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01:37 Why Many “Best Practices” Are Outdated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
32:44 Creative Event Management: Lessons from Show Business
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