The rethinking work show
Rethink How We Work, Why We Work, And What Work Should Become.
Rethinking Work is a show hosted by Rishad Tobaccowala about how work is changing and how we can change with it. In each episode, Rishad sits down with bold thinkers, builders, and leaders to explore the future of work across industries. From remote work and AI to purpose, creativity, and culture, we uncover the ideas reshaping how we live, lead, and grow in today’s world.
Subscribe to hear fresh, human conversations about what work can and should become.
How to build a portfolio career | July 23 2025
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 navigate the rapidly changing world and position themselves and their teams for success. Early career included relieving the siege of Sarajevo in 1995, McKinsey strategy consultant, turning around Coca-Cola India, COO of Google Europe and global tech CEO. In 2020 Ben cofounded The Portfolio Collective, to help professionals understand, launch, manage and grow successful portfolio careers - as a community.
How AI Coworkers Are Transforming Work | July 16 2025
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.
Andy Spence, Reskilling for the Age of AI | July 9 2025
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 better, people-centric workplaces.
Originally from Manchester, Andy now lives in Lisbon, helping CHROs and senior leaders navigate the shifting landscape of work.
Kyle CsiK, CEO and co-founder of Adaly | July 2 2025
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.
Andrew Graff, CEO of Allen & Gerritsen | June 25 2025
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.
Dan Cheetham, founder & managing principal of FYOOG | June 18 2025
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, San Francisco, and Shanghai, Dan formed FYOOG, a studio based in Austin, TX. FYOOG is devoted to creating one-of-a-kind immersive sculptures that reflect and celebrate the unique essence of each client and place in a multi-layered composition, often supplemented with elegant architectural enhancements that transform space into places that engage, inspire, and delight.
Matt Moog, Founder & CEO of Career Bird | June 11 2025
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.
Dr. Prithwiraj Choudhury | June 4 2025
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 concept, research and insights from today's guest, please consider purchasing his new book, "The World Is Your Office: How Work from Anywhere Boosts Talent, Productivity, and Innovation".