Technically Working

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...

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 ti...

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...

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 ...

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 sy...

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.
• L...

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 App...

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...

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 ...

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 w...

• 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.

• New Layout: Desk now faces the room instead of the wall, giving a more executive fee...

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?...

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 ...

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 t...

In this episode of Technically Working, Michael and Damashe dive into a variety of tech topics and personal anecdotes, all while keeping the conversation light and engaging. Here’s what you can expect:

• New Tech Adventures: Michael shares his experience with the Dot Card Metal and Dot Band, digital business cards that use NFC technology. He discusses the setup process, challenges with accessibility, and the overall functionali...

In this episode, Demasi and Michael dive into their tech routines and recent changes. They discuss the challenges and solutions for managing audio settings on Mac, the simplicity of using tools like SoundSource and Audio Hijack, and the frustrations with TestFlight on new Macs. They also share an interesting experiment involving AI and non-techie users, and Demasi's recent experience purchasing a pistol online.

The conversation shi...

TW96: Time, Energy, and the Struggle of Doing Too Much

🎙️ Listen now: TechnicallyWorking.show

Damashe’s juggling a lot—running multiple businesses, managing employees, and trying to keep things moving while dealing with exhaustion. In this episode, he breaks down what’s been working (and what hasn’t), including hiring struggles, time mismanagement, and why being too busy can actually set you back.

Michael jumps in wit...

In this episode of Technically Working, Michael and Damashe dive into their experiences with the latest AI tools and devices, including the Google Gemini and the B Pioneer wearable assistant. They explore:

• Google Gemini in Gmail: How it helps with searching email efficiently and what works better on iOS vs. the web interface.
• The B Pioneer Wearable: Michael’s initial impressions, setup process, and concerns about privacy, acce...

Show Notes:

In this episode of Technically Working, Michael and Damashe cover a range of tech topics, including the promising Bee Pioneer AI wearable, accessibility tools, and navigating virtual machines. Here’s what’s inside:

• Bee Pioneer AI: Michael orders the Bee Pioneer Edition, a personal AI device designed to convert conversations into tasks, summaries, and reminders. They discuss its potential for productivity...