Seconds, Please

When business No. 1 is done and gone, how do you find the creativity to start business No. 2?
Magazine Contributor
4 min read

This story appears in the January 2001 issue of . Subscribe »

Is there life and creativity after start-up No. 1? If you asked me that question last year, I probably would have said "No way." In the fall of 1999, after nearly five years of running my first company, Cybergrrl Inc., I decided it was time to move on to those proverbial greener pastures.

To say I had mixed feelings about leaving my start-up would be like saying a monsoon is a slight shower. My thoughts and emotions were in chaos. I felt guilty about leaving behind the company that was built on my blood, sweat, tears and increasingly gray hair. I felt irresponsible. I felt angry. I was terrified. I felt utterly drained.

Then, suddenly, I was unemployed. But I was certain I didn't want to go back to being an employee. As timing would have it, my good friend Amy was reevaluating her employment situation and feeling like revisiting the world of entrepreneurship. Amy and I began brainstorming business ideas-over cocktails, over Sunday brunch, over her kitchen table-because we had always talked about starting a company together. The mission of my first company was to empower women to get online and use technology for their personal and professional gain. I knew that whatever I did in my next entrepreneurial incarnation would have a similar mission. Amy shared that vision, as her first company was a women's online health pharmacy.

After riffing on numerous concepts, we decided to create a multilingual business site for women. Why? Because nothing existed like it, and we were certain there was a need for it. Eventually, we pared that concept down to an online network and marketplace for Hispanic women in business. We finally settled on the name EVIVA, "e" standing for electronic and "viva" for "she lives." A company was born.

As you can see, creativity doesn't stop with that first business. How have other entrepreneurs come up with the ideas for their new, new thing? For James Marciano, starting his second company, Refer-It (a directory of online affiliate programs), actually happened while still running his first, (an online community consisting of the students and graduates of the top 20 universities in the country). Explains the New York City entrepreneur, 34, "I needed to generate additional revenue for TheSquare. I stumbled across's associate program and thought it was a good idea. When I looked for others to join, I couldn't find any! So, as with TheSquare, I built it, figuring others needed the same thing."

Jeff Stewart came up with the idea for his second company,, in 1992, years before even starting his first one, Square Earth, a developer of Web-based applications for major corporations. What was his inspiration? "It was the pain of standing in line at a Kinko's only to find they had not yet finished my order," says Stewart, 31, whose New York City-based allows users to submit their documents via the Internet for high-quality printing and overnight delivery. "I'm glad I didn't pursue the idea at that time," he adds. "Without the Internet [in 1992], the business wouldn't have happened."

Stewart and co-founder/CTO David Uyttendaele sold Square Earth for equity in 1998, and over the years, they kept coming back to the idea of the hybrid printing service. After selling Square Earth, they found the time was right for Mimeo. "This is a perfect example of good things happening when you have the patience to wait," says Stewart. "I am addicted to adrenaline, and nothing could be more exciting than starting and building a business. The thrill, the fear, the danger, the possibilities of high-stakes business creation . . . there is nothing else like it."

Having a new start-up to develop was therapeutic for me, as I still felt an emptiness from leaving Cybergrrl, and I was grateful I hadn't run out of ideas. And I soon realized that one of the most important traits of an entrepreneur is the ability to constantly come up with innovative concepts, either for a current business or a new one.

Aliza Pilar Sherman is an entrepreneur and author of several books, including Cybergrrl @ Work: Tips and Inspiration for the Professional You(Berkley Publishing Group). She is writing her third book, a motivational book for women in business, for Entrepreneur Press (due Fall 2001).

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