What’s worse than pissing people off with a bold marketing campaign? Boring them.

So why is everyone following the same playbooks, recycling “best practices”, and relying on cookie cutter AI to generate the same-sounding content?

If you want to truly stand out, you have to break the rules… or at least question them.

Stephanie sits down with Udi Ledergor, Chief Evangelist at Gong and author of Courageous Marketing, to talk about how marketers can push past fear, embrace bold strategies, and create campaigns that people actually remember.

Udi shares why "best practices" are often just boring practices, how startups have more freedom to take risks than they realize, and why some of Gong’s scrappiest marketing stunts generated the biggest buzz. Plus, we dive into how AI is changing the marketing landscape — and how to make sure it doesn’t turn your brand into just another generic voice in the noise.

Key Moments:

00:00: Who is Udi Ledergor, Chief Evangelist at Gong?

01:37 Why Many “Best Practices” Are Outdated

03:27 The Courage to Be Different

06:14 Choosing the Right Company and Leadership

13:59 Creating Buzz with Content Marketing

26:54 Hiring for Potential Over Experience

31:46 The Value of Diverse Backgrounds in Marketing

35:56 Handling Failure: A Marketing Campaign Gone Wrong

45:32 Writing a Book: Insights and Sneak Peeks

51:32 The Role of AI in Marketing

58:53 Lightning Round: Quickfire Questions and Answers

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