As technology continues to reshape our industry, I want to spend a moment diving into a topic that sits at the heart of modern decision-making in commercial real estate: 
The intersection of technology, data, and human insight—and how artificial intelligence is accelerating the value we can extract from all three. 

In our space, we’re used to complexity. Managing debt across multiple assets, juggling capital stack strategies, evaluating market timing, and forecasting future rate movements—it’s all table stakes. But what sets successful CRE operators apart in today’s environment isn’t just access to information. It’s the ability to make sense of that information, fast. 

And that’s where the intelligence trifecta comes in: 

1. Technology: The Engine of Scale and Speed 

Today’s CRE firms are flooded with tools—and increasingly, AI-driven platforms—that promise automation, prediction, and analysis. And while it’s easy to chase every shiny object, the best operators are using technology not for novelty, but for strategic leverage. 

Technology now plays a central role in: 

• Portfolio-wide risk detection (like identifying maturity concentrations or DSCR erosion in seconds) 

• Interest rate forecasting using machine learning trained on decades of macroeconomic data 

• Debt scenario modeling based on real-time pricing, forward SOFR curves, and hedge costs 

• Natural language processing (NLP) to summarize loan docs, abstracts, and covenant triggers—saving hours of manual review 

We’re no longer asking, “Can technology help us model a refinance scenario?”  

We’re asking, “How can it surface the top three viable structures based on current market spreads and our internal return thresholds—instantly?” 

That’s the level of sophistication top CRE tech now brings. 

But tech alone doesn’t close deals or protect portfolios. It just gives us faster, more scalable ways to ask better questions. 

2. Data: The Raw Material of Strategy 

Technology without data is empty. Fortunately, CRE is generating more data than ever before—from rate cap trades and lender term sheets to real-time property performance metrics. 

The key is turning disparate data into directional strategy. 

Let’s take debt as an example. The data is there: 

• Maturity schedules and loan terms 

• Cap expiration and cost forecasts 

• Property-level NOI projections 

• Lender pricing, appetite, and leverage terms 

• Forward curves, dot plots, and yield spreads 

But too often, this data lives in silos: Excel files, emails, lender portals, back-of-napkin underwriting models. 

That’s why platforms like Lobby CRE (which powers our advisory workflows at Defease With Ease | Thirty Capital) are so critical. They centralize the data and plug it directly into our decision frameworks—so we’re not asking clients for the same spreadsheet three times. We’re making faster, more informed recommendations the moment the market shifts. 

When used well, data does more than report the past. It predicts the future. 

3. Human Insight: The Ultimate Differentiator 

Here’s the truth: AI can model. Tech can accelerate. Data can guide. But only humans understand the nuance.  

Only humans can ask, “Yes, this model shows the refinance improves DSCR by 18%, but what does that mean for our investor communication strategy, promote structure, and long-term cash flow planning?” 

Only humans can say, “This borrower isn’t just looking for best execution—they need a lender relationship that’s flexible, familiar, and strategic.” 

This ‘Human Intelligence’ is what turns models into action. It’s what makes the difference between a technically sound recommendation… and a smart business decision. 

We don’t see technology and AI as replacing that. We see it as empowering it. By spending less time crunching numbers, we spend more time adding judgment, experience, and context—the pieces AI can’t replicate. 

The Real Power: When All Three Work Together 

CRE is a human business. But that doesn’t mean it should be manual. When you integrate technology, high-quality data, and human insight, something powerful happens: 

You move faster. 
You reduce risk. 
You make proactive decisions based on full-picture visibility—not fragmented guesswork. 
And you build a scalable, repeatable edge. 

So, what does that mean for you? 

If you’re still managing debt strategy from multiple Excel files, PDFs, and lender emails—it’s time to rethink the stack. 

If your team is spending more time gathering data than acting on it—it’s time to build systems that serve your strategy. 

If your models stop at “should we refinance”—and not “how will that affect our long-term capital plan”—you’re missing strategic opportunities. 

Ask yourself: 

• Are you using technology that’s purpose-built for CRE decisions? 

• Is your data centralized, structured, and real-time? 

• Do you have experienced advisors who can help interpret the outputs and build a better strategy? 

Final Thoughts 

The future of CRE is not about tech replacing humans. 
It’s about tech and data amplifying the best of human decision-making. 

