How my Prototype’s failure created the next Iteration

Great things are possible only through continuous learning and improving. For years now, I’ve been nursing the idea that there is a better way to discover, read, and learn online. This has led me to form and test hypotheses around that 0.1% of timeless content that is ‘Evergreen’. This is the story of an experiment, a failed hypothesis, and a fresh attempt.

Launching a prototype did exactly what it was meant to do — showed me the weakest points in my assumptions and plans. Finding ways to fix these failure points became a guide for the new experiment.

I was inspired by the Product Hunt story, and what Ryan Hoover & Nathan Bashaw had done to create a community. They wrote some incredible posts about their early prototypes. This was what I wanted to create for life-long learners. After (not very much) consideration, it seemed a good test would be to use Linkydink to bring together a community to share great pieces.

So I did.

Things started strong. Friends, colleagues, and connections piled on, and we got a lovely stew going, with something new and interesting posted every day. Subscribers started joining, and everything looked sunny.

After taking a week off from pushing forward to see whether we had built inherent momentum, things faltered and went quiet pretty quickly. I went to have some conversations about what happened and why.

Here’s what I learned.

Problem: Poor clarity on ‘good content’

The first clear problem was with the way I structured the experiment was poor framing of what was and wasn’t a good fit for posting there. With that difficulty, contributors were unsure of what to post, which decreased total posts. When criteria is not clear, content becomes too varied and readers don’t have a clear idea of what to expect from the product.

Solution: Specific Weekly Topics; Clarifying Tagline

To reduce this effect, the new prototype will be based on one weekly topic, challenge or question (for example: Hiring.) Contributors will submit materials specifically relevant to that topic, to reduce that uncertainty.

Also, this experiment will have a Tagline (see below) that aims to clarify the purpose and more precisely characterize the community. The goal is for people to read it and immediately self-identify as interested or disinterested.

Problem: Overwhelming Content

Another problem was the volume of content-rich emails. Daily is a lot — I underestimated how easy it was to get overwhelmed with daily emails. The goal was to cure the ‘firehose’ and this actually created a smaller and much stronger stream.

This soon becomes demoralizing rather than aspirational and motivating. Delivering high-value content helpfully requires the restraint of being measured and paced.

Without a layer of curation or synthesis, anything that was suggested was distributed, whether it was on topic, repeated, or written in swiss. Obviously problematic when attempting to create a measured, paced environment.

Solution: Weekly emails of Synthesized Content

Rather than a tangled and constant barrage of daily emails, this experiment’s main attraction will be one weekly email that has been crafted based on contributor’s best suggestions with added context and narrative to synthesize into one cohesive experience.

This should feel like reading a short and lesson-dense book on the topic of the week. Nothing too far astray, nor too repetitive… a thorough examination of a topic from a variety of perspectives and mediums.

However — nothing will be wasted of the raw materials that were suggested by contributors. Everything we record will be archived in a categorized, organized library, so it will always be available as a resource to members.

With those lessons fresh in mind, here is the next iteration:

Evergreen: Weekly emails that build a Business Mind

A community of aspiring managers, founders, investors, and CEOs learning and teaching together.

Join here

Each week, we’ll feature one topic, challenge, or question and contributors are invited to submit links to posts, books, talks, courses, even personal stories — any resource you value relevant to the topic.

All submissions will be read, curated, and synthesized for that week’s email. In addition, every submission will be archived in a Library for permanent access of those in the community.

We’ll kick this off in the next few weeks. Join by sharing your email to be in from the very first week.

Let’s get better, together.

Thank you.

Thanks to Matt Donovan for his patient and insightful thoughts.
I write better posts also:
Make the Internet your Personal Library
How to College
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