Katie Robbert has been told to stay quiet, stay in her lane, and let someone else be the face of the company. She heard it from a mentor she respected. She heard it from investors. She heard it so many times she almost believed it. She didn’t.

Katie is the CEO of Trust Insights, an AI education and analytics firm she co-founded eight years ago. And she holds that title deliberately, because someone told her she shouldn’t.

In this episode, she pulls back the curtain on what it actually took to get there: the verbally abusive VP she was told to just tolerate, the investor feedback that nearly made her hand over the CEO seat, and why she’s now built a virtual version of herself to run ideas past before they get to her. The answer is always the same: it’s going to ask a million questions.

What you’ll learn:

• Why “don’t rock the boat” advice - however well-intentioned - can quietly wire you to shrink instead of lead
• What Katie did when investors told her a female CEO would tank her chances of funding
• How to tell the difference between a battle worth fighting and one that will just cost you
• Why the people who say yes to everything are the ones who keep leaving, and what Katie looks for instead
• How Trust Insights built a virtual Katie Robbert AI trained on her own decision-making style (and why the team runs ideas past it first)
• What real community looks like for founders who need someone to be honest with - not impressed by them

About Katie Robbert

Katie Robbert is the CEO of Trust Insights, a data analytics and AI education firm she co-founded with Christopher Penn in 2017. With over 15 years in AI and analytics, she has built a reputation for asking the questions other people are afraid to ask - in client work, in company culture, and in every room she walks into. Trust Insights serves organizations navigating real-world AI adoption and has been a resource in the space long before generative AI became a boardroom talking point. Katie is an introvert who runs a public-facing company, a pragmatist who works alongside one of the most innovative minds in marketing AI, and a CEO who was told she shouldn’t be one.

This episode is for anyone who has been handed advice that was really just a request to make themselves smaller — and is trying to figure out when to ignore it.

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