485: 350 Deals A Year in a Small Market (INSANE)

Dakota Bailey has quietly built a seven-year real estate operation that put 350 deals under contract in a single year — all in a small Midwest market. In this episode, Dakota breaks down how he went from car sales to running a high-volume wholesaling business, why simplifying his operation was critical to scaling, and how hiring the right acquisitions manager led to 37 deals in one month. He also talks candidly about inventory risk, leadership mistakes, hard conversations, and the mindset required to stay calm while managing dozens of active deals at once. KEY TALKING POINTS:0:00 - Intro0:49 - An Overview Of Dakota Bailey’s Business3:06 - The Importance Of Focusing On One Strategy4:36 - The Story Of How He Got Into Business11:11 - Buying Out His Partners15:46 - Sales Tips18:33 - What His Team Looks Like Now20:17 - Personal Development23:25 - His Book & Early Struggles28:17 - The Biggest Thing He Learned Last Year31:07 - Losing Money On Deals & Stress Management36:05 - How They Find Their Deals39:51 - Data They’ve Been Looking For46:13 - The Dangers Of Investing48:54 - What He’s Excited For & His Other Businesses53:24 - Closing Thoughts And Dakota’s Social Media53:39 - Outro LINKS:Instagram: Dakota Baileyhttps://www.instagram.com/dakotabailey.in Links: Dakota Baileyhttps://linktr.ee/DakotaBailey Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/