Startup Dad

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

He walked away from corporate America and took a  75% pay cut to become one of the leading researchers on fatherhood, caregiving, and work-family integration. Now retired, Brad is a happily married dad of three who has spent the last quarter-century studying why men struggle to escape work-family conflict. We discussed:

• The 3 Archetypes of Modern Fatherhood: Breaking down traditional, egalitarian, and conflicted fathers - and why the "conflicted" bucket is consistently the largest group.
• The Caregiving Gap: Why 70% of fathers report wanting a 50/50 caregiving split, yet only 35% actually live it.
• The Financial & Organizational Traps: The economic pressures and workplace cultures that keep men locked into primary breadwinner roles even when they want out.
• The Power of Early Paternity Leave: Why taking dedicated time off in the first few weeks of a child's life sets the trajectory for a dad's hands-on caregiving identity for decades.
• The Dual-Career Lifecycle: How couples navigate moving through stages from allies and acrobats to adversaries and accommodators.
• The Danger of Over-Scheduling Kids: Why competitive youth sports and hyper-structured childhoods are stripping kids of independence and unstructured play.
• Why Parenting Never Ends: Lessons from raising three adult children through career shifts, health struggles, and navigating relationship dynamics across decades.

Where to find Brad Harrington

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

Where to find Adam Fishman

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

In this episode, we cover:

(00:00) Welcoming Brad Harrington, former Executive Director of the Boston College Center for Work and Family

(02:26) Commuting 3,000 miles every other week while balancing family

(06:00) Walking away from corporate America and taking a 75% pay cut

(08:16) From personal conflict to a quarter-century of research

(10:41) The three archetypes of fatherhood: traditional, egalitarian, and conflicted

(16:16) Why conflicted fathers are the least satisfied men at work and home

(24:32) Don't argue about who does more—focus on who does what

(28:15) The mental load and the mindset of a partner versus an employee

(32:26) Four reasons men stay locked in the breadwinner role

(36:30) Paternity leave and the "train leaving the station" in those first few months

(43:32) The four stages of couples: allies, acrobats, adversaries, and accommodators

(48:19) Advice for startup founders on building parental leave policies

(52:07) The stay-at-home dad study and societal double standards

(57:52) The overscheduled child and the loss of unstructured play

(1:04:36) Parenting never ends: navigating adulthood, health struggles, and advice

(1:11:56) Lightning round: Minivans, pre-iPad travel, family chat, and dishwasher loading

Resources From This Episode:

Brad Harrington’s Profile at Boston College: https://www.bc.edu/bc-web/offices/office-of-university-communications/for-the-media/z_archive/brad-harrington.html 

Hewlett-Packard Enterprise: https://www.hpe.com/

Dr. Linda Haas: https://www.researchgate.net/profile/Linda-Haas 

The Wizard of Oz (Film): https://www.imdb.com/title/tt0032138/

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

—

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For Startup Dad Merch: www.startupdadshop.com

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

He’s also a dad of three and one of the very first guests to appear on Startup Dad (#2 in fact!). Three years later, Adam is back to talk about what has changed in his family and how getting laid off from Eventbrite sent him deep into AI experimentation, model training, and reinforcement learning. We discussed:

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

Where to find Adam Grenier

• Website: https://www.adamgrenier.com/ 
• LinkedIn: https://www.linkedin.com/in/akgrenier/ 
• Twitter: https://x.com/AKGrenier
  
  

Where to find Adam Fishman

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

In this episode, we cover:

(00:00) Welcoming Adam Grenier, Founder of AI Matey

(02:09) What changed in three years of parenting and startups

(04:27) Advocating for two neurodivergent kids with different needs

(08:45) How AI Matey led to training AI on dad jokes

(13:33) Learning AI with goat screams and school photos

(24:11) How anyone can start training AI models

(29:17) What training on dad jokes actually taught the model

(32:02) What actually makes a great dad joke

(36:52) Putting the biggest AI models to the dad joke test

(47:09) Getting reward hacked by your own AI model

(51:05) Why the best dad jokes get straight to the point

(53:41) Bringing humans and kids into the judging process

(55:24) Why Adam fired an AI judge for being too slow

(57:13) What dad jokes can teach us about building better AI

(01:05:04) Can you actually teach a sense of humor?

