Episode 144
We Got Leadership Wrong for Years. Here’s What We'd Change.
Bob and Josh frame the episode as “letters” to their future or past selves, sharing personal and leadership advice. Josh emphasizes trusting his gut even when he’s “annoyingly early,” dialing back intensity without stopping completely, continuing to make hard decisions and have difficult conversations at work and at home, and believing that “the money will take care of itself” despite economic pressures affecting his family and kids.
Bob argues that AI needs governance and a slowdown because it’s evolving too fast without thoughtful control, and he reflects on leadership as modeling—how you show up under pressure—admitting he harmed people earlier in his career and wishing he could undo it. He also stresses telling people what they mean to you and focusing on legacy: relationships, community, sustainability, and the impact you leave behind.
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