Episode 17
Ever feel stuck as a founder—uncertain about your next move, paralyzed by fear, or second-guessing what you really want?
In this episode, Jesse Pujji and Dave Kashen unpack the hidden dynamics behind “stuckness” and how founders can transform it into growth. From reframing “I don’t know” as liberation, to uncovering fear, anger, and desire as powerful guides, they show how getting unstuck is less about finding the “right” answer and more about trusting your wants, welcoming your emotions, and embracing uncertainty.
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⏱️ Episode Guide
[00:00:00] Opening – Why this podcast is about building with heart, not just grinding
[00:01:03] 10 problems vs. 10,000 blessings: gratitude framing
[00:02:33] Why founders rarely admit when they feel stuck
[00:03:27] “Growing edge” reframing – stuckness as a sign of expansion
[00:04:21] The genius trap: frustration when things don’t come easy
[00:05:24] Expecting to know vs. embracing “I don’t know”
[00:07:03] Rick Elias’ billion-dollar lesson: “We have no clue what we’re doing”
[00:08:06] Liberation in curiosity and beginner’s mind
[00:09:36] Fear as a hidden driver of stuckness
[00:10:48] Avoidance disguised as time management
[00:12:00] Clarity, murky water, and letting stillness reveal the path
[00:15:18] The unknowable nature of “right” answers
[00:17:42] Persistence vs. letting go – when forcing success backfires
[00:21:00] Why humans cling to certainty
[00:23:06] Capacity to handle uncertainty vs. obsession with being right
[00:25:12] Founders, hedge funds, and separating “being” from “doing”
[00:27:27] Knowing what you want vs. chasing the “right” answer
[00:29:24] Rebuilding the muscle of wanting
[00:31:03] Founder desires and strategy: why “want” drives company success
[00:33:09] Founder energy as the real determinant of persistence
[00:34:21] Why people don’t trust their wants (worthiness, work ethic, trade-offs)
[00:36:54] “What would have to be true?” reframing conflicting desires
[00:40:03] Anger as a signal for boundaries and wants
[00:42:00
Published on 4 weeks, 1 day ago
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