Once Upon a Time in Predictions Market.

I have made a lot of mistakes in my life. I am not ashamed to admit that. But these three nights still keep me up at night. Not because I lost a lot of money. But because I was sure that I wouldn't.

Costa Rica vs Italy - FIFA World Cup Group Stage

2014 was a different time. Prediction markets did not exist the way they do now. I was a sports bettor with a sportsbook account, a gut feeling, and absolutely no business being as confident as I was. I am not going to tell you which sportsbook. They are not paying me.

I saw Italy in the Group of Death and I put money on them without blinking. A substantial amount. Do not come at me. I thought it was free money. Buffon. Pirlo. Chiellini. I did not run a single number. I did not need to. This was Italy.

Costa Rica had five million people and three World Cup wins to their name. I did not even look up their squad.

For 43 minutes I was a genius. Italy had the ball, Costa Rica were defending for their lives, and I was already thinking about what I was going to do with the money. Then Bryan Ruiz got to the back post and headed it in off the underside of the bar. One centimetre. One centimetre is the difference between me sleeping that night and me staring at the ceiling.

Italy pushed in the second half and found nothing. Costa Rica's defence gave them no way through. The whistle went. 1-0.

South Korea vs Germany - FIFA World Cup Group Stage

By 2018 I had learned my lesson. Or so I thought. I was not the same person who threw money on Italy without looking up the opposition. I had a system now. I tracked form, I studied squads, I looked at head to head records. I was disciplined. I was methodical. And I was on the best run of my betting life that tournament.

Germany was my next move. And honestly, it felt like the safest bet I had ever made. The defending world champions. Neuer. Muller. Kimmich. I looked up South Korea's squad. I looked up their results. I looked up everything. And then I bet on Germany anyway, because nothing I found changed anything.

South Korea had lost both their group games. They had nothing left to play for except pride. Germany needed a win to advance. One does not simply eliminate the defending world champions in the group stage.

I placed a larger bet than usual. The run I was on made me feel untouchable.

For 90 minutes Germany did everything except score. 70% possession. 26 shot attempts. Nine corners. I was not worried. I had seen Germany do this before. Grind, grind, then the goal comes. By the end nobody knew if Manuel Neuer was a goalkeeper or a false nine. That should have told me something.

Then the 93rd minute. I was already thinking about where to place my next bet. A scramble in the box, a Kroos miscontrol, and suddenly Kim Young-gwon had the ball in the net. I told myself VAR would rule it out. VAR gave it. Then I watched Neuer, my goalkeeper, my last hope, standing in the South Korean half like a lost tourist while Son Heung-min rolled it into an empty net from 50 yards. I did not move. I just sat there.

I had looked up the squad. I had checked the form. I had run the numbers. 26 shots. 70% possession. Everything pointed one way. I still lost. That is the part I could not explain to myself that night. Not the result. The logic.

I have read somewhere that if you describe your pain in words it feels less. This felt like someone put Thor's hammer on my chest and I could not get up because I was not worthy. And now I am realizing that no, it does not feel any better.

Argentina vs Saudi Arabia - FIFA World Cup Group Stage

By 2022 I had moved to prediction markets. More convenient, and I can sell my position whenever I am losing. I thought that was the edge I had always needed.

Argentina were priced at 87%. Saudi Arabia at 5%. This time I did everything right. I checked Argentina's form. Thirty six games unbeaten. I checked the head to head. I checked Saudi Arabia's squad, their defensive shape, their recent results. I even checked the weather in Lusail. Everything pointed the same way. I took the position and felt good about it. Not the blind confidence of 2014. Earned confidence. There is a difference. Or so I told myself.

Messi scored in the 10th minute. A penalty, calm as ever. Argentina had three more goals disallowed for offside in the first half. Saudi Arabia had not had a single shot. I was so sure I had already won that I switched off the TV and went to do my chores. I am not even embarrassed to admit that. It was 1-0 at halftime. I had done the work. The position was comfortable. What could possibly go wrong.

I came back and almost all of my money had vanished into thin air.

Two goals. Five minutes apart. Al-Shehri in the 48th minute, squeezing it through the legs of Romero. Al-Dawsari in the 53rd, cutting inside two defenders and curling it into the top corner. A team that had not had a single shot in the first half had just scored twice.

By the time I sat back down the contract had moved so far against me that selling meant locking in a loss I was not ready to accept. So I held. And watched Messi try everything. Nothing went in. The final whistle went.

The edge was never certainty. It was speed, structure, and signals.

I have made a lot of mistakes in my life. Three of them happened during a World Cup. Two as a sports bettor with nothing but gut and a sportsbook account. One as a prediction market trader who thought having a position he could exit was enough.

What I actually needed was to discover the right markets before everyone else did. To analyze the edge instantly, not stitched together across six browser tabs at midnight. To automate my playbook so the edge did not leak between decisions.

So I stopped asking what if and built it instead.