It feels like an eon ago that I left Khan Academy to start my journey into self-employment. I'm planning to do a proper launch of Shmeppy within the next few months so I thought I'd summarize some of the story so far.

"Shipping Beats Perfection"

An ethos on Khan Academy's dev team is "shipping beats perfection" and it's an ethos I've really taken to heart.

I started my own journey of learning this ethos via my own bitter mistakes before I ever heard about Khan Academy. The most acute mistake I remember was when I was working on Galah (a product/company I was trying to bootstrap in college). I wasted a ton of time trying to achieve "engineering perfection", and ultimately the product didn't go anywhere (I think) because I didn't spend enough time on the most important work.

With this ethos in mind, last year I tried to create a minimum viable product of Shmeppy very rapidly. I looked at the long-term product I wanted to build, and cherry-picked the most important things from it. I built it as quickly as I could (which ended up being about 6 months) and then attempted to find some users.

I had limited success. The people I talked to seemed interested in Shmeppy, and I got some tentative validation, but I didn't convert anyone to actually using Shmeppy in their groups. I didn't do much of an advertising push here, mainly just went around to my friends and folks on Reddit and Discord and pitched Shmeppy, but the sense I got was that Shmeppy was far too rough around the edges.

My bar of "what's good enough to ship" seemed to be off. So coming into October I decided to focus on finding that bar.

Finding the Bar

The first thing I did was decide that I'd stop wasting time trying to show Shmeppy to random people. I had been doing that throughout the process and honestly I don't really know how helpful it was. It was certainly very emotionally taxing to keep putting my work out there over-and-over again and yelling "please notice this and like it!"

Instead I decided to try and create a regular playtesting group where I'm the DM. This way I'd be dogfooding my own product in a very real way. I figured as long as I wasn't doing that, I was just fumbling around in the dark.

It regretabbly took me a few months to get that together (I think I could've done it faster), but I now have two playtesting groups that each meet bi-weekly so I'm getting a playtesting session in one per week.

(Notably, a friend of mine had actually been using Shmeppy with a few groups of his for several months by this point, and had been feeding me useful feedback. Thank you Kitt!)

I've only had a couple playtesting sessions so far, but my sense is that Shmeppy is very close to that "good enough to ship" bar. It's fun and authentically useful.

There are certainly a lot of features that are blatantly missing (like chat, uploading premade maps, dice rolling, video conferencing, etc) but I think that's OK because most of those things are easily replaced with other products (hangouts, discord, etc). And Shmeppy's core mapping feature is unique, I don't know of any other product that makes it easy to create maps on the fly like Shmeppy does. I think I've done a decent job focussing on what's important.

"Shipping Beats Shipping"

So I'm tentatively gearing up for a conventional product launch in the next few months (or however long it takes me to do all these things):

  • I'm preparing tutorial/onboarding flows so new GMs don't drop in and immediately ask "ok, what now?"
  • I'm contacting various DnD podcasts to try and find someone to advertise with.
  • I'm looking into various online advertising channels (ex: Reddit).
  • I'm creating scripts to extract the metrics I'll need from my logs in order to diagnose how the launch is going, and defining what those metrics are.
  • I'm working on an effective landing page.
  • I'm setting up payment processing for a pay-what-you-want-during-early-access scheme.
  • I'm figuring out my terms of service and privacy policy.
  • I'm ensuring Shmeppy can handle at least small bursts of traffic.

I've never really done this before and I'm thoroughly terrified. It's reasonably likely to end in failure and the only thing increasing my chances of success is my own fumbling.

But I'm still excited. I still think Shmeppy has a great chance of being a successful product. And since my financial time pressure hasn't caught up to me yet, I have the time I need to at least give Shmeppy a proper shot.

Fingers crossed.


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