Cindy shares how she became an entrepreneur, founding three hospitality companies focused on data analytics and co-authoring over 10 industry books on topics related to the digital space and data analytics. She discusses how advocates propelled her career forward, how she chooses the people who are part of her support system, and her approach to advocating for herself. Cindy also advises people to determine what their strengths are and play to them, and the importance of a development plan.
Cindy shares how she became an entrepreneur, founding three hospitality companies focused on data analytics and co-authoring over 10 industry books on topics related to the digital space and data analytics. She discusses how advocates propelled her career forward, how she chooses the people who are part of her support system, and her approach to advocating for herself. Cindy also advises people to determine what their strengths are and play to them, and the importance of a development plan.
Hello and welcome to D E I advisors. My name is Lan Elliot on behalf of d e I advisors, and today I'm really pleased to welcome Cindy Estes Green, who is the co-founder and c e O of Kalibri Labs. One of my favorite sayings is when there isn't a seat at the table, go build your own table. And as you'll hear, Cindy is a great example of doing exactly that. Welcome,
Cindy Estis Green:Cindy. Thank you very much. Pleased to be
Lan Elliott:here. Really happy to have you here. Cindy. among your many accomplishments during the course of your career. I'm just gonna read a few of them. You founded and led three hospitality companies focused on data analytics. You've co-authored over 10 industry books on topics related to the digital space and data analytics. Which is a lot. Can you share your journey and what factors contributed to your.
Cindy Estis Green:Yeah I wrote the books actually to stay connected to the industry. I had sold my first analytics business. And my kids were young and I wanted to be connected to their world, but still maintain a strong connection to the hospitality industry. So as I was writing these books to try to explain what was happening in the digital space, which was a big transition period at that time in the nineties and through the two thousands, first decade of the two thousands. it just seemed like something that I could take advantage of my knowledge and the, of the technology, but also sharing it in a way that would allow me to have some flexibility in my own personal schedule as well. So I think that's what started the process. And and then, what I did was just build on an area of interest and decided the areas that I wanted to focus on, which, I really liked this digital technology area and I figured if I could contribute to the industry in some way, I did it initially writing these books and then and then starting another company to try to create some solutions to to deal with the changes in the market. You were really one
Lan Elliott:of the first people who saw the importance of channel distribution in a number of those new parts of the hospitality business very early on before the rest of us had heard about it. But a lot of what you do is really heavily analytical, working with a lot of numbers. And obviously we've heard. Leadership requires you to be really comfortable with numbers. So I'm just curious, did you always have a love of math and numbers, and what advice would you give to people who aren't comfortable with numbers but want to rise to leadership?
Cindy Estis Green:I don't feel like I, my strength was in math and numbers. Ironically, I was, pretty evenly balanced in my s a t scores, much to my surprise, because I never felt very strong in math. But what I realized was that I had a strength in seeing patterns in data for some odd reason. It was just something I was good at. So it wasn't so much the math, it was more like seeing the patterns and then being. Take those patterns and apply them to like real world situations. So it was more the application of the data than it was actually getting into the data itself. So I, for those who are uncomfortable with math, I considered myself more of a writer than a math person as evidenced by the books that I did. I keep going back to that, but I love, I've come to love data, but it's more what data shows us about. Actions can be taken and it's a little different, but sure, I'm comfortable in looking at the numbers, but it's only in the way that they can be used to figure out, a way forward or what is it telling us about the market or what is it telling us about a particular business? So for me it's the insights from the data more than the actual, I don't geek out so much on the data itself, but on what the data can reveal to us about what's happening in a business or in a market. right? So
Lan Elliott:it's less about figuring out how to do calculus and more figuring out what the story is that the numbers are telling
Cindy Estis Green:you. It's really storytelling and which you don't think about numbers as storytelling, but that's the thing that I realized I like the most about data. And I, I learned that about myself in grad school. Had no idea. If anybody had told me an undergraduate times that I would have a job connected to data and math related activities, I would've told them that wasn't possible. But it turns out this a different way of using data and the application of data was, is a whole. Discipline that, that I didn't realize existed. And it's exciting and it is really pertinent for the way business, any industry has to operate going forward is being able to tell a story through the data. Yeah. Yeah. Thank you for that.
