What It Really Means to Be CEO

Think back to high school. Remember those popularity polls that were the staple of all yearbooks? There was always a category for Most Likely to Succeed. We used our teenage brains to come up with the right answer and a list would form: someone with top grades, a star athlete, a boldly confident student or even sometimes the prettiest student. I would come to find out that neither looks, smarts nor confidence is the key to entrepreneurial successes. The most necessary trait? Adaptability.

When you think about what starting a new business requires of a person, think about Eric Ries’s definition for a startup: “A startup is a human institution designed to deliver a new product or service under conditions of extreme uncertainty.”

What is going to get you through extreme uncertainty? Adaptability.

When I’m approached about investing in a new company, I need to understand the product first. If it’s not ready, or it doesn’t do what it tells me it’s going to do or I don’t believe the market is there, it’s a nonstarter.

But if I do like the product, the next thing that needs to sell me is the CEO — the person who wants my money to help bring their vision to life.

Especially when companies are just starting out — because in the early days, the CEO is the company. They’re the person running the show, and one of the first things I look for is their ability to, well, run the show. To prove to me that they own any mistakes or errors, that they have vision, and that they have heart. Here are some things that are non-negotiable when I’m looking at a CEO and deciding whether or not I want to invest in them:

If you’re the CEO, the buck stops with you. I need to know that you’re ready to take full responsibility for everything that goes out the door. And that doesn’t mean I need everything that goes out the door to be perfect — we’re all human, and a typo in a printed memo isn’t the end of the world. But I want to see you acknowledge those typos and not to pass the blame — if you blame your secretary (or worse, berate her in front of me), I’ll see a CEO who isn’t ready to shoulder the responsibility of a thriving brand.

I want CEOs I work with to be invested — with money, time or energy of their own (and ideally, I’d like to see all three). That shows me that you’re just as in this as you want me to be.

Can you solve problems? If something goes wrong, can you pivot? Or do you get flustered, stuck and insistent that what you did should have worked? Even the most successful, most well-run businesses face crises, whether it’s a phone bill someone forgot to pay or an ingredient that compromises the integrity of your formula. I want to see that when the going gets tough, you, the captain of this ship, get even tougher.

Are you going it alone? If so, that’s a red flag. We’ll talk more about building a team in the next chapter, but I need to see that a founder knows when it’s time to bring in outside help, and that they know how to do that in a way that makes sense for their brand.

I’ve interviewed a ton of amazing female CEOs on my podcast. They all have different stories, different ideas, different work styles and different dreams. But after doing the show for the past year, I quickly noticed that all of these badass founders shared some innate qualities and that by listening to their stories, we get the chance to look for those things within ourselves.

So here are the questions I’d advise any aspiring CEO to ask of herself:

Are you optimistic?

If you’ve been paying attention to market trends over the last few years, you’ll know that cannabis-based products — from snacks to drinks to lotions to pet treatments — are incredibly hot. Marijuana-based goods have gone mainstream, and you’re just as likely to find an elegant CBD-infused tea in the refrigerator of an upscale home as you are a bottle of Pinot Grigio.

Hilary McCain is the founder of Sweet Reason beverages, a line of cannabis- and hemp-infused drinks with flavors like strawberry lavender and lemon rhubarb. In their chic bottles, Sweet Reason drinks offer consumers a natural way to unwind and recharge, and the brand prides itself on using high-quality ingredients (not to mention the fact that a portion of every sale goes to mental health research charities).

When I spoke with McCain, she told me that the key to an entrepreneur’s success lies in a firm commitment to optimism.

“[A sense of optimism] is just so important in the ability to survive entrepreneurship…to really look at problems optimistically and know that there is a solution to everything, that they just have to find it. And that they are able to solve it, even if they’ve never done it before.” It’s not about being in a good mood all the time, or about refusing to engage with challenges or negative feedback. It’s a firm belief that what you’re doing is the right thing and that you are the right — and the only — person who can do it.

Are you committed to lifelong learning?

I couldn’t wait to graduate from business school. Finally my education would be finished, I thought, and it would be time to leap into the world of entrepreneurship. I was ready to apply everything I’d learned to my future empire.

And I spent a lot of time in school, as most of us do. But if the day you graduate is the day you think you’re done with learning, you couldn’t be more wrong. I’ve said that a good CEO knows when she needs to know more, and in the case of many great brands, it’s that hunger for knowledge that leads to the million-dollar idea.

Whatever your field, whatever your interests — do you want to know more? Are you willing to be taught? Even if you’re already an expert, are you willing to admit you still have a lot to learn?

“There are successful entrepreneurs who didn’t even go to college, and who certainly don’t have business backgrounds. So I really think it comes down to the person, whether or not they can figure it out,” Kiri Cole Popa of The Health Examiner (more on her later!) once told me.

I love this take because it demonstrates something I think is really important to remember about becoming a CEO: it’s really and truly never too late. All those “30 Under 30” lists? Stories about wunderkind founders who sell their first apps to Google straight out of Harvard?

