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Season 4 of Welloff is officially here! We’re kicking things off with Connecticut matchmaker, entrepreneur, content creator, and former Disney Radio host Alexa Curtis.

Alexa’s story is anything but traditional. After a difficult childhood in small-town Connecticut, she moved out on her own at just 16, cold-emailed Disney, and ultimately landed her own podcast with the company. Since then, she’s built multiple businesses, launched the Be Fearless Summit, grown a successful career in content creation, and founded The Love List, now New England’s #1 matchmaking company. She also recently sold her second company, Chief Swag Officer, while remaining on as a partner.

We get into the world of modern dating, including dating-app burnout, first-date questions, red flags, background checks, and whether “once a cheater, always a cheater” is actually true. Spoiler: Gina, Alexa, and Dr. Tara do NOT completely agree.

Alexa also shares how she built her personal brand, turned cold emails into opportunities, and why she believes entrepreneurs are born, not made.

It’s a fun, honest conversation about taking chances, building something of your own, dating, branding, and creating a life that feels authentically yours.

Welcome to Season 4 of Welloff!
Follow Alexa Curtis @alexacurtis and @thelovelist

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