Lan Elliott:So before you started your first company, you had a good paying job at Hilton International but you left that and became an entrepreneur. What did you consider before transitioning from a traditional job to being a full-time entrepreneur with your own company?
Cindy Estis Green:That's always a big transition and I think I always had the idea that I would have my own business, although, honestly, I didn't know what it would be. I just knew that I was, I grew up in a family business and I, it was a children's summer camp, so a hotel for kids. But I didn't know what I was gonna do, and I wasn't sure what angle to take. I just knew that. More likely to wanna do something and create something on my own. So I had just gotten married at the end of my stint with Hilton International. And I thought this could be a transition time for me and. If I was gonna start something, I knew my role at Hilton International initially was in a corporate role doing a lot of data analytics. And I thought this is a new area that seems to be a need, and the distribution area was growing and the digital. World was growing and I thought maybe I can go back to doing something like that. Cuz my last job with Hilton International was as a general manager and I went backwards. I went from corporate to property level. But I think that for me, the decision to move into. entrepreneurship was, I knew I would do it, but then when I realized, hey, there's this, I've been doing this analytics work and there's a demand for it and a growing need to understand it, and I liked it and I thought, Hey, maybe there's a business here. So I thought I'll try it and see how it goes. And that was that was 30 years ago.
Lan Elliott:Doesn't sound like you've looked back as you've gone from one new business to another. Yeah, no great story. But you've accomplished so much in your career, but it hasn't been without its challenges. For example, we've discussed how difficult it is for women entrepreneurs to find funding and launch their business. Can you share a bit about how you did this and any lessons learned? If there are other women out there who are interested in becoming entrepreneurs?
Cindy Estis Green:The stories about fundraising for one thing, if you start a company and look for either venture funding or private equity funding or whatever, or external funding it is hard. And they talk about how few women get funding compared to men. And I certainly had that same experience. It was challenging. And I had, I was fortunate to have some. Who were early investors? I, the business that I started was an offshoot of one of the books that I had done trying to look at how the digital marketplace was changing and the impact it had on the real estate owners in in the hotel industry, and a lot of those real estate owners. Said, we need to do something about this and put seed money in for me to start building solutions to the, to dealing with the digital marketplace. So that's how Calab Labs got started. And I was fortunate that I had this core group of real estate investors who recognized that there were issues that were causing them the economics of buying and selling hotels to change. And knew that I could come up with solutions for that and were willing to fund the beginning of Calab relapse. So as, so I was fortunate because I had these relationships and they recognized what I was doing and. And actually asked me to start working on these projects, which was great. But as we grew and needed more funding and had to look to more institutional funding, it was still challenging. But I think the support that I had from those early investors got us through and actually helped us with some of that fundraising. So that was challenging. And, starting a. Especially a technology business, it's really hard and there's a lot of things that have to go right and getting it right, there's an element of luck and timing. It isn't just knowing what to do. Cuz I knew a lot about the data, so there were many obstacles, but I think. What I feel, and you hear this all the time, I mean there's an element of kind of grit and perseverance that you just have to have faith. You can do it and push through, and you have to believe that if it doesn't work out, you're giving it your best shot, and that's all you can expect to do is give it your best shot. love
Lan Elliott:that about the grit and persistence. Big big thing for entrepreneurs, for everybody. So you talked about some of your early investors. How about some early champions in your career? Who would you credit as being really impactful, and how did they support you at a crucial turning point in your career?
