Startup Failures, Learnings & Next

I recently pulled the plug on ESL Relief. It wasn't that it was a very hard decision to make by itself but it was hard to admit that the whole project wasn't really going anywhere. I've tried to distill down the learnings and key take-aways.


  • Having domain expertise is irrelevant if you don't care about the problem.
  • If you're working full time you need the startup to be super compatible
  • Market size (current or future) matters.
  • Build lean and look at a problem in search of a solution, not the other way around.

Domain Expertise < Passion

It doesn't really matter how much domain expertise you have if you just don't care about the problem. My thought process was simple: I know about ESL, it has lots of problems, I want to build a business, maybe I should build an ESL business? But now that I've spent a lot more time in startups and learned heaps in the process I've realised that I don't really care that much about ESL schools.

I didn't care enough about the problem. No amount of domain expertise can overcome that. When I mentioned this to Matthew Ho he said something that stuck with me: "You have to care about the problem, you have to care about the customer".

It's better to work on a problem you care a lot about even if you're not an expert in it than to work on something you're an expert in but don't care about.


We were trying to contact directors of studies for language schools. Turns out they're very busy people. That's fine. The more difficult part was that they're not business people and often, whilst running the school, they have no authority to authorise new expenses. The school owners are almost impossible to reach. I'd prefer to work with people who understand the ins and outs of business and have the authority to make decisions - even if they're busy.

I also work full time. That being the case it's a bad idea to be working on a startup that requires you to call people during work hours. It can be done but, given my background in SEO, it would make more sense for me to be on some sort of project where it makes little difference what time during the day I work on things.

Market Size

Current or future size needs to be significant. So you're either catering to an already large market or riding an emerging trend. If you don't have either then the best you can hope for is a sweet lifestyle business. As it stood our market was too small to even sustain a good lifestyle business.

Build Lean

When I saw the technology Skylr was building I thought it could apply to ESL schools. It's tempting to think that way but it would have been much better to start with a problem, validate, build solutions and iterate. No matter how good the technology it only makes sense to start there if it's already been proven in a highly adjacent and similar vertical. Anything else is throwing darts in the dark.

What Now?

I'm not going to rush or push myself to come up with my next idea on the spot. Instead I'm going to wait until I'm good and ready and the elements come together. I'd like to work with another cofounder on a problem or opportunity I truly care about that has a big market behind it.

It also needs to be something I can work on after work hours without that being a big problem. Some ideas include a big data + SEO play, an OH&S app or something in the recruiting/job search field. I also love the idea of building an email list as I've started doing email marketing at work and for Fishburners. Strangely I also find the process of building email campaigns quite soothing.

I'm also focusing more on things that liberate me from full-time employment so I can be at Fishburners all day.