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Learning the Hard Way as a Single Parent with Colin Anawaty, CPO | Dad of 2 · Startup Dad

• [00:00:00] Colin Anawaty: As technologists, we’re always so far ahead, whether we’re road mapping or building out the multi-year plan or thinking about where technology’s headed. Children just really live in the moment, whether it’s the smallest things walking around the neighborhood, relearning what an airplane is, or a helicopter or certain kinds of animals, that ability to see joy in things that I’ve just taken for granted now is almost like a rebirth or relearning that I’m going through. [00:00:29] Adam Fishman: Welcome to Startup Dad, the podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I’m your host, Adam Fishman. In today’s episode, I’m joined by Colin Anawaty. He’s a serial founder and lifelong technologist who has founded multiple companies in the health tech space and was a product leader at athenahealth. He’s a single dad and the father of two boys. We talked about the importance of prioritizing relationships, including yourself and why he joined a men’s group. To better focus on that, why it’s important to take stock of the good and bad from prior generations, how kids are truly more robust and resilient than we think, and the importance of letting kids explore their independence and experience accountability. We ended with a discussion on why no one ever really has it all figured out professionally or as a dad. If you like what you hear, please subscribe to Startup Dad on YouTube, Spotify or Apple. I hope you enjoy today’s conversation with Colin Anawaty. Welcome Colin Anawaty to Startup Dad, and a special shout out to Alex Cohen for introducing us, one of our earliest startup dad guests. But Colin, it is my absolute pleasure to have you on the show today. Thanks for joining me, [00:01:48] Colin Anawaty: Adam, it’s a pleasure to be here. Thanks for inviting me. Excited to do this. [00:01:51] Adam Fishman: Let’s dive in. You are recently divorced. I’m not going to spend much time on that, but you also have a 6-year-old and a three and a half year old, and then your oldest son is a 12-year-old bulldog named Benji. [00:02:05] Colin Anawaty: That’s right. Company mascot. [00:02:09] Adam Fishman: How have you been adjusting to life as a single dad [00:02:13] Colin Anawaty: Candidly and transparently? Still figuring that out? It’s been an interesting year. Won’t belabor what went into the marriage ending, but being a single dad’s hard, it’s already hard enough just being a new parent, learning all the ins and outs, but I’m recalibrating every week as I’m learning and apologizing frequently to my children asking for their help. [00:02:38] Adam Fishman: Yeah, that sounds about the only thing you can do when they’re six and three and a half. You’re just making it work, so you are a native Texan, which is fascinated me. I don’t know very many native Texans. Maybe that’s probably my fault for not getting out into the world more, but what’s childhood like growing up in Texas? You’re in Austin now, but I’m not sure where exactly you grew up and what that life was like. [00:03:01] Colin Anawaty: Yeah, great question, but also if you want to meet Texans in the summer, go to Colorado. We just flocked there, kind of like the Californian czar to Austin, but I grew up in Houston in a neighborhood where you had two acre lots that backed up to usually farmland, so there’s a bunch of cow patties right behind us. And then in this neighborhood, we also had a bamboo forest, and so I remember the Kevin Costner Robinhood movie inspiring a lot of forks, bow and arrows staffs, all carved and made out of bamboo. So it was a pretty great childhood in terms of just getting out into nature and building things. [00:03:41] Adam Fishman: Awesome. What were you like as a kid? Were you like you are now or were you different kind of kid? [00:03:48] Colin Anawaty: Yeah, great question too. Funny enough, my dad despised the TV so much so that he put this really rinky-dink tv with buddy ears because we didn’t have cable. If you were going to have cable, you had to have a satellite dish the size of a small garage in your backyard. He put that in his office, which made it really uncomfortable to ever want to go down there and watch tv. And so it was really just kind of create your own adventure, whether it was a box of Legos, which were one of my toys that I enjoyed playing with, going out into the bamboo forest. I also got into skateboarding, and so building ramps, things like that. His workshop was very accessible. He liked us learning how to use the power tools, but that was my childhood until, funny enough, he brought home a computer. He thought the computer was going to be part of what was going to change meaningfully in business to his own demise. That became my new toy, and I started learning everything from early days of dos and Windows 3.1. I ran a neighborhood bulletin board service of EBS. There’s probably some folks listening to your podcast who have no idea what that is. I [00:05:06] Adam Fishman: Certainly know what it is. [00:05:08] Colin Anawaty: Yeah, it was good times. It was the early frontier of connectivity, and then that led to downloading Duke Nukem and making Duke Nukem maps and sharing those with my neighborhood friends, and then started to learn programming languages including HTML and in high school, started working in the summer at a web development company in downtown Houston. [00:05:31] Adam Fishman: Cool. All kicked off by your dad hiding the TV and bringing home a computer instead. [00:05:37] Colin Anawaty: That’s right. [00:05:38] Adam Fishman: So that’s awesome. Well, thanks dad for that. Okay, so you have a life philosophy that I loved, which is prioritize relationships including the one with yourself. And as part of that, you joined a men’s group about three years ago, and so I’m very curious why did you do that and is that something that you’d recommend other dads? [00:05:59] Colin Anawaty: Yeah, there’s a fellow who’s written a book called Five Types of Wealth, Sunil, I forget his last name, but there seems to be a trend now, especially in my circle of technology and entrepreneurs who are looking for, call it a greater purpose or some semblance of balance as they go through the motions of building these businesses, pouring their heart and soul into it, and then assuming there’s a liquidity event, realizing that money’s not the thing that fills your soul. I joined a group thanks to a great guy in Austin who’s been here for 20 some odd years, Josh Dilworth, who’s kind of really always had an intrigue and an appetite for sense of community and developing community, and they created a program called Ari, also known as the calling, and it’s a two year program broken up into four parts, relationship with yourself, relationship with others, relationship with spirituality, so multidimensional, it’s not strictly on Christianity or we also have atheists and then relationship with the world through work. [00:07:04] Colin Anawaty: So it is to still encourage and really help entrepreneurs align at least on their next mountain, maybe your next venture, your next startup has an