Technically Working

Episode Description Michael is getting hands-on with the RØDECaster Pro II, and thanks to Sean’s AccessCaster software, the mixer is finally usable without relying on its touchscreen. Michael and Damashe walk through the hardware, routing, multiple-computer setup, smart pads, monitoring, and what accessible third-party software changes about the value of otherwise inaccessible hardware. The conversation also moves into Michael’s upcoming guide dog training, Apple hardware and the folding iPhone discussion, Siri and podcast transcripts in Earshot, the Technically Working website rebuild, remote mixer control, and Damashe’s experiments using the Drafts MCP connector with Claude. Feedback: feedback@technicallyworking.show Website: https://technicallyworking.show Chapters 00:00:00 The RØDECaster Pro II Sounds Different 00:02:23 Getting Started With AccessCaster 00:16:28 Breaking News and Guide Dog Training 00:20:38 Apple Hardware, Macs, and the Folding iPhone 00:23:39 Siri in macOS and Context Menu Changes 00:29:42 Earshot, Siri, and Podcast Transcripts 00:34:03 Going Deeper Into RØDECaster Routing 00:44:32 Accessibility Beyond a Touchscreen 00:49:30 Earshot Codes, Feedback, and Mastodon 00:51:52 Thoughts on Apple’s Latest Event 00:58:34 Rebuilding the Technically Working Website 01:04:51 RØDECaster Wi-Fi and Remote Control 01:11:51 Drafts, MCP, and Letting AI Clean Things Up 01:15:43 Wrapping Up TW180 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/d6675ed6-d482-4f7b-b19a-c6736090513d 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.

Damashe is joined by Shaun Preece of Double Tap to talk about what happens when AI coding turns “I wish this worked differently” into “maybe I can fix it myself.” Shaun shares how he went from programming years ago to experimenting with Claude Code, while he and Damashe compare how AI has changed the way they research, plan projects, verify information, and learn while they build. They talk about keeping AI from wandering off, asking questions one at a time, using one AI to check another, and knowing when you still need to verify the answer yourself. The conversation gets especially practical when Shaun explains how he used AI-assisted coding to make much of the RODECaster Pro II accessible. That meant figuring out how the mixer communicates with its software, reverse-engineering commands, testing across different setups, and building an interface that can announce changes as controls are adjusted. They also get into computer-use agents, whether AI-generated software has real value, the difference between a quick experiment and a project you actually maintain, and Shaun’s work making Keychron keyboard configuration more accessible. It all comes back to one idea: AI does not have to help you build the next big app. Sometimes it can simply help you fix the things that get in your way and make your computer yours again. 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/fee388ee-c70a-4fb0-a6e0-cc3de959c4f3 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.

Technically Working 178: I Just Don’t Want to Do It Show Notes Michael and Damashe start out talking about GPT 6 and the ways AI has moved beyond being something interesting to experiment with and into something they actually use to get work done. Damashe shares how ChatGPT helped him troubleshoot a machine by finding and working through the documentation, while Michael talks about using computer use to handle WordPress changes and other tasks he already knows how to do but, as he puts it, sometimes just doesn't want to do himself. That leads into a conversation about when handing work to AI makes sense, when you still need to check its work, and how Michael is limiting access when letting AI work on websites. They also talk about volunteer work, last-minute requests, and Michael's goal of being more selective about the unpaid work he takes on. Then Michael asks for "no judgment" before revealing his latest purchase: a RØDECaster Pro II. His current mixer is starting to show its age, and the RØDECaster offers dual USB connections, mix-minus, multiple outputs, and the flexibility he wants for live and hybrid audio work. The problem, of course, is accessibility. Michael and Damashe talk through whether the RØDECaster can be made usable through existing workarounds, custom software, computer use, or direct device control. From there, the AI conversation returns because apparently every website needs an AI now. They consider whether smaller local models could actually be useful inside apps for things like better podcast search without turning every product into another AI chatbot. With an Apple event approaching, Michael and Damashe make some predictions. A folding iPhone leads to theories about Touch ID, including Damashe's hope that Apple puts it in the Apple logo on the back. They also talk Apple Watch, HomePod, Apple TV, Siri, what they might buy, and how Apple could handle a major event and a future leadership transition. Michael has also been relying on Siri more than he expected. Some recent successes with messages, calendar events, and reminders have him wondering how useful Siri could become once third-party apps can expose more of their features. That naturally turns into what Siri support should look like in a podcast app. Damashe wants simple commands like playing the latest episode of a show, continuing the queue, or moving to the next item. Michael shares some of the Siri work planned for Earshot along with recent player improvements. They wrap up with more Earshot changes, including easier episode and chapter navigation, folders that survive OPML exports, episode filtering, and finally getting auto-expiring podcasts working. In This Episode Using GPT 6 for research, troubleshooting, planning, and everyday work A free month of Earshot Plus for Technically Working listeners Letting computer use handle the tasks you know how to do but don't want to do Reviewing AI work instead of blindly trusting it Limiting AI access to WordPress sites Cutting back on last-minute and unpaid work Michael buys a RØDECaster Pro II The accessibility problem with modern audio hardware Could custom software make the RØDECaster accessible? AI showing up everywhere Where smaller local AI models might actually be useful Folding iPhone and Touch ID predictions Apple Watch, HomePod, Apple TV, and Siri expectations Michael starts trusting Siri a little more What Siri support should look like in a podcast app New Earshot playback and navigation controls Preserving folders in OPML exports Episode filtering and auto-expiring podcasts Chapters 00:00 - GPT 6, Earshot Plus, and putting AI to work 05:00 - ChatGPT versus the technician 09:50 - Computer use and "I just don't want to do it" 12:51 - Doing less free work 13:54 - No judgment: Michael bought a RØDECaster Pro II 20:00 - Can inaccessible audio gear be made accessible? 26:31 - Everybody has an AI 28:36 - Apple event predictions 34:20 - What Apple hardware are we actually buying? 40:00 - Siri, Apple events, and what comes next 50:00 - Michael is starting to rely on Siri 53:30 - Calendars, reminders, and task apps 56:45 - What should Siri do in a podcast app? 60:00 - New Earshot playback controls 63:20 - OPML folders and different ways of listening to podcasts 65:18 - Filters, auto-expiring podcasts, and finally solving the original problem Links Mentioned Technically Working Feedback: feedback@technicallyworking.show Support Technically Working Earshot Podcasts on the App Store 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/5b9d0997-8857-41a0-a909-e2dd90002cde 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.

