Nina Kleaveland, Co-Founder & CEO, Lanyard and Founder, Female Founders in Hospitality

Nina explains why women leaders shouldn’t be defined by the traits that define male leaders, and how she motivates herself to attend networking events.  She shares the goals she set early on to improve her public speaking skills as well as the beauty of networks for collecting different perspectives and helping you make decisions.  She describes how she overcomes negative thoughts, and the value of advocating for oneself and being humble enough to ask for help, which provides opportunities to learn.

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Lan Elliott 0:04

Hello and welcome to D E I Advisors. My name is Lan Elliott on behalf of D E I advisors and today I'm really happy to have Nina Cleveland with us as our guest. Nina is the co-founder and c e O of Lanyard, and she is also the founder of Female Founders in Hospitality. Welcome Nina. Thank you for having me. Thrilled to have you here. Nina. I know you've had a really interesting career journey, and I love that everybody has a different journey to leadership in this industry. Can you share some of the inflection points in your successful career?

Nina Kleaveland 0:41

I. Sure. So I think, I started right out of school working in a hotel in Philadelphia and it was my first taste of hospitality and I just loved it. I loved being at the hotel and getting to serve guests, and so went on to work for Starwood Hotels and resorts both in a digital marketing role, and then eventually in the corporate office back when they were in White Plains. I think, I continued on and ended up going to business school, working for American Express in Hong Kong for a couple of years, and then working for Wyndham Hotels and resorts in New Jersey and really kept coming back to hospitality. I think the big inflection points in my career. Two things. One would be when I left to go to business school I had been a biology major, biology and French actually major undergrad. And so for me I didn't really understand business and I was getting deeper and deeper into that world. And so it was really helpful for me to have that foundation to be surrounded by people who. We're all thinking in that way and studying accounting and finance and and for me to know what I didn't know. And it built a great network and enabled me to launch my career from there. Helped me get the job in Hong Kong with American Express and has been really pivotal. In my career since then having gone to business school and just being part of the Wharton community. So I'd say that's the first inflection point. And then the second one was in 2020 I was working for Windham Hotels and Resorts. The pandemic hit and I got laid off. As did many people in the industry. And it was actually it was an interesting point because I had always wanted to do something entrepreneurial and so I used that as the opportunity to go in a different direction, right? No longer climb the corporate ladder and really think about, building something of my own. And I had an idea. And so started working on that in 2020 during the pandemic, and that's eventually what became lanyard.

Lan Elliott 2:44

That's incredible. I realized when you were talking about your journey that we shared a couple inflection points, and one is that during a downturn when I, when the Grand Great Recession came, I ended up leaving Starwood, and that was when I started Acacia Hospitality because. It was a great moment to become an entrepreneur 'cause there were no jobs. The other thing that we had in common I was really interested in is that we both worked overseas and I'm a big believer that you learn so much living in a different place, not just visiting and having to figure out how do you live daily life in another place and work in another culture. Can you share maybe something you learned from overseas work that has helped you afterwards? I.

Nina Kleaveland 3:29

Yeah. So first of all, I had lived my entire life in a 90 mile radius around southeastern Pennsylvania. So this was a big jump to go from New York or Philadelphia, all the way to Hong Kong. But I also loved to travel and wanted to have a different perspective, and so moved with American Express to Hong Kong and Hong Kong for them is a market level office, not a regional office, not a headquarters. And so it's a really different experience when you are it's a scrappier team. You have to be lean, you have to work quickly with limited resources, but you also have to make a lot of noise in order to get noticed. And so that's definitely something that. Stuck with me. And I think, as I worked for large companies after that, for Windham and others, it enabled me to relate to the challenges and opportunities associated with the teams out in, markets around the world that didn't necessarily have a view into everything that was happening on a day-to-day basis in the corporate office. The other thing that I think I took away from that experience is that you can build relationships and you can find common ground with anyone. And I worked with almost an entirely local team in Hong Kong. Most people were from Hong Kong. Or China or Singapore. There were a couple of of expats from the uk, Australia, but mostly local. I would be in 60 person meetings where the only reason why they were speaking English was because of me. And on the surface it feels like, gosh, that's really hard to find common ground. The cultures are different. The language is different. So many things are different. But I think, through listening and building relationships I became an integrated part of the team. I built some tremendous relationships with some of my team members over there and really enjoyed the experience.

