INTERVIEW | Make Money by Becoming an Octopus Organization with Dr. Jana Werner & Phil LeBrun

Dr. Jana Werner and Phil LeBrun are senior leaders at Amazon Web Services who help Fortune 500 companies navigate AI innovation, organizational change, and leadership transformation. Jana is an Executive in Residence at AWS, a Harvard Business Review Press author, and a global transformation leader with experience spanning financial services, startups, and DHL. Phil is the former international CIO of McDonald's, where he led technology modernization across 38,000 restaurants in 120 countries. Together, they co-authored The Octopus Organization, a book focused on helping organizations embrace decentralized leadership, AI adoption, and human-centered change. On this episode we talk about: Why most corporate transformations fail — and how to avoid “soul-destroying” change initiatives The rapid acceleration of AI and why companies are struggling to keep up How Amazon approaches AI innovation internally and encourages experimentation at scale The meaning behind “The Octopus Organization” and decentralized intelligence Why curiosity is one of the most valuable career skills in the modern economy Phil’s journey from flipping burgers at McDonald’s to becoming international CIO Jana’s philosophy of saying “yes” to opportunities and connecting the dots later Why leadership isn’t tied to a title — and how anyone can become a leader The importance of learning over certainty in today’s workplace How AI tools are reshaping organizational structures and decision making Why transformation projects fail 70–90% of the time Advice for young professionals navigating today’s corporate and AI-driven landscape How experimentation and autonomy create innovation inside large organizations The role of curiosity, lifelong learning, and ownership in career growth Why successful leaders ask better questions instead of pretending to have all the answers Quotes from the Episode: “We prefer two teams solving the same problem rather than everyone waiting for permission.” — Phil LeBrun “If AI stopped developing today, it would still take companies five years to catch up.” — Dr. Jana Werner “We train people to have answers, not ask questions.” — Phil LeBrun “My career is a strange connection of dots because I said yes to a lot of things.” — Dr. Jana Werner Connect with Dr. Jana Werner & Phil LeBrun: The Octopus Organization Official Website A Word from Our Sponsors: - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go to https://invest.modemobile.com/travismakesmoney-Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices