Mar 21, 2013 · 10 minutes

I’ve promised myself many times that I would not write about gender. And now I’m breaking that promise.

It was probably inevitable, but it has been catalyzed by the hype surrounding Sheryl Sandberg’s new book, and the litany of response editorials that are proving unavoidable for those of us who read a lot. And, not surprisingly, almost all of these articles are written by women.

That being said, all of these women are also asking men to get more involved in gender dialogue — so I’ll take them at their word. Let’s hope they actually want to hear my opinion. Furthermore, I bring a unique perspective to the conversation. Here’s why:

Seven years ago, I started a sports Web company that catered largely to male consumers. Not surprisingly, the overwhelming majority of our job applicants — and therefore our employees — were men. I interviewed hundreds of them over the years, and hired dozens of them.

(During that time, I also hired several outstanding women in approximately the same proportion as I did men, though based on a far smaller applicant base.)

What a lot of people don’t know is that I have spent the last two months quietly starting a company that caters to a predominantly female demographic, and now I am interviewing a lot more women than men.

Having started a “company for dudes” and a “company for ladies” — and having interviewed a statistically significant sample of each — I bring some great empirical insights to the conversation, and I am going to share them.

The purpose of this article is simply to share these observations. It is not to tell men or women what to do differently.

Observation No. 1: Women hear me out

Hiring women in product and editorial capacities is tough for me, because I have few inroads to the major media companies, most of which are in New York. And so I have randomly contacted dozens of talented women using LinkedIn or other “cold email” tactics. And guess what?

A lot of them are getting back to me.

They are incredibly responsive to the interest that I am showing in their careers, and I am being rewarded by having a lot of great conversations with potential candidates.

The reason for this great response rate is likely two-fold. First, I think that women are particularly introspective about their careers — they want to talk about them and think critically about their next move. Second, I think that they are great listeners. I’m not the first person to make this observation, but I have been floored by how many insightful and on topic questions I get when talking about my future venture. It only now dawns on me how often men turn a conversation about anything into a conversation about themselves (or what they think, who they know, where they’re going, etc.)

Some have suggested that listening is not a trait that leads to recognition. That’s only true if it implies not talking. The best people are great at both. And people who talk without listening are incredibly annoying.

The most important part of an interview occurs at the end, when the candidate asks the hirer questions about the business. I have routinely noticed that women are strong in this area, and it is an asset that gets noticed.

Observation No. 2: Women feel a sense of commitment, for better or worse

Yes, they hear me out. And they ask great questions. But there’s something else that these women do that surprises me.

They say “no” — before we take the conversation much farther.

In each of these cases, the “no” has been incredibly polite and reasonable. Their disinterest is rooted entirely in their commitment to their current employers. In some cases, it is because they are “extremely satisfied” with their current job. Often it is because they feel “a sense of finishing what I started.”

Men seem far more likely to leave a job after eight months to take a higher paying job. And even if they are not serious about leaving, they are much more likely to run through the motions of getting the offer, so that they can leverage it against their current salary.

As an employer, I am impressed by the trait of loyalty, and I like the honesty that women exhibit by saying “no” without wasting my time. But neither of these things is going to reflect itself well in a person’s compensation. Because the number one catalyst for getting a raise is not high-performance... it’s having another offer.

And even we startup people reward loyalty far less directly than we should. Sure, we offer equity vesting schedules that provide long-term rewards. But we also hoard our scarce capital in such a manner that unprompted raises are a rarity.

The nature of compensation — and the unfortunate short-sightedness of how we reward people — hurts women in this regard. But it’s also a problem that is incredibly difficult to solve. Heck, our entire Great Recession was ultimately the result of messed up compensation structures at banks and rating agencies. And six years later we are barely starting to address it.

(Interestingly, Human Resources is one area of a company where women have disproportionate representation. So I encourage HR leaders to keep finding ways of rewarding long-term commitment, not short-term gain. It will help gender disparities.)

If I could offer one thought to women, it would be this: Make sure that your employer deserves your loyalty. Far too often I hear women grumble about their jobs, only to say something like “...but I want to finish what I started,” or “I feel like I can help them change their way of doing things.” I’ve also heard many women say, “I know that I don’t hold shares, but I still feel a tremendous sense of ownership.”

Don’t say any of those things. Just move on. That’s not business advice, that’s a respect issue.

Observation No. 3: Women value transparency in life and in their careers

A lot has been written about "risk" and the theory that women embrace it less frequently. I’m not going to address that point, because others have already done it so many times. But there is a slightly different — and related — phenomenon that deserves its own section.

Women value transparency in work and life.

I’m amazed at how much detail women ask me to go into when I tell them about a job opportunity. Every day, I find myself saying things like, “Honestly, I don’t even know yet. I’ll have to think about that and get back to you.” It only now occurs to me how often men are ready to jump into a job without really knowing what lies ahead.

Women seem to value employers who can lay out a clear view of what the next 10 years will look like at their firm. When I worked at Credit Suisse and Deloitte Consulting prior to entrepreneurship, I was impressed by how clearly they laid out their career treks.

This created an environment where one could better anticipate and model their lives around a clear game plan. It was also an environment where one’s mentors were particularly useful, because you could emulate their successes.

Furthermore, whenever I participated in a semi-annual "goal setting" exercise for my performance review (as both an employee and executive), it was always my male colleagues (or employees) who rolled their eyes and half-heartedly participated. Women did the opposite — they were thoughtful about their goals, milestones, and plans.

And it wasn’t just at work.

In school, women will always perform better, because they actually hold on to (and read) that course plan that the teacher hands out on day one. It wasn’t until college that I even held onto mine past the first week.

My high school class sent four people to Harvard — all of them were women. They were better represented at all the top colleges. Because they were better at school.

In fact, I am generally disgusted by how long it took me to "connect the dots" on how to perform well in school, considering that the course plans and rubrics were always right there in front of me. Every year for 16 years.

But, then again, I hate rules.

I suffer two great phobias in life. The first is claustrophobia. (Packed subways terrify me.) The second — and more impactful — is my fear of knowing what I will be doing in 10 years. I don’t want to know. I want to imagine. I love the fact that I was an entrepreneur last year, a writer this year, and will likely be something entirely different in 10 years. Perhaps I’ll run for office or publish a novel. Who the hell knows, but I love that nothing is definitive.

I don’t speak for most men, but I speak for a lot of them. There are also women who share my phobia for "life transparency," just as there are women who say “screw the rules!” like it’s a mantra. But I’ve met far fewer of them.

Why is it that women have made greater strides on Wall Street and at Augusta National than they have on Sand Hill Road? Aren’t we the liberal, open-minded coast? There are plenty of women who make partner at top law firms or earn tenure at Ivy League Universities, but they are barely represented on the Forbes Midas List (and embarrassingly crammed in at the bottom as though some editor said, "Oh, wait... uh, guys... I just noticed something..?")

What does it say about Silicon Valley when the most prominent female VC had to go through Wall Street to get to Sand Hill Road? What does it say that the most talked-about female VC in Silicon Valley was in the context of a sexual harassment lawsuit?

This isn’t coincidence.

It’s not because a woman makes a bad founder or weak VC — far from it — the problem is that the journey to VC Partner is one of the most opaque and uncharted paths that a businessperson can make. Lack of female mentors is simply one of many inputs into this murky equation. Nobody knows how the hell to get into VC. That’s unappealing to most businesspeople, and I can see it being particularly unappealing to a lot of women.

The female under-representation in VC is not just about software code and semi-conductors. It’s about planning vs. improvising.

Observation No. 4: Women can do whatever the hell they want

Perhaps my greatest observation in hiring and working with women is this: Women can do whatever the hell they want with their lives and careers, and it’s not my place or Sheryl Sandberg’s place to say otherwise.

Have there been moments when I tried to hire a woman as an early leader at one of my startups, only to have her turn me down for a more "ordinary" job at a big company? Yes. And did it disappoint the hell out of me? Absolutely.

But, you know what? That’s her choice, and she can manage her own set of personal preferences however she wants, and it’s not my place to judge. Working at a company with eight months of funding in the bank is... well... not always pleasant.

Sheryl Sandberg dreams of a world where “half our companies and institutions are run by women. When that happens, it won't just mean happier women and families; it will mean more successful businesses and better lives for us all.”

Oh, will it, Sheryl?

Because I can tell you that there is nothing more miserable and soul-draining than starting a company for the first time. On paper, my experience at Bleacher Report should have been a dream — it was a success, it was about sports, and I started it with my best friends. But I enjoyed my two years at Deloitte Consulting far more than I enjoyed my tenure at my own company. It was a painful process.

I know a lot of women who put happiness pretty far up their list of priorities. And I am in no position to tell them otherwise.

Will there ever be a day when women start half the venture-backed companies in Silicon Valley? Or represent half the executives on Wall Street? Maybe.

But until you have watched a sunset in New York from your Wall Street office and realized “my day is only halfway done,” then you cannot imagine the misery — yes, misery — that a lot of bankers and executives endure in order to feel valuable.

Women are plenty capable of doing those jobs and succeeding at those jobs. But Sandberg’s vision is predicated on women wanting that life in equal numbers as their male peers. If there’s one thing I’ve learned working closely with a lot of women, it is this — do not tell women what to do with their lives and careers.

And that applies to Sheryl Sandberg as much as it does to me.