Jessica Zweig, Entrepreneur and founder of the SimplyBe Agency

February 14, 2018

Sick, tired, lonely and lost. That's the point where Jessica Zweig, founder and CEO of the SimplyBe Agency knew her path with Cheeky Chicago had ended and something needed to change.

The story of changing paths - especially when it means shuttering something that's gained public recognition the way that Cheeky Chicago had - may be a topic that some guests on our podcast #WeGotGoals would avoid.

But for Zweig, her willingness to share this journey was the perfect mix of authentic emotion and magic for the live audience in attendance for our recording of this episode during January's #SweatworkingWeek.

Zweig shared the inception and co-founding of the online lifestyle magazine that gave women nightlife, restaurant and lifestyle tips as well as deals and events in Chicago. Behind the events, the nights out and the years of hard work, Zweig told the audience that she was suffering during what should have been high moments.

"I ran cheeky for six and a half years and I was really burnt out by the end," Zweig said. "Inside I was miserable, especially for the last year or so."

In a downtrodden moment following chronic sickness and surgery, Jessica understood a nearly universal truth: that if she moved on, she would almost certainly be OK.

"If you've ever created anything, right, it like, doesn't feel like it's something that's separate from you. It's you, it's your creation. And that's how I felt about Cheeky.

The ability to learn from moments like that - we've found through episode after episode of #WeGotGoals - is what makes guests on #WeGotGoals successful. The lesson's that you'll hear Zweig share are useful for anyone not interested in learning them the hard way.


JACAre you guys ready? I think we are too, right?

JZ: Yes, we’re so ready.

JAC: OK, we're going to do this. I'm going to get my official podcast voice on.

JZ: Woo-hoo, me too, then.

JAC:  Hello, Jessica Zweig.

JZ: Hello, Jeana with two last names.

JAC: Yes, OK, good, we’re ready. I'm live with Jessica Zweig on the #WeGotGoals podcast. Hi, Jessica!

JZ: Hi Jeana, so good to see you!

JAC: Good to see you too. Thank you so much for being here with us and with our live audience during SweatWorking week.

JZ: Thank you for having me.

JAC: So on #WeGotGoals, we talk about big goals we've accomplished and big goals that we're striving to accomplish, but first we want to get to know you. So talk to us about how you spend your days and what you do for a living.

JZ: So I run an agency called the SimplyBe Agency. So we're a personal branding agency, which means we work with people as our clients versus a typical agency that works with products and businesses and brands. We work with actual human beings in developing thought leadership for our clients. So what that looks like is we help them clarify their message, build their digital platforms, launch their initiatives, help them grow audience, ideally revenue, a new opportunity to live what they love. And what do I do on a daily basis? Like every entrepreneur, it's totally different. A lot of our time is spent strategizing and building the identities of our clients because they're, they’re—we’re all brands, right? Hello personal branding. It's the space that I'm in, but a lot of our clients, a lot of people don't know how to really articulate what they bring and their value and their, their message in a way that's clear, consistent, compelling. So we really say that that's our sauce at SimplyBe is helping really define what makes you amazing and articulating that in a way that you couldn't for yourself without us.

And then a lot of our clients, we actually manage their personal brands. So we're creating content, managing their social media channels, helping pitch them for speaking engagements, all the things. So we're full service and uh, that's, that's the core of what my agency does. But we do a handful of other little things, which I'm sure we'll talk about too.

JAC: So live what you love. I love that phrase and it sounds so simple, but I bet it's more difficult, wouldn’t you say?

JZ: Absolutely. I mean I run my own business and live what I love, but it all has its own challenges. No day is perfect. You never feel like you're there, there. Where is there? I don't even think it exists. And I think you know what? People really want to do though is feel like they're getting paid and monetizing their genius and what they're good at, you know, what they're good at and what they love to do.

And sometimes those things are not always the same. You know, ideally most people are searching and striving for that. And today we live in a beautiful world where anyone can be a media channel and audience is currency, right? So if you grow your own audience, that's a commodity that you can leverage in a lot of different ways to live what you love. So that is really why I think personal branding is so relevant right now. I don't think I could have built this business five years ago. A lot of people are like personal branding that's interesting or what's, what's that? And I get either one of those reactions and I think now we live in a really exciting time where you can, if you're intentional with how you're showing up online. You can open up a lot of new doors for yourself

JAC: And obviously you're doing very well with it. You've got a team that's present here today and you’re incredibly successful. So congrats on all of that.

