I'm sort of invoking Southwest Airlines here, but not exactly. What I am invoking are the incredible number of television and radio commercials for legal gambling sites and for car insurance. Both offer rewards while requiring payment upfront. In anecdotal fact, if it wasn't for these two entities advertising on television especially, and on radio to a lesser degree, the airwaves would be a lot less redundant. I'm so used to seeing Flo from Progressive, LiMu Emu and Doug from Liberty Mutual and all sorts of familiar characters from Geico that I am actually contemplating making an insurance inquiry. Together, these insurance companies in particular have combined to nearly beat me into insurance-quote submission. The last time I changed car insurance companies was after seeing a plane at the beach flying a banner for all of us who could see encouraging us to make a call. It was – for me, the last straw. I called the company the following week and was indeed rewarded for that call: hundreds in premium savings.

Likewise, DraftKings, Fanduel and BetMGM have combined to nearly entice me into entering their world of online, sportsbook betting. Unfortunately, I have a much better grasp of the jargon and issues addressed by car insurance advertisers (having been a Certified Financial Planner in my previous profession). With respect to the sportsbooks, even though I'm a long time "sports guy," and as such understand the nature and risks of anticipating a desired outcome, I've rarely ventured outside the lines. Those lines being an NFL most-winners pool held weekly in season at my wife Dina's former employer, a season-ending Super Bowl point-totals-at-end-of-each-quarter thing, and a yearly participation in the annual NCAA's "bracketology," (which I've actually won once).

But the modern sportsbook and even the individuals hired by the radio and television networks to discuss/albeit recommend the various "plays"; the over-under, the parlays and all the extra-special, apparent can't-miss opportunities for new/first-time bettors/gamblers hyped as if there really is nothing to lose by playing and only money to win, is all too much for me to process and understand. After listening to all the noise, I really feel a need to take a class to protect myself from simply losing/throwing money away because I think I understand, but likely understand very little of the actual risk/reward dynamic. Certainly, I can appreciate the excitement of winning money at the expense of others, but as most would attest, at the very least, expecting that outcomes will satisfy your financial needs is a slippery slope at best and a rabbit hole at worst (why else the "If you become afflicted to gambling" advisories on all the advertisements).

The car insurance companies are certain we all want to save money on such necessary got-to-haves like car insurance. And the sportsbooks are betting (pun intended) that we all want to find free money and are not opposed to taking a chance to get it. A chance which if successful, might actually provide the extra money needed to pay their car insurance premiums. I fear however, that once dipping my wallet into the gambling waters, and win a little, but likely lose more, it might be difficult to extract myself from their figurative clutches. The car insurance companies are sort of the same. They entice us by advertising lower prices, then hope to retain customers by offering various other incentives such as "accident forgiveness," "vanishing deductibles" and the like. In effect, they're both trying to bait us and hope we don't switch. Their motivation is quite similar: they want our money and they want us beholden to them. It's not ideal, but it sure is prevalent. In each instance, you're "betting" money on an outcome which is totally out of your control: predicting scores and predicting whether you'll have a car accident or not. Whose to know? Not me. In addition, I've grown weary – and skeptical of the never-ending pursuit of my dollars. Besides, I got out of the predicting business as soon as I received my "terminal" cancer diagnosis in late Feb., 2009.