day and like having that connection of being able to see her wake up in all of her stages of development.

It was just, it was so beautiful to have experienced that. And I didn't expect that would become another kid and then divorce and then co-parenting you know, as it went. And that became like its own midlife crisis. And then through that process of co-parenting and seeing the challenges there, feeling so challenged myself. Also knowing that deep down I'm a technologist. I love technology, I love building, and knowing that I was a little rusty, you know, from all those years of just being a dad I decided though that it was my duty to wipe off the dust and get back in there and solve this problem with software.

[00:23:59] Adam: Yeah, and you did the, I don't wanna say the classic thing that founders do, but you did the thing where you're like, I am experiencing this problem myself.

I know that probably plenty of other people are experiencing this problem. I'm gonna build something that helps people alleviate this problem.

[00:24:17] Sol Kennedy: Totally. And you know, I would say I have not ever had quite, this experience of feeling so mission-driven. Like it's, to me, this feels like I found a vocation. I really wanna help co-parents in these situations cope and find peace. It's like through my core, I've done startups before and I felt really good about what I built, but this is the first time where I saw a need, I heard what people needed, and then I built it.

And I feel so inspired every day to wake up and keep building for them.

[00:24:52] Adam: Yeah, and the mission here, like these are like very real human problems that you're solving like and you live through it. And so it almost feels like more meaningful as a result maybe.

[00:25:04] Sol Kennedy: And Adam too. I would say that for me it was a hidden problem before I became a co-parent. I had no idea. In fact, honestly, I think a lot of people who are married don't want to even think about divorce, right? They don't want to even talk to divorced people or interact with them because they don't want to admit that could be a possibility.

And so what I am trying to do with this company is say, Hey, you know what? Like this is a real problem that people are facing. This is a really difficult relationship and there are not a lot of good solutions out there. And so, yeah, I'm jumping in and helping bring light to what can be a really dark and lonely situation for a lot of people.

[00:25:45] Adam: So this is a little bit of a funny question here, but have you onboarded your own family onto best interest, or is that like a bridge too far?

[00:25:55] Sol Kennedy: I, I'm gonna keep that one a trade secret. Uh

[00:25:59] Adam: Okay. I can only imagine how that conversation would go. So, we'll just move on. What are some of the most surprising things that you've discovered as a dad?

[00:26:11] Sol Kennedy: Oh, wow. What a good question. You know, I think the first one is just how challenging it is. I think. Everyone on some level walks into it thinking, oh, I'll be great. I'll do it better. And then you become a dad and you realize, oh man, this is bringing up a lot of shit. Oh, wow. Like, so the things that I didn't heal from my childhood at this age are gonna start coming up.

It's almost a magical portal of healing being a dad, especially when you're really open towards and oriented towards personal growth and healing. It can be such a rich and challenging experience to to become a dad. You know, and I think, like I mentioned earlier. One of the things I didn't anticipate was the loneliness that it is being a parent, let alone a co-parenting parent. And I just, I really love advocating for a shift in the way that we look at parenting and co-parenting towards more of a tribe and more of a community bringing more people together to help out. I think kids benefit when grandparents participate, friends participate, other people, neighbors, right? When they can look up to multiple adults and they're not just relying on one parent for all of their attention. I think that that is really beneficial.

[00:27:41] Adam: I had someone else on the show who said one of the most isolating places on the planet is being a dad on the playground with your kids. 'cause you're often the only dad there, or, you know, you're, especially if it's during the work week, you know?

[00:27:58] Sol Kennedy: Oh my God, yes.

[00:27:58] Adam: Anyways, that resonated with me, what you just said about the like kind of loneliness and the, you know, the isolation.

[00:28:05] Sol Kennedy: I'll echo that. Yeah, I think especially early on when my kids are really young and you know, going out to the playground specifically it was challenging as a dad because there's this really weird subtext in our culture about men and children and relationships and like questioning and doubting and that's so, it's so problematic because the dads I know are really good dads and they just want to help and they wanna be involved and the kids benefit from their involvement. And I've noticed that over the years as a dad who shows up, field trips, you know, other places where other kids are. They gravitate towards me probably because their dad probably is working or not as involved. Right? Like they feel that energy and they're like, oh, you know, kids just really, they wanna have an involved dad, they wanna have an involved mom.