Lan Elliott 5:25

That's wonderful. Stories to share about building relationships in that way, especially overseas, as you mentioned, because it is different and you need to figure out different ways of working and relating to people. I. Absolutely. Now you don't get to where you are today without taking some calculated risks. Can you share an example of success in this regard and how you prepare yourself mentally to take a risk on something?

Nina Kleaveland 5:49

So going back to 20 March of 2020 and thinking about what's next in my career and wanting to do something entrepreneurial, that was a calculated risk. I'd always worked for large companies, Starwood, American Express, Wyndham, and I thought I needed the corporate infrastructure. And so what I did was I gave myself a six month runway and I said, I'm going to work on this idea for six months and see how far I can get. I'm gonna have people put holes in it. I'm gonna see if I can build a brand. I'm gonna do the competitive. Diligence, I'm going to understand what it's like to start a company and do all the research. And so by six months I had brought on a co-founder. I built a brand, I had a, a brand name. I had a, the beginnings of a pitch deck and was getting ready to go out and raised money. And so when I think about taking risks, for me, it's always calculated and I'm the type of person that I'm very analytical. I do my homework and I feel like it doesn't feel like as big of a risk because one I've thought about all of the different factors and the potential outcomes, but at the same time, I also break it into smaller steps. I wasn't thinking about, okay, what's happening in five years from now? I was thinking, what's happening in six months from now and that feels more manageable, you can wrap your head around that.

Lan Elliott 7:09

Definitely. Absolutely. How about when things don't go your way? Have you ever had a career mistake or a setback that taught you a valuable lesson?

Nina Kleaveland 7:21

Of course I'm smiling because who hasn't? But I think most recently, so I started lanyard as a hostile brand, a mix of private and cheered rooms and seasonal destinations that would give younger travelers an entry point into market that get really expensive during peak season. And I built a brand, we had a real estate strategy, this Opco Propco model, and got about 18 months into that and, There were a lot of different factors, many of them beyond my control that made it very challenging to get lanyard in its original iteration off the ground. And there was a little bit of a grieving period. But at the same time I recognized that there was something within what I had done that was actually extremely valuable, and that was understanding the shared stay space. Understanding the employer pain points in a lot of these seasonal markets related to workforce housing. Which we had conversations with employers about that using these locations for workforce housing. And so I never would've gotten to the current iteration of lanyard, which I'm very excited about. And it has just been an incredible journey. I never would've gotten there without that setback. And so it is, it's hard in the moment, but I'll, at the same time, I also think, it's important to understand when to let something go and move on, right? There's, there's some costs there, but also sometimes you just have to keep moving and look forward.

Lan Elliott 8:53

It's a great lesson and also hard to know when, when do you keep pushing versus when do you step back and let go? From a lot of leaders, we've heard how important curiosity is to their journey and learning new skills, and sometimes people discover you need to learn new skills later. In your career that maybe weren't as important when you started out, have you had a situation like that where you discovered a skill that wasn't so strong and you said, you know what, I need to start developing this, and it's, later in my career, but now it's important.

Nina Kleaveland 9:30

I wouldn't say this is not later in my career, but this has been an ever present part of my journey for self-improvement, and that is public speaking. You and I have had conversations about this. I remember when I was in high school, I was the president of the National Honor Society, and as the president, you're required to get up on stage at the induction ceremony and give a speech in front of all of the new induction. There I am at the podium, shaking like a leaf, like so nervous and my voice cracks and I, it is just painful. And I fast forward, have had any experiences like that. And so when I went to business school, I decided that every single day in every single class, I would raise my hand to participate because those classes were. 20 people, 80 people, 200 people. But it was an opportunity to public speak. And so that was my way of saying, I'm gonna work on this and I have a very like specific goal in a specific format, timeframe, all of that. And that really helped me. I wouldn't say that got me all the way there and I'm still working on it. But that was extremely helpful. I've also taken some public speaking courses that have been useful, things that I never would've known about how to speak and body language and all of that. So that's been important in my journey. And then preparation and knowing how to prepare knowing what psychs me up and before I, before I do it. And so it's definitely something that since high school I've been working on. I have a long way to go. And. I just like it. It's something that I wanna be better at, and so I keep working on

Lan Elliott 11:15

it. Yeah, we, and we've talked about how important public speaking is. To advance people's career, and I discovered that public speaking recently, I discovered that it is people's number one fear. It actually beats death in spiders, which I found amazing. But the thing with public speaking, you only really get better not by reading about it, but by practicing. So I love that you set that goal for yourself and have been working on it for all that

Nina Kleaveland 11:41

time. I have to tell you that for me, it's not public speaking. It would be like doing acting on stage or improv. Anything like that in front of an audience would probably be above public speaking.

