The Gentleman‘s Journal brings you exclusive interviews with the world‘s most interesting tastemakers, entrepreneurs and raconteurs. Hosted by Joseph Bullmore.
Episodes
Sunday Nov 02, 2025
Sunday Nov 02, 2025
“You really have to be unwaveringly obsessed..."
Harry Stebbings’ career began at the age of 13, when he watched The Social Network — David Fincher and Aaron Sorkin’s brooding portrayal of the earliest days of Facebook. But whereas many of us watched that film and thought: “I’d quite like to be a tech founder”, Harry watched it and thought: “Gosh. I want to be a venture capitalist.”
A few years later, and with £200 pounds in the bank and not a single contact in the VC world, Harry started his podcast, The Twenty Minute VC. Now, more than 10 years and 1400 episodes later, Harry has pivoted his juggernaut-like podcast into his very own VC fund — one that has backed 13 unicorns to-date. Here, in a beautifully candid interview, Harry tells the podcast about the AI start-up sphere; why he chooses to work nine-to-nine, six days a week; how his often lonely childhood formed his entrepreneurial mindset; the dangers of social media usage; and the things that make him optimistic about the future.
Harry Stebbings’ career began at the age of 13, when he watched The Social Network — David Fincher and Aaron Sorkin’s brooding portrayal of the earliest days of Facebook. But whereas many of us watched that film and thought: “I’d quite like to be a tech founder”, Harry watched it and thought: “Gosh. I want to be a venture capitalist.”
A few years later, and with £200 pounds in the bank and not a single contact in the VC world, Harry started his podcast, The Twenty Minute VC. Now, more than 10 years and 1400 episodes later, Harry has pivoted his juggernaut-like podcast into his very own VC fund — one that has backed 13 unicorns to-date. Here, in a beautifully candid interview, Harry tells the podcast about the AI start-up sphere; why he chooses to work nine-to-nine, six days a week; how his often lonely childhood formed his entrepreneurial mindset; the dangers of social media usage; and the things that make him optimistic about the future.
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