❤️How I Met My Wife❤️ Regret is Worse Than Failure!⏳ Jay’s SCOOP | Ep. 419

Do This, NOT That: Marketing Tips with Jay Schwedelson

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.

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

Partner with Jay: https://www.jayschwedelson.com/contact

Check out Jay Schwedelson's new book: Stupider People Have Done It

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

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

Leave a comment and follow the show, it really helps us out!

More description

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.

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

Partner with Jay: https://www.jayschwedelson.com/contact

Check out Jay Schwedelson's new book: Stupider People Have Done It

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

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

Leave a comment and follow the show, it really helps us out!

2025-09-26 10 min Transcript
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