I ran across this article about Rentobo while glancing through TechCrunch the other day. This sounds a lot like the idea I had for a site I was working on from 2005-2010 called, which failed to launch after many years of trying. Instead of yet another blog posting about a success story, I figured I would write about my failure. Hopefully someone else can learn from my mistakes.

In 2005, I was in the search for a new place to rent with my girlfriend. We wanted something a little bit more like a house and turned to Craigslist to find rentals. The competition was pretty heavy, often with us sitting in the kitchen filling out applications with other prospective tenants. Much of the process was manual and often the landlords were individual people with day jobs. That made the whole process of turning in application fees more difficult. I felt there had to be a better way and why not use the Internet to do it.

This is when I did some thinking and registered the domain The site was going to be a portal for landlords to add their property, accept applications online, sign leases online and even collect their rent. The feature set was quite large and really strived to make the whole process less intensive for landlords and push the burden to us. Quite an ambitious goal for someone's first foray into the world of business.

I started development and instantly started to think about frameworks and languages to use. I started to evaluate various methods of building the site, producing these wonderful spreadsheets of pros and cons for each approach. Lots of the effort was centered upon how to cope with scaling these technologies to the size and speed of Google or Digg. This was all before I had tried to build a single prototype or even put together a single sketch of any screens. Already, I had fallen into the engineer trap and jumped to details that shouldn't matter.

As I continued my technical evaluations, I also started pitching the idea to various groups. As you would expect, I didn't get any money without any working prototype or even a remote design as to how the site would work. At this time, my girlfriend was able to take a promotion to Seattle and did for work. This left me with a limited cash flow, no girlfriend and making no traction with development. Getting discouraged, I put the idea on hold and landed a job with RIM in Seattle in 2007.

Once I got to Seattle, I dawned on me how much I really didn't know from a technical perspective. I was introduced to some very sharp individuals who taught me tons all while I got to work on RIM's consumer email solution in the cloud called BIS. To top it off, I was collecting a very nice paycheck. Over the years, I would be compensated greatly for my efforts and I loved the money. We would eat at nice restaurants, fly first class, buy all the latest gadgets and every now and then I would look at

Around 2009, I started to feel that RIM wasn't going to offer me the chance to have more influence in decisions. They kept hiring more managers and as the leaf of the organization, I stayed put just moved between branches. I wanted to return back to my idea but came to the conclusion that I couldn't do it alone. There was too much work and I needed someone to keep me honest and on track. It was around this time I decided to have some conversations with a coworker about joining me with He agreed and over beers we decided that we should partner to start the site.

Our partnership quickly fell apart since we didn't come to the table with the same mindset. Simple things like registering for Seattle 2.0 Startup Day was too much money for him to commit. I ended up going myself and meeting with advisors and attending the sessions. My partner was also interested in adding features that would penalize the landlord for mistakes - kind of contrary to our target market. The final strain on that relationship was when he said he wanted, in writing, a statement that we were equal and that I wasn't necessarily his boss.

It was around this time that I decided to focus on trying to advance at RIM. I continued to do well with my reviews and landed up working on the mail client for the PlayBook 2.0 refresh. This led to many very long days of development and constant travel for a period of months. Right after getting married, my wife kept asking why I just don't quit and focus on Well, I didn't have any connections with the startup world since I focused on RIM and the attempts I made in the past didn't work out so well. By this time, I really lost the passion for the idea.

I've since quit RIM to work at a very early stage startup (I'm employee #1) and still tinker with ideas on the side to see what the next big thing will be. My experience with has taught me some very important life lessons:

I hope Rentobo finds success and brings my vision to life. The world sure could use help making renting easier.