

❤️How I Met My Wife❤️ Regret is Worse Than Failure!⏳ Jay’s SCOOP | Ep. 419
Sep 26, 2025
Jay Schwedelson shares a personal story about love and regret, illustrating how missing his chance with the love of his life taught him that regret is far heavier than failure. He recalls the sting of seeing her with someone else and the bold decision that changed everything. Highlighting that only ten seconds of bravery can prevent a lifetime of what-ifs, Jay emphasizes the importance of acting decisively in both business and life. His heartfelt and humorous insights inspire listeners to seize opportunities without hesitation.
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Regret Beats Failure
- Jay reflects that the core lesson from his story is that regret is worse than failure.
- He says this realization has reshaped how he approaches work, risk, and decisions.
How He Met His Wife
- Jay Schwedelson describes meeting Allie at University of Florida and losing touch after college before seeing her again in South Florida.
- He chased her down at a bar, got her real number, called next morning, and they stayed together ever since.
Choose Action Over Hesitation
- Apply the regret lesson to business: introduce yourself, ask the hard question, and pursue opportunities instead of hesitating.
- Prioritize eliminating future regret over avoiding possible failure today.