It’s a blog.

It’s educational.

It’s hopefully entertaining.

It’s not investment advice.

I write about how to think about investing.

Pie by the Slice Redux
Matthew Hennessy Matthew Hennessy

Pie by the Slice Redux

Do pixels mix with pizza? What do parking tickets tell us about digital payments? How helping customers helps your stockholders.

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Week Theory
Matthew Hennessy Matthew Hennessy

Week Theory

If you don’t yell in a forest and everyone is around to listen, what happens then? How much can an investor get done in a week? How to think about time and investing.

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Not So Fast
Matthew Hennessy Matthew Hennessy

Not So Fast

Does everyone drive an EV? What happens when bankruptcy makes a company more complicated? How think about opportunity at the fork between expectations and reality.

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Pie by the Slice
Matthew Hennessy Matthew Hennessy

Pie by the Slice

Why does Costco sell pizza for $1.99? How can a company reduce its costs with different size slices? What does any of this have to do with payments processing? How lessons from Costco and Amazon fit into financial plumbing.

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Five Hours
Matthew Hennessy Matthew Hennessy

Five Hours

What’s the half-life of an investment idea? How long does it take to look foolish on the internet? What can you take away from the market’s “constructive criticism?”

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Lights, Camera, Action
Matthew Hennessy Matthew Hennessy

Lights, Camera, Action

What does good writing tell us about investing? Do good stories make good investments? How to compare investing bestsellers.

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Schrodinger's Deal
Matthew Hennessy Matthew Hennessy

Schrodinger's Deal

What does quantum physics tell us about stock prices? When is a merger both alive and dead? How to use what investors “know” to frame an investment decision.

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Let Them Eat Crab Cakes
Matthew Hennessy Matthew Hennessy

Let Them Eat Crab Cakes

How much does free crab cost? Can I just get the free part? How to unbundle weird pieces of a merger to test an investment.

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Tilting at Windsocks
Matthew Hennessy Matthew Hennessy

Tilting at Windsocks

How would Don Quixote charge at merger regulation? What’s the record on errant regulatory crusades? How to evaluate opportunity in marquee regulatory tilts.

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Stadium Seating
Matthew Hennessy Matthew Hennessy

Stadium Seating

What do stadium restrooms tell us about investing? How did the move to indoor plumbing highlight opportunity? Finding investing chances in a digital paper chain.

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The Smart Investor
Matthew Hennessy Matthew Hennessy

The Smart Investor

What makes an investment smart? What makes another intelligent? Can an investment be both? A field guide for figuring it out.

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A Tail of Two Companies
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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Dirty Money
Matthew Hennessy Matthew Hennessy

Dirty Money

What’s your role? Do economists have a sense of humor? An empirical analysis. Advice for what to do when you see money lying around.

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Cookies & Cream
Matthew Hennessy Matthew Hennessy

Cookies & Cream

What happens to ice cream sandwiches when your baker turns off the ovens? What do ice cream sandwiches have to do with digital advertising? A framework for evaluating companies in transition.

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A Cart Full of Bread
Matthew Hennessy Matthew Hennessy

A Cart Full of Bread

What’s better than a barter system? Are ways to pay for things getting simpler or more complex? Ways to think about financial plumbing.

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I’ve Got Terrible News
Matthew Hennessy Matthew Hennessy

I’ve Got Terrible News

Why is the news always bad? If the news is only bad, how do you know what news you should pay attention to? An umbrella for the rain. How to figure out what matters for an investment.

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Craps at a Poker Table
Matthew Hennessy Matthew Hennessy

Craps at a Poker Table

What happens when things goes off-script? How do you think about a new investing environment? What happens when things change? How not to play poker.

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Mise en Place
Matthew Hennessy Matthew Hennessy

Mise en Place

Want to start a bank? What do you need? What happens when a bowl of Dum Dums doesn’t cut it for customer service any more? How to cook with convenience.

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Rube Ex Machina
Matthew Hennessy Matthew Hennessy

Rube Ex Machina

How do you tell if an investment is working? What about a whole portfolio of investments? How to set up a scorecard to figure this out.

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