Startup Dad

• This Dad Makes Moms Cry (In a Good Way) | Chet Kittleson (Dad of 3, TinCan)

  In this episode of Startup Dad, Adam Fishman sits down with Chet Kittleson, serial founder and co-founder of Tin Can, an analog phone for kids that helps families stay connected without screens. He’s also a dad of three, building a hardware company from his kitchen table while raising a young family in Seattle.Chet opens up about the inspiration behind Tin Can, how his childhood landline shaped the idea, and why he believes kids need more analog connections in a digital world. He talks candidly about the challenge of being “distracted dad” while building something he’s intensely passionate about, how he and his wife run their household like a startup, and why learning to unplug is still a daily work in progress. We discussed: Creating balance at home: The systems, boundaries, and frameworks that help Chet stay grounded as a founder and father.Lessons from failure and obsession: What Chet’s learned about being present when work and family both demand everything.The art of analog parenting: How Chet and his wife teach their kids healthy relationships with technology and boredom.Raising kids is like running a business: From household “OKRs” to making space for unstructured family time.Hope for the next generation: Why Chet believes we’re entering an analog revival and what it means for parents raising digital natives.Where to find Chet Kittleson:LinkedIn: https://www.linkedin.com/in/ckittleson/ Instagram: https://www.instagram.com/tincan.kids/Tin Can: https://tincan.kids/  Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ X: https://x.com/fishmanafInstagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Introducing Chet Kittleson(02:31) The childhood inspiration that sparked the idea for Tin Can(11:13) Finding balance between family life and startup life(13:38) Lessons learned from building, failing, and trying again(16:21) Partnering in parenting and business with his wife(21:34) Building Tin Can from an idea to a real product(35:22) How parenting priorities shift as kids grow(36:16) What team dynamics look like inside a family-led startup(37:14) Early prototypes and how the family helped shape Tin Can(38:50) Seeing kids’ real reactions to the analog phone(40:02) Teaching kids to balance tech time and real-world connection(46:38) Finding optimism and practical solutions for modern parenting challenges(50:11) How to support Tin Can’s mission to connect families(53:10) Lightning round: paper calendars, dad hacks, and dishwasher rulesResources From This Episode:Tin Can: https://tincan.kids/ Paper calendar: https://a.co/d/dbPXEsG Brooks: https://www.brooksrunning.com/ The Anxious Generation (book): https://www.anxiousgeneration.com/ Brick (app): https://getbrick.app/ The Hundred-Foot Journey: https://www.imdb.com/title/tt2980648/ Chef: https://www.imdb.com/title/tt2883512/ Toy Story: https://www.imdb.com/title/tt0114709/ The Mighty Ducks: https://www.imdb.com/title/tt0104868/ Honey, I Shrunk the Kids: https://www.imdb.com/title/tt0097523/ Freaky Friday: https://www.imdb.com/title/tt0322330/ Freakier Friday: https://www.imdb.com/title/tt31956415/ The Parent Trap: https://www.imdb.com/title/tt0120783/ Little Big League: https://www.imdb.com/title/tt0110363/ Rookie of the Year: https://www.imdb.com/title/tt0107985/ The Green Mile: https://www.imdb.com/title/tt0120689/ Rewind & Play: ABC The Millennial Way (book): https://a.co/d/6GI6tdC Tween Magazine: https://tweenmag.com/ —For sponsorship inquiries, email: [email protected] Startup Dad Merch: www.startupdadshop.com

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• Why No Dad Has It All Figured Out | Colin Anawaty (Dad of 2, Flying A Capital)

  In this episode of Startup Dad, Adam Fishman sits down with Colin Anawaty, technologist and founder of Flying A Capital. He’s also a single dad of two boys, navigating the challenges of fatherhood and entrepreneurship after divorce.Colin opens up about how his kids have become his greatest teachers, why he believes accountability and independence should start young, and how joining a men’s group helped him prioritize relationships, including the one with himself. From Montessori principles to Mario Kart lessons, Colin shares how parenting frameworks and founder mindsets overlap in surprising ways. We discussed: Parenting through divorce: What it’s like to reset life as a single dad and how his kids’ resilience has inspired him.Learning from mistakes: How modeling vulnerability and apologizing to his kids has built trust and maturity.Resilience vs fragility: Why Colin believes kids are more robust than we give them credit for.Why no dad has it all figured out: Colin’s honest take on navigating career, parenting, and personal growth.The role of technology and AI: From skepticism to playful experiments, turning kids’ crayon drawings into Pixar-style characters.Where to find Colin Anawaty:LinkedIn: https://www.linkedin.com/in/colinanawaty/ X: https://x.com/colinInstagram: https://www.instagram.com/colinanawaty/Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ X: https://x.com/fishmanafInstagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Introducing Colin Anawaty(02:13) Adjusting to life as a single dad of two young boys(05:37) Why Colin joined a men’s group and what he learned(09:43) Taking stock of good and bad parenting lessons from past generations(11:49) Kids as teachers and the power of apologizing as a dad(14:31) Why kids are more resilient than we think(16:29) Teaching accountability at an early age(20:22) Montessori principles at home: independence, structure, fewer toys(23:50) Parenting lessons from Mario Kart and screen time boundaries(28:22) Bonding through haircut sessions with his boys(31:27) Helping his 6-year-old overcome fear of surfing(33:51) Social media dangers for kids and for parents(37:43) What relationship Colin wants his kids to have with technology(40:54) Using AI for parenting frameworks and creative projects(46:17) Why no dad has it all figured out(49:10) Lightning round: Parenting gear, funniest moments, and dad quirksResources From This Episode:5 Types of Wealth by Sahil Bloom: https://a.co/d/0H7Evju The Big Book of Silly Jokes for Kids: https://a.co/d/12730G0 The Expectant Father: The Ultimate Guide for Dads-to-Be: https://a.co/d/ji8u48g The New Father: A Dad's Guide to the First Year: https://a.co/d/chjTYyA Montessori Method: https://montessori.org/ Dad Jokes Instagram (Logan Lisle): https://www.instagram.com/loganlisle/ Potty Training Seat: https://a.co/d/54kwn6oLEGO: https://www.lego.com/ The Karate Kid: https://www.imdb.com/title/tt0087538/ Endless Summer: https://www.imdb.com/title/tt0060371/ Swiss Family Robinson: https://www.imdb.com/title/tt0054357/ Cars: https://www.imdb.com/title/tt0317219/ The Grinch: https://www.imdb.com/title/tt2709692/ Inside Out: https://www.imdb.com/title/tt2096673/ Indiana Jones and the Temple of Doom: https://www.imdb.com/title/tt0087469/ Nintendo Switch: https://www.nintendo.com/switch/ Duke Nukem: https://2k.com/games/duke-nukem/20th-anniversary/ Super Mario Bros: https://mario.nintendo.com/characters/ Mario Kart: https://mariokart8.nintendo.com/ Milo and Chip: https://www.youtube.com/@miloandchip/videos Athena Health: https://www.athenahealth.com/Alex’s Episode: https://www.youtube.com/watch?v=OOa9mS-CIuQJosh Jones-Dilworth & Culturati: https://culturati.info/—For sponsorship inquiries, email: [email protected] Startup Dad Merch: www.startupdadshop.com

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• Why Screen Time Limits Are Bullshit | Chad Pytel (Dad of 2, thoughtbot)

