The Hidden Benefits of Raising Kids in NYC | Dan Borok (Dad of 2, nvp capital)

[00:00:00] Daniel Borok: The things that kids do, it’s just like what are the activities that they want to engage in? Like there’s sports, there’s languages, there’s robotics, there’s the arts. They’re all great things to learn, right? You’ve just run out of time. But I think they all have huge parallels in terms of the practice. They need to really spend time to get excellent at things, and some of them have even better applications like later on, right?
[00:00:23] Adam Fishman: Welcome to Startup Dad, the podcast where we dive deep in the lives of dads who are also leaders in the world of startups and business. I’m your host, Adam Fishman. Dan Borok is a dad in a busy dual working household with two kids under 10 and demanding professional lives. He’s a partner and AI investor at nvp capital. In today’s conversation, we talked about the growing demands of kids sports, balancing schedules within a dual working household, living in New York City with kids, his paper checklist system for keeping track of the most important aspects of family health and work, and how you can practice not only in sports but also at work. If you like what you hear, please subscribe to Startup Dad on YouTube or Spotify so you never miss an episode. You’ll find it everywhere you get your podcasts. Welcome, Dan Borok, to Startup Dad. Dan, thank you for joining me today. Pleasure having you here.
[00:01:24] Daniel Borok: Well, thanks for having me on, Adam. I’m really excited to have this conversation.
[00:01:28] Adam Fishman: Okay, let’s get into it. So you have two kids. You have a nine-year-old and a six-year-old. You have a spouse who works, and from what I can tell, she has a fairly intense job in real estate investing. You work in venture capital, so you guys both move money around. Can you tell me what the two of you, you and your spouse, do to balance the schedules at home as two busy working parents?
[00:01:53] Daniel Borok: Yeah, that’s a work in progress. It’s a little bit of: do we remember on Sunday nights to talk about our schedule for the week or not? And then it’s also a lot of Google Calendar. So it’s funny because where I work, nvp capital, we have a shared Google calendar, and so if one of my teammates looks at my calendar, there’s all these notes for me and my wife Abby about what’s going on. Is she traveling? Am I traveling? What’s going on with the kids? So it’s a little bit of a stitched together calendar.
[00:02:24] Adam Fishman: Yeah. And what’s a typical — I mean maybe there is no such thing as a typical daily schedule — but what’s a typical day or a typical week in your household look like?
[00:02:34] Daniel Borok: I mean, I think there is a typical week for us and it’s sort of baselined around our kids go to school. We live in Manhattan, we live in the West Village. Our kids go to school on the east side of Manhattan, so they take the bus to school every day. So most days Abby and I are up with the kids. They have breakfast, we somehow push them out the door. Some days are better than others. We generally make it to the corner before the bus arrives, sometimes not. The other day I was running down the corner flagging down the bus, and luckily the driver stopped. That’s the sort of place setting for us — the drop off or pick up at the bus stop in the morning. And I think that’s something that unless one of us is traveling, we try and do together every week. And that’s a nice baseline because we don’t really come back together every evening because we generally have events or something else going on. So that’s our time to be together — that 6:45 to 7:30 in the morning every day.
[00:03:30] Adam Fishman: Yeah. Cool. And then do you guys have any extra help at home? Do you have a nanny — maybe less so now that both of your kids are in school — but what do you do? Let’s say both of you are traveling or something like that. How do you make that work?
[00:03:45] Daniel Borok: Yeah, well, we do have a nanny and her main thing is helping the kids do their after-school stuff. Our kids are kind of sports heavy, so getting them to the different sports, helping them. Actually my nine-year-old, who’s in fourth grade now, has homework. So this is a new thing over the last, what, three weeks — trying to figure out making sure that she’s sitting down to do her homework. But when we both have to travel, or when one of us is traveling, then we need to get more creative. So we actually live about five blocks away from where I grew up, and my parents aren’t always around, but when they are, my mom is an awesome person to fill in and get a grandmother and at the same time really help us out. Then if we have to both be away at the same time, we have to find somebody to stay overnight — that’s when it gets a little bit more complicated, and that’s when the Google Calendar really comes in handy.
[00:04:35] Adam Fishman: Yeah, the piecemeal patchwork schedule you got to sort out now. I can appreciate that for sure. Nice to have family nearby too. It makes a big difference.
[00:04:44] Daniel Borok: It’s a big deal. But we also — I mean, there’s been a number of dropped balls where all of a sudden it’s the night before and you’re like, wait. I’m like, Abby, wait, you’re traveling, but I have this dinner. And it’s like, then it’s a scramble. But every parent goes through that in one way or another. But it happens more, I think, than we’d like.
[00:05:03] Adam Fishman: Well, I appreciate you saying that on this show because I think a lot of people listen to this and think, wow, everyone on the show seems like they got it so dialed in, and it’s like — well, no, we’ve all got some balls in the air that occasionally hit the ground. So thanks for helping make that a normal part of your life.
[00:05:21] Daniel Borok: Well, relative to the other shows I’ve listened to, I think I’m the least dialed-in person you’ve had as a guest. I was very impressed with people you’ve spoken to and some of their theories and their reading and their approach to parenting. So actually I’ve learned a good amount listening to your show.
[00:05:36] Adam Fishman: Cool. Well, we do have a lot of caveats on the show. People are like, this is how it works most of the time.
[00:05:41] Daniel Borok: In theory.
[00:05:43] Adam Fishman: In theory, in theory. So I wanted to ask — I wanted to follow up — the two of you, both you and your wife Abby, have pretty intense careers. A lot of folks would — and this is becoming more common lately — a lot of people would put off starting a family. And I’m curious what the decision was like for the two of you to start both with fairly intense careers, demanding schedules. How did that come up in your house or was that an extensive conversation that the two of you had?
