Being a Dad at Two Hypergrowth AI Startups | Lee Robinson (Dad of 1, Cursor)

[00:00:00] Lee Robinson: What I want is my daughter to realize that this world is built by people no smarter than her and she has the agency and control to build things and change things and shape things. The earlier they both learned that once the second one is here, I think it shapes your mind in a way that I didn’t have that ability until I was much older.
[00:00:21] 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. When I originally reached out to my next guest, he had a five month old daughter. It took us nearly 10 months to have this conversation. That’s because not only was he raising a newborn, but he also was working at several of the fastest growing startups of all time. Lee Robinson is the VP of Developer Education at Cursor and for five years prior to that, held a similar role at Vercel. He’s a husband and the father of almost two girls. When you listen to this episode, he’ll be on the cusp of welcoming his second daughter. Today we talked about what his first year of fatherhood has been like, what it was like to become a dad in the craziness of not one, but two hypergrowth startups, the discussions behind family planning with his wife, what he was worried about and what ended up being not so scary about becoming a dad. His advice to other prospective startup dads with intense jobs and one of my favorite topics, what the future holds for AI and education. 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 Lee Robinson to Startup Dad. Lee, I am so excited to have you here with me today. Thanks for joining me.
[00:01:48] Lee Robinson: Yeah, thank you for having me. This is fun and different from the normal podcast that I do, which I think will be a good time.
[00:01:54] Adam Fishman: You will not be the first person on this show to say that. So a little backstory on how we met. I reached out to you because I saw somebody tag you in a Twitter thread about great dads and I was like mining it for potentially great guests and you were on there. I reached out to you 10 months ago. At the time you were like, well, I have a five month old, so I don’t have a lot of wisdom to share yet, but now you almost or 14 month old, it’s been nine, 10 months later, I’m finally, I’m stoked that one you can finally make the time to join me and two, I’m really excited to talk about fatherhood. This is going to be a great conversation.
[00:02:38] Lee Robinson: I was deep in the trenches at that point just trying to make it through and just getting through the difficult nights of sleep and I was like, I know there’s a time in the future where my life will be easier. Hopefully that’s in 10 months we’re going to find out
[00:02:54] Adam Fishman: And here we are.
[00:02:55] Lee Robinson: Here we are.
[00:02:56] Adam Fishman: You were also joining a new company, so you were at Vercel for five plus years and now you’re at Cursor, two companies that I love and use products of every single day. We’ll get to what it’s like being a dad while you’re also working at an explosive high growth startup. But first I just want to kick us off and say what has the first year of fatherhood been like for you?
[00:03:19] Lee Robinson: I was the type of person who wasn’t sure if I wanted to have kids, which is probably a common sentiment amongst the ambitious 20 year olds who haven’t been exposed to all of the real world yet. I thought I knew what the real world was, but I don’t think I actually realized what it was and my wife was kind of the same way When we first got together, we were like, yeah, maybe we’ll have kids one day. Maybe we won’t. Weren’t really sure. It wasn’t really something we were considering very much, and the biggest revelation of the first year of being a dad to me is I see the world differently. I have even more empathy for everyone else going on this crazy strange journey together and this whole part of the population that are parents and we’re doing this thing that I now know the difficulty of that thing the whole time, and I was kind of oblivious to the reality of the difficulty of that thing. So I have a new respect and admiration for other parents who are working ambitious jobs. I have a new respect and admiration for my parents. I mean, it’s made me look at them in a different light and we’ve had lots of shared bonding over that and seeing how they became grandparents and how they worked with our kids. So a lot of firsts, a lot of reflection and a lot of meditation on what it means to be on this floating rock.
[00:04:51] Adam Fishman: You really do develop, there’s a few things in life that you can’t quite know what they’re like until you experience them firsthand. One of them is becoming a parent. I think the other is probably joining a rocket ship company and people are like, oh, it’s really chaotic, and then you get there and you’re like, oh, this is what they meant like. Okay, cool. So on that note, you mentioned you have a newfound empathy for people who have ambitious jobs and also families. So little personal anecdote about me, when I was an very early employee at Lyft, I was the first person at the company to have a kid. We did not have a paternity leave or any kind of leave policy because we didn’t actually have that until our general counsel became a parent and then was like, oh, we should probably write a policy for this.
[00:05:41] Adam Fishman: We were raising our series B when I went out on paternity leave and I took two weeks off and I thought that was a lot. I thought that was what people did. It was just absolute madness. So you are at Cursor, you’re building this, everyone knows the revenue curve. It’s like a rocket ship faster than almost anything else that’s ever been around before. In the past and before that you were building Vercel, which is another insanely fast growing company. So what was it like to become a dad amongst all that craziness and was that part of the nervousness or the trepidation that made you think you weren’t sure if you wanted to have kids?
[00:06:24] Lee Robinson: I don’t think that work was part of the reason why I was skeptical about having kids. I couldn’t decide whether I thought I was going to be a great parent or not, which is maybe me being too critical on myself and definitely now seeing my wife in hindsight as a mom, it’s like, wow, she’s amazing at this. And if I would’ve known that from the start, I would’ve said, you’re going to be a great mom. Let’s do this thing together. So it wasn’t as much about work, but I definitely, as I started to especially start my role at Vercel, I started to feel that a bit. Luckily one thing that Vercel had that many companies do not have is a CEO with a lot of kids and specifically a high growth tech startup with a CEO with I believe he has five kids now.
[00:07:11] Adam Fishman: Wow. I should interview him.
[00:07:13] Lee Robinson: Yeah, and Guillermo, he’s a very good role model for being a parent. He won’t talk about it very often because he’s so focused on building the company and he’s been building the company for 10 years, but I would get to talk to him in private and ask him a little bit about what that was like and I don’t think he realized it, but it did help me rationalize it a bit and give me confidence if he can do it with that many kids, I think I could do this thing because I noticed that not just him but other people at Vercel who were leaders at the company who had kids, I was very impressed by their ambition and their ability to just get things done, and I was shocked because these things felt at odds, yet they were so ambitious and so good at their jobs and I thought, how could this be?
