Becoming An Empty Nester And A Trusted Advisor To Your Kids | Darin Swanson (father of 2, New Relic, Gatsby, Bounti.ai)

StartupDad_DarinSwanson-V1

Darin: She's often reminded me that if you left, the company will forget about you in about two months. You're never that critical. You're never that important. Not that it's not important what you're doing, but they will survive without you.

Your family won't.

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. And in today's conversation, I sat down with Darin Swanson. Darin is the former VP of engineering at New Relic and is now a serial advisor and interim technology executive for the past seven years across dozens of companies.

Darren is a glimpse into the future for many dads, as he and his wife have raised two daughters who are now adults in their 20s. In our conversation today, we talked about the move from being a parent to a trusted advisor, how to set up the relationship with your kids when they no longer have to listen to you, and how to work with your spouse to be the barometer of when it's time for a change, personally or professionally.

Darren brought over two decades of parenting experience, lessons, mistakes, and some advice on becoming an empty nester. I hope you enjoy my conversation with Darin Swanson. ​

Adam: I would like to welcome Darin Swanson to the Startup Dad podcast. Darin, thank you for joining me today. It is a pleasure to have you.

Darin: Yeah, this is great. Been looking forward to this for months now, I think.

Adam: Wow. Months. No one has ever told me they're looking forward to my show for that long, but hopefully I do not disappoint. So Darin, this is really interesting episode today because you are an empty nester, so to speak, you have older kids, and it's a perspective that I've always wanted to share on the show.

So I appreciate you offering to come on, but let's go all the way back and let's get started and talk about first professional background. So tell me and our listeners a little bit more about who is Darin. What do you do for work?

Darin: Yeah, so, I have happily fallen into a job I did not even know existed. Started doing it about eight years ago, seven, eight years ago advising, mentoring, interim, fractional executive, technical leader, product leader, kind of all of those different shades. I did all my learnings and mistakes. And well, I've made mistakes since then, but I did a lot of them during a tour duty at a startup called New Relic.

I was there for seven years and now it's amazing. It's seven more years after where I basically try to partner up with people leaders who are looking to increase their strategic impact as they help you know, hyper growth venture backed startup make its gear changes towards, you know, better, stronger, faster.

And yeah, I just really enjoy watching people find their stride, find how they want to be leaders. And I'm super, super excited about doing that

Adam: Awesome. That is so fun that you've been able to do that for like seven plus years now, especially after a seven year run at New Relic. Let me ask you, when you left, this is a little deviation from daddom. But when you left New Relic after being there for seven years, was it hard to figure out what you wanted to do next in life?

Or was that something where you're like, I know that this is next for me?

Darin: Nope, absolutely hard. Two things come immediately to mind. You know, we plan, God laughs. So that's the first one. And then the second one, a piece of advice I got, don't do anything into your next phase for six months. And that was actually the hardest because I had so many people come out of the woodwork.

Hey, you've left New Relic, do this.

And I didn't know what I wanted to do. I actually intended to take my running shoes and my bicycle and head off into the mountains with my wife and enjoy, explore. And that advice really stuck, you know, I did a lot of gardening, I did a lot of running, did a lot of thinking, did a lot of talking.

And that's how I fell into this role I didn't know existed or you know, not in sort of the mainstream, but being an advisor, being a yeah, a helper, a partner to those who were staying in startup land and using my experience to hopefully, you know, help them to do even better than I did.

Adam: All right. I had a very similar feeling myself when I ended a couple of bull runs at that company. So, and that, yeah, that pressure is real. People are like you mentioned coming out of the woodwork.

Darin: It was my first break. Like every other transition in my career, it was like ended Friday, started Monday. And so it was very, you know, different from anything I'd done before.

Adam: let's go all the way back in time to Darren growing up. So you're like, you know, 25 or 30 now. So let's go, we'll just go back to when you were a kid. What was life like growing up? Where are you from? And tell me about your family.

Darin: Yeah, it's not so bad just coming after the holiday season in Santa Claus. I grew up closer to the North Pole probably than most people. North Central British Columbia, a place called Prince George. One of my sayings, an amazing place to grow up, a great place to leave. You know, getting exposed to the outdoors you know, freedom, running around on your bikes till whenever, but then in terms of opportunity it basically facilitated at that time, there was no college really to speak of, there was no university. So headed south down to Vancouver Island, Victoria for school. And that was always kind of, my plan. That was one of the things my parents instilled in me was like, you know, you wanted to have a stepping stone opportunity, which was what college would allow you to explore.

Adam: What did your parents do for work when you were growing up?

Darin: One worked in the government towards a highway design. So, architecting road systems, which was interesting to me in terms of like, how do you figure that out? It looks like a simple thing, but it's relatively complex. And then the other was in the banking system, which was a game.

Looked relatively simple, but then you got into the nuance and it was complex. Yeah, whether or not they both, different phases they enjoyed their jobs, but then it was also I think both positions potentially that set up for me was like, I didn't want to be my own boss, so to speak, but I wanted to be in control of my own destiny.

And so, you know, working harder should equate to more reward and, you know, in government and banking, I don't think there was a direct path there.

Adam: Yeah. I love that way of thinking like working hard should equate to your own reward. That's a pretty good, it's a pretty good life philosophy to have there.

Darin: Yeah and then I learned that physical labor, while I loved it, I saw as I got older, like older being like 23, I was like, ooh, this is really hard on the body. And so that was you know, when you woke up in the morning, more tired than when you went to sleep. That was when I was like, okay. Physical labor has been great, but now it's time to transition to using my brain.

Adam: Yeah. do you have any siblings?

Darin: Yeah, I got a younger brother. He actually, you know, fled down into the United States earlier than I did for the opportunity. So he's been happily sequestered in California for a long time. And yeah, it's been amazing. We've eventually ended up in pretty similar spaces. And yeah, I just love the relationship towards us, you know, workshopping thinking he's a little earlier in his career with kids.

