The Remote Islander

Sacha
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A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.

  1. 3h ago

    Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury

    Nine years of remote work, two layoffs over video calls, and a journey from Jamaican radio journalist to Foundpreneur — Stephen Stanbury has seen it all, and he's not holding back. Stephen Stanbury went from getting a letter of termination two months into his first job to becoming a Director of Operations at a fully remote company — all built on grit, Fiverr voiceovers recorded from his closet, and a refusal to let his Caribbean location be a ceiling. In this episode, Stephen unpacks what the remote work landscape really looks like in 2026, what mistakes Caribbean professionals keep making, and why your LinkedIn profile might be the most important job application you never sent. He also shares the story behind his new venture, Foundpreneur — a platform dedicated to spotlighting Caribbean entrepreneurs on a global stage. What we cover: How Stephen went from freelancing on Fiverr (using his company's internet) to Director of Operations — and what it really takes to climb in remote workWhy your LinkedIn profile, personal brand, and AI searchability are now more important than your resumeHow to stand out in a global applicant pool when everyone has an AI-optimised CVThe Caribbean Remote Work Conference 2026 — and why you need to be thereReady to build your remote career on your own terms? Head to theremoteislander.com for resources, episode notes, and more. Guest: Stephen Stanbury — Remote Work Veteran, Personal Branding Strategist, and Founder of Foundpreneur | Find him on LinkedIn: https://www.linkedin.com/in/stephenstanberry/ You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    1h 36m

  2. May 25

    7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24)

    Seven companies. Zero geographic restrictions. All hiring globally - and yes, that includes you. In this episode, I break down seven remote-first companies that are genuinely worth your time as a Caribbean or LATAM professional.  Not companies that "allow" remote work - companies where remote is the foundation.  From the creative-as-a-service world of Superside to the radical salary transparency of Buffer, this is your no-fluff shortlist of employers who have already built the infrastructure to hire you, pay you, and support you across borders. Key topics covered: Why remote-first culture matters more than remote-friendly policy — and how to tell the differenceAutomattic, GitLab, Zapier, Superside, SafetyWing, Remote.com, and Buffer: what each company does and what to expect going inWhy written English is your competitive advantage — and how to sharpen it before you applyThree practical principles for actually landing a role at any of these companiesReady to take your remote career seriously? Start at theremoteislander.com. You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    20 min

  3. May 8

    Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 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 work that pays in USD. If you've ever applied to a "remote" job only to discover it's US-only buried in line four of the description, this episode is for you. I break down the actual platforms, search strategies, and scam red flags — no fluff, no gatekeeping — categorized by industry so you can move fast and move smart. In this episode: Why LinkedIn and Indeed fall short for Caribbean job seekers — and how to use them smarter9 international remote job boards that genuinely mean worldwideCaribbean-specific platforms you probably haven't bookmarked yetHow to spot scams before they waste your timeHow to get paid in USD from the Caribbean (Wise, PayPal, Payoneer and more)A 6-step action plan to execute this week, completely freeYour remote career starts with the right map — head to theremoteislander.com for more resources to help you get there. You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    18 min

  4. Apr 24

    From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 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 Oshido Christie, Remote Career Strategist and Chief Operations Officer at Careevo, to talk about what it really takes for Caribbean professionals to break into the international remote job market. Oshido shares how he went from selling resume templates on Etsy to building a full ecosystem — job board, AI-powered tools, and coaching — designed to keep Caribbean professionals home while earning what they deserve. No fluff, no gatekeeping — just the real process. In this episode: Why mindset is the biggest barrier to landing a remote job (and what to do about it)The 3-part positioning system: resume, LinkedIn, and intro scriptHow Careevo's Job Alignment Tool helps you apply smarter, not harderWhat the Authority Suite is and who it's built forThe Caribbean Remote Job Board: a centralised hub coming to change the gameReady to start your remote career journey? Head to theremoteislander.com Guest: Oshido Christie, Remote Career Strategist & COO at Careevo TikTok/Instagram: _.oshido._ | LinkedIn: Oshido Christie | YouTube: https://www.youtube.com/@UC387mOsaN5rNkRGmm-1fXEA You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    59 min

