Failure

Fear of failure is so much worse than the failure itself.

Jul 15, 2025

TL;DR

I overindexed on fear of failure as a first-time founder and with hindsight this was a huge contributor to the businesses’ failure.

“Why did Wine List fail?”

It’s been a while since someone asked me this but it came up the other day in conversation.

There’s no singular reason why my old startup Wine List failed.

In the months after I closed that business, I penned a blog post called Seven lessons learned failing my first startup, which was my own retrospective on what happened.

Hindsight is a wonderful thing.

It’s been over 3.5-years since I wrote that post.

For the first two years after that post, I coached, advised, and consulted, and saw ‘inside’ about 75 businesses to some degree.

Then for the last 2.5 years I’ve been running Ballpoint, where I’ve seen inside about 120 businesses in some way or other.

After 200 businesses, you can start to pattern match.

And with that pattern match it makes me return to my own failure with Wine List.

First let’s revisit the high-level list I did at the time.

My 7 reasons for failure listed at the time

I made too many excuses for PMF
I was terrified of turning off marketing
I acted like we had future state LTV
I fell in love with my first startup idea
I fell in love with the solution – not the problem
I lost my risk tolerance when it was suddenly my money
I lied to myself about what was needed to launch a new product

Now, some of these I still agree with. We didn’t have product market fit and I do remember making excuses for it. I was terrified of turning off marketing because I knew how high our churn was. And I definitely struggled to pivot as much maybe we should have.

But actually a lot of the other stuff isn’t how I remember the journey.

In fact there’s two things missing from that list that I left out at the time.

External factors

I once heard someone say in a meeting “if you’re going to come to the meeting with external factors as an excuse again, don’t both coming to the meeting.” Could it have been framed better? Yes, but did it stick with me? Absolutely.

For most of my career after, I avoided ever using external factors as a reason for anything.

But one thing I’ve realised since running an agency and having permanent access to 20 businesses, is that there externalities are everywhere. There are so many uncontrollable things out there. Some can be pre-empted, but lots can’t. And actually by denying that they exist, means you may be chasing ghosts.

Here was our big external factor:

Brexit meant that wine shipments were totally screwed
We were at one stage about 6 months away from break-even
But then Brexit delayed shipments every. single. month.
Every subsequent month, we brought the order forward to allow for the delays. Each delay outpaced us.
The first time, customers didn’t care. But soon they did.
We saw a gradual build of churn but a groundswell of resentment
And then one month it was particularly bad. A delivery was supposed to arrive for May 15th, so we could ship it to customers May 30th. It didn’t arrive until June 27th.
What that means is, we couldn’t ship the May delivery. We lost lots of customers.
We also relied on about 50% of revenue each month coming from additional customer purchases of their favourite wines – we didn’t get that because the initial delivery didn’t happen.
We had so much churn that month, and those that didn’t then ended up skipping lots of their June boxes, which we’d already bought and so were holding the stock. June delivery ended up being late too.
We went from being 6 months away from break-even to about 6 weeks of runway left due to the cost of the churn, the delays, the lack of revenue, and the refunds.
I don’t have the P&L timedated properly, but my memory was we burn went from about £40k to over £100k in one month owing to lost revenue, and churn. And by that point the writing was on the wall.

Don’t get me wrong, we still didn’t have PMF. Churn was still high. Acquisition costs were high. Retention was too low and worsening. But those external factors rapidly accelerated our death even if they didn’t cause it.

The mistake I made with hindsight was not realising how powerful that external factor had been. I wanted to own the mistakes so much that I didn’t ever talk that much about those factors. And instead listed all the stuff we did wrong instead.

So why didn’t I do anything about it before? Why didn’t we plan better? Why didn’t we think of alternatives.

This brings me back to what I’ve realised is one of the pattern matched things I see in first time founders again and again and again.

Fear of failure is a huge contributor to startup death

I didn’t know it at the time, but I was terrified of failing.

I grew up with no money, and I’ve never had a safety net to fall back on.

Until my 30s, I lived paycheck to paycheck and had no savings. This is a major motivator for me at a macro level – and for the most part has guided good decision-making in my life. But at that time, it also hampered it.

I was afraid of what I’d be able to do afterwards. Would I even be able to get a job? Who would employ me if I had such a failed startup hanging over me? Who would ever invest in me again? How would I pay my mortgage if this ended?

