Cheryl was a co-founder of social marketing software Attentive. Cheryl is also proud to be a co-founder of the tech inclusion initiative YesWeCode. Buy it, consume it, learn from it. Listen here. Do you need more startup expertise on your team?

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Cheryl Contee: I do a fair amount of public speaking in the course of my work. The number of black women who have raised significant seed or venture capital over a million dollars is still a very small club. Only a handful in American history. Reading Mechanical Bull Rae Williams: What is the actionable item that when people read the book, they can say yes, this is what I need to do?

The American dream is in part, around starting your own business and being your own boss and that feeling, that myth, that dream is just intrinsic to our identity as Americans. So many people dream about that, and I really wanted to write a book that makes that possible. That starts with the question of, are you really an entrepreneur?

Do you understand what that really means beyond the dream and the aspiration, the amount of hard work and the life changes and sacrifices you might need to make in order to do that, what might be holding you back? Okay, you got to pull your pitch stuff together. You need to build a team, you need to find investors, what happens when you get funded?

All the way through exiting and actually potentially selling your business, going to an IPO, or in many cases, failing. Cheryl Contee: Well, how I got into tech in general is quite a story. Essentially, it starts with my deep hatred of doing dishes.

I would rather clean a bathroom with a toothbrush, and at the time, when I was a student at Yale, I had to have a campus job as part of my scholarship. The highest paying job back in the day was working in the kitchens, because those workers were unionized.

I looked for the next highest paying job, which paid about half as much, so it was a big step down, and it was being what was then called computer assistant. Helping professors and students in the library, computer rooms, with the printer, with their computers, with the disks back when we had floppy disks.

Helping them rescue their files. I can help people. That was really my almost my second major if you will. Shadow major. I never majored in computer science, I actually majored in what was called then ethics, politics and economics at Yale, but I was able unite those two paths—all of that interest in society, but also technology—into the career I have today. Rae Williams: How did you know that you had what it takes, and how do people reading your book know if they have what it takes?

I think this is, for everyone, it is a bit of a gamble. Sometimes, fail spectacularly, flamboyantly, and yet they would get a better job than they had before. It just like classic male failing up or what is that? Even if you fail, you learn so much in the process that you can then bring into an organization. Cheryl Contee: Well, the first step was quitting my job, as it turns out. I had been passed over for a promotion that was in my offer letter at this really big PR firm that had nothing to do with my talent or how hard I was working.

It had everything to do with internal politics. This is the power of a network. Maybe you guys might make a great team. Our team went from two people to 10 people in a year. We just found ourselves in a groove. You know, really pushing hard as an individual. And there are zero successful businesses that are built around one person.

Many of those people have been there from day one. This is the key to the success and in the case of Ros and myself. Building a Team Rae Williams: How do you break down who you need on your team, and how do you do it? Cheryl Contee: In terms of recruiting the team, there are some key roles. I go into a lot more detail in the book. But for example, one of the key roles is the visionary, right?

Who is the person who has got the big idea and is great at articulating? That big idea. It can really be the void, not only the voice and the face, but really help the team stay true to that big idea.

How are we going to get it done, right? Usually people split off. You need someone who is focused on sales and marketing, often times, having someone who is focused on the product itself and really putting themselves in the shoes of the customer and being the customer advocate. Another important role, the advisor, you know? These are a few really key roles that people need to think about. Cheryl Contee: Things have really changed, I would say, in the tech industry. From top to bottom.

I think what I wanted to offer were some real solutions, right? What to do when you come up against some bias? For example, I had experiences where we actually had a product, we had a prototype, we had customers, and I sat in front of an angel network, basically a venture capitalist, whose job it was to invest in exactly people like me. Someone who had already helped build a multimillion-dollar business.

Who exactly was he imagining was going to come in and do this better than myself or my business partners? Really provide your credentials and knock on more doors than you might imagine or that someone who might look different from you might have to knock on to get the same level of investment.

Cheryl Contee: Yeah, I decided to call it Mechanical Bull just because for one thing, startups are a wild ride, right? It was a fun ride; this was great, but this train is rolling into its station. I have. When men are riding a bull, people are looking at their strength, their stamina, right?

When a woman gets on the bull, all of a sudden, the whole energy changes. People are looking at her body, the things that are jiggling, you know, they are waiting for a boob to pop out. This is part of what when they call it privilege, right? White privilege or male privilege. Part of that is not even realizing how much access or knowledge you already have walking in, that someone may not have, right?

Whether it is connections or a parent or an uncle or an aunt who is a successful entrepreneur, CEO, who is an advisor. For example, the whole notion of the friends and family round. The friends and family round is considered like a pre-seed round. Before you really start to talk to external investors. Very few people are making more, and in fact, people are asking you for money.

People are trying to bum 10 bucks off of you. That was my hope, was to really help educate people on the process, the terms, but also equip them with answers and responses and expectations that they can use to help get overcome hurdles and that come along the way that might stop them or sidetrack them. Words of Wisdom Rae Williams: If you could pass on just one piece of advice, one piece of knowledge that you think is the most important thing that they could take through with them, what would that be?

Cheryl Contee: There are so many things, gems in the book. We tried to make it a really easy read, right? Insert some personal narrative. I think that is very practical. I think the biggest step is to talk to people about your idea. Who are my potential investors, who are my customers and what do they think about it and what do they want? Who are my potential suppliers or vendors or business partners?

Talking to as many people as possible and reaching out. A Challenge for Listeners Rae Williams: If you had to issue a challenge to people reading your book, to people listening to us now, what would that challenge be?

Read the book and make a pitch deck and then start to walk it around to people. Just show it to your friends, show it to your family, you know, put it online see what people have to say about it. Rae Williams: Where can they find you to ask more questions?

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Print icon Resize icon I saw myself as a technologist, like so many in Silicon Valley. I believed that with a good idea for a product and enough gumption, I could make anything happen for my business. So when my business partner, Roz Lemieux, and I sought funding to take our new product, Attentive. We had a good product and paying customers. Yet here I was consistently being told it was a good idea but that there was a problem with me. The clear, explicit statement was that if someone else had brought it in, it would be worth it. As a woman, I can attest to the fact that we experience different challenges in society than men, and one place it shows up is how we are perceived in business.


Cheryl Contee


DIN 15435 PDF

Meet the Mentor: Cheryl Contee




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