Dare to Become an Entrepreneur

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career, today we're delighted to be speaking with Julie Gareleck and she is the CEO, author, and entrepreneur.

Julie, I had such a good time reading the book, felt like there were a lot of really good action items in it, but I felt like you were speaking from your heart to me. Just saying.

Julie Gareleck: Thank you.

Anita Brick: We'll get there. She is respected and trusted from the Northeast with Philly where I grew up and New York City and D.C. all the way down to the Atlanta area and the Carolinas. You work with startups, you work with Fortune 1000 companies and you are trusted. You're trusted because you clearly operate with integrity and innovation and you know that you want to create value for your clients so that they can create value through their products. And I love that.

Julie Gareleck: Thank you. Yeah.

Anita Brick: Yeah. Her first book is called Dare to Become: From the Corner Booth to the Corner Office. At first, I thought it was something different, and then after I read the book I'm like, "Oh, I get it now." Thank you for making the time, Julie, and maybe we'll start off with a question. We have a lot of questions that maybe we'll reveal a little bit about what corner booth means.

Julie Gareleck: Absolutely.

Anita Brick: So there was an MBA, a Booth MBA student who said your experience at your parents' restaurant was grueling and there were lots of sacrifices. It sounds like you missed a big chunk of the social side of your high school and college days. When did you realize it was worth it and not just worth it, but essential to your becoming the CEO you are today?

Julie Gareleck: This is such a great question and a great place for us to start. Yes, when you're 16 and you start working for your parents at a family business, certainly not going to be easy. As a teenager, I was a little indignant in that it felt like I was missing out on this ability to be a carefree teenager with no responsibilities. I wanted to be hanging out with my friends at the beach or doing nothing, right? And maybe I did miss a few parties and some spring break trips, but I really learned how to appreciate my time off and make the most of the time that I did have. So I really do feel like it was a perfect training ground for life. I realized pretty quickly even after college, as I entered the workforce, I would see my friends struggling to balance life in the start of a career and simple things like getting to work on time or navigating a night out in the middle of the week.

I realized it really early on that I really didn't struggle to adjust to the pace. I really embraced it and I actually felt like it was a lot easier than having worked for a family business. And so I do think it was absolutely essential to me learning how to develop a work ethic, but more importantly how that work ethic would be really the foundation for me as I started my own business.

Anita Brick: Totally agree with that. I think there's more though. I think you learned also how to manage people tricky situations, and I remember one when you became very, very good that paid off not just for you but with your husband's business as well. I remember in the book you talked about this family that was ordering everything off the menu and you ended up helping the police when they ran out on the bill among other things.

Julie Gareleck: Working in a high-stress environment knowing that there is more pressure on you, I became hyper-aware of my surroundings. I became hyper-focused on my job and communicating while I learned that my intuition has never really been wrong, but I also learned to trust it, and I think that that is such an invaluable skill that isn't tested these days. We tend to listen to what other people say as opposed to trusting this part of ourselves that's saying, "I just don't know if this is right." I did. I mean, I learned how to listen, learn, take it all in, and my intuition still serves me correct. You're right, it's helped out in many situations, especially as a business owner.

Anita Brick: I love it. Okay, so let's fast-forward from the restaurant. We know what the booth part is because in our world at Chicago Booth, it can mean something very different. So when we fast-forward, you worked in a couple of agencies, you worked in venture, and at some point. You said, "Okay, I'm done with this." So here's a question. I'm another Booth student, and she said, "It's one thing to be dissatisfied with the agency where you work and quite another to have the courage to start your own firm. How did you build that courage and how did you get over the finish line to actually launch your venture?"

Julie Gareleck: I'm not advocating for folks to quit their job and start a business, but I had reached a moment in my career where there was a force much greater than logic. I felt that I knew it was the time to make a step to take control of my career because I didn't feel as though I had control. I would say that courage is part of it. I also had a very unique experience in that I watched my parents build their own corporate careers and then ultimately took control of their future by investing in the Avenue restaurant, and so as I moved through my career, I had a sense that I knew I would start my own business one day. I just really wasn't sure what it would look like or what I would offer.

I also learned that I needed experience in order to become trusted by clients. At that last agency that I worked for, I feel like I was already starting to think through what my future could look like and I just was presented with a situation where I made a risky decision to quit and start my business the next day, but it didn't feel wrong. I don't know if that's what it took to get over the finish line, but I trusted in that decision and moved forward the way that I felt I needed to.

