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I’m working on a series of articles about mentoring for women business owners for a client of mine, and it got me reminiscing about my own mentors when I had my Internet company back in the 1990s. While my articles will be filled with tips for finding a mentor (or finding a mentee), I have to admit that my own path to my three key mentors was much more serendipitous.

At the time, I was the first woman to start a full-service Internet company in Manhattan that focused exclusively on creating content and community for women on the Web. All of our sites (Cybergrrl.com, Webgrrls.com and Femina.com) focused on a female audience and all of our clients focused on the women’s markets. But at that time, there were no women at the helm of new media companies, particularly none bigger than my own company from whom I could “learn the ropes.” Finding a mentor in my industry was a major challenge.

So here is the story of My Three Mentors. I think you’ll be surprised where I found them…or how they found me.

Mentor #1 - The Dad

While running Cybergrrl, Inc., I received hundreds of emails each day from fans of our work and spent 3-5 hours in the wee hours of every night answering each one personally. One email was from the father of a boy and girl asking me how could he engage his daughter more in computers. His son was very interested in the family computer but his daughter wasn’t.

“What web sites would you recommend for my daughter?” he asked.

“How old is she?” I asked, ready to craft a careful and appropriate list of site recommendations based around his daughters age.

“Three,” he said. I immediately loved this guy.

After more email exchange, I finally glanced at his sig file. He was, at the time, with @Ventures, one of the early Internet venture capital firms. And he offered to help me in any way. His name: Jerry Colonna who later became a partner in FlatIron Partners, an extremely influential VC firm in the early days of the Web 1.0.

Wow! A venture capitalist was offering to help ME out? I was so green in my business that didn’t know what to do with that information even though I knew it was important. I ended up visiting him periodically for advice that turned into really deep and philosophical discussions about business and life.

Jerry eventually introduced us to my company’s first major investor. Then, at the most difficult time in my business - when I was having conflicts with my business partner - Jerry was there not to judge, but to offer perspective and support. Jerry has remained a friend over the years as well as someone I truly admire.

Mentor #2 - The Straight Shooter

My next mentoring relationship came about when I received an email from a man asking for permission to use my Cybergrrl logo (a cartoon of myself that I drew by hand on my computer with a hot pink cape and bold yellow “CG” on a blue breastplate).

“I’ve actually been using it already to demonstrate an animation product I’m working on called FutureSplash,” he confessed. “Just showed it to the folks at WiRed magazine.”

Turns out, the guy was Charlie Jackson, a maverick venture capitalist from California and FutureSplash was the precursor to Adobe Flash. We immediately connected when he told me he had built an Olympic quality shooting range and that the US Olympic team was starting to use it for training. I was a gun owner in Manhattan, toting my 9mm to the range at 20 West 20th for target practice so was immediately intrigued.

Charlie ended up spending some late night phone time with me as I worked on revamping a business plan for the next rounds with VCs. He was generous with his time and unreserved with his critique. I appreciated his no-nonsense advice and gained a much better perspective of how to separate myself from my business.

And eventually, I did get a tour of the shooting range.

Mentor #3 - The Guru

The email exchange between my third mentor was very telling - about the nature of email networking, that is.

“I love the work you are doing for women online,” read the first one from Samir Arora.

We began exchanging emails periodically, and Samir was always praising me for my mission to empower women through technology.

Eventually, Samir was going to be in New York City on business, and I was thrilled to be meeting up with my email mentor.

“Let’s meet for dinner,” Samir wrote.

“Great! What do you look like? You know what I look like from photographs,” I said.

The response included “short dark hair” and “dark skin.”

And then I realized that after all these months I forgot to ask a critical question to recognizing Samir at a crowded restaurant.

“Are you a man or a woman?”

Of course, anyone familiar with Eastern Indian names would know that Samir is a male’s name, but I didn’t and for months had been corresponding with Samir without ever knowing if he was male or female.

We met for lunch or dinner on a number of occasions when Samir’s work found him in Manhattan. And our discussions were filled with references to Zen Buddhism and “finding one’s passion” and all of the terms and philosophies that hadn’t yet caught on as the “next wave of business.” Samir taught me to be true to myself, to not be afraid to run a business based on my personal integrity.

While I’m not in touch on a regular basis with any of my mentors from the 90s, I do know that I could send an email or pick up the phone and call today and all three would be there for me.

Here are some of my tips for fostering a positive mentor/mentee relationship:

1. The mentor/mentee relationship should be mutually beneficial and yet approached without any expectations.

2. That said, you should still outline your desired outcomes such as “I’d like to learn how to better handle the growth of my company.” In my case, I had distinct issues that I presented to my mentors based on what was happening with me and my company at any given time.

3. Use all available forms of communication. Back in the 90s, we had email, phone and in person. Today we have IM and audio/video conferencing such as Skype. Coordinate with your mentor based on their preferences and capabilities.

4. Don’t take the relationship for granted. Friendships do form from mentor/mentee relationships but in many cased, they do not and things stay on a purely business level. Don’t diminish the value of those relationships and the guidance you can receive from them. And remember: your mentor is NOT your psychotherapist!

5. Keep an eye toward the positive. You should never leave a mentor/mentee meeting feeling beaten down and hopeless. But don’t always expect sunshine and daisies either. Even in the bleakest situations, there are positive ways to change and grow. A mentor should be able to help you see that proverbial light at the end of the dark tunnel.

6. Know when to walk away. Not every mentor/mentee relationship is a good fit. Trust your gut and if something doesn’t feel right, be courteous and thank them as you say goodbye.

Who is YOUR mentor and what have they helped you with in terms of your business?