First Investment Stories from Personal Finance Experts Episode Five

Successful investors are process-based, rather than product based when it comes to investment decisions. Even if you are provided with the an investment vehicle with the most lucrative potential returns, making consistent profit is unlikely if you depend solely on other people to make decisions for you.  Getting proper education in investing and personal finance is one crucial way to to be a prudent, process-based investor. Here are some testimonials.


Todd R. Tresidder of, former investment hedge fund manager turned writer, money coach and financial educator

Actually, the truth is my first investment was a complete loser – 100% loss.
Believe it or not, that is how I began my investment career – as a total failure.

The lessons learned from this failed investment caused me to change everything because I learned the importance of three things :

(1) risk management

(2) investment process over product

(3) mathematical expectation vs. gambling.

The story of my first investment and the total loss that resulted is explained here…

How My Worst Investment Made me Wealthy

The explanation of investment process over the myth underlying your question about a “good investment” is explained here…

What is a Good Investment

And the difference between gambling and investing is explained here…

Gambling versus Investing

Todd TresidderThe short answer to your question is I honestly couldn’t tell you about my first winning investment because I don’t remember. It is just a process I follow now where I make thousands of investments on an ongoing basis based on mathematical expectation. I don’t remember specific results for any onedecision because I’m not attached to any of them. They just follow an unemotional process based on positive mathematical expectation.

That lesson is far more important than anything you can learn from anyone’s winning investment story. You don’t learn anything when the investment comes out right. It is only the losses that teach you valuable lessons.


Sam Dogen, founder of America’s fastest growing personal finance site, Financial Samurai.  Sam Dogen also started the largest personal finance network on the web (Yakezie) and became a millionaire by the age of 28

My first profitable investment was going to college and learning how to learn in an environment with no parents telling me what to do.  Sink or swim.  I invested four years of my life and probably 3-5 hours every night studying so I wouldn’t end up in a minimum wage job for the rest of my life.


Andrew Hallam, author of  “Millionaire Teacher: The Nine Rules of Wealth you should have Learned in School”. Read my interview with Andrew here.

Andrew HallamMy first profitable investment was a Canadian actively managed mutual fund. I invested $3000 and was encouraged to do so by a millionaire mechanic I worked with (although he didn’t recommend that particular fund company). Today, you would have to twist my arm very very hard (perhaps even break it) before I’d buy an actively managed mutual fund. I’m much prefer to buy ETFs, putting more money in my pocket and less in a salesperson’s.



See below for previous episodes in this series:

First Investment Stories from Personal Finance Experts Episode Four

First Investment Stories from Personal Finance Experts Episode Three

First Investment Stories from Personal Finance Experts Episode Two

First Investment Stories from Personal Finance Experts Episode One

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