Begin Anyway: Jessica Zweig

Today we chat with Jessica Zweig, founder and CEO of SimplyBe Agency, a personal branding agency that focuses on emerging channels to amplify their client’s brands. They turn strategy into reality and authenticity into the hottest commodity. Jessica’s journey is proof that it’s never too late to Begin Anyway- and to create something amazing.

Something that strikes anyone who meets you for the first time is your positive energy. You are a person who genuinely engages those you meet. How do you start each day and how do you maintain this focus?

Well, first of all: thank you for saying that.  Staying positive and joyful is truly a practice and how I start my day definitely makes a huge difference for me.  My morning time is my sacred time. I have a little balcony off my bedroom, and I am usually out there with my coffee by 6am to watch the sunrise. I really try to practice gratitude, in a multitude of ways. Sometimes it’s simply looking up at the sky and marveling in how beautiful it is, sometimes it’s journaling, sometimes it’s meditating (I do 20 minutes of Transcendental Meditation most mornings), sometimes it’s praying to my angels, sometimes it’s is as simple as kissing my two dogs for little longer than normal.

If I get up and workout in the morning, which I do a few times a week, I will mentally thank my body throughout the class for being healthy and strong enough to be doing the work out. It’s really all about gratitude. Gratitude is the facilitator of joy and joy is infectious.

Jessica is the CEO and founder of SimplyBe Agency, a personal branding agency that focuses on emerging channels to amplify their client’s brands.

Is there a motto or daily intention that you focus on to ensure you’re able to maintain your positivity throughout the day?

Not every day is a good day, so when I’m having a tough day, I usually repeat in my mind: “All is well, and all will be well.” This really seems to work for me.  On good days, I just try to stay in kindness. I love to compliment people, smile at strangers, give people hugs. Acts of positivity are always more powerful than affirmations or mantras.

Tell us a bit about your backstory. You and I were first introduced while you were running your CheekyChicago brand. What was that all about and how did Cheeky operate as an introduction for you into the professional world?

Prior to Cheeky, I had been an actress. I went to school for theatre and had absolutely no prior experience as a businessperson. I would joke that when I graduated college, the only things I knew how to really do were waiting tables and being dramatic. Cheeky came about really organically – it was a light bulb moment my former business partner and I had after going out in Chicago, trying new restaurants, going to events, shopping, etc., and just being young girls who loved Chicago. We were using the internet (of course) at the time to figure out where to go, and were shocked that there wasn’t an online resource for women with suggestions on where to go and what to do, so we simply decided to create it.

I always say that the key to my success was my naiveté. I thought – “If I wanted this so badly, other girls will, too.” Failure wasn’t an option. We ended up raising about $200k in seed money, quit our day jobs and launched Cheeky full time the day the site went live. It was around for close to seven years and became one of the most recognized brands for women in Chicago with close to 100k readers and over 100 national brands as clients. It was definitely a game-changing chapter for me.

And you were both so young when you started – in your mid-twenties – what was it like being both young and female while trying to make your way in the world of entrepreneurship?

On one end it was glorious. Everything was new at that time and I had a ton of energy. I mean, I was going out six nights a week! I can’t even imagine that today. But I was getting to know myself (and the city) in this entirely new context, and I saw firsthand how my own personal output directly affected the success of my business.

On the other end, it was incredibly challenging. We were so young, and learning as we went, and in many ways were the blind leading the blind. When I look back on that girl in my 20s, I just send her so much love, compassion and forgiveness. All the ups, downs, wins, losses and battle scars are a part of my story. They’re intrinsic to my success today. I wouldn’t do a thing differently.

One of the most impressive aspects, to me, about what you created with Cheeky is that you did it all before social media and viral marketing. In many ways, you were still relying on word-of- mouth, personal connections, and other types of traditional marketing. What did you learn from the ‘old school method’ that has helped you succeed in today’s world?

