Don’t love the opaque nature of AI phone calls, but I’m not sure there’s an alternative unless the AI asks if it can record the convo… and that seems like a strange first interaction sure to lead to a hang up 😆.

7 takeaways from my conversation with @aakashgupta, creator, product advisor, author of The AI Product Manager Interview, and Dad of 2. Every Startup Dad episode ends with a quick AI Corner question. We turned the whole episode into one. 1/ Taking his full paternity leave quietly cost him at work. With his first kid, Aakash took every day of leave, and even with "exceeding expectations" reviews, his standing and team size took a real hit. With his second, he took 2 weeks out of the 3 months offered, then realized his side project was earning as much as his VP of Product salary. He bet on himself full time. 2/ Aakash uses AI to spend less time on his phone in front of his kids. His "Parent OS" is a Claude Code setup with a family context library, YAML files tracking signup windows, and connections to Gmail, Calendar, and Slack. When Santa Monica swim registration opens at noon, it can text him 1 minute early with the link and the exact steps (same deal for LA's very competitive Westside Ballet signups). His wife is on the repo too, so it tells them both when someone's already handled a task. 3/ A one-off chat can't know what's already in your toy bin. Toy Scout scans his Amazon receipts in Gmail and keeps a running inventory of every toy the kids own. When the family group chat asks what to buy for a birthday, he just asks Toy Scout (a fix for the year his oldest turned 1 and got 3 identical balance bikes). It works because it lives inside the Parent OS, where it already knows the kids and the house. 4/ Bedtime stories get better when the AI remembers the last few hundred. His storytelling setup knows who the kids are, how old they are, and every story it's ever written for them. Ask for Tom and Jerry and it already knows to skip the frying pan to the head. The kids come up with the prompts ("Elsa meets Thomas the Train at Disney World"), and Aakash insists on real character development. 5/ His trip planner found a free day at a train museum in Krakow. They saved $100 on a museum they were planning to visit already. The kids, being kids, behaved exactly how they would have on a paid day. He says the same trick works at home, since a surprising number of local activities run free days and promos. It's saved their family hundreds! 6/ When we recorded, he still didn't let AI book things for him. He tried once; gave it his credit card and browser access to grab time-sensitive signups like the Dolly Parton Imagination Lab. A 30-second task took 12 minutes, which he compared to "watching your parents use the internet in the 90s." Too slow, too token-hungry, and too close to his credit card, so he went back to reminders and keeps the final click for himself. With the latest advancements it'll be time to re-test this. 7/ Since having kids, his income has gone up about 6x. He compares it to high school: you pile on extracurriculars and somehow your grades go up. He's with the kids 6:30 to 8:30 every morning and 4:30 to 8:30 every evening, skips almost all work travel because "they're never gonna be 3 and 4 again," and pays for it mostly in sleep (WHOOP band and all). Full episode: youtube.com/watch?v=Zl09WUcM… ParentOS: github.com/aakashg/parenting…

Is everyone writing ALL of their replies with AI now or am I just seeing it everywhere and assuming that's what's happening?

I have named mine Peter.