They wanna be part of that.

[00:29:03] Adam: Yeah, you mentioned a minute or so ago about, you know, having kids, brings up a whole bunch of stuff about your relationship with your own parents and things like that. I, I can certainly appreciate that myself. But I think one of the things you also mentioned to me is that your kids helped you heal relationships with your parents.

So tell me a little bit more about that.

[00:29:28] Sol Kennedy: Well, I mean, you talk about it like past tense and I would say that it's an ongoing process. Um, You know, it, it brings up a lot and I don't know what this life is all about. Still trying to figure it out. Probably will never figure it out. But one of the orientations that I have now that I didn't when I was younger, is that I believe that life is about growth.

I think that, you know, we've come here on a journey and we're learning things and we're learning things about ourselves and we're trying to get stronger and better. And we're navigating relationships. I know one of the themes in my life has been how to unravel my own codependency and stick up for myself more to shine my light writer to be more visible. I was a very shy kid and, you know, very codependent. And I'm still unraveling codependency. And my kids have really helped me because the one thing that having kids does is it does force you into connection with your parents. Because they wanna be involved and they're great with the kids. They might have been really challenging parents, not saying anything about mine, but they might have been really challenging.

But they wanna be great grandparents and usually for whatever reason, that's how it works out. They're great grandparents and so you want them to be around, you need the help. And so they create this kind of forced bond where anything that's unresolved in that relationship between you and your parents is being brought to light and you're having to work on that so that it's not constantly triggering you. It's wild how that works.

[00:31:05] Adam: Yeah. I’ve had some other conversations with folks where they're like, you know, my own parents when I was a kid, you know, they were okay, but like, wow. As grandparents, they're like off the charts like what clicks, you know, when they become grandparents. So, I don't wanna say that that's your lived experience, but it sounds like you got some great grandparents now, so.

[00:31:27] Sol Kennedy: They are the best. They are so into that position. And it's such a sacred position, like being able to jump in, relieve the parent for a little bit, and just provide a very different experience for the kids, you know, just being super present. As a parent, you're filled with all these other obligations and things in your mind and things you gotta do and your work.

And especially as a startup dad, man there's a lot going on up there, but they don't have that right. So they're able to just be really present and just get down on the floor with them and just be with them. And that's such a beautiful gift that they can give to their grandkids.

[00:32:07] Adam: Yeah, so you have now an eight and a 6-year-old, and I want to get in the time machine for a second and go back to, you know, I. Before your oldest was born, right? Before you had your first kid, and you bump into younger Sol in the time issue, which I think is actually not allowed based on the laws of physics, but let's say you do what would you tell your younger self about being a dad? What advice would you give yourself?

[00:32:35] Sol Kennedy: Are you sure about this? I mean, I would never take back becoming a dad, but I think that it's important to not take it for granted as something that everyone has to do, or it's something that you gotta tick the box and it changes your life. Like becoming a dad it is a new chapter no matter what you do, like your focus changes. For me, It was pronounced because I decided to become a full-time dad. Right. So like that, it's even different than having a career and also being a dad. But even when you're still employed, like you suddenly realize, oh, it's not about me anymore. Like biologically or whatever. You start being much more oriented towards their life, what they're up to, and realizing that if it really came down to it, you would absolutely protect them and allow your life to be taken so that they could, like, that just becomes almost overnight and that shift is such a big shift in the way you view the world.

And so would, I say don't do it. No, but just like, it's a big deal.

It's an important decision. And just make sure you, you think it through.

[00:34:00] Adam: Yeah. Appreciate the gravity of the situation for all of its, you know, challenges and opportunities and excitement, but appreciate it.

[00:34:08] Sol Kennedy: Totally. Yeah.

[00:34:10] Adam: What about in the transition from one to two kids? Like what have you learned as a dad? What would you tell yourself about maybe what you do differently with your oldest kid than you know you did?

[00:34:24] Sol Kennedy: Yeah. Well, there's definitely a few things. I think going from one to two in terms of like, daddy responsibility it's not two x, it's like 20 x. Like it's, it's ridiculous. It just becomes so much harder. But also one of the things that it taught me was that it, just don't sweat the small stuff. I look now at products that are sold to first time parents, and I'm like, oh, that's, hmm, that's awful. Like you see those baby cameras that are attached to the bassinet and it's like $2,000 and you're gonna use it for three months, and yet it's being sold like hotcakes because they're selling to the fear. And when you're a first time parent, especially when you hold your child for the first time and you look in their eyes, you're like, oh my, this is important. And you're ready to buy anything. And also, I remember just being terrified at every noise. It was crazy. Like she just, her breathing. I thought, there must be something wrong there.

