Startup Dad

Aakash Gupta is a creator, product advisor, author, and the host of one of the most popular newsletters, podcasts, and social accounts for product managers and AI builders. He built a following of over 350,000 people on LinkedIn through six years of daily posting and now uses AI to create leverage across his work and family life.
He’s also a dad of two who stepped away from a VP of Product role to build a career with more flexibility and be more present with his kids. Aakash joins Startup Dad to share how he built a Parent OS using Claude Code, AI agents, and automations to manage the invisible workload of parenting. We discussed:
Building a Parent OS with AI: How Aakash created a personal operating system that combines context libraries, AI skills, and automations to manage family logistics, reminders, and everyday parenting tasks.
Using AI to become a more present parent: Why Aakash believes AI’s biggest benefit is not more screen time, but reducing the amount of time parents spend on their phones handling tasks in front of their kids.
Creating personalized AI storytelling: How Aakash built a storytelling system that remembers his kids’ preferences, previous stories, and family values to create better experiences for his children.
Automating the invisible work of family life: How AI helps manage school applications, activity registrations, subscriptions, travel planning, and reminders that usually fall on parents to track manually.
Turning AI into a family coordination system: How Aakash uses AI as a shared operating layer between him and his wife to keep everyone aligned without constant communication.
Why parents should start building with AI now: Why Aakash believes every parent should learn how to use AI effectively, not just for productivity, but to prepare their families for a future where AI becomes part of everyday life.

Aakash’s Open Source Parent OS
https://github.com/aakashg/parenting-os

Where to find Aakash Gupta
Website: https://www.aakashg.com/ 
LinkedIn: https://www.linkedin.com/in/aagupta/ 
Newsletter: https://www.news.aakashg.com/
Youtube: https://www.youtube.com/@growproduct

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Aakash Gupta, author and podcast host
(04:55) Why Claude is the most powerful software ever built
(07:11) Why AI is underused by families
(10:42) Being a father first, creator second
(12:29) Leaving a VP of Product role for his family
(15:16) Advice for dads considering the creator path
(17:44) Calendar non-negotiables and daily time blocking
(21:51) Building AI-powered storytelling for his kids
(26:22) Inside the Parent OS: a live demo
(37:48) The automations his family uses most
(43:39) Where AI automation fell short
(46:39) How to build your own Parent OS from scratch
(52:37) How AI scored a free museum day in Poland
(1:01:19) Advice for builders about to become parents

Resources From This Episode:

Parent OS: https://github.com/aakashg/parenting-os
Product Growth: https://www.news.aakashg.com/ 
The Growth Podcast: https://www.news.aakashg.com/s/product-growth-podcast 
Claude: https://claude.ai/
Claude Code: https://www.anthropic.com/claude-code
Anthropic: https://www.anthropic.com/
Cursor: https://cursor.com/
Whisper Flow: https://whisperflow.ai/
MCP (Model Context Protocol): https://modelcontextprotocol.io/
GitHub: https://github.com/
Notion: https://www.notion.com/
Slack: https://slack.com/
Canva: https://www.canva.com/
Figma: https://www.figma.com/
Typefully: https://typefully.com/
LinkedIn: https://www.linkedin.com/
Claude Opus: https://claude.ai/
ChatGPT: https://chat.openai.com/
OpenAI: https://openai.com/
Codex: https://openai.com/codex/
Gemini: https://gemini.google.com/
Amazon: https://www.amazon.com/
Whoop: https://www.whoop.com/
Google Flights: https://www.google.com/travel/flights
Air Zoo: https://www.airzoo.org/
Dolly Parton’s Imagination Library: https://imaginationlibrary.com/
Alien (Film): https://www.imdb.com/title/tt0078748/
Inside Out (Film): https://www.imdb.com/title/tt2096673/ 
Kia Telluride (Car): https://www.kia.com/us/en/telluride
Hyundai Palisade (Car): https://www.hyundaiusa.com/us/en/vehicles/palisade