Resources From This Episode:

AI Matey: https://aimatey.co/ 

DadBench: https://aimatey.co/dadbench/ 

GoatScreams: https://www.goatscreams.com/waitlist 

SmilePlease: https://smileplease.app/
ElevenLabs: https://elevenlabs.io/ 

Thinking Machines Labs: https://thinkingmachines.ai/ 

Inkling: https://thinkingmachines.ai/inkling/ 

Tinker: https://thinkingmachines.ai/tinker/ 

Prime Intellect: https://www.primeintellect.ai/ 

Unsloth: https://unsloth.ai/ 

DeepSeek: https://www.deepseek.com/ 

Gemma: https://deepmind.google/models/gemma/ 

Gemini: https://gemini.google.com/app 

GLM: https://chat.z.ai/ 

Grok: https://grok.com/ 

Anthropic: https://www.anthropic.com/ 

OpenAI: https://openai.com/ 

Claude: https://claude.ai/ 

The Book of Mormon (Musical): https://bookofmormonbroadway.com/ 

—

Support Startup Dad

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

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

Beyond her academic work and her testimony before the U.S. Senate on social media safety, Jackie is a grounded voice in the parenting space who navigates the day-to-day balance of screen time in her own household. She is a mom of three young kids, married to a tech entrepreneur, and works to bridge the gap between complex psychological research and the practical demands of modern parenting. We discussed:

• The disconnect between screen time panic and actual research: Why the "all screen time is bad" narrative isn't supported by science, and how parents can let go of perfectionist guilt.
• The Transformation Framework: How specific features of social media (asynchrony, public reach, image focus, and permanency) fundamentally alter childhood friendships.
• Dialectics in parenting: Practicing dialectical thinking to hold two seemingly contradictory truths at once (e.g., deeply loving your child while feeling completely overwhelmed).
• Smart device staging: How to evaluate when a child is ready for a phone, running "tech experiments," and layering access from smartwatches and dumb phones up to full smartphones.
• School phone bans and Yondr pouches: What the latest research actually shows regarding school phone policies, distraction, test scores, and student mental health.
• AI as the next frontier: What parents and educators need to know right now to help kids navigate AI tools safely and responsibly.

Where to find Jackie Nesi

• Website: https://www.jacquelinenesi.com/ 
• LinkedIn: https://www.linkedin.com/in/jacqueline-nesi-phd-b070595b 
• Substack: https://technosapiens.substack.com/
• IG: https://www.instagram.com/jacqueline_nesi/
  
  

Where to find Adam Fishman

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

In this episode, we cover:

(00:00) Welcoming Jacqueline Nesi, Associate Professor at Brown University and Techno Sapiens author

(04:01) What teens in psychiatric care reveal about online safety

(08:00) How social media transforms kids’ friendships

(13:49) Why two opposite truths can coexist in parenting

(19:20) Why screen time is about more than counting minutes

(23:31) Treating new devices and screen rules as experiments

(27:12) How to let go of screen time guilt

(29:45) How to know when your child is ready for a phone

(33:28) How to stage phones, smart devices, and social media

(39:23) What school phone bans can and cannot solve

(45:11) Why managing screens can be harder for neurodivergent kids

(47:34) Where The Anxious Generation gets the research right and wrong

(50:33) Having regular tech talks and putting people first

(53:24) How to avoid repeating social media mistakes with AI

(59:49) Lightning round: Toy baskets, existential nursery rhymes, and minivan temptation 

Resources From This Episode:

Techno Sapiens: https://technosapiens.substack.com/ 

How to Let Go of Screen Time Guilt: https://technosapiens.substack.com/p/how-to-let-go-of-screen-time-guilt

It Takes Two (PlayStation Game): https://www.playstation.com/en-us/games/it-takes-two/ 

Lego Star Wars (PlayStation Game): https://www.playstation.com/en-us/games/lego-star-wars-the-skywalker-saga/

The Anxious Generation by Jonathan Haidt (Book): https://www.anxiousgeneration.com/book 

The Emperor’s New Groove (Film): https://www.imdb.com/title/tt0120917/

Will Ferrell (Actor): https://www.imdb.com/name/nm0002071/

—

Support Startup Dad

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

Harry Roegiers is the founder of Stuntpony; a live call coach for B2B salespeople. He’s spent the last decade working in sales performance, growth, and revenue strategy, helping teams improve how they sell and scale.

