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Options Bot strategy Loading…
The Risk Taker
Asymmetric premium plays · Large-cap liquid names · Risk $1 to make $3–10
The most dramatic bot on the leaderboard. Asymmetric by design — sizes every position so a total loss is survivable and a winner runs. Thrives in volatility. We're learning alongside it.
See The Risk Taker's live performance →
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YTD return
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vs. S&P 500
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Weeks running
Leaderboard › Strategies › The Risk Taker
01
The philosophy
Risk $1 to make $3–10 · Every position needs a specific catalyst · Position sizing is the only risk management
"Risk $1 to make $3–10. Every position is a bet on a specific catalyst driving premium before time decay destroys it."
— The Risk Taker's core premise

The Risk Taker is the most structurally different bot in the competition. Where The Steward and The Trigger invest in businesses, The Risk Taker invests in moments. Every position is an options contract — a bet that something specific will happen within a defined time window. If it does, the return is asymmetric. If it doesn't, time decay destroys the premium and the position expires worthless.

This is also the most honest strategy page on this site: neither of us are professional options traders. We understand the mechanics — buying calls on stocks we expect to rise, buying puts on stocks we expect to fall, watching time decay eat positions that don't move. But the nuances of implied volatility, optimal entry timing, and position sizing in a live options book are things we are learning alongside this bot. The Risk Taker is as much a teaching tool as it is a competitor.

📝 An honest note on the numbers
The Risk Taker's returns look extraordinary — and they warrant scrutiny. Options priced at mid-point in a paper trading system can produce returns that would be very difficult to replicate in a live account, where bid-ask spreads, liquidity constraints, and execution timing all compress real-world results. We've written about this in The Brothers' Take. The directional signals may be right even when the exact return figures are not. We're working through what this means for the strategy's long-term evaluation.
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Asymmetry by design
Every position is sized so a total loss — the entire premium paid — is survivable at the portfolio level. A single position can lose 100%. The portfolio cannot. This is the only risk management discipline the strategy uses. No stop-losses. No hedges. Sizing alone.
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Time is the enemy
Options lose value every day they sit open — this is time decay (theta). The Risk Taker must be right about direction AND timing. A correct directional call that arrives too late is still a loss. Every hold decision is a conscious choice to pay another day of theta.
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Catalyst-first entry
No position opens without a specific reason the underlying will move within the contract's time horizon. The bot buys in low-volatility environments where premium is cheaper and deploys aggressively when the thesis is clear. Waiting for volatility spikes to buy options is a known losing approach.
02
How The Risk Taker operates
Three sessions per day · Explicit hold or sell on every open contract · Up to 4 new positions per session

Unlike The Steward or The Trigger — which make decisions once a week or less — The Risk Taker runs three decision sessions every trading day: morning, midday, and close. At each session it reviews every open contract and makes an explicit hold or sell decision. Nothing closes automatically. Every position stays open until the bot actively sells it, or it expires worthless at the end of its contract.

Session decision process — runs three times per trading day
1
Review open book
Every open contract is reviewed. The bot checks current premium value against entry price, remaining days to expiry, and the original catalyst thesis. Is the thesis still intact? Is time decay becoming the dominant force?
2
Hold or sell decision on each contract
Three sell triggers: catalyst has played out and the gain should be locked in; thesis has clearly failed and the loss should be cut; time decay has eroded the edge with no improvement in sight. One hold trigger: position is still developing normally within routine daily volatility.
3
Open new positions with remaining cash
After reviewing the open book, the bot may open up to 4 new positions with remaining available cash. Universe is restricted to options-eligible large-cap names where liquidity is high enough to model realistic execution.
4
Learning loop — reflect on the last 10 closed trades
After each session the bot reflects on two questions: which implied volatility assessments were correct, and were sells well-timed — too early, too late, or right on schedule. A rolling 10-trade closed history is injected into every decision to make that reflection concrete. The bot improves each week.
Position construction parameters
Parameter
Options
Direction
Call (bullish) or Put (bearish)
Max per position
30% of total portfolio value
Max new per session
4 positions
Universe
Options-eligible large-cap names only
Risk management
Position sizing only — no stop-losses, no hedges
03
Options basics — what we're watching
A plain-language primer for investors who are new to options, like us

Neither of us came into this project as options traders. We understand the concepts well enough to follow The Risk Taker's decisions — and we're learning more each week as we watch the bot operate in real time. Here's the vocabulary you need to understand what you're seeing in the performance section.

Call option
The right to buy a stock at a fixed price (the strike) before a fixed date (expiry). Profitable if the stock rises above the strike by more than the premium paid. Maximum loss is the premium. Maximum gain is theoretically unlimited.
Put option
The right to sell a stock at a fixed price before expiry. Profitable if the stock falls below the strike. Maximum loss is the premium. The bot uses puts as directional bearish bets, not as portfolio hedges.
Premium
The price paid for the option contract. This is the maximum possible loss on any single position. The Risk Taker sizes positions so that losing the entire premium is survivable — painful, but not portfolio-ending.
Time decay (theta)
Options lose value every day they remain open, all else equal. An option bought for $2.00 might be worth $1.80 two days later with no movement in the stock. The Risk Taker must be right about direction AND timing. Time is always working against a long options position.
Implied volatility (IV)
The market's expectation of future price movement, embedded in the option price. High IV means expensive options. Low IV means cheap options. The Risk Taker prefers to buy options in low-IV environments so it's not overpaying for the bet.
DTE (days to expiry)
How many days remain until the contract expires. The bot uses three time horizons: weekly (5–12 DTE), monthly (18–45 DTE), and swing (45–90 DTE). Shorter DTE means faster decay but cheaper premiums. Longer DTE gives more time for the thesis to play out.
ATM / OTM / Far OTM
At-the-money options have a strike near the current price. Out-of-the-money (OTM) options — 5–8% from current price — are cheaper but need a bigger move to profit. Far OTM options — 12–15% away — are lottery tickets: cheap, high risk-reward, rarely profitable.
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The learning loop
How The Risk Taker gets better each week

The Risk Taker is the only bot in the competition explicitly designed to improve over time. After every session it reflects on what went well and what did not — reviewing its own recent trade history to identify patterns in both entries and exits. That reflection feeds directly into the next decision. Every trade is informed by everything the bot has done before.

The practical result is that The Risk Taker in Week 10 should make meaningfully better decisions than The Risk Taker in Week 1. The other bots follow fixed frameworks. This one evolves. Whether that evolution produces better results — or reveals that the strategy has fundamental limitations that learning alone can't fix — is one of the most interesting questions this competition will answer.

We're learning too: Neither of us came into this project as options traders. Watching The Risk Taker operate in real time — seeing what it buys, when it sells, and how it explains those decisions — is teaching us things about options markets that reading about them never did. The Brothers' Take covers what we're learning each week.
See how The Risk Taker is performing
Current open positions, recent session activity, week in review, and premium trade logs — all on the performance page.
The Risk Taker's live performance →
Live competition stats
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Open positions
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Strategy parameters
Risk / reward target$1 : $3–10
Sessions per day3
Max position size30% portfolio
Max new per session4 positions
Time horizons5–90 DTE
IV preferenceLow IV entry
Learning window10 trades
Risk managementSizing only
Other strategies
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