[00:08:10] Lee Robinson: Where do they have all the time in the day for this? And after getting to know them better, something that seemed very contradictory at the time now in retrospect makes a lot of sense. They were fueled to do better because of their families. They were fueled to set up a working environment and set boundaries because of their families. They were fueled to go really hard at work and then go home and enjoy their time with their family because of the passion on both sides, the passion at work and the passion at home, and that made me feel more comfortable going into the process of becoming a dad and also shout out to Vercel. They had a very generous parental and maternity leave, and I think that also helps. People are making that consideration. I think the industry as a whole has gone a lot better about that from the early days of Lyft, I’m sure it sounds like it was a much different time and a much different world there, and I think a lot of companies are much more progressive now in terms of offering that as a benefit to employees, which is good.
[00:09:11] Lee Robinson: We need to have more babies in the world.
[00:09:15] Adam Fishman: That’s right. Yeah, 2012 Lyft, very different from 2025, 2026 Vercel and Cursor I would say. When you were joining Cursor, how long have you been at Cursor? About four months. Four months, okay. So when you were joining Cursor, did you being a parent or having a certain kind of schedule, did that come up in conversation? I realize obviously companies are not supposed to be like, Hey, are you a parent? I’m not talking about HR violations. I’m talking about more like you describing what you needed because you have this small life at home that you’re partially responsible for.
[00:09:55] Lee Robinson: Yeah, it’s not only that, it was also that I worked there for five years and they were a very remote friendly company. So I live in Iowa and their headquarters is in San Francisco, but Vercel over the years expanded to many different offices around the world, probably like seven or eight, and very supportive of people working remotely. So you have a founder and CEO who has kids remote friendly environment, pretty good place to have a family. When I was entertaining the thought of joining Cursor, very different. They are at the time entirely in San Francisco. The founding team did not have kids and they were younger and I was definitely a little worried that will they understand where I’m at in life? Will my position in life being remote even though most of the company 98% is in San Francisco, will that travel work if I’m in the office maybe once a month?
[00:10:57] Lee Robinson: Is that enough? There was lots of questions I had to work through with them in terms of what it meant to be effective at my job remotely and what it meant for me to be effective in person and to get to know the team and to build trust there. But kudos to them for being open to the idea of that and then really embracing it and making Cursor a company that people who work remotely can thrive at. And now they have an office in New York. So New York and San Francisco kind forces you to adapt to a remote friendly workplace when you have people on different parts of the world. And I think it’s went pretty smoothly since then. So a lot of my initial fears were quickly calmed, but I will say the weirdest thing is it’s the first time that I’ve felt old at a company and I’m not that old. I’m 32.
[00:11:47] Adam Fishman: Whatever your skincare routine is, you’re looking great.
[00:11:50] Lee Robinson: Thank you. Thank you. I’m 32 and I’m married and I have one daughter, another daughter on the way, which we can talk more about. And most of the people I’m working with are fresh out of school. They’re 22, 23 ambitious. They’ve got their whole life ahead of them. They still see the world as this malleable thing that they can shift and build these amazing ideas and me too, but I’m like maybe a little more jaded, let’s be honest. I’ve seen some stuff. It’s been different in a good way, and also I’ve been able to learn a lot because of that, and I’ve bonded in different ways with those at Cursor who have joined and who are in a similar stage of life as me and who do have kids. We now have a parenting channel that’s really fun to be in. There’s people now who have joined who are older than me, which is great too. And yeah, it’s just given me an appreciation for the ups and the downs of being a parent and what that means to bring it to the workplace.
[00:12:50] Adam Fishman: Have you found as you’re, let’s say 10 years older than the maybe youngest employee at your company, are you drawn more towards the people that are your age, have your lived experience, maybe have families? Is it harder to connect with the YOLO 22 year olds?
[00:13:11] Lee Robinson: I don’t think so, and I think because the type of people who join Cursor are very motivated to figure out what it means to build software in the future, what is it actually going to look like with AI getting better and better and better and all of us being so interested in the art and science of building things in the world, software, maybe hardware too. What does that look like in this new world? And that’s the shared goal and mission. And even though we come from different walks of life and different backgrounds, I still have found it pretty easy to get to know and get along with some of those people. But I will say it was kind of funny. I’m in the office in San Francisco, we’re sitting down, we’re having food, we’re chatting, and I said something to the effect of, yeah, me and my daughter, and I don’t think that they meant this intentionally, but I kind of saw their facial expression be like, Lee has a kid, but damn
[00:14:11] Adam Fishman: Man, he’s old.
[00:14:12] Lee Robinson: Yeah. They’re like, oh, I was going to go to a party this weekend and have a good time. And I’m like, I’m the washed up guy, I guess.
[00:14:19] Adam Fishman: Yeah, yeah. Oh man, that’s so funny. I’ve been that person before. I’ve also been on the other side of that, looking at the people with kids and thinking like, oh man, you’re old. It happens fast though. So you mentioned by the way, you just sort of snuck that in there. You and your wife are having a second kid. Congratulations. I hope your wife continues to have a happy and healthy pregnancy. You mentioned that Guillermo at Vercel having five kids gave you a little bit more confidence that, okay, he can do this with five kids. I could do this, I could be a dad, but I am very curious what the conversation was like with you or probably conversations between you and your wife when you were like, Hey, intense job, but maybe it’s time to start a family. What were the considerations and discussions like that the two of you had?
[00:15:10] Lee Robinson: My wife and I, we met in 2018 at a bar, which is fun.
[00:15:15] Adam Fishman: No one does that anymore. That’s so romantic
[00:15:18] Lee Robinson: The old fashioned way. And we coincidentally went to the same college, but we didn’t meet in college. We met shortly after college.
[00:15:26] Adam Fishman: Was that Iowa State by the way? Is that where you went to college? Yes. Okay, alright.
