Sometimes Jay Schwedelson skips the marketing hacks and just gets real. This time he shares a personal story about nearly missing out on the love of his life and the lesson it left him with: regret is far heavier than failure. It’s raw, funny, and surprisingly relevant if you’ve ever hesitated before taking your shot in business or in life.
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Best Moments:
(01:09) The biggest turning point in Jay’s life that reshaped how he thinks about work and risk
(02:42) The sting of seeing someone you care about happy with someone else
(05:16) The bold move at the bar that changed everything
(07:45) Why you only need 10 seconds of bravery, not a lifetime of courage
(08:32) The torture of living in the land of what ifs
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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson
Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson
Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/
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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out April 21, 2026). All net proceeds are donated to The V Foundation for Cancer Research—let’s kick cancer’s butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206