Cindy Estis Green:Yeah. I don't think I could have been successful both in my career when I was employed. Company or on the entrepreneur side without champions. So when I started at Hilton International, the guy who was the head. Sales and marketing was a big champion and big advocate. It wasn't just a mentor. He actually enabled me to get in, to have a seat at the table. I would sit at executive committee meetings. I would put the reports together and be asked to actually speak to them. I had direct relationships with the. the top senior executives in the company, which for at that early stage was in my career, I had just gotten my mba, so I was a few years out of an MBA in my twenties. That was pretty impressive for him to allow me to be in those positions, and I, it made a huge difference. And then one of the big things that he did, After I was in the corporate role and I said, I wanna prove that this data and technology can make a difference to the way hotels are operated. And I asked to go into a hotel to run it, so I became the number two and then the general manager at two 400 room Hilton International Hotels, he let that happen. And he, that wasn't a normal path. And because of his paving the way for me and then the guy. Who actually took me under his wing when I was number two. He, they really made it happen. And having that kind of advocacy on my behalf made all the difference and for me to have been able to run hotels has helped me immeasurably in my career.
Lan Elliott:It's an amazing journey to recognize that you needed a skillset and go, what you said was backwards. It's not really backwards, but to go and get another skillset to leave your job and get another skillset so that could propel you forward. So I think that's really great. Advice. Let's talk a little bit about support systems. So a concept that we discuss on the d e i advisors podcast is having a personal board of directors, the people that you go to for advice, for support, for help. How do you identify who's part of your support system and when you call on them, what types of things would you call on them for?
Cindy Estis Green:I think that, a lot of people look for mentors who are others they can go to, and I think having a wide range of people to talk to. For me, there were very few women who were in senior roles, and I honestly don't. There were none that I could go to to talk to about these kind of things. Earlier in my career, there were just so few women that, and role models, almost none. There were mainly men that I went to, but it didn't matter. I As long as you start getting, you just have to be resourceful. It's like when you have a question, you have to understand that you don't know all the answers, even though you have confidence to figure it out. It's okay to reach out and to go to others who have different skill sets. So it's really a matter of when you're feeling uncertain, knowing that whoever you talk to, you can. you can say you're uncertain about it and be comfortable to say that because sometimes everyone, you'd be afraid to let on that you don't know something because you'd be afraid that would look like you're, you don't, you're not prepared to take on a bigger role. But I'd say that board of directors or that board of advisors. Has to be people that you can be comfortable to be vulnerable and to be able to say, I don't know something. Can you point me in the right direction? And it just depends on what the topic is, whether it's financial questions or operational questions or, personal ways to interact with people or, but I think the most successful entrepreneurs are super resourceful. Everything is hard to do and you just have to assume it's gonna be hard. And the reason that people are successful is not because the path was easy, it was because they were resourceful and scrappy and figured it out, and they had the grit and the perseverance to tough it out when it looked like there was no path forward. And I think that's the hard part, is that entrepreneurs don't see a wall. They see a ladder to climb and get over the wall. They don't just see a wall that they can't get past. I
Lan Elliott:think that's really great perspective is that success isn't always because it was easy or it just happened, or because it was luck. There's a lot of vision and belief and grit in, in getting there. So a common generalization that's out there is that women don't do a good job of advocating for ourselves. But you've had to do that throughout your career. And like me, you're an introvert. So how do you advocate for yourself in a way that feels authentic to you? And what would you tell people who are struggling to find their voice to ask for something that they really.
