Silicon Valley’s most privileged relationship is now dead. At the beginning of 2022, I rang up my colleagues and proposed a deal: I wanted to get together with a bunch of private equity firms and buy Twitter. …

December 9th, 2021 Dear Congressman Sherman: I was extremely impressed by your comments and questioning during yesterday’s House Financial Services Committee hearing on Digital Assets. …

While the crypto industry was busy failing to reinvent payments, it accidentally solved the biggest problem in the global economy. — I’m going to forego a long-winded introduction to the world of the crypto, and all of the arguments for why it’s a sign of the End Times, because 1) it’s 1:30am and I can’t believe I’m writing this instead of catching up on sleep; 2) we’ve all read the blog…

How toxic “philosophy” has left a generation of fintech executives morally bankrupt — As of this moment, one of the most upvoted posts of 2021 on Hacker News is an item regarding the hiring culture at Stripe, which is accompanied by a comment thread that includes many interesting anecdotes about the behavior of Stripe’s executives when interacting with others in their industry. Some…

Why the future of the tech industry isn’t the dark dystopia it appears to be. — The last time I discussed “unproductive insecurities versus productive insecurities” was about 10 years ago, in a meeting with a group of venture capitalists. The end result: they laughed me out of the room and doubled-down on their investments in companies like Snapchat. …

Take it from someone who’s seen it before: the iOS 15 “child safety” fiasco could be a sign that the End Time has arrived. — About 10 years ago, after landing at the airport in Toronto, I was taken aside for questioning at the immigration counter. “We see that you keep coming in and out of the country for a few days. What are you doing in Canada?” “Well, I’m advising a friend on what…

The Olympics composer scandal provides the world with a tiny glimpse of the biggest problem facing the Japanese economy. — Prior to the opening ceremony of the 2020 Tokyo Olympics, one of the big news stories was the resignation of the event’s musical composer. As reported by Japanese national broadcaster NHK, the story went like this: [Keigo] Oyamada resigned as a composer for the ceremony on Monday, saying that his…

Many years ago, I went to a dinner party hosted by a super-successful real estate developer. The developer and I were good friends, so he didn’t care too much as I listened in while he discussed his latest project with his mega-developer friends. “I’m like a mouse! I just slowly…

From a long-lost friend. — Whenever someone well-respected or successful passes away, there’s always a million glowing, positive stories about them. People who knew the deceased after they gained their fame or success will always come out and tell you how great the person was. As someone who’s spent quite a bit of time around…