even greater purpose and maybe more clarity around what that purpose is than just making money or building a big business. So I went through that program now in the alumni group. They started as just a group of men kind of organizing on their own and then started to branch out, and we were the first group that was kind of that first branch, and now I think they’re up to eight or nine different forums of eight men each. [00:07:38] Adam Fishman: Wow. And do things around being a dad or a parenting or maybe going through that process. Did that kind of creep, does that creep into any of those four pillars or any of the alumni interactions that you have now? [00:07:53] Colin Anawaty: For sure, and my group specifically, not all, but a good chunk of them are dads. And so we have lots of shared conversations around parenting and different philosophies. I also take a continuous improvement mindset to my own life, and so while the formal program is two years, the alumni is self-organizing, there’s not really a start and stop to this. You’re going to go through life hopefully embodying some of these frameworks and tools that pedestal and those four legs can be more stable hopefully than before. But I think you’re always kind of finding a way to do the balancing act based on the seasonality of how you’re getting pulled in different directions. [00:08:39] Adam Fishman: And is this group or another sort of something similar to it, something that you would recommend that dads get involved in their community? [00:08:50] Colin Anawaty: A thousand percent, and I’d go so far as to say whether you’re reading five types of wealth or you’re in a formal group. One thing I think a lot of men historically have struggled with is just having these conversations amongst friends. Often it’s sc or has work going. A saying that I think really resonates is the longest distance a man will journey in his life is the 18 inches between his head and his heart. And so we have a habit of just cramming those feelings down and hopefully not in an unhealthy way, but we don’t want them to blow up, explode or create other real stressors on your life. And so whether it’s a formal group, whether reading some books can self-organize a group of people in your network and just have more vulnerable conversations, and I think that’s a great step forward. [00:09:43] Adam Fishman: Okay, great. There is a particular, let’s call it a parenting style from prior generations that I think many modern parents have really moved away from. The pendulum has swung in a very different direction from maybe how we were raised. But you think, and I tend to agree that it’s really important to take stock of the good and the bad from those prior generations. So tell me about what that means for you. How are you doing that work? [00:10:16] Colin Anawaty: Yeah, maybe just restating in the old way, it was very authoritative. The patriarch model what dad or the head of household says goes, and then things kind of went over into this permissive parenting, always reward, encourage your kids, never tell ‘em they’re doing something wrong. But I do sense reading some of the thought leaders in social media or on parenting that there’s kind of a tilt back to somewhere in the middle where you’re trying to give the proper amount of guidance, the proper amount of constructive feedback, but hopefully in a way that’s not damaging. And I think that’s kind of the key to try to find ways in which you can coach your children just like you might think about coaching an employee in a startup, but doing it in a way that doesn’t hurt their feelings, create insecurities, but I don’t necessarily believe you should just have your kids running around and doing whatever they feel is appropriate, [00:11:18] Adam Fishman: Like feral animals, [00:11:20] Colin Anawaty: Like feral animals. That’s right. But that doesn’t mean you put a shot collar on him like a dog. [00:11:29] Adam Fishman: You also talked about learning at kids’ level and that kids are some of the world’s best teachers, which I thought was really what wasn’t a perspective that I ever thought about before, but I think it’s true. So how have you come to learn that your kids are great teachers? [00:11:49] Colin Anawaty: Yeah, good question. Number one, something that I think I’ve done a little bit more so than my dad’s obviously brought some great things into my life, but it’s more apparent to me when I screw up based on their reaction. And so even though they’re very young, I’ll get down and apologize for where daddy’s wrong or maybe where I need help because they’re carrying on at the dinner table and I’m now a single dad, and so I’ll ask them to help me out. And that’s leveling up their expectations of being a contributor or being an adult, and I don’t want to do that too soon, but I also want to show them it’s okay to ask for help no matter who you are. I know they look up to me as someone who I am the dad, hopefully I have a lot of answers, but it doesn’t matter where you are in life, what age you are, what experience you have, you’re going to have moments where you need help. [00:12:46] Colin Anawaty: And so that’s been an area where I’m just taking stock in myself and where I can show up and better for them and better for myself. And then number two is technologists, which I think probably a lot of your listeners are, we’re always so far ahead, whether we’re road mapping or building out the multi-year plan or thinking about where technology’s headed. Children just really live in the moment, whether it’s the smallest things walking around the neighborhood, relearning what an airplane is or a helicopter or certain kinds of animals, that ability to see joy in things that I’ve just taken for granted now is kind of that almost like a rebirth or relearning that I’m going through. [00:13:34] Adam Fishman: Yeah, kids have that really interesting way of they’re seeing everything for the first time, and so they have this curiosity because they’ve never seen, I don’t know, a leaf or a bird that looks that way or a squirrel that’s doing this thing. And parents, we kind of just wander around. We’re like, ah, yeah, that’s it. So they’re really helping you kind of shift perspective and see things through that kids’ point of view, which is great. Also, you have this perspective that which I share that kids are robust and resilient, and I often tell people, kids are made of rubber and we just don’t really appreciate that. So that’s another thing that’s been sort of talked about a little bit more as we’ve maybe, again, we had swung that pendulum in the other direction thinking that kids are incredibly fragile and obviously there are certain things that kids can’t handle, but that’s not true for a lot of stuff. So what does that mean to you? How does that robustness and resilience show up in your life? [00:14:31] Colin Anawaty: Well, the most recent event is the kids now have two homes, and that’s been arguably the hardest thing in my life to date, bar none, but I’ve just been in terms of learning from my children, just a little bit in awe of their ability to have handled this and not have them breaking down and not understanding it. And part of that’s talking to them