“Should I wear a keffiyeh to the shooting range?” Amjad Masad asked as I slid into the passenger seat of his black Mercedes sports car. The patterned Palestinian scarf has become a political lightning rod in the two years since the war in Gaza began. Masad, the founder of AI coding startup Replit, and a Palestinian by origin, wrapped it around his neck anyway.

At the shooting range in Santa Clara, we collected an assault rifle and a pistol and headed in. With the AR-22 tucked into his shoulder, Masad fired at a brisk clip, peppering bullets into a cartoon burglar. In less than two minutes, the burglar’s head was perfectly pocked with holes. 

“You should compete,” I suggested. 

He smirked. “I always compete.” 

Indeed, Masad has never been shy about his competitive streak or his political beliefs — especially since Oct. 7, 2023, when Hamas attacked Israel, setting off the war in Gaza. 

Masad, 38, has felt obliged to speak out about Gaza ever since, calling out those in tech who, in his view, have supported Israel’s “genocide” of the Palestinian people. He quickly learned just how unpopular that opinion was in Silicon Valley.

Party invitations dried up, group chats lit up with techies condemning his posts, and investors called him a “terrorist sympathizer.” One member of a firm that backed Replit publicly declared (opens in new tab) in July that he would donate any earnings from the investment to the Israel Defense Forces. 

“I felt like I was sort of expelled from Silicon Valley,” Masad said in November on the way to the range. 

But even as Silicon Valley cooled on him, the AI boom that Masad had long bet on took off. In 2024, Replit combined its coding tools with AI to create an agent that could turn plain English prompts into pre-coded apps. After nearly a decade, the company was suddenly in the right place at exactly the right time. 

Two years later, Replit is booming. In September, it raised $250 million from Prysm, Andreessen Horowitz, Amex Ventures, and others, at a valuation of $3 billion. The company hopes to create the preeminent AI coder — one so easy to use that anyone can become a software engineer. Meanwhile, Masad continues to advocate for his political beliefs. 

“People reached out to me to express that my words have been hurtful and that many have been deeply offended,” he posted on X over the summer (opens in new tab). “I finally realized that I must, from the bottom of my heart, apologize to — absolutely nobody.” 

Masad’s swagger isn’t unique among tech founders. But for many, their against-the-grain takes tend to align with the bottom line. Masad insists he speaks up even when it hurts his business. In that regard, “I’m probably the only contrarian in Silicon Valley,” he told me.

As Replit takes off, will he be able to maintain that independence?

Replit’s multibillion valuation is hitched to the AI boom. Should the boom fizzle, the company could be worth nothing. But if it holds, and AI continues to remake the tech industry and the greater economy, Masad could find himself among the Valley’s next class of billionaires. 

Replit has plenty of competition among AI code-to-product firms (which are typically built on top of the mega LLMs). Swedish startup Lovable raised $330 million last month (opens in new tab), and Israeli company Base44 was bought by website builder Wix for $80 million this summer. All told, the AI coding sector received $4.7 billion in U.S. funding in the last year alone, according to PitchBook. 

To persevere, Masad will not only have to beat his competitors with a better product but will have to earn the favor of still more investors, given the massive capital it takes to build and power Replit’s models.

For this reason, most players in AI have been pragmatic with their politics; see, for instance, how many Silicon Valley figures who previously supported liberal causes — from Marc Benioff to Mark Zuckerberg — suddenly and enthusiastically embraced the Trump White House. Or how Jensen Huang reportedly cozied (opens in new tab) up to David Sacks, hoping the AI czar would convince President Donald Trump to loosen U.S. chip restrictions and allow Nvidia to sell more products globally. Or how Sam Altman has courted Gulf royalty, landing major (opens in new tab) deals to build data centers in the region and fund OpenAI’s stateside infrastructure needs.

For the most part, Masad has been unwilling to soften his positions. With a penchant for discursive discussions on political philosophy, Masad remains eager to speak about the war in Gaza and rail against what he sees as human rights abuses committed by Israel.

