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ROOT · Root Inc. $49.14 -1.65 (-3.25%) 2026-SEP-18 12:43 EST

My allocationNot heldas of 2026-SEP-03 · allocation page ↗
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2026-JUL-16 · John Polomny · Discord post (AIA community) · Positiveinsight · read ↗ · source page ↗$55.87

In short: Wrote some cash-covered puts on ROOT. The stock has bottomed and has been in an uptrend. Increasingly interested in companies that collect large amounts of data and use machine learning to improve their business outcomes — ROOT appears to be doing this in car insurance.

In plain English

Root is a car-insurance company that prices policies using data about how you actually drive — collected from your phone/car — and machine-learning models, instead of relying only on broad categories like age and ZIP code. The idea is a flywheel: more drivers → more driving data → sharper models → more accurate pricing → better results → more drivers. Polomny likes businesses built on exactly that data-and-machine-learning loop, and thinks Root is doing it in auto insurance.

Rather than just buying the stock, he "wrote cash-covered puts." Selling a put means he gets paid a premium today in exchange for a promise to buy the shares at a set lower price if they fall to it — and he sets aside the cash to honor that promise (that's the "cash-covered" part). If the stock keeps climbing, he simply keeps the premium as income; if it dips to his strike, he buys a name he already wanted, at a discount to today's price. He's comfortable doing this now because he reads the chart as having bottomed and turned into an uptrend.

SOD $55.87

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Verbatim excerpts from the public transcripts (auto-pulled at each mention's timestamp, lightly cleaned). Timestamps link into the video; "source page" opens that commentator's full analysis at this row. Click a mention's header line to expand it (one open at a time). For personal study — not investment advice.