The Rethinking Work Show

What if your career wasn’t just one job, but a collection of roles that reflect your skills, interests, and values? Ben Legg, co-founder and CEO of The Portfolio Collective, shares how the portfolio career model is helping professionals design more flexible, purpose-driven lives, and why the future of work may look more like a mosaic than a ladder. Ben Legg helps business leaders and investors nav...

What happens when AI becomes part of your workforce, not just your toolkit? MarkeTeam.ai Co-Founder Naama Manova-Twito and Board Members Clive Sirkin and Tony Weisman, share how AI coworkers are reshaping marketing workflows and why the future of marketing will be human-led, AI-empowered. Naama Manova-Twito is the Co-Founder & CEO of Marketeam.ai, the world's first agentic Integrated Marketing Env...

How do we retrain millions of workers for jobs that don’t exist yet? Workforce futurist Andy Spence joins Rishad to talk about closing the skills gap, preparing for AI-driven change, and why retraining is the most urgent challenge facing the modern workforce. Andy Spence is a leading voice in workforce strategy, with over two decades advising global organisations and the C-suite on how to build be...

How is AI changing the way we collaborate, create, and make decisions at work? Kyle Csik, CEO and Co-Founder of Adaly, joins Rishad to explore how intelligent systems are reshaping our roles and how we can stay curious, creative, and in control in an AI-powered workplace. Kyle Csik is the CEO and co-founder of Adaly, an enterprise AI platform transforming how companies turn data into action. With...

What happens when a CEO rethinks office culture from the ground up? Andrew Graff, CEO of Allen & Gerritsen, shares why he brought his team back together—not out of tradition, but through intention, trust, and a bold redesign of how people connect at work. Andrew Graff is the CEO of A&G (Allen & Gerritsen), an independent, integrated creative agency located in Boston and Philadelphia. Andrew is a l...

Can a workspace make us feel more connected, creative, and alive? Architect and artist Dan Cheetham shares how design—rooted in art, music, and human experience—can turn ordinary offices into places of meaning and collaboration. Dan Cheetham is the founder and managing principal of FYOOG , an IA Interior Architects Company. Inspired by his musical background and after stops in New York, London, Sa...

What does a modern career path look like when the job market keeps changing? Career Bird Founder & CEO Matt Moog joins Rishad to explore how AI and data can help people navigate their skills, goals, and growth in a world without straight-line careers. Matt Moog is the Founder & CEO of Career Bird , a talent development platform helping organizations unlock the potential of their workforce through...

If work isn’t a place, how do we measure impact, build culture, or grow careers? Harvard Business School professor and author Dr. Prithwiraj Choudhury shares insights from the front lines of the remote work revolution. To dive deeper into the concepts, research and guidance discussed in this episode, please explore Dr. Prithwiraj Choudhary's new book called "The World Is Your Office: How Work from...