020 - What's It Like to Have a Full-Time Personal AI Assistant

ai.u crew continue their discussion on using new AI tools to “automate yourself,” focusing on agentic products like Claude Cowork, Microsoft Cowork, and Perplexity Computer, how to get started, and subscription costs. They note Claude’s $20/month plan is quickly token-limited and may require upgrading to a higher tier (about $125/month) for sustained use. Kevin describes Cowork controlling a browser to complete a driver safety course (with user oversight), building presentations, and scraping hundreds of sites to assemble a financial model, while cautioning that token use can make simple web tasks inefficient and that guardrails are necessary. Travis highlights common low-hanging uses like consolidating transcripts/emails into documents and raises tensions with websites that block bot behavior, the ad-driven web, and paywalls. The group debates how agents shift attention, incentives, and agency, increase output volume, distance people from work and reality, and change how they read, learn, and connect online, while noting growing experimentation across nontechnical professionals.00:00 Welcome Back and Setup00:37 Part Two on Automation01:46 Getting Started With Claude02:02 Pricing and Token Limits03:19 Kevin Tests Cowork03:53 Driver Safety Course Demo05:22 Scraping and Token Tradeoffs07:20 Travis Low Hanging Use Cases08:05 Web Bots vs Site Defenses09:54 Ads and the Agentic Web17:18 Subscriptions and Paywalls19:54 Claude Add Ins and Dispatch22:44 Building Pitch Decks Fast23:58 Agents Change Human Attention25:34 Personal Assistants and Insularity28:11 Debating an Article With AI29:28 Simulated Debate vs Humans30:06 AI Comment Slop on LinkedIn30:57 Skipping the Messy Learning32:47 Everyday People Try AI33:58 Life With AI Assistants34:58 Developers and Abstraction Drift36:23 Outcomes Over Outputs37:04 Summaries and Shrinking Attention37:59 Agents Gatekeeping Humans39:12 Whose Agent Is It40:01 Trust Without Expertise41:44 Drowning in Agent Activity43:22 Robots and Household Tasks45:49 High Agency vs Low Agency47:51 Writing for Agents Now50:15 Proximity Still Matters51:44 Subscription Agents Everywhere52:39 Wrapping Up the Agent Era53:43 Agents Talking to Agents54:26 Final Sign Off This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aiunprompted.substack.com