Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, CLASSICS]

Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, CLASSICS]

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Brad Jacob's simple principle of "think big, move fast" is one I think about often. 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 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 is a true force of nature, and I hope you enjoy his episode. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠⁠⁠WorkOS⁠⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠⁠WorkOS.com⁠⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit ⁠⁠joincolossus.com/episodes⁠⁠. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up ⁠⁠here⁠⁠. Follow us on Twitter: ⁠⁠@patrick_oshag⁠⁠ | ⁠⁠@JoinColossus⁠ Show Notes (00:00:00) Welcome to Invest Like the Best (00:02:11) 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

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Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY]

Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY]

Today, we are replaying one of my favorite conversations with Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76e...

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Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS]

Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS]

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Sean Feeney makes you want to be a...

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Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]

Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]

Today we are replaying my conversation with Justin Ishbia. Justin is the Founding Partner of Shore Capital. Shore is a private equity firm that invests in microcap businesses within industry niches. W...

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Joe Liemandt  - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]

Joe Liemandt  - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]

My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing...

26 Elo 20252h 27min

Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]

Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]

My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrop...

19 Elo 20251h 38min

Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]

Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]

My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built a notable private equity allocation platform within the wealth manageme...

12 Elo 20251h 31min

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discu...

5 Elo 20251h 34min

Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]

Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]

My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's rem...

29 Heinä 20251h 53min

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