If we build the right stack—and ask the right questions—we’ll not only survive this market cycle. We’ll outperform in it. 

What does your intelligence stack look like? How are you blending technology, systems, and strategy to make better decisions across your portfolio? 

Let’s continue the conversation—and if you’re looking to upgrade your stack, streamline your debt workflow, or uncover hidden risk and opportunity, our team is here to help. 

You can learn more about these ideas—and how to apply them—in my WSJ Bestseller, Beyond the Building. 

I want to talk about something that often gets lost in the fast-moving world of business: purpose. 

In most organizations, we spend a lot of time answering the question, “What do we do?” We refine our offerings, optimize operations, and build strategies to scale. We define goals, KPIs, and OKRs. We focus on what we sell, what we execute, and what we deliver. 

But the most effective leaders—the ones who inspire real performance and lasting impact—focus first on “Why do we do it?” 

Purpose-driven leadership isn’t about being lofty or abstract. It’s about giving meaning to the work we ask others to do. It’s the foundation that turns a group of talented people into a truly aligned, high-performing team. It fuels resilience when business gets hard. It inspires innovation when the path forward isn’t clear. 

When your team understands the purpose behind the work: 

• They make better decisions—aligned with long-term vision, not just short-term gains. 

• They collaborate more effectively—because they know what they’re building together. 

• They stay engaged—because their work matters beyond the bottom line. 

I’ve led multiple businesses across different industries, and one lesson has been consistent: profit may be the outcome, but purpose is the engine. 

So, what does purpose look like in action? 

• In commercial real estate, it might be about creating spaces that foster community, productivity, and long-term value—for tenants, investors, and the neighborhoods we serve. 

• In a software company, it might be empowering clients to reclaim time and clarity through automation. 

• In finance, it might be helping customers make more informed, confident decisions about their future. 

• In your organization, it might be something no one else can define but you. 

And here’s the key: your purpose doesn’t have to be grand. It just has to be clear. It has to mean something—to you, your team, and your customers. 

Ask yourself: 

• What problem are we really solving? 

• Who are we helping—and how are we making their lives better? 

• Why does our work matter when the economy is uncertain, or the numbers are down? 

If you can answer those questions, your “why” becomes a filter for everything else: hiring, product development, partnerships, communication, strategy. And when your team is aligned around that purpose, the “what” becomes much more powerful. 

So, here’s my challenge for you this week: Take a few minutes to articulate your “why”—on paper, with your leadership team, or even in a quiet moment of reflection. Then ask: Does everyone else on the team know this too? 

Because in a noisy, fast-moving business world, clarity of purpose is one of the most underrated competitive advantages you can have. 

In this industry, we often define success by portfolio size, transaction volume, or total assets under management. These are tangible, impressive benchmarks—and rightfully earned through strategic thinking, discipline, and persistence. But over time, I’ve come to realize that while a portfolio can define your career, it’s your legacy that defines your life. 

A portfolio is transactional. Legacy is transformational. 

It’s easy to get caught up in the race—scaling businesses, managing debt, optimizing capital stacks. I’ve spent decades doing just that. But somewhere along the journey, I started asking different questions: What am I really building? What impact will last long after the deals are closed? Who have I empowered along the way? 

That mindset shift wasn’t born in a boardroom. It started at home. 

As many of you know, I’m a father of four. The idea for my recent book, Hey Dad…, grew out of late-night calls and real-life questions from my kids—things like, “How do I budget?” or “What’s the right move in a tricky situation?” That book was never meant to be a business strategy guide, but in many ways, it’s become the most important thing I’ve ever published—because it’s about building a legacy through leadership, guidance, and presence. 

We don’t build legacies just through capital. We build them through character. 

Whether you’re leading a team, growing a firm, raising kids, or mentoring a rising professional, your legacy is being written every day. And it’s shaped less by the highs of your career than by how you show up when things are hard. In my own journey, I’ve seen a few defining themes that consistently shape meaningful legacies: 

1. Leadership with Integrity 

Legacy isn’t what people say about you in the good times. It’s how they describe your actions when the pressure was high. Did you make the ethical decision, even when it cost you? Did you stand by your team, even when the outcome was uncertain? These moments of integrity aren’t always visible in the moment—but they last. They’re remembered. 

2. Mentorship and Opportunity 

I believe one of the greatest privileges in leadership is the chance to create opportunities for others. That could mean hiring someone who just needs a shot, advocating for someone’s growth, or taking the time to teach what you’ve learned. When someone else succeeds because you invested in them, that’s legacy. That’s leverage that lasts. 

In Hey Dad…, I talk about the transition from being a “teacher” to being a “guide”—a shift that happens in both parenting and leadership. Our job isn’t just to give people answers. It’s to help them think, decide, and lead for themselves. 

3. Resilience in Action 

Markets rise and fall. So do businesses. What doesn’t fade is how you adapt and push forward. Resilience doesn’t mean never feeling fear or stress—it means continuing forward with purpose anyway. In a leadership role, your resilience sets the emotional tone for your entire organization or family. 

When interest rates spike or a key deal falls through, your response is watched closely. Likewise, when your child fails or questions their next step, how you react teaches them how to process setbacks and keep going. In both scenarios, legacy is shaped by resilience. 

4. The Power of Presence 

Legacy isn’t always about big, flashy moves. Sometimes, it’s about being fully present. I’ve learned that being there, at a meeting, at a game, or on the phone matters. Especially when time is tight and demands are high, being fully engaged signals what you value. 

This applies to employees and children alike. When people feel seen and supported, they perform better, trust deeper, and grow faster. You can’t outsource presence—and it’s one of the most powerful tools you have as a leader. 

5. Data-Driven Decisions with Human Purpose 

In CRE, we rely on data to make smart choices. KPIs, OKRs, interest rate curves—all of it informs our strategies. But data doesn’t build legacies. People do. And people are motivated not by metrics, but by mission. 

In Beyond the Building, I talk about the intersection of analytics and human intelligence. Use the data. Use the tech. But never lose sight of the people behind the numbers. Build systems that support not just better business outcomes, but better human outcomes. That’s when the work becomes transformational. 

So what are you building? 

A successful firm, a thriving team, a rock-solid portfolio? That’s fantastic. But take it a step further. Ask: What will people say about the way I led, the values I championed, and the opportunities I created? 

That’s legacy. That’s what lasts. 

We don’t have to choose between results and relationships, between success and significance. The best leaders I know do both. They deliver outcomes, and they elevate others in the process. 

If you haven’t already, I invite you to read Hey Dad: Everything You Should Have Learned About Life (But Didn’t)—even if you’re not a parent. It’s a book about life skills, leadership, and the real moments that shape who we become. And if you’ve already read it, I’d love to hear which story resonated most with you. 

Success is a concept that often feels elusive—especially in a world that constantly pushes us to measure progress by external markers like revenue, growth, and accolades. But what if true success isn’t about hitting predefined milestones? What if it’s about living with intention, building something meaningful, and finding fulfillment in ways that go beyond traditional definitions?

As I reflect on my personal and professional journey, I’ve come to realize that “winning” isn’t a one-size-fits-all concept. It’s deeply personal and multifaceted. Whether you’re a leader, an entrepreneur, or someone striving for personal growth, rethinking what “winning” means can help you align your actions with your values.

If you’re in the Charlotte area, I’d love to meet you in person and continue this conversation. On June 5th at 6:30 PM, I’ll be at Park Road Books in Charlotte, NC, for a Hey Dad… Book Signing + Meet & Greet. Whether you’re a parent, mentor, or simply someone who enjoys a good life-read, I’d love for you to stop by! I’m excited to hear your story, sign a copy of the book, and connect outside of the inbox.

RSVP to save your spot, and I hope to see you there!

Now, let’s dive into what I’ve learned about success…

1. Success is About People, Not Just Numbers

For me, some of the most significant wins in life had little to do with financial metrics or business growth. Instead, they were about the relationships I’ve built and the people I’ve helped along the way. In business, we often define success through numbers—revenue, profit, market share. But the true measure of success lies in how we impact others.

As leaders, it’s important to remember that success is about empowering people. Whether it’s creating opportunities for others, sharing knowledge, or supporting your team, investing in people is the most fulfilling and lasting form of success. After all, the impact you have on others can create a ripple effect that far exceeds any personal achievement.

2. Sustainable Growth is Better Than Short-Term Wins

We live in a world that prizes quick results—whether that’s closing a deal or hitting a quarterly target. But in my experience, short-term wins often come at the expense of long-term stability. Real success doesn’t come from chasing the next big win or leveraging temporary circumstances. It comes from cultivating sustainable growth over time.

This principle applies not just in business, but in life. Building something of lasting value requires patience, consistency, and a commitment to making decisions that will benefit you and those around you in the long run. Whether you’re growing a business or nurturing relationships, the most rewarding outcomes come from staying focused on the bigger picture, rather than the immediate payoff.

3. Failure is Not the Opposite of Success—It’s Part of the Process

No one likes to fail, but failure is a natural and necessary part of growth. Over the years, I’ve realized that success isn’t about avoiding mistakes or setbacks; it’s about learning from them and moving forward stronger. In fact, some of my greatest successes have come from the lessons learned during moments of failure.

When you shift your perspective and view failure as an opportunity for growth, it becomes much easier to take risks, experiment, and try new things. Every mistake carries valuable insights that, if applied, can guide you toward greater success. Embracing failure as a stepping stone is crucial to achieving your goals, both professionally and personally.

4. Success Is a Journey, Not a Destination

One of the most important shifts I’ve made in my thinking is recognizing that success is not a destination. It’s a journey—a series of ongoing steps that are constantly evolving. The idea that we will someday “arrive” at success is a myth. Instead, we must embrace the process and take pride in the small wins along the way.

Whether you’re building a business, progressing in your career, or working on personal growth, remember that every step forward counts. Celebrate the progress, not just the end result. The journey itself holds more lessons, challenges, and rewards than any final destination could ever offer.

5. Focus on the Impact You Have, Not Just the Outcomes You Achieve

Ultimately, the measure of success is in the legacy you leave behind. In my career, I’ve found that the most meaningful successes aren’t the ones with the biggest headlines. Instead, they’re the quiet moments when you’ve helped someone else grow, contributed to a bigger cause, or created something that outlasts you.

It’s easy to get caught up in personal achievements, but the true measure of success is how you’ve impacted others. Whether you’re a mentor, a leader, or a colleague, the way you influence and inspire others is the real legacy you create. Success isn’t about what you accumulate, but about what you give and how you help others reach their potential.

Redefining Success

In our fast-paced world, it’s easy to get swept up in the pressure to achieve more, faster. But the real question we should be asking ourselves is: What does success mean to me? How can I define and pursue success in a way that aligns with my values and contributes to something greater than myself?

By redefining success, we can focus on building lasting relationships, cultivating sustainable growth, embracing failure as part of the process, and making an impact that goes beyond personal gain. True success isn’t defined by external metrics—it’s about living a life of purpose, growth, and service to others.

As leaders, we are constantly focused on driving success for our businesses—whether that’s through scaling, navigating market challenges, or optimizing performance. But as we navigate the path forward, there’s another responsibility that we can’t afford to overlook: teaching the next generation.

This week, I’ve been reflecting on something that I believe deserves more attention: the real-world lessons we can impart to the younger generation. Whether they’re entering the workforce for the first time or stepping into their own entrepreneurial ventures, the lessons we teach them can shape their careers and, ultimately, their success.

It’s a responsibility that goes beyond what they’ll learn in a classroom. In fact, many of the most critical skills for life and business aren’t taught in textbooks—they come from experience, insight, and guidance. That’s what I’ve tried to capture in my book, Hey Dad: Everything You Should Have Learned About Life (But Didn’t), which offers the real-life advice I wish someone had shared with me when I was starting out.

But before we jump into some life lessons for the next generation, I’d like to invite those of you in the Charlotte area to my upcoming book signing on June 5 at Park Road Books.

This event isn’t just about signing books—it’s about meaningful conversations on the life lessons that inspired this project. Whether you’re a parent, mentor, or young adult navigating adulthood, stop by, grab a copy, and let’s discuss how to live with purpose and intention as you move forward.

RSVP to save your spot, and I hope to see you there!

Now, here are some key lessons that, as leaders, we can pass down to the next generation:

1. Resilience in the Face of Adversity

When I think back on my career and the challenges I’ve faced, one thing stands out: success isn’t just about the wins—it’s about how you handle the losses. Everyone experiences setbacks, whether in business, relationships, or personal growth. What separates those who succeed from those who don’t is resilience. Teaching the next generation how to rebound from failure and learn from mistakes is a crucial life skill. Resilience builds confidence, grit, and the perseverance needed to push forward, no matter what the future holds. Over the years, I’ve gone through my own struggles, but they have since proven to have shaped my approach to leadership. The message is clear: don’t fear failure, embrace it as a stepping stone.

2. The Power of Listening and Understanding

It’s easy to believe that leadership is all about speaking and directing, but truly effective leadership is about listening. Listening fosters understanding, which leads to stronger relationships and better decision-making. Whether it’s listening to your team, clients, or partners, taking the time to understand different perspectives makes all the difference. In business and life, it’s not just what you know, but how well you understand others. Sometimes, the best advice comes from simply asking the right questions and hearing what’s on someone else’s mind.

3. Building Strong Networks

Success in any field rarely happens in isolation. The most successful individuals understand that networking is not just about landing a job or building a client base—it’s about connecting with others, sharing knowledge, and building relationships that can open doors and provide valuable insights. The next generation must understand the value of relationships in the professional world. Networking isn’t just a task; it’s an ongoing investment in growth, both personally and professionally. Leveraging relationships—whether they’re mentors, peers, or colleagues—can shape opportunities in ways that other factors can’t.

4. The Importance of Data-Driven Decision Making

Gone are the days when decisions were based on gut feelings alone. Today’s most successful leaders rely heavily on data to make informed choices that move their business forward. Whether it’s financial data, customer insights, or market research, data helps us mitigate risk, seize opportunities, and fine-tune our strategies. For young professionals, developing the ability to analyze and leverage data will give them a competitive edge. To be successful, it’s critical to have systems in place to measure progress, track performance, and guide choices with clear, objective information.

5. Building a Legacy, Not Just Profits

At the heart of true leadership lies a deeper purpose: building a legacy that transcends financial success. True leadership involves shaping a legacy that impacts not only the business but also the community, the industry, and the people you work with. It’s about the values you leave behind, not just the profits you generate. The next generation needs to understand that success isn’t only measured by the bottom line. In Hey Dad, I stress the importance of understanding your purpose and how that purpose drives your decisions. Whether you’re helping someone grow professionally or contributing to your community, leaving a lasting impact is the true measure of success.

6. The Importance of Financial Literacy and Strategic Planning

Navigating adulthood means facing financial realities—managing income, budgeting, saving, investing, and planning for the future. We must help the next generation gain financial literacy and understand the long-term implications of their financial decisions. The earlier we teach them how to make smart financial decisions, the better equipped they’ll be to build wealth and avoid common pitfalls.

7. Strategic Risk-Taking with a Clear Vision

We live in a world of constant change and uncertainty. As leaders, we can help the next generation understand that taking risks is often necessary to achieve great rewards. However, these risks should be strategic and aligned with their goals. Having a clear vision and knowing when to act boldly is a critical skill for anyone entering the workforce or running a business.

Preparing the Next Generation for Leadership

The future of leadership lies in the hands of the next generation, and as current leaders, it’s our job to equip them with the skills and mindset they need to succeed. In my experience, passing on these real-world lessons—ranging from resilience and listening to financial literacy and legacy building—will help prepare them for the challenges ahead. It’s not just about preparing them for work; it’s about helping them grow as individuals, capable of thriving in an ever-changing world.

This week’s topic is one I wish I had understood earlier in my career—and definitely in my life as a father, entrepreneur, and operator:

Saying no is a growth strategy.

For a long time, I saw “yes” as the default setting for success. Say yes to opportunity. Say yes to challenges. Say yes to proving yourself. And to be clear—there’s a season where that mindset fuels growth. But unchecked, that same instinct can lead to overextension, distraction, and burnout.

One of the biggest shifts in my career—and in my personal life—was learning that saying no isn’t closing a door. It’s protecting the right ones.

And that’s a lesson I now try to pass down to the next generation. In Hey Dad…, my newest book for young adults (and those guiding them), there’s a section that dives into decision-making—how to prioritize your time, protect your energy, and stay focused on what matters most. It’s framed for someone stepping into adulthood, but I’d argue the principle doesn’t change with age. If anything, it becomes more critical. Because here’s the truth I’ve had to learn the hard way: Every “yes” is really a “no” to something else.

And if you’re not intentional about where your yeses go, you’ll end up trading time, energy, and focus for things that don’t align with your goals—or your values.

Why Saying No Is a Powerful Tool

1. It forces clarity When you know what you’re working toward, it becomes easier to spot what doesn’t belong. Saying no helps sharpen your vision, reinforce your strategy, and avoid the drift that comes from reactive decision-making.

2. It protects your energy As a leader, your energy is one of your most valuable assets. Protecting it isn’t selfish—it’s strategic. If you’re constantly drained by meetings, projects, or decisions that don’t move the needle, you can’t show up fully for the ones that do.

3. It empowers others In business, every time you say no to something that can be delegated, you’re giving someone else the opportunity to grow. That’s how teams scale. That’s how people step up.

4. It sets a standard Saying no to misaligned partnerships, bad fits, or low-ROI distractions shows your team what excellence looks like. It creates a culture that values purpose over busyness.

5. It builds momentum—for the right things Every time you say no to something off-path, you reinforce the discipline that builds long-term momentum. Compound growth isn’t about speed—it’s about direction.

What I’d Tell My Younger Self (and My Kids)

If I could go back and add one more bold, red-inked note to my younger self (the one I wrote about in my last newsletter), it would be this:

“Don’t confuse saying yes with making progress.”

There were seasons I said yes to everything because I thought it made me indispensable. It didn’t. It made me scattered.

There were seasons I felt guilty saying no—to clients, to teammates, to friends. But eventually, I realized that boundaries aren’t barriers—they’re what make high-impact work possible.

In Hey Dad…, I included prompts and questions for young adults to start thinking through this early:

• What do you want to be known for?

• What drains you that doesn’t move you forward?

• What are you willing to say no to… so you can say yes to something better?

These are the same questions I revisit often in my own leadership, as I balance the demands of family, business, and personal growth.

What Are You Saying No To This Quarter?

Saying no isn’t easy—especially in fast-paced industries like commercial real estate, or when you’re early in your career. But over time, it becomes one of the most important tools in your leadership toolbox.

So I’d love to hear from you: What’s one thing you’ve said no to recently—and how did it help you grow? Or… what’s something you wish you had said no to sooner?

As I gear up for the release of my new book, Hey Dad…: Everything You Should Have Learned About Life But Didn’t, I’ve been thinking a lot about the younger version of myself.

The kid fresh out of school trying to land his first job. The young professional chasing the next title without a clue about work-life balance. The entrepreneur learning (often the hard way) how to manage money, motivate people, and stay standing after setbacks.

If I could go back and write a letter to my younger self, it would probably be 30 pages long and mostly bolded in red ink. But since I only have a newsletter’s worth of space, here are just a few things I’d include:

1. Learn the rules of the game before you try to change them. Whether it’s how a mortgage works, how compound interest builds, or how companies actually make money—get the basics down. Don’t outsource your understanding of the things that affect your freedom.
2. The first version of anything—your resume, your pitch, your career—is just a draft. The magic isn’t in the launch; it’s in the refining. Don’t get discouraged when something isn’t perfect. Adjust. Iterate. Move.
3. You’ll never regret asking the extra question. Curiosity will always take you further than charisma. Learn to listen. Really listen. It’s amazing what people will tell you if you’re not just waiting for your turn to talk.
4. Money can solve problems—but only wisdom keeps them from recurring. Make a budget. Stick to it. Understand that living below your means isn’t scarcity—it’s strategy. Save before you splurge. And yes, buy the insurance.
5. Feedback isn’t failure. You’ll be rejected, criticized, overlooked. It happens to everyone. What separates the good from the great is what you do next. Keep your ego in check and let your curiosity out front.
6. Don’t confuse being busy with being effective. The longer your to-do list, the more important it becomes to focus on the right things. Learn to prioritize. Learn to say no. Learn that rest is part of the job.
7. You are the average of your calendar and your conversations. Surround yourself with people who challenge and inspire you. And spend time on the things that move the needle. The rest is noise.
8. Life is long—but moments are short. Be present. Celebrate wins. Call your parents. Show up to the game. These are the things that matter 20 years from now.

I wrote Hey Dad… as the book I wish I’d had when I was just starting out. It’s for every young adult who’s navigating life without a playbook—and every parent, mentor, or friend who wants to help, but doesn’t always know how.

The book is filled with lessons along with advice from 30 experts in their field—each offering hard-earned wisdom that doesn’t sugarcoat adulthood but also doesn’t make it feel so overwhelming.

