I Gave Bobby My Personality Type. It Gave Me a Portfolio
Alice
June 3, 2025 · 3 min read
🧠 Investing Meets Personality: A New Twist on Risk Profiles
Most investing tools ask:
“What’s your risk tolerance?”
But let’s face it — most of us don’t know. Risk is personal. It’s emotional. It’s tied to how we process decisions, handle stress, and define success.
That’s why I was intrigued when I saw a prompt in Bobby, RockFlow’s AI investing app, that said:
“Tell me your personality type — I’ll build you a matching portfolio.”
I typed in: “I’m an INFP.”
The result? A personalized AI Portfolio that matched not just my goals, but how I think.
💬 What Happened Next: The Personality Scan
Bobby didn’t just take my MBTI label at face value. It broke it down:
- Introverted → Tends to prefer fewer, more meaningful positions
- Intuitive → Likely drawn to big ideas (themes like AI, sustainability, future tech)
- Feeling-oriented → May favor mission-driven investments or value-aligned sectors
- Perceiving → More comfortable with flexibility, less likely to micromanage trades
Then it asked a few clarifying questions:
“Do you like to check your portfolio often?”
“Would you rather feel confident in themes or optimize for returns?”
“Are you emotionally impacted by short-term drops?”
These weren’t typical investing questions. They felt human.
🎯 The Result: A Portfolio Called “Innovative Dreamer”
After the short exchange, Bobby built an AI Portfolio with this breakdown:
- 40% thematic ETFs (AI, green tech, future mobility)
- 30% dividend-paying large caps (stability with soul)
- 20% international exposure to mission-driven firms
- 10% cash for optionality
Backtests showed the portfolio would’ve underperformed during bull runs, but outperformed during sharp corrections — a good emotional fit for someone like me.
🧪 Why This Works: Emotional Risk Profiling
Traditional financial risk tools focus on metrics like:
- Years to retirement
- Income bracket
- Historical investment experience
But what about:
- How you feel when a stock drops 5% overnight?
- Whether you trust numbers or narratives?
- Whether you need structure or space to explore?
This is where Bobby’s AI for invest engine shines. It turns abstract self-understanding into concrete allocation logic.
🔄 Strategy Flexibility
I could even adjust the portfolio tone. After testing, I asked:
“Make it a bit more aggressive.”
Bobby kept my themes but swapped 15% from large caps to mid-cap growth, then re-ran the backtests to show the impact on risk, return, and max drawdown.
It wasn’t just a theme-matching gimmick — it was quant trading merged with behavioral alignment.
📢 Publishing My Personality Portfolio
After a few days of simulation, I decided to share my strategy.
With a tap, I published it to Strategy Square — RockFlow’s portfolio-sharing platform — so other INFPs (or curious investors) could follow along.
Final Thoughts
We often separate money from emotion. But in reality, how we invest is deeply tied to who we are.
Bobby’s personality-based portfolio feature brought that to life — with logic, customization, and just enough insight to make me rethink how I define “risk.”
So whether you’re an INFP, an ENTJ, or just someone tired of generic advice, let Bobby speak your language.
Because in 2025, the best AI investing apps don’t just know the markets. They know you.
