Autonomous Agents as Digital Employees in Software

This episode took 8 years of convincing the guest to make it happen. I first met @aspenjfm at the Connaught Hotel to discuss a company we were co-investing in. I was 21 and had just raised my first fund. Jerry was one of the all-time greats, having led rounds into Twitter and managing $90BN for Insight. Today, after 8 years of friendship, I released our episode and have gone over it to condense my biggest learnings from the discussion. 1. The Shift from Assistants to Employees 🤖 We are moving beyond "copilots." Autonomous agents aren't just tools; they are becoming digital employees with identities, credentials, and the authority to make decisions. If you aren't building your software to be used by agents, you’re building for a shrinking market. 2. "Cursor is Obsolete" 💻 Native AI startups are already moving past current coding tools toward homemade autonomous agents that write code directly. In AI, you can’t think about yesterday; you have to build for where the puck is going. 3. The Rise of the "Claw Stack" 🏗️ Just as the LAMP stack fueled the 2004 web explosion, Jerry predicts a new "Claw Stack" for agents. This involves an orchestration layer that triages workflows—sending high-reasoning tasks to models like Claude and Gemini, while routing simpler tasks to cheaper open-source models like Llama. 4. ASIC Chips > General Compute? ⚡ NVIDIA is king today, but the future might belong to ASICs. As models become more specific to workloads, we’ll see models put directly onto cheaper, more tunable chips. This is why Meta is betting big on their own silicon—they’re preparing for the ASIC explosion. 5. Selling to Agents, Not Humans 💸 The buyer is changing. When agents start buying software, pricing must shift to consumption-based models. An agent doesn't care about a "seat license"; it cares about the compute and memory required to get the job done. 6. Intuition vs. Wishful Thinking 🧠 Jerry’s biggest misses? Confusing wishful thinking with intuition. He’s learned that the founders who make you feel "comfortable" are often the ones who let you down. The best founders are often socially challenged, obsessed, and possess a "sharp edge" that makes them win. 7. Money Has No Instructions ⚡ Money is simply energy. It doesn’t come with a manual. As an investor or founder, your job is to respect that energy—don't waste it on the "middle," use it to back the crazy ideas that have the power to change the world. (Link in Comments)