Mr. Winning Williams: My Best Investments

budget, debt, expenses, financial independence, FIRE, get out of debt, higher education, how we win, income, investing, personal finance, retirement, savings, savings ratio

I was thinking about what my #1 best return on an investment I’ve made to date. I used to invest in individual stocks from time to time, nothing material, but having surplus cash flow after A) paying off my mortgage and B) fully contributing into my company’s 401K plan from our high savings rate, gave investing “play” money. One such investment was a purchase of my company stock in 2009 at a discounted rate of 15% (nice company perk). I sold the stock around 2.5 years later at a ~200% gain. Not a bad profit! Of course, if I was still holding that stock today, the gain would be about 450%! Woops. While this was a great return, holding company stock can be dangerous (um Enron, etc.) as you’re doubling down risk. A scenario with getting laid off while the stock is plummeting is a disastrous combination, especially if your industry of expertise as a whole is being impacted.

Take-away: generally don’t hold more than 5% of your investment portfolio in your company stock.

The next potential top investment consideration is the return on my college education. I’ll go ahead and take credit for the work I put in, but credit is due to others as well. Thank you addicted lottery gamblers in Florida, I really appreciate the Bright Futures Scholarship for 75% of my tuition bill! (BTW, not too many investment strategies involve playing the lottery… weird huh.) With the 75% Bright Futures and my university wooing me to cover the additional 25%, I can’t say I’ll be writing a post about “OMG, College is sooo expensive I MUST take on massive debt!” (But Mrs. Winning Williams may have a thing or two to say about that) The university I attended was located within a 30-minute drive of my Parent’s house. My Parent’s were very clear about frugality, needs/wants (having my own apartment)/etc. As such, I lived at home (no rent/utilities/food costs/etc.) AND had the scholarships mentioned above. Now I also maintained one – two jobs at all times throughout college and continued to apply selectively and received additional scholarships (benefiting from my grades).  So net-net, I’ll say college cost me next to nothing and provided me with: significant career preparation and education, networking opportunities, internships, all leading to my current cushiony job. The combination of next to nothing cost and some hard work and dedication has led to my current career which is both rewarding financially and personally. It didn’t require an Ivy League or private school education and massive debt to obtain this. This investment will continue to provide me with significant opportunities down the road. From a monetary perspective: it was a grand slam investment. BONUS: I also completed my MBA, paid for by my first two companies I worked for. This was of course a deliberate action I took and considered with my selection of employment (me pay for education? Nah!). It took dedication working full-time hours followed with school in the evenings. However, I demonstrated (without need based or otherwise) getting an advanced education with little to no cost.

Take-away: College doesn’t have to be incredibly expensive 

Let’s now finish with my #1 investment. It took time commitment and a monetary investment. These investments could have backfired on me, left me not only with less money, but also with deflated ego and feelings of self-worth. Many others have tried this investment to no avail, basically falling flat on their face. What is this egregious investment then and what is the return? How is better than a 200%+ stock return and endless returns on the no-cost advanced education? Enter Mrs. Winning Williams! This isn’t a post on the tax advantages/disadvantages of marriage, financial synergies from living with someone, etc. This is a well-deserved shout-out to Mrs. Winning Williams and to others searching for their better-half. I love that we get to work together to meet our financial goals. But we have placed an emphasis on supporting and enhancing each other, and this truly brings a satisfaction better than any financial return can obtain. Having Mrs. Winning Williams by my side far exceeds any other return I will net during this life.

Take away: ha, good luck out there ☺

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