Startup Dad

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