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December 14.2025
3 Minutes Read

Exploring the Mindset That Saved Me from Brutal Startup Failure

Mindset That Saved Me from Startup Failure, thoughtful reflection.

The Evolution of Entrepreneurship: Learning from Failure

For many aspiring entrepreneurs, the dream of launching a successful startup can feel like a tantalizing goal, yet the road to success is riddled with challenges and steep odds. Recent insights from Matt Hagger, founder and CEO of Tail Tree, highlight a crucial aspect of this journey: the mindset required to navigate the brutal reality of startup failure.

In The Mindset that Saved Me from Brutal Startup Failure | TaleTree, Matt Hagger shares experiences and lessons learned in entrepreneurship, prompting a deeper exploration of resilience and creativity.

The Harsh Reality: Startup Failures

Over the past two decades, Hagger has experienced the highs and lows of entrepreneurship firsthand. Initially launching a photo-sharing app called Scatter, he dreamed of creating a platform that everyone worldwide would use. However, like approximately 95% of startups, Scatter did not become the success he envisioned. Instead of succumbing to defeat, Hagger learned to view failure through a different lens—one that emphasized resilience and growth. “Failure is great feedback,” he asserts, indicating that every setback provides invaluable lessons for future endeavors.

Courage: The Key to Entrepreneurship

Hagger's journey underscores the importance of courage in the face of uncertainty. He likens the entrepreneurial experience to “falling out of a plane,” where you often don’t know how to open the parachute until you’re closer to the ground. This metaphor speaks to the leap of faith required to start a business. “Courage comes from taking a leap, throwing yourself in because we don’t know the solution,” he explains. It’s this willingness to embrace uncertainty and learn from mistakes that can lead to eventual success.

Learning from Childhood: The Power of Imagination

Reflecting on his childhood, Hagger shares how creative freedom nurtured his entrepreneurial spirit. Although he faced a challenging education system that didn't encourage creativity, he remembers the joy of coming up with ideas and solutions to problems—such as creating a desktop news alerts protocol to save his mother from high phone bills. This problem-solving instinct translates directly to his current mission at Tail Tree, where creativity is paramount. “We need to train that spark,” he emphasizes, advocating for educational environments that foster imagination instead of stifling it.

Building a Community: Support Systems for Entrepreneurs

A vital factor in Hagger’s entrepreneurial philosophy is the role of community. He believes that having a strong support system is crucial for creative individuals and business owners. “Without community, I think we struggle,” he remarks, reinforcing that empathy and collaboration can help transform challenges into opportunities. In a world often characterized by competition, fostering community can lead to better ideation and growth.

Turning Ideas into Action: Lessons on Execution

Hagger’s insights also emphasize the critical nature of execution. Addressing the lessons learned from Scatter, he notes that being at the right place at the right time with the right technology is crucial. Luck and timing often determine which startups succeed and which ones fail. “Just because you have an idea that’s profound, if you don’t have an addressable market or the ability to distribute your idea, you might end up being eaten by somebody that arrives on time,” he warns. This advice is particularly relevant for startups aiming to make their mark in extremely competitive markets.

The Future of Creativity: How Tail Tree Empowers Children

His current project, Tail Tree, focuses on empowering children to embrace their creativity and imagination in a post-AI world. Hagger envisions a platform where children can brainstorm and share their creative ideas within a global community of like-minded peers. This initiative not only helps nurture the innate creativity in children but serves as a reminder that with the right encouragement, we can all cultivate our creative abilities throughout life. “Children shouldn’t be scared to fail,” he says. “They should be encouraged to explore and imagine.”

Conclusion: Embracing Failure and Fostering Resilience

Matt Hagger’s journey exemplifies the struggles and triumphs that characterize the entrepreneurial path. Learning from failures, embracing creativity, fostering community support, and navigating the challenges of execution are all pivotal components. Every entrepreneur must understand that the journey is as valuable as the destination and that each setback is a step toward ultimate success. As we look to the future of entrepreneurship, let Hagger’s experiences inspire current and aspiring founders to persist, learn, and dream big.

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