Three Generations Under One Roof | Eben Pingree (father of 3, founder at Kinsome)

Eben: My son was born four weeks ahead of time. I had a million things that I was going to get done in those last four weeks before he was born. And of course that all just goes out the window and similarly our, son and our daughter are four years apart and, you know, in my head, we were going to have another kid two years later, two and a half years later, and it was going to be just like me and my brothers and, you know, with miscarriages and all this stuff that just teaches you, you know, trying to plan these, big life things can be a fool's errand sometimes you just have to be grateful for the way things happen.

Adam: Welcome to Startup Dad, the podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I'm your host, Adam Fishman. In today's conversation, I sat down with Eben Pingree. Evan is a serial startup founder who is currently building a company called Kinsome, which is focused on helping grandkids better connect with their grandparents.

He co-founded and sold multiple companies over the past 10 years. He's a husband and the father of three kids. In our conversation today, we spoke a lot about what it's like growing up in the same house you were raised in. Eben and his wife live in a multi generational building, with units that also house his parents, his brother, and his brother's family.

Altogether, there are six grandkids, four adults, and two grandparents under one roof. We talked about some of Eben's earliest memories of fatherhood, parenting advice he'd give his younger self, and how he's balanced the pressures of a decades long career in startups with being present for his kids and wife.

Speaking of presents, are you worried about daylight savings time this weekend? You may lose an hour of sleep, but you can gain some merch. Visit www.startupdadshop.com S H O P dot com and check out all the best dad and mom gear to support your favorite pod.

Adam: Hello. I would like to welcome Eben Pingree to the Startup Dad program. Eben, it is a pleasure to have you here. Thank you for joining me.

Eben: Thank you for having me.

Adam: So I found you on the internet. I'm not sure how, but you started a very interesting company that I thought would be really relevant.

And your background is kind of related to this company and your priorities. So, Why don't you tell me a little bit about your professional background? What would you say you do here?

Eben: When I first graduated from school, just a couple of years ago, maybe 20 years ago I thought I wanted to be a writer. So, many people thought I was going to be the next great American writer. And I did manage to get a job working for one of my favorite authors, Dave Eggers, out in San Francisco. So, started working for McSweeney's for a little bit. Moved to a bigger publishing house and had some great experiences. Got to work on a book about Bruce Springsteen, who's one of my heroes.

Adam: That wouldn't happen to be in Nebraska, would it?

Eben: Was not the book, no, no, this was about his band, about the E Street Band.

Adam: I'm going to see Bruce Springsteen perform in two weeks in Phoenix, Arizona. My dad is a huge Bruce Springsteen fan. It's, It's part of his belated birthday present.

Eben: Is this the first show for you?

Adam: It is the first show for me. It is not the first show for my own father, who has probably seen him a hundred times in concert.

He's a huge fan of the boss. So.

Eben: That is awesome. I'm probably in the 30s or 40s, but we'll have to touch base after the show.

Adam: I will definitely do that.

Eben: Yeah, going back I realized after a short stretch that as much as I loved reading and writing, it was not what I wanted to make my career out of. Somehow made the jump to a very random world of institutional investing. Actually followed my older brother there, which is a theme for my life.

I pretty much just followed him for the first 25 years of my life. So moved into this weird world of working for endowments and helping them invest. Gravitated towards venture capital and kind of started to learn about the startup world from 10,000 foot view and eventually realized I wanted to kind of move closer to the action.

And so I made the pretty expensive decision to go back to business school to make that transition. And ended up kind of going to the other extreme. So I founded a company when I was in business school. It was a kind of private messaging app. And so I just kind of dove into the fire and that company, I made every mistake you could ever imagine, but still walked away just kind of completely hooked on the startup pace and just the, you know, waking up every day with a million different problems that you have no idea how to solve and just kind of having to figure it out. So I've kind of been in tech now for 10 or 11 years. All pretty early stage I went from there to a company called Session M that builds loyalty marketing software and was in a product role that company sold to MasterCard.

I went over to a company called EverTrue, which built fundraising software for schools. And I ran product team there for about five years. And that company also sold and that, kind of took me up to my latest adventure.

Adam: And what is that latest adventure? Tell me about it.

Eben: Yeah, so, less than a year ago, I founded a company called Kinsome which is focused on trying to strengthen the bonds between grandparents and grandkids.

Adam: Very cool. We're going to get into that a lot more. Do you have a strong relationship with your grandparents or did you, I'm not sure if they're still around.

Eben: They are not anymore. I did, I think I had a good, fairly kind of typical relationship with my grandparents in terms of kind of modern day America, but I'd say my inspiration for starting Kinsome is much more based on my kind of current family, my kids and their relationship with my parents. I live in a intergenerational building.

I live in an apartment below my parents. I'm in a two bedroom with three kids below them. And then below me is actually my younger brother with three more kids. We've got another brother across town with four kids. So we have a lot, a lot of family around and I've become a, just a huge believer in kind of how powerful those intergenerational bonds can be for my kids to have my parents kind of constantly giving them positive attention and you know, doting on them I think is very healthy for my kids, especially because my parents are just, they're at a less distracted stage of life than my wife and I.

