✍🏽 Landon’s Loop #142


This week’s newsletter is supported by 1440 & University of Chicago Graham School
What’s in the Loop this week:
🎙️ Chicago Futurist Vol. 3 with Cait Moran, Global Head of AI at Goodyear
📅 Tech events in Chicago this week
🎓 Upcoming UChicago Graham School seminar
🧠 Partner Spotlight: 1440
1440 is few things:
A Chicago-based media company focused on fact driven coverage
A daily newsletter covering global affairs, science, and technology
A community for people who love to learn
I’m one of the millions who start their day with 1440.
I’ve followed their founder Tim Huelskamp’s work for quite some time. He and the team have built an unbiased approach to news and knowledge that’s rare in today’s media landscape, and quietly grown into one of Chicago’s fastest growing companies.
Subscribe at join1440.com
If you’re interested in exploring advertising options to get in front of over 4.6 million readers, I’d be happy to connect you with Tim directly!
🎙️ Chicago Futurist: Cait Moran, Global Head of AI at Goodyear

Cait Moran is shaping Goodyear’s AI strategy as their Global Head of AI.
Goodyear is a global enterprise with nearly $19B in annual revenue, over 60,000 employees, and a long standing place on the Fortune 500.
Here’s our conversation:
Describe your day-to-day at Goodyear
CM: My day-to-day is developing deep fluency in our business - how we build, how we decide, how we move - and reimagining what our future looks like in the AI era. Some days I’m whiteboarding with executives, other days debugging trust between a team and a new AI tool.

At Goodyear, AI touches R&D, manufacturing, supply chain, and sales. How do you decide where it makes sense to build internally vs rely on major model providers?
CM: What matters is connection. When intelligence is fragmented, you get friction. When it's unified, you get momentum.
Don’t end up with dozens of smart systems that don’t talk to each other. A connected intelligence, a shared nervous system, should be a shared enterprise aspiration.
If it creates competitive advantage, it’s ours to deeply own, whether through internal build or tightly governed partnerships. We win by owning outcomes. At Goodyear, that means we're thoughtful about where proprietary intelligence creates differentiation. Our mission is to be #1 in Tires & Service. My decision making is based on what moves our top line.


The model is rarely the most interesting part. What matters is who owns the data, orchestration, feedback loops, decision rights, and the human experience with AI. Companies fixating on the model are asking the wrong question. The right question: what decision does it enable, and who owns that moment?
What characteristics make startups great partners for Goodyear
CM: The best startups understand both people and systems. They respect operational reality, move fast without breaking trust, and solve real problems - not just technical ones. Speed without empathy doesn't scale in an enterprise.
Enterprise transformation is as much about people, trust, and muscle memory as it is about technology. The best ones want to build something that lasts.
There is one Chicago founder approach that stood out to me in the last 6 months: Daksh Guard from Orcho. He asked me the right questions in person and I set my key guardrails, “No powerpoints. I’m over it. We can do better now.” One follow up conversation and my expectations were exceeded. He listened. Daksh and I crossed paths at mHUB at an AI Collective Chicago event. This is representative of the way I prefer to explore problems.
Will AI agents reshape org charts or do they only reshape how decisions get made inside existing structures
CM: I believe agentic systems will evolve how authority and work are expressed in org charts. Today, the bottom matters as much as the top. Over time, companies may shift from rigid hierarchies to orbital systems, where teams form around problems—intelligence pods, not titles. Authority may come from clarity, not control.

Goodyear was in on digital twins early. How does intelligent tire data push digital twins further now?
CM: What's happening with intelligent tires is part of a larger pattern. When physical products become data sources, the twin transforms.
We may see digital twins go through three shifts at once. First, from static to living - continuous data streams mean the twin is always current, not a snapshot from last quarter. Second, from specialist tool to enterprise or consumer asset. When a twin can explain itself in natural language, suddenly it's not just for engineers or industry specialists. Third, they become generative. Not just "what happened" or "what might happen," but "what should we try next."
Together, this creates systems that sense, reason, and suggest. Digital twins are key to the Physical AI era.
Goodyear is rooted in the Midwest. Does that influence how you think about AI differently than coastal companies
CM: Oh yes, because it influenced me to see that the Midwest is AI’s biggest opportunity in the U.S. This is where AI gets real. That is why I joined Goodyear.


When your business is physical, global, and safety-critical, AI can't be abstract. It has to work. It has to be reliable. And it has to respect the people who build things the world depends on. Midwest pragmatism cuts through hype. It’s the key advantage of the region. AI earns its place here by delivering results, not demos.
The coasts demo AI. The Midwest deploys it.
If you were advising another Midwest legacy enterprise starting their AI journey, what would you tell them to do in the first year
CM: Stop chasing tools. Start mapping decisions. Identify where time, judgment, and coordination break down, then rebuild those moments with AI. Transformation starts with truth, not technology. Be honest about where your organization loses days, clarity, or confidence. That’s your roadmap.
The more I reflect on AI, this is what I see. AI predicts futures and generates new ones. Not sequentially…simultaneously. For the first time, humanity has a tool that collapses foresight and creation into a single act. That is an entirely new relationship with possibility. And once you see it that way, you can't unsee it. In practice, this shows up as faster learning loops and better decisions. And navigating that shift? Still human work.
I’ve noticed you’re excited about quantum. How should enterprises think about quantum? Experiment now, or prepare architecturally for later?
CM: I'll answer this as a personal point of view, not a company position. I’m excited about quantum. I’ve been dead serious about it for the past 5 years. Take it seriously.
Five years ago, I was told AI wasn’t ready. It was. Now the same people say that about quantum. Enterprises don't need production use cases yet, but they do need quantum literacy. The companies that build quantum literacy early will be better positioned when the technology matures.

The convergence of AI and quantum is already underway. The time to be curious was yesterday.
🎓 Immerse Yourself in UChicago’s Academic Community
The University of Chicago’s Graduate Student-at-Large (GSAL) and Graduate Student-at-Large: Business (GSALB) bridge programs are designed for individuals looking to refine academic interests, advance their professional path, or prepare for graduate study. Tailored to your goals, the programs allow you to explore graduate study in a specific discipline, preview graduate-level courses and seminars, or pivot into a new career field.
Through GSAL, students gain the skills, credentials, and confidence needed to pursue ambitious goals. Alumni have gone on to Master’s and PhD programs in the humanities, social sciences, and biological sciences, as well as professional schools in business, medicine, law, public policy, and social work.
Program Benefits
Experience the academic depth of the University by auditing courses in a wide range of disciplines
Access an abundance of UChicago resources: University email address, library services, academic advising, and the opportunity to learn from distinguished faculty
Engage in the rigor and experiences only found at a top university
Online Information Session
Join their online information session on February 18 at noon CT. Explore unique opportunities that their programs offer to enhance academic journeys. Director of the GSAL Programs, Esther Pandian-Riske, and Dean of the Graham School, Seth Green, will share program details and admissions process.
📅 Who’s Hosting This Week
Agentic Engineering in 2026
Tuesday January 20th











