The Hill Climbing Trap
Startups, local maxima and navigating our path to success
I’m feeling pretty good about active user growth for the SpecStory Cursor Extension.
But as Andy Grove warns, only the paranoid survive. I’m paranoid about whether we’re climbing the right hill.
Are we doing this?
Only to find out we’re really here?
We talk about it as a team frequently.
We know there’s much more to solve beyond helping individuals save and share their Cursor composer histories. That’s not the question.
The critical questions surround whether our Cursor extension will lead us to the tallest peak or not. Will we fall victim to the inertia of initial success? Will we be able to achieve our vision?
Our vision stated simply: SpecStory helps entrepreneurial teams use all their tools and talents to build valuable software faster, together.
The team knows hill climbing1 only to reach a local maxima is a death knell for any VC backed startup.
If you’ve ever hiked, you know this approach will leave you higher than you started, but it runs the risk of stranding you on a false peak. This matters for SpecStory and other startups like us because we have limited runway to find product-market fit for a high value customer pain point.
Unlike the casual hiker who can backtrack to find their way to the summit, we’re on a much higher stakes climb with limited oxygen and provisions— getting as high as we can with our scant resources will determine our ultimate success.
Now back to our vision: SpecStory helps entrepreneurial teams use all their tools and talents to build valuable software faster, together.
That last word says it all.
In our case, the deadly local maxima would be to become the best toolkit in the world for individual software composers.
And so we remind ourselves that helping them is just one step along the way toward helping teams. Those emerging teams — like us — that use AI code generation tools (Cursor, Windsurf, Copilot, etc), together, every day across a mix of newly forming roles.
To that end, we’re working to build more and more great features into SpecStory that teams can use together to accelerate the benefits of AI coding when used in more complex real-world projects and workflows.
Keep an eye out for the first of these: a /cursor/rules generator that will both individuals and teams keep their AI assistants aligned with their intentions and decisions.
Newsletter subscribers will get a unique code to gain early access to the beta version of this feature. Happy climbing!
Refresher: Hill climbing is an algorithmic approach to find an optimal solution to a problem by (1) picking a starting point, (2) looking nearby for a higher (more optimal) point, (3) continuing until no nearby point is higher.