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In today’s Startup Chat, we talk about Hiten’s recent article, Why Trello Failed to Build a $1 Billion+ Business. Trello was recently sold for $400 million. Hiten’s article expressed that Trello could have been a much larger business had they monetized earlier on, focused on greater productization and thought about ways to ensure greater client stickiness. Tune-in as Hiten and Steli discuss how sound strategizing would have ensured a much larger topline and a greater customer base for this much loved company.

Time Stamped Show Notes:


00:03 – Today we are going to talk about why Trello failed to build a billion dollar business

00:28 – Hiten recently wrote an article that expressed his thoughts about Trello and how it was one of those rare businesses that could have become much larger than it did


01:51 – With minimal effort, Trello could have been HUGE


02:02 – Hiten wrote this article with good intentions since he cares deeply for Trello


02:51 – If someone criticizes you because they want you to do well, it should not make you feel bad

04:05 – A lot of people engaged with his article—both positively and negatively

04:54 – The strongest reaction came from those who just read the title


05:22 – Lessons learned from Trello’s failure to scale up


05:22 – Trello did not monetize fast enough

06:01 – They offered free services for too long to chase high growth

06:16 – Failed to study cases of how different people were using this generic tool


06:42 – They should have productized or verticalized the product to a higher degree

06:58 – Airtable is doing a great job of productizing


08:09 – Important to ensure that the product integrates with other tools which will ensure greater customer stickiness

08:53 – Important to think of how a product fits into a person’s workflow

09:51 – Integrating Trello with other tools will ensure that you do not need to log on to Trello

10:22 – Understanding customer behavior will bring about greater stickiness

11:12 – Workflow should be updated; not just in Trello, but in all integrated tools

11:51 – Trello should have attempted to emulate a tool like Dropbox in terms of its stickiness

12:58 – Trello did not capitalize on their initial success to build an enterprise model


13:16 – Read and share Hiten’s article


3 Key Points:


Do not wait too long to monetize your product—capitalize off the first-mover advantage. Do not sacrifice profits and cashflow for growth.

Integrate your product with as many different tools as possible to ensure client stickiness.

Analyze how different people use your product and work on PRODUCTIZING.


Steli Efti:


Hey everybody, this is Steli Efti.


Hiten Shah:


And this is Hiten Shah.


Steli Efti:


And in today's episode of startup chat, we're going to talk about why Trello failed  to build a one billion dollar business. This is an article that Hiten has written  recently, and it's an article that's gotten a lot of attention. It keeps getting like  ... My timeline there's not a single day that I don't get a few of  the ... A few people that I follow sharing this article of yours. But, there's  controversy, right? Not everybody loves this one. So, I thought we should chat about it.


Hiten Shah:


Yeah, absolutely. So, first of all, what I learned about myself, and I think you  can relate to this, is when I write content and I'm really passionate about it,  it turns out really well. And, this was a topic that even before Trello got acquired, was bugging me. And what I mean by that is, I've tweeted about this  even and the tweet's in there, before I even wrote about it. Before they even  sold, and they happened to sell and I'm like wait, this business could've been much  larger, right? So,

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