And for my parents to have six grandchildren under the same roof as them kind of keeps them very active, I'll say. Probably more active than they'd like, but I think is very healthy for them. And then for my wife and I, at this kind of crazy stage in life where we're trying to keep three young humans alive and, you know, starting to have to help with my parents a lot more and at the peak of our careers I think just having my parents and my kids kind of watching out for each other in their own ways is a huge, both source of joy and kind of, guilt and stress relief for me, I'd say.

Adam: Yeah. And you mentioned your older brother lives like down the street from you or nearby. Right?

Eben: He's nearby. He had too many kids to fit in the building. He has four boys and a large dog.

Adam: Oh my God.

Eben: Yeah, he was out.

Adam: Wow. There's a lot of, there's a lot of children in your family. There's a lot of grandkids.

Eben: A lot. Nine boys, too. Nine boys and one girl. We broke the curse, so I'm the automatic favorite in the family for that. We've got one daughter.

Adam: So what was life like growing up? Did you grow up in this building that you live in now with your parents?

Eben: We grew up in the apartment that I am now living in. Very recently, I switched apartments with my parents to get a, they couldn't do the stairs anymore, so I recently moved into the apartment I grew up in, which is very surreal, and we're kind of just now in the phase of kind of getting our kids set up, and it's just a constant lot of deja vu, and you know, all these daily kind of stories being remembered as they're getting settled up there.

But yeah, we grew up right in the city. My parents moved to this area in the early 70s and bought a building where they could rent a couple apartments below them. So we always had tenants. And now those are the apartments that my brother and I moved into eventually.

And it was very much kind of city living. We walked everywhere, took the T, went to school through high school, right in the city. And it's kind of the only, only life I've known. I've pretty much always lived in cities other than when I was at college and grad school.

Adam: Yeah. You mentioned the T, so I assume that that is Boston, which I think you told me in our prep,

Eben: Yep. We are right, right downtown in Boston.

Adam: Okay. So what were you like as a kid growing up in Boston? I'm curious to hear about, you're a middle child. So what was life like as the middle child growing up in your household?

Eben: I was pretty painfully shy. I think anyone that knew me back then would agree with that. I was just, some of that is probably middle sibling. My older brother was pretty gregarious and outgoing. And my younger brother was kind of, I don't know, a little wild, incredible athlete.

And I was just kind of keep me out of the spotlight. I'll just kind of hang out in the corner here.

Adam: Classic middle child, flying under the radar.

Eben: Exactly. Yeah, I mean, I was super close with my brothers. We have kind of a, like if people hear about our family they often remark on just how weirdly tight my brothers and I are.

Went to the same schools through, through college. We all moved to San Francisco and lived in a house together there for seven years after college. And now we're back raising our kids together. So somehow we've kind of managed to stay very close. I think growing up that was a big, big part of my life.

Adam: Who in the family was the first one to have kids? Your older brother?

Eben: My older brother. Yep. My older brother. I think, yeah, he was the first one married and first one to have kids.

Adam: Do you seek him out for parenting advice from time to time, or how does the parenting advice flow in your, family with, you know, 10 children within a two block, two to four block radius from one another?

Eben: I think there was a period when he actually had his first two kids, so I was an uncle twice over before I had my first but he was still living out in San Francisco, he hadn't moved back quite yet, so that was from afar so I would, get tastes of it when I'd go to visit San Francisco, but it was kind of short enough where I didn't see you know, everything that came with it.

So I don't know that it kind of fully allowed me to go into what I was doing eyes wide open. So I was still, yeah, becoming a parent was still very shocking.

Adam: You know, speaking of which. Let's talk about that. You have a partner, you have a wife, you have three kids. How did you and your wife meet each other?

Eben: This story is kind of nuts. I was working for an investment consulting firm out in California. I was running the team of associates and the company was based in Boston. So I would come back home to host trainings and because my parents happened to live in the city, I would sometimes host the new associates for drinks or whatever, after training and my wife was a couple years behind me in college, and we actually met for the first time when she came over to my parents house, which is now my house. So, it's all very, very strange. We literally met in what is now our living room.

Adam: That is strange.

Eben: It is, yeah it's hard to wrap your head around, we did not ever think we would be living there, but I worked with her for three or four years after that and the rest is history.

Adam: All right. And you have three kids. A nine year old, a five year old, a three year old. Is that right?

Eben: Yes. One's turning three in a couple of weeks.

Adam: Okay. Well, you got all the bases covered there. No teenagers yet, but you're on the way. So tell me a little bit about what your wife does for work. And then what was the decision like for the two of you to start a family? Were you like, Hey, we're in our parents, our living room now, we should, you know, what let's have kids. How'd that conversation go?

Eben: Yeah. so my wife works at Fidelity. We both went to Tuck business school, graduated a decade ago. Yeah. And she's been there pretty much ever since. So, in a lot of ways, I think you'll probably hear throughout this conversation, we are a case of opposites attract. She loves big company, stability.

She has no problem kind of navigating the bureaucracy and she loves it there. She's had a great experience. I wouldn't last a day there. But it makes for a good partnership because I am able to take a little bit more risk career wise and it's worked out pretty well in that sense.

