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Adam Fishman (author of a top business newsletter on Substack with 11K+ subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. They discuss the tough aspects of work, parenting, family, the mistakes made and lessons learned along the way. All episodes at www.startupdadpod.com.
[00:00:00] Rex Gelb: It’s a great saying from a good friend of mine, never deprive them of a struggle. And he also has a one year old, but we are starting to kind of try to work on this early because I actually think it’s something that I’m going to struggle with because I already can’t stand to watch her struggle. It’s so hard for me. But I know if I step in too much and don’t let her do her thing, I’m going to undermine her confidence. And I think that that potentially can start happening now.
[00:00:26] 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. Today, I am pleased to host a longtime Startup Dad listener who recently had his first kid and started his own company. After over 11 years at HubSpot and becoming their head of paid media, Rex Gelb left the day he was coming back from parental leave to start his new company, Summit Chase. In fact, he and his wife both quit their jobs within 24 hours of each other. He now leads Summit Chase with a growing team and as a husband and dad to a daughter who recently turned one. Rex and I discussed what it was like for him and his wife to quit on the same day and why it made sense for them. A concept he learned from a past manager that the sooner you give up, the better.
[00:01:23] Adam Fishman: And why that strange advice has been quite helpful for him. The most surprising aspects of having a newborn, how to navigate late night sleep deprived arguments with your spouse and a whole host of helpful household processes that he and his wife practice together. 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. I hope you enjoy today’s conversation with Rex Gelb. Today is a very special full circle moment here on Startup Dad because I am very excited to welcome Startup Dad’s super fan, Rex Gelb, as a guest. So Rex, thank you for joining me today.
[00:02:07] Rex Gelb: Stoked to be here.
[00:02:09] Adam Fishman: And because I said that you were a super fan, I think, and I think you agree that the story of how you became a guest on the show is pretty fun. So why don’t we do that first? How did you become a guest on this show?
[00:02:26] Rex Gelb: Yeah, I agree. It is a cool story. So you and I are in the same Slack community and when you were first getting going with the show, you would post links to different episodes and be like, “Hey, check out this cool person that I just talked to on this cool topic.” And I’ve always been interested in startups and I knew I wanted to be a dad one day. So I would check them out here and there just in passing. And then when my wife became pregnant, I remembered you and I went back and I downloaded 15 episodes and just kind of started binge listening. It was great. And then December rolled around and I saw my Spotify Wrapped. And sure enough, number one on podcast, Startup Dad, and I sent you a screenshot just to say thanks for a great show. And you graciously said, “Why don’t we get you on?”
[00:03:12] Rex Gelb: And here we are.
[00:03:14] Adam Fishman: Awesome. Love that. Full circle. You went from dad adjacent to dad expecting to full on dad to guest on the show. So that is the lifecycle progression that we are trying to go through here for a Startup Dad listener. So for those out there who are listening, you too could be a Startup Dad guest someday if you just play your cards right. But no, I say that in jest, Rex, but I’m very excited to have you on. When this episode drops, you will have just crossed the one year mark with your daughter. So she’s about nine months old right now and her name is Skylar. And before we talk about what it’s been like having a kid, I want to go back in time to shortly before or shortly after she was born. And that is, you and your wife both gave notice and quit your jobs at the exact same time and it was right after coming back from parental leave.
[00:04:12] Adam Fishman: So you had a newborn at home, you were starting to bootstrap your own business, which is what you do now. And I would not describe that decision as conventional wisdom. So why did that make sense for the two of you to take that action and both ride off into the sunset of your jobs with a new dependent and maybe not a full plan?
[00:04:36] Rex Gelb: Yes. Definitely not conventional wisdom and not necessarily something that I would recommend to the average family, even though it did make sense and I think work out for us. But for me, I’ve always been super interested in startups. And my background is I joined HubSpot about 10, 11 years ago as their first paid media marketer. And ever since I joined, I knew I wanted to do a startup one day and I stayed a lot longer than I originally anticipated. But you know how these things go. I got super lucky with HubSpot and was just having so much fun and it never really felt like the right time to leave. And then once I had my daughter, it’s like, there’s never really a great time to do this, but it doesn’t seem to be getting any better. I’m taking on all of this. There’s so many responsibilities and obligations in my future and I don’t really want to be in the thick of startup life when I have a toddler or maybe multiple toddlers at home.
[00:05:30] Rex Gelb: So there’s never an amazing time. But I kind of was like, now’s a pretty good time to do it relatively speaking. And I spoke with my wife and she was very supportive. And she was kind of like, “Yeah, from my perspective, I’m also not really necessarily ready to go back to work just yet.” So we made this plan where I would leave my job and try to get the business going and she’d leave her job and take care of the kid at least for now. So we decided to do that towards the end of parental leave. And it was exciting because at the end of parental leave, we’re doing role play with each other, practicing our quitting conversations with our boss. And then we came back and within 24 hours, we had both left our jobs, which we loved and we were at for a really long time.
[00:06:13] Rex Gelb: Yeah, not conventional wisdom, but it was fun and it made sense for us.
[00:06:17] Adam Fishman: I love that the two of you role played the quitting conversations with each other. Was anyone like the bad cop? Were either of you adversarial like, “What do you mean you’re quitting?”
[00:06:27] Rex Gelb: No, I mean, we knew it would be fine. You’ve probably quit a job before, especially when you’ve been there for a long time, there’s the sense that you’re letting people down and they’re counting on you. And it’s a tough thing to do. It went over very well for both of us. Everyone was supportive at work, but it’s still something, at least for me, I was going to practice.
