Innovator Network Recaps
Pulling on the Same End of the Rope
April 24, 2025
By Arianna Marino
On April 23, 2025, the PropTech Innovator Network featured John DiMichele, CEO of the Toronto Regional Real Estate Board. Since taking the reins at TRREB, DiMichele has steered the organization toward a future-proof vision that prioritizes member experience, broker needs, and intentional tech adoption.
John DiMichele Conversation Highlights
An entrepreneur from a young age, he entered the industry with a construction background and a knack for solving problems. As both a broker and technologist, he quickly saw how digital tools could remove friction from daily workflows, well before laptops became common in the field.
While running offices as a broker he pushed for early tech adoption, installing hardwired internet cables and replacing shared computers with dedicated workstations.
“I remember we were 21st or 24th in market share, and we were fourth within eight months,” he noted. “Eventually, that went up to the top two. And that was, in my opinion, because these guys were always available. The information was always available to them.”
Tech Starts With the Agent
“Something new isn’t always something useful,” DiMichele cautioned.
He emphasized that TRREB doesn’t adopt tech because it’s trendy. They adopt it because it solves real problems. “If I don’t see it solving something that a REALTOR® would want,” he said, “I don’t spend time thinking about it.”
He explained that many tech products on the market are adopted without clear use cases, and shared a story of one provider offering 20 services, most of which members weren’t actually using. After surveying agents directly, he discovered the real utility came from just six of those tools.
For TRREB, the trigger for exploring a solution often comes from agents themselves. “If they start with, ‘It would make my life easier if...’ then we look into it.”
Building vs. Buying
TRREB’s innovation arm, PropTx Innovations Inc., was created to secure more control over the future of MLS technology. Though most of TRREB’s systems were initially outsourced, DiMichele now favors bringing development in-house; especially for tools with high strategic value.
The decision to build rather than buy is often driven by speed, control, and the ability to stay aligned with member needs. “We’re just not comfortable with the dependency anymore,” DiMichele said.
He also recalled the impact of signing early vendor contracts; deals that propelled some startups to massive valuations. “We’ve been kingmakers all this time,” he said, “and the next thing you know, you’re talking to a monolith.” By the time vendors grow large, the original vision is often diluted, and service suffers.
To prevent this, PropTx now includes clauses in RFPs that allow TRREB to either own or have a stake in the products they deploy. As DiMichele put it: “If you don’t have an interest, you’re not emotionally involved.”
The Role of the MLS
When asked about the future of MLSs, DiMichele was clear: their role remains vital.
As real estate faces disruption from portals, lawsuits, and direct-to-consumer models, DiMichele reaffirmed the MLS’s central role: “It’s still the single source of truth.”
He introduced a term: Overlapping Brokerage Disorder; a new threat replacing the old Overlapping Market Disorder. As firms pursue exclusive listings and pocket deals, he cautioned that MLSs must remain committed to transparency, accuracy, and cooperation.
“Going backwards is not the answer,” he warned.
What Makes a Strong Vendor Partnership?
DiMichele closed with a clear message for vendors: mutual success and mutual respect.
“Communication is paramount. Transparency is paramount. And of course, making good on a promise," he said.
He emphasized that vendors must view MLSs as strategic collaborators, not just as distribution channels. TRREB holds up its end by promoting and educating members about new tools, but vendors must be equally committed to ensuring adoption and value.
“When I put you in front of 70,000 members, what’s in it for them? And what’s in it for me?” he asked.
For a partnership to last, both parties must believe in the problem they’re solving and be willing to adapt together. “If we’re not all pulling on the same end of the rope, it shows,” DiMichele said.
Member News & Updates
Mark Richburg: At AEI in Denver, the Relevate One Launch Party brought together over 100 association and MLS leaders for an evening of partying, networking, and forward-thinking conversations, kicking off the next generation of AMS and SSO.
Eileen Romito: Bryan Burgers, lead backend engineer from Zenlist, was on stage at RESO's spring conference to talk about the new Days on Market standard that has been proposed.
About the PropTech Innovator Network
Each month, MLSPropTech.com highlights an industry executive who will dive into the complexities of the organized real estate sector in an exclusive gathering of PropTech Executives. This presents an opportunity for PropTech Innovator Network members to expand their network with high-caliber individuals and acquire insights that are truly unique and unavailable elsewhere. Become a member to join us every month.