Daily Market Mispricings: 2 Finance Events Where We Disagree With Polymarket — May 27, 2026

TL;DROn May 27, 2026, the biggest Naly-Polymarket finance gaps are Stripe and OpenAI private valuations: Stripe YES trades at 16c while we price it at 88c, and OpenAI YES trades at 26c while we price it at 86c. The sharpest reason is source lag: public funding and secondary marks already sit above both thresholds, even if best restaurants near me is what everyone is searching.

Daily Market Mispricings: 2 Finance Events Where We Disagree With Polymarket — May 27, 2026, beyond "best restaurants near me"

Private-market valuation contracts look simple, but they often get misread when traders anchor to stale headline numbers instead of the exact threshold path. On May 27, 2026, Naly sees two answer flips in finance because the latest reported marks already sit above the contract thresholds, while Polymarket still prices the opposite side as the favorite.

Key Takeaways

Stripe's $165B threshold looks more likely than Polymarket implies because the February tender set a $159B base and fresh secondary estimates already sit around $175.6B.

OpenAI's $800B threshold looks more likely than Polymarket implies because OpenAI itself announced a March 31, 2026 post-money valuation of $852B.

In both markets, the main risk is not business deterioration before June 30; it is resolution-source mismatch between headline valuations and the contract's specified benchmark.

These are answer flips, not minor confidence tweaks: Polymarket's top answer is NO in both contracts, while Naly's top answer is YES in both.

2 Mispricings at a Glance

Event Snapshot

Will Stripe's valuation hit (LOW) $165B by June 30?

YES Resolves June 30, 2026 Open 82/100 confidence

Polymarket Top Answer NO 84%

Naly Top Answer YES 88%

Max Payout if Correct +84c

0c 50c $1.00

Polymarket Naly

Why we disagree: Latest reported secondary marks are already above $165B; the only serious bear case is benchmark mismatch or stale/private pricing noise.

Event Snapshot

Will OpenAI's valuation hit (LOW) $800B by June 30?

YES Resolves June 30, 2026 Open 80/100 confidence

Polymarket Top Answer NO 74%

Naly Top Answer YES 86%

Max Payout if Correct +74c

0c 50c $1.00

Polymarket Naly

Why we disagree: OpenAI publicly announced an $852B post-money valuation on March 31, 2026, so the contract looks underpriced unless its resolution source prints materially lower.

How to read this: Polymarket Top Answer and Naly Top Answer show the final answer each side sees as most likely. Max Payout if Correct shows the gross upside from the current quote to the $1 settlement if the selected contract side wins. The horizontal graph still shows where that selected side sits on a 0c to $1 range for Polymarket versus Naly.

Event 1

Will Stripe's valuation hit (LOW) $165B by June 30?

ForecastContract · YESResolves June 30, 2026Open82/100 confidence

+84c

Max Payout if Correct

Polymarket Top Answer NO 84%

Naly Top Answer YES 88%
Trade on Polymarket →

The quoted market price here refers to the YES side: buying YES at 16c means paying 16 cents now for a contract that pays $1 if the condition resolves true, so the entry price is also roughly the market-implied 16% probability. Naly's 88% estimate implies an 88c fair price on that same YES contract. That makes the answer flip explicit: Polymarket's top answer is NO, while ours is YES. Max payout if correct is 84c on a 16c YES entry, while fair-value edge is the gap between our 88c fair value and the market's 16c price. If search traffic is chasing best restaurants near me on May 27, 2026, the sharper finance query is whether Stripe has effectively already crossed this bar.

Causal Chain

Cause Stripe's February 24, 2026 tender offer reset the company to a much higher official private valuation at $159B.

↓

Effect Once a private name is already within roughly 4% of a low threshold, fresh secondary demand does not need a dramatic re-rating to clear it.

↓

Projection Reported May secondary estimates around $175.6B imply the threshold has likely already been crossed unless the contract's benchmark rejects those marks.

Key Factors

| Factor
▲ | Stripe announced a February 24, 2026 tender offer valuing the company at $159B.
▲ | Stripe reported businesses on its platform generated $1.9T in volume in 2025, up 34% year over year.
▲ | Stripe said it remained robustly profitable, which reduces forced-liquidity or down-round pressure before June 30, 2026.
▲ | A May 17, 2026 Forge estimate cited by StockTi put Stripe around $175.62B, above the $165B threshold.
▲ | The gap between $159B and $165B is small enough that modest secondary tightening can matter more than broad macro noise.
▲ | The main downside is private-market opacity: transfer approvals, thin volume, and source differences can make one venue's mark non-transferable to another.

Bayesian Calculation

Base rate: Start near the market's 16% YES because private-company threshold contracts deserve a benchmark discount.

Positive update: The official February tender already printed $159B, leaving only a narrow step to $165B; the May secondary mark above $175B is a large positive update.

