My First Options Combo: Bobby Held My Hand Through It

😬 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