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 - Intro 0:49 - An Overview Of Dakota Bailey’s Business 3:06 - The Importance Of Focusing On One Strategy 4:36 - The Story Of How He Got Into Business 11:11 - Buying Out His Partners 15:46 - Sales Tips 18:33 - What His Team Looks Like Now 20:17 - Personal Development 23:25 - His Book & Early Struggles 28:17 - The Biggest Thing He Learned Last Year 31:07 - Losing Money On Deals & Stress Management 36:05 - How They Find Their Deals 39:51 - Data They’ve Been Looking For 46:13 - The Dangers Of Investing 48:54 - What He’s Excited For & His Other Businesses 53:24 - Closing Thoughts And Dakota’s Social Media 53:39 - Outro LINKS: Instagram: Dakota Bailey https://www.instagram.com/dakotabailey.in Links: Dakota Bailey https://linktr.ee/DakotaBailey Instagram: David Lecko https://www.instagram.com/dlecko Website: DealMachine https://www.dealmachine.com/pod Instagram: Ryan Haywood https://www.instagram.com/heritage_home_investments Website: Heritage Home Investments https://www.heritagehomeinvestments.com/