Pilot Entry: Why I quit my job to do a startup

My name is Leo and this is my blog. Through this blog, I intend to document my life as a startup founder and share my mistakes and lessons learned. I hope to inspire other would be entrepreneurs as well as exchange ideas & advice with those close to the startup community. Our startup is still in stealth mode (entry on “Why Stealth” to come) so I will not directly discuss the idea until our launch this summer.

On January 31, I quit a management/strategic consulting job that I loved to pursue a startup. It was a tough decision because I enjoyed the work, enjoyed working with some of the most talented people I’ve ever met and had many opportunities had I decided to stay. I will outline how I arrived at my decision in this post. Every time I make major career changing decision, I always think of the worst case scenarios and worse possible outcomes – I believe if you’re prepared for the worst outcomes and can accept the consequences, then you will unlikely regret taking that step.

Three primary reasons why I quit a 6-figure job to do a startup:

1.       Timing/Risk Tolerance

There’s no better time to do a startup than when you’re in your 20s and it’s the only time in life when you have the freedom to be independent and do whatever you please. When you’re in school, most of us are financially dependent on our families. When you get married and have kids, you have responsibilities and lower risk tolerance. The few years between graduation and marriage, you’re financially independent and no one to really take care of but yourself.

When evaluating whether I should quit my job to do a startup, I noticed a sharp contrast in advice from those with entrepreneurial experiences and those who didn’t. Those who hadn’t started a company advised me to work a few more year, develop more experience – those who were young entrepreneurs themselves encouraged and supported my decision. After doing some research on my own, it became clear that I this is what I wanted to do. I was prepared for the emotional ups & downs, prepared to work hard and most importantly, I wasn’t afraid to fail and start from scratch doing something I love.

Paul Graham has a couple of great essays that inspired my decision: How to Start a Startup & Why to Not Not Start a Startup. My favorite quotes are:

        “If you try something that blows up and leaves you broke at 26, big deal; a lot of 26 year olds are broke.”

        “But the best way to get experience [doing a startup] if you’re 21 is to start a startup” (I’m already 25 so a bit late on the train)

My high school buddy Justin also inspired me. Justin had started a company (Kiko) right out of college to make an Ajax calendar, they worked for a year and things were looking up until Google came out with their own Ajax calendar. Kiko wasn’t wildly successful but they sold on ebay for $250k and the founders got a decent 1 year salary. Most importantly, they did something they loved and developed the contacts and skills to move right onto their next startup, Justin.tv.

2.       The Idea & the Plan

I always hear from people that ideas are a dime a dozen; it’s more about the people and the execution. Though I wholeheartedly agree with this, I believe it’s more true from an investor’s point-of-view as they’re constantly being bombarded with ideas. As a founder, the idea is crucial. Without a solid & well researched idea and a solid plan, I wouldn’t’ve quit my job to do this. I’ve batted around hundred of ideas with friends over the years only to arrive at 3 common conclusions: too many competitors doing the exact same thing, there’s no market for our product – alternatives are working well, and there’s no way to effectively monetize.

When my partner Adam & I came up with our idea back in Sept/October, we spent nights & weekends researching the idea and tried to poke holes in it until we were certain that it’s able to hold water. Maybe it’s due to our business backgrounds but we didn’t want to be another “me too” web startup with a cool application but no clear vision and strategy for monetization – the web is already too crowded for that.

3.       The Team

An equally important part of my decision to pursue a startup is because we had a great team. Although it was just me and Adam with no developer, I knew we could make this happen. We both had an obsession with internet startups & web applications and complimented each other’s strengths & weaknesses very well. When we discussed our roles in the company, we naturally gravitated to our interests & strengths and clearly defined our positions. Adam is the savvy CEO with solid analytical skills, passion for online marketing, and great people skills for interacting with investors, customers and the media. I’m the COO, I like to crunch numbers, guide product development, manage internal operations and come up with wild ideas. (Few days ago I was surprised to find that Brad Feld doesn’t believe in COOs, but after reading his thoughts, we seem to fit well in his 2% exception.)

In an early stage startup, there shouldn’t be too much redundancy in skills – when you’re strapped for cash and low on resources, redundancy just makes it more expensive to get the same work done.

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3 Responses to “Pilot Entry: Why I quit my job to do a startup”


  1. 1 The other Leo March 12, 2008 at 12:22 am

    Hey Leo, congrats on the new start! Best of luck with your plans!

  2. 2 MySelf July 11, 2010 at 9:54 am

    You FOOL! I oughtta slap you if i could time travel!

    • 3 anonymous January 6, 2011 at 5:42 pm

      Does that mean that you failed? If so why? I’m looking to quit my job and venture down your same path, only I’m not making 6 figures. So less to lose!


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