There must be I, we have to call the doctor, you know, like I was so hyper-focused and common experience. By the time my son was born, like I had been through the ringer, I'd known that everything is totally okay. Kids are very resilient. They're built like a tank.

It's fine. They're gonna survive through pretty much anything.

And so for him, like obviously that was a lot easier and I didn't buy all that crap that you don't need.

[00:35:54] Adam: Yeah. you said two things there that I, really appreciate. One is the loud breathing is a sign of imminent death, and I just remember when my dau, my, my oldest is also a girl. Just like the noises that babies make when they're sleeping, they're like grunting and like, and they're totally fine.

It's just very normal, but they're not quiet. They're like, you know, they're like, what I would imagine like an 80-year-old man is making the noises of in his sleep. So that's one. And then the idea that, you know, the kids are gonna be okay. I always tell people like, ah, kids are pretty much made of rubber, you know, they'll be fine.

[00:36:29] Sol Kennedy: They're totally fine. Yeah. And second kids get a different treatment because of that. You know, there's, I think a lot more flexibility that they're given. There's maybe even less expectations. You're kind of, in some ways, over all that stuff and it's good and it's bad. It's just a different experience.

[00:36:47] Adam: Yeah. So you talked about, you know, life being about growth, personal growth learning and I'm curious if you've developed any frameworks or guardrails for parenting or like how you've grown in thinking through what it means to be a dad?

[00:37:04] Sol Kennedy: A lot of parents, when they approach parenting they do the googos and gaagas and they like kind of, I've always wanted to treat my kids with the same level of respect as if they were adults, right? I think that we talk down to our kids sometimes thinking that maybe they don't understand or they're not ready. And I'm not necessarily saying like, use big words and be eloquent, but I just really wanna respect them and respect their personhood in the same way that I would with an adult, if that makes sense. And, you know, in addition to that I, tend to like allowing them to do it on their own when I can and to even give them responsibilities that are way above their pay grade because I think that's really fun.

I'm not afraid of giving my kids. A hammer or a power drill. You know, I figure if there's really a problem then, you know, we can take care of it. And I watch them closely. But I think I just love seeing the eyes of my daughter light up when she knows that she can hold the drill that daddy uses to build something. I think that it just gives her like this added weight and responsibility and like feeling of freedom.

[00:38:26] Adam: My kids are amazed by power tools. That's really, That's really a thing I've learned. Yeah. 

[00:38:32] Sol Kennedy: I mean, I haven't always been a builder, actually, that was something that evolved. After my daughter was born, I was always a coder and sat behind my computer, and I had this experience actually one day of wanting to get a garden bed. We were living in San Francisco at the time, so the idea of having a garden was like this exotic, crazy idea.

And so I went down to Home Depot and I said, do you have any garden beds? And, I said, oh, you know, like, it looks like they're sold out, right? So he said, oh, well, it's just wood. And I'm like, what do you, oh. oh. it's just wood. Like I could build it myself. There was, There was something that clicked that I didn't realize I didn't have to buy it from a kit.

I could just build it. And so I have since then built a lot of really great things. I love working with my hands. I've developed quite a tool collection, and I love passing that down to my kids, knowing that they can build it themselves, they can repair it themselves. We love repairing things instead of buying new things.

That's a big thing around here. I like teaching them that stuff.

[00:39:37] Adam: Yeah. And also very empowering for them to feel like I can do this. You know, it's just wood,

[00:39:44] Sol Kennedy: It's just wood. Yeah. Let's build it ourselves. Let's empower ourselves. I think in this culture, we have this outsourcing mentality where everything is assigned to a professional to do. You can't really do a lot yourself these days because it's a professional's job to do it. And I think that's actually a really big disservice. As we're facing a very uncertain future. I want my kids to know how to build things. I want them to be helpful members of their community, and I want them to be able to operate independently, run their own house, and, you know, fix things around the house without needing to employ someone for everything.

