Jimmy VS The Producers

4 Nov 2025 · 47 min · 24 chapters

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In short

Behind-the-scenes discussion of “Jimmy’s Jobs of the Future” (5-year anniversary), including how guests are sourced and what makes a strong episode, plus a debate-style “business version of The Traitors” casting thought experiment.

Guests (discussed/mentioned)

Sonny Winter (producer; also voice of some ads). Also referenced as potential “Traitors” guests: Alex the Pledge (politics), Tom Skinner (The Apprentice), Michael O’Leary (Ryanair), Simon Squibb (short-form/YouTube), Rory Sutherland (strategy/thinker), Stephen Fry, Jonathan Ross, Paloma Faith, Alan Carr, and YouTubers like Nico, Jordan Schwarzberg, Max Posh, Steven Try. Real guests booked by the show: Keir Starmer and William Hague (and earlier mentions of Tony Blair, plus Trump, Rishi Sunak, Liz Truss).

Key claims

Guest success depends on status/reach/network and “funny/charming/clever but not too clever.” Former politicians can be better guests than serving ones. The show’s metrics focus on revenue and watch time.

Notable examples

Starmer’s team initially offered short Midlands time slots; Hague appeared around the budget and before Kemi Badenoch’s leadership.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Business Personalities in Media

0:00 to 0:22

Discussion on who would make interesting guests for a business-themed show.

“And for a limited time, college students get the best of both worlds.”

Business Personalities in Media

1:24 to 2:02

Discussion on who would make interesting guests for a business-themed show.

“But like, Northern from Bradford says it how she is.”

The Appeal of Character and Edge

2:02 to 3:00

Exploring what makes a good personality for shows like Traitors.

“Because this is one of my points about business not having enough personalities as it used to.”

Guest Ideas and Dynamics

3:00 to 4:35

Brainstorming potential guest candidates for a show, discussing their appeal.

“So I think that's why we were sort of...”

The Landscape of Guests

4:35 to 6:30

Analyzing the traits of successful guests and how to attract them.

“I think he'd get a lot of public support.”

Changing Podcasting Landscape

6:30 to 8:03

Reflecting on the evolution of podcasting and its future.

Personal Insights on Podcasting

8:03 to 14:00

Jimmy shares his journey in podcasting and insights from the past five years.

“Because the show had been going for a couple of years.”

The Evolution of Podcasting

14:00 to 15:20

Explore how podcasting is evolving and the impact of traditional media.

“And I could see it was going to be a very similar model for what would happen next.”

Initial Podcast Experience

15:20 to 18:10

Hear about the early days of podcasting and how it has evolved over time.

Impact of Working in Media

18:10 to 20:50

Discover how working in media has influenced viewpoints and confidence.

“because you'd struggle to pin me down to a viewpoint in lots of areas now.”
Show all 24 chapters

Challenges of Pitching and Partnerships

20:50 to 22:10

Learn about the challenges in pitching and securing partnerships in media.

“and that sort of classic sort of analogy.”

The Process of Booking Guests

22:10 to 24:30

An in-depth look at how guests are booked and the dynamics involved.

“Because Sonny insists on filming everything.”

Behind the Scenes: Interviewing Politicians

24:30 to 28:00

Insights into the complexities of interviewing political figures on the podcast.

“But do you want to start with Starmer and Haig?”

Exploring Political Engagement on Podcasts

28:00 to 29:06

The discussion revolves around the challenges and dynamics of political figures engaging with podcasts, particularly with a sitting prime minister.

“And they'd seem to have gotten more and more up for it and they've got some interesting things and talk about even more and so on.”

Reflections on Political Backgrounds

29:06 to 30:36

A dive into the personal backgrounds of politicians, focusing on respect for their journeys in politics despite differing views.

Lessons from Podcast Metrics

30:36 to 31:41

Insights on the importance of understanding podcast metrics and how they shape content strategy and audience engagement.

“But also, I mean, to that point, right, you're starting at five years ago in your bedroom, didn't know it was going to be huge or, you know, didn't necessarily have expectations.”

The Evolution of Audience Perception

31:41 to 33:16

Exploring how perceptions of success have changed over time, particularly regarding influential guests and audience engagement metrics.

“And obviously I've talked about this a lot before but we landed on two key targets this year, an overall revenue target and an overall watch time target.”

The Value of Former Politicians as Guests

33:16 to 35:00

Discussion on the unique insights former politicians bring to the podcasting space compared to current politicians, who have less bandwidth.

“And that's a sort of tricky thing because we've started the podcast with almost the opposite problem of what most podcasters, YouTubers do, right?”

Impact of Political Events on Podcasting

35:00 to 36:59

Analyzing how significant political events, like a potential second Trump presidency, have influenced the podcasting landscape and business.

“Because we did him like the day, it was the afternoon of the budget, wasn't it?”

The Future of Podcasting and Platform Mergers

36:59 to 38:20

Predictions about the merging of platforms in the podcasting industry and the potential for broader media integration.

“and don't quite have as much sort of bandwidth to explore all those issues.”

