Latest / Startup Dad / Startups Are BETTER for Parents Than Big Tech | Jacob Bank (Dad of 3, Founder at Relay.app, ex-Google)

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Startups Are BETTER for Parents Than Big Tech | Jacob Bank (Dad of 3, Founder at Relay.app, ex-Google) · Startup Dad

• [00:00:00] Jacob Bank: When I was 23, my answer was just to brute force everything like, oh, well, I’m 23. I have no other responsibilities. I will just stay up all night writing code. I’ll just stay up all night answering support tickets. I will just do more, do faster, do better, and now that is not an option for me. That’s totally incompatible with having kids and so you can be equally intense and equally committed without having to be in a physical office from nine to nine, six days a week. [00:00:26] Adam Fishman: Welcome to Startup Dad, a podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I’m your host, Adam Fishman. One might think that in the midst of a successful high paying and stable career at a company like Google with a six month old and two more planned for the future, you might want to stay put not today’s guest. Jacob Bank left his cushy job at Google to found Relay.app when his daughter was six months old. He and his wife a pediatrician, proceeded to have two more kids and now have a family of three, a startup and a high stakes pediatrics career. Today I talked to Jacob about what the decision was like to leave Google and start a company. His framework and recommendations for entrepreneurs considering the same why startups and small teams are actually the best for parents, his double dipping principle and his framework for getting kids to behave. Imagine if I did that, what would happen. This episode is for every dad and mom who are considering taking the leap from comfortable role to high stake startup. If you like what you hear, please subscribe to startup dad on YouTube or Spotify, so you’d never miss an episode. You’ll find it everywhere you get your podcasts. Jacob Bank, welcome to Startup Dad, it is a pleasure having you here with me today, [00:01:52] Jacob Bank: Adam. I’m excited to chat [00:01:54] Adam Fishman: And I wanted to give a quick shout out to Ben Ez for introducing the two of us. I was recently on Ben’s show, the Super Insider podcast. He’s a awesome guy, and so I’m glad that he could connect the two of us. [00:02:07] Jacob Bank: Yeah, yeah, that was great. It came up in the context of, I actually was also a guest on his show and I was showing how I use all these AI agents to get work done for me, and he’s like, wow, that’s so cool. I’m a dad. I could really use that. I’m like, yes, exactly. That’s why I did it all. [00:02:22] Adam Fishman: Yes, yes. Oh, maybe we should get into that a little bit later too, so we’ll talk about that in a sec, but let’s start with the hardest of hard questions, which is your wife Sonia, is that how you pronounce her name? [00:02:36] Jacob Bank: That’s right. Yep. [00:02:36] Adam Fishman: Sonia is a pediatrician and I want to know, is that a blessing or a curse with the three young kids that you two have together? [00:02:44] Jacob Bank: 90% blessing, 10% curse. The 90% blessing is what you’d expect. She knows what dose of children’s Tylenol to give and how many hours after you can give Motrin and on what you do, what intervention, and whether that rash is a bad rash or a normal rash. So that’s all amazing because especially when you’re a first time parent, you have no idea about any of this stuff. That’s amazing. The 10% downside is because she works at UCSF, which is a major research hospital that draws sort of the most complex patients in all of northern California. She’s exposed to these one in a million, extremely rare and scary situations that I’d I’d rather not know about. She’s like, well, there’s a 99% chance this is going to be fine, but there’s a 1% chance it’s this or a tiny chance that there’s this one in 10 million eye cancer that would be terrible. And I’m like, okay. I just would rather not have known that that was a possibility, but it’s great most of the time. [00:03:48] Adam Fishman: Yeah, I thought you were going to say that you’re worried that she would be like patient one from the next outbreak or something like that, getting some sort of, [00:03:57] Jacob Bank: I mean, certainly during COVID, and also you’re right during respiratory season right now when she’s in clinic, every kid is coming in with some flulike thing, but that actually hasn’t been the problem. We all get sick all the time, obviously, but she is not the vector of disease. It’s the other three kids. It’s the three kids. [00:04:17] Adam Fishman: That’s right. It very rarely goes from parent to child. It’s almost exclusively [00:04:21] Jacob Bank: The other. Yeah. It’s like one kid brings it home and then we can just decide. We can literally do the countdown of like, this is when you’re going to get sick, and this is when Layla’s going to get sick and this is when I’m going to get sick, and then we’ll be through it in eight days. [00:04:34] Adam Fishman: That’s awesome. It feels like maybe the riskier thing is like children’s daycare and not necessarily UCSF. Okay, you’ve got a pediatrician wife, you’ve got three kids now, but you obviously didn’t always have three kids. You were at Google for a long time. You started a company before that. It was acquired by Google. You were at Google for a long time. You left Google when your oldest daughter was about six months old as far as the math that I could tell, and you proceeded to start relay, which is growing like bananas. You’ve raised a boatload of money and then you had two more kids, and so most people would tend to stick at the stable high paying job, good benefits at Google when they’re trying to grow a family, but you did not. Why is that? [00:05:24] Jacob Bank: There are three dimensions that I considered, and then I think a lot of people that I talked to in this situation consider, and this is how they broke down for me. Number one was the first question I think you have to ask yourself is what stable income is required to maintain your family’s standard of living? That’s of course your first priority, and I know a lot of people, especially in high cost of living areas like the Bay Area, there’s a relatively high fixed floor of family income that you need to have, and so I’m definitely not suggesting anyone should do something cavalier and dip below the minimum family line that you need to maintain your livelihood. Obviously, that’s the first priority of a job. The job has to pay the bills. The second and third considerations were number two, what is going to give me the most learning and growth that will catapult me forward in the future of my career? [00:06:27] Jacob Bank: And then the third dimension was what day-to-day work will I enjoy most and best suit best fit into my family responsibilities? So for me, for number one, I had worked at Google for six years. We had built up a nest egg with this sort of goal. I had been a startup founder before I knew I wanted to be a startup founder. Again, we built up a nest egg while I was earning a high salary at Google very deliberately such that I could afford to take some significant period of time, even a couple years with a much lower income and still be able to meet our family obligations. It helps that my wife also works and has an income, so we were able to reason that’s like, yes, we’re going to be fine. Will we have to reduce our income and expenditure for some period of time? [00:07:11] Jacob Bank: Yeah, of course. But that for us, the way we did the calculation is we have a baseline of things that are important to our quality of life. We’ve already stocked a waste of money for college and for retirement and stuff, and so as long as we hit that basic threshold, we’re not going to worry about maximizing some number in some vanguard account that’s not going to impact our day-to-day living anyway. I think a lot of people in tech who are earning highs get trapped into this number maximization in some Vanguard account, which is super tempting. So we ruled out number one, it’s like, yep, we can do it. Then number two, I had been at Google for six years. I loved it there. I learned a lot there. I met some amazing people there, but I looked ahead to the next six years and I was like, oh, shoot, those are going to be kind of the same as the past six. [00:07:54] Jacob Bank: My role is going to be the same. I might have a slightly larger team reporting to me. I might work on a couple slightly different projects, but it’s fundamentally the same. At the time I was 31, 31, 20, 32, I was like, I am too young to make this the terminal experience in my career where I just do the same thing, especially in a world. This was before the whole AI wave, but especially in a world as dynamic as tech, I don’t think you have the luxury of getting the Rolex after working for 40 years at Boeing, the way it used to work in the old days. That’s just not how the modern career path works. And so I knew I wanted to catapult myself into a situation where I would learn more, grow more, move faster, learn different skills. I also thought about my experience as a hiring manager. [00:08:35] Jacob Bank: This I think something people really misperceive about the risk of big company versus small company. Let me ask you this question, Adam. Let’s say you’re a hiring manager and you have two resumes in front of you. One is a PM that graduated from college and immediately spent 11 years at Google and has had no other work experience at any other