Zillow, Compass, and the AI Race: How Real Estate’s Biggest Players Are Reshaping the Industry

In this forward-looking episode of Rethink Real Estate, host Ben Brady, CEO of Harcourts Auctions, sits down once again with Tony Self, Broker Associate at Harcourts Hunter Mason Realty, to unpack one of the most disruptive moments in modern real estate. From the proposed Compass–Anywhere merger to Zillow’s partnership with OpenAI, Ben and Tony dive into how consolidation, regulation, and artificial intelligence are rewriting the industry’s playbook.They examine the potential consequences if Compass gains control of nearly two-thirds of U.S. real estate transactions, the growing backlash from agents and franchise brands, and what this could mean for competition and consumer choice. Tony brings his insider’s perspective from years in corporate real estate and tech, offering rare insight into how brokers, teams, and independent offices should prepare for what’s next.The conversation then pivots to AI’s rapid evolution — from OpenAI’s partnership with Zillow to Sora’s video generation and the new wave of real estate-focused agents and automations. Tony shares how he’s integrating AI into his business today, where he draws the ethical line on visual manipulation, and whether we’re heading toward a full-blown AI bubble reminiscent of the early 2000s tech crash.If you’re a real estate professional trying to make sense of the Compass–Zillow rivalry, OpenAI’s expanding footprint, or the future of automation in real estate, this episode connects every dot.Timestamps & Key Topics:[00:00:00] – The Compass–Anywhere Merger: Monopoly or Market Shift?[00:02:10] – What the DOJ and Regulators Might Do Next[00:04:30] – Century 21’s $2.6 Billion Problem and the Debt Factor[00:07:00] – Compass vs. Zillow: The Data War Nobody Wins[00:10:00] – Zillow’s OpenAI Partnership Explained[00:13:00] – How AI Could Redefine Home Search and Consumer Behavior[00:16:00] – What Agents Should Know About Licensing and AI Tools[00:18:30] – The Risk of Misrepresentation in AI Marketing[00:20:30] – Are We in an AI Bubble? Tony’s Tech Market Perspective[00:24:30] – When AI Becomes Native: The Next Real Estate Revolution🔗 Related Resources Below:🌐 For more information on Harcourts Auctions our non-distressed auction platform feel free to visit https://www.harcourtsauctions.com🔗 Connect with Tony Self and Harcourts Hunter Mason Realty:https://selfregroup.com/https://www.facebook.com/selfregrouphttps://www.linkedin.com/in/anthonyself/https://huntermason.harcourtsna.com/https://tonyself.harcourtsna.com/🔗 Connect with Ben Brady and Harcourts Auctions: ⁣https://www.facebook.com/Benbradyharcourts⁣ ⁣https://www.linkedin.com/in/ben-brady-0b223517⁣ ⁣https://www.instagram.com/harcourtsauctions⁣ ⁣https://www.facebook.com/HarcourtsAuctions🎯 Subscribe for more industry insights — and drop a comment with your thoughts:Will AI make real estate smarter… or monopolized?