It’s a blog.

It’s educational.

It’s hopefully entertaining.

It’s not investment advice.

How to think about investing.

Spot the Difference
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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This Investment Has Pockets
Matthew Hennessy Matthew Hennessy

This Investment Has Pockets

Are pockets in dresses really that great? What ends up in dress pockets anyway? How to evaluate an investment with some pockets of extra costs.

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Tomb Raider
Matthew Hennessy Matthew Hennessy

Tomb Raider

Do decades-old investment ideas have any value today? What if its the same idea? Evaluating investments that worked out and why they might work out again for the same reasons.

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Magic Eye
Matthew Hennessy Matthew Hennessy

Magic Eye

What parlor tricks help with investing? Can an investment make magic? How to see an investment.

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Jungle Boogie
Matthew Hennessy Matthew Hennessy

Jungle Boogie

How much do you need spend to be king of the jungle? What’s the jungle worth anyway? How to find opportunity in hyper-spending by hyperscalers and the return on that investment.

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Natural Deselection
Matthew Hennessy Matthew Hennessy

Natural Deselection

What makes a better snack: a snake or a crocodile? Why would snakes and crocodiles choose to tussle anyway? How to evaluate mergers between companies with sharp teeth and primitive instincts.

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Chips on the Table
Matthew Hennessy Matthew Hennessy

Chips on the Table

Would companies rather play poker or blackjack? What do card games have in common with investing anyway? How to evaluate the cards a company plays against its tells.

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A Heist
Matthew Hennessy Matthew Hennessy

A Heist

What’s the ROI on a bank robbery? If you’re not going to rob a bank, what’s the next best thing? Evaluating mergers for a bargain price.

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Laws and Order: Part 2
Matthew Hennessy Matthew Hennessy

Laws and Order: Part 2

If things work out, what does that look like? How do you know when you get there? How to evaluate an investment’s prospects when shares have been on a rip.

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Laws and Order: Part 1
Matthew Hennessy Matthew Hennessy

Laws and Order: Part 1

Are shares subject to any real laws — like physics — about how they behave? Can they break those laws? How to evaluate investors expectations when share price drastically changes.

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The Hour Between Dog and Wolf
Matthew Hennessy Matthew Hennessy

The Hour Between Dog and Wolf

How do you tell a dog from a wolf in the dark? What about in the markets? How long does it take to turn a wolf into a dog anyway? How to find investments using uncertainty.

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Marginalia
Matthew Hennessy Matthew Hennessy

Marginalia

What notes are worth jotting down in the margins of a book? How important are margins to value anyway? How to find opportunity when a plot twist suddenly changes a company’s business mix.

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The Comments Section
Matthew Hennessy Matthew Hennessy

The Comments Section

Is it ever a good idea to read the comments section? Is it all toxic? What if people actually try to be helpful? How to find value in digital communities with real people.

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The Great Wave
Matthew Hennessy Matthew Hennessy

The Great Wave

Where do you find the best waves? Do waves work for investors or do they crash them into the sand? How to find opportunity in consumer product cycles.

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Where the Staircase Ends
Matthew Hennessy Matthew Hennessy

Where the Staircase Ends

What’s a business’ final investment? How many steps between here and the one where shareholders get cash from it? How to evaluate shareholder-friendly policies in a booming business.

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Something Fishy
Matthew Hennessy Matthew Hennessy

Something Fishy

Do sardines make good investments? What should you do if trading in a company’s shares smells fishy? How to distinguish whether a company is trading just on vibes or something real.

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Gold Rush
Matthew Hennessy Matthew Hennessy

Gold Rush

How do you figure out if an investment’s pure gold? What about the things you need to get to the gold… like picks and shovels? How to evaluate “pick and shovel” opportunities in AI.

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Bird’s Eye View
Matthew Hennessy Matthew Hennessy

Bird’s Eye View

How would a bird look at a portfolio? Does a book of investments look different all grouped together? A look through at the business activity of the portfolio.

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2025 Scoreboard
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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Jackass of All Trades
Matthew Hennessy Matthew Hennessy

Jackass of All Trades

What’s wrong with you? Why do you make so many bad decisions? How to evaluate mistakes from the year.

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