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: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

• 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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

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: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

• The power of partnership: How Amit and his wife, Bijal, support each other in their careers while raising two young kids.
• Balancing career and family: The conscious decisions Amit and Bijal made to ensure their careers and family life could thrive together, despite the challenges.
• Shared values in parenting: Amit’s approach to instilling values like kindness, curiosity, and persistence in his children and how he aligns with his wife on these principles.
• Parenting through trade-offs: The sacrifices Amit has made to maintain work-life alignment, including how they manage time, travel, and childcare logistics.
• Raising resilient kids: Amit’s thoughts on teaching his kids resilience through boundaries and handling disappointment.
• The importance of structure: How Amit uses his love for operations and structure to maintain balance and ensure his family’s needs are met.

Where to find Amit Shah

• LinkedIn: https://www.linkedin.com/in/amitrshah1/ 

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Welcome Amit Shah, COO at Virta Health

(03:49) The decision to start a family: career executives navigating parenthood

(06:11) Shared values and partnership: aligning family and career priorities

(07:59) Logistics and support systems: the power of the one calendar rule

(29:35) Advice for career-focused executives considering parenthood

(32:46) Facing the inevitable trade-offs: making parenting and career work together

(33:16) Aligning family and career priorities: finding balance in a busy life

(34:07) Parallels between work and family: applying business skills to parenting

(34:49) Supportive work environment: the impact of a family-friendly workplace

(36:01) Favorite books to read to kids: Amit’s go-to parenting reads

(45:00) Balancing nutrition and health for kids: Amit’s approach to healthy eating

(49:34) Negotiating parenting styles: challenges and compromises in raising kids

(50:46) Fun and challenges of parenting: Amit’s personal parenting philosophy
(54:49) Lightning round: the diaper genie, minivans, and other parenting hacks

Resources From This Episode:

Virta Health: https://www.virtahealth.com/

Diaper Genie: https://www.diapergenie.com/

Minivans (Toyota Sienna): https://www.toyota.com/sienna/

Giraffes Can’t Dance (Book): https://www.amazon.com/Giraffes-Cant-Dance-Giles-Andreae/dp/0545392551 

Wonderbly (Personalized Books): https://www.wonderbly.com/

Cat & Jack (Target Clothing Brand): https://www.target.com/b/cat-jack/-/N-qqqgm 

Khan Academy Kids (App): https://learn.khanacademy.org/khan-academy-kids/

—

Support Startup Dad

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

He’s also a husband and a dad to a young daughter, with a second daughter on the way. When I first invited Lee on the show, he had a five-month-old baby and felt like he was deep in the trenches of new parenthood. Nearly a year later, we finally sat down to talk about what that first year of fatherhood was really like.

In this episode, Lee shares how becoming a dad changed his perspective on work, ambition, empathy, and priorities. He talks about parenting while working inside hypergrowth startups, navigating family planning with an intense career, setting boundaries, sharing the load at home, and how Lee thinks about AI, education, and raising kids in a rapidly changing world. We discussed:

• Becoming a dad inside hypergrowth startups: What it was like navigating new parenthood while working at two of the fastest-growing companies in tech.
• Questioning readiness for fatherhood: How uncertainty, self-doubt, and honest conversations with his wife shaped the decision to start a family.
• Miscarriage and pregnancy anxiety: The emotional challenges that came before their first daughter and how it changed Lee’s perspective on control and fear.
• Setting boundaries without losing ambition: Why prioritizing health and family actually made Lee better at his job, not worse.
• Sharing the load at home: How Lee and his wife divide responsibilities, protect evening routines, and make remote work actually work for their family.
• Raising kids in an AI-powered world: Lee’s thoughts on education, curiosity, and why he wants his daughters to believe they can build and shape the future.

Where to find Lee Robinson

• LinkedIn: https://www.linkedin.com/in/leeerob/ 
• X: https://x.com/leerob
• YT: https://www.youtube.com/@leerob
• Website: www.leerob.com
  
  

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Welcome Lee Robinson, VP of Developer Education at Cursor

(01:05) The first year of fatherhood: how becoming a dad changed everything

(03:06) Building inside two hypergrowth startups while raising a young family

(06:17) Deciding to have kids: timing, doubt, and tough conversations

(09:31) Parenting with an intense career: fears vs reality

(15:10) Deciding to start a family: timing, anxiety, and hard conversations

(20:12) What becoming a dad changed that Lee didn’t expect

(28:16) Sharing the load at home: dividing responsibilities with intention

(32:07) Protecting family time without sacrificing ambition

(35:13) Seeing my wife become an incredible mom

(37:34) Parenting challenges we’re still figuring out

(39:47) Empathy after becoming a dad: seeing the world differently

(43:46) AI and education: how Lee thinks about raising kids in a new era

(53:07) Looking ahead to 2026: family, work, and optimism

(54:02) Lightning round: parenting products, minivans, and dad life

Resources From This Episode:

Cursor: https://cursor.com/ 

Vercel: https://vercel.com/ 

ChatGPT: https://chatgpt.com/ 

Baby bottle washer: https://a.co/d/aGUSOwn 

Toy Story (Film): https://www.imdb.com/title/tt0114709/ 

Finding Nemo (Film): https://www.imdb.com/title/tt0266543/  

—

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

• The hero at home: How Pranav’s wife, Charu, has played a key role in supporting his entrepreneurial journey and balancing family life.
• Startup struggles and family life: The challenges Pranav faced starting a company with two young kids and without a local support system.
• The balance of 9-9-6: Pranav’s personal take on balancing work and parenting by dedicating quality time to his kids, especially on weekends.
• Parenting through health challenges: How a major health scare for one of his daughters shaped his perspective on family and resilience.
• Challenging kids to think: Pranav’s approach to fostering curiosity and critical thinking in his children, including using trivia and custom GPT tools.
• Building responsibility and agency: Why Pranav believes it’s crucial to instill a sense of personal accountability and how he applies this in his parenting.