And he’s keen to take meetings with anyone who might see eye to eye on Palestine, even if they don’t agree on tech policy. Masad has spoken with New York Mayor Zohran Mamdani and messaged Lina Khan, the former chair of the Federal Trade Commission and nemesis of the tech elite. He had dinner with Tucker Carlson and lasted the obligatory three hours (opens in new tab) on “The Joe Rogan Experience.”  

In short, Masad sees himself as both a champion for Palestine and a mogul in waiting. Which, particularly to other Arabs in tech, has made him a hero. “Having one of us make it in Silicon Valley — and still stay vocal on Palestine in the midst of all of this, specifically in Silicon Valley — is extremely inspirational,” said Fadi Ghandour, executive chairman at investment firm Wamda, one of the backers of Replit. 

All this is a world away from Amman, Jordan, where Masad grew up. On the drive from his home in Palo Alto to the gun range, Masad told me his youthful hobbies included drift racing on Amman’s streets and shooting guns in empty lots.  

Masad, who speaks unexpectedly softly given his combative persona, is aware of how lucky he is. He compared his circumstances to a simulation experiment in which “if you ran the world a million times, I think 90% of them, I’m in a really bad situation. I’m in prison or dead.” Instead, “somehow I keep surviving and winning.” 

Replit’s multibillion valuation was in many ways the fruits of Masad’s decades-long study of how to make it in Silicon Valley. As a teen in Jordan, he avidly followed Y Combinator cofounder Paul Graham, studying his blog posts and obsessively scrolling through Hacker News, the Y Combinator news feed. 

After getting his computer science degree in 2010 from Jordan’s Princess Sumaya University for Technology, he created the first iteration of what would become Replit: an open-source program for coders to work within a web browser, a novelty back when programmers needed to buy specialized software.

He posted a link to the program on Hacker News, where it went viral. That led to securing his first job in the U.S., as the founding engineer at Codecademy in New York. In 2013, he took a job as a software engineer at Facebook. By 2016, he and his wife, Haya Odeh, decided to revisit his old project from Jordan, officially founding Replit as an online platform to help developers build, collaborate, and publish their software. 

As a student of Silicon Valley, Masad knew that mythmaking was just as important as the product. He began live-blogging Replit’s progress, and his efforts soon caught the attention of Graham himself. “What struck me most about him, at first, was that he was a programmers’ programmer,” Graham said. “He wasn’t just working on software to make money. He’d have been writing it no matter what.”

Graham invited Masad and Odeh to apply to the Y Combinator accelerator program in 2018. They were accepted, and after completing the program, Replit landed investment from Andreessen Horowitz. With that funding and support, Replit gained traction as a tool for students to learn coding and educators to teach it. According to Masad, he turned down a $1 billion acquisition from Github, believing Replit would one day be worth exponentially more. 

Masad’s ultimate objective was to leverage his success in tech to help the Palestinian cause — a sentiment instilled in him by his mother. “She would tell me about all the great things I’m gonna do,” he said. “I fantasized as a kid about helping the Palestinians and ending the occupation and being an important force in the world.”

But in 2019, he effectively put the company on pause after his mother’s cancer took a turn for the worse. Masad and Odeh traveled to be with his father, a civil engineer with the Jordanian government. 

The experience was traumatic for Masad. In his mother’s final days, the doctors in Jordan wouldn’t let any visitors into the ICU. Masad begged, then yelled, and they finally relented — on the condition he sign a “do not resuscitate” order. He still doesn’t understand why. By the time he got to see her, she was unconscious. “I was so angry at modern medicine,” Masad said. “So angry at modernity.” She died shortly thereafter.

After a few months, Masad returned to Silicon Valley. He couldn’t stop thinking about civilization at large, about where the world was going, and if he could stand it — or if he could change it. He found himself agreeing with the Valley’s increasingly powerful libertarians. 