[00:06:47] Adam Fishman: So when the two of you put in your notice, well, I don’t know if it was remote or if it was in person, but if you did that, did you come home and you just look at each other across the table and you’re like, “Well, it’s done now. What did we get ourselves into?”
[00:07:01] Rex Gelb: It was a little less dramatic than that. We were both remote and I think she did it on a Monday and I did it on a Tuesday. So it wasn’t literally at the same time, but it was definitely kind of crazy.
[00:07:11] Adam Fishman: Yeah. Wow. Well, you have way more gumption than I have in that regard. So kudos for doing something so brave and also terrifying. You’ve got a whole bunch of parenting principles and processes that you’ve sort of developed over the last, let’s say, nine months and we’re going to talk about those eventually. But there’s a thing that I want to discuss with you before that, which is something that I don’t think across 130 some episodes we’ve ever really put on the table in this conversation. And this is related to partnership, so with your spouse, significant other. So I want to get to that too, but I think there’s one more thing that we’re going to talk about before that. And that is when you first had your daughter, before you quit your jobs, before you were like, “I’m going to go do this thing, bootstrap my company.” Did you know when she was born or before she was born that at some point you were going to go build a company and that that was going to happen in the next year or so?
[00:08:15] Rex Gelb: I think I knew that 10 years ago, but nothing had changed when I first had my daughter. So when I first had my daughter for several months, I still had every intention of going back to work and continuing down that path. It wasn’t until a couple months into leave that I kind of started nagging at me and then I started taking it more seriously and then talking about it with my wife. And really it wasn’t until the final weeks of leave where we had solidified that decision.
[00:08:44] Adam Fishman: Yeah. So you had a manager that told you something, which was a quote that I didn’t really make sense when you told this to me. So I want you to explain that. And I don’t know if this quote is related to work or parenting or both, but the quote is, “The sooner you give up, the better.” So it’s sort of strange advice, I think, on its surface, but you’ve kind of reframed this or rephrased this into a belief that basically this is about letting yourself change and notice some things and sort of letting things go and coming up with new things. So can you tell me more about this concept of giving up?
[00:09:26] Rex Gelb: Yeah, this was from my manager’s manager, and I’m sure he will let me know if I misinterpreted this because honestly at the time I didn’t really understand it either. And I just kind of nodded along and I was like, “Oh, okay.” But yeah, he said, “The sooner you give up, the better.” And now that I’ve had a kid, I think I do understand what he meant by that. So before having a kid, I used to see my friends all the time. I would play pickleball three nights a week, I’d travel, I’d go skiing, I’d go camping. And when you first have a kid, I was trying to do these things. I was trying to continue playing pickleball three to four nights a week and seeing my friends all of the time and doing fun things every weekend. And it just became very stressful to try to do all of that stuff on top of all of my new responsibilities.
[00:10:12] Rex Gelb: And the sooner I came to terms with the fact that I wasn’t going to be seeing my friends as much and I wasn’t going to be traveling as much and doing all of that fun stuff, it did kind of become easier. And so yeah, I would maybe reframe it as let yourself change because I think the sooner you give up, the better. It sounds like a little sad when you put it like that, but I think it’s not sad. I think it’s like a trade that myself and most dads are very comfortable with and are very happy about. And my pickleball career, probably never going pro and I’m going to have to come to terms with that, but I’ve got all this other great stuff now and I think it’s a good thing.
[00:10:50] Adam Fishman: If it’s any consolation, my dad is in his 70s and is an avid pickleball player now. So you could come full circle on this many decades into the future. So when your daughter’s fully grown and you too are a grandparent at some point. So the interesting thing about what you just said, this idea of letting some things go, and you actually pointed this out to me. It reminds me of this conversation that I had back in October of I think 2024, so a couple years ago of doing Startup Dad, this conversation with a guy named Rob Taylor, and Rob talked about what he calls fighting off the should gremlins, like you should do this and you should do that. Can you talk about for you what some of those should gremlins are and maybe even what they continue to be, and then what you had to do to convince yourself or get yourself in the frame of mind to fight them off.
[00:11:46] Rex Gelb: Yeah, that was such a good episode. I still think about that episode to this day all the time. I think it’s a really good insight. And pretty much what he talked about is he was like, “There’s so many things you should be doing all of the time. You should be sleeping eight hours a night, of course. You should be exercising four or five times a week. Of course, you should be working hard and making sure you have financial stability, of course. You should be blocking off 5:30 to 8:00 PM or whatever it is to hang out with your family. Of course.” All of these things, of course, these are really important things, but you start doing the math and adding all of these things up and it doesn’t work. You can’t actually do all of these things. So you end up having to borrow from different categories at different times and sometimes borrow pretty heavily.
[00:12:35] Rex Gelb: And the result of that is you do frequently just feel like if you’re working at 7:30, like, “Oh, I should be doing family time,” or if you’re not exercising, “I really should be exercising this week.” So it is hard. In terms of how I fight them off, I’m not sure I have a great answer to that yet. I think I’ve gotten a little better at dealing with it. I’m just out here like everyone else does just try to do my best. And I think that a lot of dads probably wrestle with this and it’s probably not productive to beat yourself up too bad about it. So just trying to do my best and move on and know that in the long run, hopefully all of these categories do even out.
