Narrative Crisis

I’m in Europe and it might have cooked my brain a bit because I’m back to that ever present thought: should I kill this nearly 5 year old startup of mine and move on? Does it Matter?

The story of how it got to this point is for another day, but let’s just say I have paying customers, low churn, low growth, low burn, and I’m having a lot of fun figuring out how to build and launch major features completely solo with the help of AI. The only problem is, it’s lonely and I’m not sure I’m making something people want. But the thing I know from being founder/CEO of a 70-person startup, and working for two founder/CEOs of companies that later went public is that the job is always lonely. The making something people want thing is harder because I’m making something I know I want, but I’m starting to wonder if I’m just too… weird(?) to be the model of the user.

I really enjoyed being more delusional about past startups and I wish I could go back to that sweet innocence and obsession. To the time before I could see the seams of how we repackage and sell back to people things they should really be able to do themselves better and cheaper, and now LLMs are laying so much of that bare. Before it was diligence with spreadsheets and emails (Mattermark) and today it’s diligence with Claude Code and texts (Groupthink) and I can’t help but think there must be more than this post-modern life.

But seriously, I bought the domain groupthink.com from an old friend and found it funny at the time, but then the meaning crisis caught up to me to too and I’ve been wandering in The Dark Forest til The Nothing swallowed it and then the narrative crisis silenced everyone. Or so they say. I have never been a fan of them.

And so here I am on a balcony in Rome thinking about the stories we tell to unify the world, to create a we at all, in an attempt to rein in the chaos of nature and the violence of survival and elevate it all into status games and other meaning-making tactics like religion and the state. I’m thinking about the last time I felt a strong sense of we-ness, probably when I was living in the Bay Area and felt like I was unearthing stories that should be told about startups. I had barely gotten started and on top of the data-driven narratives I wanted to write (and did) I had a whole SaaS startup to run and the writing felt like a guilt pleasure, a side quest I justified as a “content strategy”.

I can’t put my finger on what bothers me about the way the startup story is getting told now. For one, it seems (at least in my algorithmic bubble) that investors and their content machines have taken over the storytelling, and the majority of journalism is written from a place of skepticism and identity politics. It just fine that boring, like when someone says stuff you already have thought about. Rarely do I read something that surprised me or pisses me off, rarely am I asked to think hard. Then there is all the pseudo intellectual posturing, mostly on Substack but also by some people who think they’re edgy and post-rat or whatever, usually written in the intentional illegible style of critical theory to “make you think harder”. If you’re gonna struggle like that I prefer to work through truly rewarding challengers like Lacan and Ruti, or even developer first-hand thoughts on Girard.

Moral fashion and posturing becoming so much more of A Thing in tech in the last decade does fascinate me, and my theory is this is meant to apologize for AI. I’m not sure who is writing the meta take on all this, but it needs to be written and documented because it’s going to influence what happens next. It’s going to influence policy, capital, who gets funded, what gets founded, and so much more.

Each startup is a theory about how the world should be, not just a prediction of how it could be. That should requires narrative, it requires us to band together (as users) to create the we-ness that propels one narrative forward over the other. I hear so little about the customer as an individual right now, I don’t know if I’ve lived in a less customer-of-one-centric moment in tech than this one. It seems like the customers are institutions and organizations (the government, the investors, the press) but partly I think this is shaped by the kind of gaze that gets pointed at startups. It’s not enough to solve a problem for a few hundred or thousand rabid fans and then expand from there, now we need bigger stories from day one. To save the world with genes or memes.

So what about my startup?

I feel paralyzed by its smallness and my awareness of that delicacy. I feel conviction that better tools for human connection and higher inter-personal conscientiousness at work are needed, but also worry when my college sophomore nephew tells me that he thinks most of his classmates would prefer not to talk to each other at all and that only he and one other student in his biology lab make any effort to get their lab groups to make small talk. Am I building for millennials when our generation and my perspective is stale?

Being in a big international city where I don’t speak the language gives me the chance to watch people. I always do, but something is different about observing them without knowing what they say or even what the tone of voice means. I’m very driven by hospitality in everything I make and staying in a hotel is always a great way to reconnect with that. Hospitality doesn’t stay the same, it has fashions too and I don’t mean decor or food, I mean behavioral fashions.

And then some of this is rich people stuff, which is helpful if you can figure out how to democratize that. But what I think rich people have now that everyone else wants is time freedom and a sense of knowing what/how to choose among a deluge of alternatives (this complex idea we are calling “taste” in the zeitgeist).

Maybe I’m a rich millennial and that’s the most out of touch person to be making things for people? I tell people what I do and they’re nice, even crack jokes about how they hate meetings without a plan in a show of relatability. But it’s said with such an air of acceptance. This is just the way work is, and while I know individuals who are seeing huge gains from having full transcripts, summaries, automatic action items, and deep profiles on projects and clients it is massively gate-kept and hand rolled. They’re not looking for software because they rolled their own, and they did it in the time freedom they already had so they’re getting massive compounding going on that loop.

And this is where I think I get disheartened because I’m starting to think people don’t really want the free time back. Or they won’t actually get to keep it, because we have this 40-hours (and a mule, yes I am referring to slavery) work culture and employers seem to believe any efficiency gains employees create should get banked for free. So incentives work, and this leaves us with something worse than a meaning crisis or a narrative crisis. It’s an ambition crisis.

Say I gave you a tool that let you take your 40-50 hour work week and deliver on your goals in half that time or better. You’d have a really hard time reclaiming those 20-30 hours because you’d still need to make it look like you were present to answer questions nearly 24/7 on Slack, email, or wherever your team coordinates. You’d still have a random sprinkling of meetings, which would not have agendas and would not cease to happen just because your deliverables were done. In fact, you’d probably trickle them out close to the deadlines and indulge in some extra re-editing beyond the requirements to allay your sense of guilt for using AI to write a portion of it, even if it’s perfectly good and serviceable work.

So efficiency doesn’t have great incentives for the worker unless they’re in the remote work situation which makes it easy to perform productivity theater with less oversight. So maybe they could be more ambitious, except for the part where they are working at home and are more likely to be sucked into childcare, home maintenance, and other things a more flexible schedule at home makes possible (like being the primary caregiver of an aging parent, or doing a side-hustle job converting a hobby into a paying gig).

Now there is nothing wrong with any of this, to be clear I am just grappling with who my customer is here. Who is the knowledge worker and how have they changed? “Knowledge worker” is further monolithic than it ever has been. How do they segment down into smaller niches? What do they want? What are their incentives? What do they want to want, versus want because they were told to?

Something tells me not much has changed.

Perfection

Wisdom

Grace

Righteousness

Transformation

Shipped some improvements to the startup (from my phone, using AI remote controlling my laptop back in Colorado, this is still magical!) so it lives another day.