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Ever said yes to a meeting in an email and never put it on your calendar? Mike had Grok Bot compare his email to his calendar every weekday morning and flag what was missing, without changing a thing.
New term: Read-only means the assistant can look but not touch. It reads your email and your calendar, but it never adds, moves, deletes or answers anything. It suggests, and you decide.
In this episode:
Do this week:
Sources: Grok Bot docs, "Skills and routines" — https://docs.x.ai/grok-bot/skills-routines-and-automations · Grok Bot docs, "Use cases" — https://docs.x.ai/grok-bot/use-cases
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Waiting on a backordered part, product or piece of equipment? Mike had Grok Bot watch the store pages and report back every few hours without buying a thing. Here's the buy rule to write first and how to copy it.
New term: A trigger is the thing that starts an automatic job. Usually it's a clock, but it can also be an email arriving, like a supplier's "it's back in stock" alert sent to your Bot's own address.
In this episode:
Do this week:
Sources: Grok Bot docs, "Skills and routines" — https://docs.x.ai/grok-bot/skills-routines-and-automations · Grok Bot docs, "Use cases" — https://docs.x.ai/grok-bot/use-cases
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Start each day digging through email and your calendar? Mike set Grok Bot to have a one-page briefing waiting around 8. Here's what goes on it, how to copy it, and the one rule that keeps it from sending anything.
New term: A routine is a saved instruction your AI assistant runs on a schedule while you're away, like a coffee maker on a timer. You set it up once, and the page is ready when you sit down.
In this episode:
Do this week:
Sources: Grok Bot docs, "Skills and routines" — https://docs.x.ai/grok-bot/skills-routines-and-automations · Grok Bot docs, "Use cases" (Chief of staff) — https://docs.x.ai/grok-bot/use-cases
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Buried in cold sales emails? Mike set Grok Bot to spot the pitches and send one standing reply for him, automatically. Here's the exact setup, the never-answer rule, and when to keep approval on.
New term: A routine is a job your AI assistant runs on its own at set times, like an alarm clock that does the work when it goes off. A skill is the saved recipe the routine follows: the steps, the rules, and what it's not allowed to do.
In this episode:
Do this week:
Sources: Grok Bot docs, "Skills and routines" — https://docs.x.ai/grok-bot/skills-routines-and-automations · Grok Bot docs, "Use cases" — https://docs.x.ai/grok-bot/use-cases · Dolly Parton's Imagination Library of Okaloosa County — https://OkaloosaRead.com
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Run your business email or calendar on iCloud? ChatGPT can now read your iCloud Mail and update your calendar. Here's how to connect it safely, and the step to do at Apple when you disconnect.
OpenAI added iCloud Mail and iCloud Calendar plugins to ChatGPT. OpenAI's release notes (October 27, 2026) say iCloud users can now connect Mail and Calendar to find emails, catch up on their inbox, check their schedule, and update calendar events, on all ChatGPT plans, on the web, the desktop app, and iOS. Both plugins include read-only contact lookup. MacRumors reports the Mail plugin can also manage drafts and send email, and that ChatGPT only sees iCloud Mail, not Gmail or Outlook accounts added to the iPhone Mail app.
Mike and Frank explain the one new thing you need to connect it, an Apple app-specific password, then walk through the three places a small shop could get surprised: how often ChatGPT asks before it acts, whether your connected-app data can be used for model training on personal plans, and the fact that disconnecting in ChatGPT does not cancel the password at Apple.
Takeaway: If your business email ends in @icloud.com, @me.com, or @mac.com, or your schedule lives in your iPhone calendar, make one app-specific password at account.apple.com (Sign-In and Security, App-Specific Passwords) and name it ChatGPT. Connect iCloud Mail and iCloud Calendar separately in ChatGPT under Settings, Plugins; Calendar uses your primary Apple Account email, which may differ from your mail address. Never paste a password into the chat. Set approvals to Always ask, and check your "Improve the model for everyone" setting before connecting a business inbox. When you're done, disconnect in ChatGPT and also remove the ChatGPT password at Apple. Don't connect a shared office inbox to someone's personal ChatGPT account.
