Technically Working

Damashe Thomas and Michael Babcock
  • 5.0 (1)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

"Welcome to 'Technically Working', the go-to podcast for tech enthusiasts and productivity seekers alike. Hosts Michael Babcock and Damashe Thomas take you on a journey through the ever-evolving world of technology and productivity. As Mac OS and iPhone users, they share their personal experiences and tips on staying productive while using these tools. But they don't stop there - they also explore other platforms like Android and Windows to bring you a comprehensive view of the tech landscape. Tune in each episode to hear them keep each other accountable, discuss the latest tools and strategies, and share their journey to reaching their goals. Whether you're a small business owner, freelancer, or simply looking to boost your productivity, 'Technically Working' is the perfect podcast for anyone looking to level up their tech skills and get things done."

  1. 4D AGO

    Mics, Passwords, and Postmark: Getting Your Tech Stack Right

    2. Show Notes Episode 152 - Technically Working Michael and Damashe are back with a packed episode covering gear, passwords, transactional email, and how to get the most out of your AI tools. Plus, Mike hits a milestone and there's a guest teased for next week. Topics covered: Mic Talk (Mini-Series Continues) Damashe is back on the Audio-Technica ATR 2005 over USB, and explains why this style of mic remains a solid starter or travel option. The ATR 2100x and Samson Q2U both offer USB and XLR connections, making them flexible picks for new podcasters or anyone who wants a good-sounding mic for Zoom calls. Neither is recommended for run-and-gun situations, but both shine at a desk. Password Managers One Password recently raised prices for individual and family accounts. Michael's annual plan jumped from $35.88 to $47.88. That sparked a longer conversation about where people's passwords actually end up, spread across multiple apps and browsers. The guys walk through several options, including 1Password, Bitwarden (free tier available, $10 per year paid), ProtonPass, Apple Passwords, and KeePass. Apple Passwords works well for people deep in the Apple ecosystem, but the sharing and permission structure has limitations. ProtonPass got a positive accessibility mention from a listener. If you're cross-platform, 1Password and Bitwarden are still the strongest picks. Tip from a listener named Scout: ProtonPass is accessible. AI Tools and How to Use Them Well Both hosts have been using Claude heavily for scripting, Google Apps Script, and Python work. Key prompting tip: don't lead the AI with your assumptions. Instead of asking if a specific approach will work, describe what you want to accomplish and ask for options. Then interrogate the answer. Even if you don't know the subject well, asking "are you sure?" causes the model to recheck itself. This tip came from Matt Geek Gal and both hosts have been applying it regularly. Postmark: Transactional Email Made Approachable Damashe has been setting up Postmark for transactional email and invited Michael to explore it together. Key concepts broken down: servers in Postmark are essentially folders, not web servers. You verify your domain by adding two DNS records, a DKIM record and a return path record. Postmark puts new accounts in a sandbox that limits sending to verified addresses only, protecting their deliverability reputation. Getting out of the sandbox was quick, with a human review and approval happening overnight. Postmark separates transactional and bulk email into streams, and you can add additional streams for testing or staging environments. Inbound email routing is also supported. For 10,000 emails per month, pricing runs around $18 to $20. Siri and ChatGPT Siri's integration with ChatGPT has made both hosts more willing to ask quick questions by voice. Answers now come back summarized rather than handing off to a browser link. Still not perfect, especially with home automation commands, but noticeably better than two years ago. Milestone As of this recording, Michael has been with ACB for one year. Damashe points out he's automated himself into more work, not less, which is exactly the kind of employee you want to keep. Listener News A new listener was recruited by Michael while on a phone call. Shoutout to Chris for pioneering the one-time Tip Jar option. Another tip came in since then. Monthly subscribers are appreciated too. Next Week A guest is joining the show. No hints were dropped, but Damashe will be on different gear. Links and Resources Postmark: postmark.com Bitwarden: bitwarden.com 1Password: 1password.com ProtonPass: proton.me/pass Samson Q2U mic Audio-Technica ATR 2100x Subscribe on your favorite podcast app and search Technically Working Follow the hosts: Michael: @payown@dragonscave.space Damashe: @damashe@technically.social Show bot: @tw@technically.social Hashtag: #TechnicallyWorking (capitalize the T and W on Mastodon) Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/1576a4b8-1626-4323-bbd9-a22f3c8a14f7 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.

