Harry Stebbings on 996 regrets, political ambitions and building a personal brand

Freya Pratty (0:02)

Hello, and welcome to the Sifted Podcast.

Today's episode of The Pod is a fireside chat between myself and 20VC founder, Harry Stebbings, recorded live at the Sifted Summit in London in October. I really enjoyed this interview. We touched on everything from 996 to the brority in the tech world and why Harry doesn't like it, to his desire to get into politics and which company he thinks will return the 20VC fund. Harry is a very candid interviewee and was willing to get into the thorny topics and let me challenge him, which I really appreciated. Enjoy. Thank you for being here.

Mike Butcher (0:44)

No, I'm glad you're here.

Freya Pratty (0:45)

I didn't think you'd need a huge intro. Clearly everyone knows who you are. That's very sweet. But you are a very successful podcaster, founder of, what was that face? You're like...

Harry Stebbings (0:55)

Yeah, it's true.

Freya Pratty (0:56)

Thank you very much.

Harry Stebbings (0:56)

You are.

Freya Pratty (0:58)

Founder of VC Firm 20VC, which is investing currently from a $400 million fund, investments, Legora, Lovable, Fuse, some of the ones that we cover regularly. Also founder of Project Europe, which is very, very cool.

And potentially the UK's most famous VC.

Harry Stebbings (1:16)

Sure. Yeah, I'll definitely take that.

I think there's like this difference between like brand Harry. We went for a walk. There's this difference between brand Harry and actual Harry. And the most important thing to understand about like brand and content stay is nuance doesn't sell. It depends. Doth not make a viral post. And so like most people meet me and they're like, I thought you were going to be a total dick.

Quite nice. Also very good to set the bar very low, by the way.

Mike Butcher (1:45)

Very helpful.

Harry Stebbings (1:45)

I normally always wear shorts also. And so when I wear trousers, everyone's like, wow, you look amazing. I'm like, it's just jeans.

Freya Pratty (1:52)

I was going to wear shorts because I thought you might wear shorts.

Mike Butcher (1:54)

Terrible shame.

Harry Stebbings (1:56)

But you have to take a strong stance on social. And like I take very strong stances. Yeah.

Freya Pratty (2:01)

Which makes you a great interviewee.

Harry Stebbings (2:03)

Which makes you a very good interviewee. And it makes you very kind of good for social. But some of them have nuances and caveats.

Freya Pratty (2:10)

I have a lot of questions on the difference between brand you and real you.

Harry Stebbings (2:15)

I also always find these interviewees generally pretty shit. But they are because people don't ask the real questions.

You want to know how much money does the person make? What was the best year ever? What's the best investment? How much you make from that? Great. Ask anything.

Freya Pratty (2:28)

Go for it. We will do all of that. I first want to ask you, the previous panel was about the future of tech media. You clearly have lots of thoughts on this.

Where's it going? Tell us.

Harry Stebbings (2:38)

Were any of them profitable?

Oh, we have 90% margins. We make millions and millions a year.

I think people are very bad at building media businesses today. And I think they don't spend enough time trying to understand where media is going. Media is going short form. And the most important thing for me when I have a guest on the show, is I need to be a teacher. I spend 15, 20, 30 minutes before every interview. And I say, okay, in a world of long form today, the real product is clips, which means we need to change the packaging. Every answer needs to have a hook, because it's a clip in its own right. The best interviews are art and science. The art is telling the story. I was sitting on the stage with Freya. My hands were sweaty, when that clammy with nerves that she was going to ask me about, 996

Freya Pratty (3:30)

I am.

Harry Stebbings (3:31)

And not being woke.

Fire away. I don't have very clammy hands.

But I'm bringing you into the story. You're feeling a part of it. I'm giving you excessive detail about the clammy-ness of my hands. And then I hit you with, and I learned three things about what it takes to deliver a good interview. And that's the science. It's the framework that comes from that experience. And that's what makes a great interview. And so I think media is changing. I need to educate my guests to be good for that media format. And I just, I don't know if new media providers quite think like that. You also need to be like a scientist in new media. We test and iterate everything. We will test beforehand whether a guest will be successful. We've built our own models that predict the virality of a guest. We will cancel guests beforehand if the model doesn't show them to be potentially viral.