Back to all episodes Episode 22

Jacob Ross on Trusting Yourself and Building the Business You Can See

with Jacob Ross, CEO of PebblePost

September 29, 2025 | 38 minutes

About this episode

PebblePost's CEO Jacob Ross explores strategic pivots, investor signals, and the gap between good and great opportunities.

We discuss how to trust your instincts as a CEO, when to pivot your business model, and how to recognize the difference between a good opportunity and a great one.

Topics covered

  • Trusting yourself as a CEO
  • Strategic pivots and timing
  • Reading investor signals
  • Good vs great opportunities
  • Building conviction in your vision

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