Joe Conlon hit 107 deals in a single year. Sounds like success, right? Not quite. By August, he was so burned out he threw his phone in a drawer and disappeared to his cottage for weeks.
Today, Joe runs one of the largest real estate teams in Windsor and Essex County. He’s won Royal LePage’s Chairman’s Club award (top 1% in Canada) four years running. And he goes home at a reasonable hour to spend time with his two kids.
So what changed? Let’s dig into his journey from cell phone sales to building a real estate empire—and the hard lessons he learned along the way.
The Early Days: Finding His Way to Real Estate
Joe didn’t start in real estate. He worked at Tim Hortons, Starbucks, and Best Buy. He even DJed 20-25 weddings a year as a side hustle.
But it was selling cell phones at Best Buy where things clicked. Joe thought: if I can sell cell phones, why can’t I sell houses? They’re just bigger products.
At 22, he got his real estate license. He kept his DJ business and Best Buy job while getting started. Smart move, because it took him six full months to close his first sale.
Those first six months were rough. He wrote offers constantly, but nothing converted. He questioned if real estate was right for him. But then something clicked. The second half of his first year was completely different, and he hit the ground running.
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Finding His Niche
Joe discovered his sweet spot: first-time home buyers. As a 22-year-old agent in a field where the average age was in the 50s, this made perfect sense.
First-time buyers were willing to work with a young agent. They needed education about the process. And there was strong demand in this segment.
The Open House Method
Joe’s primary strategy was simple but effective. He messaged agents at his brokerage offering to hold their open houses. Back then, the market had more houses than buyers, so established agents were happy to hand off these duties.
Joe picked areas where he’d have the best chance of meeting potential clients. He met first-time buyers at open houses, then took them out and educated them about buying a home. This systematic approach built his client base steadily.
The Social Media Advantage
In 2012, Facebook was just starting to be used for business. Most agents, especially older ones, weren’t using social media professionally yet.
Joe jumped on this opportunity early. He was competing against maybe five other agents using social media effectively, not the 20-100 agents that new agents face today. Instagram didn’t even exist yet, so everyone was on one platform.
This first-mover advantage was huge. Joe built a following that has stayed loyal. He credits timing and luck as major factors in his social media success.
When Success Becomes Too Much
After two to three years of steady growth, Joe hired his first administrative assistant and rented office space. Business kept growing. By 2017, he hit 107 deals.
But the cracks were showing. He couldn’t service clients at the level he wanted. He was working extremely early mornings and late nights. Sleep became difficult. His focus suffered. He felt constantly exhausted.
Then the chest pains started. Severe anxiety set in.
By August, Joe had enough. He threw his phone in a drawer and went to his cottage for weeks. He knew he’d lose business. He didn’t care. His health had to come first.
Building the Team
When Joe returned, his brokerage manager had a suggestion. A new agent named Steve Popovich needed business and mentorship. Could Joe help him while Steve handled some overflow work?
It worked immediately. Joe then brought on Jill Wingler once she got licensed. In 2017, he officially formed the Joe Conlon Real Estate Team with three agents, an assistant, and a marketing assistant.
But even three agents couldn’t keep up. Joe realized he’d been missing tons of potential business because he was so busy with current clients. He couldn’t see how many opportunities were slipping away.
The team kept growing strategically. Steve Wild joined. Christa Smith started as an assistant, proved herself, got licensed, and became an agent. Zach Janee came on board.
Today, the team has six agents and three assistants. They have proper systems to service clients at a high level. And Joe can go home at a reasonable hour to see his kids.
The Most Important Lesson
When asked for his single best piece of advice, Joe didn’t hesitate: focus on infrastructure first.
Joe wishes he’d prioritized systems from day one instead of just chasing clients. He learned this lesson the hard way.
Without proper systems, everything becomes chaos. You’re scrambling for client information years later. You can’t track follow-ups properly. Disorganization drains your mental energy. You lose opportunities and money. And you definitely can’t take time off or delegate confidently.
With systems in place, everything changes. You can delegate easily. You can go home in the evenings. You have mental peace. You can scale. And you deliver consistent service to every client.
Joe’s team continues refining their systems, always improving. But if he could do it over, he’d build the systems first, even if it meant losing a bit of money upfront.
The Power of Taking Breaks
Joe’s story includes a dramatic break—throwing his phone in a drawer and disappearing for weeks. It cost him business, but it saved his health and ultimately his career.
Don’t be afraid to step back when you need to. Whether it’s a hiatus to recover or a complete change of scenery, taking time to figure out what you want can be transformative.
Both Joe and many successful entrepreneurs credit bold moves like this as crucial to their ultimate success. You can’t build something sustainable if you burn out first.
Where Joe Is Now
Joe confidently expects to win his fifth consecutive Chairman’s Club award. But more importantly, he has the work-life balance he wanted. He’s home with his kids. He’s not stressed like he was in 2017.
The team has strong systems and infrastructure. If they reach capacity again, they can scale properly without repeating the painful growth he experienced before.
His message is clear: build the foundation first. Create systems. Don’t just chase growth. Because sustainable success beats burnout every single time.
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