Where to find Pranav Piyush

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Welcome Pranav Piyush, Co-Founder and CEO at Paramark

(02:10) The hero at home: how Pranav’s wife supports his entrepreneurial dreams

(06:02) Raising a family as immigrants: the challenges and rewards

(22:03) Parenting principles: joining your kids in fun activities and creating memories

(25:38) Challenging your kids: encouraging curiosity and critical thinking

(30:24) Enjoying the small moments: family time, digital detox, and connecting

(32:52) Education: why pranav believes it’s broken and needs change

(33:20) Boredom in school: how it reflects a systematic issue

(34:52) Solutions beyond school: the search for engaging education

(35:49) The role of AI in education: will technology revolutionize learning?

(36:30) Why college still matters: the importance of traditional education

(41:25) Teaching personal accountability: how pranav instills responsibility in his kids

(45:11) Technology and kids: setting boundaries and encouraging real-world experiences

(47:16) Exciting family plans: what’s next for Pranav and his kids

(49:57) Lightning round: the SNOO, unlimited iPad time, and other parenting hacks

Resources From This Episode:

Paramark: https://paramark.com/ 

SNOO (and other Happiestbaby products): https://www.happiestbaby.com/ 

Zootopia 2 (Film): https://www.imdb.com/title/tt5042066/ 

Back to the Future (Film): https://www.imdb.com/title/tt0088763/

Taylor Swift (Artist/Music): https://www.taylorswift.com/

The Warriors (Basketball Team): https://www.nba.com/warriors/

CocoMelon (TV Show): https://www.cocomelon.com/

Toyota Sienna (Car Model): https://www.toyota.com/sienna/ 

Honda Odyssey (Car Model): https://www.honda.com/odyssey 

GTMN (Podcast): https://podcasts.apple.com/us/podcast/gtmn/id1845001203  

Brandformance (Podcast): https://podcasts.apple.com/us/podcast/brandformance/id1746064786  

—

Support Startup Dad

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

When his daughters were just 8 and 9, Jason and his wife quit their jobs, pulled the kids out of school, and spent a full year traveling across 11 countries. We discussed:

• Leaving work to reconnect: What prompted Jason to walk away from startup life and plan a year-long trip around the world with his wife and two daughters.
• When things go wrong: Why Jason believes travel disasters make the best family memories and how they used setbacks to teach adaptability and problem-solving.
• Building deep connections off-grid: How spending 24/7 together changed their family dynamic, from independent dinners to hard conversations.
• Teaching self-reliance through discomfort: Jason shares his philosophy on preparing kids for the real world and why he sees challenge as essential, not optional.
• From startup grind to dad mode: The binary approach Jason takes to work and parenting, and why he believes being all-in matters more than balance.
• How his daughters see him now: Why watching their dad work hard, and then totally disconnect, influenced how his kids think about careers, failure, and ambition.

Where to find Jason Smith

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Welcoming Jason Smith, Co-Founder and CEO at Klue

(01:09) What sparked a year-long trip around the world

(02:21) How planning the journey went from 6 weeks to 12 months

(05:08) The wild story of renting their house before quitting their jobs

(06:33) Early travel struggles and breakthrough moments

(09:54) Teaching kids on the road and bringing learning to life

(12:48) Volunteering in Peru and breaking the privilege bubble

(17:03) Favorite travel memories and embracing the unexpected

(24:51) Why real connection takes getting off the grid

(36:17) How his daughters see startups and business now

(39:35) Navigating AI and the new rules of work

(41:15) Building resilience by leaning into hard things

(46:27) United front parenting and avoiding the ‘ask mom, ask dad’ trap

(48:26) How the parent-child relationship evolves over 20 years

(51:44) Teaching work ethic and financial independence

(01:00:49) Lightning round: parenting quirks, movie picks, and minivan takes

Resources From This Episode:

Klue: https://klue.com/ 

Jason’s Travel Video: https://www.youtube.com/watch?v=O1vMnTDHe6c 

One More Smith (Jason’s Blog): https://onemoresmith.com/ 

Jolly Jumper: https://jollyjumper.com/ 

The Matrix (Film): https://www.imdb.com/title/tt0133093/ 

Frozen (Film): https://www.imdb.com/title/tt2294629/ 

Support Startup Dad

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

• The pivot from entrepreneurship to fatherhood: Dr. Emilio Galán’s decision to leave his startup career behind and become a stay-at-home dad after stepping away from his company.
• Balancing health challenges with career demands: How Dr. Galán manages four autoimmune conditions and the toll his previous career took on his body.
• Building a family-first life: The struggles and rewards of becoming a full-time parent to two young children and how this shift allowed him to reconnect with his family.
• The philosophy of “Wipe the Butt”: Dr. Galán explains his approach to parenting, teaching responsibility, and maintaining boundaries while staying emotionally available to his kids.
• Finding contentment in the "dopamine desert": How Dr. Galán adjusted to life without the constant hustle of the startup world and learned to find joy in small, everyday moments.
• Self-care as a priority: How Dr. Galán incorporates practices like flexibility exercises and the Happy Body method to manage his physical and mental well-being while raising his kids.

Where to find Dr. Emilio Galán

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Welcome Dr. Emilio Galán, former co-founder of Robin Healthcare, now a stay at home dad

(03:03) Early life and aspirations of becoming a doctor

(06:12) The struggles and realities of medical school

(09:04) Founding Robin: the start of his entrepreneurial journey

(12:51) Transitioning from startup life to stay-at-home dad

(17:26) Finding balance: self-care, family, and health

(21:16) Navigating parenthood, resentment, and expectations

(31:51) Advice for founders who are parents

(37:43) The long-awaited family project: creating meaningful work

(38:49) Understanding emotions, needs, and communication

(39:34) Creative expression and setting requests in parenting

(42:21) Celebrating personal growth and change as a dad

(43:55) Contrarian take: why shyness doesn’t exist

(47:08) Contrarian take: the “Wipe the Butt” philosophy

(50:51) The taco episode: a parenting breakdown moment

(58:21) Lightning round: parenting insights and funny dad moments

Resources From This Episode:

The Happy Body Method: https://thehappybody.com/the-happy-body-program/ 

Jordan Peterson: https://www.jordanbpeterson.com/

Brene Brown: https://brenebrown.com/

Gabor Maté: https://drgabormate.com/

Internal Family Systems (IFS) Therapy: https://www.selfleadership.org/

Nonviolent Communication: https://www.cnvc.org/

Alexa: https://alexa.amazon.com/

Google Home: https://store.google.com/us/product/google_home 

Land Before Time (Fil): https://www.imdb.com/title/tt0100507/

Jumanji (1995) (Film): https://www.imdb.com/title/tt0113497/

Dead Poets Society (Film): https://www.imdb.com/title/tt0097165/

Patch Adams (Film): https://www.imdb.com/title/tt0129290/

Frida Baby (Butt Frida): https://www.fridababy.com/products/windi-the-wind-reliever 

Frida Baby (Nose Frida): https://www.fridababy.com/products/nosefrida-the-snot-sucker 

—

Support Startup Dad

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

Michael, a British expat married to a German partner, shares what it was like stepping away from a demanding executive career to prioritize global experiences with his family and a deep connection with his kids. We discussed:

• Ditching routine for the unknown: What drove Michael and his wife to finally say yes to a long-held dream of traveling the world with their kids.
• Homeschooling while abroad: How they navigated state regulations, picked a suitable curriculum, and stayed on track academically from Tanzania to China.
• Teaching math in paradise: Michael shares what it was like to turn a beach in French Polynesia into a classroom and how he helped his daughter jump two grade levels in math.
• Genetic testing and pregnancy stress: The emotional rollercoaster of discovering a rare genetic match mid-pregnancy and what they learned from it.
• Redefining success: Why Michael believes happiness matters more than grades or accolades, and how he’s shaping his parenting philosophy around presence over pressure.
• Parenting far from family: The pros and cons of raising kids without extended family nearby and why Michael and his wife chose to stay in the US.

Where to find Michael Goodbody

• LinkedIn: https://www.linkedin.com/in/michaelgoodbody/ 
• Twitter: https://x.com/mcgunome

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Introducing Michael Goodbody, former Global Head of Marketing & Communications at Robinhood

(01:06) Leaving a top exec job to homeschool and travel

(02:36) Quitting Robinhood and chasing a dream

(05:04) Homeschooling logistics across 21 countries

(07:35) How they planned financially for a year off

(09:46) Learning through travel: science, history, and volcanoes

(22:50) Safari in Tanzania and chasing pandas in China

(26:28) What it’s like coming home after the journey

(29:28) A genetic testing scare during pregnancy

(33:50) Why fatherhood surprised Michael in a good way

(36:42) What he’d tell his pre-dad self

(40:05) Two principles that guide Michael’s parenting

(44:31) A/B testing parenting styles with two kids

(47:57) Redefining success for your kids

(52:02) Using AI to win parenting arguments

(58:20) Lightning round: parenting quirks, travel hacks, and dad skills

Resources From This Episode:

Robinhood: https://robinhood.com/ 

Generation Genius: https://www.generationgenius.com/ 

Waldorf Education: https://www.waldorfeducation.org/ 

Alexa: https://alexa.amazon.com/ 

Curious Kid (Podcast): https://www.curiouskidpodcast.com/ 

Greeking Out (Podcast): https://www.nationalgeographic.com/podcasts/greeking-out 

Million Bazillion (Podcast): https://www.marketplace.org/shows/million-bazillion 

Crystal Palace F.C.: https://www.cpfc.co.uk/ 

Short Circuit (Film): https://www.imdb.com/title/tt0091949/ 

Raiders of the Lost Ark (Film): https://www.imdb.com/title/tt0082971/ 

—

Support Startup Dad

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

But Andrew’s most demanding role is being a full-time single dad to his two young sons. After gaining sole custody due to their mother’s struggles with bipolar disorder, Andrew has learned to navigate parenting, entrepreneurship, and mental health advocacy all at once. Living in the Bay Area near extended family, he relies on community, resilience, and regimented prioritization to raise his boys while building a startup on hard mode. We discussed: 

• Why climate change became personal: How Andrew’s motivation to cool the planet is rooted in building a safer future for his kids.
• Building a startup on hard mode: What it’s like to raise venture capital, run a climate company, and be a full-time single dad at the same time.
• Navigating mental health and custody: Andrew’s experience gaining sole custody of his sons and why normalizing conversations around mental illness matters.
• Creating a village of support: How living near family and leaning on community makes single parenting and entrepreneurship possible.
• Choosing purpose over comfort: Why Andrew believes it’s possible to live modestly in the Bay Area while prioritizing meaningful work.
• Raising resilient, curious kids: From RV road trips to using AI as a learning tool, how Andrew encourages independence, curiosity, and grit at home.

Where to find Andrew Song

• LinkedIn: https://www.linkedin.com/in/ajsong/ 
• Twitter: https://x.com/ASong408

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Introducing Andrew Song, co-founder at Make Sunsets

(02:25) What Make Sunsets does and why Andrew started the company

(04:05) How reflective aerosols work to cool the planet

(07:01) Funding climate tech through individual “climate dads”

(09:04) From AI to climate intervention: Andrew’s unconventional career path

(10:49) Almost becoming a Catholic priest and choosing fatherhood instead

(13:27) Gaining sole custody and navigating parenting amid mental illness

(17:36) Explaining a parent’s absence to young children with honesty

(19:28) The isolation of being a single-dad-founder and seeking community

(20:47) Building a startup while raising two kids alone

(23:24) Living modestly in the Bay Area on a startup salary

(30:06) Relying on family support and rebuilding the “village”

(35:55) Traveling the West Coast in an RV with toddlers

(45:37) Lightning round: Legos, road trips, AI, and minivans

Resources From This Episode:

