607: You're on Speaker Phone with Connected

610: The Only Way to Deal with John

Jul 2, 20261h 19mSummary

In this episode of Connected, the hosts engage in a lively debate regarding recent adjustments to their annual prediction game, the Rickies. After a listener pointed out a potential structural flaw regarding bonus picks and fourth-quarter Apple events, the group discusses whether to implement a carryover rule or maintain the current system, ultimately deciding to keep the existing rules for now to avoid unnecessary complexity. Beyond the meta-discussion of their own rules, the conversation shifts to Apple software and user experience. Federico shares a troubleshooting saga involving Siri AI and outdated search settings, which serves as a springboard for a critique of complex, multi-layered iOS settings. The hosts also touch upon the evolving culture of corporate self-promotion on professional networks, the specific challenges of managing feedback from collaborators, and the curious habit of traveling with unused gaming consoles. Finally, Federico offers a brief update on his highly organized, automated workflow for his upcoming annual software review, detailing how he uses custom agents and structured databases to manage the massive influx of features and information required for his comprehensive analysis.

609: You Gotta Be Gud

Jun 25, 20261h 16mSummary

In this episode of Connected, the hosts gather to discuss a variety of tech topics, starting with project updates and the debut of a new podcast mascot, Steve the Bear Cow. The conversation transitions into a lighthearted look at a viral image of Evan Spiegel and the subsequent discussion regarding the design and ergonomics of high-end hardware, specifically focusing on how certain consumer products should undergo more rigorous internal review before launch. A significant portion of the episode is dedicated to an in-depth analysis of Apple's recent, widespread price increases across its hardware lineup. The hosts perform a comprehensive round-robin review of the price hikes affecting Macs, iPads, and accessories, expressing concern over the impact on consumers and the strategic implications of these changes. They also deliberate on why the iPhone remains the notable exception to these adjustments. Finally, the discussion moves to personal anecdotes regarding hardware upgrades, the value of various device configurations, and the ongoing shift toward higher costs in the consumer electronics landscape as resources are increasingly allocated toward the growing artificial intelligence sector.

608: Here's How to Fix a Sink

Jun 18, 20261h 22mSummary

In episode 608 of Connected, hosts Mike Hurley and Stephen Hackett navigate the summer schedule while discussing a mix of home infrastructure projects and the latest developments in Apple software. The conversation begins with a look at Stephen’s recent blog post regarding his home network cabinet, which provides a robust, failover-capable internet setup despite his humorous self-deprecation about the "tangled mess" of cables behind his walls. The hosts then shift to their ongoing exploration of Apple’s history, specifically highlighting the collaborative nature of their podcasting style when covering complex tech legacies. The core of the episode focuses on their experiences with the latest OS betas. They dive into how the new, LLM-driven Siri feels significantly more natural and capable of handling personal context across the operating system. They share anecdotes about using Siri to interact with Reminders, Health data, and Notes, noting that while the technology still has minor quirks, it marks a major shift in how users can communicate with their devices. Finally, they touch on industry trends, including third-party app integration and the rising costs of components like RAM.

606: The Rickies (June 2026)

Jun 4, 20261h 32mSummary

In episode 606 of Connected, the hosts kick off the show by discussing the joys and ironies of becoming a regular at local restaurants before diving into a fascinating segment about a community-created tool. A listener developed "ConCTL," a command-line interface for the podcast that allows users and AI agents to query show data, episode history, and even the lore of the "Rickies" game. The conversation then shifts to professional updates, with Mike celebrating the successful launch of a Kickstarter campaign for a new Apple history podcast. As the episode approaches the highly anticipated Worldwide Developers Conference, the team analyzes the potential for Apple Intelligence. Federico and Stephen share their perspectives on whether Apple can catch up in the AI space, emphasizing the importance of platform integration over standalone chatbots. Finally, the hosts transition into the competitive "Rickies" game, where they make their keynote predictions. They engage in a lively debate over the rules of the competition, specifically regarding bonus picks and scoring, while offering their initial forecasts for upcoming announcements, including a potential redesign of the Siri experience and advanced grammar-checking tools for Apple’s ecosystem.