company. The other person spent three years at Google, spent two years at a startup that did really well, spent two years at a startup that didn’t do so well, spent three years at a scale that did really well and then just came off of an 18 month experience of founding and failing in their own company. Just knowing those pieces of information, who would you rather hire? I certainly would rather hire the second person. They have a way broader diversity of skills and experiences and a talent network, et cetera. [00:09:20] Jacob Bank: And so I think people always say like, oh, it’s so risky to join a startup and it’s not risky. There is a guaranteed intermediate period of time where you have lower guaranteed earnings. For sure. I just take that as a given. You will have lower expected earnings for sure, but in the long run of your career, the extra skills and experiences you get will be so much greater than just staying at the same place for 11 years, like jumping out of a plane without a parachute that’s risky. Driving a motorcycle at 120 miles an hour on the highway, that’s risky. Those things can kill you in one moment, leaving a big company to get a new experience at a smaller company that will teach you things that’s not risky, that’s an informed trade off about the future here. So that was number two. And then number three was the biggest reason that I got frustrated at Google was I just felt out of control. [00:10:09] Jacob Bank: I was out of control of my own time meetings were just plopped on my calendar and I was in those meetings from 7:00 AM to 5:00 PM or 6:00 PM every single day. Then I’d have to do my real work on the weekends. People in big tech actually work hard because it looks like you’re working hard because in a ton of meetings all the time, I didn’t have control over my own work and especially in a situation where my wife’s work is less flexible than mine is, I felt like I needed more flexibility. That didn’t mean I didn’t want to work as hard. I want to work hard, I want to be committed to my work, but I want to have the ability to trade off two hours in the middle of the day to take a kid to a doctor’s appointment and then do those two hours later after the kid is asleep. And so that was the combined factor. We were okay on the financials for some period of time. I knew I wanted to learn and grow faster professionally, and I knew I wanted to do work that I would both enjoy more day to day and also give me more flexibility to kind of adjust my schedule around what best suited the kids. And the key dimension for both of those were just the autonomy of controlling my own time, which is why starting my own company became the obvious move after leaving Google [00:11:13] Adam Fishman: Was the calculus of, Hey, we want to have a bigger family than we have today. That’s hard to do with kind of such double rigid schedules. Was that calculus part of what went into your decision to go back and work for yourself and build something on your own? [00:11:30] Jacob Bank: Yes, definitely. Especially you know this when things are going great, yep, drop this kid off, drop that kid off, have my workday pick it off, but kid gets sick here. A kid gets sick there. One kid has a school performance that you want to go to. One kid has an art showcase that they really want you to go to. One kid’s classroom needs volunteers to help with the bread making activity or whatever, and I just, because otherwise what would happen is I would have all these meetings, I would say, oh shoot, my kid’s homesick. I can’t go to these meetings anymore. And then it cascades down and ruins your schedule. And so I didn’t fully understand it as I do now with three kids, but I had an inkling that personal flexibility was going to be even more important. Time flexibility was going to be even more important at this stage, and so one trade-off was at Google, I got a nice, whatever it was at the time, 14 week paternity leave. As a founder, CEO startup, there’s no fully off. There’s just gradations. And so that was a trade-off where it’s like if you’re in a family situation where again, you need that 12 weeks fully off, that’s pretty hard to do as a startup founder practically. But again, so much of this is not like the black and white, are you fully off? Are you fully on? But it’s like how much can you flex your time to meet your family responsibilities while also meeting your work obligations? [00:12:47] Adam Fishman: Yeah, and how did you go about setting up your equivalent of founder parental leave during the next two kids? Was that something that you agreed on with your co-founders? You had to talk to the board about how does that, that’s a very different negotiation than when you’re just w W2 employee at big company and you just plug into the system, right? [00:13:11] Jacob Bank: Yeah, I mean it’s even simpler In my situation. I’m a solo founder, I am the board. It’s only me deciding what’s good for the company and the fact that I’ve convinced these nine other people to work on this thing with me and I want to do right by them. And so the fact that I have a family has played into the entire architecture of the company, not just the architecture of the parental leave. [00:13:35] Jacob Bank: Everyone on the team is very senior and everyone on the team is someone I’ve worked with for at least five years before doing the start. One person was not, but he came in highly recommended by the one other people who was so I was like, it’s people I know that are super senior. It’s people I know who are extremely strong in their areas. And so I know that, for example, even though my historical background function is in product, I could take three months entirely off of doing product work and everything would be totally fine. Even our company philosophy, we have one team meeting four days a week for 30 to 60 minutes. If you looked at our slack, if you looked at our calendars, you’d be like, no one works at this company, but if you look at our GitHub and our Figma, you’re like, oh my god, this company has a thousand people working at it. [00:14:18] Jacob Bank: And so pretty much everyone else on the team also has young kids. So we’ve all in the same mindset of how we’re approaching our careers. That’s not to say we’re less ambitious or less committed, it’s just we can execute on that ambition and that level of commitment in a way that adapts around our family needs. And so a fully asynchronous culture was the way to go. And so if we’re doing a fully asynchronous culture and I totally trust the team to do product development, I totally trust the team to cover for me on support. What am I really required to do? I was able to pair that down to a pretty small set of emails that only I could answer. And so the way I did my paternity leave, I did it in phases where I said, for the first two weeks, I’m only going to be available for this extremely urgent set of reactive things. Then for weeks two to five, I’m going to be kind of fully on async, but doing nothing sync. So don’t expect an immediate chat from me in Slack and don’t expect me to be in any, I might show up to a meeting, I will if I can, but just don’t expect me to be in any meeting. And then at week six and beyond, it was sort of back to the new normal. [00:15:22] Adam Fishman: And so one of the thing that learned about you is that you, I’m hearing this and how you’re describing this to me, but it’s a bit of a contrarian take that startups and small teams are actually best for parents. Most people think, oh, if you’re a parent, this sort of bucks the trend of this show, but most people think that if you’re a parent, the thing to be at is a big stable company with a big team and you have lots of people who can fill in and do the work and stuff. But what I’m hearing from you is actually the opposite of that, which is small team. Your team sounds like still very small. [00:15:57] Jacob Bank: We’re 10 people, 10 humans and lots of ai, but yeah. [00:16:01] Adam Fishman: And you’ve hired a bunch of other parents who probably, because by the nature of them being parents tend to optimize more for being the most efficient with their time because the time is so precious. But what else do you think it is about small teams and startups that actually make it better suited for a parent’s lifestyle? [00:16:20] Jacob Bank: The number one by far is control over your own schedule. And the fact that we have no meetings as a company is just that is the night and day difference because in any company of any reasonable size, as soon as you have 4, 5, 6 meetings per day, you are out of control of your time. And that means you have not no flexibility to adapt things around your family, but every change comes at a huge cost. That’s by far the biggest one. So if you can get into a world where it’s small enough and high trust enough that there’s no meetings or very very few meetings, I think probably the single biggest quality of life factor, the corollary of that is aside from scheduled synchronous meetings, a lot of the work at a larger company is greasing the wheels of justice to get stuff done. Like, oh, let me send an extra message to this person to remind them that this thing is waiting on their approval, or let me put in some FaceTime over there that they like me and they’ll approve my next thing with a team of 10 people that entirely trust each other and have autonomy, you can eliminate all of that. [00:17:28] Jacob Bank: Our philosophy at a company is I give everyone the most context I can possibly give them about our strategy, our goals, our approach, what I’m hearing from