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

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