Lessons from Politicians and Business Leadership

38:20 to 39:52

Reflecting on leadership lessons learned from interactions with politicians and their relevance in business today.

“I think more people are going to have the more companies are going to.”

Future Goals and Partnerships in Podcasting

39:52 to 42:02

Discussion on the short and long-term goals for the podcast, including building partnerships that enhance content creation.

“Because you have empathy with people and you've been through it with it and you've got a greater understanding of what it's like founding a business and so forth.”

Building Long-Term Partnerships for Better Content

42:02 to 46:32

Learn how securing long-term partnerships can enhance storytelling and community engagement.

“I mean, look, short term, very practical.”

Building Long-Term Partnerships for Better Content

46:35 to 47:31

Learn how securing long-term partnerships can enhance storytelling and community engagement.

“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.”
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Transcript

Automatic transcript. May contain errors.

0:00Study and play. Come together on a Windows 11 PC. And for a limited time, college students get the best of both worlds. Get the Unreal College Deal. Everything you need to study and play with select Windows 11 PCs. Eligible students get a year of Microsoft 365 Premium and a year of Xbox Game Pass Ultimate with a custom color Xbox Wireless Controller. Learn more at windows.com slash student offer. While supplies last, ends June 30th. Terms at aka.ms slash college pc. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more.

0:42Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. Welcome to Jimmy's Jobs of the Future. Now, some of you will know that it's been our five-year anniversary recently, so we've had a lot of requests to understand more about what happens behind the show and what makes it all work, how we get guests, and all that type of information. So, today I'm joined by a voice that you may find quite familiar.

1:18It's the guy who voices some of our ads, and the producer of the show, Sonny Winter. Hello, hello, hello. yeah but actually i think i think before we get into it you were just saying off camera that um if there was a business version of traitors who would we who would we have on the show who'd we cast from yeah yeah people well the first one i instantly thought of was alex the pledge because i thought she'd be just great and she's now been in politics as well working with Rachel Reeves. So I think she's good. But like, Northern from Bradford says it how she is. It's kind of a bit like the Jay Marler character.

1:57Are we limiting it only to people that have been on our show? No, no, no. Just anyone kind of in business. Because this is one of my points about business not having enough personalities as it used to. And the sort of people being very kind of like chiseled with it. So I think it's quite interesting to think of who would be the people that would be good. And I think the public sometimes think of business as being quite duplicitous anyway. Like the Lego movie, in the Lego movie, the main bad guy is called Lord Business. And I always think of somebody who's worked as a bridge between politics and business.

2:33It's a rather worrying description of my passion. There aren't really enough Lord Businesses at the moment in politics. Although to be fair, we need to give the Scandinavians. But who's got, because I do find like, it is fascinating watching the traitors in many ways and just like how you put that kind of list together of people because it is, you know, and it's obviously quite different to what we do, but you're thinking like what makes a good sort of personality, what makes a good guest, right? So I think that's why we were sort of... No, it is actually a very good thought experiment because you want someone on Traitors that, you know, has a little bit of edge to them, you can sort of relate to, or they can be the sort of pantomime villain, which to be fair is kind of how we...

3:18not think about guests, we love all of our guests, but think about one of those episodes that really does perform well. And I was just thinking before we turned it on, Tom Skinner, the guy from The Apprentice. Yeah, yeah, yeah. He's not exactly like business genius or anything. You are, we'd love to have you on the show. But he could be quite a good personality. I wonder why he was casted for Strictly and not for Celebrators. it's interesting that isn't it I tell you who would be good Tim Campbell would be good on business celeb chaters do you think he's so nice though maybe we'll care I guess you need a couple of nice people but he's got like the yeah he's got you do need people that are the sort of proper faithful you can't have everyone just sort of looking to go after the one I was talking about I think Michael O 'Leary would be killed from Ryanair just because I think he's like he's funny as well yeah and that counts right yeah Yeah.

4:19Who else are my guests from this year? I don't think you can have politicians, because I just think they're so sort of like... I think you could tear the new one. I just don't think it works on traitors, basically, because everyone just really thinks that's basically... I think Squibb would be all right. Simon Squibb, yeah, yeah. I think he'd get a lot of public support. And it's also, I think everyone knows him from short form. How many times do you think he'd ask, what's your dream in the round table? Not enough. Not enough. I think a lot of people know him from short form, although he obviously does do YouTube as well.

4:53But I could imagine a lot of 30, 40-year-olds are like, I recognise that guy, but I'm not sure why or how. And then you'd get to know him a bit more. The interesting thing about celebrities has been, they're obviously all smart and successful, right? So it has been quite a different kind of game to what it is usually. And I do think that would be a challenge with business leaders, is that they're all, inevitably, they're all kind of pretty smart. Who else from the guests that we would have this year? You were advocating for Rory Sutherland. I don't think there's enough Rory Sutherland content out there.

