Recent Episodes

Why You Should Stop Chasing Money and Start Chasing Obsession, with Bill Gurley
March 2, 2026

Why You Should Stop Chasing Money and Start Chasing Obsession, with Bill Gurley

In this episode, Kyle sits down with venture capitalist and author Bill Gurley to talk about how to figure out your passion, what people get wrong about networking, and why pursuing your dream career isn’t such an idealistic ...
Why Emotional Intelligence is More Important Than Ever at Work
Feb. 23, 2026

Why Emotional Intelligence is More Important Than Ever at Work

In this episode, Kaila and Kyle discuss their thoughts on the age-old question: is it ever okay to be emotional at work? Listen to hear their anecdotes of crying with colleagues, surface acting vs. deep acting, and why they t...
AI at Work: What We Got Wrong (And the Use Cases That Actually Work)
Feb. 16, 2026

AI at Work: What We Got Wrong (And the Use Cases That Actually Work)

In this episode, Kaila and Kyle revisit the topic of AI (2 years after their first episode on the topic ) and discuss the major objections to AI, how the perception of the technology has changed recently, and the best ways to...
Job Kissing, AI Slop, and Our Work Life Predictions for 2026
Feb. 9, 2026

Job Kissing, AI Slop, and Our Work Life Predictions for 2026

In this episode, Kaila and Kyle share their predictions for work and work culture in 2026. From “job kissing” to the careers we think might be eliminated in 2026, you’re not going to want to miss this episode. 00:00 Intro 01:...
Everyone Feels Uncertain at Work Right Now—Here’s How to Handle It
Feb. 2, 2026

Everyone Feels Uncertain at Work Right Now—Here’s How to Handle It

In this episode, Kaila and Kyle discuss uncertainty at the individual, external, and societal level, and share their best strategies for managing and coping with the anxiety that comes with it. 00:00 Intro 03:08 Addressing un...
BONUS: What Makes a Workplace People Actually Love?
Jan. 29, 2026

BONUS: What Makes a Workplace People Actually Love?

In this special bonus episode, Kaila and Kyle sit down with Industrious president Anna Squires Levine to discuss the role that connection plays at work, the future of offices and hybrid vs. remote work, the role of leadership...

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