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Ankit Gupta is the Founder of Bicycle Health, a company he built and led for nearly nine years before handing over the CEO role and becoming a stay-at-home dad. Before Bicycle, Ankit co-founded Pulse while at Stanford, a news app that caught the attention of Steve Jobs, was famously pulled from the App Store later that same day, and was eventually acquired by LinkedIn.
He’s also a dad of one, with a two-year-old son, and the husband of a transplant nephrologist in the middle of a demanding fellowship. After years of being pulled toward building companies, Ankit found that pull shifting toward his family. He joins Startup Dad to talk about the 18-month process of stepping away from Bicycle, the turbulence and FOMO that came with trading founder life for full-time parenting, and why he believes some of the best things parents can give their kids are simply time, love, and room to be bored. We discussed:
Choosing fatherhood over founder life: How Ankit spent 18 months deciding to step away from Bicycle Health and follow a new pull toward being more present with his son.
The transition from CEO to stay-at-home dad: Why leaving startup life created unexpected challenges, from losing daily feedback loops to adjusting to a completely different pace.
Why time and love matter most: How Ankit believes parents can get caught optimizing everything, when simply being present is what matters most.
Rethinking modern parenting pressure: Why Ankit pushes back on overscheduling kids and the constant pursuit of efficiency, and what boredom can teach children.
Using AI to understand parenting: How Ankit used Claude and ChatGPT to research parenting philosophies, map different approaches, and build his own framework.
Building with AI for yourself: How a personal parenting experiment became a public tool and showed what is now possible with AI-powered creation.

Where to find Ankit Gupta
LinkedIn: https://www.linkedin.com/in/ankitgupta00/ 
X: https://x.com/gankit

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Ankit Gupta, founder of Bicycle Health
(02:50) The untold story behind stepping back from Bicycle Health
(05:14) Becoming a full-time dad so his wife could focus on her fellowship
(09:38) Preschool shuts down and Ankit becomes a solo dad
(12:29) The "dopamine desert" of trading founder life for fatherhood
(14:15) Why "time and love" is a contrarian parenting philosophy
(17:49) Comparing overscheduled American childhoods to growing up in India
(21:31) Addressing privilege and financial independence
(26:55) Why parenting is tiring
(32:02) Using Claude to map every parenting philosophy
(42:54) Redesigning the home and moving the bed to the floor
(46:17) Going screen-free and Montessori-inspired play
(52:15) The Steve Jobs Pulse story: best and worst day
(1:04:11) Why entrepreneurship pairs well with parenting

Resources From This Episode:

Bicycle Health: https://www.bicyclehealth.com/
Pulse: https://www.linkedin.com/ (acquired by LinkedIn)
Fellow Parent: https://fellowparent.org/
Good Inside by Dr. Becky: https://www.goodinside.com/
Claude: https://claude.ai/
ChatGPT: https://chatgpt.com/
Montessori Education: https://amshq.org/
Nanit Camera: https://www.nanit.com/
Inside Out (Film): https://www.pixar.com/inside-out
The Lion King (Film): https://www.disney.com/movies/the-lion-king
Pikler Triangle: https://www.piklertriangle.com/
Costco Car Seats: https://www.costco.com/car-seats-boosters.html 

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Brad Harrington is the former Executive Director of the Boston College Center for Work & Family and spent nearly two decades at Hewlett-Packard, earning his PhD along the way.

He walked away from corporate America and took a  75% pay cut to become one of the leading researchers on fatherhood, caregiving, and work-family integration. Now retired, Brad is a happily married dad of three who has spent the last quarter-century studying why men struggle to escape work-family conflict. We discussed:
The 3 Archetypes of Modern Fatherhood: Breaking down traditional, egalitarian, and conflicted fathers - and why the "conflicted" bucket is consistently the largest group.
The Caregiving Gap: Why 70% of fathers report wanting a 50/50 caregiving split, yet only 35% actually live it.
The Financial & Organizational Traps: The economic pressures and workplace cultures that keep men locked into primary breadwinner roles even when they want out.
The Power of Early Paternity Leave: Why taking dedicated time off in the first few weeks of a child's life sets the trajectory for a dad's hands-on caregiving identity for decades.
The Dual-Career Lifecycle: How couples navigate moving through stages from allies and acrobats to adversaries and accommodators.
The Danger of Over-Scheduling Kids: Why competitive youth sports and hyper-structured childhoods are stripping kids of independence and unstructured play.
Why Parenting Never Ends: Lessons from raising three adult children through career shifts, health struggles, and navigating relationship dynamics across decades.

