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Rethinking the Myth of Perfect Planning for Startups

Hosted by Casey Woo

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What you'll learn

Myth: Planning is about setting goals and budgets

Truth: Planning is about alignment—Learn how to get your team on the same page and navigate unpredictable growth.

Myth: Forecasts need to be accurate

Truth: Every forecast is wrong. They force teams to talk, align, and adjust, which is where real progress happens.

Myth: Planning follows a linear process

Planning in a startup is messy, dynamic, and anything but linear. Learn how to adapt to changes and seize opportunities

Why this topic matters

Most startups get strategic planning wrong. They focus on getting the numbers right, setting rigid goals, and hitting targets. The reality? 100% of forecasts are wrong. Planning is a human experience—aligning people, encouraging conversation, and adjusting to rapid changes. We'll flip the script on traditional planning and show you how to plan smarter in high-growth environments.

You'll learn from

Casey Woo

CEO @ Operators Guild. 7x COO/CFO with 20+ years in high-growth tech.

Casey Woo is a seasoned public market investor turned high-growth technology COO/CFO, with over two decades of experience guiding companies through the complexities of scaling. Having served as a 6x CFO and 2x COO, Casey has led businesses across various industries and stages, from early-stage startups to pre-IPO powerhouses. His expertise spans software, hardware, marketplaces, eCommerce, and more, with a proven track record in driving strategic growth, optimizing operations, and securing successful exits.


As a leader, Casey is deeply committed to building and scaling companies that not only grow fast but grow smart. His strategic approach focuses on aligning vision with execution, ensuring that every initiative is prioritized for maximum impact. Beyond his executive roles, Casey is co-founder and CEO of the Operators Guild, a community of 900+ top operators, where he shares his insights and mentors the next generation of business leaders.


Casey’s passion for strategic planning and performance management has made him a sought-after advisor and investor, helping startups navigate the challenges of hyper-growth with precision and confidence.


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