Technically Working

In this time-shifted episode of Technically Working, Michael and Damashe dive into a pile of long-overdue listener feedback. They kick things off with a detailed voice message from Lord Robin Christofferson about Cal Studio (formerly PFMM.ai), a platform for building and monetizing custom AI tools. Then it’s on to GrapheneOS—Damashe shares updates on accessibility, eSpeakNG’s new direct boot support, and what it takes for blind users to flash the ROM.

They also respond to Scout’s questions on ProtonMail, network gear placement, and smart home setups—complete with temperature sensors and leak detectors. Michael wo...

Michael got his MacBook back and shares the apps and tools he immediately reinstalled—including Audio Hijack, Raycast, Hazel, and Little Snitch—plus what didn’t quite make the cut. Damashe walks through Homebrew tips, Markdown Service Tools setup, and how to fix symlink issues for missing binaries. They also dive into Mac App Store automation with mas, speaker setup logistics for live events, and whether to send signal to a subwoofer first or last in the audio chain.

They also cover:

Michael and Damashe are back with a full update after a few hectic weeks. Damashe shares how recent life events impacted work and how his new employee got thrown into the deep end early. They talk through ongoing audio adjustments, including Michael’s Mac OS beta install on a separate APFS volume and Damashe’s experience with the iOS beta leading to voiceover issues — and how Braille saved the day. The conversation shifts to Damashe’s ongoing Pixel 9 Pro experiment, using dual eSIMs, RCS messaging, Android accessibility, and the ongoing challenge of cross-platform messaging. Michael shares his first steps into cre...

In this episode of Technically Working, it’s a quick catch-up packed with gear decisions, GPT frustrations, and accessibility discoveries. Things kick off with some behind-the-scenes updates about live streaming improvements—including why ads are gone and how latency might get better with a little server tinkering. Then it’s time for a scanner showdown. After testing models from Brother, Epson, and ScanSnap, one portable scanner wins out thanks to battery life, duplex scanning, and microSD support (plus a healthy dose of velcro). The conversation shifts to recent AI weirdness:

In this bonus-packed episode of Technically Working, Michael and Demasi share previously subscriber-only content, technical workflows, and fresh commentary on the shifting tides at Apple. Here's what you’ll hear:

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:

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 tip: Learn how to group selected items into a new folder using Command-Control-N. The duo explores Finder views (column vs. list) and relives the chaos of a long...

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...

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 dist...

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 wo...

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:

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 wi...

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 projec...

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 de...

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:

Kicking Off with a Familiar Chaos

Damashe’s Office Overhaul

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 le...

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

Plans for growth and new ideas in the next 100 episodes

Automation and Coding with Python

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.

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 functionality of these innovative tools.

Dynamic Ad Insertion: The duo discusses the pros and cons of dynamically inserted ads in podcasts and YouTube videos. They explore how AI could po...

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 shifts to productivity tools, with Michael detailing his Python script for podcast downloads and Demasi's recent upgrade to Hazel 6, highlighting its new OCR capabilities. They also touch on the importance of clipboard...

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 with some outside-the-box ideas, like tapping into Uber drivers and cleaning crews for better business logistics. They also chat about the B wearable device and whether AI-powered tools actuall...

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:

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:

In this episode of Technically Working, Damashe and Michael tackle the quirks of mute switches, explore the seamless setup of the DJI Mic 2S, and share workspace frustrations with practical solutions. The duo also reflects on their 2024 themes and the lessons learned—In 2025 we learn about Michael’s focus on education and Damashe’s drive to build infrastructure. Plus, thoughts on the ever-reliable Pixel 5, innovative workflows, and the importance of getting back to basics. A must-listen for tech enthusiasts looking for inspiration and efficiency!

In this laugh-filled and tech-focused episode of Technically Working, Damashe and Michael are joined by Sean Preece from Double Tap. Together, they explore:

Join us for laughs, insights, and practical takeaways in this fun and tech-packed episode.

Links Mentioned

In this final episode of 2024, Michael and Damashe dive into a casual yet insightful conversation about the past year, their annual themes, and how they’ve evolved. They reflect on the “Year of Purpose” and “Year of Connections,” sharing lessons learned, missed opportunities, and plans for the future.

They also discuss:

In this episode of Technically Working, Michael sits down with JJ Meddaugh, founder of Blind Bargains and AT Guys. Together, they explore JJ's journey through entrepreneurship, tech, and accessibility, offering listeners a mix of inspiration, insights, and humor.

Highlights:

The Origins of Blind Bargains
JJ shares how Blind Bargains started as a resource for finding affordable tech and accessible products, evolving into a platform for podcasts and breaking industry news.

From MobileSpeak to AT Guys
Learn how JJ transitioned from software sales to physical products and scaled AT Guys into a...

