What We Learned This Week

Waymo to Contend with Snow: Google-owned Waymo announced this week that it will begin testing its autonomous ride-hailing service in Baltimore, St. Louis, and Pittsburgh. For now, the testing will involve human drivers as the company builds the local data and infrastructure needed for eventual fully autonomous deployment - similar to what it already operates in cities like San Francisco, Austin, and Atlanta. What stands out is the geography: these are colder-weather markets with snow, ice, and more complex road conditions. Until now, Waymo has focused largely on warm-weather cities where sensors and systems operate in more predictable environments. Expanding into these regions suggests growing confidence in the technology’s ability to handle less-forgiving conditions.

This is an important step toward making autonomous transportation a mainstream reality. In cities where Waymo already operates, driverless cars have quietly become part of everyday life - no longer futuristic, just functional. Outside those markets, however, the concept still feels closer to science fiction. Tesla is also pursuing robotaxi ambitions, but with a very different strategy: using consumer-owned vehicles rather than fleet-built systems loaded with specialized hardware. Waymo’s approach is more capital-intensive but also more controlled. Both paths are shaping the future of transportation in real time. And for now, Waymo appears to be in the lead as autonomy moves from novelty to infrastructure.

Boeing Keeps Fighting Back: Boeing continues to build momentum as it works its way out of one of the deepest setbacks in its history. This week, the company’s CFO told investors that deliveries for both the 737 and 787 are expected to rise next year, on top of solid progress already made in 2025. The update helped drive the stock up roughly 10% as the market absorbed a faster-than-expected recovery trajectory. Just as importantly, Boeing now expects to generate its first meaningful positive free cash flow since 2018, with analysts estimating low single-digit billions in cash generation for 2026.

This improvement reflects more than just higher production, it signals a slow rebuilding of trust with regulators, airline customers, and investors alike. The stock, now near $200, is up over 16% this year but remains far below pre-crisis levels near $400. If Boeing continues delivering consistently and restoring credibility, there’s still significant room to run. For a company that hasn’t produced sustainable cash flow in over half a decade, that shift matters more than headlines.