Every scary movie has a monster. Mine was losing everything.
When I was 14, my parents went bankrupt. I did not get that financial education at home. I got a scar instead. I still see my mom looking for a few quarters in the couch to pay for milk. I made a promise to myself that I would never be broke.
That fear followed me for a long time. Here is the story of how I left the corporate world anyway, and what it taught me about fear.
What “Retired” Means for Me
When I say I retired early, I don’t mean I stopped working. I quit my 9-to-5 job. I don’t work for someone else, and I am free with my time. It’s more about lifestyle design than the classic retirement.
Chances are I will work until 90, as long as I have my brain.
I had this discussion with Mark, from the My Own Advisor blog. He retired in his early 50s, and he told me to stop saying I’m retired since I keep working. He prefers golfing. For me, golfing would feel like work. Pulling out the camera to record The Moose on the Loose in the morning feels good. I can see myself doing exactly this at 75 or 85.
So I retired from the corporate world. Here is how it happened.
The Sabbatical That Almost Went Wrong
At 35, I had a good job. I was a private banker. Job security, check. Good pension, check. Good salary, check.
Then I decided to take a sabbatical and go on an adventure. My wife and I jumped in a small RV with our three kids for 52 weeks. We drove across North America and Central America, and we lived in Costa Rica for a long time. It was amazing.
In Guatemala, we almost died. To get to Lake Atitlan, one of the most beautiful places I have seen, you drive down a hill with 22 hairpin turns. In a big RV, that is not the smartest idea.
At one point, I had to stop because smoke was coming out of my tires and brakes. I could not turn back. I was driving with my family, and every turn was a choice between the cliff and the mountain. When we reached a small village, I was completely burnt.
Back to Job Security?
When I left for my sabbatical, my boss offered me a higher-paying job for when I came back. The next morning, I called her to take it. No more scary stuff.
She told me the bank was not doing well, and the department was not hiring anymore. There was no job for me at that level. They would find me something, but nobody knew what.
So much for job security. I kept traveling and thinking. When I came back, I made the big jump.
Starting With a $5,000 Monthly Gap
On July 1st, 2017, I started working for myself. The business generated about $5,000 per month. I needed about $10,000 to cover the business expenses and pay myself enough for the mortgage and the kids’ school.
I had no money left in my bank account. All I had was my pension plan and my RRSP. An RRSP withdrawal is fully taxable, and I could not put that money back in. Not a good place to be.
So I had to grind, and the grind was not enough. I had to borrow money. An amazing friend supported me through this crazy adventure. Every few months, I asked him for another $5,000 or $10,000.
Each time, it hurt. I was ashamed of asking. I thought about my parents going bankrupt, and I felt my dream slipping away. I kept thinking that one day, he would say that was the last $5,000. Fortunately, he didn’t.
By the end of 2017, the business generated $98,000 in revenue. I needed about $120,000 to cover everything, and expenses kept growing with the business.
The Breakthrough: DSR PRO
In 2018, we had a crazy idea. We would build personalized reports for our members and call it DSR PRO. Members get a follow-up on every company in their portfolio, so they don’t have to wonder what is going on. We do the hard work for them.
It was a big breakthrough. We got over 100 PRO members in the beta phase alone.
By the end of the year, I was completely burnt. I could not say I was retired. I was really working, and it was not fun. We finished 2018 at $153,000 in revenue, and $108,000 came from DSR. The rest came from other blogs and my Seeking Alpha writing.
Another Scary Decision
In 2019, I dropped all my other revenue sources to focus on DSR. That was scary. With growing expenses, I was close to breaking even, and I was saying no to about $40,000.
By the end of the year, DSR sales reached $158,000. That is $50,000 more than the year before. I was starting to get a decent salary, and I could see the light at the end of the tunnel.
A New Monster: The Pandemic
Then 2020 hit. Everything shut down, and the market crashed. For a split second, I thought people would stop investing and only care about their health. I feared the business would crash and burn, leaving me with nothing again.
I could not control the pandemic. I could control how I spent my day. So I started weekly webinars for my members. Every week, I spent an hour or two answering questions and supporting investors through the crash.
Once again, it paid off. 2020 was our biggest year ever. The stock market and the economy had a V-shaped recovery, and so did my business.
In 2021, I started paying back my debts. DSR made up 93% of revenue, and we cracked $300,000. I finally felt I had a business. We invested in automation, so we no longer do PRO reports by hand, and we hired more employees.
From Investing With Conviction to Retiring With Conviction
Since then, I have focused on growth and on helping people invest with conviction. Then I added one more step: helping Canadians build their retirement plan.
Once you manage your own portfolio, you don’t want to go back to an adviser and pay $10,000 a year in fees. You don’t want to pay $4,000 for a financial plan you may have to redo next year either. So I created Retirement Loop. Now I help people retire with conviction: prepare their plan, optimize for taxes, get the maximum withdrawals and pay the minimum tax.
Fear Lives in Your Mind
Job security, bankruptcy, borrowing money from a friend, having no backup. Facing all those fears paid off.
If you are thinking about starting your business, fear is a concept that only lives in your mind. Like any good horror movie, it is not real. Most of the time, we make it up. Our brilliant imagination tends to convince us of the worst.
Out of a hundred scenarios you can imagine, the one you didn’t imagine is the one that happens.
Join My Free Webinar: 6 Retirement Upgrades
Retiring with conviction starts with a plan you understand. On Thursday, November 19 at 1 PM EST, I’m hosting 6 Retirement Upgrades, a free live webinar for Canadians. I will walk through six ways to upgrade your retirement plan, from paying less tax to what to do if the market crashes. Then I will stay on for an hour for your questions.
Can’t make it live? Register and you’ll get the replay.
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