S2E21: Specialists Optimize. Operators Build Companies. With Casey Woo (FOG Ventures + Operators Guild)
Mon Feb 02 2026
Casey Woo has spent over two decades inside the engine room of real companies, scaling startups as a 6x CFO and 2x COO across SaaS, marketplaces, hardware, eCommerce, and beyond.
After walking away from a successful career in public markets, Casey chose the harder path: joining early-stage startups, eating glass, and learning how companies actually get built under pressure. Along the way, he founded the Operators Guild, a global community of 1,200+ elite builders, and FOG Ventures, an operator-led investment platform backing the modern operator and GTM stack.
In this conversation, we unpack why generalist operators are becoming the new frontier for founders and investors. We talk about business as both physics and art, why judgment beats specialization early, what separates great operators from average ones, and why VCs increasingly back operator-led companies and platforms.
This is an operator-first conversation about craft, execution, and building companies that actually work, without startup theater.
Subscribe now
Chapters
00:02 Introduction to Operators and Generalists01:13 Casey Wu’s Journey from Wall Street to Startups03:22 The Cultural Shift: From Banking to Building05:34 The Role of Operators in Startups09:04 The Birth of the Operators Guild12:24 Defining the Roles: Founder vs. Operator15:31 The Evolution of the Operator Role16:30 The Impact of Technology on Operators22:34 Advice for Aspiring Operators22:42 The Importance of Community in Business24:23 Learning Through Experience25:40 Fundamentals of Business Success27:33 The Role of Human Relationships28:45 The Operators Guild and Knowledge Sharing34:31 Introducing Fog Ventures40:44 Customer Feedback and Product DevelopmentGuest Bio
Casey Woo is the Founder of the Operators Guild and General Partner at FOG Ventures, a leading operator-led investing platform.
A former public markets investor, Casey has spent over 20 years operating inside high-growth companies as a 6x CFO and 2x COO, guiding startups from early-stage through hypergrowth, multiple funding rounds, and pre-IPO. His experience spans software, hardware, marketplaces, eCommerce, supply chain, real estate, and professional communities.
Through the Operators Guild, Casey built a global network of more than 1,200 elite operators, the people responsible for scaling some of the fastest-growing companies in tech. Building on that foundation, he launched FOG Ventures, investing alongside operators in the modern operator and GTM software stack.
email: casey@operators-guild.com
Access All Areas.
Listen: Apple || Spotify || YouTube
Subscribe: Substack
Community & Events: Founders Circle
Connect: LinkedIn
Socials: TikTok || Instagram || X
Web: startupsdecoded.com
Music Credit
“Neptuno” – Phondupe (Album: Onykia)
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Casey Woo has spent over two decades inside the engine room of real companies, scaling startups as a 6x CFO and 2x COO across SaaS, marketplaces, hardware, eCommerce, and beyond. After walking away from a successful career in public markets, Casey chose the harder path: joining early-stage startups, eating glass, and learning how companies actually get built under pressure. Along the way, he founded the Operators Guild, a global community of 1,200+ elite builders, and FOG Ventures, an operator-led investment platform backing the modern operator and GTM stack. In this conversation, we unpack why generalist operators are becoming the new frontier for founders and investors. We talk about business as both physics and art, why judgment beats specialization early, what separates great operators from average ones, and why VCs increasingly back operator-led companies and platforms. This is an operator-first conversation about craft, execution, and building companies that actually work, without startup theater. Subscribe now Chapters 00:02 Introduction to Operators and Generalists01:13 Casey Wu’s Journey from Wall Street to Startups03:22 The Cultural Shift: From Banking to Building05:34 The Role of Operators in Startups09:04 The Birth of the Operators Guild12:24 Defining the Roles: Founder vs. Operator15:31 The Evolution of the Operator Role16:30 The Impact of Technology on Operators22:34 Advice for Aspiring Operators22:42 The Importance of Community in Business24:23 Learning Through Experience25:40 Fundamentals of Business Success27:33 The Role of Human Relationships28:45 The Operators Guild and Knowledge Sharing34:31 Introducing Fog Ventures40:44 Customer Feedback and Product DevelopmentGuest Bio Casey Woo is the Founder of the Operators Guild and General Partner at FOG Ventures, a leading operator-led investing platform. A former public markets investor, Casey has spent over 20 years operating inside high-growth companies as a 6x CFO and 2x COO, guiding startups from early-stage through hypergrowth, multiple funding rounds, and pre-IPO. His experience spans software, hardware, marketplaces, eCommerce, supply chain, real estate, and professional communities. Through the Operators Guild, Casey built a global network of more than 1,200 elite operators, the people responsible for scaling some of the fastest-growing companies in tech. Building on that foundation, he launched FOG Ventures, investing alongside operators in the modern operator and GTM software stack. email: casey@operators-guild.com Access All Areas. Listen: Apple || Spotify || YouTube Subscribe: Substack Community & Events: Founders Circle Connect: LinkedIn Socials: TikTok || Instagram || X Web: startupsdecoded.com Music Credit “Neptuno” – Phondupe (Album: Onykia)