Navigating the Entrepreneurial Landscape

Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection point—tripling revenue year over year. Rob dives deep into the pivots, setbacks, and critical decisions that turned early failure into a massive success. If you’re an early-stage founder feeling stuck, this episode will show you how patience, resilience, and radical product decisions can transform your startup.

Why You Should Listen

• How Sigma went from $0 to $100M ARR—but spent 7 years figuring it out.
• The pivot that turned years of failure into explosive growth.
• Why obsessing over speed to product-market fit is the wrong game.
• How to handle the psychological toll of startup uncertainty.
• The hidden power of building features your customers never ask for.

Keywords

product-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories

00:00:00 Intro

00:02:49 Debating speed to product–market fit

00:10:14 Quitting Salesforce and the EIR leap

00:23:12 Two years of prototypes that went nowhere

00:36:53 The Snowflake meeting and spreadsheet pivot

00:45:41 Dealing with Investors

00:52:30 Tripling three years straight to $100M ARR

00:54:46 Why most people shouldn’t start a company

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