One of the key points of Hypothesis Driven Development is that the set of questions for your startup will be unique to both the idea, and your skills and experiences. Web startups will necessarily generate a different set of questions than enterprise startups.
In this article, Ash Maurya declares that for web startups, the greatest difficulty is not developing a handful of customers, but creating scalable channels through which to reach potential customers. Rightly, he suggests that:
My experience (with web based products) has been that it's not as much the uncovering of the path but the building of the path that is troublesome. Some paths are obvious but hard, such as those built on referrals (word of mouth), SEO, etc. It's comparatively a lot easier to find 30-50 people, validate you have a problem worth solving, build a MVP, even get them to pay you - all of which is a false positive if it was predicated on a customer acquisition approach that won't scale or more importantly be applicable to how you acquire customers in the future.
Ash provides some practical advice for how to achieve this. Worth a read. Another related approach discussed here before is, of course, to build your startup around available distribution channels, with variations also discussed here on HN.
Ash is also working on a book which attempts to bring together customer development and lean startups in a web context.
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