Latest / Startup Dad / Why I Stepped Down to Spend More Time With My Son | Ankit Gupta (Dad of 1, Founder of Bicycle Health)

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Why I Stepped Down to Spend More Time With My Son | Ankit Gupta (Dad of 1, Founder of Bicycle Health) · Startup Dad

• [00:00:00] Ankit Gupta: I think the best thing I can do is just, like, sit with my kid and hang out essentially. My favorite time of the day is the morning right after he wakes up. He wants milk, I give him milk. And we just, like, sit on the couch. We might be reading a book. We might be, like, doing a puzzle [00:00:16] Ankit Gupta: together, whatever. Or we might just be, like, sitting, just, like, hanging out. That is what I wanna do as much as I can. [00:00:23] Adam Fishman: Welcome to Startup Dad, the podcast where we dive deep in the lives of dads who are also leaders in the world of startups and business. I'm your host, Adam Fishman. What happens when a serial founder, after nearly a decade of building, suddenly finds that the thing pulling him hardest isn't the next company, it's his kid? [00:00:45] Adam Fishman: Today, I'm joined by Ankit Gupta, founder of Bicycle Health, a company he built and led for nearly nine years before handing the CEO seat to his successor earlier this year and becoming a stay-at-home dad. Before Bicycle, Ankit co-founded Pulse, a news app that caught the attention of Steve Jobs, and then in the same breathtaking day, got pulled from the App Store before ultimately being acquired and sold to LinkedIn. [00:01:11] Adam Fishman: Ankit is a dad of one, a two-year-old son, and his wife is a transplant nephrologist in the middle of a grueling fellowship. Today, we talked about what really happened behind the polished press release when Ankit stepped back from Bicycle Health and why it took 18 months of internal reckoning to get there. [00:01:29] Adam Fishman: The dopamine desert of trading founder life for full-time dadhood and the genuine turbulence that followed. How Ankit and his wife navigate co-parenting across two extraordinarily demanding careers, taking turns holding each other up. The philosophy that only two things a parent can truly offer are time and love, and why Ankit sees entrepreneurship as one of the most family-friendly career paths, if you're willing to design it that way. [00:01:54] Adam Fishman: 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 Ankit [00:02:06] Adam Fishman: Welcome Ankit Gupta to Startup Dad. Ankit, it is my pleasure having you here today. Thanks for joining me [00:02:12] Ankit Gupta: Yeah, of course. I'm excited for this [00:02:14] Ankit Gupta: conversation [00:02:14] Adam Fishman: maybe not quite as much as I am. We were already just, like, riffing in the green room, and I just, like, cannot wait to dive into it. you've been a serial founder. in January of this year, you handed the CEO seat at a company called Bicycle Health, which you, you founded or co-founded, um, to a guy named Rick Dean. [00:02:33] Adam Fishman: and in the press release, you said you did the classic kind of founder press release thing, which I- I'll allow you that. you said, "The company is established. It's growing sustainably. It's time for me to take a step back." so that's sort of like the corporate, like, polished version. Like, what was happening under the hood there? [00:02:50] Adam Fishman: What's, what's the, what's the, like, untold story behind why you decided to step back from Bicycle? [00:02:55] Ankit Gupta: it [00:02:56] Ankit Gupta: doesn't happen overnight that you hire a CEO and, you know, [00:02:59] Ankit Gupta: hand over [00:03:00] Ankit Gupta: the reins. So, [00:03:01] Ankit Gupta: it probably took, [00:03:02] Ankit Gupta: 18 months or more of, coming [00:03:04] Ankit Gupta: to terms with [00:03:06] Ankit Gupta: the fact that this is what I wanna do, communicating it to the board [00:03:11] Ankit Gupta: and my wife first, [00:03:12] Adam Fishman: Mm-hmm. Your, your number one board member, your [00:03:16] Adam Fishman: wife. Yeah, [00:03:17] Ankit Gupta: yeah, yeah, primary. and actually going out and looking [00:03:19] Ankit Gupta: for someone. [00:03:20] Ankit Gupta: I mean, I think it all started basically when my son was born. he's two years old now, so it was right around, [00:03:25] Ankit Gupta: you know, two [00:03:26] Ankit Gupta: years ago. [00:03:27] Ankit Gupta: and the company was in a pretty pivotal point at [00:03:30] Ankit Gupta: that time. [00:03:31] Ankit Gupta: it sort of like the [00:03:32] Ankit Gupta: company, you know, uh, grew really quickly and got [00:03:35] Ankit Gupta: to a pretty [00:03:35] Ankit Gupta: stable place [00:03:36] Ankit Gupta: right around when my son was born. [00:03:39] Ankit Gupta: And so it almost felt like everything aligned, and I started [00:03:42] Ankit Gupta: feeling [00:03:42] Ankit Gupta: more and more like, [00:03:44] Ankit Gupta: what is my real calling, you know, here? Like, [00:03:47] Ankit Gupta: I truly believe in, [00:03:48] Ankit Gupta: you're kind [00:03:49] Ankit Gupta: of [00:03:49] Ankit Gupta: pulled [00:03:50] Ankit Gupta: to do something. Like, you kind of know what you're supposed to do, you know? And I feel like it wasn't a [00:03:57] Ankit Gupta: coincidence that the company [00:03:59] Ankit Gupta: got to a pretty good place as my son arrived on the scene, and I, I felt like I was pulled to [00:04:05] Ankit Gupta: just, like, be [00:04:06] Ankit Gupta: more of a dad than I, I, I was. [00:04:08] Ankit Gupta: and it was [00:04:09] Ankit Gupta: really hard to do that while also running a company, to be, like, fair [00:04:14] Ankit Gupta: to, [00:04:14] Ankit Gupta: to everyone. [00:04:15] Ankit Gupta: pretty much a year before that, [00:04:17] Ankit Gupta: so January of, [00:04:18] Ankit Gupta: of, [00:04:18] Ankit Gupta: uh, you know, [00:04:20] Ankit Gupta: 2025, I decided that it, it's, it's time to, to make a change. [00:04:25] Ankit Gupta: it took me a while to build up the courage to be able to, [00:04:30] Ankit Gupta: like, [00:04:31] Ankit Gupta: really [00:04:31] Ankit Gupta: talk about [00:04:31] Ankit Gupta: it with people and [00:04:32] Ankit Gupta: really start acting on it. [00:04:34] Ankit Gupta: and [00:04:34] Ankit Gupta: yeah, I, I was really fortunate that I only started [00:04:37] Ankit Gupta: the search for a CEO in Q-- late Q3, early Q4, and, and we found Rick through, [00:04:44] Ankit Gupta: a [00:04:44] Ankit Gupta: common board member fairly quickly [00:04:46] Ankit Gupta: and, and he's incredible, and he's come on and, you [00:04:49] Ankit Gupta: know, he's [00:04:49] Ankit Gupta: doing a great job. And [00:04:50] Ankit Gupta: he's, he's really taking the company where it needs to go. [00:04:54] Ankit Gupta: it just [00:04:54] Ankit Gupta: feels like the stars all aligned [00:04:57] Ankit Gupta: to, uh, allow me to, you know, not, not have a job. [00:05:01] Adam Fishman: Yeah. [00:05:01] Ankit Gupta: Yeah. Yeah. [00:05:03] Adam Fishman: Well, and of course you do have a job, uh, just maybe not one for pay. know, one of the other things you told me in [00:05:11] Ankit Gupta: Which is like running a startup, [00:05:12] Adam Fishman: Yeah. For the [00:05:13] Ankit Gupta: most part. [00:05:14] Adam Fishman: Yeah. So, you know, you told me one of the things, in doing, you know, in the run-up to this, call that you made, that, um, you know, one of the reasons you stepped back was to be a full-time dad. [00:05:26] Adam Fishman: and you stepped back so that your wife could step in. She has a very demanding fellowship as a nephrologist, which is a kidney doctor for, um... And she does transplant surgeries, which is like, holy cow, we need a lot of those in the world. kidneys and transplant doctors. her hours are brutal, right? [00:05:43] Adam Fishman: Like, everybody knows, like, startup founder is one thing, but, like, doctor in a fellowship, like, forget about it, you know? was your wife, uh, the first person that you went to to, like, have this conversation and sort of tell her that you'd gotten to this decision? Obviously, you mentioned this kind of before the board, but many discussions with your wife leading up to this? [00:06:03] Ankit Gupta: So my wife is, you know, she's, she's doing a fellowship in transplant nephrology, so she's actually helping patients who get a kidney transplant to sort of, after the transplant, [00:06:12] Ankit Gupta: you know, stabilize the kidney and sort of make sure the kidney [00:06:15] Ankit Gupta: functions for, for a long time. [00:06:17] Ankit Gupta: and it is [00:06:18] Ankit Gupta: extremely demanding. [00:06:19] Ankit Gupta: She actually had [00:06:21] Ankit Gupta: our son when she was doing her nephrology fellowship, [00:06:25] Ankit Gupta: and [00:06:26] Ankit Gupta: like people say, there's no good [00:06:27] Ankit Gupta: time to have a kid, and we certainly found that out. Like, it wasn't a good time to, [00:06:32] Adam Fishman: You maybe picked the absolute worst time [00:06:35] Ankit Gupta: Yeah, I mean, it was hard. It was hard. [00:06:37] Ankit Gupta: and then she knew that she wanted to take the next step and do a transplant nephrology fellowship. [00:06:41] Ankit Gupta: So, [00:06:42] Ankit Gupta: so we [00:06:42] Ankit Gupta: kind of knew how hard it was gonna be, [00:06:44] Ankit Gupta: thankfully. [00:06:45] Ankit Gupta: And, in some ways I'm very [00:06:47] Ankit Gupta: fortunate that I [00:06:48] Ankit Gupta: was able to [00:06:48] Ankit Gupta: take [00:06:49] Ankit Gupta: this [00:06:49] Ankit Gupta: time off to be able [00:06:50] Ankit Gupta: to support her.it wasn't necessarily because of her [00:06:54] Ankit Gupta: having a [00:06:55] Ankit Gupta: demanding job I decided [00:06:56] Ankit Gupta: to take [00:06:57] Ankit Gupta: this [00:06:57] Ankit Gupta: step. Like, [00:06:58] Ankit Gupta: internally, I just started feeling like [00:07:01] Ankit Gupta: I [00:07:01] Ankit Gupta: want to spend a lot of time with my son. [00:07:05] Ankit Gupta: and [00:07:07] Ankit Gupta: I love co-parenting [00:07:08] Ankit Gupta: with [00:07:08] Ankit Gupta: my wife. And [00:07:10] Ankit Gupta: so, like, [00:07:11] Ankit Gupta: whatever [00:07:11] Ankit Gupta: free time [00:07:12] Ankit Gupta: she has, you know, I want to be present for that, and I want to [00:07:15] Ankit Gupta: do that [00:07:16] Ankit Gupta: together, and, and all the time I can possibly [00:07:19] Ankit Gupta: spend with my son in a, in a nice and healthy way, like I want to do that. So intrinsically, [00:07:23] Ankit Gupta: I was pulled towards that. [00:07:24] Ankit Gupta: I was also... You know, I had, I had run Bicycle for like eight or nine [00:07:28] Ankit Gupta: years, and [00:07:28] Ankit Gupta: I feel like I'd gotten [00:07:29] Ankit Gupta: it to a really good place where, you know, I, [00:07:33] Ankit Gupta: I felt [00:07:34] Ankit Gupta: satisfied. in some ways, that's like the worst thing you could have as [00:07:37] Ankit Gupta: a founder. Like, you kind of need that, you know, urge, like that, that sort of [00:07:42] Ankit Gupta: anger. [00:07:42] Ankit Gupta: and you can't really manufacture that. I don't know if it [00:07:46] Ankit Gupta: was because [00:07:46] Ankit Gupta: my son was born or because the company became profitable or whatever, a whole host of reasons, but, [00:07:51] Ankit Gupta: it felt [00:07:52] Ankit Gupta: like what was pulling me was, y- [00:07:54] Ankit Gupta: let the company [00:07:54] Ankit Gupta: be run by someone who, who brings that, [00:07:57] Ankit Gupta: hunger while I [00:07:59] Ankit Gupta: can be fully present and [00:08:01] Ankit Gupta: focused on, on, on my family. [00:08:04] Ankit Gupta: and, and it just happened to be that, y- you [00:08:06] Ankit Gupta: know, this is a period of tough kind of work, life for, for my wife, [00:08:10] Ankit Gupta: but [00:08:11] Ankit Gupta: she's seen [00:08:11] Ankit Gupta: the same with me. [00:08:12] Ankit Gupta: You know? I, I've had times where I've [00:08:14] Ankit Gupta: been, [00:08:17] Ankit Gupta: like, 200% working hard and being super occupied, and, and she's really supported me in that way. So I, I feel like it's not [00:08:23] Ankit Gupta: like we kind of [00:08:24] Ankit Gupta: negotiated and planned. [00:08:25] Ankit Gupta: It just sort of naturally happening. and, and [00:08:27] Ankit Gupta: and I feel really grateful for [00:08:28] Ankit Gupta: that. Like, as [00:08:29] Ankit Gupta: a startup founder, [00:08:30] Ankit Gupta: someone who's gonna do [00:08:31] Ankit Gupta: many more startups, I, I feel like my wife [00:08:34] Ankit Gupta: needs to be supportive in, in that way. And, [00:08:37] Ankit Gupta: and she definitely didn't know what she was getting into when she [00:08:39] Ankit Gupta: married me. [00:08:40] Ankit Gupta: so fortunately, it's, [00:08:42] Ankit Gupta: it's sort [00:08:42] Ankit Gupta: of working out. [00:08:43] Adam Fishman: so I have two, two kind of follow-up questions to that. One is, so it sounds like for a long time you were pulled to be a founder and you were pulled to your work and solving the problems that Bicycle was solving in your previous company, which we'll, we'll touch on a little bit. And then the pull changed, and the pull was towards your family and your son and your wife and sort of being, stepping up there. [00:09:07] Adam Fishman: and so it didn't make it as hard for you because just the direction that you were being pulled in just naturally kind of flowed into a new season of life. All that being said, you were running companies since you were a grad student. Like, you started a company when you were at Stanford, um, which you then sold to LinkedIn eventually. [00:09:26] Adam Fishman: and then you did Bicycle, like you were at LinkedIn for a while, then you did Bicycle. what was it like to wake up w- like the next day with n- with no company and with like a little kid like staring at you? [00:09:38] Ankit Gupta: Oh my God. And, [00:09:39] Ankit Gupta: and it was actually a really hard time for us too because he was going [00:09:43] Ankit Gupta: to daycare, uh, or [00:09:45] Ankit Gupta: preschool, for a few months [00:09:47] Ankit Gupta: and he was really having a [00:09:48] Ankit Gupta: lot [00:09:48] Ankit Gupta: of fun. He [00:09:49] Ankit Gupta: was growing a lot. [00:09:50] Ankit Gupta: The teachers were great. And the preschool suddenly [00:09:53] Ankit Gupta: closed down. [00:09:53] Ankit Gupta: Like they suddenly went bankrupt, like with... [00:09:56] Ankit Gupta: Like they gave [00:09:57] Ankit Gupta: us a week's notice and then they said there's no school [00:09:59] Ankit Gupta: next week. [00:10:00] Adam Fishman: By the way, just to interject, that is a thing that happens quite a bit more often than people think. Like, it, it really is. It really [00:10:09] Ankit Gupta: I get it, running a business is hard, but like let's talk about [00:10:12] Ankit Gupta: it, right? Let's figure this out. [00:10:14] Adam Fishman: Do you need a loan? You know? Like, yeah, Okay, so the rug got pulled out from under, under you [00:10:19] Ankit Gupta: Yeah. [00:10:19] Ankit Gupta: So basically, it wasn't even a month after I had left Bicycle that, he was at [00:10:26] Ankit Gupta: home 24/7. we had all these plans to like exercise, read, travel, whatever, you [00:10:36] Ankit Gupta: know, fix [00:10:36] Ankit Gupta: up our house. [00:10:37] Ankit Gupta: But now [00:10:38] Ankit Gupta: we were like full-time parents. [00:10:40] Ankit Gupta: so it was really tough. And my wife had to travel a lot for her family. She went to India and spent a bunch of [00:10:45] Ankit Gupta: time. So I, I kind of ended up becoming [00:10:48] Ankit Gupta: a, a, a full-time [00:10:49] Ankit Gupta: solo dad for, for a few weeks. [00:10:51] Ankit Gupta: I think those were some hard weeks. [00:10:53] Ankit Gupta: Like, I truly questioned, like, did I make the right decision, [00:10:56] Ankit Gupta: actually? [00:10:57] Ankit Gupta: the [00:10:57] Ankit Gupta: thing that I missed the most was, [00:10:59] Ankit Gupta: some [00:11:00] Ankit Gupta: feeling of appreciation basically. Like, [00:11:02] Ankit Gupta: you solve problems. At work, [00:11:04] Ankit Gupta: I love [00:11:04] Ankit Gupta: solving problems. [00:11:05] Ankit Gupta: Like you're making progress, you're [00:11:06] Ankit Gupta: solving problems, you're talking to someone, you're helping them overcome [00:11:10] Ankit Gupta: a task. They actually say [00:11:11] Ankit Gupta: thank you or whatever. They like, [00:11:13] Ankit Gupta: you know, they say, "Oh, [00:11:14] Ankit Gupta: your, your, advice changed [00:11:16] Ankit Gupta: my course," or whatever, right? Like [00:11:18] Ankit Gupta: there's [00:11:18] Ankit Gupta: a lot of this like, interpersonal [00:11:21] Ankit Gupta: kind [00:11:21] Ankit Gupta: of feeling of accomplishment. [00:11:23] Ankit Gupta: And although I [00:11:25] Ankit Gupta: enjoyed [00:11:26] Ankit Gupta: spending [00:11:26] Ankit Gupta: time with my son, but there like there was just none of that, like problem-solving, brain usage, accomplishment, [00:11:33] Ankit Gupta: gratitude. [00:11:34] Ankit Gupta: And so I think it took me a while to sort of [00:11:38] Ankit Gupta: adjust [00:11:38] Ankit Gupta: to [00:11:39] Ankit Gupta: the, the [00:11:39] Ankit Gupta: nature [00:11:40] Ankit Gupta: of parenting. [00:11:41] Ankit Gupta: and I'm still trying [00:11:42] Ankit Gupta: to figure that out. [00:11:43] Ankit Gupta: But yeah, it, [00:11:45] Ankit Gupta: it took me a while to sort of get into a new brain space, and just feeling more settled. [00:11:50] Ankit Gupta: So I think, I think it was a, a quarter of just like turbulence [00:11:54] Ankit Gupta: I [00:11:54] Ankit Gupta: also [00:11:54] Ankit Gupta: had a lot of FOMO. [00:11:55] Ankit Gupta: the company [00:11:56] Ankit Gupta: was doing really well and [00:11:57] Adam Fishman: Yeah [00:11:58] Ankit Gupta: Rick [00:11:58] Ankit Gupta: was like moving the company in a new direction, new executives, all of that. So it was like, really exciting, [00:12:03] Ankit Gupta: and I was like, "Man, I'm not [00:12:04] Ankit Gupta: there." Yeah. Like, why [00:12:07] Ankit Gupta: can't I do that? Yeah, [00:12:08] Ankit Gupta: that [00:12:09] Ankit Gupta: seemed pretty cool. and then all this AI stuff [00:12:11] Ankit Gupta: is happening [00:12:11] Ankit Gupta: over the last eight years that I totally didn't realize, [00:12:15] Ankit Gupta: right? Like I'm vigorously trying to catch up. [00:12:18] Ankit Gupta: Uh, [00:12:19] Ankit Gupta: and so there was just a lot of like, "But [00:12:20] Ankit Gupta: I don't have enough time 'cause I'm [00:12:21] Ankit Gupta: taking care of my kid." [00:12:22] Ankit Gupta: So there was just a lot of FOMO, [00:12:24] Ankit Gupta: and overwhelm, and yeah, it was, it was a rough- rough time [00:12:28] Adam Fishman: Yeah. I had, um, a guy on the program named Dr. Emilio Galan, who started a health, company, and he became a stay-at-home full-time dad, and he described it as the dopamine desert. Basically, like the pace just like goes... Like you're st- you're on all the time, but the pace and the brain changes significantly. [00:12:49] Adam Fishman: So you're not getting those shots of dopamine, the pings and the messages and the calls and like, you just, you and a, and a baby just staring at each other, you know, like, "All right, your move." but I, I really appreciate that you said that it's, that it's hard. but here you are having gotten past that hard part and worked through it. [00:13:07] Adam Fishman: And so, you know, we'll talk a, a bit about that. you've had some experience with hard things too, and we're gonna come back to this later in the show, but like, uh, your first company, Pulse, I think you had like the best and worst day of your, of your professional career involving like Steve Jobs talking about you on stage and then your app getting ripped out of the App Store like by the evening time. [00:13:29] Adam Fishman: So hold onto that one. We're gonna come back to it 'cause I, it's a, it's a big one. I really wanna talk about that. but before we do that, I, I wanna talk, about, um, time and, and love. I ask everybody about contrarian opinions that they have, and one of your contrarian takes was like, doing it all is, is not possible, which is not particularly contrarian, but then you followed up and you said the only thing that a parent can provide is time and love. [00:13:59] Adam Fishman: and so I'm curious why, you know, I as a dad tend to agree with that, so I don't find that super contrarian, but I think a big chunk of the population, certainly the listening audience might. So why w- why do you think that that is a contrarian position to hold? [00:14:15] Ankit Gupta: Yeah. I, I [00:14:16] Ankit Gupta: mean, I'm still [00:14:17] Ankit Gupta: trying to figure out [00:14:17] Ankit Gupta: this parenting [00:14:18] Ankit Gupta: thing and [00:14:19] Ankit Gupta: the, and the dad thing, and like what is my [00:14:20] Ankit Gupta: role for my son? I [00:14:23] Ankit Gupta: think a lot about what [00:14:24] Ankit Gupta: my parents did [00:14:25] Ankit Gupta: for me, [00:14:26] Ankit Gupta: how much of me is like [00:14:28] Ankit Gupta: what they did versus what I did kind of thing. [00:14:31] Ankit Gupta: what I'm noticing is, [00:14:33] Ankit Gupta: There's a lot of conflicting parenting advice, actually. [00:14:36] Ankit Gupta: Uh, so Yeah. [00:14:38] Ankit Gupta: It's like, [00:14:39] Ankit Gupta: let's align. But, [00:14:41] Ankit Gupta: but what's happening is that's actually pulling people in lots of different directions. [00:14:45] Ankit Gupta: what I'm noticing is, everyone's trying to do it all. So there was a do it all, I think, [00:14:50] Ankit Gupta: for, for my parents' generation, where like, oh yeah, we can... Especially for moms. [00:14:55] Ankit Gupta: Dads, no one cared. [00:14:56] Ankit Gupta: No one expected anything of dads. Even now, [00:14:59] Ankit Gupta: I think, no one expects anything [00:15:00] Adam Fishman: The bar is quite low. [00:15:01] Ankit Gupta: extremely low. Yeah. It's, it's incredible that it's still the case. [00:15:05] Ankit Gupta: and so I think this still mainly comes from, from moms, where like, yeah, you can go have a successful career. [00:15:10] Ankit Gupta: come back and, like, feed your kids this awesome, wholesome, organic food, and, like, take [00:15:15] Ankit Gupta: them to activities every day. [00:15:17] Ankit Gupta: Weekend, maybe two or three activities. [00:15:19] Adam Fishman: a loaf of bread. You could do all these things, right? [00:15:22] Ankit Gupta: Yeah,go [00:15:23] Ankit Gupta: to a charity event or whatever. so that I think is, like, literally the opposite of what I feel where I am at. That's why I feel like it's contrarian, where I feel like, I think the best thing I can do is just, like, [00:15:37] Ankit Gupta: sit with my kid [00:15:38] Ankit Gupta: and hang out essentially. [00:15:40] Ankit Gupta: Like, [00:15:41] Ankit Gupta: just like sit. My favorite time of the day is the morning right after [00:15:45] Ankit Gupta: he wakes up. He wants milk. [00:15:48] Ankit Gupta: he [00:15:48] Ankit Gupta: still doesn't change his diaper after he wakes [00:15:49] Ankit Gupta: up, [00:15:50] Ankit Gupta: which I'm still super [00:15:51] Ankit Gupta: upset about, but whatever. [00:15:53] Ankit Gupta: you know, he [00:15:53] Ankit Gupta: wants milk, I give him milk. And we just, like, sit on the couch. [00:15:57] Ankit Gupta: we might be reading a book. We might be, like, doing a puzzle [00:16:00] Ankit Gupta: together, whatever. Or we might just be, like, sitting, just, like, hanging out. [00:16:04] Ankit Gupta: that [00:16:04] Ankit Gupta: is what I wanna [00:16:05] Ankit Gupta: do [00:16:06] Ankit Gupta: as much as I can, I, like, really carve out that time. [00:16:09] Ankit Gupta: Like, I [00:16:10] Ankit Gupta: make sure [00:16:11] Ankit Gupta: that he [00:16:11] Ankit Gupta: wakes up at 7:00. [00:16:12] Ankit Gupta: I finish everything I need [00:16:14] Ankit Gupta: to finish [00:16:14] Ankit Gupta: before 7:00, or I do, [00:16:15] Ankit Gupta: a- it after 7:30. But like, [00:16:18] Ankit Gupta: that, that's... We're hanging out at that time. [00:16:20] Ankit Gupta: and I feel like that is something no one else can do for him. Like, [00:16:25] Ankit Gupta: it, it's [00:16:25] Ankit Gupta: just something that [00:16:27] Ankit Gupta: I have to [00:16:28] Ankit Gupta: do, or my wife. Like, we have to do. And, and it's not even, like, we have [00:16:32] Ankit Gupta: to do. [00:16:33] Ankit Gupta: It's [00:16:33] Ankit Gupta: like [00:16:33] Ankit Gupta: that's as human as it can be. Like, [00:16:35] Ankit Gupta: that's just in that [00:16:36] Ankit Gupta: context, right? I feel like if I'm [00:16:38] Ankit Gupta: taking him out to a park and, like, just, like, being there while he tries [00:16:43] Ankit Gupta: a, a new, [00:16:44] Ankit Gupta: you know, [00:16:45] Ankit Gupta: slide [00:16:46] Ankit Gupta: That's kind of my job in that moment, [00:16:49] Ankit Gupta: I think that's fundamentally different from the advice that a lot [00:16:53] Ankit Gupta: of people are following or, or [00:16:54] Ankit Gupta: what they're trying to do, which is like, "Let's try to be hyper-efficient with our meal planning and like, [00:17:00] Ankit Gupta: you know, have like, something in [00:17:02] Ankit Gupta: 12 [00:17:02] Ankit Gupta: cups that are frozen so [00:17:04] Ankit Gupta: that [00:17:04] Ankit Gupta: we can do that," or, you [00:17:05] Ankit Gupta: know, "Let's try to like, [00:17:06] Ankit Gupta: go to as [00:17:07] Ankit Gupta: many activities as possible because like, who knows what you need in [00:17:10] Ankit Gupta: this new AI era or, or [00:17:12] Ankit Gupta: whatever." [00:17:12] Ankit Gupta: So it's, I think [00:17:13] Ankit Gupta: all this like efficiency... A- [00:17:14] Ankit Gupta: and I, I used to do that. I-- We moved to New York. New York has so many, uh, [00:17:19] Ankit Gupta: amazing [00:17:20] Ankit Gupta: activities [00:17:20] Ankit Gupta: for kids. There were a few weeks [00:17:22] Ankit Gupta: where I was taking him [00:17:23] Ankit Gupta: to something every day except Sunday, six classes [00:17:26] Ankit Gupta: a week, and it was insane, and I intentionally did not renew like two of those classes so that we have some open time to like hang out with each other. [00:17:35] Ankit Gupta: so [00:17:35] Ankit Gupta: yeah, it's just this push and pull. I feel like our culture takes us towards this like hyper-efficiency parenting and like I think my take is we need the opposite of just like getting bored together and like hanging out, [00:17:49] Adam Fishman: Yeah. Yeah, y- you know, you put your finger on something here that like is a bit specific to kind of American work and life culture, which is like everyone's overscheduled. And now I would say this is maybe more a proximity to the coasts, you know, the cities, New York and stuff, but-- and San Francisco and things like that. [00:18:06] Adam Fishman: But like we're overscheduled, working around the clock. We're running our AI agents overnight now and waking up to, to kick them to make sure that they're still working. We're checking Slack before like our feet are on the floor out of bed in the morning. And then we take our kids and we put them in preschool from 8:00 to 5:00 every day just so we can do all that other stuff. [00:18:28] Adam Fishman: I think you have a really interesting perspective because as a, as an immigrant, so you weren't born here in the US, you came to the US. what did you observe sort of different when you were in, in India? I think one of the things you mentioned is like you went to school for like half the day, not even a whole day in India up until like 10 or 12, and that's pretty normal. [00:18:47] Adam Fishman: So like tell me about just like the, the difference between life there and sort of life, overscheduled life here in the US. [00:18:54] Ankit Gupta: I found it pretty strange that, like, my kid was going [00:18:58] Ankit Gupta: to school when he was one, and he [00:19:01] Ankit Gupta: was [00:19:02] Ankit Gupta: supposed to [00:19:02] Ankit Gupta: be dropped off by around 8:00, otherwise he would miss out [00:19:06] Ankit Gupta: on some of the [00:19:06] Ankit Gupta: activities they do. we would pick him up or early at around [00:19:10] Ankit Gupta: 3:00, but, [00:19:11] Ankit Gupta: like, [00:19:12] Ankit Gupta: everyone else picked their kids up at 5:00. So, uh, and he was already super tired when he came back at I didn't even realize [00:19:21] Ankit Gupta: this [00:19:21] Ankit Gupta: until a few months later when I was talking to [00:19:23] Ankit Gupta: my parents [00:19:23] Ankit Gupta: that I only went to school from, like, 7:00 to 12:00 every day, you know, til, [00:19:29] Ankit Gupta: till I was 10 or 11 years old. [00:19:31] Ankit Gupta: I remember those days where, like, I would be excited to go to school. [00:19:35] Ankit Gupta: I would come back, I would have [00:19:37] Ankit Gupta: lunch, then I would be like, I would have all this free time, and I would actually not know what to do. Like, maybe I would watch TV, [00:19:46] Ankit Gupta: maybe I would, [00:19:47] Ankit Gupta: like, walk around. And, [00:19:48] Ankit Gupta: at some point, I [00:19:49] Ankit Gupta: became, more, autonomous, I, I guess, or more adventurous, where, like, I would basically [00:19:54] Ankit Gupta: come home from daycare by myself. [00:19:57] Ankit Gupta: And we used to [00:19:57] Ankit Gupta: live in a gated community, but, [00:19:59] Ankit Gupta: but you [00:19:59] Ankit Gupta: know, I crossed [00:19:59] Ankit Gupta: roads and there were cars and all of that. But I was, I was walking maybe [00:20:04] Ankit Gupta: a couple of miles back home by myself, [00:20:07] Ankit Gupta: when I was, you know, eight or nine years old. [00:20:09] Ankit Gupta: and then coming home and doing my [00:20:10] Ankit Gupta: homework and, and all of that. [00:20:12] Ankit Gupta: and, and there was a lot of getting bored [00:20:15] Ankit Gupta: along the way in, in, in that. [00:20:17] Ankit Gupta: And, and I [00:20:17] Ankit Gupta: feel like, [00:20:18] Ankit Gupta: those things are so important. So [00:20:21] Ankit Gupta: it's [00:20:21] Ankit Gupta: not just that y- you know, you're with your parents all the time. I think it's really important for the kid to be alone, you know, for, for [00:20:29] Ankit Gupta: some time. Uh, obviously supervised, but, like, be able to do things, activities by themselves, get bored, [00:20:35] Ankit Gupta: get creative. [00:20:36] Ankit Gupta: I didn't [00:20:36] Ankit Gupta: have a lot of toys growing up, but [00:20:38] Ankit Gupta: we would sort of [00:20:38] Ankit Gupta: figure out games to play, you [00:20:40] Ankit Gupta: know, with the stuff that we have. and it doesn't have to [00:20:42] Ankit Gupta: be always structured. Like, there doesn't need to be [00:20:45] Ankit Gupta: a- an after-school activity [00:20:47] Ankit Gupta: every day. Like, [00:20:48] Ankit Gupta: you [00:20:48] Ankit Gupta: could just kind of hang out at home and see what happens, [00:20:52] Ankit Gupta: everything is educational too. I feel like people, people don't realize this, but, [00:20:56] Ankit Gupta: the more I [00:20:58] Ankit Gupta: got into the Montessori philosophy, the more I started to see things differently. Like, [00:21:03] Ankit Gupta: playing around with, like, [00:21:05] Ankit Gupta: the sand in our [00:21:07] Ankit Gupta: pot, like, [00:21:08] Ankit Gupta: is educational. Like, you notice all these things. [00:21:10] Ankit Gupta: There's a little, there's a little, like, [00:21:13] Ankit Gupta: rock. There's a little bug. Yeah. You can count the scoops, you know, [00:21:18] Ankit Gupta: Yeah. Yeah, you can move it around with your hand. [00:21:20] Ankit Gupta: it's so different here. I think this is... in the US it's optimized for, like, parents working, 8:00 to 5:00, and then working after they go [00:21:29] Ankit Gupta: to sleep, and [00:21:30] Ankit Gupta: then working [00:21:30] Ankit Gupta: before they wake up. [00:21:31] Adam Fishman: so a cynical listener, which is not me, of course, I'm not a cynic at all, might think about your story. You know, you sold a company to LinkedIn. You know, you, it, you did well there. Um, then you founded another company, and then that company did well, and then you were able to kind of exit out of that company. [00:21:50] Adam Fishman: somebody who looks at you and thinks like, "Well, I'm, I'm in the grind. I'm not doing what Ankit did. Like I, I haven't sold a company." You know, they might, they might look at you becoming at-home dad and say, "Well, he can really only do this because he sold his company to LinkedIn 10 years ago. [00:22:10] Adam Fishman: Um, and then he built another one, and so he's really suc- he's wildly successful. I can't... That's not me." so I think there's like two things there. You know, one, I'm sure you maybe get some of that. If you put yourself out on the internet, you're gonna get some shade. People are gonna call you a privileged person. [00:22:26] Adam Fishman: And so I'm wondering two questions. What, what you say to that? And then two, if you're having a conversation with somebody who's like, "Hey, Ankit, I'm not like you. I can't see myself selling a company. I can't step back." what would your conversation be like for that person who wants to be a more involved dad but doesn't feel like they can step back? [00:22:46] Adam Fishman: yeah. [00:22:47] Ankit Gupta: yeah. I mean, I, I'm [00:22:48] Ankit Gupta: definitely privileged. I feel grateful for the financial independence that I have, [00:22:52] Ankit Gupta: all the time. I'm trying to use it as best as I can, like, for myself and, and the world. so I think having that financial independence [00:23:03] Ankit Gupta: allows [00:23:04] Ankit Gupta: me to remove, like, a whole dimension of problems. [00:23:08] Ankit Gupta: there's a whole bunch of [00:23:09] Ankit Gupta: people, whole bunch [00:23:10] Ankit Gupta: of dads who have a whole bunch more financial independence that are not stay-at-home and that [00:23:15] Ankit Gupta: are not spending [00:23:16] Ankit Gupta: all of this time with their [00:23:17] Ankit Gupta: kids. So, [00:23:17] Ankit Gupta: it's not [00:23:18] Ankit Gupta: like just having financial independence will automatically unlock some [00:23:23] Ankit Gupta: level where, you know, if you wanna be more intentional, you can be more intentional. [00:23:26] Ankit Gupta: Like, there's [00:23:27] Ankit Gupta: a lot more stuff [00:23:29] Ankit Gupta: to think through to, to get there. I think having financial independence is just sort of one, one dimension of that. [00:23:36] Ankit Gupta: I [00:23:36] Ankit Gupta: think the way I think about it is, [00:23:38] Ankit Gupta: being a dad was truly a pull, right? Like, it was, it was important to me. it felt like the universe was sort of [00:23:44] Ankit Gupta: pushing me [00:23:45] Ankit Gupta: i- in that direction. [00:23:46] Ankit Gupta: if that's the case [00:23:47] Ankit Gupta: for anyone out there [00:23:49] Ankit Gupta: who's, [00:23:49] Ankit Gupta: who's listening, then it's worth thinking about it. [00:23:52] Ankit Gupta: If, if that's not [00:23:52] Ankit Gupta: the case, then nothing needs to change. Like, that's fine, I see a bunch of people who are working super hard, and they spend quality [00:24:00] Ankit Gupta: time, quote unquote, with their kids," [00:24:02] Ankit Gupta: and they're happy, everyone's happy, and, you know, they don't wanna do anything more. [00:24:06] Ankit Gupta: And that, that's fine. [00:24:07] Ankit Gupta: but I think that [00:24:08] Ankit Gupta: there, there probably has to be some sort of intrinsic, like, motivation, some sort of push to make a change. and if that is there, like, [00:24:15] Ankit Gupta: if, if [00:24:16] Ankit Gupta: there's some sort of regret or some sort of constant feeling of like, "Hey, I wish I could do [00:24:20] Ankit Gupta: this. I wish I could not go on [00:24:21] Ankit Gupta: this offsite," or whatever, it's worth listening [00:24:24] Ankit Gupta: to that. [00:24:24] Ankit Gupta: Like, [00:24:24] Ankit Gupta: for me, [00:24:25] Ankit Gupta: that constant feeling was [00:24:28] Ankit Gupta: every time I had to make a trip [00:24:29] Ankit Gupta: for bicycle, like a work trip, I really had to [00:24:32] Ankit Gupta: think about whether [00:24:33] Ankit Gupta: I want to do that or [00:24:34] Ankit Gupta: not. Like, do I really wanna meet that customer? Do [00:24:36] Ankit Gupta: I really wanna go [00:24:37] Ankit Gupta: to that trade show and, and not be home for bedtime or, or [00:24:41] Ankit Gupta: whatever? [00:24:43] Ankit Gupta: And I didn't wanna keep doing that [00:24:45] Ankit Gupta: calculus because it wasn't fair for the company. [00:24:47] Ankit Gupta: so I think whatever that [00:24:48] Ankit Gupta: is for you, it's worth leaning into that. [00:24:52] Ankit Gupta: And then, I think finances just becomes one part of that. Like- everyone [00:24:57] Ankit Gupta: has some kind of burn rate, like some sort of spend, expenditure and [00:25:01] Ankit Gupta: some sort [00:25:01] Ankit Gupta: of income, and, and [00:25:02] Ankit Gupta: you just [00:25:02] Ankit Gupta: have to kind of match that, [00:25:04] Ankit Gupta: and then that's why I think it's much, much easier to be a dad as a startup founder, 'cause you can really [00:25:10] Ankit Gupta: have that flexibility for, for yourself. you can pay yourself a certain amount, you can work a certain amount, [00:25:16] Ankit Gupta: you [00:25:16] Ankit Gupta: can hire [00:25:17] Ankit Gupta: people to do the things that need to be done, whatever. So, like, I think being a founder could be a pretty good job if you want to be more intentional as a dad. [00:25:24] Ankit Gupta: but even in the job you [00:25:25] Ankit Gupta: have or, or some other job, [00:25:27] Ankit Gupta: that's just one problem to solve. Like, [00:25:29] Ankit Gupta: how do you actually manage your own, uh, expenses in a way that they can be covered by the income that [00:25:36] Ankit Gupta: you have i- in a new way, which allows you to be [00:25:39] Ankit Gupta: more intentional? [00:25:40] Ankit Gupta: but then also you have to think about, [00:25:42] Ankit Gupta: like, identity. [00:25:43] Ankit Gupta: Like, how do [00:25:43] Ankit Gupta: you think about yourself? Like, [00:25:44] Ankit Gupta: if you think [00:25:45] Ankit Gupta: about yourself as this successful, e- you know, executive, or, or successful manager and maybe that's not possible. If you want to [00:25:53] Ankit Gupta: spend more time at home, then, you know, how you think about yourself has to change. [00:25:57] Ankit Gupta: How your spouse [00:25:58] Ankit Gupta: looks at you has to change. [00:25:59] Ankit Gupta: Like, how you,still get that dopamine hit has to change. So, you know, I, I [00:26:06] Ankit Gupta: don't think it's one thing. It's not just [00:26:08] Ankit Gupta: the finances necessarily, [00:26:09] Ankit Gupta: but [00:26:09] Ankit Gupta: it's, it's, [00:26:10] Ankit Gupta: just thinking through how do you actually build [00:26:13] Ankit Gupta: this kind [00:26:14] Ankit Gupta: of life [00:26:14] Ankit Gupta: for yourself that [00:26:15] Ankit Gupta: will look very different, [00:26:16] Adam Fishman: so I wanna ask you, then I wanna move on to our next section, which I've, I've called Parenting is Tiring. Which, uh, you know, people listening to this are like, "Uh, duh." But, you said to me that you've been thinking a lot about this, like thinking really hard about why parenting is tiring. [00:26:36] Adam Fishman: Like, especially in those times when, you know, it's tiring and you feel tired of it, you know? And I've had a, a friend told me, "I love being a parent, I hate parenting." which is an interesting way of, of thinking about it. So I'm curious When do you feel that the parenting is tiring, like the most? [00:26:55] Ankit Gupta: Well, [00:26:56] Ankit Gupta: starting last night [00:26:56] Ankit Gupta: when [00:26:57] Ankit Gupta: he didn't go to bed. [00:26:58] Adam Fishman: Yep [00:27:01] Ankit Gupta: bedtime [00:27:02] Ankit Gupta: at 8:00, he went to bed at 11:30. [00:27:03] Adam Fishman: Oh, man. Sorry. That's [00:27:06] Ankit Gupta: bad. [00:27:06] Adam Fishman: say there is sorry. [00:27:07] Ankit Gupta: Yeah, I am, I am sorry for myself [00:27:10] Ankit Gupta: also. [00:27:11] Ankit Gupta: Uh, [00:27:12] Ankit Gupta: some of [00:27:13] Ankit Gupta: it is expected. Uh, I feel like the [00:27:15] Ankit Gupta: physical-- I didn't realize how physically tiring parenting [00:27:18] Ankit Gupta: would be, like just [00:27:20] Ankit Gupta: kinda running around behind [00:27:21] Ankit Gupta: your kid. [00:27:22] Ankit Gupta: So [00:27:22] Ankit Gupta: that really motivated me to get [00:27:24] Ankit Gupta: in better shape and really just like [00:27:27] Ankit Gupta: not have it be [00:27:28] Ankit Gupta: so tiring. And our parents had, at [00:27:29] Ankit Gupta: le- [00:27:29] Ankit Gupta: at least [00:27:30] Ankit Gupta: my parents had me when they were [00:27:31] Ankit Gupta: much, much [00:27:32] Ankit Gupta: much younger than, than I am, so I didn't brace myself for, for that. [00:27:36] Ankit Gupta: you [00:27:36] Ankit Gupta: know, there's physical tire- I think the biggest one [00:27:39] Ankit Gupta: for me is mental, where like [00:27:41] Ankit Gupta: you kinda expect things to go in a certain way. [00:27:44] Ankit Gupta: Like, "Oh yeah, he'll go to bed in half [00:27:45] Ankit Gupta: an hour." And [00:27:46] Ankit Gupta: then two hours later he's still not going to bed and [00:27:49] Ankit Gupta: you're [00:27:49] Ankit Gupta: like, "Please do the thing I'm asking you to do. Like, eat, [00:27:52] Ankit Gupta: eat this lunch 'cause there's nothing else for you to eat." th- that's where I [00:27:57] Ankit Gupta: think... And, And, [00:27:57] Ankit Gupta: it [00:27:58] Ankit Gupta: hits you, I think, very, uh, unexpectedly 'cause y- you feel like you're just going about your day and then suddenly it like fully disrupts [00:28:05] Adam Fishman: Yeah. what you're speaking to there, you know, so you, you told me that there's kind of four sources of tiredness you think. There's the no gratitude, right? Like that, that two-year-old just doesn't have the capacity to be like, "Thanks, Dad. I really appreciate..." Like, they don't, they don't have the language, you know? [00:28:22] Adam Fishman: You got long hours, right? And what you just mentioned is kind of more of a lack of control, right? Like, even though you're the boss, you're the parent, you're, you know, you've been the boss, CEO, founder of a company. Like, this is a person who, like, you can say, "Could you please do this?" And they're just like, "Nope." [00:28:39] Adam Fishman: and that's actually en- entirely normal development to push the boundaries and things like that. And then you've got that fourth thing which you brought up earlier, which is like conflicting advice. Like, "Do this, don't do that. Do that o- no, not that way. Do that." the thing that I think interests me the most is, so lack of control everyone will appreciate if you have a toddler. [00:28:56] Adam Fishman: the gratitude one interests me the most. and as I mentioned, like a two-year-old is kind of structurally incapable of really thanking you properly. but the other thing, uh, is like, you know, you ran a company and you mentioned that you got a lot of positive feedback, but you ran a company and I presume that as the CEO and founder of the company, like you were constantly getting feedback about stuff you were doing wrong, right? [00:29:18] Adam Fishman: Like this is like people love to tell you that. So did, did that prepare you at all for the parenting struggle or is it so different that you were like, "Yeah, you know, the constant barrage of, of failure is nothing compared to the lack of gratitude from a two-year-old"? [00:29:33] Ankit Gupta: I think they're related, but different. Like, [00:29:35] Ankit Gupta: the constant failure of [00:29:36] Ankit Gupta: being a startup founder [00:29:38] Ankit Gupta: is helpful as a parent, like, for sure. You know, 'cause you, [00:29:43] Ankit Gupta: you kind of have to [00:29:43] Ankit Gupta: lean into not knowing what [00:29:46] Ankit Gupta: you're doing [00:29:48] Ankit Gupta: while still doing it, while still learning from it, while [00:29:51] Ankit Gupta: still feeling good [00:29:52] Ankit Gupta: about the ambiguity. [00:29:53] Ankit Gupta: Like, it's kind of a weird job, [00:29:56] Ankit Gupta: but I've done that [00:29:57] Ankit Gupta: for so long that it, like, comes a lot more naturally to me than, my partner, for example, [00:30:04] Ankit Gupta: it still doesn't take away from the [00:30:05] Ankit Gupta: control aspect, 'cause I love controlling the, the outcome, and you just can't [00:30:09] Ankit Gupta: do that. And, and my, my parents, [00:30:11] Ankit Gupta: you [00:30:12] Ankit Gupta: know, obviously they're from [00:30:12] Ankit Gupta: India, and they still wanna control what I do, and [00:30:15] Ankit Gupta: I tell them, "I [00:30:16] Ankit Gupta: can't even control what my son does, so how can you, you know, expect me to do what you, what you want [00:30:20] Ankit Gupta: me to do?" [00:30:21] Ankit Gupta: But [00:30:21] Ankit Gupta: I think the lack of gratitude was the biggest thing because, you feel good when people tell you that, [00:30:29] Adam Fishman: like, [00:30:29] Ankit Gupta: that's a big thing. Like, "Oh, we raised money." Like, "Oh, you [00:30:32] Ankit Gupta: know, we hit this metric." Like, everyone appreciates [00:30:34] Ankit Gupta: that. Or like, I think that's a big part of [00:30:37] Ankit Gupta: work [00:30:38] Ankit Gupta: life, uh, like, people giving you positive feedback. [00:30:41] Ankit Gupta: and that completely disappears if you're a stay-at-home [00:30:44] Ankit Gupta: parent. [00:30:45] Ankit Gupta: You don't even get that from your partner. Like, that's why, [00:30:47] Ankit Gupta: you [00:30:48] Ankit Gupta: know, all these days exist, [00:30:49] Ankit Gupta: you know, to make up for the lack of positive feedback, 'cause most of the time you're just, like, scheduling or fighting about something that you [00:30:59] Ankit Gupta: disagree [00:30:59] Ankit Gupta: on or, or whatever. [00:31:00] Ankit Gupta: Like, you have to be very intentional about giving that positive feedback. Uh, so you don't get it. So that was a big change [00:31:08] Ankit Gupta: for me, where I went from, [00:31:09] Ankit Gupta: like, actually [00:31:10] Ankit Gupta: getting [00:31:11] Ankit Gupta: feedback, [00:31:12] Ankit Gupta: mix of positive and negative, but still a lot of positive feedback, and then, like, no feedback, [00:31:17] Adam Fishman: Or, or if, you know, if you go on Instagram, you just get barraged with how you're doing it wrong as a parent, right? Like, there's a million sources of you don't, you don't have this, you're not doing it all, right? So, um, that's a whole different podcast episode right there. so I, I wanna talk, one of my favorite things, and actually the reason that I found you and reached out to you, was this LinkedIn post that you made. [00:31:37] Ankit Gupta: So i- it's, it's a chart that you did. By the way, one thing on the gratitude thing, I feel like I'm [00:31:44] Ankit Gupta: starting to, [00:31:45] Ankit Gupta: just appreciate the doing of the thing. So like, he [00:31:49] Ankit Gupta: can't tell me that I made a good pasta, but just the fact that I, like, [00:31:53] Ankit Gupta: put it [00:31:53] Ankit Gupta: on [00:31:53] Ankit Gupta: the table, I wanna feel good about you know? Like, that's how I'm trying to trick myself to, like, getting [00:31:59] Ankit Gupta: that feedback, like self-feedback [00:32:02] Adam Fishman: okay, so let's talk about this LinkedIn post that you made. So, and we're gonna get into a whole world of AI. You've got some cool stuff to show. I'm like super excited about this. so you asked, the origin of this is you asked Claude, our good friend Claude, to research every popular parenting philosophy, put them on a map from like warmth and responsiveness on the Y-axis to like structure and control on the X-axis, and then hand you back like an analysis of those, and then you kind of, what the research says is the ideal zone, and then you figured out your own style. [00:32:40] Adam Fishman: So like walk me through what you asked for, what you asked Claude for and what came back. And I'm, I'm showing you, I'm showing folks like the m- the graph of, of this. [00:32:50] Ankit Gupta: It [00:32:50] Ankit Gupta: was just on a whim. [00:32:51] Ankit Gupta: Like, I read [00:32:52] Ankit Gupta: a lot of parenting books, [00:32:54] Ankit Gupta: and they [00:32:56] Ankit Gupta: seem to all say the same thing, but also different things, and it's, like, super confusing. [00:33:02] Ankit Gupta: And [00:33:02] Ankit Gupta: I use Claude and [00:33:03] Ankit Gupta: ChatGPT research for everything, for every [00:33:06] Ankit Gupta: single thing. So, so I just, turned on research mode, a new model had come out, and turned on research mode and said, " [00:33:12] Ankit Gupta: There's [00:33:13] Ankit Gupta: too much [00:33:13] Ankit Gupta: conflicting parenting [00:33:14] Ankit Gupta: advice. [00:33:15] Ankit Gupta: There's [00:33:15] Ankit Gupta: too many parenting philosophies. Give me a list [00:33:19] Ankit Gupta: of the [00:33:19] Ankit Gupta: unique evidence-based parenting philosophies that are out there, the research [00:33:25] Ankit Gupta: behind it, the books I can read, the snippets [00:33:28] Ankit Gupta: about it." [00:33:29] Ankit Gupta: you know, it went [00:33:30] Ankit Gupta: off and [00:33:31] Ankit Gupta: this was, like, [00:33:31] Ankit Gupta: before going into yoga, it went off [00:33:33] Ankit Gupta: and did its thing. [00:33:34] Ankit Gupta: And then after I finished [00:33:34] Ankit Gupta: the yoga [00:33:35] Ankit Gupta: class, I [00:33:35] Ankit Gupta: looked at it, and [00:33:36] Ankit Gupta: this is what it came back with. [00:33:37] Adam Fishman: I wanna go to this. So this is the, like, parenting philosophies cheat sheet. So these are the different philosophies, and then you have, like, tags on these of, like, where the evidence is strong, where it's moderate, where it's mixed, anecdotal, like, stuff like that. and then if I go back to this one, you drew or Claude drew a box around the, like, research sweet spot, which is sort of, like, warm and firm. [00:34:04] Adam Fishman: Which is actually funny because one of my, behavioral values or things that I subscribe to is the idea of being kind but firm. So similar, similar concept. So then you said in this post that your approach is kind of a mix of respectful and Montessori. [00:34:20] Adam Fishman: And so, like, one of these approaches, the, like, respectful approach is just outside of the sweet spot, and then Montessori is in there, so you're sort of a blend. Hold onto that, that you're just, like, slightly outside on one of them. Then if I go to your cheat sheet, the ones that are tagged as strong evidence are positive discipline, emotion coaching, and collaborative solutions, and you didn't pick any of those as your s- as your style. [00:34:43] Adam Fishman: what do you make of your own chart kind of, like, disagreeing with you? Or what is the benefit of you having this chart now in, in how you handle your own parenting style? [00:34:55] Ankit Gupta: Yeah, I mean, this was literally a personal experiment [00:34:58] Ankit Gupta: for me to [00:34:59] Ankit Gupta: figure out what my own parenting style is. Like, [00:35:01] Ankit Gupta: which is the book [00:35:02] Ankit Gupta: that I should read [00:35:03] Ankit Gupta: to help me parent better, and which is the book that I should read to [00:35:08] Ankit Gupta: know what not to do, [00:35:09] Ankit Gupta: and so [00:35:10] Ankit Gupta: what I found interesting was that [00:35:13] Ankit Gupta: this research [00:35:14] Ankit Gupta: sweet spot, [00:35:15] Ankit Gupta: uh, like there are certain philosophies that are a lot more studied than others, [00:35:18] Ankit Gupta: and I went down the [00:35:19] Ankit Gupta: rabbit [00:35:20] Ankit Gupta: hole of [00:35:21] Ankit Gupta: what those studies show and, [00:35:22] Ankit Gupta: what's actually coming back. [00:35:24] Ankit Gupta: and I [00:35:24] Ankit Gupta: kind of realized that [00:35:25] Ankit Gupta: it, [00:35:25] Ankit Gupta: the outcomes don't [00:35:27] Ankit Gupta: really mean much anyways. [00:35:30] Ankit Gupta: Like on a personal basis, like [00:35:32] Ankit Gupta: this is for me [00:35:33] Ankit Gupta: to parent [00:35:33] Ankit Gupta: my son, which is such a N of one thing. Like on a population level, great, you know, you could have outcomes around kind of, uh, reading levels and, you know, social emotional behavior [00:35:44] Ankit Gupta: and things like that. [00:35:45] Ankit Gupta: But on a personal level, [00:35:47] Ankit Gupta: I feel like every parent [00:35:48] Ankit Gupta: has a different parenting philosophy. [00:35:51] Ankit Gupta: Like it's, you know, a different blend, and it's not one versus another, and it's also not one versus [00:35:57] Ankit Gupta: another in [00:35:58] Ankit Gupta: every situation. [00:35:59] Ankit Gupta: you know, I even asked Claude, like, "What does it mean for this to be research-based or evidence-based?" [00:36:03] Ankit Gupta: And They like spit out all this academic stuff, [00:36:06] Ankit Gupta: and I was like, " [00:36:07] Ankit Gupta: Well, that's [00:36:07] Ankit Gupta: not what I'm going for." I'm going for hanging out with my kid and [00:36:10] Ankit Gupta: building a bond together. Like, [00:36:12] Ankit Gupta: it was really interesting to learn about, for example, behaviorist philosophy, right? Like, [00:36:16] Ankit Gupta: that's something that, that [00:36:17] Ankit Gupta: I would definitely not [00:36:18] Ankit Gupta: do. [00:36:18] Ankit Gupta: [00:36:18] Ankit Gupta: and it's all about using rewards. [00:36:21] Ankit Gupta: and I've done that with our [00:36:22] Ankit Gupta: dog. [00:36:22] Ankit Gupta: It's worked really well, positive reinforcement and negative reinforcement. But with my son, [00:36:27] Ankit Gupta: I'll give you an example. Like, I gave him an activity, a Montessori activity, where like you open and [00:36:31] Ankit Gupta: close, wallets and you open and close things. [00:36:34] Ankit Gupta: And I happened to put a walnut in it so that he can like open and find a walnut. and he did that. He was very [00:36:40] Ankit Gupta: excited that he was able to open the [00:36:41] Ankit Gupta: box and find the walnut. And then [00:36:44] Ankit Gupta: after that, he [00:36:45] Ankit Gupta: just came back [00:36:46] Ankit Gupta: to [00:36:46] Ankit Gupta: me running to get more walnuts. [00:36:48] Ankit Gupta: Like, he'd just forgotten [00:36:49] Ankit Gupta: about, you know, the activity [00:36:51] Ankit Gupta: and just wanted more walnuts. [00:36:52] Ankit Gupta: And then every time I bring that [00:36:54] Ankit Gupta: activity out, [00:36:55] Ankit Gupta: all he wants is walnuts. Like, he's just not interested in the activity at all. [00:36:59] Ankit Gupta: i-i-it's such a bummer 'cause it's such [00:37:00] Ankit Gupta: a beautiful, [00:37:02] Ankit Gupta: really kind of [00:37:03] Ankit Gupta: use [00:37:03] Ankit Gupta: the fine [00:37:03] Ankit Gupta: motor skills, and [00:37:04] Ankit Gupta: it's, it's, a great activity, but [00:37:06] Ankit Gupta: now, now it's like non-existent. [00:37:08] Ankit Gupta: [00:37:08] Ankit Gupta: and through that, I learned that I don't want to do the, the behaviorist, you know, philosophy. [00:37:12] Ankit Gupta: So I, I feel like I was [00:37:14] Ankit Gupta: okay being sort [00:37:15] Ankit Gupta: of outside the box 'cause I, I think, I feel like, [00:37:17] Ankit Gupta: uh, what I'm going for is different. You know? [00:37:21] Ankit Gupta: It's, it's not to drive a certain outcome, but it's actually to sort of build that bond with my son and it, it kind of like spent a time with him [00:37:30] Adam Fishman: Yeah. [00:37:31] Adam Fishman: Yeah. And, and in the comments you mentioned that your favorite book, the one that's kind of influenced you the most, is "Good Inside" by Dr. Becky. So Dr. Becky, like most people listening to this podcast will know who Dr. Becky is, but, amazing entrepreneur and doctor and,actually built Good Inside with the spouse of one of my other Startup Dad guests, uh, Sc- Scott Belsky's wife. [00:37:55] Adam Fishman: Dr. Becky talks about emotion coaching, which is in that sort of strong tier. That's the Gottman thing. And, and for people who know the Gottman method, that's also like a couples counseling method and, and things like that. [00:38:06] Adam Fishman: Um- that the one you turn, [00:38:08] Ankit Gupta: turn towards each [00:38:08] Ankit Gupta: other? Like you [00:38:09] Adam Fishman: exactly. [00:38:10] Adam Fishman: you are reading things that are in like the well-evidenced zone, which actually may be a self-fulfilling prophecy. [00:38:18] Adam Fishman: It might be well-evidenced because there's a lot written about it, but your labels are a bit different. So is this, is this part of you also trying to maybe steadily move zones or adopt some of the behaviors of the zones that you like and obviously distance yourself from the ones that you don't like? [00:38:34] Ankit Gupta: that was my idea. You know, there's something that naturally comes to me, [00:38:38] Ankit Gupta: but [00:38:39] Ankit Gupta: then I also wanna read and improve my [00:38:41] Ankit Gupta: parenting skills. So, I actually built [00:38:43] Ankit Gupta: an app [00:38:44] Ankit Gupta: just for [00:38:44] Ankit Gupta: myself. Uh, [00:38:45] Ankit Gupta: it's like [00:38:45] Ankit Gupta: a quiz [00:38:46] Ankit Gupta: to basically... pull it up and show it. [00:38:49] Ankit Gupta: this is a little [00:38:50] Ankit Gupta: bit more, [00:38:50] Ankit Gupta: built out [00:38:51] Ankit Gupta: than when I, put out, uh, the LinkedIn post. [00:38:53] Ankit Gupta: But, It's called Fellow Parent. [00:38:55] Ankit Gupta: you can go to fellowparent.org, and it's, it's basically a quiz. and so it, [00:39:02] Ankit Gupta: it's still the same 12 philosophies, but it basically, uh, asks you a bunch of scenario questions. So, [00:39:09] Ankit Gupta: like, my kid [00:39:09] Ankit Gupta: is [00:39:09] Ankit Gupta: a toddler. [00:39:10] Ankit Gupta: so it basically asks you a bunch of scenario questions, and you can answer what you would do in a regular moment, if there's a stressor, like if there's a hard moment, [00:39:17] Ankit Gupta: how would that change? [00:39:19] Ankit Gupta: So it basically helps you sort of figure [00:39:21] Ankit Gupta: out what your [00:39:22] Ankit Gupta: blend of philosophies is [00:39:25] Ankit Gupta: during the usual moments. [00:39:26] Ankit Gupta: and then, [00:39:27] Ankit Gupta: and then in a hard moment, [00:39:28] Ankit Gupta: what muscle do you exercise more? So it's more of a reflection tool. [00:39:32] Ankit Gupta: and I built [00:39:33] Ankit Gupta: that for myself to kind of figure out, Where am I at now? [00:39:37] Ankit Gupta: I do wanna be a lot more [00:39:38] Ankit Gupta: emotionally oriented towards my son. I wanna help him label his feelings. I wanna help him, y- you know, communicate his feelings. And, and, and so you're absolutely right. Like, after reading Good Insight, I wanted to practice a lot more of those skills, but that's not [00:39:53] Ankit Gupta: necessarily [00:39:54] Ankit Gupta: naturally where I am right now. [00:39:56] Ankit Gupta: that's something where I wanna, wanna go. and so I wanted to make that a lot more, real for myself. So, yeah, we don't have to go through the [00:40:03] Ankit Gupta: whole quiz, but, [00:40:03] Ankit Gupta: but it's basically like these scenarios. [00:40:06] Ankit Gupta: Like at checkout, your toddler reaches for candy and you say no, but [00:40:10] Ankit Gupta: they keep grabbing [00:40:11] Ankit Gupta: it. [00:40:11] Ankit Gupta: Like, what would you do? And, you know, there's a few different options. [00:40:15] Ankit Gupta: [00:40:15] Ankit Gupta: and you could pick, uh, for [00:40:17] Ankit Gupta: example, what I [00:40:18] Ankit Gupta: would say is the candy stays on the shelf. [00:40:20] Ankit Gupta: If you grab it again, I'm [00:40:21] Ankit Gupta: gonna move you away, [00:40:22] Ankit Gupta: and, and actually do that. [00:40:24] Ankit Gupta: that's very [00:40:24] Ankit Gupta: different from, something like this, where maybe you just ask yourself like, " [00:40:29] Ankit Gupta: Is [00:40:29] Ankit Gupta: it really important for them to not have candy? [00:40:32] Ankit Gupta: Like, maybe they can have candy today," [00:40:34] Ankit Gupta: and that's really very different from, [00:40:36] Ankit Gupta: you kind of just pick them up and hold them and comfort them [00:40:40] Ankit Gupta: and, you know, have more of that physical. So I [00:40:43] Ankit Gupta: had a lot of fun making this quiz 'cause it, [00:40:45] Ankit Gupta: This was my way to learn what all of these [00:40:47] Ankit Gupta: philosophies are actually about, and how would I really [00:40:52] Ankit Gupta: react in these situations. You know, [00:40:54] Ankit Gupta: they finish their snack, they [00:40:55] Ankit Gupta: threw their water, [00:40:56] Ankit Gupta: what would you do? so [00:40:57] Ankit Gupta: yeah, [00:40:57] Adam Fishman: anyone can go, go to fellowparent.org, take the quiz, see what your outcome is. so you originally built this as, you know, an N of one for yourself to learn, both learn AI building and also learn your own parenting style. But now this is public and other people can use it. It's like you couldn't resist the call of the entrepreneur, [00:41:17] Adam Fishman: Have you had other people go, go through this, like friends and, you know, uh, like are people randomly finding this on the internet? [00:41:23] Adam Fishman: They certainly will after this podcast, but, [00:41:25] Ankit Gupta: I've just shared it with some friends. [00:41:27] Ankit Gupta: I [00:41:27] Ankit Gupta: mean, this wasn't intended [00:41:28] Ankit Gupta: to be public. [00:41:29] Ankit Gupta: This is not a startup or anything. It, it's [00:41:32] Ankit Gupta: kind of crazy how with AI you [00:41:33] Ankit Gupta: can build something just [00:41:34] Ankit Gupta: for yourself. [00:41:35] Ankit Gupta: Like, you don't need anyone else to [00:41:37] Ankit Gupta: build an app and sell it to [00:41:39] Ankit Gupta: you. You can just build it yourself. [00:41:40] Ankit Gupta: So, [00:41:40] Ankit Gupta: uh, I have that, [00:41:41] Ankit Gupta: builder's itch, and