The Generation Hustle Podcast

GHP #105 - Operator #2 - The Fragility of Fake Communities and Finding the Right Career Path with Casey Woo


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Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups.


Casey now leads 700+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance and operations roles. He strongly believes that community makes a difference for start-ups and professionals. When he’s not working, Casey spends time in California’s Bay Area with his wife and three children.

00:02:30 Casey's path to tech

00:09:13 Career exploration leads to growth.

00:12:55 Trust your gut, not timelines.

00:19:23 Building a supportive community for operators.

00:23:25 Building a successful community requires authenticity, engagement, and generosity.

00:31:37 Syndicates enable angel investing opportunities.

00:38:09 Empowerment and accountability in leadership.

00:40:22 Let go and trust talented individuals.

00:49:48 Nurture meaningful relationships through community.

00:51:06 Invest time in meaningful relationships.

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The Generation Hustle PodcastBy Generation H

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