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.

<p>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.</p> <p>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.</p> <p>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 <a href="http://CLAUDE.md" rel="nofollow">CLAUDE.md</a> file that every code change gets run through the accessibility agents from <a href="http://community-access.org" rel="nofollow">community-access.org</a> before anything moves forward. No unlabeled buttons. No accessibility regressions. Just a rule that runs automatically.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p><strong>Links and things mentioned:</strong></p> <ul> <li><a href="https://bits-acb.org/" rel="nofollow">Quill (BITS Markdown writing app for Mac and Windows)</a></li> <li>LaunchBar — <a href="https://www.obdev.at/products/launchbar/" rel="nofollow">https://www.obdev.at/products/launchbar/</a></li> <li><a href="https://community-access.org/docs.html" rel="nofollow">community-access.org accessibility agents</a></li> <li>Overcast — <a href="https://overcast.fm" rel="nofollow">https://overcast.fm</a></li> <li><a href="https://technicallyworking.show" rel="nofollow">Technically Working —</a></li> </ul> <h1>Episode Notes</h1> <p>Notes go here</p> <p>Support Technically Working by contributing to their tip jar: <a href="https://tips.pinecast.com/jar/technically-working" rel="payment nofollow">https://tips.pinecast.com/jar/technically-working</a></p> <p>Find out more at <a href="https://technically-working.pinecast.co" rel="nofollow">https://technically-working.pinecast.co</a></p> <p>Send us your feedback online: <a href="https://pinecast.com/feedback/technically-working/6a089d48-76a4-43f5-b8af-6e63343769a8" rel="nofollow">https://pinecast.com/feedback/technically-working/6a089d48-76a4-43f5-b8af-6e63343769a8</a></p> <p>This podcast is powered by <a href="https://pinecast.com" rel="nofollow">Pinecast</a>. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code <strong>r-431b7d</strong> for 40% off for 4 months, and support Technically Working.</p>

<p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <p>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.</p> <h3>Topics</h3> <ul> <li>The vibe-coded podcast app: thirty-six builds, real testers, what's working</li> <li>Why Michael built it: frustration with his current app, wanting cross-platform</li> <li>PRDs as a starting point for AI-assisted projects</li> <li>Tester feedback that mattered: player controls, search, follow buttons, folders, OPML subsets</li> <li>GitHub labels and milestones for managing feature creep</li> <li>App Store Connect accessibility, or the lack of it</li> <li>Practical AI usage for non-developers: leases, tax code, things you don't know</li> <li>Verifying AI answers across different tools</li> <li>Lyft vs Uber: pricing, scheduled pickups, flight tracking</li> <li>Airport tips: leave early, turn off your VPN before you try to use the rideshare app</li> <li>Hotel shoutout: Vijesh at the Hyatt in downtown San Francisco</li> <li>Auphonic as a way listeners can support podcasts</li> <li>Tip Jar subscribers: check your email</li> </ul> <h3>Links</h3> <ul> <li>Technically Working: https://technicallyworking.show</li> <li>Feedback: [email protected]</li> <li>Tip Jar: https://technicallyworking.show</li> <li>Michael on Mastodon: @[email protected]</li> <li>Damashe on Mastodon: @[email protected]</li> <li>Show bot: @[email protected]</li> <li>Auphonic: <a href="https://auphonic.com" rel="nofollow">https://auphonic.com</a></li> </ul> <p>Support Technically Working by contributing to their tip jar: <a href="https://tips.pinecast.com/jar/technically-working" rel="payment nofollow">https://tips.pinecast.com/jar/technically-working</a></p> <p>Find out more at <a href="https://technically-working.pinecast.co" rel="nofollow">https://technically-working.pinecast.co</a></p> <p>Send us your feedback online: <a href="https://pinecast.com/feedback/technically-working/b40b48e7-5a95-4a1e-ab4d-c6f884ab7bff" rel="nofollow">https://pinecast.com/feedback/technically-working/b40b48e7-5a95-4a1e-ab4d-c6f884ab7bff</a></p> <p>This podcast is powered by <a href="https://pinecast.com" rel="nofollow">Pinecast</a>. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code <strong>r-431b7d</strong> for 40% off for 4 months, and support Technically Working.</p>

