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/