It’s a blog.

It’s educational.

It’s hopefully entertaining.

It’s not investment advice.

How to think about investing.

Matthew Hennessy Matthew Hennessy

Bridge and Tunnel Crowd

Which side of the river do you find better investments? How do companies build bridges between businesses anyway? How to evaluate companies whose value is shifting between an old business and a new one.

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Matthew Hennessy Matthew Hennessy

Spot the Difference

Can you spot the difference between an expensive bill and one that ends up with a silver lining? How to evaluate the legislative consequences on an investment.

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Matthew Hennessy Matthew Hennessy

2025 Scoreboard

Lamplighter made some predictions for its portfolio in 2025. Some things it got right. Some things it got wrong.

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Matthew Hennessy Matthew Hennessy

Paint by Numbers

Can you create a masterpiece painting by numbers? What does painting have to do with investing? How to find investment opportunities when numbers paint a bad picture.

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Matthew Hennessy Matthew Hennessy

Growing Places

Who invests better: Sequoia or Oaktree?. What kind of trees should investors look for anyway? How to follow branches to find investment opportunities.

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Matthew Hennessy Matthew Hennessy

Extinction

What does paleontology say about digging for investments? How long does it take businesses to go extinct, anyway? How to find opportunities parsing dying companies from thriving ones.

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Matthew Hennessy Matthew Hennessy

Face Plant

When will you ever learn? What did you mess up this time? What lessons to take from losses and how to use them.

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Matthew Hennessy Matthew Hennessy

Origin Story

What came first: the product or the customer? Where do customers come from anyway? How businesses organize and how that can deliver value to investors.

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Matthew Hennessy Matthew Hennessy

A Tail of Two Companies

Is it the best of times? Is it the worst of times? How Dickens might look at analyzing a cash-registers-to-calling-cards venture.

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