Ignore them. You don’t have to know you want to be a CEO from the day you start third grade, and you certainly don’t have to know you want to be a CEO the day you finish school, whether it’s after your senior year of high school or ten years into a postgraduate degree. A passion for learning — for wanting to know where, when, why and how — is way more impressive to a smart investor than the names on your résumé.

Learning, of course, leads to doing, which brings us to the next question I want you to consider.

Are you open to failure?

A good CEO is one who fails — ideally, one who fails often!

That might sound counterintuitive, especially if you’re constantly bombarded with stories of successful people who take one idea, spin it into a billion dollars and then tell you that making it to the top is easy.

But for every great idea, or great success, there are ten ideas that, well…aren’t so great. Or 10 new visions for how to run a business that sound great on paper but flop in the real world.

When we dug into the narratives about failure, Suze Schwartz said: “You’re going to fail. And failure is just a way to get better…Not everybody starts and is crushing it from day one! And most of the entrepreneur stories you’ll hear are people who started and got crushed, and then they crushed it.”

In many ways, your first big failure should be a relief. You’ve gotten over it, and you’re still here! You’ve proved to yourself — and your investors, not to mention your employees, friends and family — that you have the ability to get back up after a fall.

Casey Georgeson’s Saint Jane Beauty is an ultra-luxe skincare line that utilizes CBD in its moisturizers and serums. Georgeson was the first person to take CBD products to the high-end market, and when you’re the first, you’re inevitably going to strike out from time to time. But what Georgeson told me on the podcast is that the failures themselves don’t matter — it’s what happens next.

“Just go easy on yourself, because it’s a learning process, and you’re going to have tons of failures,” she said. “You’re going to have wins, hopefully that balance out the failures. But the failures are tough, and you have to pick stuff up and move on quickly and not let it go too deep — because there’s so much ahead!”

Are you (a little) crazy?

If I had wanted it, I could have stayed in finance. I could have stayed in accounting. And I could have stayed at Bloomingdale’s.

When I quit each of those jobs, I’m sure plenty of people in my life thought I was crazy. I was giving up good salaries, good career paths and associations with extremely prestigious companies. What more could I want?

The truth is, I am a little crazy. Because entrepreneurship is in my blood, and I believe wholeheartedly that every true entrepreneur is a little nuts.

Georgeson’s career arc looked pretty similar to mine. She had degrees from great schools and jobs at companies like CNN and Sephora. If she’d wanted to, she could probably be president of CNN or Sephora. But she knew she was meant to blaze her own trail.

“You have to be a little crazy,” she told me. “You have to be willing to put in the work, and you have to be kind of addicted to it. It’s not a decision right now. I just am so compelled to do it. And I think that’s what I didn’t expect.” When she started Saint Jane, she knew she had to go all-in, which requires a kind of willing suspension of disbelief. You have to believe that people will want your product, you have to believe that the money will come when you need it, and you have to believe that you’re going to get it right. Carly Stein, founder of Beekeeper’s Naturals, said something similar when she was on my podcast. When she told people she wanted to leave her job as a financial analyst at Goldman Sachs to focus on her brand of all- natural alternatives to traditional OTC medicines, people thought she was nuts — why give up such a prestigious (and lucrative) career. But Stein believed in her vision and was eventually able to get her product into Whole Foods, where today it’s a bestseller in their booming natural remedies division.

The lesson is: if people think you sound crazy? You’re on the right track.

Are you adaptable?

It’s important to have convictions, values and boundaries. If you don’t have those things and really root yourself and your work in them, there’s only so far you can go.

But just like the tall buildings designed to gently sway with earthquakes and hurricanes rather than break apart, you’ve also got to be adaptable.

Think of it this way: most of us have relationships with a wide variety of people. You might have parents, a spouse, kids, friends, employees, bosses, acquaintances, even frenemies. Would you interact with all of these people in exactly the same way? Would it make sense to talk to your boss the way you’d talk to your husband, or to your kids the way you’d talk to your best girlfriends?

Of course not. You’re still you during all of these interactions, but you’re a you who adapts to different people and different situations. It’s key that any CEO brings that kind of flexibility to work because work is filled with people who have different wants, needs, goals and communication styles.

Working in construction management, Angela Leet has had to deal with a wide variety of personalities — sometimes on the same job sites.

“There are times when I’ve learned to use being a female in a male industry to my advantage…If I have to be sweet to somebody, I can pour on sweet. I can pour on bitch…I can wear my yoga pants or I can wear my cowboy outfit or I can wear my formal gown. Whatever the event is, I can show up prepared in the right outfit,” she told me.

And the idea of wearing the right outfit is a great metaphor. So often our vision of the founder is Steve Jobs in his signature turtleneck, or Mark Zuckerberg in the same gray T-shirt and hoodie. But don’t you want to be a founder who uses every color of the rainbow? One who knows when it’s time to put on the ball gown or the cowboy boots?

When I’m looking to invest, my interest is always piqued by founders who can do it all, who seem as comfortable in the boardroom as they are jumping in to teach a yoga class when an instructor calls in sick. If you show people that you, too, can be flexible, it will be easy for them to envision you as the kind of CEO who can take whatever gets thrown at you.

Are you patient?

You might not be as excited about this question.

