Nobody gets to the top in this business without a lot of help.

Whether that help is asked for or merely given, need not matter.  Help comes in all different forms and delivery methods and from many different sources.

I’ve been with Bosley Real Estate my entire career; almost two decades.  There are a multitude of reasons why, as well as why I will likely never leave the brokerage, but we need not get into those today.

But one of the reasons I feel this company is different from all others is because of the collaboration among agents.

I got into this business believing in real estate stereotypes that I learned from “The Simpsons.”  Don’t people dig through each others’ garbage looking for leads?

What I found at Bosley, in addition to training that wasn’t offered at any other firm, was a genuine desire to help among experienced agents.

Agents talked so openly about the market, their business, and what they were doing.  It was astonishing.  And I found that I didn’t need to ask another agent a question; it was almost like the moment one popped into my head, somebody was there to provide advice, experience, and guidance.

Perhaps I was just lucky to be placed in “the basement” of our old brokerage at 290 Merton Street and benefit from the tutelage of three very experienced agents who were kind, caring, and eager to help.  But “kind and caring” came with a brutal honesty and the crack of a whip that wouldn’t fly out there by 2023 standards.  Well, I should say: wouldn’t fly out there – anywhere except in real estate…

Somewhere along the way in my career, I ceased to become the agent asking for help and instead became the agent being asked.

Based on the incredible amount of guidance that I received when I was starting out, I always told myself that I would return the favour.

So in addition to having an “open door,” literally and figuratively, whereby some 23-year-old rookie who can’t make eye contact can come ask for help, I’m always doing panels and Q&A’s with the company when asked.

A few months ago, I was doing an “Ask Me Anything” for the next class of Bosley-U, which is our in-house training for new agents.

I couldn’t help but notice how many of the questions were rooted in fear.

“How long did it take for people to stop assuming you’re brand-new?” one agent asked.

“What’s the biggest mistake you made early on in your career?” another agent asked.

“Did you ever think you were going to fail?” I was asked by one agent with fear in her eyes.

But then came the absolute kicker.  I mean, I’m an open book and people know that.  Here on TRB as well as in the office, but the next agent didn’t sugarcoat the question at all:

“What’s the absolute worst experience of your entire career?”

Geez.  Not even a kiss first…

But I told the story.  And what’s more is that, right then and there, I realized I had my speech for our annual company event which would take place a few weeks later.  Every year, Bosley’s top broker gives a speech and I was honestly running out of things to talk about.  And then lo and behold, here comes this great idea: our worst fears and worst experiences.

Who wouldn’t want to share that with two-hundred colleagues?

So today, let me share that story with you, in addition to giving you context by over-sharing my humble beginnings in this industry…

I found success early on in my career.

I completed fourteen transactions in my first full year in the business and I was in second-place for Bosley’s “Rookie of the Year” award.

My transactions came from all over the place.

I met a buyer at an open house.

I got a listing through a flyer.

I got another listing through an old contact when I worked at TD Bank.

A few friends of mine leased places.

I was given a lead from a colleague in the office that he didn’t want to work.

And on, and on, with no real theme among the transactions.  They came from completely different places, each and every time.

Some would argue that this is a good thing.  Casting the net wide, and all that.

But the problem was, back in 2004, that there was no real “plan” in place for business.  It just sort of fell into place.

That’s not to say I wasn’t working hard but I don’t know that I was working smart.

And as I volunteered to a room of two-hundred colleagues at our company function last month, my second year in real estate was an absolute train wreck.

My second year in the business started with a dry-spell that lasted about four months.  Imagine going four months without a transaction?  I believe I broke that streak by selling a condo for $246,500, including the furniture, but then the dry-spell continued.

And continued…

So here’s where the “worst experience” begins to take shape, as the preceding was merely for context.

To understand what I was about to go through, I needed to first explain what I had been going through for the first half of the year.

A friend of mine lived in the Beaches and her grandmother owned a ton of real estate.

It was a very odd family dynamic.  The grandmother was loaded; I don’t know how.  But the family didn’t “act” rich.

My friend, who we’ll call “Kate,” grew up in a decent Beaches house and after finishing school, she moved back home.

Her brother lived in a house that the grandmother owned, as did her sister.

Not a bad deal for the kids overall, although consider the context here: this was 2005 and the market wasn’t impossible to break into like it is today, so people thought a lot less of living in Granny’s house for free.

One of Granny’s houses had been tenanted by the same people for about fifteen years and when they gave notice and left, Granny went over and found the house to be in absolutely miserable condition.

How do people live like this?

Perhaps Granny could have done a few more visits to the property, or more upkeep, but by the time she saw the house in 2005, it was completely dilapidated.

Kate told me about the house and that Granny was contemplating what to do with it, so I asked if I could come by and meet Granny and give her some advice.

Granny lived in a massive house up on a hill.  You were almost tired by the time finished hiking up to the front steps.

Granny was very kind; the stereotype of a “sweet ole’ lady,” and she offered me iced tea – which was way before Nestea Zero or anything like what we have today.

I talked to Granny about the real estate market in general, as well as the rental market, and asked her what she thought she should do with the property.

“Well, the thing is,” Granny slowly said, “Jimmy says he wants to develop it.”

Jimmy?

Ah, right.  That was Kate’s brother.

Except Jimmy wasn’t a developer.  He was a custodian at a high school.

“Is Jimmy a developer?” I asked Granny, not being condescending as I didn’t know yet what he actually did for a living.

“Oh, no,” Granny said.  “Jimmy works over at the high school,” she answered with a smile.

“Well, development isn’t for the faint of heart,” I told Granny.  “It’s tough to break into without any experience.”

Kate complained about her brother relentlessly.  She called him a “dreamer” and said that he was always hatching hare-brained schemes.  It was one of those families where, when Kate received an A+ on a school project and taped it up on the refrigerator, her parents would rip it down immediately and yell, “How do you think this would make Jimmy feel?”

Geez.  Not entirely unlike what’s happened in public schools in 2023, but I digress… 🙂

I asked Granny if I could go by the rental property and take a look, then put together an evaluation and come back and present it to her.

She said that she wasn’t quite ready for that yet, but added that it was lovely to meet me and asked me to keep in touch.

So I did exactly that.

Two weeks later, I found myself in the neighbourhood so I knocked on her door to say “hello.”  But that “hello” turned into a two-hour hangout while drinking iced tea and chatting about how different the world was from when she grew up in Toronto eighty years prior.

Granny asked me to “make this a regular thing,” and I did.  I went over there every Friday for a month.  And after my fourth or fifth visit, Granny said, “Dave, why don’t you go over and check out the property across the street?”

So, I did exactly that.

The house was in truly miserable condition, and I soon realized that this property, which was a 2-bedroom, 2-bathroom bungalow situated on a massive 40 x 135 foot lot, was a prime piece of real estate that developers would salivate over.

I reported back to Granny the following week and asked her if she would allow me to present an evaluation for her, as well as a breakdown of my services and my sales process.  She agreed.

So I did exactly that.

I spent countless hours working on the evaluation, looking at it from several different ways.  What was this worth simply on a lot size basis?  What could you get for the property if you worked backwards from a new-build and factored in the profit for the builder?  And what were the basic comparable sales saying?

I put together a full presentation for Granny which I showed her on my DELL laptop, back when only two or three other agents in the brokerage had a “portable” computer.

I spent two hours with Granny and at the end of our meeting, she stood up, extended her hand, and said, “Dave, I would be honoured if you would list and sell this house for me!”

Kate was there.  I’ll never forget the look on her face.  She was so happy for both me and Granny, but just really happy that the two of us would be working together.

I figured that this lot was worth around $600,000 but if we listed it at $499,900 with an offer date, we had tremendous upside.

I know what you’re thinking: how can a 40 x 135 foot piece of land in prime Beaches be worth only $600,000?  Just consider how long ago this was.  Also consider that the finished house on this lot would be worth “only” $1,300,000 as well…

Granny told me that we would meet on Monday to sign the listing paperwork and that we could list on Tuesday.

I spent the weekend calling contacts and I even got some interest from a builder that I knew, who loved that it was “exclusive.”

That’s the thing about builders, right?  They all know ten agents, none of them want to buy through MLS, and they love anything that’s in your pocket or off market.

My builder friend told me he would take a look at the lot on Monday morning as he wanted to get a jump on the competition.

I took him there at about 9:00am.  I remember because it was late-June or early-July and it was 30-degrees most days, but this morning was cold and there was dew on the lawn.

We walked the lot and he didn’t say much.  He just kept nodding as I spoke.

I had done the math on this project.  The cost to build would be about $300,000 but I knew he could do it for less.  The lot would be about $600,000, give or take, but even at $630,000, there was a huge margin here.  You can’t imagine how much cheaper it was to build, twenty years ago.

My friend stood at the high point of the lot, looking downward.

“Great view of the street from up here,” he said.  “I could see a second-floor master bedroom at the front of the house, rather than the back.”

He was into it.

We slowly walked down the lot, right to the front of the property and stood there in silence as he thought.

He was so deep in thought, of course, that he barely noticed that white cube van pull up in front of the house.

I sure noticed.

And when the driver got out, slid the side-panel door open, and revealed what was inside, my heart began to sink.

Picture this: the two of us are standing there on the lawn of the property that I’m about to list for sale.

Now, picture this: the guy driving the white cube van pulls out a “CENTURY 21 REAL ESTATE” lawn sign and proceeds to hammer it into the lawn.

This happened in slow motion, I swear.

If I close my eyes, I can still hear the sound of the steel mallet hitting the steel pole that held the sign.

“CLANK…..CLANK…..CLANK…..CLANK…..CLANK.”

It took five swings to get the peg into the ground.  I distinctly remember.

Once the peg was in the ground, the guy took the second half of the sign and threaded the two pieces of metal together, making this “SSSSHOOOOP” sound.

I distinctly remember that too.

My builder friend and I just stood there in silence and watched this happen, right in front of our eyes.

The guy didn’t even say anything.  He just put the sign up, gave it a once-over with a cleaning rag, and then got back in his van and drove away.

Words weren’t coming out of my mouth.  I had no clue what to say.

But my builder friend spoke first.

He looked at me and said, “Don’t ever waste my fucking time again,” then got in his car and drove away.

I had no clue what just transpired.  I had to pinch myself to see if this was real.

I was supposed to sign this listing today.  Granny said we were listing tomorrow.  Who the hell is this agent that works for Century 21?  What the hell happened?

I called my friend Kate on the way home and she was shocked!  She said, “I’ll call Granny and figure out what happened, I’m so sorry!”

But I didn’t hear back from her.

The next day, I called Kate.  I needed an answer.

She picked up and was already sobbing.

“Hi,” she meekly said, and ended there.

Silence.

“Kate, what’s up?  Are you okay?”

Here I was, asking her if she was okay.  Why was she upset?  She didn’t do anything wrong.  I was the one who just got screwed.

“Jimmy,” she said.  “Fucking, Jimmy.”

Jimmy?  What about him?  What was she talking about?”

“It’s always Jimmy,” she said.  “My whole life, I swear.  It’s always Jimmy.”

I asked her to slow down and explain, and she did.

She said that after Jimmy found out that Granny was going to list the property for sale with me, he flipped out.  He told Granny that he wanted the property and he had big plans for it, but Granny said that she wanted to sell it.

So Jimmy did the next best thing.

He called a friend of his who worked for Century 21 in Markham and worked out a side-deal.

Jimmy pressured Granny to sign a listing with his friend, and of course, Granny acquiesced.

“Jimmy gets everything he wants,” Kate said.  “He always has.  My entire life.  It’s always Jimmy.”

But that’s not the kicker.

The kicker is that after Kate argued with Jimmy about what had happened, and why, Jimmy bragged, “My buddy is giving me ten-grand.  That’s why.”

It was disgusting.

The commission on this listing, if it sold for $600,000, would be $15,000.

Jimmy’s friend from Markham was going to give Jimmy $10,000 of that commission.

But it’s worse if you really break it down.

Assuming that Jimmy’s friend was on a 70/30 split with his brokerage, he would be paying them $4,500 (ie. 30% of $15,000), thus leaving Jimmy with $500 for his efforts.

And if you want to throw income tax into this, then Jimmy’s friend is being taxed on the whole $15,000 in gross income, which probably nets him out at a loss.

Maybe Jimmy’s friend was on an 80/20 split.  Back then, and from a crappy discount brokerage in Markham, it’s possible.

But bottom line: Jimmy’s friend wasn’t making any money on this.

Jimmy was.

And when I saw the property listed for $589,900 and sold for $570,000 after two days on the market, I felt sick to my stomach.

Nearly three-thousand words to this point, you simply can’t imagine what this experience was like for me.

It wasn’t that I lost the listing.  I’ve lost many listings over the years.  Every agent has.

But I didn’t lose this listing over the phone or over email.

And although I was completely sideswiped, I didn’t find out as I drove by the property and saw the sign, nor did my builder client see the sign and call me.

No.

I found out as I stood on the goddam lawn.

I found out as I toured my client across the lot.

I found out as I stood there, like a moron, as a sign installation company pulled up in a van and hammered a sign into the lawn, inches from my face!

Just try to picture this.  You simply can’t make this up.  You would have had to be there to appreciate just how pathetic this was.

Between myself, my builder-client, and the sign-installer – I swear we could have all been holding hands, we were in such close proximity.

And at that point of my career, in my second year of real estate, having completed one transaction in six months, it was inexplicably unexplainable.

The feeling lasted for weeks.  Months, even.

Every time I pictured myself standing on that lawn, watching a guy hammer a Century 21 sign into the lawn, I got anxious.

I replayed it in my mind, over and over, each time hearing the “CLANK” of the metal-on-metal.

The “CLANK” may as well have been the sound of nails being driven into the coffin of my fledgling real estate career.

Is this how the industry worked?

Agents giving envelopes full of cash to family members to screw over their own blood?

It was so disheartening.  It didn’t just sour me on real estate but it soured me on people in general.

Perhaps I was naive at that point in my career and at that point in my life to think so much of people that this experience came as a surprise.  Sadly, over the coming years, I learned what people were capable of, and it was a necessary learning in order to move forward in a business like this.

People like Jimmy are out there, no question.  And agents like Jimmy’s friend are rampant in the industry.

It took me a few months to move on from this and when the calendar hit December 31st, I put that awful year behind me.  The next year was a breakout, or, perhaps the previous year was an outlier.  But I learned so much from this experience, and while many people in my position might have concluded, “If you can’t beat ’em, join ’em,” I took the opposite approach.

Yeah, sure, this was eighteen years ago.

That was a long time.  There are adults that are that old!

But despite the learnings, and despite the perseverance, I’d be lying if I didn’t open up and be honest; I’d be lying if I didn’t regale you with the preceding and tell you that through almost twenty years in this business, that was the worst experience of my career…