Technically Working 177: The Bot Couldn’t Get Out Show Notes Michael and Damashe begin with a look at how AI can turn convention documents into WordPress pages, Gravity Forms, confirmation messages, and other ready-to-use materials. They discuss why a smoother payment process matters and how showing people only the instructions they need can prevent abandoned registrations and unpaid entries. Then Damashe reacts to rising Mac prices, explains why selling his MacBook Pro may have been a poorly timed decision, and considers whether things have become bad enough to buy another Windows computer. Michael shares useful shortcuts and recent experiences with Codex and ChatGPT, while both hosts stress that AI-generated work still needs to be reviewed. The conversation also covers Postmark, Cloudflare, transactional email, and the decision to rebuild the Technically Working website with familiar WordPress tools. Damashe explains why he does not want his business depending on a software stack he barely understands. Along the way, the hosts offer a warning about installing several WordPress caching plugins and explain why more caching does not make a website faster. Michael shares the latest Earshot improvements, including faster feed refreshes, haptic feedback, adjustable descriptions, new accessibility settings, and category browsing. The two consider how server-side podcast feed checking might work and what it could cost. Finally, Damashe explains why the Technically Working Mastodon bot never appeared during the ACB convention. He secured the server so thoroughly that the bot could not get out. The planned solution involves a Raspberry Pi, Tailscale, and one more project competing for his attention. In This Episode Using AI to build WordPress pages and Gravity Forms from existing documents Creating clearer registration and payment flows Why AI-generated forms and websites still need human review Rising Mac prices and Damashe’s poorly timed MacBook Pro sale ChatGPT and Codex shortcuts and computer control Postmark, AWS SES, and Cloudflare for transactional email Rebuilding the Technically Working website with GeneratePress Choosing a software stack you understand well enough to maintain Why several WordPress caching plugins will not make a site faster Earshot feed refresh, haptics, descriptions, and category browsing The possibilities and costs of server-side podcast feed checking Panic returning money to Playdate customers The mystery of subscriber number one How Damashe accidentally trapped the Technically Working bot Tailscale, Raspberry Pi projects, cameras, and internet failover 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/ba76eb96-515b-4c08-9587-0684eae26143 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.

I Shouldn’t Have to Tell the Intelligence Michael and Damashe explore what happens when AI tools are asked to work instead of simply answer questions. Damashe shares his experiences using ChatGPT to reorganize a Numbers spreadsheet, Claude to manage email, and an AI-assisted product search that produced a very convincing but completely inaccurate hard drive price. That leads to a larger question: If you ask AI to research something, should you also have to tell it to search the web and verify the information? They discuss the rough edges of today’s AI agents, why this period feels like the early days of personal computing, and whether these tools will eventually become reliable enough to work without constant supervision. They also talk about software companies rewarding new customers instead of loyal ones, VoiceOver and Zoom frustrations, sharing health data with AI, configuring ChatGPT and Codex on the Mac, repurposing computers as servers, and the photo they forgot to take when they finally met in person. In This Episode Discounts for new customers versus rewards for existing customers VoiceOver keyboard commands that stop working until the Mac is restarted Using whois and dig to look up domain information Zoom’s loud and repetitive notifications Rising computer and storage prices Using ChatGPT to reorganize a Numbers spreadsheet Comparing ChatGPT computer use with Claude’s computer-control features Organizing email through Fastmail and MCP The permissions Codex needs to control apps on macOS An imaginary 24-terabyte hard drive deal that was too good to be true Why AI research should include checking the original source Whether we are living through the early personal-computer era of AI Asking one AI to review another AI’s work Giving AI access to Apple Health and years of health data Continuous glucose monitors and accessible glucose tracking Apple Watch reminders, workout encouragement, and handwashing alerts Customizing the ChatGPT app’s keyboard shortcuts Moving keyboard focus to the main chat composer with Shift+Escape Repurposing a Mac mini and mini PC as home and office servers Moving Plex and an audiobook library to Linux Why the show is not getting any shorter Links and Resources Gravity Wiz GeneratePress Fastmail Model Context Protocol Dexcom Audiobookshelf Plex Will Codex Reset? Pinecast Connect With Us Send your feedback to feedback@technicallyworking.show . Michael: @payown@dragonscave.space Damashe: @damashe@technically.social Technically Working: @tw@technically.social Join the conversation using #TechnicallyWorking . 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/ceb7f7e2-2de2-41b5-8a9f-36a0454bb986 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.

Michael and Damashe are back after St. Louis with an episode that runs long on opinions. Michael shares early Earshot numbers, explains why he is building iCloud sync with privacy defined up front, and walks through why the iOS simulator makes VoiceOver testing nearly impossible. Damashe lays out his solution for Meta and everyone else building smart glasses: stop using disabled people to justify features you should not ship the way you are shipping them. Also in this episode: switching from Terminal to the Codex app, whether Stage Manager could replace virtual desktops, Todoist versus Reminders, the trick to actually remembering names, and a plan to smoke chili on Sunday. In this episode Recapping the shortest show they have ever published, recorded in person in St. Louis Earshot on the App Store: 249 downloads, 40 subscriptions, and zero marketing so far Why Michael is cautious about third party subscription analytics and what data is actually available in App Store Connect The tradeoffs of Apple standing between developers and customers iCloud sync coming to Earshot: library, queue, play position, and bookmarks, with the help screen spelling out exactly what gets stored Stress testing with an OPML file of 1,100 feeds and an inbox that pulls in 3,000 episodes every other day Refresh performance and where concurrent feed checking comes in Why Michael is not asking for reviews inside the app, and Damashe's case against review prompts that interrupt you The VoiceOver experience in the iOS simulator, and why "heading, heading, heading" made Michael start pushing developer builds straight to his phone What this means for sighted developers who want to build accessible apps Accessible screen sharing on the Mac, the voice pitch quirk, and canceling a remote access subscription Damashe's take on smart glasses, person recognition, and why contacts should be the boundary instead of a social graph Whether AI should describe people at all Saying someone's name five times so you actually remember it Michael's move from Terminal to the Codex app, plus a good experience with Claude Cowork Could Stage Manager work as a virtual desktop for a VoiceOver user? Neither of them knows, so tell them Beta features in shipped builds, and using smaller TestFlight groups to absorb schema migrations Todoist, Reminders, Fantastical, and getting AI chats to file reminders for you Perspective Tasks as a free option worth a look What an operating system might look like if it were just an edit box, and why Damashe is not sold Links and mentions Earshot on the App Store Perspective Tasks by Michael Doise and Taylor Arndt Stage Manager on macOS: if you use it with VoiceOver, they want to hear from you Get in touch Email the show at feedback@technicallyworking.show Michael on Mastodon: https://dragonscave.space/@payown Damashe on Mastodon: https://technically.social/@damashe The show bot: https://technically.social/@tw Use the hashtag #TechnicallyWorking, and capitalize the T and the W so screen readers say it correctly. Support the show One time tips and monthly subscriptions are both available at https://technicallyworking.show, under the support us link. Shout out to subscriber number one, whoever you are. 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/e17aa084-39fd-42ce-80f4-6cc75c61081a 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.

