Episode 466- Balancing Corporate Life While Owning Property in Jamaica & Running an Airbnb w/ Leanne Pinkard

Feb 18, 2026

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In this episode, I chat with Lee-Ann Pinkard, who was born and raised in Kingston, Jamaica, and later moved to the U.S. for college at Howard University. She built a career in construction project management and, years later, purchased a beachside property in Jamaica that she now runs as a short-term rental, a property I personally had the pleasure of staying in.

We explore what it really takes to buy property in Jamaica, the realities of managing an Airbnb from abroad, how she balances corporate life, motherhood and her long-term plan to retire back home.

In this episode, we discuss:

Lee-Ann's journey and career path – Growing up in Kingston, studying engineering at Howard University, and building a career in construction management in the U.S.
Buying and financing property in Jamaica – What it really takes to purchase abroad, how mortgages and banking differ from the U.S., and the importance of local connections
The real costs and challenges of owning an overseas Airbnb – Unexpected expenses, hurricane impacts, solar panel investments, and managing a short-term rental remotely
Investing with purpose and planning for retirement – The emotional connection to returning home, building long-term wealth, and redefining retirement beyond simply not working

What's New in the Paperback Edition of Your Journey to Financial Freedom:

A bonus chapter: When Life Happens: Staying on the Path to Financial Freedom Through Setbacks, Shifts, and Uncertainty
A book club and discussion guide with prompts, exercises, and action steps
Updated corrections from the original hardcover
Exclusive bonuses when you purchase the paperback, including:
- The Fire Starter Course
- The Find Your FIRE Number Worksheet

Other related blog posts/links mentioned in this episode:

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