It’s a blog.

It’s educational.

It’s hopefully entertaining.

It’s not investment advice.

How to think about investing.

Two Guys Walk Into a Bar
Matthew Hennessy Matthew Hennessy

Two Guys Walk Into a Bar

How low can expectations go? Kicking the tires on opportunities where investors have no expectations.

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Pompidou en Houston
Matthew Hennessy Matthew Hennessy

Pompidou en Houston

Does the game you’re playing line up with the game your investments are playing?

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Arcade Fire
Matthew Hennessy Matthew Hennessy

Arcade Fire

What are you playing at? Investors face a choice many never see: what game you play when making investments. Choosing the right one improves your odds of success.

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A Different Kind of Contract
Matthew Hennessy Matthew Hennessy

A Different Kind of Contract

What did you expect? Broken expectations. How a cocktail of a busted deal, regulatory purgatory and a strong underlying business might offer investors an attractive opportunity.

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Fine Print
Matthew Hennessy Matthew Hennessy

Fine Print

What do you know about the future? When investing, it helps to know something about that. How to think about the future without a crystal ball.

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How Are We Feeling Today?
Matthew Hennessy Matthew Hennessy

How Are We Feeling Today?

How do you respond to losses? Market downturns hurt, emotionally. But they’re bound to happen. Rather than fight them, use them to take advantage of investment opportunities.

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A World Away
Matthew Hennessy Matthew Hennessy

A World Away

How do you spot other investors’ mistakes? Bad behavior regularly crops up in investment markets. Use it to make better decisions.

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Running of the Banks
Matthew Hennessy Matthew Hennessy

Running of the Banks

What causes bank runs like the one on Silicon Valley Bank? How can you avoid that?

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Plan B
Matthew Hennessy Matthew Hennessy

Plan B

What happens when company adventures don’t go to plan? Evaluating an investment against numerous future scenarios. How investors can benefit from adaptability.

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Rabbit Holes
Matthew Hennessy Matthew Hennessy

Rabbit Holes

What to do when you run into complexity? What happens when investors focus too much on one indicator? How to find opportunity by looking for what other investors miss.

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Time Off For Good Behavior
Matthew Hennessy Matthew Hennessy

Time Off For Good Behavior

What happens when investors lose their mind? Investor fits happen frequently. How to take advantage of them?

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Staying on Deck
Matthew Hennessy Matthew Hennessy

Staying on Deck

How much can you win? How much can you lose? How to think about balancing risk and reward.

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Invest. Don’t Speculate
Matthew Hennessy Matthew Hennessy

Invest. Don’t Speculate

How do you pick a winning investment strategy? Sorting out the differences between proper investing and everything else. Thinking about risk and how you might feel if an investment goes wrong.

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