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VRS534 - Breaking Boundaries: Pioneering Paths for Women in Vacation Rentals

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This episode of the Vacation Rental Success Podcast is sponsored by
The Vacation Rental Formula Business School
The Short-Term Rental education platform to solve your business challenges

The third Vacation Rental Women’s Summit will open in Nashville on December 3rd, bringing together so many amazing women in our industry.  From the pioneers who have been around for decades to the young entrepreneurs who are just starting out, the conference rooms will be full of excitement, inspiration and hope for the future for women in our industry.

But the work we all do goes so much further than a 2-day conference.  There are so many different facets to what this business is about.  Is there a career path?  How do women who are seeking venture capital backing start out on this path?  What are the challenges they face?

In today’s episode I’m talking to the co-founder and CEO of Hostfully, Margot Schmorak about all these topics and more.  We discuss mentoring and supporting women in our industry, work-life balance, mental health,  and the challenges and opportunities for women in tech roles. 

Margot shares:

  • The challenges she dealt with along the pathway to leadership success
  • How quitting a job gave an insight into true leadership
  • Why it’s healthy to have disagreements
  • Characteristics of being a good team member
  • The importance of caring about mental health
  • Why you need to hang out with successful women
  • Reasons why imposter syndrome could be a good thing
  • Why you should be a ‘why’ person
  • Who she is inspired by

Links

Hostfully

Vacation Rental Women’s Summit

DARM Conference

Who's featured in this episode?

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Heather Bayer
It's the Vacation Rental Women's Summit next week, and we're all excited about attending one of the most innovative conferences in the industry calendar. As a lead up to it, I'm speaking to Margot Schmorak, the co-founder and CEO of Hostfully, to talk about mentoring, support, life balance, and the challenges and opportunities for women in our business.

Heather Bayer
This is the Vacation Rental Success Podcast keeping you up-to-date with news, views, information, and resources on this rapidly changing short-term rental business. I'm your host, Heather Bayer, and with 25 years of experience in this industry, I'm making sure you know what's hot, what's not, what's new, and what will help make your business a success.

Heather Bayer
Well, hello and welcome to another episode of the Vacation Rental Success Podcast. This is your host, Heather Bayer, and as ever, I'm super delighted to be back with you once again. Do you remember that song that starts, Hello, mother, hello, father? Here I am at Camp Grenada.... and it goes through about how awful it is. At the last verse, it says, Wait a minute, it's stopped raining. Guys are swimming, guys are sailing. That's exactly what I thought the other day after days and days of rain and high winds and being stuck in our tin can for long periods of time.  Then the sun came out and the sky went to blue and I found myself singing that song. You are very fortunate that I didn't inflict me singing that song on you and I just spoke the words. But you know where I'm coming from on this one. So anyway, that's my little touch on the weather for today.

Heather Bayer
I want to talk about women in business, and I want to kick off with a very personal story. My mom was a teenager at the outbreak of World War II. She married a Canadian aviator, then as a war bride of 19 years old and with a toddler, she crossed the Atlantic and into another world. Her story is captivating, it's inspiring. One day I really want to make it into a novel, because she was a woman before her time. She was brave, she was fearless, she was uncompromising. When she and my dad came back to England in the early 1950s, he remained in the [UK] military for another 25 years. So she led the life of an officer's wife. Women at that time were not expected to work. In fact, it was really frowned upon if they did go out and get a job.  But it didn't stop my mom. She got her first job as soon as I was in junior school.

Heather Bayer
She'd always followed the principle of 'fake it 'till you make it'. Her first job was as an office manager when she had no experience in the workforce whatsoever. But as she said, Your dad has been away for 6-8 months at a time on deployment. And she said, So I've had to run the house, I've had to do the accounts, I've had to fix stuff, I've had to deal with people. I am more than qualified of working in an office and managing other people, and she got the job. Then for a time, she was a catering manager at an airport and she'd never worked in a restaurant, never worked in a kitchen. She was a real marvel. She inspires me to this day.

Heather Bayer
I love to hear stories of women who defied all odds to get to where they want to be. We're going to meet a lot of these women at the Vacation Rental Women's Summit, because it brings together many amazing women in our industry. From the pioneers who have been around for decades, these are the ones that were running property management companies in the 1980s and maybe before, and to the young entrepreneurs who are just starting out. If you've never heard of Madison Rifkin from Mount, she's exactly one of these young entrepreneurs that we should be watching.

