Jackson Middleton, 34
Non-financial assets (see below)
Jackson Middleton and his father bought four Saskatchewan houses right before the market took off in the mid-2000s. They sold in 2008, and Mr. Middleton put half his proceeds into the stock market. Within several weeks, the junior oil and gas companies he bought on the advice of a friend had "lost ... about 95 per cent of their value."
The other half of his real-estate gain was used to set up a mortgage-brokerage business. This was sold in 2012 to a larger firm, where he now works as the executive editor of the OwnGrowProtect blog at mortgage broker First Foundation (firstfoundation.ca/blog).
How he invests
Mr. Middleton is one of those young adults that Henry Ford might applaud.
The American industrialist once said: "I think that much of the advice given to young men about saving money is wrong. ... I invested in myself - in study, in mastering my tools, in preparation."
Or as Mr. Middleton puts it: "I choose not to invest in stocks or funds or companies not just because I was burned, but because I do not believe any company out there will work harder with my money than I will by investing it in myself."
Right now, Mr. Middleton is investing time and money in becoming adept as the editor of a collaborative blog.
For example, he is working on becoming proficient in social media and using those skills to attract traffic to his blog. Of note is his use of Google+ to host a "public community dedicated to smart conversation around finances in Canada."
"Although I timed the housing market right by purchasing just before it went through the roof, my best move has always been to continue investing in my ability to earn."
Jumping into the stock market a few weeks before it collapsed.
Connacher Oil & Gas Ltd. was acquired at $4.62 per share and sold at 74 cents.
It's currently trading at 20 cents.
"Believe it or not, this was my best stock," Mr. Middleton declares.
"I believe people should invest in their passions rather than their bank account.
"However, I also believe that sound financial management is the best way to accomplish this."
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