In this bonus-packed episode of Technically Working, Michael and Demasi share previously subscriber-only content, technical workflows, and fresh commentary on the shifting tides at Apple. Here's what you’ll hear:

• Migrating a WordPress Site: Michael walks through how to back up and move a WordPress site from one domain to another using UpdraftPlus and Dropbox.
• Navigating the Terminal with VoiceOver: Demasi shares tips for VoiceOver users working in Terminal, including VO text selection tricks, bash vs. zsh navigation shortcuts, and piping output to files.
• Switching Back to Bash: Why Demasi still prefers bash over zsh, how to install the latest version with Homebrew, and how to set it as your default shell on macOS.
• MultiMarkdown to Rich Text: Demasi demos Brett Terpstra’s services for converting Markdown to formatted email with rich links and bullet lists.
• A Deep Dive into LaunchBar: Get a full walkthrough of Demasi’s customized LaunchBar preferences—from clipboard history to file actions—plus how to remove its Dock icon for a cleaner workflow.
• Apple’s Developer Drama: The hosts weigh in on Judge Gonzalez Rogers' ruling, Apple's hostile handling of third-party links, and what it says about Apple’s current priorities.
• Where Is Apple Headed? A passionate discussion on accessibility, developer trust, and whether Apple’s user-first culture is fading.

This episode is loaded with practical tips, frustrations, and honest conversations about tech. Be sure to follow:

• Michael on Mastodon: @payown@dragonscave.space
• Demasi on Mastodon: @demasi@technically.social
• Show bot: @tw@technically.social

Want early access to bonus clips and behind-the-scenes chatter? Support the show at technicallyworking.show and get the Tip Jar feed.

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This week’s episode of Technically Working lives up to its name—emphasis on “technically.” Michael and Damashe dive into a chaotic but honest session filled with:

• Live streaming experiments using Owncast and Cloudron
• A rundown of unexpected audio and network issues (including Michael’s mysterious Mac Wi-Fi fail)
• Why you may have only heard one side of the live broadcast
• A heartfelt update from Michael about stepping back from Club Unmute and issuing prorated refunds
• Real talk about prioritizing passion, family, and work
• Listener feedback from Tim, Robin, Shazard, and Scout
• Damashe’s upcoming trip to the Alabama School for the Blind tech symposium
• Shout-outs to Rogue Amoeba (yes, someone’s listening) and longtime fans like Matthew
• Honest download numbers and a much-needed perspective check
• Future plans for federated social, website improvements, and maybe merch—but definitely not mugs

Despite the rocky audio and robot voices, this episode is a raw behind-the-scenes glimpse of what happens when two tech heads push through chaos to keep the show going.

📧 Feedback? Send it to feedback@technicallyworking.show
🐘 Follow the show: @tw@technically.social
💬 Use hashtag #TechnicallyWorking on Mastodon to join the convo

No bonus show this week—but we’ll be back. Probably with fewer glitches.

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Michael and Damashe are back for another lively and unpredictable episode of Technically Working. As always, they jump right into the conversation—no theme music, no fluff—just two friends troubleshooting, laughing, and dropping Mac tips along the way.

This week:

Reaper, Audio Hijack, and VO shortcuts: Michael discovers Audio Hijack's behavior when blocks are disabled, and Damashe reminds us of handy VoiceOver key combos.

Finder tip: Learn how to group selected items into a new folder using Command-Control-N. The duo explores Finder views (column vs. list) and relives the chaos of a long-past Finder bug.

LaunchBar, Hazel, and file organization: Damashe shares how he uses LaunchBar to move files efficiently. Michael appreciates Hazel for keeping his Downloads folder neat.

Rage-quitting Todoist: Michael shares how missing a single day ended a streak and triggered a dramatic break-up with his task manager.

TikTok accessibility talk: Michael compares the experience between iOS and Android, and Damashe wonders about passkeys, logins, and using multiple accounts.

Doorbell drama: Listener Shahzad wants to know which video doorbell works best for blind users. Michael and Damashe dive into pros and cons of Reolink, Eufy, Ring, and Akara options—plus some thoughts on creepy listening features.

Screen recognition rants: The guys debate Apple’s screen recognition and its reliability—or lack thereof.

Chapters in podcasts? Shahzad's feedback leads to a bigger conversation about how chaotic their episodes are and whether chapters would help (hint: it’s complicated).

The future of the Technically Working website: Damashe breaks the site while trying to add pagination and a summary button. They explore self-hosting, podcast membership plugins, and maybe even building their own subscription system.

Belkin's tracking stand as a DIY CCTV: A surprise use case for a MagSafe stand shows how accessibility tools sometimes come from the most unexpected places.

Apple's new magnifier for Mac: Could your Mac become your CCTV with Continuity? Possibly.

Tip Jar perks: A teaser for Tip Jar subscribers—bonus episodes, early access, and a soon-to-be test group for new site features.

Links mentioned:

Double Tap on Air - Subscribe

Reolink Video Doorbell

Eufy Security

Belkin Auto-Tracking Stand

To share your thoughts, email: feedback@technicallyworking.show Want early access and bonus drops? Become a Tip Jar supporter at technicallyworking.show

Follow on Mastodon:

Michael: @payown@dragonscave.space

Damashe: @damashe@technically.social

Bot: @tw@technically.social

We’re not organized, but we’re still here.

Enjoy what’s next in your queue—it won’t be us. Not until next time.

