Emma Isaacs – CEO of Business Chicks & Author of Winging It

Episode 80

My guest, Emma Isaacs, is the CEO and owner of Business Chicks, which is a global women's business community. Emma just came out with her new book *Winging It* which I just read, and I highly recommend it. Emma has been an entrepreneur ever since she was 18 years old. She's had multiple successful businesses, and her book *Winging It* is about what holds women back (and what propels them forward) in business and in life. On this show, Emma talks about what she has learned as an entrepreneur, how to excel as a leader, how she has managed to have six kids and build a family while also being an entrepreneur, some of the greatest lessons and takeaways of *Winging It*, and more.

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Kara Goldin: Hi, everybody. It’s Kara Goldin from Unstoppable, and we’re so excited to have our next guest here today, Emma Isaacs. Very, very lovely to have you here, Emma.
Emma Isaacs: Thank you for having me. I’m excited.
Kara Goldin: Very, very excited. A little bit about Emma. Emma is the founder and global CEO of Business Chicks, the largest network for women in Australia. They’ve expanded with huge success into the U.S. as well. She’s here today to talk about her book, Winging It, which I just completed this weekend on my cross-country journey from New York back to San Francisco. I loved it. It was very, very inspiring, and super excited to have her here to talk about it a little bit more.
Again, back to some of her background, she’s changed how we think about business events, and has a thriving global community that operates on two continents and 11 cities, producing more than 100 events. It’s so inspiring, I mean, and really, really impressive. With past speakers including Arianna Huffington, Seth Goden, Richard Branson, Sarah Jessica Parker and more, Emma is truly a modern-day role model, proving that anything is possible for anyone wishing to strive for more in their lives. She’s a fearless leader.
I can’t wait to hear more about her journey on today’s show. We’re also going to, as I mentioned, dive into her new book, Winging It, and I’m really, really excited to have you here, so thank you for coming.
Emma Isaacs: It’s a pleasure. Thank you so much. You already know everything about me now. You’ve just read that whole bio. We can just chat.
Kara Goldin: Well, that’s basically what we’ll do, but take us back to the beginning of Business Chicks. How did it all come about?
Emma Isaacs: Yeah, sure. Well, I’m what you’d call a career entrepreneur. What I mean by that is I’ve actually never worked for anyone else before, apart from a little waitressing gig I had when I was at schools. When you have your own businesses, you need to work out how are you going to make enough money to pay the rent. You need to work out how are you going to make enough money to buy a house. Then when the kids started to come along, and how I’m going to feed them as well.
This concept of winging it is something that’s been ingrained in me from a very, very early time in my life, and I’ve had to make it up on the fly. I had my first company when I was 18 years old. It was a recruitment company. We put temporary and permanent placements into businesses, and that was really fantastic. I had that business for seven years before deciding I wanted to try something new, but it was an awesome, I suppose, learning and foundation in business.
A girlfriend actually invited me along to a Business Chicks event. At the time, I said, “There’s no way I’m going to anything that calls themselves chicks. I mean, that’s the most derogatory word. I’m a feminist. I’m a serious entrepreneur. I’m not going to anything that calls themselves anything chicks.” She said, “You need to get over yourself, and you need to come along and check this thing out.”
I went along to my first event, and just absolutely fell in love with the concept. At the next event I went to a few months later, I heard the business was for sale, and I was 25 at the time. I’d never run a membership organization. I’d never had any experience running any sort of event whatsoever, but I ran up to the lady at the end and I said, “I want to do this. Can we talk?”
A few months later I bought the business, and back then we had a membership of 200 people, and now we reach over 500,000 women globally, which is exciting. It’s been 15 years of my life, and I’m still honestly as excited and juiced about doing what I do as I was 15 years ago.
Kara Goldin: That’s awesome. You started in 2005?
Emma Isaacs: Around then, yeah. You’re testing my memory, but yeah, around 2005, sure.
Kara Goldin: My company started in 2005 as well, my company Hint. A great year.
Emma Isaacs: It was a good year for entrepreneurs.
Kara Goldin: Right, an amazing year. The book, Winging It, what’s the most important message that you want people to take from it?
