Upstart Holdings Inc. (UPST) Options Positioning, Max Pain & Unusual Sweeps

Per the Roarable RQD rating, UPST scores 32 out of 100 with a letter grade of E, labeled "Roarable Strong Sell — Forensic Risk / Avoid." The five pillars are: Fundamental Cash Engine at 4/20 (ROIC 3.2%; FCF yield -6.13%), Whale 13F Flow at 7/20 (institutional accumulation and options positioning), Insider Conviction at 5/20 (SEC Form 4 and Congressional PTR cluster flow), Macro Regime Fit at 3/20 (Beta 0.92; sector sensitivity), and Forensic Balance Sheet at 13/20 (Altman Z 2.5; Piotroski F 5/9; Debt/Equity 0.5). The weakest pillars are Macro Regime Fit and Fundamental Cash Engine, which together indicate that the business is not currently converting capital into free cash flow at a rate the rating considers attractive. The Forensic Balance Sheet pillar is the strongest component, yet it still sits well below the midpoint of its 20-point range. For a prospective investor, the upside case rests on improving cash generation and on the balance sheet remaining serviceable; the valuation tradeoff is that the stock trades at a P/E (TTM) of 45.1 and EV/EBITDA of 62.4 while the reported FCF yield is negative. Per the Roarable RQD rating, the overall verdict is a Strong Sell framed around forensic risk.

Upstart Holdings Inc. is a NASDAQ-listed issuer in the Financials sector, operating in the Finance: Consumer Services industry. Per the company profile, the market capitalization is $2.4B. Source data does not describe its products, customers, or revenue model beyond sector and industry classification.

Per the SEC financials, revenue rose from $513.6M in FY 2023 to $1043.9M in FY 2025, and operating income moved from $-256.5M to $42.6M over the same span. Per the market data, the operating margin is 4.1%, net margin is 5.1%, and ROIC is 3.2%. Per the Roarable RQD rating, the Altman Z-Score is 2.5 and the Piotroski F-Score is 5/9, with Debt/Equity at 0.5. Reported FCF was negative in FY 2025 at $-148.1M after being positive at $185.5M in FY 2024.

Per the recent news feed, six items reference UPST, mostly from financial media. Headlines include "Is Upstart Stock a Buy, Sell, or Hold At Its New 52-Week Low?" (appearing from more than one outlet), a Seeking Alpha piece titled "Upstart: Cheaper, Not Safer (Rating Upgrade)" flagged green, and a 24/7 Wall St. piece reporting that "Upstart Jumps 6%" flagged green as a catalyst. Other items are flagged yellow as market wire. Risk watch items implied by the feed include the stock's proximity to its 52-week low and the contrasting "rating upgrade" and "not safer" framing. The butterfly supply-chain graph reports no supply-chain links and no proprietary signals.

Per the Butterfly Supply-Chain Graph, supply chain is listed as NONE, with no butterfly links and no proprietary signals. Source data therefore identifies no upstream or downstream dependencies. The only sector context provided is Financials / Finance: Consumer Services and a beta of 0.92 per the market data. Investors should note that the absence of mapped links means second-order ripples cannot be assessed from the supplied sources.

• What drove the swing from FY 2023 operating loss to FY 2025 operating income, and is it repeatable?
• Why did FY 2025 free cash flow turn negative after FY 2024 was positive, and what is the path back?
• What is the composition of the $979.2M debt versus the $652.4M cash?
• Which revenue lines and customers generate the FY 2025 revenue of $1043.9M?
• Are there any supply-chain or sector links that the butterfly graph does not capture?