Episode 150 - Published February 15, 2026 Michael and Damashe celebrate episode 150 with a technical troubleshooting session that turns into a masterclass on VoiceOver settings, Audio Hijack experimentation, and podcast marketing strategies. In This Episode: VoiceOver Menu Fix (Critical for Mac Users)

The solution to broken menu bar navigation in VoiceOver Why "Mouse pointer follows VoiceOver cursor" causes problems How to configure VoiceOver Utility settings properly When mouse tracking is useful vs. problematic

Audio Hijack Exploration

Real-time compression testing and audio processing Setting up test sessions to experiment with effects The difference between recording with effects vs. applying post-production Tips for session documentation and organization

Hardware Updates

Damashe's DJI Mic Mini purchase and setup ($80 with charging case) Insta360 Flow 2 Pro gimbal for iPhone video content Loupedeck controller for podcasting workflows Apple repair adventures with MacBook Pro and iPad Mini 6

Podcast Marketing Strategy

Using Claude AI to identify clip-worthy moments from transcripts Creating video shorts with AI-generated visuals Buffer integration for multi-platform scheduling Open Claw (ClaudBot) automation coming soon YouTube growth plans and content strategy

Shout Outs

Christopher Sims - Thank you for the Tip Jar support! All our Tip Jar subscribers - You make this show possible

Mentioned Resources

Audio Hijack by Rogue Amoeba DJI Mic Mini (2 transmitters + receiver + charging case) Insta360 Flow 2 Pro gimbal Buffer for social media scheduling VoiceOver Utility settings

Contact & Support Email: feedback@technicallyworking.show Mastodon:

Michael: @payown@dragonscave.space Damashe: @damashe@technically.social Bot: @TW@technically.social

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This week, Damashe considers canceling his Claude subscription... only to immediately sign up for a more expensive plan to hire Claude as his virtual assistant. Meanwhile, Michael tackles a Stream Deck accessibility project with help from Claude Code, and the guys make potentially dangerous plans to unleash OpenClaw on their Mastodon bot. Plus: RSS reader workflows, notification rage-quitting, Bitcoin regrets, and why good help really is hard to find (whether human or AI).

AI Assistants & Claude (2:00)

• Damashe's plan to use Claude as a $100/month virtual assistant
• The $50 API credit offer (expires February 16th!)
• Why AI hasn't taken jobs... yet
• Claude Code living in the terminal

Stream Deck Accessibility Project (15:00)

• Making Stream Deck usable for blind users on Windows and Mac
• The power of profiles and context-switching
• Integration possibilities with Bunches, shortcuts, and automation

RSS Readers & Workflows (6:00)

• Net News Wire, Liray, and the eternal search for the perfect feed reader
• Why preview mode matters
• The Verge's Twitter-on-their-website approach

OpenClaw Plans (1:07:00)

• Security concerns and Leo's removal
• The bot that got itself a phone number and called its owner
• Plans to unleash it on the @TW Mastodon bot
• Building a kill switch (before the bot reads this transcript)

Good Help is Hard to Find (30:00)

• Why reliable contractors are priceless
• The 90-day test for employees who think the job is easy
• Michael's subcontractor success story

Also Discussed

• Cash App notification rage-quitting
• Uber's marketing message problem
• Bitcoin: "I would have sold it at $2,000"
• Home Assistant Yellow module installation anxiety
• Raspberry Pi 5 (16GB) for sale!

• Follow the bot: @TW@technically.social (before OpenClaw takes over)
• Claude $50 credit: Redeem in settings before Feb 16th
• Harper's blog: Early Claude Code adopter mentioned on TWiT
• Net News Wire: Open source RSS reader
• PineCast referral: 50% off first 4 months (link in show notes)

• Total downloads: 29,312 (just 688 away from 30K!)
• Episode 148: 45 downloads
• Episode 147: 154 downloads
• Help us grow: Subscribe a friend!

• Email: feedback@technicallyworking.show
• Michael: @Payown@dragonscave.space
• Damashe: @Damashe@technically.social
• Use #TechnicallyWorking to join the conversation

Support the show at technicallyworking.show/tipjar

Episode 149 • Runtime: ~1:13:00

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Check out our podcast host, Pinecast. Start your own podcast for free with no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

This episode covers a wide range of real-world tech experiments, AI tools, and the line between helpful automation and “maybe don’t give that full access yet.”

We start with money talk (not advice). Damashe shares that he finally opened a Fidelity account and bought his first stock, while Michael talks about using watch lists and trade notifications. They also explore how accessible investing apps are getting, including audio charts and VoiceOver support, plus where accessibility still falls short.

Claude Bot and AI with real power A big chunk of the episode focuses on Claude Bot, an open-source tool that lets you interact with an AI through messaging apps like Signal, WhatsApp, and more. The idea of giving an AI access to your computer is exciting… and a little terrifying. This leads to the show’s unofficial safety rule:

> If an AI tool can take actions on your system, run it on a Raspberry Pi or other isolated setup first.

They break down risks like prompt injection, why connecting AI to email and calendars can be dangerous, and why curiosity should always be paired with caution.

AI for everyday life: meet Cookie On the more practical side, Michael shares a cooking app called Cookie. It reads recipes out loud, lets you ask questions like “What’s the next step?” and even suggests ingredient substitutions. It was not originally built for accessibility, but turned out to be incredibly useful for blind cooks. A great example of AI being used in a focused, practical way.

Smarter notes and personal workflows Damashe talks about using AI with DevonThink to automatically organize documents, and why he’s eyeing Drafts with new automation features. The goal: speak a quick note and have it turn into structured data, lists, or tasks without manual sorting.

Social apps, open source, and platform politics There’s also discussion about:

• A new accessible Mastodon and Bluesky client
• Mastodon instances blocking apps built with AI assistance
• The tradeoffs of open platforms where each server sets its own rules

Linux curiosity returns More blind tech users are experimenting with Linux on the desktop again. The hosts are curious what’s improved, especially with screen readers, and ask listeners to share their experiences.

And yes… Todoist check-ins They wrap with progress (and setbacks) on staying consistent with task tracking.

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Find out more at https://technically-working.pinecast.co

Send us your feedback online: https://pinecast.com/feedback/technically-working/887fda25-0695-49dd-9853-1586cd71fe1c

Check out our podcast host, Pinecast. Start your own podcast for free with no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.