Graham Brooks of .406 Ventures might have been quoting someone last night at North Eastern's EntreTech forum event hosted at the EEC when he said “Being an entrepreneur is like jumping off a cliff without anything, but hoping that you can pull together a parachute before you hit the ground”.  He’s not so far off, but it really struck home as a wonderful way to start this blog about knowing when to leap.  I don’t have the answers, heaven knows I was not ready when I jumped into my start-up late in my undergraduate days, but in my current role as lawyer and advisor to start-ups it’s important that I can at least help my clients know that they have the tools and the fabric to put a parachute together before they jump.  If they build a para-glider, a parachute or end up with a lump of plummeting fabric is any ones guess.  So what am I blabbing about?  An issue that many entrepreneurs have to deal with – When do I leave my steady job to devote full time to my start-up. 

The biggest common denominator in dealing with successful start-ups is still luck.  Luck as I define it is being in the right place at the right time (so be prepared to be in a lot of wrong places, before the right time comes along).  You want to at least stack the odds in your favor.  Technology start-up entrepreneurs are usually smart, and have technical skills to boot which makes them very employable.  So it doesn’t come as a surprise that many start-up entrepreneurs have regular jobs working days, before coming home to work several additional hours on their concept or idea while still dealing with all the other aspects of life like family and friends, chores and errands.  They usually have some kind of team in place and some of them have gone far enough to create a corporate entity and have taken care of the usual start-up documents and legal strategy that I recommend.  However, the question still looms – When can I give my two-week’s notice?  When can I spend days and weeks working on this idea, rather than cobbling together a few hours after work and spending weekends making incremental steps? 

 Your regular job, even if it is drag, is an antithesis in the risk spectrum to your venture.  It offers security and a constant stream of cash flow.  Your start-up is exciting but will most likely result in a negative cash flow.  How do you align the two?  I often counsel prospective leapers to think about it (staying with the parachute theme) as an issue of altitude.  Think of your current job as the plane rather than a cliff.  With a plane you now have the ability to not only fly higher than the cliffs, but also to safer locations ((if there is such a thing)) to make your jump or to an area where a jump is more favorable (think updrafts, jumping over a depression etc.  Note: I have never jumped out of a plane so pardon the tortured analogies).  Like the plane, your regular job keeps you in an environment that might be able to weather certain financial storms that would adverse to any new venture.  Your job also helps you build a pool of savings that will be vital when you make the switch to go full-time into your venture.  Think of the money as altitude.  The more money you have to boot-strap your venture, the more time you have before you have to deploy that parachute.  Furthermore, use the time to build your team and pick up the technical skills that will be crucial when you are going full-time on your venture.  There’s another aspect to the job that’s intangible yet crucial - it’s a security blanket, its assurance that you have your feet on the ground.  Athletes often talk about visualizing the moves they are going to make before they get on court or on the field.  Usually this visualization happens in a calm external environment away from the field of play.  Think of the time, before you leave your full time job as the time for you to run through the visualization exercises of what you are going to do when you jump off that plane. 

On the flip side, being on a plane means that you could crash before you even get up to the right altitude or you could get seriously hurt while jumping out of a moving plane (yeah, I know we are talking about jumping from high locations in both instances, but just humor me).  Likewise, you should be aware of several risks while you are working at your current job and moonlighting as a start-up entrepreneur that could mean disaster when you make the jump.  Be aware of what restrictions apply to you while you are still with our current employer.  If you are in a senior enough position, or in a specialized role, your agreement with your employer, might forbid you to work with another entity after hours.  If you have a focused specialization, your agreements might automatically assign the work you do in a specific area while employed to your current employer.  Your employer might have certain trade-secrets and you need to be sure that you are not infringing on these.  It is possible that under your agreements, any works done on the company’s time using the company’s resources will belong to your employer.  What I am saying is make sure you know the scope of your engagement with your current employer.  This extends to restrictions that might apply once you have left like a non-compete and the inability to hire away other co-workers (this could be an issue if your co-founders are also co-workers).  The best way to deal with these problems is to first, understand your risks and second, be proactive in managing them.  I have seen cases where the former employer will sometime be the first client for a start-up (because they have figured out a way to solve a pain-point) or even be a potential acquirer of the start-up business down the line.  In both instances it helps to leave your employer on good terms and with a common understanding of the work you are going to be doing and how it does not jeopardize any existing agreements you might have. 

 In closing, there will come a time to jump, you will know it, yes it will be terrifying, but hopefully you’ll be high enough, have all the right tools and materials and know what you have to do to put together that parachute/paraglider in time.