My guest today is 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 conversation with Brad Jacobs.

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For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

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Show Notes

(00:02:11) - (First question) - Identifying key factors in a market before investing

(00:05:07) - Gleaning insights from early acquisition experiences

(00:08:43) - Delving into the seller's mindset during a business sale

(00:12:51) - Weighing pre-built against organic growth strategies in acquisitions

(00:17:20) - Defining the elements of an ideal business

(00:22:49) - Engaging constructively with Wall Street

(00:24:36) - Discussing the substantial buyback of XPO shares

(00:28:16) - Ambition as a recurring theme in entrepreneurial success

(00:30:17) - Emphasizing the need to facilitate team agility

(00:32:35) - Highlighting the joys of post-acquisition integration

(00:36:09) - Drawing lessons from Ludwig Jesselson's principles

(00:40:34) - Comparing the risks and rewards of early versus late adoption

(00:44:09) - Reflecting on errors made in trend analysis

(00:48:59) - Strategies for implementing new technologies in enterprises

(00:51:59) - The significance of thought experiments in strategic decision-making

(00:56:00) - Recalling transformative events from his early years

(00: 57:22) - Outlining what makes a meeting 'electric'

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

(01:05:02) - Strategies for maximizing team potential

(01:07:37) - Deciding the right time to step away from a business

(01:08:58) - Unveiling unexpected challenges in entrepreneurship

(01:18:45) - Philosophies for leading a fulfilling life

(01:21:04) - Finishing How To Make A Few Billion Dollars

(01:22:53) - The kindest thing anyone has ever done for Brad