Startup Dad

Jonathan Stull is the President and COO of Handshake, the career platform connecting students and recent grads with employers that recently made a massive pivot into scaling an AI product. He’s spent the last decade helping build the company from a seed stage startup working out of a house in Palo Alto into a massive platform serving millions of students, universities, and employers.

He’s also a husband to Emmy-winning journalist Emily Chang and a dad of four kids, ages 13, 11, 9, and 6. At home, he’s juggling the beautiful chaos of school drop-offs, carpools, Little League, robotics, math enrichment, ski trips, and four very different schedules. In our conversation, we talked about how Jonathan and Emily rely on their nanny, grandparents, neighbors, and community to make it all work, the challenge of being present when work is still running in the background, why kids need agency and resilience more than ever, and how becoming a dad has made him a more direct and caring leader. We discussed:

• Building a life with four kids: How Jonathan and his wife manage the beautiful chaos of school, sports, activities, and constant logistics.
• Relying on your village: Why their nanny, grandparents, carpools, neighbors, and community are essential to making family life work.
• Staying present when startup life is intense: The challenge of being physically at a kid’s game while mentally pulled into Slack, AI agents, and company decisions.
• Raising kids with agency in the AI era: Why Jonathan believes resilience, adaptability, self-starting, and passion matter more than ever.
• Parenting through direct feedback: How being a dad helped Jonathan become a clearer, more direct, and more caring leader at work.
• Embracing adventure before the years disappear: Why Jonathan tries to say yes to family trips, backyard games, and small moments of connection.

Where to find Jonathan Stull

• LinkedIn: https://www.linkedin.com/in/jonstull/ 

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) Welcome Jonathan Stull, President and COO of Handshake (and baseball coach)
(02:14) Why Jonathan and Emily decided to have four kids
(03:53) Managing the beautiful chaos of four schedules
(05:51) Building the village that keeps family life moving
(09:46) The first moment fatherhood really hit
(10:42) Growing Handshake while learning to stay present at home
(16:25) Why parents should not wait for the perfect time
(19:36) What kids teach you about resilience
(22:11) Showing up, saying yes, and protecting family time
(24:35) How parenting made Jonathan a more direct leader
(27:09) Navigating enrichment, ambition, and different parenting instincts
(30:00) Raising kids to be ready for an AI shaped future
(31:20) Why agency matters more than following a playbook
(34:10) Using AI to plan trips, pranks, and Little League schedules
(39:12) Lightning round: white noise, limericks, dad pranks, and minivans

Resources From This Episode:

Handshake: https://joinhandshake.com/ 

SNOO Smart Sleeper Bassinet: https://www.happiestbaby.com/products/snoo-smart-bassinet 

Bluey (TV Series): https://www.imdb.com/title/tt7678620/ 

The Lion King (Film): https://www.imdb.com/title/tt0110357/
Billy Madison (Film): https://www.imdb.com/title/tt0112508/ 

Braveheart (Film): https://www.imdb.com/title/tt0112573/ 

Glory (Film): https://www.imdb.com/title/tt0097441/ 

Anchorman: The Legend of Ron Burgundy (Film): https://www.imdb.com/title/tt0357413/ 

Old School (Film): https://www.imdb.com/title/tt0302886/

Wedding Crashers (Film): https://www.imdb.com/title/tt0396269/ 

Chevrolet Suburban (Car): https://www.chevrolet.com/suvs/suburban 

Chrysler Pacifica (Car): https://www.chrysler.com/pacifica.html 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected]
For Startup Dad Merch: www.startupdadshop.com

Ashish Kundra is the CEO of Conceptual, a growth agency that helps companies like Cursor, Perplexity, Superhuman, Fenty Beauty, GPTZero, and dozens more. Prior to that, he led growth at DuckDuckGo and founded two other companies.