customers, what I’m learning from the market, and they can do whatever they want to move us forward. And the default is like, do not ask for permission. Do not get, yeah, you can get feedback from other people as an FYI if you want to, but you can do your own thing. And so those two things, the fact that there’s no synchronous meetings and people’s work is never blocked on others, it completely puts all the control back in the individual contributors hands. And so if they want to go to an outing for their kids the whole morning and then work for three hours after bedtime, they don’t have to ask anything. They don’t have to do anything. They just do it and it’s totally transparent to the rest of the team. [00:18:18] Jacob Bank: And so I think the arguments in favor of a big company are number one, if you need a fixed, guaranteed high salary in general, not always in general, that’s likely to come from a big company. If you want to be able to turn off 100% for a very long period of time, that might be easier at a big company. Most of the people that I work with don’t want to turn off 100% for a very long period of time, at least not the ones who are really committed to their work. They want to be able to go to the kids’ play, they want to be able to go to the soccer game, but they’re totally fine coming back online for an hour after bedtime to check on what they missed. At least those are the kinds of people we attract into our company. If you’re the kind of person who wants to go on a month long zero computer vacation, then yeah, probably a startup is not a great fit for you, though you might be surprised. Basically every other factor is in favor of a startup. Other than those two things, I think there’s this huge myth about stability of big companies. There’s this huge myth about how safe big companies are. There’s this huge myth about how a bigger team makes it easier for any one person to be flexible. I think that’s all garbage. [00:19:28] Adam Fishman: Yeah. Well, and lately it seems like the biggest amount of layoffs have been coming from the big companies anyways. [00:19:33] Jacob Bank: Totally. What is a safer company? A 10 person, fast growing profitable startup with a super committed founder or a 200,000 person company that has said they’re at max employment, Microsoft and Google have said they’re at max employment ever. I think Microsoft specifically has said, I don’t dunno if Google has explicitly said it, that they’re going to do rolling layouts by some criteria that you don’t understand what’s safer. We have this huge misconception around what’s safe and what’s not, but the only thing that’s safe, no job is safe. No job is safe. The only thing that’s safe is if you build up a network, a package of skills and experiences that make you always valuable at a wide variety of companies. That’s the only thing that’s safe. Relay’s not safe, Google’s not safe. Open AI is not safe, nowhere is safe. The only thing that’s safe is you and the skills and network that you’ve built up. [00:20:25] Adam Fishman: In a minute I want to come back to, you’ve mentioned having a bunch of AI agents that are doing a lot of stuff to turbocharge your 10 person team. I want to come back to hearing about what you do as a dad with AI to kind of make your life more efficient. But before that, I wanted to ask a bit about support structures and things that you have in place. One of the things you’ve talked about is obviously flexibility, so flexibility’s underrated, but you tend to put a big weight on it. As a dad, your wife’s career is a lot less flexible. Pediatrician got to be there when you got to be there as a child of a doctor, I know exactly what that’s like. You don’t have to work a lot of after hours, but nine to five you got to be somewhere. So I’m curious about what sort of support structures you and your wife have had to put into place at home to enable startup dad, founder, working out of the home, pediatrician, mom, you got three kids, they’re all pretty young. I think your oldest is what, five or something like that? [00:21:26] Jacob Bank: My oldest is almost six, so [00:21:28] Adam Fishman: Five, almost six. So you’ve barely got a school age kid there. And so what do you guys do to kind of support the household? [00:21:35] Jacob Bank: For the first two kids, they were in a daycare Monday through Friday from like eight-ish to five 30 ish. Now we have a nanny that helps with the third kid and I can talk about the daycare versus nanny decision if that would be interesting and why we went nanny there. And so she’s fully occupied with the baby while my wife is working. And then critically, she can also cover if one of the kids gets sent home sick. We did not hire her to handle all three kids all the time. Her job is the baby, but if the three-year-old is sick for an afternoon, she can flex to that. So that’s a core support in the support system. And other than that, I would say her parents live about 45 minutes away. My parents live across the country, but come out every three months or so. [00:22:22] Jacob Bank: But I think the way we’ve architected, and I think with kid number one, we were like, Ooh, our collective parents are critical supports in the structure. And then we realized as we’ve gotten more experience and as our parents have gotten a bit older, we don’t want to think of them as help anymore. We have fun, we hang out, they come over for dinner, we have fun. We go on outings together. It’s not like they’re doing childcare for us. Don’t get me wrong. That’s still an extremely big support of like, oh, we can do this fun thing for the kids. We have a bunch of other friends at the same age. The big breakthrough that has come up recently is because our oldest daughter is school age now and we have some friends in the neighborhood. She goes to the local public school. We are starting to get some economies of scale with other parents like shared carpooling to activities. [00:23:10] Jacob Bank: We can do the drop off play date now where it’s like, yeah, I’m just going to ship my kid over to your house or vice versa for a couple hours. So that’s been a big unlock at age six. It’s amazing how big of a difference it is if you only have to do half the dropoffs at swimming instead of all the dropoffs at swimming. So that’s basically our plan. We cover our core. We have a nanny who helps us with the baby. Then we have lots of family and friends that are nearby that we hang out with, and then a few close friends of kids that we can lean on for these extra either logistical moments or an afternoon here or there. [00:23:45] Adam Fishman: And the logistics get a lot easier when you don’t have to strap a kid into one of those fully immobilized car seats. You could use the booster or something instead carpooling. [00:23:54] Jacob Bank: Well, the other big gadget that we discovered recently that you may know about was the rider safe vest. Have you heard of these? [00:24:00] Adam Fishman: I have heard of this, but for the people who haven’t tell us about it. Yeah, [00:24:04] Jacob Bank: So they look just like a life jacket, like a life vest basically. And they have a couple clips on them. They look like a life vest, and the way they’re designed is that they play the same role as a booster seat in preventing the seatbelt from going around the neck, which is the big reason that you’re not supposed to put a kid in the backseat with a seatbelt because basically through the life vest, they have a set of metal clips that ensures that a normal seatbelt is positioned appropriately on a small child. What this means is that you don’t need a car seat or a booster seat at all. You just need this portable life vest that’s the same size as a jacket you throw into a backpack or something and they can now ride in any car. We do still have the car seats available. [00:24:46] Jacob Bank: They’re a little more convenient if we’re just getting into our own car, but we always have two of these vests available so that if we need to throw another kid in the car or we are traveling or something, it’s been huge. For example, if my wife is taking one kid to a birthday party across town and wants to get in a Waymo, it’s like you’re not going to bring the giant car seat in the Waymo. You’re not even really able to bring the inflatable booster seat in the Waymo, but this little vest thing that you can then just put into a bag afterwards has been amazing. That’s a gadget I would highly recommend investing in. [00:25:16] Adam Fishman: Okay. Okay, cool. [00:25:18] Jacob Bank: Not endorsed. I’m not endorsed. No affiliate link here. [00:25:22] Adam Fishman: Yeah, maybe we’ll get them as a sponsorship on this episode, but we had another version of that that was more for traveling, but it was basically a device that moved the seatbelt into the proper position without having to have a booster that you sat on. So [00:25:36] Jacob Bank: Yeah, just anything. Just the amount of stuff that you have to carry is huge. [00:25:40] Adam Fishman: Yes, yes. There’s a question I like to ask folks, but I haven’t asked of a lot of guests lately. When you think all the way back to becoming a dad for the first time, what’s the earliest memory that you have of becoming a dad? [00:25:53] Jacob Bank: The earliest, earliest memory, I remember the birth experience extremely well. I remember the pizza that we had immediately after. I remember all that, but I didn’t really feel like a dad yet at that point, if that makes sense. It hadn’t sunk in for me. The real thing was going home from the hospital for the first time, our eldest had some