In this episode of What I Learned in Business (That Didn’t Kill Me!), James Stewart explores one of the most important and misunderstood challenges facing leaders, employers, marketers and boards today: how to understand and engage the next generations of consumers and workers—Gen Z and Gen Alpha.

James is joined by Anastasia Pelot, founder of House of Context and a youth-culture strategist who helps organisations decode how young people think, behave, buy and communicate. Raised across Kenya, Greece, Germany, Syria and Lebanon before moving to the United States at 15, Anastasia brings a rare global and cultural lens to the question of identity, belonging and generational change.

The conversation begins with Anastasia’s extraordinary upbringing as a Third Culture Kid (TCK), the cultural shock of settling in the US as a teenager, and how those experiences shaped her sensitivity to identity formation, emotional safety and belonging—themes that sit at the heart of her work today.

James and Anastasia then dive deep into the real differences—and overlaps—between Gen Z and Gen Alpha, cutting through stereotypes and simplistic labels. Anastasia explains why she views youth not as a “segment” but as a signal—an early indicator of where culture, leadership, work and consumer behaviour are heading next.

Key themes explored include:

• Why dividing young people strictly into Gen Z versus Gen Alpha can obscure deeper behavioural patterns
• Gen Z as the first generation to experience “public adolescence” online, and the self-protective instincts that emerged as a result
• Gen Alpha as a more AI-native, immersive and sensory-driven cohort
• How young people form identity, relationships and belonging in an algorithmic world
• The headwinds and tailwinds shaping youth development today, from mental health pressures to economic uncertainty

From there, the discussion shifts to a business and consumer lens, examining what authenticity really means to younger generations, how brands succeed—or fail—when engaging them, and why traditional measures of loyalty often miss what actually matters: community, participation, advocacy and influence.

The episode also looks forward, exploring how emerging technologies such as AI, augmented and virtual reality, digital avatars and immersive platforms are reshaping expectations—and what businesses should be doing now to remain relevant.

Finally, James and Anastasia discuss Australia’s new laws restricting access to social media for under-16s from December 2025, the potential cultural consequences, and how Gen Alpha in particular may adapt to a more regulated digital environment.

This is a wide-ranging, practical and thought-provoking conversation for anyone trying to understand the future of leadership, marketing, culture and commerce—and the generations who will define it.

This podcast is provided for general information and discussion purposes only. The views and opinions expressed by the host and guest are their own and do not constitute financial, legal, investment, regulatory or professional advice. Listeners should not rely on the information discussed in this episode as a substitute for independent advice tailored to their specific circumstances. While every effort has been made to ensure accuracy at the time of recording, no representations are made as to the completeness or ongoing accuracy of the information.

To learn more about the podcast, access episode notes, or explore upcoming guests, visit jameshstewart.com.

You can also connect with James on LinkedIn at James H Stewart GAICD.

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