The Mindset that Saved Me from Brutal Startup Failure | TaleTree, Matt Hagger

The Entrepreneurial Journey and the Power of Failure [00:00]

• The speaker has over 20 years of experience as a serial entrepreneur in the UK and Silicon Valley.
• His second company, Scatter, a photo-sharing product, did not achieve the widespread success of platforms like Instagram or TikTok, leading to its eventual cessation.
• Failure is presented not as an end, but as a source of valuable lessons and resilience, akin to acquiring "weaponry" or "armor" for future challenges.
• The entrepreneurial path is often depicted as a chaotic descent ("falling out of the plane") where solutions are discovered mid-flight.

"Unfortunately, 95% of all startups end in failure. Scatter did not become the Instagram, Tik Tok or X that we see today because it's not existing right now. When you climb that high, the fall is equally as heavy."

Cultivating Courage and Empowerment [00:40]

• Courage stems from taking leaps of faith and confronting uncertainty, especially when solutions are not immediately apparent.
• A formative experience involved a father who encouraged independence by making the speaker feel responsible for his own actions, fostering a sense of self-reliance.
• Acts of empowerment, such as belief and validation from others ("I believe in you. You can do it. You're good enough."), are vital.
• True entrepreneurs are characterized by their persistent drive to "come back" after setbacks, mirroring the resilience of children who continuously get back up after falling.

"Courage comes from taking a leap, throwing yourself in because we don't know the solution. We don't know the answer."

Tailtree: Fostering Imagination in the AI Era [01:51]

• Matt Hager, founder and CEO of Tailtree, aims to preserve imagination and creativity in children in the age of AI.
• Tailtree encourages children to brainstorm, imagine, and generate ideas in a "free space" to explore their hearts, interests, and passions.
• Prior entrepreneurial experience includes helping founders turn ideas into successful companies at Eman Venture Labs.

"Tailtree empowers children in a post AI era to hold on to the precious gift of imagination and creativity."

Embracing "Crazy" Ideas and Childhood Creativity [02:35]

• Ideas that are perceived as "crazy" by others should be taken seriously, as widespread agreement may signal that the idea is no longer novel.
• The speaker's enjoyment of creative subjects like writing, drama, and art during school contrasted with the disruption of the "bell ringing" when engrossed in creative flow.
• A realization occurred that the rigid school structure limited the creative freedom experienced in kindergarten.

"When everybody thinks your idea is crazy, you should take it very, very serious. That's more important than having everybody agree with your idea because everybody agrees with your idea, it's probably too late and somebody's already done it."

Problem-Driven Entrepreneurship and Early Innovations [03:38]

• The speaker's entrepreneurial ventures are driven by inherent problems or personal pains.
• An early experience with costly dial-up internet led to the development of a desktop news alerts protocol to efficiently check for website updates.
• This invention received a feasibility study grant from Cambridge University Science Park and was eventually rolled out as the Sky Sports News alerts platform.
• A lack of understanding of venture capital and entrepreneurship at the time meant the initial success was driven purely by problem-solving.

"I'm going to build something that prevents this from happening for me and everybody else."

The Passion Imperative and Childhood's Influence [05:19]

• Entrepreneurship is not for everyone; it requires a deep, meaningful passion to sustain oneself through extreme difficulties.
• The speaker's childhood directly correlates to the mission of Tailtree, which he feels is partly for the child he once was.
• Father's support involved enabling learning through challenges, such as using maps to plan trips and learning about cities and football statistics, fostering learning through enjoyable activities.

"I feel like sometimes I'm building tree for the child inside me."

Reclaiming Innate Creativity [06:41]

• The speaker's childhood realization was a desire to empower humanity to think creatively with authenticity and purpose.
• Children possess innate curiosity, imagination, and wonder, which often diminishes as they grow up and go through formal education systems.
• The Head Start program research by George Land demonstrated a significant decline in creativity scores from age 5 (98% genius level) to age 30 (2%).
• This decline is attributed to an educational system that prioritizes memorization and examination performance over nurturing creative thinking.

"The average genius level creativity in children, 98% of all kids that were tested were deemed as geniuses. But by the time these children reach the age of 30, it goes down to 2%."

The Importance of Community and Shared Mission [08:40]

• Tailtree aims to create a global community for children to share art, communicate, and offer compliments, fostering a sense of liberation.
• Supportive communities are crucial for entrepreneurs and creative individuals, helping to mitigate struggles.
• A deep love for the problem being solved is essential when deciding to become an entrepreneur.

"Having supportive community around you is very very important for entrepreneurs, for creative people cuz without community I think we would struggle."

Learning from Failure and Iteration [09:23]

• Eman Venture Labs invests in entrepreneurs who have failed multiple times, recognizing that each failure provides valuable learning experiences.
• Success is often a result of iteration and being closer to the solution with each attempt, though luck also plays a role.

"The ideas that started in Eman Venture Labs will always invest in a an entrepreneur that's failed three or four times because of the learnings that they get from the failure."

Scatter: A Pioneer in Photo Sharing [09:47]

• Around 2005-2006, during the early smartphone era, the speaker recognized the potential of mobile cameras for real-time sharing.
• This led to the development of Scatter, one of the first photo-sharing smartphone apps, built on the nascent Android platform.
• Explaining the concept was difficult, with many dismissing the idea of sharing personal media.
• Scatter was considered a "contrarian truth," an idea that felt right despite widespread skepticism.

"When everybody thinks it's crazy. So, all of these issues I was I was being faced with was just very negative and I couldn't really see how in the UK I could get my business going."

The Impact of Timing and Location on Startup Success [11:01]

• Luck and timing are critically important for startup success, as is having a product that a market is ready to adopt and the necessary distribution technology.
• A bold leap to San Francisco and Silicon Valley revealed a significantly more positive and supportive ecosystem for new ideas.
• The ecosystem's encouragement and support were instrumental in the achievements with Scatter.

"The whole ecosystem was just incredible. And if I hadn't have gone out there, I don't think I would have been able to achieve what I achieved with Scatter."

Navigating Early Ecosystems and Funding Challenges [11:39]

• Scatter was among the first apps on the newly launched Android market.
• The company raised over $1 million in pre-seed funding but was "too early."
• Challenges included nascent app stores, the need to help evolve these ecosystems, and the technical resource intensity of building on unstable systems.
• A profound idea needs an addressable market and distribution capability to avoid being overtaken by competitors who arrive at a more opportune time.

"We didn't have access to distribution because the app stores were new and we were launching and helping these ecosystems to evolve."

The Weight of Failure and the Need for a New Perspective [13:19]

• Working on something deeply meaningful involves pouring heart, soul, and passion into it, making it a way of life.
• The fall after such intense commitment can be equally profound and disheartening.
• Failure is reframed as valuable feedback, guiding future actions, and signifies being "the man in the arena" who takes risks.
• The relationship with failure needs to change, adopting a childlike fearlessness towards falling and an understanding that it's an integral part of the journey.

"Failure means you tried means you were actually the man in the arena, not the voice in the crowd."

Working ON the Business: Mission and Momentum [14:47]

• The distinction between working "in the business" (over-controlling, trying to be everyone) and "on the business" (mission-driven, empowering others) is critical for growth.
• A company is a collective of people with shared aims; founders should act as "chief happiness officers" by empowering their teams.
• Working "on the business" involves creating a mission that resonates deeply with every employee, fostering a shared purpose.
• Breaking down an overwhelming vision into "bite-sized moments" and achieving small milestones creates momentum, leading to miracles.

"Working on that company always as I think the difference between being good and being great."