Jimmy's Jobs of the Future

Jack and Jill: AI Agents Rewiring Hiring and Job Search

Jimmy interviews Matthew Wilson, founder of Jack and Jill, about how AI is worsening recruitment noise by automating mass applications and outbound recruiting, making traditional CV-based signaling less effective.

Matt explains Jack and Jill’s two AI agents: Jack helps individuals find and prepare for “dream jobs” through deep voice-based profiling, job matching, interview practice, and salary benchmarking (free for users), while Jill helps companies hire by capturing nuanced role needs and matching against Jack’s user network; the company has 350,000 users and thousands of companies, mainly across London, San Francisco, and New York.

Matt shares his background (Yorkshire Dales, Oxford, inspiration from a Batley-based startup), building Omnipresent (remote employment infrastructure later sold to Deel), and lessons on competitive advantage.

They discuss early-career guidance, AI tool literacy, major white-collar work changes, Jevons paradox, small high-talent teams, transparent high pay, and hiring via paid trial days and networks.

00:00 Welcome and Guest Intro
00:27 AI Hiring Spam Problem
03:19 What Jack and Jill Builds
04:03 Why Job Search Feels Random
06:45 Jack the Career Agent
08:02 Jill the Hiring Agent
08:49 First Principles Recruiting
10:04 Advice for Early Careers
12:57 From Yorkshire to Startups
16:36 Building Omnipresent in COVID
19:47 Selling to Deel Lessons
24:22 Choosing the Next Venture
25:45 AI as Patient Career Coach
29:03 Why Work Changes Lives
31:00 Reimagining Recruitment
31:44 AI Tool Fluency
34:03 Career Catapult Mindset
34:29 White Collar Disruption
36:39 Jobs Change Not Vanish
38:41 Jevons Paradox Debate
40:05 Bureaucracy Versus Leverage
42:50 Building a Lean Team
42:59 Pay Transparency Hiring
48:52 Scaling Across Markets
51:39 Fast Hiring Playbook
53:56 Paid Trial Workdays
57:09 Early Hires Through Networks
59:30 First Employees Matter
59:58 Closing Thoughts
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Sara Davies on Changing Dragon’s Den, Building a Personal Brand, and Why Small Business Is Tougher Than Ever

Jimmy welcomes Sara Davies as the first “Dragon” guest on Jimmy’s Jobs of the Future, discussing how she brought a more empathetic, collaborative approach to Dragon’s Den by refusing to be “more dragon-y” and staying true to herself.

Sara explains how her confidence grew over six years on the show, how her investing prioritizes working with entrepreneurs and impact over pure returns, and the questions she asks founders about why an idea might not work and who their real competitors are.

She contrasts hiring versus investing criteria, emphasizing cultural fit, non-verbal communication, and surrounding yourself with complementary skills. Sara also shares her personal branding process, her approach to BHAGs and thinking time, and how she uses AI to condense her own ideas rather than generate generic posts.

She also covers content strategy, the challenges facing small businesses amid Brexit, the pandemic, and economic pressures, and highlights memorable Den deals and lessons.

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Want to come on the show?
hello@jobsofthefuture.co

Sponsor the show or Partner with us:
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Check out our clips channel here! ⬇️
https://www.youtube.com/@JimmysJobsClips

Credits:
Host / Exec Producer: Jimmy McLoughlin OBE
Producer: Thuy Dong
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This is the second part of our interview with Ed Conway, Sky News Economics Editor, author of Trade World and Material World. The first part is out on all platforms.

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Ed Conway on Trade Wars, Bread Monocultures, and the Fragile Supply Chains Behind Modern Life

Sky News Economics editor Ed Conway discusses his book Trade World, based on two years of research into how bread, cars, and textiles are made and traded, arguing globalization has made goods cheaper by concentrating production into a few places, creating dangerous vulnerabilities. He highlights monocultures in crops such as wheat and bananas, focusing on the wheat disease UG99 and how industrial bread relies on just one or two wheat varieties, drawing parallels to the Gros Michel banana collapse and risks to the Cavendish.

This is the first part of our interview with Ed. The second part drops later this week.

Watch the full interview on YouTube ⁠here⁠.

Chapters

00:00 Food Supply Sword
00:29 Meet Ed Conway
02:08 Will We Run Out
05:05 Bread Still Matters
06:44 Innovation Beats Doom
13:37 Writing Material World
18:32 Three Products Focus
22:43 AI And Conversation
24:17 UG99 Wheat Threat
24:54 Monocultures And Risk
33:29 Chokepoints And Stockpiles
40:56 Tracking Product Journeys
42:17 Russia Wheat Surge
42:47 Wheat as Power
44:30 Automation and Bakeries
48:25 Lights Out Mills
52:04 AI as Job Tool
53:51 Markets Need Work
56:31 Red Flag Lessons
01:03:22 Who Makes Cars
01:10:28 China EV Shock
01:17:24 The 80 Pound T Shirt
01:20:40 Blue Plaques for Industry
01:23:02 Humans in AI Age

