Failing Forward

An honest look at my life as a wantrepreneur.

I quit my job because I wanted to see what I could accomplish on my own. But for two and a half years, I have been nothing but a wantrepreneur. If you haven't heard of that term or can't piece it together, a "wantrepreneur" is someone who wants to be an entrepreneur, but generally isn't there yet. While I have learned a ton about software development through self-directed study, as an entrepreneur I am still a failure.

In my experience as a wantrepreneur I have jumped from project to project, looking for that perfect idea that's going to lead to complete fulfillment and sustainable income for years to come. Apparently I'm very good at starting things and utterly terrible at finishing them. Here is a list of just some of the projects I started that are sitting idle.

  • VizPoint, a consultancy that specializes in quick-start business intelligence engagements (I actually had some clients and revenue from this).
  • Neato, a cloudless data analysis and visualization tool (my main project).
  • Turnout, a mobile-first event ticketing solution for managing sign-ups, payments, and check-in.
  • txxt or Shorthand (I never settled on a name), a markdown-like text editor with customizable syntax.
  • TinyPolls, tiny embeddable polls for web, social, email, and more.
  • LazySQL, a graphical interface for creating, managing, and analyzing SQLite databases.
  •, an ad-free subscription email service that doesn't invade your privacy.
  • Emoji Tale, create and share personalized stories made from emojis.

Seriously, this isn't even half of the projects in my "Projects" folder. But to be fair, many of them were just vague, half-baked ideas that often didn't make it past a quick mock-up (if even that).

Trial and Error

Other than the fact that they all sit unfinished, these projects have surprisingly little in common. This illustrates how difficult it has been for me to find a project that checks all the boxes:

  1. It's fun and fulfilling (aka, a passion)
  2. It's economically viable
  3. It has the right level of complexity
  4. It has the right amount of competition
  5. It's unique enough

A couple of my projects came close to meeting these criteria, but after devoting a few months to each one I realized they weren't quite right. I thought it would be constructive to write postmortems on these projects. You can find these in separate posts:

But to briefly summarize, the problem with Turnout was that I wasn't passionate enough about it (criterion #1). I also lack experience in third party payment aggregation, which is a risky business model that makes me nervous.

With Neato, I had the passion but was overwhelmed by the complexity (#3), the ever-growing competition (#4), and I wasn't sure if it would be a unique enough product (#5).

Next Steps

It's risk taking time. Put up or shut up. Go big or go home.

I am officially retiring all of the projects mentioned in this post and focusing all of my energy on one project, lowercase.

Lowercase is an intuitive interface for the web. It is a general purpose content management system, similar to WordPress or Ghost. It's well suited for blogs, small business websites, or any site with a need for data collection (polls, applications, etc.).

For the nerds:  lowercase is written in JavaScript on Node.js and Express. For storage we use SQLite, as it offers everything we need and nothing more.

While my old projects are being retired, many of them may have a chance at a new life somewhere in the lowercase ecosystem. For example, it's very likely that lowercase could have an official plug-in for polls (formerly TinyPolls). It also may have a plug-in for event registration (formerly Turnout). And, like txxt, lowercase's editor will use customizable markdown-like syntax.

So rather than starting from scratch, I see lowercase as an opportunity to consolidate my earlier web app efforts. I believe it will be far easier to integrate these as small, functional pieces in a larger ecosystem than building them as completely stand-alone products.

Anticipating Success

I feel good about working on a content management system. I'll explain why by touching on the criteria I outlined earlier:

  1. It's fun and fulfilling (aka, a passion)
    I really enjoy working on web applications, but there is added appeal to building something that serves as its own platform. It combines all of the geeky things I love:  data, design, branding, organization, and productivity.

  2. It's economically viable
    Automattic, the company behind WordPress, has raised money at a valuation over $1.1B. They are undoubtedly the largest player in the space (Wordpress powers something close to 25% of all websites). They had about $45M in annual revenue in 2012, and while there is no public data since then, I imagine they're now easily over $100M.

    Ghost is a relative newcomer with a very nice product that caters to professional bloggers (while I'm not a professional, this blog currently runs on Ghost). They're doing about $600K in revenue annually going into their 4th year, which is a good target to aspire to. Honestly though, if lowercase caters to businesses (which I'm leaning towards), then it could conceivably generate more money.

  3. It has the right level of complexity
    Building your own CMS isn't easy, but it's doable. What's notably appealing is that building a CMS can be very iterative, which is ideal for any new product.

  4. It has the right amount of competition
    There are a lot of content management systems out there, but many of them aren't very good. They're often unintuitive and not very accessible for non-technical users, requiring extensive training or hand-holding from the administrator. There is room for better products.

  5. It's unique enough
    It's too early to define exactly what lowercase is, but currently I'm envisioning a product that functions like a general purpose CMS, but also caters to businesses with features that focus on collecting and using data. This would be an excellent fit for companies that use their website to schedule appointments, collect applications, run polls, conduct surveys, etc. It could also be a good fit for real-time community-driven sites (like Rotten Tomatoes, RetailMeNot, and GasBuddy).


I have been using the name "Neato Software" since last year. Going forward it will officially be the name of the software business that oversees development of lowercase.

I will dissolve my consulting company, VizPoint LLC, by the end of the year and transfer all assets (domain names, equipment, furniture) to Neato Software. Neato Software will be a sole proprietorship until the point where I meet the right cofounders.

Seeking Cofounders

Which brings me to the most important part. I'm seeking cofounders who are passionate about the web and can get excited about building a new, intuitive content management system. Ideally, I would like to find partners in Las Vegas who are interested in doing this full-time. I want to equally share ownership of Neato Software and am willing to fund a good portion of our early expenses. I prefer not to take any outside investment.

To potential cofounders, here's my commitment to you:

  1. It will be fun (what's the point of starting your own company if it's not fun?)
  2. I will be fair and practical
  3. I will keep to the values that I outlined here, which I'll repeat:
    • Integrity. We do the right thing.
    • Transparency. We share as much as possible.
    • Progress. We take every opportunity to learn.
    • Balance. We value personal time as much as work time.

If this sounds good to you, please reach out.

Anyone interested in being a cofounder can reach me anytime on Twitter @cschidle.

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