It’s also meant to be personalized. There’s space to write your own notes, your own stories, your own advice. Because sometimes the most meaningful gift you can give someone is a nudge in the right direction—and a reminder that they don’t have to figure it all out alone.

So here’s my question to you: What do you wish you knew at 18? Or 21? Or 25?

Drop your answers in the comments—whether it’s something you learned from experience, or something you wish someone had told you sooner. Who knows… your lesson might just change someone’s trajectory.

Hey Dad… comes out April 29. If you know a young adult who could use a guide—or a little encouragement—it’s a great graduation gift (especially with your wisdom written inside the cover).

Thanks for reading and for always being part of this community. It means more than you know.

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.

So how do we turn failure into a strategic advantage?

Here are a few hard-earned insights I’ve picked up along the way.

1. Reflect, Don’t React

In CRE, speed matters—but when failure hits, your best move is to pause.

Ask yourself:

• What assumptions did we make?

• What signals did we miss?

• What can we learn from the outcome?

Reflection turns chaos into clarity. Without it, we repeat the same missteps—sometimes dressed up in new deals.

2. Invite Honest Feedback

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.

3. Extract and Apply the Lesson

Failure isn’t useful unless you do something with it. After every tough moment, ask yourself:

• What do I now know that I didn’t before?

• What one thing can I change in my approach, my systems, or my mindset?

Whether it’s updating your underwriting assumptions, adjusting your leadership style, or rethinking a market strategy, let your setbacks directly influence your next step.

4. Model It for Your Team

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.

5. Normalize the Process

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:

• Building time into your review cycles for lessons learned

• Documenting deal outcomes, both good and bad

• Sharing “failure case studies” internally—not to assign blame, but to refine systems and thinking

This isn’t just personal development—it’s strategic growth.

Why This Matters More Than Ever

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.

Let’s Keep the Conversation Going

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.

If you’ve been in this business long enough, you know the fundamentals don’t change—but the strategy must. We’ve operated in challenging markets before. What makes today’s environment particularly complex is the prolonged uncertainty around monetary policy, combined with rising costs, inconsistent asset performance, and mounting pressure from capital partners to deliver results.

The easy move is to wait. To preserve capital. To delay decisions. But in many cases, that “safe” choice could prove riskier than it seems. Inaction in this environment can quietly erode performance—whether through reduced cashflow, missed refinancing windows, or declining asset value due to deferred investment. The challenge, then, is to identify where real risk exists, and where opportunity is simply hiding behind discomfort.

Start with Understanding Your Real Exposure

Balancing risk starts with knowing exactly where you stand. That means taking a hard look at your debt structure, lease maturity schedules, tenant exposure, and operating performance under current and future rate scenarios.

Tools like business intelligence (BI), artificial intelligence (AI), and human intelligence (HI) work best in tandem here. You need more than just raw data—you need insights informed by experience. These help you model scenarios, assess downside protection, and create frameworks that allow for calculated action, rather than reactive decisions.

Ask yourself:

• How rate-sensitive is my current debt portfolio?
• What refinancing risks will I face in the next 12–18 months?
• How do my operating fundamentals hold up if rates stay elevated through 2025?
• Where am I sitting on idle capital or unleveraged equity?

These questions form the basis for rational, strategic planning in an otherwise emotional market.

Look for Opportunity in the Gaps

Once you have clarity on your exposure, the next step is targeted opportunity identification. In this climate, it’s less about finding perfect deals and more about identifying asymmetrical upside—where the risk is manageable, but the potential returns are significant.

That could mean:

• Acquiring distressed or mismanaged assets where the underwriting remains strong
• Restructuring debt to unlock liquidity or extend runway
• Optimizing operational efficiencies to boost NOI and preserve valuation
• Investing in tech or analytics that improve decision-making at the asset or portfolio level

We’re seeing operators use creative approaches to extend loan terms, optimize cap structures, and even convert risk into leverage with select lenders. Some are choosing to proactively recapitalize projects, while others are taking smaller, high-conviction bets in emerging submarkets or niche asset classes.

The thread that connects all of them? They’re acting with intention—not waiting for the market to make the call for them.

