Remote Work Life Podcast

Remote Work Life Podcast

At Remote Work Life, we spotlight successful location-independent entrepreneurs and established remote work professionals. Our interviews highlight their journeys and growth strategies, and their inspiring stories offer ideas for your entrepreneurial and professional ventures and reveal insights on thriving while working remotely.

Episodes

April 20, 2025 6 mins

What happens when a founder decides to step off the venture capital treadmill and build a business focused on sustainable growth instead of unicorn status? Sahil Lavigna's journey with Gumroad provides a refreshing alternative to typical Silicon Valley narratives.

Gumroad eliminated office space, stripped back to core functionality, and rebuilt around a simple promise: helping creators earn a living with minimal frict...

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Discover how Sam Rosen, co-founder and CEO of DeskPass, turned a pivotal moment in New York into a global movement redefining where and how we work. Sam's journey from designing in Chicago to building a flexible workspace marketplace will inspire you to rethink traditional office environments. 

Learn how his unique blend of creativity and technology insight has driven DeskPass to become a leader in connecting companie...

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In today's episode Ashley Widener, the Director of Marketing at GoCo, talks through her journey from the conventional office life in Houston to a fully remote work setup. She's built and led a globally distributed marketing team and her  plans to live and work from a van are intriguing. Ashley's story is not just about adapting to change but embracing it, all while maintaining a vibrant company culture.

Ashl...

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Kara Şahbaz is founder of the Untethered Minimalist, and transitioned from a holistic health coach to work in tech and automation. Kara's time in Saudi Arabia was a turning point, sparking her entrepreneurial spirit and leading her to become a digital nomad. You'll learn how her observations as a teenager influenced her commitment to finding joy in her work and how she overcame personal challenges like anxiety and agoraph...

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Imagine merging your professional skills with your deepest passions—Weston Davis has done just that. As a digital marketing freelancer with a love for martial arts, Weston shares his journey from the hospitality industry to a life of location independence. Inspired by Tim Ferriss' "Four Hour Workweek," he reveals how he carved out a niche in SEO and content creation while building a martial arts website that offers e...

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In today's episode Jim Frawley, the founder of Bellwether, describes how he went from the high-pressure world of Wall Street to becoming a sought-after change management expert.

Jim's story is a testament to the power of personal milestones—like the birth of his daughter—that catalyze profound life changes, including quitting drinking and starting his own business.

With core values of recognition, altr...

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FROM ARCHIVE With WordPress powering a third of the internet, Alex Denning offers a look at his journey and the innovative strategies his agency employs to support WordPress businesses. From his early days at Miniclip to founding WP Shout and ultimately Ellipsis, Alex's story is a testament to the power of passion and persistence.

Curious about the steps of building a successful remote team? Alex opens up about the ch...

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FROM THE ARCHIVE: Rowena Henigan shares her personal story of transitioning to remote work amidst family health challenges and how it allowed her to maintain her career while moving to Spain for her child's asthma. Discover how remote work has empowered Rowena, both personally and professionally, from her early days with a telecommunications company to her roles with large insurance companies and her aspirations as a digital n...

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Ever wondered how to combine your love for sports, travel, and helping others into a thriving business? Marlon Schadeck, the Founder/ fitness coach behind Nomad Strong, joins us to share his journey from Germany to Mexico.

He talks about the pivotal moment during an internship in Guadalajara that shifted his career path from aspiring teacher to fitness entrepreneur.

Together with his partner Joe Miller, Marlon h...

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FROME THE ARCHIVE:What does it take to build a successful remote company during uncertain times? I had a conversation with Sondre Rausch, CEO of Safety Wing back 2019 and he shared his journey from a teenage entrepreneur in Norway to a pioneer in global travel and medical insurance for remote teams and nomads.
 
Sondre shared how his early fascination with technology and entrepreneurship evolved, his educational background ...

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FROM THE ARCHIVE: This replay focuses on my conversation with Dipesh Patni, Founder of GravitasQ. Dipesh shares his journey from a high-flying sales career to mastering SEO, revealing the challenges and skills required to stand out in a competitive industry. This episode gives practical advice for anyone looking for personal and business growth within digital marketing while maintaining productivity and mental well-being.

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From the Caribbean to Kuala Lumpur and beyond, Neil Ateem's journey from working in Trinidad and Tobago’s tech and oil sectors to becoming a globe-trotting entrepreneur is extraordinary. He's a Co-Founder Of Multiplier and shares the ins and outs of transitioning to remote work, overcoming hurdles in the Caribbean, and his pivotal role at Mindvalley in Kuala Lumpur.

Neil’s passion for marketing and leadershi...

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FROM THE ARCHIVE:What if you could revolutionize your business by abandoning the office altogether? Join us as we explore the extraordinary journey of Matthew Stibbe, the founder of Articulate Marketing, who is building of a fully remote B2B marketing firm.

Ever wondered how to create a close-knit team without a physical office? Matthew shares his  strategies for team bonding and collaboration remotely, including book club...

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In a world where the traditional 9-to-5 job is increasingly being questioned, Gleb Gordeev stands out as an example of how remote work can lead to both professional success and personal fulfillment. In this enlightening podcast episode, Gleb shares his journey from working in Europe's top tech companies to founding Codebusters, a thriving product development agency.

The episode reveals his life-changing trip during t...

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What if you could trade your 9-to-5 for a life of freedom, travel, and entrepreneurial success? That's the inspiring story of Niluka Kavanagh, the visionary founder of ImagineThat.

ImagineThat is the business school for digital nomads and solopreneurs. It is for ambitious but bored professionals who want to start offering their service independently online so they can a) work for themselves and b) gain location freed...

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FROM THE ARCHIVE:Ever wondered how remote teams can truly bond and feel connected despite the physical distance? This episode of Remote Worker Life features Badri Rajasekhar, former CEO of Jam, who shares his remarkable journey from Chennai to Microsoft and beyond. Learn about his bold decision to join a startup during the 2008 financial crisis and how it led to the creation of Jam, a video collaboration app that promises to make r...

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. This episode of the Remote Work Life podcast reveals the tech essentials that can keep your remote team connected and productive without the stress of overcomplicating your setup. Greg Caplan shares his no-nonsense approach to selecting the right tools—whether it's Zoom, Slack, or Google Meet—and underscores the importance of a strong team culture to make these tools shine.


Refer a Remote Work Expert As a Guest...

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In the latest episode of the remote work life podcast, I had the pleasure of hosting Dan Yoder -  CEO of Panda Strike /DashKite - for a second time. The conversation spanned a wide array of topics including generative programming, the importance of building consentful applications, and the evolving landscape of remote work. Dan's insights were particularly illuminating, offering a glimpse into the future of tech and remote wor...

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Ever wondered how a gift from your childhood could shape your entire career? In this episode of Remote Work Life, we sit down with Alina Vandenberg, CPO of Chili Piper, who shares her incredible journey from the confines of communist Romania to becoming a leading figure in tech entrepreneurship. Alina recounts how her father's gift of a computer ignited her passion for technology, ultimately setting her on a path to pursue com...

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Discover the inspiring story of Harriet McCullough, a dynamic B2B marketing manager at Pion, formerly known as Student Beans. Harriet takes us through her remarkable journey, sharing her expertise in community building, event planning, social media management, and digital PR. Learn how she emphasizes the creation of authentic brand connections and hear about her personal goal of enhancing her LinkedIn presence, demonstrating the im...

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