Bootstrap Confidential

Bootstrap Confidential - Episode 20 - Jennie Moss


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🎧 Episode Snapshot: Rethink Everything — Lifestyle, Leadership and Scaling with Purpose — Featuring Jennie Moss, Founder and Managing Director of Rethink Events

This episode explores how backing yourself, building the right team, and staying true to your vision can transform a lifestyle-led business into a high-performing, scalable organisation.

Jennie Moss shares her journey of founding Rethink Events on her own terms, designing a business that worked around her life, not the other way around — and what it really takes to grow beyond the startup phase without losing what made it special in the first place.


Key insights include:


  • Owning your destiny: Why Jennie chose to build something of her own, and how lifestyle intentionality shaped every early decision.
  • Hiring beyond the CV: The mindset shifts required to attract, retain and empower a high-performing team aligned with your values.
  • Start-up to scale-up: Navigating the pivotal transition from founder-led hustle to a business with systems, structure and staying power.
  • Events as experience: The philosophy behind building events that leave a lasting impression on clients, audiences and communities alike.
  • Resilience in a demanding industry: How Jennie has navigated the pressures of the events world and come out stronger on the other side.

Jennie unpacks the realities of building a business on your own terms, the leadership qualities required to inspire a team that truly delivers, and the growing pains that come with stepping from scrappy startup into serious scale. This conversation offers honest, grounded insights for founders ready to back themselves, build boldly and lead with both purpose and presence.

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Bootstrap ConfidentialBy Bootstrap Confidential