[00:06:13] Daniel Borok: It really wasn’t. We got married in 2013 and we had our daughter Vivi — or my wife had our daughter Vivi — in 2016. I mean, I was a little bit older. I think we were older maybe than your average parents in the US, but it feels like we’re probably in more of the age range for parents in New York City. I feel like people do — I don’t know if the Bay Area has the same vibe — but very similar, that people put off having kids until a little bit later. So it wasn’t like a discussion, but I think we just naturally met a little bit later on. And so the timing worked. I think about myself at 25, and I wish I’d been more mature, but I can’t even imagine what it would’ve been like having a kid at that age.
[00:06:56] Adam Fishman: Yeah. So the two of you maybe waited until — obviously you met a little bit later — but also until maybe you felt a little bit more mature, a little bit more stable in your careers, and that kind of path was known for you. That’s what it sounds like.
[00:07:10] Daniel Borok: That’s right. And I do think it’s an interesting conversation because you never feel fully ready to have your first kid, and there’s this idea that so many things in our lives we can plan and practice for. You can’t really practice without having a kid. And so part of me — I kept saying, well, let’s wait another year. Something else will happen. This will get better or this will get easier. And it’s really hard. And sometimes I have friends who don’t have kids and maybe they talk about having kids and they’re in that same mindset of like, oh, well, I’m going to do one or two other things so that everything’s much easier. And I don’t know that it’s ever the right time.
[00:07:49] Adam Fishman: Yeah, that’s a refrain that’s pretty common on this show too, that there’s no threading the needle perfectly. There’s always something in your life that doesn’t feel perfectly stable, and so you just kind of have to rip it off like a bandaid, for lack of a better term. So most parents I feel like that I know in New York follow this sort of tried and true path. They live in Manhattan, they have kids, they move to Brooklyn and then they move to the suburbs — Connecticut, New Jersey, New York suburbs, something like that. But that is not your path, and I understand that you grew up close to where you live now, but you’re choosing to raise your kids in New York, and I think you have an opinion that that’s a great place to raise kids, which I can’t appreciate having not lived in New York myself. So tell me about the decision to raise your family in the big city.
[00:08:45] Daniel Borok: I think that there’s just no right way to do these sorts of things. Everybody has a different path for how they raise their kids. And I did grow up in the city. I grew up in Manhattan. My mom grew up in Brooklyn, and I dunno. So I feel like I know what it’s like to grow up in the city and maybe part of it for me is the fear of living in the suburbs because I never had. But the positive view for me is that growing up in the city for kids is a great way to learn a lot really quick and have access to a lot of great things really easily. And I think frankly, New York City or San Francisco or Chicago or whatever you choose looks a lot more like the real world than the suburbs. And so while the suburbs offer a lot of great things in raising kids in maybe nurturing environments, I feel like there’s a disservice sometimes that comes with insulating our kids too much. And so there are a lot of positives. You can hop on a train and go see artwork in a museum or go see a play and you just get a sense of what’s going on in the real world. That’s my take. There’s a lot of downsides to it too.
[00:09:54] Adam Fishman: Yeah, when we went to visit New York with our kids, I mean, we packed it in two days. We never stopped. We were just moving all the time. So I can appreciate that. I was pretty tired afterwards, so it’d be nice to spread it out a little bit more if you live there. For a listener that doesn’t live in a city, what’s something special that a listener might not know about having kids in New York? Something that you really love about it?
[00:10:22] Daniel Borok: I think it’s walking around. It’s really walkable. That’s actually one thing I love about San Francisco too. I feel like it’s a very walkable city versus maybe LA or Houston, Dallas or something. But just walking around — and for kids, it used to take forever to get anywhere when my kids were a little bit younger. They would just stop and explore things on every single block and now we move at a better pace. But there’s just something about discovering the world walking on a scooter that’s pretty cool. And the history in Manhattan — in Lower Manhattan — is amazing. It’s 400 years old. There’s where we live that used to be a farm. There’s just a lot of cool things to discover. There’s still remnants of — the Aaron Burr’s Carriage House is a restaurant in the West Village. How cool is that?
[00:11:16] Adam Fishman: That’s so cool. When you reflect on your experience growing up in New York, how old were you when you first took the subway by yourself?
[00:11:25] Daniel Borok: I was probably 12, maybe 13, right around there. When I went to high school, I had to take the subway to go to high school, so that was everyday community school.
[00:11:34] Adam Fishman: Now do you think your daughter will be the same age, a little bit younger when she takes it the first time, a little bit older? What are your thoughts on that?
[00:11:43] Daniel Borok: I heard one of your guests talking about responsibility and authentic responsibility for kids. And I don’t know — as a parent, that’s a big one for me. She’ll probably take the subway by herself when she’s 12 or 13. I think that’s reasonable. But gosh, how are we going to let go and let that happen? How does it — at the first subway ride, we’re like, all right, see you later, and she walks down the stairs. It’s going to be a tough one.
[00:12:06] Adam Fishman: Yeah, you’re going to have to send somebody ahead to meet her at the other side, right? Just to make sure.
[00:12:10] Daniel Borok: That’s right. We’re going to have to tag her. I don’t know — what’s the tracking technology these days?
[00:12:17] Adam Fishman: Yeah. Yeah. Well, I think about that because there’s that author, Lenore Skenazy, who wrote Free-Range Kids, and she wrote this article a long time ago about her kid taking the subway when he was eight years old and the world imploded when she wrote this article. And so I’m just curious how people think about — I guess — how a typical New Yorker thinks about it. Eight seems a little young to me, but…
[00:12:42] Daniel Borok: Eight seems young. But for your kids, the equivalent I guess would be — when were they able to walk places by themselves?