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Follow us on socials!
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Twitter / X: https://www.twitter.com/JimmyM
Linkedin: https://www.linkedin.com/in/jimmy-mcloughlin-obe/

Want to come on the show?
hello@jobsofthefuture.co

Sponsor the show or Partner with us:
hello@jobsofthefuture.co

Check out our clips channel here! ⬇️
https://www.youtube.com/@JimmysJobsClips

Credits:
Host / Exec Producer: Jimmy McLoughlin OBE
Producer: Thuy Dong

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Ed Conway on Trade Wars, Bread Monocultures, and the Fragile Supply Chains Behind Modern Life

Sky News Economics editor Ed Conway discusses his book Trade World, based on two years of research into how bread, cars, and textiles are made and traded, arguing globalization has made goods cheaper by concentrating production into a few places, creating dangerous vulnerabilities. He highlights monocultures in crops such as wheat and bananas, focusing on the wheat disease UG99 and how industrial bread relies on just one or two wheat varieties, drawing parallels to the Gros Michel banana collapse and risks to the Cavendish.

This is the first part of our interview with Ed. The second part drops later this week.

Watch the full interview on YouTube here.

Chapters

00:00 Food Supply Sword

00:29 Meet Ed Conway

02:08 Will We Run Out

05:05 Bread Still Matters

06:44 Innovation Beats Doom

13:37 Writing Material World

18:32 Three Products Focus

22:43 AI And Conversation

24:17 UG99 Wheat Threat

24:54 Monocultures And Risk

33:29 Chokepoints And Stockpiles

40:56 Tracking Product Journeys

42:17 Russia Wheat Surge

42:47 Wheat as Power

44:30 Automation and Bakeries

48:25 Lights Out Mills

52:04 AI as Job Tool

53:51 Markets Need Work

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Follow us on socials!

Instagram: https://www.instagram.com/jimmysjobs

Tiktok: https://www.tiktok.com/@jimmysjobsofthefuture

Twitter / X: https://www.twitter.com/JimmyM

Linkedin: https://www.linkedin.com/in/jimmy-mcloughlin-obe/

Want to come on the show?

hello@jobsofthefuture.co

Sponsor the show or Partner with us:

hello@jobsofthefuture.co

Check out our clips channel here! ⬇️

https://www.youtube.com/@JimmysJobsClips

Credits:

Host / Exec Producer: Jimmy McLoughlin OBE

Producer: Thuy Dong
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Georgia Harrison on Revenge Porn, Changing the Law, and the Real Work Behind Being an Influencer

This week, Georgia joins Jimmy to describe her work as a celebrity campaigner, author, and influencer, and explains why creating content is a real job that requires research, editing, trend awareness, and constant posting across platforms.

She recounts how a former boyfriend filmed her without consent and sold the footage online, leading her to waive anonymity, take him to court, and campaign to remove the “intent to cause distress” loophole in the 2015 revenge porn law, work that earned her an MBE.

Georgia says current rules still fail victims, calling for faster takedowns than 48 hours, a “kill switch” system, stronger enforcement on tech companies, and action on the rise of intimate image abuse and manosphere content.

She and Jimmy also discuss motherhood, online trolling in politics, LinkedIn’s professional benefits, and taking risks despite embarrassment.

00:00 Intro
01:23 Influencer Life Explained
03:11 Reality TV Journey
03:55 Why She Became Activist
04:54 Abuse And Court Fight
08:47 Going Public For Evidence
11:26 Beyond Revenge Porn
12:32 Georgia’s Law Proposal
14:32 Tech Companies Accountability
15:55 Shame Empowerment Motherhood
19:20 Politics Like Reality TV
27:32 Trolling Bots And Safety
31:48 Receiving The MBE
34:20 Tackling The Manosphere
35:38 Manosphere Money Funnel
36:58 Creator Economy Explained
38:08 Trends Algorithms Workflow
40:56 Brand Deals And Campaigns
45:18 Styling Image Strategy
47:50 Fearless Mindset Failing
50:20 Why LinkedIn Works
54:25 Paying Mum For Childcare
56:53 Early Jobs Hustle
59:01 Love Island Leap
01:01:46 Mentor Boss Can Do
01:03:24 Reality TV Business Pitch

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Follow us on socials!
Instagram: https://www.instagram.com/jimmysjobs
Tiktok: https://www.tiktok.com/@jimmysjobsofthefuture
Twitter / X: https://www.twitter.com/JimmyM
Linkedin: https://www.linkedin.com/in/jimmy-mcloughlin-obe/

Want to come on the show?
hello@jobsofthefuture.co

Sponsor the show or Partner with us:
hello@jobsofthefuture.co

Check out our clips channel here! ⬇️
https://www.youtube.com/@JimmysJobsClips

Credits:
Host / Exec Producer: Jimmy McLoughlin OBE
Producer: Thuy Dong
Learn more about your ad choices. Visit podcastchoices.com/adchoices