Entrepreneur. Philanthropist. Author. Father.
Let’s talk about something most people try to avoid: failure. Not just the word, but the experience, the emotions, and especially… the feedback that comes with it.
In commercial real estate, we’re expected to project confidence, make strategic calls, and “win” often. But here’s the truth: you don’t become a strong CRE leader by only chasing wins—you grow by navigating losses with intention.
Some of my most important business lessons didn’t come from the biggest deals or flashiest successes. They came from the deals that fell apart at the eleventh hour, the misjudged risks, the poorly timed moves, or the tough conversations where someone told me I got it wrong.
Those moments? They sting. But if you can learn to embrace that sting, to sit with the discomfort instead of rushing past it, you’ll start to find something invaluable: wisdom.
In my latest book, Hey Dad..., I talk about the kind of advice I want to pass down—not just to my kids, but to the next generation of professionals. One recurring theme is this:
“Don’t fear failure. Learn from it. Respect it. And most importantly—use it.”
That same lesson applies whether you're managing a national CRE portfolio or leading a small, growing team. Failure—when paired with intentional reflection and honest feedback—isn’t a setback. It’s a building block.
Here are a few hard-earned insights I’ve picked up along the way.
In CRE, speed matters—but when failure hits, your best move is to pause.
Ask yourself:
Reflection turns chaos into clarity. Without it, we repeat the same missteps—sometimes dressed up in new deals.
It’s easy to surround yourself with people who agree with you. But growth? That comes from people who challenge your thinking—respectfully but directly.
Whether it’s your partners, team members, or advisors, create a culture where feedback isn’t feared—it’s expected. And when it comes, listen fully. Don’t defend. Don’t justify. Just absorb.
Failure isn’t useful unless you do something with it. After every tough moment, ask yourself:
Whether it’s updating your underwriting assumptions, adjusting your leadership style, or rethinking a market strategy, let your setbacks directly influence your next step.
Your team watches how you respond to failure more than how you celebrate success. Do you blame others or own your part? Do you shut down or step up? Do you move on quickly, or take time to unpack and learn?
Being transparent about missteps and lessons learned sets the tone for a resilient, self-aware, and high-performing culture.
CRE is a long game. No matter how experienced or strategic you are, you will face adversity—economic downturns, bad timing, tenant issues, cap rate shifts, regulatory changes.
The question isn’t “Will I fail?”
It’s “How will I respond when I do?”
You can normalize this process by:
This isn’t just personal development—it’s strategic growth.
In Beyond the Building, I write about how the future of CRE is data-driven, tech-forward, and people-powered. But here’s the human truth behind all that innovation and strategy:
We only grow if we’re willing to face the hard stuff.
That includes failure. That includes feedback. That includes holding the mirror up and being willing to say, “Here’s where I fell short. Now what can I do about it?”
As CRE leaders, we owe it to ourselves—and the people we lead—to get stronger through these experiences. To model resilience. To embrace discomfort. To turn tough lessons into forward momentum.
What’s a lesson you’ve learned the hard way in CRE? Was there a time when feedback changed the course of your business—or your leadership?
Drop your story or takeaway in the comments. You never know who you might help by sharing it.
And if you’re looking for more strategies that connect personal growth with professional performance, check out my books Hey Dad... and Beyond the Building. They’re different in tone—but deeply connected in purpose.