We have all heard it at some point: a fool and his money are soon parted. You can see that we have taken Ben Franklin, that paragon of wisdom and our personal favorite of the founding fathers, to heart here at Pennywise. In fact, as I write this, the bespectacled old fellow peers out at me from another era. A photo of him sits on my desk. His wry smile and those knowing eyes peeking out over his low-riding lenses make me think that perhaps he is aware that here at pennywisepicks we are applying his tenets of thrift, industry, and hard work. He could scarcely have imagined such a thing as the internet, let alone 119 stadiums across this continent playing host to millions of people as they watch a simple, violent, beautiful game in the cool days of fall. Nor could he have conceived of how many of those millions had a betting interest in so many of those games being played. Still, much of his widom applies to this thing we call wagering.

“He that lives upon hope will die fasting.” When I was a young sportswriter I got a chance to cover some tennis in Las Vegas. It was my first trip there and I was amazed by the glitter, the glamour, the girls, but also I was intoxicated with the legality of betting. The bug bit me hard, and my wallet swelled. And then it emptied. I was near broke and as I sat sipping Irish Whiskey watching the game whose Over/Under had already blown my last parlay when a gambler walked up to me. You know what I mean by “gambler”—that peculiar breed of sleazy guy, the type with the pinky ring, the Rolex, the glinting gold-capped tooth, the slicked-back hair. He asked me my trouble. I told him. He said, “Come with me.” We went outside and stood on a corner. He lit up a Nat Sherman cigarette and pointed to one end of the strip, swept his arm the length of the street and turned until he was pointing in the opposite direction at the other end of the strip, leaving a smoke ring in the dry Las Vegas air. As he made this semi-circle he asked, “Do you see all of this?”

“Yes,” I said. He said, “It was built with two things -- the slot machine and the parlay card.”

Rule one of successful wagering: Do not play parlays with any real intention of winning. If you are playing with fun money, play any way you like. But if your real interest is season-long profits, you should never play parlays. Even linking two picks together in a two-team parlay, makes it four times harder to win the bet. I know, I know. It seems easy just to pick two winners. But that is how they get you. And it gets exponentially harder as one adds teams to the parlay.

Experience is a tough teacher, and everyone has hit a parlay at some point. But ask yourself, how often has it happened? What has been the real cost when you think about the number of losses you have incurred, all those times when you hit two out of three, or three out of four. That one loss always breaks the bet.

Rule One: Stay away from parlays. “Genius without education is like silver in the mine.” Many a gambler have I met who fashions himself a genius. One such fellow told me his system: bet on two home favorites of less than ten points and tease the lines down. Sounds good, right? Wrong. You might say that the teaser and the parlay are two sides of the same coin. The parlay lures us in with the promise of increased winnings. The teaser, on the other hand, caters to a different mindset, one that isn't greedy so much as it is self-involved. Other people may lose on this 10-point line, they think, but I will win if I bump it down to four points and I know Miami will cover, too. It happens, yes. But with almost the same frequency as wins on parlays.

Rule Two: Stay away from teasers. “Necessity never made a good bargain.” We have all done it. At noon, we go 0-2 and we are down $220. We figure we will get it back, so we double down at four o'clock. We lose. Now we are down $440. Well, we think, we can't keep losing. So we double down again on the seven o'clock ESPN game, and throw in an extra $200 to get some winnings out of the day. We lose. Now we are down $1080. And here we are near midnight, drunk and panicked and feeling that nauseous swirl of anxiety every moment, shelling out $2200 on Hawaii vs. Fresno St., a game we never would have even thought about betting back at noon. And all of this is just to get back to even. Maybe we win, maybe we lose. It doesn't matter. This is the way to bankruptcy. This is the way to more personal problems than one can possibly imagine. If this is what you do, if this is your story....stop.

The good gambler, and there are some, must have as much discipline as a Marine who has trained and trained and must now take the beach. The instinct to get back what has been lost is always there, I know, but it is a weakness that, if followed, will be your undoing.