[00:13:16] Adam Fishman: Yeah. The arc of time bends towards the truth over a very long period of time. I guess one of the things on that topic, certainly if you want to stop playing pickleball, the only person you really have to tell that is yourself and maybe your pickleball partner or people who are expecting to see you there. But if there’s things like, “I really should be home with the family, but actually tonight I have to do this other thing. I have to work or part of building a business is like, I also should be doing this.” Is that something that you and your wife had to … Were you openly talking about that? How did the two of you get on the same page when some of those should gremlins are actually things that are going to keep you from maximizing family time? Because you said it’s important to spend as much as you can, but nobody’s perfect.
[00:14:07] Adam Fishman: You can’t maximize it 100% of the time. So how did you two get on the same page around that?
[00:14:13] Rex Gelb: Yeah. So this is something that is an active conversation that we’re having a lot, kind of like work life balance and what that looks like for us and what we think about, how we want to lead by example with Skylar. I think there are things we know and there are things we’re still figuring out. So one thing that we know is it is not okay to be a completely absentee parent for a long period of time. You have to be around, you have to be around when your family needs you. For sure, we know that. We also know that five or 10 years ago, this concept of hustle culture started coming out and somehow working hard became like it had a bad connotation with it. And I think that me and my wife do not subscribe to that. I think that we were raised … Actually, there’s nothing wrong with working hard.
[00:15:05] Rex Gelb: In fact, working hard is a good thing. And I think that’s how we were raised and that’s how we intend to raise our daughter. And the other thing is there are going to be times in her life when she’s going to have to do something really, really hard. And in my experience, the best way to do that is to wake up at 5:00 AM with a big pot of coffee and saddle up and get to work and get it done. It might not be starting a business. It probably won’t. I feel like most people aren’t like me, but it might be like she wants to run a triathlon or she wants to be amazing at guitar or whatever it is. And I’m okay with her watching what I do for a three month period if I have to do something really hard and then she’s like, okay, this is okay to do that.
[00:15:49] Rex Gelb: And I think that my wife and I agree that that is something that even though the tradeoff is like, I’m not around, it’s like actually potentially a good thing for short periods of time, not for her whole life. I mean, to answer your question, we talk about this topic all the time because I am working. It’s getting a lot more fun now, but at the beginning of the business, there was a 10 week period that was just crazy, crazy intense. So we’re still figuring out what that means to us, but it is definitely a big area of conversation.
[00:16:18] Adam Fishman: Yeah. What I’ve found too is as your kids get older, it’s a little bit easier to talk to them about what hard work means and say like, “Well, I’m doing this thing and it’s because of this thing and this is what it takes.” And it’s not a forever thing, it’s temporary. But then, I mean, my kids are older, but I find when I have that conversation with them, it’s very hard to have to leave or go somewhere or not be home or something like that. I don’t want to do those things, but they’re kind of important and necessary. Kids are actually surprisingly receptive to that, I found. Now obviously a nine month old, not going to understand, not having an academic conversation with her about hard work, but as she gets older, for sure.
[00:17:04] Rex Gelb: Yeah. And maybe my point of view will change on this over time when my kids are at different ages. Right now, it’s easy for me to say that because she doesn’t know what’s going on, but I hear you.
[00:17:13] Adam Fishman: Right. What’s been the most surprising thing that you found in the first few months of having a newborn?
[00:17:20] Rex Gelb: When I thought about having a baby, I was thinking about having a giggly, smiley, playful baby crawling around and I knew this, but a newborn is not that. A newborn is like, they are a blob. Let’s call a spade a spade. They are a blob for three months. That’s why they call it the fourth trimester and they’re not engaging. The love is super one sided. It is an amazing experience and an amazing sense of responsibility. I think fun is the wrong word. Some people are like, “Oh, it’s fun.” I don’t know about that. It’s something I don’t think I expected exactly what it was. And I think part of that is I realized I actually hadn’t met that many newborns. And I think the reason for that is when you go out in your everyday lives, parents with newborns are not out and about. I go out, I see babies, I’m like, “Oh, this is what I’m expecting.” And this was kind of validated because a couple of times me and Marielle went out when we had a newborn and people would be like, “Oh my God, look at that tiny little baby.” And I’m like, “Yeah, this is how they start.” I think everyone kind of forgets it.
[00:18:24] Rex Gelb: There were definitely moments like that that were a little surprising.
[00:18:29] Adam Fishman: Yeah. So most surprising thing is when you see a movie and there’s a cute, cuddly baby, that’s not a newborn baby. That baby’s six months old and actually they’re not so cute and cuddly for the first several months.
[00:18:43] Rex Gelb: And everyone’s like, “Oh, you’re going to love it. It’s amazing. It’s so fun.” I’m just like, “I think you’re thinking of a six month old or like…”
[00:18:50] Adam Fishman: He’s just kind of holding it up like, “What is this thing?” Yeah. Sicky Chen was on the show and he referred to the baby in the beginning as just a potato that eats sleeps and poops. And he’s like, “It kind of looks like a potato.” That’s kind of it. Okay, awesome. Well, good, surprising learning. So fellow dads that are out there that are expecting to have a cute, snugly baby right away, definitely doesn’t happen. Brace yourself. But then they get super cute. I’ll bet your daughter is incredibly cute right now at nine months old.
[00:19:21] Rex Gelb: Of course.
[00:19:22] Adam Fishman: Is she crawling yet, by the way, and moving around?
[00:19:24] Rex Gelb: Yeah, she’s crawling while trying to lift herself up on things, getting into a little trouble.
