The Remote Islander

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

  1. 1d ago

    Pick, Choose, Refuse: The Remote Career Krishna Dewor Built (Ep. 29)

    Ever wondered how to get to a point in your career where you can CHOOSE your next job? Krishna Dewor has the answer. Krishna is a Client Support Concierge based in Kingston, Jamaica, with eight years of remote work under his belt. He was one of the amazing speakers at the first Caribbean Remote Work Conference in June, where thousands tuned in for his breakdown of what actually makes a resume work.  In this episode, we get into it all: over-communication as a remote work superpower, why your resume needs to change for every single job you apply to, debunking "gate-keeping" and why AI and no-code tools like Zapier are becoming must-have skills, not nice-to-haves. What we cover: How Krishna went from a hybrid role to fully remote, and why the commute was the final strawThe real meaning of ATS and why your resume gets filtered before a human ever sees itZendesk, Salesforce and the no-code tools worth learning even if you're not "technical"What to do to take your remote career to the next level - pick, choose and refuse jobs on your own termsListen to the full conversation and check out more resources at theremoteislander.com. Guest: Krishna Dewor, Client Support Concierge, Kingston, Jamaica Connect with Krishna on LinkedIn 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.

  2. Jul 24

    Remote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 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 week I sit down with Tahirah Banks-Webster, founder and strategist from Anguilla who runs AlphaNorth Global and ShipSmart Logistics. Unlike most guests on the show, Tahirah isn't looking for remote work, she's the one doing the hiring, building and leading distributed teams across the Caribbean and the US. She pulls back the curtain on exactly what employers are really looking at when your application lands in front of them. In this episode: Tahirah's three-part hiring process, and why LinkedIn's "good fit" score isn't the whole storyThe instant disqualifiers most candidates don't even know aboutWhy trust is the real barrier to tech adoption in the Caribbean, and how to build itWhat actually makes a remote candidate stand out (hint: it's not your degree)The home workspace habits that signal you're ready for remote workIf you're serious about landing a remote job, this is the episode that shows you exactly what's happening on the other side of the screen. Head to theremoteislander.com for more. 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.

  3. Jul 17

    The Real Reason Caribbean Professionals Aren't Getting Remote Jobs (Ep. 27)

    The Caribbean has genuine remote work advantages: English fluency, cultural alignment with North America, strong technical education, so why isn't the opportunity converting at scale?  In this episode, I break down the real, data backed reasons the Caribbean remote work gap exists, and it's not the reason most people think. From IMF brain drain figures to a LinkedIn presence problem that's bigger than anyone admits, this is a no fluff look at what's actually holding Caribbean professionals back, and what to do about it starting today. In this episode you'll learn: Why the "just get a degree" advice is outdated for global hiringThe truth about ATS systems and why 92% of recruiters aren't auto-rejecting your resumeWhy your location filter might be quietly killing your job searchThe staggering LinkedIn visibility gap facing Caribbean professionalsWhat Latin America's remote work boom can teach (and warn) the CaribbeanReady to stop guessing and start strategizing your remote career? Head to theremoteislander.com for more episodes, resources, and real talk on building a global career from home. 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.

  4. Jun 9

    How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 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 this episode, I sit down with Colette Guthrie, a tax professional at PriceWaterhouseCoopers Jamaica, to break down exactly what Jamaican remote workers need to know about paying their taxes correctly. We cover: How tax residency works and why it means you're taxed on your worldwide incomeThe four statutory deductions every self-employed remote worker must account forHow to set up your account with Tax Administration Jamaica (TAJ) and file as self-employedDeductible business expenses — including your internet and phoneThe biggest mistakes people make when filing (and how to avoid them)Head to theremoteislander.com for the full Jamaican Remote Worker Tax Guide, a free resource to go alongside this episode. Guest: Colette Guthrie — Tax Professional, PwC Jamaica  LinkedIn: https://www.linkedin.com/in/colette-guthrie-adit-03558062/  Instagram: @thoughtstothewise  Facebook: https://www.facebook.com/share/18ceCDK36F/ 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.

  5. Jun 1

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

  6. 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.

  7. 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.

  8. 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.

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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
    31
  • Rating
    Explicit
  • Copyright
    © 2026 The Remote Islander
  • Show Website
    The Remote Islander