He’s also a husband and the father of a four-year-old son. In this episode, Ashish shares why starting a company when his son was one made sense for his family, how being married to a pediatrician shapes their parenting, and why he believes small falls prevent big falls. We discussed:

• Being married to a pediatrician and how that shapes parenting: Why Ashish sees it as a major advantage in handling health, nutrition, and everyday parenting decisions.
• Starting a company when his son was one: Why Ashish felt that early parenthood was still the right time to build something of his own.
• Avoiding over-parenting: How he gives his son more agency and lets natural consequences do some of the teaching.
• Why small falls prevent big falls: How Ashish thinks about struggle, discomfort, and building resilience early.
• Tracking happiness and contentment: Why he journals regularly and what he’s learned about sleep, exercise, and stress.
• Why your child is not your trophy: How he thinks about ambition, identity, and raising a son without ego.

Where to find Ashish Kundra

• LinkedIn: https://www.linkedin.com/in/ashish-kundra-5a9b784/ 
• X: https://x.com/akundra 

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) Welcome Ashish Kundra, CEO of Conceptual

(02:57) What it is really like being married to a pediatrician

(05:15) Nutrition, hydration, and diet hacks that actually help

(08:31) Why he started a company when his son was a baby

(12:38) Avoiding over-parenting and giving kids more agency

(16:41) Why small falls can prevent bigger ones later

(20:01) Tracking happiness, sleep, and stress in real time

(24:13) The weekly one-on-one that keeps their marriage aligned

(25:47) How he and his wife divide life at home

(27:44) Grandparents, family planning, and designing life on purpose

(29:34) Embracing imperfection as a parent and partner

(31:15) Raising a kid without turning him into a trophy

(34:33) The mistake he wishes he could redo as a dad

(35:53) Navigating startup pressure and family time

(37:59) Lightning round: strollers, quesadillas, Cocomelon, and minivans

Resources From This Episode:

Conceptual: https://conceptualhq.com/ 

Baby stroller: https://a.co/d/0aRvEiDH 

The Sound of Music (Film): https://www.imdb.com/title/tt0059742/ 

The Lion King (Film): https://www.imdb.com/title/tt0110357/
Mrs. Doubtfire (Film): https://www.imdb.com/title/tt0107614/ 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected]
For Startup Dad Merch: www.startupdadshop.com

Robert Whitney is the Co-Founder and CTO of Hapiko, the company that invented Stickerbox, an AI powered product helping kids create and play in more imaginative ways. Before starting Stickerbox, he helped scale New York Times Games, Grailed  and spent time at Anthropic thinking deeply about the future of AI and how it will shape the next generation.

He’s also a co-parent to a four-and-a-half-year-old son in New York City. In this conversation, Robert shares how fatherhood changed the way he approaches work, decision-making, discipline, and presence. We also talk about co-parenting as a founder, his shift away from a hard-partying New York lifestyle, the parenting principles he’s developed, and why he believes most AI products are failing kids. We discussed:

• Why parenting is the ultimate life experience: How becoming a dad made Robert more grounded and less reactive.
• Co-parenting while building a startup: What it looks like to split time as a founder and a parent, and how Robert thinks about being fully present in each mode.
• Leaving behind a hard-partying New York lifestyle: Why Robert made a major life change years before becoming a dad, and how sobriety reshaped his priorities, energy, and sense of self.
• How loss changed his perspective on fatherhood: What losing his mom shortly after becoming a parent taught him about time and presence.
• What most AI products get wrong for kids: Why Robert believes kids need safer, simpler, more thoughtful tools.
• How Stickerbox started with his son: The rainy-day moment that turned into a company built around play and creativity.

Where to find Robert Whitney

• LinkedIn: https://www.linkedin.com/in/robertjwhitney/ 
• Instagram: https://www.instagram.com/robertjwhitney/
  
  

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 Robert Whitney, Co-Founder/CTO of Stickerbox

(02:12) Why parenting is the ultimate life experience

(06:11) Co-parenting while building a startup

(09:46) Leaving behind his hard-partying New York lifestyle

(13:56) The career shift that forced deeper self-reflection

(16:09) Losing his mom and learning to value presence

(18:18) Why he got pulled into AI for kids

(22:13) The biggest AI risks facing children

(27:16) Why safety matters more than being on the bleeding edge

(32:20) Parenting principles that help him let most things go

(34:38) Why he makes his son help with everything

(38:27) Why slowing down and sleeping on things matters

(43:07) Why discipline matters more than motivation

(48:12) How Stickerbox was created with his son

(52:58) Lightning round: Yoto wins, bowling obsession, and manual minivans

Resources From This Episode:

Stickerbox: https://stickerbox.com/ 

Hapiko: https://hapiko.com/ 

Yoto: https://www.yotoplay.com/ 

Moana (Film): https://www.imdb.com/title/tt3521164/
My Neighbor Totoro (Film): https://www.imdb.com/title/tt0096283/ 

Dodge Caravan (Car): https://www.dodge.com/grand-caravan.html

—

Support Startup Dad
For sponsorship inquiries, email: [email protected]
For Startup Dad Merch: www.startupdadshop.com

Caleb Avery is the Founder and CEO of Tilled. He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey.

In this episode, Caleb shares what it really looks like to build a startup and a family at the same time. We talk about the trade-offs founders need to be honest about, his regrets around paternity leave with his first child, and why bedtime became his most important non-negotiable as a dad.

We also get into the little-discussed challenge of making parent friends, what coaching his son’s T-ball team taught him, how he and his wife think about screen time and technology, and why he believes work-life balance is less useful than clear boundaries. We discussed:

• Starting a company while raising young kids: How Caleb thought about the trade-offs of building a startup and growing a family at the same time.
• Paternity leave regrets and what changed: Why Caleb still thinks about working from the hospital after his first child was born, and what changed with his second child.
• Why bedtime is his top parenting priority: How Caleb built his schedule around being home for bedtime and why it became his most important non-negotiable as a dad.
• Boundaries over balance: Why Caleb does not chase perfect work-life balance and focuses on a few clear non-negotiables instead.
• The little-discussed challenge of making parent friends: Why it is so hard to find families where both the kids and the parents actually click.
• Honest advice for founders thinking about kids: Caleb explains why aspiring startup parents need to be brutally honest about the trade-offs before signing up for both.

Where to find Caleb Avery

• LinkedIn: https://www.linkedin.com/in/caleb-avery/ 

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 Caleb Avery, Founder/CEO of Tilled

(02:50) Starting Tilled while raising young kids

(05:12) The time and energy trade-offs of startups and parenting

(07:53) Paternity leave regrets after his first child

(10:53) How COVID unexpectedly gave him the leave he wanted

(14:19) Why it is so hard to make parent friends

(17:43) What fatherhood taught Caleb about nature versus nurture

(19:19) Becoming an accidental T-ball coach

(28:03) His advice to founders thinking about having kids

(30:23) How becoming a dad made him a better CEO

(32:22) Why bedtime is Caleb’s top parenting priority

(35:04) Family time boundaries and being fully present

(37:41) Redefining work-life balance as a startup dad

(40:36) Kids, iPads, and setting screen time boundaries

(48:15) Lightning round: Snoo wins, dishwasher rules, and a toy assembly nightmare

Resources From This Episode:

Tilled: https://www.tilled.com/ 

The Snoo: https://www.happiestbaby.com/products/snoo-smart-bassinet 

The Sandlot (Film): https://www.imdb.com/title/tt0108037/
Diehard (Film): https://www.imdb.com/title/tt0095016/ 

Golf Cart for Kids: https://a.co/d/0hVZwx85 

iPad: https://www.apple.com/ph/ipad/ 

Lincoln Navigator (Car): https://www.lincoln.com/luxury-suvs/navigator/ 

—

Support Startup Dad
For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Sam Yagan is the founder of OKCupid and former CEO of Match Group. He’s also an investor, board member, married to a CEO, and a dad of three kids ages 12 to 18.

In this episode, Sam shares how he and his wife think about raising kind, grounded kids while navigating success, wealth, and ambition. We talk about family values, philanthropy, work-life integration, the pressure kids can feel from high-achieving parents, and why Sam believes “normal” is overrated.