Anita Brick: Courage. And I think a lot of self-awareness on your part is the epitome of what I learned from the book. Here's a question from an alum. "Even though I've had a very successful career as a founder, I feel like I'm starting all over again and have to prove myself once again. What are a few things you did to reestablish your credibility and your track record?"

Julie Gareleck: Yeah, it's a great question and you are always starting over again. There isn't ever a moment in owning my own business and growing my business where I sat back and was like, "Hey, things are amazing. I'm just going to sit back." Because at the end of the day, when you're in a business, especially a service business like I am, we're always unemployable, right? We're always facing the next contract, we're chasing the next deal, and some of those deals will go away. Even if you have high retention rates, it's business, right? It's unpredictable From that standpoint. What I learned, what I embraced obviously when I essentially stepped away from a career and tried to start my own business is that what I tried to focus on the most was trusting in my own ability. What can happen sometimes is we listen to all of these sound bites around $100M startup or I should be more successful or this person to my right is more successful than I am.

As an entrepreneur, you have to focus on your own path and you have to remember that you do have experience and that you do have credibility and then just work every day at that goal. And I do think it's hard, and I say this after having owned an agency for 15 years, I still have fear. I still worry about losing clients, but at the end of the day, what I do know is that I've been at my career for 25 years. I've gotten to a stage where I'm very appreciative of what I've accomplished. While it might not be as big as the next guys, it's really a solid place, and so you have to really just focus inward and just focus on what you're doing and just work against that goal every day and not listen to what everyone else is saying around you.

Anita Brick: I think it's a really good point. Two related questions. One was you had a long list of things you wanted to do day one, we all do.

Julie Gareleck: Yes.

Anita Brick: How did you decide what you could complete, what you couldn't complete, and what were your priorities?

Julie Gareleck: Yeah, so my experience had taught me when I worked with startup companies and early-stage companies, early in my career, I did have a background in business planning. I reviewed feasibility studies, I looked at marketing models, I looked at financial models. So I had had that experience and what I had learned throughout that is that it's ever-evolving. The plan that you put together today might look a little different three weeks from now or six months from now, and so I really put together an exhaustive list knowing that it was not something that I had to accomplish by the end of every day. But what I will tell you is that is business. You will never get to a place where there is nothing on your to-do list. You will never get through all of it when you think you're going to, but I wanted to lay it all out so that I could, while I was tactically executing on the day-to-day, I still saw what came next, if that makes sense.

Anita Brick: I think that you have to be open to the plan not going according to plan.

Julie Gareleck: Correct.

Anita Brick: Someone will say to me, "Amita, can you just tell me what is the micro step to get here? What is the best way to do this?" That is a real Achilles heel if someone wants to be an entrepreneur because what was best five seconds ago could be, oh, well, this change, that changed. How do you shift in the moment when it's not on plan anymore, but now you need a new plan?

Julie Gareleck: It's so difficult. I wish I could say to you that I've mastered under pressure, but I will say, I think I've heard this from other great entrepreneurs too, is that as the leader, as an entrepreneur, everything that you do, you are making a decision whether it's a decision for your employees, a decision for your clients, a decision for your business bottom line, there are a lot of decisions that have to be made, and I will say that it's important to make the decision, but also know that if it's wrong that you can correct it. So I often tell my employees this too, is that if you make a mistake, apologize, we're all going to make mistakes, but we have to also be willing to try in order to get to the next level. So we might be wrong, but we then have to adjust based on what we've learned.

As an entrepreneur, you do have to be flexible because again, I mean ask all of these entrepreneurs who didn't see COVID, coming business that's been around for 40, 50 years, that was a situation that none of us could have prepared for, but when faced with it, we had to do the best that we could to continue moving the business forward, continued to servicing clients despite what was going on in the world. So I feel like that was a great lesson for a lot of people in that you can have the best plan, but something could come out of left field and completely derail your original goal.

Anita Brick: I agree. And if you were looking at a graph of how people did big companies, small companies, when COVID came, it would be bimodal because there are people who just never recovered, and there are people who shot up. There is someone that I know and one of her clients decided this couldn't have been worse time if you think about it. In Q4 of 2019, he started a regional airline. Clearly not good timing, but [inaudible 00:12:04]. He didn't know. In the moment, he pivoted and he took that plane, reconfigured it to create space for senior executives who are not going to haul out the big corporate jet. That was really [inaudible 00:12:20]. And he was able to create a safe space for, I don't know, however many people on his planes. That took him from zero to a thousand very, very quickly.

