Annemarie Penny on Dreaming Bigger, Embracing AI, & Creating Space for What’s Next
About the Episode
In this insightful episode, we sit down with Annemarie Penny, founder and CEO of Dreamore, to talk about technology, leadership, and the mindset shifts required to thrive in a rapidly changing world. From her beginnings in Arkansas to her journey as a tech leader in California, Annemarie shares how she’s using AI, strategy, and emotional intelligence to shape a more equitable and expansive future - especially for women.
Key Takeways
Dreamore Is a Philosophy: Annemarie named her company Dreamore to remind herself and others to think beyond the now. She believes in shaping the future proactively rather than reacting passively to the present.
Attitude Is Everything: Moving to California with limited resources, Annemarie leaned on her can-do spirit. She encourages listeners to stop fearing failure and embrace a solutions-first mindset as a tool for wellbeing and momentum.
AI as a Creative Partner: Rather than viewing AI as a threat, Annemarie sees it as a tool to boost human potential. Platforms like Claude and ChatGPT can spark imagination, unlock new thinking, and drive exploration.
Use AI with a Critical Lens: Annemarie reminds us to question AI, not just accept it. Repeatedly asking "why?" deepens understanding, prevents blind reliance, and builds sharper thinkers in a tech-driven age.
The Growth Mindset, Discovered Unexpectedly: Even through online dating, Annemarie encountered the concept of a growth mindset - and it changed how she approached setbacks, learning, and professional reinvention.
The Future of Work Is Evolving: With AI, globalization, and climate change reshaping the economy, Annemarie stresses the need for women to help design what's next. She urges more feminine energy in a space currently dominated by masculine leadership.
Leadership Requires Duality: Good leaders know when to lead and when to follow. In a distracted world, focus is power - and Annemarie recommends choosing one thing to master rather than doing it all.
The Power of the Pause: After losing her home in a fire, Annemarie took a year off - and learned the value of space. When you allow silence, healing, and distance, unexpected clarity and solutions often appear.
Mentorship Is Transformational: From three pivotal mentors, Annemarie learned that mentorship is about character, not just career advice. The best guidance comes from how someone lives, not just what they say.
Don’t Wait—Ask for Help: Mentors are often just waiting to be asked. Asking thoughtful questions shows curiosity and confidence - and builds meaningful, two-way relationships.
Unleashing Her Inner Queen: For Annemarie, it’s a journey of self-trust, emotional intelligence, and quiet power. It's not a destination - it's a constant evolution of becoming more intuitive, adaptive, and open to change.