5:28Even though he does about 300 podcasts a week, I think. We're barely scratching the surface. When we have an AI clone of Rory Sutherland, finally we'll have reached the nexus. I think he would be good. I was thinking it would be so hard to pin down as well. Yeah, he would be. You'd think, oh, I've got something on him. Or he did this sort of weird telltale thing where he laughed or something. And you'd try and pin him down and you'd be stuck in a conversation with him for 40 minutes. Who would be your traitors? Do they get to decide themselves? No. Or do you decide for them? So, what, are we saying I'm going to host it as well?

6:04I'm going to be the new Claudia. Yeah, I am. I, um... Yeah, well, they pick them in the show, don't they? So, yeah, who would be good? Because they have done really well, the traitors, this time. I think it's been the best ever. Did you see someone did a post about it that, like, because the traitors are all sort of old-school media tycoons, Stephen Fry, Jonathan Ross, not a twainter,

6:35there's this weird media hierarchy in it, and they've just they've voted off all the like less well known media people there's been like a media hierarchy and there's been a sort of grandee and there's been a bit of a like sort of intellectual sort of status thing as well like that's been much more like observant in this game like the cleverer people like Stephen Fry and David have been sort of put on a pedestal whereas actually in the normal game like basically if people come across as clever they go out early yeah so it's like it's quite although Paloma Faith is quite establishment and she went out pretty early right yeah she did but then it was just Alan Carr kind of like I wonder if they do another season and they have a few more sort of established media figures if they'll get axed earlier because everyone's watched this one yeah and they might not have the halo effect who from your world of like media kind of creators YouTubers oh that would be an interesting one I'm a big fan of Nico like he's a very good prankster so i don't know if he worked in that format but like as someone who i can imagine working well it would have been him who else would be quite good the problem is i watch less and less of the sort of prankster youtube stuff and i watch more and more of the sort of in-depth essay and getting the tldr guys on traitors i'm not sure if that would work i'm clearly influencing you too much uh moving towards us um yeah it's it'd be interesting jordan schwarzberg are probably quite good you think so smart he kind of covers both sort of like business and the career i don't know if he has enough i tell you he'd be good max posh would be funny yeah he'd be good no yeah that because he's he's quite good as well in like traditional media settings yeah yeah is it yeah yeah like steven tries i think would be quite good quite funny yeah yeah i think you need a little bit of like okay so i mean what what is really coming down to then is you need to be funny you need to be charming yeah and you need to be clever but not come across as too clever yes i haven't watched the like other seasons of traitors but from what I understand on this season they're saying like oh I think you're the traitor because you're so smart and amazing and because you're such a good media person whereas from what I've read online that the other series is like you're a prick you're a traitor get out of her it's definitely been it okay well look BBC hit us up we've got we've got the next big thing trademarked no it's not trademarked but I thought we could do a little bit of casing by saying how we actually met.

9:26Yeah. Via LinkedIn. Via LinkedIn. Right. Because the show had been going for a couple of years. Yes. Also, I'm very aware that it's my voice that does the adverts for our production company. So if people haven't automatically skipped because they've heard my voice, then we're really in a good spot. Via LinkedIn. in and I applied and we had a good call and then the queen died yes which was all the guests scuppered it was it was guests and like two big contracts that we got as well we're all like not scuppered but delayed um and when you're like a small business like it's um yeah it's kind of like critical at the time like because it was right at the start of September sort of three years ago it was a really weird time to join because I remember I joined and I had to write a few substack posts and it was before ChatGPT came out which would have made my life a hell of a lot easier but then at the same time I probably wouldn't have started to understand your tone of it it was also a sort of interesting time as well because all the politics was changing and Liz Truss was Prime Minister Liz Truss and Rishi so all our clips were them I know but we got the clip from Liz Truss sort of saying how Jimmy's Jobs of the Future was her favourite podcast we milked that for about two weeks that we tried to scrub that from planet earth oh no yeah that was good well look it's been good three years being here and it's been a good five years i think um what would you say it's actually like producing a political business show if you want to call it that well i mean we sort of say don't we that i'm like the exec producer and you're kind of the producer on it and i think it's i think people would be interested to know how we kind of get guests and how we sort of assess that because that's like the big bit because you can only ask so many good questions and get answers out and i think that's the thing that i've got better at working out is like what makes a good guests what's going to travel well yeah we often talk about status reach network kind of being there the kind of key things in terms of whether something's going to do well obviously you get some people the kind of unicorns that fall into that bucket you know sort of rory sutherland's tony blair's type thing where you just know that it's gonna rocket on all of your kind of key factors but i think that's like it's been quite interesting because there's definitely been a tipping point this year of where really impressive people have started coming to us like and that that has been a big change it still means that we have to get out on the front foot approaching people but also as soon as somebody interesting comes into the inbox you basically know that's going to happen and that's interesting because we have this like master list of like 350 names on it right people and we're always interested to hear kind of guest ideas and comments and such like as well right because i think one thing that i would like to do more of next year is do more on AI, but also like sort of some of the kind of like intellectuals and academics and sort of real thinkers on it in the UK and so on.