He bonded with Marc Andreessen over politics and literature, and traveled to Malaysia to visit Balaji Srinivasan’s mysterious “startup society.” He grew to realize that the limitations he had assumed don’t necessarily apply. “There was an aspect of, like, ‘Fuck the system,’” Masad said. “‘We need to remake civilization.’” 

Masad gained a following on Twitter by bantering with tech legends about everything from coding to bitcoin to Covid vaccine skepticism. His growing stature landed him on podcasts and in glowing (opens in new tab) articles in The Wall Street Journal portraying him as a maverick. Then came the ultimate Silicon Valley validation: Graham, the idol whom he’d studied obsessively as a teenager in Jordan, started thanking him in his own blog posts.  (opens in new tab)

Meanwhile, Replit was struggling. The education market turned out to be small, and the company had trouble expanding into enterprise deals. In late 2023, Replit killed its education product and the following year laid off 30 employees — right after moving into a bigger office in Foster City. “I remember walking around the office and just feeling sick to my stomach,” he said. “I felt like I let people down as well, because I sold them this big dream, and it wasn’t working.” 

He had a plan, though, one he hoped would make his odyssey worth it. For years, he had proselytised on podcasts about how AI would turbocharge coding. Replit had spent years building an extensive database of coding materials — he just needed foundational companies like OpenAI and Anthropic to catch up and release an LLM capable of writing code. Once they did, Replit could plug those models into its pre-existing database and create a powerful app-building AI agent. 

While a new AI coding company would have to build out that infrastructure from scratch, Replit, Masad realized, could start miles ahead. After nearly a decade, he would finally have perfect timing.  

And then came Oct. 7, 2023. 

Masad had always been outspoken online. After Hamas’ terrorist attacks, as segments of the tech elite publicly lined up behind Israel, he held his ground. And his responses grew more costly. 

First, there were the public fights. Masad advised Elon Musk (opens in new tab) to “stick to his principles” when the billionaire said the slogan “from the river to the sea” was calling for genocide. (Palestinian activists say it’s a call for the peaceful liberation of the Palestinian people; pro-Israel voices say it calls for the extermination of Israel.) He clapped back (opens in new tab) at Lux Capital founding partner Josh Wolfe, who said that equating Israel’s actions in Gaza to genocide “grotesquely disgraces” Holocaust victims. And when Keith Rabois of Khosla Ventures said Masad’s “friends” (opens in new tab) were behind the Oct. 7 attack, Masad challenged him directly.

“If you think my friends did that then why don’t you confront me when you see me?” Masad replied on X (opens in new tab). 

But even as things got noisy in public, Masad met eerie silence professionally. “My calendar was suddenly empty, because I was talking about Palestine,” he said. “Replit was not a hot company anymore. We did a layoff. And at the same time, a lot of my friends were no longer my friends. I was no longer invited to parties.” 

Potential partnerships dried up. Masad became a frequent topic in pro-Israel tech groupchats, a source said, where some investors accused him of being antisemitic.  

A Replit investor who requested anonymity to speak candidly told me Masad’s public persona has been “really challenging,” and he’s had to defend the founder in investor circles. I asked if Masad had lost business because of his views. “I’m sure the answer is yes,” the investor said. 

A startup that Masad had invested in pitched another investor — and found that Masad was a liability. “He said, ‘Oh, Amjad is investing. He’s like a terrorist sympathizer. If he’s investing, I’m not investing,” Masad said he was told, though he declined to name the company or the investor.

But as Silicon Valley grew chilly, other regions beckoned.

In April 2024, with Replit a few months from launching its AI agent, Saudi Arabia’s Public Investment Fund, which is worth nearly $1 trillion, invited Masad and other AI thought leaders to stay at Ekland Safaris, a property in South Africa linked (opens in new tab) to Crown Prince Mohammed bin Salman. 

For Masad, it was a lifeline. Here were potential partners who didn’t care about his politics on Palestine. If anything, his Arab identity and his outspokenness made him more attractive.