dehydration issues, so she ended up staying in the NICU for an extra night and in the NICU there was basically a round the clock nurse that was available and she was having trouble breastfeeding. So we had this around the clock care who was teaching us everything. And it helped that my wife is a pediatrician, but still we’ve never been fully responsible. And I was like, you leave the hospital. You’re like, I just have this kid now. Well, not only are there all the things you don’t know how to do about how do I feed it, how do I change the diaper, how do I put them to sleep? [00:26:40] Jacob Bank: When do they nap? How do I do that? It’s also the feeling that’s like I can’t just go other places anymore. There was still a period of time where we were early in our cohort to have kids, and so we’d still get these texts from friends that are like, Hey, want to come to this bar at nine o’clock? And I’m like, in what world could I go to a bar at nine o’clock? I have a child. And so that was the big moment where it was just like, and that’s why kids two and three haven’t been nearly the same change because from zero to one we made the huge change to our lives. Our schedule changed, our feeling of freedom. Everything changed with kid one and then kids two and three is just more of the same, more. It’s just more of it. But that was the big one, going home from the hospital thinking like, wow, I no longer have any control over what I do in my life. Everything is governed by this little being. [00:27:31] Adam Fishman: Yeah. Oh man. And so I want to come back to the thing that you mentioned earlier about your first two kids went to daycare, now you have a nanny for the third one. And you mentioned there was some calculus there and some decision making. So I think this is probably a topic that a lot of people wrestle with, probably a lot of people who are listening to this show. So how did you and your wife think about you’ve had sort of both, what was the reasoning behind doing both of these things or doing something different? This time around [00:27:58] Jacob Bank: Our families has strong opinions. We read the Emily Oster books crib sheet and stuff, which I’m sure folks have read. And all the conclusion is basically it doesn’t matter. There’s no massively statistically significant argument in favor of either. I was pretty strongly on team daycare at the beginning for a couple reasons, and I think we both were actually. One was I just like the comfort of an institution. I drop the kid off there, there’s going to be someone there every day, they’re going to send an invoice that I pay with my bank account. They have hours that they’re open. It’s just like it’s an institution that you plug into. That for me was a huge, huge benefit with a nanny. It’s a whole other world to figure out what are the hours, how are you going to pay, how are you going to do vacation, what are the responsibilities? [00:28:42] Jacob Bank: What are you going to put in the contract? I was just like, sign me up for the institution. And then second, this was also during COVID and my wife was seeing a lot of patients, and it was worse during COVID who had just never interacted with other kids, two year olds who had never had any interaction. And she could immediately tell at the beginning of an appointment like, whoa, this kid has just been home with a nanny the whole time and never had interactions with other kids. And I was like, even though they’re not really playing with each other at six months old, I like the idea of having social interaction with other kids. So those are the two main factors that pushed us into daycare from the beginning with the first two, with the third, here’s why it flipped. Number one, three drop-offs, three pickups. [00:29:25] Jacob Bank: Just logistically the way it works, our two kids are in different schools and there’s no option for the baby to be in either. So three pickups, three drop-offs is logistically extremely chaotic. Second, if any one of the three kids is sick, there’s no give in the system. And in a typical respiratory season, one of the three kids is going to be sick a lot. And that would’ve all really fallen on me to adapt around my work schedule. Maybe I could ask my mother-in-law to come up sometimes, but again, I don’t want to over burn her. She also has another grandkid, whatever. And so those were the two things that tipped me, three pickups through drop and most important flexibility if there is an illness. And then we had to figure out all the logistics of how do you write the contract? What’s a fair amount to pay? [00:30:08] Jacob Bank: For me, it was really important that we pay over the table with taxes and benefits and all that stuff, which is not the norm in most places that I’m aware of. And then how do we find the right person and all that? And luckily we fell into the right person, and this is how it always happens for people. It’s like another family in our neighborhoods. Kids was aging out of the nanny and going to preschool and they live one block away. And so we found a great person in that way. So I would still basically, I wouldn’t do anything differently. First one, I would still definitely do daycare. Second one, I would still definitely do daycare. Third, I’m really happy that we have a nanny. [00:30:44] Adam Fishman: Yeah, the logistical aspect of it makes and the flexibility, again, kind of coming back to something that’s important for you, that makes a ton of sense because when there’s two parents, even if the two of you had to drive in opposite directions, there’s still that third kid that’s like, where does this third kid go? [00:30:59] Jacob Bank: Exactly. And just the way the schedules work out is I do pickup and drop off for both kids every day. And so add a third to that already. It’s super tight to get home from my eight 15 meeting. And so yeah, I think the overarching point of all of this is you have to design a system that acknowledges that things will go wrong, things will go wrong at work, kids will get sick. So that was, I think the problem when my wife was in residency, it was crazy. I don’t even know how we did that. She was working 80 hour weeks at the time and we just had no give, had no give in the system. And so now we’ve really tried hard to architect a system that has in software engineering, there’s security entry, there’s defense in depth, you add different layers. Now I feel like we have defense in depth where we’ve set up flexibility in multiple areas in the system such that we can digest anything that goes wrong. [00:31:47] Adam Fishman: It’s like that book anti-fragile or something like that. You’re [00:31:50] Jacob Bank: Like, exactly. You [00:31:51] Adam Fishman: Built a system that accounts for the entropy that naturally exists in life. [00:31:55] Jacob Bank: And then also it happened to correspond to our first kid was going into public school and removing that expense as the baby came along because paying for full-time childcare for three kids is pretty intense. That’s [00:32:07] Adam Fishman: A lot. That’s a lot. That’s where the Google salary really helps actually. [00:32:10] Jacob Bank: Yeah. [00:32:13] Adam Fishman: So one of the things you also mentioned in our prep for the show is you told me double dipping is an amazing tool, and I thought about that and I’m like, I don’t know what that means. I mean, I know what double dipping means in the classical sense, but what does it mean for you? [00:32:28] Jacob Bank: I don’t know that it’s a known term. It’s multitasking. But multitasking has a negative connotation where multitasking to me implies that you’re doing everything poorly. You’re trying to feed a baby and also taking a meeting and you’re doing a bad job at both things. For me, double-dipping is achieving two goals in a way that’s mutually beneficial to each of those goals. So for example, I do a lot of home chores, whether it’s laundry or cooking or mowing the lawn. I never do any of those things without a kid helping me. Now, my daughter is like, if I make dinner without letting her pull up her chair to the counter and help, she’s like, why didn’t you wait for me? Why did you do it without me? I wanted to mix to this or mix to that. And so not only am I making dinner for the family, but I’m having this bonding experience with my daughter. [00:33:13] Jacob Bank: I’m teaching her how to cook. So all household chores, perfect example, errands, my favorite part of every Saturday morning, like clockwork, me and my two daughters, we go to Costco when it opens 9:00 AM executive members at Mari. We have a whole routine around it. I’ve trained my daughters to look for when people put things in the wrong place and we have this whole fun game of, oh, wrong place, or those people didn’t put their cart back, and it’s both something I have to do. We got to get groceries, and it’s become a fun thing that we do together. So it’s not multitasking in the sense I’m not degrading the quality of each activity. Or last weekend we had to go get a birthday party gift for a friend, and I was like, oh, I’ll just throw one kid in the jogging stroller and run to the store to get a present, which is like, I get better exercise because pushing a stroller is harder than just running by myself. And B, we have this fun experience where we’re doing anything together, we point stuff out. And so that for me has been the critical technique, which is not finding ways to, not multitask, do tasks worse, but finding ways to double dip and find a task that can have a secondary benefit typically of spending quality time with one or multiple