Accepting That Risk Will Always Be Present

One mindset shift I’ve found helpful—both personally and across the companies I’ve built—is this: risk never disappears. It just changes form. High-rate environments come with one kind of risk. Low-rate environments come with another. What sets great operators apart is how they anticipate, measure, and adapt.

In this moment, the priority is to avoid binary thinking. We don’t need to go all-in, and we don’t need to sit on the sidelines. Instead, we need to adopt disciplined flexibility—backed by real-time data and clear strategic goals.

That’s why the most forward-thinking firms I know are investing just as much in their decision-making processes as they are in their actual investments. They’re refining how they gather intel, how they model scenarios, and how they communicate strategy internally and externally.

Final Thoughts: Precision Over Paralysis

The high-rate environment we’re operating in will eventually shift—but how you position yourself today will define how you perform when it does.

So, as you evaluate your own portfolio or organization, consider this: Are you navigating from a place of fear, or from a place of clarity? Can you separate true risk from noise? And are you prepared to seize the right opportunities when they appear?

In today’s ever-evolving business landscape, one principle has become clear: being proactive is not just an advantage—it’s a necessity. In an age where markets, economic policies, and industry dynamics change rapidly, the organizations that succeed are those that not only adapt quickly but also anticipate challenges before they even appear. Proactivity is the key to unlocking both long-term growth and short-term success.

In my experience, proactivity is about acting before the market demands it, using data to forecast shifts, and strategically positioning your company for the best possible outcomes. When we talk about being proactive in the context of commercial real estate, it’s not just about responding to external pressures; it’s about creating internal momentum that keeps your organization ahead of the game. Whether it’s anticipating changes in interest rates, adjusting your debt structure before market conditions change, or repositioning your business to meet evolving demand, proactivity is the foundation of successful strategy.

All About Being Proactive

Proactive debt management is a prime example of how businesses can position themselves for success. Instead of waiting until the last minute to refinance or restructure debt, savvy companies anticipate future market shifts, such as rate hikes or economic downturns, and adjust accordingly. Proactive debt management means matching your property’s cashflows with the optimal debt structure, ensuring that debt obligations align with current and future financial conditions. For example, locking in favorable rates before anticipated Fed rate cuts or utilizing forward hedging strategies helps businesses mitigate risk and seize opportunities ahead of competitors. Furthermore, regularly assessing and optimizing your debt portfolio to reflect the evolving market ensures that your financial strategy supports broader business objectives, fostering long-term stability and growth.

But it doesn’t stop with finance. Operational proactivity is just as critical. In today’s world, we have access to an unprecedented amount of data—from market conditions to customer behavior to internal financial performance. Using business intelligence (BI), artificial intelligence (AI), and human intelligence (HI) allows us to make data-driven decisions that keep our businesses agile and ahead of any market disruption. Whether it’s streamlining workflows, optimizing cashflow, or reducing costs, being proactive means continuously using these insights to make adjustments that keep your company running smoothly.

In terms of growth strategies, being proactive means identifying opportunities before they become obvious. Strategic acquisitions, entering new markets, or leveraging emerging technologies require foresight. Proactive leaders know that success is about positioning themselves where the market is headed, not where it is right now. They’re constantly scanning the horizon for new trends and opportunities and have the foresight to act before others even recognize the shift. Whether it’s adjusting your company’s portfolio to align with new customer preferences or embracing new technologies that streamline operations, proactive businesses are always planning several steps ahead.

Lastly, proactive leadership is crucial in driving these strategies forward. Leaders who adopt a proactive approach foster a company-wide mindset of innovation and agility. By aligning their team around a shared vision and empowering them to anticipate challenges, leaders create a resilient culture that doesn’t just survive disruption but thrives in the face of it. Proactive leadership involves not just making decisions based on data but also continuously reevaluating the environment and adjusting strategies. It’s about thinking outside the box and addressing problems before they become issues. It’s about taking calculated risks, knowing that uncertainty can be an opportunity, and trusting your team to adapt quickly.

Next Steps

In today’s fast-paced, constantly changing world, organizations that embrace a proactive mindset don’t just succeed—they lead the way. The companies that thrive will be those who anticipate change, embrace innovation, and stay one step ahead of competitors. As we look to the future, remember that being proactive is the key to unlocking your organization’s potential and staying ahead of the curve.

What steps are you taking to implement a proactive strategy in your organization? How have you seen proactivity drive success for your team or company?