In terms of the decision to have kids we'd always kind of just talked about it. Like it was just when we were moving into the apartment that we were in for nine years in the building, you know, it was, oh, this will be the kid's room. But I don't know that my wife might tell a different story that there was like an explicit conversation like now is the time. I think my wife tends to decide things and then they happen, so it was probably more like that but it was always just having kids was always kind of a big part of our plan and then we had one and then more came so.

Adam: Did you have any pressure from your next door neighbors slash parents to start a family?

Eben: Yeah, they were pretty excited about having grandkids, especially because the first two were still out west at the time.

So I do think we delivered the first one in Boston. And then there was this ongoing pressure to deliver the first girl. So we had, my mom and had three boys and then went on to have of the 10 grandkids, it's nine boys and one girl.

So, that, that was the main pressure. Just keep having kids until there's a girl.

Adam: Until there's a girl. That could be dangerous. You end up with a lot of a lot more kids that way.

Eben: Thankfully we got one. And at that point my mom was happy.

Adam: Yeah. What is the earliest memory that you have of becoming a dad?

Eben: I remember Cole, my oldest I remember him being born, he arrived pretty early, he was I think like four, three or four weeks early, he was kind of like a little gremlin when he was born, so he was like very small and it was, I remember just he was so little. And took him a couple of weeks to kind of fill out, but it was all very surreal.

I was in the middle of running my first startup, was very much in the thick of the startup grind. And I think in a lot of ways, brought some good perspective to that journey. And he gave us a run for our money. He was not an easy baby. He like, I think he cried for five straight months.

But eventually it was one of these cases where a switch flipped and he started sleeping and everything started getting much better, but it was rough. It was like the snowiest winter in Boston history. Nine years ago. So there were just like, you couldn't get out of your apartment.

You were snowed in with this screaming baby. It was a dark, dark stretch.

Adam: Wow. Tell me about this idea of having your first kid while you're also trying to build a company. A lot of people would say that those things are incompatible with one another, but you've made it work and you continue to make it work. So how did that go?

Eben: I'd say nowadays I'm making it work. I can't say that I made it work back then. Cause the startup didn't work. Luckily the kids worked…

Adam: Well, you know, something's going to work

Eben: The more important one worked. But these days do think. You know, there's certainly something to be said for having more hours in the day and week to work on a startup, but to me it's, the perspective of having kids and I think specifically for us we're building a company focused on better connecting families.

So it would be pretty hypocritical to, You know, not be seeing my kids and my wife and my parents and brothers. So I think it's kind of ingrained in our DNA as a company to try to find the right balance. And that doesn't mean by any stretch that it's a lifestyle business or that we're not working hard hours, but we are, we're flexible about when those hours are so that we can be there at our kids events and be, you know, parts of big parts of their lives. So I am kind of constantly working in work stuff when I'm, you know, on the train or after the kids go to bed or wherever it is, work is kind of always waiting. But when my kids have something going on they’re, the priority.

And I think that's something that I've gotten better at this time around.

Adam: So I, to ask you because you mentioned their current company now and that's focused on helping grandkids better connect with grandparents and I guess vice versa. So you have your situation where you live in close proximity, all the grandkids, all the grandparents, like right there together.

And I imagine that you've seen some real benefit from that. And so what was the Genesis for wanting to start this kind of a company? Why did you need to see something like this exist in the world?

Eben: So. Unfortunately, one of the sparks was a little over a year ago, my mom was diagnosed with Alzheimer's. And unfortunately, father in law got the same diagnosis around the same time. So it pretty quickly became a huge part of our lives. And among the many kind of reactions we had, one was just this huge increase urgency around making sure our kids developed as strong a bond as possible and created as many memories as possible with them and know, to your point, it happens naturally when you live in the same building but with my in laws, even though they're not very far away, but at this stage in life, even trying to coordinate a, you know, FaceTime call can feel totally daunting and so as we kind of thought about how we could recreate some of the magic that we see in our very unusual living situation, kind of remotely. We were just very underwhelmed with the tools that were out there and you know, talking to friends it felt like chasing the kid around with the iPad and trying to get them to sit still for 30 seconds, bribing them with, you know, anything possible to, you know, have some sort of a meaningful connection over, FaceTime with the grandparents is kind of the de facto solution and most people felt like it, left all parties pretty unsatisfied and so that's what set us down this path of thinking about what a platform that's really focused on the challenges of the relationship between people that are 50 plus years apart and what we could deliver that would solve some of those, unique challenges.

Adam: Yeah. And what's important to get right there? Like what is Kinsome do differently than me chasing, by the way, I fully appreciate the challenge of chasing a kid around with an iPad, trying to get them on FaceTime. I still don't think my kids quite, even though they're even a little bit older than yours, still quite know how to use a phone appropriately.

Like, I watch my son hold it like five feet away from his face and he's yelling at it and I'm like, no, no, up to your ear, man.

What is kinsome do to like combat that horrible painful process that parents go through?

Eben: Yeah. So a big part of our hypothesis is that we wanted to kind of take this stress off the parents plate. So we wanted to kind of remove parents as the bottleneck because there are a lot of reasons that grandparents and grandkids are kind of uniquely situated to form a really strong connection and, you know, kids need more attention now more than ever.

And grandparents need more social connection. There's a lot of evidence that's come out. The surgeon general's kind of loneliness epidemic report is highlighted some of the health impacts there. And so the need and the opportunity for those two generations to, to connect is very obvious and strong, but the problem is that parents typically have to be the facilitators.

They're the ones that are kind of situated in the middle, but they just don't have the bandwidth. Like, we talked to hundreds of parents and as much as they love the idea of that bond forming, you could just hear in their voice that, like, they're just trying to get through the day with everything going on.

And so we wanted to remove them, but we knew that you couldn't typically put, you know, a seven year old and a 70 year old on a Zoom call like this and think that they're just going to have this beautiful connection and conversation. doesn't work that way, unfortunately. And so we wanted there to be some level of facilitation, and with everything happening in the AI world, we saw this chance to basically build this conversational facilitator that was trained specifically for this intergenerational challenge.

An use that particularly on the kids side to kind of teach them to share more of their lives and open up more and learn about their family history. But do it kind of through this intermediary that is kind of based on what parents often have to do to get their kids to talk to their parents but without that burden being on the parents plate.

Adam: Wow. Pretty amazing. I'm gonna have to check this out. If you could go back in time, let's say you had a an Eben time machine, and you could rewind the clock to the right before you had your first kid, or maybe you were talking to your older brother and he already had two. What advice would you give the younger version of you or what advice did you receive that you would really like hold on to and want to pass forward to younger Eben in that situation?

Eben: I mean there's a lot of advice I would have given to myself, you know, five years before that, just about, you know, things that you will not be able to do once you have a family. So I, I think that there's definitely something to you know, taking advantage of the time before you have a family.

I think in terms of the moments leading up to right when Cole was born it's definitely cliched, but I think just the idea of like, not wishing away any of your time. I think even in those first awful days and months where he was not sleeping at all, you find yourself being like, God, if I could just wake up tomorrow and it'd be six months from now life would be so much better.

And even still, we have a three year old who won't sleep. You're constantly tempted in the middle of the night to be like, God, would, this would be great if it was his fourth birthday. But I think with a little more perspective now, I'm able to look back and try to just always remind myself that you know, you gotta find the good even in those really dark days and grab onto those and just not wish your life away at all.

Adam: Yeah. Now, what about the opposite of that? There's obviously a lot of parenting advice being thrown around in your family because there's 10 grandkids and grandparents. There's lots of generations of parenting experts in your immediate circle. So what is the advice that you've found to not be super valuable?

Or what would you tell younger Eben to ignore?

Eben: I naturally ignore most advice, I guess I'd say. My nature is to want to figure things out for myself. So I'm like the type of person who gets something new that they have to assemble or set up. And I'm like, throw out the instruction manual and I'll figure it out.

And I love figuring things out. And so, for me, you know, I wasn't reading parenting books or you know, trying to lean too much on friends and family for advice. I kind of. Just wanted to experience it and figure things out as we went. So I don't know if anything jumps to mind in terms of specific advice that in retrospect didn't turn out to be very helpful, but it's probably because I ignored it to begin with.

Adam: Oh, well, maybe that is the advice. Ignore it all. First principles only.

Eben: Right.Right.

Adam: I love that. When you think about some of this advice that you know, would give your younger self, has that translated into any kind of frameworks or guardrails is there a philosophy or something where you and your wife have kind of aligned on? A framework for raising kids?

Eben: I've been actually listening to a number of your podcasts here, and I've been very impressed and intimidated by how thoughtful some of your other guests have been.

Adam: It’s all fake, all of it.

Eben: My wife and I are very much going back to this opposites attract type thing. We have very different viewpoints and we just come into every decision probably from like polar opposite sides and we find some sort of middle ground and to date that's kind of been our, way of getting by. So, I don't know, it's related to my last answer. I think it's where we kind of just take things as we go. That's probably my side. That's unfair to my wife.

She's got things planned out far in the future. But from where I sit I wouldn't say that there's, there's a framework or strategy, again, it comes back to me feeling like why I'm attracted to starting a company. It's each day we wake up and we got new problems. And it's not worth trying to come up with some sort of framework or strategy because tomorrow's problem is going to be totally outside it and then we just have to figure it out. So that's kind of been my parenting approach.

Adam: Yeah, yeah. So I wanted to reflect on and ask you about this idea of living under the same roof as your parents, right? Even though it's an apartment, you're separated by floors and ceilings from one another. A lot of the folks that I've talked to for this show, they don't have family nearby.

They don't have a community. And, I think it's kind of acknowledged that that's hard that that can be challenging. It could also be challenging to have parents that live right on top of you. And so I guess what are some ways that you've seen your life really enhanced by living in super close proximity to your parents slash the kids, grandparents, and also, I guess, siblings and your nieces and nephews too.

what are those kind of distinct advantages that you found from everybody kind of living in one big communal household?

