Startup Therapy · 2026-05-25 · 36 min
Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility - endless rumination that produces stress, not decisions. Will shares decades of 3:00 AM worry cycles, the superstition that anxiety prevents disaster, and how even vacations get hijacked by disaster simulations (including getting hacked on the way to Comic-Con). They draw a line between real thinking that creates options and looping that creates suffering, then discuss practical replacements: box breathing to fall back asleep, gratitude to reset perspective, and self-talk that puts the “experienced founder” back in charge. The goal isn’t to stop worrying, but to channel that energy into small, solvable actions instead of spirals.
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