Kailan Boston

Kailan Boston brings a rare blend of proven results, strategic insight, and real-world experience to the classroom, making him an instructor for those eager to master the real estate landscape. Since 2019, Kailan has built a career defined by results—representing a discerning clientele of private investors, wealth managers, entrepreneurs, business owners, international buyers, and first-time home buyers & sellers. His ability to combine high-level business acumen with emotional intelligence has set him apart in the competitive world of luxury real estate.

A Milwaukee native, Kailan became the first in his family to play college football, graduate with a four-year degree, and earn a master’s degree. With an MBA from Ohio University and nearly a decade of leadership experience as an Athletic Director, he embodies resilience, adaptability, and excellence. His background in sports leadership sharpened his ability to craft winning strategies and lead with clarity—skills he now passes on to his clients and students alike.

Kailan has served on the Wisconsin Realtors Association’s Diversity, Equity, and Inclusion Committee, bringing his passion for representation and fairness to the forefront of his career. Today, he channels that same passion into teaching—helping students understand not only the mechanics of luxury real estate, but also the mindset and strategy required to succeed.

Students who train with Kailan gain more than just knowledge—they gain a mentor who lives by the belief: “If you believe it, you can achieve it.” His teaching is grounded in real-world application: from marketing strategies that capture global buyers, to negotiation techniques that create true win-win outcomes, to positioning properties so their stories are told with precision and artistry.

Whether you’re an aspiring real estate professional, needing Post-Licensing and CE opportunities, an entrepreneur expanding into luxury markets, or someone curious about building a career with intention, Kailan’s instruction offers the blueprint to achieve excellence. He teaches with the same conviction he leads his family of three young boys: dream big, act with courage, and never limit what’s possible.