Lan Elliott 11:57

I love that. Let's talk a little bit about developing a network because. One of the things I loved about the hospitality industry is that people tend to stay in this industry. So the people you meet that you work with, that you interact often become friends along the way. Can you share how you've developed your network in a way that's natural and authentic to you?

Nina Kleaveland 12:20

So I'm an introvert which may come as a surprise. And so networking is actually quite it doesn't come naturally. It makes me anxious. And so this is also something I think we've talked about within various women's groups about how, you go to a networking reception and you don't know anyone and how do you enter a conversation? And so for me the way I think about it is I try to mentally prepare, but then when I actually go to a networking event or reception sometimes I leave and I feel like that was really awkward and I. Not, I like, I wish I hadn't been there and other times there's this rush, it's like a high, because I met some incredible people and I feel like that was really productive and who knows what's gonna come out of those relationships or those introductions or, those conversations. And so that's what gets me going back every time. That's what gets me to do it right, that you never know when you're gonna have that experience where this was. Amazing and so much fun and I'm so glad I went. But it definitely is, it does not come naturally.

Lan Elliott 13:36

A fellow introvert. So I feel your pain as well walking into that very daunting room. And it does get easier over time. I would say for people who are just at the beginning of their career and starting it, it gets easier over time 'cause you get to know more and more people and you have a better chance of walking into a room and seeing somebody, which makes it a lot easier to keep going.

Nina Kleaveland 13:56

The other thing I will say is that with female founders in hospitality Now I have this incredible network of women across the industry adding to the network I already have from working for Starwood and Wyndham and all these years. But that means that any event that I go to, I immediately am gonna know

Lan Elliott 14:15

someone, which is amazing. That is amazing. I think there's a big part of it of. Launching your career and developing over time is finding your people. That can support you. Sometimes it's your colleagues, but sometimes you can find other people in the industry who support you, especially when you're not having a great day. Absolutely. Let's talk a little bit about overcoming self-doubt since we were on that subject a little bit. And I've had the opportunity to work with you on a project since earlier this year, and in that short amount of time I really come to know you as someone who is passionate about driving change. And you're definitely one of those people who wants to get things done. But do you ever have doubts or experience, imposter syndrome? What, how do you stay positive? What are some of the strategies you use?

Nina Kleaveland 15:05

Of course I do. Everyone does. I think it's human right. And this is something that I've also worked on quite a bit because I recognize that there's this negative inner monologue and. I used to think I was unique and special and that it was only me and that I started talking to other people. It turns out, hey, a lot of us have that. And I think what's important is to recognize when the inner monologue is going, when it's negative, and not give it power to shut it down. And so you have to develop strategies that you know you can do yourself, that you don't need somebody else to help with, but strategies to help you get out of that downward spiral. Spiral of negative thinking. And so for me it might be writing down daily wins reframing think you stopping and saying, okay, I'm recognizing that this. This inner monologue is happening and and the negative self-talk is happening. And so what am I gonna do about it? And I start to talk to myself and the third person and just to pause, acknowledge and reset. And so I think for me, what's really helped is just having some strategies that work. I wouldn't say that always works. It's definitely like a muscle that you need to, continue to. To work on. But one I've discovered I'm not unique, and two, it's actually really helpful to talk to

Lan Elliott 16:24

other people about it. It. It is, absolutely. And what I've discovered in doing these interviews is that it never really goes away, especially if you're continuing to grow and take on new challenges. When you do something you haven't done before, it's when it's gonna come back. And I thought this was something that people work through early in their careers, but it continues to come back each time you take on a new challenge and maybe it's a good thing, maybe it's a sign that you're trying something new and stretching yourself, which is a great way to grow.

Nina Kleaveland 16:54

Yeah, I think it's a sign of growth that you if you put yourself in those uncomfortable positions, take on a new role. Take on a new project, do something you've never done before, then of course, there's gonna some amount of self-doubt. I think that's only natural, but that's when you grow the most, that's when you're most learning.