I do think that you have to have the courage, but you created all these foundational pieces along the way. The following questions are really about how people are feeling and how you felt in different situations. So here's one, and this was an MBA student, and he said, "When you described how you felt so vulnerable when you were reaching out to your network, that is a big deal for a lot of people at Booth, outside of Booth." And he said, "I could definitely relate. That said, how did you keep going so that you weren't frustrated and got beyond your fear and being scared?"

Julie Gareleck: Yeah, no, I mean it was vulnerable. I had developed really great relationships with pretty influential folks. When I worked in Philadelphia and I worked up and down the East Coast with different venture communities, I was proud of the work that I've done. They were supportive when I was in that role, and when you start reaching out to those folks at that point, I was 30, I was young, while they thought it was a great idea and they were like, "Oh, wow, that's cool, but Julie, we really can't hire a firm that's brand new."

And I will say that it was frustrating and there were days that I made 20 calls a day and I would cry in my office and I would say, "Oh my gosh, I can't believe that this is the reaction," but what I will tell you is I kept calling and I kept reaching out and I kept living in that vulnerable state, and eventually I started scheduling meetings and I started talking with people that introduced me to potential clients. What I will say is that when you're frustrated, feel it, when you're upset, cry because that's a natural part of rejection, right?I mean, no one wants to be rejected.

Look, I went through it again when I went to publish my book, I got a ton of nos, which was very humbling --publishing houses that didn't want to publish my book because they didn't think that it was loud enough. They didn't think that I was a big enough presence and I just kept at it until I got a yes. The book's being published. So you just have to keep moving forward even when it's hard. Own up to the feelings when you have them and don't let it fester because I will tell you, when you do get the yes, it feels really incredible.

Anita Brick: You're absolutely right about that. Well, this seems to be an ongoing theme. Another alum who said, "I was surprised but not shocked by how you were treated by the entrepreneurial group that you worked for. How did you not bring forward any anger or resentment when you moved into the venture fund, which could have derailed you before you even started?"

Julie Gareleck: So I think youth has a certain type of naivety to it. From my perspective, I was living the dream, moved to Philadelphia. I got a job working for a notable organization that had reach into business communities, and I was starting my career, so I actually was truly grateful for all of the opportunities that were being presented to me. I think the biggest thing that I can, as I thought about this time in my life is that I actually didn't go into the workforce with an expectation of what it was going to provide to me. I would talk to colleagues and coworkers about being upset that I had to work late. I was expected to do all of these things. Expectation piece is I think a lot where resentment starts to bubble to the surface. I've always looked at it, the job itself isn't in existence to meet my expectation, but rather the job is there to meet the expectations of the business. In this case, it was very misaligned, but that was within my power to change, and that's exactly what I did. I gave it my best. I took advantage of those opportunities, and when it didn't align with what I wanted to see for myself, I made a change.

I think resentment, like I said, comes from missed expectation, and again, it might just be my personality too is that my glass is always full. It's just how full is it? That's where I try to focus my energy because as we all know, life is not perfect. Jobs are not perfect. Work is actually very hard whether you do it for yourself or somebody else. I didn't want to let it break my stride. I had big goals for myself, and even that role that I was in was a dream and it was one that I still look back on and say, wow, I'm so glad my boss at the time gave me that opportunity because it led me here, so I don't have time for resentment.

Anita Brick: I love that. It just seems to me like a little commentary here. A lot of people have lots of time for it.

Julie Gareleck: Yes.

Anita Brick: I think it is best to figure out a way to create value, and you are doing this. There's a question that I could really relate to, and I think there are a lot of people, if they feel they have a very limited amount of time with someone, they want to impress them, they want to make their case and they want to do it quickly, and sometimes they can be a little bit pushy and it can actually derail the process. So here's a question from an alum, and she said, "You mentioned that you listened until you had something of value to contribute to the conversation. How did you have the discipline to stick to this when you only had a relatively short amount of time to establish your credibility, impress the business and potential venture partners too?"

Julie Gareleck: Discipline is a great word, right? Because it did take discipline. For some people, they would hear someone say to them, "Hey, look, your goal is to listen and learn, not speak and be heard." I think some people might look at that and say, "Hey, wait a second. No, all voices matter." It's core though. What it taught me was that you do have to listen and learn when you listen and learn to what's being said and you're not listening to respond. This is a big thing I talk about actually a lot in my own business is that I've come across a ton of folks that listen to respond. So as I'm talking or as I'm communicating, they're already thinking about what's going to sound cool and what's going to sound really smart. And what I will tell you is that it always sounds like that's exactly what you're doing.