very thoughtfully, talking to them honestly and transparently about it, but the resilience is striking. They’re just able to move forward and granted their ages or health versus had they been teenagers, I think it would be even that much more challenging. So that’s probably the most immediate situation that comes to mind. Beyond that, I think it’s just some overprotectiveness that all parents at times will have, because you love your children, you don’t want anything to happen to them. Sometimes if it’s too much, then they’re just set up for life to always be a little bit fragile, and the real world does not care about a lot of these things. And so just encouraging them to do sports or give Acra if they fall down and skip back up, I think just reinforcing to your children that they’re going to get hurt. It’s okay, dust yourself off and don’t quit. And they’ve been pretty robust when it comes to just little things like that. [00:16:01] Adam Fishman: Yeah. One of the aspects of teaching kids about resilience and helping them see that is talking to them about how it’s okay to make mistakes and demonstrating that you talked about how you talk to your kids about mistakes. And so I’m just curious if you could add a little bit more to that When you mess something up, what do you do with your kids to show that even dad makes mistakes? [00:16:29] Colin Anawaty: It’s pretty simple, but I think often our orientation is to try to model excellence for our children in that we didn’t mess up, but for me it’s also modeling accountability. And so when dad does mess up, then whether it’s sitting him on the bed or getting on my knees to make sure I’m eye level with them and just being really straightforward and just go, dad messed up. I didn’t mean for X, Y, Z to either say those things or for that to happen. I’m sorry, do you forgive me? And so just kind of going through a simple dialogue or script around whatever it may have been that daddy screwed up with. And so sometimes having two boys who are roughhousing, more often than not, they might hurt each other. And so then because I modeled it to them so frequently, I’ll have them do the same thing but to each other and make sure they give each other a hug and then reconfirm with the other. Do you accept his apology? And then we move on? [00:17:32] Adam Fishman: Yeah. Awesome. Yeah, I have about the same distance between myself and my younger brother as your two kids are. And there was no shortage of roughhousing in our house growing up. [00:17:45] Colin Anawaty: I also have a brother similar to you, two years younger Karate Kid was the movie of the times. And so my mom will tell you stories of one of us doing the flying kick at the other, knocking ’em in the chest, knock ’em down. So try not to let them take it that far, but yeah, [00:18:05] Adam Fishman: Don’t teach your kids the crane kick until they’re older, maybe. That’s [00:18:09] Colin Anawaty: Right. [00:18:10] Adam Fishman: So aside from that very pertinent piece of advice, if you were to bump into younger Colin on the street, pre dad, Colin, knowing what you know now about raising a kid to six and three and a half, what’s a piece of advice that you give the younger version of yourself about raising family? Maybe something that you found surprising or didn’t think about much until the kids came around? [00:18:34] Colin Anawaty: So I tell this one to all expecting fathers, which is once they have a child, congratulations, you’re in the Parenthood Club. Nobody really talks to you about how hard it is, at least that first year or two. I think you have an expectation that life’s going to change, but you don’t really, and some of it is just lived experience. You kind of got to experience it. Even if I tell you it, it’s not going to resonate. But those first couple of years, the sleep deprivation, how wildly your life and calendar does change from your social life to just even your relationship with your partner, you’re just not fully prepared for it. And if anything, I would just tell myself as much as you can be prepared, you’re not going to be prepared and just lean in and have lots of conversations with both your partner and people around you and be ready to ask for help. Look for ways that your community, friends and family can also help you. So it’s an eyeopening experience. It’s one of the greatest gifts, but it’s not without a complete 180 from whatever direction you’re heading in. [00:19:48] Adam Fishman: Yeah, so two things there. So prepare for a very hard couple of years because it is hard. It’s a big change. And then also you can’t quite fully prepare. That’s [00:20:00] Colin Anawaty: Right. Yeah. [00:20:01] Adam Fishman: Best laid plans, right. Yeah. So I think that’s great. I want to talk about frameworks. You are a big believer in the Montessori method, which we have some experience with in our family, but can you talk for listeners who’ve maybe heard of it? Can you talk to me a little bit about how that showed up in your life and what aspects of it you really [00:20:22] Colin Anawaty: Liked? Yeah, it kind of tees on this idea, the Montessori program. I think some of the really strong qualities about it is it tries to encourage a sense of independence with your children, which I think is really, really important. And it even goes so far as having kids wash the windows and not as servitude within the home, but to really just start to have them embody some level of they’re responsible and they’re accountable to their toys, not to leave a big mess around. And I think doing that stuff early and allowing for them to engage in independent play as opposed to a mom and dad or the two parents always being a shadow really can develop strength at some point before they move out. You want your children to be comfortable at camp, you want your children to be comfortable doing sleepovers. There’s a lot of pride in owning your own castle or home or bedroom. [00:21:22] Colin Anawaty: And just instilling some of that structure I think is actually good for children. I think it helps them manage stress. If you have a cluttered room, a tidy place is a tidy mind, it really impacts children too. In the same way there’s a lot of science around, especially now with the availability of toys, the cheapness of toys. We can sometimes think ordering more stuff on Amazon, it will keep them engaged longer. The science actually shows the opposite. Fewer toys allows for more creativity. It’s kind of the creative constraints. And so that’s some of this stuff that I think Montessori embodies. The other part of it’s a little bit more tactical, a lot of Montessori stuff is from a product tangibleness perspective, it’s a lot of wood and real glassware and as opposed to toys that are kind of feeding the dopamine drip with electronics and lights and stuff like that. And I just think that’s a really thoughtful approach to raising children, especially in the world where there’s so many lights and flashes around, everyone’s got flat screen TVs, usually multiple TVs plus mom and dad are on laptops, plus the phones light map plus the Apple watch. There’s just a lot of stimuli. And so Montessori is kind of on the other side of the spectrum. [00:22:43] Adam Fishman: And so it’s teaching kids, you mentioned independence, so you can do things on your own. And also a hefty dose of confidence too. I can set out my plate in my cup, I can pour things. And you can do that at a very young age, maybe not without some spills or some messes, but then I can clean it up, all of that sort of stuff. [00:23:07] Colin Anawaty: Yeah, I mean, when you think about your children, they’re often looking at you and wanting to be like you and model adult behavior sooner than a lot of times I think parents are expecting. And so equipping them with the understanding and adoption of some of this stuff, they start to really get into their own and their own element. And I think it’s been really productive. I think for us. [00:23:29] Adam Fishman: On that note too, another thing that you believe really strongly, it’s sort of come up a little bit in this conversation, is accountability. And that accountability is an important thing for kids to learn about at an early age. And we probably wish plenty of people we worked with had learned this at an early age. So why is accountability so important for you? [00:23:50] Colin Anawaty: Yeah, I’ll just kind of back into it at a child level, but I think as adults, the big thing that whether you’re a founder or you’re an executive, you are kind of, the buck stops with you and you’re fully accountable to the team or to your board of directors and investors. And so embodying that maturity can sometimes be the career growth ceiling for some people who are struggling with, call it big business politicking and finger pointing, and the leaders that have coached me and that I’ve aspired to and looked up to, they’re often the first one to fall on a sword for a team and then distribute and allow their team to get the praises where appropriate. And so at a child development level, I just think it’s important. Every action has a consequence. Sometimes it’s a good consequence, sometimes it’s a bad consequence. And as someone who loves video games, one of the genius things about games are these positive and negative feedback loops. And so if we only orient ourselves around positive feedback, then sometimes that can also lead to a worse outcome, whether someone’s gaming the capital markets or someone’s gaming, how to get a promotion as opposed to really understanding and having true consequences around poor decisions, for example. So with children, try not to be too much of a heavy hand and make it feel like it’s severe punishment for making a mistake. Mistakes happen, but also just making sure they understand too that sometimes there’s consequences that could impact somebody else even if they themselves aren’t feeling it. [00:25:29] Adam Fishman: So this sort of fits in with the Montessori method, but where does accountability show up with a three and a half and a 6-year-old in your family? [00:25:41] Colin Anawaty: Wow, let’s think about that one. So I’ve been a little bit guilty now that I’m a single dad, but also selfishly wanting my kids to play some Mario Kart with me. So we just got the Nintendo Switch 2. Oh, [00:25:56] Adam Fishman: Yeah. [00:25:58] Colin Anawaty: Yeah, it’s good. They did a great job. But it’s clear to me when the video game is having a negative impact, it is a dopamine feeder and it can behaviorally cause them to get too spun up. And so if they’re struggling with listening or they’re causing fights amongst each other, then obviously it’s a privilege to be able to play the toy at a very specific level. It can be simple things like that where I don’t want to be an iPad dad, where the iPad’s the solution for everything, but then realizing that they have to self-regulate. Dad also needs to play a part in self-regulating the Nintendo, but if it has negative consequences on their behavior or their mannerisms at the table, then they lose access to it as one would historically expect. But yeah. [00:26:54] Adam Fishman: How good is your three and a half year old at Mario Kart on the Nintendo Switch? [00:26:59] Colin Anawaty: Shockingly good. And it’s even more bizarre to see the beautiful thing about games is it’s an environment with constraints and children just like computer hackers seem to figure out all the nuances. And my 6-year-old has even gone so far as to want to watch YouTubes of people playing these games. And then he’s got a photographic memory and he shocked me, showing me hidden areas and levels that he’s learned. I mean, even at three and a half and six, they’re doing Mario Kart power turns and they know when to hit the gas when the countdowns too. And then the last comment there is just their ability to, and this also teaches me when I’m doing things around the house, even if they’re not directly tuned in, they’re probably on their periphery picking things up. And my oldest and I have played Mario Kart. He’s racing. He knows what his power ups are. He’s telling me which of my power ups to throw on a split screen. He’s monitoring it all. I mean, yeah, the brain’s firing on all cylinders. [00:28:15] Adam Fishman: Whoa, he’s going to be an air traffic controller or something like that as he gets older. [00:28:19] Colin Anawaty: Yeah, it’s mind boggling. [00:28:22] Adam Fishman: So on the subject of accountability, by the way, now I need to go get a Nintendo Switch too. You’ve convinced me on the subject of accountability, you are accountable for the haircuts in your family for cutting your boys’ hair. Which one? That terrifies me mostly my own hair cutting abilities. But you described it as a really great bonding experience. So maybe, I dunno if you have a funny story about that or just what’s it like cutting? First of all, how do you cut a three and a half year old’s hair and get him to sit still and why is it such a great bonding [00:28:54] Colin Anawaty: Experience? I dunno that I have a funny story yet, but the backstory in college, I didn’t have a lot of money. And so for me, having gone to the haircutter, I had asked them, or out of curiosity, do you ever cut your own hair? And so one of them happened to show me do the mirror and how they did it. And so that’s what I did in college. I would just do use clippers and you can buy a set of clippers in the guards all the way up to one and a half to two inches. And so it’s not the best haircut, it’s not going to be layered, it’s not going to have all the things that a professional haircutter is able to do. But when you’re on a budget or you’re doing a really simple voice cut, it’s pretty easy once you get the hang of it. [00:29:41] Colin Anawaty: So I bought some clippers and then I’ll do a big guard. Their hair, two inches is still pretty long, and then just kind of do a little bit of a fade. What I don’t do are things where it’s easy to see mistakes. So like a bald fade, I’m not doing that low. Plus my former wife would kill me if I had done a ball of fade. They have beautiful hair, but it’s a great experience. I still sometimes take ‘em to the barbershop so that they can also get comfortable in that environment. But every couple of months I’ll put them on a bar seat and the kid I bought even has the magic superman cape, which was the way that we had to get them convinced to wear it. And we’ll do a little