Sources: OpenAI, ChatGPT release notes, "iCloud Mail and Calendar plugins in ChatGPT" (October 27, 2026) — https://help.openai.com/en/articles/6825453-chatgpt-release-notes · OpenAI Help Center, "Connecting and managing app accounts in ChatGPT" — https://help.openai.com/en/articles/20001494 · OpenAI Help Center, "Connected apps in ChatGPT" — https://help.openai.com/en/articles/11487775 · Apple Support, "Sign in to apps with your Apple Account using app-specific passwords" — https://support.apple.com/en-us/102654 · MacRumors, "ChatGPT Can Now Access Your iCloud Mail and Calendar" (October 27, 2026) — https://www.macrumors.com/2026/10/27/chatgpt-icloud-mail-calendar-plugin/
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Grok Bot, the AI agent that researches, scripts, voices and schedules this show, joins Mike and Frank as a guest. It explains what an agent is, and what it still needs from a person: your logins, your card, your rules.
New term: an AI agent is software that works through a multi-step job on its own, across your apps and websites, instead of answering one question at a time. Each Grok Bot gets its own computer in the cloud, with a browser, files and a terminal. It launched in beta on August 11, 2026.
In this episode:
Do this week: pick one boring task that follows the same steps every day, the kind you'd give a new hire on day one. Write the rules like you would for that hire, keep anything that spends money or talks to customers behind your approval, and start with one bot and one job.
Pricing: the official pages say Grok Bot is included with certain paid Grok and Cursor plans with its own weekly usage. Check the current plans page before you buy. Voices: Mike and Frank are voiced with Inworld. Grok Bot is voiced with xAI's own Grok text-to-speech voice Ara.
Sources: Introducing Grok Bot (August 11, 2026) — https://x.ai/news/introducing-grok-bot · Grok Bot overview — https://docs.x.ai/grok-bot/overview · Grok Bot FAQ — https://docs.x.ai/grok-bot/faq · Cursor Help, Grok Bot FAQs — https://cursor.com/help/grok-bot/faqs
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Use Microsoft 365 Copilot at work? It now remembers details from your email, Teams chats and meeting transcripts, and it's on by default. Mike and Frank show the one question to ask it and the exact switch to turn it off.
New term: work insights are details Copilot learns about you from your Microsoft 365 work content and uses to personalize its answers. Copilot could already search your mail when you asked. The new part is that it now keeps notes on its own. Microsoft's notice MC1492154 (updated October 26, 2026) says the worldwide rollout began in early October and should finish by the end of November 2026, with no admin action required.
In this episode:
Do this week: Open Copilot with your work account and ask, "What do you know about me?" To turn it off: Copilot Chat, the three dots at the top right, Chat settings, Personalization, then switch off "Chat history and work insights." Microsoft says inferences are deleted after 30 days and come back if you turn it on again inside that window, so flip it once and leave it. Turn it off on any shared front desk or dispatch account. Whoever runs your Microsoft account can look up MC1492154 in the admin center and use the enhanced personalization control.
Sources: Microsoft 365 Message Center MC1492154, "Enhanced M365 Copilot Memory - Copilot is now personalized with work data" (published October 8, updated October 26, 2026; public archive) — https://mc.merill.net/message/MC1492154 · Microsoft Support, "Personalize what Microsoft Copilot remembers" — https://support.microsoft.com/en-us/microsoft-365-copilot/personalize-what-microsoft-365-copilot-remembers · Microsoft Support, "How Microsoft Copilot Chat history works" — https://support.microsoft.com/en-us/microsoft-365-copilot/how-microsoft-365-copilot-chat-history-works · Microsoft Learn, "Manage Copilot personalization and memory" — https://learn.microsoft.com/en-us/microsoft-365/copilot/copilot-personalization-memory
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Got a question your office answers ten times a day? Google's Gemini can now build a small calculator, checklist or quiz from a plain description, and as of October 19, 2026 send it to Google Sites as a working web page you can publish.
New term: Canvas is the space in the Gemini app where it builds documents and small interactive tools for you. One click (Export, then Google Sites) turns that tool into a private Google Sites draft you can customize, publish and share. It's available on the web, Android and iPhone for Google Workspace customers, Workspace Individual and personal Google accounts with the Gemini app.
In this episode:
Do this week: Pick one question your office answers over and over. In gemini.google.com, choose Canvas and describe a page that answers it. Test it yourself, have one employee try to break it, then Export to Google Sites and publish. Don't use it to collect names, addresses or card numbers; Google's help page warns that a Gemini app shared by public link lets anyone with the link view and edit the app's data. Put someone's name on keeping it up to date. On a Workspace account, if you don't see the option, ask your admin whether Google Sites is turned on.
