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I’m Building a Prediction-Market Bot — Here’s What Information Theory Taught Me

I've been experimenting with automated prediction-market systems and building a Python-based Polymarket Trading bot.

At first, I thought the core problem was straightforward:

Find a market where my probability estimate is different from the market price, then trade.

But the deeper I went, the more I realized that probability isn't the whole problem.

The harder question is:

How much should I trust the information behind my probability estimate?

The Problem With “Just Find the Edge”

Imagine:

Market probability: 60%
My model:           70%

It looks like a 10% edge.

But what if my model is uncertain?

Maybe the real probability could reasonably be:

58% — 70% — 78%

Suddenly, that 10% edge doesn't look so reliable.

That's where concepts from information theory become interesting.

Thinking About Information, Not Just Prices

Instead of asking:

“Did the market move?”

I'm increasingly interested in:

“What information caused the market to move?”

A price change could come from:

  • genuine new information
  • low liquidity
  • a large order
  • speculation
  • temporary noise
  • correlated markets

A bot that reacts to every movement can easily overtrade.

My goal is to build a system that tries to distinguish information from noise.

Where Entropy Fits

For binary markets, entropy provides a simple way to think about uncertainty.

50% Yes / 50% No
        ↓
High uncertainty

95% Yes / 5% No
        ↓
Low uncertainty

This doesn't automatically tell us whether to trade.

Instead, it gives another dimension to consider alongside:

Probability
Market price
Confidence
Liquidity
Execution cost
Risk

The Architecture I'm Experimenting With

My current mental model looks something like:

Market Data
     ↓
Information
     ↓
Probability Model
     ↓
Uncertainty
     ↓
Market vs Model
     ↓
Risk Management
     ↓
Position Sizing
     ↓
Execution

The interesting part isn't necessarily the order execution.

It's everything that happens before the order.

What I'm Learning From Building It

One of the biggest lessons so far:

A trading bot being technically correct doesn't mean the strategy is statistically correct.

There are many ways to build something that successfully places trades but still has a poor strategy.

I'm paying much more attention to:

  • probability calibration
  • uncertainty
  • liquidity
  • slippage
  • position sizing
  • correlated positions
  • model errors
  • risk limits

My open-source experiment is here:

https://github.com/Benjam1nCup/Polymarket-trading-bot-python-V2

And the deeper write-up on information theory is here:

https://benjamincup.medium.com/information-theoretic-approaches-to-prediction-markets-building-smarter-polymarket-trading-bots-787a28c415a0

What I'm Exploring Next

I'm particularly interested in combining:

Information theory + probability calibration + Monte Carlo simulation + adaptive position sizing.

The idea is to move from:

"Do I have an edge?"

toward:

"How confident am I that I actually have an edge,
and how much should I risk if I'm wrong?"

That's a much more interesting engineering problem.

I'd be interested to hear from other indie hackers and quantitative developers:

How do you deal with uncertainty when your product or model has to make probabilistic decisions?

Contact Info
https://telegram.me/BenjaminCup

on August 4, 2026