haircut session. [00:30:25] Adam Fishman: So when will the 6-year-old be old enough to cut the three and a half year old’s hair? [00:30:29] Colin Anawaty: Ooh, good question. I’ll have to come back to you on that one. But yeah, maybe a couple of years [00:30:36] Adam Fishman: And then have either of them asked to cut your hair. [00:30:40] Colin Anawaty: So one of the ways in which I got them comfortable with it was showing it on dad’s head. Unfortunately, I can’t take the clippers off where they could do it without cutting my hair. So they haven’t physically done it, but they’ve seen dad putting up to his head and they’ve gotten really good with it. And I asked them questions, doesn’t that feel good? Dad used to fall asleep when the barber got the shavers out to do the edging and they really enjoy it now. [00:31:10] Adam Fishman: Okay, alright. Well maybe someday they’ll be giving you the fade. You never know. [00:31:15] Colin Anawaty: Yeah, who knows. [00:31:17] Adam Fishman: You have a great story about your 6-year-old and his fear of surfing. Can you tell me about how he overcame his fear of surfing? [00:31:27] Colin Anawaty: Yeah, so this was recent. This was past summer. Growing up in Houston, I would get up early, my dad and I would get up early and go surfing for the day. A lot of people joke that there’s no waves in Texas, but there are. [00:31:39] Adam Fishman: Yeah, I was just wondering about that. More seasonal. Where does one go? Surfing in [00:31:44] Colin Anawaty: Houston along the Gulf, [00:31:47] Colin Anawaty: Surprisingly right before hurricane in the wintertime or something else that kind of got popular as tanker wave surfing. So when a tanker comes in, it can push these big swells in that are rideable. And so Texas does have surfing, but for a 6-year-old, every wave’s pretty big and every wave is also pretty rideable, so light. And so this past summer he was worried about sharks or just the surfboard is. So my dad’s surfboard’s a big long board, which is the easiest for them to learn on, but it’s big. It’s a lot to handle. So we sat around the night before with my dad and watched Bruce Brown’s Endless Summer, which is just a classic. And that kind of got him excited and interested. And then we drove down the seawall and I was pointing out surfers. And then we got out there with a life vest and he comfortable kind of floating and he loves the beach, loves playing in the waves. And then my dad and I got him on the board and pushed him and he body surfed. And the second time, just like he saw in the movies, he stood up and he did arms out, legs out and he rode the wave all the way into the beach. And we were super proud of him. He was really proud of himself. [00:33:02] Adam Fishman: Wow. Warrior pose there. [00:33:04] Colin Anawaty: Warrior pose. [00:33:05] Adam Fishman: Yeah, [00:33:05] Colin Anawaty: It’s great. [00:33:06] Adam Fishman: Wow. He must have been to go from being afraid of sharks to then surfing. Impressive. He must have been so proud of himself. That was awesome. [00:33:14] Colin Anawaty: Yeah, I’m sure he still has a fear of sharks, as do I, but he overcame it. He saw so many people in the water and it was shallow and just reinforced that granddad and dad are going to get eaten before he does. [00:33:26] Adam Fishman: You’re much bigger, much more of a meal for a shark than a 6-year-old. [00:33:32] Colin Anawaty: That’s right. [00:33:32] Adam Fishman: Has a three and a half year old expressed any interest in getting out on the surfboard yet? [00:33:37] Colin Anawaty: We tried, but he was just not quite there yet, but he did. I think he rode the board with us just in embody surf motion, but he also loves the beach, loves doing the sandcastles, things like that. [00:33:51] Adam Fishman: Cool, cool. Alright. I want to talk about social media and not in the way that I think a lot of people would think about because you have a six and a three and a half year old, so they’re not on social media. We all know there’s this growing body of evidence that things like Instagram and TikTok are not the best for kids, but I think you also see them as being kind of dangerous for parents too. And so why is that? [00:34:16] Colin Anawaty: Well, number one, Texas just rolled out a policy. So there were no cell phones, electronic devices allowed in school anymore, which I [00:34:24] Adam Fishman: Saw that [00:34:25] Colin Anawaty: There are things I disagree with happening in the Texas Lodge, but this is one that I think it’s a really good thing for kids. I think with parenting, and this is true really on any topical basis, but there are a lot of people who are promoting themselves as self-proclaimed experts or call it influencers, but there’s not always a lot of ways in which we can validate, especially the way the algorithms just suggest, Hey, this is something you might be interested in. And so for me, as someone who likes, I’m a product manager by training, I always want to look at the data and look at the outcomes to help guide decisions. There often seems to be a lack of, is this a credible source? Are even the statistics that are being quoted credible or is it just manufactured for likes, follows, things like that. And unfortunately, the way the algorithms work, if you find X, Y, Z, then you’re going to get fed more of that. And so whether it’s social media or the internet, humans have a tendency to self-select. And it’s not so much invalidate my feeling, but validate it is what our tendency is as humans. And so I think that feedback loop, if it’s a call it a perverse idea, that one can be not great, getting validation that the way you may be parenting or the way you view the world is the right way. I don’t know how that gets solved today based on the way the algorithms are suggesting things based on what you’ve already looked at. [00:36:03] Adam Fishman: Maybe just it gets solved by throwing your phone in the other room or something like that. Deleting Instagram and TikTok. [00:36:10] Colin Anawaty: Well, and kind of reflecting on what your other question, which is what would I have told myself before having parents? I think animals, humans, we’ve been having and creating children since the beginning of the earth, so to speak. And we’re kind of naturally born with a gut instinct around our children. And sometimes hopefully if you’re a good human, that’s a strong instinct and you probably know what’s best for your children. You don’t always need an expert to necessarily tell you. [00:36:42] Adam Fishman: Yeah. Oh, that’s really good. Ignore the Instagram and TikTok advice. You got this parents on that note, you mentioned Texas just banned cell phones for kids. Is it all the way through high school? You can’t have them in school? I think. [00:36:56] Colin Anawaty: Good question. I think so my surface level understanding right now is just all public schools. K through high school. [00:37:03] Adam Fishman: Yeah. Yeah. We’re also working on, well, the state of California, you have to have a policy. It does not say what that policy has to say, but we’re working on our ways towards a full on ban here in our school district. When you think about the relationship that you want your kids to have with