Graham Ruddick | The Future of Risking it All

Jimmy's Jobs of the Future

Boxlight Creative Studio

Technology, Business, Careers

5 • 1.1K Ratings

🗓️ 26 August 2025

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

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Summary

Thank you to our partners at https://octopus.energy/ Want your own Brand or Business Podcast? Try out our NEW Podcast Calculator: https://www.boxlight.io/ Are you playing it safe... and losing? In this episode of Jimmy's Jobs of the Future, journalist and Risk Roulette author Graham Ruddick breaks down why risk isn’t what you think it is - and why avoiding it might be the biggest mistake of all. We dive into how visionaries like Jeff Bezos, Elon Musk, and Simon Arora used bold bets to win big, why British business culture punishes risk, and how Zuckerberg’s MMA fight became a metaphor for Meta’s strategy. From the Ratner blunder to the EasyJet playbook, this episode is a tour through the real game of business - where risk = power. Whether you're a founder, student, or future policymaker this is a masterclass in how to use risk to your advantage. 🔥 TIMESTAMPS 00:00 Intro 01:42 What We Get Wrong About Risk (and Why It Matters) 03:36 Why the US Is Winning on Risk and the UK Is Lagging 05:17 Simon Arora’s £4.3B Gamble with B&M 09:45 How One Joke Cost a CEO Everything (Ratner Story) 15:22 The Mindset of the Most Successful Entrepreneurs 23:49 Can Journalism Survive the Creator Economy? 35:04 Why Legacy Media Is Losing to Creators 35:52 The #1 Thing That Will Make or Break Media Companies 37:54 How AI Is Reshaping the Future of News 41:39 How EasyJet Disrupted Airlines with One Risky Bet 43:56 The Guests That Changed How We Think About Business 46:15 Innovation Lessons from Sport: F1, NFL & the NBA 50:46 How Turnarounds Really Happen and Who Pulls Them Off 51:25 Quickfire: Podcast, Politics & What’s Next for Graham 01:03:23 Where Business and Politics Collide ********** 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? [email protected] Sponsor the show or Partner with us: [email protected] Credits: Host / Exec Producer: Jimmy McLoughlin OBE Producer: Sunny Winter https://www.linkedin.com/in/sunnywinter/ Junior Producer: Thuy Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Welcome back to Jimmy's Jobs for the Future. I hope you've been having a great summer.
0:04.3	Today's guest is Graham Ruddick. Now Graham used to be deputy business editor at the Times.
0:10.3	And when I first left number 10, I used to write quite a bit in the Times business pages about
0:14.6	different ideas, partly as I was exploring what I was going to do next. And whenever Graham was
0:20.3	kind of on the desk, I would sort of write three different ideas
0:23.3	that I got in my head.
0:24.2	And he would always pick the one that was the sort of most different.
0:27.5	I sort of wrote about the rise of coaching and all these different types of things
0:31.6	that you might not traditionally see as much of in the time's business pages.
0:35.5	So it wasn't a huge surprise to me when he decided to go and launch his own thing,
0:39.8	which was a very bold step.
0:41.7	He launched the Off to Lunch Substack, which was a brilliant email newsletter that arrived
0:48.2	in your inbox in late morning, so not competing with all the early morning business and
0:54.0	political ones that have been often out there.
0:57.3	And he scaled this quite a lot and did really well with it.
1:02.5	But then he was actually brought out by previous guests, Richard Harpin, as part of the ever-growing business leader empire.
1:09.2	So it was really interesting to get Graham on
1:11.7	to talk about his book that he's written
1:13.9	alongside doing all these things as well
1:16.0	called Risk Roulette,
1:17.7	which looks at the different,
1:20.2	and I've got a copy of it here actually.
	...

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