So, that's been fun too, to hopefully help him where, you know, we both succeeded and failed.

Adam: Yeah. Well, good transition. So let's talk a little bit about your family now. You have a partner, wife, and two adult kids. So tell me about your family.

Darin: Yeah. It's still hard to say adult kids. I still feel like I'm 10 years younger than I am, but they've done amazing. Maybe both because of us. And in spite of us both are now, I think post college 1st oldest is in a career in computer science which has been great, but also challenging in the COVID times.

And, you know, with remote distributed work, early career, I think as an industry, we're doing a very poor service in terms of investing in people who are just coming out of college, a bit of an editorial there. And then the second is in between undergrad and grad. So applying to grad schools, and that's something I know nothing about.

And so that's been fun partnering up with her towards, you know, grad schools, opportunities, how do you weigh and cons when you got multiple opportunities? And also back to what we talked about earlier, making your own opportunity. Because this is now more pitching and lining things up towards what you want at the intersection of what your sponsor wants.

Adam: And you've got, your oldest kind of following in your footsteps, so to speak. Yes and no.

Darin: Yes and No, Yeah, Claire is wiser than me. Has what is I think a hobby and a passion and then what is a solid and fun career. And what I mean by that is creative writing. They're working on that. They're loving it, but probably realized that's not going to out of the gate, pay the bills and so found that computer science did very well in it.

So got a really amazing GPA, blah, blah, blah, and then did a minor in creative writing at school. And so now professional is funding passion and way wise beyond my years, so.

Adam: And how long have you and your wife been married?

Darin: Well, in Canada, you know, you get married when you're 12 and then…

Adam: It's a wonderful ceremony at the beer store.

Darin: Exactly. We've been married. Wow. We are coming up on 32 years. And so, yeah we met each other. It was not love at first sight. Neither of us really were that impressed with each other, but then we became really quite good friends. And then all of a sudden, like, like this little burning fire started coming up for me like, ooh she's pretty hot. And like, she's really smart. And like, that's a pretty good intersection. And so, yeah, then we started dating and got married right after we finished college and we were both relatively young in college. And then, yeah. onwards, upwards, many iterations since then.

But now it's, another fun I guess step. And that's actually been an interesting thing watching other people who post kids, like they look across in their partner, like, who are you? And thankfully we had been intentional on, you know, hey we like each other and we want to do things together.

And it wasn't just sort of two people on the same team making stuff happen independently.

Adam: That makes a lot of sense, I think that happens a lot, especially when you have young kids, and you're just trying to keep your head above water.

Darin: Yeah, it's divide and conquer and hey, I'll see you Saturday morning when we're both groggy over coffee kind of thing.

Adam: That's right. That's right. When your kids were growing up and I mean, I guess they're still, you know, they're still growing, right?

You grow all through your 20s.

We all ever and even older. Did your wife work? Or did she work outside the home? Because I don't want to minimize the hard work of raising a family.

Darin: Yeah. Initially it was going to be probably her career, it's kind of funny, Leah, our youngest, she has a story like when she was little, she's like, mom, I want to just marry somebody smart and rich like you did. And Trish sits her down and go whoa, little girl, let me tell you a story because Trish put me through college the second time.

She was a professor in management information systems for you know, MBAs. So she had her whole career track. But then, yeah, I got into computer science. We both looked back at our growing up and her experience was her, you know, one of her parents was her mom.Was there when she got home, was there, you know, to set her up and, you know, that was a decision we transitioned into as my income increased.

And yeah she was one of the earlier people doing distributed work. Like while she was having kids, she was. Teaching you know, college courses at night, async, recorded for the University of Minnesota.

And it was a little bit of a forcing function. I guess my editorial, the immigration system for the U.S. is whack. And so a spouse was not immediately able to work, even though she was more qualified than I was. And so that was a bit of a forcing function because IBM sponsored my work transition to the United States and the spouse at that time was not immediately able to work.

Adam: Now that your kids are out of the house, has your wife changed kind of her thinking around career or work? What's she doing now?

Darin: Yeah she turned a passion into helping others. She does a nonprofit for setting up women's running programs in you know, prisons for adults in custody who minimum, medium, and maximum. How do you give people a mechanism, a tool for coping when, you know, your world's been tipped upside down and also as you are moving towards going back into society, how can you change your life?

And so I think, yeah, she's north of over 1000 people have gone through the program and in a weird. Guess it's good. Less women are incarcerated, but then there's less funding for things like programs like running, etc. The men's are much more organized. So she found that gap. She's been filling it. And again, super challenging during covid.

But, one of her success metrics was she was one of the very first programs to get rebooted after COVID. Cause everybody's like, we need this mental health, physical health, you know, it was like, and so it was really fun to see that. And it's also been really fun for her scaling. She very frequently says, you know, don't use your management techniques on me.

You know, in our relationship, but then we got to talk for a bit of how do you delegate. Something you really care about so that others have opportunity and you can level up in having more impact. And that was a difficult transition for her to go from doing it all to, you know, having a group that now does the programs.

Adam: Yeah. Did the two of you always know that you wanted to have kids? What was that decision like?

Darin: Absolutely not. We were on the verge of not having kids, you know, we got married young and I think. I don't know, by mistake, by luck, by people praying for us so we didn't screw up. We didn't have kids for seven, eight years. And it was mostly, we knew we were young and we also, like, what do we want to do for careers?

What do we want to do this and that? And my memory, I think this would map for Trisha, is her dad said you should have kids so that become better people and are less selfish. So I think he was telling us, hey, you might be a little too inward looking, he was a very wise man, and I retired or I, you know, went out of a normal career path relatively early. So most of our friends don't have kids. And I think there's super amazing, impactful and valuable lives down both streams. So, I think it's more like, how are you positively impacting the world than did you have kids?