JZ: Thank you.

JAC: So, let's get to the first big question. So talk to me about a big goal that you've accomplished and how you got there.

JZ: So I've had an interesting career track and I'll, I'll keep it tight, but I used to run a company called Cheeky Chicago. We were an online magazine for women in the city. We were around for seven years. If you were a millennial girl living in Chicago between 2008 and 2014, you knew what Cheeky was and I left that business in 2014 to launch SimplyBe. And I took a kind of a winding road full of detours and I ended up working for a corporate company for two years out of those these last three years. So my goal when I quit that job to relaunch SimplyBe was just to make money and pay my rent and you know, work for myself.

It was really truly that simple. I say that 2017 was the year that I built a plane in the air. Literally that's how it felt. I was just in reaction to wanting to get away from another situation and sort of re establish myself in Chicago and I didn't really know what that was gonna look like. So unlike I think a lot of entrepreneurs in and in 2018 we've gotten clear and we'll talk about that. But you know, are all about having that plan. I always advise people have a plan and I didn't have a plan in 2000, the very beginning of 2017. I just wanted to take on some clients and make some money. And within 11 months I grew from a team of two to a team of five. I have a full roster of clients, we have our own office space in the Google building and business just keeps coming and so it's a testament to, you don't always need a plan. You should, but you don't always need a plan. You just got to put the right people around you, hustle, work, work hard, and you know, believe you can do it to half the battle.

JAC: So I'm interested to know what you learned from living that phase of your life when you didn't have a plan. Y

JZ: Yeah. You know, I think it really comes down to the people you put around you. I have the most amazing team. I will say I have the best team in the city of Chicago and I really believe that and part of it's luck. Part of it is just being in the right place and the right time on both sides, but it's also really understanding as a founder, as an entrepreneur, what you're not good at as much as knowing what you are good at and putting people around you that can fill in the gaps. Not only just a fill in the gaps because you need the gaps filled, but because they are rock stars in their own right and my job as their leader is to get out of their way and let them shine and empower them to grow careers and not just be, you know, an employee of a company. And so I would say people are definitely helpful when you don't have a plan because they'll keep you accountable. When someone's on your payroll, like as an entrepreneur, as a small business owner, like shit gets real when people work for you, you are accountable to someone's livelihood. And so that really helped me get, get clear, make better decisions faster. And also the right clients, right? So your business is defined by the clients that you say yes to as much as it is the clients that you say no to. And I took on a lot of the wrong clients right up front this last year and I learned a lot and I don’t work with those kinds of clients anymore.

Right? So I think a lot of things can attribute to not having, helping you get through a year like that or a time like that without a plan. It’s really about people, mentors, employees, clients.

JAC: So in going from sort of one phase of your life with Cheeky Chicago into this brand new phase where you're empowering people and helping them find their voice, what sort of, what sort of led to that, what sort of lead to you finding your voice, which was helping others find their voice?

JZ: Yeah, that's a great question. So I always say that. OK, so you guys need to know that I went to school for theater. I got a degree as an actress. Like literally I always, I say this a lot. When I graduated college I knew how to do two things. I knew how to wait tables and be dramatic and I was really good at both.

I still am. So I was like, no, no business, like calling myself an entrepreneur. Right. And so I started Cheeky Chicago when I was 26. I had been doing the acting thing for awhile and I was ready to be done with it. I had this light bulb moment. I had a partner. We had this joint light bulb moment and we started Cheeky and we just totally faked it until we made it and I always say that during that experience I built my own personal brand by accident. I was the face of the magazine that happened to have a lot of followers, so a lot of people were interested in me and it was the dawn of social media. You guys, this was 2008, so this was before Instagram. This is right when Facebook left the universities and anyone could use Facebook and Twitter has just exploded. And so I sort of grew up on social and by virtue of that as I was starting to get Jessica's following and so I say built my personal brand by accident and then by design and then something really incredible happened in 2014 when I left Cheeky to launch SimplyBe. People. I felt like were coming out of the woodwork wanting to work with me, and no one knew how good I was, like no one knew if I sucked or if I was actually really legit and I had this Aha moment back then. Wow, there's power in building an equity in your, in your brand name, and developing a story and a persona. Ideally an authentic persona, but a persona nonetheless that people can latch onto and believe in. And it really opened up a lot of doors for me. It made me money. It gave me opportunity, it gave me exposure. I met amazing people. I mean that was all from having a Jessica Zweig's personal brand. And so that evolution of really finding that myself and it does, it comes naturally to me. I grew up on social, so I'm able to teach it to other people and for sometimes hold their hand through that process. That’s why they hire us. And um, yeah. I don't know if that answers your question.