Lan Elliott 17:14

Absolutely. I wanted to talk about advocating for ourselves. One of the things I've seen women do really well is advocate on behalf of their companies. I wanna negotiate something, push for something that will benefit their company. I. Or their team. But when it comes to advocating for themselves, it gets very uncomfortable. And I know this applies to me too. I can go negotiate on behalf of my company, but for me, I'm not as good at doing that. Can you share a story about how you successfully advocated for yourself, either for a raise or a promotion or something along those lines? What steps did you take and what advice would you have for others?

Nina Kleaveland 17:56

I'm the same. I'm much better at asking for things and negotiate on behalf lanyard and female founders and hospitality than I am for myself. Thinking back in my career early on the second job I had out of college I was moving from a job where I was paid hourly to a salary position. And when I initially got the salary, I was really disappointed by how low it was. And so I had to really psych myself up to go and ask for more money. It's hard. It's really hard. And and I was early in my career and I thought I feel so lucky that they're considering this need for this position. 'cause I don't even have marketing experience. Am I asking for too much? Should I just be grateful that I am getting the job? And I asked the hiring manager for more money, for a higher salary. And her initial response was, we don't typically do that. Huge bit increase from your last position, but happy to ask. And she ended up coming back and saying, Yes, we can do it. And so I guess my lesson of course is if you don't ask, you're not gonna get it. But also what I've learned over the years having been on the opposite side of the table, is that I've seen people ask for way more than I ever would've myself. They go back multiple times negotiating on salary. If you can't meet them on salary, then they're asking for other benefits, right? And getting creative on other benefits and other. Value adds. And I think it's just understanding that when you only think about yourself and you're in this vacuum and you don't know what other people are doing and other, examples, it's really hard to understand that maybe what you're asking for isn't that much, but you have to believe in your value and you have to advocate for yourself because no one else will. And when you start to get a perspective on what else everyone else is doing, you'll realize that you're actually not really asking

Lan Elliott 19:54

for that much. Yeah. It's always a shock when you realize everyone else is asking and you feel like, oh, I should be grateful and just say yes. But everyone else is asking. And as you said, if you don't ask, you don't get nope. And if you don't and you know what? If they say no, you're in the same place that you would've been if you hadn't done anything. So the worst they can do is say no. Exactly. My next thing I wanted to talk about is the assertiveness double bind that women sometimes experience and. This is a situation where a woman is sometimes viewed you can't be both nice and effective at your job. If you're too nice, you're not strong enough to be a leader, and if you're too assertive too specific in what you're looking for, you can be deemed difficult, and that also makes it difficult to move forward for women. Can you share how you've. Balance this, because I know you're a go-getter. I know you go and fight for things that you believe in, especially when it's on the behalf of your company. How do you balance this idea of being nice versus being

Nina Kleaveland 21:08

kind? So I think in general, women, I. C women leaders come in all different shapes, sizes, personalities, traits. Right? There isn't one set definition of a woman leader. We're nuanced as we should be. But I also think we shouldn't be defined by the traits that define male

Lan Elliott 21:28

leaders. That's not fair. We're

Nina Kleaveland 21:30

different. I'm kind. I think that's what enables me to relate to people and what one of the traits that's made me successful in my career. It enables me to build authentic relationships because I really genuinely want to get to know other people. I'm also confident and I'm not going to apologize for that. And I just, I believe that those two things don't have to be mutually exclusive. That there is a world for both of those in a female leader, especially if you're not being compared to what a typical male leader looks like.

Lan Elliott 22:05

Absolutely. One of the things you touched on earlier was reaching out to people for support, and I wanted to talk a little bit about this concept of a personal board of directors that we've discussed several times here on our interviews. Do you have a personal board of directors that you turn to when you need advice? And how do you identify who you include in that board of directors, and what types of things do you go to them for?

Nina Kleaveland 22:37

So I don't have a. Sort of formal, you're on my board of directors, but I do have people in my network whose opinion I value and trust, and I know the types of questions I can ask them or the areas of expertise, right? So if it's related to. Problem problem solving or business development or revenue models or fee structures. And I need a partner to hash all that out with or I have one person, or if I want career advice. And I'm I'm at a pivotal point and I'm trying to think like what direction do I go in and want somebody to weigh in on that. I have another person but I also just like to generally get perspectives and opinions from a lot of different people and synthesize that into what works for me. And so that's the beauty of a network, right? That you have all these different people with different backgrounds and ideas and perspectives and and I feel like sometimes you need like the dose of reality and sometimes you need the, rosy picture. Everything's gonna be great no matter what. And so it's just a matter of figuring out who, what, where, and yeah. And when.

