The Rethinking Work Show artwork

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

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

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

Nov 26 2025
30 min

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 platfo

Nov 5 2025
36 min

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 w

Oct 22 2025
36 min

Chart trend

Position in the Careers chart (US), last 90 days.

#20
all-time peak
4
days in the top 50 since Jun 2025

Chart positions

Where The Rethinking Work Show ranks today in each Apple Podcasts chart (US, Sep 18, 2026).

#96 ▲ 74 Careers US

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