Justin Khan was 42 years old, standing outside a Silicon Valley tech conference, when he told a stranger with a camera that selling Twitch to Amazon for $970 million did not make him happy. Not for more than a couple of weeks, anyway. That admission, offered casually and without any apparent desire for sympathy, captures something the richest people at one of the largest tech conferences in America kept circling back to when pressed for their actual secret: the money was almost beside the point. The channel School of Hard Knocks spent a day cold-approaching AI founders, billionaire investors, and one Sacramento Kings owner to find out what it genuinely takes to get rich, and what to do once you get there.
The guy who made coding optional
The first billionaire stopped mid-stride after stepping off a conference stage. Amjad Masad, who turned 38 the same year he crossed into billionaire territory, grew up in Jordan, the son of a refugee father who bought his family a computer early and changed everything. His company, Replit, built a platform where anyone can describe an app idea in plain language and have it built without writing a single line of code. When asked what separates people who get rich from people who do not, he was direct: ‘It’s not about smartness. It’s people who ship, people who do things.’ He turned down a $1 billion acquisition offer in 2019 because, in his words, he wants to build a trillion-dollar company. His advice on which corner of AI to chase was deliberately non-specific: pick the industry you already know, find where AI has not touched it yet, and go. A nurse, a truck driver, a sports obsessive, anyone with lived experience in a field has a differentiated starting point that a generalist coder does not.
Justin Khan, whose origin story with Twitch began as a 24-hour personal livestream of his own life that his friend Michael Seibel and his own father laughed at over dinner, described his edge as a ‘tweaked sense of risk.’ Google got close to buying the platform, opened talks at $150 million, worked up toward a billion, and then both sides walked away. Yahoo came next and also walked at the last minute. Amazon closed the deal in 2014. Khan’s negotiation advice traced back to a book he called Negotiation Genius: never be the desperate party, always have options, and an entrepreneur who can be talked out of their idea probably should be.
A $50 arrival and a basketball court in the basement
The final interview moved off the conference floor entirely and into the Silicon Valley home of Veerabhadra Kandasamy Divekar, known as VC Divekar, owner of the Sacramento Kings, who arrived in America with $50 in his pocket and has since sold companies for a combined sum reaching into the billions, including one that was valued at $30 billion at its peak. His basement holds a full basketball court where, he mentioned without elaborating much, Barack Obama and NBA star Shai Gilgeous-Alexander have played. He joked that after finishing the house, the city changed the zoning rules so no one could build a basement that size again, comparing the city council to the Mughal emperor who allegedly had his craftsmen’s thumbs removed after the Taj Mahal was finished.
At 67, Divekar described the one trait his entire billionaire network shares as being ‘a little bit outrageous and a lot ferocious,’ then defined ferocious as chewing cactus: ‘You just chew the cactus, you listen, you smile, you learn, you adjust, and you keep moving forward.’ When asked whether everyone is built for entrepreneurship, he was blunt. If someone has to ask a speaker whether they should quit their job to start a company, the answer is already no.
The $50 and the court that cannot be replicated
The basketball court in VC Divekar’s basement sits under recessed lighting, full regulation size, inside a home the city has since effectively ruled can never be duplicated.
Ashton Kutcher, who raced through a brief conversation between a stage appearance and a flight back to Los Angeles, was asked for the single most important conversation of his career. He named asking Mila Kunis to marry him. He credited the network of Silicon Valley figures he met early, including Mark Cuban, Ron Conway, Marc Benioff, and Jason Calacanis, not for what they knew but for showing him that a faster route existed. ‘It’s like you can get from Los Angeles to San Francisco on the 405 or you can take a plane,’ he said. ‘If you don’t even know that a plane is available, you’re never going to jump on the Southwest flight.’