JAC: Yes. So let's talk about the nuts and bolts of starting SimplyBe.

JZ: Yeah.

JAC: So walking away, from Cheeky, this thing that you had built that people love, that people still talk about, what did it take to know that it was time? What did it take for you to make the leap and start SimplyBe?

JZ: All really good questions, you know, to be frank, I had a—I ran cheeky for six and a half years and I was really burnt out by the end. There were a lot of things that people didn't see that happened in that business. People were like, oh, it's so glamorous and it's so fabulous and it's so fun and to be a Cheeky Girl. And like inside I was miserable. Especially for the last year or so, I started getting really sick, I actually still get like little infections from, I developed an autoimmune disease when I was running C heeky. I got super sick and ended up having to have surgery on that sickness. I had a very challenging relationship with my partner. Um, I very indirectly created a toxic environment of employee, but there were a lot of things there that were really, really hard. Right? But it was my first business and I learned so much. I love and kiss and send light to every single moment of that experience. And every single person, I swear to God I do. They were the biggest teachers. And so by the end of that I just, I was really ready to walk away. It was like a dark night of the soul kind of moment towards the end there because—raise your hand if you're a business owner. We have entrepreneurs in the room. OK, cool.  If you've ever created anything, right, it's like, doesn't feel like it's something that's separate from you. It's you, it's your creation. And that's how I felt about Cheeky. It wasn't this thing that I created. It was me and I was it. And so how do you say out loud like I don't want to do this anymore? And it was incredibly painful experience. So when I, when I ended up taking the leap to leave and do SimplyBe very similar to this sort of last year when I created SimplyBe 2.0, I didn't have much of a plan either. I just knew I wanted to do my own thing and call it SimplyBe and do marketing and branding, consulting and get some clients and be a one woman shop and it was very reactive versus proactive. This year because I had such great success in 2017 and as I said, shit got real.

I put a plan in place, so 2018, we have a blueprint, like a very clear quarter by quarter micro down goals and metrics and numbers and multiple revenue streams that we're building out and sales and marketing strategy. It's all there now. Right. And that's. And that makes me feel really good because I think you need, you need that. And my whole team is vetted on that and it's just a different experience now. So the nuts and bolts weren't there. But here I am nonetheless. And you know, now we're moving forward with a lot more in place.

JAC: And it sounds like you almost led with intuition.

JZ: Yeah, absolutely. And that's so funny that you say that. So quick story, I was still running Cheeky. It was towards the tail end I had had that surgery. I tell this story often, but it's a life changing moment.

I was sitting, I was recovering from the surgery, which if anyone's ever had surgery, you know how intense that experience can be, and I was sitting outside in a park and I had like an emotional breakdown. Like I just started crying. I was so tired. I wanted to go back to work, but I couldn't. All I had been doing was Cheeky for, you know, six, five, six years and I have this little tattoo on my wrist. I don't know if you can see it, but it says simply be. It's written in my own handwriting that I'd gotten in my early twenties and I looked down at my wrist and I heard a voice like my intuition. And it was the first time in my life that I heard crystal clearly a voice, like another voice that came from somewhere else, but it was also within me that said, “You can, you can walk away, you can slow down, you can step out of this. You're OK. It's OK to take a break, a breather. It's OK to listen to your heart.” And I looked at my wrist and I was like, whatever I do next, and I didn't even know what it was I'm going to call it simply be as a reminder to be authentic to wherever I am in that particular time and to ideally help other people do the same. Right? Because every business you do, you should be in service, right? It's not about you, it's about what can you provide people. And so that's where that really came from. And that was, it was all intuition ever since then. And I've never stopped listening to my intuition.

