From Microsoft To Startup: Recognizing The Right Idea, and Getting Started

I am now a regular contributor to Seattle 2.0.  Here is my first post published yesterday.

One year ago, I walked into StartupDay 2009 with one question: at what point should I quit my secure job at Microsoft to work full-time on my startup? So of course Hillel Cooperman of Jackson Fish Market, the first speaker of the day, almost immediately said “don’t quit your day job”.

For the first time at StartupDay, I met successful entrepreneurs who had gone through what I was beginning, and their advice was priceless. For example, I learned there were options other than full-time job and full-time startup (e.g. consulting part-time).

I’ll never forget how StartupDay helped me rationally approach the decision to pursue my big idea and set more achievable goals. During lunch T.A. McCann, CEO of Gist, advised me not to quit my job before almost everyone I pitched my project to liked it. Suddenly I had an attainable goal to get me to the next step: fine-tune the idea first. Three months later, almost everyone we spoke to wanted to use our product, and we were ready to hit the ground running.

Beginning is the Hardest Part

The idea for LazyMeter came in June 2009. While I have business ideas every day, this one would not leave my mind, even when I tried to forget about it. I was at Microsoft for over 4 years, and I was comfortable. It was a recession and my colleagues at Microsoft were being laid off. My job was very secure and I wanted to quit? Go figure.

I met my technical co-founder at the August 2009 Startup Weekend. We were both passionate about solving the task management problem, and we went rogue to work on our unofficial project. The concept grew on nights and weekends and soon it became clear we would need to dedicate ourselves full-time to succeed. A business analyst at Microsoft, I naturally considered everything that could go wrong. I could run out of money. I could have a health problem and go bankrupt. My next big promotion was just around the corner. You get the point.

Worst Case Scenario vs. Potential Benefits

In the end, my analysis revealed the potential benefits greatly outweighed the risks. Realistically, the worst-case scenario was that I would have to get another job. However, now I would have built a product from scratch, which could mean finding a job I enjoyed more or paid a higher salary.

At age 27, this was the time to take risks. Everyone I looked up to professionally had taken a major risk in their career; most, even at Microsoft, had been involved in a startup. I also applied the regret minimization framework that I learned about at StartupDay, and it was suddenly a no-brainer.

Things Work Out

In January, I wrote a letter of resignation and clicked send. I am now a self-employed entrepreneur. My startup,, is near beta testing. I own an LLC with income from consulting. You’ve probably never heard of me, I haven’t received funding, and I’m living off a fraction of what I made at Microsoft, yet my quality of life and satisfaction have never been higher. I can’t wait to see what happens next.

Joining Seattle 2.0 As A Regular Contributor

I find it fitting that I’m submitting my first regular contribution to Seattle 2.0 this week, days before StartupDay 2010. Looking back on how I walked into the conference a year ago, and how I’ll walk in on Saturday, is extremely satisfying. My transition is still in its early days, and I look forward to updating you on my journey and lessons learned.


4 Responses to From Microsoft To Startup: Recognizing The Right Idea, and Getting Started

  1. Aaron,

    Thanks for the inspiration! I also left a well paying job and have laid it all on the line for my startup, now 1 year old. It is the best decision I have made in a long time and my quality of life has improved tenfold + . Congrats on your success and best wishes going forward. Seattle 2.0 is a great resource for both established businesses and startups. I look forward to reading more of your posts.

    Find or list business to business shared office space for rent in Seattle and nationwide at = my startup!

  2. afranklin says:

    Thanks for the note. Good luck to you as well – I will definitely consider your business when I’m ready to move out of my house.

  3. Bruno Lecoq says:

    Aaron – I was amazed by your story because mine is 99% the same as yours – For years, I was also ready to leave Microsoft and make the big jump – I also went to Startup Day 2009 and I came back home even more willing to jump off the boat! I left MS in March 2010 and started my company called BeMo ( – our product is in full beta right now. Like you, my quality of life and satisfaction have never been higher. I can’t wait to see what happens next as well – Good luck to you!

    • afranklin says:

      Thanks for the note Bruno. Congrats on moving on – it’s great to meet others going through the same experience. I almost wonder if we should have a regular meet-up group for those who left & want to leave Microsoft to found a startup. Good luck to you as well, and hope to run into you at an event soon.

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