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Turning $5M Into $100M

In 2015, Collaborative Fund made an unusually bold bet—investing $5 million—20% of a $25 million fund—into a single startup.

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Beautiful vs. Practical Advice

I heard a phrase recently: “Magazine architect.”.

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Pure Independence

A simple formula for a pretty nice life is independence plus purpose.

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The Quiet Beverage Bet Outpacing AI Hype: How OLIPOP’s Investors Are Winning

If I told you a company was on track for $500M in sales in 2024 — up from $200M in…

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Minimum Levels of Stress

A day after the September 11th terrorist attacks, every member of Congress stood on the steps of the U.S.

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I Have A Few Questions

They’re relevant to everyone, and apply to lots of things…

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America’s Superpower

“Our political leaders will know our priorities only if we tell them, again and again, and if those priorities begin…

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A Message From the Past (Thoughts on Nostalgia)

After college, my wife (who was then my girlfriend) and I got an apartment in the Seattle suburbs.

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Do It Your Way

The ultimate success metric is whether you get what you want out of life.

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Take Something Away

Ryan McFarland came from a long line of motorsports junkies given that his grandfather had been a race car engineer…

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Podcast With Howard Marks

I recently sat down with legendary investor Howard Marks, co-founder of Oaktree Capital Management.

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Cumulative vs. Cyclical Knowledge

President James Garfield died because the best doctors in the country didn’t believe in germs, probing Garfield’s bullet wound after…

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A Number From Today and A Story About Tomorrow

Every forecast takes a number from today and multiplies it by a story about tomorrow.

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A Few Little Ideas And Short Stories

I once asked a successful author how to market a book.

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Fill The Bathtub

Despite being awash in information, it seems harder than ever to uncover the truth.

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Makes You Think

A few lines I came across recently that got me thinking…

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