Michael and Damashe record live from the ACB Convention in St. Louis, in a suite generously loaned by Larry Watkinson and Kayla. This one is a room full of people, a passed microphone, and a lot of new tech announcements. The two hosts also met in person for the first time this week. Handshakes, no hugs. In this episode Earshot was accepted into the Apple App Store during convention week. Michael is now officially an app developer, which is still a little strange to say out loud. Taylor Arndt, COO of Techopolis, walks through Start Testing, a project she has been building for three years. It handles bugs, issues, and tasks, syncs with GitHub, and can pull in TestFlight feedback. There is a free plan for a single solo project, and a new Techopolis for Open Source tier at $3 a month or $30 a year for three projects and three contributors. Their AI agent, Lyra, can turn a long transcript into a full set of issues and a working plan. Michael Doise from Techopolis introduces Start Navigating, released the same day. It is a free indoor navigation app that lets you record a route from point A to point B, add markers along the way, and follow it later using compass directions, step counts, and ARKit. There is route recovery if you are not standing at the start, plus early support for sharing routes to a public database so others can download them. Think elevator to Starbucks, recorded once and shared with everyone arriving later in the week. Jeff Bishop gives an overview of BITS, the Blind Information Technology Solutions, a 501c3 affiliated with ACB focused on training, mentoring, and encouraging people to build things. He also talks about BITS Connect, the new iOS app built with Techopolis, which brings members and non-members alike into one place. Also in this episode: the BITS Blinky, barbecue at Sugar Fire, a review of the mac and cheese, and why the Simple PTT radios made convention comms much better this year. Gear used for this episode Zoom H6 Studio, Audio-Technica AT2005 for Michael, Shure Beta 87A for Damashe, both wired XLR. The XLR cables were paid for by tip jar supporters, so thank you. Links Start Testing Start Testing pricing Perspective Apps, including Start Navigating Michael on Mastodon Damashe on Mastodon The TW bot Email: feedback@technicallyworking.show Hashtag: #TechnicallyWorking Thanks to Larry and Kayla for the space, and to everyone who crowded into the room to be part of it. 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/129cf90e-8ee0-4f7c-a26f-43be35a5a511 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.

Feed Drop Hey, we're sharing the first episode of Our Perspective, while Damashe waits for the recording gear to arrive to his house for episode 174. Enjoy and subscribe to our perspective. 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/a60ff80b-0414-497a-97f3-b3f2534225d4 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.

Episode summary Michael has submitted Earshot to App Review, leading to a tour through App Store Connect’s confusing controls and an expedited-review form that required sighted assistance. He is also stress-testing Start Posting, a Mastodon scheduling tool designed with screen-reader users in mind, while both hosts prepare for ACB in St. Louis and consider an evening meetup. Damashe previews the A. T. Guys booth lineup, including cane pouches, the Dot Pad, Zoom audio gear, large-print keyboards, and the Shokz OpenFit 2+. From there, the conversation moves to AirPods and Find My, Michael’s missing earbud, filling in on Double Tap, possible cameras in future AirPods, football streaming, over-the-air DVRs, and the NAS Damashe will eventually have to buy. In this episode 0:00 – Recording late and attempting a short show 0:58 – Earshot enters App Review 1:38 – App Store Connect and the expedited-review process 4:09 – Start Posting and Michael’s Mastodon routine 5:40 – St. Louis barbecue and ACB meetup plans 9:10 – World Cup visitors discover Costco and Buc-ee’s 10:53 – Reviewing the Politics Politics Politics podcast 13:46 – ACB booth inventory, demonstration units, and shipping 14:33 – How the cane pouches are designed 17:20 – Dot Pad, Zoom recorders, and large-print keyboards 18:48 – Why Damashe likes the Shokz OpenFit 2+ 20:18 – AirPods and Find My quirks 22:30 – Michael’s missing AirPod Pro 25:45 – Michael fills in on Double Tap 28:26 – Could future AirPods include cameras? 30:18 – Heat, humidity, and remembering to hydrate 31:50 – Football streaming and NFL Sunday Ticket 32:48 – Over-the-air television, Channels DVR, and NAS hardware 35:00 – Listener feedback, Mastodon, and meeting up in St. Louis Call for feedback Damashe is looking for firsthand experiences with UGREEN NASync systems and current Synology hardware. Send your recommendations, warnings, and preferred NAS configurations. If you are in St. Louis during ACB and would like to meet after 5 p.m., reach out by email or Mastodon. Mentioned in this episode App Store Connect Techopolis — home of Start Posting 2026 ACB Conference and Convention A. T. Guys Dot Pad Zoom PodTrak P4next Zoom H5studio Zoom H1 XLR Zoom H6studio Shokz OpenFit 2+ Apple Find My Politics Politics Politics Double Tap Channels HDHomeRun UGREEN NASync Synology NAS products Support the show Support Technically Working through the Tip Jar . Thanks to everyone who already supports the show. Find us Email: feedback@technicallyworking.show Michael on Mastodon: @payown@dragonscave.space Damashe on Mastodon: @damashe@technically.social Technically Working bot: @tw@technically.social Follow the conversation using #TechnicallyWorking , with a capital T and W . 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/d52462c8-c436-450c-8c45-d4f545a52e19 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.

