Graham Ruddick | The Future of Risking it All

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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

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