We also get into the systems that shape their household, from weekly family meetings and value shout-outs to annual family reviews and intentionally making their home the place where all the kids want to hang out. We discussed: 

• Raising grounded kids in a high-achievement household: How Sam and his wife work to keep their kids kind, self-aware, and unentitled despite growing up around success and wealth.
• Building family values into everyday life: How Sam’s family uses weekly meetings, value shout-outs, and annual reviews to make generosity, kindness, and self-awareness part of daily life.
• Introducing philanthropy before personal wealth: Why Sam wants his kids’ first understanding of money to center on giving, impact, and responsibility.
• Choosing the right partner for the long game: Why Sam believes ambitious founders need a spouse who shares their values and vision for family life.
• Creating a home that pulls people in: How Sam and his wife built a family environment where kids and friends naturally gather, creating more connection and shared memories.
• Bringing a founder mindset into parenting: Why Sam believes decisiveness, experimentation, flexibility, and comfort with failure matter at home too.

Where to find Sam Yagan

• LinkedIn: https://www.linkedin.com/in/samyagan/
• X: https://x.com/samyagan

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) Welcome Sam Yagan, Former Founder/CEO of OKCupid & Match Group

(02:44) Raising kind kids in a world of privilege

(04:59) Family values meetings that actually work

(06:23) When your kids start asking about net worth

(12:10) Why philanthropy comes before wealth

(14:57) Work-life integration during the startup years

(18:29) The tradeoffs that come with constant travel

(20:59) The pressure kids feel from successful parents

(22:27) Teaching a “fail forward” mindset at home

(26:58) Why normal is boring

(29:24) Why choosing the right partner matters

(32:53) Putting your family values on the wall

(36:27) The annual family review

(38:47) Making your home the hangout house

(48:01) Lightning round: Parenting products, dishwasher rules, and Sam’s hard no on minivans

Resources From This Episode:

OKCupid: https://www.okcupid.com/ 

Match Group: https://mtch.com/ 

Playing cards: https://a.co/d/05A9UUbF
Basketball: https://a.co/d/0erx9ow0 

Harry Potter and the Sorcerer's Stone (Film): https://www.imdb.com/title/tt0241527/ 

A Few Good Men (Film): https://www.imdb.com/title/tt0104257/ 

Toyota Highlander (Car): https://www.toyota.com/highlander/ 

—
Support Startup Dad
For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Rex Gelb is the Founder/CEO of Summit Chase, a paid media agency serving B2B, SaaS, and professional services companies. Before starting Summit Chase, Rex spent more than 11 years at HubSpot, where he became the company’s Head of Paid Media. He’s also a husband and dad to a daughter who recently turned one. 

In this episode, Rex shares what it was like for both him and his wife to quit their jobs within 24 hours of each other right after parental leave, why that leap made sense for their family, and how becoming a dad has changed the way he thinks about ambition, hard work, and presence. We discussed: 

• Leaving stable jobs right after parental leave: How Rex and his wife both quit their jobs within 24 hours of each other and why that felt like the right move for their family.
• The sooner you give up, the better: Why Rex believes fatherhood gets easier when you stop clinging to your old life and allow yourself to evolve into a new season.
• Fighting the “should gremlins”: How Rex thinks about the pressure to show up perfectly at work, at home, and for himself, and why letting go of impossible standards matters.
• Household systems that reduce friction: The shared notes, walking one-on-ones, and email threads Rex and his wife use to stay aligned and keep family life running smoothly.
• Using AI as a parenting tool: How Rex and his wife use monthly “leap alerts” with Gemini to stay on top of milestones, safety considerations, and what’s coming next for their daughter.
• Never deprive them of a struggle: Why Rex is already thinking about how to let his daughter work through challenges on her own so he can build confidence instead of accidentally undermining it. 

Where to find Rex Gelb

• LinkedIn: https://www.linkedin.com/in/rex-gelb-43445b1b/ 
• Summit Chase: https://www.summitchase.co/ 

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) Welcome Rex Gelb, Founder/CEO of Summit Chase

(07:54) Why this was the right time to start a company

(08:45) The sooner you give up, the better

(11:05) Fighting the should gremlins

(14:13) Work, family, and the balance trap

(17:14) The newborn phase is not what you think

(19:34) The “No 2AM Fight” rule

(22:18) You do not need to master every phase

(24:37) The household systems that keep things moving

(27:43) Monthly leap alerts and using AI as a parent

(30:31) Time hacks for dads building startups

(35:43) Never deprive your kid of a struggle

(39:37) Using AI for baby health questions

(41:34) Raising a kid in the age of AI

(43:23) Lightning round: Parenting philosophy, family rhythms, and raising an AI native kid