Adam: That makes a lot of sense. I love her dad's advice too. That's awesome. Having kids will make you better people. You should do it!

Darin: Well, it definitely definitely challenges you in many different respects.

Adam: Yes, you mentioned that your spouse has been the kind of key metric, or the barometer, of whether you should be making changes. Tell me about what that means.

Darin: Yeah. We were chatting about this week and we, you know, we talk about because I use it a lot in my work as well. Like this advice of pretty relatively quickly comes up because it's like, hey, when I'm working with you, like, let's say you and I have Adam, we're partnering up, it would be like, you know, what are your measures of success?

And there's life and work.

And you know, one of the things we quickly go to that Trisha and I have gotten to is a couple things around, you know, are you bringing frustration home? You know, are you, no matter how good I think anyone is at compartmentalizing, if you're not thriving and that doesn't mean you're not working hard, but if you're frustrated, if you're, you know, just coming home and that leaks out into your interactions with your spouse or your partner, your kids. That was 1 of our things that was unacceptable.

So there was that. And then the other one she asked me fairly frequently. She's like, okay, whatever it is you pick this opportunity. You know, if we asked, would you drop it tomorrow?

And that one was hard, but it was also brutal honesty towards what was most important.

Adam: Yeah.

Darin: Because again that, you know, she's often reminded me that if you left, the company will forget about you in about two months. You're never that critical. You're never that important. Not that it's not important what you're doing, but they will survive without you.

Your family won't. That was really grounding advice. And making choices to what's a priority and how you work at it. So she's been very good at keeping me like humble, you know, she's God's gift, keeping my ego small, which is great. And yeah I just really appreciate that advice. Like. What you're doing is important, but you know your family if you've chosen to do that And even if you have a partner and a spouse like that's also I think that's one of the things we put on the shelf way more than we should, at the expense of career.

Oh my partner will understand. It's like no.

Adam: Oh Yep. No. Do you remember a time in your career where she kind of really had to be that barometer. Either you were bringing too much frustration home with you or just something wasn't going right. And she had to kind of set you straight.

Darin: It's pretty constant like, you know, hyper growth startups, you know, you're going through a different phase of the company every six to nine months. So there's always going to be pressure. In fact, if there isn't, you're probably doing something wrong. If you're coasting and, you know, venture backed, early stage startup. So I think it's more like just that constant reminder of how you're doing your overall prioritization and specifically… usually it was when something was in the crapper, you know, like when a project was going really poorly and, you know, somebody would be pinging on 2 PM on a Saturday. You know, because things weren't going well and I probably hadn't communicated very well because I was hiding, you know, like information hiding.

Oh, that'll make everything better. and she was like, you know, hey, have that communication with them, but tell them you're going to deal with it on Monday. You've made a mistake. So that'd be the envelope. I had made a mistake. And, you know, owning to it and then setting a timeline for dealing with it in resolution rather than it burning in your brain and everybody can tell when you're not really physically present.

Let's say at dinner or, you know, have a lot of things where we call forced family fun, which usually is like an organized event that is type two fun after the fact. Everybody's like, Oh yeah, that was really good. But ahead of time, most people would be like, yeah, I don't know if I want to do that and for me, like people, I was there, but I wasn't there because I was bzzz on the problem in the background

And, you know, individually learning how you can deal with that.

For me, it's like I, okay, I write it down. I tell the person here's where I screwed up. Here's what I'm going to do. Wrote it down and we're going to talk on Monday. Like for me, that's how I could, you know, sort of, stash it, so to speak till we really needed to deal with it.

Adam: I love that concept of type two fun. I think that's a new one I'm gonna incorporate into my lexicon here.

Darin: Yeah, it's not fun in the moment, but it's fun after it's in retrospect, everybody mostly agrees. It was fun.

Adam: Honestly, I think that's probably most of parenting. Where, like, in the moment, you're like, this is really friggin hard, and then after the fact, you're like, oh, we can laugh.

Darin: Well, otherwise, nobody would ever have a second kid, right?

Adam: That's true. That's very true. Oh, so speaking of second kids, so you have two adult children. I know it probably sounds weird for me to say adult children, but they're what? 22 and 24. I think you told me.

Darin: Yep. Exactly. Yeah.

Adam: So, you know, they've always been your kids. They'll always be your kids, even probably when they're 40, right? But they don't have to listen to you anymore. And I'm wondering how you managed through that as both you and they have gotten older.

Darin: Yeah. Yeah. It's one of the hardest things because I would say actually, as they get older, the problems get bigger. You know, they have more blast radius, they have more impact on their lives, all those kinds of things. So you have all that angst and energy and passion that you want to help them protect them, go out and smack that person who didn't give them the job interview, you know, like those kinds of things.

And yet you can't. So the biggest thing that I in quotes locked out and that my transition away from full time work to interim fractional advising mentoring coach happened when they were in later stages of high school. And so my advice or guidance I give people is however you do it, set up your communication. Like how do you talk to your kids around things that are meaningful to them and setting it up for when they don't have to listen to you.

So our success metric for that has been now for terrible things and great things They reach out to us pretty much first and like that just makes me happy. Like, obviously, I don't want to hear about terrible things, but if they call us or well, they don't call if they text us like, it's like, oh, this sucks, but I'm so glad that we have these communication things.

And as I was thinking about getting ready to talk to you about this, I think the two phases that looking back for our kids. Is like early school, like, you know, kindergarten age six age seven. And then there's that interstitial period where they remember things that I don't remember and vice versa, but it doesn't seem critically important as much.

You're there, but it's not critical. And then like grades 9, 10, 11, 12. And these are very generalizations, but that seems to be when being there, setting up the communication foundation for when they're gone. I'm super thankful for that. And, you know, I do walk and talks with my kids where, you know, I'm out for a walk and they're on the phone and then also to figuring out how both of them are individuals.

