See, the year 2020 was supposed to be a big deal. But then as the agony began of watching, as many of my friends and family were laid off or saw their businesses shutter, I started to realize that 2020 was definitely not going to be what I had bargained for. Then as the year progressed and with the aftermath of the last several months, COVID-19, the murder of George Floyd and Breonna Taylor, as well as the protests across the world that would follow, 2020 was still a big deal! 2020 was a year of reckoning for many, forcing everyone to come to grips with the end of normalcy as we've known it. COVID-19 took with it jobs and security for hard-working families across the world. Here in the United States we were slow to respond, some even slower than others. On a call with an investor, we discussed how businesses would now be tested more than ever. Some of us would come out on top (those that were fortunate), some would stay flat (also fortunate), and others would close. The pandemic would test our ability to pivot or capture new opportunities, but more than anything it would test our sanity and ability to keep our teams going when everything around us was turned upside down.
This book is different. I hadn't imagined writing it while going through a pandemic and through our generation's version of a Civil Rights movement.
Yet, in this book I'm going to go there. I'm going to walk you through how I bootstrapped my first business to how I raised millions for my second company, all while retaining majority control; all while at the onset of a pandemic. My hope is that this book will offer something that was missing when I started building as an entrepreneur. I hope that it will shed light on what seems like the impossible, and bring new ways of thinking about challenges. I hope it is a bridge to the other side of your goals, a “how-to” guide of sorts that will bring about the awakening and push you've been looking for. I hope that it is both inspirational and aspirational. Never would I have imagined that someone like me, a first-generation college student who went to school on a full Pell grant, who grew up in a six-person household while her mother brought in a $26,000 yearly salary, would make it this far. There was no one to teach me the blueprint, but I hope to show you how I built my company from literally nothing while providing a ground-up approach, one where you can start from anywhere.
This book won't be an easy ride, but neither is business. Instead, I hope it will be a journey to economic and financial freedom through ownership, as that is what building a business has been for me.
1 Coming From Where I'm From
To be a woman you have to look like a girl, act like a lady, think like a man, and work like a dog.
—Leah Chase
Attending Louisiana State University (LSU) for undergrad opened up an entirely new world for me. I come from a small town about 45 minutes outside of New Orleans, the city where my mama and her family are from.
The first time I became really aware of technology was when I was in middle school, when my mother brought home our first computer, a Dell desktop. We didn't have the Internet, but my Mama would get these AOL dial-up cards for free. Now, obviously, I would be exposed more to technology in college, but I had no idea that my journey would lead me into tech.
At LSU, I met a professor who truly pushed me and many others to go beyond the thinking of the small towns we came from. Dr. Leonard Moore would likely have the single most impactful role in my life while I was in college—so much so that I added history as a second major. Yet, more than anything, he showed how someone could manage multiple opportunities. He had written books naturally as a college professor, but he and his wife Thais had also started a program for youth, and a youth church. He was living a life that I had never imagined was a possibility. There was nothing luxurious about it, either; outwardly at least he lived very modestly but I had never seen this coming from where I was from. Over the course of my life, exposure has helped me more than anything to actually realize the possibilities of not only my work, but what my life could be like as well.
Doc would say that if you do something you are passionate about, you don't watch the clock. These thoughts of how I could use what I was good at to build something I loved wouldn't die, so entrepreneurship for me started at a young age.
I went to a large university—a Southeastern Conference (SEC) school with over 30,000 students and a national title-winning football team, so we were one of the first colleges to have Facebook. The coolest thing about Facebook then besides another place to post with your friends was that you were able to upload albums and sell and buy furniture on their marketplace.
Yet, for the most part, people were still on Facebook without a face. Instagram wasn't really a thing. Twitter was just taking off, with celebrities posting about their projects or other tidbits about their day.
I created B-NOW, a college online newspaper, when I was in school, and my first company would come when I was 22.
I've never been afraid to start something on my own. I think this goes to having confidence in your ability to figure it out even if your capabilities aren't there yet. Yes, in a way you can fake it until you make it, but eventually you're going to really have to make it. But more so, this is about starting somewhere so that over time you can become an expert at what you do and command the type of payment you used to only wish for.
Even with that, I had a lot of hiccups along the way because I had to really grasp and understand not only how to run a business but how to start a business from nothing. I didn't inherit a business and I didn't have anyone to turn to show me the ropes.
There are a lot of challenges that you are faced with when starting, and then running, a business. It's still challenging, you know, even as a second-time business owner now building a company to scale.
As a business owner, you have key responsibilities to your team, to your clients, to your investors if you have them, to the IRS—you name it.
You have to ensure that your business is legally sound. You have to ensure that you are paying people correctly, whether they are a W-9 or W-2 employee. You have to decide when and if you want to go from W-9 employees to W-2 employees and know the differences between them. There is so much foundational work that goes into play in building a business, particularly one you plan to grow, that if you don't do certain things correctly they will come back to haunt you.
Then there is the actual work: going after contract opportunities, and building and selling whatever product or service you are offering to bring revenue into your company.
Most importantly, you have to make your business make sense. When you're trying to get people in the door or contracts closed you will feel the pressure to take what sticks or whatever someone is offering you. It will on first sight look like an opportunity, but could be anything but. I talk later about upside-down contracts. When you are venture-backed you might take on a customer where the financial gain might not be as rewarding but the benefits you receive from the deal, because of a prominent logo or other reason, might be worth it, whereas if you are bootstrapped this might be a luxury you can't afford.
As a bootstrapped company one thing you have to learn quickly is how to monetize what you are seeking to do. People know that one of my favorite things to remind entrepreneurs of is that you are in business to make money; otherwise, what you're doing is solely a passion project. What I've found is that the real magic happens when you can be both. If you prioritize one over the other you'll likely start to question yourself and whether it's worth it. Passionate about a business that doesn't make you money? You'll certainly suffer from fatigue and burnout, and eventually your business will most likely fold because you can't sustain a business that's not profitable. Only in it for the money? The initial rush of having money will satisfy a part of you, but the longing for something more will without doubt catch up with you and that's a different type of fatigue and burnout in itself.
Triple Threat
As a business owner I was a “triple threat”—and not in a good way. I was Black, a woman, and young. And so, in many ways,