#149 — Adam Brotman: Building the Mindset of an AI‑First CEO

Adam Brotman is the former Chief Digital Officer of Starbucks and Co-CEO of J.Crew, and co‑author of the e‑book AI‑First: The Playbook for a Future‑Proof Business and Brand. At Starbucks, he helped create one of the most admired digital customer experiences in the world and was named Chief Digital Officer of the Year. Today, as co‑founder of Forum3, Adam helps executives navigate the next era of business transformation—one where AI is no longer optional, but foundational.Over the past two years, Adam has interviewed some of the most influential voices shaping artificial intelligence—Bill Gates, Sam Altman, Reid Hoffman, and Ethan Mollick, among others. Through those conversations, he’s uncovered what separates companies that simply experiment with AI from those that truly transform.In this episode, we unpack what it really means to become an AI‑first leader—someone who doesn’t need to code or build models, but who develops the instinct and conviction to guide their teams into this new frontier.In this episode we cover:What it means to be an AI‑first CEO and why it starts with an authentic “aha moment.”Bill Gates’ perspective on AI as a tool for qualitative uplift, not just productivity.The idea of the “middle era” of AI—why it feels messy, and how visionary leaders navigate it.Lessons from Starbucks’ shift from digital‑first to AI‑first thinking.Why the real ROI of AI lies in better decisions, faster, across every function.Episode Timeline: 00:00 — Highlight from today’s episode 01:15 — Introducing Adam + today’s topic 02:30 — The AI‑first mindset: where transformation really begins 06:00 — Bill Gates on why AI is bigger than any past tech shift 10:00 — Quantitative vs. qualitative productivity 12:00 — Inside “the middle era” of AI 16:00 — Defining the AI‑first company and leader 25:00 — Beyond ROI: reframing AI’s value 28:00 — Research insights: why AI improves decision quality 31:00 — From skepticism to the CEO’s “aha” moment 33:00 — What’s next after the middle era 38:00 — Closing reflections + how to keep learning from AdamAdditional Resources: LinkedIn: https://www.linkedin.com/in/adambrotman Book & Company: https://www.forum3.com/ai-first-bookThank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast