I just got back from a short trip to Scottsdale, AZ for a family reunion on my wife's side. As always, I ran into a couple of successful entrepreneurs who have built large businesses (one employed over 600 people before exiting, another recently sold to a major tech company). Despite coming from a completely separate industries and business models, they both had two things in common:
1) Fear
2) Multiple irons in the fire
Fear:
The first entrepreneur spoke at length about how scared he was while running the business. He ran a manufacturing plant that employed 600+ people. In order to keep up with the competition, he had no choice but to outsource some of his technical work to India and China. The problem was, he was deathly afraid that they would steal his IP and begin competing with him. He took a leap of faith (the fundamentals behind the decision weren't difficult to analyze) and sent some work overseas. Ultimately, this boosted the company's growth, created even more US based jobs, and gave him the ability to exit the company at an incredible payout.
Entrepreneur # 2 experienced fear primarily after the company sold. Will he have a job in 2 months? Will he get the payout that he's expecting? What will he do next? ....etc.
The bottom line is that there's no way to escape fear as an entrepreneur. But, those that can harness this fear and transfer it into motivation seem to be the most successful in their ventures.
Multiple irons in the fire:
This one's tricky. As with most entrepreneurs, both of these guys were working on multiple investments at the same time. But....and this is a HUGE "but", they focused nearly all of their time and energy on one venture. Their other investments were managed nearly 100% by other entrepreneurs. I've seen way too many entrepreneurs get sidetracked trying to run multiple ventures at the same time. It's nearly impossible for one person to devote the type of management that a startup requires to more than one venture at a time. It can be done, but it's not a probably not a good idea. Let's face it, every entrepreneur has a million "next ideas". They'll all come in time. But, it's important to focus on your venture at hand or they'll all go nowhere!