"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

E23: “Founder Mode"? Setting the Record Straight with Jim Cook


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When Y Combinator's Paul Graham released his viral essay "Founder Mode," it sparked a firestorm in the tech world. Based on a private talk by Airbnb's Brian Chesky and endorsed by the likes of Elon Musk and Patrick Collison, the piece garnered over 20 million views. Enter Jim Cook, legendary Silicon Valley CFO (Netflix, Intuit, Mozilla) who just wrote a counterargument to set the record straight. Cook challenges the simplistic notion of founder supremacy — where only 10% succeed — and offers a different Leadership Mode framework for building high-performance, generational companies.


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LINKS:

Cook’s Playbooks https://jcookflix.substack.com/

Founder Mode PG https://paulgraham.com/foundermode.html

Lenny’s Podcast episode with Brian Chesky https://www.youtube.com/watch?v=4ef0juAMqoE

Product-CEO Paradox by Ben Horowitz https://a16z.com/why-founders-fail-the-product-ceo-paradox/

Hard Thing About Hard Things by Ben Horowitz https://a16z.com/books/the-hard-thing-about-hard-things/

Scaling People with Claire Hughes Johnson https://www.goodreads.com/book/show/63063173-scaling-people


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X/SOCIAL:

@sashaorloff

@cookflix


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TIMESTAMPS:

(00:00) Episode preview

(00:26) Intro

(00:51) Founder Mode essay

(04:13) Challenges of polarized arguments

(07:44) Importance of leadership mode

(10:59) Balancing founder and scaling modes

(15:01) Sponsors: Netsuite | Metaview

(16:49) Trust and transparency in leadership

(20:41) Importance of creating a culture

(24:57) Leading with values and behaviors

(29:48) Sponsors: Brave | Omneky

(31:13) Importance of documentation

(36:45) Balancing founder and manager roles

(39:06) Structuring ownership and accountability

(43:06) Founders as Coaches and Captains

(48:12) Specialized operators in finance

(50:41) Scaling company to public

(53:50) Wrap

...more
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"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance TechBy Puzzle, Turpentine

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