So you have to figure out what are things that are different for them and, you know, finding commonalities not assuming that you think about things the same way or look at things the same way. And then, yeah, coming to terms with that they're adults. Like, that's probably the biggest mistake I've made.

I would say is not talking to them about bigger topics earlier. You know, about things like some of that stuff, like both of them were interviewing for jobs. So a more recent example, and it took a while for them to really be honest about how nervous they were and anxious they were and how much they were worried that they were heading down a path towards failure. And I was like, they like, but and dad, well, you know, look at how successful you are, whatever that means. Like, whoa, let's stop here. Let's walk through, you know, after I had my first biology degree and I had 115 rejections and had to go work, you know, at a part time job just so I didn't feel totally well, not depressed, but, you know, on whatever I needed something for my energy. And so I think sharing, I know I had a bias towards, you know, happy path stories or oh, don't worry about this, you know, whether verbalized or not. And I think sharing both your fears. Yeah, your fears I think shows them that they're not being unrealistic or particularly I think, you know, getting into the modern day social media, everything is either like massively terrible or totally fake and awesome.

Adam: Yeah.

Darin: And, telling people there is this path in the middle, your kids, where, you know, anxiety and fear and like sweating during an interview is perfectly normal.

So, yeah, I think maybe it comes out of sheltering, wanting to shelter them a little bit. But just having them be honest, and it's amazing how many times they did things because I thought that's what Trisha and I wanted them to do.

And we were like, well, no, we thought you wanted to do that. And if we would have just been a little bit more honest on conversation, could have probably worked things out.

Adam: I want to kind of go back to what you said at the beginning of that, which was , making sure that your kids see that you are vulnerable, that you do have failure as an adult, that you their dad has that. And I think it's interesting because when your kids are younger, you want to be so infallible, right?

You're the superhero for them. and that's important, right?

Darin: They want you to be that initially in that stage.

Adam: They need you to be that rock. And then there's a point that you reach where actually that's not what they need anymore. They need to know that like, it's okay. And that mom, dad. We're successful despite some setbacks and that's actually more helpful for them over the long term.

Darin: Exactly. And I see a lot of parallels to, you know, leaders in startups, you know, picking when to be vulnerable, picking when to be strong, picking when to be decisive, picking when to, I don't know. You know, those are some of the biggest weaknesses I see. And, you know, leaders little L or big L in terms of…

you should show people that you don't always have the answer to allowing them to either partner up with you to get to the answer or not. And yeah, same for kids. Like, you know, like I mentioned, my, brother's kids are younger and, you know, that I think somewhat they see my wife and I as like, ooh, these, you know, people who are amazing. And I'm like, well, wait a minute. Like, no.

Adam: Yeah.

Darin: And then my kids, they want to see and have us as a backstop as a stable ground, but then also. Recognize that we make a lot of mistakes and that they are normal when they make mistakes and not even mistakes, but just what's important and what you shouldn't worry about.

Like, one of my biggest things I really had to work on is I care way too much or used to care way too much. What people thought about me, like friends in high school told me this later in high school, we thought you were all stuck up. We thought you were stuck up because you were, you know, insular and you didn't interact as much.

And really what it was is I was just absolutely scared of them rejecting me.

And so I was always the one to make the jokes. I still make jokes, my user manual I give to companies like I take negative feedback personally and I try it. That's not their problem. That's my problem to adapt. So you should still give it to me.

And then I always try to lighten the mood by the joke. And that sometimes serves me well. Sometimes it comes across as cavalier or never taking anything seriously.

Same for you know, helping my kids. Both of them have an amazingly good sarcastic humor, but sometimes it's too biting in the moment.

Adam: Yeah.

Darin: And they're learning how to use that with some feedback from us. Sometimes it's like, hey, that was not good. That was too much.

Adam: Yeah. Well, it's either going to be you that pulls them aside and says that or it's going to be someone in their professional lives or…

Darin: Exactly. So again, having the radical candor type, Kim Scott type thing as your kids get older, I think is important.

Adam: Yeah, so I want to ask you kind of a follow up to this, has it been hard for you to watch your kids grow up and now as, computer science professional or, you know, graduating from college, has it been difficult to watch them go and make different decisions than maybe what you would have made in that moment?

And how do you walk the line of letting them make their own decision, but also giving them that fatherly advice without coming on too strong. Like it's a balance, right? How have you struck that balance?

Darin: Yeah, I probably fall too much to being prescriptive, you know, like, do this and mostly it's like Trish and I looking back, you know, our early days, like, like, you know, we're just coming up to the Christmas break, you know, the holiday break from Christmas to New Year's. Perfect example, like early married years, we would go back to family.

And we just played video games for two weeks straight. Nothing else. That is all we did. We ate their food. This is Trisha's family. We ate their food. We played video games and slept. That was it. And I look back on that. What a waste of time. Like, oh, mama, like, you know, just pick 10 percent and do something like, you know, and so trying to weave that into my, and then, but then at the same time, they're like, well, but that's the only time in their life they can do that. And so it's kind of trying to walk and balance that.

So it’s a bit of a healthy balance and. Yeah. I think to just you know, telling stories like, hey, here's what we did. And here's how that, and I think that's back to showing who you are. You know, like financial is a perfect area of opportunity and landmines, right?

Like, hey, have you started, you know, your 401k or hey, have you started saving or have you done this or have done that? And it can sound just like a laundry list of mom and dad are in my face again, as opposed to, well, here's the things we did. And this set us up to a lot of pain or a lot of, you know, potential and mostly that's resonated for them.

And you know, I think, you know, we've, you know, thankfully for the last, whatever, 10 years, like money as a thing hasn't been something like, you know, it's not a hand to mouth existence for us, yet teaching our kids the value of a dollar. You know, that's also that's been relatively tricky business.

Yeah, the hardest part is when you fundamentally see them doing something that's like, I don't know about that. But, you know, you can just tell them your experience and they have to be their own people and then just be there for them. It's a lot of like the disagree and commit into work contents.

It can't be disagree and commit and then I told you so. Like, that doesn't help anybody. And so, yeah, everybody, there's very many things people just have to experience on their own. And so far, thankfully, we haven't seen anything that's like, ooh, ooh, okay, pull the red cord. We gotta have something here. I don't think we've had that. COVID was, was really tough. Our kids were both in college and COVID. And initially for them, back to like my wife and I, like, they just loved insular reading books, video games, and they didn't understand why their moods were getting grumpier and grumpier. They didn't understand the value of community.

And, that was one of the things I think, you know, once we got over there, what are that flattening the curve and the kids were home for like forever. Like how do we get you reintroduced into the world when all of community, you know, college your friends, church, whatever, nobody was there because everybody had been like closed their door and…

Adam: Yeah

Darin: Didn't know what to do. So yeah yeah it's amazing journey. And at the same time, the, probably the biggest thing that wakes me up in the middle of the night is like, how do I help them?

Adam: So I want to go all the way back because you probably weren't thinking about this when they were newborns. Like you said, the problems get maybe fewer but bigger and they change shape. And so I wanted to ask you what the earliest memories that you have of becoming a father are?

Darin: Well, it's a family joke. So our first kid, first two years, we joked that Leah, the second kid, is lucky to have been born. Cause, we were those parents where everybody looked across and like, what are you doing? Cause I remember, Claire was born and we were in that place where they were washing the kid up and I had this vivid memory and I'm the only one who has it because I was the only one there and everybody's looking at me and my kid's the one screaming in the corner and everybody else is like, you know, cuckoo, look at the cute little baby.

And so there was that. And Leah, the second was the opposite. Yeah. Pretty amazing for the first two years. And then some button, some bit got flipped super challenging as a toddler. But in general, I guess my favorite memory is twofold. There's the laying on the couch with the kid on my chest.

And either reading or falling asleep, and like that closeness was just, like, that's amazing. And the other is a great memory, but also a sad memory, of when the last time I held both of my kids hands.

And, so if you're a parent and you're still holding your kids hands, treasure that.

Adam: Yeah,

Darin: Because it stops.

Adam: How old do you think they were when that stopped?

Darin: We got lucky. We did a tour uh, one year international assignment in China, in Beijing. And it was very common for kids to hold their parents hands way later than in the United States. So we got that one extra year where they reached out and held our hands. Not because they were, because it was just what everybody was doing.

Adam:Culturally it made sense.

Darin:And really it really solidified how much there's sort of cultural pressure in both directions.

Because these kids had grown up in the United States until that point. And then that, you know, six months to a year in China and they changed. And I was like, Oh, this is so awesome. But then we came back and like, boom, it was gone. So that's that we got lucky that was when they were ten and eight.

So now with, yeah, with my niece and nephew who are younger, it's already hard, like even hugs or hands or, yeah,

So it culturally, I think we're a little weak, bad, whatever that is on that front.

Adam: Yeah. So you have two decades, a little more than two decades parenting experience now, what would rank as sort of one of the top one or two most surprising things that you've discovered as a dad?

Darin: Probably how different kids are with the same environment, with the same parenting general, processes and practices, how they react differently and how adaptive you have to be because they're individuals, like they had the same parents and we've done mostly the things the same, but how different they could or would react.

I think the other one is both how similar they can be to you and then also how different they can be to you in terms of reacting or growing or interacting. And sometimes the similarities you glom onto those because you want to mini me and I don't think that's super healthy, you know, whether living vicariously through them.

Or assuming that, you know, they're going to be, you know, marching towards and that's hard because you want to have things that you're common with your kids. So if you see like, ooh, you really love this and I really love this and boom, it's like, well, no, that's not really. And then they, you know, either they drift away from it and you don't want to let it go.

So yeah, you have to be super adaptive.

Adam: Yeah. Have you developed over the course of your kids lives any particular frameworks guardrails for parenting? I know we don't usually think about parenting in terms of frameworks like we do professionally, but you know, maybe we could come up with one on this episode. I don't know if there's something that sticks in your mind?

Darin: Yeah. No, it definitely does. Similar to work like, you know, proactive communication from either party, maybe this is a stretch too far. We're workshopping here, but you know, in performance management in work, right? The classic pattern is you wait and you wait and you wait, and then you have to tell the person things are really not going well. I think similarly with parenting, if you know, you see good or bad or, you know, whatever, you start talking about it, like, hey, you know, when you're coming home from school, you seem to be grumpy, like just talking about it and getting it going. So it's familiar and not something that you let build and build until there's an explosion

Or something, you know, unacceptable happens.

I think, yeah, just making communication of both the fun and the deeper stuff. Very natural.

I would say is what's most important. Like no topic should be off bounds in terms of, you know, exploration and you can say, here's what I fundamentally believe. Here's what my truths are. And here's how we have lived as a family.

And as they get older, you got to get more and more degrees of freedom for them to be like,they're no longer just doing what you've said, they're now figuring out what they are doing and how are you gonna get ready for that? How are you gonna kind of again back to work, like, you know, if you fundamentally believe in some form of mechanism of you know leadership or management or in my space like software development, can you embrace that someone does it fundamentally different and it could be successful? My example was, I always was an individual who liked being part of a team, but give me my work and then I'll bring it back to the team

Adam: Yep.

Darin: And, you know, I'll give Rebecca credit, but there was a number of people involved, but, you know, she fundamentally proved to me that team driven or swarm or pair programming in the right situations in the right environment could be massively more productive.

And I was like, initially, no, absolutely not. But I was smart enough that recognize that she knew what she was talking about. And so similarly with kids you know, like, yeah, like when Claire was like, oh, I want to do a, you know, a minor and create a writing, like, why, like, why not just keep it as a hobby?

But instead it kind of got formalized into, well, fundamentals and foundationals and like things that if I'm going to want to pursue this, I should also get some classic training in it. 