Emma Isaacs: Well, given my work speaking to women, I’ve really spent the past 15 years talking to thousands of women, and it’s been a beautiful journey to uncover what holds women back and uncover what propels them forward. Through this collective wisdom, I was able to write this book, because it’s completely sacred, what these women have to tell us. Unfortunately, though, it is still women who are plagued with a unique set of problems. You know, we do often wait for permission, and we do often wait to be tapped on the shoulder, and we do often wait until we have every single skill before we go for the job promotion.
We all know this whole concept, of you’ll see a job advertisement and a woman will think, “I’ve only got six or seven of the ten qualifying criteria, so I’ll never apply,” and a guy will have three and he’ll think, “Oh, yeah, I’ll just go for it.” I really wanted to write this book to be able to encourage women to give their dreams a go, to have a shot, to progress without having all the answers. That’s really what Winging It is all about. It’s about backing yourself, and having the confidence to press on without having a roadmap of where it’s going to take you.
I really think this is the year of winging it. I don’t know how you feel, but I think we’re all getting served up hundreds of lessons in this time about what it’s like to lead businesses and lead families in a time of massive uncertainty, when none of us know when we’re going to be allowed out of our houses, none of us know when we’re going to be able to go to live events again. I mean, my business has been decimated. We can’t have any gatherings of any sort, and instead of it being a blip on the radar, it’s been a full-on, head-on collision.
What this time has required from leaders is a set of skills that, I suppose, encourage our people to say, “Hey, listen, I don’t have the answers either, but we’re going to progress ahead and we’re going to be as gentle as possible and try to figure it out as we go.” That’s what we’re seeing, with great leaders in this time are the ones who can wing it, to a degree. I think this book is really, really timely.
Kara Goldin: Yeah. No, absolutely. I was thinking a lot about this as I was reading your book too. It’s just a different type of leadership that is required during times like this. I think certainly there will be businesses that will be asked, “How did you react as an entrepreneur?” I think it’s such an important point.
Was there a point when you realized that you were an entrepreneur growing up? I mean, obviously you’ve always worked for yourself, but I waitressed as well when I was in university. I always tell people I actually call myself an accidental entrepreneur, because I never sat there and put a stake in the ground and said, “I’m an entrepreneur.”
Emma Isaacs: “That’s my job title.” Yeah, no one does. Yeah. I mean, I don’t think anyone does, right?
Kara Goldin: Actually, I think more men do it than women.
Emma Isaacs: Right, right. Yeah.
Kara Goldin: I don’t think women really say that, but I’d be curious to hear.
Emma Isaacs: Yeah. I mean, these days you can go to college to become an entrepreneur. There are courses in entrepreneurship, and we are seeing people come through saying, “I want to be an entrepreneur,” which I find really fascinating, because I had my first company for probably a good, I don’t know, five or six years before even knowing what the word entrepreneur was. It just wasn’t an option for us back then. It was just I had a business and I was just building it, and I was making money and I was going through the motions, but no one told me I was an entrepreneur.
I think if you rewind the clock a little bit and look back in my childhood, my parents would tell you I was an entrepreneur from a very early age. We had a little chat just about birth order before we started this recording, and I’m the eldest of three kids. The archetype of an oldest child, typically … it’s generalizing, but typically … is one of leadership. What I would do is get all the kids in our neighborhood together in our backyard, and I’d stand up on a little stool thing and say, “All right, here’s what we’re going to do. I want you all to go out and borrow some money from your parents and bring it back.” They’d all come with their little coins and bills, and I’d count up the money.
Then I would go up to the local store and I’d buy all this candy, and I’d bring it back in the packets and we’d all open it together and divvy it up into little smaller packages. Then we’d sell it back to the parents at a really, really inflated price. I think I was about seven or eight when I was doing those little entrepreneurial exercises.
Kara Goldin: That’s hysterical.
Emma Isaacs: Yeah. I think we all have clues, right? I know a bit about your story, and there were clues, if you again turn back time, that show you that you have some skills that it takes to succeed as an entrepreneur. I certainly showed some of those in my childhood.
