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Advice / Succeeding at Work / Break Room

When Things Get Complicated With A Co-Founder of a Different Gender

There’s a giant push for more female entrepreneurs right now, headed up by empowering initiatives and resources like Change the Ratio,Women 2.0WITI—and of course The Daily Muse. With so much support and encouragement from the growing women-in-tech community, now is definitely a great time to run after your dreams.

But, it’s not always easy. As an entrepreneur myself, I’d like to share one of my experiences as a female starting up in tech.

This is a very personal story that has been hard for me to share. It may also be an unusual story. But it does happen—and I hope that my experience and missteps can help other women avoid similar situations.

The Search for a Soulmate

The search for a co-founder isn’t that different than the search for a soulmate. You’re looking for someone who really gets you, your way of thinking, and your goals with the company and the product. You’re looking for someone who—at least on your good days—you’ll be completely in sync with. And this can create a rather challenging situation for female entrepreneurs seeking a technical co-founder, most of whom are male.

I left my first job shortly out of college to work on my startup. I’d been working with a guy I knew from high school, and when he learned I was working on a side project, we met up for coffee. We had a great conversation, we really hit it off, and he offered to help me on the technical side of my project. We thought on the same wavelength, we were able to bounce ideas off each other, and we enjoyed hanging out together. We were a solid, well-balanced team. Or so it seemed.

The seed of the problem came when he admitted that he liked me. I told him I wasn’t interested in a relationship and he let it go. I thought that was that—we were trying to start a business, and we kept working together.

The Breaking Point

He soon quit his job to join me full-time, and we started working out of his apartment. A few months in, business was going well, and we were looking to take our company to the next level.

But that wasn’t the only thing that he wanted to get to the next level. In the midst of investor meetings, he sat me down and told me he was in love with me. I was still was not interested. After that, things turned sour. His demeanor completely changed. He became bitter and uncooperative, and we started arguing over even the smallest things. His willingness to hear my point of view on the product was gone. We could no longer work together.

But, he still gave me one last chance to keep our startup alive. His ultimatum: “I can make anything happen for you—if you were to be with me.”

I was thrown into a state of shock, disgusted and insulted by how he was trying to take advantage of the situation. I refused. The experience was crushing, but the horror story didn’t end there.

After we finally agreed to shut the company down, he decided to launch the product on his own—an entrepreneur’s worst nightmare. (In retrospect, don’t worry about that so much if it happens to you—it’s not as big of a deal as you think.)

Lessons Learned

Afterward, I spent a long time reflecting and trying to figure out what happened. What went wrong? What could I have done to prevent it? Does this happen to anyone else?

You might not be able to prevent a similar situation from happening, but there are some things you can do so that you go in to any co-founder partnership with your eyes wide open. Here are some of my lessons learned.

Don't Be Desperate

First-time entrepreneurs are very vulnerable to picking the wrong partner. When you first think you’ve finally found that person who gets you and who thinks on your wavelength—you’re tempted to jump. It’s natural want to forge a partnership immediately. You have a great idea, and you want to execute it! But when you move too quickly, it’s easy to overlook those slight uneasy feelings lurking underneath. If your gut is telling you that things might get complicated (romantically or otherwise) with the person across the table—pay attention.

Understand Motivation

It’s not enough that you and your co-founder think alike and get along. It’s important to understand his or her motivation—because that’s what will drive his or her behavior over the coming years. No matter what she says or how he behaves, if someone doesn’t enter a business relationship with the right intent, it’s never going to work.

Lay Down the Ground Rules

In male-female partnerships, it’s possible to confuse romantic interest for professional compatibility or make professional decisions that are subconsciously driven by a romantic interest. Although it’s not common, it can and does happen—and it’s important to be cognizant if such a situation is arising. Avoid problems by making sure that you’re both on the same page, and lay down the rules ahead of time.

Speak Up

Be firm on where you stand in tough situations. I’ve always been hesitant to speak up, be assertive, or confront others—but people will take advantage of this. In some situations, you need to lay down the law so there’s no room for second guessing. And don’t worry that you’re coming off as harsh or arrogant—you probably aren’t half as harsh as you think you are.

Don’t Give Up

This is the most important point! Don’t be daunted. Get back on your feet. After my company fell through, I spent a week or two reflecting and learning from the situation, got back into a full-time job—and then worked to revive my startup on the side, with a different team.

This quote from Cindy Gallop’s WITI interview really sums it up best:

Female entrepreneurs face many more obstacles than men, the playing field is not level… know that, just grit your teeth, and make your startup happen…The only person to make things happen for you is you.”

It’s embarrassing to explain that such an unprofessional thing killed our startup. But the lessons learned through this experience extend across areas that are applicable for both male and female entrepreneurs—like figuring out if someone will actually be a good co-founder. Take it from me—you need to make sure you know what you’re getting yourself into.

Recommended Reading

Want more? Here’s a list of articles and discussions that prompted me to finally write about this topic:

  • NYTimes: For Women, Parity Is Still a Subtly Steep Climb
  • WITI Summit: Cindy Gallop on NYC startup scene and funding for women
  • HBR: Four ways women stunt their careers
  • Change the Ratio: Women, apply to YC!
  • TED: Sheryl Sandberg on Why we have too few women leaders
  • On Startups: Choosing a cofounder
  • Mark Suster: Why aren’t there more women entrepreneurs
  • Photo courtesy of Vancouver Film School.