Rule Three: Never increase your wagers after a loss. “An investment in knowledge still yields the best results.” Another mistake I have often seen made... Say a fellow bets on five games. Two of them, he thinks, are mortal locks. About the others, he is unsure. So, he wagers $100 on the first two games, and $50 each on the other three. Do you know what happens? The two that he thought were cinches become losses, and the three he was unsure of, become wins. Thus, despite the fact that he went 3-2 on the day, he lost $50!

Whatever you wager, you must wager the same amount on each game. This way your betting day won't be about the surety you feel regarding games. Rather, the day will be about wins and losses. Not that you need to be told this, but perhaps you do. More wins than losses should always equal success.

Rule Four: Equalize your betting unit for each game.

“Dost thou love life? Then do not squander time, for that is the stuff life is made of.” Many of my friends cannot believe this, but I try not to watch many of the games on which I have bet. Nothing I hope or feel or scream at the television will change the outcome. Watching games can be excruciating when you lose, as well as exhilirating when you win. If you are playing for fun, watch all you want, but I have found that if you are playing for earnings it is better to look at final scores than to suffer along and wait out the result, especially since losses may ruin your day and make you sour company for loved ones and friends.

With this in mind I make all my bets for the day at once. This is one of my own personal rules and one that you may not follow, but it has served me well since I am only making bets with a clear head, a head unclouded by desperation or desire. Rule Five: Make all your bets at once and then do something with the day other than just watching games. To synopsize, our rules for successful gambling are:

1. Don't bet on parlays.
2. Don't bet on teasers.
3. Never increase your wagers after a loss.
4. Bet the same amount on each game.
5. Make all your bets for the day at once.

“Who is rich? He that is content. Who is that? Nobody.” Wealth does not bring happiness, merely ease. No one gambles to lose, and yet most of us do. Why? Because when we are winning, we risk more. We get greedy. When we are losing, we risk more. We get desperate. The key to winning lies in between those two poles. Don't get greedy and don't be desperate.

After of all these words, let me add one final ironic quote from our wise, good friend, Franklin: “He is a fool that cannot conceal his wisdom.” A Note on the Kelly Criterion There is a sure-fire way to win. It is called the Kelly Criterion, and it was invented by a Bell Telephone engineer named John Kelly. It is a simple concept, so simple, it is elegant. Increase the amount of your wagers when you're winning, and decrease the amount of your wagers when you are losing. Sounds ridiculous, but simple math is behind it. The amount you bet, and the time at which you bet it are the single most important decisions you make as a gambler. Stated as simply as possible, the amount of your wager should be equal to the advantage you have in the bet. As your bankroll rises or falls, so too will your wager amounts. So, how do you determine your advantage in college football? Through your past performance. If you are paying 10 percent juice (i.e. Laying $11 to win $10) the equation looks like this: W-[L/.91] where W is the winning percentage and L is the losing percentage. So, in pennywisepicks.com's case, where have hit at a 58.6 percent clip (college and pro records combined) over the last four seasons, the equation would look like this 58.6 - [41.4/.91]. You do that little part in brackets first, so 41.4 divided by .91 is 45.5. Then 58.6 (our winning percentage) minus 41.4 equals 17.2.

Thus, our Kelly Criterion advantage says that we should wager 17.2 percent of our bankroll. Say, our bankroll is $1000, this means we would be wagering $172 that week. So if there are five picks, we would lay $34.40 per game. Winning percentage is, of course, calculated weekly and thus, a losing week will mean we wager far less money the next time out, while a winning week means we will bet more.

We do not look at our record outside of the current season to come up with our Kelly number, and you shouldn't either, since this can be a game of streaks. Really, it is a simple philosophy and quite logical -- you want to conserve when you are down, and bet heavier when you are up. You can see how this plays into our belief concerning an equalized betting unit from game to game.

Good luck!