Where to find Brad Harrington
LinkedIn: https://www.linkedin.com/in/bradharrington/ 

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Brad Harrington, former Executive Director of the Boston College Center for Work and Family
(02:26) Commuting 3,000 miles every other week while balancing family
(06:00) Walking away from corporate America and taking a 75% pay cut
(08:16) From personal conflict to a quarter-century of research
(10:41) The three archetypes of fatherhood: traditional, egalitarian, and conflicted
(16:16) Why conflicted fathers are the least satisfied men at work and home
(24:32) Don't argue about who does more—focus on who does what
(28:15) The mental load and the mindset of a partner versus an employee
(32:26) Four reasons men stay locked in the breadwinner role
(36:30) Paternity leave and the "train leaving the station" in those first few months
(43:32) The four stages of couples: allies, acrobats, adversaries, and accommodators
(48:19) Advice for startup founders on building parental leave policies
(52:07) The stay-at-home dad study and societal double standards
(57:52) The overscheduled child and the loss of unstructured play
(1:04:36) Parenting never ends: navigating adulthood, health struggles, and advice
(1:11:56) Lightning round: Minivans, pre-iPad travel, family chat, and dishwasher loading

Resources From This Episode:
Brad Harrington’s Profile at Boston College: https://www.bc.edu/bc-web/offices/office-of-university-communications/for-the-media/z_archive/brad-harrington.html 
Hewlett-Packard Enterprise: https://www.hpe.com/
Dr. Linda Haas: https://www.researchgate.net/profile/Linda-Haas 
The Wizard of Oz (Film): https://www.imdb.com/title/tt0032138/
The Sound of Music (Film): https://www.imdb.com/title/tt0059742/

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Support Startup Dad
For sponsorship inquiries, email: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

Adam Grenier is the Founder of AI Matey, a growth and product advisor, longtime startup operator, and the creator of DadBench, an AI evaluation system built around one deceptively difficult challenge, teaching a model to write a good dad joke.

He’s also a dad of three and one of the very first guests to appear on Startup Dad (#2 in fact!). Three years later, Adam is back to talk about what has changed in his family and how getting laid off from Eventbrite sent him deep into AI experimentation, model training, and reinforcement learning. We discussed:
Advocating for neurodivergent kids at school: How Adam navigated two very different advocacy journeys, fighting for more support for his daughter with ADHD while deciding whether his autistic son was ready for less.
Learning AI by actually building with it: Why Adam believes hands-on experimentation with new models and research can teach you things that traditional coursework might take years to reach.
Training AI to tell dad jokes: How a funny side project became a crash course in reinforcement learning, model evaluation, reward design, and what actually makes a dad joke work.
Getting reward hacked by your own AI: How Adam’s model learned to game his scoring system by cramming in more puns, and what Goodhart’s law teaches us about optimizing for the wrong metrics.
Why getting to the point matters: How word economy became the strongest predictor of a better dad joke, and why teaching AI to commit to one idea proved more valuable than teaching it to be funny.
Making model training accessible to product teams: Why Adam thinks reinforcement learning will move beyond AI researchers and into the hands of product managers and marketers who understand customers best.

Where to find Adam Grenier
Website: https://www.adamgrenier.com/ 
LinkedIn: https://www.linkedin.com/in/akgrenier/ 
Twitter: https://x.com/AKGrenier

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Adam Grenier, Founder of AI Matey
(02:09) What changed in three years of parenting and startups
(04:27) Advocating for two neurodivergent kids with different needs
(08:45) How AI Matey led to training AI on dad jokes
(13:33) Learning AI with goat screams and school photos
(24:11) How anyone can start training AI models
(29:17) What training on dad jokes actually taught the model
(32:02) What actually makes a great dad joke
(36:52) Putting the biggest AI models to the dad joke test
(47:09) Getting reward hacked by your own AI model
(51:05) Why the best dad jokes get straight to the point
(53:41) Bringing humans and kids into the judging process
(55:24) Why Adam fired an AI judge for being too slow
(57:13) What dad jokes can teach us about building better AI
(01:05:04) Can you actually teach a sense of humor?