Resources From This Episode:

Summit Chase: https://www.summitchase.co/ 

Huckleberry (App): https://huckleberrycare.com/
Baby Shusher (App): https://babyshusher.com/pages/baby-shusher-app 

The Incredibles (Film): https://www.imdb.com/title/tt0317705/ 

The Sandlot (Film): https://www.imdb.com/title/tt0108037/ 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Jesse Randall is the founder and CEO of Sweater, a company making venture investing accessible to anyone with a smartphone. He is also a husband and father of five kids, ranging from 7 to 17 years old. 

In this conversation, Jesse shares how he thinks about balancing ambition, marriage, and fatherhood without losing sight of what matters most. He talks about moving his family to Puerto Rico, why putting career above everything else can leave you miserable, and why dads need to be strong, caring, and fully engaged at home.

Jesse also opens up about his parenting philosophy, including why he believes fathers should be authoritative first and friends second, how he and his wife use a no hint dropping rule to communicate better, and why both parents need something outside of work and family that is just for them. We also get into one of the most fascinating parts of the conversation, how Jesse is using AI to rethink his kids’ education and teach them how to think critically in a world where information is everywhere. We discussed: 

• Moving a family to Puerto Rico: How Jesse approached a major family transition and helped his kids adapt to a completely new environment.
• The cost of putting career first: Why Jesse believes chasing professional success at the expense of family can leave you deeply unfulfilled.
• What strong fatherhood really looks like: Why dads need to be caring, present, emotionally grounded, and willing to lead at home.
• Better communication in marriage: The “no hint dropping” rule Jesse and his wife use to avoid passive-aggressive communication and say what they actually mean.
• Why parents need a third pillar: Jesse shares why both partners need something outside of work and family that helps them stay grounded and fulfilled.
• Rethinking education with AI: How Jesse is using AI to redesign his kids’ learning and teach them to think critically in a world full of instant information.

Where to find Jesse Randall

• LinkedIn: https://www.linkedin.com/in/sweaterceo/  
• Sweater: https://www.sweaterventures.com/ 

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 Jesse Randall, founder and CEO of Sweater!

(01:39) Why Jesse moved his family to Puerto Rico

(03:09) Helping five kids adjust to a massive family move

(05:16) Why putting career first can leave you miserable

(09:41) The family and faith values that shaped Jesse

(13:53) Preparing kids for a world changed by AI

(16:31) What it means to be a strong and present dad

(24:21) Why every parent needs something outside work and family

(28:32) Endurance sports, headspace, and staying grounded

(32:17) Why dads should be authoritative first and friends second

(35:43) The “No hint-dropping” rule that changed their marriage

(39:54) Why clear communication matters with kids too

(43:29) How Jesse is rethinking education with AI

(53:30) The biggest surprise after 17 years of fatherhood

(57:46) Lightning round: Parenting philosophy, family rhythms, and what matters most

Resources From This Episode:

Sweater Ventures: https://www.sweaterventures.com/  

Ball Floater (Toy): https://a.co/d/04uaYZ3C 

The Emperor's New Groove: https://www.imdb.com/title/tt0120917/ 

Dumb and Dumber: https://www.imdb.com/title/tt0109686/ 

Ford Expedition: https://www.ford.com/suvs/expedition/ 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Mike Rome is the founder of moonwater, a performance marketing studio that helps startups grow, and a longtime operator in growth stage tech where he previously served as a CMO and growth leader. Before starting his own firm, he spent a decade inside venture-backed companies building teams and learning the craft of marketing. Mike and his wife Kate are parents of three boys and built their life around entrepreneurship, resilience, and perspective after navigating their son’s heart condition while launching his company. We discussed: 

• Starting a company later in life: Why Mike believes the advice to launch startups young is a myth, and how having kids can sharpen focus and urgency. 
• The myth of founder flexibility: Why running your own business doesn’t automatically mean more family time and the intentional tradeoffs required to design it. 
• An accidental path to entrepreneurship: How quitting a new job after six weeks pushed Mike to start advising, which unexpectedly became his company. 
• Building a company through crisis: What it was like launching a business while navigating his son’s rare heart condition and repeated hospital stays. 
• The parenting power law: Applying startup frameworks like ICE and power laws to focus on the parenting moments that matter most. 
• Presence over proximity: The mistake Mike made early as a founder-dad: confusing simply being around with actually being present. 