Recorded with questionable Finder settings and occasional muting that wasn't muting.

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We’re back with a full plate: broken email, fixed automations, and a few new toys on the desk. Michael walks through how he’s rebuilding a Google Sheets to Word workflow to handle Zoom links, Clubhouse flags, and ACB Media stream details. Plus, some Word macros are now baked right into the default template—finally.

Damashe shares updates on spinning up a streaming server with AWS, possibly tying it into Audio Hijack, and revisiting automation tools like Bunch and Keyboard Maestro. We also dive into Joplin for cross-platform note-taking, prompt storage, and maybe even shared show notes down the road.

Also in this episode:

• Michael’s first impressions of the Insta360 Link 2 webcam
• The camera mount Demasi didn’t want to give up
• Early thoughts on Surf.social
• Prompt-crafting tips, saving specs, and getting ChatGPT to stop rambling
• Rants about TikTok comments and the ChatGPT sidebar

Thanks as always to our Tip Jar subscribers—you get this one a little early. Let us know what stood out: feedback@technicallyworking.show.

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In this episode of Technically Working, Damashe and Michael kick things off with an unexpected Reaper backup and a PSA about Loopback and Rogue Amoeba’s ARC plugin update. Damashe walks through his workaround using debug mode to temporarily resolve broken audio routing after the update, while Michael cautiously avoids the update altogether—at least until after his next live stream.

From there, the conversation jumps into LaunchBar indexing fixes, email quirks in macOS Mail, and whether podcasting is still worth the time investment (spoiler: it is). They also dive into small business operations, exploring the often-misunderstood distinctions between W-2 employees and 1099 contractors. Damashe shares his recent HR frustrations and the need to implement clear employee agreements, even in small teams.

Later, they get transparent about download numbers across multiple shows (Technically Working, Shell Phone Show, and Unmute Presents), and emphasize how consistency is still the most effective form of podcast marketing. Expect honest talk, a few AI tool rants, and maybe a podcast name for your washer.

Topics Covered:

• Loopback & ARC plugin update issues and workaround
• LaunchBar indexing fix walkthrough
• Email navigation and link preview fixes in macOS Mail
• When to use W-2 vs. 1099 in small business hiring
• Pros and cons of payroll vs. contractor systems
• Honest download numbers across podcast projects
• Thoughts on burnout, consistency, and podcast marketing
• Experimenting with Perplexity and ChatGPT Pro for workflow support

Resources Mentioned:

• Loopback Debug Mode: Help menu > Relaunch in Debug Mode
• macOS Mail Fix: Uncheck "Show Link Previews" in Preferences > Composing
• Perplexity AI (Free & Pro tiers): https://www.perplexity.ai

Send feedback to: feedback@technicallyworking.show
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Damashe surprises Michael with the return of a legendary piece of gear—the Sound Devices USBPre 2. He breaks down why he repurchased this pricey, hardware-only audio interface, how it's now integrated into his workflow, and why going back to basics sometimes means investing more for long-term reliability. The conversation dives into practical audio setup tips, why sliders still hold a place in our hearts, and how a trusty backup system can save the day.

They also cover unexpected changes to work routines, reflections on managing employees and hiring backups, and how simply talking to people (like postal workers) can solve logistical headaches. Plus: nostalgic radio moments, movie theater trade-offs, and the eternal struggle of naming smart home devices.

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In this episode, Damashe uncovers a hidden switch that finally makes his mute button work the way he wants—after months of assuming he needed to rewire it. Meanwhile, Michael shares a chaotic behind-the-scenes story from an in-person board meeting, complete with misbehaving audio gear, last-minute fixes, and some DIY mix-minus routing.

The two dive into:

• Why assumptions and leading questions can steer you wrong—even with AI.
• Lessons learned from a tough live audio setup and the temptation to beat yourself up over tech failures.
• Creative ideas for talkback communication systems using Shokz, Zello, and even FaceTime Audio.
• Android experiments: Michael’s iMessage-on-Pixel attempts, thoughts on BlueBubbles, and the appeal of the Pixel 9.
• VM cleanup strategies and the case for consolidating multiple virtual machines into one solid Windows environment.
• Decisions around Google Workspace vs. DIY setups for small teams—and why simplicity may win.

Plus, a quick reminder: new episodes drop Monday evenings. Follow the TW bot on Mastodon to stay updated.

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In this episode, Michael admits he never called Apple—no surprise there—and shares what happened instead: experiments, frustrations, and the joys of not resetting VoiceOver live. Damashe breaks down his complicated relationship with to-do list apps, from OmniFocus quirks to why he’s sticking with Todoist (despite some platform inconsistencies).

We also dive into ChatGPT’s deep research mode and how Michael used GPT and Google Apps Script to streamline weekly workflows—what used to take hours now takes seconds. There’s talk of accessibility in Google Sheets and Docs, frustrations with VoiceStream Reader, and Bluetooth weirdness with Apple’s audio routing.

And yes, that one setting in Parallels that makes Mac/Windows integration so much better? We finally figured it out. You’ll want to hear this if you use SharpKeys and Keyboard Maestro.

Bonus rants: the B device still sucks, the Plod is promising, and surprise—your notifications don’t mean what you think they mean.

Links Mentioned:

• Review: “I Outsourced My Memory to AI and All I Got Was Fan Fiction” – The Verge
• Technically Working Tip Jar

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This podcast is powered by Pinecast. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.