Adam: Yeah.

So I wanted to ask it, sounds like you and your wife had developed a really good partnership across, you said, 32 years of marriage. So that's a, that's a long time. And partnership is super important when you have kids. I mean, I know this, but, I want add that it's really, it's impossible to agree 100 percent of the time with your spouse.

So if you think back through the last couple of decades of raising kids, what's something that you and your wife haven't always seen eye to eye on when it comes to parenting?

Darin: Yeah. I'm not as naturally empathetic as I should be. So if someone falls down or hurts themselves or mostly physically, but sometimes emotionally, I'm like, you know, suck it up, let’s go.

Adam: hmm.

Darin: Like, and that somewhat that's my own coping mechanisms to just quickly move past it. And Trisha was like, come on, just give them a hug.

And so it wasn't like sort of a foundational thing we differed on, but she was making me better on recognizing like the suck it up mechanism shouldn't always be the default.

Adam: Yeah, the tough love parenting strategy isn't always the best one.

Darin: Tough love and, you know, kind of like anything can be pushed through in a quick moment just by effort.

And sometimes pausing in that, wow, that really sucked. Or that hurt, like, I'm still not good at it. still gives me like the kick out of the table towards that.

So I would say that's where it is. Yeah. Thankfully, looking back, Most of the time we were just so tired that in the early days that, you know, it kind of just we survived and we're thankful the kids did as well as they did you know, parenting is hard.

And so, you know, and both of our kids were super early morning people. So, you know, we had a schedule for, you know, who had to get up at five a. m. when the kids got up.

Adam: Yup.

 Darin: And you celebrated when it was not your day

Adam: You get to sleep in until maybe 7 AM.

Darin: Yeah. I think that in terms of differing and you said partnership and I think that's where you can embrace your differences towards making you a better partnership. And Trish has always been better to it. You know, I'm more would have the fluffy conversations, you know, and she's been much more.

And for me, it was like my reaction, like maybe from my upbringing, I don't know, you know, that's where I'd have to get on the couch and we'd really have to dive into things. But classically, I think from my upbringing, we stayed more fluff topics than like diving into like, you know, no, I asked you how your day was.

I wasn't looking for good. I was looking for, how did it actually go?

Adam: Yeah. Yeah.

Darin: And that's also cultural, like, it's amazing how much we negatively respond when someone actually tells us, when you ask them, when you just want, hey no, I just wanted good.

Adam: Right. Right. Right.

Darin: Like, you know, I, for me that's become the true definition of a friendship is where you're sharing where you're at and not just the fluff.

Adam: Yeah. Yeah. When you think back across your parenting, what would you say is a mistake that you've made as a father? You've had a lot of opportunities to make mistakes.

Darin: I alluded to it already starting to talk and tackle bigger topics earlier. You know, I was waiting who knows for what, but you know, whether it's on, you know, what do you fundamentally believe about the world, you know, or faith or finance or interacting with others or even big topics like you see out there.

You know, it's like, oh, their kids don't bring that up.

They are getting it somehow somewhere, particularly, you know, as soon as your kids are going to school, already your sphere of influence or your sphere of interaction is massively decreased

And, you know, pick your thing, war or, you know, crime or whatever.

It doesn't matter. They are getting exposure to it. And so if you don't want it to just be passive. And you want it to be, you know, conversational interaction and not telling them what to think, but allowing them to explore it in a safe way. I'd say that's my biggest mistake. Waiting for, you know, like we talked about my anxiety, my sort of need for approval of others, financial planning.

Oh, they don't have money. I think that's another big western culture thing. Oh, never talk to your kids about how much money you have or all this kind of stuff. And we've really moved to like, no, full disclosure.

Here's where we're at and, you know, I think mostly they've respected that we trust them with that information.

And I think it's just healthy for, you know, helping them to understand where you're at, what you do and why you do certain things. And the world is amazingly complicated and interesting. And so if you can use that towards, all this generational crap, like every generation is so fundamentally different.

Like, no, let's find some continuity and some commonality. And let's talk about those things because these people. Young, middle, old all have just different perspectives that we classically like to marginalize because, oh, you're Gen X or you're millennial or you're boomer. Like, no, like that bugs me and we really segregate by age.

And so start with your kids. Like how many other kids do you get to talk to or 20 year olds for me? Like I have no interaction really with other, 20 year olds.

Adam: Right. Just startup founders.

Darin: Yeah. Ouch. Yeah. No. We do sometimes talk about my company kids and yeah it's a lot of ways it's similar. Cause you're seeing what they're doing and you're both like, Oh, they're going to be successful. Oh crap. That's not going to go well. So yeah.

Adam: Yup. Normally I ask people about how they feel about startup hustle culture and how that fits in with family life, but for you, I actually want to ask a slightly different question, which is. If you can think through kind of the phases of your kids lives, how has your relationship with work changed at the different ages that your kids were?

Darin: Yeah, it's interesting, the different ages, like, don't know if I'm classic for my generation, I just talked about generations. You know, basically in their middle years, it was like transactional.

It was like helping them get up or helping them get to school or helping them get to bed.

I mean this in the most loving way, they weren't that interesting yet. They were, you know, they were forming, they were young, they were, you know, reading or watching Blues Clues at the time. Like that wasn't that interesting. But I think the key part was we still had intentional touch points, talked about forced family fun and Trish was really good at that.

Like I, I do, I did a lot of running. I still do a lot of running. And then there was work and, you know, she gave me space. Okay. You ran your marathon. Cool. We're going to the zoo now. Like, no, you're not sitting on the couch the rest of the afternoon. You are doing family stuff. And I had my 40 minutes to get ready and, you know, deal with the chafing and then get out to pushing the kids at the zoo. And so like, that was great. So I think that was that middle stage. Like there's the early baby stage where all, you know, your diapers and whatever, and then there's the, the early childhood. And then the next stage is where you got to be there for those moments where they want to start interacting and showing who they are.

