July 6, 2000 Entrepreneur of the Month by Maria Di Benedetto, Bizzed.com

Armed with only $1000 in her pocket, no job, no ties and nothing to lose, Catherine left corporate America to pursue her passion for travel in Asia in the early 1980s. Never did she imagine that she would eventually spearhead Silicon Alley's first IPO, or be the first female CEO to take a company public at 33 years old.

Catherine captures the bizzed entrepreneurial spirit by combining work with her life passions for travel and risk-taking.

Prelude to Entrepreneurship: Maybe Computers Will Be Big In the Future

Catherine graduated from Columbia University's Barnard College with a B.A. in Computer Science in 1980. This was actually the first year that Columbia offered students the option of a Computer Science degree. At the time, Catherine pursued it because she figured it would be easier than a Math degree. Ironically, she remembers saying to herself, "Maybe computers will be big in the future." She describes herself as, "Being a geek long before it was cool to be a geek. Back then, it was really uncool," she adds with a laugh.

After graduation, Catherine worked for three years as a computer programmer with a small company, then worked on Wall Street as an engineer. She wanted to go to business school, but with no financial support, she would have to pursue it at night for many years while working during the day. She did not want to get stuck in the grind.

She remembers thinking at the time, "I know I can do better than this. This is not really what I want to do with my life." This was her call to action. Instead of feeling trapped in her own life, she decided to take control.

Her Asian Inspiration

Catherine loved the author James Clavell, who wrote Shogun, Tai Pan and Noble House. Influenced by all of her reading, she was inspired to travel to Asia. Everyone thought she was crazy at the time, including her parents. Yet, her risk-taking nature riveted her to explore the unknown. A true entrepreneurial spirit. "So with no money, no job and knowing no one, I hopped on a plane to Hong Kong. I said to myself I'm 25 and I have nothing, so I have nothing to lose," she recalls.

After two weeks in Hong Kong, she found a job with Apple Computer's largest distributor and was first introduced to the world of multimedia. "For the first time, computers were being used for multimedia, entertainment, and education instead of just plain old word processing and spreadsheets," she says. Isn't it hard to imagine this was only 13 years ago?

A Visionary

At the time Catherine remembers saying to herself, "In the future, every PC will have a built-in CD-ROM." This seemed radical, but gave her an idea for her first business. Why not combine her own passion for travel (and desire to share that passion with others) with the technology of the future? She decided to set-up a company that would create and publish travel CD ROMs about the great cities and wonders of the world — a passion that heavily inspired her own life. Her idea was to devise 25 different electronic travel books with pictures and sounds.

Finding the Funding

But, where would she find the funding and support to get started? Again, everyone thought she was crazy. "Women just didn't start companies back then," she says. Catherine's drive and her relentless persistence gave her the courage to sell her idea to the right people in order to obtain funding. "Something deep inside told me that if you wanted something badly enough, you are going to figure out how to get it." She attributes this drive in part to being an avid marathon runner. In fact, she once ran a marathon in 3:17 on a 90-degree day. Catherine is a self-proclaimed extremist. "Somehow my mother subtly drilled it into me," she says.

She eventually sold her idea to the chairman of Merrill Lynch for all of Asia-Pacific. Hence in 1989, Catherine's first company, InterOptica Publishing, Ltd. was born. As one of the world's first interactive multimedia publishing companies, it became a multi-national company with offices in Hong Kong, Shenzen, China, San Francisco and New York. She eventually sold the VC-backed company to private investors, who moved it to the U.S. and took it public. It is currently traded on Nasdaq and has grown from $5 million to $300 million in sales.
Company #2: Hang in There. It Gets Easier Every Time

Catherine advises entrepreneurs, "The first time is the hardest. After you've done it once, it gets a lot easier...the personnel problems, real estate, customer service, everything..." And, she knows from personal experience. In 1993, she started her second company called Wanderlust. Her love, or should we say LUST, (Nasdaq: LUST) for travel inspired her idea to create children's educational CD-ROM games.

Wanderlust was using CD-ROM publishing long before the Internet was popular, but Catherine realized she needed a big brand name behind her to make her idea work and to remain competitive. Her brainchild was to license the Pink Panther for her educational games, but she knew it wasn't going to be easy. So, she used her stop-at-nothing attitude to approach MGM/UA for licensing rights. MGM replied, "This is our crown jewel — we can't just give you the Pink Panther!"

Catherine didn't take no for an answer. She was persistent, wrote up a proposal, and raised the large sum of money that MGM required for licensing rights. She had succeeded: She actually licensed the Pink Panther for her CD ROMS! Today, The Pink Panther's Passport to Peril is published in 18 languages, 25 countries, and has been a huge hit around the world.

In March 1996, Catherine oversaw Wanderlust's Initial Public Offering, which was Silicon Alley's first IPO. That made Catherine the youngest female CEO of a public company in America. Believe it or not — she never thought of doing anything like this when she was growing up.
Company Three: Forward Thinking and A Passionate Vision

Catherine started her next company, Soliloquy (www.soliloquy.com), in mid 1997 with 60 people and a passionate vision. Soliloquy will enable people to interact with the Internet by speaking. The company's goal is to make on-line shopping conversational and interactive.

"That's what every science fiction writer from Star Trek to Space Odyssey 2000 has always imagined — to be able to hold two-way dialogues with computers as if they were talking to a real person," Catherine adds. "The whole wireless world screams out for voice interfaces."

Catherine refers to Soliloquy's vision as the Next Generation of how we will interact with the Internet. "Voice recognition is the ears, and our technology is the brain behind the ears," she says. Soliloquy's Experts enable shoppers to hold intelligent two-way dialogues with websites by typing (or speaking) in natural language — using their own words. Talking to a Soliloquy Expert feels like chatting with a live person — except that it has total knowledge of all products, is available round-the-clock, and is a fraction of the cost.

"Voice recognition is not quite ready yet for prime time, but it is on the verge," she notes. The company anticipates introducing voice recognition functionality in early-2001, when it predicts the market will finally be ready for it on a large scale.

Catherine's Mantra

What are Catherine's secrets to successful entrepreneurship?
Be willing to take risks and live on the edge.
Be persistent and stop at nothing to follow-through with your goals.
Be organized and follow-up.
Learn how to schmooze and make friends in the industry.
Be passionate about what you do and love every day.
Never miss opportunities.
Time is more precious than money.
Travel!

We then asked Catherine if she had any regrets during her entrepreneurial journey. She replied, "One thing that is very important to me is to never have any regrets. Just go for it. Live each day to the fullest. Living a rich and full life is very important to me, so that I can never say 'I wish I had done this or that.'"

Finding Time for Balance as a Busy Entrepreneur

Catherine's work and play are rolled-up into one. Her social life — parties and dinners — are often work-related. "You could go to three or four Internet parties every night in New York. It is a very socially active community," says Winchester. It's not just a job; it's a lifestyle.
Making time for travel, her passion, is a priority. Every year, the week between Christmas and New Years — when business is very slow — she makes sure to take an exotic vacation. This year she will go to Burma. Last year she went to Bhutan. She has already visited over 70 countries. "Eventually, I will cover the whole world," she adds.

Managing and Motivating Human Resources in a Small Business Environment

Catherine's philosophy is that day-to-day business is the solving of a continuous series of problems. She believes that once you anticipate and accept this, it gets easier. "My first employee resignation in 1989 felt like a punch in the stomach," she adds wistfully. "But the second one was easier, and after all, it is inevitable as a business owner."

The sweat and tears involved in building a business may cause that first resignation to feel like a personal assault. However, in her 11th year of entrepreneurship, Catherine says she's calmed down a lot, reiterating the idea that it all gets easier after the first time.

She stresses the importance of making sure all new employees share the same vision and mission as the company. Catherine even wrote up her own human resources mission statement, which she uses when she interviews new employees. She spends at least x hour with each person before she hires them — no matter how busy she is. Catherine has not had a single resignation at Soliloquy, which she attributes to the way she runs her company — and to hiring the right people.

She even confesses to bizzed that some potential hires told her, " ' this feels too much like a cult.' " But, others told her " ' that they literally wept when they read our mission statement.' " She emphasizes that trying to find the right match before making a new hire is crucial to small business owners. "We are like one big family. We have a requirement that every single person has to be totally passionate about the company. If you want a job where work and play are all rolled into one, then this is the place."

She advises CEOs to give people a lot of responsibility and move the power down, but demand accountability. Frequent feedback and good communication are also crucial. "We are producing some of the coolest, most leading edge technology in the world, and radically changing the way people shop online, and this is enormous motivation in and of itself," she adds.