[00:12:49] Adam Fishman: Yeah, it started pretty — well, so our daughter’s a little bit older, but our son is just a little bit older than your daughter. And it started about this time for him, but we live in a kind of boring suburb, and so there’s not much that can happen as he walks through the park to the little corner store. But yeah, I mean, I imagine that you would let your daughter go down the street to a store or something where she knew the place or you weren’t too far away maybe when she’s a little bit older versus getting on the subway.
[00:13:20] Daniel Borok: Right. Right. And you’re right. And that’s the unique thing I think about a city — just the density of people and there’s a perception that really bad things can happen. I’m not sure if that’s 100% accurate, but there’s always that chance. I think you’re right — you think about things differently. I do think about the self-sufficiency of kids, and I dunno if this sort of vibes with your experience, but it’s like when my kids got to be four-plus, they were their own little people. They could dress themselves — maybe not that well — but they could dress themselves, go to the bathroom by themselves, and it was a different category of self-sufficient kid. And now that I have a nine-year-old, I think there’s that next level of self-sufficient kid, which is, I don’t know, it depends how mature different kids are, but it’s like seven or eight where they can kind of be by themselves a little bit. They’re not going to light the house on fire, blow anything up, or do anything really, really stupid. And that’s the next level of self-sufficiency. And I think going places by yourself is right around then — or maybe a little bit older.
[00:14:22] Adam Fishman: It’s sort of these phases and step-function changes that you go through. Yeah, that makes a lot of sense. Okay, I want to talk about sports. You mentioned you’re a very big sports household. So tell me about — what are your kids into? You’ve got six and nine, so what kind of sports do your kids do?
[00:14:40] Daniel Borok: My daughter does soccer and tennis, and my son does soccer and tennis also.
[00:14:46] Adam Fishman: Awesome. And I think you mentioned your daughter — does your daughter play golf too?
[00:14:50] Daniel Borok: She does. She does. And the thing that happens is you run out of time. And so I think at this stage we’re trying to get her and my son to play as many sports as they can fit in. And then I don’t know — over time I think they’ll decide what they really like to do. My wife played soccer growing up, and my daughter just loves soccer. So if you ask her her top three sports, it’s like soccer and then everything else. And part of me is like — is that because she just loves soccer so much, or because my wife loves soccer so much? But that’s how things have been netting out right now.
[00:15:26] Adam Fishman: So you must have competing weekend games and practices and stuff like that. So you and your wife have to split up on the weekends and go to different locales and things like that.
[00:15:38] Daniel Borok: We do. And I think that’s a common refrain. And you know what? It’s one of those things I just always said, we’re never going to be those people who have kid sports demands. And then it just happens. I guess team sports really are so structured and so scheduled around a lot of different kids’ teams. So soccer is just one of those sports where the weekend games can be anywhere within the hour drive of the city, and you’re kind of beholden to those schedules. Tennis is a little bit different — more kind of a one-on-one practice.
[00:16:12] Adam Fishman: Yeah. So I’m curious — so your daughter’s also into golf. Have you read Training a Tiger and are you taking the Earl Woods approach to raising a golfer?
[00:16:24] Daniel Borok: I’ve not read that, and I think unfortunately the ship has sailed for taking a Tiger Woods approach to raising a golfer. What were his top two principles?
[00:16:35] Adam Fishman: I haven’t read the book. I think my brother has. He mentioned it on the pod, but I think he was pretty intense. He’s known as being a fairly intense hands-on guy. I think he started Tiger Woods when he was two or three and could hold a plastic golf club or something. So clearly we’re not there in your household. But I had to ask. So maybe it’s time for you to read it — I don’t know.
[00:16:55] Daniel Borok: I might have to. I do have a friend who’s taking that approach to his son’s tennis career. He’s got him with a plastic tennis racquet at two, so…
[00:17:03] Adam Fishman: Wow. Okay. Okay. So my experience — I want to stick on golf for a second. My experience with golf is fairly limited. I’ve played, I don’t know, a half dozen times. I’m pretty terrible at it. My understanding of caddying is rooted in the TV show Psych, which is a great show if you haven’t watched it, but I think probably not super accurate. You have been a caddy for your daughter at some tournaments. So can you tell me what that experience is like? Is it super stressful for you as a dad?
[00:17:34] Daniel Borok: It’s one of the coolest experiences and also one of the most stressful. So my daughter — she does play golf. She likes golf. She’s a decent golfer, but by no means top talent, just because she doesn’t play as much as other kids. But she can go out and play on a course, which is kind of amazing for me to see, because when I first started teaching her golf, my goal was always like if the four of us — me and my wife and my son and daughter — could all play together, we’d have our own foursome, which would be amazing. So caddying for her is great. You just get to walk with your kid for three hours, and you’re just out there with the other parents and the other kids, and it’s just an amazing break. That’s the positive. The negative is if you have any sense of trying to control things, which most parents probably do, you’re just watching your kid succeed or fail, and it’s really stressful.
[00:18:25] Daniel Borok: And for me, the first time we did it, I don’t know, I just had to look away. I think there was one hole where she chipped back and forth four or five times and maybe hit five putts, which is a lot. It was really difficult for me to watch. I’m not saying I could have done any better, but it was very stressful. But once I detached from that and just said, hey, we’re out here having a good time — every once in a while she’ll let me give her a read on a putt — it got a lot of fun.
[00:18:53] Adam Fishman: That’s cool. Now the rest of the time, so you said every once in a while she’ll let you give her a read on the putt — the rest of the time is she batting you away? She’s like, no, Dad, I got this.
