102: How to Pivot Your Business When You Feel Trapped by Its Success with Jason Van Orden

8 Dec 2025 · 56 min
Episode

8 Dec 2025 · 56 min

0:00

Jason Van Orden built a successful business that left him feeling trapped, so he took an 18-month sabbatical and eventually moved on. He talks about depression returning during the pivot, finding help through a mastermind group, and using frameworks like the 3Vs (vision, value, voice) and 3Rs (relevance, resonance, remarkability) to rebuild his identity and find what's next.

Questions this episode answers

June 3, 2018.

Jenny mentions 8 million downloads (over ~10 years).

Planned: 90 days (experiment). Actual: ~18 months.

Success trifecta (vision, strategy, execution); refined into 3Vs (vision, value, voice) and 3Rs (relevance, resonance, remarkability).

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