My Startup Lesson Learned

A few years ago, I quit my job to build a bootstrapped startup called SandwichBoard–a content management system for restaurants. Patrick Joyce and I put $5,000 into the business and made a leap of faith to live off savings and occasional consulting gigs.

After we got the sales routine down, we were growing at a steady pace, but not early or fast enough for our personal lives. We both really wanted to marry our girlfriends. We needed money, and ultimately had to ditch the bootstrapping salaries. I was elated to be marrying the woman I had been waiting for my whole life, but throwing-in the startup towel felt like a huge loss. It was something I had been working towards for a long time, but giving it up to marry my wife was the best decision I ever made.

Now that I’ve had time to reflect on what went well and what didn’t, I have my own list of lessons learned–things I would do again or make sure never to go near when building a business or product. But you’ve already seen that sort of list before. Instead of dumping a bunch of do’s and don’ts on people, I would rather leave them with an encouragement–one that will give someone else the courage to take that leap of faith.

My lesson learned: even though the startup plane may come to a fiery end, the pilots have ejection seats.

Our efforts were not wasted. While building SandwichBoard, we became proficient in Ruby on Rails, resulting in a great product and more than two significant open source contributions. This helped land Patrick a position at a company called Hungry Machine and me a job at Razoo. Taking that risk propelled us from working typical IT jobs into the startup world. I’ve had fun just about every day since I took that leap of faith, become a better engineer at an accelerated rate, been able to work with incredible people, and turned that savings loss into a short-term investment.

Patrick’s employer renamed itself LivingSocial, and his first major responsibility was to develop a small site called LivingSocial Daily Deals. (Maybe you’ve heard of it.) I rejoined Patrick this July and am leading the technical team responsible for building LivingSocial’s latest local-commerce product: Takeout & Delivery–restaurant takeout and delivery ordering (currently only in Washington, DC). It’s a fitting end to the SandwichBoard story.

Results may vary, but I still think it’s worth a try. Give it a go; jump off that cliff!

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