Kara Goldin: Yeah. I wrote about this on LinkedIn the other day. A friend on Facebook reminded me about the story when I was 11 or 12. I used to love to get the large boxes at the grocery store that were used for toilet paper or paper towels. I would always go into the grocery store and I’d ask for those boxes, ever since I can remember, and I would color them, because I thought that they were just these amazing things. I’d put my stuffed animals in when I was little, and I’d make these towns and hotels.
When I was 11 or 12, I asked my friend Robin if she wanted to do a camp with me, and she said, “Well, what would we do?” I said, “Oh, we’ll create a city of these boxes.” I told my parents that we were going to do this and everybody. It was in Arizona, and it was like 120 degrees in the summer. I said, “You have to take the cars out of the garage, and we’re going to put the boxes in the garage so that the sun isn’t beating down on these people.”
I don’t think my parents actually thought that anyone was going to come to the camp. Talk about winging it. We took our signs out on the corner to parents and were like, “Drop off your kids for $5 for the day.” It was like word of mouth. “Those people, they’ll take your kid for five bucks for the day.” We had to turn people away. We laughed at that. I mean, we had so much fun. Then we said, “Oh, we’re actually not going to build a city. We’re going to build a town.” We made up dialogue along the way. I mean, it was hysterical.
Then my brothers came home and they said, “You can’t just keep everybody in the garage all day. They have to have some exercise.” We took them to the local canal and we said we’re going crawdad fishing. We took a string. Again, my friend Robin was laughing. I mean, we had like 30 kids each week, and we did it for two weeks. Then we were like, “Oh, we’re bored.”
Emma Isaacs: “We’re done,” yeah.
Kara Goldin: We had done it. I look back on that story, and actually it’s funny, that one was not in the book that I have coming out, but I said I don’t know why it wasn’t in the book, because I said I would just wing it and make up stuff along the way. That was so funny. What was your first memory of really winging it?
Emma Isaacs: I probably would say buying the Business Chicks business was one of them. Having the grit or the goal, I suppose, to start a company when I was 18 years old was one of them. I come from a very academic family. Out of my 17 or 18 cousins, I’m the only one without a university degree, which is hilarious. I do remember going to university for six months, and dropping out without telling my parents.
I am Australian. I come from Sydney, Australia. I’ve been living in California for almost five years now, but grew up in Sydney. My university was across the Sydney Harbor Bridge, if anyone knows it. I remember, after about six months of being very frustrated with my studies, I remember it was just going far too slow for me and I wanted to get out into the real world.
One of my trips back home from university, crossing the Sydney Harbor Bridge cost $2, right, to give the toll person who was sitting there. I remember looking in my purse for the money and I couldn’t come up with the $2, and I thought, “I’m completely broke. I can’t even pay the $2 getting across the bridge here. I hate university. My life is going far too slow. I know I’m not an academic learner. I know I’m an experiential learner.” I remember in that absolute moment, I just decided I’m going to drop out of uni.
I had zero plan of what I’d do next. I was terrified to tell my parents I’d done it, but I did. I made that swift decision, and it was a real sliding-doors moment for me because a matter of weeks after that, I met my first business partner and went on to found that company with her. I’m a big believer that sometimes one door has to close for another one to open. That was certainly the case for me in that first winging-it moment.
Kara Goldin: Incredible. I should also mention, and you talked a little bit about birth order, but you have six of your own kids.
Emma Isaacs: I do.
Kara Goldin: That’s so awesome. I was saying to Emma before we got on the phone that I’m always the one with the most kids. I have four, and hearing Emma has six, I’m like, “What?” That’s crazy. I love it. What are the ages?
Emma Isaacs: My oldest is eleven, and they range from eleven, nine, seven, five, three, and the little guy is three months old. I just had him three months ago.
Kara Goldin: Oh, my gosh. Wow. You’re still in the zone, in the thick of it.
Emma Isaacs: I’m in it. I’m in it.
Kara Goldin: That is wild.
