The shoeless disrupter: How Steve Hilton’s bet on Trump cost him his startup

In 2014, Steve Hilton — the Republican now running for California governor — was a barefoot tech executive with plans to change the world.

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Hilton’s company, Crowdpac, was a kind of Kickstarter for politics. The nonpartisan platform aimed to help first-time candidates fundraise from grassroots supporters. The site aspired to bring an insurgent, punk ethos to the political world.

With Crowdpac, “you can get elected without the big party machines, without the big donors, without the special interest constraining what you have to do,” Hilton said in a 2016 speech.

At the office, former Crowdpac employees say Hilton embraced the stereotype of an iconoclastic startup founder. He biked everywhere and led whiteboard strategy sessions while seated on the table, his shoeless feet dangling from the edge. Hilton had a tortured relationship with his industry’s products; he didn’t own a cellphone, a quirk that wore thin for staff who sometimes had to track him down for meetings or order his Ubers.

Hilton’s politics were right-of-center, but in unpredictable ways. In the UK, he’d helped catapult the Conservative Party into power by moderating its image. He spoke admiringly about U.S. Sen. Bernie Sanders, I-Vt., helped lead the charge on Brexit, and wrote about the horrors of factory-farming. At his home in the suburbs of Silicon Valley, he raised chickens.

Then came Donald Trump’s 2016 election win.

First-time candidates — almost all Democrats — began to flock to Crowdpac, making Hilton, a Trump supporter, an increasingly awkward face of the company. Then, in 2017, Hilton accepted a weekly show on Fox News and increasingly spent his weekends defending the president.

It was a jarring split screen for many of the company’s left-leaning employees. The same CEO who preached democracy reform was now championing a movement many Crowdpac users saw as autocratic.

Democratic activists balked, Hilton stepped down and investments dried up. By June 2019, the once-promising platform was effectively dead.

To skeptics inside Crowdpac, Hilton’s pivot to Fox News and Trump endangered the platform’s efforts to reform partisan politics. Hilton says his politics didn’t shift; he calls it “positive populism,” a project he argues is broadly aimed at establishment power.

As a Trump-endorsed candidate for governor, Hilton has continued to rail against powerful political machines — made literal in recent AI-produced ads — of Sacramento Democrats, unions and business groups. He’s run ads targeting anti-Trump voters, casting himself as a “pragmatic problem solver.” But down by 25 percentage points to Democrat Xavier Becerra in a recent poll, he has yet to meaningfully assert independence from the unpopular president.

Hilton’s Crowdpac years sharpen the question for voters: Is his brand of anti-establishment disruption part of a bigger project to empower voters, or, as some former colleagues argue, a cynical play for attention?

In interviews, eight former employees and business associates of his tech company described Hilton as a creative thinker and gifted communicator. His approach managed to win over at least one former colleague ahead of the November election — a longtime Democratic voter who sees Hilton as a provocateur who can shake up a political class that they feel has grown out of touch and complacent.

“I believe he’s genuine,” said the colleague, who like most people interviewed, spoke on the condition of anonymity to speak freely about their experiences at Crowdpac.

But some ex-Crowdpac employees say Hilton sometimes lacked focus and seemed more interested in winning attention than execution. They say Hilton’s move to Fox amounted to a betrayal of the company’s guiding values.

“Steve is an opportunist, so he goes where the music is,” one said.

The ‘blue sky’ thinker heads to California

Hilton’s time in California started as a yearlong sabbatical.

Fed up and on the outs at London’s 10 Downing Street, where he was a senior advisor to then-UK Prime Minister David Cameron, the London-born Hilton would spend a year in California with his family.

It seemed like a natural fit for the “blue sky” thinker who’d never quite found his place in the Conservative Party he’d helped build. Hilton had helped moderate the party’s public image on issues like the environment, orchestrating Cameron’s 2006 visit to a melting Arctic glacier. But Hilton had grown impatient as his radical vision for Cameron’s UK — decentralizing power, slashing the civil service — succumbed to political realities.

Cameron, who had a falling out with Hilton, wrote in his 2019 memoir, “For the Record,” that his old friend struggled with the transition from opposition to government.

“I knew that to be successful in government you have to play the game,” Cameron said. “And he had no interest in playing the game, just tipping it over and throwing the pieces all over the floor.”

Then there was the harsh glare of the British media, where Hilton’s reputation as a shoeless spin doctor inspired a character in a fictional TV series.

In 2012, Hilton set off to join his wife, Rachel Whetstone, then a senior executive at Google. He never permanently returned.

