Proper is Shutting Down October 29th, 2014

This post originally appeared on Since its publication, that site has been taken down. This was a fairly popular post, so I’ve decided to archive it here for posterity sake. If you have any questions about what it contains, please contact me at my personal email:

I’ve decided to shut down Proper—the overwhelmed octopus is heading back down into the depths of the ocean.

On October 29th, 2014, I’ll be turning off the servers and deleting the master database. Don’t fret: I’ve added data exports so you can get your data out of Proper. Login to the app and visit this page to export a .zip file with all of your contracts, templates, agreements, clients, and invoices. If you are currently a customer, your most recent payment will be refunded.

Make sure to do this before October 29th (I’ll be sending out a handful of reminders leading up that date)! On November 29th, I’ll be deleting the backup database and redirecting the website.

Okay, so, why are you shutting down bub?

Unfortunately, I’ve failed to turn Proper into a viable business. Over the past year, I haven’t seen the activity I was hoping for, nor have I invested the amount of time or energy required to nudge the app forward. To put it plainly: I got burned out early on in the game and the app took a backseat for the better part of 2014. If you’ve been following along, you probably got a hint of me being zero’d out shortly after launch from posts like this.

Unless you’re interested in a detailed postmortem, you can call it quits here. Again, if you are or were a Proper customer at any point, make sure to login and export your data by October 29th, 2014.

Okay, on with the postmortem…

Personal Limits

If you were following along with the development of Proper, you’ll know that save for the logo and illustrations on the site (thanks, Tyler!) and the majority of the blog writing (thanks, David!), I was responsible for all of the design and development of the website and app. This does wonders for your ego but also works as a great way to deplete energy. It took about 4 months to complete Proper from start-to-finish. When all was said and done, I’d effectively squashed my mojo into oblivion by the time I’d launched.

The lesson learned here is that if you’re going to work by yourself (whether intentionally or for a good amount of time): pick an idea that fits within your personal limits. I love the idea of Proper and still feel that it could be a solid business, but in retrospect running it on my own wasn’t a bright idea. The application was just big enough that, in combination with my own lack of organization, became unruly. Managing code felt like a chore as opposed to a joy and I quickly fell behind on updates and fixes.

You may be thinking “you must be lazy, I wouldn’t let that happen.” Perhaps not, but heed the warning: you will get tired, you will burnout, and things will fall by the wayside at some point if you do not:

  • Organize your process: task management, code wrangling, product development etc.
  • Ensure that you understand the underlying aspects of the business (the “how you’ll make money” part).
  • Choose an idea that fits within your personal limits.
  • Continuously and consistently improve and promote your product.
  • Develop habits around all of the above.
  • Focus on one thing at a time.


Proper was written using the Meteor JavaScript framework and has remained at version (as of writing the framework is at version 0.9.3) for its entire life. This caught me off guard. Being burned out meant that updates to the app weren’t happening. Of course, plenty was changing with the framework and the community and I failed to keep up. The end result was that the framework got far enough ahead of Proper that it became entirely too overwhelming to update. This isn’t the fault of Meteor, but of myself. I knew going in that things would change and that I’d need to be prudent about keeping up to date. Unfortunately, I didn’t do that.

The warning here is to be careful about the technology you build your product on and your willingness to evolve with it. I love Meteor and had I kept things up to date I’d be a happy camper. But because I wasn’t able to stay on track, the app ultimately suffered. If there’s even a hint of a chance that you may fall behind: take a close look at your product’s foundation’s and ask if you’ll be able to get away with a bit of slack (99% of the time the answer will be “no”).


When Proper launched, I’d been running my own freelance business for just about two years. I made the mistake of thinking that running a freelance business and running a software business were one in the same. They’re not. The reality is that while a few of the skills from my first business overlapped, a lot of stuff was left with a big ol’ question mark. Moreover, it’s safe to say that while I was able to support myself, my freelance business wasn’t growing much beyond me.