[00:15:30] Lee Robinson: Yep. So a few years later we met at a bar and we were together for a few years before getting married and when we got married we kind of started the conversation and we talked about it, but we kind of both mutually agreed. It didn’t really feel like it was yet the time. I can only speak for myself here, but internally I felt a lot of angst that I wanted to make sure that our relationship was as strong as possible before we put the additional thing on top of like, oh yeah, I have to raise another human. And that is an infinite slope and there’s always more work to do. The treadmill keeps on going, so I knew that eventually you’re never fully ready and you’ll have to just decide. But I wanted just to make sure, I wanted to be married for a few years and just make sure everything was feeling good before we decided to take that non reversible life decision.
[00:16:24] Lee Robinson: And so we had been married for a few years, everything was going great. We started to talk about what it would actually look like for us to have kids and it was a lot of conversations. It was a lot of conversations about how would you be a parent? How would you do this thing? What do you want our kids’ lives to look like in the future? How would you want to raise kids? What names would we have for kids? All of these things, especially when I think most of at that point, let’s call it 2021, 2022, most of our friends did not have kids yet either, so they were kind of in the same stage of life as us. So we had a lot of those conversations and we decided, okay, it’s time to give this a shot. And it was not a straight line between I think we want to have kids and actually successfully having our first child.
[00:17:12] Lee Robinson: Lots of ups and downs, bless my wife’s soul. We had a miscarriage along the way, which was very difficult and emotionally challenging and also makes you realize the fragility of life and actually successfully having a child. I remember it was the day we were going to the hospital for our first daughter’s birth and my wife made some comment about the birthing process is scary and things can go wrong, and I don’t know why, but at that point it never really set into me that there’s still so many things that can go wrong during the delivery of the child, not only for the child, but for my wife. All these alarm bells went off in my head. I was like, I’m like, wait, how common is it that there’s complications during the birthing process? And there was just so many levels of anxiety that triggered. Little did I know that was only the beginning of the anxiety of just having a kid and trying out these new things.
[00:18:11] Lee Robinson: But yeah, it was such not a straight line from I think we want to have kids to successfully having our first child and seeing our daughter grow and learn and do all these things and then again deciding we want to have another one too. I think ultimately for me, when I am rocking my daughter to sleep at night and I’m trying to just soak in every last minute of that experience because at the time I was sitting here thinking this might be the last time I might not do this again. We might only have one child and she’s only ever going to be this small one time and there’s only going to be so many sleeps, so many bedtimes, so many books to read. And I really wanted to just enjoy the good times while we were in the good times because it’s a fleeting moment and the thought of, well, I guess we could do this again if we had another kid and we talked about it more and we’re like, okay, this is definitely going to be hard. There’s going to be a lot of new things and a lot of new challenges. But you know what? I think that we’re pretty good parents. I think we’ve learned a lot of things and I think it would be great for our daughter to have a sibling and now having another sister. So having that relationship for them to be close together I think eventually led us to be like, okay, this is scary, but we’re going to do it.
[00:19:35] Adam Fishman: Yeah, awesome. What a journey and it’s going to be amazing and you’ll get to do it all over again. So you mentioned that you were nervous checking with ChatGPT a lot. I think a lot of dads are nervous wondering, I hear it a lot on this show wondering, am I going to be good at this? Is it going to come naturally to me? And for most dads it takes a little bit of time to warm up to it. So you were worried about a bunch of stuff. What did you discover right after your daughter was born that ended up maybe not being as scary as you thought it was going to be or as anxiety producing as you thought it would be?
[00:20:12] Lee Robinson: I’m kind of one of the younger ones in the broad family tree. So I hadn’t spent a lot of time holding babies, playing with babies, being around young children, and I think I was worried that that was going to feel weird or awkward or I somehow would be bad at that. But yeah, immediately that was like, oh, this is a no brainer. I immediately picked that up and that part wasn’t difficult at all. I also think that you often hear a lot of anecdotes from parents that can make being a parent sound scary or intimidating or difficult, and now in retrospect I kind of understand where they’re coming from. It’s not necessarily that they’re always wanting to just vent about something. I think it’s more of when you’re doing that with another parent, you can really empathize and it’s kind of a fun way of saying, I know what you went through.
[00:21:06] Lee Robinson: I feel that too. And even though it was difficult, we all know that it was worth it, but at the time, not having went through it, I remember being like, wow, this seems scary. That’s a lot of diapers I’m going to have to change. There’s a lot of things that could go wrong here. When in reality none of that stuff really mattered, like changing diapers, whatever, it didn’t really matter. All of that stuff was just the day-to-day actions of actually taking care of the child. Nobody could have prepared me for what it felt like in the moments in between seeing her, seeing this baby that my wife who I love together created a physical human, a real person with both of our DNA and all of these great qualities to see this person, see this child learn things for the first time to say mama and dad, it’s like mind bending how that would make me feel to the point where I would travel for work and I would be out in San Francisco, I’m trying to go to bed, I’m laying in this hotel bed and I’m just thinking about picking up my daughter and putting her into the air and giving her a hug and how she fell asleep on my shoulder and wanting to get home as fast as possible just so I can put her to bed again.
[00:22:22] Lee Robinson: I would’ve never thought that or been prepared for that.
[00:22:25] Adam Fishman: Yeah, it’s really interesting. A long, long time ago, one of my earliest episodes, I had a guy named Matt Greenberg on and he talked about you don’t really know the capacity that you have for love until you have a kid, and then when you have another one you’re like, I couldn’t possibly love any more than I already do, and then it just expands again. It’s like a balloon that just keeps going. So that sounds a lot like what you’re describing there. Yeah. So if you were talking, and I’m sure you do talk to dads, you’ll probably be talking to some people at Cursor at some point who will be like, oh, what’s this? I’m nervous about this too, but if you’re talking to a dad who’s, sorry, a potential dad who’s working at an intense and fast paced job and maybe they’re a few years behind where you are, is there any advice that you would give them or what would you do to give them a bit of a pep talk around this?