[00:19:29] Adam Fishman: You’re well past the potted plant stage of a child where you could just set them down and they just sort of sit there. Okay. So I promise that we would get to this, but one of the things that we haven’t talked about too much on this show, and in fact, in my recollection, maybe at all, I think it’s because a lot of parents, either they forget or it’s just not a thing that they want to talk about publicly. So maybe it’s a little uncomfortable, but I think far more people experience this than actually admit it, which is when you have this really young baby at home, there are a lot of late night and early morning arguments that happen between couples. Like you’re sleep deprived, you’re stressed, no one is operating at their best. And you brought this up in our prep for this show.
[00:20:11] Adam Fishman: And so I just kind of wanted to hear about your experience and how did you work through that? Was that something that somebody else told you to expect? How did you give yourself some grace on that?
[00:20:24] Rex Gelb: Yeah. So there’s this piece of advice that older couples like to tell younger couples, which is never go to sleep upset with each other or never go to sleep in a fight or something like that. And I think generally speaking, that is the dumbest piece of advice. For me personally, I think it is especially dumb if you have a newborn. I mean, so you’ve got two people that are sleep deprived and stressed out. There’s baby poop, there’s some accident and somebody snaps at someone and the other person snaps back. It’s like, you know what the exact wrong time to resolve this fight is? It’s like right now.
[00:21:02] Rex Gelb: I don’t know when is right, but not right now. So just like, I think me and my wife both agreed with that. Anything said after 2:00 AM doesn’t count. Just go to bed and we’ll figure it out in the morning. And I think that that is absolutely a better piece of advice because you go to sleep and you wake up 99% of the time this is a non-issue. It’s just like you were both exhausted and in the 1% of the time you happen to both coincidentally be thinking clearly, it’s like, okay, now there is something to talk about, but we’re both well rested and levelheaded and now we can have a civilized conversation. In no situation are you better off dealing with that at night.
[00:21:44] Adam Fishman: Yeah, that’s awesome. That’s awesome. I love that. We’ve just completely upended the never go to sleep unhappy. And we’re actually like, when you have a newborn, terrible advice, you’re not going to resolve anything. You’re not getting less tired staying up talking about it. The best thing to do is catch up on some sleep and then when you’re in a better place, talk about it the next day.
[00:22:05] Rex Gelb: If it’s still an issue, which it probably won’t be.
[00:22:06] Adam Fishman: Which it probably won’t be. So it’s funny that nobody really talks about this, but it happens a lot, tons of arguments because you’re exhausted. You just can’t function rationally. All right. So I often ask dads on this show to give some advice to their pre dad selves, but I wanted to ask you a slightly different version of that question, and that is, what is something that took you a while to figure out in the first year of your daughter’s life?
[00:22:35] Rex Gelb: I think the thing that I realized later is just like whatever the challenge is, you don’t necessarily have to figure it out and become a master at that level. You just have to get through it
[00:22:45] Adam Fishman: Because it’s not going to be there pretty soon.
[00:22:45] Rex Gelb: Because it’s not going to be there pretty soon. So in the beginning, you don’t know how anything works or what anything is. It’s like, what is a nipple shield? What is a bottle warmer? How do I wash this bottle? Can I dishwash this bottle? You don’t know anything. And then by the time you figure it out, it doesn’t matter in two months anymore anyway. And then you’re onto the next thing and it’s like, oh my God. So we had to deal with … Have you heard the term witching hour?
[00:23:13] Adam Fishman: Oh, yes. For the sake of people who haven’t, tell us about that.
[00:23:16] Rex Gelb: So there’s this thing that happens where newish babies, I think it happens around two to three months and they just start screaming and crying. For us, it was at 6:00 PM every night for three weeks and no one knows why this happens and there’s really nothing you can do except deal with it. So you’re dealing with that and trying to figure it out. And then by the time you kind of know what’s going on, you’re onto the next thing. I think that this has become enough of a pattern at this point where it’s like when a challenge comes up, and this probably goes on through their teenage years, there’s just always a new challenge. And now we can kind of pattern match and we’re just like, “Oh, this is a really annoying thing. Maybe we can’t figure it out, but if we can just hang in there for a couple of months, we probably won’t have to deal with this anymore.”
[00:24:03] Adam Fishman: But then it’s sort of like if your baby comes with an instruction manual, every couple of months you burn the instruction manual and you get an entire new instruction manual, right? The things that they need, how they operate, all this stuff, it’s a constant moving target, which is really funny. And I don’t think anybody really explains that to you when you have a kid. You just have to figure it out on your own. This is why anybody who gives you a snapshot piece of advice is like, yeah, that’s good for that whatever one month period of time, but it’s not going to be good six weeks from now. I want to talk about some of the household processes, and that’s what I would call them that you and your wife have. So the first one, I really can relate to this a lot, but the first one is lists.
[00:24:48] Adam Fishman: So you keep a lot of lists and you said you keep way more lists than you did before you had a kid. Why is that?
[00:24:56] Rex Gelb: Yeah. So when I was only responsible for myself, I feel like I had enough memory and CPU to … I could just keep track of everything. And I knew what I had to do. I knew all of the appointments I had to go to. I was probably at the brink of capacity. I was writing things down, but then you just drop a child into the mix and it’s just like there is no chance. So now I just know if I don’t write it down, there’s like a 90% chance I’m just not going to get to it or not going to remember. And so if it’s important and I want to be a reliable, responsible adult, which I do, I just write down everything. Even if I’m mid conversation, I’ll pause the conversation and be like, “I’m so sorry. I have to write this down,” and I’ll put it on my note because I know if I don’t, it’s gone.
[00:25:41] Adam Fishman: Yeah. It’s like an LLM that when the baby comes, it just explodes the context window and you’re like, “Anything that’s not related to this kid, it’s gone. It’s out of there. I’ve forgotten it all.” So got to add it back into context. Okay. So list keeping, number one. The second one, as corporate as this sounds, I actually love this, which is that you and your wife have planned one on ones. So tell me about your one on ones with your wife.
