Drew and Dan in the Morning

Drew Benson and Dan O'Leary
  • 5.0 (3)
  • Entrepreneurship

Dan and Drew talk tech, projects, problems and Apple pie.

Episodes

  1. Sep 28

    Making a Press Kit

    Claude’s hang-up, Nvidia / Hugging Face news, Press Kits in depth, building with Kickstart or Claude, when to send, and clipping campaigns. Vitamin B2 - Riboflavin! Chapters 00:00 Welcome!00:10 Riboflavin linked to lower dementia risk01:01 Nvidia buys Hugging Face02:20 Why you NEED a press kit04:16 Mercury Weather's press kit06:37 Building with Kickstart and hosting hurdles09:06 Building a press kit with Claude11:34 People don't browse for apps anymore12:31 When to send your press kit16:18 Clipping campaigns and influencer marketing18:58 Claude can hang up on you Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: How to Make an App Press KitMercury Weather Press KitKickstart Press KitPhotoCal AI Press KitThe Midst Press KitRiboflavin Cuts Dementia Risk by Half Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  2. Sep 6

    Watermarked, banned, and denied

    NYC ditches AI in classrooms, Anthropic quietly watermarks Claude's every word and code it writes, and Dyson wants $499 to let a camera into your mouth. Drew and Dan dig a little to get a better sense of who Apple’s new CEO, John Ternus, really is. (Drew has a list of bugs waiting for him!) Is the Apple Upgrade (lease) program with Klarna a bait-and-switch? The AI boom turned a $5K Mac Studio into an $11K one. Chapters 00:00 Welcome00:26 NYC Schools Ban Generative AI04:00 Anthropic Watermarks Claude Text11:05 Does AI Use Count as Research?16:36 Why Students Still Need Fundamentals21:00 Dyson's $499 AI Toothbrush24:16 Meet New Apple CEO John Ternus29:11 Hopes for Hardware-First Apple33:36 Apple's Nagging Software Bugs44:56 Foldable Phone and Touchscreen Mac Rumors53:43 Klarna Lease Denial Mystery1:00:42 AI Boom Inflates Hardware Prices Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: NYC public schools bans AICtrl-Alt-Speech PodcastAnthropic text watermarkingDyson CameraJetJohn Ternus 1993 High School picKlarna Apple Leasing issues Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  3. Aug 26

    Dan's glasses (and other things)

    Today we discuss user feedback, Dan's glasses, smart glasses, subscription fatigue, Apple's new hardware leasing program, Swift Dictionary key surprises and the challenges of the Apple TV remote feature on iPhone. Plus tips for crafting a great Press Kit for your app. Chapters 00:00 Welcome to Episode 10!00:59 Dan's Glasses - and other user feedback06:31 Subscription fatigue and sustainable app pricing12:29 Syncing subscriptions with your own server15:08 Swift Dictionaries - key surprises!28:08 Xcode 27 resizable window support28:56 Apple's new leasing program32:24 Tips for your app's Press Kit + competitor analysis36:22 Drew's Apple TV iPhone Remote app frustrations40:32 Wrap up Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: ObjectIdentifierHow to Make an App Press KitApp Store Competitor AnalysisMercury Weather’s Press KitApple Upgrade (leasing) Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  4. Aug 15

    App Intents and 737 Hacks

    How Dan is implementing App Intents and App Entities in The Midst iOS app, integration of Siri AI features for iOS 27, plus a coin-sized device that can hack a Boeing 737 Chapters 00:00 Welcome!00:54 Integrating App Intents in The Midst01:51 Minimum Deployment Target and User Base03:19 Implementing Siri AI Features04:02 "Hey Siri, check me in with The Midst"07:30 Letting Siri search saved places and talk back13:02 Duplicate SwiftData schemas wipe out years of check-ins16:29 CloudKit saves the day!17:27 Syncing with CloudKit20:15 More Siri integration22:25 Siri result cards with App Intents29:51 Yikes! Coin-sized device spoofs Boeing 737 FMC and MCDU systems Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: App IntentsUnicorn ChatThe MidstMaking app entities available in SpotlightCoin-sized device can hack a Boeing 737 Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  5. Jul 30

    Shipping Relay Team Finder, OpenAI hacks Hugging Face, Agent Smith safety harness

    Dan ships Relay Team Finder, OpenAI’s hacks Hugging Face, Drew's open source Agent Smith structured agent safety harness, and how to price your app. Chapters: 00:00 France bans social's for under-15s00:38 App Store social media questions01:54 Inside the Declared Age Range API07:03 OpenAI hacks Hugging Face15:11 Paperclips17:03 Agent Smith: Structured safety harness25:30 The Coffee Test - how to price your app29:40 Dan ships Relay Team Finder36:29 Build by Tony Fadell Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: Declared Age Range APIDeliver age-appropriate experiences in your app (WWDC25)ExploitGym on GithubOpenAI's hack of Hugging Face Post-mortemAnthropic’s ConstitutionDrew’s macOS Agent SmithPaul Hudson’s How to price an app: the coffee testRelay Team FinderTony Fadel’s book, Build Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  6. Jul 13

    The Cost of Our Tools: How much is too much?

