Invest Like the Best with Patrick O'Shaughnessy
Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS]
27 Jun 2025
Full Episode
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are end of one conversations with end of one people. Charlie Songhurst is a brilliant strategist, an accomplished executive, and a prolific angel investor. It's one of my all-time favorite conversations, not just on the podcast, but period. I hope you enjoy it.
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I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
You can find Colossus Review along with all of our podcasts at joincolossus.com.
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My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies through his career. I met Charlie at an event hosted in New York, and you can tell within one minute of meeting him that his mind is sparkling with ideas and curiosity.
It's no wonder he's been among the most commonly requested guests when I asked several top investors and CEOs who I should have on the show. We discuss the lessons he's learned about business, investing, and people from such a large sample size of companies. I won't reveal any more here. I highly recommend you just listen to Charlie and learn. Let's dive in.
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