Emma Isaacs: It’s amazing. You know, I never set out to have this many kids. If you’d asked me when I was 20, “Do you want to have a large family,” I wasn’t even convinced I wanted to have children. It wasn’t this lifelong, “Oh, I must be a mother or else I’ll be a failure at all.” We had the first one, and it was a lot of fun. Then the second one came along, and we just kept on going. I mean, I think my husband and I are a little … I don’t want to say reckless, but we just let life surprise us, and we’ve found that it’s a really beautiful way to live.
These little guys have been such a joy to have around whilst we’re all working from home. My kids are doing online learning. It’s just been a real joy to have him in the house for the past three months. I’ve been lucky. I love being pregnant, and I can do it. You know, I know there’s many. My sister gets hospitalized from morning sickness, but I’m lucky to be a good pregnant person.
Kara Goldin: You’ve been able to?
Emma Isaacs: Yeah. I’ve been able to carry on. I work up until 41 weeks. My kids are always very late, but I work the whole way through, and then I have these beautiful births. I birthed all my six kids at home in the living room.
Kara Goldin: Oh, my gosh.
Emma Isaacs: It was extraordinary. We had the little guy in the pandemic, obviously, and it was at the height of the Black Lives Matter protests. As I was birthing him, there were helicopters whirring around above, and it was a moment of intensity, I’ve got to tell you. It was just a very heavy time for all of us, and a time of deep exploration and confusion and everything being thrown upside down as we know it. I decided to livestream that birth on Instagram.
Kara Goldin: Oh, my gosh. Wow.
Emma Isaacs: I know.
Kara Goldin: What were people saying?
Emma Isaacs: It was beautiful.
Kara Goldin: Yeah, I bet.
Emma Isaacs: It was beautiful, and I want to say it was very PG. I mean, I was in the tub and everything, but it wasn’t like the camera was like right there. It was beautiful.
Kara Goldin: Emma, I want to hang out with you.
Emma Isaacs: We can hang out. We can hang out. We can do it. It was really beautiful. Obviously, at the time I was not focused on what people were saying on the comments. A couple of days later I got to have a look at it, but it was like this beautiful moment of connection and community. people were just, I think, glad to have the distraction of the heaviness of what we’re all going through with a pandemic and airing conversations around race and anti-racism, and people were just … they were gorgeous, the comments. I mean, 60,000 people or something tuned in, which was really crazy. They were just saying things like, “Oh, this is beautiful,” and, “One more push.” It was a great experience. I loved doing it.
Kara Goldin: I love it. I was thinking about this when my son who was now 18, when he was 11 or 12, I think Lean In was just coming out and Sheryl was being interviewed, and the TV was on. We were at the dinner table. I’ll never forget. He said, “Mom, I just realized that women aren’t CEOs.” I’m thinking, “Okay, where is he going with this?” I was like, “Yeah, no, doesn’t happen all the time.” He said, “Why?” I said, “Well, that’s a really good question.” He said, “Well, you’ve always been a really good CEO and a great mom too.” It was at that point when I realized something that no one had ever said to me, which was that I was actually teaching my son things that society maybe really wasn’t as helpful in really teaching. He was asking these questions, and continued to ask all the way through high school.
He played a ton of tennis, and he would come to me and he’d say, “Mom, why is it that the tennis teams in high school are separate? Why are there girls’ teams and there’s boys’ teams?” He said, “I actually like to play with the girls. They’re some really great teams, but why do you think there aren’t co-ed teams?” I’m like, “You should change it.” I feel like what you’re going to hear … and your kids are still a little young, right … what you’re going to hear out of your kids is that what you’ve done is actually helping them to be better humans, better leaders, better managers, better spouses.
Anyway, I just love telling that story because I really think, as hard as it is sometimes when you’ve got one kid or lots of kids, I think that being a working parent and doing this while you’re juggling and trying to figure it all out, it’s worth it, right? You’re doing something for society that I think is so needed, right, that you are teaching these kids to be better at so many different things, and so anyway.
Emma Isaacs: I hope so. I love that you give a nod to that, because you know we’re all in it together, and we all have moments of, “Oh, gosh, I hope I’m making the right decisions here.” I mean, I think when you’re very clear on why you do something, we’ve all heard and studied about needing to know our why, but I think when you’re very, very clear, when there’s clarity around your why …
Kara Goldin: Totally.
