3 Years Ago, I Designed the Life I Always Wanted

On July 1^st, 2017, I came back from a one-year RV adventure with my family that crossed North America and Central America. I then officially quit my job and started my new venture as an entrepreneur.

I had very little money.

I barely had a business at all.

I did it anyway. Why? Because I wanted more from life and I wanted more life for my family.

Here I am 3 years later, writing about my progress and failures. My goal today is to inspire anyone who once had a great idea but then let it sit on the shelf so they could go back to their secure, and let’s be honest, safe, but boring life.

That security many thought existed blew up in their face in 2020. The pandemic created a climate of instability where many lost their jobs. Job security is a seducing concept that is rarely applied to real life. In fact, when things go wrong in your department, you are usually the last one to know about it. And then, it’s too late.

The mirage of job security

Back in 2003, I started my career in the financial industry. I got my first job in the back office of a bank to clear futures and options transactions. I was thrilled to learn about the stock market and eager to get my first promotion. The problem was that my job wasn’t that exciting. After a couple of months of learning how it works, I was pretty much balancing excel spreadsheets all day and calling traders who kept making mistakes on their orders. The worst combination of attributes for a young man trying to make his mark in his professional career is being bored and cocky at the same time.

I certainly didn’t approach my boredom the right way when I look back at how I acted. To make a long story short, I started to get on my colleagues’ nerves as I was doing the job faster than anyone in the office. I was complaining about my boredom and kind of putting it in their face. I had my first evaluation after 6 months and my initial employment probation was not waved as my manager didn’t appreciate my attitude. While I understood her point, I didn’t like being called on the carpet and half of what was written in my evaluation was based on hearsay coming from my “dear” colleagues. I ended-up quitting the following Monday.

I soon realized that job security doesn’t exist. Nobody cared about me in my previous job, and I was replaced in a heartbeat. That told me that I needed to first shut my mouth and second to become more “employable”. I rapidly got a new job where I used my recent learnings religiously. I found a mentor who helped me obtain several skills that I not only needed but also would look good on my resume.

For more than a decade, I worked at the National Bank developing my new skills. I took Excel classes, completed my securities courses, obtained my CFP title and finally completed graduate school and earned my MBA with Honors. My plan was to make sure I had a solid resume in the event of losing my job. Yet despite completing my plan I wanted more.

Building an asset from scratch

While I was pursuing my career goals, I also knew that having a solid paycheck wasn’t enough. What if I lose my job and there is no new job in my field due to a recession? What if I had to endure a toxic work environment or a petty boss? I needed a way out.  I needed a better path.

In 2006, I started blogging. Back then, nobody thought they could make money blogging. In fact, there were less than 100 financial bloggers in Canada and possibly in all of North America!

It took me 6 months of hard work to earn my first $100. Assuming I was working 10-15 hours per week on this sideline business, this didn’t look like a venture that offered a fair return on my investment in time. Then, in 2008, everything changed. My partner and I realized we could make money through buying blogs and selling advertising. We created a corporation and started doing business “the right way”.

This side business led me to buy The Dividend Guy Blog in 2010. Two years later, my entire portfolio was shifted towards dividend growth stocks and in 2013, we created an asset that has now changed my life forever: Dividend Stocks Rock.

In 2014, my wife and I decided to quit everything and go for a one-year trip. We then worked on this plan for two full years. We found solutions to all the obstacles we encountered in realizing our dream:

Can’t quit my job, but I can ask for a sabbatical!

Can’t lose my house, but I can rent it while I’m away!

We did not speak Spanish, but we could learn along the way!

Our kids could not miss school, but we could arrange to homeschool them!

We did not have enough money saved for the trip, but I can build an asset that will generate money as we travel.

You read that last sentence correctly. When we left for this crazy adventure in 2016, we had about $3,000 in our bank account. No other savings. I obviously had an investment account, but I didn’t plan on withdrawing from my retirement nest egg. The plan was to work hard enough on DSR so it could generate the income to pay for our trip.

Starting a business losing $6,000 per month

The plan worked for the most part, but I ended-up borrowing about $20K to complete our trip. When I came back in 2017, I was literally broke, and I had piled up a RV loan + 20K in debt to finish our trip. I decided I wouldn’t come back to my high paying job as a private banker and continued to work on DSR instead.

This could have been defined as a stupid decision by many.

Going back to the bank was the easy route as within a year I would have paid back our 20K of “love money” debt and moved on. Instead, I decided to jump off the cliff and concentrate on DSR. But, DSR generated enough money for me to live in my RV parked on the beach in El Salvador. Let’s just say the cost of living in North America is slightly higher. Assuming my “new salary”, the company was losing $6,000 per month. This was far from ideal!

I did an update last year around the same time (you can read about my entrepreneural life here). I discussed how I had to work relentlessly to pay my bills. I also had to rely on more love money back then. I wasn’t proud of that. But I knew where I was going. It all made sense starting in early 2020.

