Best: Starting my own business. Thanks to this, I’m in WAY better shape financially today than my crappy credit rating would imply. I have mid-six-figures in a corporate bank account in PR (ready to draw on if I need to, but for now just continuing to grow) and am earning, for almost no recurring effort, almost as much money from the business as from my “day job”…all of it free of federal income tax until I repatriate it by “paying myself”. When the business income becomes greater than the “day job” income (this will most likely happen sometime next summer) I plan to “retire” and just focus on new ways to make money for the business.

Runner up (for “Best”): Falling in love with a woman who was about to come into a large inheritance. (No, I’m not marrying her for her money. But having the money does mean we were able to buy an extraordinarily wonderful house, with all the room we’ll ever need, when we’re only 31…and that may prove in the long run to be even better for my finances than the business.)

worse move – not taking money out of the condo and investing in a Roth IRA sooner.

The most painful money move was when, in 2001, I began investing in investment notes with a profitable, publicly traded company called American Business Financial Services. They made loans to subprime homebuyers and small business owners. To fuel growth, they sought funding from investors in the notes. Great rates (I think the highest note paid 12%) and I received an interest check in the mail every month. Things were looking great, and I doubled down: I received an offer from my credit card company for a convenience check at 2.99% for the life of the balance. I took out my limit- $30,000, and put nearly all of it in these notes. In 2004 my first note matured. I requested redemption (they had an auto-renew policy) and received my check. Thinks looked great, but in late 2004, the company announced the SEC would not allow them to issue new notes. I don’t exactly remember why, just that the company announced that without incoming funds, they would have difficulty paying interest and upcoming redemptions. I don’t have to tell you the rest of the store. The company filed for bankruptcy in January 2005 and soon converted to Chapter 7. I haven’t gotten a cent back and probably will never (most assets have been liquidated already and secured creditors are still owed).

My best money move was to become a value investor. Three years ago I began studying Warren Buffett and Benjamin Graham, and their ideas are now ingrained in my thought processes. Value investing is a long term program, though I have had some early successes (take today, when Outback agreed to be privatized. My gain is roughly 25% over 6 weeks!).

I suppose we all learn from our early mistakes. I continue to make them, but the mistakes are less frequent and not as severe these days.

Worst: Getting a credit card in college. I was not mature enough (nor smart, savvy and educated enough) to handle it properly. It got me in 5-figure debt by my early 20s. And it took me years to dig out of the hole.

Best: Getting a credit card in college. It led to the biggest money lesson of my life: If I can’t afford to pay cash, I don’t need it. These days, I never carry a balance on my credit card from month to month. It took a hard lesson, but I finally learned how to handle plastic.

My best move- early acceptance into nursing school (fall of my senior year in high school)- giving me huge ammounts of time to apply for scholarships and grants. I paid for half of my education this way! By the time I needed to pay, I had a year and half saved up- graduated free & clear of any loans whatsoever. This gave me the advantage for years!

Best move: reconciled somewhat later in the startup’s growth cycle and ended up getting about $180K with my stock options. Second best: staying at home for awhile after college and buying a condo instead of renting an apt.

In terms of stocks, my worst move was sensing a wonderful opportunity in TXU, the Texas electric and gas utility, a few years ago when its CEO was on the rocks. I bought at $20, it tanked down to $10, and slowly crawled back to $21, where I sold. It’s now a split-adjusted $169, and for exactly the reasons I thought – they fired the old management team and the new one cleaned up the place. It sucks to be right and wrong at the same time…

Stockwise, my best move was to never get involved with the dotcom Kool-aid, although I worked at several dotcoms during the boom and still live in Silicon Valley. Having worked with them, I knew there were few technical or business barriers to entry for most of these companies, so I figured the market was being suckered.

Best Money Moment:
I’m contributing to my company’s 401k that matches up to 6% and offers profit-sharing. we receive up to $2,000 a year that is placed into our 401k automatically.

stayed invested in some internet stocks during the bubble (made more than $1 million on $50000)

stayed invested in internet stocks during the crash (lost most of it again.)

Guess if I were smarter I would not have made so much nor lost so much.