Episode 150 - Published February 15, 2026 Michael and Damashe celebrate episode 150 with a technical troubleshooting session that turns into a masterclass on VoiceOver settings, Audio Hijack experimentation, and podcast marketing strategies. In This Episode: VoiceOver Menu Fix (Critical for Mac Users)

The solution to broken menu bar navigation in VoiceOver Why "Mouse pointer follows VoiceOver cursor" causes problems How to configure VoiceOver Utility settings properly When mouse tracking is useful vs. problematic

Audio Hijack Exploration

Real-time compression testing and audio processing Setting up test sessions to experiment with effects The difference between recording with effects vs. applying post-production Tips for session documentation and organization

Hardware Updates

Damashe's DJI Mic Mini purchase and setup ($80 with charging case) Insta360 Flow 2 Pro gimbal for iPhone video content Loupedeck controller for podcasting workflows Apple repair adventures with MacBook Pro and iPad Mini 6

Podcast Marketing Strategy

Using Claude AI to identify clip-worthy moments from transcripts Creating video shorts with AI-generated visuals Buffer integration for multi-platform scheduling Open Claw (ClaudBot) automation coming soon YouTube growth plans and content strategy

Shout Outs

Christopher Sims - Thank you for the Tip Jar support! All our Tip Jar subscribers - You make this show possible

Mentioned Resources

Audio Hijack by Rogue Amoeba DJI Mic Mini (2 transmitters + receiver + charging case) Insta360 Flow 2 Pro gimbal Buffer for social media scheduling VoiceOver Utility settings

Contact & Support Email: feedback@technicallyworking.show Mastodon:

Michael: @payown@dragonscave.space Damashe: @damashe@technically.social Bot: @TW@technically.social

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This week, Damashe considers canceling his Claude subscription... only to immediately sign up for a more expensive plan to hire Claude as his virtual assistant. Meanwhile, Michael tackles a Stream Deck accessibility project with help from Claude Code, and the guys make potentially dangerous plans to unleash OpenClaw on their Mastodon bot. Plus: RSS reader workflows, notification rage-quitting, Bitcoin regrets, and why good help really is hard to find (whether human or AI).

AI Assistants & Claude (2:00)

• Damashe's plan to use Claude as a $100/month virtual assistant
• The $50 API credit offer (expires February 16th!)
• Why AI hasn't taken jobs... yet
• Claude Code living in the terminal

Stream Deck Accessibility Project (15:00)

• Making Stream Deck usable for blind users on Windows and Mac
• The power of profiles and context-switching
• Integration possibilities with Bunches, shortcuts, and automation

RSS Readers & Workflows (6:00)

• Net News Wire, Liray, and the eternal search for the perfect feed reader
• Why preview mode matters
• The Verge's Twitter-on-their-website approach

OpenClaw Plans (1:07:00)

• Security concerns and Leo's removal
• The bot that got itself a phone number and called its owner
• Plans to unleash it on the @TW Mastodon bot
• Building a kill switch (before the bot reads this transcript)

Good Help is Hard to Find (30:00)

• Why reliable contractors are priceless
• The 90-day test for employees who think the job is easy
• Michael's subcontractor success story

Also Discussed

• Cash App notification rage-quitting
• Uber's marketing message problem
• Bitcoin: "I would have sold it at $2,000"
• Home Assistant Yellow module installation anxiety
• Raspberry Pi 5 (16GB) for sale!

• Follow the bot: @TW@technically.social (before OpenClaw takes over)
• Claude $50 credit: Redeem in settings before Feb 16th
• Harper's blog: Early Claude Code adopter mentioned on TWiT
• Net News Wire: Open source RSS reader
• PineCast referral: 50% off first 4 months (link in show notes)

• Total downloads: 29,312 (just 688 away from 30K!)
• Episode 148: 45 downloads
• Episode 147: 154 downloads
• Help us grow: Subscribe a friend!

• Email: feedback@technicallyworking.show
• Michael: @Payown@dragonscave.space
• Damashe: @Damashe@technically.social
• Use #TechnicallyWorking to join the conversation

Support the show at technicallyworking.show/tipjar

Episode 149 • Runtime: ~1:13:00

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This episode covers a wide range of real-world tech experiments, AI tools, and the line between helpful automation and “maybe don’t give that full access yet.”

