Real Estate Magazine shares insights, experiences and advice from top-performing teams and agents across Canada. If you’d like to nominate yourself, or a colleague or team, send us an email.
From an accidental entry into real estate at 18 to building one of the GTA’s most productive teams, Matthew Regan has spent more than two decades refining a model built on leverage, systems and database discipline. What began as a solo operation grew into a 16-person team spanning Etobicoke, Mississauga, Oakville, Burlington, Hamilton and Muskoka, closing nearly half a billion dollars in volume in 2024.
Today, co-led with partner Alex Irish, Regan Irish & Associates runs on a clear division of labour, a 1:1 staff-to-agent ratio and a conviction that the best lead source is the one you already have.
Team & brokerage: Regan Irish & Associates, Re/Max Escarpment Realty Inc.
Agents: 16
Staff: 16
Markets: Etobicoke, Mississauga, Oakville, Burlington, Hamilton, Muskoka
2024 production: $436,032,650
2025 production: $453,000,000
REM: When did you first get into real estate?
MR: I first got into real estate at 18. I was sitting in a U of T lecture hall wondering why I was there. I was questioning my future and said to heck with it: today is the day I’m getting my licence. I essentially dropped out of school, intercepted the tuition invoices from my parents, paid them myself and with pimples on my face, a suit and tie, and a shabby old car, I went to work with my dad in real estate.
REM: When did you decide to build a team?
MR: There are two answers. I started a team by accident. We always had an assistant and a few agents asked if they could work with us. We had little structure at that point. The real story begins on Jan. 1, 2016, when I picked up Jim Collins’s Good to Great. It opened my eyes to the fact that I needed to start treating my business as an actual business. We implemented clear roles and divisions of labour, got the right people in the right seats, and asked those who didn’t belong to leave. I stepped out of selling that year and a true team was born.
REM: What role do you play today?
MR: I oversee most of the business from 1,000 feet up. I learned early that you should double down on your strengths and hire people who are talented at what you’re not. Just over a year ago, I partnered with Alex Irish. It’s been an eye-opener to watch someone who’s at the top of their game. She doesn’t like this title, but she is a rainmaker. She has an innate ability to get deals done. We take a divide-and-conquer approach, and it’s very rare that we don’t see eye to eye.
REM: What were the first three hires that changed your business?
MR: First, an administrative assistant. Tammy Snow came in and built systems upon systems that gave everyone the confidence to do their job, in their lane and be more efficient. Second, licensed assistants and agents. Allison Addison was my right hand; she filled in the gaps where I fell short. I could hunt for business and she could service clients beyond what I could ever do. Jackie Noble was my lead agent — dependable, honest and hardworking. Third, a bookkeeper and financial controller. I was being bogged down by accounting I hated doing and it wasn’t my core competency. Every agent doing half-decent business should have a bookkeeper, and every team at $1 million or more in GCI should have at minimum a fractional controller.
REM: What advice would you give a team leader making their first hire?
MR: Hire for the future you envision for your business, not just where you are today. That advice from Rosa Viviano has been invaluable.
REM: What are your top three lead sources?
MR: Database, database and database. We’ve all heard this, but the best ROI comes from the people you already know. If you’re working your database properly, effectively and consistently, referrals become a huge lead source. And when I’m wondering where my next lead is going to come from, I dive back in and start with the basics: birthday videos sent through Loom or BombBomb.
REM: How does a new lead get handled in your system?
MR: The lead comes in and is immediately logged in our CRM. An ISA calls or emails to pre-qualify. If there’s an existing relationship with a team agent, the lead goes there. If not, we assign it based on who gives us the best chance of winning — full stop. This isn’t house league and not all leads are equal, but it must be fair.
REM: Typical response time goal?
MR: 30 minutes or less.
REM: Do you use inside sales agents?
MR: Yes. At our size and scale, an ISA keeps us accountable and ensures follow-up happens in a timely manner. Our agents love it because it keeps them on track.
REM: What’s in your tech stack?
MR: Follow Up Boss as our CRM. For finance, we use Xero. Monday.com and Google Tasks are non-negotiables (anything important ends up in tasks). Alex and I also built a proprietary client portal that lets clients see all their marketing assets, feedback and analytics in real time. It’s a huge time-saver for agents and admin alike.
REM: How do you think about money and ROI?
MR: About 25 per cent of revenue goes back into marketing and 12 per cent into staff. The only number that truly matters is net profit and margin: knowing your margin tells you whether you’re profitable off an agent split and whether your initiatives are generating a positive return. We aim for a 30 per cent margin.
REM: What kind of agents thrive on your team? And what does a $500k–$750k take-home producer do differently on your team?
MR: Self-starters — people who not only want to excel but who, on a daily basis, make the small, consistent moves that lead to winning. They lean into our systems, leverage our operations, stay out of marketing and administrative work, talk to their database constantly and leverage the brand. Those common denominators are clear.
REM: What behaviours do you reward? What gets someone benched?
MR: Winning gets rewarded. Laziness and excuses get you benched.
REM: When moving into a new market, what’s non-negotiable?
MR: A strong agent who ideally lives in that market and is involved in the community. To think you can enter a new market with advertising alone is high risk and will most likely be a waste of money over time.
REM: If a team leader has $5,000 a month to invest into their business, where should it go?
MR: Anything related to staying in touch with your database.
Lightning round
Favourite Canadian market insight people don’t believe: Most sellers do not contact the agent who sold them their home when it comes time to sell.
One tech you’d fight to keep: Monday.com.
Marketing hill you’ll die on: A personalized video to someone in your database — birthdays, anniversaries, life events.
Agents fail because… they don’t do the little things consistently. Talk to more people, every day, all the time.
Teams win because… leverage and scale usually yield a greater chance of success — more opportunity, more listings, a greater chance of winning.
