“Most Decisions Are Reversible” – A Masterclass in Decision Making with Zapier’s Ryan Roccon

In this episode, CJ sits down with Ryan Roccon, CFO of Zapier, to explore the power of storytelling in finance, decision-making frameworks, and the company's commitment to extreme transparency. Ryan highlights the significance of storytelling in finance to connect complex data with company strategy. He explains how he adapts a story for a specific audience and how he avoids “robot mode” when repeating it. The discussion delves into Zapier's unique approach to transparency, how this plays out, the benefits of it, the challenges of it, and how it has become an integral part of the company’s culture. Ryan unpacks the unique dynamics of being a remote-first, bootstrapped company with a cash flow break-even or better requirement. The conversation also covers the importance of effective decision-making, where Ryan suggests that most decisions are reversible and breaks down different frameworks for effective decision-making and fostering organizational buy-in.

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TIMESTAMPS:

(00:00) Preview and Intro

(02:34) Sponsor – RightRev | Brex

(06:31) What Storytelling Is in Finance

(09:01) Adapting Your Story for the Audience

(12:19) Avoiding “Robot Mode” When Repeating a Story

(17:30) Sponsor – Planful | Vanta

(19:37) Frequently Used Analogies

(21:33) The Cohort of Companies Zapier Compares Itself To

(23:33) Storytelling to Potential New Employees

(24:38) Zapier’s Extreme Transparency

(26:08) The Challenges of Extreme Transparency

(29:36) Avoiding Creating Anxiety by Oversharing

(31:11) Zapier’s Cash Flow Break-Even or Better Requirement

(34:18) Other Rules and Ambitions at Zapier

(34:55) Burdening the P&L by Product Line

(37:24) Getting People to Use the DACI Framework

(40:51) The “Fist to Five” Framework

(44:51) Making It Safe to Fail While Expecting Excellent Performance

(48:35) What Ryan Would Most Like to Automate

(49:46) The US Steel and Stanley Cup Story

(52:21) Long-Ass Lightning Round: A Mistake Made Early in Ryan’s Career

(53:31) What Ryan Wishes He Had Known Earlier in His Career

(54:27) Finance Software Stack

(55:25) Craziest Expense Story