business
Hosted by Sacha · business · EN-US
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
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Contact path
Public web form
Booking probability
30%
Guest openness
Selective
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Signup to Generate a PitchThe Remote Islander is hosted by Sacha. The show has published 33 episodes to date.
Recent episodes include "Is Virtual Assistant Work Right for You? Honest Talk with The VA Mom, Desi-Ann Gordon" (13 October 2026, 83 minutes), "Remote work Gatekeeping called OUT! (Ep. 30)" (14 August 2026, 12 minutes), and "Pick, Choose, Refuse: The Remote Career Krishna Dewor Built (Ep. 29)" (31 July 2026, 72 minutes).
The Remote Islander publishes roughly every two weeks, with episodes averaging 38 minutes across 33 episodes.
Booking probability for The Remote Islander is 30%, and the host is rated Selective on guests. The Remote Islander requires a Pod Score of 80 or higher. The Remote Islander's contact route on record: public web form.
The strongest fits for The Remote Islander are Staffing & Recruiting and Business & Management Consulting. The Remote Islander has a business audience.
Sacha hosts The Remote Islander, a business podcast with 33 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.
Episode #31
Ever wondered if your organizing skills could become a business that serves clients around the world, from home? Remote Islanders, this one is for every boss organizer out there. I sat down with Desi-Ann Gordon, founder...
Episode #30
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...
Episode #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...
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 week I sit down with Tahirah Banks-Webster, founder and strategist from...
Episode #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...
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 this episode, I sit down with Colette Guthrie, a tax professional at...
Episode #25
<p>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.</p><p>Stephen Stanbury went from...
Episode #24
<p>Seven companies. Zero geographic restrictions. All hiring globally - and yes, that includes you.</p><p>In this episode, I break down seven remote-first companies that are genuinely worth your time as a Caribbean or...
Episode #23
<p>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.</p><p>If you've ever applied to a "remote" job...
Episode #22
<p>Landing a remote job from the Caribbean in 90 days or less — is it actually possible? This episode breaks down exactly how.</p><p>Sacha sits down with Oshido Christie, Remote Career Strategist and Chief Operations...
Episode #21
<p>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.</p><p>In this episode, I break down the 2026 version of...
Episode #20
<p>Lost your remote job? Here's how one Caribbean professional went from contract terminated to new retainer client — in under a month.</p><p>Priscilla McClure (aka Pris vs. The World) is a Jamaican copywriter and...
Episode #19
<p>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.</p><p>In this episode, we break down the AI conversation honestly. No hype...
Episode #18
<p>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...
Episode #17
<p>In the episode, I interview Crisha Sarah Bowen about her 10-year journey as a coach, her unique path to starting a co-working space, and her message of "living in your purpose". Crisha details her spontaneous start...
Episode #16
<p>In this episode, I talk with my longtime friend, Crystal Duncan, about the power of support systems in a remote career. Crystal, who has served as a cheerleader and guide to many new remote workers, shares the...
Episode #15
<p>Wondering how to level up your remote work career? </p><p>In this episode of The Remote Islander, we dive into the strategies for career growth when you're working remotely. </p><p>We cover how to stay visible to...
Episode #14
<p>Level up your remote work game in the second part of our "Complete Remote Worker's Guide"! </p><p>This episode, "The Technical Toolkit," focuses on the essential hard skills and digital tools that empower efficient...
Episode #14
<p>Dive into the essential human elements of working from anywhere in the first part of our "Complete Remote Worker's Guide"! </p><p>In this episode, "The People Side of Remote Work," we unpack the crucial soft skills...
Episode #13
<p>Are you feeling uninspired or unproductive in your home office? You're not alone! Your workspace plays a HUGE role in your daily focus and overall wellbeing. </p><p>In this episode, we dive deep into the world of...
Recent guests on The Remote Islander. Study who booked and why before you pitch.
PriceWaterhouseCoopers Jamaica
Careevo
WorkBetterNow
PitchCentric classifies The Remote Islander under these industries. Guests from them are the closest fit, and each links to the best podcasts in that industry.
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