Anita Brick: You're right. Oh my gosh, it is so transparent.

Julie Gareleck: It's very transparent. And I do think what comes from listening and learning is that you can actually get the full context so that if you do want to impress whether it's a manager or a boss or you want to add value, make sure that you're paying attention and that you're finding maybe those areas that are unclear for others where you can provide clarity. Obviously, in my role, people obviously want to meet my expectation, but I would say to you that I appreciate more of the folks that are consistent, the folks that are constantly learning and wanting to apply that learning. Even if they do contribute and maybe it's not quite right, it's that they're not just sharing to share, they're sharing because they've actually thought through that process.

It does take discipline. I will say it's changed since I was in my early career that there is this narrative that everyone needs to speak and be heard all of the time. But I do think that there is immense value in getting experience and listening and learning to people around you if you do that. I look at where I'm at in my career and my whole career is based off of what I heard and what I experience. And then as I went through my journey, I applied those learnings. I didn't ever go into it as if I knew everything. I had to learn it, and then I developed my own path. But it's hard.

Anita Brick: It's true, and it's also challenging if you are CEO of your own company or even if you're in a large company and you are leading in some way, but I think even more so if you have your own organization. I think you alluded to it a little bit in your last answer, but how do you create a culture that isn't toxic? Let me put it in the positive, that is supportive, inclusive, and all of those things in an intergenerational environment. So I kind of combined two questions. One was from another alum and the other friend of CareerCast. "How have you been able to do that with different priorities as you have new people come in?" I remember one example, and not to give you 12 questions all at once here, but you gave the example of someone who kept telling you, well, their friends have more of this, so they have better snacks or this or that. How did you not want to fire that person and how do you also create a culture that is respectful and innovative and allows for people to be themselves?

Julie Gareleck: I will say it's definitely been probably the hardest part of growing a business is learning how to develop the right culture. I can tell you that having worked in environments that did not necessarily have my best interest at heart or didn't serve what made me feel comfortable. When I started my business, I swore to myself that I was going to create an environment that was reflective of one that I had hoped that I would have. I remember how it felt when I was mistreated or when there was an adverse situation. I never forgot how that made me feel. And I swore to myself that I never wanted to have an environment that people felt less than, where people felt like it was dog eats dog, where they felt like the loudest voice was the only one that was heard.

As I developed the business, obviously, we weren't huge. And when the employee that you referenced that I do talk about in the book, some of it I take from just youth in their own career, which is when you're telling the boss how good everybody else has it, it typically tells me that that person is not happy with themselves or where they are. And it was hurtful and I was upset about it, but they were a great employee. They did a really great job in my role. It's like you can't just discount it because they make these comments here and there. It certainly didn't make me feel great, but I will tell you, and I will tell anyone that's starting their own is don't create an environment that feeds into these narratives.

So I'm in the agency space. When I started my agency, it was super big for agencies to have ping pong tables and happy hour at four and scavenger hunts and paintball trips and things like that. That's not how I identify. For me, what I identify with is that I want to come into an environment. I want to get out on time, and I want to be able to spend time with my friends and family outside of work. Every job I'd ever had, I was on call 24/7. Rather than listening to what other people thought was cool, hence the ping pong table and the happy hours, what I did was just build an environment that respected employees' boundaries. They get to work on time, they leave on time. We all leave together. In fact, at the end of the day, we're not in the office until 6:30 or even seven o'clock at night. We leave at five.

Because if we come into work and we work hard that entire time we're here, we can all leave together. And so I think it's evolving, and I do still think that there are definitely preferences that people have when they come into an environment. I try my best to tell folks before they join the company what it's really like. We work really hard, but I respect the boundary, I respect their time, and I also respect them for their contribution to the team. As you look at multi-generations, I think we all have something to learn from each other. It isn't just the loudest generation that should get the most attention.

Anita Brick: I agree. Agree. Do you have time for one more question, Julie?

Julie Gareleck: Of course, yes.

Anita Brick: Oh, excellent. Okay. So we are a very practical group here. I like to think of it as practical, actionable encouragement. So when you think about it, if you were advising someone, and clearly, you are because you're here today, what are three things you would advise someone to do to create the kind of entrepreneurial venture that would allow them greater happiness and greater success in their career and in their lives?

