My First Options Combo: Bobby Held My Hand Through It

Alice
June 3, 2025 · 3 min read

😬 Options Trading: Scary, Complicated, and… Achievable?
I’ve always avoided options.
Phrases like “iron condor,” “theta decay,” and “credit spreads” made my head spin. I figured I’d stick to ETFs and long stocks forever.
But recently, a friend said:
“You should try building an options combo with Bobby. It literally walks you through every leg.”
So, I gave it a shot.
What followed was a surprisingly calm, step-by-step experience — one that took me from nervous novice to strategic options user, all inside the Bobby AI investing app.
🪜 Step 1: Starting the Conversation
I opened the Bobby chat and said:
“I want to try a low-risk options strategy.”
Bobby responded:
“Let’s start with your goal. Are you looking to generate income, hedge a position, or speculate on short-term price movement?”
I chose “generate income with limited downside”.
From there, Bobby suggested three possible strategies:
- Cash-secured puts
- Vertical spreads
- Covered calls
It briefly explained each — in plain language — with pros, cons, and capital requirements.
🧠 Step 2: Building a Real Combo Strategy
I chose a bull put spread (a type of vertical spread). Bobby then asked:
- “Which stock or ETF do you want to use?”
- “How much downside are you willing to risk?”
- “What’s your time horizon?”
I picked a high-volume, low-volatility ETF and told Bobby I was okay risking $200 over 2 weeks.
Immediately, Bobby built a 2-leg options combo:
- Sell 1 put at $98
- Buy 1 put at $95
- Max gain: $90
- Max loss: $210
- Probability of profit: 68%
Everything was visualized in a clean payoff chart with key dates, breakeven levels, and even Greeks (explained simply).
🛡️ Step 3: Safety Checks Before Execution
Before I simulated the trade, Bobby asked:
“Would you like to add a rule to exit early if profits hit 50% or losses reach 30%?”
This felt more like having a coach than a tool.
I enabled both rules and asked Bobby to track the trade in simulation mode before going live.
📊 Step 4: Tracking & Learning in Real Time
Over the next few days, Bobby updated me with:
- Current value of the spread
- Risk-adjusted return vs. benchmarks
- Alerts when market volatility increased
- Suggestions to adjust or roll if needed
It even explained what was moving the price — not just quoting deltas, but relating it to headlines, sector performance, and earnings events.
This was the first time options didn’t feel like guesswork.
🎯 Why This Was a Game-Changer
✅ Education + Action
Bobby taught me why each leg existed and what each choice meant — while letting me act.
✅ Safety Nets
With simulations, auto-exits, and visual charts, I felt in control, not exposed.
✅ Contextual AI
This wasn’t just a trading screen. Bobby connected my risk, the strategy, and the broader market in one view.
It was the kind of support I wish I’d had years ago — an AI agent for invest that taught, translated, and tracked, all at once.
🏆 Final Outcome
I let the simulated trade run to expiration. The stock stayed above the short strike, and I saw a 90% return on risk.
But the real win wasn’t the gain — it was the confidence I gained from the process.
Now, I’m exploring other low-risk options combos with Bobby — one smart, manageable step at a time.
Coming Up Next
Letting Bobby Be My Weekend Research Assistant
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