[00:40:21] Adam: Yeah. Speaking of building, you have built a lot of technology products in your life. Your entire career has been building things like starting companies and building products. You know, your kids are getting to the age where and society is getting to the place where like technology is deeply ingrained in our lives.

And I'm curious what you want your kids' relationship with technology to be as they're getting older?

[00:40:50] Sol Kennedy: You know, we're, we're watching the airplane being built while we're flying in it, right? And I think this AI change is much bigger than we really can fully grasp 'cause we're in the soup. and so I definitely have my mind on that when I am seeing what they're learning in school. Obviously the public school system's not adapting very quickly to this. Education in general is not adapting very quickly to this, and I'm really uncertain what the future's gonna look like for them. You know, when they are old enough to get a job, will there be jobs? Right? What will the jobs look like?

How are we going to define what productive work is? Is it going to be just being really good at managing a bunch of AI agents? Maybe. I think that there's a lot of, let's wait and see and let's just find out what happens. My daughter is an amazing artist and we did this great thing with the new chatGPT I don't even know if there's a brand on it.

The new cartoon tool. the new image generator. Oh my gosh. Such an amazing tool. I was a mid journey guy for a long time, and this is just miles beyond. So what we did is she's super creative. She just started drawing these amazing animal cups, I think could be an a to a product.

Absolutely. And she draws them and she's like, we'll get requests on Facebook. And she draws on requests and it's really fun. I thought, what if we popped this image that she drew into ChatGPT and ask, make it real. Right. And. Sure enough, it made this amazing plastic in, you know, in a real cafe and it just, it was so, I could tell it was so inspiring to her to be able to see the reality of what she's making.

And I can see that as being something that will be very helpful in the future is, the humans being the spark of the inspiration that leads to the product, right? that it's all about ideation, individual creation. And so for me, when I am thinking about that future, I really hope and would love to inspire my kids to be entrepreneurs themselves and to be thinking about what they wanna put into the world, the reasons why, how to come up with a good idea, how to be a self-starter. And also honestly, I think being an artist is really important. And I think that is perhaps going to be the way that we are communicating with these machines and understanding them is through art, through storytelling. And we'll see. We'll see where it goes.

[00:43:32] Adam: Yeah, you're echoing is something that I've heard from, you know, a growing number of dads on this show, which is using technology as an active participant and as a tool for that growth that you describe. Right. And so how amazing at some point for your daughter to be able to go from, like, I drew a picture to maybe this thing can be produced physically, now, this picture that I made, what a cool concept.

[00:43:59] Sol Kennedy: AI is going to make it so that you can have an idea and you can make a real version of it, literally in an hour or less, right? And it's gonna come up with a marketing plan, and it's gonna know where to distribute and it's gonna make the connections. And your AI agents, it's going to be such an incredibly explosive time of creation. And so then my question is, what is that world gonna be like to live in? Right? That's where my fear is, is just being overwhelmed by all the great products and ideas and apps. It's like, how are we gonna be able to consume all of that?

If I succeed in this parenting thing and launching them, I really hope to launch them into being a little entrepreneurs themselves.

[00:44:46] Adam: Hmm. That's awesome. On the flip side. What would you say is a mistake that you made as a dad?

[00:44:55] Sol Kennedy: I've made several. So I think the biggest one that I have the most regret about, honestly you know, it's interesting to admit this in a public setting, but I like to live my life openly. I think it's this memory I have of when my son was three he was like deeply into that three-year-old energy of feeling the frustration of the world not conforming to your wishes, and then not being sure what to do with that energy and channeling it into aggression and anger. And as his father, it was pretty frightening and overwhelming to experience that. And he would start punching on his sister and punching on me and like being able to produce a fair amount of pain. And so that I knew wasn't gonna stand and I didn't know what to do. And so I remember in one of my iterations of trying I tried to holding him so that he couldn't like, but then that felt like weird, like I was restraining him and it didn't seem to help him at all.

