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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Kicking Off with a Familiar Chaos

• Michael and Damashe reflect on how their episodes often start mid-conversation instead of with a structured intro.
• Michael notes that this mirrors their real-life calls—jumping straight into discussions without formal greetings.

Damashe’s Office Overhaul

• New Layout: Desk now faces the room instead of the wall, giving a more executive feel.
• Tech & Workspace Adjustments:
• Boom Arm Swap: Back to the Rode boom arm for smoother, quieter adjustments.
• Microphone Change: Using the Beta 87A after stashing away the Earthworks mic.
• Acoustic Challenges: Removing boxes increased reverb—plans to install sound dampening panels.
• Networking Upgrade: Exploring Ethernet setup, possibly running cables through the attic.
• Additional Changes & Plans:
• Coin sorter and bill counter now have dedicated spots.
• New storage system for organizing cables and tools.
• Plans to mount wall cabinets for more space.
• Top Wish List Item: Better climate control—the office lacks central heating/AC, making it challenging in extreme weather.

Michael’s Office & Flexible Workstyle

• Garage Setup:
• Two-tier sit-stand desk (mostly used sitting).
• Logitech MX Keys keyboard, Mackie 1204FX mixer, and Vocaster 2 audio interface.
• OWC dock connects everything neatly.
• Living Room Workstation:
• Uses the DJI Wireless 2 Mic for portable calls and recordings.
• Primary workspace: the living room couch with his MacBook Pro and headphones.
• Recording process: Quickly reconnects his setup in the garage, ready to go in seconds.

Apple’s Surprise Improvements

• Audio Switching Just Works™:
• macOS now remembers and restores audio devices when reconnected—something that was unreliable in the past.
• No more manually resetting inputs and outputs after unplugging an interface.
• MacBook Battery Life = Game Changer (but we won’t say that)
• Long-lasting battery means less time tethered to power, more time working from anywhere.

Cellular Upgrades with US Mobile

• Damashe switched his personal and business lines to US Mobile, now offering:
• AT&T and Verizon network switching for better coverage.
• Unlimited data on a second line for free when both lines are on the same phone.
• Future dream: MacBooks with built-in cellular, making tethering a thing of the past.

Closing Thoughts

• Thanks to Tip Jar subscribers for the support! Your contributions help keep the show going.
• Expect a new Mastodon bot account to automate episode release posts.
• Reminder: Tell a friend about the show! Repost on Mastodon or share with someone who’d enjoy it.

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Michael and Damashe tackle an episode packed with tech, automation, and a little unexpected humor. From Zoom mischief and Audio Hijack quirks to Loopback mysteries, they navigate the complexities of their audio setups—sometimes solving problems, sometimes creating new ones.

Then, they dive into Gravity Forms and how it might replace an entire workflow currently running on Google Sheets. Could automation save hours of manual work? Probably. Will Michael drop everything to build it right now? Almost certainly.

Meanwhile, Damashe wrestles with business finances and OCR woes, looking for ways to automate receipt tracking (because let’s be real, OCR is still a mess). Plus, the two discuss Mistral’s new OCR tool—will it finally solve their document headaches?

And in an unexpected turn, Michael realizes that Coke deliveries have taken over Damashe’s life. Not that Coke—the kind that keeps vending machines stocked. Ever wondered what it’s like to have a “Coke guy” on speed dial? This one’s for you.

• Why Apple Music as a stream filler may or may not be a terrible idea
• The real reason Windows still has a place in their workflow
• The importance of good Mac apps (Rogue Amoeba, Hazel, TextExpander, and more)

If you enjoy geeky deep dives, automation hacks, and tech chaos, this episode delivers.

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In this celebratory 100th episode of Technically Working, Michael and Damashe reflect on the journey so far, share some big personal and professional news, and look ahead to the next hundred episodes.

What to Expect in This Episode

• Hitting the 100th Episode Milestone
• Reflections on how the podcast has evolved since the DM Series
• The importance of consistent weekly recording and publishing

• Plans for growth and new ideas in the next 100 episodes

• Automation and Coding with Python

• How Michael’s Python scripts are automating repetitive tasks
• Using GitHub Copilot and ChatGPT to assist in code development

• Tips on iterating and refining your automation projects

• Managing Email and Information Overload

• Why unsubscribing doesn’t always work—and the alternatives
• Considering tools like Clean Email and SaneBox

• Balancing minimal inbox management with real-world demands

• Damashe’s Vending Route Updates

• The ups and downs of hiring and training employees
• Lessons learned about delegating, scheduling, and logistics

• How better planning and a solid team are freeing up more time

• Michael’s New Role at ACB

• Transitioning into Membership Services Administration
• Immediate projects, including large-scale event coordination

• Embracing new workflows, audio streaming, and hosting technology

• Looking Ahead

• Preparations for upcoming travel, conferences, and conventions
• Potential for new interviews with a wider variety of guests
• Continuing to refine workflows, gear, and future episode content

Stay Connected

• Send us your feedback:
  feedback@technicallyworking.show
  Let us know what you’d like to hear in future episodes or share how you’re tackling similar challenges.

• Find us on Mastodon:

• Michael (Payown) at @Payown@dragonscave.space
• Damashe at @Damashe@technically.social

• Use #TechnicallyWorking (please capitalize T and W for accessibility)

• Tip Jar Subscribers
  Thanks to all our supporters! Your contributions help us keep the mics on and the episodes rolling. Want to join in? Check the show notes in your podcast app for our Tip Jar link and receive extra content as a thank-you!

Thanks for celebrating with us on this journey to 100 episodes. We appreciate every listener and supporter who’s helped us reach this milestone. Here’s to the next hundred!

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This week, we’re figuring things out as we go—talking about smart assistants, digital business cards, and how we’re using AI to simplify work.

• Podcast Growth the Direct Way – Inspired by Allison from Podfeet.com, we discuss an aggressive (but effective) approach to getting people to subscribe.
• Would You Buy a ChatGPT Speaker? – Damashe is diving into Home Assistant and debating whether a locally run AI assistant is worth the setup.
• Plod vs. B: The AI Recording Showdown – How do these two AI-powered recording devices compare, and which one makes more sense for real-world use?
• GitHub for Beginners – Michael’s learning GitHub, and Damashe thinks it might be time for a mini-series.
• Digital Business Cards Done Right? – Michael gets his Dot Card working but runs into some accessibility quirks.

Also, Tip Jar subscribers got an exclusive 21-minute bonus episode where we went deep into navigating the Mac’s Terminal, Zsh vs. Bash, and some quick navigation tricks. If that sounds like your kind of thing, you might want to check it out.

Got thoughts? Find us on Mastodon or email feedback@technicallyworking.show.

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