Dakota Bailey shares how he built a real estate operation doing 350 deals a year in a small market by simplifying his systems, trusting the right people, and staying disciplined as volume scaled.
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/