On this episode of Flying Solo, Cec Busby sits down with trailblazing entrepreneur Lisa Messenger, founder of The Collective Hub. Known for her fearless approach to reinvention and disrupting the status quo, Lisa Messenger has built an extraordinary career, from launching a globally celebrated print magazine at the height of “print is dead,” to growing her business from three staff to 36, traversing the highs and lows of entrepreneurship, and making a purposeful pivot to a lean, AI-powered education and community platform for founders. Lisa reflects on business failures, the courage to start and close ventures, lessons learned from scaling too quickly, the power of knowing your purpose, and the importance of adaptability in a rapidly changing world. She shares insights into teaching herself AI, creating digital communities, the joy and challenge of motherhood after a long IVF journey, and her new adventure as a fiction writer. Listeners will get the inside story of how Collective Hub is relaunching for the digital age and practical tips for solopreneurs looking to thrive with fewer resources and greater impact. Key topics 1. Reinvention and Business Evolution Lisa Messenger discussed shifting from running a large team (36 staff, hundreds of freelancers) to now having zero staff, emphasizing that "bigger isn't necessarily better" 02:26. She explored how staying attached to her purpose of "igniting human potential" allowed her to change delivery mechanisms—from print magazine to digital products and an AI-powered platform 05:10. Reinvention involved learning new skills such as AI and collaborating with past team members to relaunch the Collective Hub community and membership 13:10. 2. Lessons from Success and Business Failure Lisa Messenger highlighted the courage it took not only to launch the print magazine but also to close it down publicly, stressing the importance of not letting ego or identity keep you stuck in a failing business 07:06. The rapid growth led to challenges she was unprepared for, like managing 17 different revenue streams and teams in 37 countries, which ultimately was unsustainable 08:20. She emphasised the need for business acumen and possibly bringing in the right COO or 2IC earlier to balance visionary leadership with operational competency 09:09. 3. Embracing and Teaching AI for Solopreneurs Lisa Messenger became a certified prompt engineer and now uses over 50 AI tools, with ChatGPT as her central “motherboard” for orchestrating tasks and business automation 16:02. She runs AI retreats, guiding participants from various backgrounds (including corporate heads) through practical applications, showing skeptics how AI can streamline and empower their businesses 18:17. Practical takeaway: she encourages solopreneurs to simply start with ChatGPT, building familiarity through step-by-step personal “training” of the AI to work as their digital twin and assistant 22:17. 4. Personal Growth, Motherhood, and Work-Life Balance Lisa Messenger reflected on how becoming a mother, after a long IVF journey and surrogacy, fundamentally shifted her priorities and business direction 28:47. She described consciously downsizing her business model for more freedom, focusing on purpose and high-impact tasks rather than scale and staff 26:17. Motherhood changed her outlook: she now blocks out specific time for projects, controls her schedule, and puts family at the forefront, contrasting her earlier years of relentless work 27:49. Time-stamped overview 00:00 Starting a magazine despite skeptics 06:50 Starting and shutting a print magazine 10:22 Building Opportunities and Relaunching with Jade 11:41 Attempting new print format 14:38 Adapting to New Business Challenges 19:52 Building your virtual team 22:17 Getting started with ChatGPT 27:16 Balancing writing projects and freedom 30:32 Balancing career and IVF journey 33:08 Transitioning to traditional publishing 36:01 Finding inspiration from Save the Cat 39:53 Creating digestible content for entrepreneurs 42:04 Creating a community leaderboard Learn more about your ad choices. Visit megaphone.fm/adchoices