Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! Today I’m joined by my friend Steve Trang, founder of Objection Proof AI, host of Real Estate Disruptors, and one of the most respected sales trainers in the real estate investing world.

In this episode, Steve and I dive deep into the intersection of real-world sales fundamentals and artificial intelligence. Steve has trained thousands of salespeople and consulted with nine-figure companies — and now he’s building AI tools that reinforce the exact sales skills he’s taught for years. We cover everything from empathy and active listening to call scoring, role-playing bots, and the future of voice agents that can qualify leads, schedule appointments, and eventually help close deals.

Episode Timeline & Highlights

[0:00] – Introducing Steve Trang and his evolution from top sales trainer to AI innovator.

[1:03] – Why Steve built Objection Proof AI and what problems it solves for sales leaders.

[2:55] – How the AI now handles call reviews, training, follow-up, and appointment setting.

[3:47] – Steve’s background: thousands trained, hundreds coached, and deep experience in real-world selling.

[7:56] – The real definition of empathy and how it translates into AI behavior.

[9:01] – Why robots can be better sales trainers than charismatic “natural” closers.

[11:58] – The classic sales mistake: offering solutions before understanding the problem.

[17:15] – Pattern visibility: how AI finally reveals true agent performance.

[19:19] – Using call reviews and feedback loops to help agents improve faster.

[23:20] – Role-playing bots as a training tool AND a hiring filter.

[27:55] – The gold mine in your CRM: reactivating old leads with AI.

[29:12] – Why outsourced call centers kill deals and how AI solves consistency.

[33:37] – The future of AI underwriting and real-time offer parameters.

[38:30] – Why AI will outperform low-level staff, not A-players.

[40:02] – Building companies made up only of top performers.

[47:33] – How to try Objection Proof AI and test the role-play or voice agent demos.

5 Key Takeaways

1. Empathy is the core sales skill — not emotion, but demonstrating true understanding. That’s what builds trust and closes deals.
2. AI amplifies real sales training, not scripts. It reinforces the exact skills top reps use.
3. Call scoring at scale changes everything. AI uncovers performance patterns no manager could ever catch manually.
4. Voice agents solve massive inefficiencies, from missed calls to dead follow-up sequences to reactivating CRM gold.
5. AI doesn’t replace A-players — it replaces C-players, allowing teams to run leaner, sharper, and more profitably.

Links & Resources

• Objection Proof AI – Upload a call or transcript for a free AI call analysis.
• Role-Play Bot Demo – Text ROLEPLAY to 33777.
• AI Appointment Setter Demo – Text CASH to 33777.
• SmartPhone – The only phone system built for real estate investors. Claim 5,000 free minutes.
• ThatRealEstateTechGuy.com – Explore all episodes and exclusive tech discounts.

Closing

If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with another investor or sales leader who wants to future-proof their business with better systems, better training, and smarter AI. More great conversations with industry innovators are coming your way!