Losing Money. Time to Learn.

I have been running my mouth for months about how I am basically unbeatable in a PredictIt “mention market.” For those of you who are new to SSG and political gambling,  “mention markets” are bets you make about whether or not politicians will “mention” certain subjects during a public appearance, like a debate or State of the Union. I am a complete and total savage in this space and went undefeated from 2018-2020 betting on what politicians would talk about. Unfortunately, every dynasty must fall at some point. Tom Brady and his six Super Bowl rings just got crushed at home by the Tennessee Titans. And I just lost money for the first time on a Dem debate mention night.

This post will be dedicated to understanding WHY I LOST MONEY and HOW ALL OF US CAN LEARN FROM MY MISTAKES.

It comes down to fundamentals. My winning streak in mention markets was in a by-gone era when all you had to do was bet on IF a topic would be discussed at a debate. Now most of these things are bracketed by HOW MANY candidates will talk about each topic. It’s not enough for Elizabeth Warren to talk about “billionaires” — you have to forecast if Mayor Pete and Uncle Joe will too. This means building positions piecemeal and allocating risk by buying multiple brackets.


Because of the boner-inducing possibility of buying positions that could yield a 4X return (“3” at 23 cents, for example), my betting strategy failed due to one thing:


Per my pre-debate post, I predicted the wrong outcome in three markets. Here is a summary of what I picked and what it cost me:

— “Impeach Mentions” — 1 or 2 — 20 cents/share

— “Soleimani” Mentions –  1 and 2 — 38 cents/share (I told you not to bet on this but I am a degen with a problem so I didn’t take my own advice)

— “Most Speaking Time” — Bernie at 33 cents (I also took Warren as a hedge at 30 but with only 1/2 the number of shares)

How did these markets resolve?

— “Impeach” — 3 mentions. LOSS. (I picked 1 & 2)

— “Soleimani” – 0 mentions. LOSS. (I picked 1 & 2)

— “Most Speaking Time” — Warren. PARTIAL LOSS.

How much would it have cost for me to be less greedy, and stop trying to commit a massive bank robbery with a huge 3-5x multiple? To play it safe by buying JUST ONE MORE BRACKET in each of my losing picks? Let’s see:


— Cost of my picks: 20 cents/share

— Adding the winning pick: +20 more cents/share

— Total winning cost: 40 cents/share

— ROI: 150 percent


— Cost of my picks: 28 cents/share

— Adding the winning bracket: +15 more cents/share

— Total winning cost: 43 cents/share

— ROI: 132 percent


— Cost of my pick: 33 cents/share

— Adding the winning pick: +30 cents/share

— Total cost of winning: 63 cents/share

— ROI: 59 percent.


— 113.67 percent.

The takeaway is…

I tried to make a 3X-5X returns on my bets last night. In so doing, not only did I lose money — I missed a chance to more than double my cash

greed is good.gif

WRONG, Gordon. Greed is BAD. Now listen to DMX and learn.


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