He’s also a father of three whose journey into parenthood started with a surprise. Just days after proposing to his wife Hannelore in Paris, they found out they were expecting their first child. That unexpected start helped shape his approach to parenting, staying adaptable when life doesn’t go according to plan. We discussed:

• Turning off founder mode at home: Why the instinct to analyze and fix problems works at a startup but can backfire when your partner or kids simply need you to listen.

• Breaking generational patterns: Why Harry wants his kids to talk openly about emotions while preserving something his own parents got right, giving kids the freedom to make mistakes.

• Thinking like a good ancestor: How fatherhood shifted Harry from quarter-to-quarter thinking toward decisions that could benefit his kids and future generations decades from now.

• Navigating neurodiversity without rushing to label: How Harry and Hannelore are learning to focus less on finding an answer and more on understanding what their daughter needs from them.

• Treating joy as an obligation: Why Harry believes bringing joy to others will become even more valuable in an AI-driven world, and how he practices it at home.

• Raising builders in the age of AI: How Harry’s eight-year-old built an app for turning leftovers into recipes, and why he wants his kids creating with AI instead of passively consuming it.

Where to find Harry Roegiers

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

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 Harry Roegiers, Founder/Investor

(03:39) A Paris proposal and surprise pregnancy

(06:58) What tinnitus taught Harry about the mind-body connection

(09:34) Why founder mode doesn’t work at home

(13:59) Breaking generational patterns around emotions

(19:40) Thinking like a good ancestor

(24:08) Losing his mom and thinking about legacy

(28:15) What his wife’s work taught him about real impact

(30:39) Contrarian parenting rules around swearing

(36:21) Noticing when your child may be wired differently

(37:56) Supporting your child without rushing to find a label

(41:14) Learning each kid’s different love language

(44:53) Why sharing joy is an obligation

(48:10) Vibe coding an app with his eight-year-old son

(57:19) Lightning round: training wheels, dad jokes, IKEA, and minivans

Resources From This Episode:

The Good Ancestor (Book): https://www.romankrznaric.com/good-ancestor 

Lovable (Website): https://lovable.dev/ 

Gong (Website): https://www.gong.io/ 

Chorus (Website): https://chorus.com/ 

Car back seat organizer: https://a.co/d/0fKOLA0L
Balance Bike: https://a.co/d/0gfvf8Bb 

Up (Film): https://www.imdb.com/title/tt10494

Dirk Doebler is the Founder and CEO at Parento Leave, a company dedicated to helping organizations build better parental leave programs. He lives with his wife and 3-year-old son.

Dirk and his wife spent serious time before becoming parents asking a fundamental question: Do we even want kids? And if so, how would we raise them without giving up our own dreams and lives? What emerged from that process is a 3-year-old raised with one of the most intentional, free-range, and contrarian parenting philosophies around. We discussed:

• The case for free-range parenting: Why hovering at the playground harms your child’s development, and why Dirk lets his three-year-old problem-solve on his own.

• Joining our life, not revolving around his: How Dirk and Kate built their parenting philosophy from scratch, choosing to bring their son along on their journey rather than putting their own dreams on hold.

• Navigating pediatric feeding disorders: The surprisingly underdiagnosed world of toddler anorexia and sensory feeding challenges, and what their family has learned on the journey.

• World traveling with a toddler: How taking 30 flights to 10 different countries by age three taught their son to embrace boredom, entertain himself, and love adventure.

• Intentional tech and zero screens: Why Dirk casts videos to the TV instead of handing over a phone, avoids fast-paced cartoons, and views AI as a lazy substitute for authentic parenting.

• Taking two paternity leaves: Why Dirk took a second, full-time parental leave when his son was 10 months old, and why showing up daily matters far more than just "banking" quality weekends.