[00:26:08] Rex Gelb: Yeah. So we say that as a way of poking fun of corporate America. We were living the same life. I was at HubSpot. She was at Dropbox, so very tech one on one life. So we started doing it to make fun of that life, not to take it seriously, but yeah, we do. So we have a shared Apple Note and when we think of things throughout the day, if they’re not time sensitive and it’s something we can do on a walk rather than at a desk, we’ll throw it on the shared one on one and then we go on a walk after work most nights and we tackle all of the bullets then and it’s just way better that way because otherwise you’re inside trying to squeeze it in a busy day and it didn’t have to. Why not go out? It’s a nice day and figure it out all outside.
[00:26:51] Adam Fishman: What’s an example of something that finds its way into the Apple Note?
[00:26:55] Rex Gelb: Anything that’s more than two seconds. So I recently realized we haven’t cleaned our gutters since we moved into this house. Hey, we’re going to have to figure that out. It doesn’t have to be right now. It’s just like, put it on the list for later. Or recently we started talking about, do we want to do anything for Skylar’s one year old birthday? That’s something we can absolutely do outside on a walk. So anything that’s more than a two second thing and it’s not time sensitive, we’ll throw it on there and figure it out after work.
[00:27:21] Adam Fishman: Awesome. Awesome. So this is related to something that we’re going to come back to, and we’re going to talk a little bit about AI towards the end, but one of the things that you do in these one on ones each month is something you called a leap alert. So like leap, like taking a leap, and it’s a check in that you do, you try to do monthly. This is also a way that you use AI as a couple. Tell me about what a leap alert is.
[00:27:45] Rex Gelb: Yeah. So it started out as a newsletter. We had subscribed to this newsletter when she was born and you put in her birthday and every month they send you what they call a leap alert. These are the developmental milestone things to look out for. These are safety considerations. These are things to look forward to. And at some point the newsletter stopped coming. I don’t know what happened. So now we have just a calendar reminder on her birth month day, whatever. And every month we pull up Gemini and we say pretty much the prompt is something to the effect of like, Skylar’s about to turn nine months. What are some developmental milestones that we should look out for? Are there any safety considerations, anything we should look forward to? Things like that. And it’s super helpful because it’ll be like, you should really start babyproofing your house or your car seat.
[00:28:29] Rex Gelb: If you haven’t adjusted it, she’s probably pretty scrunched right now. And we’re like, “Yeah, we got to adjust the car seat,” or “You should really start introducing allergens now,” whatever it may be. And it tells us things to look out for and fun things coming up. And then we’ll have a conversation with Gemini and ask follow up questions. So that is a fun and practical thing that we do every month.
[00:28:50] Adam Fishman: It’s like a pseudo hands on pediatrician meets the Wonder Weeks book or something like that. Very cool. Has it ever hallucinated and told you something like, “Better lock your alcohol cabinet because she’s going to start raiding it,” or something like that?
[00:29:04] Rex Gelb: No, nothing obvious, but it’s possible it hallucinated something not obvious that I just didn’t know.
[00:29:09] Adam Fishman: Okay, cool. I just had to ask. Okay. So another thing is, and I can relate to this, I feel like most couples are texting back and forth constantly throughout the day. You think of something and you like, boop, it either goes in the Apple Note or in this case goes in a text message, but you and your wife email each other back and forth, which is awesome. How did the two of you delineate between what warrants a text message and what goes in an email?
[00:29:34] Rex Gelb: Yeah, that’s another kind of corporate thing, huh? And I do think it is somewhat unique to us, although it’s interesting to hear that you do it, so maybe it’s not unique, but we kind of realized when we’re texting, things get lost. You can’t thread texts like you can with Slack, right? So things just go up, up, up, up, and if you don’t get to something, it’s gone. And sometimes we need to have 10 conversations at once. If it’s not a really quick thing that you can reply to right away, it’s something to think about or we need to review it. We’ll do an email and then for the course of the next few weeks, we’ll go back and forth and do email. I just think it’s a little more efficient and things are less likely to get lost.
[00:30:15] Adam Fishman: I think it’s probably a thing that maybe more couples should lean into. Embrace it. It doesn’t have to be just for work. So I did hear of a couple, at least one couple that had a Slack thread with each other or a Slack workspace or something. And that I found pretty interesting. So I want to hear about some of your busy startup dad time hacks. You’ve got a bunch of time hacks that you’ve sort of implemented because you find yourself just having less time as founder of a company and also new dad and things like that. So tell me about some of these time hacks that you have.
[00:30:51] Rex Gelb: Yeah. So some of these are going to probably seem pretty silly, but just keep in mind starting this company already totally crazy and then throw a kid into the mix. Yeah.
[00:31:01] Adam Fishman: This is a judgment free zone. We’re all just doing our best.
[00:31:05] Rex Gelb: Yeah. So there was a 10 week period that was really, really intense. I did not see daylight. So these are ways I was trying to find time. So I’ve always kind of meal prepped. So I was making a batch of chili, which would last me for a couple of weeks. And I realized that I could get a second Crock Pot, spend 10% more time, make two Crock Pots of chili at the same time, batch them all up. And for five more minutes, have double the food for two more weeks. I was doing that. Probably will keep doing that. I started just multitasking everywhere possible. So I used to keep up with paid media mostly through reading. I was on a lot of newsletters and reading a lot of blogs. Paid media is what I do. I still do read a lot before bed to try to keep up, but now, so if I’m on the elliptical for 30 to 45 minutes, I put a TV in front of the elliptical and I queue up just a bunch of different YouTube videos about paid media, the new features, how people are using them, what’s working for people, different debates about how to use different things.
