Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS]

Welcome to this classic episode. Classics are my favorite episodes from the past ten 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.

Hello and welcome, everyone. 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 joincolosis.com. Patrick O'Shaughnessy is the CEO of Positive Sun. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Some. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of positive sum may maintain positions in the securities discussed in this podcast.

To learn more, visit psum.vc. 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 curios. It's no wonder he's been among the most commonly request guests when I asked several top investors and CEOs who I should have on the show. We discussed 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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