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. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. AI at Work: Finance

    18/09/2025

    AI at Work: Finance

    What happens when AI rewires the workflows of modern finance? Bin Ren, founder and CEO of SigTech, explains how artificial intelligence is transforming how financial institutions design, test, and execute investment strategies, and why the future of finance depends on smarter, faster, and more adaptive ways of working. Before founding SigTech at the start of 2019, Ren was the Chief Investment Officer of the Systematic Investment Group (SIG) at Brevan Howard Asset Management where he managed multiple quantitative investment funds. He started his career at Barclays Capital as an equity exotics trader managing quantitative investment strategies across all major asset classes. Before university, Ren skipped two grades in school and won three first prizes in the Chinese National Olympiads. After earning a Bachelor’s degree in electrical engineering at the national gifted education program of Shanghai Jiaotong University, Ren was directly admitted with full scholarship to the PhD program for computer science at Cambridge University, UK. While there he researched Xen which was chosen by Amazon as the cornerstone of the world’s first cloud-computing platform AWS that generates over $100 billion annual revenue 20 years later. 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.

    42 min
  7. The Courage to Choose Yourself

    10/09/2025

    The Courage to Choose Yourself

    What if the most important approval you’ll ever need is your own? Author and coach Jillian Reilly discusses her book The Ten Permissions, and why we struggle to let go of others’ expectations, and how to start giving ourselves permission to live and work on our own terms. Jillian Reilly is a founder, author, and keynote speaker. Having spent her 30-year career working in social, organizational, and individual change across Africa, Asia, and Central Europe, Jillian’s focus is on helping people unlock their ability to navigate change and accelerate growth and learning. Jillian’s upcoming book, The Ten Permissions, guides readers in permitting themselves to update how they operate in the 21st century and design lives that fully leverage the possibilities of this disruptive world. Jillian is a TEDX speaker and podcast host who has been published on international affairs in the Washington Post, Newsweek and the LA Times. Her memoir, Shame: Confessions of an Aid Worker in Africa, chronicles her early career in international development and the profound lessons it offered on the failings of the aid industry to drive growth across the developing world.  To learn more about Jillian and where to purchase her book: https://tenpermissions.com/ 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.

    45 min
  8. How AI Reshuffles The Knowledge Economy

    03/09/2025

    How AI Reshuffles The Knowledge Economy

    How is AI reshaping who holds power in the knowledge economy? Sangeet Paul Choudary, the best-selling author of Platform Revolution and Reshuffle explains how artificial intelligence is re-stacking the way knowledge is created, distributed, and monetized, and what this means for workers, companies, and the future of competitive advantage. Sangeet Paul Choudary is the best-selling co-author of Platform Revolution and the author of Reshuffle. He has advised CEOs at more than 40 Fortune 500 companies as well as pre-IPO tech firms. Sangeet has been recognized as a Young Global Leader by the World Economic Forum, and his work on platforms has been featured four times in the Harvard Business Review Top 10 Must Reads compilations. He is currently a Senior Fellow at the University of California, Berkeley, and was formerly the co-chair of the MIT Platform Strategy Summit and a member of the Ministerial Advisory Committee at the Ministry of Housing and Urban Affairs, Government of India. He has served on the advisory boards of leading financial institutions including the ING Group, Standard Bank, and the Monetary Authority of Singapore. As a frequent keynote speaker, Sangeet has presented at leading global forums, including the G20 Summit, the World50 Summit, and the World Economic Forum. Order Sangeet's new book Reshuffle here: https://www.amazon.com/dp/B0DTKW6NQV 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

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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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