[00:23:15] Lee Robinson: I think that for my family, for me and my wife, part of the reason why we have been able to raise our daughter welcome in a second daughter in a successful way I think is we really wanted to make sure everything else in our life was stable and healthy and ready before we embarked on this new journey, which we thought in the most ideal scenario, that’s what you would do. Obviously mistakes can happen, you can get pregnant early, all that stuff happens, but in the most ideal scenario, you and your significant other would have spent a lot of time thinking about, talking about preparing for this world. So for us, we felt as prepared as we could be. Obviously, what’s the Mike Tyson quote about everyone has a plan until you get punched in the
[00:24:05] Adam Fishman: Mouth. Yes.
[00:24:07] Lee Robinson: And sometimes that’s literally getting punched by your flailing arms of a baby. I feel like that would be the first thing that I would recommend is for someone who’s wanting to consider being a dad, working in a potentially difficult job, a high growth job, a demanding job where it’s asking a lot of you and a lot of your time and mental energy is ideally the other things in your life can be stable because it’s hard to deal with more than one crisis at a time. And I think we all know this, when you get sick and the only thing you want is to not be sick, that’s the only thing you can focus on. I just wish I wasn’t sick. This sickness really sucks. It makes you forget everything else and be like, yeah, health is actually extremely important. I need to prioritize that. It’s kind of similar where if you’re going to have a kid and that’s going to become this very important thing in your life, you don’t want to have these other unresolved bits of baggage that you needed to work through or you needed to talk through.
[00:25:04] Lee Robinson: And obviously no relationship is perfect. My wife and I have had to work on many things and grow and evolve together and there were certainly things we had to just spend time talking and learning how to love each other better and learn each other’s the way we like to communicate, the way we like to handle conflicts. And once we did that for a few years, I was like, okay, I think we’ve done this thing to where we feel like we’re ready to take on this new challenge. So that’s the first big thing. I think the second thing is, okay, you decide that you want to have a kid and hopefully everything goes great and you end up having a kid. Then there’s also the practice of how do I put my priorities for my life into effect for showing up every single day? And that’s going to look different for everybody, but for me, the way that looks is health and then family, friends and work.
[00:25:57] Lee Robinson: And it might seem weird that work is so far down below all of those things, but I still take my work very seriously. I want to be exceptional at what I do and I care about it a great deal, but you can only focus on one crisis at a time, and if I don’t have my health, I can’t properly take care of my daughter. And if I’m having issues with my wife, then it makes it hard to take care of a daughter and make sure she’s growing up in a healthy environment. So there’s this cascading preference of priorities where I need to make sure that the foundations are in place before I can get to what’s going on at work, and I think it’s definitely worth making sure you’ve spent time on those first.
[00:26:37] Adam Fishman: Yeah. Okay, so to summarize that, that was incredible advice by the way. Thank you. I would boil it down to two things that came out of what I just heard. One is very bluntly, get your house in order as best you can, right?
[00:26:50] Lee Robinson: Yeah, exactly.
[00:26:51] Adam Fishman: Figure your shit out. Try not to have a bunch of fires burning before you throw another one right into the mix. So that’s sort of one. And then the second one is just be clear about what your priorities are and understand the prioritization because it’s probably really hard to do that when you’re tired and maybe a little grumpy or something like that. So
[00:27:13] Lee Robinson: Yeah, it’s kind of like in a very broad meta way it is what do you want out of life? What game are you playing? And as long as you know the game you’re playing and the game you’re signing up for, you’re going to optimize your life for those conditions. If you have unclear priorities on what actually matters the most to you, then you can very easily end up in a situation where you’re working all the time. It’s not very clear how you set boundaries between your work and your family time. And you don’t have to be in a situation where you’re pitting work against family time. You can still have that priority system and do it in a way where you can still go extremely hard on doing the best work of your life and also close your laptop and go take care of your family and have that separation. They don’t have to be at odds, even if the world has conspired to make it feel that way.
[00:28:05] Adam Fishman: Yeah. So you sort of alluded to this a few times, this idea of prioritization and you talked about your wife a lot and having good partnership with her. I’m curious about how the two of you try your best to share the load at home, and do you have a particular practice that you follow or have you just winging it or are you doing some sort of ritual or something like that to sort this out? What’s that?
[00:28:34] Lee Robinson: My wife prior to having our first daughter was doing real estate and doing it very successfully, and we had a conversation after I came back from paternity leave, what do we want to do here? Do you want to keep doing this? And if you want to still focus on your career and invest here and kind of split time with that and being a parent, I totally support that and I respect it. For me, the answer was I did still really care about my career. Even if I wasn’t getting paid to build things, I would just naturally gravitate towards this thing. I’m very interested in it and I enjoy doing the work, so it’s something I want to do and I want to be a dad. The answer for her was, I want to spend as much time as possible with my daughter and now daughters soon as humanly possible, and if we have the financial means to do that, let’s do it.
[00:29:31] Lee Robinson: So for us, she decided to stay at home with our daughter, which has been a huge blessing and I’m very grateful and thankful that we’re able to do that with my job. That has allowed us to then have a conversation about what things is she taking and what things am I taking to kind of share the load. Even though she’s able to spend more energy on taking care of our daughter, there’s still so much stuff. It’s just crazy how the stuff keeps coming up, the hits start coming and they don’t stop coming. It’s literally that. It’s like we joke, my wife is the CEO of the house and I’m kind of the board basically, but she’s the CEO, she’s also all of the employees and she takes my opinion sometimes and then mostly just discards them, which is fine. I get it. I respect it.
[00:30:21] Lee Robinson: But the way we share the load is I try to set some strict boundaries with work and then be flexible when I can. So I try my best to be done by 5:00 PM every single night, and I have this window from five to seven ish where I’m going to get to spend time with my daughter and take over for my wife and then put her to bed. So I do all of the bedtime work, and that’s worked really well so far. That’s not perfect. Sometimes I have to flex and change my schedule a little bit. Sometimes we have meetings late on California time when I’m on central time things happen and we try to adapt just based on that, but that’s my general rule of thumb. And then the second thing is one of the big blessings of being able to do remote work is I can schedule my day and structure my day to where I can still be very productive and also make time to see my daughter and help out if needed.
