Work 2.0: The Podcast

In this episode of Work 2.0 , Rachel Wells sits down with Erin Gajdalo , CEO of Pluralsight , to unpack the surprising results from Pluralsight’s 2025 Tech Skills Report , and what they reveal about the disconnect between executive priorities and real employee learning support. From AI-powered upskilling to the hidden cost of abandoned projects, this conversation exposes the leadership blind spots...

What does the CEO of one of the world’s largest online learning platforms think about the future of skills? In this episode, I sit down for an exclusive conversation with Greg Hart, CEO of Coursera, to unpack how the global workforce is being reshaped by automation, AI, and shifting employer demands. We explore the skills that will be in high demand over the next decade, and what learners can do t...

What happens when a U.S. university partners with a Caribbean nation to reimagine the future of work? In this episode, I sit down with Scarlett Howery, Vice President of Public Workforce Solutions at DeVry University, to explore their ground-breaking upskilling initiative in St. Lucia. We dive into: * Why DeVry chose St. Lucia as a strategic partner * How upskilling can transform economies * The s...

I sat down with Glassdoor expert Morgan Sanner and asked the questions every job-seeker wants and needs to know: * How is AI really used in the recruitment process? * How can job-seekers use AI and ChatGPT to optimize their job search strategy and land their dream job? * What's one thing all recruiters and HR managers wish candidates would get, that job-seekers currently aren't getting? Morgan pul...

What does it really mean to be an entrepreneur in 2025? In this episode, I sit down with Oliver Yonchev — co-founder of Flight Story alongside Steven Bartlett, and one of the most forward-thinking voices in modern marketing — to unpack the raw truth about freelancing, creativity, AI, and what it takes to build something sustainable in today’s noisy world. We get honest about: * Why freelancing is...

In this electrifying episode of Work 2.0, I interview a Fiverr freelancer, Harlan Rappaport, who has made over a million dollars and shares exactly how he reached the top. In this episode, we candidly discuss: * Practical advice on when to leave your day job * Why email marketing is an in-demand skill and a great way to make money online * Essential skills you need as a freelancer 🎧 Available now...

In this unfiltered episode of Work 2.0 , we sit down with Derrick Morgan , a former student-athlete turned remote IP attorney, who built a seven-figure solo legal practice on Fiverr . Derrick shares: * How he made his first $1 million freelancing as a trademark attorney * Why he finally decided to hire a paralegal (and how that changed his business) * What it’s really like working as a digital nom...

I sat down with Elise Awwad, DeVry University’s first female CEO in its 90+ year history. She’s making waves, headlines, and pushing boundaries as an innovator and thought leader in tech, AI, and education—three areas that consistently shut out women and ethnic minorities and are typically represented by Silicon Valley “tech bros.” The last time Elise and I sat down for a second candid conversatio...

The era of one job, one paycheck, and one career path is over. In this episode of Work 2.0: The Podcast , I sit down with Janel Abrahami — Glassdoor’s Career Pivot Strategist — to break down the rise of portfolio careers, the future of work, and why diversifying your income streams is a non-negotiable. A recent survey by Glassdoor found that 67% of professionals say their primary motivation for a...

In this solo episode of Work 2.0, I’m breaking down the memo making headlines — Amazon CEO Andy Jassy’s bold prediction that AI will replace a significant portion of the workforce. What does this mean for your career? Is your job safe? And more importantly, how do you stay future-proof when even the biggest companies are signaling massive disruption? Read it for yourself, here . Get full access to...

In this episode of Work 2.0: The Podcast, I sit down with Jon Bostock — CEO, author, and investor, to unpack how leadership is being reinvented in the age of AI, disruption, and rapid change. We explore Jon’s personal journey to the top, why the traditional CEO role no longer works, and what the next generation of leaders and professionals must do to stay relevant, future-proof, and ready to thriv...