Cindy Estis Green:I think early on I would say to myself, what's the worst thing that can happen if I ask this question? Or if I try to push to get something? I think there's this tendency, and I share the same kind of tendency as many other women to be hesitant to, I look like I'll. I'm tough and I'll ask anything and I don't mind pushing forward, but I do have that hesitancy and certainly earlier in my career, even more the concern that somehow I, if I push too hard, I would be viewed in an unfavorable light. And there is a tendency for women to be looked at, that sort of double standard. But I think by being able to say to myself, what's the worst thing that can happen? And just ask and just figure if I don't get what I. you're never gonna get anything if you don't ask. So I just kept my eye on the target and just kept pushing forward. And I think, having the willingness to do that and to not be afraid if somebody pushes back or says no, and to just push past it and just know that there's gonna be lots of nos, but you have to ignore them and you have to amplify the positive things that happen and those negatives. And I think. That's a tough thing to learn to do and it's something that I've gotten much better at over time. But a lot of men will claim to be able to do something before they are able to, and women will tend to be more honest and say I don't really know how to do that. You can't really talk that way. Like you just have to make the assumption that you'll figure it. And talk as though you can and just fake it till you make it. There's something to that and there's nothing wrong with that to be able to push forward.
Lan Elliott:Yeah. I had an early mana, early manager tell me, if you don't ask, you don't get. And that resonated with me just in a way he looked at the world, which I hadn't thought about before. And it's it's similar to your, what's the worst thing that could happen? You could be exactly where you are right now. So one of our favorite questions at D E I advisors is what advice would you give to your younger self? And I think it really speaks to the importance of reflection in helping in one's personal growth. What would you want your 22 year old self to know looking. From this
Cindy Estis Green:perspective. So I would say three things. One thing is really learn your aptitudes. Like I didn't know, I didn't know about this ability to seek patterns and data, like I didn't. It took me a long time to recognize that and realize how that could fit into a job or a business. The whole point is to play to your strength. So if you can't force yourself to be what you're not and you don't wanna try to do that. So if you understand your aptitudes and there's career counseling and all kinds of tools to help do that much more even than when I was. At an earlier stage in my career. So I think learn your aptitudes and play to your strengths to try to really build something around what you truly have an aptitude for. And then the second thing is, the misses and the things that don't go right, you have to view them as just bumps in the road. You just can't look at them as oh my God, I failed. They are just bumps in the road and you just have to move past them as quickly as you. And I'd say the third thing is and I wish I was better at this earlier in my career, but I've gotten much better now. Very few things are so monumental that they're showstoppers, but they feel that way. And you just feel like when something doesn't go right, you cannot consider it monumental. Life changing. It's just get over it. What I said about the bumps in the road, but some things you say, oh, that's not just a bump in the road. That's a huge, job I didn't get, or assignment or promotion, or. Very few of those things are so monumental that they're gonna actually change the trajectory of your career and your life. So you just have to know that there's, there are five other paths you can take, even when it feels like it's the biggest thing in the world. Just know that very few of them are gonna be life changing and immediately work on another.
Lan Elliott:Yep. I heard recently someone say that the recovery is actually the important part, right? It's not so much about running into a bump in the road. But like you said, your perspective, how you handle it, how you recover from it that really is what's going to make the difference going forward. So
Cindy Estis Green:yeah, you really don't wanna agonize over things because. Life is too short and you don't wanna spend your time agonizing over what might have been. It's like you can make your path forward and you have to believe that you will make the path forward. If you're waiting for a path to open for you. You could be waiting for 30 years. So just know that the path is there. You just have to take out your machete and start cutting through the jungle to find it. And that's, it may seem hard to do that, but you have the power to do it and you should do it. If you're determined to accomplish something, then pull, let your machete and start cutting through the jungle because we all have the capacity to do that. That's great advice.