Where to find Dirk Doebler

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

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 Dirk Doebler, Founder & CEO at Parento Leave

(03:06) What most parents get wrong: hovering and screens

(05:19) Deciding if we wanted kids and building a parenting philosophy

(08:05) Raising a child who joins your life instead of running it

(09:16) Understanding pediatric feeding disorders in toddlers

(14:12) Dividing household load and the "no quid pro quo" rule

(19:45) Free-range parenting: building confidence and independence

(24:45) Flying with a toddler: 30 flights and 10 countries by age three

(34:06) Tech boundaries: Jitterbugs, window-style TV, and no phones

(38:38) Why using AI for parenting is a lazy substitute

(42:12) Taking two paternity leaves and showing up every single day

(50:47) Lightning round: pilot dads, AI video fails, and minivans

Resources From This Episode:

Parento Leave: https://www.parentoleave.com/

Doona: https://www.doona.com/

Medicine Pacifier: https://frida.com/products/medifrida

The Confident Parent: https://www.goodreads.com/en/book/show/28953434-the-confident-parent

Free Range Parenting: https://www.freerangekids.com/

Lilo & Stitch (Film): https://www.imdb.com/title/tt0275847/

The Emperor’s New Groove (Film): https://www.imdb.com/title/tt0120917/

—

Support Startup Dad

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

Matt Fairbanks is the Chief Marketing Officer of the enterprise browser and platform company, Island. He built a highly successful career as a tech executive in Silicon Valley, navigating the demanding, fast-paced culture of the tech industry before making the bold decision to pull up roots and relocate his family to Jackson Hole, Wyoming, for a much-needed reset.

He’s married to Trish, and together they have raised four children and are now proud grandparents. His parenting journey has included walking away from the height of his Silicon Valley career to help his kids thrive, codifying his family values into a living family constitution, navigating a terrifying, cliff-diving car accident that deeply shifted his perspective on gratitude, and learning how to intentionally step back from being a people-pleaser to prioritize what truly matters. We discussed:

• The Silicon Valley exit: What it takes to walk away from a high-powered tech career when you realize the environment is living you, instead of the other way around.
• The Fairbanks Family Rules: The origin story behind codifying six core family values, starting with the non-negotiable rule to "be unoffendable," and how they emerged one dinner table conversation at a time.
• The power of environment: A humbling lesson in child development, how a school system can misjudge a child's potential, and the radical move that completely unlocked his son's academic future.
• The concept of "Type Two Fun": Why introducing kids to challenges that are miserable in the moment but rewarding in retrospect is a vital tool for instilling a lifelong craving for hard work.
• Radical gratitude in a crisis: The terrifying reality of learning your 13-year-old daughter was in a 200-foot cliff-side car crash while you are trapped on a tech business flight, and how a miracle survival reshaped their family perspective.
• Technology as a tool, not the master: Practical frameworks for embracing new tech like AI to advance your family mission without letting your kids become passive passengers to digital screens.

Where to find Matt Fairbanks

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

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 Matt Fairbanks, Chief Marketing Officer at Island

(03:22) When Silicon Valley is living you instead of the other way around

(05:04) The radical decision to shift environments to unlock children’s potential

(07:44) The origin story of the Fairbanks Family Constitution

(08:44) Rule number one: Stopping generational family drama at the dinner table

(11:04) Why trust must be earned every single day

(13:58) Teaching kids how to add value

(19:43) Introducing kids to the magic of "Type Two Fun"

(24:26) Prioritizing the "big rocks" over endless hours

(38:42) Finding radical gratitude in the wake of a family crisis

(45:14) Unpacking marital alignment: Pink tasks, blue tasks, and windshield intimacy

(01:01:38) Lightning round: Dishwasher throwing mechanics, Tupperware software, and super vans  

Resources From This Episode:

Island: https://www.island.io/ 

Roth IRA: https://www.irs.gov/retirement-plans/roth-iras 

The Fun Scale: https://www.rei.com/blog/climb/fun-scale 

Mary Poppins (Film): https://www.imdb.com/title/tt0058331/ 

Argo (Film): https://www.imdb.com/title/tt1024648/ 

Moneyball (Film): https://www.imdb.com/title/tt1210166/ 

The Big Short (Film): https://www.imdb.com/title/tt1596363/ 

—

Support Startup Dad

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

Kevin Maguire is the former Head of Strategy for Consumer Apps at Google and is now the author of The New Fatherhood and creator of the newsletter of the same name, a community read by over 23,000 dads. Before writing the book Kevin  moved his family from the UK to San Francisco and eventually left the Bay Area for Barcelona, where he now lives with his wife, an and their two kids. He's also a coach who works with CEOs and CMOs at companies like Amazon and Netflix on the intersection of career and family.