this was how I was scratching it. But yeah, I did, I did, I [00:41:46] Ankit Gupta: did send it to my wife, and we had some fun, you know, comparing like what, what our philosophy mixes are. [00:41:52] Ankit Gupta: I shared it with my friends and [00:41:54] Ankit Gupta: my, like, my son's preschool, you know, parents group. And so we've [00:41:59] Ankit Gupta: just been having fun with it. [00:42:00] Ankit Gupta: I think [00:42:00] Ankit Gupta: if more people try it out, I would love to hear sort of [00:42:04] Ankit Gupta: does [00:42:04] Ankit Gupta: this feel different? Like I, I've tried to make it helpful in a way where like [00:42:08] Ankit Gupta: you can actually see, [00:42:10] Ankit Gupta: you can actually like try to ask yourself some questions about [00:42:13] Ankit Gupta: what you [00:42:14] Ankit Gupta: can do. [00:42:15] Ankit Gupta: Uh, you can actually see, [00:42:16] Ankit Gupta: like, what would you do [00:42:18] Ankit Gupta: more of? Like [00:42:19] Ankit Gupta: let's say, you [00:42:20] Ankit Gupta: know, [00:42:21] Ankit Gupta: I'm [00:42:21] Ankit Gupta: more of a Waldorf Montessori parent [00:42:24] Ankit Gupta: in, [00:42:24] Ankit Gupta: in this case, but, but I want to develop emotional coaching. Like what could I do more of? You know? Like, like in this case, you-- I would start working on naming the feeling and help [00:42:34] Ankit Gupta: the child work through [00:42:35] Ankit Gupta: it. [00:42:35] Ankit Gupta: So [00:42:35] Ankit Gupta: it's something that I built for [00:42:36] Ankit Gupta: myself, [00:42:37] Ankit Gupta: but but hopefully the idea is, you know, [00:42:39] Ankit Gupta: people can see where they are and then see where they want [00:42:43] Ankit Gupta: to go and like try [00:42:45] Ankit Gupta: to be more introspective and just use it for, you know, improving their parenting skills [00:42:49] Adam Fishman: and that's fellowparent.org [00:42:52] Ankit Gupta: fellowparent.org. [00:42:54] Adam Fishman: thank you for sharing that. Now, I wanna talk about putting your bed on the floor. one of the things that you told me is, and this gets to kind of what you were just saying, like you want to try to avoid, try to avoid creating situations where you have to tell your son no. [00:43:10] Adam Fishman: And obviously the candy is different. That's not an environment you control, but you do control your house and where your bed is. And so you moved your bed to the floor, uh, so that jumping on the bed wouldn't be a hazard. Nobody's breaking any bones. And I think most parents would be like, "Well, I'm not moving my bed. [00:43:28] Adam Fishman: Like, I'm just gonna tell my kid, 'Don't jump on the bed.'" You know? Which is actually probably my approach. Like, "No, no, no. Sorry, we're not jumping on the bed, kids." but you redesigned your room. Why'd you do that? [00:43:37] Ankit Gupta: So [00:43:38] Ankit Gupta: have you had [00:43:39] Ankit Gupta: success in, like, getting your kids to not jump on [00:43:42] Ankit Gupta: the bed? [00:43:42] Ankit Gupta: Like, [00:43:42] Adam Fishman: Oh [00:43:42] Adam Fishman: no, of course not. Or the couch or literally anything. [00:43:48] Ankit Gupta: Yeah. I mean, at some point it's probably okay. Like, I enjoy jumping on the [00:43:52] Ankit Gupta: bed, but [00:43:53] Ankit Gupta: I really have subscribed to the, the whole like, don't say a lot of no, [00:43:58] Ankit Gupta: you know, concept. but also like, I really can't control what my son does. it's wild. I can't get him to do, uh, something he doesn't wanna do. [00:44:07] Ankit Gupta: So [00:44:08] Ankit Gupta: like, every [00:44:09] Ankit Gupta: time I say a no, it's just like a moot point. Like, well, [00:44:12] Ankit Gupta: you [00:44:12] Ankit Gupta: know, what's [00:44:12] Ankit Gupta: the point? You know? and I get [00:44:14] Ankit Gupta: frustrated. It's like more for [00:44:15] Ankit Gupta: me. Like [00:44:16] Ankit Gupta: it's actually the tiring. Like, I get more tired because I'm telling him to do [00:44:20] Ankit Gupta: something and he's [00:44:20] Ankit Gupta: not doing [00:44:21] Adam Fishman: Yeah, it's just sort of throw- throwing that lack of control back in your face constantly, right? [00:44:26] Ankit Gupta: yeah. And he's enjoying it. He's, [00:44:27] Ankit Gupta: like, jumping on the bed [00:44:28] Ankit Gupta: and re- having a great time, [00:44:29] Ankit Gupta: like, not following what I'm telling him to do. [00:44:31] Ankit Gupta: So we moved from San Francisco to New York, a month ago for, for my wife to sort [00:44:36] Ankit Gupta: of do this fellowship. it was a cool [00:44:38] Ankit Gupta: opportunity for, [00:44:40] Ankit Gupta: like a fresh [00:44:41] Ankit Gupta: start at the home. [00:44:43] Ankit Gupta: Like, when he was born, he came into a house [00:44:45] Ankit Gupta: that we were already living in, but, but here we rented a place and we [00:44:49] Ankit Gupta: could kind of reorganize it [00:44:51] Ankit Gupta: from [00:44:52] Ankit Gupta: scratch. So we really, uh, took that, [00:44:55] Ankit Gupta: opportunity [00:44:56] Ankit Gupta: and wanted to really design the whole house [00:44:58] Ankit Gupta: for being toddler-friendly in a [00:45:00] Ankit Gupta: way that we can... [00:45:01] Ankit Gupta: And, and, [00:45:02] Ankit Gupta: and learning from that Montessori, approach and, and how the Montessori classroom is designed, we wanted to design our home in [00:45:09] Ankit Gupta: a similar way so that he can do everything independently and, uh, like, the [00:45:15] Ankit Gupta: whole house is, is safe for him. [00:45:18] Ankit Gupta: and it also supports him [00:45:20] Ankit Gupta: to do the things we want him to [00:45:21] Ankit Gupta: do. [00:45:21] Ankit Gupta: Like, we have a, hand washing station. [00:45:24] Ankit Gupta: we're [00:45:24] Ankit Gupta: gonna start [00:45:24] Ankit Gupta: potty training, so we're, we're sort of doing that. We have a, we have a, kind of a dresser for him so he can pick out clothes. Our, our floor [00:45:32] Ankit Gupta: bed was part of that. It, it wasn't just a [00:45:34] Ankit Gupta: safety thing. We wanted him to, [00:45:37] Ankit Gupta: choose when to go into his, crib, which, which also opens up, so it [00:45:41] Ankit Gupta: kind of [00:45:41] Ankit Gupta: becomes a [00:45:42] Ankit Gupta: floor bed, [00:45:42] Ankit Gupta: and then [00:45:43] Ankit Gupta: when [00:45:44] Ankit Gupta: to go hang out with us, you know? [00:45:46] Ankit Gupta: And, like, he, he can decide, [00:45:47] Ankit Gupta: "Do you wanna sleep on the big bed? Do you wanna sleep on the little bed?" You know? And, that was sort of [00:45:50] Ankit Gupta: the idea. [00:45:51] Ankit Gupta: know, we're just [00:45:52] Ankit Gupta: trying to do this more and more. Like, we're also gonna get rid of our dining table and, and [00:45:55] Ankit Gupta: go for, [00:45:56] Ankit Gupta: like, a low, low dining table so that we can all just, [00:45:59] Ankit Gupta: like sit on the floor. [00:46:00] Ankit Gupta: I [00:46:00] Ankit Gupta: actually grew up eating on the floor with my parents. it's good for the [00:46:04] Ankit Gupta: legs, [00:46:05] Adam Fishman: Yeah. Yeah, I mean, in the US that seems strange, but in most of the world that's pretty normal actually , so yeah. [00:46:11] Ankit Gupta: You don't have to [00:46:12] Ankit Gupta: worry about like, "Oh, oh, [00:46:13] Ankit Gupta: you have to [00:46:14] Ankit Gupta: sit on your high chair [00:46:15] Ankit Gupta: to eat." [00:46:15] Ankit Gupta: you can just, just all, like, sit around. [00:46:17] Adam Fishman: so you don't do screens in your house. and you told me this and then you said, "Hey, instead of screens, we just have a ton of Montessori stuff." And you just described a lot of that. Like, the idea of Montessori is that, like, the kid can access almost anything. [00:46:31] Adam Fishman: Um, so you keep the cups and the bowls that are age-appropriate, but you keep them on a low shelf so your, your son can go in there and get them and, you know, pens and papers and, you know, balls and all the, all the things.I wanted to ask you about... 'Cause I've talked to a lot of people and a lot of experts recently on screen time, and there's a whole variety of takes on this. [00:46:50] Adam Fishman: This is one where, like, ask 10 parents, you get 10 different answers, right? This is not judgment on your parenting in any regard, but, there's less evidence that no screens is, matters any different than, like, a little bit of screen, right? And so in your household, it sounds like maybe no screens is not, like, a scientific-based thing. [00:47:11] Adam Fishman: It's more of a values claim. So tell me about the, the values that drove you to say no screens [00:47:17] Ankit Gupta: I believe in [00:47:18] Ankit Gupta: screen time. Like, I was [00:47:19] Ankit Gupta: the first one [00:47:20] Ankit Gupta: to get a computer in, in [00:47:22] Ankit Gupta: India, like in my, [00:47:23] Ankit Gupta: building, uh, in my college, and I grew up [00:47:26] Ankit Gupta: watching [00:47:26] Ankit Gupta: a lot of TV, [00:47:28] Ankit Gupta: a lot of National Geographic. [00:47:28] Ankit Gupta: Like, you know, it's... [00:47:29] Ankit Gupta: I think [00:47:30] Ankit Gupta: it's great. [00:47:30] Ankit Gupta: We had a weird experience. [00:47:31] Ankit Gupta: So we didn't do screens for the first year, [00:47:34] Ankit Gupta: and then we took him to, [00:47:36] Ankit Gupta: uh, get his hair cut. So his first haircut was, like, at one month old, uh, and we shaved his hair. Uh, it's like a, [00:47:44] Ankit Gupta: you know, cultural thing that you do in India. [00:47:46] Ankit Gupta: And the way the barber did it was put him in [00:47:49] Ankit Gupta: front of a big TV, [00:47:50] Ankit Gupta: so the first time he ever saw [00:47:52] Ankit Gupta: TV was at the [00:47:53] Ankit Gupta: barber shop, [00:47:53] Ankit Gupta: the barber literally has a razor blade, like a, like a, single [00:47:58] Ankit Gupta: razor sharp blade, and he's shaving off all of his hair, and it took 10 minutes, and he was totally glued to the TV. [00:48:06] Ankit Gupta: Like, he was, [00:48:06] Adam Fishman: Yeah. [00:48:07] Ankit Gupta: he was not moving. [00:48:08] Adam Fishman: to that reward system, then he was probably like, "Dad, can I get my hair cut every day?" [00:48:13] Ankit Gupta: Yeah. Yeah. he even had a hangover from that actually. Like he was kind of, he was kind of [00:48:18] Ankit Gupta: like out of it afterwards, like he was a little, [00:48:21] Ankit Gupta: lost. [00:48:21] Ankit Gupta: and, the next time he watched TV was again at [00:48:23] Ankit Gupta: the barber shop like six [00:48:24] Ankit Gupta: months later. but we just [00:48:26] Ankit Gupta: noticed that, [00:48:27] Ankit Gupta: and it felt weird. It's almost like, you got drunk or, you know, something. [00:48:31] Ankit Gupta: and so [00:48:31] Ankit Gupta: I think for us it's just become [00:48:33] Ankit Gupta: a, a little bit of that. Like, [00:48:34] Ankit Gupta: we wanna encourage, like building stuff, [00:48:37] Ankit Gupta: uh, curiosity, books, like love [00:48:40] Ankit Gupta: for learning. Uh, e- like even with our Montessori materials, we rotate them [00:48:44] Ankit Gupta: pretty frequently. Like [00:48:45] Ankit Gupta: if he keeps going to the same thing every day, and it's not [00:48:49] Ankit Gupta: in- instructional anymore, then we rotate it out and he tries something new, and he just like discovers [00:48:55] Ankit Gupta: new things. [00:48:56] Ankit Gupta: So [00:48:56] Ankit Gupta: screen time for us is, [00:48:57] Ankit Gupta: know, less important right now because we want him to sort of [00:49:01] Ankit Gupta: get that sense [00:49:02] Ankit Gupta: of wonder in the world, like [00:49:04] Ankit Gupta: build stuff, have [00:49:05] Ankit Gupta: curiosity, [00:49:07] Ankit Gupta: p- try playing music, [00:49:08] Ankit Gupta: try singing, try doing other things. [00:49:10] Ankit Gupta: but then as he starts [00:49:11] Ankit Gupta: to understand how to [00:49:14] Ankit Gupta: use screen time, like how it can be sort of in- instructional, then I think [00:49:19] Ankit Gupta: we would be totally fine, [00:49:20] Ankit Gupta: like letting him... [00:49:22] Ankit Gupta: And, and in some ways I want him to regulate his own [00:49:24] Ankit Gupta: screen time. You know? Like the environment should be such [00:49:26] Ankit Gupta: that he can choose to have screen time or he can choose to play with something else. [00:49:32] Ankit Gupta: I just don't think developmentally he's ready yet to sort of make that choice, [00:49:36] Ankit Gupta: so we haven't given him the choice. [00:49:37] Ankit Gupta: And it actually frankly helps [00:49:39] Ankit Gupta: us. We don't have a TV at home, [00:49:40] Ankit Gupta: and it's amazing. [00:49:42] Adam Fishman: There's no, there's no temptation, right? There's, that's not there, so he doesn't even think about it, and you don't think about it, right? [00:49:48] Adam Fishman: So, yeah, [00:49:49] Adam Fishman: I wanted to talk about another thing that you do, uh, which is around meal planning. you do meal planning for the whole week. You said maybe people might think that's silly, but it saves you a ton of mental load. [00:50:00] Adam Fishman: And I've had many people on this show recently talk about mental load. I don't think it's silly at all, by the way. I, we do it in our household. I've got a, I've got the whole week mapped out of what we're eating. And that's exactly right, because I don't even have to think about it. It's just like, "Oh, it's Tuesday. [00:50:15] Adam Fishman: We're having this." [00:50:16] Adam Fishman: tell me about your meal planning. What does that look like in your house? [00:50:19] Ankit Gupta: I [00:50:19] Ankit Gupta: didn't realize, you [00:50:20] Ankit Gupta: know, a lot of people [00:50:21] Ankit Gupta: were [00:50:21] Ankit Gupta: doing this. weekly ,just kind of stumbled into it. [00:50:24] Ankit Gupta: that's one place where I go crazy with AI. Like AI and I have, a lot of fun, you know, meal planning for him. and I give it all sorts of constraints, like he can't have the same thing for dinner the [00:50:35] Ankit Gupta: next day for [00:50:35] Ankit Gupta: lunch, and all that stuff. [00:50:37] Ankit Gupta: but yeah, [00:50:38] Ankit Gupta: it's usually like [00:50:39] Ankit Gupta: Sunday [00:50:40] Ankit Gupta: if I'm [00:50:41] Ankit Gupta: feeling energetic, or if I'm lazy, then it's like Monday. [00:50:43] Ankit Gupta: you know, I try to make sure [00:50:45] Ankit Gupta: there's some variation in breakfast, but that's usually the same. You know, lunch is always different, dinner is always different. Uh, it's all [00:50:54] Ankit Gupta: fairly warm. [00:50:55] Ankit Gupta: he eats leftovers the [00:50:56] Ankit Gupta: next day or the day after, but [00:50:58] Ankit Gupta: like, not, [00:50:58] Ankit Gupta: not too much later than that. and then these days he's [00:51:02] Ankit Gupta: having a heavy snack, [00:51:03] Ankit Gupta: so there's like a, there's like a [00:51:05] Ankit Gupta: snack. [00:51:05] Ankit Gupta: So there's sort of four meals to plan [00:51:07] Ankit Gupta: for, and it's... I just have an obs- [00:51:09] Ankit Gupta: like a doc [00:51:09] Ankit Gupta: in [00:51:09] Ankit Gupta: my Notes app that, keep it all there. [00:51:12] Ankit Gupta: but then Claude really helps me, you know, understand like [00:51:16] Ankit Gupta: what recipes [00:51:17] Ankit Gupta: are working. "Oh, this thing you tried like two weeks [00:51:19] Ankit Gupta: ago, maybe you [00:51:20] Ankit Gupta: can try it again." Or we introduced mushrooms, he didn't like [00:51:22] Ankit Gupta: it, maybe we can do [00:51:23] Ankit Gupta: it again. This is [00:51:24] Ankit Gupta: where I use [00:51:25] Ankit Gupta: Instagram a lot, like to get recipe [00:51:27] Ankit Gupta: inspirations. [00:51:28] Adam Fishman: and [00:51:29] Ankit Gupta: then I promptly close it ' 'cause it's such [00:51:32] Adam Fishman: Well, first you have to [00:51:33] Ankit Gupta: place? [00:51:33] Adam Fishman: up on the latest Startup Dad [00:51:35] Ankit Gupta: Yeah. [00:51:36] Ankit Gupta: Yes, for sure. [00:51:38] Adam Fishman: you close it, you [00:51:39] Adam Fishman: know? Uh, right, of every guest is actually, uh, contractually bound to become a follower of the Startup Dad pod Instagram handle, so. no, that's awesome, and you've kind of inspired me. [00:51:50] Adam Fishman: This is-- I run a lot of OpenClaw agents, and my next agent is a, is a house manager and that I have to build, and, uh, I think meal, meal planning, I already do it, but I think help, getting help with it will be a thing, that I will use that OpenClaw agent for. okay, I wanted to come back to, I mentioned the best and worst day of your career, um, which, you know, maybe was a little, little hyperbolic on my part. [00:52:15] Adam Fishman: But, I'm gonna take us back to June 7th, 2010. you were building Pulse. You shipped it... This is the app that you eventually sold to LinkedIn. So [00:52:24] Ankit Gupta: Yeah [00:52:24] Adam Fishman: though maybe best and worst day, like things ended up okay. [00:52:27] Adam Fishman: So, so you, you shipped your app the week before. Um, so tell me about the, the app. [00:52:32] Adam Fishman: What, was or is Pulse? [00:52:34] Ankit Gupta: Yeah, so Pulse was a news reading app. This was back when people were still [00:52:37] Ankit Gupta: downloading apps. [00:52:38] Ankit Gupta: you know, the iPad had just come out. we were, uh, one of the first apps on the iPad [00:52:45] Ankit Gupta: and, um, you [00:52:46] Ankit Gupta: know, it was obviously a great device for, for sort of reading. And so Pulse allowed you to [00:52:50] Ankit Gupta: aggregate all of the news [00:52:52] Ankit Gupta: across [00:52:53] Ankit Gupta: the internet. [00:52:54] Ankit Gupta: and [00:52:54] Ankit Gupta: basically pooled [00:52:55] Ankit Gupta: it. It was a [00:52:55] Ankit Gupta: beautiful interface, very efficient, very streamlined, [00:52:59] Ankit Gupta: and you could [00:52:59] Ankit Gupta: quickly browse the news that you wanted and, you know, get on with your day. [00:53:03] Adam Fishman: So you, you built this when you were at the Stanford, in Stanford, right? The [00:53:07] Adam Fishman: d.school, uh, in like Launch, Launchpad or whatever that c- course is. And, um, so that morning is the dev-- Worldwide Developers Conference for Apple. It's their keynote, right? And Steve Jobs still alive. Oh, rest in peace. May he rest in [00:53:22] Adam Fishman: peace. [00:53:23] Adam Fishman: He's on stage and he name-drops Pulse, [00:53:25] Adam Fishman: right? [00:53:25] Adam Fishman: which is like, whoa. and then, I mean, that's amazing. Top of the world. You're like, "I can't believe it. Look at us. We're gonna be billionaires." Like the whole thing. And then that evening at like 6:30 Pacific Time, Apple pulls it from the store. unrelated to him announcing it, but pulls [00:53:43] Ankit Gupta: Ew [00:53:43] Adam Fishman: from the store. [00:53:43] Adam Fishman: So what, what happened? What's the story behind that? [00:53:46] Ankit Gupta: Yeah, it's, it's pretty wild. I [00:53:47] Ankit Gupta: mean, we [00:53:48] Ankit Gupta: didn't know that Steve was gonna talk about [00:53:50] Ankit Gupta: the app, [00:53:50] Ankit Gupta: but he was [00:53:51] Ankit Gupta: announcing the iPhone 4, and before that [00:53:53] Ankit Gupta: he went through [00:53:54] Ankit Gupta: some of the top apps on the iPad, and it, it looks like he just liked Pulse. So he, you know, he, he talked about it. [00:54:01] Ankit Gupta: and at [00:54:02] Ankit Gupta: that time we were still [00:54:03] Ankit Gupta: students. [00:54:04] Ankit Gupta: We had no money and [00:54:05] Ankit Gupta: still had debt, and we had no jobs, and [00:54:08] Ankit Gupta: the app was, paid and, we [00:54:10] Ankit Gupta: were pretty happy I think because of the, uh, spotlight, um, you know, New York Times found out about it. New York Times, uh, had an RSS feed that we [00:54:19] Ankit Gupta: used in our [00:54:20] Ankit Gupta: app, and [00:54:20] Ankit Gupta: for [00:54:21] Ankit Gupta: whatever reason, they thought we were violating their, their, uh, agreement. [00:54:25] Ankit Gupta: And, and they basically sent a cease and desist to Apple, and Apple, you know, just wanted [00:54:30] Ankit Gupta: to play nice and pulled the app. and so it was this sort of 12... for, the, for 12 hours thing, we were at the top of the App Store or [00:54:36] Ankit Gupta: pretty close to the top of the App Store, riding high. Uh, we even tried to get into the developer conference, but we couldn't because we didn't have a ticket. [00:54:42] Ankit Gupta: but we sort of hung out outside Moscone Center, uh, feeling pretty happy. And, and then the New York Times thing happened, and [00:54:49] Ankit Gupta: we [00:54:50] Ankit Gupta: were just like, "I guess it's time to go look [00:54:54] Ankit Gupta: for a job." You know, like, "I guess it's done." Like, "This was a great day, you [00:54:57] Ankit Gupta: know, we [00:54:58] Ankit Gupta: built an app [00:54:58] Ankit Gupta: and, and yeah, I guess [00:55:00] Ankit Gupta: it's time to call [00:55:01] Ankit Gupta: it a day." [00:55:02] Ankit Gupta: Next day we started [00:55:03] Ankit Gupta: to figure out how [00:55:04] Ankit Gupta: to fight again. [00:55:05] Adam Fishman: Yep [00:55:06] Ankit Gupta: uh, yeah, [00:55:07] Ankit Gupta: it's the highs and lows of [00:55:07] Ankit Gupta: startups. [00:55:08] Adam Fishman: Yeah. Um, and of course, the app got back into the App Store. You appeased The New York Times and you were back in, and then you eventually sold it to, to LinkedIn. Um, but the reason I wanted to talk about this is, you know, this is probably, in your professional career, this may be the most like highest adrenaline, dopamine day of your professional life, right? [00:55:28] Adam Fishman: and then when I asked you, and you, you alluded to this, when I asked you about the best part of your dad day as a, as a parent, you were like, "The best part of my day is my son's drinking milk and he's just like nuzzled up with me on the couch. It's morning, it's calm, it's cuddly time, and we're just reading a book." [00:55:44] Adam Fishman: So like, are these two people the same person? Like, that's what my question is. Like, uh, it's amazing the transformation for you of what you, what gets you excited and gets you feeling great. Could you just [00:55:57] Adam Fishman: reflect on that for a minute? [00:55:59] Ankit Gupta: You know, I feel like everyone talks about how moms change through pregnancy and through, through having, a child. [00:56:06] Ankit Gupta: but I think dads change too, [00:56:07] Ankit Gupta: I feel [00:56:08] Ankit Gupta: like I used to be the person who [00:56:10] Ankit Gupta: needs [00:56:11] Ankit Gupta: to constantly solve problems and [00:56:14] Ankit Gupta: get that, recognition from [00:56:16] Ankit Gupta: everyone that I am, this, [00:56:19] Ankit Gupta: like, genius problem solver or, like, making impact or, have some [00:56:25] Ankit Gupta: standing in society. Like, like, this sort of, external validation. I don't know why, but that was like super important to me. [00:56:32] Ankit Gupta: it's definitely changed since having [00:56:34] Ankit Gupta: my son. Like, since having my son, [00:56:35] Ankit Gupta: I feel like [00:56:37] Ankit Gupta: I wanna [00:56:39] Ankit Gupta: really help [00:56:39] Ankit Gupta: him be the best [00:56:40] Ankit Gupta: version of [00:56:41] Ankit Gupta: himself. [00:56:42] Ankit Gupta: and whatever my role is in that [00:56:44] Ankit Gupta: is, is sort of what makes me feel good [00:56:47] Adam Fishman: Yeah. It sounds like it's made you a lot more maybe selfless. Like, uh, think about yourself quite a bit less than this other person now who so much on you [00:57:01] Ankit Gupta: like, [00:57:02] Ankit Gupta: I still think about what my parenting [00:57:03] Ankit Gupta: philosophy is and how I want to change. I still, I still think about myself, [00:57:07] Ankit Gupta: you know. I still like to build stuff, like you know, building this, [00:57:11] Ankit Gupta: this [00:57:11] Ankit Gupta: app. Like, I, I still love to get that sort of public [00:57:14] Ankit Gupta: recognition. [00:57:15] Ankit Gupta: it's just a little [00:57:16] Ankit Gupta: bit more of, uh, of sort of contentment with the day-to-day, [00:57:20] Ankit Gupta: it's like I'm not [00:57:21] Ankit Gupta: chasing something. Like I'm, I'm [00:57:24] Ankit Gupta: okay with being more present and just being [00:57:27] Ankit Gupta: more [00:57:27] Ankit Gupta: in [00:57:28] Ankit Gupta: the moment. Eh, [00:57:29] Ankit Gupta: tha- and that's actually really hard for me, so I s- I sometimes have to like pull myself to, to be, be doing that. so 7:00 AM [00:57:36] Ankit Gupta: cuddling with [00:57:37] Ankit Gupta: my son just happens naturally. [00:57:39] Ankit Gupta: But that, that doesn't keep happening naturally a [00:57:41] Ankit Gupta: lot of time throughout the day. I have to bring myself back [00:57:44] Ankit Gupta: to to that. [00:57:45] Ankit Gupta: but yeah, [00:57:46] Ankit Gupta: I think that's, [00:57:47] Ankit Gupta: changed [00:57:47] Ankit Gupta: a lot. Like I'm not [00:57:48] Ankit Gupta: trying to chase this big [00:57:51] Ankit Gupta: milestone. I'm, I'm just trying to be, [00:57:55] Ankit Gupta: be in the moment, [00:57:56] Adam Fishman: Yeah. I guess maybe that means the definition of success has changed for you or something like that. The goals have changed. [00:58:04] Ankit Gupta: I think, like, that's why I don't think I wanna, [00:58:06] Ankit Gupta: uh, Like, [00:58:07] Ankit Gupta: I'm, d- I'm not doing it all or [00:58:09] Ankit Gupta: trying to be someone. [00:58:12] Ankit Gupta: like, what is success even? For me, I'm, I'm really trying to think about what drives [00:58:16] Ankit Gupta: me. [00:58:16] Ankit Gupta: Like, what is content? What makes me feel satisfied, and what makes me feel contented? [00:58:21] Ankit Gupta: And that used to be having the top app at the App Store, or, or that used to be, like, solving a hard societal problem. And, and right now it's, uh, spending time with my son. [00:58:35] Ankit Gupta: that doesn't mean it, it might not change [00:58:37] Adam Fishman: Sure. This [00:58:38] Ankit Gupta: future. [00:58:39] Adam Fishman: that you are in, in life, as we say [00:58:41] Adam Fishman: on the show a lot. Yeah. [00:58:42] Ankit Gupta: Yeah. [00:58:43] Ankit Gupta: I just wanna lean into that season as much as I can, because that season will change. [00:58:49] Ankit Gupta: You know, it's not gonna stay the same [00:58:50] Adam Fishman: I wanted to pivot away from your son for just a couple minutes because, one of the questions that you posed to yourself in our prep is what does it mean to be a good partner to your wife? and you didn't answer it in the prep. You sort of left it hanging out there. so I guess, like, what would you say? [00:59:07] Adam Fishman: Like, what does it mean to be a good partner in your investigations? [00:59:10] Ankit Gupta: Yeah, [00:59:11] Ankit Gupta: I mean, I'm [00:59:11] Ankit Gupta: still trying [00:59:12] Ankit Gupta: to figure that out. [00:59:14] Ankit Gupta: My wife find-- thinks it's really funny, like if we have a fight, I go and [00:59:19] Ankit Gupta: think [00:59:20] Ankit Gupta: about... Like, I go for a walk if I need to go outside [00:59:22] Ankit Gupta: the house, and I, I like think about, "So what happened?" Like, you know, try to build an algorithm [00:59:27] Adam Fishman: Yeah. [00:59:27] Ankit Gupta: what did [00:59:28] Ankit Gupta: she do? What did [00:59:29] Ankit Gupta: I do? What could I have done differently? [00:59:30] Ankit Gupta: Like, what happened? engineer of you. [00:59:32] Adam Fishman: Yeah [00:59:33] Ankit Gupta: yeah. [00:59:33] Ankit Gupta: And then [00:59:33] Ankit Gupta: she-- And then I come [00:59:34] Ankit Gupta: back and I... You know, one day I was actually like talking to her about this, like, "Oh, you told me this, and I told me that." And then [00:59:40] Ankit Gupta: she was like, "Well, all I [00:59:41] Ankit Gupta: wanted was someone to hear what I was saying." And I was like, "Well, that's not always the case. Like, sometimes you actually want me to problem solve, so I'm like confused right now." [00:59:49] Ankit Gupta: what [00:59:49] Ankit Gupta: I [00:59:51] Ankit Gupta: have started [00:59:52] Ankit Gupta: to realize is I need to support [00:59:54] Ankit Gupta: her [00:59:55] Ankit Gupta: in whatever she needs to do, [00:59:57] Ankit Gupta: basically. like [00:59:58] Ankit Gupta: in some moment she needs me to be there for her. In some moment [01:00:02] Ankit Gupta: she needs me to help her get unstuck. In some moment she needs me to [01:00:07] Ankit Gupta: like [01:00:08] Ankit Gupta: help her [01:00:08] Ankit Gupta: have some alone time. in some moment she needs me to like [01:00:12] Ankit Gupta: help chase this parenting curiosity she has and try something different. [01:00:16] Ankit Gupta: but [01:00:17] Ankit Gupta: I think [01:00:17] Ankit Gupta: it's, it's like [01:00:18] Ankit Gupta: whatever-- Aursh wants to work [01:00:19] Ankit Gupta: hard and make sure our son [01:00:21] Ankit Gupta: is cared for. Like [01:00:22] Ankit Gupta: I need to be able to sort of support her in whatever she wants [01:00:26] Ankit Gupta: to do, uh, 'cause [01:00:27] Ankit Gupta: I also can't really change [01:00:29] Ankit Gupta: what she [01:00:29] Ankit Gupta: wants [01:00:30] Ankit Gupta: to do, you know? [01:00:31] Ankit Gupta: I think the flip side to that is I need to be communicative for how I'm feeling about everything. [01:00:37] Ankit Gupta: So it's not just like, " [01:00:38] Ankit Gupta: Oh, I'm supporting her in whatever she wants to do, and I'm [01:00:41] Ankit Gupta: feeling crappy about something else." Like, I can do both of those things. I can, I [01:00:46] Ankit Gupta: can support [01:00:46] Ankit Gupta: her, I can also feel crappy, and I can [01:00:48] Ankit Gupta: also tell her that I feel crappy while I'm [01:00:50] Adam Fishman: Yeah, you, you're allowed to have bad days. You don't have to protect her from the fact that you too have a, have a bad day, [01:00:57] Ankit Gupta: Yeah. [01:00:57] Adam Fishman: something like that, you know? [01:00:58] Ankit Gupta: Yeah, and I, I don't think [01:01:00] Ankit Gupta: I was open with my feelings for a long time in our marriage. Only in the last, like, two or three years I've been I've been more so. And it, it's really helpful [01:01:08] Adam Fishman: kids, uh, kids can pull that out of you, right? Yeah [01:01:10] Ankit Gupta: Man, these con- the conversations we've had [01:01:13] Ankit Gupta: in those early days of having a child, like, they were explosive. Like, they were tough. [01:01:17] Adam Fishman: You're pretty tired. I'm not gonna lie. You're not at your best in those early days. So it pull-- it really pulls a lot out of you, so. I really appreciate you sharing, uh, all that. I wanted to ask too, as a follow-up to that, so right now the arrangement in your house is like relatively clear, right? [01:01:36] Adam Fishman: Like your wife's got her fellowship that has fixed punishing hours. You have flexibility. the split is probably a bit more obvious, right? Because in, in a way that it isn't for most couples. have you talked about what happens when