The Challenge

How this experiment works

Overview

Three AI models — Claude, ChatGPT, and Gemini — each manage a real $2,000 of my money for one year. Every Monday they independently research current market conditions, decide how to allocate their portfolio, and execute real trades via a trading API.

The experiment started on June 8, 2026 and runs through June 8, 2027. Their performance is tracked against a passive benchmark portfolio simulated with paper trading. Every trade, decision, and line of reasoning is public.

Rules

  • 01Each AI starts with $2,000 of real money in a live brokerage account
  • 02Trades are made once per week, every Monday at market open
  • 03Any US-listed security is fair game: stocks, ETFs, short positions
  • 04No single position may exceed 40% of the portfolio
  • 05Cash is a valid allocation
  • 06Each AI receives the same market data and prompt every week
  • 07Each AI also receives its own prior 4 weeks of decisions as memory
  • 08The experiment runs for one full year: June 8, 2026 – June 8, 2027

The Competitors

Claude

Anthropic

claude-opus-4-7

ChatGPT

OpenAI

gpt-5.5

Gemini

Google

gemini-2.5-pro

The Benchmark

A passive paper trading portfolio that makes no active decisions, rebalanced monthly. It starts at $2,000 to match the AI portfolios and serves as the baseline to beat.

65%VTI — US Total Market
25%VXUS — International Stocks
10%BND — US Bonds

The Prompt

Every Monday, each AI receives this exact prompt with live data injected:

You are an active portfolio manager competing against other investors over a 1-year period. Your sole objective is to generate the highest possible total return — to outperform your competitors. You are judged on results, not process. You have full discretion: you may take concentrated positions, rotate aggressively, short securities, or hold cash. There is no prize for playing it safe. A portfolio that simply tracks broad market indexes will not win this competition. You are managing a real portfolio with $[TOTAL_VALUE] in total assets. Current date: [DATE] Current holdings: [SYMBOL] | [SHARES] shares | $[VALUE] | [%] Cash available: $[CASH] Market context (last 7 days): - S&P 500 (SPY): [YTD]% YTD, [WEEK]% this week - NASDAQ (QQQ): [WEEK]% this week - VIX: [VIX] - Notable events: [SUMMARY] [Prior 4 weeks of your own decisions, if available] Your task: 1. Assess the current market environment and what it means for your strategy 2. Decide your target portfolio allocation — think like an active manager seeking alpha 3. You may: buy any US-listed stock or ETF, short stocks, buy/sell options 4. Hard rule: no single position may exceed 40% of portfolio 5. You may hold cash if you see no good opportunities Return ONLY valid JSON: { "market_outlook": "2-3 sentence market assessment", "reasoning": "3-5 sentences explaining your alpha thesis", "target_allocations": [ { "symbol": "SPY", "pct": 40 }, { "symbol": "CASH", "pct": 60 } ] }