Balancing Career Ambition With Your Prime Parenting Years | Casey Woo (father of 3, founder of Operators Guild)

Startup Dad

Casey Woo is the founder of Operators Guild, a community of engaged ops professionals who help each other navigate the issues that arise when scaling a company. He is a reformed Finance leader who found his passion growing a community. He's a husband and father of three kids.

In this episode we discuss:

• How I discovered Casey through a LinkedIn post
• His wife's career and their decision to start a family
• How he explains his job to his kids
• How to lean into your children's strengths
• His favorite (and least favorite) kids books
• Parenting frameworks
• The concept of Cash vs. Lotto tickets
• Rapid fire!

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Where to find Casey Woo

- Twitter / X: https://twitter.com/caseyswoo

- LinkedIn: https://www.linkedin.com/in/caseywoo/

- Operators Guild: https://operators-guild.com/

Where to find Adam Fishman

- Newsletter: https://startupdadpod.substack.com/

- Newsletter: https://www.fishmanafnewsletter.com

- LinkedIn: https://www.linkedin.com/in/adamjfishman/

- Twitter / X: https://twitter.com/fishmanaf

- Instagram: https://www.instagram.com/startupdadpod/

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In this episode, we cover:

[1:38] Welcome and introduction

[1:57] Our LinkedIn connection

[5:39] His childhood/background

[14:02] All about his partner

[17:05] All about his kids

[19:06] His wife’s career

[20:21] Their decision to start a family

[22:23] His earliest memory of being a dad

[23:27] What work/life balance means to him

[25:42] Explaining his job to his kids

[27:34] Carving out time with your spouse

[29:54] Most surprising thing about being a dad

[32:07] Leaning into his kids' strengths

[34:18] Favorite/least favorite kid’s book

[36:32] Parenting frameworks

[38:48] Partnership

[41:24] Cash vs. lotto tickets

[45:39] What he had to give up to become a dad

[47:16] His mistakes as a dad

[48:33] Where to follow/find Casey

[49:40] Rapid fire

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Show references:

Casey's LinkedIn Post - https://www.linkedin.com/feed/update/urn:li:activity:7090030457370644480/

Operator's Guild - https://operators-guild.com/

FOG Ventures LinkedIn - https://www.linkedin.com/company/fog-ventures/

West Point - https://www.westpoint.edu/

Harvard University - https://www.harvard.edu/

Goldman Sachs - https://www.goldmansachs.com/

Morgan Stanley - https://www.morganstanley.com/

WeWork - https://www.wework.com/

McKinsey & Company - https://www.mckinsey.com/

Microsoft Excel - https://www.microsoft.com/en-us/microsoft-365/excel

The Wolf of Wall Street - https://www.imdb.com/title/tt0993846/

The Big Short - https://www.imdb.com/title/tt1596363/

Innovation Endeavors - https://www.innovationendeavors.com/

The Incredibles - https://en.wikipedia.org/wiki/The_Incredibles

The Gruffalo - https://www.gruffalo.com/

Hot Shots! Part Deux - https://www.imdb.com/title/tt0107144/

Umbrella stroller - https://www.amazon.com/Kolcraft-Lightweight-Stroller-Multi-Position-Reclining/dp/B019DHBCXE

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Production support for Startup Dad is provided by Tommy Harron at http://www.armaziproductions.com/

Episode art designed by Matt Sutherland at https://www.mspnw.com/