In this episode, I sat down with Bobby Kough, a West Point grad, former Army football player, and real estate operator who’s done over a thousand deals and is now running a direct-to-seller business pushing 300 deals a year. We broke down the “clear and reload” mindset he learned through sports psychology at West Point and how that reset tool translates perfectly to real estate when you’re getting rejected nonstop or taking hits on deals. Bobby shared how he started during COVID, how a quick early win gave him confidence, how one ugly “dumpster fire” house taught him the hard way to build a tight buy box, and why going to work for a proven operator helped him shave years off his learning curve. We also got into what it really takes to scale across multiple markets, the marketing channels they’re using, why direct mail still works, and why leadership and people are the hardest part of building a real company.
About Bobby:
Bobby Kough is a real estate entrepreneur and operator who helps build and scale direct-to-seller home buying organizations in St. Louis, Little Rock, and Wichita. He played football at West Point, graduated in 2015, and commissioned as a Second Lieutenant in the U.S. Army. While serving, Bobby discovered BiggerPockets and began studying real estate in his spare time.He purchased his first property in 2018, saw early success, and used that momentum to start buying distressed homes. After completing several deals, Bobby made a major career pivot — walking away from an engineering path to become an acquisitions representative, where he learned the business from the ground up by sitting at kitchen tables with sellers.
Since then, Bobby has partnered with operators to build full-scale organizations focused on sales, operations, and culture. Last year, his teams completed over 300 deals across multiple markets. Bobby is passionate about creating systems that serve sellers with integrity, developing strong leaders, and helping real estate teams grow sustainably while keeping people at the center of every transaction.
Connect with Bobby
Instagram: @bobbykough99
Podcast: The Knock Podcast
About Justin:
Justin Colby is the host of The Entrepreneur DNA and The Science of Flipping podcasts and a best-selling author. He is a serial entrepreneur with over and a seasoned real estate investor with over 20 years of experience.
Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence.
Connect with Justin:
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.