kids. [00:34:24] Adam Fishman: Yeah. It sounds like you’re also turning, what would other biases be? A mundane activity into something that is fun. It’s building a bond with your kid or kids. It’s turning it into a game. It’s playing. Find the cart that’s not back in the right spot. It’s getting exercise. It’s like all the things. So you’re right, it’s not diminishing the task itself or making you less good at it, or it’s actually making it better. It’s enhancing it in a way by [00:34:52] Jacob Bank: Doing. Lemme give you an example of triple dipping that I did this last weekend, which was awesome. So I’ve just gotten my daughter into juujitsu, which is I’ve always wanted her to do a martial art, great for discipline and body control and confidence. And I did juujitsu back when I was a kid. So I got her into it, and then I got so inspired, I was like, I should do the adult class. It’s been 20 years, but it looks like so much fun and I would love to get back into it. And so I signed up for the adult class, which is right after the kids class. So I now help out and volunteer in the kids class, which makes it way more fun for my daughter. And she listens better and the instructors really appreciative. And then when I stay after for the adult class, she eats her lunch in the little viewing area and likes watching the adult class. [00:35:33] Jacob Bank: And we have this whole bonding thing. And then one of her friends also does the class. So last weekend I was like, oh, why don’t we just have your friend also stay and you guys can play and eat lunch? And they had a blast. They were hanging out eating their lunch, watching the adult class. The other parents were super grateful. I basically took their kid off their hands for three hours doing a no screen time activity that he totally loved. That’s an example of how when you can connect all these things to click, it feels so satisfying. [00:36:03] Adam Fishman: I love that man. That is like a pro dad chess move right there. [00:36:08] Jacob Bank: And then afterwards we were going back in the car and they were like, can we do this every week? That was so much fun. And I was like, we can do it every week. It was so much fun. [00:36:18] Adam Fishman: That’s awesome. That’s awesome. Speaking of fun, I had a dad on the show not too long ago, and he’s older kids and he was significantly older, and we were talking about how do you talk to your kids about work? And he was like, ah, my kids don’t want to listen to me talk about work. They’re into their own things. They could care less, but that’s not, I’d say it’s mixed bag in terms of what I’ve heard from other dads. And you actually find it to be the complete opposite, that you love talking to your kids about work and your kids like to listen. [00:36:47] Jacob Bank: I’m so surprised to hear that because kids are so curious. They’re so curious about everything. And so I find that, especially because I work from home and sometimes they’ll be reading their book on the couch. Sometimes we like to do our work together where they read their little books or color on the couch and I’m doing my work on the computer, or sometimes they’re overhearing a live meeting that I’m happening or I teach a lot of classes for work, and they’ll be like, oh, did that customer decide to buy your product? And I’m like, oh no, they didn’t decide to buy it. She’s like, why didn’t they decide to buy it? I’m like, well, it turned out there was an it restriction. What’s it? Well, it turns out there are these people at a company that makes sure nothing dangerous happen. Well, what dangerous could happen? [00:37:28] Jacob Bank: Well, some people are worried about emails getting sent to the wrong person. What kind of wrong person? It’s fun. It’s fun little outlet. I can do this little stress relief where one of the things I find, this was always one of my management techniques pre kids is a lot of managers feel the need to insulate their teams from all problems, and the best managers bring their teams into the problem. We’re just like, yeah, I had this really frustrating meeting with a customer where I was unable to communicate this specific point to them. Often when you bring your team into it, Hey, it’s cathartic because you get it out. B, you get some rubber ducky effect and see they might help you solve it. And it’s the same with kids where the kid is just like, oh man, you’ve seem really frustrated about that call. What happened? You always tell me, turn it back at you. It’s like you always tell me to not get frustrated about stuff like that. And so I’ve just been shocked, even with a three-year-old, how mature their thoughts can be when you do bring them into things. And also how valuable. It’s to try to re-explain from the beginning why something is the way it is. Like, well, why do it departments exist? Maybe that will unlock some interesting thought in how I could frame this to the customer. [00:38:35] Adam Fishman: That’s funny. Yeah. Kids are naturally first principles thinkers because they don’t have any other principles. [00:38:41] Jacob Bank: You have to, what else are you going to start from? Yeah, [00:38:44] Adam Fishman: They have no cynicism. They have no prior knowledge, so everything is fresh. [00:38:48] Jacob Bank: That’s been one of the best. For example, when our kids go to the store and they ask for something, and my parents were always just like, no, no, no, no, no, no, no, no, no, no, no, no, no, no. And I’m bit that. I’m a bit of that too. No, lemme show you the price of that. That’s actually really expensive. Let me show you the price of that relative to the price of this. Do you think that makes sense that we would pay that for this thing rather than this for this thing? And then you see them start to apply it. They’re like, oh, yeah, that would have to be something we could only get for a birthday or something. I’m like, exactly, for a birthday or space in our house, they’ll see the giant teddy bear from Costco that’s like two a hundred pounds. [00:39:27] Jacob Bank: And I’m like, where would we put that? Help me solve this problem. Where would we put that in our house? She’s like, well, we could put it in your bed. Well, then where would I sleep? It’s often another big thing is with sweetss and candies and stuff, because I’m worried about their teeth. She’s already had a cavity in one of her teeth, and I’m just like, you were at the dentist appointment too. You heard what the dentist said. What do you think I should do in this situation? I’m kind of responsible for making sure you have healthy teeth as an adult. Do you want to be toothless? And then it’s like, I don’t know. Just in general, I found that bringing kids into the problem, not in all situations, but in almost all situations, has been very, very effective for me personally. Maybe it doesn’t work for everyone. [00:40:06] Adam Fishman: Oh, that’s cool though. And it’s very similar to your idea of double dipping where you’re bringing your kids along for the ride and whatever activity is happening. [00:40:15] Jacob Bank: Yeah, I remember hearing that of with a baby, you should always be narrating everything you’re doing just as a way of language development. But it works for older kids too, because it’s totally different if they see you distracted on your computer and not knowing what’s going on. Or you say like, oh, I’m sorry. I just need to take a moment away from reading this book because I’m dealing with this problem at work, and it’s actually really urgent. Here’s why it’s urgent. A refund request didn’t go through properly, and so they really need to get their money and I need to get help, get their money back. Let me do that for five seconds. Then I’ll come back and read the book. And then by the way, when I come back, they’re like, what’s a refund? And then we talk about that for half an hour. That’s [00:40:53] Adam Fishman: Awesome. That’s awesome. Do your kids ever end up on the camera or in one of the classes that you’re teaching or something like that? Any fun cameos that they’ve had? [00:41:01] Jacob Bank: Yeah, yeah. I try not to have that happen too often, but it does occasionally. [00:41:06] Adam Fishman: Okay, awesome. [00:41:07] Jacob Bank: Not like the famous, I mean, there’s that classic COVID one where someone is giving some very important speech and the kid comes through in the background. [00:41:14] Adam Fishman: Yeah, the B, b, C dad, that was a whole meme forever. So one of the things that I don’t get the chance to ask too many dads, because I don’t talk to that many dads that have more than one or two kids, but a lot of dads don’t talk about the kind of feelings that are associated with becoming a father for the first time or the second time or the third time. And so I’m curious, as you’ve gone through that progression and your kids are still pretty young and pretty close together, what is something that you’ve noticed about yourself through each successive kid that’s born? [00:41:48] Jacob Bank: Probably the biggest thing I’ve found myself developing is I’m such a more patient, forgiving, less judgmental person with each kid that comes along. You just have to learn how to process your frustration. I remember with kid number one, you’d run into resistance and you kind of battle it, right? You’d be like, no, get your shoes on now. No, we got to go get your shoes on now. And they’d be like, no, I want to fish my art. They get your shoes on now. I want to fish my art. Get your shoes on now. And now I’ve realized it’s just back to the point of flexibility. If we build enough flexibility, I can then be