In this episode, we cover a lot—and we’re not just talking about real estate. First, we dive into the fundamentals of investing in rental properties and why they remain one of the most reliable paths to passive income. Then, we switch gears to talk about how we personally unwind after long, chaotic days (spoiler: usually involves a bourbon on the rocks).

We also read and react to the hilarious (and slightly unhinged) comments from our viral clip about 100 men vs. 1 gorilla. Plus, we take on the heated debate: could a scratch golfer actually make it on the PGA Tour with the right coaching and unlimited time?

To wrap things up, we reflect on our brokerage’s journey—breaking down what’s fueled our growth over the past 6 years and what’s ahead.

In this 100th episode special of the Jay Pitts Show, we kick things off with bold predictions for this year’s Kentucky Derby winner. Then we pivot to the Louisville housing market for an insightful update on inventory trends. Next, we dive into a Broke Agent Media article claiming that more Americans are delaying or cancelling major purchases due to the economic ripple effects of rising tariffs. We also explore a major shift in the real estate industry: what happens as a wave of older agents retires, and how it could impact the business of working realtors. Finally, we lighten things up (sort of) by answering the internet’s viral debate: Could 100 men defeat a gorilla in a fight? Our answers might surprise you.

In this episode, we dive into the biggest challenges facing new real estate agents over the next five years—and what you can do, not just to survive, but thrive. From striking the right balance between investing in your business and saving for the future, to staying organized amid the chaos of commissions, taxes, and marketing budgets, we’re talking about the real behind-the-scenes hustle of building a lasting career.

We also explore whether long-term investing or reinvesting back into your business is the smarter move for new agents just starting out. Plus, we weigh in on Zillow’s recent ban on certain listings.

Whether you're a brand-new agent or a few years in, this episode is packed with practical tips, financial insights, and a few laughs along the way.

In this episode, we dive into the latest market shake-up—stocks and bonds are both down, and we unpack what that means for mortgage rates moving forward. Plus, the U.S. has raised Canadian lumber duties to 34.45%. What impact could that have on housing prices and construction? We also explore how home buyers find and choose their agent, and dive into what today’s buyers are really looking for in an agent. And to cap it off, we share our picks for The Masters and who we think has the edge this year on the green.

Managing money as a realtor isn’t easy—Jay and Ryan break down the smartest ways to keep your finances in check. They also swap stories about their wildest celebrity encounters, react to GameStop’s bold move to buy Bitcoin as a reserve asset, and unpack how NAR's latest MLS rule change could hurt sellers more than help them.

Jay and Ryan dive into the latest chaos in UofL basketball, break down the drama surrounding GLAR Day at the Races, and debate just how many yard signs realtors really go through. They also spotlight Scottie Scheffler’s legendary Masters Champions Dinner, take a deep dive into how Zillow Flex operates, and expose the reality that realtors—not the general public—are Zillow’s true customers. Buckle up for rants, insights, and plenty of industry hot takes!

Co-founder of ResiClub Lance Lambert shares misleading information about Zillow forcing realtors to push their Zillow leads to use Zillow Home Loans for their mortgage. How will the stock market pullback affect the housing market? Gary Vee believes that wealthier people are more unhappy. Jay and Ryan do a draft of their favorite things about March Madness.

This week on the Jay Pitts Show, Jay and Ryan discuss the demographic of people interviewing to join the brokerage and how it's different from previous years. Could the warmer weather affect the market and produce more listings? And why are there realtors who are still trying to take their own listing photos?