Crazy Story About How I Became The Top-Rated Uber Driver In My Area

Since this is my first blog article EVER (knees are knocking), I’ll give you a bit of background and explain how one thing led to another for me to become the top-rated Uber driver in my city, and perhaps even the entire country.

I’m a college graduate, now 34 years old, with a background in sales. I had the privilege to play hockey on a full scholarship to pay my University so I didn’t carry any student loans after that. Once my hockey career was over, I didn’t have much money, but luckily I also had no student debt, and I immediately dove into the rat race working world. My entry goal in 2009 was to make $60k per year and live the American dream along with a wife, 2 kids, a dog, and a white picket fence. My first sales job was selling photocopiers, just like how Robert Kiyosaki started his own path for success in Rich Dad Poor Dad (an amazing book to read to get you in the entrepreneur mindset). I crushed the $60k mark I had aimed for and wanted more. Back then I was highly motivated by money only because the people around me were directly correlating money with success. If you were highly decorated at work because of your sales achievements and numbers, it meant you were raking in a lot of cash. That job was very hard (cold calling door to door, cold phone calls) but was also good for your confidence. The company had a good recipe to keep that little pony going so they could consistently bring in more money. That’s slavery capitalism 101 as an employee. Once I realized I had the potential to make even more (remember, for me making more meant being viewed as more successful in life by my peers) I jumped into what I considered the NFL of sales job: medical device sales.

In my first year of medical device sales, I doubled my income which made me feel amazing. My competitive nature was happy because I was getting a huge promotion into an industry that almost every other salesperson wanted to get into. I got the job after 5 interviews and presentations in a pool of 30 interviewing candidates. My human nature was also delighted because I was able to help doctors and clinicians save peoples’ lives. It was the best place to be in my professional life based on my own success mindset.

The medical device company for whom I worked for was literally a sales person’s paradise. We had amazing innovative products to sell, great teammates always looking to help, a great boss who would provide me with the tools I needed to succeed and fight for me internally, and an amazing founder of the company which was still around to inspire positive changes in healthcare. We were growing by 30% year over year and life was good!!

Suddenly things changed… In 2017, our founder/owner was getting older and our numbers were so good that it put us on the radar for major publicly held biotech companies to buy us. The transaction was passed and we became engulfed in a major publicly owned corporation that’s on the NYSE. The name of the game now became: let’s do what needs to be done for our share price to increase every year even if it’s detrimental in some other areas. The following words came out of our new CEO’s mouth during our National Sales Meeting: “My only job here as the CEO is to do anything in my power to make that share price go up.”

It was hard to see our leaders get packaged out. The new company promised us better more support, given that logically there were more resources within a larger corporation. We were promised better more opportunities for advancement since there were more jobs in a bigger company and more turnover. We were promised a lot of things, but our daily lives as salespeople only worsened.

They put absurd sales targets in front of us that had never been achieved in the history of the company. To top that off, the FDA came in to inspect our production lines after the merge (we were now on the FDA’s radar as part of this new huge corp) and shut our main product line down because it was posing a potential health risk because of lack of documentation. We lost the ability to sell our main product, but our sales targets still increased dramatically. Our benefits were lowered. Everything went to shit and we started leaving one by one. We knew that we would get fired anyway because we couldn’t reach the sales quotas.

A move now or never

After 9 years in sales here I was, unemployed, with decent money set aside for retirement and more money aside for a business opportunity. I always wanted to have my own company and I was confident I could make it happen. At this stage in my life, it was now or never. I could use my savings to build a business or I could get back in the corporate rat race that left a sour taste in my mouth. If I went back to work, I would be “locked-in” 50+ hour workweeks, along with the business travel schedule, and it would take me through another decade without giving me an attempt to build my own business. Then I would be in my 40s, it could be a bit too late to risk something like starting a new business. I was now 32 and decided it was now or never; worst case I would fail and fall back to my previous industry to find another sales job. That was my psychological safety net, it was a risk I was willing to take. I’d much rather be in the “I tried and failed” column than in the “I should have done it when I had the chance” column. I knew whether I succeeded or failed, it would be an experiment that would pay off, monetarily or in the department of life experience.

At the age of 32, I started an online retail business and was able to turn the page on my previous life as a corporate slave employee. I also had online investments that were paying off, which I may or may not disclose on this blog in the future. I worked my ass off to get it off the ground and once it was up, I was only spending about an hour per day to manage it. I automated most of what needed to be done and it freed up all of my time.

Isn’t that what everyone wants? Money coming in and all the time in the world to do what you want? I feel deep down like we’re the architects of our own lives and that I had built what I ultimately wanted… but something was still missing…

Even though I had acquired financial independence from my investments and my online retail business, the people around me still had a 9am-5pm, Mon-Fri work schedule. My life is here, I can’t disappear for 2 months on vacation in Asia, I have many human and financial commitments that prevent me from leaving for more than 3 weeks at a time. I signed up to a private golf course and I could catch my buddies playing at 7am sharp for 9-holes or after 4pm, but during the day, it was all old folks or retired people (like myself duh !?!). I can’t complain, the summers are great and I plug-in 100 rounds of golf per season, playing mostly with my other entrepreneur friends that don’t operate on a conventional work schedule. But that’s the summer, the winter is another story. I live in Montreal Canada and the winters here are brutal. If you don’t find a way to enjoy the winter and snow, it’s a shitty 5 months. I trade golf for ski in the winter, but again, find myself looking for buddies who can’t go during daylight. Long story short, I fucking hate the winter and am bored up to my tits! There… I said it! My first winter in my new entrepreneur shoes was extremely miserable and I couldn’t wait for the spring to show up so I could be at the golf course again. At the end of my 2nd season of golf as an entrepreneur, I needed a plan to prevent a possible depression during the upcoming winter. I also knew that I was going to miss all the socialization that occurs in one single day when you’re hanging out at a Country Club.