[00:32:11] Rex Gelb: And if I’m exercising right now, I’m just downloading paid media YouTube videos. Or if I’m on a walk, not listening to music anymore, I will just download, if it’s not Startup Dad, pretty much everything else is just like same thing, just like paid media, like what’s the latest, what’s working for people, things like that. So it’s like my new way of keeping up. And then same thing, if I’m on a flight, I used to just be normal and put on Netflix or something. And now before the flight, I assume there’s no internet and I’ll just queue up five hours of articles about paid media. I’ll just crank through them throughout the whole flight. So really it’s just like a lot of multitasking, trying to find pockets of time where I can.
[00:32:53] Adam Fishman: That flight one is probably advice that I should follow because I often go to a flight and I’m like, “Oh, I’m going to be so productive. I’m going to get on the Wi Fi. I’m going to do all this stuff.” And then inevitably it never works. And then I just end up like, “Ah, shit. I don’t have access to any of this stuff.” The unlock for me and what you said was like, “I just assume the Wi Fi is not going to work,” which I think probably a lot of other people have figured out, but I certainly haven’t. So I just need to get with that program. So I also love just you’re just figuring out ways of multi threading activities. So watching the video while you’re also exercising or listening to the important competitive insights, like updates while you’re going on a walk. So love that.
[00:33:36] Adam Fishman: Have you gotten into using NotebookLM to turn written things into a podcast so that you can listen to them on your walks yet?
[00:33:44] Rex Gelb: I tried it one time and it didn’t really work and I didn’t come back, but I should.
[00:33:49] Adam Fishman: My problem is I don’t really want the summary. I want the thing. I don’t want the reduced summarization of it for most things. Some things fine, not most things. Okay. So I want to come all the way back to, we talked about how you move past the 2:00 AM sleep deprived battles with your wife. And I’m glad that the two of you are thriving in that now, but where is an area where the two of you are still trying to sort things out during the non sleep deprived moments?
[00:34:19] Rex Gelb: Yeah. So the big thing right now, and it’s definitely not a battle or a big disagreement, but the thing we’re still trying to figure out is what work life balance looks like in our house, how much I should be working, how much I should be around, the different tradeoffs there, because we really do want Skylar to be tough and resilient and be able to work hard and move a mountain if she has to. But we also want me around a lot as well, especially when I have to, I think it’s a fluid discussion. And I think to your point, it actually might look different right now than it does in five years. I think it will probably be an ongoing thing.
[00:34:55] Adam Fishman: Yeah. Well, I imagine one of the things that’s tough for you and that you’re running kind of a small sort of paid media consultancy is that if you’re not working, you’re not getting paid. The meter’s always running kind of when you work for yourself for the most part. And there’s probably some exceptions to that, but I can see how that would be challenging as opposed to salaried employees maybe was a little different or something like that. I could see how that would be challenging.
[00:35:22] Rex Gelb: Yeah. I did just consulting and advising for a really long time. Now I have an actual paid media agency where I’ve got employees and it’s not quite as bad on that anymore, but you are right, there’s a clear tradeoff. If I’m not growing the business, and I think this is probably with most startup dads, it is one or the other.
[00:35:43] Adam Fishman: I want to come back to what you talked about like hard work. And I’ve talked to some other dads on this show relatively recently, actually, this sort of concept that you picked up from a friend, which is this idea that you really shouldn’t deprive your kids of struggle. And so I’m curious, the dads that I talked to on the show about this, it was like they all had older kids. So it was like, well, you want your kid to be independent and get some things wrong and get some lumps in life and stuff like that. But how does that manifest for a dad of a not yet one year old? What does struggle look like with a nine month old?
[00:36:26] Rex Gelb: Yeah, it’s a great saying from a good friend of mine, never deprive them of a struggle. And he also has a one year old and he takes it actually even further than I do. But we are starting to kind of try to work on this early because I actually think it’s something that I’m going to struggle with because I already can’t stand to watch her struggle. It’s so hard for me, but I know if I step in too much and don’t let her do her thing, I’m going to undermine her confidence. And I think that that potentially can start happening now. So yeah, in practice for a nine month old, for example, she had a toy stuck under her high chair. She couldn’t reach it because her head was getting in the way of the beam and it would’ve been very easy for me to go over and get the toy from her and give it to her, but decided not to do that.
[00:37:12] Rex Gelb: Or I’m sitting on the floor and she wants to get past me. I could just move and get out of her way, but I don’t. I let her crawl over me or go around me or figure something else out or I let her tumble and fall. Nothing that would actually hurt her, of course. But an example the other day, so she’s at that age where she can reach up to a low shelf and pull herself up and stay. She’s not walking yet, but she can get up. There was a low shelf and she put one hand on the shelf and she started to hoist herself up and she put her other hand on a ball that was on the shelf and she grabbed onto that and I’m watching this and I’m like…
[00:37:48] Adam Fishman: I shouldn’t be laughing, but I know exactly what’s going on.
[00:37:51] Rex Gelb: I’m watching this. I’m like, I know this isn’t going to work. She’s going to think she can grab onto that ball and hoist herself up. And of course she did and it didn’t work and she fell on her butt and she was unhappy for a second, but it would’ve been very easy for me to go and catch her and say that’s not going to work. But I think it’s actually not in her best interest. I think let her realize, yeah, that ball isn’t mounted in, not going to work. And then now she learned and I think she probably won’t do it again.
