Silicon Valley can be a wild ride for an entrepreneur, especially if you’re a woman or a minority or both. If you have big ideas, the fact that you’re not a white dude from Stanford shouldn’t stand between you and startup success. CEO Cheryl Contee, author of Mechanical Bull, shares her entrepreneurial journey and leads the way in telling us exactly how this can be done.
Cheryl Contee: I do a fair amount of public speaking in the course of my work. It’s often about politics and technology, but it’s also increasingly now about the entrepreneur’s journey that I’ve been on. Attentive.ly, my tech startup that I built with Rosalyn Lemieux who was a contributor on the book, is as far as we know, the first tech startup with a black female founder to be acquired by a NASDAQ company.
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.
More people have been to the moon than have done what I’ve done and am doing—talking about our story and representing the work and answering questions from aspiring entrepreneurs.
I really got a sense of what types of information would be most helpful to folks who say, “Wow, show me how it’s done.”
So, from that standpoint, I wrote to a certain extent, the book that I wish that Ros and I would have had when we first started our journey as entrepreneurs.
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?
Cheryl Contee: I want people to come away from this book or even as they’re going through the book and use it as a blueprint and a manual for how to get it done. 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?
But then, really taking people all the way through the lifecycle of what can you expect that’s going to happen next?
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.
The action that I want people to take away from this book is that, “Ah, I have everything I need now to start my own business and rock it.”
Cheryl Contee’s Background
Rae Williams: How did you get into tech?
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.
They paid a lot of money—like $17 an hour. But I hate washing dishes, and the thought of working 20 to 30 hours a week washing dishes, you know, I’d rather go to hell.
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. As an innocent young person, 19, I had put together my own Mac SE—yes, I’m dating myself. So, I was like, “I’m great at computers, how hard could this be? I can help people.”
As it turned out, it was harder than I thought, but I learned so much. 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?
Cheryl Contee: I really didn’t know, to be honest that I had what it took to a certain extent. I think this is, for everyone, it is a bit of a gamble. When I first came out to Silicon Valley, I did think it was strange that people’s startups would fail. Sometimes, fail spectacularly, flamboyantly, and yet they would get a better job than they had before.
I was like, “How does that work? It just like classic male failing up or what is that?” But instead, now that I’ve been through the process, I totally get it.
Even if you fail and fail hard, which apparently the stats are 90% of American small businesses will fail in their first year, there’s a good chance you might fail.
Even if you fail, you learn so much in the process that you can then bring into an organization. So, to a certain extent, I didn’t know. But at that point, I had seen so many other people try, sometimes succeed, sometimes fail, and I said, “They’re not smarter than me. And they’re not willing to work harder than me. I’m going to give it a try.”
The Power of a Network
Rae Williams: What was your first step that you took when you decided to give it a try?
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. Something in me said, “It’s time to go.”
It started with me quitting my job, walking out, and tweeting.
This is the power of a network. I mean, I put out a tweet that said, “Look, I find myself available, who wants to work with me?”
I actually got a lot of income from that one message, including what turned out to be a fateful message from the then boyfriend, now husband, of my co-founder, Ros Lemieux. He said, “Hey, you should talk to Ros. She’s also thinking about doing her own thing. Maybe you guys might make a great team.”
Long story short, we started working together, and it was magical. Our team went from two people to 10 people in a year. We just found ourselves in a groove. I think that’s one of the points that I make in the book, is that you can’t do it alone.
I think particularly for non-traditional founders, women and minorities, by the time you ginned up enough confidence to start your own business, you’ve operated for so long as an army of one. You know, really pushing hard as an individual.
And there are zero successful businesses that are built around one person. Instead, even if there’s one person who appears to be out front in the face of the business, like Jeff Bezos, I can promise you that behind the scenes, he has a really strong team working with him. Many of those people have been there from day one.
And so, you know, building that team and understanding that you are good at the things that you’re good at and you need to figure out what are the things that you’re not so good at and don’t know about and recruit those people. This is the key to the success and in the case of Ros and myself. Ros is good at all of the things that I’m not good at and I think, vice versa, over the years, we’ve learned a lot from each other and I think now there’s more of an overlap in our skills. But that’s really central.
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.
Then there’s the geek, right? If you’re talking about a tech startup in particular, but I would say, any startup now, who is the person who is ground zero? How are we going to get it done, right? Covering all of that information, and sometimes this person is the same person, but I would say that it’s pretty uncommon.
