November 1st, 2025. Bloomberg News. Today, we are here with Alan Wang. CEO of Pitch-22. “So Alan, what is the inspiration behind Pitch-22?”
“Well, it was kind of obvious, our optimization culture was destroying our social fabric. You know. Many of my close friends I made while waiting for the bus…but now buses are always on time. I didn’t have to talk to the cashier anymore or even step outside most days. I created Pitch-22 to make society inefficient again. You know. Late buses. Long checkout lines. I feel like this is the solution our society needs.”
Pitch-22 had just raised their Series C at a valuation of $1.5B. Alan was a wiry kid from Stanford, who took golds at the Math Olympiad in high school.
“Our entire company culture follows this unoptimization philosophy. Our website is 40% slower than competitors. Our hiring page, 80%. Our office layout is inspired by shopping malls, so it takes employees longer to get to their desks.”
Sequoia Capital’s Vinod Sharma was very excited about the company. “I think this is the sort of innovation that advances not just our country, but civilization. When I was young, the power would go out and all the kids would run to the terrace. These sort of inefficiencies are what the company promises. We’re very excited to work with Pitch-22 to see them fulfill this dream.”
Jeremy, a golden-haired skateboarder, one of the first users of Pitch-22, told us about his experiences: “I mean. Dude. This app is insane. The subway timings are always wrong. I can order food through the app, but I have to pick it up at the restaurant. No delivery. It gives me the slowest walking directions. Ever since I’ve started to use the app, I’ve just been more zen bro.”
One of the engineers chimed in: “We’ve partnered with restaurants, stores, and transportation agencies across the country who now follow our deoptimization protocol. This allows us to horizontally integrate across every industry, making our super-app a one-stop shop.”
Alan’s co-founder, Zack, a Phd philosophy drop-out from Stanford, is one of the quiet geniuses behind the start-up. He explained that Pitch-22 uses a novel pluralistic optimization method. “Of course, simple utilitarianism is insufficient. There is more to human life than reducing suffering! There is beauty, existence, diversity, and many other values that existing models couldn’t capture. We came up with a highly pluralistic value engine, and to prevent us from trying to optimize it, we use AI to create a black box algorithm!”
One of the interns at the company, Shreya, had posted a day-in-the-life video of working at Pitch-22. She was a bright-eyed computer science student at Cornell, who had joined last November. “Every day is a new challenge …. quite literally! I’ve never been asked to think so out of the box. Today, I was reading papers on the organization of pre-colonial Spanish societies. They had a remarkably high societal-trust-score, which we are trying to replicate. We’ve identified a high correlation between lack of self-sufficiency and societal trust.”
Yet, Pitch-22’s app’s own social media “The Field” has revealed some concerning details about their recent updates. In one case, a flight booked through the app to Geneva but was re-routed mid-flight to Uruguay. Carol was visiting her family but was surprised to be greeted in Spanish when she arrived at the terminal. One of the engineers responded: “It appears that our novelty-serendipity-engine was incorrectly weighted in your case. We apologize for the inconvenience.”
Carol’s family had filed a class-action lawsuit against the company after they had refused to reimburse the flight tickets, as it would be “antithetical to the company’s vision, and we must maintain fairness for everyone.” Brigham, the company’s executive lawyer, declined to comment further.
Recently, a16z, concerned about the company’s reputation brought in some “external talent” from their other ventures to help stabilize the company. This led to a schism within Pitch-22, with many outraged by the new ROI goals and performance benchmarks. Moreover, they had fixed the elevator, eliminating all serendipity, one employee complained. Jeremy noted that a new app feature now allowed him to pay extra for longer wait-times at restaurants.