605: Being Completely Awesome

May 28, 20261h 14mSummary

In episode 605 of Connected, the hosts gather to discuss a variety of tech-related topics, starting with a review of their 2026 predictions—the so-called Rickies. The discussion touches on the accuracy of their past forecasts regarding hardware, software, and corporate leadership changes. The team also dives into some recent Apple-related news, including the confusing rollout of new icons for various creator studio applications and a less-than-ideal experience during a visit to the Regent Street Apple Store, sparking a broader conversation about store layout and staffing challenges. A significant portion of the episode focuses on a major technical shift as Steven details his transition from WordPress to Hugo, a static site generator, for his long-running website. He explains the motivations behind the move, specifically citing concerns over hosting costs and performance during traffic spikes. He highlights the benefits of simplicity, speed, and the unique workflow of managing a massive archive of posts through static files, while acknowledging the loss of a traditional content management interface. The hosts explore the trade-offs of this "old school" development approach, reflecting on the complexities of long-term digital maintenance.

604: The Floor of the Street

May 21, 20261h 17mSummary

In episode 604 of Connected, the hosts dive into a wide-ranging discussion on technology, design, and industry trends. The conversation begins with a lighthearted catch-up before moving into listener feedback regarding the history of the iPhone’s interface, specifically the ability to customize the iPod app’s tab bar—a feature the hosts argue should have been preserved. They also discuss a clever web tool for tracking the International Space Station and explore the nuances of iOS accessibility, including the evolution of "Type to Siri" and potential future design changes in the mobile interface. A significant portion of the episode is dedicated to the recent Google I/O event. The hosts express skepticism regarding Google’s current organizational structure and its focus on AI-driven image and video generation tools. They share concerns about the societal implications of these technologies, particularly regarding media literacy and the ease of creating deepfake content. The discussion concludes with a critical look at the industry’s ambitious, often hyperbolic, narratives surrounding the future of artificial intelligence and the responsibilities that come with such powerful technological advancements.

600: Tommy Siri

Apr 23, 20261h 33mSummary

In this milestone 600th episode of Connected, the hosts mark the occasion with a blend of reflection and lighthearted banter. Rather than opting for a traditional clip show, the team utilizes a special, listener-created website to explore nostalgic audio fragments from the podcast’s earlier years, sparking discussions on how their voices, perspectives, and production quality have evolved since the show’s inception. Beyond the anniversary celebrations, the hosts tackle the significant news of Tim Cook’s upcoming transition from CEO to executive chairman at Apple, with John Ternus poised to take the helm. While acknowledging the importance of this leadership change, the conversation shifts to the broader implications of corporate governance and the public reactions that follow such announcements. This leads to a humorous and incredulous deep dive into a social media post regarding the transition, which serves as a springboard for a broader discussion on the intersection of technology, politics, and the surreal nature of modern communication. Between these topics, the hosts share personal updates regarding their technical setups and data management workflows, grounding the episode in the practical, tech-focused spirit that defines the show.

599: Then I Went a Step Beyond... Actually Two Steps

Apr 16, 20261h 27mSummary

In this episode of Connected, the hosts delve into a series of technical deep dives and predictions for the upcoming WWDC. The conversation begins with a discussion on the MacBook Neo, noting the surprising discovery that users can now purchase replacement parts in various colors, regardless of their specific machine’s original hue. The primary focus then shifts to the hosts' struggles with data management and backups. One host recounts a challenging transition away from Backblaze, detailing the process of repurposing an older MacBook Pro as an always-on server to host a large Dropbox account locally. They explore the complexities of utilizing external SSDs, remote desktop solutions like Tailscale and Screens, and the potential of switching to iDrive for cloud storage. The discussion touches on the nuances of maintaining a robust, reliable backup strategy in an era of changing service policies. The episode concludes with a forward-looking segment on WWDC expectations. The hosts share their hopes for AI integration within Siri, the possibility of iPadOS regaining more intuitive windowing systems like Split View, and a wish for a sandboxed terminal app on the iPad to empower power users and developers.

598: 8TB of Space in a Trash Can

Apr 9, 20261h 37mSummary

In this episode of Connected, the hosts delve into a variety of listener feedback and industry news, beginning with updates regarding the older trash can Mac Pro. While some users are successfully running modern versions of macOS on these machines using legacy patcher tools, the hosts discuss the inherent risks and technical complexities involved. The conversation then shifts to the persistent challenge of managing cloud storage. The hosts explore potential strategies for backing up extensive Dropbox libraries, balancing the desire for low-maintenance solutions against the limitations of current file-provider APIs. This leads to a broader discussion on hardware choices, storage requirements, and the merits of maintaining a local server versus cloud-based alternatives. The episode also highlights the unexpected success of the MacBook Neo. The hosts examine how Apple’s reliance on binned chips has created a unique supply chain challenge as demand for the entry-level laptop grows. Furthermore, they discuss the competitive landscape, noting that the MacBook Neo’s hardware quality and integration continue to set a high bar that many Windows-based PC manufacturers struggle to match at similar price points.