In 1998, a former British paratrooper named Karl Bushby stepped off a roadside in Chile and started walking home to England. No plane tickets, no trains, no “I’ll skip this part and come back later.” He gave himself two rules: No mechanical transport. He would not go home until he got there on foot. Twenty seven years later, he is on the final stretch. Roughly 30,000 miles behind him, about 2,000 miles to go. He has crossed war zones, jungles, the Bering Strait, and even swum nearly 200 miles across the Caspian Sea when geopolitics blocked his path. I watched that story and could not stop thinking about the parallels between his long-game journey, and the AI transformation in commercial real estate. Not because most of us are going to fight off polar bears on the way to automating leasing reports or financial underwriting, but because serious careers and serious firms in CRE transform the same way: one uncompromising step at a time, over a very long period of time. AI Transformation In CRE Is A 30,000 Mile Journey Most conversations about AI in CRE still sound like a short-term plan: 3 months to test a tool 6 months to “roll it out” Another or two and “we’re there” Then the market moves, budgets get cut, a key sponsor leaves, or a vendor disappears, and suddenly the plan is off course. Karl’s journey is a reminder that the real game, especially with something as foundational as AI, is measured in years, not months. Over 27 years he has: Crossed continents and climates he never could have fully planned for at the beginning Lived through multiple wars, financial crises, and technological revolutions Lost loved ones he knew he would not see again before they passed Adapted from total isolation (no smartphone) to a world where 350,000 plus people follow his journey on TikTok The destination never changed. The route changed constantly. That is exactly what becoming an AI native firm will look like. The models and vendors will change The interfaces will change The language we use will change The direction, if you choose it, does not change: “We are building a firm where professional work alongside digital coworkers, and where human judgment and relationships are augmented by machines that understand CRE work end to end.” The Rules You Choose Matter More Than the Route Karl chose two rules at the beginning that made everything harder in the short run and more meaningful in the long run: No mechanical transport No going home until he walked there In CRE, we quietly choose similar rules for ourselves and our firms. On the investment and operating side, rules like: “We underwrite what we own, with real rigor.” “We do not take reputational shortcuts, even if it costs us a fee.” On the AI side, rules like: “We will become an AI native firm, where every team member understands AI’s role in the firm” “We will not outsource thinking to a black box. AI will explain itself and be checkable, with final decisions made by people.” “We will give every person on the team the AI tools and training necessary to succeed long-term.” Those rules increase friction today. They demand more thought, more testing, and more discipline. They also define who you become over 2, 5, 10 years. Once you choose those rules, the route is allowed to change: You may start with one tool and end with another You may begin with point solutions and consolidate to a platform You may pilot in one group and then roll out across the firm The long game is not about getting every step exactly right. It is about refusing to abandon the rules that keep you pointed at the right destination. You Cannot Skip Your Miles, But You Can Share The Load Karl could have flown over the Darién Gap, taken a ferry across the Bering Strait, or booked a short flight when visas fell through. Instead, when one path closed (Russia, Iran), he found another that still honored his rules. In one case, that meant swimming 200 miles across the Caspian Sea. In our world: You cannot skip the work of understanding your own data, models, and risk. You cannot skip the time it takes to redesign processes around AI instead of just stapling tools on top. You cannot skip the conversations with teams who are understandably skeptical or tired of buzzwords. But you can decide whether you are carrying everything on your own back, or using the tools available to you. That is how I think about AI and digital coworkers in CRE. You still have to: Decide which markets and strategies you believe in Choose which risks you are willing to take as a firm Stand behind the deals and asset decisions that come out of your shop AI will not walk those miles for you. What it can do is carry some of the weight: First pass underwriting, data gathering, and comp pulls Drafts of IC memos, leasing reports, and investor updates Routine asset management reports, checks, and workflows You still walk the 30,000 miles. You just do it with a better pack, better shoes, and someone next to you who never sleeps.