The 1 Thing Experts Miss About Taking the Startup Leap

Leaps are fun, dangerous, and scary but do you have a choice?

For as long as I can remember, experts have expressed the decision to start a company as “taking a leap“. The metaphor is obvious -the actual moment you leap is fraught with fear. People leap into marriage (think about jumping over the broomstick). People leap off bridges attached to a bungee cord (this is the image I have in my brain and a framework for the rest of this article).

In order for the metaphor to work or at least create enough drama, the difference between the starting point and the ending point has to be wide or deep. There has to be a considerable distance between the before and the after.

The typical startup leap is the one from a corporate job to a startup role. The leap is perceived as even greater if your corporate role comes with role prestige, compensation, or any of the corporate trappings (remember a car allowance?).

For some reason, I don’t see the startup leap metaphor working if you exit college and join or create a startup. There is not enough distance in that movement to warrant characterizing your move as a leap. It feels like you are jumping from the sidewalk to the street.

One of the other key components of a leap has to be the level of commitment to the jump. If you are just ideating on your idea and working it at night and on weekends, I don’t think you can tell your friends that you made the leap. The leap has to be an all-in affair where there are no other options available to you after you jump.

Experts also weigh in on when the right time is for a leap. I think about the time and effort you need to do to bring you to the point of the jump. It is only after you reach your personal minimum level of preparation will you be ready. That moment is different for everyone.

I have written many times about the individual preparation you can undertake that helps you get ready. Think of these elements like researching the organization that sets up the bungee jumps, reviewing their safety procedures, talking to friends to get psychologically ready, etc.

In Startupland, these preparations can be viewed in four different areas:

  • financially,
  • emotionally,
  • physically, and
  • intellectually.

Until you address each of these to your personal satisfaction, you will not be able to jump.

So, what is the one thing that experts miss about taking a startup leap? It is that leaps are fundamentally based on leaving something behind.

All the mental work in the world will not prepare you if you are not ready to leave the past behind you.

That past can be a job (with all of the accouterments) or a standing or position with your family or community. The past can be a certain important aspect of your personality. It does not matter what the past is – it is only important to know that once you leap, you leave all of that behind you.

Speaker, investor, mentor, startup founder. One of 3 or 4 Co-Founders of MapQuest (sold to AOL for $1.2B). Managing Director of $25M Venture Fund in late 90's. CEO, COO or President of various companies ranging from $200k to $20M in size. One of two Managing Directors of The Startup Factory (35 investments across 7 cohorts), founder and MC of the Big Top Reverse Job Fair and national writer and speaker waxing poetic around startups and startup communities. Currently EIR @ Techstars with Brad Feld ~ Startup Communities, to help community leaders around the world grow their startup community.

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