Man and Machine Ep. 237: A Strong May in Review, Gatekeeper Launches, and a Ross Stores Dividend Play

A big May in review — King AI, King Condor, and King AI Turbo iron condors put up standout numbers, and Gatekeeper heads out of beta. Then a deep dive on Ross Stores (ROST) leads to a clever dividend-capture trade idea. Plus why PeakBot's skipping Robinhood.

June opens with a victory lap. In episode 237 of Man and Machine — part of The Pulse on the Tradier Hub — Dillon and Ben close the book on a strong May for the PeakBot bots, welcome a new strategy out of beta, and turn a look at a discount-retail stock into one of the more creative trade ideas they’ve floated in a while.

First, a quick bit of housekeeping that’s worth noting for anyone automating elsewhere: when a viewer asks whether PeakBot will integrate with Robinhood, the answer is a clean no — Robinhood doesn’t offer an open API, so third-party automation there is a question mark. The moment that changes, they’re in. For now, they point to Tradier as the best home for automated options trading on fees alone, and they contrast the “build your own bot” tools popping up at other brokers with PeakBot’s model of automating proven, partner-run strategies.

The stock in real life is Ross Stores (ROST), and it turns into a genuine “judged a book by its cover” moment. Public since August 1985 at $17 a share, Ross now carries a market cap around $75 billion, runs roughly 2,270 locations between Ross Dress for Less and its DD’s Discounts chain, and has ripped from about $140 to $231 over the past year — a ~60% run, even through a volatile stretch. Set against TJX (which owns TJ Maxx and Marshalls at a ~$171 billion cap), it’s a reminder of how much money sits in off-price retail. Both pay steady quarterly dividends.

That dividend is where the episode earns its Maverick streak. With Ross’s ex-dividend date about eight days out and a payout at the end of the month, the guys improvise a dividend-capture structure on the fly: sell an in-the-money cash-secured put to get assigned the shares, sell a call at the same strike so those shares can be called away at that price, and collect premium from both contracts plus the dividend — aiming to break even on the stock itself. It’s the kind of one-off, opportunistic idea no bot would ever flag, and they’re clear it’s cash-intensive and not financial advice.

Then comes the heart of the episode: the May scorecard for the automated strategies, all 1DTE iron condors on SPX unless noted. King AI took 11 trades for about $700 per unit with a single loss, and it’s up roughly $3,480 since launch. King Condor — the more aggressive 20-delta member with a built-in stop — won 60% of its May trades for about $830 per unit. King AI Turbo, the most aggressive of the family, put up around $1,710 per unit at an 85% win rate and sits north of 250% cash-on-cash since its November launch. Gatekeeper, the momentum bot that can hold up to seven positions at once, had a flat-to-red May as it came out of beta, and Shorebo, the zero-DTE opening range breakout, added about $250 with new updates on the way. For fun, they tally what maxing every bot on a $199 subscription would have returned — roughly $6,600, about a 34x return on the subscription — plus a wheel trade on TQQQ that netted around $412.

They close with the week’s calendar, flagging Friday’s non-farm payrolls as the event that shuts the fixed-logic condors off, while the AI bots decide for themselves.

 



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