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. HACE 46 MIN

    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
  2. Turbocharge Human Talent

    4 FEB

    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
  3. The Shift Work Revolution

    21 ENE

    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
  4. How Small Teams Do Big Work

    11/12/2025

    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
  5. The Future of Workforce Mobility

    26/11/2025

    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
  6. Reinventing How Companies Access Talent

    05/11/2025

    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
  7. Death of the Corporate Job

    22/10/2025

    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
  8. Culture as Competitive Advantage

    01/10/2025

    Culture as Competitive Advantage

    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 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.

    47 min

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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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