๐Ÿ“ถ 17 Lessons from Charlie Songhurst (Angel Investor in 500+ Companies)

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Good morning ๐Ÿ‘‹

This weekโ€™s deep dive is on Charlie Songhurst, an angel investor in 500+ companies that most of you probably havenโ€™t heard of.

Despite making a huge impact in the startup world, Charlie prefers to invest behind the scenes.

He is hard to find online, selective with where he does interviews. The majority of our takeaways came from two pieces of media.

This was one of our favorite investor deep dives, and we hope you enjoy.

Read the full post below, and explore all investor deep dives here.


When you are managing ten or less people, they are actually managing you by influence because they can understand your desires. You no longer have these personal connections as you scale.

The angle of decline between productivity-per-person is what separates good startups from great startups. Great startups are all A+ players; good startups still have some fat to cut.

Study inversion. Focus on what causes failures, and try not to do that.

Itโ€™s hard to be smarter than everyone else. Itโ€™s easier and better to have a unique insight because you inhabit a unique position.

Talented people have more options than ever. To increase your chances of hiring well, the best thing you can do is compete on variables.

You can ruin your company by hiring too fast and too poorly. You can see 100 person companies that are much less productive than they were as a 10 person startup.

Interesting and complex ideas attract the smartest people. If you hate competition (which all investors claim they do), you should avoid the interesting and complex.

The most mis-valued asset in the world are entrepreneurs in markets that are non-obvious. If youโ€™re looking to beat the market, you wonโ€™t find a better bet.

Some of the smartest people out there are the least interested in being noticed. Charlie is one of the smartest investors I have studied, and Iโ€™m willing to bet that <5% of you have ever heard of him because he has no online presence.

Geographically disparate networks and travel help you gain insight. Avoid defaulting to a US perspective on everything.

If you are interested in other people, you will eventually become interesting. Get out there and mix it up.

The absence of conflict in Europe is underpriced. France and Germany will not fight each other due to the scars of two World Wars and decades of defense underinvestment.


“What you’re looking, for as an investor is high utilitarian outcome, and the ability to capture it.โ€

“People get a dopamine from things they have made money in before.” This allows for marketing ploys that are meant to cloud judgement.

“Where are the incredibly qualified people in the weakly competitive labor markets?”

โ€œIn boring and complex businesses, the spiritual reward of the industry are lower, and so you get fewer entrepreneurs. Therefore, the chances of succeeding in boring and complex businesses is significantly higher.โ€

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Clay and Tyler

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