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Vagabond: Beating Casinos Around the World
03 November 2026

Vagabond: Beating Casinos Around the World

Gambling With an Edge

About
This is a throwback episode that I cut from 2 episodes in 2019.

Vagabond has played in over 100 countries. A former Air Force interrogation analyst who spent five years at Fort Meade working for the NSA. He talks about how that training shapes the way he questions dealers, how he moves cash across borders.

Show Notes
00:00 Introduction — Vagabond, 100+ countries (and a bad mic)
00:45 How he got started — Deuces Wild in Finland, The Frugal Gambler
02:07 Moving to blackjack — overcoming shyness, talking to dealers
04:50 Intelligence background — NSA, Fort Meade, interrogation analyst
07:19 The Don Johnson inspiration
08:49 Avoiding backoffs — travel anywhere, leave when heat comes
10:06 Carrying cash and customs — Vietnam, the $100 ask
14:27 Currency traps — Colombia, Argentina pesos, Peru soles
16:34 Staying connected — SIM cards, Google Fi
17:34 Cambodia — tracking two eight-deck shoes, $40,000 win
20:30 Favorite and least favorite countries — Mexico, Vanuatu, Afghanistan, Kuwait, Trinidad
23:58 The 15% loss rebate game — triple-down, multi-card surrender, $100K swing
29:59 Madagascar — $70,000 declaration, tiny limits
33:29 Traveling with his wife — and her two passports
35:24 Cheating abroad — Mexico City, Cambodia second-dealing
37:09 Currency headaches — Peru, Chile, India
42:04 Taking notes — detailed casino notes, information broker
45:08 Backoffs abroad — Griffin/OSN, polite Korea tea ceremony
47:49 Coupon AP — Lowe's, Kellogg's, Starbucks, Walgreens
56:36 Staying safe traveling with cash
60:06 Wrap-up