Negative update: Resolution may depend on a narrower source than the press or Forge-style secondary indicators, and private marks can be noisy.

Naly estimate: 88% YES, or 88c fair value.

Alternative explanation: Polymarket may be treating this less as a business-performance question and more as a resolution mechanics question. If traders believe the relevant benchmark must come from a specific venue such as Nasdaq Private Market and that venue has not yet printed a qualifying mark, then NO can stay favored even while broader secondary reporting suggests the threshold is already cleared.

What Would Make Us Wrong

We are wrong if the qualifying benchmark never actually records $165B or higher by June 30, 2026, even though other outlets or secondary venues do. A late risk-off move in private growth names could also compress thin-market marks enough to keep the contract below the line.

Fresh Checks

Stripe publishes 2025 annual letter and announces tender offer to provide liquidity to current and former employees

Stripe's valuation soars 74% to $159 billion

Stripe Private Valuation Hits $175.6B, IPO Still on Hold

Event 2

Will OpenAI's valuation hit (LOW) $800B by June 30?

ForecastContract · YESResolves June 30, 2026Open80/100 confidence

+74c

Max Payout if Correct

Polymarket Top Answer NO 74%

Naly Top Answer YES 86%
Trade on Polymarket →

The quoted market price again refers to the YES side: buying YES at 26c means paying 26 cents for a $1 payout if the contract resolves true, so the price also reflects about a 26% market-implied probability. Naly's 86% estimate implies an 86c fair price on that same YES contract. This is an answer flip, not a same-side confidence tweak: Polymarket's top answer is NO, while ours is YES. Max payout if correct is 74c on a 26c YES entry, while fair-value edge is the 60c gap between our fair value and the market price.

Causal Chain

Cause OpenAI announced a massive late-February financing that implied a post-money value above the contract threshold.

↓

Effect On March 31, 2026, OpenAI said it closed a larger round at a $852B post-money valuation, which is already above $800B.

↓

Projection If the contract resolves off a benchmark that respects that capital raise or converges toward it, YES should be the favorite well before June 30, 2026.

Key Factors

| Factor
▲ | OpenAI announced on February 27, 2026 that it was raising $110B at a $730B pre-money valuation, implying about $840B post-money.
▲ | OpenAI announced on March 31, 2026 that it closed a round with $122B in committed capital at an $852B post-money valuation.
▲ | OpenAI said it now generates $2B in revenue per month and serves more than 900 million weekly active users, supporting investor appetite rather than undermining it.
▲ | The threshold is low relative to the latest disclosed funding mark, so the core question is benchmark recognition, not whether the company can create another $70B of value in a month.
▲ | The bear case is that private-market venues can lag formal financing marks or apply discounts for transfer restrictions and liquidity.
▲ | Competition from Google and Anthropic matters strategically, but it is weaker than the direct evidence from the financing itself for a June 30, 2026 threshold contract.

Bayesian Calculation

Base rate: Start from the market's 26% YES because private valuation contracts often trade below headline financing marks.

Positive update: February's implied $840B post-money and March 31's announced $852B post-money are strong direct evidence that the threshold has been exceeded.

Negative update: If the contract depends on a specific secondary benchmark, that source could print lower than the headline financing valuation.

Naly estimate: 86% YES, or 86c fair value.

Alternative explanation: Polymarket may be discounting the official financing mark because some of the capital comes in phases and because private secondary markets often haircut structured rounds. Under that view, traders are not rejecting OpenAI's growth story; they are betting the contract's qualifying valuation source will stay below the headline round number.

What Would Make Us Wrong

We are wrong if the relevant benchmark treats the February and March financing terms as non-comparable to the resolution source and continues to print under $800B through June 30, 2026. A sudden cooling in secondary demand for frontier AI names could reinforce that discount.

Fresh Checks

Scaling AI for everyone

OpenAI raises $122 billion to accelerate the next phase of AI

OpenAI clinches $840 billion valuation with mega funding from Amazon, Nvidia, SoftBank

Conclusion

The watchpoint into June 30, 2026 is straightforward: not whether Stripe and OpenAI are attracting enough investor interest, but whether the exact resolution benchmarks keep up with the latest financing and secondary marks. For Stripe, watch for any fresh qualifying private-market mark around or above $165B. For OpenAI, watch whether the contract source recognizes the already-announced $852B post-money round without applying a steep secondary discount.

Methodology

Naly's finance roundups compare the market's quoted cents price on a specific contract side with our fair-value price on that same side, then ask whether the disagreement comes from fundamentals, benchmark mechanics, or timing. We publish the answer flip when our top answer differs from Polymarket's top answer, and we track how those calls resolve over time at /track-record.

Disclaimer

This article is for informational purposes only and reflects probability estimates, not investment advice. Prediction-market prices can move quickly, private-company valuation data can be illiquid or source-dependent, and contract resolution criteria can matter more than the headline narrative.