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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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.

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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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.