566: 14 Years of Wholesaling Taught Them This episode artwork

EPISODE · Jul 24, 2026 · 37 MIN

566: 14 Years of Wholesaling Taught Them This

from The DealMachine Real Estate Investing Podcast · host Obi Dorsey, Shelby Dorsey, David Lecko

Join Us for DealMachine Unveiled: https://www.dealmachine.com/unveiled Fourteen years of wholesaling and fix and flip in Jacksonville, Florida, and Obi and Shelby Dorsey of Freedom Home Buyers are still at it while most investors have come and gone. In this conversation with David, they walk through what's actually kept the business alive across every market shift since 2011, from a disciplined buy box to a hard rule on marketing spend. They get candid about why scaling their team past 20 people backfired and how they settled into the leanest, most profitable version of the business yet. They also cover self-managing 35 rental properties and how they use DealMachine data inside their Salesforce CRM to find and close deals.   KEY TALKING POINTS: 0:00 - Meet Shelby & Obi 2:53 - Why Wholesaling Is Their Focus 4:40 - How It All Started 14 Years Ago 9:38 - Shelby Joins the Business 12:30 - Evolving Their Marketing Channels 14:35 - Using DealMachine Daily 16:13 - Lessons From Scaling Up 19:59 - The Truth About Marketing Methods 24:27 - Their Perfect Buy Box 29:29 - Property Management Tips 32:18 - Advice for New Investors 34:01 - Where to Find Them & Name Stories 36:55 - Outro LINKS: Facebook: Obi Dorsey https://www.facebook.com/obi.dorsey   Facebook: Shelby Dorsey https://www.facebook.com/shelby.dorsey.9   Website: Obi Buys https://www.obibuys.com/   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/ 

Episode metadata supplied by the publisher feed · Published Jul 24, 2026

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A husband and wife team breaks down the discipline that's kept their wholesaling business profitable for 14 years while most investors burned out.

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566: 14 Years of Wholesaling Taught Them This

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