Jason Calacanis Talks Crypto, Startups, and Wild Ideas

• Jason Calacanis was an early investor in Uber and Robinhood, trusting his instincts before others saw the potential.
• He approaches crypto cautiously, often criticizing hype-driven projects and promoting honest discussions through his podcast and ventures.

Jason Calacanis was not born into a family of investors. Born and raised in Brooklyn, his life used to be full of simple routines. However, his high curiosity made him never satisfied with just being a spectator. He entered Fordham University and studied psychology, but who would have thought that the direction of his life would change far from Freud’s theories.

Before being known as an investor who made gold from Uber and Robinhood, Jason managed a technology magazine in the 90s called Silicon Alley Reporter.

It could be said that when other people were still doubtful that the internet would survive, he had already started discussing small technology companies that are now giants. From there, his sensitivity to reading opportunities became sharper.

Jason Calacanis: Timing It Right With Uber and Beyond

If anyone is curious about how someone can become a millionaire just because they are “on time,” then Calacanis could be the most obvious example. He became one of the earliest investors in Uber.

Yes, when people didn’t know that there would be an application to order a car with just one touch, Jason had already seen the potential there. Something similar happened when he entered Robinhood, a stock trading platform that has recently become popular among young people.

But of course, not all investment decisions always go smoothly. Some of the technology projects he funded did not always explode. However, his instincts proved strong. Now, he is said to have invested in more than 300 startups, and his writings about the world of startup investment in the book “Angel” are often used as references by many novice investors.

A Cautious Step Into Crypto Space

On the other hand, his involvement in the crypto space was not as fast as his run to the startup sector. Jason tends to be selective. He did not immediately declare himself a crypto supporter, but rather often criticized several projects that he thought had no direction.

For example, in early 2025, he openly criticized GameStop’s decision to buy Bitcoin. He considered the move to be just camouflage for a business that did not have a strong foothold.

However, he continued to follow discussions and developments in the crypto ecosystem. In fact, he even provoked debate after stating that maybe it was time for a “better Bitcoin”. This statement made some of the community upset, but there were also those who agreed and saw it as critical thinking about the future of digital payment systems.

Interestingly, Jason also did not hesitate to call XRP a “centralized security.” For those who only watch from the sidelines, comments like this may seem sharp. But that’s Jason, he doesn’t like small talk, especially about projects that he thinks deviate from the initial spirit of crypto.

From Bold Proposals to Global Podcasts

Furthermore, he had proposed a fairly controversial idea: a crypto tax. The goal is to build strategic reserves. However, this proposal was immediately rejected by other figures such as David Sacks. Such quick reactions are indeed commonplace for Jason. But at least, he is not afraid to throw out ideas that may sound crazy to some people.

Even so, he doesn’t just sit in the investor’s chair. Through Founder University and the All-In podcast that he manages with several colleagues, he continues to be involved in conversations that influence the way the public views the world of technology and investment. In fact, his podcast has won the top position globally in the technology category several times.

When Calacanis Pays Attention, So Does Everyone Else

On the surface, Jason Calacanis may seem like someone who’s fierce toward new trends. But in reality, he just chooses not to follow suit if he doesn’t understand or is not sure. In a crypto space full of hype and sweet promises, this kind of skeptical approach can actually be a healthy filter.

Will he dive deeper into the crypto space? Not necessarily. But if suddenly there is an altcoin project that enters Jason’s radar and he decides to get involved, it is certain that many people will follow suit. After all, his reputation as someone who is “one step ahead” has been proven many times.