What is the safest amount to use for a first CLI trade?

Use a small test amount that you can fully afford to lose, often in the $10 to $50 range for first validation sessions.

Do I need programming experience for this workflow?

No. You need basic command execution and clear prompts, plus strict risk guardrails and execution confirmation.

Should I execute immediately after analysis?

No. Always run a dry-run, confirm downside, and only then execute with explicit approval.

Your First CLI Trade: Safe Beginner Runbook (10-15 Minutes)

TL;DR: If you are new to terminal trading, do this in order: install one CLI, set strict risk limits, run a market scan with your AI agent, place one tiny test order, and log the trade. This guide gives you a repeatable first-trade workflow that is actually safe and useful, not just a demo.

Who This Guide Is For

This guide is for:

First-time CLI traders who want a real workflow, not a gimmick
Non-programmers who can follow simple command and prompt examples
Traders who want agent-assisted execution with tight guardrails

If you want broader context first, read What Is CLI Trading?, then come back here.

What You Need Before You Start

A Mac or Linux machine (Windows with WSL is also fine)
Claude Code installed
A small, predefined risk budget for this test (recommended: $10-$50 max)
10-15 focused minutes

Safety First: 6 Non-Negotiable Rules

Before placing any order, commit to these rules:

Use only a small test amount for your first session
Do not use leverage
Use markets with clear resolution criteria
Never place a trade you cannot explain in one sentence
Always do a dry-run prompt before an execute prompt
Log every trade so you can learn from outcomes

These rules protect you from the two biggest beginner mistakes: oversizing and impulsive execution.

Step 1: Install and Verify the CLI

Open your terminal and install the tool:

brew install polymarket

Verify it:

polymarket --version

If you see a version number, you are ready. If not, check your shell PATH and rerun the install command.

Related tool page: Polymarket CLI

Step 2: Open Claude Code and Set Guardrails

Launch Claude Code:

claude

Then send this guardrail prompt first:

You are my trading assistant.
Rules:
1) Use read-only analysis first.
2) Do not place any order unless I explicitly say "EXECUTE".
3) Keep first trade size <= $25.
4) Show me market, spread, volume, and resolution criteria before suggesting any trade.
5) Explain downside in plain English.

This single prompt dramatically reduces accidental orders and low-quality analysis.

Step 3: Scan Markets with a Structured Prompt

Now ask Claude:

Show the top 10 most active Polymarket markets.
For each market, include:
- current YES and NO prices
- 24h volume
- bid/ask spread (if available)
- one-line explanation of what resolves the market
Then rank the top 3 by clarity and liquidity for a beginner.

You are looking for markets with:

Clear resolution wording
Enough liquidity to avoid large slippage
Reasonable spread
A time horizon you understand

If the output is messy, ask Claude to present it in a simple table.

Step 4: Evaluate One Market Before Trading

Pick one market and run this analysis prompt:

Analyze this market as if I am a cautious beginner:
1) What is the exact claim being priced?
2) What evidence would change conviction?
3) What is the strongest argument against the trade?
4) What are 3 failure scenarios?
5) Give a position size recommendation for a $25 max-risk budget.

Use this quick quality checklist:

Check	Why It Matters	Beginner Threshold
Resolution clarity	Avoid ambiguous outcomes	Wording is explicit and unambiguous
Liquidity	Reduces slippage	Prefer higher-volume markets
Spread	Better entry pricing	Prefer tighter spreads
Time horizon	Easier risk control	Short enough to monitor comfortably
Thesis clarity	Prevents random bets	Can explain edge in one sentence

If any row fails, skip the market.

Step 5: Dry-Run the Order, Then Execute a Tiny Trade

First, ask for a dry run:

Prepare the exact command for a $10-$25 test order.
Do not execute it. I want to review first.
Include:
- side
- amount
- current price
- worst-case loss
- what could invalidate the thesis

Once reviewed, execute:

EXECUTE the previously proposed test order exactly as written.
Then confirm execution details and summarize post-trade risk.

The goal of trade #1 is process validation, not profit maximization.

Step 6: Journal the Trade (Critical for Improvement)

Immediately after execution, store a short post-trade log:

# Trade Journal Entry
- Date/Time:
- Market:
- Thesis (1 sentence):
- Entry price:
- Size:
- Max loss:
- Invalidation condition:
- What would I do differently next time?

Without journaling, you cannot separate luck from skill over time.

Common Problems and Fast Fixes

Problem	Likely Cause	Fast Fix
`command not found: polymarket`	CLI not in PATH	Restart shell and rerun install
Agent gives vague analysis	Prompt too open-ended	Ask for explicit fields and table output
Fear right before entry	Size is too large	Cut size until emotional pressure drops
Cannot explain your thesis	You are copying momentum	Skip the trade and reassess
Regret after order	No invalidation rule	Define exit conditions before next trade

A 7-Day Beginner Progression

If you want fast improvement, follow this sequence:

Day 1: One tiny test trade with full journal entry
Day 2: No trade, only analysis of 5 markets
Day 3: One trade with pre-defined invalidation
Day 4: Review both trades and extract 3 lessons
Day 5: Repeat with stricter sizing discipline
Day 6: Compare your notes to market outcomes
Day 7: Write a one-page personal trading checklist

This builds process quality before increasing risk.

FAQ

Do I need to know programming?

No. You need to run a few commands and write clear prompts. That is enough to start.

Should I start with stocks or prediction markets?

Prediction markets are often simpler for a first workflow. If you prefer equities/options, start with Alpaca MCP Server and use the same guardrail pattern.

What is the biggest beginner mistake in CLI trading?

Treating AI speed as trading edge. Your edge is process quality: clear thesis, small size, repeatable risk control.

What to Do Next

Learn interface strategy: CLI vs MCP — When to Use Which
Expand your stack: browse CLI tools, MCP servers, and Skills
Move from first trade to repeatable system: What Is CLI Trading?

A Note on Risk

This guide uses prediction markets because they are accessible and easy to understand. The risk is still real.

Start small, stay process-focused, and increase size only after your journal proves consistent decision quality. See our full risk disclaimer.