[00:31:21] Lee Robinson: So sometimes that might mean taking my daughter to daycare if we need to take her in for the day or there’s an errand that just needs to get done and I need to be able to go and do that. Sometimes I can flex in and do that in the day, even though I can just maybe work a little bit later that night after our daughter goes to bed. So that’s I think helped a lot with sharing the load. Another blessing of remote work is being able to see my daughter in passing, so I go upstairs to get some food or get water, which I had to move my office downstairs, which was a great idea because it would’ve been impossible. I did that right before we had our daughter. I was like, I should probably move my office to a place where I can close the door and actually have my space
[00:32:06] Adam Fishman: A little separation important.
[00:32:08] Lee Robinson: And that has been an amazing decision. So I go upstairs, need to get some water, get some food, have lunch or whatever. Being able to see her in those moments, it feels like I get to add so many more hours back to my day that I’ve done the jobs where I commuted for an hour a day, 30 minutes there, 30 minutes back. I’ve done that. It’s possible and necessary sometimes, but in the option where I don’t have to, it’s a huge blessing that I’m able to structure my day to maximize the amount of time where I can be helpful to my family.
[00:32:39] Adam Fishman: Yeah. You mentioned between the five and 7:00 PM hour, you really try to protect that time and you like to put your daughter to bed and probably there’s a whole routine around that. I imagine having been putting kids to bed for 13 years, I can appreciate it. Are there other rituals in your family that are really important to you or your wife?
[00:33:04] Lee Robinson: We’re just getting started on this journey of figuring out what our rituals are, but it’s something I really want to do. I want our kids to grow up and be able to describe this is the way our family operates. We have these things that we do that are our rituals that give us an identity. I don’t know that we necessarily have those yet other than we try to always eat our dinners together and do it in a way which does not involve screens, which I think is probably non-controversial. I think it’s almost more so for me and my wife than anything else because our daughter’s eating food. She’s not super engaged in the conversation yet, right? She’s babbling. But it’s good for us too to start that ritual now such that when our daughters are a little bit older and they’re contributing to the conversation, it will be something we can really enjoy. So that’s one I’m looking forward to starting. And my wife is a great chef, so her making food is always really fun as well. But yeah, I think we’re still on the journey of figuring this one out. Do you have any good ones you would recommend?
[00:34:09] Adam Fishman: Well, I was going to say as a fellow and former mid-westerner, although still have a bunch of family back there, I can really appreciate the dinner ritual. That one was super important for me growing up. We still do our best with that now even though kids as they get older have all kinds of crazy stuff. It’s still a thing that we try to do most of the evenings and it’s really important reconnecting on the day. It’s when we hear most of the information from our kids now as they’re getting older and can talk to ’em about what’s going on and talk about what’s about to happen and stuff like that. So that’s a pretty big one for us. And then I think as our kids have also gotten older, we’ve baked in certain destinations or trips that we like to go on or certain things around holidays that are routine and predict kids like routine. They like to know, oh, this is a thing that I’ve done before and I’m going to do it again, and that’s really fun. So we’ve worked in some of that stuff that’s been really important. You too will discover the rest of your rituals. I’m certain of it. I wanted to ask you about, we’ve talked a little bit about your wife and I’m very curious to hear about something that you learned about her or discovered after she became a mom.
[00:35:22] Lee Robinson: I would say she probably feels the same, but we didn’t really know what it was going to be like to be parents and if we would be good parents and I think optimistically, I thought I would be a good dad optimistically. She thought that she would be a good mom. There’s an element to it of figuring out as you go, I guess. She’s an amazing mom. She’s so good. It comes so naturally for her. I think she’s really enjoyed it, but also it’s been fun for me to see that relationship with her and our daughter knowing that as they get older, they can be built in best friends. And once we get to the teenage years, we can revisit that part, right? That might be a little bit more difficult then maybe she’ll be more closer with me then we’ll see. But I think that I have a lot of admiration for the job that she’s done as a parent and adapting to this new strange world and I have so much of an appreciation of what women have to go through to be pregnant and then birth a child now watching my wife be pregnant again and bless her heart, she’s had difficult pregnancies where lots of throwing up uneasiness.
[00:36:43] Lee Robinson: Some people really enjoy pregnancy. Some people, some women go through it and they have a good time. Unfortunately that has not been the case for my wife, and it’s like earlier I mentioned when you’re sick, the only thing you want is to be healthy again. And I was just talking to my wife last night, she was really not feeling great. She was throwing up, her stomach was hurting and she was like, I have five more months of this, and I’m just like, oh my gosh, you are doing the greatest service ever for our family to go through this and then to create a child that we’re going to love just like we love our first child. It’s given me a whole new appreciation for her, for our family, for what she contributes to the family. I definitely could not do it without her, that’s for sure.
[00:37:32] Adam Fishman: Yeah. So there are two things that I want to call back to from earlier. One is we talked about rituals a minute ago and you talked about we’re still kind of working those out as a family, and that makes a ton of sense. The other piece of it is you’ve talked a lot about how you and your wife had to get on the same page before, get your house in order as we discussed. So I’m curious, is there an area of parenting where you are still negotiating is maybe not the best word, but something the two of you’re still navigating your way through when it comes to parenting rules and practices?
[00:38:09] Lee Robinson: So the one that’s really funny is that I am too easy. My daughter will crawl over to me. She can walk, but she doesn’t really want to walk.
[00:38:21] Lee Robinson: She’s kind of in that phase. She’s like, I can kind of do this thing, but I would much rather you pick me up and you hold me instead. And my wife gives me shit. It’s so funny because I was way too gullible. She would come over and she would look at me and be like, will you pick me up? And I’d be like, yes, of course. I’ll pick her up. Meanwhile, my wife is the majority of the day being trying to establish like, okay, I’m not going to pick you up every single time. You need to play independently and learn on your own. So she always gives me crap about that, which I think is kind of funny and I’ve probably got a little bit better at it. The second one that we’re still negotiating over is finding names has been really hard. We debated names for our first daughter for so long and it took forever to find one that we agreed on. I wanted more simple names. She liked a little bit more exotic names and now we’re doing it all again with the second child. I think we’re close. I think we’re narrowing in on something, but yeah, it’s been harder than I expected.