technology, and obviously like you said, your product manager by trade, you work in technology, you invest in technology, you’ve built technology companies. It is hard to think about it a little bit because your kids are six and three and a half. But what do you think about the relationship that you want them to have with technology as they get older? [00:37:43] Colin Anawaty: Also, a really good question that I’m just candidly starting to struggle with. I don’t see science and technology by any structure of the imagination going away. It’s going to be a cornerstone to how societies even survives wherever the earth is going, so to speak, from climate change and just general sustainability. But with the rapid pace of innovation in ai, I’m now starting to worry where is that entry level opportunity for everybody to learn your trade, learn your craft, because those are the jobs that are already getting wiped out. The idea that I need a business and the list is now Claude or ChatGPT, the idea that I need an entry level engineer to write some unit tests or do some bug squashing, that’s an AI native IDE now. And so I’m just kind of generally worried about where they can take a career and especially in a decade from now when this stuff’s so much further along, that’s going to give them the right jumping off point to become a master in whatever that thing is that they’re interested in. [00:38:54] Colin Anawaty: So for me today, it’s still introducing them to technology, but also as a parent, not trying to force them round peg into a square hole. Just because dad was a technologist doesn’t mean they need to follow that path. I think they’d, both of them have their own natural intuition, and I’m already seeing strengths and weaknesses in each. I think at the end of the day it’s cliche, but wherever they’re really, really passionate about, I think there’s so much energy when you find something that you truly love, that especially this day and age, you can make money doing anything. You just have to become kind of the best or really, really have the expertise that sets you apart. And I think the only way you really get there is continued investment in that area, a lot of mentorship and just really leaning into that thing that you love that just keeps you up at night. And so as much as I’d like them to maybe one day have a family business that we’re kind of working around, I don’t know that it’s going to necessarily be modeled or the expectation from me is that it has to be a pure play technology company. In fact, I’ve started to look and explore, it’s something private equity has done really well, but where can we build some service-based businesses that are family owned and then bring some technology expertise behind the scenes but are a little bit more anti AI so to speak? [00:40:28] Colin Anawaty: Is AI really going to replace some of these other, call it blue collar type industries? [00:40:34] Adam Fishman: Very likely not unless you can get a fully functional robot that can do plumbing. And I think we’re ways away from that. So [00:40:41] Colin Anawaty: Yeah, agreed. [00:40:42] Adam Fishman: Yeah. Okay. Speaking of AI, I’m very curious about your use of AI as a parent. So what’s the most creative thing that you’ve done with AI as a dad? [00:40:54] Colin Anawaty: Yeah, so this sounds like I’m talking out of both sides of my mouth, but I have definitely used AI for helping me understand certain kind of conversational or parenting frameworks around how to talk to the child about a certain situation, specifically the divorce, so to speak, [00:41:13] Colin Anawaty: But in a more playful sense. Funny enough, this is what I saw on social media or Reddit, but it was taking their drawings and then prompting it to create this kind of realistic 3D version of what they had sketched and blew my mind, blew their mind. Also, you could just, the sparkle in their eye when they saw their character that they had loosely done with crayon really come to life. And I just thought it was one incredible at how accurate and specific the AI was able to see what was sketched so loosely and turn it into something. It just was mind boggling. But then it just kind of reinforced their creative engine. They just wanted to keep drawing and do more of it. And so it was kind of a cool experiment for the both of us. [00:42:06] Adam Fishman: Nice. And so that was kids draw something like a monster or a building or something on a piece of paper with crayons, and then you sort of feed that into ChatGPT and say, Hey, turn this into the real life version of the thing. [00:42:24] Colin Anawaty: They’re into the Nintendo obviously, but I certainly watch cars a million times. So I mean, you can prompt it stylistically, make this look like a Pixar movie or make it look like a Nintendo Mario in terms of the rendering and the kind of stylistic characteristics. And it comes out just like that. It’s pretty shocking. [00:42:42] Adam Fishman: Oh, awesome. Very cool. Well, maybe we can link to some of those in the show notes. You told me, and you kind of mentioned this and I can hear it a little bit when we’re talking, is that you have a little bit more maybe fear and skepticism over AI than unbridled optimism, and that’s a first for you. So I’m curious about why that is. [00:43:06] Colin Anawaty: I like to fancy myself as kind of someone who is an entrepreneur who’s trying to do work in an area that’s going to super serve society. And for the most part in the last 10 years, it’s been financial access and healthcare. And so my worry with AI is not how impressive it is or that it can create, call it super contributors, people who are just able to have this co-partner, so to speak, that’s almost a reflection of their already great qualities. But it’s kind of what we talked about, which is where are entry level folks going to really learn what I’ve learned through 20 years to be able to prompt it the right way to have so much experience to kind of know how to guide the AI to produce the output and the results that embody some of that experience and learnings along the way. [00:43:59] Colin Anawaty: And so as I mentioned, I’m already seeing numerous companies where they’re freezing success roles or they’re freezing these entry level roles or business analyst roles and those just aren’t getting hired. And so where over the last couple of decades, whether it’s 2008, whether it was the pandemic, we’ve had groups of people coming out of college where the job market was just not healthy. And I think it’s kind of had long-term impacts on some of those folks. And so now this one’s even broader for the most part, and it’s continuing to kind of chew its way from the bottom up. So that’s what keeps me up at night because it’s not just about the kids in college right now, it’s also how in 10 years is this going to really reflect things for the kids? My optimistic way of looking at this as someone who has their dual citizenship in Italy and looks forward to retiring in Europe, maybe it means we get time back as a society in a way that America has not embodied very well to be able to do some of those cultural or crafting, whether it’s to open a bakery and really become as good as the French are and