“In a way, I think he was too California for the UK,” said Mason Harrison, a GOP communications strategist who worked alongside Hilton at Crowdpac and later helped lay the groundwork for Hilton’s gubernatorial campaign.

In Silicon Valley, Hilton found actual blue skies and people who appreciated his brand of offbeat thinking. He began teaching classes at Stanford’s design school, famous for its freewheeling brainstorming sessions, and found a receptivity toward new ideas that London lacked.

“I felt truly at home here in California in a way I haven’t felt anywhere else before,” Hilton said in an interview with the Bee.

A new way to fundraise

Hilton said the idea for Crowdpac partially came out of his desire to equip first time candidates with a platform to launch their political career. In 2013, he launched the company alongside Gisel Kordestani, a former colleague of Whetstone’s at Google who is married to prominent tech executive Omid Kordestani.

The startup was part of a wave of civic tech organizations like Brigade Media, Represent.Us, and Change.org that were fueled by 2010s optimism about tech’s ability to address thorny governance issues.

Kordestani and Hilton had a kind of “mom and dad show” in front of colleagues, said Salim Shariff, a progressive digital strategist and Crowdpac’s former engagement director. Hilton was the “ideas guy” while Kordestani handled the nuts and bolts of the business.

Early iterations of Crowdpac used campaign finance data and voting records to assign scores to candidates on overall ideology and specific issues. Several years of iterating led the company to become the fundraising platform it would best known as. Candidates or groups could gauge interest in their cause by setting up conditional fundraising, where donors committed money but only paid if a target was met.

Former Crowdpac employees said Hilton could be exacting on phrasing and design questions but largely trusted staff to take risks. Staff described him as easygoing and charming, though privately dismissive of the tech titans in his social circle whom he saw as out-of-touch elites. One former employee described Hilton as the best boss they’d ever had.

Hilton was fun and witty, a good guy to have a beer — or several — after work. But several former coworkers described moments where he was unpredictable. At a 2015 company retreat in Los Angeles, they say Hilton gave his colleagues a scare after he disappeared from a bar where they’d gathered — unreachable thanks to his cellphone policy. He showed up at the company Airbnb in the Hollywood Hills in the early hours of the following morning, having walked home. Another night on the retreat, Hilton allegedly got into a verbal tussle with a karaoke bar bouncer, causing staff to intervene and usher him away. (A spokesperson for Hilton didn’t respond to a request for comment on these episodes).

Hilton’s favored metrics involved attention rather than revenue. Staff delivered him printouts tracking pageviews and news clips. Former staffers said the focus on winning attention led Hilton to be unfocused, chasing projects based on the potential for clicks and coverage rather than business value.

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“It was like having a golden retriever in the office,” one former employee said. “Every time there was a shiny object, he wanted to go after it.”

Hilton called such criticism “fair” and said that experience and his time in the UK taught him the importance of dialing in to more specific goals. He told The Bee his gubernatorial campaign, with its oft-repeated populist economic promise of $3 per gallon gas and no tax on the first $100,000 of income, was a reflection of that focus.

A global populist revolution

For most employees, Hilton came off as a right-leaning centrist who liked to stir the pot.

Shariff, who joined Crowdpac after working on Hillary Clinton’s 2016 presidential campaign, said Hilton would “play devil’s advocate all the time in a cute, ‘I’m a conservative for the Bay Area kind of way.’”

In his 2015 book, “More Human: Designing a World Where People Come First,” Hilton called for less centralized and bureaucratic government, but gestured at a worldview that went beyond traditional conservative rallying cries. He said tax breaks for corporations should be accompanied by mandatory wage increases for workers and called for an end to factory farming.

Outside of Crowdpac, Hilton was working both publicly and behind the scenes to advance Brexit, after spending years pillorying what he viewed as excessive European Union mandates. Brexit’s success didn’t register much thousands of miles away at Crowdpac, but it cost him his friendship with Cameron, who was opposed to the move, and set the stage for what Hilton was coming to see as an upsurge in global populism.

As Trump emerged as the avatar of that movement, Hilton saw the reality show host’s disruptive potential earlier than most. While Hilton had been initially impressed with former Ohio Gov. John Kasich, a moderate Republican, Trump’s blow-it-up political ethos proved irresistible given Hilton’s anti-establishment bent.

At Crowdpac, Hilton laughed about Trump’s latest tweets and urged eye-rolling Democrats to take his campaign seriously. Conservative pundit Steve Bannon and Fox News owner Rupert Murdoch made stops at the office, and Hilton made a few cable news appearances stumping for Trump. But few of Hilton’s coworkers believed him to be a MAGA diehard.

Hilton’s Nov. 1, 2016 opinion piece on Fox News reflected his views of the race. He said Trump was the candidate who would make the “most positive, practical difference in the real lives of real people” while knocking him for “a string of offensive remarks” and “displays of almost crazed indiscipline.”

The Fox News pivot

The backlash to Trump’s win brought a wave of new Democratic candidates to Crowdpac, some of whom have gone on to durable careers in Congress: Rep. Lauren Underwood, D-Ill.; U.S. Sen. Andy Kim, D-N.J.; and Rep. Haley Stevens, D-Mich., who narrowly lost a Senate primary in that state last week.

When Hilton got the offer to host a weekly Fox News show on the global populist movement in 2017, he thought it would help his company. Almost 90% of the candidates using Crowdpac were Democrats, Hilton said. Here was a chance to reach Republicans and prove that his company could live up to its nonpartisan aspirations.

The first episode of “The Next Revolution” aired on June 4, 2017. It showed signs of Hilton’s heterodox politics. He proposed a year of national service to help unify the country, and, in a crusading segment named “Swamp Watch,” decried the revolving door between the banking industry and government. He called out Trump’s treasury secretary, Steve Mnuchin, as part of the problem.

In another episode a year later, Hilton rattled off the Trump administration officials who’d used taxpayer funds to upgrade their offices or go on extravagant trips — an affront to what he described as Trump’s “vital” drain-the-swamp agenda.

“Too many people there seem to think it’s business as usual,” Hilton said.

But as the show went on, Hilton increasingly steered programming to traditional Fox News fare: slamming sanctuary cities, attacking then-Speaker of the House Nancy Pelosi, and dismissing Trump’s critics as “idiots” and “elitists.”

Democratic activists and politicians took notice, calling for boycotts of Crowdpac in the spring of 2018. The mood inside the office soured. The platform had gotten some traction — revenue doubled from 2017 to 2018, Kordestani told Vox — but failed to achieve the kind of critical mass it needed to impress investors after burning through $15 million in venture funding.

“When the money that was going through the platform was not adequate to even pay recurring costs, let alone investment costs, it just becomes pretty clear that it’s not going to work,” one business associate said.

Hilton, and to a lesser extent, Kordestani were absent from the office for stretches. One employee recalled staffers openly interviewing for new jobs in the office.

Hilton eventually agreed that his Fox gig was hurting the company’s bottom line. In May 2018, Hilton stepped down from Crowdpac and an acting CEO, Jesse Thomas, said the company would temporarily suspend Republican candidates’ access to the platform, describing the move as a “stand against Trumpism.”

Hilton said he encouraged staff to “really lean into” the partisan messaging because he wanted the platform to succeed. But it was too late. A year later, Kordestani announced the company had run out of financial runway and was closing. It was purchased later that year and relaunched as CrowdBlue in 2025.

The rebranded version targets only Democrats and is led by Bart Myers, the CEO and founder of the former civic tech company Countable.us.

The aftermath

In many ways, Crowdpac succumbed to the inevitable.

“Right at the beginning, everybody told me that wouldn’t work — that politics is very tribal,” Hilton said. “I had this naive belief that we could bridge both sides.”

In his own political journey, Hilton’s political nomadism eventually landed him firmly in MAGA world, culminating in the Trump endorsement in April. For a man who was once so outspoken about the corrosive influence of insider-dominated, money-driven politics, Hilton has been notably silent as the president earned a record $1.4 billion last year while in office, accepted a $400 million Qatari jet, and used taxpayer dollars to renovate the White House.

Shariff speculated that his old boss had drifted to the right ideologically but also saw opportunity in the Trump era.

“He likes attention,” Shariff said. “And this was a pathway towards getting more attention that was a lot cleaner than trying to build a legitimate business.”

Hilton rejects the argument floated by some of his former colleagues that his scruples became a casualty of his ambition.

“I completely disagree with the idea that supporting a Republican administration is in opposition to the idea of democratizing politics,” Hilton said. “I don’t think Democrats own the idea of democratizing politics because Democrats have big donors too and have very entrenched interests.”

To Hilton, the throughline that connected Crowdpac, Brexit and Trump was “putting power in people’s hands” and boosting the welfare of workers. But a decade later, he conceded the goals remain largely unrealized.

“I think it is still very much an unsolved problem,” he said. “And that’s the real focus of what I’m running on in this election.”

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