This is a great question, and totally relates to personal branding. (Wink, wink.) Honestly, when you live, breathe, drink, sleep, die for something, people feel it. You are your own best business card. I totally started Cheeky on the premise of guerilla style marketing (i.e., going door-to-door putting Cheeky post cards in the windows of small businesses), but it was my passion for what I was doing that fostered such intrigue and traction. That was my biggest lesson from that time, and it still applies today.

Beyond marketing and branding, are there any other career or lifelong lessons that you took from your time building and expanding Cheeky? How have you been able to transfer and scale those ideas effectively with your new pursuits?

How much time do you have? Ha. I learned who I was as a person and as an entrepreneur during that chapter, on a really, really deep level. It was probably my biggest growth period to date.

I made a lot of mistakes running Cheeky. I wasn’t always the most effective manager, I said “yes” a lot when I really meant “no,” I operated from scarcity when things got tough; but, more importantly, I learned to value myself in an entirely new way: the way I communicate, my unique strengths and weaknesses and most of all, my time. Running Cheeky gave me the clarity, runway and courage to move on and to really following my dreams.

Talk about the importance of networking in your professional career – particularly in the areas where you operate? Any best practices for networking and creating genuine connections?

Yes! Networking gets such a bad wrap. I think people find it cheesy, slimy and uncomfortable, which is just not the case. When you’re doing networking right, it’s all about bringing value to other people and asking for nothing in return. Literally.

Networking is about opening doors, making introductions for people and paying it forward. That’s how you create the strongest relationships – because people never forget. That kind of professional generosity creates a boomerang effect beyond what you might be able to see today. I have had some of my biggest, most game changing clients come to me through a contact a year after I did them a huge favor. Operating from a place of sincerity and the genuine desire to get to know people and help them is networking. It’s become one of the most effective tools in my business.

And, as a side note: networking does require you to put yourself out there. So find events, panels, conferences, etc, where you can meet people face-to-face. There’s no stronger format than in-person connection.

Tell us about what you are working on now. You’ve recently created the SimplyBe Agency. What is your focus and what types of clients are you working with?

I actually launched SimplyBe in 2014 as a marketing and branding consultancy. I pivoted the agency in 2016 to focus on personal branding, after seeing the power of what it created for my career (post Cheeky) and how the space in general is exploding. We help our clients not only build audiences, but build an identity, a value and a clear message. It’s not about vanity or self-promotion, but about creating impact for others. We work with everyone from top national executives, to entrepreneurs, to spiritual leaders. It’s so diverse, and it’s so much fun.

What are your goals and ambitions with the agency? Do you have a five-year plan for growing your business?

I want SimplyBe to not only become synonymous with personal branding, but also with being authentic and living an authentic life. (Hence the name.) That’s my vision from a brand standpoint.

From a business standpoint, I absolutely have a five year plan to build out a larger team, have key clients to sustain the agency and ultimately develop online courses, digital masterminds and in-person retreats. I am launching my personal brand website in the fall,, as a sister site to the agency to create content and to promote workshops, products and public speaking to support this plan as well. I believe true entrepreneurs have multiple streams of revenue. They themselves are the enterprise…not just one business.

Talk to us about the importance of mentorship for your personal and professional growth; who were some of your mentors?

Mentorship is LIFE. I talk to my mentors almost every day. I have two key women who I consider my closest mentors. Denise Senter, who I met in yoga and became my business advisor at Cheeky. She then offered me the opportunity of a lifetime to come work under her at an international travel company where I traveled around the world for her for almost two years. She’s my ass-kicker. Calls me out on all my bullshit, while giving me the love and empowerment to really believe in myself.

The second is a woman named Kathy Quinn, who I met right after I left Cheeky. Kathy’s a huge corporate consultant who develops leadership workshops and trainings, and coaches major CEOs around the country on how to better operate their organizations. She’s quite possibly one of the most brilliant people I know and she has really taken me under wing, and has taught me so much of what I know about building a consultant career. My dad is also my mentor; my sage advice-giver and my biggest fan.

