Seven BIG Lessons from Seven Years of “CEOing”

I’ve been the Chief Executive Officer (CEO) of Infamous Mothers, LLC for almost seven years. When I coach or mentor new CEOs, I often explain to them that they are “chief problem solvers”— especially as small business owners. Over the years, I’ve faced hundreds of issues, challenges, and barriers. Working through them has taught me quite a lot about starting and running a company. And yet, each year seems to come with “the big lesson from these past 12 months” or the most important message from that period.

Below, I offer those year-by-year highlights. You should be aware that, if I were writing about the basics of running a company, what I share below may or may not be included in that piece. I think that’s why these lessons are so important: every CEO needs to know them, but often these big “ahas” are left to chance or experience. I think enough of you to give you a heads up and to share a few secrets. You can make other discoveries on your own. There'll be plenty to come :).

YEAR 0 (Pre-Business): Build a strong brand

Before I built a company, I built a brand. I didn’t do it on purpose. I didn’t even know that I was doing it. I just knew that when people encountered Infamous Mothers, I wanted them to have an experience. And so, I worked to make that happen.

The whole feel of the company was inspired by a photograph. I was clicking through our photographer’s website, and I landed on a picture of a woman. She had deep brown skin, smoldering eyes that stared right at you and full, plum-colored lips. Around her neck, she wore a bold statement piece made of gold and cowrie shells. Without having the language to describe what I was looking for, I told our photographer and graphic designer that I wanted Infamous Mothers to feel like her. Over time, that came to mean that I wanted the brand to be bold, unapologetic, defiant, strong and unflinching. And I wanted it to be beautiful.

I didn’t have any products or services. But people hired me to speak and they sponsored the mission to create classes, workshops, and other programming because they were drawn to the brand. We had a manifesto, and we were clear about the woman we wanted to serve. Everyone was clear about her story and her journey. And they wanted that woman to win. And so, they put money behind the idea of her. We raised $25k through a Kickstarter campaign for the completion of our first book and what would be our initial Infamous Mothers product. I titled it Infamous Mothers: Women Who’ve Gone through the Belly of Hell and Brought Something Good Back.

Today, we have a company. We have products and services, marketing, distribution channels, a value proposition…and a sales strategy. We are a real business. And I have 100% ownership. I haven’t taken out any loans. And I have gotten the support of major sponsors and grants to build Infamous Mothers. I attribute a large part of that success to my investment in creating a brand first.

But what does that mean? At the bare minimum, it means that I put a lot of time and effort into creating an image for our company— logos, high quality photography, creating a color palette and using consistent fonts, establishing a persona that represents the business. The brand is all about perception. Again, I didn’t know that then. I just started with what I could control at the time. There were so many pieces of the building-a-business puzzle that I didn’t understand. To not stall the process, I focused on the part that did make sense to me: the art, the language, the tone and the feel. I didn’t know that the brand would carry the actual company. I didn’t know that it would be the thing that drew dollars and ultimately built the business. I get it now when people say this about Coca Cola or Nike: “You’re paying for the name.” As you build your company, how much energy are you putting into what people associate with your company’s name? It’s worth just as much as the products and services you offer, if not more.

YEAR 1: Respond to the call

Year one of being in business, I was getting calls from everywhere to do so many things. The most consistent calls I was receiving were invitations to speak and requests for trainings.

Shonda Rhimes’s “Year of Yes” was published in November 2015. By the end of 2016, I had gotten my hands on it. Quietly, I declared to myself that over those next 12 months, I’d step out of my comfort zone and agree to attend any and everything (within reason) that I was invited to. During that time, I was asked to deliver a TEDx talk and to be the opening speaker for the Women’s March in Madison. I was asked to give talks on trauma-informed care and other subjects that required me to do more than show up. I had to research and study and write and practice. Every request required me to become more than what I was at the time of the invitation. And yet, I didn’t turn down the opportunities. Each time, I responded, and I rose— not without difficulty, of course. But whatever the struggle, I made it through.

In hindsight, my year of yes was about something more than I understood at the time. On the one hand, it was about what others saw in me and what they believed I was capable of doing. On the other, it was about my future self. Each time I received an invitation, I had to see myself in the future. For a second, in my mind, I had to visit who I’d be six months or three weeks from that moment. And in seeing myself, I knew that if I responded today, tomorrow, I would be ready to make good on that call. I didn’t think of it that way then. I just knew it was my year of yes. But that year taught me the importance of not letting today’s feelings of inadequacy stop me from the fulfillment of tomorrow’s mission. Year one taught me the importance and necessity of responding to the call.