We start with money talk (not advice). Damashe shares that he finally opened a Fidelity account and bought his first stock, while Michael talks about using watch lists and trade notifications. They also explore how accessible investing apps are getting, including audio charts and VoiceOver support, plus where accessibility still falls short.

Claude Bot and AI with real power A big chunk of the episode focuses on Claude Bot, an open-source tool that lets you interact with an AI through messaging apps like Signal, WhatsApp, and more. The idea of giving an AI access to your computer is exciting… and a little terrifying. This leads to the show’s unofficial safety rule:

> If an AI tool can take actions on your system, run it on a Raspberry Pi or other isolated setup first.

They break down risks like prompt injection, why connecting AI to email and calendars can be dangerous, and why curiosity should always be paired with caution.

AI for everyday life: meet Cookie On the more practical side, Michael shares a cooking app called Cookie. It reads recipes out loud, lets you ask questions like “What’s the next step?” and even suggests ingredient substitutions. It was not originally built for accessibility, but turned out to be incredibly useful for blind cooks. A great example of AI being used in a focused, practical way.

Smarter notes and personal workflows Damashe talks about using AI with DevonThink to automatically organize documents, and why he’s eyeing Drafts with new automation features. The goal: speak a quick note and have it turn into structured data, lists, or tasks without manual sorting.

Social apps, open source, and platform politics There’s also discussion about:

• A new accessible Mastodon and Bluesky client
• Mastodon instances blocking apps built with AI assistance
• The tradeoffs of open platforms where each server sets its own rules

Linux curiosity returns More blind tech users are experimenting with Linux on the desktop again. The hosts are curious what’s improved, especially with screen readers, and ask listeners to share their experiences.

And yes… Todoist check-ins They wrap with progress (and setbacks) on staying consistent with task tracking.

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This week starts nerdy and only gets nerdier in the best way. Michael and Damashe bounce from Apple rumors to AI customer service fails, with plenty of practical tech talk in between.

We dig into the rumors around Apple’s AI direction and what it might really mean for Siri, a possible Home hub device, and Apple’s partnership with Google’s AI models. Are we finally close to a version of Siri that feels truly useful? We share what we’re hopeful about and what still feels like vaporware.

From Perplexity to Amazon Q, we talk about the shift from “AI that tries to know everything” to smaller models trained for specific tasks. Why focused AI might actually be more helpful and less likely to make things up.

Michael has been setting up Amazon SES and got a firsthand look at Amazon’s built-in AI assistant, Q. We talk about how tools like this can make complex platforms like AWS more approachable, especially when you can ask follow-up questions in plain language instead of digging through documentation alone.

Michael walks through why he’s moving WordPress email over to Amazon SES. The big takeaway: sending email at scale can be shockingly inexpensive if you’re willing to do a little setup yourself. We also cover SPF records, sending domains, and a few beginner tips to avoid common mistakes.

From smart locks that won’t unlock to garage lights that randomly stop responding, we share real-world smart home frustrations. We also talk about Matter, Thread, hubs, and why the future of smart homes should mean fewer extra boxes and more reliable automations.

Damashe shares a frustrating experience with an AI phone system that slowed everything down instead of helping. We talk about what good AI customer service should look like and how companies are missing the point when bots just add extra steps.

Apple now has a Creator bundle subscription that includes Final Cut, Logic, and more across Mac and iPad. We break down who it might make sense for and when it’s probably cheaper to just buy what you need.

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Show notes (Technically Working, Episode 146) This week starts with a dramatic voice demo and turns into a practical conversation about TTS quality, accessibility, and the friction that slows down real work.

In this episode, we talk about:

• More expressive on-device voices (and why “emotion” in TTS can be impressive but unpredictable)
• Why some AI voices drift over long reads (like losing low end after a few thousand characters)
• The practical fix: chunking text around 3,000 characters at sentence or paragraph boundaries
• The jarring side of expressive TTS: when the tone suddenly shifts mid-training

• Mac code editor accessibility and workflow:

• VS Code feeling clunky with VoiceOver navigation

• Nova being close, but still having VoiceOver quirks (like wrapped-line re-reading)
• Missing the flexibility and simplicity of TextMate
• A quick audio reality check: room reverb, mic position, and loud breathing in the mic
• Why it’s worth listening back sometimes, even if you usually don’t
• “Personal intelligence” assistants: Gemini connecting deeper with Gmail, Calendar, Photos, and Drive, and what that could enable
• Stream Deck Plus on sale (knobs!) and the bigger question: is the software accessible enough?