12:43So that's quite an interesting kind of area for us. And it's, yeah, it's something where I spent just quite a lot of my time reading, right? And trying to find interesting sub-snackers and that type of thing to get the information across. but again that doesn't necessarily mean that somebody's going to translate into a good guest either but like when you imagined it that i will obviously figure out what we talk about and we'll do the title and thumbnail afterwards which is also a bit of a sneak behind the curtain but you know if the title of the video is you know how i accidentally built a media brand yeah then if you go down that route and you're saying okay five years ago five and a half years ago there must be things where you're like oh i didn't imagine it to be as cool or glamorous and there's other things we were like bloody hell that was that was really in the trenches yeah I mean definitely there's quite I could see what was happening with the podcasting world right like I could see the direction that was going to go in and I could see that everyone was going to have one and my ethos on this has always been like it's going to be like sort of blogging of 15 20 years ago right which was like just at the start of when I was entering the professional world in the late noughties um And I did quite a lot of blogging at university and so on.

14:01And I could see it was going to be a very similar model for what would happen next. And it's quite interesting. In the last couple of weeks, The Times have launched their business podcast and so on. And what happened to the blogging, the blogosphere, as it was called, was it basically got swallowed by the traditional media. So you had all these different writers, particularly in the political blogosphere thing. and then most of them essentially got taken over or people like Ian Dale, for example, now is at LBC, etc. So I think it's quite interesting. I could basically see that that was going to happen with podcasting again and there was just an opportunity to do something that was fun and interesting.

14:43And also, when I was starting five years ago, it was partly just the middle of a pandemic and it was to keep me sane. you must have had like some like the first time you hit upload like there must be some sort of vision of like a Joe Rogan I mean who was big podcast back then like a Joe Rogan or something some element of like this is going to be really big yeah but I I mean you do and you don't when you're doing that right because you're just like I genuinely wasn't sure it would go much further than the eight episodes but I thought it was a good experiment and a good prototype to take and I definitely thought there was something in it and after I'd uploaded the first one I and the feedback that we got from it I thought we're definitely on something here so that's there's probably a bit of a different kind of like marker moment of like a week later after it like I remember both Nick Robinson and Kate McCann getting in touch sort of being like BBC and Sky News Times Radio now just being like thought it was great thought it was really interesting and I remember thinking okay that's that's cool that's that's cool and that's like that's proper kind of like social proof on it as well um and yeah so I sort of knew there was something in it all um but I didn't I didn't know where it was and I think that's the thing is like it's evolved quite a lot right like in terms of guests like the first 50 episodes were all about entrepreneurs talking about jobs of the future and so on it was basically it was like after 40 real 50 episodes i was like there's only so often i can hear software engineers or data scientists right now that's really changed and so on and i was like we need to kind of like update it and do some other kind of interesting people in interesting fields because one of the things that i've also sort of realized over these years is that actually the jobs in the public sector are often more interesting than jobs in the private sector in some ways so I think that's been kind of like one of the one of the big things so you sort of like trying to marry all these various bits together of what makes kind of an interesting job and so on but you're trying to get out of me you just want me to say that like I just knew it was gonna be the biggest and best show in the world no no yeah I mean of course that is what I do want I mean you said it before when we were talking about uh celebrity trade business celebrity traitors uh and i was sort of struggling to even come up with some good names that from the youtube world but i think in truth if we look at how working here has changed me and i'd be curious to see how having this show has changed you i am i've definitely got a lot more keen interest in business a lot more keen interest in politics and I'd watch about it in my free time.

17:38It's fun. And it's also, it's nice not having, it's nice not having any specific take. Like you talk about the fact that you've sat down with 200, 300 geniuses in their field. Yeah. I've had to listen to them for hours on end editing them and things. And it's made every single position of mine completely wishy-washy because I've heard an expert take directly opposing every single view. Yeah. So I think in that sense it's made me more balanced but also less balanced because you'd struggle to pin me down to a viewpoint in lots of areas now. Yeah. Well, I think that's fair, right? But I always remember one of the first things, one of the first lectures I had at university, in fact it was the very first, but at the end of it, the tutor called Peter Kerr just said, look, you're 18, 19 years old, you're studying politics, there's quite a strong chance that you're going to have strong views on the world.

18:39And he's like, it will be the biggest shame if you leave here in three years' time with exactly the same views for exactly the same reasons. He's like, if you end up leaving with similar views, make sure they're for different reasons. And so it's always kind of like, which I wouldn't often say was the most valuable thing at a university. Because it's just like, you've just got to keep adapting, keep learning, staying curious about it all, et cetera. Did your views change at uni? I think so. I mean, it was like, I was there between like 06 and 09. So it was like quite a, the world changed a lot during that sort of period.

19:16We had the new prime minister, the US president, financial crash, et cetera. Um, so yeah, but I mean, I was kind of pretty green and wet behind the ears when I started. Right. And I do think it's interesting working with all you guys now, like of a much younger generation. I think you're much more, and this is like inevitable in some ways, I suppose, but much more informed about the world and have a much broader view of what's going on. And I think you get a lot more opinions kind of thrown at you as well, partly because of the sort of like evolution of content and so on. So I just find that quite interesting.

19:54Like all of you will come in with quite different takes on different things and so on. Whereas, you know, my generation, it's not that long ago, but I realise it very much is a different one. Yeah, probably had those core sort of set of beliefs sort of earlier, perhaps. Yeah. Although that is a fair, even though maybe I can understand more viewpoints and I'm a little bit more sort of centrist, wishy-washy now than I was when I joined. in terms of how I actually operate as a person, this job has definitely made me a lot more confident, a lot more decisive when I'm talking to people. Because you realise people respect you if you've got a very clear ask.

20:39We've got a lot better at that, right? I think when you started, we were... I don't know, we were sort of... We very much are kind of like building the aeroplane as we go along, right? and that sort of classic sort of analogy. But it was interesting. I was talking to somebody that we tried to pitch to a couple of years ago for a brand partnership, and they were sort of saying, like, you know, I think we made a mistake not doing it, and so on. Like, it's been nuts to kind of watch the last few years. But I was like, in fairness, we probably didn't put together a very compelling thing. Like, it was all a bit sort of, like, messy.

21:17Whereas, like, one of the big things we did, obviously, last year, was like separate box light out a bit and kind of make that and make that um make that sort of kind of clear and so on for when we're having kind of like conversations with people it's still hard now right like i mean you know but people still think as a podcaster you can do a lot of stuff for free and you'll want to go to these events and whatever and sort of host a podcast at a live event etc and all that stuff is kind of like it is quite sort of it's interesting how that sort of power and those dynamics are kind of shifting as well like it's been really interesting to sort of watch that uh and kind of learn and i think we still need to do it all as well i mean like there's you know there's a lot more costs on the business as we've talked about um than there were when we sort of like started and so on and it's all a classic kind of like entrepreneurship um challenges and so on um but it is just quite i think that's been like one of the big things about communicating our products and what we're doing and how we distribute etc etc um has been quite interesting yeah cost in the business reminds me we do need to get some more hard drives after we stop recording um but no i do you own a hard drive company would you like Yeah.

22:40Seagate, Toshiba, who else? Sandisk. We'd love all of you guys. The amount we'd love to spend on. Yeah, I know. Because Sonny insists on filming everything. Western Digital. We're a big fan as well. 12K. You want to get one of those big server things, right? You've been talking about that for ages. Who makes them? Give them a shout out. You can't remember. A quick 30 second. Tresonet or Flash System or Pure Storage. We're big fans. Get in touch. No, on your proposal thing, and that reminds me of a post I saw the other day on LinkedIn, which is a superb platform.

23:25And they said about how they, it was a company that was going out to pitch and they were trying to get investment and they made notes of the sort of 30 VCs that they'd approached and all the feedback they got yeah and i think it was like vc number 25 gave them feedback and they also didn't invest that vc number 25 but it gave them very good feedback which was every time that they'd done a pitch they took note of the feedback implemented on their deck and changed it and changed it and it was number 25 that said like your product seems good but your pitch deck is almost like pre-empting all the problems this was this is phoebe from brolly yeah yeah and i i think obviously completely independently of that post we had a very similar thing where we were sort of designing our decks to sort of match the brand colors of their thing and trying to sort of mold ourselves very much to them rather than saying this is our product we refine it yeah you can buy our product rather than what can we do for you which i think was a big change yeah i think that helped a lot yeah but yeah no no i think that's i think that's true I think that's true I've invited Phoebe on the podcast by the way she's now head of insurance at Monzo it's really interesting Monzo my IPO in London I already had to see that, that would be cool shall we talk about some of the guests and how we booked them yeah go on I actually know there's like a two part which is how we get guests and I've put them into buckets but I'll be curious to hear what your buckets are and then also from the other side is your perspective versus my perspective on what makes a good guest.

25:01Yeah. But do you want to start with Starmer and Haig? Because I actually would put them in a similar bucket in terms of booking. What? Yes. I suppose you would put them in a similar bucket because they both approached us to start with. Yes. and also it was like a very, it was a classic. Next Tuesday. Yeah, they were quick, right? Well, so, with Starmer, we had not approached him. I mean, obviously, you'd love to get the Prime Minister on the podcast, but I also know how kind of like busy they are and just when you make that approach, you're going to be, you know, you kind of get what you're given, right?

25:53in terms of that now what was different about it was they came to us and said you know initially can you come to you know i remember as well it was like friday afternoon at like half past four and they called and said can you come to the midlands at 9 a.m monday to do six minutes with the pm and i was just like i just thought back to my time at number 10 and thought this is absolutely classic somebody's because i said the first thing i was like look i've got to try and make this work logistically with childcare and whatever because i do all the drop-offs as you know and i was just like can you tell me whereabouts in the midlands right try and assess the viability of it and it was like they said oh we can't we can't sort of and i was like i know you can't tell me for security reasons exactly but you know midlands is quite a big place like you can be a kind of like thing an outline of this and then they were like no and i thought to myself i thought the amount of friday afternoons i've been running around in number 10 trying to sort stuff out for the monday morning kind of brought back memories of like jimmy can you find us a life sciences business based in this kind of constituency which is always hard because that's always like the first bit of it is they want to plan generally something on a constituency basis but actually most constituencies aren't going to have that many businesses they're all big businesses that are kind of ready to take that phone call on a friday so that's some funny stories of like you know just trying to get through to people and uh and so on um and in the in the end i called you and was just like i just think it's i think it's too much hassle for six minutes and whatever like but it was kind of like fun to explore and then they came back and were like look can you do a conference later in the week you can kind of kind of have like 12 minutes and we're like again it's still not kind of like really sort of what we're after which is obviously then i'm having these reflections during in this process of these odd moments that kind of...

