Why Trello Failed

This is probably one of my favorite ever articles, and it's probably the article that I read and thought, you know what, I'm beginning to understand this thought leadership stuff, just a little bit. And it's why Trello failed to build a billion-dollar plus business, as by Hiten Shah. And probably the most important thing to take away from this, the really big overarching thing that this does well, is the framing. Because the topic that we're covering here is something that is actually fairly generic, fairly overdone in some cases.

The conventional formulation of this, the thing you might see other people write about on this topic, would be something like "Trello's growth strategy" or "How Trello grew to $425 million" or "How Trello got acquired." And that's interesting, and there is lots of good stuff you could learn from that article, but it's also quite generic and quite samey. And what Hiten does is he turns that narrative completely on its head.

Because Trello is generally regarded, rightfully so, as a successful company. They grew to a big size, lots of people use them, it's become a bit of a household name. But he's actually making a very compelling argument for the fact that it is a relative failure because the potential of Trello was so much bigger than where they ended up. So, this is the kind of classic counter-narrative opinion Hiten is taking, a truism, something we all believe to be true, and he's turning it on his head and making a convincing argument for why it's not the case. The narrative is actually the opposite of what we thought.

So, why Trello failed to build a billion-dollar business capitalizes on schadenfreude. We all enjoy a quiet look at the failures of other people, and it's just a much more interesting articulation of this idea. And one of the risks of writing this type of content, even if you are Hiten Shah, somebody who is innately very credible because he is a multiple-time successful software founder, is the risk of being an armchair critic. We were not at Trello, we were not privy to the decisions they had to make to end up in the situation they were, and if you've been involved in any type of business, you know how opaque and complicated and confusing and difficult it can be to make decisions.

So, the risk of this type of content is you come off looking like a jerk, and you are not very credible because you're commenting on things that you just have no exposure to. The way Hiten gets around that, I think, is just the intense level of detail and research that has gone into this. The entire blog post is just absolutely rife with concrete data and facts and statistics and quotes from people that were involved. And that builds confidence in Hiten's ideas. But importantly, the data is in service of an overarching narrative and not the other way around.

So, what quite happens, what happens a lot with this type of content is you do a ton of research, and you put the research on the page, and you kind of leave the reader to connect the dots together. And in the worst-case scenario, you're almost actively delegating away your authority because you're saying, "Yeah, this is my blog post, but actually, it's built on the back of lots of other smarter people's research." That is not the vibe of this article at all. There is a very, very strong narrative structure. Like, these are the problems they had, here's how I would recommend solving it. And if you took away the data, this article would still be interesting and it would still work. It's better for having that data because there's a kind of one-two punch here of the narrative supported by the data. But crucially, the data is not the thing that is carrying the article in its own right. There is a narrative structure here, and that is so, so important for thought leadership.

There's also lots of jargon, you know, talking about SaaS, SMBs, API integrations, horizontal SaaS products, things which are not, you know, laboriously defined by Hiten because he expects the reader to either understand what they are or at least to go out and find that information for himself. And again, that is a great way of proving his credentials and his authority. He doesn't define this stuff because these terms of art are things that he uses all day, every day, throughout everything that he does. It would be insincere and weird of him, almost, to define them for the reader.

And one thing I really liked at the end as well is Hiten explicitly addresses what I think of as the jerk problem, which is if this is a whole article tearing down the failure of Trello, well, it doesn't come across as particularly nice. But as Hiten says here, hindsight is 20/20. Building a company that's worth $10 million is impressive, let alone a company that's worth $425 million. So, he has basically gotten ahead of this potential criticism and said, "Yeah, you know, this is an amazing thing. It's still worth reflecting on how things could have been different and potentially bigger because that's a useful exercise. But ultimately, we should not forget that this is an incredible thing that Joel and the Trello team did."

So yeah, absolutely a huge fan of this article and Hiten's work generally.