• Capture friction and follow-up problems:

• Getting ideas out of your head fast

• Using automation to sort notes into reminders, drafts, and follow-ups
• Why the Apple Watch action button might help reduce steps
• PLAUD recording devices: improved hardware button design, but app accessibility still matters
• Local processing ideas: Raspberry Pi options for local transcription and LLM workflows
• Listener feedback: Squarespace questions and a quick look at support options (tip jar vs Buy Me a Coffee)

Feedback and contact: feedback@technicallyworking.show

Support the show: Visit technicallyworking.show and click “Support Us” to leave a one-time tip or set up a recurring amount.

Mastodon: @payown@dragonscave.space @damashe@technically.social @tw@technically.social

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Episode 145: Teaching Tech, Tethering Pain, and a Little CES Talk

This week we bounce between real life and real tech: why tethering still makes us want a MacBook with built-in cellular, what passkeys look like in the real world, and how Google Family Link pushes you into creating Gmail accounts for kids. We also talk honestly about teaching tech, why we often prefer working with people who are ready to level up their productivity, and how listener feedback shapes where the show goes next. Plus, a quick CES roundup with a few gadgets and ideas that actually stood out.

• Late-night work limits, and planning so tomorrow doesn’t get wrecked
• Tethering frustration, and the “just give us a MacBook with cellular” wish
• Michael’s living-room recording setup: Vocaster + OWC dock + Zoom, no virtual device chaos
• Google Workspace security alerts: suspicious login emails and what to check
• Passkeys: what’s great, what’s still confusing, and why some services still ask for a code
• Family Link and kids’ Google accounts: why Google requires @gmail.com, and how passkeys fit in
• Shared iCloud Passwords groups so parents can manage kids’ logins
• Password manager friction on Mac: Apple Passwords prompts vs 1Password workflows
• Listener feedback and the point of the show: it’s not a weekly “how-to,” it’s real conversations
• Teaching tech: beginner wins, real frustrations, and why “productivity level” training can be a better fit
• CES notes: mobility tech, batteries, smart locks, and a few other items that caught our attention
• Quick Surf app check-in: progress, but still clunky in places
• Support and contact info, plus Mastodon handles and the show hashtag

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This episode is a wide-ranging, very on-brand Technically Working conversation that starts with audio workflow testing and ends with bigger-picture decisions about the future of the show.

We spend time digging into what actually happens when we record with the Zoom Podtrack P4Next, , how computer audio is handled, and why VoiceOver and other system sounds can be harder to separate than people expect. A key takeaway is that once audio leaves your computer, it is just stereo audio, and whatever comes out is what gets recorded unless you do very intentional routing ahead of time.

From there, we revisit the idea of switching from Cleanfeed back to Zoom. The main driver is flexibility. If one or both of us are away from a computer and need to record from an iPhone or iPad, Cleanfeed is not an option. Zoom gives us more freedom, removes a extra subscription, and opens the door to potential YouTube livestreams. We also talk about Zoom’s Original Sound setting and why it finally feels usable.

Michael shares ongoing Raspberry Pi frustrations, including re-imaging systems, adding hardware based on advice from others, and why using separate microSD cards for different projects can be the right call. This turns into a broader conversation about hobby projects, learning by doing, and knowing when to ask for help.

Damashe walks through discovering damage to his MacBook Pro screen in a very real-world way while trying to complete an ID verification process. That discovery leads to a plan involving AppleCare, backups, wiping machines, storage limitations, and the general annoyance of migrating between Macs with different capacities.

We also talk about Bluetooth audio switching, why Apple’s automatic device switching is often more frustrating than helpful, and how shortcuts and third-party tools can give you back control over where your audio goes.

Later in the episode, we read and respond to listener comments and reviews. We talk candidly about the structure of the show, why it does not follow a traditional format, and who it is actually for. We acknowledge critic

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Check out our podcast host, Pinecast. Start your own podcast for free with no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.