The Rethinking Work Show

Justin Billingsley, co-founder of Simbioniq and former Global CMO of Publicis Groupe, builds AI-driven marketing tools and writes on orchestration. He discusses moving from big-company life to entrepreneurship. He explains using AI to simulate people for better market research. He argues leadership should orchestrate systems, not act as heroes. He urges rapid experimentation, embracing failure, and making work not just faster or cheaper but truly better.

Are we preparing students for the world of work or a world that no longer exists? Authors Alexandra Levit and Stephanie Loeck explore how work-based learning can close the gap between education and employment, and why real-world experience, not just classroom instruction, may be the key to building adaptable, future-ready talent. Purchase and learn more about their book Make School Work here: https://makeschoolwork.org/ Alexandra Levit is the founder and CEO of Inspiration at Work, a futurist consulting firm dedicated to helping organizations and their employees thrive in a rapidly evolving business landscape. A former nationally syndicated columnist for The Wall Street Journal, Alexandra is the bestselling author of They Don’t Teach Corporate in College, Humanity Works, and Make School Work, which addresses the American youth employment crisis through work-based learning. She holds a certificate in strategic foresight from the University of Houston and advises leading organizations including Deloitte, American Express, Adecco, and Upwork on leadership, workforce transformation, technology adoption, and skills development. Alexandra has collaborated extensively with U.S. government agencies, including the Department of Labor and Department of Defense, and her work has been featured in outlets such as The New York Times, Forbes, CNN, and NPR. Recognized by Thinkers50 and the American Management Association, she lives in Chicago. Stephanie Loeck is Vice President of Strategic Development at GPS Education Partners, where she leads national growth initiatives advancing work-based learning and expanding career-connected opportunities for students. A passionate workforce and education advocate, Stephanie brings expertise across strategy, policy, communications, and economic development to help modernize the transition from school to work. At GPS Education Partners, she shapes long-term growth strategies, builds partnerships, and drives thought leadership around learner-centered program design. She played a key role in developing GPS Ed’s signature six-part work-based learning framework, which supports program implementation, continuous improvement, and sustainable impact. Previously, Stephanie served as Vice President of Partnerships at America Succeeds, engaging business leaders in education reform initiatives such as Durable Skills and Age of Agility. She has also worked in economic development and with technology startups. Based in Colorado, Stephanie serves on national advisory boards championing authentic, career-connected learning aligned with the future 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.    

What if the future of careers isn’t about résumés or job titles but about fit? Avi Steinlauf and Tomas Chamorro-Premuzic, co-founders of myTrudy, explore how personality science and AI are reshaping career decisions, helping people move from static search to dynamic, human-centered reinvention in a rapidly changing world of work.Avi Steinlauf is the CEO and Co-Founder of myTrudy, a personality-driven career intelligence platform using validated psychometrics and AI to help individuals and organizations make better, fit-first career decisions. At myTrudy, Avi is building a new category at the intersection of human potential, data platforms, and the future of work. Prior to myTrudy, Avi spent more than two decades at Edmunds, where he served as CEO and led the company through its successful sale to CarMax. Under his leadership, Edmunds scaled into one of the internet’s most trusted consumer marketplaces, known for its data-driven products, industry transparency, and market influence. Avi holds an MBA from the Kellogg School of Management and earned his undergraduate degree from Yeshiva University.Tomas Chamorro-Premuzic is the chief science officer at Russell Reynolds Associates, a professor of business psychology at University College London and at Columbia University, a cofounder of MyTrudy.com, and an associate at Harvard’s Entrepreneurial Finance Lab. He is the author of Why Do So Many Incompetent Men Become Leaders? (and How to Fix It) (Harvard Business Review Press, 2019), upon which his TED talk was based, and  I, Human: AI, Automation, and the Quest to Reclaim What Makes Us Unique, (Harvard Business Review Press, 2023). His latest book is Don’t Be Yourself: Why Authenticity Is Overrated (and What to Do Instead)(Harvard Business Review Press, 2025).     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.    

As AI reshapes the marketing landscape, what makes human talent more essential not less? Jeff Levick, CEO of We Are Rosie, shares why performance-based compensation, flexible teams, and the right culture are key to unlocking the full power of people in a tech-driven world.Jeff Levick is a 20+ year veteran leading media, marketing, and digital growth companies from early stage through IPO. Currently, he serves as the Chief Executive Officer at We Are Rosie, an agency that’s imagining and building a better future for the advertising industry with fractional talent and teams as well as a community-based approach. Prior to joining We Are Rosie in 2023, Levick was the COO of Redesign Health, a venture studio firm focused on the health and wellness vertical. Before that, he was the CEO of The Players’ Tribune, a new media company founded by Derek Jeter that provides athletes with a platform to connect directly with their fans, in their own words. Jeff led the company’s acquisition by Minute Media in December 2019. Jeff served as Spotify’s Chief Revenue Officer from 2011 to 2016, leading the company’s commercial business and its global acceleration from 1mm subscribers to more than 40+mm subscribers. He also grew Spotify’s physical footprint from 11 countries to over 60 markets worldwide. Prior to Spotify, Jeff served as President of Global Advertising and Strategy at AOL from 2009 – 2011 where he was responsible for the overall revenue business including premium display, Advertising.com, research, marketing, ADTECH, and branded entertainment. Before AOL, Levick held various global leadership roles at Google in the US and Europe from 2001 to 2009 where he was also an original member of its advertising team. A frequent lecturer on topics related to media, marketing and digital trends, Levick is also an Executive Director at NYU’s Entrepreneurial Institute. He holds a B.A. from New York University and a law degree from DePaul University in Chicago.  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 bring dignity, flexibility, and innovation to the millions of hourly workers who keep our world running? Jarah Euston, President and Co-founder of WorkWhile, shares how behavioral data and community-driven design can reshape frontline work and why the future of labor starts on the warehouse floor.Jarah Euston is the President and Co-founder of WorkWhile, a workforce-as-a-service platform. Previously, she co-founded the DataOps platform Nexla and was founder and CEO at Famous Media, a pioneer in hyperlocal content acquired by McClatchy. She also led the analytics and marketing teams at Flurry, an innovator in mobile app analytics acquired by Yahoo, where she was VP of Product. Jarah was formerly a consultant at Boston Consulting Group and started her career in hourly work as a retail associate. She is a member of EY Entrepreneurial Winning Women. Jarah holds an MBA from the Wharton School at the University of Pennsylvania and a BS from New York University. 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.    