  Chad Pytel is the founder and CEO of thoughtbot, a product development consultancy, and co-founder of 12 Sided Studios, a gaming and production company. He’s also the longtime host of the Giant Robots Smashing Into Other Giant Robots podcast, a husband, and the father of two teenagers.In this episode, Chad and I talk about raising kids while running companies, blending family life with creative projects, and the importance of designing systems at home, just as you would at work. He shares stories about parenting teenagers, shaping company culture around sustainable pace, and why even the smallest rituals matter when time with your kids feels fleeting. We discussed:Building systems at home: How collaborating with his kids on routines turned daily battles into shared ownership.Parenting teenagers with balance: Why being relaxed, supportive, and flexible helped his kids thrive through responsibility and independence.Dinner as a cornerstone: The daily ritual that kept his family connected through the busiest startup years.Redefining company culture: How Thoughtbot built practices like sustainable pace and four-day client weeks to make room for life outside of work.Embracing differences: The importance of parenting each child as an individual, not a template, and adjusting expectations along the way.Where to find Chad PytelLinkedIn: https://www.linkedin.com/in/cpytel/ X: https://x.com/cpytelWhere to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Introducing Chad Pytel, founder and CEO at thoughtbot and dad of two(04:37) Exploring the aging space with AI(06:06) Starting a gaming and production company(08:43) Navigating teenage years(18:33) Balancing work and family life(19:23) Sustainable pace and company culture(23:48) Parenting realizations(24:56) Frameworks for parenting(25:21) Daily routines and systems(27:17) Sunday date concept(29:50) Parenting styles and screen time(35:34) Halloween traditions(37:37) Keeping up with the Joneses(41:19) Lightning Round: Being a relaxed and reasonable dadResources From This Episode:Giant Robots Smashing Into Other Giant Robots (Podcast): https://podcast.thoughtbot.com/thoughtbot: https://thoughtbot.com/12 Sided Studios: https://12sidedstudios.com/ Critical Role (Actual Play Series): https://critrole.com/ Dimension 20 (Actual Play Series): https://www.dropout.tv/dimension-20 American Society on Aging: https://www.asaging.org/ Wall-E (Film): https://www.imdb.com/title/tt0910970/Monty Python and the Holy Grail (Film): https://www.imdb.com/title/tt0071853/Kia Rondo (Car Model): https://www.edmunds.com/kia/rondo/ thoughtbot: https://thoughtbot.com/ 12 Sided Studios: https://12sidedstudios.com/ —For sponsorship inquiries email: [email protected] Startup Dad Merch: www.startupdadshop.com

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• Work-Life Balance is a Myth | Jonathan Jamil (Dad of 2, Springboard)

  Jonathan Jamil, founder and CEO of Springboard, shares his story of growing up in a two-bedroom apartment with six family members, building a business powered by stay-at-home moms, and raising two daughters while redefining what success means.In this episode, Jonathan opens up about his entrepreneurial journey, the lessons he has carried from his upbringing, and the realities of being a dad and founder at the same time. We discussed:Why work-life balance doesn’t exist: Jonathan explains why he believes balance is a myth, and instead focuses on being fully presentRedefining success as a father and founder: He shares how his definition of success shifted from chasing cars and houses to prioritizing comfort, family health, and presence.Breaking generational patterns with love: From hugs to family vacations, Jonathan reflects on how intentional affection and kindness help him parent differently than he was raised.Partnership and parenting: He talks about how he and his wife share the load, why he ignores outdated cultural norms around gender roles in parenting, and the promise he kept to support her becoming a stay-at-home mom.Why nice guys don’t finish last: Jonathan describes how leading with empathy and kindness has shaped Springboard’s culture, strengthened client trust, and fueled growth.Where to find Jonathan JamilLinkedIn: https://www.linkedin.com/in/jjthatcxguy/ Springboard: https://www.springboardhq.com/ Instagram: https://www.instagram.com/thejonathanjamil/ X: https://x.com/jjthatcxguyWhere to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://ww.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Welcome Jonathan Jamil(03:55) Starting Springboard and working with stay-at-home moms(06:41) Why Springboard never posts job listings(08:33) Building a business while raising a newborn(10:19) Why work-life balance doesn’t exist(13:27) Redefining success as a dad(14:46) Why you can’t parent alone without community(16:06) Advice to his younger self before becoming a dad(18:23) Never stop dating your wife(20:35) The power of vacation and taking breaks(24:14) His simple fatherhood framework: Show up, listen, love(26:22) Espresso-fueled speeding ticket during the colic phase(28:54) Parenting disagreements: Screen time and sugar(30:56) Tech boundaries and raising daughters in a digital world(32:55) Using AI to plan family vacations(34:39) Why “nice guys finish last” is a myth(37:14) Lightning round: Parenting wins and toy assembly failsResources from this episode:Jambys: https://www.jambys.com/Disney Store: https://www.disneystore.com/toys-plush/toys/ Lime Green Bed Sheets: https://www.amazon.com/Lime-Green-Bedding/s?k=Lime+Green+BeddingCocomelon: https://www.youtube.com/channel/UCbCmjCuTUZos6Inko4u57UQWreck-It Ralph: https://www.imdb.com/title/tt1772341/Ratatouille: https://www.imdb.com/title/tt0382932/Home Alone: https://www.imdb.com/title/tt0099785/ The Santa Clause: https://www.imdb.com/title/tt0111070/Play-Doh: https://shop.hasbro.com/en-ca/play-dohToyota Sienna: https://www.toyota.com/sienna/Siqi Chen’s Episode: https://www.youtube.com/watch?v=I2Nm5Mkj0s0Cape May: https://www.capemay.com/Ocean City: https://www.ocnj.us/Rehoboth Beach: https://www.rehobothbeachde.gov/Disney World: https://disneyworld.disney.go.com/UPPAbaby: https://uppababy.com/Boppy: https://www.boppy.com/Jamby’s: https://www.jambys.com/—For sponsorship inquiries email: [email protected] Startup Dad Merch: www.startupdadshop.com

