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From Yesteryear to Today: A Generational View of Real Estate
Posted on September 30, 2025
Authored by Jonathan Hammer Levy
Jonathan Hammer Levy
C.E.O.
ConfirmBuyer.com
Being a third-generation real estate professional, I have witnessed this industry from every vantage point—first as a curious youngster listening to veterans tell their stories, sweeping floors. cleaning out construction waste then as an assistant gaining my footing, and ultimately as an adult executive leading as a REIT manager, builder, and a digital developer of real estate platforms. With that perspective, the contrast between the past and today could not be clearer.
The Pride of Yesteryear
In earlier decades, real estate was as much about pride and purpose as it was about profit. Professionals wore their role like a badge of honor. Job ownership, mentorship, and loyalty defined the profession. Young agents absorbed wisdom from seasoned leaders, and brokers prided themselves on creating strong teams rather than just counting closings.
Excellence was earned through relentless effort. Long hours, weekend work, and unwavering dedication set the standard. Managers were builders of bridges, connecting agents to clients, developing ancillary business, and nurturing newcomers. Success wasn’t measured by short-term convenience but by long-term legacy.
The Reality of Today
Fast-forward to now, and the motivation to earn more still drives the business. Yet the approach has shifted. Many prefer to work within the safety of a 9-to-5 schedule, leaning on a handful of top producers while offering little to those still developing. Too many brokers settle for the security of a paycheck, benefits, and a comfortable office. But for what? Without or with minimal mentorship, innovation, or expansion, businesses risk stagnation.
The New Advantage: Data and Analytics
Here lies the sharpest difference between yesterday and today. In the past, brokers relied on instinct, experience, and trial-and-error. Real-time insights simply did not exist. As recently as recent months, the industry lacked/lacks the kind of immediate feedback loops now possible through data and analytics.
Today, brokers and managers have an unprecedented advantage: the ability to measure in real time what works, what doesn’t, and where opportunities lie. Properly analyzed, data can reveal client behaviors, agent performance, missed opportunities, and new revenue streams that were once invisible. This is the modern toolkit for leadership.
But here’s the warning: opportunity without consistent execution is wasted. Brokers and managers who fail to embrace and use data consistently are choosing obsolescence. Without adaptation, today’s leaders risk becoming tomorrow’s dinosaurs, outpaced by those who marry traditional work ethic with modern analytics.
The Constant That Remains
Even with all these changes, one truth ties the generations together: ambition and effort matter. Those who still work harder, innovate boldly, and use every tool available rise above mediocrity. Yesteryear’s pride and perseverance remain essential—but today, data has joined the equation.
A Call to Today’s Leaders
So the question is this: Will you cling to comfort, or will you embrace both the old values of pride and mentorship and the new power of real-time analytics? Will you depend on yesterday’s top producers alone, or will you use data to nurture tomorrow’s?
Real estate has always been about building bridges—between people, between opportunity and achievement, between dreams and reality. History and experience taught us that excellence comes from relentless effort. Today, data gives us sharper tools than ever before. Together, they offer a path not just to survival, but to real, sustainable growth.