EP 4: Evan Yudell – Trust, Creativity, and the Future of Leadership

Changing Shapes – Episode 4
“Wonder. What if. Let’s try.”

In this episode of Changing Shapes, I speak with Evan Yudell—founder and CEO of Sales Made Simple—about what it takes to build trust in teams, navigate failure, and lead creatively in a world increasingly shaped by AI.

Evan left a corporate leadership career to bootstrap his own SaaS company, not because he always wanted to be a founder, but because someone asked him a question at the right time—and he had the vision (and humility) to say yes.

Our conversation explores:

• Why real trust takes time, humility, and inclusion

• The creative side of leadership (and why jazz drumming might be the best training for it)

• What AI can and can’t replace when it comes to human connection

• The danger of skipping hard lessons when juniors are replaced by language models

• What advice Evan gives to the next generation of leaders in a post-AI world

We also talk about how his own neurodivergence shaped his leadership style, why he avoids "us vs them" hierarchies, and how he builds loyalty by letting people into the process—because, as Evan puts it, “asking for someone’s opinion is one of the clearest signals that you trust them.”

This one’s full of hard-won wisdom, punchy honesty, and plenty of unexpected moments.

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