Startup Dad

Jonathan Stull is the President and COO of Handshake, the career platform connecting students and recent grads with employers that recently made a massive pivot into scaling an AI product. He’s spent the last decade helping build the company from a seed stage startup working out of a house in Palo Alto into a massive platform serving millions of students, universities, and employers.
He’s also a husband to Emmy-winning journalist Emily Chang and a dad of four kids, ages 13, 11, 9, and 6. At home, he’s juggling the beautiful chaos of school drop-offs, carpools, Little League, robotics, math enrichment, ski trips, and four very different schedules. In our conversation, we talked about how Jonathan and Emily rely on their nanny, grandparents, neighbors, and community to make it all work, the challenge of being present when work is still running in the background, why kids need agency and resilience more than ever, and how becoming a dad has made him a more direct and caring leader. We discussed:
Building a life with four kids: How Jonathan and his wife manage the beautiful chaos of school, sports, activities, and constant logistics.
Relying on your village: Why their nanny, grandparents, carpools, neighbors, and community are essential to making family life work.
Staying present when startup life is intense: The challenge of being physically at a kid’s game while mentally pulled into Slack, AI agents, and company decisions.
Raising kids with agency in the AI era: Why Jonathan believes resilience, adaptability, self-starting, and passion matter more than ever.
Parenting through direct feedback: How being a dad helped Jonathan become a clearer, more direct, and more caring leader at work.
Embracing adventure before the years disappear: Why Jonathan tries to say yes to family trips, backyard games, and small moments of connection.

Where to find Jonathan Stull
LinkedIn: https://www.linkedin.com/in/jonstull/ 

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcome Jonathan Stull, President and COO of Handshake (and baseball coach)
(02:14) Why Jonathan and Emily decided to have four kids
(03:53) Managing the beautiful chaos of four schedules
(05:51) Building the village that keeps family life moving
(09:46) The first moment fatherhood really hit
(10:42) Growing Handshake while learning to stay present at home
(16:25) Why parents should not wait for the perfect time
(19:36) What kids teach you about resilience
(22:11) Showing up, saying yes, and protecting family time
(24:35) How parenting made Jonathan a more direct leader
(27:09) Navigating enrichment, ambition, and different parenting instincts
(30:00) Raising kids to be ready for an AI shaped future
(31:20) Why agency matters more than following a playbook
(34:10) Using AI to plan trips, pranks, and Little League schedules
(39:12) Lightning round: white noise, limericks, dad pranks, and minivans

Resources From This Episode:
Handshake: https://joinhandshake.com/ 
SNOO Smart Sleeper Bassinet: https://www.happiestbaby.com/products/snoo-smart-bassinet 
Bluey (TV Series): https://www.imdb.com/title/tt7678620/ 
The Lion King (Film): https://www.imdb.com/title/tt0110357/
Billy Madison (Film): https://www.imdb.com/title/tt0112508/ 
Braveheart (Film): https://www.imdb.com/title/tt0112573/ 
Glory (Film): https://www.imdb.com/title/tt0097441/ 
Anchorman: The Legend of Ron Burgundy (Film): https://www.imdb.com/title/tt0357413/ 
Old School (Film): https://www.imdb.com/title/tt0302886/
Wedding Crashers (Film): https://www.imdb.com/title/tt0396269/ 
Chevrolet Suburban (Car): https://www.chevrolet.com/suvs/suburban 
Chrysler Pacifica (Car): https://www.chrysler.com/pacifica.html 

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

Ashish Kundra is the CEO of Conceptual, a growth agency that helps companies like Cursor, Perplexity, Superhuman, Fenty Beauty, GPTZero, and dozens more. Prior to that, he led growth at DuckDuckGo and founded two other companies.

He’s also a husband and the father of a four-year-old son. In this episode, Ashish shares why starting a company when his son was one made sense for his family, how being married to a pediatrician shapes their parenting, and why he believes small falls prevent big falls. We discussed:
Being married to a pediatrician and how that shapes parenting: Why Ashish sees it as a major advantage in handling health, nutrition, and everyday parenting decisions.
Starting a company when his son was one: Why Ashish felt that early parenthood was still the right time to build something of his own.
Avoiding over-parenting: How he gives his son more agency and lets natural consequences do some of the teaching.
Why small falls prevent big falls: How Ashish thinks about struggle, discomfort, and building resilience early.
Tracking happiness and contentment: Why he journals regularly and what he’s learned about sleep, exercise, and stress.
Why your child is not your trophy: How he thinks about ambition, identity, and raising a son without ego.

Where to find Ashish Kundra
LinkedIn: https://www.linkedin.com/in/ashish-kundra-5a9b784/ 
X: https://x.com/akundra 

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcome Ashish Kundra, CEO of Conceptual
(02:57) What it is really like being married to a pediatrician
(05:15) Nutrition, hydration, and diet hacks that actually help
(08:31) Why he started a company when his son was a baby
(12:38) Avoiding over-parenting and giving kids more agency
(16:41) Why small falls can prevent bigger ones later
(20:01) Tracking happiness, sleep, and stress in real time
(24:13) The weekly one-on-one that keeps their marriage aligned
(25:47) How he and his wife divide life at home
(27:44) Grandparents, family planning, and designing life on purpose
(29:34) Embracing imperfection as a parent and partner
(31:15) Raising a kid without turning him into a trophy
(34:33) The mistake he wishes he could redo as a dad
(35:53) Navigating startup pressure and family time
(37:59) Lightning round: strollers, quesadillas, Cocomelon, and minivans

Resources From This Episode:
Conceptual: https://conceptualhq.com/ 
Baby stroller: https://a.co/d/0aRvEiDH 
The Sound of Music (Film): https://www.imdb.com/title/tt0059742/ 
The Lion King (Film): https://www.imdb.com/title/tt0110357/
Mrs. Doubtfire (Film): https://www.imdb.com/title/tt0107614/ 

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

Robert Whitney is the Co-Founder and CTO of Hapiko, the company that invented Stickerbox, an AI powered product helping kids create and play in more imaginative ways. Before starting Stickerbox, he helped scale New York Times Games, Grailed  and spent time at Anthropic thinking deeply about the future of AI and how it will shape the next generation.
He’s also a co-parent to a four-and-a-half-year-old son in New York City. In this conversation, Robert shares how fatherhood changed the way he approaches work, decision-making, discipline, and presence. We also talk about co-parenting as a founder, his shift away from a hard-partying New York lifestyle, the parenting principles he’s developed, and why he believes most AI products are failing kids. We discussed:
Why parenting is the ultimate life experience: How becoming a dad made Robert more grounded and less reactive.
Co-parenting while building a startup: What it looks like to split time as a founder and a parent, and how Robert thinks about being fully present in each mode.
Leaving behind a hard-partying New York lifestyle: Why Robert made a major life change years before becoming a dad, and how sobriety reshaped his priorities, energy, and sense of self.
How loss changed his perspective on fatherhood: What losing his mom shortly after becoming a parent taught him about time and presence.
What most AI products get wrong for kids: Why Robert believes kids need safer, simpler, more thoughtful tools.
How Stickerbox started with his son: The rainy-day moment that turned into a company built around play and creativity.

Where to find Robert Whitney
LinkedIn: https://www.linkedin.com/in/robertjwhitney/ 
Instagram: https://www.instagram.com/robertjwhitney/

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Robert Whitney, Co-Founder/CTO of Stickerbox
(02:12) Why parenting is the ultimate life experience
(06:11) Co-parenting while building a startup
(09:46) Leaving behind his hard-partying New York lifestyle
(13:56) The career shift that forced deeper self-reflection
(16:09) Losing his mom and learning to value presence
(18:18) Why he got pulled into AI for kids
(22:13) The biggest AI risks facing children
(27:16) Why safety matters more than being on the bleeding edge
(32:20) Parenting principles that help him let most things go
(34:38) Why he makes his son help with everything
(38:27) Why slowing down and sleeping on things matters
(43:07) Why discipline matters more than motivation
(48:12) How Stickerbox was created with his son
(52:58) Lightning round: Yoto wins, bowling obsession, and manual minivans

Resources From This Episode:
Stickerbox: https://stickerbox.com/ 
Hapiko: https://hapiko.com/ 
Yoto: https://www.yotoplay.com/ 
Moana (Film): https://www.imdb.com/title/tt3521164/
My Neighbor Totoro (Film): https://www.imdb.com/title/tt0096283/ 
Dodge Caravan (Car): https://www.dodge.com/grand-caravan.html
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Support Startup Dad
For sponsorship inquiries, email: [email protected]
For Startup Dad Merch: www.startupdadshop.com

Caleb Avery is the Founder and CEO of Tilled. He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey.

In this episode, Caleb shares what it really looks like to build a startup and a family at the same time. We talk about the trade-offs founders need to be honest about, his regrets around paternity leave with his first child, and why bedtime became his most important non-negotiable as a dad.

We also get into the little-discussed challenge of making parent friends, what coaching his son’s T-ball team taught him, how he and his wife think about screen time and technology, and why he believes work-life balance is less useful than clear boundaries. We discussed:
Starting a company while raising young kids: How Caleb thought about the trade-offs of building a startup and growing a family at the same time.
Paternity leave regrets and what changed: Why Caleb still thinks about working from the hospital after his first child was born, and what changed with his second child.
Why bedtime is his top parenting priority: How Caleb built his schedule around being home for bedtime and why it became his most important non-negotiable as a dad.
Boundaries over balance: Why Caleb does not chase perfect work-life balance and focuses on a few clear non-negotiables instead.
The little-discussed challenge of making parent friends: Why it is so hard to find families where both the kids and the parents actually click.
Honest advice for founders thinking about kids: Caleb explains why aspiring startup parents need to be brutally honest about the trade-offs before signing up for both.