  5. Apr 17

    How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 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 it. In this episode, I break down the 2026 version of BairesDev: what's new in their application process, who they're actually hiring (hint: it's not just developers), and how Caribbean and Latin American professionals can position themselves to stand out in a pool of over 2.4 million applicants a year. Straight facts — what you need to know before you apply. What's covered: How BairesDev's AI-driven talent matching system actually worksWho's being hired in 2026 — including non-technical roles in HR, marketing, and financeWhy Caribbean professionals have a structural nearshore advantage5 practical tips to sharpen your application right nowThe truth about the talent bench and what silence really meansReady to go remote? Start at theremoteislander.com You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    10 min

  6. Apr 10

    From Fired to Hired: Pris vs. The Remote Job Market (Ep. 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 (aka Pris vs. The World) is a Jamaican copywriter and marketer who built her entire remote career from scratch during COVID lockdowns. In this episode, she sits down with me to talk about losing her remote job, bouncing back fast, and the no-nonsense strategy she used to land a new opportunity before most people even update their resume. Key topics covered: Why "quality over quantity" wins the remote job search every timeHow to stand out in interviews by showing up like you're already on the teamWhy your LinkedIn profile is your remote work marketing page — and what Caribbean professionals are missingUsing AI in your content and job search without sounding like a robotBuilding your personal brand now so opportunities find you before you go lookingVisit theremoteislander.com for more resources on building your remote career from the Caribbean. Guest: Priscilla McClure — Copywriter, Content Marketer & Remote Work Creator 📱 TikTok/Instagram: @prisvstheworld | LinkedIn: Priscilla McClure | YouTube: https://www.youtube.com/@prisvstheworld You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    1h 21m

  7. Mar 30

    AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 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 episode, we break down the AI conversation honestly. No hype, no fear-mongering — just a clear-eyed look at what AI and AI agents actually are, what they can do for your remote career right now, and where the real structural challenges lie for Caribbean and LATAM professionals specifically. This is the episode that turns confusion into strategy. What we cover: The difference between AI tools and AI agents — and why it matters for how you workWhich jobs and tasks are genuinely at risk (and which aren't)Why multilingual AI is a game-changer for our regionThe cultural bias problem in AI — and your role as a cultural editorConcrete steps to future-proof your remote career starting todayReady to go deeper? Visit theremoteislander.com for resources, guides, and everything you need to build your remote career from the Caribbean. You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    14 min

  8. Mar 1

    Building the Burnout-Proof Year (Ep. 18)

    Happy (late) New Year, Islanders! We are almost to the end of the first chapter of 2026, and if you’re already feeling "winded," you aren't alone. While the rest of the world is watching their resolutions gather dust, the "Burnout Beast" is already knocking on the door for many remote workers. In this episode, we define what burnout looks like in 2026—hint: it’s more than just being tired. We’re diving into: The "Sunday Scaries" on a Tuesday: Why your nervous system might be in a constant "threat response".The "Blur": How to escape the 8 AM to 7 PM chair trance.Tactical Recharges: Moving beyond the "scrolling reset" to a true sensory shift.Resources Mentioned: Grab the 30-Day Burnout-Proof Audit: theremoteislander.com.Co-working in Trinidad: Visit Crisha Sarah Bowen at Purpose Spaces.Remote Community: Join Debra Paul-Burgess on the Remotely TT Facebook Page.Level Up Your Schedule: Listen to our previous episode on Time Management & Deep Work.You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog EF SET 15-minute test *Edit: Payoneer has stopped its referral program but you can sign up for an account here.

    10 min
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About

A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.

Information

  • Creator
    Sacha
  • Years Active
    2024 - 2026
  • Episodes
    27
  • Rating
    Explicit
  • Copyright
    © 2026 The Remote Islander
  • Show Website
    The Remote Islander