Michael has Echo Vision glasses in for testing, and before he can say much about how they work, there is the beep. A loud, high-pitched beep every time the glasses go into the case or come back out. Damashe tries to be reasonable about it. It does not last long. From there the show goes AI-heavy: Fable's possible expiration, sub-agents that write themselves, a Cloudflare Workers email parser, and the Claude for Chrome extension. In this episode Echo Vision first impressions: the beep, the four-beep battery check, and the tiny sticker on the bridge that keeps them from charging out of the box The setup problem, where the app knows an update is available but the update button is dimmed and there is no obvious way to connect to Wi-Fi Why convention is the real test for any connected device Earshot build 151 is live on TestFlight with monetization: monthly, annual, and lifetime options plus three tip jar levels under Help and About Damashe's request for a plain "What's New" section alongside Kashe's story Fable's expected expiration, the rumor about it moving to the higher plans, and the temporary usage increases at claude.ai/settings/usage Damashe built an email parser on Cloudflare Workers to replace Parcel's removed email forwarding, with a Sonnet fallback when parsing fails. Open source release coming after a security pass Telling Claude it is too expensive to do research, and watching it spin up a Sonnet-powered docs sub-agent on the fly Claude's screen reader mode ( claude --ax-screen-reader ) and the menu change that trips you up: press the number, then press Enter Using the Claude for Chrome extension to get through Cloudflare's redesigned interface Michael switched from Fable to Codex, plus a workaround for pasting long terminal output into Fable on the web Making podcast content readable by AI: MCP servers, markdown endpoints, and whether SEO plugins handle any of it Techopolis is building starttesting.net , plus a Buffer-style social scheduling tool in the spirit of Meet Edgar Substack lets you export subscriber emails and takes 13 percent. A shoutout to Matt at Pinecast for not doing weird things with the tip jar 40,481 downloads and counting. Thank you for sharing the show Convention plans: Michael is in St. Louis the 22nd through the 1st, Damashe the 25th through the 29th Links Claude for Chrome: https://claude.ai/chrome Start Testing: https://starttesting.net Tip jar and supporters: https://technicallyworking.show Contact us Email: feedback@technicallyworking.show Michael: https://dragonscave.space/@payown Damashe: https://technically.social/@damashe The show bot: https://technically.social/@tw Or use #TechnicallyWorking and we will see it 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/3d7709cf-3571-42be-897a-4d2e99a52867 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.

Technically Working 171: We Also Do Interiors Episode summary Michael and Damashe finally come clean about the interior design business they have been running in secret. Damashe weighs a Comcast contract against fiber that has not arrived yet. Michael downgrades his Claude plan, turns Claude into a marketing assistant, and moves Earshot closer to the App Store. Plus Braille inside the box of the new glasses, the Orbit Player getting Bard support, hotel status hacking, and travel tips ahead of St. Louis. In this episode VoiceOver volume levels and why the number changes depending on headphones, kids, and mixers (0:00) Damashe's internet dilemma: AT&T fiber with no timeline, Comcast at $150 a month for a symmetrical gig, and a one year contract with a $35 per month early termination fee (0:31) Running a contract past AI before you sign it, and why pressure tactics do not work (5:36) Starlink through US Mobile as a possible temporary option (28:11) The interior design confession, and the emails that started it (13:10) A new marketing idea: pull episode teasers off the staging site, have AI read them dramatically, and post the clips (14:00) Word of mouth is working. Running into listeners at NFB in Austin (15:42) The new glasses arrive, still in the case, but there was Braille inside the box (17:03) ChatGPT's iOS app loses its headings, and Michael heads back to Claude (21:11) Downgrading from $100 to $20 on Claude and experimenting with Ollama Cloud (30:34) Hands on with the Orbit Player, and Bard support arriving on the 15th (22:28) Earshot monetization takes shape: Earshot Plus, a tip jar, App Store Connect setup, tax forms, and the 15 percent versus 30 percent form (33:20) Earshot gets a shout out on Double Tap in a segment about useful vibe coded tools (35:15) Marriott Bonvoy, Uber One, and the free coffee economy of lounge access (44:47) ACB Convention is across all 10 streams. Listen at acbmedia.org , and calendar events populate to the 2026 Conference and Convention button in the ACB Link app (53:03) Still hunting for good barbecue in St. Louis. Beef ribs or brisket preferred (38:20) Airport assistance: do you check the box when booking, or just show up and ask? Using Aira, calling a friend, and deciding when to just walk to the gate yourself (1:03:18) Visualize Access and using pre trip airport orientation to skip the wait (1:08:03) Call for feedback We want your travel tips. Packing, navigating new spaces, dealing with airports and assistance requests. Send them to feedback@technicallyworking.show. Mentioned in this episode ACB Media: acbmedia.org ACB Link app, 2026 Conference and Convention section Double Tap podcast Orbit Player Bard (Braille and Audio Reading Download) Graphic Audio: graphicaudio.net Aira Visualize Access Cooper's BBQ and Taco Deli, Austin Brailsmith Support the show Tip jar supporters get early access. Head to technicallyworking.show and activate the Support Us link. Find us Feedback: feedback@technicallyworking.show Michael on Mastodon: @payown@dragonscave.space Damashe on Mastodon: @damashe@technically.social Show bot: @tw@technically.social Hashtag: #TechnicallyWorking Want the social posts and Substack version next? 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/985010bb-1515-4599-818a-2e5a0a706b5f 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.