JAC: Incredible. How did you hone that? Have you always sort of been intuitive?

JZ: I think we're all intuitive. I think we're all intuitive. We just need to give ourselves some space and time to hear it.

But that was a pivotal moment. That's when I really started meditating more. That's when I started getting into more spiritual thought leaders. I've always been a little bit into the woo-woo, but now I'm like majorly into the woo. It's like the biggest part of my life. Ask anybody that knows me well. And so ever since—and, and just to be clear, once you hear your intuition, doesn't mean that you're never going to not ignore it. Like you're, you're never gonna be perfect. Once you listen to your intuition, you're still gonna make mistakes and be led down a path where you're like, yeah, my gut is telling me not to do this, but I'm gonna do it anyway because my head and my heart and the people around me are saying this is good. Right? I've had plenty of those experiences. But it comes from sharpening your intuition and getting really quiet with yourself more often than not.

JAC:So you accomplish this big goal of doing this thing that allows you to help other people tell their own stories and build a legacy.

JZ: Yeah.

JAC: Let's talk about legacy. What, what do you sort of define legacy as for your clients? And what do you want yours to be?

JZ: That's a great question. Um, so we're, you know, we all want to make money, have a job, build a career. But a legacy is different. Legacy is what do you want? Really, what do you want to leave when you're, when you die? What do you want people to say about you when you're not in the room? What do you want your name to represent in perpetuity? And I think that for, for, you know, for my clients, it's really—we're kind of, we're kind of elitist in the sense that if you don't want to leave a legacy, we don't really want to work with you.

I don't really want to work with people who just want to be Instagram famous. Sorry, I don’t. I want to work with people who want to leave a legacy, who want to help future generations who want to make the world a better place. Not the whole world because you can't. I just had this conversation yesterday with one of my clients. He was like, I want to change the world. He's in the railroad industry, he's a technologist, and he's like, I mean, I know I can't change the whole world, but my little lot of land. And there's 8 billion of us and if we all did that, if we all made the world a better place, the world would be a better place. So that's how I'm changing the world and I have chills just  now thinking about him answering that question. It's like, that's, that's really what it's all about.

Just change your life. If you can make the lot of land you sit on better, then you're making a legacy, then you're leaving a legacy. And for me, what's my legacy? Honestly, I really want to create space for women to unapologetically love and accept themselves. I, that's my challenge here on this planet. You know, I was reading this book called Material girl, Mystical world by Ruby Warrington. It's a great book and she has this whole chapter on motherhood. She's like 40, I'm 36. Jury's out if I want kids. And she. And she's like, I'm clear. I don't want kids, whatever, you know, Oprah doesn't have kids. Diane Sawyer doesn't have kids—like all these, like amazing, like thought leader women don't have kids because they feel she's like, I align to that feeling and to that purpose because I feel so maternal in creating businesses and creating impact, whatever it might be, and to be honest, I feel that way about my team.

I feel like my legacy is to make, to give them careers and to make them like super boss, amazing women. And if I can play a small role in that and their future of their lives and they love themselves and create more reverberations for more women than I, then I'm living a legacy to be honest. Like, yeah, I love being an entrepreneur and making money and doing personal branding, but I really love doing that. That's really what I love to do.

JAC: And that you can do anywhere.

JZ: Anywhere. That's the thing about building a personal brand of a higher calling that has a legacy to leave.

JAC: Incredible. So let's talk about the future. Yeah. Accomplished incredible things. What does the future look like? What's the big goal that you want to accomplish in the future and how do you plan to get there?

