The Remote Islander

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

The Remote Islander is a business podcast hosted by Sacha, with 32 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Sacha hosts The Remote Islander, a business show with 32 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #30

  Remote work Gatekeeping called OUT! (Ep. 30)

  Aug 13, 202612 min

  What if the real gap between you and a remote job isn't information, it's action? This episode, I'm getting into something that's been on my mind for a while: the claim that Caribbean remote work voices like Krishna Dewor, Priscilla McClure, and Oshido Christie are gatekeeping opportunities from the rest of us. Spoiler: they're not, and I'll walk you through what's actually happening instead. In this episode: Why the "gatekeeping" label gets thrown at career creators everywhere, not just here What competing in a truly global remote job market actually looks like The nine months it took me to land my next role after sixteen years in an office Seven concrete moves to make this week if you're serious about landing remote work The one thing most people skip: actually asking for help Head to theremoteislander.com for more tools to help you land your next remote role. Also check out the Global Caribbeans job board and the recap of the Caribbean Remote Work Conference 2026 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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  Episode #29

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

  Jul 30, 20261h 12m

  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 straw The real meaning of ATS and why your resume gets filtered before a human ever sees it Zendesk, 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 terms Listen 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 .

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  Episode #28

  Remote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 28)

  Jul 23, 20261h 6m

  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 story The instant disqualifiers most candidates don't even know about Why trust is the real barrier to tech adoption in the Caribbean, and how to build it What actually makes a remote candidate stand out (hint: it's not your degree) The home workspace habits that signal you're ready for remote work If 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 .

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  Episode #27

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

  Jul 16, 202631 min

  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 hiring The truth about ATS systems and why 92% of recruiters aren't auto-rejecting your resume Why your location filter might be quietly killing your job search The staggering LinkedIn visibility gap facing Caribbean professionals What Latin America's remote work boom can teach (and warn) the Caribbean Ready 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 .

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  Episode #26

  How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 26)

  Jun 8, 202642 min

  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 income The four statutory deductions every self-employed remote worker must account for How to set up your account with Tax Administration Jamaica (TAJ) and file as self-employed Deductible business expenses — including your internet and phone The 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 .

  ListenShow Notes

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