    1h 18m

  2. FEB 22

    Mic Check: Video Mics, Audio Interfaces, and Vibe Coding Wins

    This week, Damashe and Michael dive into a hands-on comparison of the DJI Mic Mini and DJI Mic 2, talking through what makes these wireless lapel mics shine for video content and where they fall short for audio-only podcasting. You'll hear Damashe's mic in action throughout the episode. Damashe kicks off a new series where he'll rotate through several audio interfaces, using the same Beta 87A microphone as a constant, so listeners can hear real differences and eventually land on a recommended setup alongside Michael. This episode features the DJI Mic Mini. Future episodes will feature the Vocaster One, the Zoom H5 Studio, the Soundcraft MTK 12, and others. Damashe also reveals that his go-to recording microphone has been the Earthworks Ethos condenser, and explains why he picked it over the Beta 87A as his studio mic while keeping the 87A as a travel option. For most listeners, his current recommendation for a podcasting mic is the Beta 87A, typically found between $200 and $215. On the tech side, the guys talk about vibe coding updates, including how Michael used Claude in planning mode to shrink his Builder app's load time from around 30 seconds down to about two seconds by switching to lazy module loading. They also discuss IFTTT webhooks, Pushover notifications, and how Damashe built a system to get push alerts whenever the podcast gets a new tip or reaches a download milestone. Other topics include Bluetooth auto-connect annoyances and how to fix them on Mac, the Project Hail Mary movie coming to Prime, and a quick update on Damashe's MacBook Pro and iPad mini repair situation with Apple. Marketing Plan Notes (not written out yet, just the approach): When you're ready to build the marketing content, the main angles to plan around are: The audio interface series as an ongoing hook, giving people a reason to tune in each week The vibe coding / Claude planning mode moment as a standalone clip or short The DJI Mic Mini review content, which plays well for video creator and accessibility audiences The IFTTT + Pushover automation walkthrough as a practical tip post or thread Listener shoutouts and the tip jar mention as community engagement touchpoints Let me know when you want to build that out. Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/9b72d4fb-7c95-4540-b721-aaafad285f0a 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.

    1h 10m

  3. FEB 14

    Fixing VoiceOver Menus, Audio Hijack Deep Dives, and Our Social Media Marketing Strategy

    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 Hashtag: #TechnicallyWorking (please capitalize the T, T, and W) Support the show: https://tips.pinecast.com/jar/technically-working Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/2134cc23-ed56-489d-a590-a3019dc674a0 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.

    1h 16m

  4. FEB 8

    Hiring Claude as a $100 Virtual Assistant

    Episode 149: Hiring Claude as a $100 Virtual Assistant Episode Description 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). Topics Discussed 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! Links & Resources 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) Show Stats Total downloads: 29,312 (just 688 away from 30K!) Episode 148: 45 downloads Episode 147: 154 downloads Help us grow: Subscribe a friend! Contact 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 Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/05cb5ac5-15af-4793-b9dc-33816faea911 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.

    1h 13m

  5. FEB 1

    Cookie, Claude Bot, and the “Run It on a Pi” Rule

    Show Notes 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. Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working 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.

    1h 38m

  6. JAN 25

    AI Everywhere: Smart Homes, Smarter Servers, and Dumber Customer Service

    This week starts nerdy and only gets nerdier in the best way. Michael and Damashe bounce from Apple rumors to AI customer service fails, with plenty of practical tech talk in between. 🤖 Apple, AI, and the Future of Siri We dig into the rumors around Apple’s AI direction and what it might really mean for Siri, a possible Home hub device, and Apple’s partnership with Google’s AI models. Are we finally close to a version of Siri that feels truly useful? We share what we’re hopeful about and what still feels like vaporware. 🧠 General AI vs. Specialized AI From Perplexity to Amazon Q, we talk about the shift from “AI that tries to know everything” to smaller models trained for specific tasks. Why focused AI might actually be more helpful and less likely to make things up. ☁️ Amazon Q and Learning AWS the Easy Way Michael has been setting up Amazon SES and got a firsthand look at Amazon’s built-in AI assistant, Q. We talk about how tools like this can make complex platforms like AWS more approachable, especially when you can ask follow-up questions in plain language instead of digging through documentation alone. 📧 Why Michael Is Switching to Amazon SES Michael walks through why he’s moving WordPress email over to Amazon SES. The big takeaway: sending email at scale can be shockingly inexpensive if you’re willing to do a little setup yourself. We also cover SPF records, sending domains, and a few beginner tips to avoid common mistakes. 🏠 Smart Home Wins and Headaches From smart locks that won’t unlock to garage lights that randomly stop responding, we share real-world smart home frustrations. We also talk about Matter, Thread, hubs, and why the future of smart homes should mean fewer extra boxes and more reliable automations. 📞 When AI Customer Service Goes Wrong Damashe shares a frustrating experience with an AI phone system that slowed everything down instead of helping. We talk about what good AI customer service should look like and how companies are missing the point when bots just add extra steps. 🎬 Apple’s New Creator Subscription Apple now has a Creator bundle subscription that includes Final Cut, Logic, and more across Mac and iPad. We break down who it might make sense for and when it’s probably cheaper to just buy what you need. Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/e1bbbb85-c1d5-48ad-bd90-4aa7d9cf011e 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.

