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No. of Recommendations: 8
Nice thought-inspiring post.

I think your thoughts are just a subset of "stickiness". At first I was going to leave it there but I actually want to go a step toward the extreme and say this is dangerous if taken as a blanketing thought that would prevent a truer understanding. What I mean by this is that each company (for the most part) has a unique blend of stickiness concepts. The first two are explored in the original post I think:

1. Switching costs.

2. Network effects can be sticky if they prevent people from moving away when a solution. For example one that is required for multiparty interaction like Zoom meetings. It means a group has to decide to move together or individuals have to be willing to use multiple solutions or miss out (e.g. switching away from using Facebook with friends).

....there are a number of others. Here are just a couple:

3. Integration complexity. a) If a company sells a platform which users then build further solutions on top of, switching away can be a big project. b) the solution could integrate with other things, like security systems or workflow automation systems, and all of that might need to be re-created too.

4. Proprietary data. If a company generates a lot of valuable data within a system then that data either needs to be processed and migrated, if possible, which can be a big undertaking. Think about switching from GoogleDrive to...whatever else people might use. You'd have to go document by document to export it and then import it, and even then the document formatting might not translate perfectly and need fixing. You may even need other tools or custom software to do this.

5. More...

"Ultimately, this train of thought has come from thinking about how Fastly caught me by surprise and has me rethinking my conviction in DataDog..."

This is where I think things might get dangerous. These are so completely different. Fastly (and Cloudflare) CDN business is not real sticky but it is funding the ongoing development of their underlying edge networks and other services. I think you went wrong by not knowing this detail of their business. The other businesses at both of these companies can be much stickier then CDN services. This has absolutely nothing to do with DataDog's business however.

My point is this: This thread is a nice thought primer but just like we don't have a magical stock screener to find good investments I don't think you can sum up tech in this way. When you dive in to build a thesis on stickiness per company I think, to use a food analogy, you build a palette and the flavors start to taste different from each other. Also, sometimes it doesn't matter at all. It all depends.
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