After all, who likes waiting? I’m guilty of this myself — when you’re an ideas person, it’s easy to get swept away by thinking of a future in which your idea has debuted to tons of fanfare. How many founders have come up with a great product and instantly envisioned it on the cover of a magazine (or those same magazines doing cover stories on them and their runaway smash hit)? There’s a huge gulf between the idea and the Forbes 500, though, and if you focus too much on the latter you run the real risk of not even getting off the ground.

“I think patience is probably number one,” said Tara Dowburd, founder of the uber-busy and in-demand Make Up Therapy, a glam squad based out of Los Angeles. “You really have to be patient because to really build a great business, it doesn’t happen overnight.”

I’ve seen so many founders, many of whom were incredibly smart and talented, flame out. Maybe they launched too soon, scaled too fast or shared details about proprietary ideas before they were fully sketched out. And I know it’s tempting to shout everything from the rooftops, especially in an age when so many of us use social media to communicate and to crowd-source feedback.

But just like Dowburd said: a great business doesn’t happen overnight, and anyone who tells you otherwise isn’t telling you the whole story. Same goes for anyone who tells you it’s easy: I can count on one hand the number of times I’ve truly taken a day off, and owning your own business also means being constantly available. It might mean working tirelessly after the kids are in bed or ordering takeout instead of cooking so you can prep for a big presentation. But in the end, this work is the work you have to do, especially when you’re just starting out.

There’s an old canard: you only get one chance to make a first impression. So why not slow down and make it count, knowing you’ve worked your butt off to make it the best first impression it can be?

Here’s a final question I want you to be thinking about. It’s a little harder to quantify, but it’s maybe the most important question we’ll ask in this book.

Do you have chutzpah?

You might know this Yiddish term by another word: moxie. Or in Spanish: cojones.

Do you have the guts, the gall, the audacity to take your shot?

A good idea and a tightly knit team are important, but it’s mostly about the chutzpah. It’s an ineffable quality that demonstrates that you’ve got the right combination of strength, skills, drive and heart to jump off the cliff and into the ocean of your future. I talked about chutzpah with Victoria Montgomery Brown, cofounder and CEO of leading digital media knowledge company BigThink, and she said something that I think really cuts to the center of what makes this quality so important. “To be a successful entrepreneur takes a great idea, the understanding that there’s a market for it, that you’ve researched, that is differentiated, that you and your partners…are uniquely positioned to build the business. And then, going for it. I just think it’s mostly about chutzpah and taking the leap.”

It’s about saying to yourself: I’ve done my due diligence and put my sweat equity into this project. I’ve done my homework and checked it twice.

It’s time to go for it.

I also want to share a story Angela Leet told me about those pivotal moments in which we discover the chutzpah we didn’t even know we had:

“I had a subcontractor who was out working on an old pipeline. It had asbestos on it. They were responsible for removing the pipeline and putting a new pipeline in, and they weren’t following the procedures that needed to be done. So I went out there to basically say, ‘Here’s the things that we need to do to make sure that we’re complying with the laws.’”

And I remember him patting me on my hard hat and saying ‘Look, missy, we’ve got this under control.’

And you either say, ‘All right, this guy is scaring the shit out of me.’

Or you say, ‘You know what? I know what I’m doing. And I’m going to tell you how this is actually going to happen.’

And that’s what I did. I stood up to him. And I probably hadn’t been on the job more than three months at this point. And I said, ‘Well, sir, let me tell you actually how this is going to happen. I hold your work permit. And if you want to continue to have your crew out here today, you’re going to follow our rules.’

And his tone completely changed. And then we had to have a discussion because he realized, ‘Wait a minute, she could kick me of the job site. And then I don’t get to pay my guys today. I might lose the job because I get behind on the schedule.’ Now he had to make a choice, too. He was either going to actually attempt to have a conversation and we were going to come up with a compromise that worked, that met everybody’s criteria; or instead of being a badass, he was going to be a jackass and he was going to have to kick his crew out. For me, it kind of set a tone in my career.”

When celebrity chef Giada De Laurentiis was preparing to open her first restaurant in Las Vegas, there was a team of restaurant veterans and businessmen ready to tell her how things had always been done.

But De Laurentiis hadn’t gotten to where she was by doing things the way they’d always been done, and her vision for this restaurant, too, was her own.

“I wanted these five windows that open up so that you feel suspended over the Strip, and you could actually feel the Bellagio fountains — so it felt like you were literally suspended over them,” she told me on my podcast.

But no one had pulled off that kind of design before, and the team was hesitant.

“And at the end of the day,” De Laurentiis continued, “I just got up and I said, ‘If you don’t give me the windows, then I will sue you and I will get out of this contract. I will not open this place without these windows.’”

And De Laurentiis’s windows? She got them.

And that, to me, is the beauty of chutzpah. It’s not about walking around strutting your stuff 24/7, acting like the toughest kid on the playground.

It’s about knowing your power — and not being afraid to use it.

The above is an excerpt from How to Be a Badass CEO: Slay the Competition and Reach the Top by Mimi MacLean. Legacy Launch Pad Publishing, 2021. All rights reserved.