Getting the Goalpost to Stop Moving

There aren’t many iron laws of money. But here’s one, and perhaps the most important: If expectations grow faster than income you’ll never be happy with your money. One of the most important financial skills is getting the goalpost to stop moving. It’s also one of the hardest.

Read more

How to Do Long Term

Long-term thinking is easier to believe in than accomplish.

Read more

Announcing $200M in New Funds for Entrepreneurs Pushing the World Forward

Today, we’re proud to announce that we’ve raised $200 million across two new funds — Collaborative V and Collaborative Growth.

Read more

The Optimal Amount of Hassle

Steven Pressfield wrote for 30 years before publishing The Legend of Bagger Vance. His career leading up to then was bleak, at one point living in a halfway house because it had cheap rent.

Read more

Play Your Own Game

Michael Jordan said he had to reconstruct his body when he went from basketball to baseball back to basketball. Baseball favored strong arms and chest; basketball required a leaner figure with a stronger core and legs. Part of the reason Jordan’s basketball return was rusty was because he was still lugging around his baseball arms. “Looking back, I didn’t have enough time to get back to a basketball body,” he said.

Read more

The Limits of Investing Sanity

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

Read more

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.

Read more

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.

Read more

A Few Short Stories

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

Read more

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.

Read more

Sign up for more Collaborative Fund content