JZ: So I'm deeming the year 2018, the year of experiences. I think we're so like on our phones all day long in email all day long and the most impact I've experienced is when I've gotten out and traveled to a new place or met a new group of people or gone to an event like this and like learned something. That's how I've expanded, right? And so I want to create that for my business and we want to actually launch, we are launching a various series of high-touch experiences. So we, we do the agency work, we support clients as a revenue stream, but this year we're launching workshops, live workshops where you can come work with me for a day or two and we do personal branding, deep dive intensives. And then I’m also launching, I’ve launched global retreats, so three different masterminds that are happening throughout the year in Bali, Costa Rica and Italy. And these were all like visions that I had in 2017 for where I wanted the business to go and we've set timelines and revenue goals against each and marketing plans behind each. So I mean, behind it all it’s, you know, facebook ads, it's um, you know, launch marketing emails, influencer outreach, all of the things, right. So those are, those are big goals. I essentially want to double my revenues from 2017 to 2018 and that's, that's the, that's the big goal, right. And to get there, I want to open up some other streams of revenue and of course, to be in service and to be creating experiences for people that I believe in that I know will help people.

JAC: And in turn probably hiring a bigger team.

JZ: Yeah. We don't want to get too much bigger. And we have two interns on staff with us now and they're like rock stars. And I have a core team of women. There's another woman that works for me. She's not here, she's in Nashville, but we'll probably hire a couple more people and then freelance out as we need.

And yeah, I don't, I don't really want to build this huge team like 20, 30, 40 a hundred people. That's not my style. I want to keep it boutique and like family.

JAC: So how does someone find these retreats?

JZ: You can go to simply be magic dot com. They are happening in March in Bali, Italy's and May, Costa Rica as a November. They are, um, five day experiences. I partnered up with a master life coach. She's actually a spiritual life coach. So you get one full day with her one full day with me one full day with both of us. And we've built in Cultural Immersions, surfing, you know, going to the water temple in Bali, doing wine tours in Italy, going to the jungle and seeing the monkeys in the animals in the jungle in Costa Rica and all food, organic, included themed dinner parties at night. It's going to be really magical. That's why we're calling the magic mastermind.

JAC: I put Bali on my vision board for this year. So it feels like we're going to have to talk.

JZ: We should definitely this. This room is filled with a lot of women. So I'm wondering what’s one to two pieces of advice that you would give to women who want to find their voice or start anew.

JAC: So you know, I always say that you can't be all things to all people or you'll end up being nothing to no one. Know that when people go to the internet or social media or their phones, they don't go to see how cool you are or skinny you are or what you ate for breakfast. They come to help themselves. They come to better their lives to be educated and inspired, to get information to help their families or their business, whatever. So knowing that when you create content, don't just add to the noise, provide something of value.

Always be in the value mindset so that, that's how you really grow audience. And that's how you grow affinity. When people really feel like you've got something for them and that you're not just all about yourself. And then back to the nothing, everything to everyone and nothing to no one, having a relatively clear topics, right? So if you're talking about how much you love your cat one day and the next day, you're talking about where you're traveling to next and the next day you're posting a recipe and the next day or bitching about your boss and the next day you're talking about, should I move to another neighborhood? Like I don't know who you are and I don't know why I should follow you and I don't know what you have to offer. So really thinking about the core pillars of your life, the things that you really are passionate about that you could talk about every single day, and create what I call content buckets and just try and stay consistent.

So the way you grow an audience online is consistency, clarity, and constancy. That's how you compound. I call it the three Cs. If you really want to grow an engaged following, you gotta, be consistent. Pick your platforms. You've got to be constant, be there all the time and be clear in your message. You can't talk about just one thing because you're going to be boring. But if you talk about 20 things, you're confusing. So coming up with the  things that you really that really move you that you love, know and do really well and just be known for that. So that's from a personal branding standpoint, what I always sort of recommend from a high level.

JAC: Perfect. From the audience. We're going to open it up for questions. You'll actually come up to the microphone today and ask your question. So would anyone like to ask a question, of Jessica? Hannah, I knew you would. Get up here.

AUDIENCE MEMBER: So first off, I actually used to love Cheeky. Get the free prosecco at HUB51.

JZ:Oh my God, yes, the Cheeky Card.

AM:I used to love it. Very obsessed, now I’m obsessed with aSweatLife instead. Swap out my obsession. But you did kind of touch on that Cheeky became a little bit toxic. And are there some lessons learned at Cheeky that sometimes now in your new company an event will happen, and you're like, oh my God, because of x, I know to do y.