Eben: I think there's very like practical day to day things that that certainly add up over time. I mean, we are, we kind of approach life as a pack. So, you know, someone's car needs to be moved because of street cleaning. It's, you know, someone else jumps in and then takes it.

Someone's at the store, they text the six adults in the building to see if anyone else needs anything. You know, you run out of sugar, there's two apartments you can check. So there was very practical day to day things. I think at a higher level what I really appreciate is, and this goes back to trying to run a startup is, you know, there are times when I'm not able to be there, but knowing that my kids are with my parents or with my brothers or with their cousins I think it, certainly reduces the guilt that I feel because I think that, you know, developing those bonds with their family, spending that time with their grandparents is well worth it.

So I think that is a big part of how I make this work both from a emotional standpoint and then practically speaking, like the number of days I have to call my parents and say, Oh, you know, I'm going to be late. Can you run and grab Cole at school or can you listen to the monitor while Beckett's napping, so I can, you know, run out and take this meeting. And so…

Adam: Mm hmm.

Eben: In a lot of ways, I can't fathom how we would do it without all this support. And I should mention my in laws they're not far away, too. So we are very spoiled in terms of the support we have. My sister in law, who lives below me, is a pediatrician. And we've got, like, the full…

Adam: Oh, wow.

Eben: Setup.

Adam: This is like old school village, you know, compound child rearing. Wow. This is amazing. I, can I come and move in, in your building? Is there room in a closet or something for me?

Eben: I mean, unfortunately, I think we've maxed out too many kids at this point.

Adam: We're a full occupancy.

Eben: My older brother would be pretty mad if I let you in when he was not allowed in.

Adam: Right.

Eben: But I, I've been definitely putting myself in my wife and my sister in law's shoes as the two non originally non Pingrees in the house.

Like, they're the ones that have certainly had to adapt a lot more. Luckily, they can vent to each other about, you know, how crazy we all are and how stubborn we all are and but I think we're very lucky that, they get along really well with my parents and each other. And then I think we all just think having the cousins grow up basically like siblings is pretty amazing.

Adam: That is pretty amazing. But someday I'll have to have your wife on the show and she can spill all the tea about the…

Eben: Oh boy.

Adam: It's okay. Nobody listened to this show. They'll never know. All right. So speaking of which I have found that partnership is super important when you have kids and it is also very difficult to fully agree 100 percent of the time with your significant other. What is a point of friction or what's something that you and your wife don't necessarily see eye to eye on when it comes to parenting?

Eben: I mean, this, how much time do we have here? This is, uh. We, like

Adam: I think this is going to be a good one

Eben: I'd say just child discipline is probably the most, most obvious one. We are a polar opposite ends of the spectrum there. My wife is, I would say, very uh, accommodating with the children. I'm not sure she has a single rule.

And I like to have some level of order. So, we kinda have to meet in the middle there. I think the kids get very different tastes of parenting when it's just one of us home. When we're not balancing each other out. yeah, we've definitely got, like, the good cop, bad cop routine, so.

Adam: You know, that is really funny because it is the opposite of your professional lives. Right? Like you chaos personified as a startup and she works in a big company and loves the structure and bureaucracy of a company, but not so with parenting.

Eben: I know. We get home from work and we need a taste of the other side, so.

Adam: yeah, it must be because you've got to find something that you can have control over in your life.

Eben: Right. Exactly. Right. Yeah.

Adam: Building a company…Lord knows. Yeah, that is hilarious. So you've built a, you know, you built a career, at least the last you mentioned decade plus in technology, starting companies, building technology companies.

Your company now is, a technology company designed for kids to be on a device, communicating with, grandparents, things like that. How do you think about the relationship that you want your kids to have with technology as they get older?

Eben: It's something I think a lot about, and maybe I'm just justifying our lack of screen time control right now, but I I worry more about it as like my oldest starts to reach tween and teen years. Reflecting back on being a kid and just how shy and insecure I was. I think that it would have been very dangerous to be in this kind of social media world and I can only imagine how it would have amplified some of those issues. So I definitely think a lot about, like, how we will control and teach the kids about kind of, the world of social media and how to try to kind of brace themselves against the kind of pack mentality of people judging you online and whatnot.

The other end of the spectrum we've kind of just wave the white flag in terms of screen time with our children now. I, feel very ashamed listening to some of the other guests, but our kids right now. I think we are fairly relaxed about what they watch. But we try to balance it with kind of being outdoors, playing sports, getting out as much as possible.

So for us, it's less about how much they watch and more whether they balance it with other things right now.

Adam: Yeah, that makes a ton of sense. And don't let these other guests fool you. They're probably sneaking in some screen time to

Eben: I mean, our kids have just been terrible sleepers and I just, I don't know if I'd be alive today without the iPad in the morning.

Adam: Without that Saturday morning, 5 a. m. ipad time.

Eben: It's our savior.

Adam: So, aside from sleep, what is something that you've had to give up to become a father?

Eben: I mean, I'm a big believer in like trying not to give up a lot of my hobbies. This is a very non answer, but I definitely have tried to kind of get my kids into the things that I love and been fairly successful and in a lot of that, I've got my older son is a diehard Boston sports fan. My daughter loves helping me with gardening and I do a lot of like woodworking and outdoor chores.

