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. 2d ago

    Doing More With Less

    What if building a bigger business doesn’t require building a bigger team? Tim Huelskamp, co-founder and CEO of 1440, shares how a small, focused team reaches millions of readers, and why staying lean, curious, and intentional can create outsized impact. Tim Huelskamp spent a decade in private equity helping scale growth businesses before building one of his own. He's the co-founder & CEO of 1440, a community for the knowledge-obsessed. Every day, the 1440 team scours the internet, cuts through the noise, and delivers fact-based, insights that help millions of readers keep learning. Along the way, 1440 has been named one of Inc.’s Best Workplaces three years running, and ranked among the Inc. 5000’s fastest-growing private companies. Before 1440, Tim invested in and helped grow businesses at a $20B private equity fund, serving on the boards of companies across a range of industries. He also co-founded Fifth Star, a philanthropic venture fund providing "friends and family" capital to underrepresented founders. They've backed more than 30 founders to date. Based in Chicago with his wife, Jennifer, Tim is passionate about building businesses, lifelong learning, and great conversations.  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.

    Doing More With Less
  2. Aug 12

    Career Rewired

    How do you keep evolving when the world around you won’t stop changing? Marketing leader Lou Paskalis explores what it takes to reinvent your career, stay relevant through disruption, and embrace change before it’s forced upon you. Lou Paskalis is CEO and Founder of AJL Advisory, a consultancy focused on helping marketers to improve their business narrative and tech companies to better understand marketers and their needs. He also serves as Chief Strategy Officer of Ad Fontes Media a Public Benefit company that is dedicated to increasing advertisers’ investments to reach audiences in quality news journalism with a unique technology that allows them to measure, mitigate and monitor bias and reliability in a manner consistent with their values and principles. Paskalis sits on the advisory boards of Ebiquity, Nielsen and POSSIBLE, among others and is very active with the Association of National Advertisers (ANA) in several key areas, including their ongoing efforts in supply path optimization. Previously, Paskalis was President and COO of MMA Global, a trade association focused on architecting the future of marketing. In that role, he was responsible for driving innovation and change across a broad portfolio of functional areas, initiatives and forward-looking activities centered on shaping the future of marketing. Prior to MMA, Paskalis spent three decades of client-side leadership experience, having led Global Communications Planning, Media Investment, Marketing Data Strategy and Brand Safety and Suitability at Bank of America; Media, Content and Mobile Marketing at American Express. He is well-known as an outspoken champion for marketing innovation, governance and the advancement of the art and science of marketing as well as a strong advocate for ad-supported journalism and marketers’ unique responsibility to support news organizations in their valiant efforts to uncover, disseminate and defend truth. He makes his home in Manhattan and is a lifelong F1 fan and enjoys international travel. 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.

    Career Rewired
  3. Jun 24

    Rethinking Career Growth

    Is career success measured by moving up or moving forward? Cliff Maxwell, co-founder and CEO of Vocation, explores the difference between career progression and career progress, why fulfillment matters as much as advancement, and how individuals can take greater ownership of designing meaningful careers in a rapidly changing world of work. Cliff Maxwell is the Co-founder and CEO of Vocation, an AI-powered career coaching platform for students and professionals to discover their next step. Prior to Vocation, Cliff spent several years investing in early-stage technology startups and was the Chief of Staff to the late Professor Clayton Christensen who developed the theory of 'disruptive innovation'. Cliff's career began as a CPU design engineer. He holds an MBA from Harvard Business School and graduated from Brigham Young University with a BS in Electrical Engineering. He resides in Salt Lake City where he is busy raising three boys.  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.

    Rethinking Career Growth
  4. Jun 18

    Identity Reinvention

    What happens when you leave the career you've spent decades building? Julie Fedele, a Future of Work strategist and portfolio career mentor, explores why career transitions are as much about identity as opportunity, and how more professionals are moving beyond traditional employment to build a body of work that’s truly their own. Julie Fedele is a Future of Work strategist and portfolio career mentor based in Melbourne, Australia. A former C-suite leader and venture builder across Australian and European startups in HealthTech, ClimateTech, and Media, she works at the intersection of individual career transition and organisational workforce design. Julie helps women in mid-to-senior career stages move from the corporate model to what she calls the Hollywood Model: a shift from employee to talent, where you build a body of work, move between productions, and own your career narrative and income mix. Her methodology blends strategic business frameworks with diagnostic tools for energy and decision-making. She writes rawmaterials, a weekly newsletter on identity, income, and the real work of building something that's yours, and is currently writing Off Script, a book on the structural shift reshaping how we 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.

    Identity Reinvention
  5. Jun 3

    Collaboration Revolution

    In a world overflowing with productivity tools and AI assistants, are we actually working better together? Toby Daniels, co-founder of ON_Discourse and Domain, explores why the future of work depends on better collaboration, stronger networks, and systems that help us think and not just work more effectively. Toby is the Co-Founder of ON_Discourse, a global network of technology, business and innovation leaders, investors and entrepreneurs and Co-Founder of the (domain), an AI collaboration platform that connects your work to your network. Domain is now available as a free public beta: ondomain.ai Prior to this, he was the Chief Innovation Officer at Adweek, the leading source of news and insight serving the brand marketing ecosystem. Toby was also the Founder & Chair of Social Media Week, which Adweek acquired in January 2021. Prior to the acquisition, Social Media Week was owned and operated by Crowdcentric Media, which Toby led as CEO for over ten years. Before Crowdcentric, Daniels led business development in the US for Mint Digital and prior to that was the Managing Director of Online Creative Communications, a London based digital agency that he managed for 7 years. Toby is also an advisor to a number of companies including Adweek, Legends, a confidence-training program for elementary schoolers, building legendary kids in 5 minutes a day, and Simon Data, a SaaS marketing platform that helps clients deliver better customer experiences using data.  He was also an advisor to BOND, which sold to Newell Brands in 2016. As a thought leader in media, marketing and technology, Toby has been featured in mainstream and trade media, including articles on CNN.com, The NY Times, The Next Web, Huffington Post, AdWeek, PSFK and Fast Company. He speaks regularly at conferences and has given talks at PdF Latin America in Chile, Social Media Brazil, The Co-Creation Conference, Phoenix and SXSW. In 2013, The Next Web named Toby as one of New York's 50 NYC Tech Entrepreneurs You Need to Know About. In 2014 Toby co-curated the book On! The Future of Now, with the proceeds going towards supporting clean water projects in the developing world. 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.

    Collaboration Revolution
  6. May 13

    The Talent Shift

    As AI transforms marketing and reshapes organizations, what skills and leadership qualities will matter most? Richard Sanderson, Partner at Spencer Stuart, explores how companies are rethinking talent, adapting team structures, and balancing automation with human judgment. Richard Sanderson is a Chicago‑based Partner and Consultant at Spencer Stuart, where he advises CEOs, boards, and people leaders on recruiting and retaining transformational marketing, customer, and growth executives. His work spans all industries, and he is retained to solve some of the most complex leadership mandates that require a nuanced understanding of modern marketing, product, and customer strategy.  Over the years, Richard has shaped high‑impact executive searches ranging from Chief Marketing Officers to senior customer, brand, digital, growth and experience leaders across a range of Fortune 500 companies, middle-market private equity backed businesses, and early-stage category disruptors. 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.

    The Talent Shift

Ratings & Reviews

4.9
out of 5
7 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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