4 Keys to Startup Success From 25 Years of Wins and Failures (With Matt Hagger of Taletree)

4 Keys to Startup Success From 25 Years of Wins and Failures


Building a startup can feel like jumping out of a plane without knowing how to open the parachute. You are in free fall, trying to work it out before you hit the ground.

Matt Hagger knows that feeling well.

He spent around 25 years building companies in the UK, Los Angeles, and Silicon Valley. He created one of the first smartphone photo‑sharing apps, worked with the early Android team, watched his big bet, Scatter, fail, and is now the founder and CEO of Taletree, a company built to protect children’s imagination in a post‑AI world.

As he puts it:

“When you’re working on something that means everything to you, you’re putting your heart in it, your soul.”

From that journey came four hard‑earned keys to building and surviving a startup:

  1. Say “yes” when everybody says “no”
  2. Never start a startup without deep love for the problem
  3. Treat failure as armor, not a scar
  4. Work on the business, not in the business

This story walks through those four keys, using Matt’s experiences, missteps, and comebacks as the guide.

Founder walking through a modern office with charts and startup visuals in the background.

Matt Hagger In One Glance: From Dial‑Up To Taletree

Matt grew up in Cambridge, England. At school he loved writing stories, drama, and art. What he hated was the bell. It kept ripping him out of that deep creative flow.

Once, he refused to leave the classroom because he was finishing a story. His teacher tried to send him to math. He stayed put. That small act captures a theme that never left him: protect creativity at all costs.

As a teenager, he discovered the internet through dial‑up. Each session was slow and expensive. His favorite football club’s website rarely changed, yet every visit cost money because of the phone bill. His mum eventually put the bill in front of him and said, “You’re going to have to pay for this.”

His answer was simple: build something.

He created a desktop news alert tool that checked a site for updates as soon as you connected. If there was breaking news, your computer showed it, so you no longer had to reload the page over and over.

That small project turned into:

  • A feasibility study grant from Cambridge University Science Park
  • A product that became Sky Sports News alerts for Premier League clubs and Sky, one of the UK’s biggest broadcasters

Matt still did not call himself an entrepreneur. He was just solving his own problems.

Later, he would run Eman Venture Labs in Los Angeles, helping other founders turn ideas into products and companies. Then came his boldest swing: Scatter, a smartphone photo‑sharing startup that arrived years before Instagram.

Scatter did not make it.

But its failure set the stage for Taletree, which gives kids a creative companion and a global community of kind, creative children so they can hold onto imagination in a world filled with AI tools.

If you like learning from founders who turned long periods of struggle into repeatable wins, stories like Loïc’s repeatable SaaS playbook show similar patterns from a different angle.

Now, let’s break down the four keys Matt learned the hard way.


Key 1: Say “Yes” When Everybody Says “No”

Matt believes you should pay close attention when people call your idea crazy.

“When everybody thinks your idea is crazy, you should take it very, very serious.”

That is often where real opportunity hides.

From dial‑up pain to a real product

His first startup‑style project came straight from personal pain:

  • Dial‑up internet that crackled and whined
  • A static football site that rarely changed
  • A furious parent holding a high phone bill

Instead of stopping, he asked, “How do I fix this for me and everyone else?”

He built a small protocol that, on connection, checked your favorite site for fresh news, then pushed alerts to the desktop. No more constant reloads. No more surprise bills.

“I need to solve this problem because I’m costing my mother a lot of money.”

That little idea pulled him out of his bedroom and into talks with big organizations. It became the backbone for live sports alerts used by major football clubs and Sky Sports News.

The pattern: problem first, product second, market third.

Scatter: A photo‑sharing startup before the world was ready

Around 2005–2006, smartphones were just starting to appear. Windows Mobile devices were out. The iPhone and Android were still rumors.

Matt was fascinated by one thing: the camera in your pocket.

For the first time, people could capture what they saw and share it in real time. He decided to focus on that and built Scatter, one of the earliest smartphone photo‑sharing apps.

Almost everyone told him it would fail.

  • “People get photos developed.”
  • “Nobody wants to see other people’s media.”
  • “This will never take off.”

In the UK, investors and advisors shrugged. The mainstream still lived in a world of printed photos.

Matt felt the idea was right, but the environment was wrong. So he took a leap and moved to the US, especially San Francisco and Silicon Valley, where he found something different:

  • Positivity around bold ideas
  • People willing to back non‑obvious bets
  • An ecosystem built to support founders

There, he met a member of the original Android team, working under Google co‑founder Sergey Brin. They invited him into a cohort of innovators and handed him the very first G1 Android device, running an early beta of Android 1.0.

He got access to the developer kit and, for the first time, could connect a native app to the camera on a smartphone. Scatter launched on Android Market when there were only about 150 apps.

They even raised over a million dollars in pre‑seed funding.

So what went wrong?

The brutal lesson: you can be right and still fail

Scatter did not become Instagram, TikTok, or X.

Matt’s main lesson: being early is not the same as winning.

He had:

  • A strong product idea
  • Access to the bleeding edge of Android
  • Real excitement in the Valley

He did not have:

  • Mature app stores with real distribution
  • Stable mobile infrastructure
  • An addressable market ready to adopt photo sharing at scale

The team spent huge amounts of time and money trying to keep Scatter working on unstable systems while the platforms themselves were still forming. They became an unpaid R&D lab for companies that would ship smoother versions years later.

As Matt puts it, if you cannot reach a market at the right time, a better‑timed rival can “eat you” even if your original idea was more profound.

If you want to see how other founders handle timing and distribution, stories like From Shark Tank rejection to Amazon acquisition show different, but related, timing choices.


Key 2: Never Start a Startup Without Deep Love For The Problem

Matt is blunt about this.

“If you don’t have a deep and meaningful passion, that scratch that you want to itch, you should not do it.”

Startups are too hard to build around a casual interest.

His own path is a chain of problems he could not ignore:

  1. Dial‑up costs → desktop news alerts so he would not burn money on static pages
  2. New camera power → Scatter, so people could share what they saw in real time
  3. Loss of childhood creativity → Taletree, so kids can keep their imagination alive in an AI‑heavy world

Learning courage from a father who “threw him in”

A lot of Matt’s courage comes from how his dad raised him.

They traveled around England to watch their soccer team play. On each trip, his dad handed him the map. Matt would:

  • Find the city
  • Read about its history
  • Learn about the team they were visiting

His dad then quizzed him on game stats and local details. Matt felt like he was exploring the country and learning through something he loved.

The same thing happened in other areas. His father would “throw him in,” but in a safe way.

“I think my father threw me in knowing that he was there, I guess, if I went wrong, but made me feel like I was on my own doing it. And that was powerful.”

That mix of support and independence is the same kind of empowerment Taletree tries to give kids. You do not hand them all the answers. You give them space to explore their own ideas, with a safety net nearby.

Taletree and the crisis of lost creativity

Taletree exists because Matt believes something precious fades as we grow up: the fearless creativity of kindergarten.

He points to a creativity study NASA asked scientist George Land to run. Land tested the divergent thinking of children over time. As summarized in this overview of George Land and the NASA study, the results look like this:

Age group“Genius‑level” creativity
3–598%
1030%
1512%
Adults2%

Matt shares a simple example. Hold up a pen in front of a child and ask, “How many uses can you think of?”

Kids will see:

  • A sword
  • A lightsaber
  • A rocket
  • A magic wand
  • A paper clip substitute

They may list 15 or 20 ideas. Adults usually come up with one to three.

The difference is not that kids are smarter. They are less scared to be wrong.

Matt believes that between ages 5 and 30, school and society slowly dim that spark. We are trained to memorize, repeat, and pass exams. We are not trained to stay curious.

Taletree is his attempt to push back. When a child arrives there and adopts a companion, they start brainstorming and imagining. It is a free space to explore what is on their heart, what they care about, and what interests them. Kids can then share their creations with a global community of kind, creative peers.

In other words, he is building the product he wishes he had as a child.

If you like frameworks for building products around a clear itch, the founder who shared From idea to $100K MRR: proven SaaS tactics uses a similar “scratch your own pain” pattern in SaaS.

Flat lay of a laptop, notepad, and startup finance diagrams on a desk.


Key 3: Treat Failure As Armor, Not A Scar

Matt does not sugarcoat the numbers.

He quotes the common stat that about 95% of startups fail. That number shows up in many analyses, like this breakdown, 95% of Startups Still Fail, which argues that even with better tools and funding, the odds have not really changed.

Scatter’s collapse hit him hard. He had poured everything into it. The fall felt just as big as the climb.

He describes feeling low and depressed. He wanted Scatter to become something the whole world used. Instead, it disappeared.

Yet, with time, he started to see failure differently.

“Failure is great feedback. It tells you all the things that you don’t want to be doing next time.”

He sees three main gifts inside failure:

  • Clarity: You learn what does not work, which is priceless.
  • Armor: After you have been embarrassed in public and survived, you fear it less.
  • Signal: Failure means you were “the man in the arena,” not just a voice in the crowd.

Matt also noticed that in Eman Venture Labs, they preferred to back founders who had already failed three or four times. Those people had scars, but also pattern recognition. With each attempt, they got closer to something that worked.

Compare that to many first‑time founders who hit early success. They may be gifted, but they are also often lucky. When their first real setback comes, they have no practice dealing with it.