[00:39:25] Adam Fishman: Yeah, you’ll have to check out, I think Claire Vo vibe coded a baby naming app, so go check that out somewhere. I think it’s been really interesting and helpful for people. I obviously have not played around with it because I don’t have to name a kid, but you’re right in the wheelhouse. You’re the ICP. Okay. That’s a funny one though. And good luck to the both of you. I know how hard that can be.
[00:39:46] Lee Robinson: Yes, thank you.
[00:39:47] Adam Fishman: I want to come all the way back to this thing you mentioned at the very onset of our conversation, which is that you’ve developed since becoming a dad, a much deeper empathy for other parents and that has kind of broadly changed your worldview. So I’m curious what you’ve seen has changed as a result of becoming a dad.
[00:40:07] Lee Robinson: When I used to travel and I travel quite a bit for work and I would see kids at the airport, it was almost like I didn’t fully take it in. I didn’t really fully appreciate their presence there. I was in my own world kind of doing my own thing and you get on a flight and sometimes you have a baby crying. You might think, oh man, I wish that baby wasn’t crying, but whatever. We’ll get through it. I’m not the person who’s anti kids on an airplane. I was always like, ah, that sucks. I feel bad for ’em, whatever. But I didn’t really know what that felt like until I was the person on a plane with my daughter. I swore I did everything. I was so prepared, and then she was just crying and bawling. I’m like, I swear she had food. We prepared for this.
[00:40:56] Lee Robinson: The flight got delayed. I tried my best and she was just crying like crazy and I’m trying my best to shush and help her go to sleep and just did not want to go to sleep. And the whole time I just can’t stop thinking, I feel so bad for everybody else. They have to listen to this. I feel bad for my daughter. And the next time I was on a plane and there was a baby crying, all I could think is like, yep, I feel you been there. I am not mad in the zeroth bit. Good luck. I’m going to give you all the kudos in the world. It’s hard. You’re going to get through this and that same thing, even though that’s probably a common example, I’ve seen it in almost every part of life. Even little things at a kid’s baseball game and you see kids who are just a little bit older than my daughter and you see their interactions with their parents and maybe in the past I would’ve saw that and thought, oh, that’s a kid with their parents.
[00:41:55] Lee Robinson: I wouldn’t really thought about it. And now I see it and I see myself and I see my daughter and I see our future and I see videos of dads and their daughters and being a girl dad and what that’s like and when their daughter becomes a teenager and what that journey is like, and it just hits an emotional nerve that I didn’t know existed. It’s like this whole new arc of life that I’m about to discover. My TikTok algorithm has honed in on that. I’m sending my wife things, I’m just crying in my room watching these TikToks of dads holding their teenage daughter and it’s like she doesn’t remember it, but there was once a time and then it’s like her as a baby. I’m like, oh my God, that’s going to be my daughter and the blink of an eye and it just reminds me I have to be so present in the moment and really take it all in love. The ups and the downs love the hard times and I think it’ll be worth it.
[00:42:57] Adam Fishman: Cool. I love hearing that changing perspective and I especially like the part about the flight, what you described is the very definition of empathy there. You don’t know what has happened to that parent whose kid is crying leading up to that moment. You don’t know if they’ve had 17 flight delays and they’ve been traveling since yesterday. And you also don’t appreciate until you are in that situation that there is no one on that flight that wants their kid to stop crying more than the person who that kid belongs to. They’re trying everything. So as we kind of wind down to a close here, there’s something that we haven’t talked about yet that I’m really very curious about and I’ve really wanted to talk to somebody about this on the pod for a long time, and that is for you, it’s this Venn diagram overlap of your job and when you think about your role and AI and education for kids, so your job is to teach developers how to use Cursor, mostly adults I would assume, although maybe like a cracked 16-year-old or something like that.
[00:44:06] Adam Fishman: But it’s to teach them how to write better code with Cursor and how to use Cursor to accelerate their progress and what a tool it is. By the way, I am really curious how you think about your daughter’s a little young for this, but there’s just a debate raging in schools right now about what to do with this technology. Do we lean into it? Is it a tool for cheating? Is it going to make our kids dumber and less capable? This is an unsolved problem currently. There will be legislation, there will be things that solve it. There will be rulings and principles established by school boards and stuff. But I’m just really curious, given your role at Cursor and at Vercel and what you’ve seen, what do you think about how we should be teaching our kids AI in schools? And I will caveat this is your opinion and not Cursor’s opinion.
[00:44:57] Lee Robinson: I’ve actually thought about this a lot. What world am I bringing my daughters into? What is this new world? And I have to give you kudos because the stage of where your children are at, you are in the eye of the storm. It is happening right now, and I think it’s tough. If I was in your shoes, I would really be in a, it’s a pickle. It’s hard to figure out what to do and how to think about these things. I think I’m going to have a few years for the technology to learn and grow, and then I think it’ll probably be a different conversation by the time that they’re ready. But it feels very similar to screens or no screens type conversations or technology or no technology conversations for kids in a much more dramatic way. It is important and we all collectively have to kind of figure this out.
[00:45:46] Lee Robinson: The way I’ve kind of reasoned through it is one time we didn’t have the internet and people went to school and they went to the library and they had to go find books and look up things like cavemen. They couldn’t just Google what is the answer to this problem. And when I was in school and we had calculators, everybody thought, well, you can’t use a computer here. We got to use, you’re not going to have access to a calculator at the job. You’re not going to have that. It’s like, well, actually it’s a little more advanced to that now. I think whenever there’s a new disruptive technology, it’s very easy to want to restrict it in a way because we’re worried that maybe you won’t learn in the same way or the kids won’t learn in the same way that you learned and you thought the way that you learned was inherently better and thus you want to hold back that progress or not allow people to use it.
