“An empty table with chairs in a dark basement” by Jonny Clow on Unsplash

I Have Seen The Startups, And I Have Wept.

Daily Blog #66

This is the business of creating a new paradigm, raising it up from a disparate collection of ingredients and pre-existing pieces of technology and outlandish wizardic ideas.

This is the business of rejecting old paradigms, and finding a reason why after the fact.

This is the business of the dotcom crash, that we’d like to pretend was either a cyclical inevitability or a one-off occurrence, depending on what we stand to lose or gain.

This is the business that no government has been able to tame. That lives in such hubris that we debate and discuss whether governments even have a moral imperative to try, or whether we have so far transcended the mundanity of regulatory compliance that we should be pure and untouched by the leprous fingers of the public and their representatives.

There’s artistry to it, in many ways.

The art of the con comes to mind; devising products that don’t have a need, carefully designing the need itself and manufacturing its pain from perhaps a mild source of mass discomfort. There is the art of a Baroque painter, who presents a scene that captures the imagination, and shows movement and desire that is impossible to ignore and improbable to resist.

The founders are equal parts of each, with some sliver of visionary genius too, and perhaps a little arrogant rockstar, and perhaps a little of the poet, the prophet and the two bit huckster.

This is a business that we love, and fear, and hate, and decry and bitterly criticise and sometimes with a wide eyed sense of wonder, praise to high heaven, for its promise that we might reach it.

This is the business of startups.


When I first came into contact with this world, I felt that sense of wonder more than anything else. It was a burning, bright light and I was smitten. Love was looking at the world and knowing that the people I called friends were going to change and transform it. Love was knowing that anything was possible.

I have worked in tech companies, and communicated what they had to say the best that I could. I have sold dreams as commodities and half finished leaky rowboats as mighty liners that would have shamed the Queen Mary. I have sold software that didn’t fucking work (but what if, one day, it did?) and founders who hadn’t worked a day in their life (and heaven forbid, that one day they might!) and I’ve done it to carve out my face on the towering cliffs of the future.

For months at a time, I have chain smoked my way through the long days and the long nights and the quiet, nagging doubt, the question, the fear. What if the bright promise of utopia that is, for now, just a well crafted collection of words on a slide deck, will never transcend PowerPoint and benefit society in the way that I’ve promised and been promised? What if we’re building the wrong future? What if we’re building nothing at all?

I’ve grown to be an embittered and cynical reprobate. I find myself mocking idealism as naivety and feeling optimism to be almost pornographic.


I think the moment it shifted, for me, was on a long-haul flight. I was on my way home from Amsterdam, from a tech conference where every talk but mine had been in my native tongue (that my Grandfather never taught me) and I happened to be seated next to a young founder. He was making a product, he told me and everyone else who would listen, that would put faith on the blockchain. It was a Christian startup, funded by his indie church and a VC arm of a megachurch.

Or perhaps the moment was when I was told that a $20,000,000 investment was small change, by a guy with an AI algorithm who couldn’t have been older than 25, who had grown up in this warped and weird world, and was skewed in a way that was profoundly depressing.

Or it might have happened gradually, with every horror story, from every woman I’ve met in tech, about the men with their hands and their eyes and their exclusion and their superiority complex and their vapid ideas about masculine superiority that they sweatily cling to, in sheer avoidance of their own responsibility as builders of the future to ensure that it doesn’t reflect the sexist vagaries of the past.

But then…

Then it shifts back. Slightly, occasionally, completely, depending on my mood and my surroundings.

Because in all of this, in all that I want to fight and yell and kick and scream and burn with the heat of a thousand suns over, I see good people. People who take on the mantle and the responsibilities of technology, and are guided by a sense of ethics, a sense of right and wrong. I see people to whom a startup represents their best shot of putting a mark on the world — not their mark, individually, but the mark of their people and their pride and their tribe.

I see people who appreciate the moment when a duct taped machine works for the first time, for the moment itself and not what it means to a cap table. I see people who understand the pain of displacement, the crisis of the refugee and the power of technology that could help them communicate and find their way and create their own compass.

Because this world has a better side. A kinder side. A side where the idealism isn’t based on a lack of real world experience, but an abundance of it. The people who represent that side are many, and growing. They know that space is a wonderful thing even without an X after the word itself. And I believe in them.

I know the struggle they’re going to face, the struggle of finding money and paying their rent and fighting the fight against bitterness in the same way that I do. I know that when they reach their goals, and build their companies and finish their software, they’ll see the holes and the flaws and take them to heart, and see the future they’ve built and doubt it all over again, and I know it’s going to hurt. In the best way, in the worst way.

It’s not going to be easy, and my cynicism won’t help them.

I shift back, and the bitterness falls away, and I keep it at bay. This time, this time. I have seen the startups, and I have wept, and sometimes it’s with anger and frustration, and sometimes it’s with joy and inspiration.


I write from a hole in the wall cafe where bleary eyed, laptop slinging caffeine addicts line up to pretend they, like Tim Ferris’ fantasy of a perfect founder, drink only green tea even as they knock down black coffee. They tap on their keyboards, and they talk about astronomical numbers as commonplace, as banalities. $5,000,000 here, $10,000,000 there.

Looking past their valuations and decks and a few dropped hints about their next standup meeting, I can’t help but think about how it feels to plan and to believe and to hope and to want to make the world a better place. I can’t help doubting that there’s anything nefarious in chasing billionaire status along the way.

I remember that there are people whose dreams do not sell blockchain powered swampland, and I remember that these half awake hackathon survivors and iPhone punks could be among them.

I can’t help but see them as dreamers, and think back to these words:

“A dreamer is one who can only find his way by moonlight, and his punishment is that he sees the dawn before the rest of the world. “
— Oscar Wilde