Startup Dad

Walter Velazquez Taboada is a consultant and former operations leader at Winning by Design, where he helps executive teams navigate complex decisions and organizational change. Originally from Cuba, Walter has lived across Spain, Mexico, and China, bringing a global perspective to both work and family life.

He’s also a father of two, navigating parenting with an 8-year-old daughter and a seven-month-old son while balancing differing parenting styles, cultural perspectives, and the realities of modern technology. We discussed:
Parenting without a playbook: Why Walter and his wife skipped the parenting books and learned by adapting in real time instead of following rigid frameworks.
Having kids eight years apart: How becoming a dad again later in life completely changed Walter’s perspective on stress, presence, and enjoying the newborn stage.
Letting kids find their own path: Why Walter believes children aren’t blank canvases and how he tries to guide his daughter without forcing his own ambitions onto her.
Using FBI negotiation tactics in parenting: How Chris Voss’ “Black Swan” framework helped Walter uncover what his daughter was really feeling.
Navigating parenting disagreements with your partner: How Walter and his wife work through different views on screen time, hygiene, and risk tolerance.
Helping kids navigate technology and AI: Why Walter is delaying full internet access and thinking carefully about screens, AI, and digital habits.
Where to find Walter Velazquez Taboada
LinkedIn: https://www.linkedin.com/in/walter-velazquez-taboada-87244529 
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 Walter Velazquez Taboada, Architect at Winning by Design
(02:32) The Disney rollercoaster story that traumatized his daughter
(04:56) Growing up across Cuba, Spain, and Mexico
(07:32) Starting a family young and figuring it out as they went
(08:33) Having kids eight years apart changes everything
(13:44) Parenting without a playbook or parenting books
(17:31) Screen time, hygiene, and parenting disagreements
(19:43) Why Walter doesn’t believe in a perfectly unified parenting front
(22:53) The crocodile soccer ball rescue mission
(27:50) Why kids mirror everything their parents do
(30:28) Letting kids find their own path in life
(35:55) Using FBI negotiation tactics to understand his daughter
(41:42) How fatherhood changed Walter’s leadership style
(46:30) Helping kids navigate screens, AI, and the digital world
(53:55) Lightning round: diaper genies, minivans, and terrifying Halloween costumes
Resources From This Episode:

Winning by Design: https://winningbydesign.com/ 
Never Split the Difference (Book by Chris Voss): https://a.co/d/0hv2cKv1 
Diaper Genie: https://diapergenie.com/ 
Inside Out (Film): https://www.imdb.com/title/tt2096673/ 
Alien: https://www.imdb.com/title/tt0078748/ 
Charlie And The Chocolate Factory (Book): https://a.co/d/0iZ25Y78 
Willy Wonka & the Chocolate Factory (1971) (Film): https://www.imdb.com/title/tt0067992/ 
Charlie And The Chocolate Factory (2005) (Film): https://www.imdb.com/title/tt0367594/ 
Wonka (2023) (Film): https://www.imdb.com/title/tt6166392/ 
Electric Screwdriver: https://a.co/d/0881w1k7 

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

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