Top takeaways from my conversation with Ankit Gupta, founder of Pulse (acquired by LinkedIn) and Bicycle Health, who handed off his CEO seat this year to be a full-time dad. 1. You can't manufacture founder hunger. Bicycle reached a stable place and turned profitable right around when Ankit's son was born, and he felt satisfied (which he calls "the worst thing you could have as a founder"). He spent about 18 months coming to terms with that, told his wife first, then the board, then hired Rick Dean to bring the hunger he'd lost. Ankit describes it as a pull toward his son, and he followed it. 2. The dopamine desert is real. Less than a month after Ankit left Bicycle, his son's preschool went bankrupt with a week's notice, and his wife traveled to India, leaving him a solo dad for weeks. He questioned the whole decision, mostly because he missed solving problems, making progress, and hearing someone say thank you (2-year-olds are structurally incapable of this). His workaround: his son can't compliment the pasta, so Ankit is learning to feel good about putting it on the table. 3. Time and love are the only things a parent can provide. Ankit's favorite part of the day is 7am: milk, the couch, his son leaning on him, maybe a book or a puzzle. In New York he had his son in 6 classes a week, then deliberately didn't renew 2 of them so they'd have open time to get bored together. He grew up in India going to school from 7 to noon, then walking a couple miles home alone at age 8 or 9 and figuring out what to do with an empty afternoon. 4. A founder's real job is to build a team that doesn't need them. Ankit ran Bicycle's last board meeting before his son's birth from the labor room restroom, and told the board his paternity leave started the next day and they had 90 days to get the bridge money in place. He came back 2.5 months later to a profitable company with cash in the bank. His advice for founders expecting a kid: make yourself a figurehead CEO, because the time to parent has to come from somewhere. 5. He asked Claude to map the major parenting philosophies, then built himself a quiz. Claude plotted 12 philosophies on warmth vs. structure and boxed the research sweet spot; Ankit's own blend (respectful parenting plus Montessori) landed partly outside it. He's fine with that, since parenting one kid is an N of 1 and his goal is the bond. He turned it into fellowparent.org, which shows how your style shifts between everyday moments and hard ones, to hold himself accountable to more emotion coaching (he's a big Dr. Becky fan). 6. Design the house so you say "no" less. After moving from San Francisco to New York, they set up their rental like a Montessori classroom: floor bed, hand washing station, a dresser so his son picks his own clothes, and soon a low dining table (Ankit grew up eating on the floor). There's no TV, partly because his son's first exposure to one was at his first haircut, where he sat frozen in front of a big screen while a barber shaved his head with a straight razor, then seemed hungover afterward. Ankit's logic: every "no" he can't enforce just makes him more tired, so he takes away the reasons to say it. 7. Entrepreneurship might be the most parent-friendly job there is. Ankit's dad ran 4 companies and was always around, and at Bicycle Ankit blocked off every Friday for his son. Founders control their calendar, their pay, and who they hire, and he points out that investors pay you to start a company you're arguably unqualified to start. His advice for parents starting one: skip the business plan, find your first user, then the next 10, then the next 100. Full episode: youtube.com/watch?v=seACVprm…

100% agree with this. Amazon represents the kind of shopping that isn’t all that enjoyable (unlike browsing a beautiful retail storefront that is experiential). People just want their transaction and banning agents is silly. They did it to protect their ads business. A shopping marketplace for agents is on the horizon. @Shopify should be the one to build this.

Yes.

Ankit Gupta ran a board meeting from the labor room bathroom the day his son was born. Then he handed over the Bicycle CEO seat to be a full-time dad. Full episode with @gankit: youtube.com/watch?v=seACVprm…

The answer is @yourgirlhils

A simplified UI.

Yes, if we just redesign the app so it works exactly for this guy then it’ll be great for everyone. 1.2B people use this thing. Across a bunch of devices. And they’ve grown faster than pretty much any product in history. While the models are getting so good that every few months there’s an entirely new way you could interact with them that wasn’t possible before. It’s an incredible set of capabilities we’ve never had before in our lives. I’m gonna give them a little bit of grace here. I think they’ll get this right eventually.

This reminds of Uber slashing fares and telling drivers “but you’ll make the same or more money because demand will go up!” (Conveniently leaving out the fact that drivers now had to do more rides to hit the same earnings). I’m not complaining about the move because they were subsidizing the crap out of Pro200 by every logical measurement. Just think the announcement is meh.

I love this so much and also... the way this is all playing out on the timeline is so f-ing predictable: Step 1: Founder yells about something and thumps chest publicly. Step 2: Person defends themselves "I could never / would never do that / lies lies lies" Step 3: Founder/CEO of new company jumps in to say the same thing, "This would never happen, lies lies lies." Step 4: VCs start engaging because they have nothing better to do with their day Step 5: @clairevo turns it into a banger that points out how ludicrous it all is. Put down twitter everybody, go outside, touch a blade of grass.

One thing I've been finding myself trying to do since yesterday is command+space "dot" and hoping it'll open Codex. @thsottiaux can you make this work :-) What about if it also responded to its name.