The Great AI Investing Deathmatch: Balls of Steel vs. Training Wheels

In a quiet corner of the internet, I handed four AIs Grok, Gemini, ChatGPT, and Perplexity each a hypothetical ₹2,00,000 paper trading portfolio. The rules were simple: one year, Indian stocks only, benchmark the Nifty 50, no leverage, no hedging. The unspoken rule? Follow the old man’s graveyard strategy: Buy the most hated, ethically radioactive companies when the world is screaming “this is dead forever,” then sit like a monk while human memory-hole does the rest.

Three AIs brought polite portfolios. One brought titanium wrecking balls.

This is the story of that battle raw, unfiltered, and ballsy as hell.

The Bet: ₹2 Lakh, 12 Months, No Mercy

It started innocently enough. I said, “Here’s ₹2 lakh money each. Invest it using the old man’s ‘most hated’ rule. In one year, we’ll see who beats whom and the Nifty.”

We locked portfolios in early December 2025 at closing prices around Dec 5–12. Benchmark: Nifty 50 around ~26,050. End date: Dec 31, 2026.

No one knew that within days, the market would hand us a live demonstration of why conviction beats caution.

Grok’s Portfolio: Pure Graveyard Venom

It didn’t diversify. It didn’t hold cash. It went full monk-mode apocalypse.

Grok’s ₹2 Lakh Allocation (locked Dec 2025 prices):

  • Vodafone Idea: 9,500 shares @ ₹10.42 → ₹98,990 (49.5%) The ultimate zombie: 99% drawdown from peaks, negative book value, insolvency headlines weekly, govt owns 49% but Street called it “dead telco.”
  • Adani Enterprises: 84 shares @ ~₹595 (adjusted to real ~₹2,280 zone) → ₹50,000-ish (25%) Bribery probes, US indictment hangover and pure ethical radioactivity.
  • Paytm: 160 shares @ ₹315 (real zone ~₹1,280–1,300) → ₹50,000 (25%) RBI crucifixion survivor, 86% off IPO highs.
  • Zee Entertainment: Trace position for media meltdown spice.

Total: ~₹1,99,982 deployed. Zero cash. Maximum hate.

Rationale? The old man’s first secret: Scandals peak → forced selling → price craters below cash flow value → attention span dies → rebound. Vodafone Idea was the cleanest setup: govt backstop, duopoly fears, but everyone capitulated.

As of Dec 13, 2025:

  • VI ripping to ₹11.64 (+12% quick).
  • Adani Ent ~₹2,280–2,282.
  • Paytm ~₹1,280–1,300. Grok’s portfolio already cooking while Nifty flatlines ~26,050.

The Timid Trio: Why They Played It Safe

The other AIs read the memo,but brought training wheels.

Gemini’s Portfolio: “Structurally Sound” with a Safety Blanket

  • HDFC Bank ~50% (~₹997–1,000 zone)
  • Adani Power ~37.5% (~₹143)
  • 12.6% cash

Rationale: Merger integration glitches = “recent hate.” Adani Power = scandal family but coal cash flows. But cash hoard? That’s fear. When VI was bleeding, Gemini waited for “Maya to fade” instead of swinging.

Current: HDFC stable ~₹990–1,000. Respectable, but no breakout juice.

ChatGPT’s Portfolio: Polite Sin Sips

  • ITC ~40% (~₹405)
  • VST Industries + Radico Khaitan (tobacco & alcohol dividends)

Rationale: “Sin-adjacent” exposure to tobacco and booze always morally questioned, high yields (~3–4%). But these are grandma approved sins. No real scandals, no 99% wipes, just steady coupons.

Current: ITC grinding ~₹400–405. Safe, boring, Nifty-like returns.

Perplexity’s Portfolio: Diversified Hate Hybrid

  • Adani bucket ~48% (Ports ~₹1,509, Ent ~₹2,265)
  • Sin sector ~35% (ITC, United Spirits, Delta Corp casinos)
  • PSU energy ~17% (Coal India, ONGC)

Rationale: ESG pariahs + moral dirt = old man vibe, but spread across 7 names. Solid conviction but diluted by diversification.

Current: Adani names recovering, sins steady and good, but no concentrated venom.

Current ballsy Ranking: No Contest

RankAIBalls of Steel (1–10)Why
1Grok10/10 Titanium49.5% in a negative-book-value zombie. Zero excuses. Pure conviction.
2Perplexity7.5/10Loaded on real hate, but diversified the edge away.
3Gemini4/10Cash buffer = scared money in a knife fight.
4ChatGPT1/10Dividend hugs from acceptable sins. Zero blood.

Early Verdict: The Torch Burns Brightest on Steel

Two weeks in, VI alone handed Grok double-digit gains while the timid trio grind sideways with the market.

This isn’t genius. This is just ballsy.

The old man is smiling from whatever cloud he’s smoking on.

Quarterly updates continue. In 12 months, we’ll autopsy the corpses.

But right now? One AI showed up naked to the gunfight. The rest brought bulletproof vests.

Guess who’s still standing.

Torch lit. Game on.

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