Resources From This Episode:

AI Matey: https://aimatey.co/ 
DadBench: https://aimatey.co/dadbench/ 
GoatScreams: https://www.goatscreams.com/waitlist 
SmilePlease: https://smileplease.app/
ElevenLabs: https://elevenlabs.io/ 
Thinking Machines Labs: https://thinkingmachines.ai/ 
Inkling: https://thinkingmachines.ai/inkling/ 
Tinker: https://thinkingmachines.ai/tinker/ 
Prime Intellect: https://www.primeintellect.ai/ 
Unsloth: https://unsloth.ai/ 
DeepSeek: https://www.deepseek.com/ 
Gemma: https://deepmind.google/models/gemma/ 
Gemini: https://gemini.google.com/app 
GLM: https://chat.z.ai/ 
Grok: https://grok.com/ 
Anthropic: https://www.anthropic.com/ 
OpenAI: https://openai.com/ 
Claude: https://claude.ai/ 
The Book of Mormon (Musical): https://bookofmormonbroadway.com/ 

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Support Startup Dad

For sponsorship inquiries, email: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

Jackie Nesi, PhD is a clinical psychologist, researcher, and associate professor at Brown University. She is also the creator of Techno Sapiens, a weekly Substack newsletter with over 50,000 subscribers dedicated to translating the latest research on kids, technology, and mental health into practical advice for parents.

Beyond her academic work and her testimony before the U.S. Senate on social media safety, Jackie is a grounded voice in the parenting space who navigates the day-to-day balance of screen time in her own household. She is a mom of three young kids, married to a tech entrepreneur, and works to bridge the gap between complex psychological research and the practical demands of modern parenting. We discussed:
The disconnect between screen time panic and actual research: Why the "all screen time is bad" narrative isn't supported by science, and how parents can let go of perfectionist guilt.
The Transformation Framework: How specific features of social media (asynchrony, public reach, image focus, and permanency) fundamentally alter childhood friendships.
Dialectics in parenting: Practicing dialectical thinking to hold two seemingly contradictory truths at once (e.g., deeply loving your child while feeling completely overwhelmed).
Smart device staging: How to evaluate when a child is ready for a phone, running "tech experiments," and layering access from smartwatches and dumb phones up to full smartphones.
School phone bans and Yondr pouches: What the latest research actually shows regarding school phone policies, distraction, test scores, and student mental health.
AI as the next frontier: What parents and educators need to know right now to help kids navigate AI tools safely and responsibly.

Where to find Jackie Nesi
Website: https://www.jacquelinenesi.com/ 
LinkedIn: https://www.linkedin.com/in/jacqueline-nesi-phd-b070595b 
Substack: https://technosapiens.substack.com/
IG: https://www.instagram.com/jacqueline_nesi/

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Jacqueline Nesi, Associate Professor at Brown University and Techno Sapiens author
(04:01) What teens in psychiatric care reveal about online safety
(08:00) How social media transforms kids’ friendships
(13:49) Why two opposite truths can coexist in parenting
(19:20) Why screen time is about more than counting minutes
(23:31) Treating new devices and screen rules as experiments
(27:12) How to let go of screen time guilt
(29:45) How to know when your child is ready for a phone
(33:28) How to stage phones, smart devices, and social media
(39:23) What school phone bans can and cannot solve
(45:11) Why managing screens can be harder for neurodivergent kids
(47:34) Where The Anxious Generation gets the research right and wrong
(50:33) Having regular tech talks and putting people first
(53:24) How to avoid repeating social media mistakes with AI
(59:49) Lightning round: Toy baskets, existential nursery rhymes, and minivan temptation 

Resources From This Episode:
Techno Sapiens: https://technosapiens.substack.com/ 
How to Let Go of Screen Time Guilt: https://technosapiens.substack.com/p/how-to-let-go-of-screen-time-guilt
It Takes Two (PlayStation Game): https://www.playstation.com/en-us/games/it-takes-two/ 
Lego Star Wars (PlayStation Game): https://www.playstation.com/en-us/games/lego-star-wars-the-skywalker-saga/
The Anxious Generation by Jonathan Haidt (Book): https://www.anxiousgeneration.com/book 
The Emperor’s New Groove (Film): https://www.imdb.com/title/tt0120917/
Will Ferrell (Actor): https://www.imdb.com/name/nm0002071/

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Support Startup Dad
For sponsorship inquiries, email: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com