Jimi Hendrix was one of my favourite artists once I grew out of rap and hip-hop and started listening to classic rock in my early 20s. He was a trailblazer of the electric guitar, revolutionizing the sound and style of rock and roll. With his innovative playing and virtuosic solos, he left an indelible mark on the music world. As most of you probably know, like many others in his ear, his life was cut short when he died at 27. My story is very different

Saving my First Downpayment

After a short career as a manager at Foot Locker for a few years, I joined the family business, a piano retailed in Toronto. The hours were unlimited and it was a straight commission position, but I was making an above-average income of $80,000 CAD ($60,000 USD). The money was good but wasn’t life-changing. I liked the idea of building the family business and was being groomed to have an ownership stake. I also enjoyed the structure of working long hours in a competitive environment. It was stimulating. In the early years, I learned a lot about retail, wholesale and general business practices. But, I was unhappy, out of shape, emotionally disconnected, and generally frustrated with where my life was.

My First Investment Property

I’ve always been good at spending money. Some friends called me frugal. Others downright cheap. I didn’t care. I had ambitious financial goals since I was very young and lived on a shoestring budget. I started slowly stacking my chips. By my mid-20, I had amassed a decent net worth. My landlord at the time convinced me to purchase my first home a few years earlier in Oakville, ON. She was a successful real estate investor and successful entrepreneur. She trusted me to the extent that she offered to match my downpayment as a no-interest loan to help me get into the market sooner.

94 Richmond Rd, Oakville, ON — My First Home

We found a great little detached bungalow on a big lot with the potential for a basement apartment. It was perfect. With the proceeds of a refinance 8 months later, I paid her back and purchased my second home, an investment property in Hamilton, ON. The renovations on both properties took longer than expected, and I ended up living through a nightmare reno. But it was all worth it.

Leaving my Career

While this was happening, my work environment started to become less stable. I was promoted to Director of Sales after 5 years with the company. There was a new Chief Operations Officer had been hired to shake up the company culture. I directly reported to him, and after a few months, he started putting more pressure on me. I was already underpaid compared to my coworkers, and his squeezing me didn’t go over well. After many altercations with this individual and my father, I drew a line in the sand. “Pay me fairly, or I’m leaving.” I wasn’t ready to go out on my own, but I knew I could get paid more selling cars, real estate and several other products with my skills.

I gave my notice the summer I turned 26 but agreed to stay on for another 6 months to ensure that I completed all the projects I was working on and delivered the inventory I had sold. During that time, the COO made several serious mistakes and was eventually fired. Although I was still working hard, I was mentally checked out and already thinking about my next steps. So when I asked to stay for the long term with the increase I had been demanding, I turned down the offer. It was tempting to stay since I was comfortable there, but I was too excited about the prospect of a new adventure in life and business.

Wendy — My Mentor and Inspiration for Becoming a Real Estate Investor

Becoming a Full-Time Investor

During those few months, I thought a lot about my next steps. I considered getting into the automotive business and had a few interviews at some luxury dealerships. I also was tempted to get my real estate license, but after being in sales and customer service for the past decade, I was sick and tired of dealing with clients. But, in the back of my head, I kept coming back to the idea of becoming a full-time real estate investor. My friend and long-time mentor gave me the confidence I needed to go out on my own and kept telling me, “you have a great eye for real estate.”

Financially I wasn’t ready to go on my own. I had access to a few hundred thousand dollars in cash and credit and about $60,000 CAD in commissions banked that I was still drawing on. But, I knew without a full-time job, my access to credit would quickly run out. I knew that I wouldn’t be able to get approved for mortgages as a self-employed individual. If I didn’t quickly grow my portfolio and start acquiring profitable properties, I would need to get “a real job.”

149 Strathcona Ave N, Hamilton, ON — My First Investment Property

That following summer, I left my job, sold my home in Oakville, and moved to the semi-finished basement apartment in the triplex I owned in Hamilton. I had 2 apartments above paying my mortgage, about 100K cash from the proceed of my home in the bank. I went from 75 hours in the office grinding out deals to living life on my own terms. It was incredibly liberating and motivating. I’ve never felt freer in my life.

Building my Portfolio

I immediately started hunting for my next renovation project and potentially a place to live and call home. I had been exploring an up-and-coming neighbourhood in Hamilton called West Harbour, as the locals called it, “The North End.” Historically, it was one of Hamilton’s roughest neighbourhoods and was located in Hamilton’s historic port. It was still rough, but when I drove through there for the first time in 2010, I immediately fell in love. It had stunning waterfront views and access to nature, and the proximity to downtown Hamilton which was starting to gentrify was a huge plus.

I must have seen 50 homes and scoped out 100’s more online before we found my next buy. It was a cockroach and catshit-infested shithole and was currently being squatted by the owner’s kids and their friend. I had to wear an N95 mask when going through the place. The stench was so bad it made me sick. But I smelt money, and the location was excellent. I was also looking at another home close by that was less exciting but a cheap deal. I ended up putting both under contract and, as they say, “begging, borrowing, and stealing” to get these deals closed.

My First Gut Renovation

I knew nothing about renovating homes, and both places needed a gut. I had spoken with a few contractors but convinced my cousin TJ McIntosh to drive up from Buffalo and help me get started. I still don’t know why he agreed to do this, but he believed in me and wanted to help. I knew nothing about construction, and TJ was already an experienced tradesperson. He gave me a crash course on home homes work, mechanical systems, flooring installation, drywall, plaster, and more. I’m so grateful to this day for his help on that property.

414 Bay St N, Hamilton, ON — Purchased for $245,000, Sold for $530,000

My First Big Cheque

After the renovations were completed on both, I was financially maxed. I decided to sell the second and smaller of the two properties I had purchased and moved into the one near West Harbour. That year the market jumped more than 20%, and I refinanced all of my money out of the property and then some. This was the biggest cheque I had ever received in my life. Once I knew the refinance was coming, I immediately searched for my next deal. For the first time in my life, I felt like I had financial security.

I had settled into my new home at 414 Bay St North
I was receiving cash flow coming in my triplex a had purchased a few years earlier
I made a quick $70,000 CAD profit on the property I had sold
I refinanced the property I was living in and extracted my initial investment

We found a dilapidated 3000-foot-old victoria semi in the Stinson neighbourhood in Hamilton on Emerald Street South. It was a very rough part of town. But within 5 min of walking into the place, I knew it was the one. It was listed for $199,000, and I scooped in a bidding war for $236,000. The deal wasn’t scheduled to close until the fall, so I decided to go on a vacation for the first time in my life. I had always dreamed of going to Europe. I had been to Amsterdam on business once and was dying to return. I found something magical about the history, architecture, and way of life appealing.

Ford Focus Wagon Rental Car, Amsterdam, NL

My First Taste of Freedom

I convinced a few buddies to come to Europe with me and make an epic 8-week road trip. Starting in Amsterdam, we drove to London, Paris, Andorra, Barcelona, Nice, Slovenia, Budapest, Prague, Berlin, and back to Amsterdam. I was the designated driver, so I rented the cheapest car we could find, only to show up and realize that it was the smallest car we had ever seen. It didn’t even fit our luggage. It was ridiculous and had a whopping 80 hp. I begged the guy at the desk to hook us up with something a bit bigger. About 20 min later, they pulled out a tired-looking Ford Focus station wagon. It didn’t look pretty, but it had a 5-speed manual transmission and a diesel engine. Perfect. I kicked the shit out of the thing so badly we needed a second set of front tires by the time we reached Italy.

That trip completely changed my life. Exploring some of Europe’s greatest cities, staying in hostel dorm rooms, drinking and eating like broke students, and just relaxing on the beaches on a Tuesday was incredible. I met incredible people on that trip, some of which I still keep in touch with. And for the first time in my life, I finally felt free.

As I reflect on that period of my life and the decisions that I made, I realize that there is never going to be a “right time” to start a new life and go out on your own. Those formidable years in my late 20s changed me forever and were really the start of my nomad and entrepreneurial journey.

**Bio**
International Real Estate Investor and Entrepreneur
Founder **@Offshore Freedom** | Host of the **@CaribbeanRealEstatePodcast**

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This article is for informational purposes only; it should not be considered financial, tax planning or legal advice. Consult a financial or investment professional before making any major financial decisions.

Jimi Hendrix Died at 27 — I Decided to Start Living