Swimming with Sharks

An interview with Christine Comaford, managing director of Artemis Ventures.
by Sally Richards

She's young, she's hip, she's happening - and she's so smooth and stealth-like when swimming with the sharks who infest the venture capital pool in which she makes a living. Everything about Christine Comaford says she's going to retire a very wealthy woman. It's been a long road, but she's had a blast every mile, and the journey isn't over yet.

Comaford has learned from her mistakes and grown from her successes. But you don't wake up one morning and say hey, I'm going to be a venture capitalist. Far from it. You build up to success in this business, it's somewhat akin to a Girl Scout merit badge sash - you have to earn one badge at a time, each badge needing the complete mastering of a single skill, each successful achievement raising the bar a little higher until the sash is completed.

This story begins when a younger Comaford began learning life's lessons about risk-taking and its rewards. It started out with a call to Microsoft. Comaford placed a cold call to MS headquarters and told a total stranger at the other end of the line that she could help with their software's limitations. Nothing ventured, nothing gained, right?

"I came across Microsoft Windows and I called them up and said 'Hey, this Windows thing is a great idea but it's a really lousy design and if you want a real butt kicker you're going to have to fix it,'" says Comaford of her introduction to Microsoft. "And this guy - Scott Somebody, who got fired shortly thereafter - I called him Mr. Tiled Windows because he said no one would ever want overlapping windows. He was into tiled windows and he eventually got booted by the lack of vision department. 'Well,' he said, 'if you're so smart, why don't you come and fix it?' I said, 'great, I'll be there in an hour.'

"When I came on board it was decided that maybe Windows wasn't doing so great. And we were going to do OS2, this was '86. We did the OS2 graphics engine and I got to see what it's like to develop code with IBM, which was an absolute nightmare. They'd send the code to us at night because there were five development shops working around the clock from different time zones. Often we'd have to rewrite it because the engineers were paid by the line of code, so their code was so friggin' sloppy that we just couldn't stand it and had to rewrite it. It was grueling."

Comaford was brought on board as a contractor to help Microsoft build a better product. When the Labor Board came down on Microsoft about contractor laws, the company held a meeting and said it was going to have to lay off its contractors until it could find a company to take them and contract them back to the company. Comaford stood up and said "I have a company, I could do that."

This was 1987 and Comaford was 27. With the chutzpah of someone who knows no fear, she took out her Visa, pulled out Inc. Magazine and looked in the back ads for a company that could incorporate her. She then called PayChecks, established a payroll account and extended her credit to the max to pay her staff.

"My first venture capitalists were MasterCard and Visa," jokes Comaford. "Then, I made a deal with Bill that I would give these people back in two years." That was Comaford's first company. The serial entrepreneur bug bit her and she founded four more successful companies. With each sale she garnered more business finesse and confidence. A little more than 12 years later, she's advised several Fortune 1000 companies and has given advice to President Bill Clinton, Vice President Al Gore and First Lady Hillary Rodham Clinton. She moves in the "in" circles and with a phone call can change the course of history for any company she believes in.

Women all over the world look to Comaford as a role model, but life wasn't an easy rode for her.

"I think a lot of things about women in technology starts early," Comaford says of the mindset instilled early in young girls. "Women are discouraged from science and math classes early. So encouragement really starts with the parents, and I didn't really get that type of socialization when I was growing up. Deciding that you're going to do something with your life either comes from your parents, or it comes from tragedy. I think tragedy is a really brilliant motivator. People will either say I can't handle this pain, I'm going to crawl under a rock, or they say I am going to survive! That's where my school of thought came from. I said hey, my home life is an absolute disaster, I am going to survive, I'm out of here, I'm going to forge my own way. I'm going to make mistakes but it doesn't matter, they're going to be my mistakes and that's fine. The silver spoon thing is not necessary to be a successful woman in business. The Harvard MBA thing is also not necessary, it's not like I grew up in this household where every morning there was a fresh sticky note on my mirror saying Oh, you rock! How fabulous you are! You have to do that for yourself. I put those sticky notes up myself.

"I totally believe you create your own destiny, and everyone has opportunities in their lives, everyone is responsible for building their own self-esteem. People have to get within themselves and find their strength, whether it is through spirituality, or whatever and say I am worth a lot, I have amazing potential."

Comaford has come a long way, but she never lost her inner-faith, although it may be kind of tough to find on some mornings. "There are days when I say - hey, this business world, man, I'm sick of it! Sometimes I feel like I've been swimming upstream for so long that I'd love to be Martha Stewart and just worry about what type of blow torch I should buy to make my crème brulee perfectly? What a great problem to have - a shopping challenge."

Working 24/7 in a world where everything moves at the speed of light - including money transfers and your competition's IPOs, it's easy to lose perspective of what's important. On those days when a deal falls through, or when she's wishing she was Martha Stewart, what does Comaford do to get herself back online? "I reconnect and think about how grateful I am to have what I have in my life. How lucky I am to be in this industry at this time - to be around all these amazing, smart people - some who are incredibly philanthropic and use this opportunity for great good, and how inspiring that is. I just look at my life and say this is a great life, what can I go out and contribute today?"