Lesson #38

Payday . . . And Lessons from the IPO Road Show

One of the most exciting—although occasionally frightening—aspects of any business adventure and running a company is not knowing what the future holds or what issues of seemingly gargantuan proportions a CEO will confront. It can be a variety of issues and events—lack of money, incredibly difficult competition, recalcitrant employees, or grim economic conditions. The fact is that the more positive you make the journey—and the more you can gain satisfaction from solving the problems—the less you'll drive yourself to the brink with worry.

However, after a lengthy period of growth and reinvention, the next logical phase for every entrepreneur and his or her team is the payday, which rewards investors, employees, and yourself with some serious folding money. Most entrepreneurs continually reinvest money back into their company as a means for funding it and giving themselves the best chance of establishing something of real value, as well as staving off dilution as others invest alongside the entrepreneur. But there's always a point when the entrepreneur should take money off the table. Deciding exactly when this should be takes a combination of intuition, reading the tea leaves correctly, and realizing—in some cases—when the party might be coming to end. There are always signs pointing the way. The trick is to prepare to make the move before a crisis erupts or the trends turn in the wrong direction—because once that happens, ...

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