Bill Gurley (@bgurley) is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. His new book
Life is a use-it-or-lose-it proposition.
Shouldn’t you spend it doing something you love?
This book will teach you how to find your dream job and avoid a career you’ll regret—from a leading venture capitalist, based on his viral college talk.
Shouldn’t you spend it doing something you love?
This book will teach you how to find your dream job and avoid a career you’ll regret—from a leading venture capitalist, based on his viral college talk.
This title will be released on February 24, 2026.
AI summary:
- AI as a "Real Technology Wave" with Speculation (0:23-1:39): Bill Gurley discusses how every significant technology wave, like AI, inherently attracts speculation and "bubble-like behavior" due to rapid wealth creation. He emphasizes that a real technological shift and speculation often go hand-in-hand.
- "Circular Deals" in AI Investments (3:06-3:52): Gurley explains "circular deals" where large companies like Microsoft invest in AI startups (e.g., OpenAI), and those startups then agree to purchase services from the investor. He views this as a questionable and non-transparent accounting practice.
- Concerns for Retail Investors in AI SPVs (4:20-5:28): Gurley expresses concern for retail investors getting involved in AI-related Special Purpose Vehicles (SPVs). He warns that many promoters of these SPVs may not even have the underlying stock, calling it the "wild wild west" and advising extreme caution.
- Challenges of Private Company Investing (7:10-8:06): The video highlights two main problems with the public investing in private companies: the majority of VC-backed private companies go to zero, and there's a lack of information transparency compared to public markets.
- Angel Investing Strategy in AI (9:05-9:30): For angel investing in the current AI landscape, Gurley suggests looking for individuals who are highly curious, actively using AI tools, and bring a unique perspective from a specific industry that gives them an advantage.
- Institutional Investor Focus on AI-Only Deals (9:50-10:41): Currently, institutional investors have "zero interest" in non-AI deals. This means that if an angel-funded deal isn't AI-related, it risks "dying of neglect" as it won't attract future institutional funding.
- Protecting Your Career with AI (10:43-11:08): Gurley advises everyone, regardless of their field, to start "playing with this stuff" (AI). He believes that being the "most AI-enabled version of yourself" is the best way to protect your career from potential displacement by AI.
- Investing in "Off the Beaten Path" AI Verticals (12:28-13:05): When investing as an angel, Gurley recommends focusing on "deeper verticals" or niche industries that are not high-priority targets for large AI companies like OpenAI (e.g., waste management). These verticals often involve specific workflows and proprietary datasets that big models won't easily "crush."
- Importance of Proprietary Data Sets and Workflows (13:16-14:06): Successful AI investments in specific verticals will likely involve proprietary data sets and the ability to build software around existing "workflows"—tasks that need to be automated and integrated with AI, like booking tours in real estate.
Bill Gurley — The AI Era, 10 Days in China, & Life Lessons from Bob Dylan, Jerry Seinfeld,, and More - YouTube @Tim Ferris
wisdom for career: "don't half-ass it" => rocket fuel for life!