Over the last year and as a result of a boatload of business reading, I realized that I simply didn’t understand a lot of the fundamentals. From what I read I’m not alone, but don’t take that as an excuse to dive in without doing your homework. Understand what you’re getting into or at the very least, know what you need to know about your particular business and then actively pursue learning it. Don’t be arrogant and think you’ll “just figure it out.” It’s very likely that you won’t.

Take an extra couple of weeks (or months) to learn how to do it right and really evaluate what you’re doing to make sure you’ll achieve the goals you’re setting out to meet. A few recommendations:

  • The E-Myth Revisted by Michael E. Gerber is a great book about setting up your business structure and process and avoiding the “technician” trap. It’s an eye-opening read and highly recommended if you’re looking to start a new business.

  • The Personal MBA by Josh Kaufman is worth a read as well. It’s easily digestible and is chocked full of fundamental lessons on business. This is a good one to read through and then continue picking up every couple of months to review.

  • Seeking Wisdom: From Darwin to Munger is a book about human behavior. This is an excellent book that helps you identify pitfalls in your own thinking and logic. I’m about halfway through as of writing this and it’s significantly changed how I think about my work and my life.

I should note: there is no official manual for this stuff. Anyone who tells you they’ve got it figured out is lying–or not telling the entire truth. There are, however, a lot of people that have come before you and can share insight into what to watch out for and what to avoid. I caught myself getting discouraged a few times because I’d read books or articles that contradicted how I felt about my own business. Don’t let this happen.

If you read something that doesn’t agree with your own thinking, make a note to evaluate it and figure out why you don’t like it. Try to answer: “what about this don’t I like? If I do this, what are the consequence for my business? what if I don’t do this? will this impact how customers perceive my business?” Essentially, be conscious. Don’t make unnecessarily brash decisions. Think stuff through.


The last area that I failed to grasp was tone. When I started work on Proper, I was enamored with companies like MailChimp: fun, playful, and not too serious. One of the bigger mistakes I made was branding Proper with a confusing message. It looked like something fun and lighthearted, but in reality it had to do with something serious. In my own eyes I “got the joke,” but others didn’t.

The lesson learned here is to match your branding, tone, and voice to the nature of your product. That doesn’t mean you have to be dry or lifeless, but consider how your product looks from a third-person perspective. It’s a balance: don’t silence your creativity (stuff like MailChimp is awesome) but don’t jeopardize your product because you failed to consider what you’re selling and to whom.

Swing and a miss, kid.

Ultimately, I’m actually quite happy with how Proper turned out. It was a massive learning experience and allowed me to squash a lot of the fears and misconceptions I had about writing and operating a piece of software. Hint: it’s not as scary as you think. In reality, what matters is the same stuff that mattered before the internet: understanding business fundamentals, selling something people want, and building your product up to offer more value over time. Reading that sentence I’m thinking “duh,” but it’s less obvious than you think when you’re in the thick of it.

I’m far from done with making things on the internet. I’ve actually got a new project (that’s much more manageable for an army of one) coming together that will be announced in a few weeks (follow me on Twitter @rglover for updates).

In summation, I think that’s the moral of the story: don’t be discouraged. Keep working, keep learning, and keep trying. One failure, ten failures, a hundred failures. Just keep moving toward what excites and interests you. Making money is only part of the equation—don’t forget to have fun and enjoy yourself.

From Seeking Wisdom:

A child is curious and asks ‘why?’ As grown-ups we seem to forget the ‘whys’ and accept what others say. We should all be children again and see the world  as if through the eyes of a curious child without preconceptions.


Thanks to everyone who was a customer, signed up for an account, shared one of our articles, or gave a pat on the back when it was needed. Proper was a beast and I couldn’t have done it without your support!

I’d like to close this up with a personal favorite: Bill Hicks on how life is just a ride. Enjoy:

– Ryan