June 30, 2007

Bootstrapper Confessions: From the Beginning

Bootstrapping your own business can be difficult and stressful, to say the least. Below are my trials and tribulations as a bootstrapper over the last year and a half.

November 11, 2005: Dawn and I move into our first house which is a classic fixer-upper. It needs a ton of work.

November 17: I start looking for a better way to stay in touch with friends and family. Little did I know that this simple search would lead me down a long and windy road on the way to building a full-fledged social web application.

December 12: After realizing that existing forum platforms won’t suit my needs, I realize I am going to have to hunker down and learn how to program the application from scratch.

December 31: The Apple retail store I manage shuts down. I have no back up plan for employment.

January 1, 2006: First mortgage payment of $1600 is due.

January 7: We take a free trip down to the Florida Keys thanks to the future in-laws. My beach reading? PHP and MySQL Web Development.

January 20: Still no job in site. My time is split between learning PHP, fixing up the house, and looking for a job.

March 21: You guessed it: Still no job and Dawn and I are really starting to feel the financial pressure. The good news is that I completed the first version of Echonote and my family starts using it.

April 24: For better or for worse, I finally have a job. I’m an engineer at an electrical utility company.

June 1: After testing Echonote for a couple of months, I still won’t let anyone except my family into the site because I think it’s not perfect.

June 23: Echonote’s code becomes unmaintainable as I am a horribly sloppy programmer. I decide to start from scratch and rebuild the site. This time I use slightly better coding techniques.

July 1: I hire a javascript programmer through elance.com to build a single dynamic feature into the site. Promised completion date: one week later.

July 7: One week later: the programmer is not finished.

August 13: Five weeks later: I haven’t heard from the programmer in almost 3 weeks. I spend about an hour a day for the next 2 weeks trying to work with the programmer and elance to come to an amiable resolution.

August 25: Eight weeks later: After much aggravation and stress, the programmer delivers an incomplete project. It was the hard way, but at least I learned a lesson on hiring outside help.

August 31: The rebuild of Echonote is going painfully slow; work is taking up too much time. My free time outside work is consumed by Echonote, and I start to neglect Dawn, friends and family.

September 18: The second version of Echonote is done. My family starts using it and I realize that I added overly complicated features and dropped others that were essential. Usability testing is gold.

October 15: I still won’t let anyone use the site besides my family because I think it’s not perfect yet.

Feb 15: Down to Mexico for a week and again I have a programming book on hand. I finish reading Code Complete and am motivated to take on rebuilding Echonote for a third time.

February 22: I’m pretty sure I have contracted internet induced ADD.

March 2: I realize I want to make Echonote something more than just a hobby. I am somehow able to convince Dawn to let me spend a good chunk of our savings on a web designer.

March 7: I spend hours and hours searching for logo and website designers in the hopes of avoiding the situation last summer.

April 5: With a logo designer and website designer on board, the third version of Echonote begins to take shape. We hope to finish by June 1.

May 1: I make a commitment that I will become a full time web developer and entrepreneur by year’s end.

May 15: My relationship with Dawn is suffering. I am too focused on Echonote.

Jun 1: Echonote is no where near complete. I am distracted by other things in life and haven’t been giving the designers enough direction.

June 27: I get Pownced by Kevin Rose of Digg. Not only does Pownce have many of the same core features as Echonote, the consensus by internet users everywhere is that Pownce is a useless application. Is this an early death for Echonote?

June 28: After picking myself up after the Pownce debacle, I’m ready to move forward once again with Echonote.

Now all I have to do is finish programming Echonote myself, continue to guide the web designer, keep Startup or Bust up to date, and begin my next startup. This all is to be done while I build a patio for our house, plan our wedding, have a social life, spend time with Dawn, raise a puppy and oh yeah, work at my full time job.

Isn’t the bootstrapping life great?