She Tried to Be the “Nice” CEO—Here’s What Went Wrong (Devin Bramhall)

Devin Bramhall has been a VP of marketing, a CEO, a fractional CMO, and now an author, but none of that came without falling on her face multiple times.

In this episode, Devin opens up about the mistakes that got her fired (twice), the time she unknowingly helped commit financial fraud, and the zero-tolerance plagiarism incident that backfired in the worst way. Through all of it, she’s held onto her belief that everything from leadership to content strategy is made up, and that’s exactly why you can rewrite the rules.

Devin shares what it means to lead with bravery and curiosity, how ambition nearly derailed her career, and why making space for nuance, not just kindness, is the real growth path for leaders.

Devin opens up about:

- Getting fired from two leadership roles and what she did next

- Why "servant leadership" backfired as a CEO

- The difference between plans and actual strategy (and how she learned it the hard way)

- Escaping financial fraud… and nearly getting questioned by the FBI

- The power (and downside) of trying to make work feel “safe” for everyone

Things to listen for:

(00:00) Intro

(01:37) Devin's early life and entrepreneurial spirit

(09:02) Transition to professional life

(09:17) Thank you to our sponsor, ThriveStack

(10:35) Entering the tech world

(19:07) Discovering marketing and content creation

(23:56) Major career mistakes and lessons learned

(30:36) The strategy presentation disaster

(31:25) Learning from painful experiences

(32:59) Balancing leadership and empathy

(34:44) The importance of boundaries

(36:08) Handling plagiarism and setting expectations

(37:58) Navigating leadership challenges

(39:50) Transitioning to CEO

(45:03) Dealing with job loss and resilience

(48:35) The power of choice and perspective

(54:24) Promoting bravery and curiosity

(55:51) Everything is made up and that’s where your power is

A huge thanks to this episode’s sponsor:

ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/

Resources:

Connect with Devin:

LinkedIn: https://www.linkedin.com/in/devinbramhall/

Devin’s official website: https://www.devinbramhall.com/

Pre-purchase Devin’s book, B2B Content Marketing Strategy: https://www.amazon.com/B2B-Content-Marketing-Strategy-Media-First/dp/1398622516

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching