Startup Dad

Nate Quigley is the co-founder of Chatbooks, the photo book company that helps families preserve their memories from Instagram photos. He started the company after a wave of nostalgia hit as his oldest child approached leaving home, only to spend years building a product nobody wanted. Then his wife Vanessa stepped in, suggested they simply print Instagram, and became the accidental co-founder who helped turn the company around.
He’s also a father of seven, a grandfather of two, and officially the first Startup Dad guest to also be a Startup Granddad. Nate brings a rare perspective on what it means to build a company while raising a big family and then watching those kids grow into adults with lives of their own. He shares how parenting has taught him to release control, stay curious, and create family rituals that give kids a place to come back to. We discussed:
Co-founding with your spouse: How Vanessa’s intervention saved Chatbooks and what it’s been like building a company together for more than a decade.
Treating the company like a family farm: Farm families don't talk about work-life balance because work and life are the same thing.
Parenting seven very different kids: How Nate’s approach changed from child one to child seven and why one parenting playbook never works for every child.
Learning to let go: Why Nate believes the hardest parts of parenting and leadership come from guiding people without trying to control every outcome.
Creating family rituals that stick: The traditions that helped Nate keep a household of nine connected.
Helping kids navigate technology: How Nate thinks about phones, social media, AI, and using tools that create better conversations instead of just tighter controls.

Where to find Nate Quigley
LinkedIn: https://www.linkedin.com/in/natequigley/ 

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 Nate Quigley, Co-Founder and CEO of Chatbooks
(02:23) Raising seven kids and becoming an empty nester
(04:13) How Vanessa became the accidental co-founder
(05:39) The simple pivot that saved Chatbooks
(10:05) Treating the startup like the family farm
(12:47) How parenting changed from kid one to kid seven
(14:39) Learning to let go as a dad and leader
(17:36) Birding, curiosity, and observing your kids
(21:51) Advice for founders who want to become dads
(25:06) Family night and the Quigley Creed
(28:50) Creating family rituals that actually stick
(30:53) The 15-year-old adventure tradition
(32:53) Why letting kids grow up is so hard
(37:01) Parenting through phones, social media, and screen time
(48:15) Lightning round: fly fishing, minivans, and dishwasher rules
Resources From This Episode:
Chatbooks: https://chatbooks.com/ 
Chatbooks’ Instagram: https://www.instagram.com/chatbooks/ 
Bark: https://www.bark.us/ 
Analog: https://goanalog.co/ 
Brick: https://getbrick.com/   
A River Runs Through It (Film): https://www.imdb.com/title/tt0105265/

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Gabe Larsen is the CRO of Atonom, an AI company building always-on AI agents. He has spent his career leading go-to-market teams at high-growth companies, including Kustomer, Meta, and InsideSales.com.

He’s also a father of five boys, ranging from six months to 14 years old, along with his wife Carolyn. In this conversation, Gabe shares why he believes fatherhood doesn’t slow down ambition, it sharpens it. We talked about how raising kids has made him more focused, more empathetic, and more direct as a leader, and why the same skills that matter at home -  prioritization, hard conversations, and presence - show up every day at work. We discussed:
Fatherhood as leadership training: Why Gabe believes becoming a Dad can make you more focused, empathetic, and effective at work.
Kids expose wasted motion fast: How parenting forced Gabe to cut through busy work and get clearer about what actually matters.
Building a family operating system: The family mission, values, and quarterly goals Gabe uses to help his five boys grow.
Monthly one-on-ones with each son: Why Gabe creates structured time for hard conversations, check-ins, and connections.
Work-life integration: How Gabe thinks about ambition, presence, travel, marriage, and making the moments at home count.
Raising AI-native kids: Why Gabe is cautious about phones and social media, but wants his kids to learn how to use AI productively.

Where to find Gabe Larsen
LinkedIn: https://www.linkedin.com/in/gabelarsen/ 

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 Gabe Larsen, CRO of Atonom
(02:37) Why kids can make you a better leader
(03:48) How family sharpens ambition and focus
(04:57) The brief, mission, debrief rhythm
(06:23) Why kids expose wasted motion fast
(07:43) Building a family mission and quarterly goals
(10:29) Having hard conversations at home and at work
(14:17) How fatherhood shifted Gabe’s emotional center
(16:53) Letting go of balance and finding integration
(19:54) Gabe’s advice for founder parents
(22:17) How Gabe and Carolyn made a career shift work
(28:04) Marriage, pressure, and playing to your strengths
(31:30) Choosing presence when your phone pulls you away
(43:07) Lightning round with binkies, dad robes, Dora, and minivans
Resources From This Episode:
Atonom: https://atonom.ai/ 
Dora The Explorer (TV Series): https://www.imdb.com/title/tt0235917/ 
The Karate Kid (Film): https://www.imdb.com/title/tt0087538/
Back To The Future (Film): https://www.imdb.com/title/tt0088763/ 
Remember The Titans (Film): https://www.imdb.com/title/tt0210945/ 

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

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