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The executive to entrepreneur transition
Having conquered the world of big business, many corporate executives set there sites on small business or a start up as something new. Why? There are many reasons - change of scenery, change of pace, try something new, aim for the big buy out or IPO, etc. The transition is usually more difficult than most former executives are willing to admit. There exists this idea among large company executives that moving into a small business is easier than managing a large business because small businesses are, well, small.  So it must be easier, right?
Unfortunately, the transition from big company executive to entrepreneur is usually a painful one. Here are a couple of examples:
- Inside of a big business if the executive needs a copy, they send their admin down to the company’s internal copy center to do it for them. In the start up, the executive drives down to Kinko’s in the middle of the night to make his own copies.
- Speaking of admins, you usually don’t have one in a start up, which means you do all your own grunt work. Â
- At big companies most executives work predictable hours. In a start up you may still be up working at 1 am and have a 6 am meeting that same morning.
- Big company executives stay in nice hotels and fly first class. Entrepreneurs use orbits and stay at the Ramada.
- Big company executives focus on doing one thing (finance, sales, etc). Entrepreneurs have to do many things and must have a wide range of knowledge in many things.
- In big companies opportunities are usually understood and strategy is usually well defined. In start ups opportunities are often made instead of handed to you and strategy usually changes on a constant basis.
- Big company executives spend their time managing momentum. Entrepreneurs create momentum. Â
- In big companies you usually have the resources you need to get your job done. In a start up you are constantly fighting to make it work with limited resources.
The list could go on and on. The bottom line is the transition is hard and throws off many unsuspecting former corporate executives. Start ups are more fluid, which causes anxiety in many former executives. The instability is usually crushing.
I used to work in a big software company. My schedule was very predictable. I always dealt with the same people, I always had the same issues come up, I always knew what to expect. I think this is what a machine would feel like if it could feel.
Last year I was the CEO at 10Speed Media. I went back and looked at my calendar. Here was one of my days last July:
6 am to 7:00 am - check email, review calendar for the day and drive to first appointment
7 am to 8 am - breakfast meeting with a guy I was trying to recruit
8 am to 9:30 am -Â Sales meeting
9:30 am to 10 am - catch up on email
10 am to Noon - accounting and finance review with accountant
Noon to 1 pm -Â lunch meeting with new employee
1 pm to 2 pm - call with potential partner
2 pm to 3:30 pm - meeting with outsourced Web development guy to discuss building a new web site.
3:30 to 4 pm - drive to sales call - have phone meeting on the way to the 4 pm meeting with investor.
4 pm to 5 pm - meeting with potential client
7 pm to about midnight - review the business plan, catch up on email for the day, chat with CTO for an hour on development projects and fine tune the investor presentation.
As you can see the diversity of activity is incredible. Because of the narrow skill sets of most executives the learning curve is steep and crushing in a start up. Most executives didn’t want to or need to dive into these types of issues inside their former employers business. Now with so many issues on hand the new CEO is faced with two options: learn it or roll up into a ball and suck your thumb.  Â
All that said I have never met an executive turned entrepreneur who regretted the move. Entrepreneurship is exciting - it’s a drastic departure from most old school corporate environments. There is nothing like the feeling of blood pumping through your veins again.
Here’s my advice to executives thinking about making the switch to a start up. You need to first get educated. Dump your pride and talk to entrepreneurs and small business owners. Get their advice. Ask a lot of questions. Honestly evaluate your skill set. Ask co-workers to evaluate your strengths and weaknesses. Figure out your real level of commitment.
Once you’ve got that figured out and once you’ve committed - go to work and get it done.
And let me be the first to welcome you to the jungle.