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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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 Pytel
- LinkedIn: https://www.linkedin.com/in/cpytel/
- X: https://x.com/cpytel
Where to find Adam Fishman
- FishmanAF 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 dad
Resources 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/
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For sponsorship inquiries email: [email protected].
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