The Rethinking Work Show

Rishad Tobaccowala

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.

  1. Work Enabling Learning

    5D AGO

    Work Enabling Learning

    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 CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    36 min
  2. Beyond The Resume

    FEB 18

    Beyond The Resume

    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 CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    43 min
  3. Turbocharge Human Talent

    FEB 4

    Turbocharge Human Talent

    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 CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    40 min
  4. The Shift Work Revolution

    JAN 21

    The Shift Work Revolution

    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 CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    37 min
  5. How Small Teams Do Big Work

    12/11/2025

    How Small Teams Do Big Work

    How can small teams now match, and even outperform, the output of much larger organizations? The team at Fourth Wall Advisors shares how AI-driven workflows, intentional design, and diverse, non-overlapping expertise are reshaping how work gets done. From reducing friction to unlocking deeper creativity and faster iteration, they explore why the future of high performance belongs to small teams built for curiosity, adaptability, and human connection.   Joseph Thumpasery is the Managing Partner of Fourth Wall Advisors. He brings over 15 years of experience on Wall Street, with the last 10 spent running 9-figure portfolios for macro hedge funds. Most of Mr. Thumpasery's buy side career was spent as a Portfolio Manager at Bluecrest Capital, which was arguably the top macro hedge fund in the world while he was there, posting returns ranging from 20% to 153%. He has never hit his 5% "stop-loss" during the course of a trading year and has never finished the year down money, in over 10 years of money management. The strategy currently deployed at Fourth Wall Advisors LLC was researched and run by Mr. Thumpasery at multiple hedge funds. Samantha Rhoads is the Head Data Scientist of Fourth Wall Advisors. Passionate about studying human behavior, she began her journey as a quantitative social scientist during her joint Bachelor’s/Master’s program at Columbia University, before moving into the people analytics sphere. After 7 years spearheading diversity analytics, machine learning, and automation projects at a NYC law firm, she's now leveraging her experience in a new domain of human behavior: finance. Samantha has a keen interest in mixed methods: supplementing the quantitative with the qualitative, which is one of Fourth Wall's key tenets. Anika Harode is a Financial Analyst at Fourth Wall Advisors, where she contributes to investment research and portfolio strategy. She studied Mathematics and Statistics at the University of Virginia, bringing a quantitative foundation and a deep interest in applying data-driven methods to financial markets. Prior to Fourth Wall, Anika worked as a machine learning researcher at the University of Virginia. She has worked on projects analyzing and decomposing long-term, value-oriented investment strategies. Anika is a driven self-starter and contributes heavily to the research library at Fourth Wall. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    43 min
  6. The Future of Workforce Mobility

    11/26/2025

    The Future of Workforce Mobility

    What if where people live became a core part of how they work? Gary Brown, president and co-founder of Furnished Quarters, shares how workforce mobility is changing in a hybrid world, and why companies are shifting from hotels to flexible housing, what employees need to thrive on remote assignments, and how thoughtful living solutions can strengthen culture, retention, and performance. As Co-Founder and President of Furnished Quarters, Gary manages the sales and financial efforts to ensure the company achieves sustained growth. Before co-founding Furnished Quarters, Gary worked as a certified public accountant and attorney in New York and Connecticut. With a sharp sense of where the real estate industry was heading—and inspired by the Brown family’s long-standing family business in furniture sales—Gary, alongside brother Steve Brown, identified an untapped need for high-quality furnished accommodations in New York City. In 1998, the brothers founded Furnished Quarters to serve that need. Starting with a handful of furnished apartments in a New York City brownstone, the venture saw immediate success, with high demand leading to continued growth for over 25 years. Gary has spent most of his career developing and investing in Manhattan real estate and continually identifies key trends and opportunities within the alternative accommodations space.  EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    31 min
  7. Reinventing How Companies Access Talent

    11/05/2025

    Reinventing How Companies Access Talent

    What if companies could access top creative and marketing talent as easily as opening an app? Lara Vandenberg, founder and CEO of Publicist, shares how she built a platform that connects global brands with premium freelance talent, and why the future of work depends on flexible, trusted systems that empower both companies and creators. Lara Vandenberg is the founder and CEO of Publicist, a freelance management system and premium talent marketplace redefining how global enterprises access and manage marketing talent. With thousands of pre-vetted professionals spanning communications, creative, media, content, and production, Publicist enables companies to build and scale flexible, high-performing teams through one trusted platform. Before launching Publicist, Lara worked across brand strategy, communications, and technology, where she saw firsthand the growing gap between how companies hire and how top talent wants to work. She founded Publicist to bridge that divide—creating a solution that brings efficiency, transparency, and opportunity to the freelance economy. Recognized as a next-generation leader in the future of work and marketing innovation, Lara continues to champion a more flexible and inclusive workforce model, helping companies and creators thrive in the modern economy. EPISODE CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    36 min
  8. Death of the Corporate Job

    10/22/2025

    Death of the Corporate Job

    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 CREDITS Produced, edited and mixed by Ria Tobaccowala Artwork designed by Ben Damiano Additional music licensed through Premium Beats LINKS Explore more about the new frontiers of work at Rethinkingwork.io For 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.

    36 min

Ratings & Reviews

5
out of 5
6 Ratings

About

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.

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