Entrepreneurial Engineer

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Conversations First Thesis

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Conversations First

Conversations First Thesis

An evergreen, ever-updating piece

KimSia Sim
Dec 24, 2022
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Conversations First Thesis

www.entrepreneurial.engineer
Photo by Dall-E. Prompt is “many speech bubble and many people talking, digital art”

I’m in Rob Fitzpatrick’s Outcome-Oriented Community (OOC) Builders Community. Anyone interested in being entrepreneurial on the internet will be familiar with the typical ways to package value to sell.

  1. Software

  2. Content

  3. Paid Course

  4. Community

As an entrepreneurial engineer, I was definitely interested in the Community way as well. What swung the deal for me to join OOC Builders is because Rob seemed to have a slightly different take on what a community should be.

After more than 6 months in the OOC Builders, I’m starting to form my own opinion about the topic which I have already written inside the OOC Builders. I feel there’s enough for me to expose my own thoughts in my own space.

⚠️ Since the ideas are still relatively alpha stage, I expect to change some of the ideas here and also to append more.

Consider yourself properly warned


Focus on Tech / Platform / Conversions is Putting the Cart Before the Horse

Paul Graham has a famous essay, calling founders to "do things that don’t scale". Here’s a list of the examples he cited.

Worrying about which technology to use, which platform to build before you even regularly produce content, or have a ready audience in the first place is the opposite of what Graham recommends.

A similar concept but one that’s more familiar to engineers is the idea of "premature optimization".

But what does Do Things That Don’t Scale look like in terms of "building a community"?

An example can be found in Clay Shirky’s Here Comes Everybody when he quoted Caterina Fake of Flickr. In his book, he wrote that Fake

… said she’d learned from the early days that “you have to greet the first ten thousand users personally.” When the site was small, she and the other staffers would not just post their own photos but also comment on other users’ photos, like a host circulating at a party. This let the early users feel what it would be like to have an appreciative public, even before such a public existed.

Excerpt From Here Comes Everybody by Clay Shirky. Emphasis mine.

Flickr was and still is an image hosting Software as a Service (SaaS). But, they identify as a community early and often. Go to their website and you’re likely to be greeted by this.

Flickr calls themselves a community

Therefore, instead of starting with scaling efforts, start by having conversations. But how do we generate conversations?


To be updated from time to time

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