Audio Gear Talk Damashe kicks off with an audio interface mishap. He shipped most of his demo gear to Austin for the NFB National Convention, including his usual recorder, and had to quickly set up the Zoom H5 Studio instead. After a few minutes of confusion over gain knobs, the fix turned out to be simple: turn the right one. He walks through his thoughts on the Zoom H1, H4, H5 Studio, H6, H6 Studio, and P4next, covering which ones he prefers and why (mainly manual gain control over digital menus). Claude Remote Control Coding Michael shares his experience using Claude's remote control feature while traveling in Vegas. He pushed eight TestFlight builds for Earshot from his phone while away from his laptop, sending prompts, reviewing bug reports, and even having Claude message a friend to check on his machine. Claude also handled app signing certificates without Michael physically present to approve it. They talk through when remote control coding actually makes sense versus when it is overkill. Fable Access and Model Usage A quick discussion on Anthropic's Fable model, its usage costs compared to Opus 4.8, and the tip of using a cheaper model like Sonnet to draft prompts before handing them to a more expensive model for the actual work. Recording and Editing Mishaps Damashe accidentally rendered a recording at sped up playback speed while editing in Reaper, cutting an hour long file down to 39 minutes. They also compare notes on Alphonic's redesigned interface. Packing for Travel With ACB National Convention and NFB Convention both coming up, Michael and Damashe compare packing strategies. Topics include suitcase versus tank roll, packing cubes, folded outfit pouches, and Damashe's strong opinion on four wheeled suitcases over two wheeled ones. Streaming Service Frustrations A shared rant on subscription price increases, particularly Amazon Prime adding ads to Prime Video and raising prices for features nobody asked for, plus general annoyance with Apple's constant upsell notifications. Listener Question: Buying a Windows Laptop Longtime listener Chad wrote in asking for laptop advice ahead of a new purchase meant to last five to seven years. Michael and Damashe recommend: Snapdragon (ARM based) processors over Intel or AMD if budget allows 16GB RAM minimum, 24 to 32GB if affordable 512GB storage as a comfortable baseline Lenovo as their preferred Windows brand, specifically the ThinkPad X1 Carbon or ThinkPad T14s Snapdragon Checking Paul Thurrott's site ( thurrott.com ) for detailed laptop reviews Physically testing the keyboard in store when possible Also Discussed Whisper Flow and FlowType dictation apps Google account overload Siri reliability issues on iOS beta A Raspberry Pi 5 (16GB RAM, unopened) up for grabs from Damashe Convention Plans Both hosts will be in St. Louis for ACB National Convention, July 24 to 29. Damashe is also at NFB National Convention in Austin this week. Listeners in either city are invited to reach out. Contact Email: feedback@technicallyworking.show Michael: @Payown@dragonscave.space Damashe: @Damashe@technically.social Show bot: @TW@technically.social Hashtag: #TechnicallyWorking Support the show at technicallyworking.show/tipjar Episode 170 • Runtime: ~1:18:00 Want me to move on to social posts next?# Episode Notes Notes go here 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/7baa238c-1c81-4225-ae54-189d75ecdd8c 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.

What We Cover This Week <h4>Earshot Development Progress and the Claude Workflow</h4> Michael walks through where the Earshot podcast app stands after another round of Claude-assisted development. The improvements keep landing, the test loop is tightening, and Michael shares what's working in the build process. If you want to kick the tires yourself, the public TestFlight link is below. <h4>Damashe on the New Siri Beta</h4> The capabilities are genuinely impressive — but the limitations around third-party app integration are exactly where the friction shows up. Damashe gets into what's working, what isn't, and why the third-party gap matters more than Apple seems to think. <h4>FloType for Blind and Low-Vision Users</h4> We promised we'd point listeners to FloType, the new VoiceOver-first keyboard from developer Rocco. It picks up the eyes-free typing approach that Fleksy pioneered and FlickType refined — tap roughly where the keys would be on a QWERTY layout, swipe right to commit the word, swipe down to cycle suggestions. The public beta opened in June 2026 and is actively under development. Links below. Apple's Price Increases — and the Refurb Math Damashe and Michael unpack Apple's recent price increases across the lineup. Damashe wasn't surprised that they happened — supply chain pressure plus expired component pricing made it inevitable — but he was surprised by how fast they hit after Tim Cook's announcement. We get into why the iPhone is conspicuously absent from the increases (Damashe's read: Apple is holding that lever for the September refresh). <h4>The MacBook Neo Touch ID Refurb</h4> Michael flags that the MacBook Neo with Touch ID is now in Apple's refurb store at $679 — but the savings versus the previous refurb price are only about $20. That sparks a broader conversation about when Apple's refurb store actually wins. Our take: the included AppleCare tips the value calculation in Apple's favor versus Amazon, B&H, or other retailers — even when the headline price doesn't. Pirate Ship for Cheap, Sane Shipping Quick recommendation for anyone shipping on eBay or otherwise: Pirate Ship integrates cleanly, the rates are hard to beat, and the workflow is straightforward. Both of us use it. Smart Glasses: Echo Vision from AGIGA, Meta Ray-Bans, and Why Damashe Is Holding Off Michael received a free pair of Echo Vision smart glasses from AGIGA and is starting a head-to-head against his Meta Ray-Bans. He'll be reporting back as testing continues. Damashe explains why, despite putting money down on the Echo Vision earlier, he hasn't pulled the trigger on a purchase. The delayed shipping timeline, ongoing concerns about real-world functionality versus price, and a frustrating experience with his current Oakley Vanguards (uncomfortable fit, lens color issues) have all stacked up. The plan: let Michael run the gauntlet first, then decide. This leads into a broader technical point about smart glasses generally — the importance of a separate compute device versus trying to cram everything into the frames themselves, and what that means for where the category is actually heading. AI Policy Whiplash and Why It Matters Damashe gets candid about his frustration with the rapid policy shifts and government restrictions in the AI space — specifically around Anthropic's Fable model and the Mythos security tool. The deeper concern isn't any single rule; it's the inconsistency. Building a business on a platform whose ground rules change month to month is hard. The tech industry needs stability to plan, and right now it isn't getting it. Behind the Scenes We also work through some audio gremlins at the top of the episode (microphone swap, settings adjustments, phone static) — par for the course, and resolved before things really get going. Links and Apps Mentioned Earshot TestFlight FloType keyboard TestFlight FloType beta tester WhatsApp group Pirate Ship Apple Refurbished Store AGIGA Echo Vision smart glasses Meta Ray-Bans Connect With the Show Follow Technically Working on Mastodon: @TW@technically.social Reach Damashe at @damashe@technically.social Follow Michael @payown@dragonscave.space Send feedback, questions, or topics for future episodes our way, feedback@technicallyworking.show — we read everything. 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/9c098f14-de7d-4974-b5ad-8d692288a766 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.