[00:19:02] Daniel Borok: Yeah, she keeps her own counsel. I’m like, hey, maybe you should hit a seven iron, which is one of the clubs. And she’s like, no, no, I’m going to hit my pitching wedge. So a super dad fail though: the first tournament we went to was — maybe it was a year and a half ago — it was in May, early May in New Jersey, and it was cold and it was rainy. And I said, hey, we’re going to go and we will see, maybe it’ll get canceled, it’s raining. But I didn’t pack any extra clothes for her. So she got wet and her sweatshirt got wet and that was it. And she was just such a champ, but she was shivering by hole three — there’s nine holes.
[00:19:43] Adam Fishman: Oh…
[00:19:43] Daniel Borok: My God. And she ended up wearing my clothes. So she was just layered in clothes that were way too big, trying to swing the club, shivering, and it was a pretty big dad fail.
[00:19:53] Adam Fishman: Oh, well, lesson learned, I suppose. So May in New Jersey — very unpredictable, very unpredictable. When you think about, reflect on your time as a dad, what would you say are some of the more surprising things that you’ve discovered that maybe you didn’t appreciate about parenthood before you became one?
[00:20:12] Daniel Borok: I think it’s that kids are just so amazing at learning, and I didn’t fully appreciate that. I mean, we talk about neuroplasticity and the fact that juvenile brains are wired to learn, but when you see it happening, it’s pretty amazing. And I think I’ve underestimated how quickly kids can pick stuff up and how smart they are, if that makes sense. And I’m kind of constantly amazed by that.
[00:20:38] Adam Fishman: Yeah, I love that. Kids’ minds are like a ball of clay in that way. Parents, maybe less. But let’s say you’re rewinding the clock and you run into Dan from 10 years ago on the street, maybe you’re on the subway, and it’s right before you’re about to have your first kid, your daughter. What would you tell younger Dan from a decade ago about having a kid? What advice would you dispense to Dan?
[00:21:04] Daniel Borok: There’s the first advice, which is — everyone’s first kid, it’s like you’re putting bubble wrap around them and you don’t need to. I don’t know if this is your experience, but with our second kid, Jack, we were a lot more laissez-faire in a good way. I think that’s the biggest thing. Not every mistake is the end of the world. Not every decision is life or death. There’s a little bit of just learning and giving yourself the chance to learn.
[00:21:27] Adam Fishman: I like to say that kids are made of rubber way more than we think. What about the opposite, though? I don’t know if you got a bunch of advice when you were becoming a dad — maybe you said you’re a little later in life, so maybe you had friends who already had kids. Is there anything, any piece of advice that you got that you would be like, no, that ain’t it, just ignore that advice?
[00:21:48] Daniel Borok: That’s such a good question. I don’t know that — I didn’t go around asking for a lot of advice and I’m not sure I got a lot of advice, or maybe that says something about me as a person. So I don’t have anything that’s top of mind. I think that some of the extremes out there around, let’s say, consuming content — we take a middle-ground approach. So I think some people can be just so cut and dry when it comes to how they think about technology for their kids. I tend to think that there’s just a middle ground for a lot of stuff. So being too absolute is tough. I dunno, I think of it as — somebody was saying, hey, maybe they don’t let their kids have any screen time, and screen time can be really negative, I think, in the wrong way. But I also remember when I was in grade school, there was one kid who didn’t have a TV, and I always felt like her parents had the best intentions because TV is bad and maybe you don’t learn a lot and you waste your time. But she also lost the social angle of doing what her peers were doing. I felt like maybe that was a negative.
[00:22:53] Adam Fishman: Yeah, that’s interesting. You can’t have that TV kid water-cooler conversation. You don’t know what’s happening with American Idol or Dancing with the Stars or whatever.
[00:23:02] Daniel Borok: Or Scooby-Doo when I was growing up.
[00:23:05] Adam Fishman: I guess we didn’t have a lot of that reality TV. We had Gilligan’s Island, that was what we had. I want to stay on this topic actually, because I’m curious. So you invest in a ton of early-stage technology companies, primarily, as I can tell, in AI — sort of vertical AI tools, which I hear is a big thing. And I’m curious — you sort of alluded to this a little bit — but when you think about the relationship that you want your kids to have with technology, you’ve seen probably the best and worst that technology can offer, being an investor in it. When you and your wife talk about this and when you talk with your kids about it, how do you think about that relationship?
[00:23:43] Daniel Borok: We talk about it a lot because I think it’s a conversation that’s happening all around us at school. And yeah, my firm, nvp capital, we’re pre-seed and seed stage, focused on B2B companies building in vertical AI. So I live this at work. The conversation’s really interesting. I think the delightfulness of technology are things like talking to ChatGPT. It’s just mind-blowing that you can do that today and it feels like you’re in the future. Or the Waymos on the road in San Francisco — that’s a glimpse into the future. So I think there’s some really positive components of technology, and I think for kids, leaning into using technology to build things I think is really positive. And actually that’s kind of a parent fail on our end, which is: our kids do a lot of sports, but they’re not doing robotics or they’re not doing coding, even if maybe coding itself might go away, but the logic of it’s really helpful. They’re actually not doing a lot of that stuff. So not quite your question, but I do think a lot about — in the same way that we learn sports because they’re great social dynamics and they teach us about practice and they teach us about what’s possible — the building component of technology I think offers a lot of that too.
[00:24:59] Adam Fishman: I love that. And I think don’t beat yourself up too badly. Your kids can always get into that later. It’s going to be there. It’s not going to go away, as far as I can tell. So they can enjoy the sports for now. But the robotics and stuff can become as demanding as a sport. We’ve got friends who are in it in high school and their kids are way into it and they’re traveling all over the place and they’re winning competitions. I mean, it’s super intense and you almost have to trade that for the sports if that becomes your singular passion, which is really interesting.