Heather Bayer
The conference rooms are going to be full of excitement and inspiration and hope for the future for women in our industry. But the work we all do goes so much further than a two-day conference. There are so many different facets to what this business is about. Is there a career path? How do women who are seeking venture capital backing start out on this path? What are the challenges they face? In today's episode, I'm talking to the co-founder and CEO of Hostfully, Margot Schmorak, about all these things. She's going to share her experience not only as a woman in tech in other industries before she joined the vacation rental business, but also her experiences in mentoring and supporting other women who are growing in this and other businesses. Without further ado, let's move straight on over to my interview with Margot.

Heather Bayer
I am super happy to have with me today from Hostfully, the co-founder and CEO, Margot Schmorak. I've talked to your other co-founder, David [Jacoby], so many times. I don't know why we've never done this before, Margot. We had a chat, a very brief chat at VRMA in Orlando and decided that it was high time you came on to have a talk with me. So welcome.

Margot Schmorak
Thank you. Thank you so much. I'm so excited to be here. I've listened to your podcast and heard your interviews with David. I love all the creative ideas you have for talks and stuff. And so I'm just thrilled to be here chatting with you.

Heather Bayer
Well, I'm looking forward to this one because we're going away today from the ordinary, dare I say mundane world of vacation rentals and revenue management and marketing. And we're going to be talking about something very, very different. And that's a little bit more about inclusiveness and diversity and welcoming women into this industry and particularly in tech roles, something that I really haven't covered too much before. I'm excited about this. As we lead into the Vacation Rental Women's Summit this upcoming weekend, I think it's high time that we had this discussion.

Heather Bayer
But I want to kick off, Margot, with asking you to share your journey with us to becoming the CEO of Hostfully, because it's a little bit unconventional, I guess, because most people who come into this industry, when I talk to them and ask them that question they say, I bought a property. I had a couple of properties and I started out and then somebody else asked me to manage theirs, and here I am. But tell us your story.

Margot Schmorak
All right, where to start? Actually, the story for Hostfully begins in the conference room of another company called Service Source, where I worked, and I really loved that team. It was a small publicly traded company. We were making recurring revenue management solutions for big companies like Dell and VMware and Salesforce. And I remember looking around the room at all these smart people and thinking, I think if the culture was better, you could just have a better company. You could do better for customers. You could do better for employees. People would be working instead of at their 50% capacity, they could be at 80 or 85% capacity. And I want to be part of that culture. I want to be in a company where that happens. I actually didn't have aspirations to be a CEO or to be a founder, but I went on a little bit of a spiritual journey. I actually quit that job. I was promoted to head of marketing after having my second kid, and I did the job for a little while. And then I was like, I just don't want to do this job anymore. I don't know what's in it in the future, but I don't want to keep going down this career path.

Margot Schmorak
So I quit, which I'd never done in my life. I worked since I was 14 every chance I worked. I was a nanny. I was a barista in a coffee shop. I worked in a bakery. I was a research assistant in college. I helped someone with disabilities in Boston over a summer. I worked basically as a call center person, as a medical assistant in a pediatrician's office. I did lots of random jobs. But I was like, I want to create... I'm not going into politics, so I'm not going to change the world that way. I'm not going to nonprofit. I'm not going to go build houses for Habitat for Humanity, but I really want to do something good for the world. And I think it's going to be in business, because I had this nice career up until then. So I was like, I want to create something that has an amazing culture where people just love the jobs that they do. And then I was like, So what industry should I be in? And I thought education, travel, and health care.

Margot Schmorak
So I started pursuing ideas in those spaces and try not to get distracted with the... I remember one idea I had was an app that would automatically stock your fridge with Amazon items. And I was like, Well, I don't... Okay, that might happen, but I don't really want to do that one. So I just nosed around in a bunch of ideas. I met a couple of other people. I was actually CEO of an education startup for a month, and then it was all about using iPads with kids. And I was like, I don't want my kids to be using iPads more than they already do. And then, I know, I was like, no, this is not it. And then I met my co-founder, David, and he was working on an idea around the guest experience for his short-term rental. And I thought it was a terrible idea because his idea was to make money by selling affiliate revenue by basically selling coupons to restaurants. And I was like, that just seems like a really low margin business, very difficult. But David seems like a really good guy. Our kids went to school together and he was like, come to this Airbnb Open thing. We'll see if this idea works. So we just started exploring from there.