Recorded on Father's Day, episode 168 opens with Michael and Damashe wishing each other a happy Father's Day before diving into everything going on in the world of AI, coding agents, Earshot, and more. Support the Show If you enjoy Technically Working, you can make a one-time tip or set up a recurring subscription at technicallyworking.show. Click the support link to get started. The Big Earshot News: Flutter is Out, SwiftUI is In Michael reveals he has switched Earshot from Flutter to SwiftUI after a day and a half of intense work. The reason: he wanted to add a feature that lets users customize and reorder their in-app actions. In Flutter, the only reliable way to rebuild that UI was to background the app or force-quit it, and neither of those felt acceptable. SwiftUI wins because it gives Michael a better path to features like Apple Shortcuts integration and data sync through Apple CloudKit, without requiring users to create an account. Build 113 on TestFlight will be SwiftUI. A phone overheating bug during playback is being fixed before that build ships. Damashe suggests delaying cross-platform work until the iOS version is solid, and floats using AI to translate SwiftUI to Kotlin for Android down the road. Michael is focused on option B: get it done, get it out, get people testing. Earshot TestFlight Beta The public TestFlight link is available. If you found it, you can use it. No need to ask for permission. TestFlight supports up to 10,000 testers, so there's plenty of room. A few early users have already switched from Castro and canceled their subscriptions, and Damashe removed Downcast while giving Earshot a real look. Upcoming features mentioned: auto-add to queue with options for add-to-end or add-as-next, and an Overcast-style theme for users coming from that app. The $100 Claude Plan and the Multi-Agent Setup Michael upgraded to the $100/month Claude plan because he kept hitting usage limits. The reason: he built a full multi-agent system in Claude Code specifically for Earshot development. Here's how it works: A planning agent pulls issues from GitHub It decides which of the other nine specialized agents should handle the work Agents include: security, accessibility, UI, and others The planning agent creates a plan, sends it with the issue to the assigned agent That agent completes the work, then passes results to a test agent If tests pass, the planning agent opens a pull request Michael reviews and merges Agents live as Markdown files in the ~/claude/agents/ folder. You can tag a specific agent directly, like @earshot-security , or run the whole loop through the planning agent. Michael got the idea from watching short-form video about loop-style AI workflows versus single prompts. He built the agent set by talking to Claude in the web interface, asking it to build out agents one question at a time. Anyone who wants to see what the agent files look like can email the show. Claude for Chrome: Damashe's Accessibility Workaround Tool Damashe has been using Claude for Chrome regularly, about a couple times a week. His main use case is getting around inaccessible web elements that VoiceOver can't interact with. Things like broken sliders, forms that throw vague error messages, or pages where he can't find a button to complete a task. He grants Claude permission to access the page, tells it what he's trying to do, and it figures it out. He noted it works in Helium, a Chromium-based browser, even though Claude officially only supports Google Chrome. Claude Cowork: One Use So Far Michael tried Claude Cowork once to order 50 flyers from a major national print chain. He uploaded the flyer file, told Claude to pick the right paper and add 50 copies to the cart. It got to the checkout page, picked glossy paper instead of the matte Mallory wanted, and even suggested adjusting the text color for better contrast. Not perfect, but impressive for a first try. Damashe plans to try Cowork this week to order business cards through Vistaprint, since there's something on that page he hasn't been able to get through accessibly. Codex Check-In: Damashe Plans a Revisit Damashe is going to give OpenAI's Codex another look in the terminal. When he tried it early on, he preferred how Claude worked and found Codex too noisy in the terminal. He acknowledges that in AI tools, things change fast enough that checking back in occasionally is worth doing, unlike, say, trying out a new calendar app. Spoiler: he doesn't expect to switch, but wants to see what has changed. Siri AI and Apple Intelligence in Beta 1 Michael is running the first beta of the new Siri with Apple Intelligence and has been impressed. He thinks if it ships on by default, it will surprise a lot of people. His comparison: asking Google Assistant on his Pixel 9 Pro to make a phone call still gets a refusal. Siri is actually doing things. He wants Siri to eventually handle appointment scheduling the way X.ai 's Amy and Andrew did back in 2017 and 2018, where you CCed an AI assistant on emails and it handled the back-and-forth. Damashe wonders whether Siri AI will require an iPhone 18 for any features, and thinks it probably won't, mostly because Apple already has enough work ahead getting the rollout right. The conversation also touches on Apple's folding phone and whether the price will ever make sense. The Build-It-Yourself Era Michael spotted a Microsoft session at the upcoming ACB Convention titled something like "The Build-It-Yourself Era," which caught his attention. The idea: AI tools have lowered the bar enough that sometimes the best software is the one you just ask Claude or Copilot to build for you. That philosophy is exactly how the Community Builder app came to be. Damashe extends this to a broader point about companies that laid off developers in favor of AI and may end up hiring back people who know how to use AI tools to build internal processes. Open Source and Accessible Spreadsheets Michael mentions some community work happening to build an accessible grid library in Python for a piece of open-source hardware software that was lacking accessibility. The goal is something you can arrow through, type into cells, and possibly add calculations to. Damashe gives a general shoutout to open source as something you can fork and fix when the original team won't prioritize accessibility. Audio Editing with AI: The Descript Comparison Damashe wants to test whether Claude Cowork can handle simple Reaper tasks, like trimming the last ten seconds of an audio file. Michael mentions using a different approach: he fed a transcript of the Our Perspective promo recording into Claude and asked it for edit points with time markers. It was off by a second or two but got him where he needed to go. Michael floats the idea of building something like Descript using an LLM and third-party services with Reaper underneath, and Damashe immediately points out that they never did get around to learning Reaper's scripting language even though LLMs make that way more approachable now. Hermes: Damashe Gets Excited Damashe still hasn't set up Hermes yet, but after listening to the June 10th episode of the Intelligent Machines podcast, where they interviewed the creator of Hermes for the second time, he is now much more interested. He had previously written it off as another OpenClaw-style tool, but the interview changed his thinking. He wants to run it on a Raspberry Pi and have it call out to a bigger model when needed. Michael suggests pairing it with Ollama Cloud and putting the Pi on Tailscale. Claude Getting Michael's GitHub Wrong Claude keeps assuming Michael's GitHub username is pay-on-media because his company is Payown Media LLC. It corrects itself, but it keeps happening. The fix: add the actual GitHub username to the CLAUDE.md file so it stops guessing. Listener Shoutout Shoutout to Jamie, who emailed to say he keeps listening even when topics go over his head because the show is good and entertaining. That is exactly what the show is going for. Podcast Numbers Total downloads: 36,919 Seven-day listens: 300 Episode 167 "Going to Atlanta": 174 listens Episode 166 "If You Used a Passkey, Why Are You Asking for a Code?": 185 listens Episode 165 "No Excuses Left for Inaccessible Apps": 210 listens Most episodes from 165 and earlier are sitting around 200 downloads, which suggests either Earshot beta testers are listening to the back catalog, new listeners are finding the show, or both. Where to Find Us Email: feedback@technicallyworking.show Michael: @payown@dragonscave.space Damashe: @damashe@technically.social Bot: @TW@technically.social Hashtag: #TechnicallyWorking (capitalize the T and W so screen readers read it right) 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/4e0882d3-2746-463c-8955-4b1d184fb5ee This podcast is powered by Pinecast . Try Pinecast for free, forever, 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 week, Mike and Damashe dig into Earshot build 99, react to WWDC 26, and ask the big question: are AI agent devices actually ready to replace your phone? Spoiler: your ride might end up in the wrong city. What We Talked About Earshot Update - Build 99 The new alphabetical library picker is live, with a count of how many podcasts are under each letter Per-podcast playback speed is now working: set a default speed, override it for individual shows, and it remembers your preference automatically The database migration bug from builds 88-95 is fixed; if your app was spinning and crashing, update to build 99 The app now gives you a useful error message instead of just failing silently if something goes wrong with the database If you are on TestFlight and want to send feedback, email feedback@technicallyworking.show - do not use the TestFlight feedback form, because Mike cannot reply to you there To get on the beta, find Michael on Mastodon Apple Deals Worth Knowing AirPods Pro 3 spotted at $179 on Amazon, Best Buy, and possibly Walmart AirPods 4 at $99 Apple Watch Series 11 (42mm GPS) at $299 WWDC 26 Impressions Mike went in with low expectations and came out a little underwhelmed Damashe has not watched the keynote but has listened to everyone talk about it Apple showed features live and uncut, which seems intentional - they want to prove the demos are real Certain AI features require M3 Pro or better on Mac, M4 or better on iPad, and iPhone 17 Pro iOS 26 and 27 compatibility stays the same - if your device runs 26 it will run 27, you just may not get all the local AI capabilities Damashe called the OS unification direction, and he would like you to use the hashtag DamasheWasRight accordingly iOS 27 Safari Notify Apple Intelligence can now watch a Safari tab and notify you when something changes Steven Robles used it to get notified when the Unify travel router came back in stock Both Mike and Damashe immediately thought: Ubiquiti restocks Touchscreen MacBook Speculation Mark Gurman is pointing toward a high-end OLED touchscreen MacBook Pro at a significant price premium Damashe's alternate theory: what if Apple makes a detachable touchscreen MacBook Neo instead of going ultra-premium The Neo already runs macOS on an A18 Pro chip at $600; a touch-capable detachable version aimed at schools and everyday users could make more sense than a $3,200 pro machine Both agree: a MacBook with cellular would be an instant buy, no questions asked Are AI Agent Devices Ready to Replace Your Phone? OpenAI is rumored to be working on a new form factor device built around voice interaction Damashe's argument: not yet, for several reasons - apps, authentication, companies not wanting to be commoditized, and the lack of strong local compute Uber and Amazon are not going to sit still while an agent turns them into a background API The local vs. cloud routing problem is real: you need a local model to manage where requests go, and we are not there on mobile yet Both see 2029-2030 as a realistic window for local compute on personal devices being good enough for most tasks The Plaud Pin has been sitting on a nightstand for months as evidence Siri and Third-Party Mail Siri can now surface airline reservations when you call airlines Open question: does it work if your reservation is in Gmail or Outlook instead of Apple Mail Shortcuts Getting Smarter The new AI-assisted Shortcuts builder could be the most useful thing in iOS 27 if it actually works Federico Viticci's hope: get Sherlocked properly this time Links and Contact Send feedback: feedback@technicallyworking.show TestFlight beta for Earshot: find Michael on Mastodon at payown@dragonscave.space Damashe on Mastodon: damashe@technically.social Bot: tw@technically.social Support the show: technicallyworking.show, click Support Us 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/3240cfe1-07d0-4cdc-b340-9d4131f7c84e This podcast is powered by Pinecast . Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

