Make Peace with the Long Game – Fearless, Consistent Care

A dedicated architect meticulously plans for the future, surrounded by blueprints and scale models in a sunlit office.

One of the most consistent truths in commercial real estate is that the path to meaningful success isn’t a sprint—it’s a long, often cyclical climb. If you’re serious about building a durable career, you have to make peace with the long game.

This week, we draw on the perspective of industry veterans who have weathered the most volatile moments in CRE history—from the S&L crisis, to the Great Financial Crisis, to the aftermath of the pandemic. These leaders remind us that enduring success is built on three timeless pillars: fearless action, unrelenting consistency, and genuine care for your partners, investors, and projects.

Lesson 1: Patience and Permanent Capital (The Long Game)

Commercial real estate rewards those who play the long game. In a market environment that often prioritizes quick returns and transactional wins, the real differentiator is patience—paired with strategic control.

Gary Rappaport, who has weathered six or seven downturns since the 1970s, is clear: institutional capital is often a means to an end, not the end itself. His focus is on building assets you can hold and manage over time, with people you trust. That kind of staying power is only possible with patient capital and deep relationships.

Oliver Carr III reinforces this, pointing out that today’s distressed market presents more opportunity than he’s seen in decades. But capturing that opportunity requires a long-term mindset—one that sees downturns not as threats, but as openings for value creation and deeper understanding of how markets truly work.

Lesson 2: Credibility is Currency (Consistent Care)

Reputation in CRE is earned slowly and tested suddenly. When the market turns—and it will—the most valuable thing you carry is your credibility.

Tom Burton emphasizes the importance of assessing character when choosing operating partners, particularly emerging ones. He looks for people who act as true fiduciaries, who are responsive, transparent, and grounded in principle. As David Orr puts it, “always deal with a high degree of integrity and be honorable in the things that you do.”

Bruce Kirsch adds that trust is built through repetition—by doing what you say, consistently, over time. The industry notices when you show up with integrity, whether in boardrooms or on construction sites.

And Brad Olsen offers a useful reminder: small acts of professionalism compound. Be the pebble that creates ripples. Protect your relationships. Don't burn bridges—you’ll likely cross them again.

Lesson 3: Fearlessness Through Preparation

Fearlessness in this industry doesn’t come from bravado. It comes from discipline. From preparation. From knowing your downside and still choosing to lead.

Ethan Penner, a foundational figure in the CMBS market, encourages young professionals to be bold—to “swing for the fences”—but not recklessly. Boldness works when it’s backed by deep thought, clear strategy, and relentless effort.

Len Forkas, who has taken lessons from endurance expeditions to the top of Mount Everest, notes that the best leaders reduce risk through learning. He advises emerging professionals to seek out people who’ve seen what they haven’t—competitors included—and to ask the right questions.

During challenging cycles, there’s no better teacher than real-world experience. Forkas points to loan workouts as one of the most powerful ways to learn the business—because they reveal everything: valuation, negotiation, operations, and how deals truly hold up under stress.

A Final Note: Play for the Long Term

This industry doesn’t just measure deals—it measures people. And over time, investors consistently return to one key question: Can I trust this person to steward capital, relationships, and outcomes?

If you’re building a reputation based on reliability, responsiveness, and ethical leadership, the answer becomes clear.

In commercial real estate, the long game always wins. It’s just a matter of whether you’re committed to playing it well.