27:41I'm pulling my hair out of this. Catch you out, where it's like, we're actually just saying no to the Prime Minister here. For the second time in a week. The second time in a week. I went ballistic. But I was sort of confident and kind of new, and I thought, and then they were like, look, will you come to number 10 the following week or whatever and do like 15 minutes and so on. And I was like, actually 15 minutes of a sitting PM's time is like quite a decent chunk, actually. And they'd seem to have gotten more and more up for it and they've got some interesting things and talk about even more and so on.

28:11And I was just like, and I was keen to take the team to number 10, right? Like it's an amazing building and whatever. So there was that sort of element to it. And it was quite, I mean, the whole interview was interesting at a number of things as well, because obviously it's a year ago to the week that Donald Trump went on Joe Rogan, right? Which is when the kind of political and communications landscapes dramatically sort of collided and have changed irreversibly, I think. although the UK is still taking quite a long time to kind of like catch up in some regards. So they're clearly sort of wanting to kind of explore that.

28:44But it's difficult with a sitting prime minister to be able to dedicate three hours to appearing on a podcast. Obviously Trump was the kind of main challenger at that stage. So there's a bit more time on that. So I think it's kind of interesting for where that goes. And like, yeah, I'm a Tory, right? but it's the reading about Starmer in the background of him and reading Tom Baldwin biography I was I was quite taken with like how working class his background was actually and like his whole dad as a toolmaker meme has kind of been like overdone I think he kind of recognized that in his conference speech a little bit as well but actually reading all about it and I known for example that his um mum had been disabled but hadn't realized how early in life and so on and i just thought like there's loads i don't agree with starno right but i did think actually it's quite remarkable that the guy has become has managed to get to the top of two of our sort of probably hardest professions in law and politics and that deserves respect and so on and one of one of the interesting things post it because i know you want to talk about haig as well but is that it's just a vitriol that is chucked on our channels about him and Sadiq Khan and so on like it is kind of like it's sort of nuts to have these kind of like glimpses into it yeah you feel you do feel bad sometimes because you don't know if everyone has the same sort of thick skin that you do but actually I don't know if you feel this unless they're completely mischaracterising you if they've just sort of nailed you in the same way that like one of your mates might rib you down the pub then that is sort of engagement and that still shows that you're having an impact on someone's day enough for them to sort of giggle to themselves and comment something out.

30:37Yeah. So it can be funny sometimes. But also, I mean, to that point, right, you're starting at five years ago in your bedroom, didn't know it was going to be huge or, you know, didn't necessarily have expectations. Partly because, you know, I had no idea about like what was good, right? Like genuinely, like going into this sort of space I didn't know, you know, was 150 listens good or was... Having the Prime Minister's office call you three times over the course of a week and a half, that's pretty bloody good. Yeah, yeah, of course, right? And you said no. Yeah. Yeah, yeah, no, definitely. And there were...

31:14Yeah, but it was... Had to phrase it that way for a clip. Getting it right. But the metrics point, I think, is really important here, actually. and I also think it's like one of the skills of the future to go to the core bit of the podcast, right? It's like we have so much kind of data from like so many systems and whatever now and it's like what of this stuff actually matters, right? Like what are we trying to do? And obviously I've talked about this a lot before but we landed on two key targets this year, an overall revenue target and an overall watch time target. It's like those are the kind of like, but just going back to when you launched it and whatever, I just got absolutely no idea about any of that kind of like data and what was going to matter.

31:59And, you know, if somebody had listened to 15 minutes of a 45 minute show, is that a good or bad? Yeah, it's just like all these things that you're just on this kind of like continual learning journey about. To be fair, the same for me. I mean, I definitely knew about all the analytic stuff. But if we're here in the office and we're saying, oh, you know, we're going to do Jeremy Hunt next week. and I'm getting excited, I'm like, everyone will love that. You know, I can't wait to get a picture with Jeremy Hunt. Would I have cared four years ago? I don't know. Like, do you know what I mean? As a normie.

32:34Yeah. Do you know what I mean? Or William Haig. William Haig is amazing, by the way. He's someone maybe who should have gone on the Traitors show. He would be so good on that. Well, the thing is, I'm not a traitor. Would I have cared about meeting William Haig? I don't know, but now I'm really excited about it. So in that way, I've learned more of the things that you find as success markers. And maybe you've learned some of the things that I find or the wider team find as success markers. Yes, I think that's true. I mean, I've always said this to you, yeah, when sort of various born prime ministers and they say, oh, I really enjoyed your show with this, that and the next thing.

