Fail Early, Fail Often - Startups and the Fear of Failing

written by: Richard Kastelein

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It is an uncomfortable fact of business life that four out of five start-ups end in failure. It's even more complicated when you have three daughters, a wife, and are a stranger in a strange land – an expatriate.

But I wouldn’t have it any other way.

Some weeks I feel like a simian – flying from tree to tree – looking for the next branch to grab and never quite sure if there’s one there when I am up in the air. Some might think that’s stressful. It can be. Some may think it’s unsteady. It is. Others may think it’s just plain nuts.

But I wouldn’t have it any other way.

There’s nothing more exciting and gratifying then making it happen, dreaming up and building cool things that will affect people’s lives in a positive way. Of sharing knowledge with others to drive innovation – and open-sourcing intelligence because it’s better for the birth and early days of an emerging industry.

18 months ago, I started to write about newborn subjects like Social TV, Multiplatform Engagement, Transmedia, TV Apps and Connected TV. It was nowhere near the zeitgeist and was a play – a pure poker play if you like. I purposely decided to publish everything for free – no pay walls, no advertising, no reports. My publishing friends thought I was nuts.

I threw in my sweat equity with the idea that by building thought leadership – I could build a business organically, based on the idea that untapped knowledge has value and that value can be converted to building a company. And not just a consulting company – but one that creates intellectual property, by connecting the dots and by digging deep into the creative half to come up with innovative ideas and projects.

As someone who sailed around the world before I was 30, travelling to more countries than I can remember – who took chances as a young vagabond that make the risks I take now look tame in comparison, entering the startup world in my mid-thirties and starting a family at the same time seemed to fit naturally.

In this world, “Fail Early, Fail Often” is a motto – born from Silicon Valley where the heartbeat of technology drives thousands to the West Coast of the USA – like starlets to Hollywood. “Fail Fast” was another cliché that drifted around Venture Capital (VC) circles for some years.

Of course we entrepreneurs fear failure and that’s unavoidable. The challenge is manage the fear so that it doesn’t have the effect of making big failures more likely.

Or perhaps the real challenge is not worrying about future failure, but holding on to that drive forward – after knowing when to move on to something else. Or holding on to that drive despite months of couch surfing with old friends in a foreign city, hunting down the nearest Starbucks for the next meeting with a potential partner… Keeping one’s wife and kids in another country because it just makes sense.

What always seems to be around the corner – the birth of a new industry and landscape – seeded from the desire to be on the cutting edge – rather than taking up space in the middle. It’s now coming to life. And the fear of failure is a fear that is dissipating.

And I wouldn’t have it any other way.


About the Author

Richard Kastelein
Founder of The Hackfest, publisher of TV App Market and global expert on Media & TV innovation, Kastelein is an award winning publisher and futurist. He has guest lectured at MIT Media Lab, University of Cologne, sat on media convergence panel at 2nd EU Digital Assembly in Brussels, and worked with broadcasters such as the BBC, NPO, RTL (DE and NL), Eurosport, NBCU, C4, ITV, Seven Network and others on media convergence strategy - Social TV, OTT, DLNA and 2nd Screen etc.

He is a Fellow of the UK Royal Society of Arts (RSA) and UK Royal Television Society (RTS) member.

Kastelein has spoken (& speaking) on the future of media & TV in Amsterdam, Belfast, Berlin, Brussels, Brighton, Copenhagen, Cannes, Cologne, Curacao, Frankfurt, Hollywood, Hilversum, Geneva, Groningen (TEDx), Kuala Lumpur, London, Las Vegas, Leipzig, Madrid, Melbourne, NYC, Rio, Sheffield, San Francisco, San Jose, Sydney, Tallinn, Vienna, Zurich...

He's been on advisory boards of TEDx Istanbul, SMWF UK, Apps World, and judged & AIB awards, Social TV Awards Hollywood, TV Connect & IPTV Awards.

A versatilist & autodidact, his leadership ability, divergent and synthetic thinking skills evolved from sailing the world 24000 miles+ offshore in his 20′s on sailboats under 12m.

He spent 10 years in the Caribbean media & boating industry as a professional sailor before returning to Europe, to Holland.

A Creative Technologist and Canadian (Dutch/Irish/English/Metis) his career began in the Canadian Native Press and is now a columnist for The Association for International Broadcasting and writes for Wired, The Guardian & Virgin. His writings have been translated into Polish, German and French. 

One of Kastelein's TV formats was optioned by Sony Pictures Television in 2012. 

Currently involved in a number of startups including publishing TV App Market online, The Hackfest and Tripsearch TV. As CSO for Worldticketshop he helped build a $100m company.

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