Lan Elliott:I'm gonna ask you a question that wasn't on our original list, but that you alluded to a little bit earlier. And. About the double standard that sometimes it's difficult for women to be nice, kind, likable, and also be viewed as being good at their job, being being. competent at doing their work. And it's sometimes a choice, but it's really more about a balance and how to walk that line. And you've had to do that in your career. Going out there and promoting your business and talking with people, how do you try and find that balance between being nice and kind versus being good at your job, which shouldn't be, it shouldn't be that you have to choose, but sometimes it feels
Cindy Estis Green:I guess I just have a mission and a goal and I'm just going to accomplish it, and I, as I've gotten older and further along in my career, I worry less and less about what others think of me. because, I think about wanting to be fair to people and looking back and not feeling like I would regret any way that I behave toward anybody. So it's more kind of integrity, wanting to maintain my own personal integrity and behaving in a way that I can be proud of my behavior. So it's not like I'm so goal driven that I would, run over anybody no matter what, but it's my own rules about, moral morality and integrity that I wanna follow. And in following that and trying to achieve my goal, that's naturally. results in a balance because I am driven and I am very determined and I have a mission and I intend to succeed, but it's not at the expense of other people. But I never, and I always think about this, I never. The way I treat people, I wanna look back and feel good about it, not just in the heat of battle, but even later I wanna look back and say, I did the right thing. And like during Covid for example, there were a lot of tough decisions to make to just survive and not know what was in the future. And I wanted to make sure that, when the, when things calmed down and things stabilized, two years later I would look back and say I did the right thing. So I think and I feel I did, and I, I wanted to be fair to people and be respectful. So I think that if I. Follow that rule. And I know other people may choose a different way to do things, but following my own personal guidelines for integrity and being fair to treat people fairly and to also achieve my goals. I feel like that's the balance that I've struck. Whether others agree with it, I can't say that. That everyone thinks I, am behaving that the way they want me to but it's I have to live with myself and feel good about what I've accomplished and what I've left behind in making sure that I don't leave any debris in my wake that I would regret.
Lan Elliott:that's a great approach, especially with our industry. It's so relationship driven and you see the same people again and again. So that's a great perspective about how to handle it. All right, so as we're coming to the end of our session As the mission of D e I advisors is to empower personal success. So Cindy, what advice do you have for ex aspiring women and underrepresented groups to better prepare themselves for career advancement, either within a company or as an entrepreneur?
Cindy Estis Green:I think that some people wait for someone to give them like a plan or development plan. I think you need your own development plan. And again, this goes back to something I mentioned earlier about knowing your aptitudes and trying to match your aptitudes with. a growth area that you know is happening in the industry that you wanna work in or the segment of the industry you wanna work in. So I think that once you set a guideline and it's not so rigid and strict that it's like very specific steps that you're gonna take or very specific jobs you're gonna get along the way. Cuz I think if you're too rigid, you. Feel like you're failing all the time, or it'll be too hard to work with a plan that's so restrictive. But I think build a development plan for yourself, whether your employer helps or not match your aptitude with a growth area in the industry that, is something that will be developing and growing. And, just accept that not everybody wants to be CEO of major corporation, for example, or, not everybody needs to start their own business. Be a technology entrepreneur or whatever it is that you choose you, that's gotta be what you choose. That would be fulfilling and be prepared to make changes as you go down this path. But I think if you have a development plan, you can grow your. Skillset down that path and make sure that whether it's training classes or exposure to certain organizations or networking, whatever the elements are, it's worth actually documenting and thinking about that development plan for yourself. And you may learn things. When I graduated from college, the work that I do didn't even. So it wasn't like I could have had this plan and figured it out cause it didn't exist. So there's a lot of younger people coming out of college or within 10 years of having graduated who may do things in their career that doesn't even exist today. But if you think about doing the kind of work that you are most interested and enjoy the most, and then just try to start down that path and then be opportunistic as things pop up, which is exactly what I did. I didn't know what distribution was. Digital marketplace, none of that stuff existed. But as things pop up that look interesting to you, be prepared pivot and move down that path. But I think skill-wise, prepare yourself by building the skills that you need in order to take advantage of those opportunities. That's really wonderful
Lan Elliott:advice. Thank you so much, Cindy. I'm going to put up our website, which is d e i advisors.org. Thank you so much, Cindy, for your time today and your wonderful advice to our viewers. And if our viewers would like to check out other videos, you can do that at our website. So thank you very much. Thank you. Land.
Cindy Estis Green:Good to be here.
Lan Elliott:Nice to
Cindy Estis Green:have you.