Make Sunsets: https://www.makesunsets.com/
Termination Shock - Neal Stephenson: https://www.goodreads.com/book/show/57094295-termination-shock
Terraform Industries: https://www.terraformindustries.com/
Y Combinator: https://www.ycombinator.com/
Bloomberg: https://www.bloomberg.com/
ChatGPT: https://chat.openai.com/
Sora: https://openai.com/sora
Alva Learning App (Educational app used by Andrew’s kids): https://www.alvalearning.com/
Scale AI: https://scale.com/
Monarch Money (Personal finance app Andrew references): https://www.monarchmoney.com/
World Book Encyclopedia: https://www.worldbook.com/
Doom: https://doom.com/
Pinocchio: https://www.imdb.com/title/tt1488589/
Star Wars: Episode IV – A New Hope: https://www.imdb.com/title/tt0076759/
Joshua Tree National Park: https://www.nps.gov/jotr/index.htm
iPad: https://www.apple.com/ipad/

—

Support Startup Dad

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

From redefining balance and sharing mental load to leading through crises and building parenting systems that actually work, this episode captures the hard-earned wisdom from a community trying to do both: build companies and raise kids without losing their minds. We discussed: 

• What balance really means: Why Startup Dad guests reject work-life balance in favor of integration, trade-offs, and showing up fully wherever they are.
• Systems that protect what matters: From calendar blocks to structured rituals, the frameworks Dads use to stay present and sane.
• Raising resilient kids: Why letting kids fail, struggle, and make decisions is key to building confidence and grit.
• Mental load and invisible work: How Dads are learning to share not just chores, but the cognitive labor of running a household – and how far we still have to go.
• Building true partnerships: What it takes to communicate clearly, divide responsibilities, and support each other in parenting and work.
• Letting kids lead: From college choices to daily decisions; why modern fatherhood means preparing kids to own their path.

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Startup Dad’s biggest year yet and what’s coming next

(02:12) Why balance is a myth and integration is the goal

(09:23) Letting kids struggle so they grow stronger

(13:54) When everything falls apart and you keep going anyway

(21:55) What it really means to be the lead parent

(25:41) The invisible work that’s burning parents out

(30:05) Tech boundaries that actually work at home

(37:37) Guardrails for parenting when you’re tired and overwhelmed

(44:31) Becoming a dad doesn’t happen all at once

(47:05) Helping your kid own their journey after high school

(50:09) Making marriage and startups work at the same time

(52:10) Why you need a village (even if it’s a group chat)

Support Startup Dad

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

But Dan’s most demanding portfolio companies might be his two young kids. He and his wife, Abby, a real estate investor, are raising their family in Manhattan’s West Village, just blocks from where he grew up. Whether he’s sprinting to catch the school bus, navigating dual-career logistics, or caddying for his daughter in junior golf tournaments, Daniel brings the same thoughtful, systems-driven mindset to parenting as he does to investing. We discussed:

• Why mornings are sacred: How Daniel and his wife start every day as a family, despite their busy careers.
• Balancing careers and family: From nannies to grandparent backup, Dan shares how they manage the scheduling puzzle.
• Letting kids fail on the golf course: Dan reflects on caddying for his daughter and learning to let go of control.
• Raising kids in New York City: Why Dan believes the city is one of the best places for kids to grow up.
• The importance of practice at work and home: Lessons from sports that translate into career and parenting growth.
• Why he tracks family time like OKRs: Dan shares the analog system he uses to ensure he’s prioritizing what matters most.

Where to find Daniel Borok

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Introducing Daniel Borok, Managing Partner at nvp capital

(02:10) Balancing two careers in a dual-working household

(04:35) How the family manages childcare and travel schedules

(07:10) Starting a family later in life

(08:45) Raising kids in Manhattan vs. the suburbs

(14:40) The family’s big sports focus and weekend logistics

(17:34) Dan’s experience as his daughter’s golf caddy

(20:12) Most surprising parts of parenting

(23:43) How Dan thinks about tech exposure for his kids

(26:26) Using a weekly checklist like OKRs for parenting

(30:35) How he uses AI to reflect on weekly habits

(35:01) How he uses AI tools with his kids

(37:39) Helping kids discover their passions

(39:31) Applying sports practice frameworks to venture investing

(42:03) Lightning round: walkie-talkies, golf tees, dishwasher chaos

Resources From This Episode:

nvp capital: https://nvpcap.com/ 

The Disengaged Teen (Book by Jenny Anderson and Rebecca Winthrop): https://www.thedisengagedteen.com/ 

Training a Tiger (Book by Earl Woods): https://www.goodreads.com/book/show/546636.Training_a_Tiger 

Atomic Habits (Book by James Clear): https://jamesclear.com/atomic-habits 

Scooby Doo, Where Are You! (TV Show): https://www.imdb.com/title/tt0063950/ 

Bunk’d (TV Show): https://www.imdb.com/title/tt4591680/ 

The Goonies (Film): https://www.imdb.com/title/tt0089218/ 

iPad: https://www.apple.com/ph/ipad/ 

—

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

In this episode, we explore Oji’s philosophy on parenting through the lens of resilience, how it’s shaped, why it matters, and the role adversity plays in preparing kids for the real world. Oji shares a perspective informed by his multicultural upbringing, his frameworks for fostering independence, and the intentional choices he and his wife have made while raising two teenagers in a dual-career household. We discussed:

• Building resilience: What resilience means to Oji and why discomfort and challenge are essential for kids.
• Independence through decisions: How his 10,000-hour framework helps kids practice choice-making and responsibility.
• Learning through mistakes: Why micro-failures matter and how parents can stop rescuing children from small consequences.
• Kids as expanders: How children rise to expectations and adapt when treated as capable from an early age.
• Shepherding, not owning: Why parents should guide their kids’ path rather than shape them as extensions of themselves.
• Balancing careers and family: How he and his wife navigate dual careers and maintain steady routines and connections.