<p>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.</p> <p>Topics covered in this episode:</p> <ul> <li>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.</li> <li>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.</li> <li>Marriott vs Hilton: Damashe is collecting Bonvoy points and would pick a Marriott most days.</li> <li>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.</li> <li>Using Claude to generate the show artwork and learning how to push back when an AI says it can't do something.</li> <li>Substack update: Michael started a Substack at <a href="http://payown.substack.com" rel="nofollow">payown.substack.com</a>. AI helps draft posts based on what he's been working on each week. Search Payown on Substack to follow.</li> <li>GitHub featured Michael's video about Builder on LinkedIn to their 6.4 million followers.</li> <li>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.</li> <li>bag review update: the zipper finally gave out under heavy packing. Still a solid bag, but worth knowing the limits.</li> <li>Pirate Ship plug for shipping AT Guys demo gear and saving real money on labels.</li> <li>Wingstop talk, dry rub preferences, and the new Citrus Mojo flavor.</li> <li>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.</li> <li>San Francisco meetup: Michael will be in the city May 20 through 23. Reach out if you want to connect.</li> <li>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.</li> <li>Travel app idea: a Lyft vs Uber price comparison app that did not quite work. Still searching for a good one.</li> <li>Backup recording confession: Michael forgot to start Audio Hijack again.</li> </ul> <p>Get in touch: Email [email protected] Mastodon: @[email protected], @[email protected], @[email protected] Hashtag: #TechnicallyWorking</p> <p>Support the show: tip jar link in the show notes.</p> <p>Support Technically Working by contributing to their tip jar: <a href="https://tips.pinecast.com/jar/technically-working" rel="payment nofollow">https://tips.pinecast.com/jar/technically-working</a></p> <p>Find out more at <a href="https://technically-working.pinecast.co" rel="nofollow">https://technically-working.pinecast.co</a></p> <p>Send us your feedback online: <a href="https://pinecast.com/feedback/technically-working/6ac4263f-0786-437b-a083-5a93e61bb0d5" rel="nofollow">https://pinecast.com/feedback/technically-working/6ac4263f-0786-437b-a083-5a93e61bb0d5</a></p> <p>This podcast is powered by <a href="https://pinecast.com" rel="nofollow">Pinecast</a>. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code <strong>r-431b7d</strong> for 40% off for 4 months, and support Technically Working.</p>

<p>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.</p> <p>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.</p> <p><strong>In this episode:</strong></p> <ul> <li>Audio Hijack, Loopback, and SoundSource updates</li> <li>Travel boom arm review and mobile recording setup</li> <li>Our Perspective podcast launching early June</li> <li>Listener question: free options for starting an email list (MailChimp, <a href="http://Groups.io" rel="nofollow">Groups.io</a>, Kit)</li> <li>Teams, SharePoint, and syncing files locally</li> <li>Lucid radio follow-up and deploying them in a business</li> <li>Office move update: twice the space, front-to-back access</li> <li>Home Assistant vs Homey Pro, Ubiquiti Access, and sensor plans</li> <li>Perkins Bloom: $300 to turn your Brailler into a Bluetooth keyboard</li> <li>Throwback to Braille 'n Speak, Braille Lite, and Mountbatten</li> <li>Linux vulnerability PSA: update your machines</li> <li>Tailscale for remote access while traveling</li> </ul> <p>Support Technically Working by contributing to their tip jar: <a href="https://tips.pinecast.com/jar/technically-working" rel="payment nofollow">https://tips.pinecast.com/jar/technically-working</a></p> <p>Find out more at <a href="https://technically-working.pinecast.co" rel="nofollow">https://technically-working.pinecast.co</a></p> <p>Send us your feedback online: <a href="https://pinecast.com/feedback/technically-working/bb830347-99fa-41f1-aaeb-177fa457b8af" rel="nofollow">https://pinecast.com/feedback/technically-working/bb830347-99fa-41f1-aaeb-177fa457b8af</a></p> <p>This podcast is powered by <a href="https://pinecast.com" rel="nofollow">Pinecast</a>. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code <strong>r-431b7d</strong> for 40% off for 4 months, and support Technically Working.</p>