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? Having someone on your team, even if they’re not there day to day, they usually won’t be, but someone who can as from not only a more objective place, but from a place of having done it before, provide you with some insight that will help you make better decisions and make fewer mistakes.
These are a few really key roles that people need to think about.
Rae Williams: How do you navigate the issue of gender and sometimes race and being an entrepreneur in an industry that doesn’t seem to be female friendly?
Cheryl Contee: Things have really changed, I would say, in the tech industry. There’s definitely more awareness of the special challenges that women and minorities face in right now, mostly white and certainly very male dominated industry of tech. From top to bottom.
That said, I wrote the book because I think in the startup world, there’s still not necessarily as much discussion about the specific challenges, just an awareness that there are challenges. 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. Minorities.
Basically, he said, “Wow, this is a really great product, but I don’t know that you specifically are the person who can actually make this a success.”
He was talking to someone who was at that point someone who had created a nationally renowned blog, that really impacted a lot of the political discussions you see today. Who had been on every major media network, CNN, Washington Post, et cetera. 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?
So, you are going to come up against people who look at your product or your idea and look at you and aren’t able to make the connection and aren’t able to take that journey, which means you’re probably going to have to talk to more people. There’s just no way around it. No matter what you may have done in the past, if this is your first startup, you’re going to have to essentially behave as if you’re starting over and prove yourself. 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.
Why Mechanical Bull
Rae Williams: Why did you decide to call it Mechanical Bull?
Cheryl Contee: Yeah, I decided to call it Mechanical Bull just because for one thing, startups are a wild ride, right? One day, you think to yourself, “I’m going to be queen of the world, it’s going to be great, we’re going to be millionaires.” And the next day you think, “It’s over. It was a fun ride; this was great, but this train is rolling into its station.”
Startups are absolutely a wild ride, and part of the challenge is staying on that bucking bronco as long as you can. However, I called it Mechanical Bull because it’s different when women ride.
I don’t know if you’ve ever been in a bar, where there’s a mechanical bull, or if you’ve even been on a mechanical bull yourself. I have.
It’s a completely different experience. When men are riding a bull, people are looking at their strength, their stamina, right? How long can they stay on, what’s the form?
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. It’s just a very different experience, and I would say, a startup to a certain extent is a little like that.
Not only is the challenge to ride, but you’re under a completely different set of scrutiny and expectations and challenges when you’re a nontraditional founder.
A Word of Caution
Rae Williams: What is the detriment of not kind of following some of this advice?
Cheryl Contee: Well, the detriment of not following some of my advice is that you know, you’re going to get bucked off that bronco a lot faster. You may find your startup journey, mileage may vary without this book and you know, that’s kind of why I wanted to write.
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.
You may be raising money from your friends and your family, and yet, particularly if you’re a minority, if you’re a technologist, you’re already making the most money in your family, right? 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.
There’s no friends and family round, just a non-starter. There’s no one who is going to be like, yes, here’s a check for $100,000.
That’s just not a real expectation. So, helping people to understand how they can even answer that question—“How did your friends and family round go?” Yeah, my friends and family don’t have the same circumstances that I have, so I need to go straight to seed.
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. There’s a lot in there, though. I think that is very practical.
I think the biggest step is to talk to people about your idea. I would say particularly in minority communities, there’s often this, I don’t want to tell someone because someone might steal your idea.
Look, that’s the furthest from the truth, for one thing. Most people aren’t as ambitious as you, so they might hear about that idea and think it sounds cool, but they’re not going to do a thing with it.
For another, you need to talk to as many people as possible about your idea so that you can figure out “Who are my team members,” right?
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. Putting stuff up on AngelList and saying, “Hey, I’ve got this idea, who wants to join?”
Once you start putting that energy out, you’re going to see that energy start to come back.
If you’re just noodling in your journals, alone, thinking about your idea and kind of hoarding it to yourself, your idea’s never going to find life and it certainly isn’t going to find investment or customers.
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?
Cheryl Contee: The challenge would be to make a pitch deck, right? There’s a whole section of the book that’s all about how you don’t need a business plan. It doesn’t have to be that detailed. It’s daunting, and most busy professionals don’t have time to do that.
It’s not that hard to do a pitch deck, and the pitch deck is really going to help you focus on the answers that you need in order to see if this is a real thing or not.
Read the book and make a pitch deck and then start to walk it around to people. Don’t worry about getting investments right away. 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?
Cheryl Contee: You can always find me on Twitter, it’s @ch3ryl. I’m easy to find on Twitter, or of course Instagram or Facebook.
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