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• Raising Twins on Hard Mode | Adam Lieb (Dad of 2, Gamesight)

  In this episode of Startup Dad, I sit  down with Adam Lieb, the founder and CEO of Gamesight, a marketing technology company that helps video game studios connect with players and launch their biggest titles. Adam started his first gaming business at just 11 years old and has spent his entire career building in the industry ever since.As a dad of 11-year-old twins and husband to Camille, a lawyer who now leads the legal team at Gamesight, Adam shares what it’s like to grow a company and a family at the same time. From the challenges of raising twins to why he doesn’t believe in separating work mode from dad mode, Adam offers an honest look at the overlap of parenting and entrepreneurship. We discussed: Raising twins while building a company: Why he compares it to running three startups at once.The sleep training strategy: How it became the most important defensive move for survival with twins.Work mode vs dad mode: Why Adam believes in being the same person everywhere.AI at home: Creative ways his kids use AI for learning, projects, and fun.The mantra “show up and try”: Why presence is the foundation for leadership and parenting.Where to find Adam Lieb:LinkedIn: https://www.linkedin.com/in/adamslieb/ X: https://x.com/adamslieb Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ X: https://x.com/fishmanafInstagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Introducing Adam Lieb(02:16) What Gamesight does and how Adam started in gaming(05:32) Raising 11-year-old twins with his wife, Camille(07:38) Running “three startups” at once: company and twins(09:34) Working with his wife inside the business(10:01) What’s unique about having twins, and why sleep training mattered(16:05) Why doesn’t Adam separate dad mode and work mode(18:30) Cheering from the baseball field while sending emails(20:13) The mantra that guides parenting and leadership: show up and try(24:30) Lessons learned since becoming a dad and mistakes along the way(26:17) The balance between coaching your kids and supporting them(29:16) Aligning with his wife on parenting philosophy(31:29) Setting limits on video games and tech at home(39:46) Raising kids with AI and creative projects they’ve built(47:16) Lightning round: indispensable products, useless gear, quirks, and dad superpowersResources From This Episode:Gamesight: https://gamesight.io/ Collapsible Wagon: a.co/d/dmFVnSI Table For Two: https://buytablefortwo.com/ Alexa: https://alexa.amazon.com/ Happy Gilmore: https://www.imdb.com/title/tt0116483/Happy Gilmore 2: https://www.imdb.com/title/tt31868189/ The Lord Of The Rings: https://www.imdb.com/title/tt0120737/ —For sponsorship inquiries, email: [email protected] Startup Dad Merch: www.startupdadshop.com

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