At 25, Riley Simmons decided the safe path wasn’t his path. After a stint in the Marine infantry and a climb into corporate finance, the promotion he’d been eyeing crystallized one truth: he didn’t want that life. So he saved, simplified, and bought a one-way ticket. In this episode we unpack the real planning behind a bold leap—monthly burn, student loans, keeping an apartment, and why Southeast Asia is his “in case funds dip” landing zone. We map the early route (Frankfurt → Berlin → Casablanca/Taghazout → Florence), talk surfing world-class Anchor Point, hostel living, Workaway gigs, staying safe in unfamiliar cities, and growing from zero social presence to daily updates. Also starring: Iris, the border collie he hopes to eventually reunite with abroad.
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If you’re in Germany, Morocco, Italy, Greece, Turkey, Poland, Romania, Lebanon—or on a great surf break anywhere—DM Riley. Local tips, hikes, cheap eats, and spare couches welcome.
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Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.
