Which Would You Rather Earn? 20% or 148%?
Wednesday, February 18, 2026
Time for a pop quiz! Here we go: Here are the results of two investments.
About 632 articles by Matthew Milner
The #1 Way to Profit from Startups in 2026
Wednesday, February 11, 2026
One of my old buddies from business school is a venture capitalist. When I started Crowdability about ten years ago, I asked him what the biggest myth was about early-stage startup investing.
SpaceX + xAI: What It Means for You
Wednesday, February 4, 2026
Did you see the news yesterday? Elon Musk announced that SpaceX is acquiring xAI. This deal — the largest M&A transaction in history — brings together rockets, satellites, billions in cash flow from Starlink, and AI.
Y Combinator’s New Bet Reveals Where You Can Make 41x Your Money
Wednesday, January 28, 2026
Here’s one of the most reliable ways to take advantage of big new investment trends early: Follow the investors who consistently spot winners before anyone else. In the startup world, one of those investors is Y Combinator (YC).
Betting on Home Prices: A New Way to Play Real Estate
Wednesday, January 21, 2026
There’s a new way to bet on real estate. Now you can bet real money on whether home prices in a specific city will finish up or down during a certain month, quarter, or year.
Your Invite to “The Next Chapter” of Venture Capital
Wednesday, January 14, 2026
Venture capital has always moved in chapters. There are periods of exuberance.
The Billion-Dollar Bet to Bring Back the Dodo
Wednesday, January 7, 2026
Not so long ago, the dodo was a punchline. The flightless Mauritian bird vanished in the 17th century.
The Stock Market Isn’t the Stock Market Anymore
Wednesday, December 17, 2025
For years, if we wanted our money to grow, we’d invest in the stock market. And for years, this was fine.
Missed the AI Rally? Here’s the Big Opportunity Today…
Wednesday, December 10, 2025
My buddy Jamie teaches high school in Boulder. He called me in a panic last week.
13 Reasons Now’s the Time to Invest in Startups
Wednesday, December 3, 2025
A few weeks before Thanksgiving, my 6-year-old came home with a Labubu. Not a boo-boo, which he often comes home with after a rough soccer match.