Steven Bartlett dropped out of university with nothing. No money, no connections, no safety net. By 28 he was worth over £100 million and sitting in the youngest-ever Dragon's chair on BBC's Dragon's Den.
The gap between those two realities? Failure. Lots of it. And a relationship with failure that most people never develop.
Across 450+ episodes of The Diary of a CEO, Steven has returned to the topic of failure more than almost any other subject. Not in a motivational-poster way — in a raw, specific, sometimes uncomfortable way that reveals exactly how he thinks about setbacks, mistakes, and the moments that feel like the end.
This is every significant thing Steven Bartlett has said about failure across his podcast — organized by theme, with the episodes where he said them.
Table of Contents
How Steven Bartlett Redefines Failure
Most people treat failure as a verdict. Steven treats it as data. This distinction runs through nearly every conversation he has — whether he's interviewing billionaires, psychologists, or athletes who've hit rock bottom.
This isn't toxic positivity. Steven doesn't pretend failure feels good. He's been vocal about the depression, anxiety, and self-doubt that came with his early business failures. But he draws a hard line between experiencing failure and being a failure.
In his conversations with Carol Dweck — the psychologist who coined the term "growth mindset" — Steven explored how the language we use around failure literally rewires our brain's response to setbacks. Dweck's research shows that people who say "I failed" recover faster than those who say "I'm a failure." Steven has referenced this distinction in dozens of subsequent episodes.
Steven's Personal Failures (In His Own Words)
What makes Steven's perspective on failure credible isn't philosophy — it's biography. He's been remarkably transparent about the failures that shaped him.
Dropping Out and Going Broke
Steven dropped out of Manchester Metropolitan University after one lecture. He's called this decision both "the smartest thing I ever did" and "the most terrifying moment of my life." He lived in extreme financial difficulty, sleeping on floors and scraping by while trying to build his first business.
Failed Businesses Before Social Chain
Before Social Chain became a publicly traded company, Steven had multiple ventures that went nowhere. A wallpaper app. Various websites. Projects he poured months into that never gained traction.
Leadership Failures at Social Chain
Even after Social Chain took off, Steven has been candid about his failures as a leader. He's spoken about hiring mistakes, culture problems, and moments where his ego got in the way of good decision-making.
In his conversation with Simon Sinek, Steven opened up about a period where Social Chain's culture deteriorated because he was too focused on growth metrics and not enough on people. Sinek's response — that "leadership is not about being in charge, it's about taking care of those in your charge" — became one of Steven's most-referenced lessons.
On the Fear of Failure
Steven draws a critical distinction between failure itself and the fear of failure. He argues the fear does more damage than any actual failure ever could.
This theme came up powerfully in his episode with David Goggins, who described how the fear of failure kept him trapped in a 300-pound body working a dead-end job. Goggins' breakthrough came when he realized that the pain of staying the same was worse than the pain of trying and failing.
Steven has also explored the neuroscience behind fear of failure with Dr. Andrew Huberman, who explained that our brains are literally wired to overweight potential losses versus potential gains — a survival mechanism that no longer serves us in modern life.
The "Regret Minimization" Approach
Steven frequently references a framework he's adapted from various guests: when facing a decision where failure is possible, project yourself to age 80 and ask which you'd regret more — trying and failing, or never trying at all.
This came up in his conversations with Tim Ferriss, who calls it "fear-setting" — the practice of writing down the worst-case scenario of any decision and realizing it's almost never as catastrophic as your brain makes it seem.
Failure as a Learning System
Perhaps Steven's most practical contribution to the failure conversation is his insistence that failure without reflection is just suffering. He's built a systematic approach to extracting value from setbacks.
The Post-Failure Audit
Steven has described a process he uses after every significant failure:
- What happened? — Strip the emotion out and describe the facts
- What did I control? — Separate your decisions from external factors
- What would I do differently? — Be specific, not vague
- What did this teach me that success couldn't? — Find the unique lesson
- What's the next action? — Convert reflection into movement
He discussed this framework extensively in his episode with Ray Dalio, whose book Principles argues that "pain + reflection = progress." Dalio told Steven that Bridgewater Associates — the world's largest hedge fund — literally has a culture of documenting and analyzing failures the same way they analyze market data.
The Compounding Effect of Small Failures
In his conversation with James Clear, Steven explored how small, frequent failures are actually more valuable than big, rare ones. Clear's Atomic Habits framework applies directly: if you can fail fast, fail small, and fail often, you compound learning at a rate that makes eventual success almost inevitable.
Alex Hormozi reinforced this in his appearance, telling Steven that his first gym failed, his first supplement line failed, and his first attempt at scaling failed — but each failure took less time and cost less money because he was learning faster than he was failing.
What His Guests Taught Steven About Failure
Some of the most powerful moments on The Diary of a CEO happen when guests share failure stories that visibly change Steven's perspective. Here are the ones he's referenced most.
Arnold Schwarzenegger — "Useful" Failure
Arnold told Steven that every failure in his life — losing bodybuilding competitions, box office flops, political scandals — taught him something specific he couldn't have learned any other way. His framework: ask "Was this failure useful?" If yes, it wasn't really a failure at all.
