The Rethinking Work Show

What if being a company of one wasn’t just a structure, but a strategy? Flavia Barbat, editor-in-chief of Brandingmag, shares how professionals can build careers around clarity, substance, and intention in a world where content is everywhere but meaning is rare.As founder of Brandium, Inc. and Editor-in-Chief of Brandingmag, Flavia has been responsible for nurturing and promoting the creation of purposeful thought leadership for over a decade. She represents undiscovered talent within branding and beyond, and vouches for the industry’s collective responsibility to safeguard human creation in an age of synthetic content. Flavia also consults leading B2B organizations on building scalable content platforms through her “editorial marketing” mindset. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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 Environment. Naama brings over 20 years of global marketing leadership across startups, enterprises, and public companies. She’s driven $50M+ in investments, M&As, and IPOs through strategic planning and brand growth. Her expertise spans industries like Technology, Consumer Products, AdTech, AgeTech, E-Commerce, and Cloud Computing.Clive Sirkin serves as the head of Marketeam.ai's board of advisors. He is a seasoned global CPG executive with over 30 years of leadership experience across multinational companies, known for driving innovation, transformation, and shareholder value. Most recently, Clive served as Chief Growth Officer at the Kellogg Company, where he was part of the Executive Committee and led R&D, Innovation, Sales, Marketing, and Analytics. Prior to Kellogg, Clive was Chief Marketing Officer at Kimberly-Clark, where he oversaw global marketing across both B2B and B2C divisions. Clive’s career began at Leo Burnett, where he spent over 16 years rising through the ranks to become Group Managing Director of Leo Burnett Worldwide.Tony Weisman serves on the advisory board for Marketeam.ai. He is a globally recognized marketing executive with over 30 years of experience leading iconic brands through digital transformation and growth. He served as CMO of Dunkin’ US, where he rebranded the company, launched successful product innovations, and led record sales for the business. As CEO of Digitas, he led a 2,000-person team and built the industry's largest data science group. Tony sits on the boards of Klaviyo, Later, InMoment, and others, and advises top private equity firms. Known for building dynamic, diverse teams, he’s also a frequent speaker and was named a Forbes World’s Most Influential CMO. Tony currently serves on the Board of the Mobile Marketing Association. He was also the former Chairman of Chicago Public Media (WBEZ). EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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. His experience spans Big 4 consultancies, start-ups, and his own advisory firm, with clients including the NHS, John Lewis Partnership, Novartis, Deloitte, Corporate Research Forum, CIPD, ADP, Wikistrat, and McLaren. His work bridges sectors—from tech and think-tanks to universities and non-profits. Andy has delivered keynotes and executive workshops across the world—from London and Paris to Singapore, Sydney and Shanghai. Audiences value his ability to distil global megatrends into actionable insight, blending data-driven analysis with compelling storytelling. He publishes the popular Work 3 Newsletter, followed by 30,000+ professionals weekly, and his pioneering work with Don Tapscott on blockchain in the workplace has influenced entrepreneurs and technologists globally. Industry recognition includes being named a Top 100 HR Tech Influencer by HR Executive Magazine and a Key Opinion Leader in the Future of Work by Onalytica. He holds a Master’s in Cognitive Science (AI) from the University of Birmingham, is a Fellow of the RSA, Senior Industry Fellow at RMIT, and a professional member of the Center for Evidence-Based Management. Originally from Manchester, Andy now lives in Lisbon, helping CHROs and senior leaders navigate the shifting landscape of work.  EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

Kyle Csik, CEO and Co-Founder of Adaly, an enterprise AI platform, shares his insights on how AI is revolutionizing workplace dynamics. He discusses the challenges of managing fragmented data and introduces 'enterprise cognition' for improved decision-making. Kyle emphasizes AI's dual impact—both job displacement and new opportunities, especially for Gen Z. He advocates for a partnership between AI and humans, pinpointing the need for quality data and nurturing relationships to achieve success while fostering creativity and purpose in work.

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 leader who challenges the status quo and believes deeply in the power of creativity to transform brands, businesses and communities. Andrew's agency, A&G, works with some of the most recognizable brands, from Dunkin' to Amazon/One Medical and Blue Cross Blue Shield, to Meet Boston and the world renown Boston Symphony Orchestra. He's been recognized as an EY Entrepreneur of the Year finalist, as one of the most influential business leaders in Boston by Boston Magazine and Boston Business Journal, and Adweek has honored him as one of the top 100 advertising leaders in the U.S. A&G has been recognized by AdAge, Boston Business Journal and The Boston Globe as a best place to work. He’s also a frequent speaker on topics including 'Marketing to the Ageless Generation', featured in Fast Company and the Age Tech Collaborative. To drive transformative change, Andrew gets involved in the advertising industry leadership as an Executive Board Member for the national advertising agency association, 4As. Speaking and judging for the ANA (Association of National Advertisers), Chair Emeritus of the Ad Club of Boston and recent past Executive member of the Greater Boston Chamber of Commerce. He serves on the advisory board for an ad tech company, Pixability. Andrew is deeply invested in community impact, serving as Board Chair of Big Sister Boston (now part of Big Brother Big Sister of Eastern Massachusetts) and on the boards of The Sports Museum and the Boys & Girls Clubs of Dorchester. Andrew resides in Boston with his wife and proudly embraces his role as a father to his two daughters. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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 skills-based career paths and learning plans. Career Bird empowers individuals to understand where they are, where they want to go, and how to get there, while giving companies the tools to retain top talent and foster continuous learning cultures.With a focus on clarity, accessibility, and speed to value, Career Bird is built for modern teams navigating a rapidly changing world of work. The platform serves employees, managers, and HR leaders with tools for skills assessment, role clarity, job architecture, and internal mobility.Matt is also the Managing Director of Wavetable Studio, a venture studio he founded to launch startups that combine mission, creativity, and scalable impact. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.    

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 Anywhere Boosts Talent, Productivity, and Innovation." Available for purchase on Amazon.Dr. Prithwiraj Choudhury is the Lumry Family Associate Professor at Harvard Business School, and one of the leading thinkers on how work is evolving in a post-office world. His research focuses on the changing geography of work—exploring everything from remote work and “work from anywhere” models, to what drives or prevents geographic mobility. Before Harvard, Raj taught at Wharton, and before academia, he worked at McKinsey, Microsoft, and IBM. He brings not only academic rigor but real-world experience to his ideas. Raj’s work has been featured everywhere from the New York Times to Freakonomics to Harvard Business Review—and in 2023, he was named to Forbes’ Future of Work 50 list. EPISODE CREDITSProduced, edited and mixed by Ria TobaccowalaArtwork designed by Ben DamianoAdditional music licensed through Premium BeatsLINKSExplore more about the new frontiers of work at Rethinkingwork.ioFor more actionable insights that inspire subscribe to Rishad Tobaccowala's free weekly substack: The Future Does Not Fit In The Containers Of The Past. This show is also available on YouTube which includes visual supplements. Rishad's Book Rethinking Work is available in print and audio. Click here for where to buy.