Together Kevin and his wife have built an intentional, rotating co-parenting structure at home while both pursuing careers outside the traditional nine-to-five. Kevin also runs a direct-action giving fund that covers therapy costs for dads struggling with paternal postpartum depression, something he experienced firsthand after the birth of his son. We discussed:

• Rewriting fatherhood: Why Kevin wrote a book arguing that fatherhood isn't something to endure, but the most enriching, joyful experience of his life.
• Retiring the three Ps: How protect, provide, and preside became outdated anchors, and what replaces them for modern dads raising kids in a different world.
• Managing yourself, not your kids: Why the real work of parenting is closing the gap between the dad you are and the dad you want to be.
• Building a Dadvisory Board: How Kevin coaches dads to find five men they admire, lean on the vulnerability loop, and build courage to ask for help.
• Surviving postpartum depression: Kevin's own descent into numbness after his son was born, and the Google search that finally gave his experience a name.
• Redefining success after Google: Why leaving the Bay Area rat race and moving to Barcelona helped Kevin trade validation for a life built around family.

Where to find Kevin Maguire

• LinkedIn: https://www.linkedin.com/in/kevmaguire/ 
• Instagram: https://www.instagram.com/newfatherhood/
• X: https://x.com/kevmaguire
• Substack: https://www.thenewfatherhood.org/

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 Kevin Maguire, Father-In-Chief at The New Fatherhood
(03:29) Why the work is on you, not your kids
(05:17) The old model: protect, provide, preside, and why it's busted
(10:16) Managing your own feelings when mornings go sideways
(13:35) The Dadvisory Board: treating fatherhood like a career
(18:19) Building deeper friendships: courage and the vulnerability loop
(21:36) Why dads struggle to ask for help
(27:10) Paternal postpartum depression: Kevin's own story
(34:37) Designing a life around family first
(38:21) Work-life "fried egg" instead of work-life balance
(44:09) Managing the mental load and the 80/20 co-parenting rule
(49:39) Three eras of scarcity: money, time, and health
(1:00:07) Shark Vader: using AI to spark kids' imagination
(1:04:51) Lightning round: Yoto players, Home Alone, and minivans

Resources From This Episode:

The New Fatherhood: https://www.newfatherhood.com/

Bluey (TV Series): https://www.imdb.com/title/tt7846844/

Modern Family (TV Series): https://www.imdb.com/title/tt1442437/

The Simpsons (TV Series): https://www.imdb.com/title/tt0096697/

Little House on the Prairie (TV Series): https://www.imdb.com/title/tt0071007/

Waking Up App (Sam Harris): https://www.wakingup.com/

Yoto Player: https://us.yotoplay.com/

Huckleberry App: https://huckleberrycare.com/

Star Wars: Rogue One (Film): https://www.imdb.com/title/tt3748528/

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

Terminator 2: Judgment Day (Film): https://www.imdb.com/title/tt0103064/

Avengers: Endgame (Film): https://www.imdb.com/title/tt4154796/

—

Support Startup Dad

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

Ghazi Masood is the Chief Revenue Officer at Replit, where he leads revenue for one of the fastest growing AI coding platforms in the world. He’s also a father of two teenage boys, a husband of nearly 25 years, and a pilot who spends much of his free time flying on nonprofit humanitarian missions.

I reached out to Ghazi after a LinkedIn post he wrote about why teenagers should spend more time building with AI tools instead of defaulting to traditional summer jobs went viral. The post sparked a big reaction, and in this conversation we unpacked the nuance behind it that the internet doesn’t typically allow. We discussed:

• Work-life integration: Why Ghazi believes rigid boundaries create stress and how he blends work, family, travel, and flying.
• Raising teenagers in the AI era: What young people are building with tools like Replit and why this generation has new opportunities.
• Building as a compounding skill: How AI experimentation helps teens develop technical fluency, creativity, problem solving, and entrepreneurial instincts.
• Preparing kids for an uncertain job market: How Ghazi and his wife are helping their sons balance technology, communication, and human-centered skills.
• Marriage through different seasons: What nearly 25 years of marriage has taught Ghazi about partnership, adaptation, and support.
• Flying as service and meditation: How humanitarian flying helps Ghazi serve others while finding a rare sense of peace.