[00:25:34] Daniel Borok: And I think that’s a really good point because the things that kids do — it’s just like, what are the activities that they want to engage in? And there’s sports, there’s languages, there’s robotics, there’s the arts — they’re all great things to learn. You just run out of time. But I think they all have huge parallels in terms of the practice, the need to really spend time to get excellent at things. Again, some of them have even better applications later on in life.
[00:26:03] Adam Fishman: Cool. We’re going to come back a little bit later to that topic of practice. I want to end on that, but first I want to talk a little bit about frameworks. You told me that your firm, you’re big on OKRs. Now, I know it’s hard to have a one-to-one translation of OKRs to home life — you can’t necessarily run your household on OKRs. I mean, you could, but that’d be a little intense.
[00:26:26] Daniel Borok: You have to get your kids to buy in. What would their key results be?
[00:26:29] Adam Fishman: For those listening who maybe have never heard of OKRs — I wrote a piece about this — OKRs stand for objectives and key results, and it’s popularized by, is it John Doerr? I think that’s right. And the practice originated with Google. And anyways, it’s basically how you set goals and hold yourself accountable to keeping those goals and working on the most important stuff. So, you have OKRs at work, and then at home you’ve got a piece of paper that you keep in your closet, and that’s sort of got some important things that you need to do each week. So tell me what’s on that piece of paper and why do you do it?
[00:27:07] Daniel Borok: I have a piece of paper in my closet, and the reason it’s a piece of paper and it’s in my closet is I want it to be physical and I want it to be right in front of me in the morning and at night. So I see it and I kind of know what I’m doing and what I’m not doing. And I keep a pen next to it and I make checks next to the list of, I think, 15 things that I’d like to do every week. And I feel like if I do all those things every week, then it was a pretty good week. There’s three boxes for spending quality time with my son Jack. There’s three boxes for spending quality time with my daughter Vivi. There’s a box — or I guess only one box — for spending quality time with my wife. Maybe I need to bump that up.
[00:27:49] Adam Fishman: Or maybe you’re doing just fine. Who knows?
[00:27:51] Daniel Borok: We’re doing just fine. There’s one for calling my parents if they’re away or visiting them if they’re around. Those are the family things that I think — any week might go by and maybe I don’t do all those things, but if a month goes by and I’m not doing them, then I feel like I’m not doing what’s important in building a family. I think just showing up is really important. And so that’s the family thing. And then there’s a workout thing, which is: I want to run and go to the gym and be active every week. And that’s another thing — maybe it’s a week where that doesn’t happen; it’s like an Atomic Habits kind of approach. But it’s like, if a month goes by and I’m not doing that stuff, that’s not good. And I think that the thing with working out and being healthy is that just gives you the platform to be better at everything else.
[00:28:43] Daniel Borok: If you’re upset with your kids — they do something wrong, or maybe they didn’t, but you get really annoyed and you yell at them — is it because they did something that they deserve to get yelled at, or is it because I’m tired or maybe I’m hungry? Preparing yourself physically so that you can make the best decisions and engage the right way is, I think, really, really important. So that’s the workout section. And then even though I do have OKRs at work and me and my partner, Vaughn, talk about our objectives and how we’re going to get them done with our team on a regular basis, I do have a list of things that I think are the most important things — my objectives at work within a given week — and that’s on that list too. And so that’s my list and I try and check as many boxes as I can.
[00:29:28] Adam Fishman: Yeah, awesome. I also wanted to come back to the workout thing. So, also very helpful to work out if you’re going to be lugging a golf bag around on the golf course for your daughter. So, super.
[00:29:37] Daniel Borok: Yeah, except kids’ clubs are tiny, so… It’s true. I feel like a giant when I put those on my back. I’m like, I’m so strong and this is great.
[00:29:46] Adam Fishman: It’s good. This is a hot tip for dads listening: carry kids’ golf clubs and you’ll feel like the Incredible Hulk.
[00:29:52] Daniel Borok: Exactly.
[00:29:54] Adam Fishman: I love that. So you’ve got themes for work, family, and health — that’s kind of your OS, your objectives. And then you’ve got key results, are the checklist of things like, I’m checking this off, I’m doing it. So that’s good. I like it. And then the idea of keeping it in a physical location written down so that you can actually take action on it and you can see it and remind yourself every day, I think that’s awesome.
[00:30:20] Daniel Borok: And I keep it over — I’ll do, my sheet will have six weeks of time, and then I take a picture of it, and I’ve been saving those. And every once in a while I’ll drop them in GPT and just sort of get some feedback on what I’m doing, which is kind of a fun thing to do.
[00:30:35] Adam Fishman: Ooh, I love that. I love that. Okay, a couple more topics I want to touch on. One that you mentioned to me as we were preparing for the show is — we’ve talked a lot about aging parents on this show. We are all of the age, as parents, that our parents are becoming quite a bit older and the relationship that you have to your parent kind of changes. And you mentioned that your dad is 94, which — wow, that’s an incredible run. I hope I make it to 94. That’s why I have that workout column, too. So has having a 94-year-old dad changed your relationship to time or how you think about the passage of time?
[00:31:13] Daniel Borok: My father had me later in life when he married my mom. That was his second marriage. So I actually have brothers and sisters who are in their fifties and sixties. So it’s kind of interesting to see that progression. But you grow up with your parents at whatever age they are. And so I’d never really thought about how it impacted my perception of age, but we all do — you see your parents, in this case my dad, because my mom’s a bit younger, getting older, and it makes you think of a lot of things. One is: what can I do to take better care of myself so that if I’m lucky enough to live into my nineties, it’s really quality time? My dad’s mobility is limited. And so what’s the quality of life as you get older, where mobility is limited? I don’t know. So those are some of the things that I think about. I don’t know if that’s a great core takeaway.
