Jack Dorsey is kind of a ghost in his own machines. Most people still think of him as the "Twitter guy" with the long beard and the nose ring, but honestly, that version of Jack is long gone. If you've been following his moves lately, it’s clear he’s trying to dismantle the very idea of the corporate social media giant he helped invent.
He’s currently the head of Block Inc., but even that feels like a temporary title for a man who seems more interested in being a digital monk than a Silicon Valley CEO. While most billionaires are busy building bigger walled gardens, Dorsey is out here handing over millions to open-source developers and telling everyone to leave the platforms he started.
It’s weird. It's fascinating. And it’s exactly why he remains the most misunderstood American entrepreneur of the last twenty years.
The Bluesky Breakup Nobody Saw Coming
The biggest shocker recently was his sudden exit from the board of Bluesky. Remember, Bluesky was his baby. He started it as a research project inside Twitter back in 2019 because he was tired of the "company" part of social media. He wanted a protocol—something like email—where no one person or board could decide what you see.
But then Bluesky became a company. It got venture capital funding. It started building moderation tools.
Jack hated it.
He basically said they were repeating all the same mistakes he made at Twitter. To him, if you have a board of directors and a "block" button that the company controls, you aren't building freedom technology; you’re just building another cage. He deleted his account, left the board, and now he’s telling people that Elon Musk’s X is actually closer to his original vision of "freedom technology" than the platform he actually funded.
It's a bizarre pivot. But if you look at his obsession with decentralization, it starts to make sense. He doesn't want to be in charge. He wants the code to be in charge.
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"Bitcoin is Money, Not Crypto"
If you want to understand Dorsey in 2026, you have to stop using the word "crypto" around him. He’s a Bitcoin maximalist to his core. For Jack, Bitcoin isn't an investment or a digital gold bar; it’s literally the future of how every person on earth will buy coffee.
Through Block Inc., he’s been pushing projects like Bitkey (a self-custody wallet) and Proto (his Bitcoin mining hardware). He’s betting the entire house on the idea that Bitcoin will eventually replace the US dollar. He recently stated that he expects BTC payments to become a straight peer-to-peer flow with zero fees by the end of this year.
Most CEOs wouldn't dare say the dollar is dying. Jack says it while wearing a "Satoshi" t-shirt at the Super Bowl.
The "And Other Stuff" Era
While he still runs the show at Block, his heart seems to be in a new nonprofit collective he’s backing called "and Other Stuff." He dumped $10 million into this group to build apps that don't need the internet to work.
Take Bitchat, for example.
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It’s a messaging app he helped launch that uses Bluetooth mesh networking. Basically, you can text people nearby even if the government shuts down the internet or a hurricane knocks out the towers. It uses something called the Nostr protocol, which is Jack’s current obsession. Nostr isn't an app; it’s a way for data to move around without a central server.
He’s also backing weird, niche projects like:
- Sun Day: A tool for tracking UV exposure.
- Shakespeare: An AI-driven platform for building social apps on the Nostr protocol.
- White Noise: A privacy-first messenger.
He isn't trying to build the next Facebook. He’s trying to build a digital toolkit that makes companies like Facebook obsolete.
What Most People Get Wrong About His Wealth
People see the $4 billion or $5 billion net worth and assume he’s living the typical billionaire life. But his #StartSmall initiative has been quietly draining that wealth for years. He’s donated hundreds of millions to everything from universal basic income pilots to independent journalism through groups like BBC Media Action.
He’s also a notorious "single-tasker." He doesn't do "multitasking." If he’s in a meeting, he doesn't have a phone. If he’s eating, he’s just eating. This monk-like focus is what allowed him to run two public companies at once, but it’s also what makes him seem detached. Former employees often describe him as "aloof" or "idealistic to a fault."
Is he a genius or just lucky? Probably a bit of both. But you can't deny that he's the only founder from that original era who is actively trying to destroy his own legacy to build something more honest.
Actionable Insights: How to Think Like Dorsey
You don't need a billion dollars to adopt the "Dorsey mindset" regarding technology and work. Here is how you can actually apply his philosophy today:
- Audit Your Data Sovereignty: Start looking into "self-custody." Whether it's your Bitcoin or your personal photos, try to move away from services where one company can delete your entire life with a single "Terms of Service" update.
- Look at Protocols, Not Platforms: Instead of worrying about the next big app, look at the tech underneath. Learning how protocols like Nostr or ActivityPub work will give you a better idea of where the internet is heading than any TikTok trend.
- The Power of "No": Dorsey is famous for his "Don't" list. He doesn't do breakfast. He doesn't do most meetings. Identify the one thing that actually moves the needle in your career and ignore the rest.
- Support Open Source: If you’re a developer or a creator, contribute to projects that aren't owned by a corporation. The "freedom technology" Jack talks about only works if people actually build on it.
Jack Dorsey is effectively betting that the era of the "Big Tech CEO" is over. He’s trying to be the last one out the door, and he’s leaving the lights on for whoever wants to build something that no one can own.