The lifestyle I wanted is happening

Last year, I mentioned that I planned on taking a 1 month adventure away every year with my family. That started with Vietnam this year. This was a crazy adventure! We did the “entire” country from Sapa to Ho Chi Minh city. We experienced night trains and sleeping buses more than we wanted, but this was part of the trip! Here are some of our best moments:

One amazing thing happened during that trip: the business was running without me! I worked about 10 to 15 hours per week, but the team I had in place took care of almost everything! I could finally see it happening: my dream lifestyle is slowly but surely taking shape. A lifestyle where I work because I love it, but where I can also take several weeks off without hurting my business.

For 2020, I expect I’ll have between 7 and 8 weeks of what employees call vacation. I do work 1-2 hours each day during that time, but it’s a small price to pay to have such freedom. While the covid-19 may or may not influence our plan for 2021, we will have the budget ready for another trip next year. We would like to go to Portugal for 3 weeks at the end of August 2021.

A (short) episode of great fear and great pride

The month of March 2020 was a crucial month earlier this year. The market crash created by the pandemic frightened me. Not because my portfolio was doing down, but because I feared that investors would drop the ball, sell everything and, obviously, cancel their subscriptions to my service.

I realized that I could be playing with the future of my business during that month. Instead of hiding under my desk and hoping the virus went away, I decided to work even harder. I usually do 1-2 webinars per month, but I was doing 3-4 webinars per week! I first supported my members with “ask me anything” webinars and my weekly newsletter. I’ve helped them navigate through this storm while I was also doing free webinars for my other readers. We all worked through this crisis and have now emerged stronger than ever as both individuals and in our DSR community.

Then, the moment of great pride arrived. Here’s a little timeline on how we lived the month of March in the past 3 years:

March 2018: We had just launched DSR PRO (a customized report sent quarterly to all our Pro members). I worked days and nights to pull it off and I was completely drained. We had our Ycharts and server annual renewal that month. We didn’t have enough money in the bank account, and we had to rely on love money (read more money injected in the business) to get through this month.

March 2019: In a year, we went from 35 beta testers for DSR PRO to hundreds of members. It was still a lot of work, but a good part was automated. The business made enough money over the past 12 months that we now had a line of credit at our bank. We had to withdraw money to pay for our annual renewals. At least, we didn’t need love money this time (we were pretty much out of love anyway!).

March 2020: We now have 4 people working part time on DSR PRO and most of our process is automated. We generated over 400 reports that month without breaking a sweat. Cash was strong enough that we didn’t touch the line of credit for our annual renewals. In fact, we even struck a deal to pay for 2 years upfront to benefit from a rebate offer.

When I realized we could pay several thousand more in fees upfront without borrowing money, I realized everything we had achieved over the past 3 years. We now have a real business with real positive cash flow!

What changed in the third year

When you look at new business stats, you see that many small businesses don’t survive their first five years. We are talking about 40% of companies that don’t make it past 5 years (Canada, US source). In my experience, the first two years were filled with promise as we saw the growth, but there was a consistent need for new capital. Then, during the third year, we were shifting toward the other direction. Cash flow was stronger, and we rarely had to draw on the line of credit. In fact, we have started to pay down on some of the love money debts and our other debts.

Last year, I wanted to hire a full-time employee, but it didn’t happen. The person I had in mind decided to go another route, and I came to realize that hiring a full-time employee working in finance would be more difficult than I thought. It is a very rare individual that wants to take the risks I’m taking. Why would you go work for a small but dynamic business when you can lock-in a secure job at a big firm? Plus, I couldn’t afford to pay what the big financial firms offer for comparable talent.

We then decided to again get creative and hired independent contractors (part time workers) for specific tasks. It appeared to be a lot easier to cover smaller tasks and it forced us to become more efficient. Today, I don’t think I will hire a full-time employee in 2021. I would rather direct my cash flow towards retiring debt and investing in new technology!

What’s going to happen next?

Believe it or not, I did my first cash flow project about a month ago. Over the past 3 years, I’ve simply focused on growing and making more money month after month. I was in survival mode and then shifted toward “okay, but let’s keep rolling” mode. For the coming year, I will enter “planning” mode.

I guess this is what I should have done from the start. If I hadn’t had so much pressure to find money, I might have done it differently. In the end, a better plan will likely bring more business. But life happens and the theory doesn’t always apply! The entrepreneur life has one and only one constant element: change!

For the next twelve months, I want to plan better and make sure we shift from our historic linear growth to exponential growth realization. The business is growing, we get more and more customers referred by our own members which is awesome, but I want this venture to fly.

I will identify my growth vectors and make sure I allocate the necessary resources to capitalize on those growth opportunities. I have a few ideas in mind that include some technological upgrades I’m working on. DSR members should be very happy to see these ideas come to fruition! I just don’t know when they will happen, but I’m usually not a patient person!

We have a larger and stronger team to work towards those new objectives today. Without them, our venture wouldn’t have grown as it has. DSR would not be in a position to help over 1,500 investors to invest with conviction and enjoy their retirement without the talent we have managed to attract to our organization. I want to thank Vero, Dick, Oli, Davide, Sneha and William for their amazing work. I truly feel this is not just the beginning of a real business, but we have evolved into a growth stage that will be incredibly exciting for us all!

If you have any questions about how to start a blog or create a part time business to get away from your 9-5 golden cage, let me know in the comments or by email (or even through Twitter!), I’m always available. ?

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