The eternally pessimistic playwright Samuel Beckett isn’t the kind of person you’d expect to be a cheerleader for the start-up sector (not least because he died in 1989). However, one line of his late work, Worstword Ho - “Try again. Fail again. Fail better.” - mirrors a current mantra driving entrepreneurial thinking.  

The buzz-phrase “Fail Fast, Fail Often” has been heard so regularly in pitches and board meetings it’s almost become a start-up cliché. Yet, at its heart is an attempt to reposition success in a world where technology means you can start up (and wind up) enterprises incredibly quickly.   

It’s a concept infused with Silicon Valley-style sunniness. Removing the stigma around failure frees people to learn from their mistakes and try again with something different. By failing fast (the idea goes), you let bad ideas rapidly die and provide the market space to allow good ones to flourish.   

This philosophy also offers solace to the serial entrepreneur: your last five businesses may have crashed and burned, but that’s nothing to be down about: success may be just around the corner.  

This evolving attitude to failure is reflected in events like F*ckUp Nights, a global movement that spans 150 cities in 50 countries. It’s like a classic boosterish entrepreneur gathering, as seen through the looking glass. Where at most start-up events people come to boast about what went right (and give their recipe for success) – here they discuss how things went very, very wrong.  

“During the night, we have four to five entrepreneurs talking about their failures,” says Alessandro Palmieri, who runs the London event [].   

“These failures are often big. We’ve heard from people who have had to close down a company worth £2.5m and been made homeless, or have gone through £6m of funding in six weeks. You hear about the personal side of failure too and how it affects people’s personal lives and their families.“  

Each event follows a strict format where the guest entrepreneurs answer a set of four questions covering what went wrong and what they’d do differently next time.   

Part of the appeal is hearing people admit failures in a culture that only tends to value success. And Palmieri adds that learning why other people have failed can give the audience a better idea of what will work with their own enterprises.  

“There are lots of events where people talk about success, but very few that are about failure,” he says.   

“If you learn what the reasons for failure are, you’re more likely to succeed. There are entrepreneurs in the audience who want to hear other entrepreneurs talk about this – and those who may need a bit more courage before starting their own enterprise and want to hear other people’s experiences.”  

He says that, although each story is different, there have been recurring themes throughout the presentations. The main reasons for failure are around choosing the wrong team, getting the timing wrong for your launch and not having enough skills, he explains.  

“We see lots of people with amazing skills, but they’re not the right ones you need to run a successful company. Or people want to start an enterprise because they’re creative but then don’t want to do the business side.”  

So is the way we view failure slowly starting to change? Forums like F*ckUp Nights are helping find new ways to discuss what was once a taboo subject out in the open.  

In America, birthplace of Silicon Valley, the naturally upbeat culture tends to make it easy for people to be bullish about business failures (just ask Donald Trump). Meanwhile, in the UK, we have a strong tradition of self-deprecation that perhaps lacks the self-aware edge that allows us to analyse exactly what went wrong.   

“I think people are becoming a bit more open to talk about failure,” adds Palmieri.  

“For the last night, we left a moment for the audience to share failures of their own, like an open-mike session. At first we thought no one was going to want to come forward, but then we had to stop because we had too many people and we were running out of time. So I think that if you have a safe space to share failure, people will definitely talk about it.”