JZ:Yes, absolutely. Great questions. What didn't I learn a Cheeky that I apply today. It was my first business. I was 26. I ran it for seven years. I mean that's a long time. I learned a lot. Cheeky was my first experience in managing people, so the culture got toxic, right. And I was like 28 maybe at the time when we first started hiring real people and these were like 21 and 22, 23, 24, 26 year old girls. So they were, they were not that much younger than me. They were, we were peers in a way and I wanted them to like me so much. I wanted to be friends. I wanted to hang out, I wanted them to like think I was the coolest boss and you can't, you can't be liked first. You have to be respected first. And I was so afraid of making them mad at me, right? So that when I, when I was, when I had to reprimand them, I, it was awkward like they resented me because they were like, you're my friend. We were just talking about boys an hour ago and now you want to tell me I sent that, that email out wrong. Like that was, it was a line I just did not know how to walk. And with this team, I have a team that respects me first and I respect them and they like me as much as they respect me. And that's a balance I will say. I think I strike pretty well. Now I have a no asshole policy. One of my core values is to be kind. We didn't even have core values at Cheeky. We didn't even have core values. We had a philosophy like to be Cheeky is to be fabulous to be nice to each other, but we were nice to everyone else but each other internally.

At least that's how it felt. You know, when you're running a business as a founder, you're not at your desk a lot, right? So your team, there's an expression when the cat's away, the mice will play. And that was very true for me at Cheeky. And I got burned really bad by that. And I know that when I'm away from my desk at this business, my team is working. And they're having fun, but they're not gossiping, you know, messing around on Facebook and pinterest all day like they're getting their work done. And that's a precedent that I set from the beginning. So that's just an example of it really is about team and as a leader, everything starts with you and it's a note that I set completely differently at SimplyBe.

AM:I would love to know now since you still own your own business and it probably does still feel like a lot of you is in the business. What do you do now to separate and to create boundaries for yourself and to feel good just on your own terms?

JZ:Yeah, well I definitely meditate. I work out a few days a week, so it's a non negotiable. Like I carve out time in the mornings usually before work to go to the gym or to go to a studio. I go to Pure Barre Bucktown shout out it's right across the street from my house. So good. And so there's that right? And I mean I work 24-seven, like I don't like to turn it off. I love to work. It's part of who I am. However, I will say that I brought on Tamara Edwards this year, one of my teammates. And she helps me with my, she came in within two days, she was like, you're doing all of these things and spending all of your time on things you don't need to do. This is not CEO level, this is like staff level and this is like she started policing my schedule, um, and helping me really prioritize what's really worth my time and what, where you going to get the best of me and how I should be spending the most energy and the least.

And I think again, just going back to team, like having people who can really see things you can't and push you to be your best, keep you in line is really helpful. So, you know, and I, when I ran Cheeky, I was single and you know, was like out all the time. Now I'm married, I have a dog, two dogs actually. And I love to be home and so I've just put boundaries innately around my life so I have more balance. But you're still gonna work all the time. So having, having people who can, you know, put that boundary around you to help you do that has been really instrumental.

AM:OK. For the listeners, I really would love for you to tell everyone here about, you know, we, it's this culture. I think what makes, I think all of us who have work experience. It's really the culture that you create that creates productivity and trust and those working relationships. Can you talk a little bit about our Monday meetings? Because that's why I show up on Monday. I just think it's, I just think it's so important, um, for any, any person, entrepreneurs, business owners, just something to think about. I've just always been about this and you actually put it into like an agenda.

JZ: Cool. OK, cool. So every Monday morning we hold a 90 minute meeting. It's all about what's on deck for the week. It's a very intense meeting. It's a one, one time a week. We all got together as a team to do work and to set the tasks for the week. It's very task oriented and at the very end of the meeting I have four core values that I set in my business. Simply be bold, simply be relevant, simply be true and simply be kind. And we just implemented simply be in service, but all the same. To be bold means to step and think outside of your comfort zone. I think we need more bold women in the world like in general, let’s celebrate our boldness, like beyond. To be relevant. Like we want to know what's going on in our industry. We take classes, we read blogs, we keep up, we follow the right influencers were like, we're going to be the experts. We have to. We have to be the experts. To be true is to be authentic, to be yourself, always make no apologies and to be kind is obviously to be kind.

So at the end of every meeting we do a core values roundtable where I have every one of my staff go around and ackno