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Careers · Rishad Tobaccowala

The Rethinking Work Show

by 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.

Latest episodes

Showing 20 · updated from the feed

The Hidden Work Crisis

What if the crisis of work and the crisis of mental health are actually one and the same? Kristen Beveridge, founder of phae, explores why finding work that fits who we a

Oct 21
41 min

The Reputation Gap

As companies retreat from public commitments and corporate values, what are they risking in the process? Haider Nazar, co-founder and CEO of MAHA Global, explores the gro

Oct 7
34 min

The Price of Easy

As AI makes work faster and easier, what might we lose along the way? Bala Muthiah explores the hidden cost of convenience, why productive friction strengthens learning a

Sep 24
32 min

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

Sep 2
45 min

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 throug

Aug 12
38 min

The Human Edge

As AI becomes more capable, what will make humans indispensable? Matt Lewis, founder and CEO of Transformental, explores why the future of work depends not just on smarte

Jul 22
31 min

Finding Your Fit

How do you find work that aligns with who you are, not just what you can do? William Vanderbloemen, founder and CEO of Vanderbloemen Search Group, explores how understand

Jul 16
29 min

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 pr

Jun 24
39 min

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 transitio

Jun 18
43 min

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 w

Jun 3
44 min

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 c

May 13
42 min

Dynamic Teaming

What if teams weren’t built around roles, but around problems? Britt Gage, founder and CEO of oAT (of All Trades), explores the shift from static org charts to dynamic te

Apr 29
31 min

The Capability Stack

In a world where skills expire faster than ever, how do you stay relevant? Veronika Kryuchkova explores the idea of the “capability stack", a dynamic mix of core, human,

Apr 16
36 min

Rethinking Compensation

What if we stopped paying for time and started paying for outcomes? Matt Seiler, founder and CEO of Excelerators Inc., explores why traditional compensation models are br

Apr 1
37 min

The Orchestration Era

As AI accelerates and traditional corporate structures strain under pressure, what does leadership look like in the next era of work? Justin Billingsley, co-founder of Si

Mar 19
39 min

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 th

Mar 4
36 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

Feb 18
42 min

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, flex

Feb 4
39 min

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, sh

Jan 21
36 min

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

Dec 11 2025
43 min

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