We go to Vermont a lot and she loves helping with all that stuff. So definitely try to like involve them in the things that I love to do so that selfishly, maybe I don't have to give them up, but I think so that I can kind of help them figure out what they love to do at an early age. it's hard to say besides sleep because that would be my number one answer.

Like I've had to give up sleep. I've been tired for 10 years now since my oldest was born.

Adam: Between the companies and the kids. Not a lot of time for sleep.

Eben: No, no.

Adam: So, what would you say is a mistake that you've made as a dad?

Eben: I think early on, when my wife was pregnant for the first time, kind of, as we did kind of start to think about, like, what our life is going to look like and what the schedule of events was going to be I think we didn't fully appreciate just, you know, how much things could go differently than your plan. You know, my, my son was born four weeks ahead of time. I had a million things that I was going to get done in those last four weeks before he was born. And of course that all just goes out the window and similarly our, son and our daughter are four years apart and, you know, in my head, we were going to have another kid two years later, two and a half years later, and it was going to be just like me and my brothers and, you know, with miscarriages and all this stuff that just teaches you you know, trying to plan these, Big life things can be a fool's errand sometimes you just have to be grateful for the way things happen. So, I don't know, that's not, that's kind of a rambling answer, but I think learning to just go with what life gives you, particularly with these big events, and we're pretty lucky with how everything's turned out.

Adam: Yeah. Yeah. You started multiple companies and that comes with a cost, right? It's time consuming. It takes you away from your family from time to time. If you get an important meeting, they got to meet right now. And you usually can't say no to that sort of stuff. You talked a little bit about this at the beginning or earlier part of the episode around this idea of balance and leaning in some areas and then making sure that you're present and others. But how do you think about this sort of startup hustle culture pressure and how that fits in with family life? And how have you tried to sort of set the best example for your kids or the example that you want them to take away when they think about working dad, working mom, that sort of thing.

Eben: I mean, I'm definitely in the camp that like there, there's no way to turn starting a, a startup where you have big aspirations for the impact you're going to have and turning that into a lifestyle thing. It's just, I don't think that's possible. So as nice as it would be to, you know, work 30 hours a week and have all this other time with my kids, I don't see how that is possible.

So I think that is certainly something that I knew full on when I was starting my second company here that I wasn't going to have as many hours, but one thing like the hobbies that I have I try to kind of involve the kids in the work, whether that's when I'm working on the weekend, my kids will come into the office with me and like, it's easier with our product, my kids are top beta testers, so that's a unique benefit that we have that my son is designing features for the app and my daughter's recording voices for videos that we're putting out there. So I have a little bit of an advantage there, but yeah, I don't think there's any getting around just how hard it is and that comes both in terms of hours and stress.

We've taken investors money, you know, family, friends, angels. And I think if people are going to take a bet on me and my co founders, we're going to do everything we possibly can to make that a good decision on their part. And I think that I would want my kids to see that.

So the idea of like true balance is not something I guess I, fully believe in, but I believe in doing things that you're passionate about, and I believe in trying to make an impact, and I think if Kinsome's a success, it'll do a lot of good for the world, and that's something that I'm proud to show my kids, and, you know, seeing that it takes a lot of hard work to achieve things like that, I think is a good lesson as well, so, just trying to kind of figure it out day by day.

But I really do because when I'm not with them, they're with family. That's a huge part of what eases some of the guilt, I'd say.

Adam: Last question for you. You've got three kids in a two bedroom apartment. You've got a startup, also your child. And you have a partner, you have family, sometimes probably family pressure. What do you do when it seems like everything's going to crap and you need to recharge your batteries? What do you reach for?

What do you do when that happens?

Eben: We have this place in Vermont, which I think is an escape for me. There's, you know, endless outdoor stuff to do there. I am not, like, going there to go skiing…for me, it's, I go there and I go outdoors and I do, my brothers make fun of me, like I enjoy manual labor.

Adam: Chop down a tree!

Eben: I, like, oh absolutely, chopping, splitting wood is up there, building a stone wall, whatever it is.

I renovated an entire barn by myself up there. That stuff is where I can kind of really just get in the zone and lose myself. I learned enough from my dad to be dangerous with various tools. And so I do a lot of building and repairing and I love just getting that type of stuff done gives me both doing it allows me to kind of zone out but then kind of checking off these chores around the property give me a sense of satisfaction so I love being up there and being outside.

Adam: Awesome. Every time you mentioned Vermont, I just was thinking like maple syrup. You must live on like a maple syrup farm or something that that's what I know about Vermont. That’s it.

Eben: There's plenty of syrup around. We are not yet making it but I've got a long list of like dreams for the property, probably when the startup is no longer all encompassing or the kids are in college before we get like chickens and maple syrup and all that, but it's on the list for the future.

Adam: What is it about everybody and chickens? You know, I used to own some chickens myself. It feels like that's a thing that's many people aspire to at some point. Maybe that means you've made it when you have chickens.

Eben: Yeah, I don't know. I don't know what it is as a city boy that's just a totally. Foreign concept to me.

