The Limits of Investing Sanity

Jerry Seinfeld had the most popular show on TV. Then he quit.

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Investing At The Later Stage

Collaborative Fund’s focus is investing in startups at the beginning of their journey. We have seeded dozens of new businesses over the last decade, and have even been one of the first investors in some special companies like Gumroad and Scopely, Magic Spoon, among others.

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The Spectrum of Optimism and Pessimism

At one end you have the pure optimist. He thinks everything is great, will always be great, and sees all negativity as a character flaw. Part is rooted in ego: he’s so confident in himself that he can’t fathom anything going wrong.

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A Few Short Stories

Thirty-seven thousand Americans died in car accidents in 1955, six times today’s rate adjusted for miles driven.

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The Big Lessons of the Last Year

History is one damned thing after another. A war ends, a boom follows, then a crash, then an uprising, then a pandemic, a breakthrough, a new boom, a new war. On and on, from agony to awe.

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Five Investing Powers

Rare and helpful:

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Too Much, Too Soon, Too Fast

Some things scale well. Double their size and you get double the output (or more). Other things don’t, and my God is it important to know which is which.

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Investing: The Greatest Show On Earth

Let me share two quick stories that have nothing to do with investing. I want to convince you of something important and overlooked: Investing is a broader field than it looks, and there is so much to learn about it outside of the narrow lens of finance.

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The Fed Isn’t Printing As Much Money As You Think

The risk of rising inflation over the next few years is probably the highest it’s been in decades. Inflation happens when too much money chases too few goods, and Covid-19 closed a lot of businesses and gave people an unprecedented amount of money. The stars align.

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When Everyone’s a Genius (A Few Thoughts on Speculation)

The end of a speculative boom can be inevitable but not predictable. Unsustainable things can last a long time. Identifying something that can’t go on forever doesn’t mean that thing can’t keep going for years. Years and years and years.

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