Joseph Thumpasery, Managing Partner of Fourth Wall Advisors, brings a wealth of Wall Street expertise, alongside Samantha Rhoads, Head Data Scientist, and Anika Harode, Financial Analyst. Together, they explore how small teams can leverage AI-driven workflows and diverse skill sets to outperform larger organizations. They delve into the importance of character in hiring, the impact of automation on client service, and their innovative approach to quantifying policy chatter with NLP. The discussion highlights how curiosity and collaboration fuel high performance in the evolving work landscape.

Gary Brown, president and co-founder of Furnished Quarters, dives into the evolving landscape of workforce mobility in a hybrid world. He discusses the shift from hotels to flexible housing, emphasizing how thoughtful living solutions can enhance employee experience and retention. Gary also highlights unique challenges like medical travel demands and visa constraints, all while maintaining a personal touch in customer service. With insights on adapting to post-COVID trends and the impact of technology, he reveals how the corporate housing market is transforming.

Lara Vandenberg, founder and CEO of Publicist, discusses her journey in creating a platform that connects companies with top-tier freelance marketing talent. She highlights the importance of agility in workforce models and how the pandemic reshaped hiring dynamics. Lara explains the shift from traditional worker classifications to flexible W-2 solutions, and the benefits of having a talent 'bench' for quick access to specialists. She also dives into the role of AI in transforming job functions and anticipates exciting new marketing roles for the future.

What if the corporate job is no longer the default path to a meaningful career? Alex McCann, founder of TrueNorth, explains why so many young professionals feel lost at work, how Gen Z is redefining success, and why the future may belong to those who start with self-discovery instead of job titles.Alex McCann is a writer, community builder, and founder of TrueNorth, an AI-powered career coach designed to help people build meaningful careers by starting with self-discovery, not job titles. Through TrueNorth, his MidWeek events in London, and his newsletter Still Wandering, Alex helps people in their 20s and 30s navigate uncertainty, question outdated career narratives, and define success on their own terms. His work is grounded in a simple belief: you can’t build a fulfilling career until you understand what meaning means to you. Alex now focuses on giving Gen Z and Millennials the tools, language, and community to design lives and work they can truly stand behind. 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 culture was the key to competitive advantage? Alastair Creamer and Doug Milliken, co-founders of Creamer Milliken, share why accelerating culture change is essential for growth, how leaders can make transformation stick, and why the companies that thrive tomorrow will be the ones that reinvent from the inside out.Alastair Creamer is a cultural change consultant and co-founder of Creamer Milliken. He began his career at Unilever, where he created Catalyst, an award-winning program that ran for seven years and transformed creativity across the company’s UK operations. Since then, Alastair has worked with leaders, teams, and organizations worldwide, helping them unlock creativity and accelerate meaningful cultural change. In 2012, he co-founded Eyes Wide Opened, a coaching program supporting people at professional crossroads—from quarter-life crises to later-life reinventions—guiding them toward clarity and personal purpose. His work continues to focus on enabling individuals and organizations to adapt to change with confidence and creativity. A lifelong creative, Alastair is also a musician, writer, and artist. In 2023, he published a book of prose-poems about his relationship with his son, Ollie. Today, he finds inspiration in the arts and in gardening, which he calls one of his most creative pursuits.Doug Milliken is a co-founder of Creamer Milliken and a seasoned transformation leader with over 35 years at The Clorox Company. During his career, he led marketing, innovation, and cultural transformation initiatives across the global organization. Most recently, Doug spearheaded Clorox’s Digital Transformation, shifting from mass marketing to personalized, data-driven approaches that generated over $50 million in incremental profit. He previously created the company’s brand-building process and redefined strategy, insights, consumer experience, and media across multiple teams worldwide. Doug is the only employee in Clorox’s history to win the CEO Award for Outstanding Leadership twice. He also co-led the company’s enterprise-wide “Growth Culture” initiative, designed to help 8,000 employees act simpler, faster, and bolder. With an MBA from Kellogg, Doug has also served as an adjunct professor at INSEAD. He lives in Northern California, where he enjoys music, hiking, biking, and restoring his property after the 2017 wildfires. 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.