[00:32:08] Adam Fishman: Yeah, no, I think it is great. You see your dad a little bit as a mirror of yourself and you are like, I want my future self to maybe be slightly more, so what do I have to do now in my forties and fifties to make sure that when I’m 90 I can still walk around the golf course with my daughter? Speaking of which, has your dad seen your caddying skills?
[00:32:31] Daniel Borok: He’s not a golfer, so he hasn’t been out there with us, but he has seen my kids play tennis.
[00:32:35] Adam Fishman: Oh, good.
[00:32:36] Daniel Borok: And actually, when I was in high school, my dad — he played tennis recreationally — but he decided to get certified as a USTA instructor, sorry, tennis instructor. And when I left — I was on my high school tennis team — when I left and went to college, he started volunteering at my school as the coach. I went to a public school, and so basically they would just tap any random teacher as the tennis coach. So the drafting teacher, which is mechanical drawing, happened to be the tennis coach, but he didn’t really play tennis. So my dad subbed in and he was the tennis coach and then liked doing that. So he actually started coaching kids for free at city parks. So that was kind of a cool thing that he did later in life that I thought was an awesome way to give back.
[00:33:24] Adam Fishman: Yeah, that’s amazing. And also you mentioned your drafting teacher. I was thinking about my own drafting teacher in high school — I mean, the guy looked like Santa Claus. He was not teaching any kind of tennis or any sort of sport. So glad that your dad could step up there and help out — somebody who actually knows the game.
[00:33:40] Daniel Borok: It was nice. I wish we’d had a professional when I was on the tennis team.
[00:33:45] Adam Fishman: Yeah. Okay, couple more questions for you. One is — I always love to ask this not to start fights in the household, but just to hear the dynamic of couples. So what is something that you and your wife, Abby, have a difference of opinion on when it comes to parenting? Where do you have different styles or standards, maybe?
[00:34:06] Daniel Borok: One thing is in sports, but I’ll give you a real one too. But with sports, Abby’s gone all in on soccer and I’m all in on tennis and, to a lesser extent, golf. And sometimes — you pointed out — those schedules conflict. So that’s a point of discussion: are we going to the soccer game or are we going to the tennis practice? And so that comes up fairly often. I’d say that Abby is — by the way, the kids both love, if the kids had to choose one parent to spend the weekend with, it would be Abby. So I’m constantly fighting that. And we disagree, and I’d say that Abby might be stricter than I am. For some reason that doesn’t matter because the kids still like her better. So lots of places we disagree, but it’s not to my benefit.
[00:34:50] Adam Fishman: Alright, I love that. Okay, two more for you. Since you invest in a ton of AI companies, tell me how you and your kids are using AI together.
[00:35:01] Daniel Borok: So one way that I was using AI — I don’t know if this is together — was just coming up with bedtime stories. That was two years ago, let’s say. And that was kind of an interesting unlock. You’re always racking your brain to come up with the ongoing dragon bedtime story and you run out of stuff to talk about. And just the ideation of OpenAI was kind of game-changing. I do think more recently I’ve just been chatting with — we talked about this earlier — but I’ll just use the voice function on ChatGPT with my daughter and we’ll have a conversation. And it’s just so cool to see her interacting with the intelligence in AI. And so we have far-ranging conversations. I think that’s kind of cool.
[00:35:50] Adam Fishman: What are some of the topics that you two go deep on with your friend ChatGPT?
[00:35:55] Daniel Borok: Vivi and also Jack just have a ton of questions about stuff. So it was during the US Open — after one of the matches, Vivi wanted to know more about a tennis player. So she was sort of like, where did this player grow up? Have they won any majors? What’s their record? And we’re just going deep on a subject, to the point where the kids now, instead of saying like, Dad, what’s the answer to this? They’re like, Dad, can you just look this up for me and give me the answer? So I’ve been bypassed.
[00:36:27] Adam Fishman: Yeah, my kids like to say, hey, Dad, search it up. Yeah, that’s what they say. And I’m like, kids, I don’t know if you’ve heard this, but search is circling the drain. It’s all about conversation now. So they don’t quite get it yet. They don’t know what that means. So, cool. I love that. I love that. And actually, now that I think about it, it’d be really cool in the future to be able to look back at that — at how your daughter and your conversation with ChatGPT change and evolve over time as she gets older. That’d be a really interesting artifact to have for the two of you and look back on.
[00:36:59] Daniel Borok: Yeah, that really would be.
[00:37:00] Adam Fishman: Maybe I’m inventing a product here. We’ll see. I know a guy who invests in AI companies, so maybe we’ll pitch that to you after the show. Once we hit stop, we’ll do that pitch. Okay. So I wanted to end our conversation on the topic of practice. You alluded to this earlier in the conversation, but you mentioned to me that you really like to connect with people over how they’re working on themselves and areas to improve. And so I’m curious to hear from you — what’s something that you’re working on right now maybe as a parent? I mean, there’s obviously professional stuff, but I’m curious what’s the thing that you’re working on personally right now?
[00:37:39] Daniel Borok: As a parent? I read a book not too long ago called The Disengaged Teen. Have you come across that?
[00:37:45] Adam Fishman: I have heard of this book, but I’ve not yet read it. I probably should, given that my daughter’s about to become a teenager.
