To Top

Meet Jessica Zweig of SimplyBe. Agency in Wicker Park

Today we’d like to introduce you to Jessica Zweig.

Jessica, please share your story with us. How did you get to where you are today?
I started my career in 2008 as an entrepreneur, back before being an entrepreneur was cool and trendy, by launching a magazine called We became the largest online magazine for women in the city of Chicago for seven years. I started the venture out of pure passion and instinct, having no real business background. As a theater major, I had no technology experience (and no business starting a website). Some people don’t believe in the “fake it ‘till you make it” mindset and motivation, but I do. In fact, I am a case study and living example of what that could be. I set my intentions to learn more about digital marketing and I worked hard to discover the world of social media, content marketing, and events. During my time at CheekyChicago, I built an incredibly strong network and developed my passion for digital marketing.

The online publication taught me something very important about myself: I am fascinated by and devoted to the concept of authenticity. I always say, your authenticity is your hottest commodity—your truth is sexy. I realized the power of a personal brand dedicated to authenticity; so, after CheekyChicago, I combined my passion for people and my experience with digital to form SimplyBe. In one week, with one email and one Facebook post, I made $20,000 for my new company. I wanted to share the power of personal branding as a tool you can take wherever you go, as long as you are consistent, authentic and committed to results. SimplyBe was originally supposed to be a marketing consultancy. However, when I saw what personal branding had done for my personal and professional growth as well as how it was shaping the digital marketing industry, I decided to pivot my entire company to focus only on it. Now, we have 20 clients of ultimate status, prestige and success, and a full-time team of six. I pinch myself every day.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
I don’t think entrepreneurship is a smooth road at all! I’ve struggled with business partnerships, hiring the wrong people, hiring toxic people, and being surrounded by difficult egos in business. Unfortunately, I think it’s not something anyone knows how to prevent. I have a tendency to fall in love with people so easily—it is one of my biggest gifts and one of my biggest downfalls.

Clients have also caused hardships. I’ve learned that who you associate with professionally is just as important as the people you allow in your personal circles. I have deprioritized myself and prioritized other things in the past due to toxic relationships with clients. My email took control of my health, my rest, and my self-care. When I say self-care, I don’t mean getting my nails done—I mean taking precious time to restore my body in solitude, spending time with good company, and enjoying time alone.

Entrepreneurship is a journey for everyone. Sometimes, I take on more than I can handle because I am determined to please people. I say yes when I really mean no, and I overpromise and can’t manage to deliver—not for the lack of trying or caring, but due to putting too much on my plate. Over the years, and with the growth of my public brand and reputation, I’ve become good at focusing on the positive and cutting out all the unnecessary noise.

We’d love to hear more about your business.
SimplyBe. is a personal branding company. We specialize in branding people. It’s very interesting to brand a person over a product; we’ve come up with a very specific, strong, trademarked, and exclusive methodology in our practice. We specialize in brand identity, brand strategy, brand management, and execution. We are full service, from content development, social media management, PR support to graphic design.

I am so proud of my team and my culture. I am proud that SimplyBe. is a space full of love, support, and positive energy. I have an all-women team—and I can say that with confidence. My biggest passion is grooming my team to be #bossbabes; that is my life’s work. SimplyBe. is a place where you can work with great clients, do great work, and be supported in the field of your choice, but it is all about working to become your best self first. I foster and manifest in a culture and company that prioritizes fun, play, learning, exploration, and travel. I want every single person that works for me to experience those things.

Our totally kind and hands-on approach to our work sets us apart from any other company or agency. Our hearts are in it.

What are your plans for the future? What are you looking forward to or planning for – any big changes?
We are about to launch a video series called SimplyBe. TV featuring our clients, influencers, and team members on what personal branding really is. To complement SimplyBe. TV, we have launched a blog on our website! We are also conducting a two-day workshop in October that will be led by the entire team. There are bigger things coming up in 2019 that I cannot speak of yet…so stay tuned!


  • You can hire the team at $695 for two hours of consulting that includes a deep dive into our brand kits, which you get for free and gives you a great running start. Each brand kit is a $300 value.
  • To work with Jessica one-to-one is $995 for two hours.

Contact Info:

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

Leave a Reply

Your email address will not be published. Required fields are marked *

More in