Margot Schmorak
And as David and I grew together as co-founders, we really share a lot of ideas, especially around culture. He's also a dad, very involved with his kids, and he really wants to create a great culture company. But I think at some point, I realized that I had to be the leader and not maybe the sole leader, but I had to be the leader of the company in order to the culture in the way that I wanted to. And that means inclusivity, finding new ways for women to move through the passage to motherhood more easily with pre-maternity leave, maternity leave, coming back in a flexible way, but also looking at things. How do we make sure that every single person at the company loves what they do? Just like... They are just happy. They're in their flow state when they're doing onboarding, when they're doing customer support, when they're doing engineering. So we do a ton of personality assessment stuff before we take people on and just make sure and also check in with people. And if it's not a good fit, we help them find their next gig. So it's just honestly a dream to be here.  But it all comes from culture, not vacation rentals. But I love vacation rentals.

Heather Bayer
Well, that is the best, isn't it? When you're tying in passions, which are very different passions. I love that story of doing so many different jobs along the way. You must have drawn things from some of those jobs that you bring to where you are now. Are there any of those that come to mind?

Margot Schmorak
I think the first thing is just a lot of empathy for any work that anybody is doing. It doesn't matter whether somebody is taking out the trash or whether they are doing the financials for your business. They deserve the same amount of respect as everybody else. And I can say that because I've been in a lot of those jobs and I noticed who was kinder to me than others. And I learned a lot in every single one of those jobs, by the way. There's no one job that's better than any other job. So I think the biggest thing that I took away that benefits me as a CEO is just knowing that you don't know anyone's life, they're living it, and they have this contract of work with you, which is to do a job. But don't make other assumptions about what their life situation is, where they came from, what they're capable of, because it might be totally different than what they're doing right now. But working hard. I also just love to work. Maybe that's a sickness, I don't know. I love working.

Heather Bayer
Tell us about a day in the life then of Hostfully for your staff, because I want to hear a little bit more about how this culture is reflected in how people go through that day?

Margot Schmorak
Yeah. Well, so we have a lot of culture on coaching, which actually it took me to... Somebody else outside the company pointed this out to me, and I didn't really understand it, but we don't do a ton of meetings. We have a pretty small window of meeting time in the morning. And then there's a lot of individual coaching that's going on for any function. So one of the things that's the most important for any new employee at the company is that we have a very, very robust onboarding program that lasts about 2-3 months. And they meet with around 15 people at the company, including all the co-founders. And then I have regular meetings with everybody on the team twice a year. But I think that there's a really healthy balance of not jumping straight into the work. So there's a lot of.... in the beginning of a meeting, you're going to find people joking around with each other, talking about a recent trip that they were on or congratulating somebody on a new baby or asking how they are if they were in the hospital. There's a lot of team building that goes on that's integrated with the work.

Margot Schmorak
And I think that's really important. And we have really funny things that pop up. And I think one of the things I love about the culture is that it's pretty flexible. So, for example, during the World Cup, we had people from Argentina and France on our team. And so there was a channel called World Cup Trash talk. And it was like most of the company was in there and people were just bragging on each other and having tons of fun. And I love that it was just an organic thing that popped up. We have another really active channel called Into Trader Joe's or the Best of Trader Joe's. And it's like all the great things you can buy at Trader Joe's, which is like a supermarket. But you've got to just go with it when creative things pop up. I think making more space to build those relationships and coach people is great.

Margot Schmorak
And then it also allows for people to transition. So if they don't love the work that they're doing, it's okay. And we can find something else for them to do at the company, or not. And we try to be very gracious about departures, which is something a lot of businesses don't do very well, I think. They cut you off and then you're out. And as company, we talk about it in advance. We send out a message. We allow people to say goodbye. We tell people to stay in touch. They do. We've had people come back into other roles. So I'm really proud of all those things.

Heather Bayer
Yeah, I love that. My experiences go back into a time when it was much more the traditional workplace. I worked for, I was a training officer at Reader's Digest in London and then out in the country for a number of years. I remember the time that I reached the end of what I could do in that role and I wanted to go out on my own and do the entrepreneurial thing. I have never forgotten the day I walked into my manager's office and I gave her my letter of resignation and her face just changed. I became the one who had-.

