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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Pickles & Pasta EP10 - Evolving, Connecting, & Dating
A candid, fast-moving conversation about why evolution isn’t optional—whether you’re running a business, building a personal brand, or navigating modern dating. Steph & Jay trade stories on adapting to new tech, being authentic on (and off) social, and finding connection in a swipe-first world—plus a light, laugh-y rapid-fire to close.
Topics Covered
- Evolving in business & life: ditch “always done it” thinking.
- Marketing reality: ad spend, stock fails, real service.
- Social media shift: photo → video, founder-as-face.
- Putting yourself out there: balance IRL + online.
- Modern dating: apps, city vs. small-town, friend-first.
- Personal growth: therapy, routines, action drives outcome.
If you’re into honest takes on creativity, business, and real-life connection—with a few laughs along the way—this one’s for you.
14 episodes