YEAR 2: Make bold requests to the right people

In year two, I knew that we needed money— a lot of money. I hadn’t quite figured out how to monetize what I was doing, not in a way that would yield real income and a profit. But I had a long history with sponsors and grants, as both assisted with my tuition costs throughout my academic career. Until I figured out how to build a business to customer (B2C) strategy, I was going to have to rely on dollars from other businesses to stabilize and grow Infamous Mothers. I told “my people” about my plan to build a business to business (B2B) company, and I explained to them that we needed to raise $297,000 to give our young venture a fighting chance. It was also my way of avoiding investors and sharing control of a business I was still learning about. I didn’t want to sign away a portion of what I didn’t quite understand.

In all fairness, I didn’t have the confidence to even believe raising $297,000 was possible. I think that I could’ve comfortably asked for $50k or $75k. Fortunately, at the time, I was working with a black man who was looking to become a part of Infamous Mothers. And he told me I was low-balling myself. With this in mind, I found the nerve to actually write up a budget and figured out what we truly needed to make the company sustainable. It was $297,000. I didn’t have that kind of money. But I knew people who knew people. So I asked my people to make introductions to philanthropists and potential sponsors.

They did. I was put in the room with all kinds of Executive Directors, managers, etc. who had the resources to help us reach our goal. That year, we didn’t raise the $297,000. But it was the year that I learned it was possible. I just had to keep making bold requests to the right people.

YEAR 3: There’s success in failure

I know you’ve heard this a million times, “learn from your mistakes” or “there’s success in failure.” Trust me, that’s a lesson that never gets old. In case you think so, humor me anyway. And read on…

In year three, like Kimberly Elise from “Set It Off,” we needed that money— maybe more than ever. In 2019, I ran our third crowdfunding campaign. Guess what the goal was? $297,000. Learning from the mistake of our second campaign, I planned for months. We created graphics. We told people in advance. We asked businesses to sponsor our rewards. Even after all that preparation, we failed…miserably. We raised $5,000 of the almost $300,000 we needed. We didn’t just fail. We did so publicly, out loud in front of “God and everybody.”

And yet, we didn’t fail. During that campaign, we caught the attention of a major player in this city. She was a woman of color with access to sponsorship and grant dollars. She reached out to me and invited me to have a discussion with her over coffee. I told her my plan and mission and why I was fighting to raise that $297k. I explained to her why I wasn’t a non-profit and how I was hoping to make an impact in our community as a for-profit leader. She listened and said two things to me that I’ll never forget. First, she said, “You’ll never raise the money you need the way you’re doing it.” And then she said, “I’ll be the first to put dollars behind you. I’ll set the example for others to follow.” We received our first $25,000 from a foundation per her recommendation. I was able to then show a precedent for support to other funders, with another $30,000 trickling in. Again, we didn’t reach our goal, but we were building the kind of relationships that would making the possibility of doing real.

Year three showed me what Fantasia meant when she said, “Sometimes you have to lose to win.”

YEAR 4: “Your way is just as right as other people’s way”

In 2018, we hosted our first Infamous Mothers conference. We called it the Talk Back. That year taught us that we had to move our conference and most of our company to an online space. Women with children wanted professional development opportunities, and they wanted to network and connect with other women, but they didn’t have babysitters.

When I announced that we would be hosting our next conference, which was scheduled for 2020, and building our programming, all online, people laughed at us. They told us they wouldn’t attend our sessions. They declared our work would be a flop. And then, 2020 came, bringing with it the pandemic. People were registering left and right for so many reasons. Events had been canceled. People needed community. Folks were trying to figure out “how to do the virtual thing.” And we had become the go-to place for those experiences, lessons and a bit of inspiration. By the end of year four, we had secured our $297,000 and were well on our way to becoming the company we had been working so hard to grow into.

During that time, I was reading a book by Nathalie Molina Niño called “Leapfrog: The New Revolution for Women Entrepreneurs.” And one of the things she told her readers was that their way is as good as anyone else’s. In the case of taking our company virtual, that was true. Year four taught me to trust myself. Trust my research. Trust my approach. Trust that I do the work and that I do it well.

As an entrepreneur, you’re going to make decisions for your company that isn’t going to make sense to others. But if you’ve done your due diligence, trust that you’re making the right call.

YEAR 5: Move in silence

With dollars in our account, we had begun the work of fulfilling our promises. We upgraded and expanded our programming, recorded the first season of our podcast, created new marketing materials, developed new course materials, strengthened our branding and more.

We didn’t announce any of it.