fully engaged with her for two minutes while she finishes the drawing, and then she’ll put on her shoes by herself and we’ll go out the door. And so I think the biggest thing is some combination of flexibility and patience and going with the flow might be a good way to describe it, but it’s just see where the, with three kids especially, it’s really hard to jam them all into the box that I want them to be in. [00:42:49] Jacob Bank: It’s much more about seeing how they’re all flowing and then adapting the box around it, if that makes sense. [00:42:55] Adam Fishman: Yeah, it does. Each successive kid has kind of pushed the walls of the box a little bit more [00:43:01] Jacob Bank: With tin one. There were two on one. We could of battle her into the box a little bit. Now it’s not really possible. Yeah. [00:43:09] Adam Fishman: So I want to ask you about early as very beginning of the show. You talked about the steps that you went through when thinking about going back and starting a company, and that’s what worked for you. If you’re talking to some other people who are listening to the show and they’re at a stable big company and they’re [00:43:27] Jacob Bank: Making a lot of money [00:43:29] Adam Fishman: Stable as we’ve just defined, and they’re thinking like, oh, should I go start a thing? I’m passionate about this thing, but I also am a little nervous about what that’s going to mean for starting a family. What advice would you offer to other entrepreneurs who are maybe thinking about the same thing, but they’re a few years behind you? [00:43:49] Jacob Bank: Number one, understand your family needs and your financial constraints. Number one, a startup will always take longer to get revenue than you expect at the beginning. Not always, of course, but almost always. So if you think you can get away with six months of expenses, maybe go for more like a year. If you think you can get away with a year, maybe go for more like two years. So have a very honest financial picture in mind as soon as you have a financial picture that you can tolerate. And again, try to distance yourself from the, but I’m giving up so many gains in my Vanguard portfolio. The number could be so much higher if I did blah, blah, blah. Distance yourself from that. What do you enjoy doing with your time? And do you have enough money to afford that? Do that. As soon as you’re comfortable with that, just go. Just start. People make all sorts of excuses. I’m waiting to hit this milestone, blah, blah, blah. I’m waiting for the perfect idea to hit me. I’m waiting for the perfect co-founder to be available. I’m waiting for this. I’m waiting for that. People just make endless excuses to kick the can down the road. As soon as you feel like you can financially afford to make less income or no income for some period of time, immediately go immediately, and then you’ll figure out the rest along the way. [00:45:04] Adam Fishman: Yeah, yeah. Is there anything on the flip side of that that you, in hindsight realize you were wrong about? Or you would tell them like, Hey, don’t do this thing that I did that I found to not work, or something like that? [00:45:21] Jacob Bank: Just the only thing is the thing I mentioned earlier, which is like, it’s going to take longer than you expect. [00:45:28] Jacob Bank: Yes, cursor went from zero to a billion revenue in two years. It can happen. It is possible. But almost everyone’s story, even the hyper successful story, look at two other hyper successful companies right now, clay and Gamma, if you look at the story of play, took them four years, I think, or five years to get from zero to a million in ar. Then they went from one to a hundred in two years, and they were, in this case, VC funded quite well. But that means that you’re taking either a minimal VC funded salary because you don’t raise VC money to pay yourself a huge salary. That’s not, [00:46:01] Adam Fishman: That doesn’t work well with a vc [00:46:03] Jacob Bank: Or you’re bootstrapping and taking no salary. Just be aware that it’s going to take longer. And A, that means you have to plan for it financially. But B, it means you have to digest it psychologically because it’s tough when you see the headlines of this company raised this money and this company raised that money and this company hit that milestone. It’s really tough on your psyche because in a corporate job, it’s very easy to throw your dart and then paint a target around it and say, woo, we succeeded. Yay, we did the launch. Doesn’t matter if no one’s using it. We did the launch. Everyone high fived. In a corporate environment, there are all these fake celebrations of meaningless milestones that doesn’t exist in a startup. You only get to celebrate things that are real. And so it does require a certain amount of fortitude that I would not go into lightly. [00:46:57] Adam Fishman: That’s very helpful, thank you. So you shared a framework with me, which is imagine if I did that, what would happen? Tell me about that framework. [00:47:06] Jacob Bank: Yeah, that’s my go-to parenting framework right now where if a kid, for example, is having a tantrum that they can’t get some dessert, some piece guy, he’s like, I’m just like, what would happen if I was at Trader Joe’s and they were out of the cheese I liked and I just fell down on the floor screaming and crying. Really? What would happen? She’s like, huh, well, I’ve seen any adult do that. I’m like, yeah, you’ve never seen any adult do that. And I’m like, what would happen? She’s like, what would happen? And I was like, they would probably kick me out of the store. They might have to forcibly remove me. I might get arrested for disorderly conduct. I might be banned from the store in future. I can’t do that. As adults, we don’t get to have that behavior. There’s real consequences to that behavior. [00:47:51] Jacob Bank: Everything about my parenting style is try to bridge the gap between us. We’re not living in two different worlds. Your school is not so different from my war. You wanting to get your dessert is not so different from me wanting the thing that I want at a restaurant. Our lives are not so different. And so for everything you’re going through, there’s some analogy that I experienced in my life. What if I handled it that way? What if one of my customers decided they didn’t want to pray the price out? Could I hit them in the face? What would happen? What would happen if I was in a sales call and the customer said something frustrating to me and I hit them in the face again? Really play it out. What would happen? Is that an acceptable, would that be an acceptable and worthy outcome for that? [00:48:33] Jacob Bank: No, of course not. And so that’s the whole thing, and that again, because it’s so easy when someone’s having a rolling on the floor tantrum to be like, oh man, it’s a 2-year-old having a rolling on the floor tantrum. But I’ve always found, at least for me personally, it has worked better to treat them the more they’re acting like a baby, treat them more like an adult and just bring them up to the level and then yet make it relatable. I experience things like this all the time too. Sometimes I’m late for things. Also, sometimes the clothes I want to wear today are also dirty. This stuff happens to me all the time. Do I have a screaming tantrum on the floor? No. [00:49:10] Adam Fishman: It’s funny because you’re describing that as treating them more, but what I hear in those examples is actually you’re kind of hitting them with a dose of empathy, which is like, Hey, I see that you’re upset about your clothes are dirty or they’re out of the thing. That happens to me too. I understand that feeling. And then you’re kind of changing, another dad used the term [00:49:33] Jacob Bank: Change and then here’s how an adult reacts to it. Yeah, [00:49:35] Adam Fishman: Right, exactly. And so you’re kind like, imagine what would happen if I did that, and then it kind of actually stops your kids in their tracks like, yeah, what would happen if dad, [00:49:45] Jacob Bank: Because then they really have to think about it. They’re like, what would happen? She’s like, well, I could get your laundry out of the laundry room. I’d be like, that’d be super nice, but would you [00:49:55] Adam Fishman: Love that, that you mentioned that through three kids being a dad, each one has sort of increased your patience and sort of your level of tolerance and just ability to slow down and be more flexible. Has that been the same effect on you as a leader or a founder, or have you noticed other things that becoming a dad has had an impact on when it comes to work life? [00:50:20] Jacob Bank: I mean, the biggest thing is just change of perspective about my goals. Again, I’m still very ambitious and committed the success of the company, but my version of success is different. So for example, my version of success is not having as many employees as possible. My version of success is having as few tight-knit, highly competent employees as possible because that’s going to enable me to maintain the flexibility and high quality. It’s not raise the largest amounts of venture capital so that we can have the biggest boomer bust IPO. It’s more like, well, we’re profitable and growing really quickly, and so why would we need to raise additional venture capital? Do I really want to be Mark Zuckerberg, Jeff Bezos? No, of course not. And so I think, yeah, the biggest thing has changed for me is not so much how I operate in the role, but it’s given me a lot more clarity around the kind of company I want to build and what success looks