The Decisions That Changed Everything

People often ask me what the secret was to building a business that sold more than three times the number of investment properties than any other firm in New York City for 14 consecutive years. They expect the answer to involve a particular strategy, a recruiting philosophy or some proprietary marketing technique. 

The truth is much simpler. 

When I look back over more than four decades in commercial real estate, I don’t believe my career was built by thousands of decisions. It was built by a handful. Most days were ordinary. I showed up, worked hard, made calls, met clients, negotiated transactions and tried to improve a little each day. 

But, every so often, a decision came along that permanently altered the direction of everything that followed. Those are the moments that shape careers, companies and, ultimately, lives.

The first came before my career even began. As a student at Wharton, I thought I wanted to become an investment banker. That was the prestigious path. Then I spent a summer at Coldwell Banker in commercial real estate. I loved the entrepreneurial nature of the business, the direct connection between effort and results, and the opportunity to build relationships rather than simply analyze transactions. I returned the next two summers and joined Coldwell Banker full time after graduation in 1984. Looking back, that single decision determined the course of the next 42 years (and counting).

A few years later, Paul Massey and I decided we wanted to start our own company. We walked into Chemical Bank seeking a loan to finance our dream. They laughed at us. No one wanted to lend money to two young brokers with little more than ambition. 

Instead of abandoning the idea, we spent the next two years saving every dollar we could. By November 1988, we had accumulated $400,000 and launched Massey Knakal. At the time, it felt like an enormous leap into the unknown. Today, it simply looks like the obvious beginning of a successful story. Success has a way of making yesterday’s uncertainty disappear.

The decisions that followed became increasingly consequential. By 1999, every sales territory Massey Knakal had in Manhattan was covered. We had to decide whether to become a full-service real estate company or expand geographically while remaining specialists in building sales. We chose to stay focused on what we believed we could do better than anyone else, and opened offices in Queens and then Brooklyn. 

That decision reinforced a lesson I have come to appreciate throughout my career: Growth does not always come from doing more things. Often it comes from doing fewer things over a larger field.

The most significant decision of my career came immediately after Sept. 11, 2001. While much of the industry was reducing staff and preparing for a prolonged downturn, we made the opposite bet. We believed in the future of New York City. 

Up until then, Paul and I had personally interviewed every prospective employee. We hired a director of human resources and began recruiting aggressively. When the attacks occurred, we had 21 employees. Two years later, we had hired approximately 150 people. 

It was the greatest business risk we ever took. Had the market failed to recover, the company almost certainly would have gone bankrupt. Instead, New York rebounded, and, because we already had experienced professionals covering every market, the years that followed became by far the most dominant period in our firm’s history. What appears courageous in hindsight felt terrifying in real time.

Not every inflection point involved taking a risk. Some involved deciding not to act. In 2007, we negotiated the sale of our company to CBRE for $50 million. The transaction ultimately did not happen, but the experience taught us something invaluable. We learned how acquisitions worked, what buyers valued, and what they expected from founders after a sale. Rather than viewing the failed transaction as a disappointment, we treated it as preparation. 

Seven years later, when we sold the company to Cushman & Wakefield for $100 million, we were far better equipped because of what we had learned from the deal that never closed.

Other decisions were driven by painful experiences. After leaving Cushman and moving to JLL in 2018 with 53 colleagues (all of whom were with me at Massey Knakal), I had no interest in starting another company. The memories of the Global Financial Crisis, when we were forced to lay off people we cared deeply about, were still too vivid. I simply did not want to shoulder that responsibility again. It took another six years, another unexpected career change, and enough distance from those difficult memories before I realized it was time to become an entrepreneur once more. 

Founding BKREA in April 2024 was not simply the result of being fired. It was the result of recognizing that no existing platform could help me serve clients better than the one we could build ourselves.

There is an important lesson hidden inside all of this: None of these decisions came with certainty. There were no guarantees, no spreadsheets that could predict the future, and no one who could tell us with confidence which path would prove correct. Every one of them required judgment. 

Judgment is what allows you to make sound decisions when information is incomplete. It is developed through experience, pattern recognition, curiosity and countless ordinary days spent learning your craft.

Most of our careers are built quietly, one disciplined day at a time. But, every once in a while, life presents an inflection point. In those moments, your future is determined less by the options in front of you than by the person you have become before the decision ever arrived. The decision may change your direction. Becoming the kind of person capable of making that decision is what changes your life.

Robert Knakal is founder, chairman and CEO of BK Real Estate Advisors.