Startup Postmortem

“My first company was destined to fail,” entrepreneur James Routledge told a captive audience at a recent Startup Postmortem event.

Hosted by Runway East and chaired by Cathy White, founder of CEW Communications and GeekGirl, the event saw four startup founders and former-CEOs take to the stage to bear all and divulge the nitty gritty on why their respective ventures ultimately crashed and burned.

Routledge shared his story of co-founding MatchChat – a social network for sports fans, which pivoted into an AdTech product and subsequently failed.

“I started MatchChat for the wrong reasons – I was at university, I watched The Social Network, read TechCrunch and I just thought ‘let’s build an app, raise a few million, sell it and we’ll all be happy, become angel investors and write a Medium blog post’. If you’ve heard the word ‘wantrepreneur’, that was me,” he explained.

“Basically the business had no vision. We wanted to do a football app because we liked football, not because we wanted to solve any sort of problem.”

The 26-year-old said the company managed to raise £600,000, but due to the founders’ lack of experience, they were easily persuaded to make changes to the direction of the business.

“We were 21 at the time, so any time an investor or some guy with white hair who we thought was really smart said: ‘Why don’t you try this?’ We were like: ‘Ok sir, let’s do that.’ So we just pivoted and pivoted and pivoted until we basically ended up with an AdTech product. It was serving 50 million mobile ads per month, but I hated advertising.”

Routledge had a business mentor who said he could see MatchChat was struggling. “He could see we were slowly dying,” said Routledge. The mentor advised him to take his team away for a few days for a change of scenery and to ask each other some really fundamental questions.

“I finally took his advice and we went to Brighton, booked an Airbnb, just got out of the office and took some time for ourselves and, for the first time, asked the big questions, like: ‘Are we enjoying this? Do we want to work on this for the next five years?’ The answer was ‘no’ and two weeks later we decided to shut it down,” he explained.

World of bother

Routledge said that when he closed MatchChat he was in a “world of bother” and developed a deep loathing of the whole startup ecosystem.

“I hated startups, I hated TechCrunch, I hated pitch decks and VCs. Just everything about the ecosystem was making me angry. I blamed other people a lot. I blamed the market, I blamed investors, I just blamed everything and was really really bitter,” he explained.

It took some time, but the founder eventually took responsibility for the failure of his startup – he recognised it was his fault MatchChat took money and advice from the wrong people.

“Then I grieved. The only thing I can liken shutting down a company to is a mixture of a divorce and a death. It is difficult, it’s a big part of your life that you have to mourn,” he said.

“The startup was my entire life. It consumed everything. If you looked at my life as a pie chart, it was 95% startup. Then you take that 95% out and you basically have a gaping hole in your chest and you’re left thinking: ‘Who am I now? What do I do with my life?’.

“That’s where I was, I was in a really bad place. My mental health was really affected. I had no money, I’d burnt myself into the ground and was left thinking ‘why?’”


It was going through this that helped Routledge find something he is really passionate about: mental health. In April last year, he founded Sanctus – a startup aiming to change the perception of mental health, increasing open conversation around this area and advising businesses on how to create environment where mental health problems are accepted.

Routledge said that, before founding MatchChat, he wished he had asked himself: “Do I really want to do this for the rest of my life?” If he had have asked this, the answer would have been “no”.

“The business I have started now, I genuinely would like to think I could work on it for the rest of my life. And that’s really important to me because it’s f****** hard, it’s not fun a lot of the time. You work long hours, you’re not going to get paid well – as jobs go, it’s s***, so it needs to be something you’re passionate about,” he said.

Routledge rounded off by reiterating his key pieces of advice for startup founders and wannabe entrepreneurs. Firstly: Don’t focus solely on building towards exit, concentrate on creating something you’re passionate about. Secondly: Don’t be afraid to admit defeat. If you’re burning yourself into the ground, stop and ask yourself: “Is it worth it?”. We all have bad days, but if day after day, week after week, you ask yourself this question and the answer is “no”, it is time to stop – your mental health is more important than the need to keep a failing business alive.

Image via Twitter