like. [00:51:18] Jacob Bank: And so I’m sure there are other successful paths Relay could take. We could be a 50 person team rather than a 10 person team right now. We could have raised a bunch more venture capital. We could have done things differently. I’m not saying those are bad or invalid ways to run a company. Many of our competitors are doing just that. It’s just not the way I want to run the company. And so I feel much more confident just saying, this is the way I’m going to run the company and feel okay about giving up alternative paths. I think that’s the thing that I’m most comfortable with. I’m okay giving up alternative paths. I just need one path to be really good. [00:51:51] Adam Fishman: Yeah. Yeah. And because this is your second time founding a company, if you rewind back to the time where you founded your first company, do you feel like you’re a very different person? Your perspective on things very different now? [00:52:04] Jacob Bank: Totally different. I mean, I think about this a lot. The difference between founding a company like 23 versus 33 or eventually 43, there’s no doubt that I was smarter then in terms of processing power, intellectual horsepower, it’s not even close. I was way smarter then. Now I have a way better network, and I’m way more experienced personally for me, I’m a way better founder this time than last time. For me, the balance has been that experience and network and discipline and efficiency has more than outweighed my drop in processing power. Maybe it depends on what kind of company you’re building. Yeah, because when I was 23, my answer was just to brute force everything. Like, oh, well, I’m 23. I have no other responsibilities. I will just stay up all night writing code. I’ll just stay up all night answering support tickets. I will just do more, do faster, do better. [00:52:58] Jacob Bank: And now that is not an option for me. One of the things that kind of, I don’t want to say it bugs me. I get it, is all these people posting on Twitter, you’re not a serious founder if you’re not grinding hard on weekends. And it’s like, yeah, of course if I was 23, I’d be grinding on weekends, which I was doing when I’m 23, but you want to hang out with my kid for 12 hours. That’s just any company who’s like, oh, we’re a 9, 9, 6 company and culture. It’s just like, well, that’s totally incompatible with having kids. And so that’s not to say that’s the wrong way to build a company. If you want to hire all 23 and 25 year olds, you can build great, great companies that way. But for me, I’m just building a different kind of company and that the key thing I try to communicate people is you can be equally intense and equally committed without having to be in a physical office from nine to nine, six days a week. [00:53:54] Adam Fishman: That makes a lot of sense. [00:53:55] Jacob Bank: For me, the intensity and the commitment is more important than the time spent because I do believe there are 10 X engineers and a hundred engineers that can do that much more with every unit of time. So I’d rather find those people [00:54:08] Adam Fishman: And have fewer of them, like you mentioned. [00:54:09] Jacob Bank: Yeah. [00:54:10] Adam Fishman: So I want to get to our AI questions, but before I do that, I want to ask you one more thing, and this is a little bit of a fun question. It’s not particularly fair because your wife is a pediatrician, but I am curious if there is still something that you and her don’t agree on when it comes to parenting. [00:54:30] Jacob Bank: We’re pretty aligned, and when we’re not, I usually defer to her the one thing that we might not be a hundred percent aligned, and it’s like physical risk will play on the playground. I’m just a little bit more comfortable with physical risk. And again, because she has to treat all these kids with the this and the that and that, she’s like, no, don’t climb on that thing and do that, or don’t put that thing in your mouth where I’m just like, eh, whatever. If they fall off the thing, they’ll learn not to fall off the thing again. That’s probably the one difference where I have a little more laissez-faire attitude about physical risk, but other than that, we’re pretty aligned. [00:54:58] Adam Fishman: She knows that the greatest breaker of arms in society is the monkey bars on the playground. So she knows. [00:55:03] Jacob Bank: Yeah, and also, for example, she sees really scary stuff, a kid who fell out of a non-child proof window, and you can imagine what happened falling from a second story. And so again, she’s right in our area of misalignment. She’s totally right. It’s just like I don’t have that same experience or instinct. Yeah. [00:55:22] Adam Fishman: Yeah. I love that. And I also love that you made sure to say that she was right there, which she is. Let’s be honest. So let’s talk about AI stuff. So first tell me, I didn’t get a chance to listen to you talking about this with Ben, but tell me what have you done with AI to make your parenting life easier? [00:55:40] Jacob Bank: So this is kind of a funny thing where I use a ton of AI and technology at work, but very little, very little in my personal life. The one example is, again, in the same spirit of letting kids follow thread. Like yesterday we were reading, we listened to the audio book in the car of Little House on the Prairie, and she was super curious about, well, how long would it have taken to go from here to there in a wagon and why did they have to do it? Why did they have to build the house that way and where’s the real thing? And in the olden days, you have to string together a bunch of Google searches, where now literally I go to CHA two T and I’m just like, my five-year-old daughter is really interested in understanding the deeper backstory, little house on the prairie. She’s specifically interested in these things. Can you help us with that? And then we’ll just follow the thread and use that as our interface for exploring a topic. That’s the one. But honestly, other than that, I do not use AI very much in my personal, occasionally yell for travel planning, I’ll use cha BT instead of a traditional Google search, but I don’t think I have anything particularly interesting to share. [00:56:45] Adam Fishman: That’s okay. And still your use is somewhat similar to how I’ve started using it with my older kids, which is like, we’ll put it on in the car on voice mode and talk about a thing that we are curious about the history of something or whatever. And because it comes through my Bluetooth and my speakers now, my son thinks that we’re actually talking to a real person a lot of the time. He’s like, was that somebody on the phone that you were talking to? I’m like, no, no, no. That’s ai that’s on my phone. It’s not somebody we’re calling. [00:57:14] Jacob Bank: And it’s crazy how not just tech native, but AI native, this generation is going to be like they’re living in a totally different world. [00:57:22] Adam Fishman: Spoken commands are going to kind of be the default, I think, for kids. So that’s actually a really good segue because when you think about, obviously you built an entire career in technology, you use it a little bit at home, but a lot professionally. What is the relationship that you want your kids to have with technology as they get older? [00:57:40] Jacob Bank: Maybe I’ll separate this into childhood and then in their careers, and it’s so hard to predict because what is AI going to look like in general in childhood, as much as possible, I want them to have real life experiences that are not on screens out of nature or whatever. I think that’s pretty common these days. But on the other hand, I want them to become fluent in all the tools that are available to them. And so I don’t know that it’s that different. In principle from graphing calculators, when we were in high school, I really respected the teachers who were like, I know you have a graphic calculator can do this, but here’s why I’m teaching you how to do it by hand. I’m teaching you to do it by hand so that you have intuition about how it works and why it works. And I’m not saying I’m going to have them code a transformer from scratch, but I do think you can use the AI tool with an understanding of here’s how a large language model takes in a prompt and produces a response, and here’s how you think about what context it has, and here’s how you can model this, and you should be able to still write a high quality essay long form. [00:58:47] Jacob Bank: You should still be able to do these math problems by self, but you should also know how to do them with the tool. I think it’s just you got to be an expert in both. You have to be an expert in doing without the tool when relevant to build intuition, of course, there’s a line, most programmers don’t know how to write assembly anymore. So there’s a line where at some point the higher level abstraction of the tool becomes enough that you don’t need to learn the lower level version. But yeah, in general, I think the big thing is that I’m worried about is, and I was always worried about this myself in school too, is there’s so much pressure to get grades and get the right answer on the test, that it’s very easy to just shortcut your way there where it’s like, oh, I’m just going to pattern match based on this exact problem in the book, and I know it looks like that. So I stick that number in here and I would way rather my kids get a lower score on the test, but have more deep intuition about how the thing works. And so that’s a general thing. I think that’s going to be relevant in the age of ai. Again, my