In the heat of the day, a hunting guide sped Masad and other guests, including Tareq Amin, the future CEO of Saudi AI company HUMAIN, across 30,000 acres to kill kudu and wildebeest. By night, guests feasted in a grand ballroom while Masad demoed his not-yet-released AI coding agent to Saudi officials. 

“We’re going to be able to give a software engineer to every person,” Masad told Amin. “Anyone in the world will have a software engineer on demand.”

Amin said he thought then that Replit was on “a path to build a game-changing technology.” Indeed, if the agent worked, and if the AI boom Masad had been betting on came to pass, everyone in that room stood to benefit.

Replit launched its AI agent in September 2024 and within a year, revenue had reached $150 million. Amin and Masad closed a deal for Replit to be the exclusive AI coding software for Saudi governmental agencies, a partnership Masad expects to lead to “hundreds of millions” of dollars worth of business. 

And just like that, Silicon Valley wanted back in. Replit landed enterprise deals with Atlassian and Zillow, with a Meta deal in the wings, according to Masad. Replit raised its $250 million round and scored its $3 billion valuation. 

It helped Masad that, in the two years since Oct. 7, there’s been rising public disapproval (opens in new tab) of the Israeli government. He also gained strength in numbers: There have been high-profile movements (opens in new tab) within Google, Amazon, and other tech giants, with employees speaking out in support of the Palestinian cause.

“Today, the tide in tech has shifted,” Masad posted to X in September. (opens in new tab) “If you’ve been holding back, now is the time to speak out and call out anyone supporting or celebrating genocide.”

With Silicon Valley warming back up to him — he was on a16z’s podcast in October (opens in new tab) — Masad was invited to larger, and more controversial, audiences. He drove hours to record at Carlson’s rural Maine cabin, nodding politely when the host marveled on air at his perfect English. In July, he sat down with Rogan, talking about everything from Gaza to the Covid vaccine, which Masad has refused to take. 

“I tend to have a negative reaction to anyone forcing me to do something,” Masad said, prompting a “Good for you” from Rogan. “It was the same thing now with talking about Palestine and things like that. The more they come at me, the more I want to say things.” 

He appears now to have the capital, both financially and socially, to draw hard lines. “There are a lot of people who care about the Palestinians but who are afraid to speak out publicly,” said Graham, who has also been an outspoken advocate for Palestine. “What Amjad and I have in common is that we don’t have to worry about being fired if we do.”

Masad said Israel’s Ministry of Education had reached out around 2016 to work with Replit. “We got very close to a deal, but they were very overbearing,” he said, adding that the government had what he viewed as cumbersome requirements, like fining Replit if the service went down. The ministry did not respond to a request for comment. 

He says he would never work with Israel now. “I think it’s an illegitimate and criminal government,” he told me during our gun safety training. “I mean, [Benjamin] Netanyahu is a war criminal.” 

When I pointed out that Saudi Arabia has its own abysmal human rights record, Masad drew a contrast.

“I just think about how Replit is going to be used. Like, Israel is actively committing genocide and ethnic cleansing, and if you sell to the government there, it’s possible that they’re going to use it for that,” he said, pointing to the country’s use of Microsoft cloud services to track Palestinians’ phone calls. (After an investigation by The Guardian, Microsoft said it disabled the services that made the tracking possible in September. (opens in new tab))

It’s a careful, and conveniently self-serving, justification. This logic allows Replit to work with countries that Masad finds tolerable. Whether that line will hold as Replit scales is unclear.

After the shooting range, we drove through a thick forest fog to the restaurant The Mountain House in Woodside. Over grilled venison, Masad talked about Replit’s next challenge: expanding its user base from corporate clients to everyday users. This isn’t essential — plenty of companies thrive selling enterprise software. But Masad wants Replit to be an engine for socioeconomic mobility around the world, letting anyone, anywhere, easily create apps and businesses.

Masad acknowledged that if he succeeds — if Replit goes public and he becomes a billionaire — he will have the capital to make real change for Palestine, though he’s light on details. “It’s hard to plan for 20 years in the future,” he shrugged. “I just know that wealth is a prerequisite.”