In this episode of Sky’s the Limit, Mike sits down with Jithu Sajeevan, real estate investor, agent, and founder of Team CheckMate and DIG Chess.

Jithu shares his journey from professional chess player to entrepreneur and real estate investor, including how he purchased his first 2-family property in Bristol, Connecticut at just 19 years old. Since then, he has acquired 8 properties totaling approximately 40 units, sold more than 100 homes as an agent, and built a real estate team that now closes close to 100 deals a year.

We break down what motivated Jithu to choose real estate over the stock market, the challenges he faced qualifying for financing as a young investor, and the lessons he learned from his first deal. From persistence and problem-solving to building a business and investing at a young age, this episode offers practical insight for anyone looking to get started in real estate and build long-term wealth.

Useful Links:

• Our Website: https://www.skytreeinvestments.com/podcast
• Facebook: https://www.facebook.com/profile.php?id=100063717056842
• Instagram: https://www.instagram.com/mikedohertyrealtor/

Connect with Jithu!

• Email: jithu@teamcheckmate.com
• Instagram: https://www.instagram.com/jithu_ctrealestate/
• Facebook: https://www.facebook.com/jithu.sajeevan.2025/
• LinkedIn: https://www.linkedin.com/in/jithu-sajeevan/

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