March 13, 2026
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Ep 4: The Big Ass Calendar & Radical Outreach Strategies

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Taylor Prokes: Scaling the Big Ass Calendar & Radical Outreach Strategies

Taylor Prokes is the co-founder and CEO of the Big A## Calendar and the creative engine behind Jesse Itzler’s portfolio of brands . In this episode, Zach Schofel dives into the "unordinary" life of a founder who went from a finance degree to living in a Jeep, to running 100-mile ultra-marathons. 

Taylor shares the exact blueprint she used to get on Jesse Itzler’s radar, making 100 videos in a single year and how that evolved into a partnership that has seen the Big Ass Calendar grow by 60% year-over-year.

In this episode, you’ll learn:

  • The "No Ask" Outreach: How to build a relationship with someone you admire by providing value and entertainment for a year before asking for anything .
  • Planning for Legacy: Why Taylor believes you should schedule your life's adventures before your work meetings .
  • The Resilience of an Ultra-Runner: What rim-to-rim-to-rim in the Grand Canyon taught Taylor about grit and surviving when you're "dead after four hours".
  • The Hard Truth of Scaling: Lessons from moving 60,000 units in two months and managing the "fires" that come with rapid growth .