    When a useful tool asks for too much? Drew and Dan trace the new reality of AI identity verification, age-verification laws, anonymity, who you'd trust to hold your ID, and Drew's saga of getting flagged and verified. PLUS: The best way to localize your app into 35+ languages. Chapters • 00:00  Icon Composer fix • 02:56  AI + politics • 06:53  Identity verification and the Hawthorne Effect • 09:23  Nothing to hide • 15:48  Who holds the keys? (Persona) • 22:14  Localizing your app into 35 languages • 27:02  Accessibility & becoming dependent on your tools • 29:34  Privacy tradeoff: What's the solution? • 35:08  Drew's Claude refusal & the Cyber Verification Program • 42:59  Weird Private Cloud Compute limits Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: Icon Composer 2Drew’s LocalizationSuperPrompt.mdCyber Verification ProgramAnthropic Identity Verification Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  7. Jun 26

    News You Can Use

    "Apps violating guidelines may face removal from the store." Fresh App Store changes, Performance Improvement Plans, Icon Composer 2 tips and gotchas. New Hide My Email problems, group and volume subscriptions, moving subscription handling to your server and loss of App Store Connect's Trends tab. Chapters 00:00  Intro02:14  Apple's crackdown on early review prompts04:05  Removing App Store "clutter"08:47  Developer Performance Improvement Plans13:28  Icon Composer gotchas and tips17:41  Problematic changes to Sign in with Apple & Hide My Email22:38  Group & volume subscriptions30:54  Moving StoreKit handling to your server38:48  App Store Connect loses Trends tab?!41:20  Wrap-up Finding Drew: BlueskyX / TwitterYouTubeGithub Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: Grandma’s MarathonApp Review GuidelinesWWDC 2024 App Store server APIsWWDC 2026 Group subscriptionsIcon Composer 2Relay Team Finder (TestFlight beta)The Midst (app)OpenAI omni-moderation API Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  8. Jun 9

    WWDC26 Special Delivery

    Drew and Dan chat about WWDC 2026: Parental controls, Siri improvements, Liquid Glass’ new volume knob, Foundation Models enhancements, MacOS Golden Gate, enhancements to Swift, SwiftUI, Xcode and more. Plus, saying goodbye (to UIDesignRequiresCompatibility and Intel Macs). Chapters 00:00 WWDC 2026 Keynote Overview03:03 Liquid Glass gets a Volume Knob05:59 Child Protection Features and Parental Controls08:52 Siri Improvements and User Experience11:53 New Features in macOS Golden Gate14:51 Apple Intelligence and Foundation Models17:56 Swift UI and Observable Properties23:24 Enhancements in Swift and Swift UI27:11 Exploring Xcode 27 and Watch OS Development29:22 Understanding App Intents and Schemas32:23 Platform Improvements and Accessibility Challenges 36:18 Transitioning to New Technologies and Features Finding Drew: BlueskyX / TwitterDrew’s YouTube live stream coding channel, @DrewBensonCodes Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: WWDC 2026 KeynoteWWDC 2026 Platforms State of the UnionDonny Wals on The Difference between Macros and Property Wrappers Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  9. Jun 7

    Data-Nuking Prompt Injection

    Drew and Dan explore how a single line of text in a public repo can ruin your day, what happens when AI coding agents go off the rails near your data, and the thorny questions of AI safety and ethics. Google has bad news for back-button hijackers. Drew shares lessons learned and challenges from making his apps accessible, and the two get into how optimizing for the wrong metric can quietly steer AI somewhere nobody intended. Chapters 00:00 Google Punishing Back-Button Hijackers02:31 Data Nuking Prompt Injection12:43 App Accessibility Lessons and Challenges20:48 AI Metrics and Unintended Consequences Finding Drew: BlueskyX / TwitterDrew’s YouTube live stream coding channel, @DrewBensonCodes Finding Dan: BlueskyInstagramDan’s Certainly Swift blog Mentioned in this episode: Google Punishing Back-Button Hijacking - Google’s policyData Nuking Prompt InjectionAccessibility Nutrition LabelsDrew’s MacOS Agent Smith agent harnessDrew’s Sight Words: First Words Match appDrew’s FunVoice Reverse Audio Singing appGoodhart’s Law Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercastDeezer

  10. May 28

    Beyond the button: Sign in with Apple, Server-Side Up

    App types and activities Apple prohibits in their App Review Guidelines, App Store ratings and reviews, best practices for keeping in touch with your customers, the use of the GitAPI MacOS app for testing endpoints, and a deep dive into Sign in with Apple, detailing the app-side integration as well as the server-side setup. Chapters 00:00 Welcome back!00:43 App Store review/rating guidelines04:00 Triggering the review prompt: what not to do09:01 Tool of the week: GetAPI (and why not Postman)13:00 Sign In With Apple: the app part18:25 The missing manual: SIWA on the server21:40 You only get the email ONCE23:55 Bearer tokens, keychain, and the 2nd launch31:35 Dan's Gotcha32:21 Win-back emails and "Hide My Email" trickiness33:42 Thanks! Finding Drew: BlueskyX / TwitterDrew’s YouTube live stream coding channel, @DrewBensonCodes Finding Dan: BlueskyInstagramDan’s Swift on the Server blog, Certainly Swift Mentioned in this episode: App Review GuidelinesApple Human Interface GuidelinesRequesting App Store reviews (sample code)GetAPI (dead-simple HTTP client)Fork (Dan's preferred Git GUI app)Sign in with Apple using SwiftUI and VaporSign in with Apple REST APIVapor (Swift on the server) Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercast

  11. May 17

    Scandal! + UI (AI?) Accessibility

    Drew and Dan talk about the shocking new China scandal, app review guidelines, animating SF symbols, and the importance of app accessibility. Drew makes a bold prediction about WWDC 2026. Chapters 00:00 Scandal!02:58 App Review Guidelines update06:03 Dan's Dazzling Discoveries: Animating SF Symbols08:53 App Accessibility11:29 Accessibility Nutrition Labels and The Bold Prediction14:39 App Intents vs Accessibility Labels20:18 Preparing for WWDC 2026: Accessibility and Nutrition Labels28:07 Final Thoughts and To-Do List Finding Drew: BlueskyX / TwitterDrew’s YouTube live stream coding channel, @DrewBensonCodes Finding Dan: BlueskyInstagramDan’s Swift on the Server blog, Certainly Swift Links for things mentioned in this episode: Drew's MacOS Accessibility Client on GithubWWDC 2026 Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercast Thanks for joining us!

  12. Apr 20

    Aspiring Finishers

    Drew and Dan break down real-world software development—what’s working, what’s not, and where things are going. Topics range from app development and AI to conference takeaways (Deep Dish Swift), technical deep dives, and the occasional detour into reverse engineering and industry absurdities. Practical, opinionated, and grounded in actual experience. Chapters 00:00 Hello!06:13 App Development and AI11:58 Deep Dish Swift Conference19:04 Technical Insights and Challenges26:10 Reverse Engineering and Humorous Presentations Finding Drew: BlueskyX / Twitter Finding Dan: BlueskyInstagram Links for things mentioned in this episode: Dan’s new Swift blog, Certainly SwiftDrew’s YouTube live stream coding channel, @DrewBensonCodes9 to 5 Mac’s story on 4-star reviews:App Store ratings ‘broken’ as your 4-star review could hurt a developerDan’s social check-in (and Swarm replacement) app,, The MidstRelay Team Finder - releasing in August  - for Aspiring FinishersDeep Dish Swift 2026Adam Tow and his great talk on being adaptable, The Long Game: 30+ Years as an Indie Apple DeveloperDavid Beck’s talk, Surviving in Low ConnectivityChad Etzel’s awesome talk on Reverse Engineering the macOS Genie Animation Drew and Dan in the Morning can be found on: Apple PodcastsSpotifyYouTubeOvercast Thanks for joining us!

  • 12 Episodes

5
out of 5
3 Ratings

About

Dan and Drew talk tech, projects, problems and Apple pie.

Information

  • Creator
    Drew Benson and Dan O'Leary
  • Years Active
    2026
  • Episodes
    12
  • Rating
    Clean
  • Copyright
    © 2026 Drew Benson and Dan O'Leary
  • Show Website
    Drew and Dan in the Morning

You Might Also Like