Bren— Brown — Vulnerability and Failure
Bren—'s research on vulnerability gave Steven language for something he'd felt but couldn't articulate: that the willingness to fail publicly is the same muscle as the willingness to succeed publicly. You can't have one without the other. Her concept of "the arena" — that the critic doesn't count, only the person in the arena matters — became a recurring reference point for Steven.
Gordon Ramsay — Rock Bottom as Foundation
Gordon shared the story of losing his first restaurant and the humiliation that followed. His takeaway: "Rock bottom became the solid foundation I built my life on." Steven has said this episode fundamentally changed how he views his own lowest moments.
Dwayne "The Rock" Johnson — Depression After Failure
Dwayne's candid discussion of his depression after being cut from the Canadian Football League gave Steven permission to talk more openly about the emotional toll of failure — not just the eventual comeback story, but the darkness in between.
Sara Blakely — Her Dad's Dinner Table Question
Sara Blakely, founder of Spanx, told Steven that every night at dinner her father would ask: "What did you fail at today?" If she had nothing to report, he was disappointed. This reframed failure from something to hide to something to pursue. Steven called this "the single best parenting advice I've ever heard on this podcast."
Jordan Peterson — Meaning Through Suffering
Peterson's perspective added a philosophical layer: failure and suffering aren't obstacles to a meaningful life — they're prerequisites for one. Without them, success has no weight and no meaning. Steven has said this conversation shifted his relationship with discomfort more than any other.
Practical Frameworks for Handling Failure
Across hundreds of episodes, Steven has distilled his approach to failure into actionable frameworks anyone can use.
1. The 10-10-10 Rule
When a failure happens, ask: Will this matter in 10 minutes? 10 months? 10 years? Most failures that feel catastrophic in the moment don't register at the 10-year scale. This perspective instantly reduces the emotional charge and lets you think clearly.
2. Separate Identity from Outcome
Your business failing doesn't make you a failed businessman. Your relationship ending doesn't make you unlovable. Steven learned this from Dr. Julie Smith, whose work on cognitive distortions shows that we habitually merge events with identity — and it's the merging, not the event, that causes lasting damage.
3. Speed of Recovery Over Avoidance of Failure
Steven argues that the most successful people don't fail less — they recover faster. His conversation with Mark Manson (author of The Subtle Art of Not Giving a F*ck) reinforced this: resilience isn't about never falling, it's about how quickly you get back up.
4. Public Failure Builds Trust
Counterintuitively, Steven has found that being open about failures builds more trust and connection than only sharing wins. He's referenced research discussed with Robert Cialdini showing that admitting weaknesses actually increases persuasiveness — a principle Cialdini calls the "weakness-first" strategy.
5. The "Quitting vs. Failing" Distinction
Steven draws a hard line between quitting and failing. Failing is running out of road despite your best effort. Quitting is choosing to stop before the road runs out. He respects both — but argues you need to be honest about which one you're doing.
How to Apply Steven's Failure Philosophy to Your Life
Here's the practical takeaway from 450+ episodes of Steven Bartlett talking about failure:
If You're Afraid to Start
- Use Tim Ferriss's fear-setting exercise: write down the absolute worst-case scenario. It's almost never as bad as your brain imagines.
- Remember: the fear of failure does more damage than failure itself. Inaction has a cost too — and it compounds.
- Listen to the David Goggins episode when you need a jolt of courage.
If You've Just Failed
- Run Steven's 5-step post-failure audit (above). Don't skip it.
- Separate the event from your identity. You experienced failure. You are not a failure.
- Give yourself a defined recovery period — then move. Wallowing has diminishing returns.
- Listen to the Mel Robbins episode for the "5 Second Rule" to override analysis paralysis.
If You Keep Failing at the Same Thing
- You're not learning from the failure — you're just repeating it. Ray Dalio's "pain + reflection = progress" only works if you actually reflect.
- Change your approach, not just your effort. Working harder at the wrong thing is still the wrong thing.
- Consider whether you're pursuing someone else's definition of success. The Naval Ravikant episode on finding your unique leverage is essential listening here.
If You're Helping Someone Through Failure
- Use Sara Blakely's father's approach: normalize failure by celebrating the attempt.
- Don't rush to fix or minimize. Bren— Brown's work on empathy (vs. sympathy) shows that sitting with someone in their failure is more powerful than offering solutions.
- Share your own failures first. It gives them permission to be honest about theirs.
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The Bottom Line: Failure Is Not Optional
If there's one thread that runs through every Diary of a CEO episode about failure, it's this: failure is not something that happens to unsuccessful people. It's something that happens to everyone. The only variable is how you respond.
Steven Bartlett didn't succeed despite his failures. He succeeded because of them. Not in some abstract, motivational-poster way — in a concrete, documented, lesson-extracted way that he's shared across hundreds of hours of conversations.
The question isn't whether you'll fail. It's whether you'll build the systems, mindset, and resilience to make your failures count.
Related Episodes to Watch
- Steven Bartlett — The Full Story
- Alex Hormozi — $100M Offers
- David Goggins — Can't Hurt Me
- Carol Dweck — Growth Mindset
- Ray Dalio — Principles
- Bren— Brown — Vulnerability
- Tim Ferriss — Fear-Setting
- Jordan Peterson — Meaning Through Suffering
- Naval Ravikant — Leverage & Happiness
- Mel Robbins — The 5 Second Rule