Today, we are replaying my conversation with Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He has also written a book that will be out in January, titled “How to Make a Few Billion Dollars”. Brad’s energy is infectious and our conversation unpacks his strategies for M&A, his propensity for speed, and methods for earning team buy-in. Please enjoy my great conversation with Brad Jacobs.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

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Show Notes

(00:00:00) Welcome to Invest Like the Best

(00:07:11) Identifying key factors in a market before investing

(00:10:07) Gleaning insights from early acquisition experiences

(00:13:43) Delving into the seller's mindset during a business sale

(00:17:51) Weighing pre-built against organic growth strategies in acquisitions

(00:27:49) Engaging constructively with Wall Street

(00:29:36) Discussing the substantial buyback of XPO shares

(00:33:16) Ambition as a recurring theme in entrepreneurial success

(00:35:17) Emphasizing the need to facilitate team agility

(00:37:35) Highlighting the joys of post-acquisition integration

(00:41:09) Drawing lessons from Ludwig Jesselson's principles

(00:45:34) Comparing the risks and rewards of early versus late adoption

(00:49:09) Reflecting on errors made in trend analysis

(00:53:59) Strategies for implementing new technologies in enterprises

(00:56:59) The significance of thought experiments in strategic decision-making

(01:01:00) Recalling transformative events from his early years

(01: 02:22) Outlining what makes a meeting 'electric'

(01: 06:53) Sharing experiences with exemplary leadership

(01:12:37) Deciding the right time to step away from a business

(01:23:45) Philosophies for leading a fulfilling life

(01:27:53) The kindest thing anyone has ever done for Brad