[00:46:44] Lee Robinson: Even while acknowledging that there’s challenges and constraints to that. It seems like what we’ve seen through multiple generations of that is that humans find a way to automate the boring stuff and become more creative and expressive. I think if you, in retrospect, look at what happened with calculators, what happened with the internet and what’s happening now with mobile phones, but then now what’s happening now with AI, I think that we’ll probably see something similar. It’s just going to be strange and weird and probably kind of messy to get there. So the way I’m thinking about it is in its best state, AI is like a hyper-personalized tutor that can teach you everything that you need to know. It remembers everything that you’ve learned so far, and it can give you information at just the right difficulty so that you’re constantly being pushed and interested in learning new topics in a way that I maybe never got when I was in high school at a very small public school with 30 people in my class, I was kind of weird.
[00:47:53] Lee Robinson: I liked things that nobody else liked and there were not people in my class who shared those same interests and I didn’t have this thing that I could talk to and bounce ideas off of and go deep on these rabbit holes that maybe other people thought were weird. When I was downloading bootleg versions of the Adobe Creative Suite to edit videos and photos, that was me in high school. I feel like that is going to be transformative for people even though there are lots of risks and things to try to mitigate in the same way that there was a lot of risks with cell phones and the internet and what it meant for internet to be on your phone in your pocket as a youth. And I am of the strange age where I grew up without the internet and with the internet and without phones and with phones when I was a kid from ages zero to eight, I guess it was like Game Boys.
[00:48:48] Lee Robinson: And it was things that I wasn’t connected to the internet always. I didn’t always have a personal computer on me at all times. And I’ve kind of lived both of those worlds. And I think my generation in particular is kind of the only one who’s lived in that. They were on the line when it happened and what the before times were like and what the after times were like. And I think right now it’s that same thing, but maybe 10x in the amplitude of it or in the intensity of it for AI. It’s a long-winded way of saying I plan to introduce my daughters to AI soon. I don’t know when I was talking to my wife about it exactly, but I think maybe four or five in a very controlled and restricted way. It’s not open unfederated access to Google anything just like that was a bad idea anyway.
[00:49:46] Lee Robinson: And why there are parental controls on things, but in a way for them to have tools for thoughts and tools to try things and to ask questions to famously kids ask a bunch of why’s. Right? And I haven’t even gotten to that stage yet. I only know that it’s a thing. My daughter hasn’t hit me with the why. I know it’s coming and I know I’m going to enjoy it and it’s going to be fun. But when she hits me with the why maybe a little bit into the future and she’s just curious about the world, I’m excited to give her tools with my guidance and my control to help her explore some of those things. I think that by the time, let’s call it four more years, hopefully the ChatGPTs of the world have really robust parental controls. I think right now they don’t as far as I can tell, and I think there’s a lot of work to do there, especially as you get into the more extreme situations of what can happen with access to an AI that can gaslight you into thinking something or can feed you wrong information in a way that’s just different from Google results.
[00:50:53] Lee Robinson: It’s different in a way that the highs can be very high and the lows can be very low. Even though I benefited so much as a child from having access to the internet, I was on random forums, learning things, downloading software, downloading music, I can’t be too hypocritical because that unfederated access was very beneficial to me at a certain age. So it’s like I’m grappling with what exactly that means.
[00:51:18] Adam Fishman: Yeah, yeah. Well, I really appreciate that perspective. I think it’s what I heard there was controlled exploration and you’ll evaluate what are the limitations of the tools, what kind of controls are in place, and that’s going to determine just how hands on or off you are with your kids. So
[00:51:41] Lee Robinson: What I want is my daughter to realize that this world is built by people no smarter than her, and she has the agency and control to build things and change things and shape things. The earlier they both learned that once the second one is here, I think it shapes your mind in a way that I didn’t have that ability until I was much older. When I was young, I was building things with Legos or Lincoln Logs or playing Game Boy. There wasn’t the ability to just make things like actual software in a way that’s just different from building with Legos. And I think that world is strange and weird and we’re kind of figuring out what it’s going to look like. But I am optimistic for what it will look like in 10 years.
[00:52:23] Adam Fishman: Yeah. It’s the first time as an adult that I’ve found something to be magical in the same way that I did as a kid. Oh, that’s very well said. I’ve just been thinking about this building with Cursor with other sort of coding products. It’s just amazing how it works and if you can say something, you can will it into existence, which is pretty, again, as an adult, as a cynical two old people like you and me, it’s magic. And it’s the first time that I’ve been in awe and in wonder of something new since I was a kid probably. Yeah, I love that. I love your perspective on this, so thank you. By the time this episode releases, it’s going to be 2026, I’m curious what you are optimistic about as we continue into 2026, and this could be your family professionally, all of the above. What are you looking forward to in 26?
[00:53:22] Lee Robinson: I am looking forward to, knock on wood, a happy, healthy, successful birth of our second daughter and that transformation in our family. And I’m optimistic it’s going to be better than I expect. I think there’s challenges with two kids. There’ll be lots of things to learn, but I think it’s going to be great.
[00:53:43] Adam Fishman: Awesome. Well, I hope and wish for that for you as well. So to end before lightning round, how can people follow along or be helpful to you?
[00:53:52] Lee Robinson: Leerobb.com is where you can find all of my information online, including socials, blog posts, all that good stuff.
[00:53:58] Adam Fishman: Cool. We will send people there in the show notes. Alright, let’s bring it home for lightning round. This is going to be real interesting to hear how your perspective on these questions changes after you have a second kid, but we’ve only got one now, so we’ll start there. Okay. What is the most indispensable parenting product that you’ve ever purchased?
[00:54:18] Lee Robinson: I think so far getting a baby bottle washer, it was so helpful. I didn’t think it would be that helpful, but it was just incredibly helpful. I absolutely loved it, even though I’ll have to bust it out here again soon. We haven’t had to use it as much now. Yes.
[00:54:33] Adam Fishman: Okay. On the flip side, what is the most useless parenting product that you’ve purchased so far?
[00:54:38] Lee Robinson: We bought one of those nice rotating swings and our daughter was like, yeah, I don’t want that.
[00:54:44] Adam Fishman: And they’re so expensive.
