Episode 523 Creating a Future-Ready Agency with Rishad Tobaccowala

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Oct 12, 2025

Rishad Tobaccowala, an agency veteran and author of "Rethinking Work," shares his insights on the evolving work landscape. He discusses five transformative forces like technology and demographics that are reshaping how teams operate. Rishad emphasizes the shift towards flexible work environments and the importance of fostering leadership without traditional hierarchies. He also highlights the benefits of fractional roles and the need for agencies to attract talent by reimagining their office spaces, aligning with emerging generational values.

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INSIGHT

Purposeful Work Shapes Life

Meaningful, purposeful work strongly influences life satisfaction and longevity.
Between 2019–2029 work will change more than in the prior 50 years, driven by five major forces.

INSIGHT

Five Forces Reshaping Work

Five broad forces reshape work: demographics, technology/AI, new marketplaces, freelancing trends, and COVID's deeper existential shift.
COVID accelerated trends and made people question why they work and who they work for.

ADVICE

Leverage Smallness, Not Big Capital

Small companies gain advantage as power shifts from capital to talent and from large to small firms.
Focus on closeness to customers, knowledge, and speed rather than owning capital or infrastructure.

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Welcome to another insightful episode of Build a Better Agency! In this thought-provoking conversation, host Drew McLellan welcomes acclaimed author, agency veteran, and thought leader Rishad Tobaccowala to the show. Together, they dig into the rapidly evolving nature of work and what it means for agency leaders and teams in the years ahead.

Rishad draws on his decades of agency experience and his latest book, "Rethinking Work," to outline the powerful shifts transforming how, where, and why we work. With unmatched clarity, he breaks down the five key forces—ranging from technology and AI to shifting demographics and the post-COVID mindset—that are redrawing the boundaries between work and life. Rishad also challenges traditional agency norms by explaining why flexibility, purpose, and autonomy are now at the heart of attracting and retaining top talent.

Listeners will come away with fresh ideas for structuring their agency teams, from leveraging fractional and freelance talent to reimagining office space as dynamic hubs for creativity and collaboration. Rishad and Drew also tackle leadership evolution, with candid advice on moving from "boss zones" to genuine zones of influence that inspire trust and independence.

If you’re ready to shake off old models and embrace the future with optimism, this episode is a must-listen. By the end, you’ll be eager to reimagine your agency’s structure, ignite your creativity, and cultivate a workplace where both people and business can thrive in our new era of work.

A big thank you to our podcast’s presenting sponsor, White Label IQ. They’re an amazing resource for agencies who want to outsource their design, dev, or PPC work at wholesale prices. Check out their special offer (10 free hours!) for podcast listeners here.

What You Will Learn in This Episode:

- Why work is changing faster than ever—and how agencies can get ahead
- Shifting from “bosses” to leaders to attract and retain top talent
- Embracing a flexible workforce: full-time, freelance, fractional, and AI “employees”
- Redesigning office space to encourage purposeful, in-person collaboration
- Rethinking organizational structures—moving from rigid hierarchies to “jazz ensemble” models
- Leveraging AI and technology to boost revenue per employee and agility
- How agency owners can reimagine their business for resilience and future growth