There was an unusually long time between when deepseek released R1 and the reaction in the public market. It was all anyone could talk about in SF last week, but the market didn’t move for another 6-7 days. Makes me wonder what is really driving the tech rally.

Large language models are all trained on the same dataset (the open internet). And the open internet includes content that is generated by AI models. This reminds me of a recursive math problem. It is a benign reason for why new models generate similar outputs as old models.

One of my themes for 2025 is "software goes mixtape". Using AI tools, anyone can make a personalized version of a software product and have it up and running in a few hours, no coding know-how required. The only problem is that I have no idea how to make money on this yet.

For two decades, I’ve invested in the technology shaping the future. AI is no different—except for the speed. The pace of innovation today is unlike anything we’ve seen before. AI is making software engineers more productive, helping investors analyze companies faster, and

Shipt was not supposed to work. It was a second-tier player in a crowded category. It was competing against a Sequoia and YC-backed company that had already raised hundreds of millions of dollars. It was headquartered in a city that didn’t have a direct flight from San

Had a great discussion with Sara Ittelson (Accel), Casber Wang (Sapphire Ventures), and Krystal Hu (Reuters) at HumanX on how AI is transforming industries. One key takeaway? AI is making software more modular and adaptive—enabling companies to remix, fine-tune, and deploy

Every local building department, architectural review board, and zoning board should be 90% automated with AI today. Local government is probably the last market anyone wants to build for, but every small town and village is understaffed in these departments.

𝗠𝗼𝘃𝗲 𝗳𝗮𝘀𝘁—𝗮𝗻𝗱 𝗳𝗶𝘅 𝘁𝗵𝗶𝗻𝗴𝘀. When systems scale faster than they communicate, failure is just a matter of time. SVB was the country’s 16th largest bank with roughly $190 billion of deposits. Most deposits were locked up under long-term credit agreements, so a

In 2019, we wrote a $1 million seed check to Marc Asch, a first-time founder, based on a six-slide pitch deck. Today, that investment is set to be among the largest venture-backed M&A outcomes in New York City history. Most people have never heard of Hidden Road, but many

Wisdom of the crowds beats the genius of a few. Have you ever wondered how YouTube, Instagram, and TikTok know exactly what you want? A decade ago, a team of researchers at Google turned text into vectors, laying the foundation for a new way of understanding information. That

GenAI is now applied to portfolio construction.

I attended the Berkshire Hathaway annual meeting on May 3rd, along with forty thousand other people who showed up to hear the oracle speak. For all the famous one-liners, I think the real story wasn’t on stage, it was whispered in hallways, “What happens to a firm built in the

I will take the other side of this debate. I bet: 1.) Yale invests in funds with audited books, which means marking to public comps vs. rounds from 4 years ago 2.) Yale’s VC secondary goes through and the discount is small (if any) We will see.

Mamdani’s plan for NYC: Increase the tax bill for existing grocery stores by 50%, and use that “found money” to launch new government-owned grocery stores that are staffed by people who weren’t good enough to get jobs at the DMV. (Apparently people in Brooklyn loved this idea)

2025 is the “Year of the Vibe”. First, it was vibe coding with Cursor. Then vibe design with Lovable. Then vibe video with LTX Studio. Each tool collapsed a time-intensive task into something fast, intuitive, and creative. Now millions of people use these tools daily to fuel

Humans are bad at understanding the power of compound growth and second order implications. Covid is a prime example - all the signs were there in Jan 2020, but nobody really understood. This is the story with AI today. Recent college grads are the canary in the coal mine.