Charlie Songhurst – Lessons from Investing in 483 Companies

**Patrick O'Shaughnessy** (0:00)
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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**SPEAKER_2** (1:42)
Patrick O'Shaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit PSUMVC.

**Patrick O'Shaughnessy** (2:11)
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 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.
Charlie, I like starting these things in a unique way, and one idea that you've had is to have people stack rank their vices of power, money and fame. I'd love you to begin by explaining why you're interested in this idea and what you've learned from the answers over the years.

**Charlie Songhurst** (3:00)
So it's a two-part question. One is the virtues, which is working with people you like, working on amazing problems and having impact. And then the three vices, power, money and fame. And you can't avoid them. They have to be stacked rank separately. And it's really trying to get at the differences between, there's no good answer, but there are definite good fit answers. So someone who's interested in power tends to be better at execution. Someone's more interested in money tends to think more about some capital efficiency. I tend to avoid people interested in fame. But if you were doing something in showbiz, it would presumably be the number one criteria. If you think about the difference between sort of impact, intellectual interest, working with people, you really get the impression of where people are going to be happy and where they're not going to be happy. You also start to understand why certain organizations do so well. So SpaceX, if you think about it, stacks high on all three. It's intellectually interesting. You're working with amazing people. You have huge utilitarian impact in the world. Whereas if you're working for FinTech, you're less likely to have that utilitarian positive impact.

**Patrick O'Shaughnessy** (4:02)
Any especially memorable or interesting series of answers that you've gotten on the two stack ranks that come to mind?

**Charlie Songhurst** (4:09)
A lot of people have negative utility from fame. A lot of people start with power, and then when you push them, it's actually money, but they don't want to say it. And that's more true outside of the US culture than it is in the US. It's particularly true with Europeans. And so a lot of it is trying to get people to actually say what they truly believe as opposed to say what they think they should say.