Throughout his tenure, Brad Jacobs has built multiple billion-dollar companies. While there is no "playbook" for growing a business, he focuses on a few factors above all else in every company he operates, and in this conversation, he reveals them all. Shane and Jacobs discuss how to read anyone during an interview through a series of intentional questions, the exciting role of AI and technology in the future of business, and where money-making ideas hide in companies. Jacobs also shares how his training in math and music made him a better business operator, the one thing he focuses on to grow his businesses, how to spot big trends before everyone else, and the only thing a company should focus on for success. Brad Jacobs has started five companies from scratch and led each to become a billion-dollar or multibillion-dollar enterprise. These include three publicly traded companies: XPO Logistics, where he serves as Chairman and CEO, United Rentals, and United Waste Systems. Before starting XPO in 2011, Jacobs founded United Rentals in 1997 and led the company as Chairman and Chief Executive Officer. In 1989, he founded United Waste Systems. (00:00) Intro (04:44) The future of AI (07:21) How to think rationally (08:48) The major trend (10:57) The research process (13:29) On asking better questions (19:35) On rearranging your brain (22:23) On music, math, simplicity, and business (32:26) Leverage, debt, and optionality (35:11) What it takes to take contrarian bets (40:45) Confidence and parents (50:21) Why negative-only feedback is detrimental for employees (56:14) Money lessons (58:13) A deep dive on M&A (Jacobs' secret sauce to growing his companies) (01:07:51) Questions to immediately get to know anyone (01:11:14) On boards and board meetings (01:16:57) On decision-making (01:23:37) The role of capital markets (01:25:41) The type of person you don't want to hire (01:31:16) The best capital allocators (01:33:53) Biggest lesson Jacobs learned from the past year (01:37:20) On success
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