Podcast Episodes
Back to SearchRemote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 28)
Episode 28
What does it actually take to get hired for a remote job, straight from the person on the other side of the table making the hiring decisions?
This we…
4 hours ago
The Real Reason Caribbean Professionals Aren't Getting Remote Jobs (Ep. 27)
Episode 27
The Caribbean has genuine remote work advantages: English fluency, cultural alignment with North America, strong technical education, so why isn't th…
1 week ago
How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 26)
Episode 26
If you're earning money from a foreign employer and living in Jamaica, you have a tax obligation - and it's yours to manage, not your employer's.
In …
1 month, 2 weeks ago
Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury (Ep. 25)
Episode 25
Nine years of remote work, two layoffs over video calls, and a journey from Jamaican radio journalist to Foundpreneur — Stephen Stanbury has seen it …
1 month, 3 weeks ago
7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24)
Episode 24
Seven companies. Zero geographic restrictions. All hiring globally - and yes, that includes you.
In this episode, I break down seven remote-first comp…
1 month, 4 weeks ago
Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 23)
Episode 23
Stop wasting time on job boards that weren't built for you — here's exactly where Caribbean professionals should be looking for legitimate remote wor…
2 months, 2 weeks ago
From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22)
Episode 22
Landing a remote job from the Caribbean in 90 days or less — is it actually possible? This episode breaks down exactly how.
Sacha sits down with Oshid…
3 months ago
How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21)
Episode 21
BairesDev is still one of the best doors into USD-paying remote work from the Caribbean — but the way in has changed, and most applicants don't know …
3 months, 1 week ago
From Fired to Hired: Pris vs. The Remote Job Market (Ep. 20)
Episode 20
Lost your remote job? Here's how one Caribbean professional went from contract terminated to new retainer client — in under a month.
Priscilla McClure…
3 months, 2 weeks ago
AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 19)
Episode 19
AI is reshaping remote work fast — and if you're a professional in the Caribbean or Latin America, you need to know exactly where you stand.
In this e…
3 months, 3 weeks ago