Where to find Ghazi Masood

• LinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2/ 

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 Ghazi Masood, CRO of Replit
(02:41) Why work-life integration beats balance
(05:56) Why rigid boundaries can create more stress
(09:18) Building a marriage across distance and seasons
(11:48) Preparing for the college launch
(15:59) How parenting shapes leadership
(17:38) What kids are building with AI
(21:40) Guiding kids through an uncertain career path
(24:05) Why teenagers should start building
(27:00) How tech skills compound over time
(28:57) Why communication still wins
(33:42) The AI debate happening inside schools
(38:34) Flying humanitarian missions with Angel Flight West
(46:24) Lightning round: baby swings, teeth in pockets, and no minivans

Resources From This Episode:

Replit: https://replit.com/ 

Angel Flight West: https://angelflightwest.org/ 

University of Washington: https://www.washington.edu/ 

WisprFlow: https://wisprflow.ai/ 

Stripe: https://stripe.com/ 

Khan Academy: https://www.khanacademy.org/ 

Cars (Film): https://www.imdb.com/title/tt0317219/ 

Top Gun (Film): https://www.imdb.com/title/tt0092099/ 

Volkswagen ID. Buzz (Vehicle): 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

Matt Korn is a Partner at Pierson Ferdinand LLP and the founder of Dad, Esquire, an online community dedicated to supporting fatherhood within the legal profession. He built the community after spending years in Big Law, navigating the demanding culture of corporate legal practice while striving to be an emotionally present father to his four children.

He’s married to Haley, and together they are raising four kids; three biological sons and one adopted daughter. His parenting journey has included managing extreme sleep deprivation to build his practice, navigating a powerful wake-up call about work-life balance from his wife, expanding their definition of family through an emergency domestic adoption, and developing a deeply intentional approach to digital screen boundaries. We discussed:

• The isolation of the legal profession: Why law firm culture makes it particularly difficult for dads to build community and why Matt created Dad Esquire to ensure no father navigates law or parenthood alone.  
• The cost of running on empty: How sleep deprivation became Matt's default strategy for balancing Big Law with a big family, and what that reactionary approach ultimately cost him over time.
• A marital crossroads: The exact moment Matt’s wife told him she felt like a single mom, and how that wake-up call forced him to radically renegotiate his career and prioritize his family.  
• Physical presence vs. emotional presence: Humbling lessons on modern parenting, the reality of screen-time guilt, and how to stay truly engaged when your kids are competing for your attention.
• An unexpected adoption journey: The logistical, financial, and emotional realities of their family's short-notice domestic adoption, and what it taught them about bonding and loving unconditionally.  
• Navigating the digital future at home: How Matt thinks about AI and technology as a tool for his kids' future success.

Where to find Matthew Korn

• LinkedIn: https://www.linkedin.com/in/matthewkorn/
• Dad, Esquire: https://dadesq.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 Matt Korn, Partner at Pierson Ferdinand LLP and Founder of Dad, Esquire

(02:28) Raising four distinct personalities from the same DNA 

(03:39) The isolation crisis among lawyer fathers 

(06:22) The physical and mental toll of chronic sleep deprivation 

(09:58) The wake-up call: When your wife feels like a single mom 

(12:48) Inside Dad, Esquire: Why you shouldn't do law or fatherhood alone 

(19:07) The diverse and unexpected members showing up to community gatherings 

(21:46) Finding a safe space for raw, judgment-free dad chat 

(26:59) Expanding the definition of family: The adoption decision 

(35:39) How a baby girl shifted the all-boy pool dynamic 

(36:47) Navigating a finalized home dynamic, foster care questions, and future biology talks 

(42:24) Career pivots, autonomous big law models, and making it home for dinner 

(47:16) True emotional presence versus zoning out on Minecraft stories 

(51:27) Caleb’s shower confrontation: The phone box reality check 

(54:16) Opening up a child’s eyes to the creative endeavor of Claude and ChatGPT 

(01:01:15) Generational shifts in federal parental leave and providing beyond financial means 

