21 August 2025



One year ago today, I announced I was leaving Apple after 21 incredible years.

This past year has been one of the most rewarding chapters of my life. I’ve recharged, reconnected with friends, and created lasting memories with my family. But I’ve also been busy listening and learning.

I’ve had meaningful conversations with leaders across technology, AI, media, sports, entertainment, gaming, education, healthcare, and investing. My goal was to better understand the challenges they face and the opportunities ahead. Through these discussions, two key takeaways emerged:

AI is profoundly reshaping many aspects of our lives — how we work, learn, play, create, and tap into our potential.

Even exceptional leaders need fresh perspectives. Successful founders, CEOs, and investors told me they hunger for insights beyond their inner circles. They want voices that cut through groupthink and open new paths forward.

After three decades building transformative products and platforms, I’m channeling everything I’ve learned into my next chapter: 55 West, my new advisory and investing firm focused on helping visionary leaders accelerate their impact.

The name honors 55 West Lawn, my address during my final year at UVA. Living on the Lawn represented possibility, community, and new beginnings — values that continue to guide my work today. At 55 West, I partner with companies shaping tomorrow, from bold startups to established brands, focusing on strategy, product, and growth.

Building something remarkable? Let’s connect.

Here’s to what’s next.