What could fill the gap?

I looked at my professional needs and my current assets. I needed something easy to manage in my schedule that I would enjoy doing very much. I knew that if I found something that enabled me to socialize with other cool humans, I would enjoy it even if the pay was average. I joked earlier in the article about the fact that I was like a retired person, but that’s literally how I felt when I wanted to find a social sideline. Many people retire at 60, and then get bored and go back and work to do something they enjoy. They’re not doing it for the money, they do it for fun, socializing, staying sharp, and to get a tap in the back for work well done. That’s what I was looking for.

web wizard media tesla uber
My black Tesla Model 3 Dual Motor

Play the cards you’re dealt. My assets were these: sales experience, money savings, a laptop, a cell phone, a car, a house, a shitload of time. Hold on… I have a car and it’s a Tesla, it’s something I enjoy and feel grateful for every time I get into it. It costs nearly nothing to operate. Wait… I’m a business owner and write off mileage expenses for using my car for work. Now I’m putting two and two together.

But being an Uber driver doesn’t seem too sexy. It’s not like being a top medical sales rep. Would I disclose that sideline to my friends, isn’t it embarrassing? Those were my thoughts when the light bulb flashed in my head and at the same time I was telling myself “Jay you would do this because you CAN and WANT, so you can have fun and meet awesome new people; your friends, on the other hand, are working at a job they don’t really like because they HAVE TO!” That’s not embarrassing at all. Moreover, I would be leveraging a liability (an expensive car) and turning it into an income-generating asset (btw a Tesla Model 3 is by far the best car for Uber and I will prove it to you in future posts). Now that’s smart to play your cards like that! Again, Robert Kiyosaki’s book was speaking to me loudly. So, what’s the worst that could happen?

I manage all my decision making by evaluating the risk of the worst-case scenario. When you are about to make a decision, ask yourself: “What’s the worst-case scenario here and can I live with it?” If the answer is yes, then you should pull the trigger and make the move. The statistical chances of you getting the best case or worst case scenario are slim; you’ll probably land somewhere in the middle.

For becoming and Uber driver, I already had all the assets to be able to operate (car, cell phone, driver’s license, no medical problems). All I still needed was to get my 4C class on my driver’s license and I could flip the switch to ride-sharing whenever I felt like doing it. My worst-case scenario if I didn’t like it would merely be having lost some of my time. That’s not bad at all! There’s no money lost in the process. The risk is very minimal. Like many things in life, I wanted to try and experiment with it. No one really had concrete numbers about how much money could be made as an Uber driver in Montreal, and even if you found information, it’s so area-specific that it’s hard to guess how much you could make as an Uber driver in your area.

I went to get my 4C class and decided to treat this as an experiment and document it. You’re currently sitting in the front row to learn all about it. It’s now been 3 months since my first ride and here’s how I feel about becoming an Uber driver in Montreal.

Is it worth it?

I ABSOLUTELY LOVE IT! It’s exactly what I was looking for. My girlfriend leaves the house at 7am, I unplug my fully charged black Tesla Model 3 Dual Motors and hit the road for a few hours. I give about 5-12 trips per day, mostly business people, and I get to have great conversations with them. When I get back home and switch the driver app off, I’ve racked up between $150-$275 of after-tax net income which equates to $22-$25/hr after taxes and expenses. That’s the equivalent of my friends making $50/hour pre-tax or $100k per year if you calculate 2000 working hours in one year. I was completely shocked to see those numbers and there is a recipe for success not everyone is going to make that much. You need specific tools and tactics to make this much as an Uber driver. I’m starting this blog to document my findings, not necessarily to teach people. If I teach people, it means I’m taking a great part of responsibility for their actions, success and/or failures. If I document my findings, you’ll have the information in front of you to make your own decisions based on my case study. It’s also going to be much easier for me to write in a documentary-style fashion than teaching you like a professor during a course.

Uber driver rating

This opportunity has given me exactly what I was lacking in my day to day life during the winter. I’m meeting new people, chatting and learning new stuff from my riders, teaching them a thing or two, making great sideline money, and most important of all, getting recognized for the quality of my work. I’m proud to share that I have a perfect 5.0-star rating after more than 400 trips in the last 3 months. Customers are shocked and intrigued by my rating when they get ride-matched with me, I hear it often. When I drop them off, then they understand why I have a perfect rating. If you’re interested in owning a Tesla and/or using it for ride-sharing services like Uber, this is the perfect place to learn about the recipe for making $100k per year with UBER and being a 5-star driver.

Please let me know below if you have any questions about owning a Tesla or being an Uber driver that you would like me to address in future posts.


Disclosure: This post may contain affiliate links for products I use and love. If you take action (i.e. subscribe, make a purchase) after clicking one of these links, I’ll earn some coffee money ☕ which I promise to drink while creating more helpful content like this. This does not incur any additional cost to you.

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