Being a Woman CEO and Overcoming Bias

Meg Ansara

I grew up in a family of organizers and teachers. So from an early age, I was taught to believe in the power of people — all people — to create change. Leadership was a verb, something you do, rather than something that someone was born being. This meant that I had to pool my Halloween candy with the younger kids on my block, so that we all got those coveted Reese’s peanut butter cups, and I was expected to stand up to playground bullies. These values are also what led me to dedicate my career to organizing. 

No one better exemplifies this style of leadership than my friend and colleague, Cheryl Contee. 

Over the course of her career, Cheryl has had numerous successes, including co-founding the first tech startup with a black female founder on board in history to be acquired by a NASDAQ-traded company. You can always count on her for the smartest of ideas and most creative of concepts. She’s a straight talker, always saying what she thinks, even when it’s hard. And, she is steadfast in her belief in others. As CEO of our sister company, Do Big Things, she’s led that company to be one of the freshest and most interesting voices in digital media, in less than a year. Quite simply, she’s a rockstar. 

Cheryl has just published a best-selling book to share her wisdom and lessons learned about leadership, particularly when it comes to being a woman CEO and a person of color. 

It’s never easy being a CEO, but as women there are particular biases and challenges we face when we lead companies, organizations, and government agencies. These challenges are even more significant for a woman of color. Every organization and good idea needs funding, but for a person of color, there are additional obstacles to fostering belief or even simply being seen.  Cheryl has continually broken through those barriers, in a wide variety of settings, and her book explains how she did it. 

At this moment in time, in Trump’s Washington DC era, we’ve seen both a rise in women stepping up to lead and more explicit, aggressive and violent prejudice and harassment. If ever there was a time for us to support each other, and a new and different generation of leadership, it is now. 

It is incredibly powerful to be part of an ecosystem with fellow partners at 270, with Betsy Hoover at Higher Ground Labs, and with Cheryl at Do Big Things. 

Cheryl has been a trail blazer and I’m grateful that I have the opportunity to work and learn from her every day. I encourage you to take a look at her book, Mechanical Bull: How You Can Achieve Startup Success, and use it as part of our broader work to support more women and minority-led companies that are making a difference in the world. 

The following strategies for overcoming bias are adapted from her book, and written by Cheryl. As an organizer, team-builder, and believer in the power of excellent education, I recommend adapting her ideas about overcoming bias for yourself!

Overcoming Bias to Secure Funding 

By Cheryl Contee

When my business partner, Roz Lemieux, and I sought funding to take our product, Attentive.ly, from side hustle to main gig, I was fortunate that I didn’t know how rare it was for black female founders to get funding of any kind. 

I saw myself as a technologist, like anybody else in Silicon Valley, with a good idea for a product. I had a certain amount of micro-celebrity from my days at Jack and Jill Politics, which had been a popular blog, and from television appearances. Fission Strategy had experienced millions of dollars in revenue. I felt I was qualified. I was used to people returning my calls and responding to my emails.

Fighting Discouragement

Having to be persistent with people to even get a response was discouraging at times. When I finally got in the room, getting people to watch a demo was challenging. My impression was that people didn’t believe that I had a real product that was worth their time. I once met with an angel investor contact who was working for, believe it or not, an organization specializing in diverse founders. He vetted ideas before presenting them to the actual investors. He sat through the demo politely and at the end said, “This is interesting software. I can definitely see where this could make a difference. I just don’t know if you are the person who can actually take this product to market.” He said this to my face.

At the time, I could only assume that race or gender or both influenced his comment because I knew that I had as good of a track record as anybody else walking through that door. We had a good product and paying customers. The group he was part of was dedicated, at least in their mission statement, to helping folks like me get funding. He told me he thought it was a good idea—not that it was a bad idea or that it wasn’t a worthwhile product—but that there was a problem with me. The clear, explicit statement was that if someone else had brought it in, maybe it would be okay.

I kept my composure and said, “Okay, it’s fine if you don’t get it. I believe in this product, and we’re going to find the folks who get it, but thank you for your time, and if you know anyone that you would recommend, we’d be glad to talk to them.” I just shut it down. It was clear we couldn’t expect much from that group.

My instincts might have been to give him a roundhouse kick in the nose as I had to the playground bullies in elementary school, but the Silicon Valley investor community is small. All the investors somehow seem to know each other, although this is changing as the pool of investors grows and diversifies. Nevertheless, you don’t want to alienate anyone unnecessarily. It’s okay to call someone out, but it’s also in your best interest to thank them for their time, stop the meeting, and leave. 

Finding Our Investor 

Roz and I talked about it. For half a second, I wondered if I had to hire a white guy to represent our product to investors. We fought doubt that we’d ever get funding. We took a deep breath and agreed we and our product were as good as the others looking for funding. It took us longer, and we had to knock on more doors, but we found the investor who got the product, got us, and funded us.

Christie George, Executive Director of New Media Ventures, had this to say about funding our startup: 

“Because the investment world is so demographically homogenous, my sense is that most investors simply don’t relate to people who don’t look like them or founders who are solving different problems than the ones they’re used to seeing over and over. So the “pattern recognition” investors are so used to deploying fails them when faced with founders who break the pattern.

Ultimately, we moved forward with Attentive.ly because of how absolutely thoroughly Cheryl and Roz understood their target customers. Attentive.ly wasn’t serving a hypothetical need but rather a need that had come up time and time again in the context of the consulting work Cheryl and Roz had been doing.” 

Sometimes even if you have a great idea, people, including investors, will dismiss it because you’re the messenger. The same idea presented by an upper-middle-class white male to another upper-class white male might be received in a different way.

What’s more, conventional wisdom says men tend to be overconfident and overblown in pitches, way into the so-called moonshot category. Therefore, investors in their mind often calculate a 20 to 50 percent reduction in the funding they’ll provide, whereas female founders tend to be conservative, modest, and humble. (Sorry, taking a break to roll my eyes.) The problem is investors take that modest, conservative, realistic estimate and cut it in half. Men need to dial it down a notch, and women usually need to dial it up. In order to get to a decent level of capitalization, such that you can be successful, you’ve really got to talk to that moonshot level.

As you talk to investors or prospective customers, you might get some of that. Don’t waste time on people who can’t go with you on that journey. If their imagination is that narrow, they’re not going to be a good adviser or investor anyway. 

As quickly as possible, assess if the person in front of you is serious or not, and if not, just keep knocking on doors.

***

For more advice on starting your entrepreneurial journey, read 270 Strategies partner and Do Big Things President Jeremy Bird’s blog post, “Mechanical Bull: A Step Forward in Diversity and Inclusion in Tech.” He shares Cheryl’s tips on filling a gap in the world and testing ideas. 

Cheryl Contee is the award-winning CEO and co-founder of 270’s sister company Do Big Things, which brings together a diverse team that uses new narrative and new tech like blockchain, AI, bots and machine learning to make the world a better place for everyone. Previously, she was the co-founder and CEO of Fission Strategy, co-founder of groundbreaking social marketing software Attentive.ly at Blackbaud (the first tech startup with a black female founder on board in history to be acquired by a NASDAQ-traded company). She is also co-founder of #YesWeCode, which represents the movement to help low-opportunity youth achieve high-quality tech careers. 

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