Emma Isaacs: … it’s much easier to make the decisions that you need to make as a leader and a parent. That’s been something that I decided very, very early on in my parenting journey, that I was going to be very, very clear on who I wanted to show up as a parent and who I wanted to be as an entrepreneur as well. Of course, there are times when both collide and they’re at opposition with each other, but I’m really, really clear with my kids why I work. It’s not just about taking holidays to Hawaii or wherever. It’s very much about me wanting to be a role model to my six children, about wanting to play a really active role in society, about wanting to shift stuff that doesn’t feel right for me.
I remember a mentor saying to me when I had my first baby, who is now 11, she said to me, “As much as, when you have your first child, you look down at them and you project onto them and you think, `I wonder what you’re going to do with your life and what are you going to make of yourself,’ as much as you’re thinking that about them, they’re looking up at you and thinking, `Hey, Mom, what are you going to make of yourself? What are you going to make of your life? What impact are you going to have?'”
That’s really buoyed me and motivated me to just keep on striving in my career, because I want to be able to inspire them, and I want to be able to inspire other women to know that it is possible to be a great parent and to be a great businessperson as well. You know, those two can coexist. They can.
Kara Goldin: Yeah, no. There, I feel like high school for me was really where I saw, and I won’t lie. There were moments, right? They’re teenagers, right, where you’re just like, “I don’t know if they really respect me, if they’re gaining what I ultimately want to do or whatever,” but I felt like even in the teacher sessions or things where I would talk to the teachers, the stuff that my kids knew, everything from raising money to building teams and how important product is and community, that I never even thought about as a high school kid.
I’ll share one more story with you. When one of my kids was applying to college, and they didn’t get in to their first-choice school and they went to another school, and then they were deciding whether or not they wanted to stay at that school, they were having feelings. I said, “Why don’t you go and apply to the school that you ultimately wanted to go to?” They said, “Because they rejected me.” I was like, “I’ve been rejected lots of times.” It hurts when you get rejected, right? I’m sure you’ve been rejected, right? It hurts, and I’m not going to lie. It really does hurt.
I think I remember smiling when I said this, and she said, “Why are you smiling?” I said, “Because I know that you’re so passionate and you’re so smart that you’re going to do something really big, and one day someone’s going to ask you the question, like, `What didn’t happen that you think should have happened,’ or whatever, and you’re going to be like, `Oh, that school, they rejected me.’ If they end up rejecting you twice, then you’ll be like, `Look where I am today.'”
Emma Isaacs: All the stronger for it, yeah.
Kara Goldin: She was like, “Oh, so you don’t think I’m going to get in?” I was like, “No. The point is it’s still a great story.” Of course, she gets in, yeah.
Emma Isaacs: That’s awesome.
Kara Goldin: Yeah. Anyway, I feel like that kind of stuff along the way is what they learned from you as an entrepreneur. A lot of it is winging it, right? A lot of it is. I mean, that’s what I loved about your story so much, that I’m similar. I mean that sincerely, like I feel like you’re my girlfriend over here, that it’s like attitude and action and really making sure that you’re you’re doing things that you ultimately want to be doing, of course, but also I don’t think so much of this is brain surgery. I think you talked about [inaudible 00:26:40] in your book too. I think that understanding who you are and understanding where you want to go, those things change along the way.
I think that that was something that was so inspirational in reading the book. It’s a quick read, too. That’s the other thing. I hate heavy books, especially during COVID. I’ve been reading tons of books. I think for me, the book was long enough, but it was also just super inspiring, and the people. I mean, you have Richard Branson and lots of people who wrote blurbs for the book. They don’t write blurbs for just anybody. I mean, that’s really impressive. Seth Godin, who else? Oh, Randi Zuckerberg.
Emma Isaacs: Yeah. We’re friends, yeah. She’s gorgeous.
Kara Goldin: She’s awesome. Really, really super, super awesome. What’s next for you?
