Lessons from a Startup Life
Doug LevinAI and enterprise adoption, governance and trust, founder and board perspectives, and the evolving dynamics of VC, PE, blockchain, and crypto—offered through a free-plus-subscription model with select essays free and deeper, real-time analysis for sub's.
| Platform |  | Pricing | Freemium | Publishes | Daily |
|---|---|---|---|---|---|
| Issues | 661 | Founded | 5 years ago | Last Issue | 5 days ago |
| Active | |||||
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douglevin.substack.comLatest Issues
Angel Investing is Dead
The traditional angel investing involves making an initial seed investment with the expectation of follow-on VC rounds and eventual exit is no longer viable.
Recent data from Andrew Ross Sorkin’s DealBook (here) reveals a funding landscap...
What YC’s New Wishlist Tells Us
Y Combinator just published its Fall 2026 Requests for Startups, and the message is unmistakable: AI is done living inside a chat window. YC’s essay collection this batch reads like a map of where the smartest people in venture think intell...
New Titles Because of AI and Beyond
The New Org Chart: How AI Is Rewriting Job Titles
I’m getting used to seeing corporate and startup executives and staff carrying entirely new titles and mandates, reflecting how quickly organizations are restructuring around AI. A few exam...
What 600,000 AI Sessions Reveals About Today’s Web Traffic
As generative AI becomes a primary gateway to information, understanding how GAI assistants such as ChatGPT, Claude, Gemini, and others discover, and reference online content is becoming as important as traditional search engine optimizatio...
The Middle Manager Extinction Event Has Begun in the Tech Industry
The biggest tech fad of the past 30 years was the dot-com era, when companies were valued on eyeballs instead of earnings and investors poured billions into startups with no viable business model. It was a reminder that fads aren’t an anoma...
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Authors
The writers behind this newsletter.
Strategic, candid startup insights from Doug Levin—HBS Fellow, 4x CEO, Black Duck founder. Cutting through AI hype for founders, operators, investors & directors who want to know what actually matters.
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