Where to find Oji Udezue

• LinkedIn: https://www.linkedin.com/in/ojiudezue/ 
• X: https://x.com/ojiudezue
• Website: https://www.productmind.co/
  
  

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Oji Udezue

(03:12) Starting a family while holding high-pressure, fast-growing careers

(05:26) Early parenting years: maintaining identity and bringing kids into adult life

(07:16) Defining resilience and why modern parenting often gets it wrong

(10:45) The 10,000 hours of independent decisions framework

(13:16) Lessons from Nigerian boarding school and developing early autonomy

(17:15) Letting kids fail safely: micro-failures, consequences, and growth

(19:51) Evaluating resilience through reactions under pressure

(22:31) Kids and career visibility: why children don’t care what you do for work

(24:27) Individuation: why Oji’s teens want their own paths, not his

(26:21) Rituals, routines, and staying connected in a dual-career household

(28:13) Advice for new parents: clarity of purpose, instinct, and overcoming fear

(31:17) Core parenting frameworks: oxygen mask, expanders, and shepherds

(43:10) AI, technology, and raising creative lateral thinkers in a changing world

(50:19) Lightning round: humor, parenting quirks, and closing reflections

Resources From This Episode:

Building Rocket Ships (Book by Oji Udezue & Ezinne Udezue): https://a.co/d/0nMe2WM  

ProductMind (Substack Newsletter): https://productmind.substack.com/ 

ProductMind.co (Website): https://productmind.co/ 

Lenny’s Podcast (Episode featuring Oji & Ezinne): https://www.lennysnewsletter.com/p/how-ai-is-reshaping-the-product-role

The Time Machine (Book by H.G. Wells): https://www.goodreads.com/book/show/2493.The_Time_Machine

Typeform: https://www.typeform.com/

Calendly: https://calendly.com/

Atlassian: https://www.atlassian.com/

Bridgewater Associates: https://www.bridgewater.com/

Microsoft: https://www.microsoft.com/

Amazon Echo: https://www.amazon.com/echo 

Big Hero 6 (Film): https://www.imdb.com/title/tt2245084/

—

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

In this episode, we talk about the concept of cognitive labor, how it’s defined, why it’s disproportionately placed on women in heterosexual partnerships, and the emotional and mental toll it takes. Allison shares insights from her years of research, including interviews with over 170 individuals in diverse family structures, shedding light on how cognitive labor impacts both professional and personal lives. We discussed:

• What is Mental Load and Cognitive Labor: Defining and explaining these concepts and her research.
• Understanding cognitive labor: How the mental work of anticipating needs, making decisions, and following through often falls disproportionately on women.
• Real-world examples: The everyday household tasks where cognitive labor shows up and how couples can divide this invisible work more equally.
• The Superhuman and The Bumbler: How gendered expectations shape household dynamics, with women often taking on the “Superhuman” role and men the “Bumbler” role.
• Breaking the mental load myth: Why cognitive labor isn’t about personality traits but about societal pressures and norms that influence how responsibilities are shared at home.
• Strategies for rebalancing: Practical ways couples can collaborate on household responsibilities, including setting up routines, improving communication, and managing expectations.

Where to find Allison Daminger

• LinkedIn: https://www.linkedin.com/in/allisondaminger/ 
• Website: https://www.allisondaminger.com/
• Substack: https://allisondaminger.substack.com/
  
  

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Allison Daminger, assistant professor of sociology at the University of Wisconsin-Madison

(02:44) Defining cognitive labor in the home and workplace
(04:27) Real-life examples of cognitive labor
(07:56) The invisible mental load: What it means for parents
(13:42) Research on cognitive labor and family dynamics
(19:53) Household dynamics and gender roles in domestic labor
(26:01) Rationalizing the imbalance in cognitive labor at home
(46:56) Exploring gender roles in household leadership
(48:11) Motherhood and cognitive labor: The unseen work
(48:43) Ideologies vs realities of balanced households
(49:15) Career dynamics and household roles: The juggling act
(49:54) Challenges in achieving cognitive labor equality
(55:04) Balanced households: Structures for satisfaction
(01:15:36) Personal insights and reflections on cognitive labor

(01:27:47) Lightning Round: Final Thoughts and Quick Tips

Resources From This Episode:

What's On Her Mind (Book by Allison Daminger): https://www.amazon.com/Whats-Her-Mind-Mental-Workload/dp/069124538X 

The Daminger Dispatch (Newsletter): https://allisondaminger.substack.com/
The Second Shift (Book by Arlie Hochschild): https://www.goodreads.com/book/show/51848.The_Second_Shift
Fair Play (Book by Eve Rodsky): https://www.amazon.com/Fair-Play-Game-Changing-Solution-When/dp/0525541942 

Love To Dream Swaddle: https://lovetodream.com/ 

The Little Mermaid: https://www.imdb.com/title/tt0097757/ 

University of Wisconsin, Madison: https://www.wisc.edu/

NYT Wirecutter: https://www.nytimes.com/wirecutter/gifts/

—

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

In this episode, Jamie shares his honest and often hilarious take on building a company with your spouse, creating parenting systems that actually work, and why sometimes the best way to help your kid process big emotions is to scream right along with them. We discussed: 

• The value of routines and structure: How simple systems like Pizza Friday and bedtime rituals help reduce friction and create predictability for young kids.
• Why “screaming it out” works: Jamie shares how he defuses tantrums by yelling alongside his kids, helping them process their emotions without shame.
• Teaching negotiation and responsibility: From chore taxes to bedtime story debates, Jamie’s approach helps his kids understand how the world really works.
• Practicing perspective as a parenting superpower: Whether it’s a hard week at work or spilled art projects, Jamie explains how he reframes moments to build resilience.
• “Anything is possible” parenting: How Jamie’s confidence borders on delusional (his wife’s words), and why he’s intentionally passing that belief on to his kids.

