For our first interview of 2018, we’re kicking off the year with the ultimate Windy City boss babe: Jessica Zweig.
There’s a good chance that, if you live in Chicago and you’re also a millennial female, you’re already familiar with Jessica. Or at least who she used to be. In 2008, Jessica co-founded the website, Cheeky Chicago, just as blogging and online magazines were becoming a thing, and the site quickly became a hit for its hyperlocal content, corresponding events and its insider-y social media presence that gave a peek at the best shopping, parties, and nightlife in the city.
After running the site for six years, however, Jessica had a change of heart. She’s still an entrepreneur, but her latest venture, Simply Be Agency, capitalizes on one of the most important things she learned while running her site: personal branding. Here, we talk to Jessica about leaving Cheeky behind, the power of strong personal brand, and the most important lessons she’s learned as an entrepreneur. (And she’s SO insightful, you’re going to want to read ’til the end …. )
YOU STARTED YOUR CAREER BY LAUNCHING CHEEKY CHICAGO, WHICH YOU RAN UNTIL 2014. WHAT DID THAT EXPERIENCE TEACH YOU?
What didn’t it teach me? It taught me how to be a true entrepreneur. It taught me the true highs and lows of being in business for myself. They tell you that when you work for yourself, you don’t have to answer to anyone else, but the distinction is you have to answer to everybody. It’s a true 24/7 lifestyle. You never stop working, you never turn it off. For some people, that doesn’t work. I learned for me that it does. I learned the power of relationships and the power of creating relationships with the right people, the right partners, the right clients, and the right team. I got my heart broken during Cheeky (a couple times over). Those were the best lessons and the greatest gifts, more so than all the success that I had. I also learned that you can figure anything out. It’s just a matter of believing in yourself. I am a true classic case study of “fake it until you make it,” and everything I basically learned about being an entrepreneur—with the exception of taking classes and having mentors and advisors—I learned by DOING. I think I learned my own sort of personal power in that experience with Cheeky.
IT WAS SO SUCCESSFUL – WHAT MADE YOU DECIDE TO GO IN A DIFFERENT DIRECTION? HOW DID YOU KNOW IT WAS TIME?
I ran it for six and a half years. When I started Cheeky, I was twenty-six. And by the time I left, I was thirty-two. My ambitions, desires, and experience level had changed. I really wanted to be more challenged. I loved it, but I remember saying to a friend, in a totally life-changing coffee date, “I feel like I can do Cheeky in my sleep.” And she looked at me and said, “Well, why would you want to be asleep?” In that moment, I realized I had to do something that really challenged me and pushed me outside of my comfort zone, because Cheeky had become comfortable.
At the time, I had also started getting asked to consult for brands on the side, and I was loving it. It made me realize that I was good at other things and had something to provide other businesses—not just my own. And that’s why I was inspired to create SimplyBe.
YOU NOW OWN YOUR OWN PERSONAL BRANDING AGENCY, SIMPLY BE. WHAT DREW YOU TO PERSONAL BRANDING?
I have a passion for storytelling online. But I didn’t want to be another marketing agency, because the world doesn’t need another one of those. I also don’t think the world needs another technology, or widget, or fancy coffee drink. I think the world needs more humanity. I think the world needs more people who show up fully expressed with no apology for who they are. People who have something to give of themselves to better the world. I know that sounds lofty, but we live in a digital age, and anyone can be a media channel, so why not use that tool and use your voice for good? And that’s why I believe in the power of personal branding. That’s why I was drawn to it. It’s also a space no one is exclusively in from an agency perspective, and I like to be a trailblazer.
I did it for myself, and it’s true that I learned the power of it from my own career. It comes really naturally to me, and it’s something I want to teach because it’s something I do, consistently and effortlessly for myself.
WHO ARE YOUR TYPICAL CLIENTS, AND WHAT DO YOU DO FOR THEM?
My typical clients are leaders across various industries. People who are in C-level positions, people who are heads of departments, entrepreneurs and founders, directors of organizations, etc. We help our clients master their message, build their digital platforms and presence, and launch them and their ventures online so they can live what they love and get more exposure, opportunity, and revenue.
WHY IS PERSONAL BRANDING SO IMPORTANT TODAY?
Personal branding is important for so many different reasons. Personal branding allows you to create a platform for yourself where you can call your own shots and make a business out of your own name (beyond your business). Having a strong personal brand is better than having a strong resume. Google now makes your resume obsolete. If you’re talking to an entrepreneur who’s trying to raise money, having positive public perception is going to help you do that. A strong personal brand makes you a better leader. It makes you a more conscious team player within your own culture and your own organization.
Building an audience is currency that you can monetize. You can make money from a personal brand, if that’s your ambition. You can also provide something valuable.
WHAT ADVICE DO YOU HAVE FOR WOMEN, REGARDLESS OF INDUSTRY, ON BUILDING THEIR PERSONAL BRAND? IN OTHER WORDS, WHAT SHOULD EVERYONE BE DOING TO BUILD THEIR BRAND?
Think about who you want to be. What do you want to be known for? What do you want people to say about you when you’re not around? If you were to die tomorrow, what’s your legacy? How did you make the world better? How did you make your job better? How did you make your company better? How did you make your friendships better?
Your personal brand isn’t just at work. It’s all day long. It’s an expression of you. And really understanding what your X is. Not your X factor, but your X. When people think of you, what do you want them to think about?
It’s important to do some soul-searching, deep work, and vetting to really understand what that message is. And that’s where you start. Having that understanding of who you are will give you clarity around what social channels you should be on and how you should present yourself.
WHAT IN YOUR CAREER DO YOU OWE TO HAVING A STRONG PERSONAL BRAND?
I launched my personal brand by accident. And then by design. The fact that I was the founder of a magazine that had a lot of followers and readers helped launch my own brand. Over the years, I’ve done a lot of self development work. And I still do the work. I make sure to show up with a signature style—from the lipstick I wear to how I appear on social media. It all matters. I have a very strong understanding of who I am. I think that, more than anything, is why I’m able to just do. I grew up in social media, so it’s become a second language to me. It’s become this place where I promote my business and myself.
WHAT’S DIFFERENT ABOUT RUNNING SIMPLY BE AND CHEEKY CHICAGO?
I have an incredible team of women that both like and respect me. (And vice versa.) It all comes down to the team, the culture, and the people. They believe in the mission. They have fun. They see the future for themselves. They have ambition that I can’t teach them, and it matches my fire, which is vital.
While I’m a solopreneur and call my own shots, my team makes it all work. Having been through Cheeky, I now understand what works and what doesn’t. I’ve learned my hard lessons. I’m making better decisions. I’m rebounding quicker. I have slightly more balance in my life than I did before, so I enjoy my career more. And I’m reaping the benefits of that, and I feel an abundance versus scarcity.
WHAT ARE THE BIGGEST LESSONS YOU’VE LEARNED AS AN ENTREPRENEUR?
Failure is a myth. Not starting is failure. Not doing is failure. It’s all about your people, and you really have to keep a very tight inner circle of people who not only believe in you but will tell you the truth and push you to be better. Because no one’s an island. And lastly? Don’t fucking care what anyone else thinks. Do it anyway.
WHAT’S THE BEST PIECE OF CAREER ADVICE YOU’VE EVER RECEIVED?
Believe it or not, if you’re going to be an entrepreneur, don’t worry about making money—just build something great. Build something people want. Build something people care about, and the money will come.