#01: The Finances Behind the 12 International Trips She Takes Per Year episode artwork

EPISODE · Jun 9, 2026 · 38 MIN

#01: The Finances Behind the 12 International Trips She Takes Per Year

from How Do You Afford This? · host Ashley Feinstein Gerstley

Ally Case has traveled to 58 countries and takes around 12 international trips a year. She's a content creator, part-time flight attendant, and the CEO of digital marketing agency Uppercase Media, which she runs with a team of five. In our very first episode, she sits down with me to break down how she actually affords the lifestyle. Ally and I walk through exactly what she spent on her recent 8-day trip across Dubai, Abu Dhabi, Oman, and Qatar, the six income streams that fund the fabulous life she’s crafted and the trade-offs she had to make to get there. Plus, she shares how much she gets for free as a travel influencer and her favorite travel hacks the rest of us can use. Ally reveals what’s changed about money in her relationship since getting engaged, the money visualization that drives her career, and why she considers her gold jewelry part of her investment portfolio.Get the travel budget template Ally and Ashley use. https://www.thefiscalfemme.com/travel-budgetConnect with Ally on Instagram at @allycase1 and @uppercase.media, and on TikTok @allycase1.Check out Ashley’s Money Club to join a community of women unabashedly going after their money goals. Take this quiz to get a personalized Wealth Building Blueprint.

Episode metadata supplied by the publisher feed · Published Jun 9, 2026

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Ally Case has traveled to 58 countries and takes around 12 international trips a year. She's a content creator, part-time flight attendant, and the CEO of digital marketing agency Uppercase Media, which she runs with a team of five. In our very first episode, she sits down with me to break down how she actually affords the lifestyle. Ally and I walk through exactly what she spent on her recent 8-day trip across Dubai, Abu Dhabi, Oman, and Qatar, the six income streams that fund the fabu...

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#01: The Finances Behind the 12 International Trips She Takes Per Year

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