I will never forget standing on a stage at an Enterprise Nation conference, being interviewed by Emma Jones CBE about the success of my business, while backstage, in my own head, I was in the middle of a fundraise I already knew was failing. I said all the right things. I was warm, articulate, confident about where the business was heading. None of it was a lie exactly. But it wasn’t the whole truth either, and that’s the thing nobody tells you about scaling a business: you’re never being dishonest, you just have to project positivity at all times, in every room, on every stage, long after you’ve privately stopped feeling it.
I built that business, Upper Street, with my sister. A design your own shoe brand, one of the earliest of its kind, and we scaled it into a proper venture backed, high growth company. Along the way we raised close to two million pounds, across bank debt, early angels, two VCs and through crowdfunding, which meant hundreds of ordinary people, not just professional investors, had put money into believing in what we were building. For years afterwards I described the whole experience the same way, like being on a high speed train I could not get off. Not thrilling, not even exhausting exactly, just relentless, a weight that got heavier the faster it went.
What I didn’t say for a long time, because it felt too close to admitting failure, was that I had asked for the ticket.
We weren’t reckless from the start, and that matters, because it’s easy to tell this story as if ambition made me stupid from day one. Eighteen months in, after some good press, two well known VC firms came fishing, big Mayfair offices, glass doors, the works, offering two to three million pounds to scale us fast into the US. We seriously considered it. We also said no, because we knew we had more to learn about our customers first and the trajectory wasn’t right yet. That was good judgement, and I want to be honest about that, because the point of this isn’t that founders are reckless by nature. It’s that the judgement gets harder to hold onto the longer you’re in it, not easier.
Eventually we did raise for growth, first from VCs, then through crowdfunding, hundreds of people putting in ten pounds, fifty pounds, a few hundred, because they believed in the story we were telling. That’s a different kind of promise to the one you make an institutional investor. A VC understands risk. A stranger who backed you for fifty pounds because they loved your shoes and your story does not particularly want to hear that the story has changed. Every fresh round of funding didn’t just buy us runway, it bought us a wider audience we now owed an outcome to.
Once the money was in, we thought big, because that’s what you’re conditioned to do as an entrepreneur, and it genuinely matched my ambition at the time. We took on a flagship retail space, grew the team ahead of revenue, invested in a new website and product range and even acquired our US competitors. Every one of those decisions got nodded through in board meetings. What none of us properly asked was the boring, unglamorous question underneath all of it: what happens to this if the bets don’t pay off? Nobody sat across the table from me and made me answer that, because the board I had was built entirely from people who already believed in the plan.
They were genuinely good investors. That’s not a complaint about them, it’s an observation about the structure. A board built from people who backed you because they believed your story is not the same as a board built to challenge that story. An independent, non executive voice, someone with no stake in the story being right, might have asked the question none of us were asking. I didn’t have that. It’s one of the clearest lessons I took out of the whole experience.
In the end, the business didn’t survive a funding gap that opened up in a second crowdfunding round. Our lead investor had reached the limit of what they were allowed to put in, and without a lead, the rest of the campaign never gathered enough momentum. We closed the company and sold our assets to a competitor for a song. That’s not the ending anyone plans for when they’re standing on a stage projecting confidence, and it’s precisely why I think it’s worth telling honestly now, rather than only telling the version with the better ending.
That was over ten years ago now. Most of the decade since has been spent working directly with female founders on fundraising, growth strategy and leadership, watching this exact pattern play out again and again from the outside. It’s only more recently that the board and governance side of it has become the main focus, partly because of exactly what I didn’t have back then, someone structurally independent enough to ask the hard question.
For women, there’s a second lock on that door that most of my male peers never have to think about. Nearly every investor I pitched to for Upper Street was a man, and plenty of the questions I got were some version of “do women really buy that many shoes” or “isn’t this just a nice lifestyle business you can run around your kids.” It’s hard to hold onto your own certainty about your ambition when the room keeps quietly implying you shouldn’t have that much of it in the first place. So you don’t admit doubt when it shows up, because in a room like that, doubt doesn’t read as one founder being honest, it reads as evidence for exactly what they already suspected about women and ambition. You perform even harder instead of easing off, which is the opposite of what doubt actually needs.
I felt that on stage at Enterprise Nation that day, and in dozens of investor meetings before and after it. I’ve watched almost every woman I’ve worked with since make the same calculation, usually without ever saying it out loud, not even to themselves.
You don’t get off a high speed train by jumping, and sometimes, whatever you do, it comes off the rails anyway. What actually would have helped wasn’t wanting less. It was having someone in the room, structurally independent of the story, whose job was to ask the question I couldn’t ask myself, before the bets were placed rather than after. That’s not a smaller kind of ambition. It’s the same commercial judgement you’d apply to anything else you were responsible for steering, and it’s the piece almost nobody builds in early enough.