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If you’re going to discuss the significance of Donald Trump’s presidential election win for the tech industry, then a podcast studio is as good a location as any.
Harry Stebbings, the 28-year-old podcaster-turned-investor, is used to asking the questions around the studio table in London, having interviewed an array of tech founders, executives and venture capitalists since the first episode of his 20VC show in 2015.
But on this occasion, a few days after the Trump victory, he’s giving answers – on the significance of podcasting to the president-elect’s media strategy and what the tech industry secretly thinks about a Republican White House return.
Meeting Stebbings, you’d think he could suit either world, having the sociable, can-do nature that makes him an obvious fit in both settings. He dropped out of a law degree at King’s College London within months of starting it and launched his successful 20VC podcast series by conducting an interview with Silicon Valley investor Guy Kawasaki from the kitchen of his family home.
Big names have followed, including OpenAI chief Sam Altman, Shein chair Donald Tang and LinkedIn founder Reid Hoffman. “The true benefit is you meet the world’s most powerful founders, then you build relationships with them,” he says.
Nine years after that Kawasaki chat, Stebbings is a major venture capital player in Europe, having raised a third fund worth $400m for his venture capital firm – also called 20VC – with backing from the Massachusetts Institute of Technology and Josh Kushner, founder of OpenAI investor Thrive Capital.
There were many losers from the US election result, but podcasting and tech were on the other list. Trump validated podcasting as a powerful alternative to the established media ecosystem by making well-listened-to appearances on shows like The Joe Rogan Experience, while the fortunes of tech billionaires soared in the wake of the poll, reflecting expectations of a benign tax and regulatory environment.
Sections of the tech industry openly embraced Trump; Elon Musk was the most high-profile political and financial supporter, followed by powerful VC figures such as Marc Andreessen, Ben Horowitz and David Sacks. Peter Thiel, a staunch Silicon Valley libertarian, backed Trump but did not donate to his campaign.
But, according to Stebbings, there were other, less vocal Trump supporters in US tech. He said he had had “many billionaire founders on the show” who didn’t say who they were going to vote for, but the minute they stopped recording, “they said they were [pro] Trump”.
In a recent post on X, he indicated that 90% of his guests were quietly pro-Trump – a message that was viewed 750,000 times including by X’s owner, Musk, who replied: “In 2020, every independent voter I knew was voting for Biden. In 2024, every independent and many former Dems are voting for @realDonaldTrump.”
Musk wasn’t one of the quiet ones, obviously, but Stebbings says the reason why others supported him was simple: from the tech industry’s perspective, it’s good for business. For instance, the likely departure of Lina Khan, the head of US competition watchdog the Federal Trade Commission, is raising hopes among tech execs that acquisitions by major tech groups will be back in vogue – providing an outlet for tech founders to cash in.
“We finally might get some liquidity back into the venture ecosystem. That is a very significant and important part of our business – selling on,” he says.
Stebbings had also warned last month that tech entrepreneurs would leave the UK “en masse” if Rachel Reeves announced a significant increase in capital gains tax in the budget. In the end there was no vertiginous CGT hike, which means the reaction from tech founders has not been “as bad as expected”, says Stebbings, although he was no fan of Reeves’s statement in general: “This is not an economy of growth.”
Stebbings, and others, have pointed to Trump’s wholehearted embrace of podcast media as being a key factor in getting his message across to voters. Trump spoke to Rogan, Theo Von, Adin Ross and other right-leaning podcast stars, while Harris veered away. Nonetheless, she did lengthy interviews with popular podcasts including Call Her Daddy.
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“People are totally not getting the power of the podcast,” he says. “This is the first election where we’ve seen the core reason why Trump won is because he understands the power of decentralised, grassroots media.”
Trump also capitalised on a section of the media environment that is overtly male. And that is another similarity between the podcast and VC worlds: gender. Last year, the House of Commons treasury committee flagged that less than 5% of total VC investment in the UK is in companies with female founders. And figures showed that less than 2% of VC funding went to black- and ethnic-minority-led businesses.
It is a male-dominated investment environment that replicates itself in the companies it selects for funding; Stebbings says more female investors will close the gap.
“I don’t think there’s enough female investors who have decision-making power. I think the source of capital, a lot of the time, just dictates or determines the distribution of capital,” he says, adding that it is the same issue with black- and ethnic-minority-led businesses.
Stebbings is addressing this through one aspect of 20VC’s investment strategy, where it gives funds to panels of tech executives who can keep the returns – although 20VC can also choose to invest alongside them. One of the panels is all-female and 25% ethnically diverse. “The way to get more female founders funded, rightly or wrongly, is to get more female investors,” he says.
Stebbings says his mother, Juliet, who has multiple sclerosis, “taught me, bluntly, there is nothing you cannot achieve if you truly set your mind to it”. He and his mother, who has trained as a pilates instructor since her diagnosis, walk a marathon every weekend around London. “Walking marathons and becoming a pilates instructor, it’s super hard,” he says, adding that he takes another piece of advice from his mother into investing and, when he’s on the 20VC podcast, interviewing.
“My mother always tells me: ‘It’s not what you say, it’s not what you do. It’s how you make people feel’.”