How do you focus on mentoring and helping others to grow within your own businesses?

I don’t manage my team: I lead them. I lead by example, but also by coaching and empowering them to see their own capabilities and greatness. It’s an enormous responsibility I feel, and therefore an enormous focus in my company.

At the end of last quarter, during her review, one of my employees told me that she felt more confident when she looked at herself in the mirror because of working with me. I literally could have died and gone to heaven in that moment…like, “My work here is DONE!” That’s how good that felt and that’s what I intend to do with all the people whom I get to lead.

You recently hosted a seminar focused on empowering female entrepreneurs called, the Fear Paradox. Tell us more about your focus on empowering others, and other women, in particular.

Here’s what a lot of people don’t know about me: for most of my young adult life, I was awkward, gawky, uncomfortable in my own skin…not cute. I didn’t have a real circle of girlfriends (in fact, girls were mean to me most of high school) and the boys never paid any attention to me. I had to really dig deep to learn to love myself and know myself.

At this point in my life, after having gone through a bunch of shit to know my own worth, women empowerment has become a cornerstone in my career. I will always seek to find ways to bring women together to create community and conversation around lifting each other up and moving each other forward.

Cheeky was that in a lot of ways, but the Fear Paradox is about something so much deeper and more vulnerable. We hosted our first conference in July and we had 350 women sign up in our first year. The content was incredible – all about the notion of fear and how we as women let it dictate so much of our lives. Women left transformed. To be honest, it was probably one of the best experiences of my whole entire life. I have never felt so in service.

So what have been some of your biggest professional fears and how have you conquered them?

I am afraid every day in some small way. What people think (it used to be a huge mental track), going broke (happened once), disappointing my clients (happened a few times) and just overall balancing everything I’m doing (balance is a fallacy).

Conquering these fears comes back to the gratitude practice. To staying in the light and being a positive magnet for what I want to create. Like attracts like. It’s science…also known as Quantum Mechanics. Do some research on it and start practicing its principles. Once you do, you’ll find fear is pretty much just an illusion and construct of your mind.

“I find authenticity to be so attractive, and that comes from developing a strong relationship with yourself.”

We spoke earlier about how young you were when you created your first business. What advice would you give to a young person looking to build a network and a
brand organically like you have? What are some important qualities to foster and can you suggest any individuals, books, or talks to check-out?

I find authenticity to be so attractive, and that comes from developing a strong relationship with yourself. Invest in coaching, mentors, therapists, workshops, retreats, conferences and your spiritual path. Seriously – do the work and find your passion, your mission and your why. When you operate from that place, you become unstoppable.

I personally love Danielle LaPorte, Tony Robbins, Gary Vaynerchuk, James Altucher, Tim Ferriss and people who are just really doing big shit on this planet in the service of others. Find the people who inspire you, and take pages from their books but of course do it in your way. Remember – for as cheesy as this sounds – everyone is a snow flake. No one has your unique perspective, experience, vantage point, heart and mind. That’s your commodity. Share it with the world without apology.

What do you find most enjoyable about building a company. What is the most rewarding?

Two things: watching my clients succeed and watching my team flourish.

Thank you so much, Jess. You shared some really outstanding insight. One last question. You’re enjoying your favorite cocktail. What are you drinking and who would you love to be sitting across from?

Stevie Nicks. She’s my spirit animal. I love the stories that she tells through her songs and how vulnerable she’s been with sharing her whole life with the world through music. She’s a living Goddess, someone who lives and breathes Divine Femininity and grit. I would be drinking a glass of brut Champagne, French and dry. We would talk about love, heartbreak and always staying true to your witchy, weird, beautiful self.

A huge thank you to Jessica for sharing his Begin Anyway story with us. Be sure to check out SimplyBe Agency and all the amazing the amazing work her and her team do!

Leave a Reply

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