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Exploring the Analogy of Cash versus Lotto Tickets in Balancing Personal and Professional Pursuits
Exploring the importance of distinguishing between cash flow and risky investments in navigating personal and professional pursuits for sustainable growth.
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!
Listen, watch and subscribe: Apple, Spotify, YouTube, Overcast and Google.
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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: http://startupdadpod.substack.com
- Newsletter: http://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/
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Listen to the best highlights from the podcasts you love and dive into the full episode