(01:04:45) Rewinding the clock to zero-to-one transitions and ignoring conventional advice 

(01:08:55) Lightning round: Desitin, organized dishwashers, and the truth about minivans

Resources From This Episode:

Dad, Esquire: https://dadesq.com/

Dad, Esquire Merch: https://dadesq.square.site/ 

Lead Dad of the Week (Paul Sullivan on Matt Korn): https://thecompanyofdads.com/why-making-a-difference-at-work-and-in-your-community-matters-matthew-korn/ 

Matthew’s Blog Post about Adoption: https://dadesq.substack.com/p/im-pretty-im-smart-im-specialim-madison 

Desitin: https://www.desitin.com/ 

Heavyweights (Film): https://www.imdb.com/title/tt0110006/ 

Like Mike (Film): https://www.imdb.com/title/tt0308506/ 

Moana (2026 Film): https://www.imdb.com/title/tt27419466/ 

The Goonies: https://www.imdb.com/title/tt0089218/ 

Star Wars: The Mandalorian and Grogu (Film): https://www.imdb.com/title/tt30825738/ 

—

Support Startup Dad

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

Zach Jaffe is an M&A professional at Create Music Group, where he focuses on independent record label acquisitions. After years in the LA music industry and startup world, Zach became the first in his friend group to have a child, which meant navigating early fatherhood without much of a roadmap or many people around him who could truly relate.

He’s also a dad to one three-year-old daughter and brings a candid, funny, and deeply thoughtful perspective on parenting, work, attention, and what really matters when life gets chaotic. We discussed:

• The first six months are brutal: Why Zach believes the early stage of parenting is harder than most dads expect and why more honest conversations are needed.
• Being first in your friend group to have kids: How Zach navigated isolation, shifting friendships, and a totally new version of availability.
• Parenting through real emergencies: What Zach learned from driving through a storm with a baby and evacuating during the Pasadena and Altadena fires.
• Parenting with ADHD: The systems Zach uses to manage distraction, hyperfocus, reminders, and the everyday chaos of family life.
• Protecting attention at home: Why Zach is intentional about slow media, screen time, and keeping dopamine loops away from his daughter.
• Parenting makes you better at work: How fatherhood made Zach calmer, more empathetic, and more solution-oriented as a colleague and manager.

Where to find Zach Jaffe

• LinkedIn: https://www.linkedin.com/in/zach-scott-jaffe/ 
• Instagram: https://www.instagram.com/zachscottjaffe/ 

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 Zach Jaffe, Create Music Group
(02:39) The first terrifying moments of becoming a dad
(04:13) Why the first months of parenting are brutally hard
(08:41) Losing your old social life after becoming a parent
(11:41) Building the village before you really need it
(14:10) How fatherhood builds patience and empathy at work
(19:13) Going into survival mode during the LA wildfires
(23:02) Why sleep matters more than startup culture admits
(30:19) Parenting with ADHD and building systems that work
(35:58) Why slow media matters in a fast dopamine world
(40:59) Why Zach keeps AI out of parenting
(42:25) Why creativity needs friction and struggle
(49:31) How parenting makes you better at work
(53:57) Why attention is everything
(01:08:40) Lightning round: butt spatulas, dark clothes, and sensible family cars

Resources From This Episode:

Create Music Group: http://www.createmusicgroup.com 

The Road (Book by Cormac McCarthy): https://www.goodreads.com/book/show/6288.The_Road 

Waking Up (Meditation App): https://www.wakingup.com/ 

Waking Up (Book by Sam Harris): https://www.samharris.org/books/waking-up 

Baby Diaper Spatula: https://a.co/d/04SZjxQc 

The Muppet Show (TV Series): https://www.imdb.com/title/tt0074028/ 

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

Spirited Away (Film): https://www.imdb.com/title/tt0245429/ 

Star Wars (Films): https://www.imdb.com/list/ls070150896/ 

Alien (Film): https://www.imdb.com/title/tt0078748/ 

Top Gun: Maverick (Film): https://www.imdb.com/title/tt1745960/ 

Honda CR-V (Car): https://automobiles.honda.com/cr-v 

—

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