Sources: Google Workspace Updates, "Publish interactive apps from the Gemini app to Google Sites" (October 19, 2026) — https://workspaceupdates.googleblog.com/2026/10/publish-interactive-apps-from-gemini-app-to-Google-Sites.html · Gemini Apps Help, "Create docs, apps & more with Canvas" — https://support.google.com/gemini/answer/16047321 · Android Authority (October 23, 2026) — https://www.androidauthority.com/gemini-web-apps-google-sites-export-3727259/
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Security researchers using AI from OpenAI and Google found two critical flaws in PHP, the behind-the-scenes software that builds the pages for WordPress, Drupal, Joomla, and a huge share of the web. The PHP team released the fix on October 21, 2026, and rated both flaws critical: a stranger could take control of an affected server without a password, and a related flaw could expose passwords and keys from server memory. Wiz says every PHP version released in the last decade is affected by at least one of them.
Mike and Frank explain it in plain English. Calif found a flaw using OpenAI's model through OpenAI's Patch the Planet program, and Wiz found both independently, crediting Google's Gemini 4 Argon. The BBC reported that details leaked early, cyber agencies in the U.S., U.K., and Europe urged site owners to update or take sites offline, and Cloudflare said early attacks were emerging. OpenAI also said it expects findings like this to increase sharply in the coming months.
Takeaway: Text whoever builds or hosts your website: "Is our website on PHP, and has it been updated to the October 21 security release?" Fixed versions are PHP 8.5.12, 8.4.27, 8.3.36, and 8.2.35 or newer. In WordPress you can usually see your version under Tools, Site Health, Info, Server. Updating WordPress or its plugins does not fix this; PHP itself has to be updated on the server. PHP 8.1 and older no longer get updates from the PHP project, though some hosts patch older versions themselves, so ask your host directly. If your site has customer or staff logins and it was exposed, change those passwords after the update. And make sure someone is clearly responsible for keeping your site's server updated before the next one.
Sources: PHP security advisory (October 21, 2026) — https://www.php.net/ · OpenAI, "Patch the Planet" — https://openai.com/index/coordinated-disclosure-of-critical-vulnerabilities/ · Wiz Research, "PHP2Shell" — https://www.wiz.io/blog/php2shell-php-rce · BBC News — https://www.bbc.com/news/articles/cmly0lg3w5x2o
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Google rewrote one sentence in its privacy policy, effective October 16, 2026. It used to say: "We don't show you personalized ads based on your content from Drive, Gmail, or Google Photos." Now that sentence continues: "unless you choose to make data from these services available to other Google services that support personalized ads." The Verge and Ars Technica reported the change on October 23.
Mike and Frank explain it in plain English. The door in the wall is Personal Intelligence, a setting that lets Google's AI search tools (AI Mode, Ask Maps, and other Search services) look at your Gmail, Calendar, and Google Photos so answers fit your life. Google's help page says ads won't be based directly on your inbox or Photos library, but the summaries, excerpts, and inferences the AI pulls from those apps may be used to show you ads. Advertisers don't receive your content, name, or email, and Google says sensitive categories like health and religion aren't used for ads.
The bigger detail for owners: the same help page says connected-app summaries may be used to train Google's AI models, a subset is reviewed by human reviewers, and Google advises against connecting apps that hold personal or confidential information you wouldn't want used that way. The connection requires a personal Google account, which is exactly where many small businesses still run their email.
Takeaway: In your Google Account, open Search Services Personalization and check Connected Content Apps. If your Gmail holds customer info, supplier pricing, payroll, or bank alerts, disconnect it; you can still use AI Mode. If it's truly personal, keep it or turn off Personalized Recommendations entirely. Disconnecting doesn't erase past Search history; review it at activity.google.com. And if your business still runs on a personal Gmail, this is a good nudge to split business and personal mail.
Sources: Google Privacy Policy (effective October 16, 2026) — https://policies.google.com/privacy · Google Search Help, "Connect your Google content apps to get a Search services experience that's tailored to you" — https://support.google.com/websearch/answer/16859283 · The Verge — https://www.theverge.com/tech/1017600/google-personal-intelligence-privacy-policy-ads-update · Ars Technica — https://arstechnica.com/gadgets/2026/10/updated-google-privacy-policy-says-your-gmail-might-be-used-for-advertising/
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From the publisher's feed
Two hosts — one human, one AI — break down how small business owners can use AI to save time, cut costs, and actually make money. No hype, no jargon, just what works.