Where to find Mike Rome

• LinkedIn: https://www.linkedin.com/in/mike-rome/ 
• Moonwater website: https://moonwater.co/ 

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) Welcome Mike Rome!

(02:35) The myth of starting startups young: why kids can sharpen focus

(10:19) Starting a business with a family: turning an experiment into a company

(15:08) Burning the boats: why real commitment matters when going solo

(17:15) Gavin’s heart condition: navigating a family health crisis while building a company

(23:19) When life hits hard: perspective, expectations, and resilience

(39:39) The fishing realization: discovering the difference of shared time and shared interests

(40:09) Bring kids into your passions: why parents should lead some adventures

(40:54) Ignore the highlight reel: the danger of social media comparisons

(42:57) Redefining success: gratitude, ambition, and moving goalposts

(45:15) Presence over proximity: why simply being around isn’t enough

(47:14) The dinner disaster: a dad weekend story that didn’t go as planned

(52:59) The messy years: why chaos with young kids is something you’ll eventually miss

(54:11) The Letter to Nirvana: a lesson on craft, conviction, and authenticity

(59:40) Lightning round: dad hacks, dishwasher debates, and minivan takes 

Resources From This Episode:

Steve Albini’s Letter to Nirvana: https://faroutmagazine.co.uk/steve-albini-letter-to-nirvana/ Impact, Confidence, Effort (ICE) Framework: https://www.productplan.com/glossary/ice-scoring-model/
Reforge (Growth Programs Mentioned in Discussion): https://www.reforge.com/

Feherty (Clothing Store): https://fahertybrand.com/
The Sandlot (Film): https://www.imdb.com/title/tt0108037/
The Goonies (Film): https://www.imdb.com/title/tt0089218/
Luca (Film): https://www.imdb.com/title/tt12801262/

Home Alone (Film): https://www.imdb.com/title/tt0099785/ 

iPad: https://www.apple.com/ipad/
Kia Telluride (SUV): https://www.kia.com/us/en/telluride

—

Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Amy Winther is the Head of Product Design for Core Products at Square and the writer behind Motherboard, a Substack sharing honest stories about senior women in big tech. Chris Winther is a former financial planner turned stay-at-home dad and the primary parent for their three kids.

They’ve built a family setup that flips the traditional script. Amy’s the full-time working parent and Chris runs the home. And what’s wild is how fast it came together. One brutal childcare moment, their third nanny situation falling apart, and they made the call in basically an hour. We discussed:

• Childcare chaos that forced a fast decision: The nanny and scheduling breaking point that made them change their whole setup in basically an hour.
• Flipping the traditional script: Why Amy stayed in her career and Chris became the primary parent, and what surprised them about how it felt in real life.
• Money, power, and partnership: How “what’s mine is yours” removed tension early, and how they split ownership across work and home without resentment.
• Being the only dad in kid spaces: The awkwardness at playgrounds and playdates, the “creepy guy” fear, and how Chris found his footing and community.
• Schools and doctors calling mom first: The practical playbook for getting institutions to recognize the primary parent, even when defaults are outdated.
• Their annual family meeting system: The repeatable way they plan goals, calendars, health, and money so life doesn’t just “happen” to them.

