By Fred Vogelstein 

Many still believe AI optimization is an oxymoron. You can’t optimize something as complicated and inherently unpredictable as a neural network. Even if it could be done, what AI chatbot would grant outside companies database access like that? That’s how they’re competing - on the proprietary quality of their data and algorithms. And why bother? AI chatbot training databases change infrequently. Even if you succeeded, it might take months before you saw results. 

By Om Malik

Dennis Crowley has built his career at the intersection of emerging technologies and human behavior. Twenty years ago, as a 25-year-old inspired by Harry Potter's Marauder's Map, he created Dodgeball—turning text messaging into a way for friends to find each other in the city. When the iPhone emerged, he launched Foursquare, riding the convergence of GPS, apps, and our growing comfort with social networks to transform how we interact with places around us.

Google bought Dodgeball in 2005 and eventually shut it down in 2009. Dennis left Google to start Foursquare with his co-founder Naveen Selvadurai. Foursquare rose like a meteor, and much of its core functionality was subsumed by Facebook. Mark Zuckerberg has no qualms about copying others’ ideas and then presenting them as his own. Foursquare, sadly, has since lost its preeminence in the location sweepstakes.

By Fred Vogelstein

When Shiv Rao was a cardiologist and investor in Pittsburgh, he saw a patient with a 10-year-history of breast cancer who seemed particularly tense during the appointment. “At the end of the encounter I asked her if there was something I did or said to make her so anxious. She told me that since her initial diagnosis of breast cancer her husband had come to every single encounter … and took notes. He couldn’t be there that day. She told me that him taking notes meant she could feel liberated to be present in the conversation knowing that they could go home and research all of his notes, Google them, and learn about all the different medical terminology that was discussed.”

By Om Malik

It’s Saturday in South Park. Kids are squealing. A man shadowboxes behind me. Sitting across from me on a not-so-clean bench are Bethany Bongiorno and Imran Chaudhri, partners in both life and work. They are co-founders of Humane, the San Francisco company behind AI Pin, arguably the first AI personal computer. (Also: What is an AI Pin?) We were meeting to discuss the next step in the company’s evolution. And what better place than the fabled South Park—erstwhile home to Twitter and Instagram, before they moved to a bigger future?

They launched about six months ago. Their promised device, the AI Pin, was supposed to free us from the tyranny of the phone and its screen. The square screenless device is a tad bigger than a smartwatch. It magnetically clips to your clothes. It looks like something right out of a “Star Trek” future. Press the device and ask it to make appointments or call an Uber.

What came into the hands of reviewers and eventually customers was nowhere close to the nirvana many had imagined. The gulf between the promise and reality had reviewers frothing at the mouth. One very influential reviewer called it the “worst product he had reviewed.” Others were equally or even more brutal.“The problem with so many voice assistants is that they can’t do much — and the AI Pin can do even less,” The Verge reported. The device had poor battery life, and heating issues, the laser display was subpar, and more importantly, the device felt quite laggy. The biggest cardinal sin, though, was that it didn’t really have a killer app in the traditional sense. For me, “AI” was that killer app.

By Om Malik

I first met Matthew Prince in 2010, the day he launched Cloudflare at TechCrunch Disrupt. His original pitch for Cloudflare was “Content Delivery Network (CDN) for the masses” that would take a few minutes to set up. Others like Akamai offered similar services, but for big-budget customers. Cloudflare was going after a burgeoning ecosystem of apps and relatively young services. That simple elevator pitch hid the real “why” of Cloudflare nicely—in the future, Prince and his co-founders Lee Holloway and Michelle Zatlyn wanted to build a network that would not only offer simplicity and speed but also protect their customers from emerging internet threats such as denial-of-service attacks.

Having seen the emergence of Akamai and a few other similar companies, it was clear Cloudflare was the one to watch. Their simpler, cloud-centric approach was novel. It was the way the modern internet was being built. It resonated with me. I decided to stay close, not only to Prince, who is a charming and eloquent communicator but also to keep close tabs on Cloudflare.

Fast-forward to today — that vision has turned Cloudflare into a $32 billion (in market capitalization) company with almost $1.3 billion in 2023 revenue. Those numbers don’t tell the full story of Cloudflare and its role in the internet’s infrastructure and smooth functioning. Just last month, the San Francisco-based company warded off a world-record 3.8 Tbps DDoS attack. DDoS attacks are very much a routine problem for large infrastructure providers.

By Fred Vogelstein

I remember when Bill Gross launched GoTo.com back in early 1998. The idea seemed nuts. Search was broken. Spammers had polluted results. In many cases they’d become just a list of who’d paid the most for placement. Google wasn’t even a company until the end of that year. But GoTo’s solution - to just be up front about spammers’ deception - seemed completely wrong. “Pay for search? That’s making it worse, not better,” most in Silicon Valley said. A chunk of the audience actually hissed at Gross when he was done unveiling GoTo at the 1998 Ted Conference in Monterey, he said..

Today we know what happened instead: The idea behind GoTo changed the world. GoTo was the first meaningful pay-for-performance search ad company - and half of what became Google Adwords four years later. When Google married pay-for-performance ads with its superior search results, it revolutionized the modern internet. No one thought you could make a dime with traditional search until Google did this. Google today is worth more than $2 trillion because it did.

Gross should have made a zillion dollars from this, but as he’ll tell you himself, he screwed it up. The idea seemed so obvious to him that he didn’t immediately think to patent it. And by the time he’d realized his mistake, during his first conversations with investment bankers wanting to take GoTo public, pay-per-click, as it came to be known, was unpatentable. 

Welcome to Crazy Stupid Tech, a newsletter about the tech-of-technology that shapes the future

If you don’t know us, here’s a quick introduction.

• I am Fred Vogelstein, an investigative technology and biotech journalist. I’ve been writing about Silicon Valley mostly for Wired, The New York Times Magazine and Fortune since 1998. I’m also the author of “Dogfight: How Apple and Google went to war and started a revolution.” 

• I am Om Malik, partner emeritus at True Ventures. I was the founder of GigaOm, a pioneering technology blog and media company. I have been writing about technology since the early 1990s, mostly for Forbes, Red Herring, Business 2.0, Fast Company and The New Yorker. I also wrote “BroadBandits: Inside the $750 Billion Telecom Heist.” I blog atOm.co