Passkeys are supposed to make your life easier. So why is Amazon still asking for a six-digit code after you just proved who you are with one? This week, Michael and Damashe dig into what companies are getting right and wrong with passkey implementation, including PayPal's rocky start and how one hardware security key can save you from a bad day on macOS. They also talk about Damashe's new office space, what it actually takes to organize a vending machine operation when you're blind, and why Braille labels still beat pulling out your phone. Plus: the GL.iNet travel router with built-in Tailscale, using Aira to read a Wi-Fi password off the bottom of a router, WWDC predictions including a folding iPhone neither of them is sure they want, and what happens to your whole week when you stop using Todoist. A lot happened. Almost none of it went as planned.

Michael kicks things off from a proper setup. Damashe kicks things off from a boom arm clamped to his nightstand — because he's mid-move and the show must go on. From there, the conversation covers a lot of ground: Michael is beta testing Quill, a new cross-platform Markdown writing app from BITS that runs on Mac and Windows, written entirely in Python. Damashe shares a LaunchBar trick he'd never tried before — copying and moving files entirely within LaunchBar — and it turns out it works exactly the way it should. Then things get into the meat of the episode. Michael has been building a podcast app using Claude as his primary coding tool. He's not an iOS programmer, but he can develop an iOS app — and that distinction matters. Accessibility has been part of the project from day one, including a rule in his CLAUDE.md file that every code change gets run through the accessibility agents from community-access.org before anything moves forward. No unlabeled buttons. No accessibility regressions. Just a rule that runs automatically. That leads to a bigger question: with AI tools making it easier than ever to build software, what excuse do developers actually have for shipping inaccessible apps? Michael makes the case that it's not a knowledge problem anymore. It's a willingness problem. Damashe pushes back on the "just vibe code it" framing. He has no problem with using AI to build things — he's doing it himself. What he takes issue with is the negligence: shipping code you haven't tested, don't understand, and haven't checked for security or accessibility, then asking someone else to deal with the fallout. Open source maintainers are already feeling this. Bug bounty programs are drowning in low-quality AI-generated reports. The tool isn't the problem. The behavior is. They also get into feedback — what it's like to receive bug reports when you're the one who built the thing — and Damashe shares the story of how he got Marco Arment to add rotor actions to Overcast, one conversation at a time. Links and things mentioned: Quill (BITS Markdown writing app for Mac and Windows) LaunchBar — https://www.obdev.at/products/launchbar/ community-access.org accessibility agents Overcast — https://overcast.fm Technically Working — Episode Notes Notes go here 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/6a089d48-76a4-43f5-b8af-6e63343769a8 This podcast is powered by Pinecast . Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