33:08You know, to me, that means more than 100 ,000 clocking up on YouTube and so on. People that I don't know, right? And that's a sort of tricky thing because we've started the podcast with almost the opposite problem of what most podcasters, YouTubers do, right? Which is that we started off with a core audience of 1 ,000 to 2 ,000 people who are quite influential in Westminster and the budget holders, that type. So it was just kind of a funny thing, whereas that, for most people, that's the apex of where they're trying to build their media empires to. We started with that bit. Yeah. Yeah. I mean, in a way, that makes me think of some of the more traditional YouTubers.

33:59They get like two or three minutes with a politician or a big business leader. Yeah. And I feel very much the way they approach content is it's like the concept, and then you've got this very thin layer of five minutes with that politician or business and it's stretched across it, but it's the framework of it. Whereas we're very, like foie gras, we're very rich and dense with the thing. We don't sort of spread it across a content thing, which I'm not saying there's one correct way or wrong way of doing it, but we are very gravitas dense. I don't think I've said it really well. No, I'm not. Completely lusted.

34:36Are you going for a foie gras? sponsorship I'm not going to turn that down no okay yeah Hague Hague was similar though right yes well I think that's kind of like I'd always said to him like and there's quite a few people that we have this with right where it's like you kind of have an open invite to come on right but I also appreciate there's got to be something in it for you etc and so on and it just as it happened he was running for the kind of Oxford presidency at that time and And, you know, William Hague also came of an age where social media wasn't kind of a big thing, didn't have that much kind of like actual traction on social media.

35:16So he was able to kind of come here. Because we did him like the day, it was the afternoon of the budget, wasn't it? It was like after the budget, and then a few days before Kemi became leader of the Tory party. And Trump. Yeah, yeah. So it was like really like getting the tenses right in that episode as well. But the clips did well. because it was like so I was just like yeah like speaking to him about all of that so it ends up being like an hour and a half episode or so on assuming Kemi gets it what advice would you have for her as leader and then he said it and it worked yeah yeah but it was like I think I was just making the point about whoever wins the leadership you know what would you what advice would you kind of give them and so I think that was yeah it was it was amazing and I've always said this as well maybe we'll talk about Tony Blair later as well but it's just that you do end up with a I find it strange interviewing politicians from my childhood you sort of put them on a completely different plane and obviously a lot of my professional career I've sat in rooms with them and advised them but there is just something from seeing someone from your really formative years that sort of just changed it And you can talk to people like William, you can just talk to about anything and he will have an interesting take and so on.

36:41And that's been one of the big revelations that we've had over the last year is former politicians, you've had a little bit of time to sort of reflect and think about the way that things do and don't work, are very good guests, almost better than those that are serving, because those that are serving are busy, particularly those in government positions, and don't quite have as much sort of bandwidth to explore all those issues. So that was probably why a William Hague episode was so good. And he was also talking about what impact a second Trump presidency was going to have on the world. And we were sort of...

37:15Yeah, Putin, the judo thing. And I do think, I mean, we might want to talk about it, but the Trump victory and the way that it came about undoubtedly has been a sort of benefit for our kind of wider business and people beginning to realise just how important podcasting is and for them to get their kind of own setups and so on. And that was less than a year ago. I think it's partly because Trump, he's just been such a kind of whirlwind that it's difficult to sort of remember that's only been in place for a year, that sort of moment of like where people, you know, because it was, you know, in the last four weeks, or since September, you have had Nick Robinson launch a new show, Amal Rajan launch a new show, you've got Ramesh Ranganathan, Michelle Hussain, like you've got a lot more interview podcasts being launched and so on.

38:07And I just, you know, people sometimes say, oh, hasn't the world got enough podcasts and so on? Of which I always say, nobody ever says that about TV shows or books. And actually I think that we are just, you know, we are still so early in the kind of like podcast revolution. I think more people are going to have the more companies are going to. Isn't Spotify podcast coming to Netflix soon? We can see Jimmy's Jobs on Netflix pretty soon. I can't wait for that. It's done with a production company specifically. Oh, it's like new ones. It's new ones. You know my theory on this is that all these platforms are just going to merge slightly into one another anyway, just in the same way that you've been able to put video on Spotify in the last year and so on.

38:49And I think at some point we'll be uploading full episodes to LinkedIn. I think that'll be the way that it goes as well. I mean, just a little bit of housekeeping there. William Hayes came on our show and ended up winning the presidency or the chancellorship and many people are saying it was us that did it. I think that just shows that... We are the new, the new The Sun. And James Valls came on the show and then they got, William's got the first podium. First podium, there you go. I mean, we are the media company that moves mountains. Rishi Sunak and Liz Trust both came on the show and they were both Prime Minister have been the next six weeks.

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39:27That's just... If you've got any more accommodations, let's bleep that one. You want a draw? There's been a few where it's not been quite as successful. Which I actually think, going back to your point, when you spoke to Blair, you said you think you'd make a better Prime Minister now, having been in the private sector for a bit. I'll put the same thing to you. Do you think you'd be a better business spad having been out for five years? Unquestionably so, yeah. Why? Because you have empathy with people and you've been through it with it and you've got a greater understanding of what it's like founding a business and so forth.