He just got worse. And then one day I thought, well, I'll put him in his room. Well, we're in a house with two doors on his room. So that didn't really work very well. He just ran outta the other door, so, whoops, dad. And so I thought, okay, well maybe if I just, 'cause I had this notion maybe from when I was a kid, I don't know, go to your room when you're upset, right? And so I thought, well, maybe I'll just put 'em in this closet. And, you know, maybe that'll calm him down. Well, it calmed him down immediately, and I opened the closet and the look on his face was just like, it was so sad. Like, I feel sad even relating that or thinking about that image, he was so sad. And so in that moment I thought, oh, I'm never doing that again. That's not something that I'm ever gonna try. And what I have learned since is that it's really about I don't wanna ever push my kids away or even create separation, right? Because kids are, they're governed by wanting association with you. That's how they feel. Safety. So if you're pushing them away and saying, you're now disconnected from the tribe, go, you know? That's the worst feeling in the world. That's like, as an adult that's torture for a kid. So I try to never do that. But what I do is I help show him ways to use and manipulate that energy in productive ways. And so I try to redirect it. And so we started doing was I would take him to a different room with me.

I'm there with him, and then showing him and doing it myself too. But like punching, punching a pillow, something safe, right? Allowing him to push against me while I hold him right? And just being okay with that energy being directed at me. And that really helped, honestly. And I think that I would imagine that is helping him learn how to be in relationship with that energy. Those emotions that are so strong that honestly will be part of his, my whole life. So I want him to have a good relationship with his anger, with his sadness. So Yeah. That was

[00:48:19] Adam: Wow.

[00:48:19] Sol Kennedy: a mistaken in learning.

[00:48:20] Adam: Yeah, and I mean, thank you for sharing that story. I would imagine it's more common than we might think to have something like that happen. And it sounds like you've learned a good lesson about not trying to quiet the energy, but just redirecting it into a different, more productive place or allowing it to be there, but away from harm or anything like that.

[00:48:45] Sol Kennedy: Yeah. I love what it's allowing the energy to be present but directing it into a place that's more productive and safer for everyone. Including it rather than excluding it.

[00:48:57] Adam: Yeah. Well, that sounds like a great thing to end on, a great lesson to end on. So I appreciate you sharing that. How can people follow along or be helpful to you on your journey?

[00:49:12] Sol Kennedy: Well, for any of your listeners that are co-parents themselves you can look me up. I run a podcast called Co-Parenting Beyond Conflict, where we specifically talk about how to cope with and thrive in this sometimes very challenging situation of being a co-parent. So you can look us up on Apple Podcasts wherever you get your podcasts. And also if you're interested in co-parenting with Best Interest, Best Interest allows you to create peace and can be a very difficult situation using AI as a tool to moderate all communication between co-parents. You can experience peace. So you can look us up on bestinterestapp.com.

[00:49:52] Adam: Okay. Well thank you for those. We'll link to both of those places in the show notes. So appreciate you sharing that. Are you ready for our lightning round?

[00:50:02] Sol Kennedy: Sure.

[00:50:03] Adam: No one is ever officially ready for lightning

[00:50:06] Sol Kennedy: I thought I was off. Shoot. Okay.

[00:50:08] Adam: Okay, here we go. What is the most indispensable parenting product that you have ever purchased?

[00:50:15] Sol Kennedy: This one's great. So it's a little bug catcher that has a little sliding trap door. And whenever you find a bug in the house, you can go and just take it safely outside. And I think that that is such a great image or a great experience for the kids. Not only do they get to look at the bug 'cause it has a nice magnifying glass in it. They can learn about bugs, but it also teaches them that it's better not to kill things. we love it. Every time we see a bug get the bug catcher, dad. There's no panic. It's just like, go do this thing.

[00:50:47] Adam: That's awesome. What is the most useless parenting product that you've ever purchased?

[00:50:52] Sol Kennedy: Earlier in the interview I was talking about these products that are sold to first time parents. Honestly, I think it's, pretty awful. As a first time parent, I would highly encourage you, get only used things, don't buy new stuff. Definitely don't buy technology. Your baby's not gonna die. I mean, SIDS is a real thing. Absolutely. But not at the level that you're afraid of it right now. Don't buy that fancy $200 sock that'll monitor. It's just gonna go on the wastebin. You know, it's like not, not helpful. So just keep it simple and get all your stuff. Hand me down.

[00:51:24] Adam: This is the second time, probably in a week or two, that somebody has said that the, that baby sock, that monitors is a terrible idea. The last person said it's because the baby sock makes you think that your kid is always dying.

[00:51:37] Sol Kennedy: I never used the baby sock, but I definitely thought about buying it and yeah, I now, no, in hindsight, no, it's not a good use of your time or money.

