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Aug 11, 2025 28 min

Episode 0060 The Problem with Timing

from Sippi Hosted by Christopher Spence, Caleb Brown

According to Freakonomics author and podcast host, Stephen J. Dubner, “The difference between success and failure is sometimes just…timing.”. At least that’s the argument he makes in his Episode 563, “How to Succeed at Failing, Part 3: Grit vs. Quit (Update)”, which Caleb & Chris reference in this week’s episode. They even play a short clip from that episode, which offers a really poignant and layered example of Dubner’s point. Caleb & Chris then relate this concept to entrepreneurship, highlighting how atypical journeys and perceived failures might simply be nothing more than incorrect timing or a rigid definition of success. They encourage listeners to embrace their unique paths and not to succumb to negative self-talk, suggesting that even challenging experiences can be valuable, life-enriching (not defeating) lessons. Check out this episode on the podcast player of your choice and let the guys know if you agree or disagree! Special thanks to Chris for editing this episode, and a very special thanks to the Freakonomics Podcast Team for producing valuable content that inspires and creates thought provoking discussion. We highly recommend all of our Sippi listeners check out their full episode here.

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Episode 0060 The Problem with Timing

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