Episode 1: “The Business That Broke Me, The Mindset That Fixed Me”

The Show

Most of what holds us back isn’t real—it’s just the way we’ve been taught to see things. Welcome to The Failosophy Show, where we stop letting old stories about success and failure define us. Because when you change how you think, you take control—not just of what’s possible, but of who you become.

The Guest

Issue one features Failosophy show guest and newly appointed Failosopher Jamal Ayton-Brown

The Journey

Jamal Ayton-Brown’s journey is a raw narrative of ambition, resilience, and reinvention, marked by devastating setbacks and transformative growth. Over a decade as an entrepreneur, Jamal encountered numerous failures, from ill-fated tech products to a nootropic e-commerce venture. His story reveals a life lived on the edge of insecurity and ambition, with failure as a companion and a relentless teacher.

In the early years, Jamal’s failures stemmed from technical limitations and an unwillingness to build the right partnerships, compounded by a crippling fear of rejection. The pivotal moment came in 2018 with a browser app project. Teaching himself to code, he developed a functional product but hit a wall due to financial constraints and a lack of advanced technical skills. This led to profound self-doubt and a six-month depression—the darkest chapter of his journey. It was here, however, that Jamal’s mindset began to shift.

He reframed failure as an essential ingredient of success, embracing its lessons instead of fearing its weight. Failosophy’s principles resonate deeply with his approach, especially the focus on adaptability, identity evolution, and using failure as feedback. Jamal now views ambition as a double-edged sword—both fuelled by insecurity and tempered by a relentless drive for self-improvement. He’s learned the power of seeking objective feedback, iterating constantly, and recognising when to pivot or let go.

Despite enduring failures, including his last business closure, Jamal continues to push forward. His ultimate goal is impact, valuing contribution over recognition. His journey mirrors the Failosophy ethos: failure is not a destination but a path to identity, resilience, and enduring growth.

The Formula

As a recap, here's the Failosophy Formula:

This formula breaks failure into five elements: ambition, energy, expectations, adaptability, and emotion. It helps us understand why failure happens and how to minimise its impact or risk.

Failure (Impact or Risk) = (((Ambition × Energy) × Expectation) / Adaptability) × Emotion

Jamal's evolution across the five components of the Failosophy formula feels like tracing the arc of a man who's learned to turn his scars into maps. His journey, laced with failures that could've buried most, instead chiselled a deeper understanding of himself and his purpose. Let’s break it down.

Ambition: The Engine That Never Stopped

Jamal’s ambition has been a double-edged sword. Early on, it fuelled a drive to prove himself, born from insecurities rooted in his school years. This ambition was raw, almost desperate – a need to prove to others and himself that he could be someone. Over time, though, this hunger matured. It’s no longer just about reaching an end goal; now, Jamal sees ambition as a process of pushing boundaries and exploring his potential. He’s split it into two layers: the destination he aims for and the vehicle of becoming his best self. That shift – from external validation to intrinsic growth – is a sign of someone who’s wrestled with failure and come out transformed.

Energy: Burning the Right Fuel

In the beginning, Jamal poured energy into his ventures like a man sprinting a marathon – all intensity, little sustainability. The 2018 collapse of his tech product “Browse” showed how his unbalanced investment of effort, without proper support, led to burnout. But the man learned. He started focusing on daily skill-building and smarter allocation of his energy. Now, it’s less about brute force and more about precision. Jamal’s energy is no longer scattered; it’s deliberate, focused, and replenished by the lessons of his past.

Expectations: From Rigid Ideals to Flexible Realism

Expectations were once Jamal’s silent killer. He clung to rigid visions of success, thinking failure meant he wasn’t good enough. The early projects – a string of efforts that couldn’t get off the ground – were proof of his misaligned expectations. But failure taught him to loosen his grip on perfection. Now, he approaches new ventures with tempered optimism, realistic targets, and a willingness to adapt. That shift from obsessing over outcomes to valuing contributions shows a man who’s finally made peace with the messy, uncertain nature of growth.

Adaptability: Building Muscle from Pain

Adaptability wasn’t always in Jamal’s toolkit. His early failures were marked by a fixed mindset, his stubbornness leading him into dead ends. The aftermath of 2018, when he spiralled into depression, was a crucible. Emerging from that darkness, he realised that rigidity was his downfall. These days, Jamal is all about pivoting. He asks for feedback – even when it’s brutal – and keeps his ego in check. He’s learned to embrace failure as a signal to adjust course, not as a verdict on his abilities. Adaptability, for Jamal, has become less about reacting and more about anticipating.

Emotion: Harnessing the Chaos

Here’s where the rawness of Jamal’s evolution hits hardest. His early failures weren’t just professional setbacks; they were deeply personal blows. The man once defined himself by his mistakes, letting shame and insecurity run the show. But the 2018 breakdown was a turning point. He learned to face the emotional weight head-on, allowing himself to feel, process, and then move forward. Jamal has since developed a healthier relationship with his emotions – balancing vulnerability with resilience. He doesn’t wallow anymore; he reflects, recalibrates, and keeps going.

Final Course

Jamal’s evolution through the Failosophy formula reads like a redemption story. He’s shifted from being a man paralysed by the fear of failure to one who sees it as a badge of honour. His ambition is refined, his energy sustainable, his expectations grounded. He’s built adaptability like a survivalist and mastered his emotions like a monk who’s wrestled demons. Jamal is no longer running from failure; he’s running with it, using it as a compass to navigate life’s wild terrain.

And that’s the beauty of it – he’s not done yet. The man is still cooking, still learning, still failing. And isn’t that what makes the journey worth it? The grit, the grind, the scars that tell the story of a life well-lived.

The Failosophy

Jamal Ayton-Brown’s journey and Failosophy reveal a treasure trove of insights into embracing failure as a critical component of growth.

Tip: Learn to Sit with the Chaos

Challenge: Jamal found himself spiralling into a deep depression following his app failure in 2018. The weight of perceived inadequacy and a lack of alternatives kept him paralysed.

Jamal’s Response: He didn’t fight the emotions immediately. Instead, he allowed himself to feel the full brunt of the experience—anger, disappointment, confusion—before choosing to move forward. This raw confrontation with his feelings became a turning point.

Application: When failure strikes, don’t rush to escape the discomfort. Take a moment, or several, to acknowledge and feel the chaos. Journal your thoughts, vent to a friend, or sit silently. Then, when ready, recalibrate and strategise. Let the dust settle before you chart your next move.

Tool: The Feedback Loop

Challenge: Jamal admitted to fearing rejection and avoiding feedback, leading to blind spots that stunted his progress.

Jamal’s Response: Over time, he embraced the discomfort of constructive criticism, seeking honest feedback from colleagues and collaborators. This consistent input became a compass, guiding his adjustments and growth.

Application: Develop your own feedback loop. After any project or failure, ask trusted individuals for specific, actionable critiques. Use tools like anonymous surveys or feedback apps if personal confrontation feels daunting. Build resilience by viewing feedback not as judgment, but as a blueprint for growth.

Technique: The Failosophy Reflection Method

Challenge: Early on, Jamal’s mindset was too rigid, preventing him from seeing opportunities in setbacks.

Jamal’s Response: He started documenting failures, breaking them down into causes and lessons, and storing this “failure ledger” for future reference. This practice rewired his approach to setbacks, turning them into opportunities.

Application: After every failure, conduct a debrief. Write down:

What went wrong?

What external and internal factors contributed?

What can I learn?

What would I do differently next time?

Treat these notes as a personalised Failosophy archive—a guide to your past, informing your future.

Bonus Insight: Mastering Ambition’s Duality

Jamal’s ambition evolved from a singular drive to succeed to a dual-focus system: achieving end goals and becoming the best version of himself in the process. His transparency about insecurity fuelling ambition is an invitation to own our vulnerabilities and channel them productively.

Challenge: How do you balance chasing goals with improving yourself along the way?

Jamal’s Response: He identified self-awareness as the linchpin, accepting responsibility for his shortcomings and committing to continuous growth.

Application: Cultivate daily self-reflection. At the end of the day, ask yourself: Did I progress toward my goal? and Did I grow as a person? Use this practice to ensure you’re climbing the right ladder—not just any ladder.

Jamal’s philosophy and Failosophy’s frameworks remind us: failure isn’t just inevitable—it’s vital. Embrace the mess, learn the lessons, and forge ahead, carrying those scars like badges of honour. Life’s greatest flavours come from the grit and grind, not just the garnish.

The Framework

Failure isn’t the enemy—it’s the process. But most people spend their lives running from it, letting fear dictate their choices. The Fear to Freedom Framework lays out the five stages of that journey—from avoiding failure entirely to using it as fuel. It’s not about making failure painless; it’s about making it useful. Wherever you are on the path, this framework helps you move forward—because staying stuck is the only real failure.

Avoidance Stage: Fear of Failure as a Limiting Force

Insight: "I definitely was somebody who was very scared to fail... I had a lot of judgment on myself around that concept of what it meant to be a failure."

Guidance: Jamal started out seeing failure as a personal verdict—a judgment, a brand, a reason to play it safe. If you’re in this phase, paralysed by what failure might say about you, ask yourself: whose definition of failure are you living by? Jamal’s journey proves that the fear is often a mirage, reinforced by stories of overnight success that leave out the bruises. If you avoid failure at all costs, you’re also avoiding the version of you that’s waiting on the other side of it.

Awareness Stage: Recognising but Resenting Failure

Insight: "The biggest failure for me that had the biggest impact actually happened around 2018… I kind of gave up. And what ended up happening off the back of that was that I went into a deep depression."

Guidance: This is the messy middle—the point where failure isn’t an abstract idea, but something that’s knocked you flat. You know failure is part of the game, but it still stings. Jamal’s 2018 breakdown wasn’t just about the failure itself—it was about his perception of it. If you’re in this phase, take a hard look at your expectations. Are you punishing yourself for not moving faster? Are you stuck between knowing failure is necessary but still feeling like it’s a personal loss? Awareness is uncomfortable, but it’s also where growth begins.

Engagement Stage: Using Failure Instead of Running from It

Insight: "I ensure that any situation that I'm in, if it looks like it's going to fail... I'm analysing, okay, what can I do differently here? What other ways are there to circumvent this failure?"

Guidance: Jamal learned to flip the script—failure wasn’t about self-worth anymore, it was data. He stopped taking it personally and started taking notes. If you’re here, the question isn’t if you’ll fail, but how you’ll use it. Are you treating failure like an open wound, or are you breaking it down for parts? Start treating failure like an engineer, not a victim. Look at it, pull it apart, and build something better.

Integration Stage: Failure Happens FOR You, Not TO You

Insight: "I don't see a point personally of looking back. I know that in that moment, I did the best with what I had at that time with the information that I had."

Guidance: Here’s where the weight starts lifting. Jamal stopped looking at failure as a tragedy and started seeing it as just another moment in motion. If you’re in this phase, your identity isn’t shattered by setbacks anymore—it’s shaped by them. You’re starting to see that failure isn’t just a cruel accident, it’s the very thing refining you. The next step? Stop resisting. Accept the lesson, integrate it, and move.

Mastery Stage: Failure Becomes Neutral Data, Not Emotional Trauma

Insight: "I’ve come to realise that anybody who’s succeeding is actually constantly iterating and constantly receiving feedback... If you’re only getting positive feedback, then you’re going to be very much blinded to mistakes."

Guidance: At this level, failure is just part of the process—no drama, no spiral, no existential crisis. Jamal gets that now. He actively seeks out criticism because he understands it’s the only way forward. If you’re here, your challenge isn’t avoiding failure—it’s making sure you don’t get comfortable. Are you still pushing? Or have you started coasting because failure doesn’t scare you anymore? Keep moving.

The Quotes

"I look at failure now as a key to success. Success is 100% impossible without failure, and actually, failing now is something I embrace. I love failing because it means I’m doing something I’m not yet good at but can improve and grow from."

"The question shouldn’t be, ‘How do we get away from failure?’ because we need failure if we want to get anywhere in life. The real question is, ‘How can we prepare ourselves mentally to deal with failure?’"

"I taught myself to code to build an app. I failed because coding wasn’t my strength, but that taught me to acknowledge what I’m not passionate about and what I need others for. That’s how I’ve grown."

"Allow yourself to feel failure—sit with it, blame the world if you need to—but don’t stay in that place. At some point, you have to say, ‘I’m ready to move forward.’"

"The knowledge and acceptance that if I’m not where I want to be, the issue is me. It’s not anything external. I need to look within and understand what I need to change about myself to get there."

"I’ve always been fearful of rejection and negative feedback, but I’ve come to realise that anyone succeeding is constantly iterating and receiving feedback, mostly negative. That’s how you grow."

"Failure taught me truths about myself, about my limits and strengths. It was in that harsh reflection that I began building a more authentic and capable version of me."

"You don’t always need brute force to get through a problem. Sometimes you need to step back, re-evaluate, and find another way."

"Ambition comes from knowing that I’m capable but not yet where I need to be. That self-awareness is what drives me forward every day."

"I love to create. Failure is part of that—it’s the raw material I work with, refining my ideas and myself every time something doesn’t work."

The Future

Hope you enjoyed this first edition of The Failosopher. Look out for the upcoming shows, featuring guests including Kelly, who sees failure as the blueprint for building identity, resilience, and a purposeful life; James, who, after numerous boardroom battles, brought Malibu and Baileys Irish Cream to our shores; Konrad, who overcame international prejudice to become a trailblazer in British skiing; and Alex, who was forced to recalibrate his expectations after failing one of the most challenging entrance exams for a prestigious business school. All this and more to come!

Oh, and let’s not forget—the Failosopher (Quest) Edition lands mid-February, offering a deeper, more introspective look at the themes we explore on the Failosophy Show. And as if that wasn’t enough, also in February, we launch the Failonomics Show—where we dissect how failure shapes industries, economies, and organisations.

Phew. That’s a wrap on this first edition of the Failosopher (Guest) Edition. Take care. Chris.

Links

Listen to this episode of the Failosophy Show Podcast

Visit the Failosophy Show Website

Visit Jamal’s LinkedIn Profile Page