November 19, 2021

Why isn't it okay for startup founders to admit when they're failing?

Entrepreneur and investor Helena Murphy talks about the mental and physical toll of her startup's failure and why she felt so afraid to talk about it.

Helena Murphy

4 min read

Raising Partners

£100,000 worth of personal debt, stress-triggered hair loss and alarming weight changes. This is the ugly side of entrepreneurship that founders don’t talk about.

Where had I, a once successful and admired founder, gone wrong? 

It had all started so well. When I graduated from university, I turned my flourishing side hustle into a full-time business, launching my own sustainable fashion ecommerce site. 

My business enjoyed a lot of early success: strong sales, flattering press and even my very own team in our very own office. I was buoyed by flattery and praise — my friends and family were in awe of what I was achieving — and my inbox was bursting with invitations to events, awards and fashion shows.


At one of these events, someone offered to invest — my first experience of raising capital. It was the serendipitous blend of a seating plan, a conversation over dinner and a handshake. The next week I had a cheque in my hands. It all seemed so easy. 

I was arrogantly convinced that my entrepreneurial flair, which until now had been so lauded, would be enough

I began burning through cash at an exorbitant rate, transfixed by vanity metrics — top-line revenue and positive press — rather than the fundamental barometers by which to measure my company. 

I was delusional and strategy-less, operating as a cash-in, cash-out business at a scale that was entirely unsustainable. I wasn’t leveraging the most basic of business tools or resources and instead was arrogantly convinced that my entrepreneurial flair, which until now had been so lauded, would be enough. 

It was when I needed more investment — this time to the tune of £1 million within six weeks — that I realised I was in trouble. My angel investor, previously so casual and calm, looked at my numbers and swiftly declined my request, explaining that I’d taken my eye off the ball. 

My head was wrenched from the sand, and I was left with two options. Either to attempt the impossible and raise the necessary funds or to cut my losses and bow out gracefully, taking on £100,000 worth of personal debt to pay off my suppliers, bills, staff and investors. At the ripe old age of 23, I chose the latter.

Failure is inevitable, staying silent doesn’t have to be 

What followed next was a very dark period of my life in which I was grossly unwell, both mentally and physically. My sense of self was demolished and my shame was all-consuming, but I knew that while I grieved for my folded business, I also needed to analyse what exactly had gone wrong. For five long, agonising months, I dissected my mistakes. I consulted accountants, lawyers, advisers and investors for an honest account of what I should have done differently, and I resolved to never make the same mistakes again. 

While I did actually learn some very important lessons about business during that time, I realise that I perhaps missed the most important lesson until recently. 

That it’s more damaging to stay silent about failure than to speak about it.

Risking failure is at the heart of what it means to be an entrepreneur. Yet too often we are only fed the highlight reels

To this day, I have friends and family who don’t know the extent of what happened, and some of them might be reading this now. I hid my failure — just as I covered my alopecia bald patches — because I was overwhelmed with shame. 

Risking failure is at the heart of what it means to be an entrepreneur. Yet too often we are only fed the highlight reels, celebrating company growth and market domination, distracting us from the unavoidable truth: things do go wrong. For every Sifted article on a company’s investment round, there will have been countless mistakes, sleepless nights and headaches behind the scenes. This isn’t meant to be, and should never be, easy. 

Failure is inevitable, but staying silent doesn’t have to be. 

Don’t be an arrogant founder 

Everyone believes that their first startup will conquer the world. It’s this ambition that keeps entrepreneurs going. But arrogance breeds complacency, making it one of the worst traits a founder can have. What’s key for success is being arrogant enough to start, but humble enough to survive. 


If you’re not careful, the same confidence that sees you burst out of the starting blocks can prevent you from listening, learning and adapting later down the line. It shouldn’t take a disaster (and mine was a complete, unmitigated disaster) to appreciate the power of humility. If I had acknowledged my weaknesses, confronted my knowledge gaps and sought help when needed, my business might have survived. Sometimes you just have to accept that you aren’t always going to know most of the answers, let alone all of them.

If we want to normalise failure, this polished founder image must change. If we’re honest about our mishaps as they happen in real-time, we can reframe them as an inevitable part of the journey, rather than a ruinous dead end.