Part of the reason we worked so quietly was because we really wanted to focus. People and organizations had trusted us to deliver, and we didn’t want any distractions. Another less fortunate reason is this: We didn’t want any one replicating our programming. Other places with larger budgets are doing similar work, but not like us. I’ve had to learn the hard way that when you share your vision, strategy or products too soon, people can execute them before you. And our stuff was so good, I wasn’t going to give anyone the chance to copy neither our approach nor our materials. In the past, I’d speak freely about my plans, share my vision and strategy with people I trusted, just to see our discussion play out a few weeks later in their organization. When my friends or family noticed this happening, they didn’t hesitate to tell me. I’d shrug it off saying, “I’m not a one-trick pony. I have others ideas. Maybe they needed that one more than me.”

But not this time. This time, I was going to go through the process of watching my ideas come alive from start to finish. If people copied them later, so be it.

Finally, we were quiet because, as a company, we were trying to heal. As a small business owner, you have to be scrappy and resilient and persistent. In my case, I had to give a lot of myself to clients and customers and audiences. While I loved every bit of it, and still do, over time, the cumulative effect of that kind of pouring out, combined with a poor self care regimen, weighed on me. I don’t think I have ever worked as hard in my life as I had in that silent period. But since I was away from social media and wasn’t really connecting with people outside of our contractors and the women we were piloting programing with, I was able to improve my overall wellbeing.

Year five taught me that there is a time to make your plans and intentions heard, and a time to do more and say less.

YEAR SIX: Plan for the growing pains

I thought that money would cure all of our small business problems. It didn’t. In fact, I learned from experience that the saying is true: “Mo’ money, mo’ problems.”

With increased funding, we were able to expand our team from two contractors to twenty. I thought that by having qualified people working alongside me, that meant all of our prayers would be answered and that my life as an entrepreneur would be easier. I’d work less hours, have less stress, make more money and Infamous Mothers would make a larger impact in the community.

Not quite.

While I had managed to bring on some of the best contractors that our new money could afford, I didn’t realize that organizing and synchronizing their work required a new set of skills (that I hadn’t yet acquired) and a new set of software (that I hadn’t learned). Part of the problem was that my new team were all contractors. They didn’t work for Infamous Mothers. They worked for themselves. Some people didn’t want to attend meetings. Others didn’t want to talk to anyone at all. Others were uncomfortable using the project management software we were licensing. I didn’t have time to figure out all of that stuff. Life was supposed to be easier. Instead, it was posing a whole new set of challenges.

That was one group of growing pains. Another set of pains was waste. You know how restaurants often throw away food at the end of the night? That’s what I felt about me and my team. Time and money were being thrown away. We were throwing them at missed deadlines. We were throwing them at learning curves we weren’t aware were happening. We were throwing them at unfulfilled contracts. Entrepreneurs struggle with mental health issues at a higher rate than people in the workforce. Some of our contractors were really dealing with extreme burnout and anxiety and depression. I paid them even when their work wasn’t completed and we had to part ways because, from a human perspective, it felt like the right thing to do. And I don’t regret it. I do, however, think about how I could've handled things better from a business perspective.

Another thing I think about is the fact that I rarely challenged a vendor’s price. I know there is a wealth gap for people of color (black people, in particular) when compared to white households. As a business owner who is black and female, I set my pride on not haggling contractors about their fees. In hindsight, there are a few companies that I should have at least questioned their rates. I believe that doing so would have resulted in dollars saved. To be clear and fair, I wouldn’t say that I squandered money by paying higher rates. I am saying that paying more wasn’t always the best use of our dollars.

Year six has taught me that scaling is hard. It’s beautiful and fun, stressful and overwhelming. Some years ago, I had taken a class with a teacher who had warned us about the dangers of growing too fast, so I had prepared myself as best I could. But there is no teacher like experience. Trust and believe she “got me right.”

YEAR SEVEN: Rest is required

We’re heading into year seven of Infamous Mothers. I had a “year of yes.” This will be my “year of rest.”

For almost seven years, I have run this business like I was still in college— long work days, pizza, a crash-and-burn sleep schedule, and impossible deadlines. Rest, for me, means trusting that we’ve laid a strong enough foundation, trusting that we know the demands and processes, and trusting that we have built out strong enough products and services for the company that I can lead from a place of authority and power and not fear.

The message is not that rest is earned only when things are properly structured and in place. The message is that my approach to running my business was that I didn’t allow myself to rest until we reached this point. This was in part because I kept thinking that if I just did a little bit more, I’d get to a place where I could take a break. “A little more” turned into almost seven years. That’s seven years with no real vacations. That’s seven years of irregular sleep. That’s seven years of a frantic and unsure mind, feeling anxious and out of control and unsure of— always anticipating but not quite arriving at— rest.

