170: ‘Kicking Dirt on Them While They’re on Fire’ With Ben Thompson

Episode Summary

Executive Summary: The episode is a wide-ranging discussion of Apple, Google, Twitter, and emerging hardware/software trends. Major themes include Apple Music/iTunes friction, AirPods and Apple Watch usability, the Dash app controversy, Twitter’s acquisition prospects, Google’s Pixel and Assistant strategy, Siri’s shortcomings, and AR versus VR. The hosts repeatedly contrast Apple’s integrated, consumer-friendly approach with Google’s stronger technology but weaker business model, while emphasizing trade-offs between openness, security, and usability.

Main Topics: Apple Music, iTunes, and offline media management (Priority: 5/5): John explains a workaround for syncing an entire music library to a new iPhone using a smart playlist and discusses the frustration of Apple Music/iCloud Music Library blocking the old sync model. The conversation broadens into a critique of cloud-only media access, especially for travel and low-signal environments. AirPods, Siri controls, and watch-based playback (Priority: 5/5): They revisit AirPods’ strengths and limitations, correcting earlier assumptions that Siri can’t control volume or track navigation. The discussion highlights the lack of physical playback controls, the usability trade-offs of Siri, and how the Apple Watch can partially compensate. Apple Watch design, fitness tracking, and hardware reliability (Priority: 5/5): The hosts discuss the Apple Watch’s changing role, especially as a fitness tracker, plus a recurring issue where stainless steel watch backs detach from the charger. They also debate whether the watch’s interface and crown/buttons are being used in the most sensible way. Dash app removal and App Store power dynamics (Priority: 5/5): A nuanced debate about Apple removing Dash from the App Store over alleged review fraud. They stress the imbalance between Apple’s power and an indie developer’s livelihood, the complications of international banking/cultural differences, and the need for Apple to show more process and grace. Twitter’s strategic crisis and acquisition rumors (Priority: 4/5): They analyze Twitter’s overstaffing, declining efficiency, and the possibility of a sale or leveraged buyout. The hosts argue Twitter’s service is valuable but structurally bloated, and that its business model and organizational scale are misaligned with its product. Google Pixel, Google Assistant, and business-model transition (Priority: 4/5): The Pixel is framed as a hardware vehicle for Google Assistant rather than just a phone. The discussion argues that Google’s assistant-first future makes sense technologically but conflicts with its ad-based business model, which relies on giving users options rather than definitive answers. Siri, voice computing, and AR vs VR (Priority: 4/5): They criticize Siri’s inconsistency, poor multi-step support, and cutesy failure modes, while noting that dictation has improved a lot. The episode closes by contrasting Apple’s preference for augmented reality with Facebook’s immersive VR vision, and why AR better fits Apple’s product philosophy.

Key Arguments: Apple deliberately makes full-library music syncing harder on iPhone, likely to avoid storage issues on lower-capacity devices, but the result is user frustration, especially for offline use. A smart playlist workaround can force a full music download on iPhone, but the need for such a workaround shows Apple’s system is intentionally constrained. AirPods are compelling because automatic pause/resume works well, but the lack of physical track/volume controls still makes them less convenient than wired headphones in some situations. Siri actually can handle volume and track commands through the AirPods, but its latency and inconsistent understanding make it feel less reliable than hardware buttons. The Apple Watch’s crown and buttons are underutilized; if music is playing, the crown should arguably control volume from the watch face. The Apple Watch back detachment issue appears common enough to have a known Apple support script, and Apple is replacing affected units even out of warranty. Dash’s removal illustrates a real due-process problem: large platforms can destroy an indie developer’s business based on partial information, and cross-border banking/account setups can look fraudulent when they are not. Apple should remain closed to sideloading on iOS because openness would increase malware risk and make the platform less trustworthy for mainstream users. Twitter’s core product is simple and valuable, but the company has too much overhead; a reset or buyout may be necessary to save the business. Google Assistant could justify Pixel hardware if Google uses phones as the distribution vehicle for its best assistant, but this only works if Google is willing to shift from ads to hardware economics. Google’s ad model depends on offering options; an assistant model depends on giving direct answers. Those are structurally different business logics. Siri’s biggest weakness is not just poor capability but user disappointment: people feel silly for trying it and then stop experimenting, which suppresses adoption even when the technology improves. Apple’s strength is integrated hardware/software products; Google’s strength is iterative services and machine learning. Each company is optimized for what the other wants to do. AR fits Apple’s philosophy better than VR because Apple tends to build tools that augment real life rather than immersive escapes from it.

Data Points: Music library size: 21 gigabytes - John says his library contains 4,000 songs totaling 21 GB, which should fit on a 256 GB iPhone. Song count: 4,000 songs - Used to illustrate that his local library is large but still manageable on modern storage. Smart playlist size threshold: 300 megabytes - The workaround for syncing all music to iPhone uses a smart playlist that matches files under this size. Apple Watch replacement turnaround: 3 to 5 days - Amy’s defective Apple Watch was sent in for service and expected back within this window. Backblaze price: $5 per Mac per month - Sponsor read describing unlimited backup pricing. Backblaze trial: 15-day free trial - Free trial offered via sponsor link. Harry’s blade price: $2 per blade - Compared with $4+ at drugstores. Harry’s free trial set: Free with shipping only - Includes razor, five-blade cartridge, and shaving gel. Away carry-on price: $225 - First luggage size in the sponsor read. Away medium price: $275 - Second luggage size in the sponsor read. Away large price: $295 - Third luggage size in the sponsor read. Away battery capacity: 10,000 mAh - Built-in removable charger in the luggage. Pixel phone sizes: 5-inch and XL model - The hosts discuss ordering the 5-inch Pixel. Pixel storage options: 32 GB and 128 GB - They debate which storage tier to buy. Tesla high-end sedan sales: More than BMW and Mercedes combined - John cites a market comparison showing Tesla outselling the Mercedes S-Class and BMW 7-series combined in a high-end segment. Twitter revenue per employee: $462,000 - Referenced from a comparison showing Twitter near Yahoo-level efficiency in 2015. Twitter profit per employee: -$130,000 - Used to argue Twitter’s structural unprofitability. Google revenue per employee: $1.1 million - Part of the revenue-per-employee comparison. Facebook revenue per employee: $1.4 million - Part of the revenue-per-employee comparison. Apple revenue per employee: $2 million - Highest figure in the cited comparison.

Pivotal Quotes: "It is the heaviness of macOS that allows iOS to be so light." — John Gruber: Used to explain why macOS and iOS should remain separate rather than being merged into one compromise system. "The problem for the future is that Apple has the right business model, but the bad technology. And Google has the good technology, but the bad business model." — Ben Thompson: A summary of the hosts’ comparison between Apple’s and Google’s strategic strengths and weaknesses. "The number one feature of any messaging app has nothing to do with the interface... The number one feature of any messaging app is, do your friends and family use it?" — Ben Thompson: Used in the discussion of iMessage, Duo, and why messaging products become sticky.

Implications: The episode underscores how platform control, business model, and product philosophy shape user experience. Apple’s closed system improves safety but can frustrate power users; Google’s stronger AI may matter more if it can build hardware and distribution; Twitter and Siri both need structural fixes, not just feature tweaks.