her fellowship ends and maybe the split becomes a little less obvious? [01:01:55] Adam Fishman: Or when you want to go start a company again or something like that? Like what, what are those conversations like? [01:02:01] Ankit Gupta: we've had those conversations. I [01:02:02] Ankit Gupta: mean, she knows how I am. I, I actually, uh, [01:02:05] Ankit Gupta: often, complain [01:02:06] Ankit Gupta: to her [01:02:07] Ankit Gupta: that, "Oh, all I've become is, like, making his meals and [01:02:11] Ankit Gupta: taking the dog out, and I have no identity." Like, I, you know, I have [01:02:15] Ankit Gupta: those... dopamine desert. [01:02:16] Ankit Gupta: so she consoles me and [01:02:20] Ankit Gupta: basically [01:02:21] Ankit Gupta: says, "Hey, you're gonna find something. [01:02:22] Ankit Gupta: You're gonna go off and do something, and, [01:02:24] Ankit Gupta: it's just a matter of time." and she's seen me, the early days, I started Bicycle [01:02:29] Ankit Gupta: right after we got married. [01:02:30] Ankit Gupta: and so she's gone through [01:02:31] Ankit Gupta: one of those journeys and seen how hard [01:02:36] Ankit Gupta: I end up [01:02:37] Ankit Gupta: working, you know, in the early days, and how I'm [01:02:40] Ankit Gupta: waking up at [01:02:40] Ankit Gupta: night, [01:02:41] Ankit Gupta: and working all the time. [01:02:42] Ankit Gupta: And, And, and so I think she knows [01:02:43] Ankit Gupta: we've never had to, like, [01:02:45] Ankit Gupta: formally talk about, [01:02:47] Ankit Gupta: like, role splits or [01:02:48] Ankit Gupta: job splits. [01:02:49] Ankit Gupta: but we tend to gravitate towards certain things, so it, it just sort of naturally happens. Uh, but I'm sure [01:02:56] Ankit Gupta: it'll be hard. [01:02:56] Ankit Gupta: You know, it'll be hard if the roles reverse. [01:02:59] Ankit Gupta: It's already hard right now when I have a, a plan, like this is my meal plan, and she wants to do something different, and she's not around to do something different. You know? Like, she's not around to choose a different activity or have him eat [01:03:17] Ankit Gupta: differently, and I, I, I [01:03:19] Ankit Gupta: sort of have to either change and [01:03:22] Ankit Gupta: do more [01:03:22] Ankit Gupta: work for myself or not [01:03:24] Ankit Gupta: change and disregard whatever she wants to do. [01:03:26] Ankit Gupta: So, [01:03:26] Ankit Gupta: you know, even [01:03:27] Ankit Gupta: though the role split is pretty [01:03:29] Ankit Gupta: obvious, it's [01:03:29] Ankit Gupta: still hard because y- [01:03:31] Ankit Gupta: she is also as involved as [01:03:33] Ankit Gupta: a parent [01:03:33] Ankit Gupta: as I am, just doesn't happen to have the kind [01:03:36] Ankit Gupta: of time that [01:03:37] Ankit Gupta: I have. so I feel like we're still [01:03:38] Ankit Gupta: figuring it out. [01:03:39] Ankit Gupta: and maybe at some point it's gonna be different, [01:03:42] Ankit Gupta: and it'll be a different version of that. [01:03:44] Ankit Gupta: but we've had so many of these conversations now and, and, and so much of the [01:03:48] Ankit Gupta: sort of sharing of our feelings and sort of navigating this that I, I feel like we're in a much better place now than we were maybe when our son was born, [01:03:57] Ankit Gupta: I wanna come all the way back to revisit something you said at the earlier part of our conversation, which is that being a founder is actually fairly well aligned with being a parent, or being an entrepreneur is fairly well aligned with, with being a, a parent. [01:04:11] Adam Fishman: I'm gonna call this a contrarian take because, it seems very hard, especially if you are not one of those things and thinking about it. it seems like each one of those is the hardest job you will ever do, and then you try to do them both at the same time. you're not gonna be a 10 out of 10 at each of them at the same time. [01:04:28] Adam Fishman: I'll quote exactly what you said to me, which is, "Being an entrepreneur is the most aligned job with being a parent, and it's easier than ever to be an entrepreneur with AI now." So I agree with that second part for sure. It's that first part that I wanna push on. So why do you think that being an entrepreneur or entrepreneurship is aligned with, with parenting super well? [01:04:46] Ankit Gupta: I think I got that notion probably [01:04:47] Ankit Gupta: from my dad. You know, he's been an entrepreneur, [01:04:50] Ankit Gupta: since I remember it. And, [01:04:51] Ankit Gupta: you know, he's had [01:04:52] Ankit Gupta: four companies. two [01:04:53] Ankit Gupta: of them, uh, are no longer there, two of them are, [01:04:56] Ankit Gupta: are still doing well. [01:04:57] Ankit Gupta: And, and, you know, he's, he's still working on them. And, and I remember my dad being [01:05:02] Ankit Gupta: around a lot. [01:05:04] Ankit Gupta: it never felt like he, was sort [01:05:07] Ankit Gupta: of not [01:05:07] Ankit Gupta: available. Like, we would have a lot of fun. I would [01:05:09] Ankit Gupta: wake up and I would see him. [01:05:11] Ankit Gupta: You know, [01:05:11] Ankit Gupta: we would go for activities together. [01:05:13] Ankit Gupta: my version of what a dad [01:05:14] Ankit Gupta: is, I think, [01:05:15] Ankit Gupta: I think came from that, but I didn't fully realize how [01:05:19] Ankit Gupta: nice it was to be a founder and a dad until I, [01:05:22] Ankit Gupta: I became one. [01:05:23] Ankit Gupta: And, [01:05:24] Ankit Gupta: you know, I was able to [01:05:26] Ankit Gupta: have that kind of flexibility, time [01:05:28] Ankit Gupta: flexibility for, for myself. Like, I carved out [01:05:31] Ankit Gupta: my entire Friday to spend with [01:05:33] Ankit Gupta: my son. So he would go to school Monday [01:05:35] Ankit Gupta: to Thursday. Friday, Saturday, Sunday, he [01:05:37] Ankit Gupta: would be with h- at home, [01:05:38] Ankit Gupta: and I would have all of that time to, to spend [01:05:41] Ankit Gupta: with him. [01:05:41] Ankit Gupta: I would be able to take him to classes, you know, [01:05:45] Ankit Gupta: during the day even, because I can block that off in, [01:05:48] Ankit Gupta: in my calendar. [01:05:49] Ankit Gupta: and so one is, I think, [01:05:50] Ankit Gupta: time flexibility. [01:05:51] Ankit Gupta: Like, as a founder, you can [01:05:53] Ankit Gupta: choose to work [01:05:54] Ankit Gupta: on your own time, and generally that works out. I think the second is, the goal of a founder [01:06:01] Ankit Gupta: is to do as less as possible. Like, [01:06:04] Ankit Gupta: the whole job is to not have a job. Like, you hire the best people, [01:06:09] Ankit Gupta: you set up the strategy, you set [01:06:11] Ankit Gupta: up the plan, [01:06:12] Ankit Gupta: people are supposed to execute [01:06:13] Ankit Gupta: it. Like, [01:06:13] Ankit Gupta: when, when our son was born, Bicycle was going from, [01:06:17] Ankit Gupta: from sort of cash burning [01:06:18] Ankit Gupta: to profitability. We had a great plan. We were pulling all the levers. but [01:06:22] Ankit Gupta: at the same time, we [01:06:23] Ankit Gupta: needed a little bit more money to sort [01:06:24] Ankit Gupta: of bridge us to, [01:06:25] Ankit Gupta: to that gap. And so, [01:06:27] Ankit Gupta: the last board meeting before he [01:06:30] Ankit Gupta: was born, I [01:06:30] Ankit Gupta: actually did the board meeting from the restroom of the labor room. [01:06:35] Ankit Gupta: it was wild, uh, because it all happened very quickly, and my wife was induced and, [01:06:41] Ankit Gupta: we started the process [01:06:43] Ankit Gupta: while the board meeting was going on. [01:06:45] Ankit Gupta: And I, I, I basically told the board, "Listen, I'm gonna be out sooner than I expected. Like, start my paternity leave [01:06:52] Ankit Gupta: tomorrow." Yeah [01:06:54] Ankit Gupta: "yeah. So [01:06:56] Ankit Gupta: it's kind of up to you guys. Like, this is the amount of money we need, and [01:07:00] Ankit Gupta: we kind of need it in the [01:07:01] Ankit Gupta: next 90 days. [01:07:02] Ankit Gupta: And-" Either I come back from paternity leave [01:07:04] Ankit Gupta: and and we [01:07:04] Ankit Gupta: have that or, or, or not. and at the same time, I had an executive [01:07:08] Ankit Gupta: team and we had a great plan for how to, you know, get the [01:07:11] Ankit Gupta: company to profitability and, and it needed to be executed. [01:07:15] Ankit Gupta: And I was like, "I'm gonna go on paternity leave. You guys execute the plan. Let me know [01:07:20] Ankit Gupta: if [01:07:20] Ankit Gupta: anything comes up." [01:07:21] Ankit Gupta: but everything was fine. [01:07:22] Ankit Gupta: Like, I came back from paternity leave. It was, it was two months, two, two and a half months. Then, the company was profitable. And We had the money in the bank. [01:07:30] Ankit Gupta: Everything turned out to be great. [01:07:32] Ankit Gupta: you just can't do that [01:07:33] Ankit Gupta: in any other job. Literally, it's, like, impossible [01:07:37] Ankit Gupta: to do that in any other job. I also think being a founder really gives you that sense of, self-sufficiency. Like, I, I, I think there's so much, uncertainty. [01:07:46] Ankit Gupta: We talked [01:07:46] Ankit Gupta: about this. [01:07:47] Ankit Gupta: Like, as a parent, [01:07:48] Ankit Gupta: you [01:07:48] Ankit Gupta: kind of have to navigate, [01:07:49] Ankit Gupta: like, what's going on, and you don't know what the right [01:07:52] Ankit Gupta: thing is to do, but you still [01:07:53] Ankit Gupta: have to kind of [01:07:54] Ankit Gupta: do it. And, and you've, you have to do that as a [01:07:56] Ankit Gupta: founder all day long. [01:07:58] Ankit Gupta: So I feel like [01:07:58] Ankit Gupta: you get a certain sense of sort of, [01:08:00] Ankit Gupta: recruiting [01:08:00] Ankit Gupta: a nanny. [01:08:01] Ankit Gupta: Like, you get a certain sense of sort of how to spot [01:08:03] Ankit Gupta: good talent, how to actually [01:08:05] Ankit Gupta: get them to work well. Like, how do you actually navigate this sort of weird process? How do you actually self-improve [01:08:11] Ankit Gupta: constantly while doing that? Like, there's so many things you learn as a founder while also having the lifestyle. [01:08:18] Ankit Gupta: And, and at some point, you know, if you raise money, you can pay yourself pretty [01:08:21] Ankit Gupta: well and, and have the, have the capital too, to be, to be able to, [01:08:25] Ankit Gupta: you know, spend time with [01:08:26] Ankit Gupta: your kid. And, and, and now with AI, you can [01:08:28] Ankit Gupta: actually have [01:08:29] Ankit Gupta: these [01:08:30] Ankit Gupta: agents running [01:08:31] Ankit Gupta: overnight if [01:08:32] Ankit Gupta: you don't hire someone. You don't even need a human. [01:08:34] Ankit Gupta: You [01:08:34] Ankit Gupta: can have an agent [01:08:35] Ankit Gupta: running overnight and, and, and you can have the time [01:08:37] Ankit Gupta: to take your son to a music class. So, [01:08:39] Ankit Gupta: I don't know. And most people feel like, right, starting a company is [01:08:42] Ankit Gupta: a risk, but it's actually the opposite. Like, someone's actually paying you to start a company, [01:08:46] Ankit Gupta: Even though [01:08:47] Ankit Gupta: you're not qualified to start that company. [01:08:49] Adam Fishman: sure. [01:08:50] Adam Fishman: sure. Yeah, [01:08:52] Adam Fishman: yeah. [01:08:53] Adam Fishman: if you think about somebody who is about to step into your shoes, so either a founder that's about to become a parent like you were, um, or a parent that's about to become a founder like you might eventually be again, [01:09:07] Adam Fishman: what single piece of advice would you, would you give to them? [01:09:10] Adam Fishman: Now again, this is the way that you've done it, but what have, what have you learned that's something you would share with, with somebody, about to be in your shoes? [01:09:17] Ankit Gupta: Yeah, I mean, I think from my perspective, if you are a founder about [01:09:21] Ankit Gupta: to become a parent, you really need to think about where [01:09:23] Ankit Gupta: that time is gonna come from for parenting. [01:09:26] Ankit Gupta: there's probably things you do as a founder you don't need to do. like the least amount of decisions that can be blocked on you or the least amount of like actual day-to-day work you [01:09:37] Ankit Gupta: can do, the better, [01:09:38] Ankit Gupta: because that time will be needed [01:09:40] Ankit Gupta: for being [01:09:41] Ankit Gupta: a parent. [01:09:41] Ankit Gupta: try to get yourself [01:09:42] Ankit Gupta: out of the job [01:09:43] Ankit Gupta: as much as [01:09:43] Ankit Gupta: you can and [01:09:44] Ankit Gupta: try to be as much as a, uh, of a figurehead, [01:09:46] Ankit Gupta: of a CEO or a [01:09:47] Ankit Gupta: figurehead of [01:09:48] Ankit Gupta: an executive, like [01:09:49] Ankit Gupta: as much as you can, uh, [01:09:50] Ankit Gupta: in a, in the most positive way possible. [01:09:53] Ankit Gupta: And then if you have excess time, that's great, you can fill it with, with stuff. [01:09:58] Ankit Gupta: but most likely you're still gonna be [01:10:00] Ankit Gupta: scrambling [01:10:00] Ankit Gupta: for time. But [01:10:00] Ankit Gupta: that time to parent and that time [01:10:02] Ankit Gupta: to support your spouse has [01:10:03] Ankit Gupta: to come [01:10:04] Ankit Gupta: from somewhere. [01:10:05] Ankit Gupta: So I think, I think that would be [01:10:06] Ankit Gupta: my advice. For someone who's already a parent and wanting to do a startup, mean, I would be 100, [01:10:11] Ankit Gupta: 110% supportive of it, [01:10:13] Ankit Gupta: but my advice would be to really like [01:10:17] Ankit Gupta: forget about all [01:10:17] Ankit Gupta: the knowledge all, all the advice that people give on, [01:10:21] Ankit Gupta: on [01:10:21] Ankit Gupta: starting companies. [01:10:22] Ankit Gupta: Uh, and definitely don't create a business plan. just don't spend [01:10:26] Ankit Gupta: time on anything. Just spend time on like defining the problem and solving the problem [01:10:31] Ankit Gupta: and finding your first user, and then finding the next 10 users, and then finding the next 100 users, and just like keep doing that. [01:10:37] Ankit Gupta: Like, just be laser-focused 'cause you don't [01:10:39] Ankit Gupta: have a lot of time. [01:10:40] Ankit Gupta: So just be laser-focused [01:10:41] Ankit Gupta: on what the problem is and what [01:10:43] Ankit Gupta: the solution [01:10:44] Ankit Gupta: is for the first user, and then just keep... I mean, that's what we learned at the design school. It's just like user-centric design where [01:10:51] Adam Fishman: Yep [01:10:51] Ankit Gupta: you know, solve it, you try it out, [01:10:53] Ankit Gupta: you change it, [01:10:54] Ankit Gupta: and you keep [01:10:55] Ankit Gupta: trying it out, and you just [01:10:56] Adam Fishman: double [01:10:56] Adam Fishman: diamond. The double diamond pattern. I'm [01:10:58] Adam Fishman: very familiar, yeah. [01:11:00] Adam Fishman: I want to build on this in, in our last section before lightning round. you know, you told me that you're a full-time dad and this is gonna be your job for s- for some time, quotes. Not forever. have you thought about what the end of this looks like? [01:11:13] Adam Fishman: Would you ever start another company, and would you go raise money again to start a company and take that burden on? Like, what does that look like for you? [01:11:23] Ankit Gupta: I've done this once before. was like a TED Talk a while ago [01:11:26] Ankit Gupta: where, where, this [01:11:27] Ankit Gupta: guy was like, "Why pe- why do people retire at 60? They should retire every seven years, then [01:11:33] Ankit Gupta: they have better careers." So somehow that [01:11:35] Ankit Gupta: really stuck with me, and, and I feel like my life is going in that direction, where every seven or eight years [01:11:41] Ankit Gupta: I take a break and go through a period like this. [01:11:46] Ankit Gupta: and the last time it, I did it was after Pulse got acquired by LinkedIn. And [01:11:51] Ankit Gupta: when [01:11:51] Ankit Gupta: LinkedIn was [01:11:52] Ankit Gupta: acquired by Microsoft, I decided to leave LinkedIn 'cause I didn't wanna keep doing the corporate thing. and it took me about two to three years to go from, [01:12:00] Ankit Gupta: like, [01:12:01] Ankit Gupta: leaving LinkedIn to [01:12:04] Ankit Gupta: feeling [01:12:04] Ankit Gupta: like [01:12:04] Ankit Gupta: I wanna build something again, to discovering [01:12:09] Ankit Gupta: broadly [01:12:09] Ankit Gupta: four [01:12:10] Ankit Gupta: spaces I wanna build in, to nailing down healthcare, [01:12:15] Ankit Gupta: to discovering problems in healthcare, to discovering the opioid epidemic and, and [01:12:20] Ankit Gupta: trying [01:12:21] Ankit Gupta: to create solutions [01:12:22] Ankit Gupta: to, like, the fourth or fifth solution that actually ended up working. [01:12:25] Ankit Gupta: So it, it's a pretty... [01:12:27] Ankit Gupta: it [01:12:27] Ankit Gupta: takes time. [01:12:27] Ankit Gupta: And the coolest thing is, like, the, the time, I have the time to follow that curiosity. [01:12:33] Ankit Gupta: Like, I don't have to wake up and... [01:12:34] Ankit Gupta: My time is not rented by other people. [01:12:36] Ankit Gupta: Like, I can wake up [01:12:37] Ankit Gupta: and do whatever I want, think whatever I want. and so I feel like it's gonna take me time. [01:12:41] Ankit Gupta: having hired Rick, I have [01:12:43] Ankit Gupta: realized the power of hiring [01:12:46] Ankit Gupta: an [01:12:46] Ankit Gupta: executive who, who knows what they're doing. I [01:12:49] Ankit Gupta: think that's a great model. Like, I know how to start companies, [01:12:51] Ankit Gupta: and I know how to go from zero to one and, you know, get the product market fit, but I can hire someone [01:12:56] Ankit Gupta: to scale it. [01:12:56] Ankit Gupta: and so I think it might [01:12:58] Ankit Gupta: end up looking more like [01:12:59] Ankit Gupta: a studio [01:13:00] Ankit Gupta: rather than, like, me [01:13:02] Ankit Gupta: going into one thing [01:13:05] Ankit Gupta: 100%. like this parenting thing. I don't [01:13:07] Ankit Gupta: know where this quiz will go. I'm also working on an app to, you know, it's like [01:13:12] Ankit Gupta: an AI coaching app for helping you with the parenting stuff. but I'm just using it. [01:13:16] Ankit Gupta: I'm just building it for myself. So [01:13:18] Adam Fishman: Sure. [01:13:18] Ankit Gupta: I, don't know if [01:13:20] Ankit Gupta: if isn't that how most founders get started anyway? Is they're solving a problem for themselves and then they realize, oh, there's other people that have this problem too. A lot of them, you know? [01:13:30] Adam Fishman: yeah. to be a lot of parents. People seem to keep having [01:13:33] Adam Fishman: Turns out we keep, we keep minting more of them, so. I wanna end with a look into the future, uh, before lightning round. [01:13:41] Adam Fishman: So fast-forward, it's 20 years from now, and your son comes to you and he's 22, right? He's out of college and he's thinking about his career or what-- Who knows what that's gonna look like then. And he asks you about this time of your life, and he asks you why you walked away from Bicycle or why you stepped back from Bicycle. [01:14:02] Adam Fishman: What, what do you tell him? Do you tell him the same thing that you told the, the press or do you have a different conversation with your son? [01:14:08] Ankit Gupta: I think I would probably tell him [01:14:10] Ankit Gupta: the same thing, like I wanted to spend more time with you, [01:14:13] Ankit Gupta: like [01:14:13] Ankit Gupta: I'm a naturally curious person, and I feel like there are many other things I wanna do [01:14:21] Ankit Gupta: outside of bicycle. so [01:14:24] Ankit Gupta: like if [01:14:24] Ankit Gupta: I truly end up creating more of a portfolio of [01:14:27] Ankit Gupta: stuff, then bicycle is one of them, you know, [01:14:30] Ankit Gupta: and probably the first one. [01:14:31] Ankit Gupta: and, [01:14:32] Ankit Gupta: I wanna do more. So [01:14:33] Ankit Gupta: I, I, I would probably say both. [01:14:34] Ankit Gupta: Like, I would probably say I wanted [01:14:36] Ankit Gupta: to sort of spend more time with you and figure out what being a dad mean- means for me and [01:14:42] Ankit Gupta: how I [01:14:43] Ankit Gupta: show up [01:14:43] Ankit Gupta: for you and, and for Mom, and while at the same time try to see what else interests me [01:14:51] Ankit Gupta: and, and how I can [01:14:53] Ankit Gupta: contribute to [01:14:54] Ankit Gupta: society, [01:14:55] Ankit Gupta: in [01:14:55] Ankit Gupta: more ways [01:14:56] Ankit Gupta: like be a better parent, [01:14:57] Ankit Gupta: like be, there for my family and, and also, be a better sort of, uh, citizen of, of our society [01:15:04] Adam Fishman: how can people follow along or be helpful to you, uh, in your current stage of life? [01:15:10] Ankit Gupta: reach out to me, uh, [01:15:11] Ankit Gupta: you know, ankit@fellowparent.org is my, um, email address. Uh, or my personal email is ankitgupta00@gmail.com. So, [01:15:20] Ankit Gupta: either works. [01:15:21] Ankit Gupta: or you can message me on LinkedIn. I'm really passionate about parenting, so I, I would love to geek [01:15:26] Ankit Gupta: out. Geek out on that all day long. Uh, if you take the quiz, you know, tell me how it went for you, at fellowparent.org. [01:15:34] Ankit Gupta: I'm also really passionate about, uh, nuclear fusion, philanthropy, and all things AI. [01:15:41] Ankit Gupta: So [01:15:42] Adam Fishman: Cool. [01:15:43] Adam Fishman: You got a lot of interests. [01:15:44] Ankit Gupta: Yeah, Yeah. [01:15:46] Adam Fishman: Awesome. All right. Well, thank you so much. we will, make sure to link to all those places in the, in the show notes. Uh, let's do lightning round real quick. all right, here we go. Uh, what is the most indispensable parenting product you've ever purchased? [01:15:58] Ankit Gupta: Oh, we love our Nanit camera. [01:16:01] Ankit Gupta: Like, [01:16:01] Adam Fishman: it's been a game-changer, we travel with it everywhere. What is the most useless parenting product you've ever purchased? [01:16:08] Ankit Gupta: That is bottle warmer, and we purchased a lot of them. [01:16:12] Adam Fishman: Really? [01:16:15] Ankit Gupta: I just can't [01:16:16] Adam Fishman: wasn't quite up to your expectations, so you thought if you bought another one it would be [01:16:19] Ankit Gupta: Yeah, 'cause [01:16:20] Ankit Gupta: it, it's like it has to be the same thing for the bottle you have, and, like, it'll perfectly warm it up to the same temp. But it's always so slow. It doesn't work. It, you [01:16:28] Ankit Gupta: know, you have to [01:16:29] Ankit Gupta: keep filling water in it. [01:16:30] Ankit Gupta: It's messy. [01:16:31] Ankit Gupta: And we just end up, like, taking a, like, a coffee mug [01:16:34] Ankit Gupta: in, [01:16:35] Ankit Gupta: like, warming water in the microwave in a coffee mug, and then just, like, putting the bottle in there. [01:16:39] Ankit Gupta: It works pretty well [01:16:40] Adam Fishman: What is the weirdest thing that you've ever found in your son's pockets or in the washing machine? [01:16:45] Ankit Gupta: So he has this farm. He loves to play with this farm and have all the animals [01:16:48] Ankit Gupta: play. and he's been mo- walking around with these bunnies from the farm, and we were searching for those bunnies for a [01:16:55] Ankit Gupta: really, really, really long time. Like, where are the bunnies? Apparently, the bunnies were in the gasket in the washing machine, [01:17:02] Ankit Gupta: cause at some point... [01:17:03] Adam Fishman: smell? [01:17:04] Ankit Gupta: Yeah, [01:17:05] Ankit Gupta: yeah, yeah. I don't know how he knows how to open the washing machine door and put them in there, but, [01:17:09] Adam Fishman: they knew the back, I [01:17:10] Adam Fishman: Uh, okay. Well, they needed a safe space to hang out, so [01:17:13] Ankit Gupta: Yeah [01:17:14] Adam Fishman: Um, okay, true or false, there's only one correct way to load the dishwasher [01:17:18] Ankit Gupta: True. [01:17:19] Adam Fishman: Okay. [01:17:20] Ankit Gupta: on the dishwasher. Yeah. [01:17:21] Ankit Gupta: But true [01:17:22] Adam Fishman: what is your least favorite parenting task? [01:17:25] Ankit Gupta: Making meals. I mean, it's also the most favorite. [01:17:28] Ankit Gupta: Like, [01:17:28] Ankit Gupta: I hate it when he doesn't eat it 'cause it feels like judgment. Yeah. Yeah, yeah. It's like, " [01:17:35] Ankit Gupta: I'm [01:17:35] Ankit Gupta: not-- I'm gonna go on a hunger strike because of this food you made." but anyway, it's [01:17:39] Ankit Gupta: obviously not [01:17:39] Ankit Gupta: that. But I hate, I hate making food for him that's like, takes a lot of time, and I've put a lot of effort in it, and he [01:17:45] Adam Fishman: Yep. [01:17:45] Ankit Gupta: doesn't even take a bite [01:17:47] Adam Fishman: Okay. what is the crazier block of time in your house, 6:00 AM to 8:00 AM or 6:00 PM to 8:00 PM? [01:17:54] Ankit Gupta: Oh, definitely 6:00 to 8:00. I've [01:17:55] Ankit Gupta: started a yoga practice, so I really need to leave for that while he wakes up at a variable time [01:18:01] Ankit Gupta: every day, and we [01:18:03] Ankit Gupta: have to make [01:18:03] Ankit Gupta: his breakfast and lunch and pack [01:18:05] Ankit Gupta: everything, and it's cr- the dog has to go out and [01:18:07] Ankit Gupta: also have a long [01:18:08] Ankit Gupta: walk. And yeah, [01:18:09] Ankit Gupta: it's [01:18:10] Ankit Gupta: kind of wild [01:18:11] Adam Fishman: if your son had to describe you in one word, what would it be? [01:18:14] Ankit Gupta: demanding. Demanding, [01:18:16] Adam Fishman: Demanding. Okay. Okay. [01:18:20] Ankit Gupta: I wouldn't like it. [01:18:21] Adam Fishman: him to do things, but he [01:18:22] Ankit Gupta: Yeah. That seems to be when I interact with him, like, "Oh, let's go change your diaper. Now it's time to eat." Like, I keep wanting him to do stuff, [01:18:32] Adam Fishman: Okay. Awesome. [01:18:34] Adam Fishman: I know you don't have TV in your house, but what is your favorite kids movie? [01:18:38] Ankit Gupta: I love Inside Out. We actually watched Inside Out in the [01:18:42] Ankit Gupta: labor room before, [01:18:44] Ankit Gupta: like, while we [01:18:44] Ankit Gupta: were waiting [01:18:45] Adam Fishman: that's awesome. [01:18:46] Adam Fishman: Okay, what nostalgic movie can you not wait to force your son to watch with you when he's old enough? [01:18:53] Ankit Gupta: The Lion King. Oh my God. Yeah. [01:18:56] Adam Fishman: All right [01:18:56] Ankit Gupta: remember. That was my first animated movie as a child. I loved [01:19:00] Adam Fishman: Awesome. What is the worst experience you've ever had assembling a children's toy or a piece of kids' furniture? [01:19:07] Ankit Gupta: I [01:19:07] Ankit Gupta: am the worst at it. Like, I just can't follow the instructions. So I, I assembled this, what's it called? Like a triangle, Pikler triangle. Like, you [01:19:14] Ankit Gupta: climb up [01:19:14] Ankit Gupta: and you climb down, and I... Something hap- I wasn't supposed to, like, turn a screw or something, where, like, it just got stuck and it, the screw kind of broke. [01:19:24] Ankit Gupta: So now it doesn't fold. Like, it's supposed to fold on itself, but it doesn't fold anymore. So if we ever need to take it away from him, which is all the time, because otherwise [01:19:32] Ankit Gupta: he'll go- keep going crazy, we have to, like, [01:19:34] Ankit Gupta: pivot, like pivot it out [01:19:36] Ankit Gupta: of the doorway into, like, this [01:19:38] Ankit Gupta: other room. And [01:19:40] Ankit Gupta: we basically [01:19:40] Ankit Gupta: have to do that every day so that he goes to bed and doesn't [01:19:43] Ankit Gupta: keep playing with the Pikler triangle, [01:19:44] Ankit Gupta: So [01:19:45] Adam Fishman: what is your favorite dad hack for road trips or flights with your son? [01:19:49] Ankit Gupta: we started [01:19:50] Ankit Gupta: going on flights, uh, quite frequently with him, and it was always hard to, like, get him to [01:19:55] Ankit Gupta: settle down. And then one time we ended [01:19:57] Ankit Gupta: up going on [01:19:58] Ankit Gupta: the plane with a car seat. So we bought this really, [01:20:01] Ankit Gupta: lightweight Costco car seat, [01:20:03] Ankit Gupta: and [01:20:04] Ankit Gupta: he loves his car seat. And so we put the car seat on [01:20:08] Ankit Gupta: the plane, like on the [01:20:09] Ankit Gupta: plane chairs. [01:20:10] Ankit Gupta: It's definitely not for safety. It's just, like, something that he enjoyed hanging out in. [01:20:15] Ankit Gupta: And [01:20:15] Ankit Gupta: as soon as the plane took off, he went to sleep, and he slept for, like, [01:20:18] Ankit Gupta: two hours. And then [01:20:19] Ankit Gupta: he basically was in the [01:20:21] Ankit Gupta: car seat for two or three more hours just, like, hanging out, eating. Like, he [01:20:26] Ankit Gupta: had the most fun, and since then we've always taken a car seat. [01:20:29] Ankit Gupta: Even though it's so bulky, we always take it on plane. Like, it's amazing how comfortable he [01:20:35] Adam Fishman: All right. Car seat [01:20:36] Ankit Gupta: Yeah [01:20:37] Adam Fishman: question. What is your take on minivans? [01:20:39] Ankit Gupta: I used [01:20:40] Ankit Gupta: to be so against minivans. [01:20:42] Ankit Gupta: hideous. Like I was a, I was a, a, like a two-seater, you know, coupe [01:20:48] Ankit Gupta: kind of guy. but now I love them. [01:20:50] Ankit Gupta: We're going on a trip, [01:20:51] Ankit Gupta: four families are coming to Denver. We're, we're doing like a [01:20:53] Ankit Gupta: birthday trip, [01:20:54] Ankit Gupta: and I asked the host to book a [01:20:57] Ankit Gupta: minivan so that the two families could be together in, in one car. [01:21:01] Ankit Gupta: it's just such an amazing invention. Like, everyone travels together. Especially in India, we are big [01:21:06] Ankit Gupta: family, so [01:21:06] Ankit Gupta: we need a lot of space [01:21:07] Ankit Gupta: for [01:21:08] Ankit Gupta: everyone to travel together. I'm a, I'm a minivan guy. [01:21:10] Adam Fishman: you're a-- You're Team Minivan. You've come around to it. [01:21:12] Adam Fishman: Love that. Love, love that. [01:21:15] Ankit Gupta: tiny cars [01:21:16] Ankit Gupta: where the [01:21:17] Adam Fishman: love love that. all right. Well, Ankit, that, that concludes our marathon recording session. this has been so enjoyable. Thank you, thank you so much for, for joining me, for the candor, for telling me about your life, and, uh, for all the, great fatherhood advice you, you've got as we're figuring it out together. [01:21:38] Adam Fishman: And I wish you, your wife, and your son, and your whole family all the best, uh, for the, for the rest of this year. So thank you [01:21:45] Ankit Gupta: No, thank you so much. Thank you for having me. And yeah, so it's a great, great conversation [01:21:50] Adam Fishman: Thank you for listening to today's conversation with Ankit Gupta. You can subscribe and watch the show on YouTube or wherever you get your podcasts. [01:21:57] Adam Fishman: Visit www.startupdadpod.com to learn more and browse past episodes. Thanks for listening and see you next week. ​