I think the challenges of Zulip were more product challenges than GTM challenges, per se—in particular:
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I think we could have benefited from a strong visual designer as a cofounder—the product never really popped from a UI perspective, which I think hindered its adoption
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Our model was really different than what people were expecting. Now, it happens to be really different in a way that’s actually much more productive—but it requires you to use the system for ~two weeks to get the hang of it, to see that that’s true.
My feeling for any new thing is that you either need to:
- Meet your users where they are (so it’s obvious on day 1 how to use the product, and it already fits into your established workflows, etc.), OR
- Ask the user to do something new, but demonstrate to them in the first 30 seconds why this new way of doing things is going to be much better for them than the old way of doing things.
At Zulip, we asked you to do something in a new, different way, but the payoff was fairly delayed, which was challenging.