Julie Gareleck: If someone were to say to me, "How do you build a business?" Well, I've got three things for that. I would say if you want to focus forward on longevity and having success over your career, I do think it starts with listening and learning. I still feel like I listen and I learn a lot. Even after being in business for 25 years, I don't know it all, and I learn something new every day. Be curious. And be curious in that you want to learn and you want to continue to listen to others and develop a path. So that's the first thing I would say is never stop listening, never stop learning.

The other thing I would say is have a plan. So whether you are going into a corporate career or you're starting a business, have a plan for what you want to see for yourself. Don't be afraid to put down on paper what your goals are. To this day, every January I have an Excel spreadsheet where I map out my goals for my life, my family, business, my financial goals, and I've done it every year since I graduated from college and I save for them. So it's really great to look back. I think just having a marker or having a series of things that you want to accomplish is a great way for you to just be mindful of what's next so you don't get stuck in a rut. And you can modify that plan and you can modify the goals as you go. But just to have some structure of like, Hey, here's what I want to get out of the next year. Here's what I want to get out of the next five years. And believe it or not, that will actually help you take the steps to get there.

And then the last thing I would say is just execute. Execute often. Execute always. Success really is in those details and success is in the execution, you can have the best idea, you can have the best goal for yourself, the best dream. And I can sit here and say to you that all of the things that I have wanted to accomplish for myself, I have done. But I've done that because every day I execute. Every single day I tackle something that's going to get me closer to that goal. And so without it, it's just an idea, but I promise you, if you execute consistently every you will get there.

Anita Brick: I love it. That's great. Well, I have one final question. It's kind of a little bit of a big question. I am very curious. You have twin daughters.

Julie Gareleck: Yes.

Anita Brick: Your family is very, very important to you.

Julie Gareleck: Yes.

Anita Brick: How do you do that and still be a CEO who is creating quality and growth?

Julie Gareleck: That is a big question. I would say my greatest gift, my greatest accomplishment are my children. It was definitely a hard road to have them, and it was a hard road. Once I came, I had to learn how to be a mom, a wife, a CEO. Very, very difficult. And it still is difficult. I did what I knew best, which was how do I create a structure that's going to allow me to be present for all things. I look at how I structure my day. I get my kids ready for school every day. I put them on the school bus. Fortunately, they go to school really early. So for 7 AM. Created a structure where I'm present for them. And then when I am in the office or when I turn work on, I'm on. And I've set a very clear boundary. As I mentioned, talking about leaving the office at five, I don't just leave the office at five because it's great optics. I leave because that's the time for my children until they go to bed. I've set a clear structure for myself, and I will tell you from time to time, I don't stick to those boundaries, it ends up manifesting whether my children are unhappy with me because I'm stressed out or at work. I'm stressed because I have 25 things to do for my kids. I really just try to compartmentalize them when I can. When situations arise where I can't or my daughter gets sick or I have a huge presentation, I just try to do the best that I can. And I will tell you it's ever-evolving.

Anyone who's had kids knows it's not predictable and things don't always go as planned, but you know what? Business is like that too. So I would just say set a clear boundary for yourself and really try to be present. And I will say that it's made me a better leader because children are the rawest form of anything, right? I mean, they're honest, they don't have bias. They'll tell you exactly how they feel, and sometimes it's hard to hear that. But I will tell you that they keep me reminded of those things. And so I just try my best, regardless of what role I'm in, is to just do the best that I can and know that I will fail. Sometimes I reference that in my book, how I missed an event for my children at the end of the year, a recital. And I literally worked around the corner and I missed it by an hour. In that moment, I felt like such a failure. But you know what? That's life. Try to do my best.

Anita Brick: And clearly you are passionate about what you do and very authentic and real. What a great model for other people to observe, listen to what you have to say, learn, and then modify it for themselves. But thank you. I am so glad you didn't give up. Your story is inspiring and accessible at the same time, so thanks for doing that, and thanks for making time for us.

Julie Gareleck: Oh, thank you. I mean, this has been a great opportunity, and I appreciate that you saw value in having me here and that you did read the book. Look, the goal with the book, I do wake up and want to add value wherever I can. And I think if the book can help one person, whether they're in a tough spot or whether they're unsure of where to go or they just need a story to laugh at, if I can provide that to one person, then I've done my job because we're all on different journeys, but the path to get there, we share a lot of similar things. So it's helpful when you share those and learn that other people are going through just what you are as well.

Anita Brick: Absolutely. And thanks again.

Julie Gareleck: Yes, thank you.

Anita Brick: And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep it dancing.