[00:37:50] Daniel Borok: It talks about — it’s not just teenagers, it kind of starts when kids are younger. And I guess a core takeaway for me was this alignment of interest and achievement. There’s this idea that some kids are just really good at doing stuff, but they’re just doing it because they want the praise or the feedback, and then maybe you run out of steam. And then there’s some kids who are totally disengaged because they just don’t feel connected. And there’s some kids who are good at stuff, or at least really care about things and get good at them — they really care, they’re really engaged. So I’ve been trying to get better at paying attention to what really moves my kids and trying to see if maybe I can direct more of their energy to the things that they’re most excited about. And it’s a little bit of a balance. You want kids, I think, when they’re younger, to try out a whole bunch of different stuff and they might not love something today, but they might love it tomorrow, or the experience. But I do think there’s something that — somebody phrased it as, what do kids do when they have free time or when they’re not scheduled? Is that kind of indicative of where they could be leaning in more? So that’s something I’m paying attention to, trying to get a little bit better at that for the future.
[00:39:01] Adam Fishman: Great. I love that. And I’m going to have to check out that book too — The Disengaged Teen. Again, given that I’m about to have a teenager, I should probably speed-read that thing.
[00:39:10] Daniel Borok: You should speed — or just let AI summarize it.
[00:39:14] Adam Fishman: Yeah. Okay. So tell me about the parallels between practice in sports — when we think about practice, we think about sports usually — but there’s parallels between that and work. So how does one practice at work?
[00:39:31] Daniel Borok: I wrote a LinkedIn post on this because my partner, Vaughn, and I were talking about it and my teammate, Sky, and I were talking about it. We all played sports growing up and we were talking about the parallels between sports practice and work and practice. Because at work you’re kind of always on, right? It’s sort of like you’re always — maybe you feel like you’re just playing the game. And so sometimes there’s practice in between the games, but what is practice really? It’s sort of like getting reps at doing something well. And I think at work, practice is getting reps identifying great founders, would be an example. So how do you get more reps at identifying more great founders and talking to more great founders, and then providing a feedback loop so that when you get those reps, you know what those conversations meant and you know what great looks like and what less than great looks like.
[00:40:18] Daniel Borok: And then there’s the practice of preparing for those conversations, and I think that has to do with reading and research and knowing the subject matter. So those are two things that we’ve sort of identified. And I think a third is being physically able to do what you need to do. So if you think about practice in sports, a lot of it isn’t maybe related directly to the skill that you’re going to have to hit a ball or shoot a basketball. It’s more like you’re going to be physically able to execute at the level that you need to execute at. And I do think that investing is very much like that, where you have a limited set of decisions you have to make on any given day, and are you going to be mentally and physically in the best place to do that? So those are the three things that I see as parallels between investing and sports and practicing for both.
[00:41:09] Adam Fishman: Cool. I love that. And we will have to find and link to that LinkedIn post in the show notes. I’m sure I can find it. I spend a lot of time on LinkedIn — some might say too much, but no, the right amount. Okay. To end, how can people follow along or be helpful to you on your journey?
[00:41:29] Daniel Borok: Well, my journey parenting — if you see me on the street, say hello and say hello to my kids. And then for investing, we love founders using AI to reinvent industries. So if you know a great founder who’s just getting started, send them our way.
[00:41:48] Adam Fishman: Cool. Will do. And you invest at the earliest, pre-seed and seed stage — so, the idea stage, we’re putting words to paper. Awesome. Very cool. Alright, well, Dan, are you ready for lightning round?
[00:42:03] Daniel Borok: I’m ready.
[00:42:03] Adam Fishman: Okay, here we go. What is the most indispensable parenting product you’ve ever purchased?
[00:42:10] Daniel Borok: The phone, because my wife and I are constantly talking about our schedules.
[00:42:15] Adam Fishman: Okay. What is the most useless parenting product you’ve ever purchased?
[00:42:19] Daniel Borok: Oh, we got walkie-talkies when my daughter was born so that we could monitor her room, but we could hear her crying anywhere else in our apartment.
[00:42:26] Adam Fishman: Necessary New York apartment — thin walls. Okay. What is the weirdest thing that you’ve ever found in your kids’ pockets or in the washing machine?
[00:42:35] Daniel Borok: So many golf tees. Golf tees, golf tees — more tees all the time.
[00:42:41] Adam Fishman: Awesome. I think that’s a first for this podcast. Good. Okay. True or false — there’s only one correct way to load the dishwasher.
[00:42:48] Daniel Borok: That’s a question mark for me. What is your version of the correct way?
[00:42:51] Adam Fishman: Well, I think there is a way, a correct way to load it, and it’s nicely organized and everything has its place and all the plates are vertical and the stuff on the top rack and the bottom rack and things like that. But there’s the alternative approach, which is just: let chaos reign — fit as much as possible into the sanitation machine as possible and just let it rip. I’m more of the organized structure.
[00:43:15] Daniel Borok: Yeah, that second option sounds awful. I am Adam Fishman-aligned on this.
[00:43:20] Adam Fishman: I organize the thing, you team Adam. Are we all aligned in your household on this, or is this like a mixed bag?
[00:43:26] Daniel Borok: So my wife Abby would say that I actually don’t adhere to order on the top level of the dishwasher. I don’t put the mugs in the right way. So we’re aligned in that we want to do it, but maybe not how we do it.
[00:43:38] Adam Fishman: Got it — the execution in theory. And what about when your kids help you load the dishwasher, is that just chaotic or…?
[00:43:45] Daniel Borok: We don’t let them. They put things in the sink.
[00:43:49] Adam Fishman: Very precise. Okay. Maybe related, but what is your least favorite parenting task?
[00:43:55] Daniel Borok: Getting my kids out the door in the morning. It’s also a great time to spend with them, but the feet-dragging in the morning is just unprecedented. And I’m like, this bus is going to leave whether we’re on it or not. Come on, kids.