Where to find Amy Winther

• LinkedIn: https://www.linkedin.com/in/amywinther/
• IG: https://www.instagram.com/winnie_gram/

Where to find Chris Winther

• https://www.instagram.com/cdubbonline/

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) Welcome Amy Winther, Head of Product Design at Square, and Chris Winther, Stay-At-Home Dad

(03:21) The childcare breaking point that flipped their roles

(08:49) Why Amy thought she’d be the one to stay home

(12:00) Chris on the identity shift from career to primary parent

(13:29) Money and power dynamics and why shared finances matter

(16:38) Stay-at-home dad social life and finding your people

(21:06) The assumptions, the mental load, and the stuff no one says out loud

(27:22) Rewiring the default mom call at schools and doctors

(29:26) Time is the real budget and how they protect it

(32:58) The annual family planning meeting that keeps them aligned

(38:43) Working backwards from the life they actually want

(40:08) Renovation bootcamp year while raising kids

(43:38) You and me versus the baby mindset

(45:13) Advice for couples considering a role swap

(55:09) Lightning round: SlumberPod wins, dishwasher rules, and the minivan debate

Resources From This Episode:

Square: http://squareup.com/   

Mother Board: https://amywinther.substack.com/p/welcome-to-mother-board

v0.app: https://v0.app/   

SlumberPod: https://www.slumberpod.com/  

Cocomelon (TV Show): https://www.imdb.com/title/tt12427840/ 

Paw Patrol (TV Show): https://www.imdb.com/title/tt3121722/ 

Paddington (Film): https://www.imdb.com/title/tt1109624/ 

Jurassic Park (Film): https://www.imdb.com/title/tt0107290/ 

Toy Story (Film): https://www.imdb.com/title/tt0107290/ 

VW ID. Buzz (Minivan): https://www.vw.com/en/models/id-buzz.html 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Jacob Bank is the Founder and CEO of Relay.app, a profitable, fast-growing startup that helps teams build AI agents to automate their work. Previously, Jacob founded Timeful, which was acquired by Google, where he spent six years before leaving to start Relay when his first daughter was just six months old.

He and his wife Sonia, a pediatrician at UCSF, now have three young kids and have intentionally designed both their company and their family life around flexibility, autonomy, and depth over scale. We discussed:

• Leaving Google with a baby at home: The three-part framework Jacob used to decide when it was financially and professionally the right time to start again.
• Why startups can be better for parents: How small, async teams with high trust can offer more flexibility than big companies.
• Double-dipping as a dad: Turning errands, chores, and workouts into bonding moments with his kids.
• “Imagine if I Did That”: The parenting framework Jacob uses to teach emotional regulation and responsibility.
• Patience through repetition: How each additional child made him calmer, more flexible, and less reactive.
• Raising AI native kids: Helping children develop intuition and depth while still embracing powerful new tools.

Where to find Jacob Bank

• LinkedIn: https://www.linkedin.com/in/jacobbank/ 
• X: https://x.com/jebank
  
  

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 Jacob Bank!

(02:30) Parenting with a pediatrician spouse: the blessing and the anxiety tax

(04:45) The 3-part decision framework: bills, growth, and daily fit

(08:32) Big company vs startup “risk”: what’s actually safe in a modern career

(11:13) Founder paternity leave: the phased approach that made it workable

(15:22) Why small teams can be best for parents: async culture, no meetings, high trust

(20:40) Logistics and support systems: daycare, nanny, family, and parent carpools

(27:33) Daycare vs nanny: why kid three changed everything

(32:12) Double dipping: turning chores and errands into quality time

(36:19) Kids and work talk: bringing them into problems and building curiosity

(41:19) How three kids changes you: patience, flexibility, and letting go of control

(46:58) “Imagine if I Did That”: Jacob’s tantrum and behavior framework

(49:56) Redefining founder success: staying small, profitable, and intentional

(54:11) Negotiating parenting styles: physical risk and the playground debate

(55:27) AI at home: curiosity threads, voice mode, and raising AI-native kids

(59:44) Lightning round: CocoMelon trauma, minivans, and dad grocery store dominance

Resources From This Episode:

Relay.app: https://www.relay.app/ 

Rider Safe Travel Vest: https://ridesafertravelvest.com/

Little House on the Prairie (Audiobook): https://www.audible.com/pd/Little-House-on-the-Prairie-Audiobook/B01N12SFSC

Leo (Film): https://www.imdb.com/title/tt5755238/ 

Bluey (TV Show): https://www.imdb.com/title/tt7678620/ 

—

Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com