Adam: There was once an article about startup folks and tech workers in Silicon Valley who were getting chickens. I think it was like a New York Times story. Interviewed some people that I knew, which was awesome. But yeah, check it out. Maybe I'll send you that link. Maybe we'll include it in the show notes for people who are curious about chicken life.

Eben: I'm, to be clear, I'm not looking to have chickens in downtown Boston. This is purely, we are on a farm up in Vermont where chickens will be happy. So.

Adam: No, no, I can't imagine there's any more room for anything in your two bedroom apartment.

Eben: Nope.

Adam: Okay. So you're living now in the place that you grew up in. And so is your wife, not the place she grew up in the place you grew up in.

Has there been a sense of urgency around like changing things so that it doesn't feel like the place that you grew up in? Like, are you out there with a sledgehammer knocking down walls and repainting things? Slash is your wife. Or what has been your approach there to kind of make it feel like your own while I guess also not losing touch with the nostalgia of the place you grew up.

Eben: We are literally like a week or two into this apartment switch. So I should, I should clarify that we are no longer in the two bedroom apartment as of like a week or two ago. We are now living in the apartment that I grew up in, which has an extra bedroom. So, Yeah, we're, we've made it. But, um, absolutely some of the, like, turns and conditions of making this switch. And for 10 years we were not planning to stay here. It was always like, next year we'll go find a house somewhere and it just and you know global pandemics…

Adam: I don’t know. Have you seen interest rates? I don’t know that I would.

Eben: Right exactly so it just kept staying and then eventually for a variety of reasons this plan to switch apartments with my parents came about and but my wife was very clear that she was going to be able to make pretty much any changes she wants as part of that and that was something that she wanted to make sure my parents understood and my brothers and I guess my brothers were the ones pushing her more to make sure that she knew that they understood that it was going to be her house and our house and she didn't need to be like checking with them to like paint a bookshelf or something.

So we are in the early days, there's definitely some tension of like, she's going to destroy my like childhood, whatever to…

Adam: Yeah.

Eben: But no, for the most part, it's been healthy and we’re, again, my younger brother is a, an architect and runs a design build company with my best friend. So

Adam: It just keeps coming!

Eben: I know, I know. So we've got some talented people as we're kind of reimagining this space for ourselves. So.

Adam: You should just like charge a membership to your building and then anyone could come and get architectural advice, pediatrician services. I mean, people would pay top dollar for the startup advice, financial advice, you got all the bases covered.

Eben: It’s all in one. If Kinsome doesn't work out that's plan B.

Adam: Yeah. Can I buy a Pingree membership, that's what I want to know. All right. How can people be helpful to you or follow along with your journey if they feel so inclined?

Eben: We are just starting to build out our team. I should clarify. We're very early in this journey. So we are just making our 1st couple kind of founding team hires. My co-founder Mike is an incredible engineering leader. So he's hiring the 1st engineer to work with him. We'll probably add a product designer pretty soon.

So definitely making a couple of hires if our mission moves people. And then kinsome.com is the website and LinkedIn's probably where we're most active.

Adam: All right. Sounds good. We will link to those things in the show notes. Now, with that, are you ready for the rapid fire round?

Eben: Let's do it. 

Adam: All right, let's get going here. What is the most indispensable parenting product that you have ever purchased?

Eben: iPad.

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

Eben: I can't remember all the names, but we bought every sleep contraption you could ever, we bought them all, and they didn't, 

Adam: None of them worked!

Eben: None of them worked. It's such a vulnerable time to get at a parent when they're in the middle of the night. There's no amount of money we wouldn't have spent, but we tried them all.

Adam: This has come up on multiple episodes along with the Snoo, which could be priced at a million dollars and people would still buy it at 2 am.

Eben:Yeah, that is a reasonable price. Yeah.

Adam: All right, finish this sentence. The ideal day with my kids involves this one activity.

Eben: Not an activity, but just laughter. I love, my kids all have incredible, totally different laughs. My daughter has this cackle that just like lights up a room. They all just, I don't know, anything that makes any of them laugh is a great activity.

Adam: That's awesome. I love to hear that. What is the most frustrating thing that has ever happened to you as a dad?

Eben: I would say some of our like medical care adventures when we've had to take kids into the E.R. and wait, you know, we had one last night. I luckily drew the longer straw. I mean, I didn't have to go. My wife had to take my youngest to the E.R. last night and, you know, four hours later came home. So we've definitely had some pretty frustrating medical visits.

Adam: Pingree Pediatric Services failed you that…

Eben: Right, yeah, well, that I should mention that we've saved probably 80 percent of the visits we would have made by going downstairs. But,

Adam: E.R. visits. Not fun. I agree. What is your go to dad wardrobe?

Eben: I think I'm probably wearing it just my finest sweatshirt here. My wife is much more stylish than me and not a fan of my wardrobe.

Adam: All right. What is the favorite age for your kids?

Eben: I would say my oldest is at a pretty incredible age. He's nine. Just at this phase where, you know, none of the teenage kind of jadedness has sunk in yet, just full of optimism and enthusiasm, old enough where he's hilarious, like making me laugh, definitely kind of at this place where it feels more like you're hanging out with your best friend than your kids. So, he's at a really fun age.