    1h 32m

  7. JAN 18

    Chunk the Text, Treat the Room, and Let Your Assistant Do the Follow-Up

    Show notes (Technically Working, Episode 146) This week starts with a dramatic voice demo and turns into a practical conversation about TTS quality, accessibility, and the friction that slows down real work. In this episode, we talk about: More expressive on-device voices (and why “emotion” in TTS can be impressive but unpredictable) Why some AI voices drift over long reads (like losing low end after a few thousand characters) The practical fix: chunking text around 3,000 characters at sentence or paragraph boundaries The jarring side of expressive TTS: when the tone suddenly shifts mid-training Mac code editor accessibility and workflow: VS Code feeling clunky with VoiceOver navigation Nova being close, but still having VoiceOver quirks (like wrapped-line re-reading) Missing the flexibility and simplicity of TextMate A quick audio reality check: room reverb, mic position, and loud breathing in the mic Why it’s worth listening back sometimes, even if you usually don’t “Personal intelligence” assistants: Gemini connecting deeper with Gmail, Calendar, Photos, and Drive, and what that could enable Stream Deck Plus on sale (knobs!) and the bigger question: is the software accessible enough? Capture friction and follow-up problems: Getting ideas out of your head fast Using automation to sort notes into reminders, drafts, and follow-ups Why the Apple Watch action button might help reduce steps PLAUD recording devices: improved hardware button design, but app accessibility still matters Local processing ideas: Raspberry Pi options for local transcription and LLM workflows Listener feedback: Squarespace questions and a quick look at support options (tip jar vs Buy Me a Coffee) Feedback and contact: feedback@technicallyworking.show Support the show: Visit technicallyworking.show and click “Support Us” to leave a one-time tip or set up a recurring amount. Mastodon: @payown@dragonscave.space @damashe@technically.social @tw@technically.social Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/1396d590-a7dc-4a88-8455-1b3da1991eb2 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.

    1h 18m

  8. JAN 11

    Teaching Tech, Tethering Pain, and a Little CES Talk

    Episode 145: Teaching Tech, Tethering Pain, and a Little CES Talk This week we bounce between real life and real tech: why tethering still makes us want a MacBook with built-in cellular, what passkeys look like in the real world, and how Google Family Link pushes you into creating Gmail accounts for kids. We also talk honestly about teaching tech, why we often prefer working with people who are ready to level up their productivity, and how listener feedback shapes where the show goes next. Plus, a quick CES roundup with a few gadgets and ideas that actually stood out. In this episode Late-night work limits, and planning so tomorrow doesn’t get wrecked Tethering frustration, and the “just give us a MacBook with cellular” wish Michael’s living-room recording setup: Vocaster + OWC dock + Zoom, no virtual device chaos Google Workspace security alerts: suspicious login emails and what to check Passkeys: what’s great, what’s still confusing, and why some services still ask for a code Family Link and kids’ Google accounts: why Google requires @gmail.com, and how passkeys fit in Shared iCloud Passwords groups so parents can manage kids’ logins Password manager friction on Mac: Apple Passwords prompts vs 1Password workflows Listener feedback and the point of the show: it’s not a weekly “how-to,” it’s real conversations Teaching tech: beginner wins, real frustrations, and why “productivity level” training can be a better fit CES notes: mobility tech, batteries, smart locks, and a few other items that caught our attention Quick Surf app check-in: progress, but still clunky in places Support and contact info, plus Mastodon handles and the show hashtag Support Technically Working by contributing to their tip jar: https://tips.pinecast.com/jar/technically-working Find out more at https://technically-working.pinecast.co Send us your feedback online: https://pinecast.com/feedback/technically-working/c074c0cd-6feb-44da-bde8-e4a9321fd9f3 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.

    1h 19m
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About

"Welcome to 'Technically Working', the go-to podcast for tech enthusiasts and productivity seekers alike. Hosts Michael Babcock and Damashe Thomas take you on a journey through the ever-evolving world of technology and productivity. As Mac OS and iPhone users, they share their personal experiences and tips on staying productive while using these tools. But they don't stop there - they also explore other platforms like Android and Windows to bring you a comprehensive view of the tech landscape. Tune in each episode to hear them keep each other accountable, discuss the latest tools and strategies, and share their journey to reaching their goals. Whether you're a small business owner, freelancer, or simply looking to boost your productivity, 'Technically Working' is the perfect podcast for anyone looking to level up their tech skills and get things done."

Information

  • Creator
    Damashe Thomas and Michael Babcock
  • Years Active
    2023 - 2026
  • Episodes
    157
  • Rating
    Clean
  • Copyright
    © Copyright 2026
  • Show Website
    Technically Working

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