Where to find Jamie Nacht

• LinkedIn: https://www.linkedin.com/in/jamienacht/ 
• Website: https://havium.com/

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Jamie Nacht, co-founder and CEO of Havium

(01:56) Building a startup with your spouse while raising kids

(06:58) Parenting frameworks that actually work

(07:05) Why perspective is Jamie’s superpower

(09:32) How much of your kid’s personality is already baked in

(15:06) Pretending to be a mermaid changed my parenting

(27:51) Teaching negotiation and real-world responsibility

(33:34) Your kids hear everything (even when you think they don’t)

(35:57) The rule we use for yelling in our house

(37:25) Giving kids tech that’s just annoying enough

(40:04) Using AI to make custom coloring books for your kids

(42:51) Why my in-laws moved 5 minutes away

(48:09) The bond with your kid doesn’t always start right away

(51:58) What I hope my kids learn from me

(56:35) Lightning Round: Must-haves, Laughs, and Dad hacks

Resources From This Episode:

Havium: https://havium.com/

Do Not Ring Doorbell Sign: https://a.co/d/4AK9A3j 

Amazon Fire 7 Kids Tablet: https://a.co/d/glUlvO5 

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

Sword In The Stone (Film): https://www.imdb.com/title/tt0057546/ 

Ferris Bueller’s Day Off (Film): https://www.imdb.com/title/tt0091042/ 

The Little Mermaid: https://www.imdb.com/title/tt5971474/

Migration: https://www.imdb.com/title/tt6495056/?ref_=fn_t_1

Kia EV: https://www.kia.com/us/en/ev

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

Listen to the whole episode for an amazing discount code at Soapbox! 

In this episode, Dave shares insights about the changes he faced when becoming a parent and how he’s adjusted his role as a CEO to manage his new responsibilities at home. We talked about the systems he and his wife have in place, the challenges of balancing work and parenting, and his personal frameworks for being a present and intentional Dad. We discussed:

• Parenting adjustments: How becoming a dad led Dave to shift his focus and say no to professional commitments to be more present with his son.
• Family support systems: The importance of clear communication and shared responsibilities with his wife to manage their dual-working household.
• Time management lessons: How being a parent has made Dave more intentional with his time, balancing professional and personal priorities.
• Parenting frameworks: The trifecta of clear communication, consistent boundaries, and overflowing affection, all modeled after his experience in education.
• Leadership lessons from fatherhood: How watching Noah learn to walk has taught Dave about perseverance and leadership.

Where to find Dave Simnick

• LinkedIn: https://www.linkedin.com/in/davidsimnick/ 
• Instagram: https://www.instagram.com/davidsimnick/
• Soapbox: https://www.soapboxsoaps.com/ 

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Welcome Dave Simnick, founder and CEO at Soapbox, and Dad of one

(02:12) Preparing for fatherhood as a CEO

(05:47) Adjusting time management after becoming a parent

(07:07) Saying no to professional commitments for family time

(09:05) Balancing work and parenting responsibilities

(11:12) Family systems for a dual-working household

(13:39) Learning from being a parent: the surprising aspects

(15:36) Time management hacks post-parenthood

(17:04) Parenting frameworks: communication, boundaries, and affection

(19:36) Embracing imperfection in parenting

(22:39) Leadership lessons from fatherhood

(25:09) Advice for younger self about parenting

(30:53) Parenting disagreements and challenges

(33:00) Soapbox’s mission and global impact

(37:10) Parenting superpower: joy

(41:00) Lightning Round: Parenting hacks and travel tips

Resources From This Episode:

Soapbox: https://www.soapboxsoaps.com/
Teach for America: https://www.teachforamerica.org/
Bum Brush (Poop Spatula): https://a.co/d/2ONUFid
Bluey: https://www.bbc.co.uk/cbeebies/shows/bluey
Mulan: https://www.imdb.com/title/tt1856101/
The Sandlot: https://www.imdb.com/title/tt0108037/
Kia Carnival: https://www.kia.com/us/en/carnival
Kia Telluride: https://www.kia.com/us/en/telluride 

Mike Malloy’s episode: https://www.youtube.com/watch?v=eJ9K0oR1nt4

Discount code: startupdad15

Baby Brezza: https://babybrezza.com/

Tulum: https://www.tulum.com/

Little Blue Truck: https://www.littlebluetruckbooks.com/books/

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

Chet opens up about the inspiration behind Tin Can, how his childhood landline shaped the idea, and why he believes kids need more analog connections in a digital world. He talks candidly about the challenge of being “distracted dad” while building something he’s intensely passionate about, how he and his wife run their household like a startup, and why learning to unplug is still a daily work in progress. We discussed: 

• Creating balance at home: The systems, boundaries, and frameworks that help Chet stay grounded as a founder and father.
• Lessons from failure and obsession: What Chet’s learned about being present when work and family both demand everything.
• The art of analog parenting: How Chet and his wife teach their kids healthy relationships with technology and boredom.
• Raising kids is like running a business: From household “OKRs” to making space for unstructured family time.
• Hope for the next generation: Why Chet believes we’re entering an analog revival and what it means for parents raising digital natives.

Where to find Chet Kittleson:

• LinkedIn: https://www.linkedin.com/in/ckittleson/ 
• Instagram: https://www.instagram.com/tincan.kids/
• Tin Can: https://tincan.kids/  

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• X: https://x.com/fishmanaf
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:
(00:00) Introducing Chet Kittleson
(02:31) The childhood inspiration that sparked the idea for Tin Can
(11:13) Finding balance between family life and startup life
(13:38) Lessons learned from building, failing, and trying again
(16:21) Partnering in parenting and business with his wife
(21:34) Building Tin Can from an idea to a real product
(35:22) How parenting priorities shift as kids grow
(36:16) What team dynamics look like inside a family-led startup
(37:14) Early prototypes and how the family helped shape Tin Can
(38:50) Seeing kids’ real reactions to the analog phone
(40:02) Teaching kids to balance tech time and real-world connection
(46:38) Finding optimism and practical solutions for modern parenting challenges
(50:11) How to support Tin Can’s mission to connect families
(53:10) Lightning round: paper calendars, dad hacks, and dishwasher rules

Resources From This Episode:

Tin Can: https://tincan.kids/ 

Paper calendar: https://a.co/d/dbPXEsG 

Brooks: https://www.brooksrunning.com/ 

The Anxious Generation (book): https://www.anxiousgeneration.com/ 

Brick (app): https://getbrick.app/ 

The Hundred-Foot Journey: https://www.imdb.com/title/tt2980648/ 

Chef: https://www.imdb.com/title/tt2883512/ 

Toy Story: https://www.imdb.com/title/tt0114709/ 

The Mighty Ducks: https://www.imdb.com/title/tt0104868/ 

Honey, I Shrunk the Kids: https://www.imdb.com/title/tt0097523/ 

Freaky Friday: https://www.imdb.com/title/tt0322330/ 

Freakier Friday: https://www.imdb.com/title/tt31956415/ 

The Parent Trap: https://www.imdb.com/title/tt0120783/ 

Little Big League: https://www.imdb.com/title/tt0110363/ 

Rookie of the Year: https://www.imdb.com/title/tt0107985/ 

The Green Mile: https://www.imdb.com/title/tt0120689/ 

Rewind & Play: ABC The Millennial Way (book): https://a.co/d/6GI6tdC 

Tween Magazine: https://tweenmag.com/ 

—

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

Colin opens up about how his kids have become his greatest teachers, why he believes accountability and independence should start young, and how joining a men’s group helped him prioritize relationships, including the one with himself. From Montessori principles to Mario Kart lessons, Colin shares how parenting frameworks and founder mindsets overlap in surprising ways. We discussed: 

• Parenting through divorce: What it’s like to reset life as a single dad and how his kids’ resilience has inspired him.
• Learning from mistakes: How modeling vulnerability and apologizing to his kids has built trust and maturity.
• Resilience vs fragility: Why Colin believes kids are more robust than we give them credit for.
• Why no dad has it all figured out: Colin’s honest take on navigating career, parenting, and personal growth.
• The role of technology and AI: From skepticism to playful experiments, turning kids’ crayon drawings into Pixar-style characters.

Where to find Colin Anawaty:

• LinkedIn: https://www.linkedin.com/in/colinanawaty/ 
• X: https://x.com/colin
• Instagram: https://www.instagram.com/colinanawaty/

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• X: https://x.com/fishmanaf
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Colin Anawaty

(02:13) Adjusting to life as a single dad of two young boys

(05:37) Why Colin joined a men’s group and what he learned

(09:43) Taking stock of good and bad parenting lessons from past generations

(11:49) Kids as teachers and the power of apologizing as a dad

(14:31) Why kids are more resilient than we think

(16:29) Teaching accountability at an early age

(20:22) Montessori principles at home: independence, structure, fewer toys

(23:50) Parenting lessons from Mario Kart and screen time boundaries

(28:22) Bonding through haircut sessions with his boys

(31:27) Helping his 6-year-old overcome fear of surfing

(33:51) Social media dangers for kids and for parents

(37:43) What relationship Colin wants his kids to have with technology

(40:54) Using AI for parenting frameworks and creative projects

(46:17) Why no dad has it all figured out

(49:10) Lightning round: Parenting gear, funniest moments, and dad quirks

Resources From This Episode:

5 Types of Wealth by Sahil Bloom: https://a.co/d/0H7Evju 

The Big Book of Silly Jokes for Kids: https://a.co/d/12730G0 

The Expectant Father: The Ultimate Guide for Dads-to-Be: https://a.co/d/ji8u48g 

The New Father: A Dad's Guide to the First Year: https://a.co/d/chjTYyA 

Montessori Method: https://montessori.org/ 

Dad Jokes Instagram (Logan Lisle): https://www.instagram.com/loganlisle/ 

Potty Training Seat: https://a.co/d/54kwn6o

LEGO: https://www.lego.com/ 

The Karate Kid: https://www.imdb.com/title/tt0087538/ 

Endless Summer: https://www.imdb.com/title/tt0060371/ 

Swiss Family Robinson: https://www.imdb.com/title/tt0054357/ 

Cars: https://www.imdb.com/title/tt0317219/ 

The Grinch: https://www.imdb.com/title/tt2709692/ 

Inside Out: https://www.imdb.com/title/tt2096673/ 

Indiana Jones and the Temple of Doom: https://www.imdb.com/title/tt0087469/ 

Nintendo Switch: https://www.nintendo.com/switch/ 

Duke Nukem: https://2k.com/games/duke-nukem/20th-anniversary/ 

Super Mario Bros: https://mario.nintendo.com/characters/ 

Mario Kart: https://mariokart8.nintendo.com/ 

Milo and Chip: https://www.youtube.com/@miloandchip/videos 

Athena Health: https://www.athenahealth.com/

Alex’s Episode: https://www.youtube.com/watch?v=OOa9mS-CIuQ

Josh Jones-Dilworth & Culturati: https://culturati.info/

—

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

In this episode, Chad and I talk about raising kids while running companies, blending family life with creative projects, and the importance of designing systems at home, just as you would at work. He shares stories about parenting teenagers, shaping company culture around sustainable pace, and why even the smallest rituals matter when time with your kids feels fleeting. We discussed:

• Building systems at home: How collaborating with his kids on routines turned daily battles into shared ownership.
• Parenting teenagers with balance: Why being relaxed, supportive, and flexible helped his kids thrive through responsibility and independence.
• Dinner as a cornerstone: The daily ritual that kept his family connected through the busiest startup years.
• Redefining company culture: How Thoughtbot built practices like sustainable pace and four-day client weeks to make room for life outside of work.
• Embracing differences: The importance of parenting each child as an individual, not a template, and adjusting expectations along the way.

