Having been in this business since 2015, I’ve seen the industry evolve through multiple phases—from the direct mail era, to the rise of cold calling and texting, and now into the AI-driven, compliance-heavy environment we face today.This post breaks down how my wholesaling operation is structured in 2025, what’s changed, and what systems I use to consistently close deals in today’s market.A Brief History of My Wholesaling Journey (2015–2022)2015–2018: Direct Mail Dominance: Back when I started wholesaling in 2015, the primary way to generate deals was through direct mail.

AI is the system.

It's important to remember that you don't need AI to do the math...

yeah the AI posts with different fonts and bold, 27 emdashes, an ending that says "in conclusion" and 25 graphics instead of bullets, then the person tells you "that was not AI" 

Ive driven by and if the exterior is any indication of the interior, its going to need some work. 

You are using AI as an agent. 

That’s worked well, but as I look toward the next phase (and eventual retirement), I want to intentionally shift from appreciation-driven growth to stable, income-focused investing for retirement income  I’m considering deploying ~$2M to buy 4-6 properties in all cash.

Quote from @Adam Macias: Handwriting letters has been more effective right now than anything AI can do for me in real estate.But a real handwritten letter. 

The dominant amenity might be a lake, trails, glamping units, or even community-driven programming, but the takeaway is the same: you’re underwriting an operating business, not just dirt.

I am not in commercial real estate, but I think there is a lot of opportunity on that side with AI - I havent even looked into it but your question made me think about it, I imagine there is a way to identify opportunities for commercial properties that are undervalued strictly based on the current rent ( easiest value add in my opinion.