Lan Elliott 23:50

Yep, absolutely. I think there is a moment, especially as a woman in the real estate field, I felt a lot, like I had to know all the answers. I couldn't turn to other people for help, but it would've been so much more powerful if I would've asked other people who had been there and gotten their advice. Love that. All right. One of our favorite questions on D E I advisors is what advice would you give to your younger self? And we've talked in the past about how this is something that really leads to self-reflection and the ability to look back over the course of your career and think, what do I wish my 22 year old self would've known that I know now?

Nina Kleaveland 24:32

Yeah. So it's funny you mention that you wish you had this network of people that ask questions to, and that you had the confidence to ask. Because I think throughout my career there were many instances where I felt like, It was assumed they are, I already knew and I didn't ask. And so those are opportunities for growth, right? If you ask, if you are humble and you say, I don't know. I would love to learn, but I don't know the answer to that. Then that gives you an opportunity to learn. And so I think that it's okay to admit that you don't know the answer. And I don't think I always felt comfortable saying that. I feel much more comfortable saying it today and I'm pretty confident with what I know and what I don't know. But that took many years to get

Lan Elliott 25:21

there. I love that. I read recently that vulnerability is a great way to connect with people and that people connect more with people who are willing to be vulnerable than someone who is the know-it-all and has all the answers. So that definitely gave me some food for thought along those lines.

Nina Kleaveland 25:39

Yeah and actually that's a great, it's a great point. We see that in female founders in hospitality. We have these small cohorts of founders getting together on a monthly basis on Zoom, and the discussion is so rich and so powerful when people are willing to be vulnerable.

Lan Elliott 25:58

Yeah, absolutely. As I thought we are running short on time, Nina, because I could spend a lot of time with you and look forward to spending time with you later. Yeah, same but. As we come to the end of our interview, do you have one final nugget of advice for our audience? Keeping in mind that d e I advisor's mission is around empowering personal success, what would you share with our audience who are struggling and looking to advance their careers?

Nina Kleaveland 26:31

So one of the things I didn't talk about so far, but I think is really important is the role of sponsors in my career. So when I was working at the hotel right out of college, I had a sponsor. And by sponsor I mean someone who knows you, knows what you're capable of, and we'll go to that for you and isn't in a, and is in a position of influence. Or power right? Is able to do something to help you. And so those are relationships you build and you cultivate over time. They don't just happen when reach out for a favor. That's not what I'm talking about. But I was fortunate that the general manager of the hotel, a woman took an interest in me and was that sponsor for me. Then when I. Moved into the Starwood corporate office. My my boss was also a sponsor in helping me think about my next career in advocating for me to go to business school. And then when I Wanted to move to Asia with American Express. There was this incredible woman who also went to Wharton who helped make that happen. And she was one of the first people I had met at Amex, and I'd gotten to know her and had a really good relationship with her, but she helped facilitate that. And then when I was at Wyndham the head of development and m and a took an interest in me and once again was a sponsor and helped facilitate the, me taking over and building out the corporate strategy function. And so sponsors have been incredibly important in me being able to progress in my career and find new opportunities, go in directions that I might not have otherwise considered. Like marketing, like corporate strategy. But when you have someone who's going to bat for you and who believes in you and is telling you could do this, that's pretty powerfully. And

Lan Elliott 28:25

I'm really grateful. Absolutely. No, that's that. Those are wonderful stories and I think when I was coming up, people knew what a mentor was, but this idea of champions or sponsors was new to me. I wish I'd found out about it earlier, but it's wonderful to have them that help you along the way. Yeah. Absolutely. Thank you so much, Nina. So appreciate all the advice that you've offered and your stories along the way. Such powerful stories to be able to help people with their careers and hopefully inspire them. Thank you.

Nina Kleaveland 29:01

Thank you so much for

Lan Elliott 29:02

having me. Absolutely. It's been a pleasure and for It's been a pleasure, Nina, and for our audience, if you've enjoyed this interview with Nina, I hope you'll go to our website, dei advisors.org, where you can find interviews with other wonderful leaders in our industry. Thank you.