Weekly Spotlight #9: Tokens, Agents, and Mortgages
Three conversations about the infrastructure we're building and the infrastructure that's failing us.
When Vlad Tenev pitched Robinhood at a Palo Alto bar, investor Jason Calacanis thought the idea was insane: get young people who don't care about the future to trade stocks for free. Ten years later, Robinhood just joined the S&P 500, and Tenev is pushing an even bolder vision. His latest experiment involves tokenizing private companies like SpaceX and OpenAI, making shares available to retail investors through blockchain technology.
The regulatory pushback has been fierce, but Tenev argues this democratization is essential as AI reshapes the economy. "These AI companies are getting into valuations of hundreds of billions with zero retail ownership," he warns. His solution involves treating tokenized stocks like stablecoins, backing digital tokens one-to-one with actual shares held in reserve.
For: Anyone curious about how traditional finance meets crypto innovation.
Physical autonomy has outpaced digital autonomy in 2025, a counterintuitive reality that OpenAI's platform leaders explore with striking clarity. You can take a fully autonomous Waymo across San Francisco, but you still can't reliably book a flight ticket with an AI agent. The reason: self-driving cars operate in a structured world of roads and traffic laws, while AI agents are "dropped in the middle of nowhere" with little scaffolding to guide them.
Their enterprise deployments tell a different story. At T-Mobile, OpenAI models now handle customer support calls with supernatural voice quality. At pharmaceutical giant Amgen, they're accelerating drug development that could impact hundreds of millions of lives. The secret isn't just better models but "forward deployed engineers" who embed deeply with customers, building custom integrations and defining what success looks like through rigorous evaluations.
For: Business leaders wondering how AI actually transforms operations beyond the hype.
California's housing market is flashing warning signs that cut to the heart of American inequality. With inventory skyrocketing in markets like Los Angeles and typical home values exceeding $700,000 statewide, the math is brutal: a 7% mortgage translates to nearly $5,000 monthly payments. This makes California the most expensive state for homeownership, with payments $700 higher than second-place Massachusetts.
The core issue isn't just demand or interest rates but California's fundamental inability to build housing at scale. Despite being home to the world's most innovative companies, the state remains trapped by regulatory complexity that makes new construction prohibitively expensive and slow. The question isn't whether prices will drop, but whether California can solve its housing crisis before it drives out the very workers powering its economy.
For: Real estate investors, policymakers, and anyone wondering about California's economic sustainability.