138: ‘I’ve Been Using Mine More in Bed’ With Joanna Stern

Episode Summary

Executive Summary: A wide-ranging tech conversation centered on 2015’s blurred line between tablets and laptops, especially the iPad Pro and Microsoft’s Surface devices. Joanna Stern argues both Apple and Microsoft are chasing the same productivity future from opposite directions, while also discussing Apple Watch quirks, smartphone buying choices, carrier changes, battery life, CES, Yahoo’s decline, and the increasing social conscience of big tech leaders.

Main Topics: iPad Pro as a laptop alternative (Priority: 5/5): The discussion explored how the iPad Pro’s larger screen changes real-world use for documents, comics, video, and shared viewing, while still leaving major gaps like file management and true desktop-style multitasking. Surface Book and Microsoft’s hardware ambitions (Priority: 5/5): They assessed Microsoft’s move into premium hardware, praising the Surface Book’s design, trackpad, and overall ambition while noting early bugs, SSD issues, and the tension of Microsoft competing with its OEM partners. Limitations of iOS versus OS X/Windows workflows (Priority: 5/5): A major thread focused on how iOS remains constrained by its file system, app-to-app workflows, and multitasking compared with desktop operating systems, even as Apple adds features like split view and improved text editing. Phone choice, battery life, and setup friction (Priority: 4/5): They debated iPhone sizes, contract-free buying, and the frustration of restoring phones from backups versus starting fresh, emphasizing battery life as the biggest unresolved pain point for many users. Apple and Microsoft as converging platform makers (Priority: 4/5): Both speakers framed Apple and Microsoft as trying to merge tablet and laptop concepts from opposite ends: Apple with a phone-first OS and Microsoft with a complex desktop OS. Big tech’s social posture and leadership style (Priority: 3/5): The conversation shifted to Mark Zuckerberg’s pledge to give away 99% of his wealth and Tim Cook’s increasingly visible emphasis on human rights and making the world better through technology. Yahoo’s unclear product identity and decline (Priority: 3/5): They questioned what Yahoo still is as a consumer product company, arguing that its business narrative outpaces any meaningful product excitement and that its future likely depends on what can be spun off or sold.

Key Arguments: The iPad Pro is genuinely useful for some document-heavy, media-heavy, and casual laptop-like tasks, but it still lacks fundamental desktop capabilities like file-system management and flexible multitasking. Microsoft’s Surface Book represents a major hardware leap and may be the best Windows laptop yet, but early manufacturing/software issues undermined confidence in the launch. Apple and Microsoft are both trying to solve the same computing problem, but Apple is constrained by an iPhone-era OS while Microsoft is constrained by the complexity of Windows. For many users, the decision between iPad Pro and Surface Pro/Book is less about raw power and more about peripherals, multitasking, and app availability. Starting a new iPhone as a fresh device can be preferable to restoring from backup because it avoids clutter and can improve the sense of a clean, fast phone. Battery life remains the most important unresolved issue on the iPhone; a thicker phone or revised priorities could be worth it if it materially improved runtime. The Apple Watch still lacks a smooth migration path for activity data between phones, and that should be added as an opt-in cloud sync feature. Tim Cook comes across as especially sincere and emotionally engaged when discussing human rights and social issues, more so than when discussing Apple products. Yahoo’s value proposition is hard to articulate from a product perspective; its relevance is more about business restructuring than consumer enthusiasm.

Data Points: Online holiday purchases on mobile devices: 64% - Black Friday / holiday shopping weekend purchases were reportedly made on mobile devices. Wealthfront standard management fee: 0.25% - Advertised fee for automated investing service above the free threshold. Wealthfront traditional advisor fees: 1% to 3% - Comparison point for why the service is cheaper than a financial advisor. Wealthfront minimum to start: $500 - Minimum amount to begin investing. Wealthfront promotional fee threshold: $15,000 - Listeners’ special deal delayed fees until assets exceed this amount. Mobile device shopping share: 64% - Used to illustrate how central mobile shopping has become. Surface Book starting price: $1,500 - Entry-level pricing discussed for the Surface Book. Apple Watch / phone restore setup steps: Many steps / indeterminate sync time - Described as a frustrating, lengthy process when restoring a new iPhone. Zuckerberg giving away fortune: 99% - Mark Zuckerberg and Priscilla Chan’s pledge in a letter to their daughter. Gates foundation pledge: 95% - Referenced as a comparison for billionaire philanthropy commitments. Zuckerberg annual donation cap: Up to $1 billion per year for 3 years - Described as part of the initial funding plan. Wearables / iPad sizes used: 3 iPad sizes - Joanna noted she has all three iPad sizes available for testing.

Pivotal Quotes: "“the matrix has gotten very complicated”" — Joanna Stern: On how hard it is now to recommend the right computer or tablet for different users. "“Apple’s got a phone operating system ... and Microsoft is approaching it with a more complex legacy operating system”" — John Gruber / Joanna Stern discussion: Summarizing why both companies are converging on similar devices from opposite directions. "“I think I’ve actually ditched the entire idea because it’s too hard”" — Joanna Stern: About her abandoned column idea to build a decision framework for what computer people should buy.

Implications: 2015’s computing landscape is defined by convergence and compromise: tablets are becoming laptops and laptops are becoming tablets. Buyers must choose based on workflow, not specs alone, and the next big breakthroughs will likely come from software, battery life, and camera improvements.