Startup Dad

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

Matt Pasternack is the co-founder and CEO of Once, a science of reading-based software that teaches children ages three to seven how to read. He built the company after watching his wife teach their daughter to read in just 15 minutes a day during the pandemic, and realizing every parent could do the same.
He's also a father of three, with kids ages six, eight, and ten. His parenting journey has included launching a startup while raising young children alongside his wife Becca, an OB-GYN, navigating the demands of her residency with a newborn at home, and developing a deeply intentional approach to raising independent, curious kids. We discussed:
Building a reading company as a parent: How Matt launched Once during the pandemic while homeschooling his daughter and became his own proof of concept.
Fixing a broken system from the inside: How years of classroom teaching shaped Matt's belief that schools alone can't solve the reading crisis.
Keeping startup stress in perspective: Why Matt believes that teaching a child to read matters more than any company milestone he'll ever hit.
Taking an evidence-based approach at home: How Matt and his wife Becca stay aligned on parenting decisions, from sleep training to screen limits to raising independent kids.
Letting kids own their own lives: Why Matt believes in giving children real responsibility early, from making their own lunches to managing their own social calendars.
Choosing books over screens in a distracted world: Why Matt limits devices, teaches reading as a daily ritual, and believes literacy is the greatest gift of independence a parent can give.

Where to find Matt Pasternack
LinkedIn: https://www.linkedin.com/in/mattpasternack/ 
X: https://x.com/mattpasternack
Web: https://tryonce.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 Pasternack, Co-founder/CEO of Once
(02:17) What Once is and how it teaches kids to read
(03:00) Is having a doctor spouse a blessing or a curse
(04:14) The three parenting books every new parent needs
(04:49) The Happiest Baby on the Block and the five S’s
(05:31) The Good Sleeper and teaching babies to sleep
(06:10) Oh Crap Potty Training and the one-day method
(08:02) Raising autonomous kids and the Montessori mindset
(12:45) Why where you live is your biggest parenting decision
(18:31) What is the science of reading
(25:46) Why every parent can teach their child to read
(34:00) The US reading crisis and why it hasn’t moved in 50 years
(49:30) Advice for founders starting a family
(52:16) Finding the screen time sweet spot for kids
(01:02:57) Lightning round: diapers, the SNOO, and Magic Tree House
Resources From This Episode:
Once (Reading App): https://tryonce.com/
The Happiest Baby on the Block (Book/Video): https://www.happiestbaby.com/blogs/baby/happiest-baby-on-the-block
The Good Sleeper (Book): https://www.amazon.com/Good-Sleeper-Essential-Guide-Healthy/dp/0761177582
Oh Crap! Potty Training (Book): https://www.amazon.com/Oh-Crap-Potty-Training-Everything/dp/1501122983
SNOO Smart Bassinet: https://www.happiestbaby.com/products/snoo-smart-bassinet
Tin Can Phone (Toy): https://tincan.kids/ 
Tin Can Founder on Startup Dad: https://www.youtube.com/watch?v=7MmdPkMhqe8
Skylight Calendar: https://www.skylightframe.com/
Sold a Story (Podcast): https://features.apmreports.org/sold-a-story/
The Magic Tree House (Book Series): https://www.magictreehouse.com/
Ramona (Book Series): https://www.amazon.com/Ramona-Complete-Collection-Beverly-Cleary/dp/0062228641
Batteries Not Included (Film): https://www.imdb.com/title/tt0092494/

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