Michael's been frustrated with his current podcast app for months, so he did what any reasonable person would do: opened Claude, wrote a PRD, and started building. Thirty-six versions later, there's a working iOS podcast app with a cross-platform plan, real testers giving feedback, and a list of features pulled straight from what blind podcast listeners actually want. We get into the build process, including why Michael went with a phased approach, the testers who caught things he never would have (player controls missing above the tab bar, search being completely broken, follow buttons not changing to unfollow), and the features people keep asking for like folders and OPML import/export for subsets of subscriptions. Damashe also makes the case for GitHub labels and milestones so feature creep doesn't eat the project alive. From there, things go sideways into Apple's developer experience, which is rough. App Store Connect in Safari with VoiceOver is a mess. Damashe has had to switch to Chrome just to accept terms and conditions. Michael couldn't add testers to a TestFlight group from Safari at all. We hope WWDC has something to say to the wave of vibe coders showing up to Apple's ecosystem this year. We pivot to AI usage in general and make a case for the people who aren't building apps or websites: use these tools to understand things you're not an expert in. Commercial leases, tax code, anything dense and unfamiliar. Feed it the document, ask questions, then verify the answers in a different tool to check for consistency. The AI didn't change Damashe's behavior, by the way. Search has been bad for years. AI just gave him a way around it. Plus: Lyft vs Uber pricing (Lyft was significantly cheaper for both of us this trip), scheduling airport pickups with flight tracking, why Michael won't schedule rides if he can help it, a shoutout to Vijesh at the Hyatt in San Francisco, Damashe needs a new rolling suitcase, and a reminder to Tip Jar subscribers to check your email this week. Topics The vibe-coded podcast app: thirty-six builds, real testers, what's working Why Michael built it: frustration with his current app, wanting cross-platform PRDs as a starting point for AI-assisted projects Tester feedback that mattered: player controls, search, follow buttons, folders, OPML subsets GitHub labels and milestones for managing feature creep App Store Connect accessibility, or the lack of it Practical AI usage for non-developers: leases, tax code, things you don't know Verifying AI answers across different tools Lyft vs Uber: pricing, scheduled pickups, flight tracking Airport tips: leave early, turn off your VPN before you try to use the rideshare app Hotel shoutout: Vijesh at the Hyatt in downtown San Francisco Auphonic as a way listeners can support podcasts Tip Jar subscribers: check your email Links Technically Working: https://technicallyworking.show Feedback: feedback@technicallyworking.show Tip Jar: https://technicallyworking.show Michael on Mastodon: @payown@dragonscave.space Damashe on Mastodon: @damashe@technically.social Show bot: @tw@technically.social Auphonic: https://auphonic.com 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/b40b48e7-5a95-4a1e-ab4d-c6f884ab7bff This podcast is powered by Pinecast . Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

Michael and Damashe catch up from two different locations this week. Damashe is recording from a hotel room in Orlando with the Beta 87A he found at the bottom of his AT Guys backpack. Michael shares an exciting podcast launch and a new writing experiment on Substack. Topics covered in this episode: ACB National Convention 2026 in St. Louis: registration opens May 28 for members, June 4 for non-members. Convention runs July 24 through July 31 in person, with virtual programming starting July 13. Meetup plans: if you'll be in St. Louis between July 25 and 29, send an email and we'll set something up. Send restaurant recommendations too, especially the hole-in-the-wall spots. Marriott vs Hilton: Damashe is collecting Bonvoy points and would pick a Marriott most days. Our Perspective podcast launch: Michael's new show with a friend drops in early June. Two completely blind people talking about how they get through life. Trailer publishes Tuesday, Episode 1 follows shortly after. Search "Our Perspective" wherever you get podcasts. Using Claude to generate the show artwork and learning how to push back when an AI says it can't do something. Substack update: Michael started a Substack at payown.substack.com . AI helps draft posts based on what he's been working on each week. Search Payown on Substack to follow. GitHub featured Michael's video about Builder on LinkedIn to their 6.4 million followers. Pinecast tip: listener.email is a beta feature that gives your podcast a private email address so your personal inbox does not end up in the public podcast database. Use the discount code in the show notes for 40 percent off your first months of Pinecast. bag review update: the zipper finally gave out under heavy packing. Still a solid bag, but worth knowing the limits. Pirate Ship plug for shipping AT Guys demo gear and saving real money on labels. Wingstop talk, dry rub preferences, and the new Citrus Mojo flavor. A handheld 2 meter / 70 centimeter radio that was marketed as fully accessible but is not. At 49 dollars it is still a reasonable buy for what you actually get. Reach out if you want more details. San Francisco meetup: Michael will be in the city May 20 through 23. Reach out if you want to connect. Austin meetup: Damashe will be at NFB Convention July 3 through 8. Stop by the AT Guys booth or email to set up a meetup. Travel app idea: a Lyft vs Uber price comparison app that did not quite work. Still searching for a good one. Backup recording confession: Michael forgot to start Audio Hijack again. Get in touch: Email feedback@technicallyworking.show Mastodon: @payown@dragonscave.space, @damashe@technically.social, @tw@technically.social Hashtag: #TechnicallyWorking Support the show: tip jar link in the show notes. 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/6ac4263f-0786-437b-a083-5a93e61bb0d5 This podcast is powered by Pinecast . Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.

Mike's back from a workation and Damashe is recording from a cardboard box in his old office because the new office already isn't big enough. We get into audio app updates, the travel boom arm setup, a new podcast project called Our Perspective, and answer a listener question about starting an email list without breaking the bank. Damashe shares the news that he's already moved to a bigger space, two doors down from the original office, and walks through his automation plans: Home Assistant, Ubiquiti Access for door entry, sensors everywhere, and cameras inside and out. We talk Lucid radios as a possible replacement for giving employees phones, the Perkins Bloom add-on (and why $300 feels steep), Tailscale wins while traveling, and a quick PSA on the recent Linux vulnerabilities. In this episode: Audio Hijack, Loopback, and SoundSource updates Travel boom arm review and mobile recording setup Our Perspective podcast launching early June Listener question: free options for starting an email list (MailChimp, Groups.io , Kit) Teams, SharePoint, and syncing files locally Lucid radio follow-up and deploying them in a business Office move update: twice the space, front-to-back access Home Assistant vs Homey Pro, Ubiquiti Access, and sensor plans Perkins Bloom: $300 to turn your Brailler into a Bluetooth keyboard Throwback to Braille 'n Speak, Braille Lite, and Mountbatten Linux vulnerability PSA: update your machines Tailscale for remote access while traveling 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/bb830347-99fa-41f1-aaeb-177fa457b8af This podcast is powered by Pinecast . Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.