Startup Dad

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 

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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/ 

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

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

Jamie Kaler is a former Naval Officer turned actor, stand-up comedian and stay-at-home dad. He is best known for his role on TBS's "My Boys" and decades of work across television and commercials, from Friends and Will & Grace to How I Met Your Mother and The Family Stone. He spent five years as a U.S. Navy officer before moving to LA at 30 with no connections to pursue acting, eventually becoming one of those guys everyone vaguely recognizes but can't quite place.
He's also the father of two daughters, ages 11 and almost 13. When "My Boys" wrapped and his wife's career took off, Jamie stepped back from the road to become the primary caregiver, cooking, driving, coaching soccer, and homeschooling two kids on iPads for 18 months during the pandemic. That experience became the foundation of his stand-up comeback, his viral Soccer Dad persona on Instagram and TikTok, and a whole new chapter in his career at 60. We discussed:
Becoming a stay-at-home dad at 50: How Jamie walked away from touring after "My Boys" wrapped and became the primary caregiver for two daughters.
Applying military structure to parenting: Why Jamie runs his household like a ship, schedules, reveille at 6:30, and uniforms during pandemic Zoom school.
Going viral as Soccer Dad: How a spontaneous sideline rant at his daughter's first club game launched a brand, a T-shirt army, and a touring stand-up act at 60.
Why sideline parents have lost the plot: Jamie's take on delusional sports parents, the reclassing phenomenon, and why he got red-carded as a coach.
Stand-up as therapy: How Jamie uses comedy to process fatherhood, and why he now asks his daughters' permission before telling stories about them on stage.
Raising kids who can talk to people: Why Jamie runs improv and public speaking drills at home, and why he believes verbal communication will be the most valuable skill of the next generation.

Where to find Jamie Kaler
LinkedIn: https://www.linkedin.com/in/jamie-kaler-b6143452/ 
IG: https://www.instagram.com/jamiekaler/ 
Web: https://jamiekaler.com/ 
Who Needs Podcast: https://jamiekaler.com/who-needs/ 

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 Jamie Kaler, Actor and Standup Comedian
(02:50) Breaking down Jamie's wild resume: Navy, bartender, improv, and Hollywood
(03:07) Why he pivoted from naval officer to stand-up comedy
(09:22) Moving to LA at 30 with no connections to become an actor
(10:13) What his military family thought about leaving the Navy
(11:27) Becoming famous as "that guy you vaguely recognize"
(15:38) Transitioning from red carpets to stay-at-home dad at 50
(20:04) How he became a stay-at-home dad
(24:23) The most lost he's felt as a dad and his "survive and advance" philosophy
(26:54) The origin story of Soccer Dad going viral
(38:16) Why parents on the sidelines are delusional and the re-classing phenomenon
(38:21) Getting red-carded as a coach and the walk of shame
(42:05) What pulled him back to stand-up and touring again
(01:00:33) Rewatching "My Boys" 20 years later what he remembers (nothing)
(01:04:29) Advice for new dads: accept that you don't know everything
(01:08:28) Lightning round: dishwashers, dad wardrobes, minivans, and Full House

Resources From This Episode:

Who Needs (Podcast by Jamie Kaler & Mike Bunin rewatching "My Boys"): https://jamiekaler.com/who-needs/ 
Flappers Comedy Club (Burbank, CA): https://www.flapperscomedy.com/
Punch Line San Francisco: https://www.punchlinecomedyclub.com/
Homeschooled (Album by Jamie Kaler): https://music.apple.com/us/album/homeschooled/1582539985
Bringing Up Bébé (Book by Pamela Druckerman): https://www.amazon.com/Bringing-Up-Bebe-Pamela-Druckerman/dp/0143122967
Dad Is Fat (Book by Jim Gaffigan): https://www.amazon.com/Dad-Is-Fat-Jim-Gaffigan/dp/1451669747
My Boys (TBS Series): https://www.imdb.com/title/tt0758745/
The Family Stone (Film): https://www.imdb.com/title/tt0356618/
Full House (Series): https://www.imdb.com/title/tt0092359/
American Housewife (Series): https://www.imdb.com/title/tt5578850/
Tacoma FD (Series): https://www.imdb.com/title/tt8242858/
Robot Chicken (Series): https://www.imdb.com/title/tt0437745/
The Loud House (Series): https://www.imdb.com/title/tt4847782/
Olukai Slippers: https://www.olukai.com/

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

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor gear brand built around fighting poverty and doing good in the world. Before stepping back as CEO after a decade of leading the company, Davis grew Cotopaxi at 85% CAGR into one of the most purpose-driven brands in the outdoor industry. He left and moved with his wife and four kids to be a mission president for his church in Brazil, leading nearly 500 young missionaries from 24 countries over three years.
He's a dad of four, married to his wife who studied family science and served as a court-appointed special advocate for foster children, and together they've raised their kids across Latin America, Brazil, and the United States with a family culture built around service, faith, intellect, travel, and hard work. We discussed:
Leaving a dream job to serve others: Why Davis walked away from the CEO role at Cotopaxi at the peak of its growth to lead 500 young missionaries in Brazil for three years.
Building intentional family culture: How Davis and his wife created five core values tied to the letters S-M-I-T-H, complete with rituals, traditions, and a weekly family meeting.
Values as a compass, not a club: Why family values should guide behavior rather than be used as a weapon when kids fall short.
Unconditional positive regard: How loving your kids and missionaries no matter what gets better results than demands, disappointment, or conditional approval.
Raising kids with financial discipline: The Bank of Smith Savings, the 50/40/10 rule, and why Davis matches whatever his kids save by age 16 for a car.
Letting kids go through hard things: What Davis learned watching his daughter struggle through a mission in the Philippines and why he believes difficulty is essential for growth.

Where to find Davis Smith
LinkedIn: https://www.linkedin.com/in/davismsmith/ 

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 Davis Smith, Founder & Chairman at Cotopaxi
(02:37) Why Davis walked away from his dream job as CEO
(05:12) Moving the whole family to Brazil for three years
(07:23) What almost broke him in the first year
(09:36) Why stepping away from comfort at a young age is transformative
(13:53) Survival trips with his daughters and the origin story
(16:18) How Davis built intentional family culture at home
(21:03) Breaking down the SMITH family values
(24:08) Unconditional positive regard and how to lead with love
(28:19) The Bank of Smith Savings and the 50/40/10 rule
(32:06) The most surprising things he's discovered as a dad
(33:32) What the teen years and adult kids have taught him
(38:59) Advice for parents who are building companies
(41:04) Frog Mouse bedtime stories and using AI as a dad
(43:18) Lightning round: smoothies, Back to the Future, and minivans

Resources From This Episode:

Cotopaxi: https://www.cotopaxi.com/
H2O: Just Add Water (TV Series): https://www.imdb.com/title/tt0814976/
Back to the Future (Film): https://www.imdb.com/title/tt0088763/
Peace Corps: https://www.peacecorps.gov/
Brigham Young University (BYU): https://www.byu.edu/

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