I recently watched an excellent video from Gary Vaynerchuk called “You can have both…Jobs”. In that video, Gary talks about his personal experience in building his internet brand while working a full time job, and suggests that it’s very possible to pursue your start-up dream without leaving your job.The questions for most entrepreneurs are how to manage two jobs, how to determine when it’s time to either abandon or pursue your start-up dream full-time, and how to properly measure the risk involved.

Mike and I met in late 2006 with a former classmate of mine from high school who had started numerous successful online businesses. He liked our elevator pitch and asked a simple question: do you have kids? Sure – I had three (Mike had 2). He proceeded to talk about the effort in starting a technology business and pointed out that it was not a coincidence that most founders of technology startups are young and single. He talked about crazy hours, the hard work, sleeping under desks, and many more things we had read about in stories about technology companies. He wanted to make sure that our eyes were wide open to what we were about to experience.

In 2006 and throughout 2007, I maintained a very active law practice – I was a partner in a Chicago law firm and was representing U.S. and International clients in all types of complex commercial and intellectual property disputes. It was – in many ways – crazy to think that I could maintain an active law practice and pursue a dream I had from early childhood – ever since my family emigrated from Kiev, Ukraine – to start a technology company. I had opportunities in 1998 and 1999, right before the Internet bubble burst, but never found something that I was passionate about (probably a good thing). crowdSPRING was different.

I decided not to leave my law practice in 2006 to pursue crowdSPRING full time. We had not yet committed to forming a company (we did that in May 2007) and we hadn’t even decided that it could be a successful business. So – I was faced with an early choice – how much effort to put forth in doing the research and in trying to figure out whether we could make something of crowdSPRING.

In his video, Gary talks about having to work hard. Real hard. And it’s true. Ultimately, while bootstrapping is a popular practice, it’s not always so easy – both for professional and personal reasons. Mike and I set two milestones. The first was to give ourselves time to research, plan, debate, and determine whether we could build a successful business. We gave ourselves until the end of 2006 to do that. After we decided in late 2006 that we would aggressively pursue our dream, we set a second milestone – my transition from my law practice to crowdSPRING.

Meeting the first milestone – for me – was much easier than meeting the second. I was fortunate to have learned good time management skills early in my career and it was not difficult to replace many of my interests (movies, books, sports) to instead focus on crowdSPRING during the latter half of 2006. By the end of 2006, we decided, after much research, analysis, debate and planning, that we would pursue our dream.

In early 2007, I had to decide what to do about my law practice. We had not yet raised a penny in funding, hadn’t even incorporated our company, and were six months away from writing a single line of code. I had a very successful law practice, was working with my friends and mentors, and was fortunate to make a good living doing what I loved.

After much discussion (with Mike and with my wife), I decided that I would maintain my law practice and work on crowdSPRING until such time that doing both would negatively impact either my law practice or crowdSPRING. At the time, it wasn’t clear when that would happen, but it was really important for me to set a milestone tied to an event – a negative impact on either of my jobs. If I hadn’t set that milestone, I could have drifted for a long time and both could have easily suffered.

It was not easy to set that milestone. It would have been much easier to just leave my law practice. My friends know that I’m not afraid to take risk. But it wasn’t fear of risk that moved me to maintain an active law practice – it was the reality of startups. Most startups fail in their first year. Of those that survive past the age of one, most fail. Leaving at that time would have been foolish – while there are stories of young adults founding successful internet companies and selling them for hundreds of millions of dollars – those stories are scarce. There are far more stories about those who didn’t make it.

At the time, we had no idea how successful crowdSPRING could be. We knew we were on to something important and exciting. We knew that we desperately wanted to pursue our dream. And we committed to work hard to do so.

For me, the most important decision at that time was the time investment necessary to work two jobs. I recalled our conversation in 2006 with my former classmate and his caution about technology startups and the time required to run them successfully. I wasn’t afraid of hard work, but I was terrified that I could not balance two jobs and my family. In early 2007, my oldest daughter was 8, my son was 5 and my youngest daughter was 1. My wife and I discussed the pressure this would put on our family, the need for her to take on more responsibility with the kids, and the extra work I would have to do to continue to create some balance of work/family.

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