In this episode of Technically Working:

TW88 Damashe records from home, sharing mic challenges with the Shure Beta 87A while Michael humorously notes their avoidance of news. They introduce a special offer for 'tip jar' subscribers and discuss Jetpack CRM, highlighting a 40% discount until December 31, 2025, and the importance of data privacy. The duo explores marketing funnels and analytics, touches on Jetpack CRM accessibility, and shares insights on hidden business costs. They also discuss Mac battery life and keyboard shortcuts before wrapping up with podcast preferences, expressing gratitude for their supportive listeners.

Support Technically Working by contributing to their tip jar: https://tips.pinecast...

In this episode of Technically Working, Michael and Demasi dive into the tech tools that have recently saved their day. From office heaters and robot vacuums to the intricacies of setting up tech for a wedding, they cover it all. They also discuss the pros and cons of various tech services, including Zoom, Riverside, and different CRM tools. Plus, they share their experiences with ChatGPT and MacGPT, and how these tools have integrated into their workflows.

Key Topics:

Office Heaters and Robot Vacuums: - Michael's search for a small office heater. - The allure of...

Show Notes for TW86:

This week, Michael and Damashe are joined by Taylor Arndt, a WordPress plugin developer and all-around AI enthusiast. Taylor shares how she’s using AI to do everything from coding smarter to managing accessibility projects, and even navigating the quirks of driverless cars (spoiler: grass patches may be involved).

Here’s What We Covered:

In this episode, Michael and Damashe vent about the headaches of web browsing with screen readers and dig into why keyboard shortcuts don’t always work the way they should. They talk about using VoiceOver, JAWS, and other tools to navigate the web, sharing what’s been working—and what’s just plain broken.

The conversation shifts to managing tech workflows, including tips on handling digital clutter and writing smarter LinkedIn posts with AI. It’s a mix of tech gripes, practical fixes, and the usual back-and-forth you’ve come to expect.

Support Technically Working by contribut...

In this episode, we kick things off discussing call recording on iOS and some tips to make it easier. We also dive into payroll setups and the difference between contractor versus employee roles, sharing insights on managing payroll smoothly. Michael shares plans to handle audio for a wedding and explores the best setups to ensure high-quality sound throughout the event. Plus, we get into hybrid setups for meetings and how to adapt tech for various event needs.

Michael and Damashe discuss optimizing work setups, from Mac Minis to automation tools like Hazel, and weigh the benefits of DIY versus ready-made membership systems. They also share updates on Unmute Presents and plans for a new Q&A format.

Episode Resources

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In this episode of Technically Working, we dive into the intricacies of desk setups and the importance of having a boom arm for your microphone. We also discuss the challenges of maintaining a clean and organized workspace, and the benefits of implementing a stretching routine to alleviate back pain and improve overall physical health. Our hosts share their personal experiences and tips for staying physically fit while managing a busy work schedule.

We also explore the world of portable scanners, with a focus on finding the best options for scanning receipts and invoices on the go. Our...

In this episode of Technically Working, Damashe and Michael dive into their hands-on experiences with tech setups, both in the studio and on the go. Damashe struggles with Riverside's mobile app not supporting USB microphones on iPhones, leading to frustrations during a test run. Michael shares his latest adventures in managing live audio for events, wiring complex setups to integrate Zoom calls and in-room speakers seamlessly. They also touch on Apple’s newly released iPad mini, discuss the frustrations of Seeing AI resetting first start settings, , and discuss future projects involving IVR systems and automated transcripts for their podcasts. Al...

Show Notes:

In this episode of Technically Working, Michael and Damashe dive into the complexities of audio setups and workflows. Michael shares his intricate setup involving a Mackie ProFX12, the Shure Beta 87A mic, and the Vocaster Two. The duo discusses balancing inputs, managing audio channels in Reaper, and troubleshooting issues with VoiceOver playback. Damashe also reveals a new discovery about Zoom’s ability to select specific input channels, which could streamline audio management during calls.

As the conversation shifts, Michael reflects on organizing personal and professional life, including the importance of having a clear pu...

Show Notes:

In this episode of Technically Working, Michael and Damashe share their recent tech struggles and solutions. Michael’s trusty Lenovo laptop finally bites the dust, forcing him to switch to Mallory's MacBook Air—sparking a discussion on the pros and cons of Mac vs. Windows and the importance of having solid backup systems. Damashe highlights the significance of testing backups and restoring them, sharing some recent issues with restoring systems that didn’t go as planned.

The duo also dives into the quirks of using AI tools like ChatGPT for task management and troubl...

In this episode, learn what Damashe sent Michael, what Michael bought, our thoughts on the Meta Announcement, and how Damashe has ... tried to use META AI!