Reboot Podcast Episode Wisdom for Work #29 – Frameworks for Leading & Managing People

Ali brings together her decades in a variety of startups (as an operator, managing projects-teams-and-human resources, and developing brands) with a lifetime of soul-based explorations to the field of leadership development. Ali joined Jerry Colonna in 2013 to create life-changing CEO and Founder Bootcamps, both in the US and abroad. In 2014, she co-founded Reboot.io with Jerry Colonna and Dan Putt.

Her book, The Art of Being Human at Work, is a collection of essays that explores the core philosophy of Reboot’s unique approach to business and leadership: that a combination of practical skills and radical self-inquiry are both necessary parts of what it takes to grow, build, and sustain a great company. Tackling issues like burnout, the perils of perfectionism, fear of change, building trust, weathering failure, and defining success, it teaches us that if we are to work and lead well—with authenticity, courage, integrity, and compassion—we must first do the necessary inner work of becoming a better human. It pays to be conscious about not only what we’re doing but how we’re doing it, and this book provides a roadmap for leaders and CEOs to do just that.

As Managing Partner of Reboot Ventures, the creative lab of Reboot, Ali is the spark behind Reboot Supervision, which offers coaches transformational support with coaching supervision, group supervision, and 3-Day Coach retreats. She also oversees Reboot Press, an imprint for indie authors. 

As an executive coach, entrepreneur, and musician, Ray helps leaders orchestrate possibility. He works with those who sense there’s a deeper way to grow their organizations—one that honors strategic precision and creative freedom.

Drawing on his experience in systems thinking, entrepreneurship, and performance, Ray helps leaders recognize and strengthen the patterns that make their organizations uniquely valuable. His approach combines artistic sensibility with practical business acumen, demonstrated through his role as CEO and co-founder of an award-winning brand experience company. There, he helped global leaders like Apple, Google, Nike, and Pepsi find their authentic voice through music and sound, learning firsthand how organizations can maintain creative vitality while scaling.

Ray is deeply committed to nurturing the next generation of creative leaders, regularly working with emerging artists and entrepreneurs to build organizations that generate multiple forms of value. This work keeps him connected to the ever-evolving patterns of innovation.

His approach to leadership development explores essential questions: How can we create organizations that honor both structure and spontaneity? What becomes possible when we view leadership as an artistic practice? How can we design systems that enable natural growth?

As a musician, builder, and inventor, Ray brings a craftsman’s attention to detail and an artist’s eye for possibility to every engagement. He finds joy in helping leaders discover their unique artistry in building organizations that matter, creating value that resonates deeply and ripples outward to enrich the larger systems they’re part of.”