Where to find Caleb Avery
LinkedIn: https://www.linkedin.com/in/caleb-avery/ 

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcoming Caleb Avery, Founder/CEO of Tilled
(02:50) Starting Tilled while raising young kids
(05:12) The time and energy trade-offs of startups and parenting
(07:53) Paternity leave regrets after his first child
(10:53) How COVID unexpectedly gave him the leave he wanted
(14:19) Why it is so hard to make parent friends
(17:43) What fatherhood taught Caleb about nature versus nurture
(19:19) Becoming an accidental T-ball coach
(28:03) His advice to founders thinking about having kids
(30:23) How becoming a dad made him a better CEO
(32:22) Why bedtime is Caleb’s top parenting priority
(35:04) Family time boundaries and being fully present
(37:41) Redefining work-life balance as a startup dad
(40:36) Kids, iPads, and setting screen time boundaries
(48:15) Lightning round: Snoo wins, dishwasher rules, and a toy assembly nightmare

Resources From This Episode:
Tilled: https://www.tilled.com/ 
The Snoo: https://www.happiestbaby.com/products/snoo-smart-bassinet 
The Sandlot (Film): https://www.imdb.com/title/tt0108037/
Diehard (Film): https://www.imdb.com/title/tt0095016/ 
Golf Cart for Kids: https://a.co/d/0hVZwx85 
iPad: https://www.apple.com/ph/ipad/ 
Lincoln Navigator (Car): https://www.lincoln.com/luxury-suvs/navigator/ 
—
Support Startup Dad
For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Sam Yagan is the founder of OKCupid and former CEO of Match Group. He’s also an investor, board member, married to a CEO, and a dad of three kids ages 12 to 18.

In this episode, Sam shares how he and his wife think about raising kind, grounded kids while navigating success, wealth, and ambition. We talk about family values, philanthropy, work-life integration, the pressure kids can feel from high-achieving parents, and why Sam believes “normal” is overrated.

We also get into the systems that shape their household, from weekly family meetings and value shout-outs to annual family reviews and intentionally making their home the place where all the kids want to hang out. We discussed: 
Raising grounded kids in a high-achievement household: How Sam and his wife work to keep their kids kind, self-aware, and unentitled despite growing up around success and wealth.
Building family values into everyday life: How Sam’s family uses weekly meetings, value shout-outs, and annual reviews to make generosity, kindness, and self-awareness part of daily life.
Introducing philanthropy before personal wealth: Why Sam wants his kids’ first understanding of money to center on giving, impact, and responsibility.
Choosing the right partner for the long game: Why Sam believes ambitious founders need a spouse who shares their values and vision for family life.
Creating a home that pulls people in: How Sam and his wife built a family environment where kids and friends naturally gather, creating more connection and shared memories.
Bringing a founder mindset into parenting: Why Sam believes decisiveness, experimentation, flexibility, and comfort with failure matter at home too.

Where to find Sam Yagan
LinkedIn: https://www.linkedin.com/in/samyagan/
X: https://x.com/samyagan

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com 
LinkedIn: https://www.linkedin.com/in/adamjfishman/ 
Instagram: https://www.instagram.com/startupdadpod/ 
X: https://x.com/fishmanaf

In this episode, we cover:
(00:00) Welcome Sam Yagan, Former Founder/CEO of OKCupid & Match Group
(02:44) Raising kind kids in a world of privilege
(04:59) Family values meetings that actually work
(06:23) When your kids start asking about net worth
(12:10) Why philanthropy comes before wealth
(14:57) Work-life integration during the startup years
(18:29) The tradeoffs that come with constant travel
(20:59) The pressure kids feel from successful parents
(22:27) Teaching a “fail forward” mindset at home
(26:58) Why normal is boring
(29:24) Why choosing the right partner matters
(32:53) Putting your family values on the wall
(36:27) The annual family review
(38:47) Making your home the hangout house
(48:01) Lightning round: Parenting products, dishwasher rules, and Sam’s hard no on minivans

Resources From This Episode:
OKCupid: https://www.okcupid.com/ 
Match Group: https://mtch.com/ 
Playing cards: https://a.co/d/05A9UUbF
Basketball: https://a.co/d/0erx9ow0 
Harry Potter and the Sorcerer's Stone (Film): https://www.imdb.com/title/tt0241527/ 
A Few Good Men (Film): https://www.imdb.com/title/tt0104257/ 
Toyota Highlander (Car): https://www.toyota.com/highlander/ 
—
Support Startup Dad
For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com