If I could go back in time, I’d see self-care as a crucial part of my business strategy. A good night’s sleep means I am a sharper thinker. More water intake means I am more energized. Mindful eating means less stress. And regular movement means more confidence and better problem solving.

BONUS LESSON: Don’t Flail

“Don’t flail.” That’s what my late business coach, Dr. Amy Gannon, used to say to me when I found myself backed into a corner financially. Over the years, I’ve been backed into many of those corners— even recently. For a second, I always flail. In other words, I move frantically and uncontrollably. I make desperate decisions. Have desperate conversations. Do desperate things. Flailing never works. In fact, it makes things worse.

Because of my trauma, what I’ve gone through with poverty and struggle, that survival thing often kicks in first. And then I hear Amy say, calmly, “You’re flailing. Stop flailing.”

But what does it mean to not flail when you feel that you’re about to lose everything? It means compartmentalize. The stakes are high and the pressure is even higher. Focus on what you can control and methodically work your way out of that corner. For me, it meant building a brand when I was still trying to understand what it meant to build a company. It meant writing sales pages when I was too burnt out to write chapters for a book, knowing that I was up against a deadline. It meant building relationships with prospective sponsors when I didn’t have the budget to market to my customers. To not flail means to revisit the plan, put your head down and work until the crisis is over. It means not making things up as you go. It means not throwing ideas out in the air and just hoping they stick, like spaghetti against the wall. It means trusting yourself enough to believe that even though you may not have planned for this catastrophe or problem, you did plan. And it means if you have to pivot, you will create a new plan— one that is thought out, researched and executed from a place of control. Not flailing is about not reacting, but being proactive.

There has never been a year that I didn’t flail. But there’s also never been a year that I haven’t managed to regain composure and come back for the win because there’s never been a year that I haven’t heard my late mentor in my ear saying, “Don’t flail. You got this.”

May you and I always regain control and come back for the win.

Bonus 2: Build a company that’s bigger than you

I often talk and write about how entrepreneurship is about solving problems. A new vegan restaurant, for example, is built in a community because one hadn’t yet existed in a place where people were looking for more healthful dining alternatives. An energy-efficient car is created to put less tax on the environment.

Sometimes, the problem being solved might be one that the founder of a company has experienced personally, but unless she plans on having a market size of one (meaning, one individual), the problem has to be one that others struggle with, as well. And the solution has to be just as big. It has to be bigger than her. The product or service being created has to alleviate the pain of enough people who are willing to pay for it. And that market of people has to be large enough to sustain a business, along with bringing in a profit.

More than that, here is something else to consider: a company should make a social impact. It should be bigger than the product or service, in the same way that it should be bigger than the CEO. Through business, are you seeking to close the wage and wealth gap for your employees and contractors? Are you looking to address health disparities? Does your company solve the problem of daycare for working moms? Are portions of the profits being funneled to local nonprofits or small businesses looking to get started? Is there an internship program for high school students?

As the CEO of Infamous Mothers, a large part of my mission has been to build a company that is committed to closing the wealth gap for people of color and women by addressing the trust, health, and technology disparities that entrepreneurs often face. Because this is our focus, the infrastructure of the company has been built with these goals in mind. For example, Covet is the health and wellness arm of 3rd Space Virtual Coworking, created for our members to build health alongside their wealth. We build relationships with community banks and credit unions so that we can pipeline our women into institutions they can trust, scaling their businesses or buying homes with more confidence and less struggle.

These are just a few examples of what we’re doing to build a company bigger than any one person. What are you doing? If you’re not there yet, what would you like to do? As entrepreneurs, we can do good and well at the same time. The two are not mutually exclusive, nor should they be. In fact, according to Simon Sinek’s “Start with Why” — award winning author, speaker and deliver of one of the most watched TED talks (over 56 million views)—starting with a “why” that’s bigger than them were the keys to the success of Apple, Martin Luther King’s “I Have a Dream Speech” and the Wright Brother’s aircraft. Making your company bigger than you just be the key to your success, as well.

Stay Connected

If you like this blog post, share it on your social media or follow us on ours. If you want want to know more about Infamous Mothers, our products and services, and Infamous Mothers University (IMU) visit us at www.infamousmothers.com. If you want to know more about this blogger, read below.

About the Blogger

Dr. Sagashus Levingston is an author, entrepreneur and PhD holder. She has two fur babies, Maya and Gracie, six children (three boys and three girls), and they all (including her partner) live in Madison, WI. She loves all things business, is committed to reminding moms of their power, and is dedicated to playing her part in closing the wealth gap for people of color and women. She believes that mothering is a practice, like yoga, and she fights daily to manage her chocolate intake. The struggle is real, y’all…and sometimes it’s beautiful.

Contact info: sagashus@infamousmothers.com