Punching above your weight with big mediums

#313 | In this episode, Udi Ledergor joins Dave to break down the ideas behind his new book, Courageous Marketing, and why most B2B marketing fails because it plays it safe. He also shares his journey from marketer #1 to CMO to Chief Evangelist at Gong, where he led category creation, brand, and marketing through massive scale. They unpack how Gong built a brand that actually stood out, what it means to punch above your weight as a B2B marketer, and how to think about brand ROI without fake dashboards.

Timestamps

• (00:00) - – Meet Udi and his path into marketing
• (08:16) - – Early career lessons and building marketing from zero
• (15:16) - – How Gong found product-market fit and nailed positioning early
• (19:26) - – Courageous Marketing: why Udi wrote it and what it really means
• (23:16) - – Brand first: personality, positioning, then visuals
• (28:20) - – Campaigns that punched above their weight (billboards, experiments, perception hacks)
• (35:10) - – Proving brand impact: soft ROI, pipeline, and exec buy-in
• (47:40) - – The future: product-led marketing, AI, and courageous teams

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