Where to find Chad Pytel

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Chad Pytel, founder and CEO at thoughtbot and dad of two

(04:37) Exploring the aging space with AI

(06:06) Starting a gaming and production company

(08:43) Navigating teenage years

(18:33) Balancing work and family life

(19:23) Sustainable pace and company culture

(23:48) Parenting realizations

(24:56) Frameworks for parenting

(25:21) Daily routines and systems

(27:17) Sunday date concept

(29:50) Parenting styles and screen time

(35:34) Halloween traditions

(37:37) Keeping up with the Joneses

(41:19) Lightning Round: Being a relaxed and reasonable dad

Resources From This Episode:

Giant Robots Smashing Into Other Giant Robots (Podcast): https://podcast.thoughtbot.com/

thoughtbot: https://thoughtbot.com/

12 Sided Studios: https://12sidedstudios.com/ 

Critical Role (Actual Play Series): https://critrole.com/ 

Dimension 20 (Actual Play Series): https://www.dropout.tv/dimension-20 

American Society on Aging: https://www.asaging.org/ 

Wall-E (Film): https://www.imdb.com/title/tt0910970/

Monty Python and the Holy Grail (Film): https://www.imdb.com/title/tt0071853/

Kia Rondo (Car Model): https://www.edmunds.com/kia/rondo/ 

thoughtbot: https://thoughtbot.com/ 

12 Sided Studios: https://12sidedstudios.com/ 

—

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

In this episode, Jonathan opens up about his entrepreneurial journey, the lessons he has carried from his upbringing, and the realities of being a dad and founder at the same time. We discussed:

• Why work-life balance doesn’t exist: Jonathan explains why he believes balance is a myth, and instead focuses on being fully present
• Redefining success as a father and founder: He shares how his definition of success shifted from chasing cars and houses to prioritizing comfort, family health, and presence.
• Breaking generational patterns with love: From hugs to family vacations, Jonathan reflects on how intentional affection and kindness help him parent differently than he was raised.
• Partnership and parenting: He talks about how he and his wife share the load, why he ignores outdated cultural norms around gender roles in parenting, and the promise he kept to support her becoming a stay-at-home mom.
• Why nice guys don’t finish last: Jonathan describes how leading with empathy and kindness has shaped Springboard’s culture, strengthened client trust, and fueled growth.

Where to find Jonathan Jamil

• LinkedIn: https://www.linkedin.com/in/jjthatcxguy/ 
• Springboard: https://www.springboardhq.com/ 
• Instagram: https://www.instagram.com/thejonathanjamil/ 
• X: https://x.com/jjthatcxguy
  
  

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• Instagram: https://ww.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Welcome Jonathan Jamil

(03:55) Starting Springboard and working with stay-at-home moms

(06:41) Why Springboard never posts job listings

(08:33) Building a business while raising a newborn

(10:19) Why work-life balance doesn’t exist

(13:27) Redefining success as a dad

(14:46) Why you can’t parent alone without community

(16:06) Advice to his younger self before becoming a dad

(18:23) Never stop dating your wife

(20:35) The power of vacation and taking breaks

(24:14) His simple fatherhood framework: Show up, listen, love

(26:22) Espresso-fueled speeding ticket during the colic phase

(28:54) Parenting disagreements: Screen time and sugar

(30:56) Tech boundaries and raising daughters in a digital world

(32:55) Using AI to plan family vacations

(34:39) Why “nice guys finish last” is a myth

(37:14) Lightning round: Parenting wins and toy assembly fails

Resources from this episode:

Jambys: https://www.jambys.com/

Disney Store: https://www.disneystore.com/toys-plush/toys/ 

Lime Green Bed Sheets: https://www.amazon.com/Lime-Green-Bedding/s?k=Lime+Green+Bedding

Cocomelon: https://www.youtube.com/channel/UCbCmjCuTUZos6Inko4u57UQ

Wreck-It Ralph: https://www.imdb.com/title/tt1772341/

Ratatouille: https://www.imdb.com/title/tt0382932/

Home Alone: https://www.imdb.com/title/tt0099785/
The Santa Clause: https://www.imdb.com/title/tt0111070/

Play-Doh: https://shop.hasbro.com/en-ca/play-doh

Toyota Sienna: https://www.toyota.com/sienna/

Siqi Chen’s Episode: https://www.youtube.com/watch?v=I2Nm5Mkj0s0

Cape May: https://www.capemay.com/

Ocean City: https://www.ocnj.us/

Rehoboth Beach: https://www.rehobothbeachde.gov/

Disney World: https://disneyworld.disney.go.com/

UPPAbaby: https://uppababy.com/

Boppy: https://www.boppy.com/

Jamby’s: https://www.jambys.com/

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

As a dad of 11-year-old twins and husband to Camille, a lawyer who now leads the legal team at Gamesight, Adam shares what it’s like to grow a company and a family at the same time. From the challenges of raising twins to why he doesn’t believe in separating work mode from dad mode, Adam offers an honest look at the overlap of parenting and entrepreneurship. We discussed: 

• Raising twins while building a company: Why he compares it to running three startups at once.
• The sleep training strategy: How it became the most important defensive move for survival with twins.
• Work mode vs dad mode: Why Adam believes in being the same person everywhere.
• AI at home: Creative ways his kids use AI for learning, projects, and fun.
• The mantra “show up and try”: Why presence is the foundation for leadership and parenting.

Where to find Adam Lieb:

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

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com 
• LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
• X: https://x.com/fishmanaf
• Instagram: https://www.instagram.com/startupdadpod/ 

In this episode, we cover:

(00:00) Introducing Adam Lieb

(02:16) What Gamesight does and how Adam started in gaming

(05:32) Raising 11-year-old twins with his wife, Camille

(07:38) Running “three startups” at once: company and twins

(09:34) Working with his wife inside the business

(10:01) What’s unique about having twins, and why sleep training mattered

(16:05) Why doesn’t Adam separate dad mode and work mode

(18:30) Cheering from the baseball field while sending emails

(20:13) The mantra that guides parenting and leadership: show up and try

(24:30) Lessons learned since becoming a dad and mistakes along the way

(26:17) The balance between coaching your kids and supporting them

(29:16) Aligning with his wife on parenting philosophy

(31:29) Setting limits on video games and tech at home

(39:46) Raising kids with AI and creative projects they’ve built

(47:16) Lightning round: indispensable products, useless gear, quirks, and dad superpowers

Resources From This Episode:

Gamesight: https://gamesight.io/ 

Collapsible Wagon: a.co/d/dmFVnSI 

Table For Two: https://buytablefortwo.com/ 

Alexa: https://alexa.amazon.com/ 

Happy Gilmore: https://www.imdb.com/title/tt0116483/

Happy Gilmore 2: https://www.imdb.com/title/tt31868189/
The Lord Of The Rings: https://www.imdb.com/title/tt0120737/ 

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