Some of it was definitely the identity thing. I’d gone on this big journey of telling everyone I was going to be a founder. Friends, colleagues, family. Family who didn’t really understand it but knew it was risky, they were proud. I’d gone through all of it with them. I liked the sound of it. I identified with being a wine founder. I liked that label.

I had hired this team of people who I thought were great and I did not want to let them down. I’m very fortunate now that one of that team is my number two at Ballpoint, our head of ops and creative studio lead Fiona, (huge shout out to you). Because of this, this group of people became some of the strongest people around me.

And then there’s obviously some of that imposter syndrome that sneaks in. Was there part of me that deep down maybe felt like I was playing entrepreneur? I’d managed to get all these customers to believe in it, and the investors, and the suppliers, and the team. Somewhere there was that imposter syndrome terror that I wasn’t good enough for it and actually failure was hanging around somewhere.

So fear of failure hung in the background throughout.

And how did that manifest?

I didn’t ask for enough advice or help – with hindsight, finances and operations both needed more support than I realised. Finances in particular, I should have been a lot more on top of than I was.
I didn’t pivot enough if it meant disrupting my status quo. That signalled failure. And so we didn’t rip up the core business model. I didn’t make most of the team redundant and start over. Instead, I grounded everything in ‘this isn’t working yet but here’s what we’re doing to fix it.’ Rather than ‘maybe we need a total 360.’
I ignored the writing on the wall. The churn figures don’t lie, the acquisition costs don’t lie. This plays into the ‘fear of turning off marketing’.
I lost confidence in myself. I’m pretty good at Facebook ads. I have the deep confidence to say that now because I run an agency that manages £15m of spend a year. But I also was pretty confident about it before Wine List too: I’d grown Thriva from 0 to 100k customers all with Facebook Ads. And yet, I started telling myself that maybe I just wasn’t doing them well enough.

And in fact of the list of 7 lessons, the ones which I still believe in hold true because of the stemming from this fear of failure.

I see this in other founders all the time

Last year, we worked with two brands who did not have product market fit. We spoke about this a lot, and the response in both instances was similar to how I’d have responded at the time. Head in the sand.

Interestingly after I wrote the initial post in 2021, I had dozens of founders reach out and share that they were experiencing the same problem. Last time I did a headcount, most of those businesses have gone under too.

And what is it that drives the head in the sand? In most of those examples I saw – and I’m making external assumptions here – but my guess is its fear of failure.

“You’ve failed a company and it doesn’t matter”

So what happened.

In my next business now, I don’t fear failure in the same way. I fear churn, yes. I fear not providing a good enough service. But I fear those things in a way which feels relative to running any business. A friend once said “never lose that, it’s a competitive advantage to think like that.” Maybe.

But it’s distinctly different mentally for me.

And the reason comes back to: I’ve now failed once and in the words of one of my investors, I’ve realised: “it doesn’t fucking matter.”

No-one else is feeling this thing as intently as you are. People are willing you to succeed. And if you don’t, they don’t laugh or judge, they feel empathy. Yeah, some investors might be annoyed that they lost their money, but any decent investor treats investments as what they are: a high risk, low probability model where a single investment is by design going to return the high majority of flops.

I actually think unhampered with the fear of failure, there’s a good chance I’d have called Wine List quits far earlier. If it were my second business, it wouldn’t have got that far.

Failing once freed me. It matured me. It helped me grow more than I would have done without that failure.

Life goes on. People forgive and forget.

You’ll find another job. In fact, if there’s been one thing I’d recommend to make you indefinitely hireable: it’s have a failed startup. I’ve not actually wanted a job since I finished Wine List but I’ve had no shortage of offers, something I was never sought out for before being a failed founder.

So if you’re in this position, let that fear go. Know that it doesn’t matter. Now re-evaluate your business. Maybe you don’t have PMF because you’ve not yet found the answer, but maybe you don’t have it because the product doesn’t solve a problem. Maybe it just doesn’t work, and that’s okay.

There’s no glory in hanging on.

You also realise that life is both short and long.

I spoke to a founder recently who was struggling with PMF. And part of me wanted to already impart that advice I was given “you’ve done it now, you’ve failed a startup and you realise it doesn’t matter” but I think maybe it’s too early.

This might just have to be one of those great lessons that you need to learn yourself. Or maybe you benefit from the fact that you don’t fear failure by default.

I’ll leave you with one of my favourite quotes that has gotten me through so much in my life:

“Nothing is either as good or as bad as it feels at the time.”

Early Stage Growth • Ballpoint

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