[00:51:46] Adam: All right. What is your signature Dad's superpower?

[00:51:50] Sol Kennedy: Yeah, I mentioned it earlier. I think it's my, my calm, my grounding. I tend to be able to navigate all situations with my kids with like, calmness and I really like to help them redirect that energy..

[00:52:04] Adam: Now, in your household, are you team swings or team slides?

[00:52:09] Sol Kennedy: I really, I love doing things together with my kids. And I think I like slides and I think my kids really like slides too. We don't have a slide. We have a swing. Swings are cool because you can do it together. I love pushing my kids on a swing. It's like the best thing. I'll be so sad when they stop asking me to push him on a swing.

[00:52:29] Adam: Yeah. If your kids had to describe you in a single word, what would it be?

[00:52:34] Sol Kennedy: Is it the first word that comes to my head? I don't know. Maybe nice Daddy. I actually don't know.

[00:52:42] Adam: Yeah, that, that checks out. That's probably good. What is your go-to dad wardrobe?

[00:52:48] Sol Kennedy: I am all about efficiency, as you can tell. I love hoodies. I love warmth. And honestly, I've never been fashionable. But I was a little bit more fashionable than now. Now I'm just like, ah, whatever.

Just put it on. I don't even care about my hair when I drop off the kids at school.

Like, who am I trying to impress? Noone.

[00:53:07] Adam: It's all about convenience. Yeah. What is your go-to bribe for good behavior with the kids?

[00:53:14] Sol Kennedy: Well, we do this thing here that is actually really cool. It's worked pretty well. So we have a token system and I have somehow trained them that tokens are the reward and that they can use the tokens for things that they want. And so we have this system that's set up where, you know, if they do something good, like clean their room, then they get a token. And then if they wanna do something like watch on the tv, it costs a couple tokens. And so it's like an early introduction to chores. We're starting to adapt the token system to be convertible to money. So there's kind of a mapping to money and they were able to buy something with tokens.

And so there's kind of that going on. But I really like disintermediating reward with like. Work. I never liked the idea of like, okay, if you do this thing, I'm gonna give you this candy. Like that's just not, and oftentimes the reward doesn't always follow. So I like this idea that they have a duty to clean their room.

And that's not always gonna map to them watching right after. But they know that when they're building up those tokens and later they're gonna be able to get the reward.

[00:54:26] Adam: Yeah, maybe when they're older you could build a little app for them that they could keep track of their tokens

[00:54:31] Sol Kennedy: Don't. No, don't get me started. I'm already busy. Adam. Busy.

[00:54:37] Adam: Okay. Speaking of rewards in purchasing things, what is the most absurd thing that one of your kids has ever asked you to buy for them?

[00:54:45] Sol Kennedy: Well, okay. It's not exactly absurd, or at least it didn't start that way. My son got a stuffed piggy. I don't know if it was like a gift or I don't really know how it came into our lives, but he loved that stuffed piggy so much. And this would've been probably almost two years ago now. Loved it so much that the piggy started going back and forth between the two homes. My kids aren't like big into bringing things back and forth. Somehow that's actually pretty good. It's pretty easy. But this pig would go back and forth in his backpack and it was like on the order of being a little too big for his backpack.

So, but then I think I may have made the mistake of buying him another piggy. And then that piggy became three and suddenly three piggies were going back and forth. And that was when daddy put his foot down, said, no, you can't do that. That's too many piggies for school. So, I made the ingenious decision to tell him, okay, I'll buy you three new piggies and then you can have, keep those three piggies at the ones you have at your mom's house and keep three piggies at my house. And we're good. Right? We're good. You don't have to take him back and forth. And he's like, yeah, good. And I thought that was it. So now we have 36 pigs. He's proud to tell you, 36 pigs. And it didn't work. They go back and forth. They're, we have pigs everywhere. I don't know what's going on.

But that was not a good solution.

[00:56:10] Adam: You need a separate vehicle just to transport the pigs. It's like moving a football team back and forth.

[00:56:15] Sol Kennedy: We have moved pigs in boxes before. Yes.

