Jimmy’s Jobs of the Future – “Jimmy VS Producers | Easter Special” (April 7, 2026) Podcast Host: Jimmy McLoughlin
Co-host: Sunny Winter
Produced by: Boxlight Creative Studio

Episode Overview

This Easter Special marks an informal, behind-the-scenes quarterly wrap-up between host Jimmy McLoughlin and producer Sunny Winter. Moving beyond their usual interviews with leading entrepreneurs and politicians, the episode provides a candid look at the growth of the podcast, insights on their evolving production process, recent milestones, and what lies ahead. The conversation blends light banter, reflections on personal and show achievements, and discussions about how podcasting itself—and the world of work—are changing.

Key Discussion Points & Insights

1. Reflecting on Milestones and Growth ([01:11]–[08:58])

• YouTube Silver Plaque & Audience Growth
  • Sunny: “It’s got to be going past 100K.” ([02:18])
  • The team celebrates surpassing 100,000 YouTube subscribers and receiving the coveted silver plaque, a childhood milestone for Sunny.
  • Both note the shift in ambition: “The next one now is a million, which feels like a lot to 10x from here.” (Jimmy [02:46])
• Award Recognition
  • Their Tony Blair interview won the “Interview of the Year” at the Political Podcast Awards, a “genuine surprise” for Jimmy ([03:44]).
  • Both discuss the importance of supporting smaller podcasts, with Jimmy describing a focus on “help[ing] other people, inspire them into it as well.” ([05:03])
• Pushing the Envelope
  • Reflections on how “status markers” like awards or social metrics affect motivation and the broader media landscape, referencing past guest Will Storr and his ideas on status. ([05:22])

2. Behind the Scenes – Production, Guests & Challenges ([08:58]–[18:49])

• Studio Evolution & Hosting High-profile Guests
  • Sunny highlights the transformation from humble beginnings (two chairs, a lampshade, and Tom Tugendhat as their first guest in the studio) to now, hosting Secretaries of State and distinguished leaders. ([07:13]–[08:22])
  • “Movie magic” means the studio looks more glamorous on camera—reality is far more DIY! Sponsors for curtains are openly solicited, with Sunny humorously describing their current setup ([08:39]).
• Guest Logistics and Status
  • “It’s amazing how many people they kind of rock up with.” (Jimmy [09:11])
  • Discussion about meetings, how “being at the meeting” is a status symbol in government and media, and the proliferation of entourages ([09:32]).
• Managing Pace and Adrenaline
  • High-pressure filming days, the adrenaline of “being on show,” and the new normal of leading a growing production company. Guest and former footballer Mathieu Flamini is mentioned regarding channeling adrenaline from sport into business ([12:41]).

3. Guest Insights & Episode Highlights ([18:19]–[23:13])

• The Diego Interview: Unusual Jobs in Modern Britain
  • Jimmy and Sunny reflect on the episode with Diego, a viral pickpocket-catcher, noting the surprising crossover appeal and the show’s reach beyond traditional business/political guests.
  • “Maybe more than any other guest recently, the people in my circles [reacted],” says Sunny ([20:05]). Diego’s work reveals the serious, organized side of street crime—a long way from “twee Victorian” stereotypes ([18:51]).
• Show Evolution & Audience
  • They observe audience segmentation: while their core listeners are “driven, ambitious, but maybe a little bit directionless” 20-somethings, the largest growth in audience comes from the over-50s and people listening while driving ([23:53], [35:36]).

4. Spin-Offs, Side Projects & Innovations ([23:13]–[30:05])

• Launching a Leadership Podcast: “What We Don’t Know”
  • New joint venture hosted by Dr. Hayaatun Sillem CBE (former CEO of Royal Academy of Engineering) and Matt Brittin CBE (ex-Google UK), focused on practical leadership insights ([23:14]–[26:15]).
  • Targeted towards current and aspiring C-Suite leaders, but with broad relevance ([24:46], [26:39]).
• Anthropy Conference at Eden Project
  • Highlights from Cornwall’s Anthropy conference—panels on jobs, AI, and the future of work, with panellists like Will Hutton, BIM Afolami, Kamal Ahmed, and Claire Cookson ([31:36]).
  • “Panels were kept to three… I think the perfect panel is basically two or three.” (Jimmy [31:33])

5. The Future of Work, Craft & Technology ([36:30]–[44:57])

• Media Partnership with Nation of Artisans and British Craft Prize
  • Plans to become media partner for an initiative celebrating modern artisans who blend traditional and contemporary skills—“people that are reinvoking traditional craft via modern technology” with a £60k prize fund ([36:44]).
  • Reflections on the satisfaction of tangible, skilled work (“direct relation to your work”), referencing both craft and digital content creation ([39:02]).
• AI & Podcast Production
  • Experimenting with AI guest selector tools, “guest radar,” and even a “Jimmy bot” to model guest fit ([42:41]–[44:01]).