[00:54:46] Lee Robinson: Yeah. So uninterested just did not want
[00:54:49] Adam Fishman: It. That’s amazing. If you could build yourself one personal AI agent to make parenting easier, what would it be?
[00:54:57] Lee Robinson: If there was a way to understand what my daughter wanted before she had the words to describe it through advanced alien sign language that I can’t understand. It’s like, okay, her diaper, it’s not her diaper. She’s not hungry. I don’t think she’s receiving, what is it? If there was a technology for that, that’d be amazing.
[00:55:19] Adam Fishman: You need an agent that can do visual and audible interpretation of your daughter and then be like, this is what she needs. A toddler translator is what you
[00:55:26] Lee Robinson: Need there. I would pay good money for
[00:55:28] Adam Fishman: That. Okay, cool. True or false, there’s only one correct way to load the dishwasher.
[00:55:33] Lee Robinson: False, because my way does not match my wife’s way, and you know what? We’re going to leave it at that.
[00:55:41] Adam Fishman: I love that. That’s incredibly diplomatic answer to that question. So what is your least favorite parenting
[00:55:49] Lee Robinson: Task? My daughter is currently in the stage where she just loves to wiggle around and changing clothes is so difficult, changing diapers, whatever. It’s fine, but changing clothes for some reason, she just hates it.
[00:56:06] Adam Fishman: So
[00:56:06] Lee Robinson: We’ll get through it. We’ll get over it. Okay.
[00:56:08] Adam Fishman: Awesome. What is the crazier block of time in your house? 6:00 AM to 8:00 AM or 6:00 PM to 8:00 PM
[00:56:15] Lee Robinson: Definitely nighttime. My daughter is usually in great spirits when she wakes up in the morning, but at nighttime the crash happens hard.
[00:56:23] Adam Fishman: Yeah.
[00:56:23] Lee Robinson: Yeah.
[00:56:24] Adam Fishman: The ideal day with your daughter involves what activity?
[00:56:28] Lee Robinson: She really likes to be outdoors, which now that we’re in winter is challenging, but she likes to be outdoors. She likes to just stare at scenery, so getting her outdoors, getting to play, going to a playground, I think will continue to be fun as she grows up.
[00:56:43] Adam Fishman: Okay, cool. How many dad jokes do you tell on average each day?
[00:56:50] Lee Robinson: I’m good for at least a few. Yeah, they come naturally now. I enjoy dad
[00:56:55] Adam Fishman: Humor. Okay, great. With your daughter, I assume eating solid foods now, what is the strangest mashup of food items that you have tried
[00:57:07] Lee Robinson: The other day? We ran out of eggs and we were making cornbread, and we
[00:57:12] Adam Fishman: Used, as far as I know, you need eggs for cornbread. You do. You do.
[00:57:16] Lee Robinson: And my wife used one of our daughter’s pouches, liquid pouches as a egg replacement in the cornbread, and it was actually pretty good. I was like, wait, is there a secret recipe hack here? This actually tastes really good. So yeah, I’m just eating my daughter’s food in our cornbread.
[00:57:36] Adam Fishman: Awesome. Love that. I’m glad that worked out for you all and maybe you’ve discovered something new and even healthier, so who knows what nostalgic movie can you just not wait to force your daughter and eventually daughters to watch?
[00:57:49] Lee Robinson: I’m excited to rewatch a lot of the classics that I literally haven’t watched since I was a kid. I don’t think I’ve watched Toy Story since I was a kid.
[00:57:55] Adam Fishman: Wow.
[00:57:56] Lee Robinson: I really like Finding Nemo. It’s a good one. That one will be fun. Yeah. There’s so many good kids movies. I’m excited.
[00:58:04] Adam Fishman: Okay. What is the worst experience that you’ve ever had assembling a kid’s toy or a piece of furniture?
[00:58:10] Lee Robinson: Well, that’s actually my task for tonight is I’m going to set up a new storage container for the toys in the toy room, so we’re going to see how it goes, but it’s always difficult. I swear. I’ve never was been like, wow, you know what? Setting up this furniture was so
[00:58:27] Adam Fishman: Easy. Yeah. This set of instructions was wonderful. Yeah. Okay. Well, good luck to you. I appreciate that. How long can a piece of food sit on the floor in your house and you will still eat it?
[00:58:39] Lee Robinson: Probably too long.
[00:58:42] Adam Fishman: Okay. We’ll just leave it at that.
[00:58:44] Lee Robinson: I should probably be stricter on that.
[00:58:45] Adam Fishman: What is your favorite dad hack for road trips or flights?
[00:58:50] Lee Robinson: I don’t know if it actually helps, but we tried to simulate the dark room sleeping environment as much as we can. When we were on the plane. We’ve flown, I think three times and we probably look ridiculous. We’ve got a sheet over us. We’re like, sh, I swear it’s going to work.
[00:59:09] Adam Fishman: It’s like when you try to put a bird to sleep and you just cover its cage with a towel or something. Basically it’s that. But on overdrive, on hard mode. Yes. Okay, cool. What is your take on minivans?
[00:59:23] Lee Robinson: I am pro minivan.
[00:59:25] Adam Fishman: Okay.
[00:59:25] Lee Robinson: I do not have one myself, but I think my brother-in-law might be getting one, and I told him it’s a good idea, so we’re going to
[00:59:34] Adam Fishman: See. What about your wife? How does she feel
[00:59:37] Lee Robinson: About minivans? Doesn’t want one.
[00:59:39] Adam Fishman: No, man. Okay. There’s always one in every family.
[00:59:42] Lee Robinson: Yeah, she’s very anti minivan.
[00:59:43] Adam Fishman: Yeah. Awesome. Okay, well hopefully you will navigate that successfully. Lee, that does it for our episode today. Thank you so much for this conversation. I really enjoyed it, and best of luck to you and your growing family throughout 2026. Thank you.
[01:00:02] Lee Robinson: Thank you, Adam. This was fun.
[01:00:03] Adam Fishman: Thank you for listening to today’s episode with Lee Robinson. 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, and see you next week.