pastries and things like that. [00:45:11] Colin Anawaty: And so maybe we’ll slow down a little bit because we’ve got all these worker agents doing the things that people are spending 60 hours a week and not spending time with their children. So I’m going back and forth on what this is going to mean for society [00:45:27] Adam Fishman: Every week. A different thought on this one. So yeah, who knows? And like you said, your kids are still really young, so a decade from now they’ll be in high school, not even yet college. So who knows what that’s going to look like. But yeah, I think that’s really interesting. And yeah, it is. AI is quite an interesting and disruptive for good for bad technology. So time will tell, we shall see. I wanted to end with a couple of things. One is somebody might listen to this conversation and think, oh, Colin, he’s got it all figured out. He seems really calm and in control. And I think you’ve said you’ve had some people tell you that before and you don’t really feel that way. And so I’m curious why that is. And yeah, I’m just curious about that [00:46:17] Colin Anawaty: Since I was young in kind of spirit of my comment on find something that you just really absolutely love. For me, it really was technology. In the nineties, there weren’t a whole lot of people or curriculum to teach you how to program or the way the web was shaping up. And so a lot of that was just knowledge that I accumulated through self-teaching my way through what is now my career. But part of that was a lot of conviction that I knew that this is what I love doing. And so as a byproduct of that, sometimes people felt like, oh, well, Colin’s off to the races. He knows exactly where he is going in life. We kind of let started this conversation off, I am a single dad and I can tell you this has been the hardest thing in my life and I’m going through a complete reset, both understanding and taking on new parenting roles that sometimes were associated with my partner to having my whole social network. [00:47:15] Colin Anawaty: Now all my friends generally are married with kids, and so I have time now where I don’t have the children, but I don’t have a lot of friends to hang out with. Kind of just introspectively reflecting on the marriage and where I wasn’t showing up appropriately as a partner. And then through the sale of my last business in November, just having to reset as an entrepreneur, what do you want to do next? And so for me, while I feel like I have strong opinions about things or I’ve figured some stuff out historically, the next chapter is very unwritten Right now it’s scratch notes, I’m crumpling things up, throwing ‘em away more often than I’m feeling really good about. So yeah, I think life is a journey. Fortunately, I’ve got great friends. I love my children, I love what I do. So there’s bright spots that help me stay oriented, but I’m still to get to this, even though you can see the stars in the moon, it’s a long process to get there. [00:48:17] Adam Fishman: Yeah. The journey is the destination, as they say. So you’re in that journey again. Okay. Well, to end, how can people follow along or be helpful to you on this journey? [00:48:30] Colin Anawaty: Oh, great question. Well, I am not as active on social media like I used to be, but I welcome any feedback, advice. Send me an email Collin, C-O-L-I-N, at flying a capital.com or find me on LinkedIn and drop me a note and I’d love to hear it if anyone has any advice on single parenting and kind of the next mountain. [00:48:50] Adam Fishman: Okay. We will direct folks there in our show notes. Let’s end with lightning round, very simple rules. I ask you a question and you say the first thing that comes to mind, and this is a safe space and a judgment-free zone. So are you ready Colin? [00:49:09] Colin Anawaty: Let’s go. [00:49:10] Adam Fishman: Okay. What is the most indispensable parenting product that you’ve ever purchased? [00:49:16] Colin Anawaty: The toilet bowl thing. That makes it smaller for the children to easily sit on and learn how to poop on their own and get rid of diapers. [00:49:24] Adam Fishman: Amazing. What is the most useless parenting product you’ve ever purchased? [00:49:29] Colin Anawaty: Oh God. Probably too many to count. Probably these novel cups that just don’t seem to work well to get a child to drink from ‘em. I just have found, barring in mind, the ones that help not spill, there’s just too many of these assistive eating and drinking things, and most of ‘em just don’t really work well. You just need them to learn how to use a cup. [00:49:49] Adam Fishman: Yeah, the Montessori method would say, just give ‘em a cup. Just let ‘em spill. What is the weirdest thing you’ve ever found in your kids’ pockets or in the washing machine? [00:50:00] Colin Anawaty: Probably one of dad’s screwdrivers or tools along with some screws and wondering what was end done. [00:50:10] Adam Fishman: Yeah, there’s a two-parter there. There’s boy, what is in the pocket here. And then there’s also, where did this come from? [00:50:17] Colin Anawaty: Yeah, what chair’s about to fall apart. [00:50:19] Adam Fishman: That’s right. True or false, there’s only one correct way to load the dishwasher. [00:50:23] Colin Anawaty: Oh, this is a great question. True. You are either a rabid raccoon who just throws everything in the dishwasher with food on it, or you’re kind of an architect and you pre-wash. I think of the dishwasher as a sanitation device because once that heater turns on, if there’s food on it, it’s stuck on it. [00:50:42] Adam Fishman: So you’re more of a pre-wash, put it in there. Very nicely organized. Every dish has its place. Okay, cool. [00:50:48] Colin Anawaty: That’s right. [00:50:49] Adam Fishman: Same, by the way, same. What is your signature dad’s superpower? [00:50:53] Colin Anawaty: I like to think I’m still a child at heart, whether it’s games, love sitting down with the kids and playing with Legos. So for me, it’s kind of continuing to enjoy the things that I had always grown up really liking. And so whether it’s playing Mario Kart or letting our imagination run wild with Legos, I enjoy it. I will spend hours in front of the Lego box. [00:51:16] Adam Fishman: Awesome. What is the craziest, crazier a block of time in your house? 