6. The Award Ceremony Circuit & Community Feedback ([44:57]–[52:42])

• City A.M. Awards & Industry Events
  • Jimmy describes being a judge at the City A.M. Awards, lauding the energy, the innovative companies post-pandemic, and the evolving fintech/neo-bank ecosystem ([45:02], [49:03]).
  • Playful debate on how awards should be structured—“Does any award deserve a speech?” “Maybe that’s it. Maybe that’s your controversial opinion.” (Sunny, [50:10])
• Audience Interaction & Suggestions
  • Both encourage listeners to submit guest suggestions, engage on social media, and check out the new leadership podcast ([51:20], [52:00]).
  • “We especially like it if you… have an amazing connection to this really interesting or important person.” (Sunny [51:20])

Notable Quotes & Memorable Moments

• On Podcasting Status & Awards:
  “But it's funny how these things matter, isn't it? Like, you know, it's a lovely shiny silver plaque.”
  — Jimmy ([02:46])

• On Supporting Other Podcasters:
  “I consider it a real thing to try and support them and I. Yeah, it's still really… Grinds my gears that someone whatsapped me…”
  — Jimmy ([05:03])

• On Studio Realities:
  “It just looks incredible. But… it's all a bit of movie magic. What you can't see is that as a guest you're sort of looking at quite a lot of lights and cameras and things like that.”
  — Sunny ([07:13])

• Celebrity Guest Impact:
  “Maybe more than any other guest recently, the people in my circles… got such a huge reaction.”
  — Sunny reflecting on the Diego episode ([20:05])

• On High-Pressure Production:
  “You’re basically on show for five hours… a lot kind of relying on you.”
  — Jimmy ([10:56])

• On Tangible Work & Fulfillment:
  “One of the things that makes people happy is having a direct relation to their work and working with their hands and so on.”
  — Jimmy ([39:02])

• On Their Audience:
  “I am thinking of the 20 something in their first or second job that has just got a job for the sake of getting it and is now thinking about what they want to do with their career next.”
  — Jimmy ([23:24])

• On Change and Experimentation:
  “The fact that we're not over planned. It's a feature, not a bug you could say, which is my new favorite phrase.”
  — Sunny ([28:34])

Timestamps for Key Segments

• [00:55] – Episode Introduction; the Easter Special concept.
• [02:18] – Celebrating 100K YouTube subscribers and winning “Interview of the Year.”
• [07:13] – Studio transformations and ‘movie magic’.
• [10:56] – High-pressure filming, adrenaline, and reflections on onsite shoots.
• [18:19] – Behind the scenes with Diego, the viral pickpocket-catcher guest.
• [23:14] – Introduction and discussion of new leadership podcast, “What We Don’t Know”.
• [31:36] – Anthropy conference panel insights and reflections.
• [36:44] – Media partnership with the Nation of Artisans and thoughts on craft in a digital era.
• [42:41] – Experimenting with AI guest selection and the “Jimmy bot.”
• [45:02] – City A.M. Awards and observations on post-pandemic company growth.
• [51:20] – Urging audience engagement, guest recommendations, and plugging their leadership show.

Tone, Style & Banter

The conversation is light-hearted, self-deprecating, and informal. Both Jimmy and Sunny toggle between tongue-in-cheek jabs and earnest reflections. The duo openly discuss challenges and learning curves, drop pop culture references, and break the fourth wall by directly addressing superfans and even their own parents. They swing from serious industry observations to making fun of their curtains and AI guest radar, all in the spirit of transparency and community-building.

Final Thoughts

This special episode is as much for dedicated listeners as it is an accessible entry point for newcomers; it shows the personalities, values, and ambition that fuel “Jimmy’s Jobs of the Future.” The team’s willingness to “try stuff with you guys”—from unconventional guests to AI-driven experiments—keeps the show dynamic, while their commitment to both craft and change points to an evolving future for both jobs and the podcast itself.

Listen if you want:

• A candid, behind-the-scenes look at how an award-winning podcast is made
• Stories about the intersection of status, craft, and technology in modern careers
• A glimpse at innovative guest booking strategies and audience insight
• Practical wisdom (and humor) from the trenches of British business and media

Contact & Engagement:

• Guest suggestions and feedback: hello@jobsofthefuture.co
• New leadership podcast “What We Don’t Know”: details in show notes
• Stay tuned for industry partnerships, award coverage, and upcoming visual experiments
• Follow and tag on LinkedIn/Twitter for a shoutout!

Happy Easter from Jimmy, Sunny, and the whole team!