Emma Isaacs: Gosh, I mean, you know what we just did? My husband did a crazy thing. We’ve bought this ridiculous RV.
Kara Goldin: Oh, very good.
Emma Isaacs: I think the turbulence of COVID has just presented this crossroads for so many people. It’s, again, coming back to that question of what do I really want from my life, and am I really living the life that I dreamed and have the potential to live? For us, we want to get on the road a little bit more and take some more trips, and really start to enjoy ourselves. I mean, I’ve been an entrepreneur for over 20 years now, and it comes with 16-, 17-hour days and often working seven days a week. It’s time to try and enjoy some of the fruits of that labor, but I’m writing my second book as well. Just more of the same.
I am really blessed to be able to have built some amazing relationships, some of the people you mentioned that are featured in the book, and I’m always up to something. I’m always thinking of the next project or the next event. I mean, we’ve stabilized the business, and as we’ve pivoted to online event delivery, but I hope when the world opens up and the borders open up, we can get back to eventing again and have some very exciting adventures.
For now, it’s just being grateful for what these past few months have taught us. It’s really about continuing to stay calm in the face of complete uncertainty and just do our best, be kind to ourselves. You know, that’s what you can ask of yourself.
Kara Goldin: I love it. Are you going to leave soon to go on your adventure? Do you guys have a plan to take off?
Emma Isaacs: We’re thinking maybe we’ll take some time between Thanksgiving and New Year, and we’ll see where it takes us. Yeah, we don’t really have too much of a plan. He’s actually just flown to Pennsylvania to pick up the RV, and he’s bringing it back here. I’m like, “Where are we going to store it?” He’s like, “Oh, I haven’t worked that out yet.” It would not be [crosstalk 00:29:46].
Kara Goldin: He’s driving it back, across the country?
Emma Isaacs: He is, with two of our daughters. Again, it’s probably going to take him five or six days, but yeah. He’s seeing it as an adventure. I think that’s a beautiful thing. If you can see life as an adventure, then most everything else falls into place.
Kara Goldin: I love it. I bet they’ll have lots of stories. I’ve driven across the U.S. actually a few times, but a few years ago, and one of our daughters wanted to go but the rest of them were like, “No way, we are not going to sit in the car.” We still laugh about some of those stories across the U.S. and some of the places … we didn’t have an RV … some of the places that we stayed, and it was definitely an adventure. I think the U.S. is a really beautiful, big place, with lots of different things along the way to see, definitely the national parks. They’re going to have a great time, but definitely you guys will enjoy that. What makes you unstoppable? I always ask this final question.
Emma Isaacs: Oh, I love that. I love that. If I think about what’s led me to any level of success that I’ve had in my career so far, I think I’d come back to relationships. That’s what makes me unstoppable, the relationship I enjoy with my team members. A lot of my team members have been with me for 10 or 12 years, and are still kicking on strong. I love that. I’ve been the emcee at their weddings and been by their hospital beds the day after they’ve given birth.
Kara Goldin: I love it.
Emma Isaacs: It’s a beautiful family. The relationships we have with our talent and our speakers are really, really important to me. It’s something I’ve spent a lot of time trying to nurture and cultivate, is the relationships that I have with people. I love what Dr. Lois Frankel says about that. You know, she says that when you need a relationship, it’s too late to build one, so you should always be looking at your networks and relationships and trying to work out how to do favors for other people and be there for other people, without an expectation of it being returned to you. I think that’s what makes me unstoppable.
Kara Goldin: I love it. I love it. The book is called Winging It. Where is the best place to purchase it?
Emma Isaacs: You can get it everywhere. Barnes & Noble, Amazon. Sounds True is my publisher. IndieBound, Target. Yeah, just do a Google search. I’d love for you to rate it. Thank you.
Kara Goldin: Businesschicks.com. Check them out definitely, and then Emma Isaacs on social as well, and very, very fun. Thank you so much, everybody, for listening. Definitely if you like this podcast, then definitely give Emma a great review, and let’s all subscribe to it as well, so you can see the rest of the very, very amazing people that I have for you all to learn from. Thank you, everybody. Have a great rest of the week.