What in My Ears?
I spend a lot of time listening (to books, podcasts, and music) mostly while walking, running, or biking. It’s how I learn, think, and reset. And I particularly like to listen to things that are adjacent to leadership rather than straight-up leadership podcasts. I find I learn more from different perspectives.
This week, I thought I’d share three podcasts that I'm listening to at the moment, and what they reveal about leadership.
We Regret to Inform You
Also known as The Rejection Podcast, this one dives into how wildly successful ideas were rejected again and again: Mad Men, Netflix, the Rubik’s Cube, women in the Boston Marathon. Their tagline is “never, ever give up,” but I think the deeper lesson is really about timing, luck, persistence, and experience coming together. Success isn’t linear. It’s messy, unpredictable, and often depends on whether you’ve developed the skills to seize the opportunity when it finally arrives. (I’d recommend scrolling back to the early seasons: the storytelling is especially good there.)
Leadership takeaway: Great leaders don’t just push through rejection; they evolve through it.
Acquired
My newest obsession. Each episode is a masterclass in business storytelling, unpacking the history, strategy, and culture behind iconic companies. I recently listened to the episode about Trader Joe’s, a fascinating story of how they built a grocery empire by intentionally doing the opposite of everyone else. Instead of chasing scale, they focused on small, densely stocked stores, private-label products (which they branded with personality and humor), and a fiercely loyal niche customer base. Did you know they started as a competitor to 7/11? There may have even been ammo as part of their initial offerings.
Leadership takeaway: The most successful leaders don’t follow the market. They define their own lane and double down on it.
Under the Influence with Terry O’Reilly
A classic, Terry explores how brands are born and how ideas spread , always told through clever, well-told stories. He covers brand trends over time, Luxury Advertising, Candid Commercials, Arch Enemies (about rivals), Mad Women who changed advertising, and so many other brilliant episodes. It’s a reminder that influence isn’t about shouting louder; it’s about understanding your audience so deeply that you can speak their language.
Leadership takeaway: Great leaders and great brands both succeed by knowing their audience and communicating with clarity, empathy, and consistency.
I also mix in The Bridge (Peter Mansbridge, for the Canadians reading this) and What Now? with Trevor Noah. Both explore current events with nuance and curiosity.
Listening to different voices helps me notice patterns and trends, and anticipate what’s ahead.
What's in your ears these days?