In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'. 

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

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SPONSORS:

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This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

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LINKS:

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

Fog Ventures: https://www.fog.ventures/

Casey's Linkedin: https://www.linkedin.com/in/caseywoo

Casey's contact: hello@operators-guild.com

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X/Twitter

@sashaorloff (Sasha)

@caseyswoo (Casey)

@FogVentures (Fog)

@turpentinemedia

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TIMESTAMPS:

(00:00) Preview

(02:00) Life as a banker

(04:06) Story following numbers or numbers following story

(04:39)How banking prepared Casey for working in a startup's finance team

(07:00) Deciding that working in a startup is a right fit

(09:10)Hiring a CFO

(11:20) Advice for bankers transitioning to operating roles

(12:41) First things to accomplish when stepping into a role

(14:05) Sponsor: Attio

(14:52) Interview question to see if a founder takes finance seriously

(16:16) Advice for CFOs to change the dynamic that finance has in the company

(18:08)Casey's time at WeWork as CFO for Western US and Canada

(22:00) Casey's experience being Global Head of Strategic Finance at WeWork

(29:40 Advice for founders in dealing with different growth or recessive cycles

(32:57) Probabilities

(34:00) Time spent on fundraising vs supporting the founder as a CFO

(35:26) Operator's Guild and Generalists

(42:00) How can operators thrive in a transition role

(47:28) The number one piece of advice Casey would give to CFOs

(49:38) Wrap