Real Estate Magazine is dedicated to providing invaluable insights, experiences, and expert advice from the most successful real estate professionals and teams across Canada. We believe in sharing the strategies that drive exceptional results. If you, a colleague, or your team exemplify innovation and excellence in the Canadian real estate landscape, we encourage you to reach out and share your story with us.
In the dynamic and competitive world of real estate, few journeys exemplify strategic growth and sustained success quite like that of Matthew Regan. From an unplanned entry into the industry at the tender age of 18, Matthew has dedicated over two decades to meticulously crafting and refining a business model built on the pillars of leverage, robust systems, and unwavering database discipline. What began as a singular pursuit has blossomed into Regan Irish & Associates, a formidable 16-person team co-led with partner Alex Irish, extending its reach across the Greater Toronto Area (GTA) and beyond, including Etobicoke, Mississauga, Oakville, Burlington, Hamilton, and the picturesque Muskoka region.
Their collective efforts have culminated in remarkable achievements, with the team closing nearly half a billion dollars in volume in 2024 alone. The operational blueprint of Regan Irish & Associates is characterized by a clear and efficient division of labor, an impressive 1:1 staff-to-agent ratio, and a profound conviction that the most potent lead source is often the one already nurtured within one’s own sphere of influence – the existing database.
Regan Irish & Associates, operating under the esteemed banner of Re/Max Escarpment Realty Inc., stands as a testament to what focused vision and strategic execution can achieve in real estate. Let’s delve into the specifics that define their success:
Team & Brokerage: Regan Irish & Associates, Re/Max Escarpment Realty Inc.
Agents: 16 dedicated professionals
Staff: 16 highly skilled support personnel
Markets Served: Etobicoke, Mississauga, Oakville, Burlington, Hamilton, Muskoka
2024 Production Volume: $436,032,650
2025 Production Target: $453,000,000
REM: What was your initial foray into the real estate industry, and what prompted that decision?
Matthew Regan: My journey into real estate began at a pivotal moment when I was just 18 years old. I found myself sitting in a University of Toronto lecture hall, grappling with a profound sense of questioning about my future and the path I was on. In that moment of introspection, I made a spontaneous yet definitive decision: “To heck with it, today is the day I’m getting my license.” I essentially redirected my academic path, personally managing my tuition invoices to alleviate my parents’ financial concerns. Armed with youthful determination, a suit and tie, and a somewhat worn-out car, I embarked on my real estate career, working alongside my father. This unconventional start laid the groundwork for everything that followed, imbuing me with a hands-on understanding of the industry from a very early age.
REM: When did you transition from a solo agent to making the strategic decision to build a team?
Matthew Regan: There are effectively two answers to that question, reflecting distinct phases of growth. Initially, the formation of a “team” was somewhat accidental. We always had an administrative assistant, and over time, a few agents expressed interest in collaborating with us. At that stage, our operation lacked formal structure or a strategic vision for team building. The true inception of a deliberate team-building effort can be pinpointed to January 1, 2016. That was the day I picked up Jim Collins’ transformative book, Good to Great. Reading it was an epiphany; it fundamentally shifted my perspective, making me realize the imperative of treating my real estate endeavors as a genuine business, not just a collection of individual efforts. This realization spurred immediate and decisive action. We began by implementing clear roles and responsibilities, ensuring a precise division of labor. We focused intently on getting the right people into the right positions, and critically, we had to make the difficult decision to part ways with individuals who weren’t aligned with our new direction or couldn’t adapt to the structured environment. That pivotal year, I consciously stepped away from direct selling, allowing a true, strategically built team to emerge and flourish.
REM: What is your primary role within Regan Irish & Associates today, given the team’s growth and structure?
Matthew Regan: Today, my role is primarily that of an overseer, managing the business from a strategic, “10,000-foot” perspective. I internalized an essential leadership lesson early on: amplify your strengths by hiring individuals who excel in areas where you do not. This principle was powerfully reinforced just over a year ago when I forged a partnership with Alex Irish. Collaborating with Alex, who operates at the absolute pinnacle of her profession, has been incredibly enlightening. While she might shy away from the title, Alex is undeniably a rainmaker—she possesses an extraordinary, almost innate ability to bring deals to fruition. Our partnership thrives on a “divide and conquer” approach, leveraging our complementary skill sets. It’s genuinely rare for us to find ourselves not seeing eye to eye, which speaks volumes about the synergy and mutual respect within our leadership.
REM: Reflecting on your growth, what were the first three hires that proved most transformative for your business model?
Matthew Regan: The strategic deployment of human capital has been paramount to our success. The first truly transformative hire was an **administrative assistant**. Tammy Snow joined us and, with her expertise, established comprehensive systems and processes. These systems provided an unparalleled level of confidence and clarity for every team member, ensuring they could operate efficiently within their designated lanes. This foundational layer of organization was absolutely critical.
Secondly, the addition of **licensed assistants and dedicated agents** marked another significant leap. Allison Addison, in particular, became my indispensable right hand. She adeptly filled the operational gaps where my own focus was lacking, allowing me to concentrate on business development while she provided exceptional client service that far surpassed what I could manage alone. Simultaneously, Jackie Noble emerged as a leading agent—her dependability, honesty, and tireless work ethic were instrumental in driving sales. This combination allowed for both expansion and improved service quality.
Thirdly, integrating a **bookkeeper and financial controller** was a game-changer. I found myself perpetually bogged down by accounting tasks, which I not only disliked but also recognized were not my core competency. Delegating this crucial function freed up immense mental bandwidth. My strong advice to any agent doing even moderately well is to hire a bookkeeper. Furthermore, for any team generating $1 million or more in Gross Commission Income (GCI), securing at least a fractional controller is an absolute necessity to ensure financial health and strategic oversight.
REM: What crucial piece of advice would you impart to a team leader embarking on their very first hire?
Matthew Regan: The most vital piece of advice, which I learned from Rosa Viviano and have found to be invaluable, is this: When making your first hire, don’t just hire for the immediate needs of your business today. Instead, **hire for the future you envision for your business**. This forward-thinking approach ensures that your initial team members can grow with you and contribute to your long-term strategic goals, rather than becoming bottlenecks as your business expands.
REM: What are the top three, most effective lead sources for Regan Irish & Associates?
Matthew Regan: The answer is undeniably clear and consistent: **Database, database, and database**. We’ve all heard this mantra before, but its truth remains immutable—the highest return on investment (ROI) consistently comes from the relationships you’ve already cultivated within your existing network. If you commit to working your database diligently, effectively, and with consistent engagement, referrals will naturally become an exceptionally powerful lead source. Whenever I find myself contemplating where the next stream of leads will originate, my first instinct is always to return to the fundamentals. This means diving back into our database and initiating simple, personalized outreach, such as sending heartfelt birthday videos via platforms like Loom or BombBomb. These small, consistent gestures build enduring relationships and trust.
REM: Can you describe the process by which a new lead is efficiently handled within your sophisticated system?
Matthew Regan: Our process for handling new leads is meticulously structured for speed and effectiveness. The moment a new lead arrives, it is immediately and thoroughly logged into our Customer Relationship Management (CRM) system. Following this, an Inside Sales Agent (ISA) promptly initiates contact, either through a call or email, to pre-qualify the lead. This crucial step assesses their needs, urgency, and readiness. If there’s an existing relationship or prior contact between the lead and any specific team agent, the lead is directed to that agent to maintain continuity and leverage established rapport. If no such relationship exists, we assign the lead strategically based on which agent has the highest probability of successfully converting that lead—full stop. This isn’t a casual “house league” scenario where all leads are treated identically; we recognize that not all leads possess the same value or require the same approach. However, while strategic, our assignment process is always rooted in fairness and maximizing conversion potential.
REM: What is your typical response time goal for new leads?
Matthew Regan: Our unwavering goal for lead response time is **30 minutes or less**. In today’s fast-paced market, speed is paramount for capturing attention and demonstrating professionalism.
REM: Do you utilize Inside Sales Agents (ISAs) within your team structure?
Matthew Regan: Absolutely, yes. At our team’s current size and operational scale, the role of an Inside Sales Agent (ISA) is indispensable. ISAs serve as a critical accountability mechanism, ensuring that all follow-up actions are executed promptly and consistently. Our agents deeply appreciate this support, as it allows them to remain focused on high-value activities while the ISAs expertly manage the initial qualification and nurturing stages of the lead pipeline, keeping everyone on track and optimizing conversion rates.
REM: Could you outline the key components of your current real estate technology stack?
Matthew Regan: Our tech stack is carefully curated to maximize efficiency, organization, and client experience. **Follow Up Boss** serves as the backbone of our operations, acting as our central CRM, where all client interactions and lead statuses are meticulously tracked. For robust financial management and accounting, we rely on **Xero**. Project management and task organization are non-negotiables for us, and for these, we use **Monday.com** and **Google Tasks**. Anything of importance or requiring action inevitably finds its way into these task management systems, ensuring nothing falls through the cracks. Beyond these commercial tools, Alex and I have collaboratively developed a proprietary **client portal**. This innovative platform grants our clients real-time access to all their marketing assets, comprehensive feedback received on their properties, and detailed analytics. It’s an enormous time-saver for both our agents and administrative staff, fostering transparency and enhancing the client experience significantly.
REM: How do you approach financial management and the concept of Return on Investment (ROI) within your business?
Matthew Regan: Our financial philosophy is grounded in strategic allocation and a relentless focus on profitability. Approximately 25 percent of our total revenue is reinvested directly into marketing initiatives, ensuring continuous lead generation and brand visibility. Another 12 percent is allocated to staffing, underscoring our commitment to supporting our agents with a robust administrative and operational team. However, the only metric that truly captures the health and efficiency of our business is **net profit and margin**. Understanding our margin allows us to critically assess the profitability of each agent split and, more broadly, to determine whether our various strategic initiatives are generating a positive return. Our overarching financial objective is to consistently achieve a 30 percent margin, indicating healthy and sustainable business growth.
REM: What specific qualities define the agents who truly thrive and excel within your team? And what distinct actions do your top producers, those taking home $500,000 to $750,000, undertake differently?
Matthew Regan: The agents who consistently thrive on our team are unequivocally **self-starters**. These are individuals who not only possess an inherent drive to excel but also, on a daily basis, commit to the small, consistent actions that collectively lead to significant wins. They demonstrate a proactive engagement with our established systems, effectively leveraging our comprehensive operational framework. Crucially, they understand the value of focusing on their core strengths, thus staying out of administrative and marketing tasks, which are handled by our dedicated support staff. Our top producers consistently engage with their database, recognizing it as their most valuable asset. They actively talk to their contacts constantly, nurturing relationships. Moreover, they expertly leverage the established brand and reputation of Regan Irish & Associates. These common denominators—self-motivation, system adherence, focused activity, and brand utilization—are unmistakably clear in their success.
REM: How do you manage team performance in terms of rewarding positive behaviors and addressing underperformance?
Matthew Regan: Our philosophy is straightforward: **Winning gets rewarded**. This isn’t just about closing deals, but about consistent effort, positive contributions, and adherence to our core values. Conversely, **laziness and excuses will inevitably lead to being benched**. We cultivate a high-performance environment where accountability is paramount, and every team member is expected to contribute actively and effectively.
REM: When considering expansion into a completely new market, what are the non-negotiable prerequisites for success?
Matthew Regan: For us, the absolute non-negotiable when venturing into a new market is securing a **strong agent who ideally resides within that specific market and is deeply integrated into the local community**. The notion that one can successfully penetrate a new market solely through advertising is fraught with high risk and, more often than not, results in a significant waste of financial resources over time. Genuine community connection and local expertise are irreplaceable assets.
REM: If a team leader had a monthly budget of $5,000 to strategically invest into their business, where would you recommend they allocate those funds?
Matthew Regan: Without hesitation, I would advise investing that $5,000 monthly budget into **anything and everything related to staying in consistent, meaningful touch with your database**. This includes client appreciation events, personalized outreach tools, CRM enhancements, or any initiative that strengthens those existing relationships. The ROI from your database far surpasses any other potential investment.
Lightning Round: Rapid-Fire Insights from Matthew Regan
Favourite Canadian Market Insight People Often Doubt: The surprising reality is that most sellers, when the time comes to list their property, do not contact the agent who originally sold them their home. This highlights the critical importance of continuous relationship nurturing, even post-transaction.
One Essential Tech Tool You’d Fight to Keep: **Monday.com**. Its flexibility and comprehensive capabilities for project management, workflow visualization, and task tracking are absolutely integral to our operational efficiency and team coordination.
The Marketing Principle You’ll Unyieldingly Defend: The unparalleled power of a **personalized video message** sent to someone in your database. Whether it’s for birthdays, anniversaries, or significant life events, this level of personal touch creates profound connections and fosters enduring loyalty that generic marketing simply cannot achieve.
Primary Reason Agents Fail: Agents typically fail because **they consistently neglect to do the “little things”**. Success in real estate is built on daily, persistent efforts: talking to more people, every single day, all the time. Inconsistency is the silent killer of many real estate careers.
The Winning Formula for Real Estate Teams: Teams consistently achieve greater success because **leverage and scale inherently yield a significantly higher probability of winning**. With a well-structured team, there are more opportunities, more listings, enhanced support, and ultimately, a much greater chance of securing success in a competitive market.
The journey of Matthew Regan and the strategic evolution of Regan Irish & Associates offer a powerful blueprint for aspiring and established real estate professionals alike. Their dedication to systems, database discipline, strategic hiring, and a client-centric approach demonstrates that intentional growth, combined with a clear vision, is the ultimate driver of unparalleled success in the Canadian real estate landscape.