Getting back your kindergarten mindset

Matt keeps coming back to one picture: a kid learning to walk.

Children fall, get up, fall again, and keep trying. They do not feel shame about it. Nature does not feel shame about failure either. Seeds fail to sprout. Animals miss prey. The system keeps going.

Adults react differently. When we “fall” in our work or our startup, we often:

  • Hide
  • Change direction too fast
  • Carry the shame for years

Matt’s advice is simple, not easy: try to live like a kindergarten kid for life. Fall, stand up, try again.

He uses a pen test to make that real. When you treat a pen as a possible sword, rocket, or spaceship antenna, you are loosening the grip of shame on your thinking. You are giving yourself permission to look silly again.

If you want to dig deeper into how much of startup success comes from people and culture, not just product, Startup success secrets beyond the product is a helpful companion to Matt’s story.

Three professionals around a table, planning and problem‑solving together.


Key 4: Work On The Business, Not In The Business

After years inside different companies, Matt noticed a clear divide between good founders and great ones.

Good founders often do everything themselves. They are in every meeting, answer every email, review every pixel, and approve every feature. For a while, this helps. Then it strangles the company.

“If you work inside it for too long, you can suffocate and stifle the growth of the business.”

Great founders learn to step out of the weeds and work on the business, not inside every corner of it.

“Company” means people, not you

Matt likes to strip the word “company” back to its core. It means people together. Not just the founder.

When you try to be every role for too long, several bad things happen:

  • You block decisions because everything waits for you
  • You drain your own energy and your team’s energy
  • You hire good people, then do not let them do their jobs

He jokes that some founders would be better titled “chief happiness officers” than CEOs. The best leaders he knows:

  • Bring in the right people at the right time
  • Understand what kind of person the company needs next
  • Give those people a mission that feels like their own

With Taletree, Matt plans to hire in a way that every role, from CFO to the person preparing food in the office, has a deep connection to the problem. If they do not care about children’s creativity, they do not belong there.

This matches patterns you see in other high‑performing founders too. For example, Lucy Guo’s daily habits for startup success show how a strong mission and strict focus help her decide what to own herself and what to delegate.

Miracles from momentum

Big visions can feel crushing. Matt talks about “breaking down the miracle of the vision into bite‑sized moments.”

He likes to say:

“Miracles come from momentum. Momentum comes from a succession of moments.”

In practice, that means:

  • Set a clear mission and long‑term vision
  • Break it into small, concrete steps
  • Treat each finished step as a win
  • Keep that rhythm day after day

This approach helps in two ways:

  1. The team does not freeze under the weight of the big picture.
  2. You build a culture where steady progress is normal, not rare.

That quiet, daily push is usually what separates a good company from a great one.

If you are looking for more examples of founders who used simple, repeatable systems to grow, the story of Loïc’s repeatable SaaS playbook shows a similar “work on the system, not inside each task” mindset.

My Experience: What I Learned From Matt’s Story

Hearing Matt’s journey shifted how I look at startups in a few concrete ways.

First, I used to focus almost entirely on the idea. Now I pay more attention to timing and distribution. Scatter showed me you can have a brilliant product and still lose if the market is not ready or the channels do not exist yet.

Second, his point about loving the problem hit hard. I have worked on projects where my interest was mostly “this could make money.” Every time things got tough, my motivation collapsed. Comparing that to Matt building Taletree, partly for the child inside himself, makes the difference very clear. When the struggle comes, love for the problem is often the only fuel left.

Third, I like how he links courage to small “throws into the deep end.” It made me rethink how I learn. Instead of waiting until I feel fully prepared, I now try to say yes slightly before I am ready, then trust that I can figure things out on the way down.

Finally, his kindergarten mindset changed how I treat my own ideas. I am less quick to label something as silly. If a five‑year‑old would proudly share that idea, maybe I should at least write it down before I judge it.

Conclusion: Building Your Startup With Childlike Courage And Adult Patience

Matt Hagger’s journey is not a clean “overnight success.” It is 25 years of experiments, wins, and painful failures that shaped a simple, powerful set of principles.

The four keys he keeps coming back to are:

  • Say “yes” when everybody says “no” if your idea solves a real problem
  • Never start a startup without deep love for the problem you are tackling
  • Treat failure as armor, not shame, and keep your kindergarten mindset alive
  • Work on the business, not in the business, so the mission can outgrow you

Underneath all of it sits one belief: your imagination is not a childish toy, it is your main edge as a founder. Taletree is Matt’s way of protecting that in kids. Your job is to protect it in yourself.

If you want more stories like this, where founders share the messy middle, you will find plenty through other profiles on this site, from Lucy Guo’s daily habits for startup success to From idea to $100K MRR: proven SaaS tactics.

The next move is yours. Which of these four keys will you apply to your own startup this week?

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