Adam: Okay. 180 degree opposite from that. What is the least favorite age for your kids?

Eben: I, the early days were not for me. Two and under was just it took me longer to kind of build the bond and that was very much just survival mode and it didn't get particularly easier with all of them. So, luckily when, with the second and third I kind of got the duty of keeping the older child alive while my wife probably bore the brunt with the younger ones.

But, yeah, three, kind of once they hit three and up is has been a lot more enjoyable for me.

Adam: It's when you're in the clear, minus the ER trips.

Eben: I wouldn't say the clear, but it's getting clearer.

Adam: Less foggy, perhaps. Have you ever secretly thrown away a piece of your kid's artwork?

Eben: We do this every single day. My daughter is a prolific artist, and there's just no way to keep the amount of art that comes home, so we put her to bed, and then we do some recycling.

Adam: Yeah, I'll bet. What is the most absurd thing that one of your kids has ever asked you to buy for them?

Eben: I took my son to a Celtics game for his, I want to say his seventh birthday, and through some insane connection, one of my best friends from college surprised us, and we got just these incredible seats, like, courtside seats. And so now, anytime we're going to any sporting event, that is his bar.

And so he's like, Dad, can you just upgrade to like being on the field? So we've had to work on kind of reestablishing his expectations there.

Adam: Yeah, that's good. Now, with three kids, at three different ages, you've probably watched a lot of different kids movies. Which kids' movie is your favorite?

Eben: We're now entering the phase with like my oldest where he can watch movies that I like truly enjoy. He watched uh, Princess Bride recently, which was just an incredible parenting moment. I actually wrote a blog post about that recently. So we're getting to the point where you know, I've got the list of movies that I'm very excited to watch with them. I think the younger kids, Oh, Robin Hood the old fox one.

Adam: Ah, The fox yes, that is a classic.

Eben: That was a big, yeah. Love that one.

Adam: Yeah. Okay, you mentioned you're the type of person that just gets the furniture and throws the instruction manual out and just builds it. What is the worst experience that you've ever had assembling a children's toy or a piece of furniture?

Eben: This is what I live for. I love assembling things. So, that's my. That's right in my wheelhouse. Yeah, I don't…

Adam: This is gonna go inside the Pingree Prime membership, is Eben's assembly services. We've got finance, we've got architectural, we've got pediatrics, now we have assembly and construction. So, we've got it all. All the bases are covered. Okay. For only 99 dollars a year. You too can be a member. How long can a piece of food sit on the floor and you will still eat it?

Eben: There’s no time limit. It's case by case, but I just have to look at it and I just know whether it's going to kill me, but it's, it's a long, it's a long time.

Adam: It's a real time assessment of the risk factors

Eben: Yeah, exactly. There's so many different things you have to consider.

Adam: I love that. You mentioned the Princess Bride, also a favorite of mine. My grandparents used to have that on a VHS tape and I watched it until it did not work anymore. What is another nostalgic movie that you cannot wait to force your children to watch?

Eben: Stand By Me.

Adam: Oh, another good one.

Eben: Just the soundtrack everything. Love, love that movie.

Adam: Speaking of which, how often do you tell your kids back in my day stories?

Eben: It's started to ramp up with my oldest. He's kind of getting into sports and I've got this kind of little window here where I can tell those stories before he's gonna realize that I wasn't a very good athlete. So, I'm piping it up right now. There's, there's been a lot.

Adam: The old four touchdowns in a single game glory day story.

Eben:Yep. Exactly. Exactly.

Adam: Two more questions for you. One, with three children and another seven in proximity, what is your take on minivans?

Eben: Big fan. Big fan. They were a part of my childhood. We had VW like the big vanagans. We had several of them. And we did a lot of driving as a family. So just having your own space. I remember when they went from the bench seat to like the two captain's seats in the middle. And that meant, one brother got one, one got the other, and then someone got the whole back row.

And that was, It was for three or more kids. It's, it makes a big difference. So I'm a big fan. We moved on to the, an Aerostar when I was older and my parents somehow parked that in downtown Boston for our whole teen years.

Adam: Okay. All right. And last question for you. We're pulling this one from the question archive. Where is the strangest place that you have ever found a diaper?

Eben: I don't know about strange. I've like some gross places like, found just, you know, tucked under the couch, had clearly, but unlike food, like, old diapers definitely have a short expiration window so.

Adam: Unlike a fine wine, they do not get better with age.

Eben: No, not at all yeah, so definitely found some where they shouldn't have been, but I don't know about strange, just, just gross.

Adam: Well, on that wonderful note, finding a diaper under the couch months later. Thank you very much, Eben for joining me today.

It was a pleasure having you. I wish you and Kinsome all The best of luck. And it sounds like a product that needs to be out there in the world. So I'm excited for some people to discover it.

Eben: Thank you so much, Adam. I really appreciate it.

Adam: Thank you for listening to today's conversation with Eben Pingree.

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 10,000 subscribers and stay up to date on all 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.