[00:38:21] Adam Fishman: Yeah, yeah. I think that’s a great example to come back to what we have talked on this show a little bit before, which is like, you obviously don’t want your kids at any age to do something that is really going to put them in harm’s way, but small bumps on the road or small failures, like age appropriate failures are really good. And that’s a perfect example of an age appropriate failure. She’s not at the top of the stairs teetering off the edge, about to tumble down. She’s pulling herself up from about zero inches to five inches, and then she’s going to just sit down hard on her butt when she reaches for the ball that is not a stationary object. That makes a ton of sense. So it also probably is a bit of a training for you because the desire for you to intervene is probably only going to increase over time.
[00:39:16] Adam Fishman: So if you can’t get it right now, how are you going to get it right when she’s two or five or eight or whatever? So good training for you.
[00:39:27] Rex Gelb: Yeah. And I do frame it that way of like, they say with sleep training, it’s like, this is kind of for the baby, but really the hard part is on the parents, probably a similar thing here.
[00:39:36] Adam Fishman: Yeah. All right. I said we were going to revisit AI and so we are, because I’m not sure if you’ve heard of it, but it’s kind of a big thing right now. So I want to revisit AI and parenting, which is that you use AI a lot for baby related health things. And so I’d love to know how you use it when it comes to that stuff.
[00:39:57] Rex Gelb: I don’t know if this is anything particularly creative that we do, but we do reach for AI all the time. It’s just like our first line of defense. Skylar had a rash all over her face. We’re like, “What is going on?” So snap a picture of it. It’s like, “Oh, baby acne. Who knew? That’s a thing.” Or the witching hour thing, that’s how we discovered what that was when she was just crying every night at 6:00 PM or if she’s inconsolable, any sort of symptoms. It’s just our first line of defense, but I imagine probably that’s the same for a lot of new parents.
[00:40:29] Adam Fishman: Yeah. I’m willing to bet that even ChatGPT recently released their health tracking thing. I’m certain there are a lot of people using this as an alternative first line defense to a 24/7 pediatrician. I think it’s a great starting point. Certainly there’s probably some risks in following treatment patterns to the letter of the law, but it’s a good starting point for sure.
[00:40:54] Rex Gelb: It’s a start. And if it didn’t make sense, we wouldn’t do it. If it’s like, this is a thing, then here are pictures of baby acne, here’s a picture of your baby. It’s like, yeah, okay.
[00:41:02] Adam Fishman: Have you thought at all about as she gets older, your daughter is going to grow up truly in an AI native world. Obviously you are using it a lot. She’s nine months. She will absolutely be exposed to it. I mean, just like kids who grew up in the cell phone era and stuff started to get exposed, but she’s going to be a core likely user of AI. I’m sure it will be in her education and we don’t even know what it’s going to look like, but I would be shocked if it’s not. Have you thought at all about how you’re going to navigate that with her?
[00:41:40] Rex Gelb: A little bit. I think it’s a little too early to say how it all goes down, but I think that there’s going to be a healthy balance. Definitely not going to take it away. It’s going to be very, very important that she’s familiar with the tools and knows how to use them. But you do read stories of people getting a little too carried away with whether just chatting with AI all day every day or kind of like social media. And I’ll have to think about it more as things evolve. But I think the way I frame it right now is it’s kind of like any addiction. Take teenagers and alcohol, for example, it’s like, I think probably the right thing to do is not take it away in full and give them no exposure and no practice in how to handle that. But you also don’t want to give them a blank check and trust them to be responsible before they know how to be responsible.
[00:42:33] Rex Gelb: And I think probably it’s the same thing with AI and social media. Let’s use it a little bit with supervision. Definitely understand the upsides here and understand the downsides and let’s figure out how we do this responsibly.
[00:42:47] Adam Fishman: Awesome. Well, I think that’s a great thing to end on. And before we do, I wanted to ask, how can people follow along or be helpful to you?
[00:42:58] Rex Gelb: Yeah. I’ve got a paid media business. If anyone ever wants to chat paid media, summitchase.co is our site, or feel free to connect with me on LinkedIn, especially if you’re in B2B or SaaS or professional services, that’s what we do best. But really, if anyone wants to chat paid media, feel free to connect with me and it’d be a lot of fun to talk to other Startup Dad listeners.
[00:43:19] Adam Fishman: Cool. All right. Well, we will link to all that in the show notes. Now it’s time for Lightning Round. Are you ready?
[00:43:35] Rex Gelb: Ready.
[00:43:35] Adam Fishman: One of my favorite parts of every episode. Here we go. What is the most indispensable parenting product you’ve ever purchased?
[00:43:35] Rex Gelb: It’s an app called Huckleberry.
[00:43:38] Adam Fishman: What is Huckleberry?
[00:43:40] Rex Gelb: You log a child when they eat or sleep, like the time and the amount, and then it predicts with eerie accuracy. It’ll send you a push notification when they’re going to be hungry or tired again. Super convenient.
[00:44:01] Adam Fishman: Wow, that’s awesome. I maybe need this for myself. What is the most useless parenting product you’ve ever purchased?
[00:44:01] Rex Gelb: We bought something called a Shusher, which was actually great until we realized we could do it on our phone and then we didn’t need the product anymore.
[00:44:07] Adam Fishman: Yeah. So no need for the standalone device because it’s just sort of built onto your phone. Yeah.