40:04So it's just yeah, a kind of like clearer idea of what it takes to kind of build a business, build a brand that is moderately successful. Do you think you were too harsh to people and now it's true? Any conversations until you go back and change? No, not really. I'm... God.

40:27No. No, not really. I mean, there were quite a lot of tough conversations at various points, obviously with businesses and businesses being sort of unhappy with Brexit and all the kind of uncertainty that it would create, etc. Little did we know the challenges that were coming down the track, but yeah. I've got visions of you, like you know calling an entrepreneur and prodding them hire more people hire more people but now you're like i would often make the point i wouldn't specifically not hiring more people i would often ask people whether they would consider opening northern bases or places like that that would be sort of the big thing so rather than more just hiring people per se it would be more like regional stuff regional stuff like if you consider this we can say that we're doing this in leeds and that in manchester so there's quite a bit of that I suppose should we close it out what's next what can people look forward to well why don't we both answer this question yeah where would we well answer it in twofold you're going to answer it first but it's like where would we like to be by this time next year like and I'm not talking metrics here but just sort of general things like what would we like to have done?

41:52And then maybe like some longer moonshots as well, like further in the future, where do you think it can go? And maybe that's a broader question about the industry as well. Yeah, okay. I mean, look, short term, very practical. I'd like to build our partners out. I think having longer term partners allows us to make better content, not have to worry so much about pitching or the financials. I think we've got really amazing partners at the moment. in Octopus Energy and we've got a new one being announced soon as well which really hits two major points. I think we don't have a good partner within the sort of financial literacy space that we can point people to and the wheels and ins and outs of entrepreneurship.

42:33I think if we can secure one of those for the better part of next year that would be really nice as a producer. And then I think it's the same thing we're always looking at but how do we do it in a way that's actually good which is some way where the audience can own a part of the show you know i hesitate to say merchandise but some form of ownership element i don't know what that looks like um through events as well i think always just looking at that and yeah hopefully bigger and better things hopefully we can grow the show without having to dilute telling amazing stories i've been there yeah there's two big things there it's like community we definitely want to sort of like grow out and whatever and we've been looking at a number of other podcasts and the way they've been doing stuff and it's not just like about financial metrics in in this it is genuinely i think fascinating how these communities are kind of being built what people are getting out of them what people would want out of them etc uh and we've talked about this a number of times yeah we've got such a kind of like listenership it would have arguably been easier to design a community model when i first started when it was much smaller now it's just kind of like a bit more spoiling and what people want from that is sometimes difficult to know and then just want to be keeping this sort of guess high and i think we're very good at getting politicians and businesses on you know i am fascinated by people that have done careers in other industries particularly the sort of creative sports sectors and those people that have made interesting transitions you know we think you know getting James Vals on was really interesting in the kind of like starting at that kind of journey a little bit in terms of like what sports people do after they've been sports people and so on and what the jobs are around sport and how they think about it and so on because it has become this huge kind of like economic sector over the last 25 years kind of professional sports that didn't sort of almost really kind of exist before so I think that would be really interesting to kind of do we've obviously done a few comedians but doing more of that because i think it's really interesting how the kind of constant reinvention happens and i suppose this is partly me thinking this and trying to be a bit of a magpie and steal other people's ideas but it's yeah i've seen now like quite a few comedians sort of come they do one or two great stand-up shows and then there's a bit like okay what's the sort of like what's the next thing like and some are becoming a bit more kind of activist and a bit more kind of like campaigning on issues that they sort of care about and i think all of that is kind of really interesting so like you know um we obviously talked briefly earlier about romish's new show and stuff like that and sort of that diffusion of media um i think is really interesting as well um but just like trying to keep it innovative and fresh and remaining true to our kind of like core values um and the fact that you know we won't trade our kind of like principles of what we're trying to do here be you know positive about the future explore people creating jobs and stand up for job creators as well like those core things like remain at the heart of kind of like what we do and it would be easy to kind of divert from them at various points in terms of chasing numbers and metrics and so on and but we we don't want to do that because we're kind of core in what we're about as a show.

46:01So you also don't want to diverge too much from that as well. That's true. Right. Let us know in the comments who you'd like coming on, what community features you want, and would you like Sonny and I to do this again at some point?

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From the publisher

Behind the Scenes: Building a Media Brand & Exclusive Guest Insights

In this special episode, we take you behind the scenes of Jimmy’s Jobs of the Future. Producer Sunny joins Jimmy to reflect on five years of building the show - from its early days to becoming one of Britain’s go-to business and politics podcasts.

They talk about the art (and chaos) of booking high-profile guests, the evolution of the podcast, and what it really takes to grow a modern media brand. There’s also a fun twist — a “Business Version of Traitors” thought experiment — plus stories, lessons, and plenty of honesty about the highs and lows of life behind the mic.

🎙️ Subscribe for more conversations about the future of work, business, and leadership.

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