Before Rock Star: The Story of How We Quit Our Jobs


When it comes to how we both quit our jobs it would be fun to think that we just got up one day, confidently flipped the bird to our bosses, and walked out in a blaze of glory.

Unfortunately, it didn't happen with such epic drama.

It was more like we quit our jobs over a series of several months. Looking back we're not sure if it was confidence or pure naivety.

We regularly meet people who want to quit their own jobs and ask us to lay out the simple, step-by-step plan for doing so.

Unfortunately, all of our backgrounds, obligations, skill sets, and finances are very unique so there's no such thing as a cookie cutter plan.

However, we have been fortunate to watch many people now create multiple streams of income from doing all sorts of different things.

Today we're going to share some of the lead-up to quitting and going it alone in the hope that it somehow offers a little bit of value to you.

It's impossible to share all of the details but we've tried to include many of the important moments.

With that, we present you with...

The Back Story of How We Quit Our Jobs
& Started Rock Star Real Estate

A fairly new Rock Star Member bumped into me at one of my son’s league soccer games and mentioned that he was aware of how we started Rock Star with Nick working in a closet-sized office, both of us sharing one Acura TSX for investor property tours, and licking stamps in my basement but he wanted to know what really made us quit our jobs.

He believed that we were fairly analytical people and wouldn’t just “quit” without some expectation of success. 

And he was right.

The lead up to changing our life’s course and “going it alone” happened over a course of several years.

For context, Nick and I are children of immigrant parents. Our father came over on a boat after escaping out of Yugoslavia and our mother came over on a plane from a very poor upbringing in Scotland.

We saw our father get up every day at 5:00 am to work in unfinished houses putting up drywall. His friends told us he was slightly crazy because no matter how dark or how cold it was he would always be the first one on the job site and the last to leave. 

Our Mom is an incredibly hard worker as well. She worked as a lab technician and then when our father started his own drywall company with a couple of friends she began working in the office taking care of just about everything.

From our point of view, both our parents had an insanely high work ethic.

Our family vacations were often trips to Croatia where we would hang out on our grandparent’s farm helping out with all the chores that go along with raising cattle, pigs, chickens, and farming land. We loaded donkeys with potatoes, watched cows eat grass, and played soccer on the rockiest patches of turf you’ve ever seen. It was awesome.

Once the family drywall business began to make some money we had some great vacations that involved going skiing up north at Horseshoe Valley and a couple of times our Mom took us to Disney World.

School was always fairly easy for me. I was never going to win any athletic awards but I was on both grade-school and high-school sports teams. I was almost effortlessly getting 90% or higher in most of my classes during high school before cars, girls, and sports became such a distraction that I dropped into the 80% range. Nick, five years younger, was always more athletic and played the more aggressive sports. I was the volleyball guy, he was more the football type.

We both breezed through high school and went further. I went to University, Nick to College.

Right after university, I spent $13,600 I didn’t have to attend a post-graduate I.T. school. I did it because I called the “career ads” in the Toronto Star and asked several hiring managers what skills they needed. They all said something like “database, Internet, C++ programming, or Visual Basic.”  So when this school opened up on Bay Street in Toronto offering to teach these things for, what was then, a huge sum of money I immediately signed up. In fact, I was the first student registered for the new Toronto location. My friends thought I was crazy. I thought of it as a low-risk way to get a chance at a good job. Before graduating I had an offer from the Royal Bank and then shortly afterwards an even better offer from Oracle Corporation.

Nick would join the corporate world a few years later working for the Region of Peel in their Information Technology department.

At this point, I think we both realized the corporate world wasn’t going to be in our lives for very long. 

Somehow I stumbled onto the book, Think & Grow Rich, by Napoleon Hill and that began a journey that would eventually have both of us quit our jobs.

As I began working in the corporate world I continued to spend my money on information. Mostly on books and audio programs. The topics ranged from personal finance, to motivation, to sales and public speaking.

Neither of us were big readers before entering the corporate world but somehow once we started we both found a lot of value from all sorts of books, they became our mentors.

I’m not sure if it was Rich Dad. Poor Dad. by Robert Kiyosaki, that got us both thinking about real estate but by the time Nick was 21 or 22 years old he had purchased his first “flip” after spending $8K on a weekend real estate boot camp. Next, he bought a student rental and found another one that we teamed up on together. I then flipped a property and bought another rental and our journey into real estate began.

We were both working in the Information Technology fields by day but thinking and reading about real estate at night.

A lot of these types of books also encouraged you to get good at sales and marketing so I changed into a sales role at Oracle where Nick joined me briefly before he began direct selling products to the public with a friend outside of his corporate life.

Getting sales experience gave us a whole new perspective on making money. We were no longer tied to a set salary, you were paid for your performance. This changed our thinking around money in a big way.

Right around this time, the Internet was taking off and we both began reading about websites and search engine optimization, and putting articles online.

I recall reading some marketing books that kept saying something like, “you can have everything you want in life if you help others get what they want.” 

For some reason that resonated with me and on a trip to Cuba shortly after getting married I kept asking my wife, Carol, what people wanted, what did they really want? And then it hit me … women want sales! They want to know where the sales are! They really, really want them!

I went off and spent about $4,000 of money we really couldn’t afford to spend on a 5-page website that offered to email you a list of sales in Toronto in exchange for your email address. To this day I can’t recall how people began finding out about it but I was spot on with the idea.

As a quick aside, over the years I found that while a lot of my responsible friends would take $5,000 and “top up” their RRSPs, I would find ways to take that money and spend it on a course, a program, or a website of some sort. Looking back I now realize that I was investing in myself instead of my RRSP.

The little website began getting two to three people giving us their email address every day. That quickly changed to five, then fifteen, then twenty. Then a friend called and said a national magazine had featured my site that month so we ran to a bookstore to find our site as a little feature in their “What’s Hot” section. The email addresses kept pouring in and shortly afterwards we shut down the entire thing down.

Neither Carol or I actually enjoyed gathering up all the sales in Toronto and we quickly realized that a lot of the sales weren’t actually great sales. Looking back it was rather silly to close it down, especially since would go on to go public on the stock market, with a similar business model, many years later for about a billion dollars!  I just wasn’t the right person, at the time, to turn the idea into a real business.

But the lessons that came from that experience were priceless. Things like website creation, email collection, email follow-up, the value of offering people what they wanted, search engines, the power of the written word in emails and on websites, etc. 

I think that was the first time I really understood the saying, "You don't have to get it right, you just have to get it going."

The process of starting something, even if didn't end up the way I wanted, taught me a lot.

It also became obvious that you could run a pretty fun business if you helped people get what they wanted instead of trying to sell them something they didn’t - which is what I felt like I was doing in my corporate sales job.

Right about this time Nick stumbled into selling satellite equipment direct to consumers as that market was exploding. He was making more sales - faster, and easier than ever. It was another example of the power of “giving people what they wanted.”

Over the next few years, I tried trading stock options and read everything I could about the stock market. I began trading puts and calls for about a year I believe. I can’t recall if I lost money or made money but at some point, I got distracted and left it. 

At one point a few years earlier I even bought a “commodity trading program” on VHS tapes and asked Carol to watch them every night with me for weeks on end. We were going to be commodity trading millionaires! I think I made one trade, lost money, and never went back to it.

Around 2001 or 2002 our Mom told us she was going to a “Millionaire Mind” seminar in Red Deer, Alberta. It was led by some guy named, Harv Eker, and for some reason, I took a week’s worth of vacation and joined her. I think I was trying to protect her from spending all her money at this thing but before the end of the seminar, I was calling home letting Carol know I had enrolled both of us into some sort of Warrior boot camp or something, for about a thousand dollars. Again, it was money I really couldn’t afford to be spending. To this day I have no idea how Carol supported me through all of this.

Around this time Nick had bought a property in Hamilton, renovated it and refinanced it, extracted all his downpayment, and was still left with a cash flowing property. That refocused me on real estate and I flipped a property with a friend shortly after that.

Both Nick and I kept working in typical jobs during these years but we both came to realize that real estate had a lot of potential. Every truly wealthy person we were reading about had real estate in their lives.

It was also about this time that I bumped into the concept of “direct response marketing.” The idea with this type of marketing blew us away. Instead of advertising just to “build your brand,” or to get your name “out there,” you strategically designed ads that prompted possible customers to call you.

This seemed intriguing and we dove into it hard. We read all the marketing books we could find on the subject. We even uncovered old marketing books from the 1950’s and 60’s on the subject. It was like a brand new world opened up to us.

These authors were explaining that if you “give people what they want” in an ad, and then followed-up correctly, you could build a real business. They explained that by tracking the number of responses to get a customer you could boil business down to a mathematical equation.

And then if you figured out the cost to obtain that customer and sold them something that was worth more than the cost to acquire them, by some magic, you had a profitable business.

This was the first time we had heard a business strategy mapped out so simply and so clearly. And it matched with our past experiences around the value of giving people what they wanted.

At this point we still didn’t really have any idea about creating Rock Star Real Estate, instead, we began to toy around with the thought of getting our real estate licenses and perhaps quitting our corporate type jobs to get into real estate full time. 

Our thinking was that we could keep buying properties for ourselves and perhaps earn commissions from real estate to buy even more. So both we both got our licenses and joined a brokerage in Oakville as “part-time,” non-committed, licensed real estate professionals.

Nick had his license before me and listed a flip we were doing in Oakville to earn his first commission. I then helped a friend flip a property in Oakville and made my first real estate commission.

Right at that time, my corporate income from my job was exploding. I had gone from crossing into six figures for the first time in my life and then doubling that the next year. I was using all the sales training information I had been reading about and putting it to use as best I could. 

A bunch of us from Oracle then left to join a company called NetSuite as it was preparing to go public. I thought joining a start-up would be exciting, and it was, but the daily grind of a corporate role didn’t allow me to express myself fully. I felt trapped, like I wasn’t fully living or something.

I had all this knowledge around sales, marketing, and real estate that I felt I wasn’t putting to use. As a sales manager at NetSuite, I asked the marketing department in California to tweak their marketing to better match what our customer was looking for and the idea was shut down without much consideration. No one from sales ever engaged the marketing department regularly so I don’t think they knew what to make of me.

I began to feel like the corporate world was a prison. I was making great money, in a growing company about to go public, I had stock options, great sales awards, cool vacations, and a great sales team - and I was completely miserable.

I vividly recall being stuck in traffic one day on highway 403 on my way into the Mississauga office from my home in Oakville and having this thought, “Wow, all this real estate opportunity is available to me and Nick in Hamilton and there’s no traffic at all going that way … but here I am stuck in traffic with everyone else going this way, the wrong way.” 

It was like a metaphor for my life. Why was I going the same way as everyone else? Why wouldn’t I go the way I felt I should go, the other way? Why did I have to keep working in a good job if I just knew my heart wasn’t in it? 

This would be around the year 2005 and for the next five or six months these thoughts just ate away at me. I poured myself into reading even more about sales, marketing, personal finance, and real estate. I began my old practice of meditating and visualizing again. I was on some sort of strange personal mission to force my life into a new direction.

I would carry around index cards with my list of priorities on them: read this book, review that idea, consolidate my finances, increase my credit line, find another property, increase free and clear cash flow. I began a deep dive into the details of direct response marketing.

At the time I was thinking if Nick and I both quit our jobs and used good marketing for “regular real estate” maybe, just maybe, we could make a go at it. I remember having one of the clearest thoughts I had ever had around it, I asked myself, “Why hasn’t someone else just used this type of direct response marketing to create a business around real estate investors? If I could just have a little example of it to prove to myself that it could work I would quit my job right now. Even with a 4-year-old, a six-month-old, a mortgage, and Carol at home with the kids I would do it. I know I could do it.”

And then it happened. Perhaps a week or so later I was reading a marketing newsletter that I was paying $50 U.S. a month for and the author mentioned Rob Minton in Ohio who was working solely with investors and that he used direct response marketing to do it.


I literally raced over to the computer in my kitchen, found his website, and filled out a little form to send me some real estate information.

And then, right at that time, I got one of the biggest commission cheques I had ever received from my job. And life was glorious. I forgot all about my dislike for my corporate life. That cheque distracted me from my pain. I completely dropped the idea of quitting my job. Somehow that cheque temporarily made everything OK.

But this guy Rob kept following up with me. Letters began arriving in the mail, emails were hitting my inbox, and eventually, my frustration with the corporate world bubbled up again.

I got ripped apart in front of the other sales managers for my team having a horrible month.

This was right after having a record month the month earlier. I was pretty pissed off with what I saw for the next ten years of my life.

Going from "here to zero" every thirty days was no way to live.

When I got home that night I ripped open the envelopes that guy, Rob Minton, was mailing and called him for more information. He then FEDEX’d a letter that said for $30,000 U.S. he would share “some” of his marketing ideas with me and would sit down with me for 1.5 days in a group environment to share how he was working with investors in his real estate brokerage.

I immediately called Nick, told him that I was about to spend 30,000 U.S. dollars that I didn’t have, and that I was doing it the next day. I explained that I had reached a boiling point and that I was going to quit my job and begin working with investors.

Thankfully, by some miracle of miracles, Nick, on the spot, said he was with me 100%. And thank goodness he did. I didn’t realize it then but looking back it's clear that it would take both of us to launch Rock Star.

I took a couple of vacation days from work and we drove to Ohio to see first hand what this guy Rob was up to.

Sixty days later we ran our first ad. Twenty four people responded to it. Three asked for more information from us and set an appointment to meet us. One person actually showed up to become our very first member in September 2006.

Much of what we had learned from Rob in Ohio wasn’t applicable to Canada or Canadians but we took the principles of what we saw and tweaked them to our liking.

We sold our first property to an investor in October or November and earned our first commission cheque in December 2006. In January 2007, I gave notice to my sales VP that I would be quitting sometime over the next six months and that I didn’t know when but that I would give two weeks notice at some point soon.

When people hear that they can’t believe the company didn’t chase me out of the place on the spot but at that time it wasn’t in their best interest to get rid of me. I was running one of the top performing sales teams in the company and they were about to go public, so sales numbers and sales volumes were analyzed carefully by investors. They weren’t in the mood to get rid of me and disrupt a good sales team and I always maintained good relations with this VP. I actually learned a lot from him and stay in touch with him today. He doesn’t know it but he was a mentor to me in many ways.

Also, to start the business Nick quit everything to focus on it full-time and we needed some income to support my family and his. He was about to be married and was putting everything on the line. 

I used a credit line that Carol and I had on our family home to pour money into the start of this new business. We went $80,000 in debt before we could blink. But Nick kept working in the closet-sized office that we were renting out from an Oakville real estate brokerage and I worked with him early morning and late evenings. He was running ads, returning phone calls, making appointments, and probably wondering what the heck we were doing.

I began taking two-hour lunches at my job to go find good properties for investors. At one point I promised an investor I’d find tenants for him and began showing his property in Brampton on my lunch. 

In May I finally quit officially and joined Nick full time. We felt that we were generating enough income at that point to not solely rely on credit lines to finance us.

The very next month, Nick and I worked with multiple investors to buy properties and lost out on nine straight deals. One night as we were leaving the office we looked at each other and wondered out loud if we had made the right decisions. We had both walked away from good opportunities to do this and at that moment we were both living off credit lines and financing this little business with more debt.

Somehow we kept believing and we kept running our little direct response marketing ads, kept following up, kept working with investors, and kept trying to offer people something that they wanted.

It was as if everything before that moment gave us what we needed to succeed. Our parent’s work ethic, a knowledge of real estate, marketing, sales, and websites all combined at the right time.

The next month we made a bunch of sales helping investors find good properties in good areas. We slowly crawled out from the debt we had accumulated and began making a real profit.

It feels like a lifetime ago.

Looking back we were insanely naive. And thank goodness for it.

About three years ago, my old company, NetSuite, was having a sales kick-off at the Mississauga Convention Centre the same night we were hosting a Member Event. My old Sales VP was there that night. He had been scoping out the registration table and was blown away at what he saw … hundreds of people showing up to hang out with Nick and me. It was one of those amazingly surreal moments, like life had come full circle.

Today we work with an amazing team in our own brokerage and somehow get the opportunity to work with hundreds and hundreds of amazing members.

In 2015 Rock Star was named one of Canada’s fastest growing companies by Profit Magazine.

We can’t cover it all in such a blog post like this, we’ve left out many of the real estate boot camps that Nick and both spent money attending, the conferences we’ve travelled to, the mentors we’ve had, the properties and tenants that challenged us... but we hope this gives you some context around what we’ve been through. We also left out all the people that told us we wouldn't make it, how the first real estate brokerage we joined told people not to work with us, how another brokerage tried to directly copy us, or how our second office landlord went bankrupt and we had the doors chained shut on us with all our computers, desks, files locked inside. The list of crazy experiences could go on for days!

But hopefully, there's something in this summary that you can use, something to help you on your own journey.

A couple of weeks ago we sat down with a long time Rock Star Member who explained that he quit his job to become a consultant, has several properties, and now has started an online business. 

He was thrilled and so were we. 

You could tell he felt in control of his life and that is a very liberating feeling.

Someone once told us that in life you can pick FREEDOM or you can pick SECURITY. If you pick security you get neither but if you pick freedom you get both.

It's proven to be very true.

Until next time … Your Life! Your Terms!

Related Articles

0 comments on “Before Rock Star: The Story of How We Quit Our Jobs”

  1. Thanks Tom & Nick for a truly inspiring post! Just what I needed to read 😉 Thank you for all that you guys do!

  2. Thanks Fadi, coming from you that means a lot to us. We're very grateful to have crossed paths with someone of your character.

    - Tom.

  3. That ... was awesome!!!

    Origin stories of Tom & Nick and Rock Star are always my favorite. Hearing all the work and effort you put into what you have now, it makes me believe I can find my own way and do it too.

  4. Hi Tom . Thank you for all the insight . I too feel like I'm on a similar journey . I can relate to all you write . I've been reading so much that sometimes I can't keep track of where I read it . There was something I read by you that stated your morning routine broken down by activity and time spent on it . It also mentioned your current journal practice and the book where you got it from , but for the life of me I can't remember where it is . Can you refresh my memory please?

    Thanks again and keep it coming

  5. Stefano!

    Thanks for the feedback. Good to know someone out there is reading our stuff 😉

    I can't recall where we share that either, it's always changing but here it is:

    10min: Meditation/Visualization/Reading (so if no meditation that day, then 10min reading as a min.)
    5min: play offence, outline my 4-Quadrants as per Stephen Covey's 4 Quadrant system for organizing your tasks.

    If I do this I'm ready to rocket through the day.

    There's also sleep, nutrition, exercise etc. but that 20min routine is magic for me.


crossmenu linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram