On this episode of The Real Experts Podcast, Brett Jennings welcomes Kyle Whissel, the CEO of Whissel Realty Group, recognized as the top real estate team in San Diego.

Kyle’s introduction to real estate came with a surprising twist—he initially hated it. But after seeing an opportunity during the 2008 housing crash, he pivoted from commercial real estate to residential sales and started building his brokerage. “I’ve always thought about streams of sales, not just one transaction,” Kyle explains. This mindset has driven his approach to building a team and a business that thrives even in tough markets.

In this conversation, Kyle dives into the critical mistakes he made early in his journey, like hiring anyone willing to work, which cost him over $100,000 in one year. He shares how identifying the right team members and adopting the EOS (Entrepreneurial Operating System) helped him create a culture rooted in core values. From there, Whissel Realty Group grew to over 110 agents, closing nearly 900 deals annually.

Kyle also talks about leveraging technology to streamline operations and scale effectively. But it’s not just about tools—it's about the people using them. “The right person with the right platform can achieve extraordinary results,” he notes.

Whether it’s structuring his team based on performance quartiles or setting expectations that are enforced across all levels, Kyle’s leadership style ensures accountability and fosters consistent growth. This episode highlights the importance of thinking big, staying disciplined, and building a team culture that lasts.

Here are the key takeaways:

(2:32) How a $17k sale started a real estate career

(5:56) The $100k hiring mistake that changed everything

(9:52) How relationships built a real estate network

(13:39) Core values and systems: fixing the hiring process

(15:00) Why isn’t your CRM delivering results?

(19:37) Defining core values the right way

(28:05) Why do performance quartiles work?

(30:04) The role of expectations in team retention

(33:21) The model that balances support and autonomy

(34:07) The danger of blinders in real estate

(36:53) Shiny object syndrome: the real estate trap

(38:51) The three-thing rule for business growth

(40:54) The power of partnering for growth

Join us as we explore Kyle’s journey and the systems that have made Whissel Realty Group a standout in the industry.

About Kyle Whissel

Kyle Whissel is the CEO and team leader of Whissel Realty Group, brokered by eXp Realty. With over 16 years of experience, Kyle has built a top-performing team in San Diego, recognized as the #1 real estate team in the county by The Wall Street Journal. His leadership focuses on leveraging systems, technology, and a team-oriented approach to deliver exceptional results across three locations in San Diego County. Kyle is also a national speaker and a prominent figure in the Fast Forward Movement at eXp Realty.

Contact Kyle at:

Website

LinkedIn

About Brett Jennings

Brett Jennings is the founder of Real Estate Experts and a recognized figure in the real estate industry, known for his expertise in luxury home marketing and negotiation, certified by Harvard Law. His achievements include being named in the top 1/10th of the top 1% of real estate groups by the Wall Street Journal. Beyond accolades, Brett is passionate about coaching clients through real estate decisions to impact their lives positively. His unique approach combines real estate knowledge, financial insight, and life coaching, ensuring clients navigate the market confidently.

Contact Brett at:

LinkedIn

Website