And I think that's hard in startup life because startup life is sort of the expected, like you're swimming, living, breathing it all the time.

Adam: Yeah.

Darin: And you know, there's been tons of talk of work life balance and distributed work and remote work and, you know, I don't have all the answers but I think again, as my kids have gotten older, just being honest with them, like, hey, I'm thinking about this.

And even sometimes just. You know, sort of walking it through them and some, yes, totally. Sometimes our eyes completely glazed over and I'm like, okay, not interested. Other times it was like, holy crap. They want to hear what I'm saying here. This is kind of fun and a new perspective. So yeah I think startups are hard because they have that sort of like leaky into your life.

Adam: Yeah.

Darin: And I'm still not good at this, but what I've embraced is making time to think for work. That isn't part of the allocated time for family. I think maybe that's what I would put like, there's the work and then again, I would very generalize work. Western culture doesn't think of thinking as work

Adam: Right.

Darin: and which like, okay, whatever. But then there's people then cheat. And so when you're at the dinner table or you're at your kid's soccer game. And you're, that's when you're thinking and everybody knows you're not there.

Adam: Yeah. Yeah.

Darin: And that's what I really tried to do is into my work and the people I work with is like value thinking time and make that explicit, you know, however you do it.

Classically, it was like focus time on your calendar, like, okay, whatever. But like, how are you actually going to get into that zone in that time?

For me, it's walking and running. Like I found that is how I can get all my body and my mind to align that, yeah, this sucks. I'm suffering, but then my brain's free.

Adam: I love that. That's a fantastic piece of advice, too, to just make sure that you build in the thinking time into your work day, or at least into your non-family time.

Darin: Yeah, exactly. Because otherwise, I think it just takes over all that because your brain, atleast most of the people I've, you know, we all think differently, right? We all work differently, but I think most people benefit from sort of background processing and rumination and aggregation of information.

And if that's only happening when you're supposed to be interacting with your family. You're cheating your family

Adam: Yeah.

Darin: And, you know, being intentional on that when you're talking with people at work on valuing thinking time instead of how full your day is. like how many times do we actually have epiphanies in meetings?

Adam: Almost never. Zero. Zero, perhaps. Yes, I agree.

Darin: Let's go to let's be definitive

Adam: Yeah. I like that.

Darin: And, you know, invention and epiphanies and, you know, massive sort of aha moments. You know, there are some people who can do it in a meeting, but there's also a ton of people that. That will not happen just because of how they're wired. And I think we're marginalizing their input as well.

So it's not just making your family, whether you have family or partner, whatever, it's also those who think and work differently. And we should be enabling that.

Adam: What is the absolute worst piece of parenting advice that you have ever received?

Darin: We were talking about this because, you know, you share the questions ahead of time to give me a little bit of a preview. And my wife and I were talking and we struggled to come up with that. Maybe it's because we like mostly kind of came up with our plan of action on our own I would say the probably the biggest is, you know shelter your kids, you know don't expose them to that or you know, whatever.

Or force, you know a close corollary would be they have to believe what you believe or they have to be in line with you.

You know, allowing exploration and every topic is something that you can dive into, I think is solid.

So yeah, the worst is, I think, you know, whatever that, you know, like the solar wind protect your kids at all costs type advice. I think. You know, sample size of not that big. But what I've seen is then the kids, when they get into exploration mode, which they will in whatever dimension, they don't have the framework for communicating with you or framework for learning in a way that, you know, is not at a minimum, you know, a pause in their development and a maximum, you know, destructive towards how they move forward.

Adam: Yeah. All right, last thing for you. How can people follow along or be helpful to you in your journey?

Darin: I like feedback you know, async constructive criticism I really appreciate that. because I certainly don't have all the answers, like mostly I just maybe know how to ask the questions, but I think is. Really, I think the way you can help me, it's all like I live and breathe startup space, right?

Like, that's one of my key things. And I would just love us to move away from it being a zero sum game and continue to building community and sharing practices.

One of the things like you and I have gotten to know each other by sharing practices and successes and failures in our space.

Adam:That’s right.

Darin: And I really think we do a poor job of that in general.

You know, we have tech conferences where we go and talk about the latest whatever language and how it's doing async this or that. Boring. That's a means to the end, right? The people and organizational and how we work and what we've learned. I think we should be way less that's not a secret sauce.

Adam: Yeah. And if somebody wants to find you on the internet and share feedback or share some interesting cultural or, or maybe a startup that's looking for an advisor, what's the best place to find you on the internet?

Darin: That's a tough one. I like this. I used to, I would have said Twitter not all that long ago, but that's completely dead to me. Probably email like, you know, my email is just my name, darin.swanson@gmail.com you know, because that would be a start. And then I'd be like, hey, let's do a coffee walk. Like, that would be my, that would be my progression.

Adam: Okay. You might be inviting a lot of unsolicited email.

Darin: Well, and, you know, like, that's fine. Because the two things, right? Like, I love giving people metric for wow. Awesome. Let's go forward or considered and rejected. They're both equally valuable, and it's not a measure of good or bad, it's just a measure of, like, what I'm going to invest my time in.

And again, considered and rejected, a lot of people were like, whoa, like, no, like, at least I didn't, you know, I'm not going to ghost you.

And for me, like, that's the, bleh, terrible. Like, considered and rejected I really thought about this, and no that's hugely valuable.

Adam: All right. And with that,

Darin: Lightning round!

Adam: It's time for the rapid fire or lightning round. Darin, here are the rules of the rapid fire round. Really, there are no rules, but I'm going to ask you a question and you are going to say the first thing that comes to mind, and then we are not going to pontificate on that thing, we're just gonna move to the next question. Are you ready?

Darin: Oh, I'm not so sure, but yes, absolutely.

Adam: Question number one. What is the most indispensable parenting product that you have ever purchased?

Darin: Nintendo.

Adam: What is the most useless parenting product you've ever purchased?

Darin: Baby monitor.

Adam: Which one of your kids is your favorite?

Darin: Depends on the day.

Adam: What is the most frustrating thing that has ever happened to you as a dad?

Darin: Not being able to protect my kid from a painful experience.

Adam: Alright. Speaking of which, did you ever drop one of your kids as a baby?

Darin: I have a vivid memory of almost dropping both of them. My memory is I caught them. Their memories, I dropped them, I'm sure.

Adam: Well, they don't have that memory because it's been knocked out of their head.

Darin: Exactly, yeah, yeah, yeah.

Adam: What is the favorite age for your kids?

Darin: Now.

Adam: What about the least favorite age for your kids?

Darin: Right around two. Both of them. That was a transition time.

Adam: All right. What is your take on minivans?

Darin: We were cool in that one dimension that we never had a minivan.

Adam: Okay. Okay. I noticed that you also think minivans are where Cheerios go to die,

Darin: Cheerios go to die. I've never gone into a minivan that if you roll, pull back the floor mat you don't see a biological experiment going on.

Adam: True. How many dad jokes do you tell on average each day?

Darin: My kids basically think I am one big dad joke, right? Like, like everything I do their eyes roll and they're like, come on. Like, so yeah, I, you know, do I follow certain groups that seed those? Yes, for sure. And I love a bad joke

Adam: Me too. Speaking of which, what was the most embarrassing thing that you've ever done in front of your kids?

Darin: Ooh, I'm sure that one's hard, like to instantly, I'm sure there must have been some running race or something where I, you know, did a quick change. And both of my kids are like, like dad, what were you doing? But that would be probably my guess, but they probably, I should ask them that one.

Adam: We'll follow up on that one.

Darin: Yeah.

Adam: We can ask them.

Darin: Next time when Darren's kids come on to tell the truth.

Adam: That's right. Okay, have you secretly thrown away a piece of your kids artwork?

Darin: So much, yes, so much of it is bad.

Adam: That's right. And there's so much of it too, right?

Darin: Oh, like, yeah, I think the teachers are just out to get us with the massive amount of bad art that, or like how many plant pots and, you know, in the old, my day it was, you know, cigarette holders. At least we don't do those or whatever. Ashtrays. There's the word.

Adam: Yeah.

Darin: Now it's not, they can't do ashtrays. Now we have to do plant pots that don't hold water.

Adam: Yep. Yep. Don't you ever think that's funny that as kids we made ashtrays in, like, pottery in

Darin: Oh, totally. Like I, I remember forming those and my kid, my parents didn't smoke. So it was also weird. Like what do we do with this? 

Adam:Same.

Darin: Like, yeah, but it was just the thing that you did.

Adam: Yep. Just make an ashtray.

Darin: Yeah

Adam: Very normal.

Darin: Yeah.

Adam: What is the most absurd thing that your kid has ever asked you to buy for them?

Darin: It was pony. It was the classic, you know, that phase where we, our yard's big enough, we can have a, you know, we can't have a horse, but we can have a pony. Like, no.

Adam: No, we cannot.

Darin: For me, like, pets should end at fish tanks. And I've gotten, you know, overridden on that. We've had dogs but something that can, an automatic feeder and you can go away for three weeks.

Adam: Love that. Yep. Yep. Do you have a Disney or Pixar movie that you are secretly or maybe not so secretly a fan of?

Darin: Yeah, Pixar. I really liked them until recently. Yeah, like, I will admit sort of embarrassingly some of the new live action Disney's.

Adam: All right. On a scale of one to ten. How good are you at assembling children's toys or furniture?

Darin: Oh, I’m terrible, so like one, I get super frustrated and, you know, I blame the instructions, but it's me I just don't have the patience and. I am not skilled at assembly.

Adam: What is the worst experience in memory that you have of trying to assemble a toy or a piece of furniture?

Darin: It would have been, yeah, trying to put together their, early beds, you know, the toddler bed, I think that's what they were called. And yeah, just, you know, stripping the screws, like trying to just get them in there and like, or like. Yeah, it was terrible. The only good part is the bed didn't last that long because they grew out of it.

Adam: Right, right.

Darin: And then, you know, being the proud parent and setting up the, I remember trying to set up the cribs and stuff. And it's like 11 o'clock at night and you're trying to put this thing together. It's just not a good experience though.

Adam: It’s always 11 o'clock at night. Okay, last two for you. Have you ever accidentally mixed up your kids names?

Darin: Not their names, but both Trisha and I, we have remapped history to changing stories. Like, who's the central character and our kids are like, how can you possibly have done that? But it was you! It was like, no, it wasn't me.

Adam: Love that.

Darin:Yeah, that's that's just, you know, humans, like, I love those things that, you know, eyewitness reports are like the most fallible in the most terrible form of truth.

And that's kind of like how we've, some of our stories have been remapped.

Adam: Alright, my final question for you. How often do you tell your kids back in my day stories?

Darin: That's like the dad joke. Like, is there any other way to start, you know, back when I did this? Yeah, quite a bit. More than I want. That's actually one of the things. My grandparents, my parents, us, our kids, you know, Trisha and I and some of our closer friends, we look at each other and like, and I mean this in the love, most loving way, but we are going to hold each other.

So we don't do that. Like how do we make it so that we don't do continue that pattern of you know, back in my day. It's like, yeah. Yeah, but I do it way too much.

Adam: Alright, well good to know I'm not alone in that regard.

Darin, that brings us to the end of our rapid fire round. Thank you so much for joining me on the Startup Dad Podcast. You did a fantastic job and good luck raising two new adults.

Darin: Yeah. Well, you know, the world is the receptacle of them. So hopefully it does amazing. It's almost all of us now. It's a community raising them now.

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

You can join a community of over 9, 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.