Ramblings about biting off more than you can chew

I’m going to be presenting to a class of aspiring web developersand designers, and this post is practice articulating one of a couple lessons I learned in my couple years as a tech entrepreneur.

College Itinerary is a hobby project thatexists to help students create a calendar of all the relevant application dates and deliverablesfor their prospective colleges; then students get alist of their upcoming deadlines in a weekly email. I won’t get into the business case in much detail in this post.Instead, I’m going to say something about the limited scope of the project and its distinctandmanageablevalue proposition. And, in this light,College Itinerary should stand in stark contrast to YourSigma, a startup with a vision and scope so grand it was debilitating.

YourSigma (or the unexpected virtue of ignorance)

YourSigma was borne after manyhappy hours with Chris Webb, Jason Heller, and Alfonso Pacheco, during which we discussed the idea of a better learning management system for big businesses. It was going to be a cutting edge social learning tool, a la Grockit.com, to help employees prepare for certification exams and enhance their skillset. Between us, we had worked for some ofbig companies: AIG, Citigroup, Medco, GE, Lehman Brothers, and found thatthey all shared outdated, almost unusable internal online learning platforms – if they had themat all.

Meanwhile, we had healthy imaginations. And we had Chris Webb. Chris is a whiz programmer and knows it. At one point he commented:

Almost anythingyou can think of is technologically possible. Seriously.

I’ve spent the last two years watching Chris do some masterful work, and I have learned to do some myself. I have come to learn that Chris was right, anything is possible. Every day, there’s a new API, a new framework, thatpaves the road to some previously unreachable place. It becomes a bigger challenge just unearthing that Github repo, that node.js module that someone built to do what you need. In fact, the abilityto find“prior art” is now an indispensable skill.

Back to YourSigma. We were talking about a sophisticated single page application. And, the vision would have been overwhelming it it weren’t for Chris’ can-do attitude. Here’s a video demo if you have 2 minutes to kill (or run it at 1.5x):

However, once we got going, I realized how far we had strayed from a “lean startup” approach. Ours was now ahuge project, fit for Fortune 500 organizations with hundreds of thousands of employees each. The experienced entrepreneur (me, now?), when bootstrapping a new business, would have focused on theminimum viableproduct.

The consequences of setting out to build a web application so grand are 1) a helluva lot of building before testing on users, which is a huge risk, 2) the seemingly insurmountable amount of work – even if it is all technologically possible, and 3) all this on top of the many other challenges you face as a first-timeentrepreneur: no income, no textbook or person with all theright instructions, and no one to blame.

Doing things differently

I recently have been asked to give a public presentation about my startup experience at IronYard here in Austin, TX. When I give it, I will speak in part aboutchoosing a small, specificproblem you want to solve when starting out; so specific it fits in the palm of your hand; so specific that there is no question that you have solved it.

And, I want College Itinerary to be the proof of that concept. The specific problem is simply that students applying to more than a couple 4-year colleges (10-15 is the norm these days) have to check 10-15 websites for application deadlines, requirements, essay questions, and other information. If they’re organized, theycollect all this information on paper, in excel, or in evernote. How long does that process take? 5-10hrs?

That’s it. That’s all College Itinerary should do – save studentsthat 5-10 hours, then email them just often enough to be helpful.

Does it work?

It would be nice to conclude this post with a clear example of how this served me well. Unfortunately, I can’t devote my full time to it. But, I can tell you this:

  1. I wanted the typical use case to be so simple that it could all happen on the home page. That saved me time I was going to spend thinking up copy, pretending to be a graphic designer, and then watching that part of the funnel – how often users click through the homepage.
  2. If I wanted the user to start and finish the workflow on the homepage, then I had to focus on clarification (remove the impurities, the fat). You have toreduce the number of steps wherever possible. All this talk of clarification and reduction – I should have titled the blog post “cooking up an app”.
  3. Hopefully, this keeps you from building anything extra, and you can get an MVP out quickly.
  4. Then, test it out immediately. Get some users on it. Pay some people to try it. Use Intercom to ask your usersabout it. Demonstrate it in front of people.
  5. If you nailed it, your users will appreciate its simplicity and pass it on. Ifyou didnot, you’ll know it quickly – you won’t have to worry about the funnel, because users did not have to navigate through your site.

So, in myearly testing of College Itinerary, I learned that I didn’t heed my own advice well enough. The workflow was still too complicated.There werestill too many choices each user had to make.

I also found that the email feature was notas valuable to students as knowing their chances of admission. The college counselors I talked to also wanted help confronting students with the cold, hard facts – their likelihood ofgetting into certain schools, or how theirodds dramatically improved by applying early decision, and so on.

I’ll make a post of my user research later. I’ll conclude here by emphasizing this: you’ll enjoy working on a big project, but you’ll kick yourself if you build something peoplewon’t use. Meanwhile, I suspect most developersexhibit a decreasing marginal return on their time and energy. Such as, you can accomplish more in your first 3 months on a project than you can in the 3 months after that. Groundbreaking apps don’t have to look like“evernote meets asanameets powerpoint”, so distill your project down to the bone and release it into the wild quick.