kids are too young for me to know exactly how to apply that yet. [00:59:44] Adam Fishman: Yeah, no, that makes a lot of sense. Before we wrap up and get to lightning round, two final questions for you. One is, what is one thing that you’re really looking forward to doing with your kids this year? [00:59:56] Jacob Bank: I am most looking forward to spring break. We are going to San Diego and we’re going to go to Legoland. And I was super into Lego as a kid in those days. I didn’t have the sets, it was just the blocks. And now my kids are super into it, and I’ve never been to Legoland myself. And so I’ve heard from everyone. It’s amazing. And so I’m very, very excited for that [01:00:21] Adam Fishman: As someone who has been to Legoland a couple of times with my kids, the first time being when they were about the same age as yours, it is very fun. You will love it. I’m excited for you. So [01:00:32] Jacob Bank: Yeah, I think I’ll probably have more fun than the kids do, but we’ll see. [01:00:35] Adam Fishman: Okay, cool. And my last question is how can people follow along or be helpful to you? [01:00:40] Jacob Bank: So professionally, I work on Relay.app, which is a product that helps people build AI agents that help them get their work done. I post a ton on LinkedIn about specific AI agents that I’m using or building or working with customers on. That’s probably the best way to follow along what I’m up to. And I also teach a bunch of live classes. I teach ’em free ones, I teach some paid ones. But if you are wondering how to use AI productively in your work, I hope I can teach you something valuable. [01:01:06] Adam Fishman: Cool. I might have to take one of those classes. I’m always, always [01:01:09] Jacob Bank: Excited. People seem to like ‘em and I love teaching them. It’s super fun because there’s so much fun, so much hype that it’s really satisfying to just show people like, no, this is an actual thing. I know it works. I know it works, so I use it myself. Here’s exactly how to do it and why to do it. It’s very satisfying. [01:01:25] Adam Fishman: Awesome, awesome. Alright, well we will send everybody to your LinkedIn and to Relay.app, so Okay. Rapid fire. Lightning round time. Are you ready? [01:01:35] Jacob Bank: I’m ready. [01:01:35] Adam Fishman: That’s good. Okay. [01:01:35] Adam Fishman: What is the most indispensable parenting product you've ever purchased? [01:01:40] Jacob Bank: I think it's the rider. Say fest, Thery. Say fest. [01:01:42] Adam Fishman: Yes. What is the most useless parenting product you've ever purchased? [01:01:47] Jacob Bank: The green light, red light wake up thing. You know that thing where like you're sleep training the toddler and you're like, oh, if it's red, stay asleep and if it's green you wake up. That shit did not work for us at all. Like 0% success rate. [01:01:59] Adam Fishman: Yes. That's awesome. Okay. What is the weirdest thing you've ever found in your kids' pockets or in the washing machine? [01:02:06] Jacob Bank: Oh, it's gotta be like necklaces made of various breakfast cereals, like in various states of disintegration. [01:02:12] Adam Fishman: Mush. Yeah. [01:02:14] Jacob Bank: Yeah, [01:02:14] Adam Fishman: or false? There's only one correct way to load the dishwasher. [01:02:18] Jacob Bank: true. Very true. Very, very true. [01:02:20] Adam Fishman: is, do your wife and you share [01:02:21] Jacob Bank: Me, me, me, me. I load the dishwasher. I, if, if I see someone else has put something in, I rearrange it. [01:02:29] Adam Fishman: Oh man. After my own heart. what is your signature? Dad's superpower. [01:02:34] Jacob Bank: I think it's taking kids to grocery stores. [01:02:37] Jacob Bank: Like [01:02:38] Jacob Bank: taking, taking kids to grocery stores. Like most people. Treat it as like a really painful, annoying chore. I absolutely love it. [01:02:45] Adam Fishman: Yes. Okay. 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 [01:02:52] Jacob Bank: Night, night, night night. Yeah. Bedtime [01:02:55] Jacob Bank: dinner, bed, bath. Yeah. [01:02:57] Adam Fishman: Yeah, just the, just that trifecta of craziness. [01:03:00] Jacob Bank: yeah. [01:03:00] Adam Fishman: If your kids had to describe you in one word, what would it be? [01:03:04] Jacob Bank: Uh, I don't know that they'd say anything very particularly nice. Probably loud. They would probably say loud. [01:03:12] Adam Fishman: My kids might say the same thing about me. [01:03:14] Adam Fishman: what is the funniest thing that one of your kids has ever said in public? [01:03:20] Jacob Bank: It was also at the grocery store. I, um, I was getting like a piece of yo a, jar of yogurt out of a shelf and I drop it and it splattered. And I was O-S-H-I-T and then my daughter was like one and a half at the time. And so she was just like, we were incarcerated. She's like, oh shit. Oh shit. Oh shit. And I was like, yes, the ocean is beautiful. [01:03:44] Jacob Bank: Like, [01:03:45] Adam Fishman: That's funny. That's funny. My daughter once at a very young age, somehow learned the F word, [01:03:51] Jacob Bank: yeah, [01:03:51] Adam Fishman: at, the playground or something from an older kid. And so we had to like redirect her doing the exact same technique and it [01:03:59] Jacob Bank: yeah, [01:04:00] Adam Fishman: So, [01:04:00] Jacob Bank: yeah. yeah. [01:04:01] Adam Fishman: how many dad jokes do you tell on average in a given day? [01:04:05] Jacob Bank: eh, about three, probably three. [01:04:07] Adam Fishman: a good number. Hopefully that number goes up over [01:04:09] Jacob Bank: Yeah. Yeah. A solid three. [01:04:12] Adam Fishman: What is, uh, the most absurd thing that one of your kids has ever asked you to buy for them? [01:04:17] Jacob Bank: So we were on a walk, by the marina in San Francisco where people have all their super fancy yachts, and she's like, those boats look cool. Can we buy a boat? I'm like, oh my God, that boat costs like five times what our house costs. No. And she's like, oh, could we rent a boat? And I'm like, we could ride on a boat. [01:04:38] Adam Fishman: Right. Right. That's awesome. what is the most difficult kids TV show that you've ever had to sit through? [01:04:46] Jacob Bank: Coco Mellon. I can't stand Coco Mellon. It's not a, I know it's not a show. It's like a, it's a, it's an empire now, but those little bobbing faces, like, I cannot stand Coco Melon. [01:04:56] Adam Fishman: Coco Mellon is the number one most difficult show as quoted on this program. So [01:05:01] Jacob Bank: Yeah, it's horrible. It's like it should be illegal, [01:05:04] Adam Fishman: Yeah. On the flip side, what is your favorite kid's movie? [01:05:08] Jacob Bank: We don't watch many movies. TV show would definitely be bluey. I would watch Bluey by myself for fun. That show's amazing. The only movie we've watched, which we did like a lot, was Leo, the Adam Sandler. Bill Burr won. Uh, it was really good. [01:05:20] Adam Fishman: Okay. Only a couple left here. What, um, nostalgic movie can you not wait to force your kids to watch with you? [01:05:27] Jacob Bank: I guess I have to think about what age, what age group? Probably the Matrix. Probably the Matrix, like when they're in high school or something. [01:05:34] Adam Fishman: Yeah. Okay, cool. have you started to tell your kids any back in my day stories, [01:05:41] Jacob Bank: Every day, at least five. [01:05:42] Adam Fishman: is your favorite one that you like to tell them? [01:05:45] Jacob Bank: The one that comes up the most often is that whatever was on the tv, you just had to watch that. Because like, you know, we, we let them pick one show to watch before bedtime and they sometimes they have to agree. The two have to agree before we can watch, you know, whatever the seven or 15 minute show, I'm like, back in my day we just watched whatever was on. [01:06:07] Adam Fishman: And it was the news. [01:06:09] Jacob Bank: Yeah. And whatever it was, that's what we were all watching. [01:06:13] Adam Fishman: Okay. What is your favorite dad hack for road trips or flights? [01:06:18] Jacob Bank: Audio books. Audio books. Yeah. [01:06:20] Adam Fishman: And finally, you've got three kids, but you do, I think, live in San Francisco. What is your take on minivans? [01:06:28] Jacob Bank: We have a minivan. I'm 100% pro minivan. [01:06:31] Adam Fishman: all right. [01:06:32] Jacob Bank: our two vehicles very San Francisco are. The cargo bike, the e-bike, which is my main vehicle for getting the kids to and from school, and then the minivan for road trips and for Costco. [01:06:44] Adam Fishman: Okay. you go. There you go. All right, team. We got another vote for team minivan. I love [01:06:49] Jacob Bank: Yeah, [01:06:50] Adam Fishman: Uh, the only way. It's the only way with three kids, [01:06:53] Adam Fishman: that that is, that is true. it is also true as I've been looking at the data around this show that most often you have to have three kids before the minivan starts to tip into [01:07:03] Jacob Bank: right? [01:07:04] Jacob Bank: Yep, yep, yep. I agree with that too. [01:07:06] Adam Fishman: Well, Jacob, it has been my absolute pleasure having you on this program today. Thanks for joining me, and I wish you and your family all the best for, uh, 2026. [01:07:17] Jacob Bank: Thanks so much, and to you as well. [01:07:19] Adam Fishman: Thank you for listening to today's episode with Jacob Bank. You can subscribe and watch the show on YouTube or wherever you get your podcasts. [01:07:27] Adam Fishman: Visit www.startupdadpod.com to learn more and browse past episodes. Thanks for listening, and see you next week.