[00:44:11] Rex Gelb: And
[00:44:12] Adam Fishman: that Shusher is like, it’s like a little standalone speaker thing that kind of makes a shushing noise, right?
[00:44:16] Rex Gelb: Yeah, exactly.
[00:44:17] Adam Fishman: True or false, there’s only one correct way to load the dishwasher.
[00:44:21] Rex Gelb: False. No worries.
[00:44:22] Adam Fishman: Oh, okay. Would your wife agree or disagree with that statement?
[00:44:27] Rex Gelb: She would disagree.
[00:44:32] Adam Fishman: Oh, awesome. Awesome. What is your signature dad superpower?
[00:44:37] Rex Gelb: Distracting Skylar.
[00:44:39] Adam Fishman: Okay. What is your least favorite parenting task?
[00:44:43] Rex Gelb: Diaper changes.
[00:44:45] Adam Fishman: Have those gotten easier or harder as she’s gotten older?
[00:44:49] Rex Gelb: Harder.
[00:44:50] Adam Fishman: Because she’s more active and aware.
[00:44:52] Rex Gelb: More wiggly and more gross.
[00:44:55] Adam Fishman: That’s true. 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?
[00:45:01] Rex Gelb: PM.
[00:45:02] Adam Fishman: Okay. Nighttime. Craziness. What is the ideal day with Skylar? What does that involve?
[00:45:10] Rex Gelb: Long walk to get froyo.
[00:45:12] Adam Fishman: Okay. She big into frozen yogurt?
[00:45:15] Rex Gelb: No, I am. We’ll have a little bit.
[00:45:19] Adam Fishman: Awesome.
[00:45:20] Rex Gelb: I
[00:45:20] Adam Fishman: love that. If she had to describe you, I know she’s not talking at nine months, but if she had to describe you in one word, what would it be?
[00:45:27] Rex Gelb: I think silly.
[00:45:28] Adam Fishman: Okay, good. What is your go to dad wardrobe?
[00:45:32] Rex Gelb: Shorts, hat, and a T shirt.
[00:45:34] Adam Fishman: Okay. Awesome. How many parenting books do you have in your house?
[00:45:40] Rex Gelb: None. All Startup Dad episodes. The full education.
[00:45:44] Adam Fishman: Okay. And now how many episodes of Startup Dad have you listened to end to end?
[00:45:49] Rex Gelb: I’m going probably 30.
[00:45:53] Adam Fishman: Yes. Pretty good.
[00:45:53] Adam Fishman: I’ll take it. I’ll take it. How many dad jokes do you tell on average each day?
[00:46:00] Rex Gelb: 1.5.
[00:46:01] Adam Fishman: And those are probably told to your wife or like a colleague?
[00:46:04] Rex Gelb: Yeah, anyone.
[00:46:06] Adam Fishman: Okay. Do you have a favorite baby food?
[00:46:09] Rex Gelb: Berries.
[00:46:11] Adam Fishman: Like mashed up berries or just like regular berries?
[00:46:14] Rex Gelb: Just half blueberries. It’s the only food that Skylar will eat right now anyway.
[00:46:19] Adam Fishman: Okay. I love it. I also see why the diaper changes are challenging. What is your favorite kid’s movie?
[00:46:27] Rex Gelb: The Incredibles.
[00:46:28] Adam Fishman: Oh, great. Great series. What nostalgic movie can you just not wait to force Skylar to watch with you?
[00:46:36] Rex Gelb: The Sandlot.
[00:46:37] Adam Fishman: Another classic. Yeah. What is the worst experience that you’ve ever had assembling a kid’s toy or a piece of furniture?
[00:46:45] Rex Gelb: It wasn’t assembling it, but we went to pick up a crib and it didn’t fit in the car and it took us a long time to realize it wasn’t going to fit.
[00:46:54] Adam Fishman: What did you do when you realized that?
[00:46:57] Rex Gelb: I think we had to reassemble it and give it back. I know.
[00:47:02] Adam Fishman: Okay. How long can a piece of food sit on the floor and you will eat it still?
[00:47:08] Rex Gelb: Not too long. There’s no time for getting sick right now. Couple seconds and I’m out.
[00:47:12] Adam Fishman: Okay. And with the age that Skylar is, you don’t have a lot of options here, but what is your favorite dad hack for road trips or flights?
[00:47:21] Rex Gelb: Snacks.
[00:47:22] Adam Fishman: Snacks. It’s also the favorite hack for me. What is your take on minivans?
[00:47:27] Rex Gelb: We don’t have one, but they seem super convenient. They seem great.
[00:47:30] Adam Fishman: Okay. Has this come up in conversation yet with your wife?
[00:47:34] Rex Gelb: Yes, it has. And I think we’ll probably be a minivan family at some point.
[00:47:37] Adam Fishman: Oh, wow. She’s also team minivan?
[00:47:40] Rex Gelb: Yeah, she is.
[00:47:41] Adam Fishman: Wow. It’s a rare treat to have a two parent household that’s both on team minivan. Yeah, according to my Startup Dad statistics at least.
[00:47:49] Rex Gelb: Yeah, there you go. Okay. Interesting.
[00:47:51] Adam Fishman: Well, good. She’s in good company. All right. Well, hey, Rex, this was awesome. Thank you so much for joining me on the show today. And I wish you and your wife and Skylar all the best for 2026 and a happy one year birthday to her because when this comes out, she will have just turned one. So thank you.
[00:48:13] Rex Gelb: Awesome. Thanks so much, Adam. This was a blast. Appreciate it.
[00:48:16] Adam Fishman: Thank you for listening to today’s conversation with Rex Gelb. 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.