6:00 AM to 8:00 AM or 6:00 PM to 8:00 PM [00:51:25] Colin Anawaty: To your point about school starting, it’s definitely 6:00 AM to eight to 8:00 AM [00:51:30] Adam Fishman: Morning’s a little chaotic, huh? [00:51:32] Colin Anawaty: Yeah. [00:51:32] Adam Fishman: Yeah. [00:51:33] Colin Anawaty: Breakfast, packing the lunches, getting them dressed, getting them out the door so they’re not tardy. And daycare, you don’t have to worry about that, but with public schools, they have to be there between seven 30 and seven 40. [00:51:46] Adam Fishman: Ooh, that’s early, man. If your kids had to describe you in one word, what would it be? [00:51:52] Colin Anawaty: Hopefully engaging. Hope. That’s the word that they would say. [00:51:55] Adam Fishman: Cool. What is the funniest or perhaps most embarrassing thing one of your kids has ever said in public? [00:52:03] Colin Anawaty: A lot that I can’t even repeat. They’re just not a proof. Probably one that came up was questioning gender of someone. I think it was the chef at a restaurant and asking me, dad, is that a man or a woman? Loud enough for them to hear. But that was an awkward moment. [00:52:24] Adam Fishman: Okay. We’ve gotten a few of those like that on this show. So you’re not alone. You’re not alone. What is your go-to dad wardrobe [00:52:34] Colin Anawaty: On the weekend? It’s probably some athleisure flows. I’ll not name any brands, but probably the thing I’m doing most often now is I’ve got a dad purse loaded with snacks, sometimes a charging device, but I’m frequently seeing now with my man Mers. [00:52:56] Adam Fishman: Okay. Your cross body bag, as they say, that’s the technical term, which also the athleisure brand sell, so there you go. [00:53:03] Colin Anawaty: That’s right. [00:53:03] Adam Fishman: How many parenting books do you have in your house? [00:53:06] Colin Anawaty: We used to have a ton. I no longer feel I need the parenting books yet. I’ll probably revisit them when they start to become tweeners teenagers. But yeah, there’s some really great ones out there. Titles are escaping me now, but happy to send you some links to ’em. [00:53:22] Adam Fishman: Would you say that you’ve ever read any of them cover to cover? [00:53:26] Colin Anawaty: I did. There were I think two books. Gosh, I wish I could think of the name right now. But I did read them cover to cover. And one of the books that I think is also important, especially in a traditional husband wife scenario, is just understanding what your wife is going to go through this first couple of years being the primary nurturer to the children because they’re dependent on her for food. So understanding not just the child rearing, but also the supportive role. [00:53:56] Adam Fishman: Okay. Well if you do think of them, send ‘em to me. We’ll put ‘em in the show notes, but no worries. If not, it’s okay. Alright, we’re in the home stretch. How many dad jokes do you tell on average each day? [00:54:08] Colin Anawaty: It’s increased, and again, talking out of both sides of my mouth, there’s a really funny Instagram just filled with dad jokes. Sometimes they feature babies telling these dad jokes and they’re hilarious. And then I did buy a book just for kids’ jokes and my oldest loves it. And we’ll sit around. I mean, they’re the silliest things, knock who’s there type jokes, but we’ll sit around and read those out and he loves ’em. [00:54:33] Adam Fishman: Okay. What is the most absurd thing one of your kids has ever asked you to buy for them? [00:54:40] Colin Anawaty: The Nintendo Switch 2. [00:54:41] Adam Fishman: Okay. And you [00:54:42] Colin Anawaty: Did? And I did. It was their one. They’d gone through this big life transition, and then my oldest started kindergarten last week. He was very demanding about it for months because somehow he got exposed to it. And so I try to not shower them with presents, make it birthday Christmas and not spoil them. But this one I felt he was deserving of. And [00:55:05] Adam Fishman: Also, it’s fun for you too. It’s fun [00:55:08] Colin Anawaty: For me too. There you [00:55:09] Adam Fishman: Go. What is the most difficult kids TV show that you’ve had to sit through? [00:55:15] Colin Anawaty: Barring the repetition of Pixar movies, like cars that I think I’ve watched at least a million times. The one as of late is Milo and Chip, which is based on Minecraft. And the voices are nails on a chalkboard and they love it. [00:55:34] Adam Fishman: Okay. Okay. What is your favorite kids movie [00:55:39] Colin Anawaty: Seasonally? I really liked the new Grinch, the one that was filmed, created in 2019. I thought it was awesome. They also loved to watch that all the way through spring so it didn’t feel so seasonal. And then the Pixar movies, especially ones as of late, like the one about emotions. I thought that was a Yeah. Inside [00:56:00] Adam Fishman: Out. [00:56:00] Colin Anawaty: Inside Out. Yeah. [00:56:01] Adam Fishman: What nostalgic movie can you just not wait to force your boys to watch with you? [00:56:08] Colin Anawaty: This one was a little bit too soon and so I had to turn it off, but it was Indiana Jones. [00:56:13] Adam Fishman: Oh yes. Temple of Doom. Temple of Doom. Do you remember that movie is rated G and there is a scene where a man pulls a still beating heart out of another man’s chest. That doesn’t seem like a G rated movie to me. [00:56:27] Colin Anawaty: No. And that’s when I had to turn that one off. But the one that we did watch that I grew up and I still love, and it inspired some of the Bamboo activities as a kid with Swiss family [00:56:37] Adam Fishman: Robinson. Oh yeah. And they love that one. Okay. What is the worst experience you’ve ever had assembling a kid’s toy or a piece of furniture? [00:56:45] Colin Anawaty: I wouldn’t say I’ve had a bad experience. I grew up, I’ve got a garage full of power tools, so I might just reframe it as the best experience. And my oldest and I built their bunk beds. [00:56:58] Adam Fishman: Oh, nice. [00:56:58] Colin Anawaty: And it came flat packed and it was a project, but it was great. We built it and then now he sleeps in it. Cool. So I think he’s really proud of it. [00:57:07] Adam Fishman: Colin, this is where you and I would be opposites because that would be the worst experience for me. But I’m glad it worked out for you. Two more for you. Do you have a favorite back in my day story to tell your kids yet? [00:57:22] Colin Anawaty: Gosh, I’m going to sound like an awful dad, but it’s talking about the original Mario in NES and it was just not, it was 2D. It was very blocky. And so when we got the switch, you can see on there, you can download the emulators and play the old games. So because he’s heard me talk about it so much, he loves the Super Mario series and he really wants to play that one [00:57:47] Adam Fishman: Still. I would say some of the greatest video games of all time are the 2D Super Mario series. So you don’t feel bad about that one in the least. Okay. Last question. What is your take on minivans? [00:58:02] Colin Anawaty: I am not a minivan dad. I would probably never buy one. Although I’ve had my fair share traveling with the kids of renting one. And I understand, I understand why they are so great for families. Double sliding doors, all that good stuff. [00:58:21] Adam Fishman: Yeah. But you draw the line right now at the Mers? At the wearable, [00:58:25] Colin Anawaty: At the me. [00:58:26] Adam Fishman: Okay. Alright. Well, Colin, that sounds like a great place for us to wrap up. Thank you so much for joining me today. Congratulations to your oldest for starting kindergarten, and I wish you and your fam all the best of luck as you head into this school year. And the rest of this year. [00:58:45] Colin Anawaty: Hey, likewise, Adam. This was really a unique pleasure. Really excited to hear the podcast and appreciate you me on. [00:58:52] Adam Fishman: Thank you for listening to today’s conversation with Colin Anawaty. You can subscribe and watch the show on YouTube or wherever you get your podcasts. Just visit www.startupdadpod.com to learn more and browse past episodes. Thanks for listening and see you next week.