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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Michael shares some recent work slip-ups tied to automation and explains how a small formatting mistake threw off email quick links for thousands of people. He walks through how he’s checking Zoom links more carefully now using JAWS sounds and VoiceOver tweaks—and vents a bit about Apple's pronunciation settings and table editing headaches on the Mac.

Damashe jumps in with thoughts on where VoiceOver stands in Apple’s priority list (spoiler: not high), and they both trade tips for avoiding Safari freeze-ups and digging into macOS settings. There's also some behind-the-scenes talk about how automation projects are making them think more like coders, even if they’re just feeding prompts to GPT.

They talk about:

• Renting vs. buying speakers for events (and how hotel AV pricing is wild)
• Michael’s growing collection of smart appliances (yes, Sniffy McGee the vacuum makes a return)
• Network upgrade ideas, attic fails, and future cable runs
• Damashe’s vending machine script to automate reporting from Cantaloupe
• Using Hazel with GPT to build automation rules on the Mac

Toward the end, Michael shares a serious PSA about a family member who nearly fell for a phone scam—and why it's time to have a plan in place before you get a scary-sounding call. Damashe adds tips for protecting yourself as deepfakes and voice cloning get better and easier to pull off.

They wrap it up with a quick look at download numbers, what’s working with the “live to tape” style, and why Damashe regrets not buying that fancy Dyson fan when it was on sale.

Links & Mentions:

• Email us at feedback@technicallyworking.show
• Follow the show: @tw@technically.social
• Michael: @payown@dragonscave.space
• Damashe: @damashe@technically.social
• Use #TechnicallyWorking on Mastodon to chat with us
• And yeah—huge thanks to our tip jar supporters. You're the real MVPs.# Episode Notes

Notes go here

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Tired of bloated apps and broken automation? Damashe and Michael dig into the everyday tech that actually works—and what still needs fixing. From Todoist frustrations to FaceTime workarounds, they share tools and tips that make their workflows smoother. In this episode, Damashe and Michael talk through weather delays, podcast recording quirks, and the growing complexity of Zoom and Slack. They discuss how apps often overreach—like Zoom trying to do everything but its core job—and why Apple and Google are both struggling with balance. Michael shares why he's using Todoist again, the quirks of its Mac app, and details on his upcoming beginner workshop. They dive into RingCentral’s AI call summaries, SuperWhisper transcription workflows, Gemini’s privacy quirks, and how Tailscale can fake out your apps into thinking you’re always home. They wrap up with Android typing tips that might just change your life.

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Michael and Damashe are back with a longform bonus episode full of tech tangents, gear talk, and plenty of laughs. In this laid-back catch-up:

• Michael recaps CSUN takeaways, airport barbecue, and zinc-powered travel hacks.
• Damashe shares how ChatGPT helped him sound-dampen his room and why Velcro tape is now a top-tier solution.
• They both talk backpacks—Michael stuffed his to the brim, Damashe vacuum-sealed his—and share why they're both oddly excited about compartments.
• Talk turns to running live audio setups, prepping for conventions, and dreaming about better comms gear (Zello, Sonobus, or something smarter?).
• Michael might reset his Mac. Damashe might buy a Mac Studio. Both are eyeing new mixers.
• The Home Assistant rabbit hole begins—will Damashe become that guy? Stay tuned.
• Shoutouts to Scout, an unnamed dinner guest, and every Technically Working listener who's still with them after 90+ minutes.

Plus: Homebrew, MASS, Clubdeck, AutoGain, chickens, cilantro, and the ultimate tip—don’t hand someone a mic with a used windscreen.

Follow the Show:
@TWE@technically.social on Mastodon for episode drops, bonus links, and future livestreams.

Support:
Big thanks to Tip Jar supporters. Want to help us buy more random gear? You know what to do.

Contact:
Email: feedback@technicallyworking.show
Michael: @payown@dragonscave.space
Damashe: @damashe@technically.social

Let me know if you want this trimmed down or need a shorter version for Mastodon/threads too.

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