Startup Dad Learning the Hard Way as a Single Parent with Colin Anawaty, CPO | Dad of 2
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/colin
- Instagram: https://www.instagram.com/colinanawaty/
Where to find Adam Fishman
- FishmanAF Newsletter: www.FishmanAFNewsletter.com
- LinkedIn: https://www.linkedin.com/in/adamjfishman/
- X: https://x.com/fishmanaf
- Instagram: 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 quirks
Resources 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/54kwn6o
LEGO: 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-CIuQ
Josh Jones-Dilworth & Culturati: https://culturati.info/
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For sponsorship inquiries, email: podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com