All your startups turn to dust.

All your startups turn to dust.

I asked a question to Reddit’s r/startups recently, wondering how the community overcame the challenge of transience when working on startups, and often software or web-based products in particular. I’ll admit… I don’t have THE ANSWER, but I thought to share here some of the gist of what I was feeling and what others suggested as well.

I’d been suffering some existential angst, inspired by the realization that every few years so much of my work product vanishes. Nothing left of an entire startup — sometimes years of a team’s effort — but old press coverage, broken links, and ghostly left-over Trello boards.


Ghost towns. This Current Sprint board was last used in 2014. It’s like we all just up and vanished.

I‘d almost expect to see vines and ivy, dust and weeds, overgrown upon their presentation, appropriate to the decay and reclamation of time — yet, there’s nothing. If you load the old Google docs and Trello boards, it’s all still there, as if one day it would just start back up, the old band getting back together.

I always held on to these archives dearly, as to me, they represented the history of my effort. All my own growth was bundled up in old whiteboard images, specifications, wireframes and the digital, working capture of our progress in management and workflow. Now though, I wonder if these ghosts, always tugging at your attention from overstuffed Dropbox archives, portfolios and the past, do more harm than good.

I examined briefly if the pain I felt surrounding the transience of work in early stage startups was my own, or if it was inspired, like a seed taking root, by something Alain de Botton said in The Pleasures and Sorrows of Work:

“Our exertions generally find no enduring physical correlatives. We are diluted in gigantic intangible collective projects, which leave us wondering what we did last year and, more profoundly, where we have gone and quite what we have amounted to….

How different everything is for the craftsman who … can step back at the end of a day or lifetime and point to an object — whether a square of canvas, a chair or a clay jug — and see it as a stable repository of his skills and an accurate record of his years, and hence feel collected together in one place, rather than strung out across projects which long ago evaporated into nothing one could hold or see.”

Quite what we have amounted to. I think that’s the line that does all the lasting damage. The chairmaker can see in the years past an improvement in his skills, literally in technique and style — moving from an Adirondack to a ladderback to a Windsor chair and beyond, in his own application of ornamentation and personality. He can see that skill and say, ah — that is me.


Yet… we that build startups are hunting epic, intangible milestones on which to hang our hats. I raised a round. Check it off the list. I sold a business. Check it off the list. I hit $4M yearly revenue. Check it off the list. But does tracking our bucket list of milestones really prove growth? When you look back on a career filled with milestones but you only had to perform each once or twice, how good can you really be? The problem with wearing so many hats, the oft-mentioned requisite in early-stage projects, is that it becomes so easy to only need a passing capability in the requirements of each. A lifetime of just passing.

One might hope then, that when we peek in to our Dropbox archives something of a trajectory can be seen. If we can’t see our growth as clearly as the chairmaker, we should at least be able to see how that project in 2010 paled to the quality of the work we’re making now, in 2018. Is it damning then, when it doesn’t? The challenge is that what we see is only the summary of the resources we had at that given time. I’ll be the first to admit — I released a few weaker, less crafted and less “skilled” projects in 2016, than I did in 2012.


How do we handle when what we build isn’t always better than the last?

The burden of responsibility to make a better product is always on the team, and the product lead most assuredly, but as you move through your career you’ll discern that for one project the actual challenge is an overbearing CEO with a strong SENSE OF DESIGN, and for another an unresponsive offshore team, and yet maybe another is some other small, insignificant thing that seems foolish now, but at the time so heavily affected your product that when you sit it upon a shelf, beside the rest of your career, it looks something like a joke.


A masterpiece, for only so long as it exists.

Perhaps the only reasonable approach to working in early-stage startups is to admit and accept the ephemerality in much the same way mandala-painting monks create a masterpiece only to brush it away. Keep doing the work, and trust that you can examine it and improve, but only so long as you’re still doing it — mandala after mandala, startup after startup.

I imagined the first comment response to this post would surely be:

Well, just stop making shitty startups that fail and you won’t have to worry about this.

And I want to at least congratulate that #firstcommenter for winning the grand prize in the obvious category. Yes, one Slack or one Facebook and suddenly you’re not in this club of those who question the history of their work. Their growth or their legacy. Yet… 99% of us will work on building these products for our entire lives and we won’t be Slack or Facebook. So, sure… I get your point. That doesn’t mean the grand majority of people aren’t out there doing the work, and maybe wondering how they can handle how all this makes them feel? I’d rather talk about that fellow’s question than your criticism.

“And on the pedestal these words appear:

‘My name is Ozymandias, king of kings:

Look on my works, ye Mighty, and despair!’

Nothing beside remains. Round the decay

Of that colossal wreck, boundless and bare

The lone and level sands stretch far away.”


The 3 Types of Startup Founders to Avoid (and One to Not)
June 30, 2017
All your startups turn to dust.
May 1, 2018
The Craftsman, The Constraint
January 21, 2019
The best laid plans of founders and spreadsheets…
May 22, 2018
Building a Home for the Curious Creative
December 9, 2018
10 steps to creating better remote work culture (on Slack)
March 13, 2020
When we stopped being proud of working in tech
May 9, 2018

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