Episodes

  • #169 – Apple's Price Hikes, Smart Glasses, and AI Policy Whiplash

    #169 – Apple's Price Hikes, Smart Glasses, and AI Policy Whiplash
    Jun 29 2026
    What We Cover This Week Earshot Development Progress and the Claude Workflow 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. Damashe on the New Siri Beta 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. FloType for Blind and Low-Vision Users 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). The MacBook Neo Touch ID Refurb 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 TestFlightFloType keyboard TestFlightFloType beta tester WhatsApp groupPirate ShipApple Refurbished StoreAGIGA Echo Vision smart glassesMeta 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.
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    1 hr and 2 mins
  • #168 – Multi-Agent Madness: Rebuilding Earshot the Hard Way

    #168 – Multi-Agent Madness: Rebuilding Earshot the Hard Way
    Jun 23 2026
    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 GitHubIt decides which of the other nine specialized agents should handle the workAgents include: security, accessibility, UI, and othersThe planning agent creates a plan, sends it with the issue to the assigned agentThat agent completes the work, then passes results to a test agentIf tests pass, the planning agent opens a pull requestMichael 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 ...
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    1 hr and 1 min
  • #167 – We're Going to Atlanta

    #167 – We're Going to Atlanta
    Jun 15 2026
    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 letterPer-podcast playback speed is now working: set a default speed, override it for individual shows, and it remembers your preference automaticallyThe database migration bug from builds 88-95 is fixed; if your app was spinning and crashing, update to build 99The app now gives you a useful error message instead of just failing silently if something goes wrong with the databaseIf 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 thereTo get on the beta, find Michael on Mastodon Apple Deals Worth Knowing AirPods Pro 3 spotted at $179 on Amazon, Best Buy, and possibly WalmartAirPods 4 at $99Apple Watch Series 11 (42mm GPS) at $299 WWDC 26 Impressions Mike went in with low expectations and came out a little underwhelmedDamashe has not watched the keynote but has listened to everyone talk about itApple showed features live and uncut, which seems intentional - they want to prove the demos are realCertain AI features require M3 Pro or better on Mac, M4 or better on iPad, and iPhone 17 ProiOS 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 capabilitiesDamashe 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 changesSteven Robles used it to get notified when the Unify travel router came back in stockBoth 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 premiumDamashe's alternate theory: what if Apple makes a detachable touchscreen MacBook Neo instead of going ultra-premiumThe 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 machineBoth 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 interactionDamashe's argument: not yet, for several reasons - apps, authentication, companies not wanting to be commoditized, and the lack of strong local computeUber and Amazon are not going to sit still while an agent turns them into a background APIThe local vs. cloud routing problem is real: you need a local model to manage where requests go, and we are not there on mobile yetBoth see 2029-2030 as a realistic window for local compute on personal devices being good enough for most tasksThe 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 airlinesOpen 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 worksFederico Viticci's hope: get Sherlocked properly this time Links and Contact Send feedback: feedback@technicallyworking.showTestFlight beta for Earshot: find Michael on Mastodon at payown@dragonscave.spaceDamashe on Mastodon: damashe@technically.socialBot: tw@technically.socialSupport 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.
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    1 hr and 16 mins
  • #166 – If You Used a Passkey, Why Are You Asking for a Code?

    #166 – If You Used a Passkey, Why Are You Asking for a Code?
    Jun 7 2026
    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.
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    1 hr and 20 mins
  • #165 – No Excuses Left for Inaccessible Apps

    #165 – No Excuses Left for Inaccessible Apps
    Jun 1 2026

    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

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    1 hr and 7 mins
  • #164 – Building the podcast app I actually want

    #164 – Building the podcast app I actually want
    May 25 2026

    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

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    1 hr and 6 mins
  • #163 – Our Perspective Launches, Substack Experiments, and Hotel Room Recording

    #163 – Our Perspective Launches, Substack Experiments, and Hotel Room Recording
    May 17 2026

    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.

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    58 mins
  • #162 – Already Outgrown: Moving Two Doors Down

    #162 – Already Outgrown: Moving Two Doors Down
    May 10 2026

    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

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    56 mins