How to Transition: Experiments, Time-Bound Trials, and Permission

Bill Gurley (@bgurley) is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. His new book is Runnin’ Down a Dream: How to Thrive in a Career You Actually Love.

This episode is brought to you by:

• Momentous high-quality creatine for cognitive and muscular support
• Our Place’s Titanium Always Pan® Pro using nonstick technology that’s coating-free and made without PFAS, otherwise known as “Forever Chemicals”
• Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business
• Coyote the card game​, which I co-created with Exploding Kittens

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Timestamps:

• [00:00:00] Start.
• [00:01:43] The book that gave Jerry Seinfeld permission to pursue comedy and inspired Runnin’ Down a Dream.
• [00:03:59] AI bubble or not?
• [00:06:33] Circular deals and SPV chaos.
• [00:12:01] Angel investing in the AI era.
• [00:14:32] Why you should be the most AI-enabled version of yourself, regardless of field.
• [00:20:47] China deep dive: Ten days, six cities, high-speed trains, and a Xiaomi SU7 factory tour.
• [00:22:43] Communism misconceptions.
• [00:25:40] Lei Jun: The Steve Jobs of China.
• [00:29:17] Jack Ma, ByteDance’s invisible CEO, and the risks of prominence in China.
• [00:32:11] America vs. China (Lawyers vs. engineers).
• [00:41:01] Keys for US competitiveness.
• [00:43:47] Bill is bullish on these countries.
• [00:47:30] Matthew McConaughey’s “Don’t half ass it” moment.
• [00:49:45] Runnin’ Down a Dream thesis: Helping people pursue X instead of A, B, or C.
• [00:51:03] The 80,000-hour question.
• [00:52:47] The self-learning test.
• [00:56:58] Bob Dylan as music expeditionary.
• [01:00:27] Go to the epicenter where the action is.
• [01:10:56] Danny Meyer’s pivot.
• [01:13:30] Working for free.
• [01:19:37] Never too late: Tito Beveridge started Tito’s Vodka at 40.
• [01:21:51] AI sanity checks.
• [01:25:59] AI-proof bets.
• [01:29:13] Sam Hinkie’s Moneyball moment.
• [01:32:37] Competitive strategy, avoiding false failures, and regret minimalization.
• [01:43:46] Purpose, Progress, and Prosperity — the P3 Policy Institute.
• [01:47:18] Regulatory capture explained.
• [01:51:55] Why the IPO market is broken.
• [02:01:52] Stablecoins putting Visa and Mastercard on notice.
• [02:03:40] Hopes for Runnin’ Down a Dream and parting thoughts.

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