[00:44:10] Adam Fishman: I love that. I think maybe I know the answer to this question, but what is the crazier block of time in your household? Is it the 6:00 a.m. to 8:00 a.m. block or the 6:00 p.m. to 8:00 p.m. block?
[00:44:21] Daniel Borok: It’s definitely the morning.
[00:44:22] Adam Fishman: Yeah, I could tell that that was going to be the case. If your kids had to describe you in a single word, what would it be?
[00:44:29] Daniel Borok: Goofy.
[00:44:31] Adam Fishman: Okay. What is the funniest slash most embarrassing thing that one of your kids has ever said in public?
[00:44:40] Daniel Borok: I don’t think it’s safe for a podcast.
[00:44:43] Adam Fishman: Okay, we’ll hold that one for post-recording. Okay. What is your go-to dad wardrobe?
[00:44:50] Daniel Borok: T-shirt and khakis.
[00:44:52] Adam Fishman: Awesome. How many dad jokes do you tell on average each day?
[00:44:58] Daniel Borok: None. Because if I’m forced to come up with a joke, I just can’t. I really can’t think of any good jokes, so I’m a zero for that.
[00:45:04] Adam Fishman: Well, as your daughter’s getting older, you really got to work on your reps there, because your singular job is to embarrass her at every possible opportunity.
[00:45:12] Daniel Borok: I’m doing such a good job on that anyway, even without the jokes.
[00:45:14] Adam Fishman: Okay. Well, speaking of which, what is the most embarrassing thing you’ve done in front of your kids? Or what would maybe your daughter tell you is the most embarrassing thing that you’ve done?
[00:45:23] Daniel Borok: It’d probably be giving her advice when I was caddying for her in front of the other kids.
[00:45:28] Adam Fishman: Like, Dad, I know what I’m doing. Don’t tell me what to do.
[00:45:32] Daniel Borok: The eye-rolling has already started.
[00:45:35] Adam Fishman: It does start in fourth grade. The eye-roll starts so early. It starts in fourth grade. Yeah. What is the most absurd thing that one of your kids has ever asked you to buy for them?
[00:45:42] Daniel Borok: A pony. A legitimate pony. And I was just like — the joke in the house is like, you’re not getting a pony. But at one point, yeah, there was a request for a pony.
[00:45:53] Adam Fishman: In the Manhattan apartment, in the spare bedroom or something?
[00:45:58] Daniel Borok: Exactly. We just keep it out on the sidewalk.
[00:46:00] Adam Fishman: Outside, just tethered. Okay. What is the most difficult kids’ TV show that you’ve had to sit through?
[00:46:06] Daniel Borok: Oh, there’s this live-action — it might be like a Nickelodeon or Disney show — called Bunk’d. Have you watched that?
[00:46:16] Adam Fishman: I have not. No, no.
[00:46:17] Daniel Borok: It’s about these tweens at camp. Real painful.
[00:46:20] Adam Fishman: Okay. On the flip side, what is your favorite kids’ movie?
[00:46:25] Daniel Borok: So it’s really a TV show, but there are movies of it too. I mentioned before — it’s Scooby-Doo, and I just have such fond memories watching Scooby-Doo as a kid, and my kids watch it now. It’s on Netflix and Prime and it gets pushed for some reason. So I don’t know, I just think that multi-generational enjoyment of one show is kind of cool.
[00:46:45] Adam Fishman: Okay. Is there another nostalgic movie that you just can’t wait to force your kids to watch with you when they’re old enough?
[00:46:53] Daniel Borok: Goonies.
[00:46:54] Adam Fishman: Oh, great film.
[00:46:55] Daniel Borok: Is that going to hold up, you think?
[00:46:56] Adam Fishman: Oh, it will hold up. It is — by modern standards, there’s a few things that maybe we don’t agree about these days — but it definitely holds up. Okay. How often do you tell your kids “back in my day” stories?
[00:47:11] Daniel Borok: More than I’d like, but I think sometimes in jest. Back in my day we had to walk uphill all the time with no shoes on and it was very snowy, that kind of thing.
[00:47:21] Adam Fishman: Now, is that helped or hindered by the fact that you live very close to where you grew up? Do you get to point out things and be like, well, back in my day that bodega used to be a farm or something?
[00:47:32] Daniel Borok: Adam, you just nailed it. You know what? I didn’t even realize how often I do it, and now that you say that, yeah, I do it all the time. All the time. And I do get eye-rolls.
[00:47:40] Adam Fishman: Awesome. Okay, two more for you. What is your favorite data hack for road trips or flights?
[00:47:47] Daniel Borok: I mean, it’s the iPad. Does that make me a bad dad? It’s TV and the iPad.
[00:47:51] Adam Fishman: Sure does not. Sure does not. You’ve got a lot of nodding heads on that one. Okay, last one. You do live in Manhattan, so what is your take on minivans?
[00:48:03] Daniel Borok: I feel like SUVs have replaced minivans, so that’s my hot take. We all convince ourselves that SUVs are so much cooler and get the job done anyway, but they’re just the modern-day minivan. That’s my take.
[00:48:15] Adam Fishman: Okay. Alright. Well, Dan, it has been an absolute pleasure having you on the show with me today. Thank you for joining me, and I wish you and Abby and your two kids best of luck in life, in parenting, and in work for the whole rest of the year and beyond. So thank you again.
[00:48:32] Daniel Borok: Adam, I really enjoyed the conversation, and these are great questions. Thanks for taking some time to chat with me.
[00:48:38] Adam Fishman: Awesome. Thank you for listening to today’s conversation with Dan Borok. You can subscribe and watch the show on YouTube or wherever you get your podcasts. Visit www.startupdadpod.com to learn more and browse past episodes. Thanks for listening. See you next week.