[00:56:18] Adam: This is my, this is the equivalent of my son with penguins. Same thing. He doesn't have to move him back and forth, but he does like to bring a penguin or two on a trip,

[00:56:25] Sol Kennedy: Yeah. You know, I don't know what it is. I think it might have something to do with like, he feels known by his association with piggies. Obviously he likes 'em, but this is like the piggy king of his school. Like all the other kids know that he loves pigs and they barter pigs with him. Like they give them their stuffed pigs that they don't want.

Like this guy’s got, he's got piggy game.

[00:56:50] Adam: Swimming and swimming in pigs. He's got real riz when it comes to pigs. So as the kids say what is your favorite kids movie?

[00:56:59] Sol Kennedy: You know, there's a lot of crap out there. I think what I like the best is sitting down with them, with Pixar. I think Pixar is pretty much always good and I love how it's entertaining for me and for them, and it just works for everything. Yeah that's my go-to.

[00:57:13] Adam: Okay. All things Pixar. What is the worst experience that you've ever had assembling a kid's toy or a piece of furniture?

[00:57:22] Sol Kennedy: My kids are very lucky because they have a dad who is quite handy. My grandfather actually growing up, I remember he was so handy and was able to do anything and build anything for me when I was little and I would always looked up for that. And so I loved being able to be that for my kids, but also teaching them how to build stuff too, and like incorporating that in.

I'm not gonna do it all for them, but I'm gonna teach them how to do it so they can do it with me. And so, yeah, I wouldn't say that I've ever had any struggles with building anything and I love building things with them and making my own stuff and, yeah.

[00:57:58] Adam: Awesome and an amazing rarity in a dad I find these days.

[00:58:02] Sol Kennedy: Really? Oh, that's surprising.

[00:58:05] Adam: Uh,

[00:58:06] Sol Kennedy: It's just wood.

[00:58:07] Adam: It's just wood. I love that. That's gonna be the title of this episode. How long can a piece of food sit on the floor and you will still eat it?

[00:58:15] Sol Kennedy: Oh, I don't know. I mean, uh hmm. I am pretty sensitive to my digestion and I'm actually fairly critical of not eating things that, you know, when in doubt throw it out. That's.

[00:58:30] Adam: All right. I think it's a good rule to live by. Yeah. Okay, two more for you. What nostalgic movie can you just not wait to force your kids to watch with you?

[00:58:41] Sol Kennedy: Star Wars. We're still waiting on that one.

I think maybe about a year ago. Like I, I opened it up a little bit too early and like there was some fear that I sensed, so we stopped it. But God, I can't wait. Can't wait to show them Star Wars.

[00:58:55] Adam: Yeah. Now will you go, so there's nine of them now. Will you start at the very beginning or will you go like the original order that they were released? What do you think?

[00:59:04] Sol Kennedy: I think original order. You got to, I I don't even, I think I'll just pretend like the other ones don't exist and let them discover them on their own. One, two, and three.

[00:59:13] Adam: Not worth

[00:59:14] Sol Kennedy: I'll let them disappoint

[00:59:15] Adam: Yeah. Yeah. Okay. Finally only have two kids, but you do have a lot of pigs. So what is your take on minivans?

[00:59:24] Sol Kennedy: Well, you know, I'll tell you, it's a complicated take. I think that there is a choice you get to make as a parent when choosing cars. You can either be the parent that drives every single kid around everywhere all the time. If you wanna do that, get the minivan. If you wanna have a little bit more peace and less responsibility and have your kids be driven around, then get the normal five seater. That's what I chose.

[00:59:55] Adam: Mini Cooper.

[00:59:57] Sol Kennedy: Yeah. Right. Motorcycle, sidecar.

[01:00:02] Adam: I love that. Sidecar just for the pigs actually, so, yeah. Okay. Well, Sol, it has been my absolute pleasure having you on Startup Dad today. Thank you so much for joining me and best of luck to you, your family, and your burgeoning app. Best Interest, I'll have to go check it out.

[01:00:21] Sol Kennedy: Thank you, Adam. I really appreciate it.

[01:00:24] Adam: Thank you for listening to today's conversation with Saul Kennedy. 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 has a YouTube channel. You can find it by searching Startup Dad pod on YouTube. If you're a startup founder, leader, or just want to get better at your job in tech as a growth practitioner, product manager or executive. You can join a community of over 11,000 subscribers and stay up to date on my thoughts on growth and product by subscribing to the Fishman AF newsletter at www.fishmanafnewsletter.com.

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