Episode 466- Balancing Corporate Life While Owning Property in Jamaica & Running an Airbnb w/ Leanne Pinkard
Journey To Launch
Jamila Souffrant
4.9 • 1.7K Ratings
🗓️ 18 February 2026
⏱️ 59 minutes
🧾️ Download transcript
Summary
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:
- Listen to my episode "What My Recent Trip to Jamaica Reminded Me About Wealth, Gratitude, and Resilience"
- Get your paperback edition of Your Journey To Financial Freedom if you haven't already.
- Apply to Share Your Journeyer Story, here.
- Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
- Join The Weekly Newsletter List to get updates, deals & more!
- Leave Your Journey To Financial Freedom a review!
- Get The Budget Bootcamp
- Check out my personal website here.
- Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
- YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
- What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!
Connect with Lee-Ann & Learn More About Sea Miracle Jamaica:
Connect with me:
- Instagram: @Journeytolaunch
- Twitter: @JourneyToLaunch
- Facebook: @Journey To Launch
- Join the Private Facebook Group
- Join the Waitlist for My FI Course
- Get The Free Jumpstart Guide
Transcript
Click on a timestamp to play from that location
| 0:00.0 | When you fly Emirates on business, you can relax from the start. |
| 0:04.3 | You get a complementary chauffeur-driven transfer from your door to the airport. |
| 0:08.5 | Then when you land, your chauffeur will be ready to take you wherever you want to go. |
| 0:13.1 | It's exclusive for Emirates First and business class travellers. |
| 0:16.7 | And with world-class service in the Emirates Lounge and exceptional comfort on board, |
| 0:21.6 | it's just a better way to do business. |
| 0:23.8 | Book now on emirates.com. |
| 0:28.3 | If my work is because I want to. |
| 0:30.6 | It should be something that fills my soul. |
| 0:32.7 | Like, I want to go and just work maybe I'm going to go volunteer here or do this or run a little Airbnb or whatever, |
| 0:39.4 | but something that should be pleasurable to me and not something that I have to do it in order |
| 0:43.5 | to live. |
| 0:43.9 | That is my fear. |
| 0:46.2 | It's not planning properly enough for retirement that I still have to work. |
| 0:53.0 | Welcome to the Journey to Launch podcast with your host, Jamila Sufron. |
| 0:57.7 | As a money expert who walks her talk, she helps brave journeyers like you, get out of debt, save, invest, and build real well. |
| 1:07.5 | Join her on the Journey to Launch to Financial Freedom in five, four, three, two, one. |
| 1:19.6 | If you want the episode show notes for this episode, go to Journey tolaunch.com or click the |
| 1:25.8 | description of wherever you're listening to this episode. |
| 1:28.8 | In the show notes, you'll get the transcribed version of the conversation, the links that |
| 1:33.8 | we mentioned, and so much more. Also, whether you are an OG journeyer or brand new to the |
| 1:39.6 | podcast, I've created a free jumpstart guide to help you on your financial freedom journey. |
... |
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