He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni

Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M.

In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M didn't stop them from staying stingy, and the LinkedIn playbook that turned 6,000 connections into a 90% response rate.

Why You Should Listen

• Why losing every deal doesn't mean the idea is wrong—and how to know the difference.
• Why real differentiation shows up as "wow" moments in demos, not signed contracts.
• The LinkedIn social-selling playbook that built Omni's first pipeline.
• Why hiring sellers from your old industry hands you their Rolodex on day one.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Omni, Colin Zima, Looker, business intelligence, BI tools, enterprise SaaS, AI analytics, social selling, LinkedIn outbound, founder-led sales, innovator's dilemma

Chapters

• 00:00:00 Intro
• 00:01:58 The Moment of True Product Market Fit
• 00:06:16 Losing All Five Deals and Doubling Down
• 00:10:43 Leaving Looker to Compete With Looker
• 00:17:39 Founding With $30M and Staying Stingy
• 00:22:09 A Hundred Demos Before the Flywheel
• 00:32:15 No Silver Bullet—Just Do More of Everything
• 00:38:32 The LinkedIn Social-Selling Playbook
• 00:46:07 Hiring the Best People You've Worked With

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