Margot Schmorak
Ah defected, right?

Heather Bayer
Yes.

Margot Schmorak
I know.

Heather Bayer
She just closed up. My two weeks of working out my notice were horrendous because she would not talk to me. Interestingly enough, I went on to build a training company that she then sent her staff to.

Margot Schmorak
That's crazy.

Heather Bayer
I built a customer service training course and then she was putting her staff through this course. I was actually going back into the company to do the training, which was interesting. It says a lot about her, actually, rather than the company itself, but it was a bit more of a cultural thing. When somebody says they don't want to work there anymore, then you don't want to talk to them any longer.

Margot Schmorak
I know. It's so funny. That last experience that you have with people, I have the same memories. I mean, people just get really cold and you feel like you've put in so much hard work for this company and these people, and then all of a sudden they just shut you out. It feels terrible. I totally agree. But one thing I was going to say is that you said you've had a lot of jobs. The last CEO that I worked with, his name was Chris Carrington at Service Source. I went to him and I said, I just have to leave. It's not the company. I love this job. I love the people. It's just me. I need to do something different. And he said, Well, is there anything I can do to change your mind? And I said, No. And he said, Well, my door is always open. And I was like, That was huge. It was a huge moment. And that's the framing, really, that every leader should have when someone decides to leave, because you can't think about it like we're in these closed networks anymore. I mean, we're all connected with each other.  And also why not be gracious about it?  It's easier.

Heather Bayer
Exactly. It's that graciousness. In terms of your role right now, you mentor, you support women who come to work at Hostfully, and I'm sure you do it for the men as well. But we're focusing on the women at the moment. So I've heard you talk about that commitment. So in terms of being a mentor and a coach, how rewarding is this for you? What benefits do you actually get from helping people to succeed in their chosen career or to move forward?

Margot Schmorak
I don't know if I could quantify what it is. First of all, I feel great, but actually there's nothing that.... I'm just like this in general. There's nothing that makes me happier than to see someone who I've been helping succeed. And I don't feel like it's a zero sum game. I feel like there's just always more and there's always just more we can do with each other and for each other. And I think the human experience is so filled with these anecdotal memories, which have to do with emotion and people connection and stuff. And we just don't know how we're going to influence anybody else at any time. Maybe somebody's having a great day and you can just give them little tip that puts them over the top and makes them feel amazing about their self. Maybe they're having a hard day and you're the one who's going to give them a little bit of a lift. That can be so meaningful. And I hope that... I know actually, some of my most proud moments actually at Hostfully are when women on the team have disagreed with me in public. And I think this is something that women just need to learn how to do better.

Margot Schmorak
The first time it was actually a woman who said, do not do a merger with ORBI Rentals. Our PMS, this was early days in the company, and I was like, Awesome, I'm so glad you're telling me this. Tell me more. What do you think? And now it's things like whatever, we always have stuff that we disagree on. I don't have any specific examples right now, but I think it's really healthy to have those disagreements and show people that even when they happen, there's no damage to the relationship. So what do I get out of it? I mean, I just get to live an easier life. It's just easier, everything.

Heather Bayer
Well, you're also a mom of three. You have several other interests outside of work and Hostfully, how do you balance all that? Because being a CEO, I was there for 20 years, is not an easy task. I'm sure you sometimes go to bed thinking of it and you wake up in the morning and it's the first thing you think about. How do you balance all that with all your other personal responsibilities that you have out there? And I know it sounds a little like talking about work-life balance, because we tend to look at it in a different way now. But what advice can you offer to others who are seeking that similar balance?

Margot Schmorak
Yeah, well, it's really about team. So I don't think about my life in isolation. It's about me and my husband working together with parenting. It's about we have a wonderful nanny named Letitia, and we're transitioning to a new person actually soon named Sophia. And these are very integral parts of our team, our family team, and we really treat everyone as a leader in the whole picture.

Margot Schmorak
But same thing with the company. I've got all these other interests. I've got an acapella group that I'm in. I've got VC-Backed Moms that I'm like a co-founder of this community of women who are running companies. And it's all just team, team, team, team, team. So I think the better teammate you can be, which means you need to be optimistic, you need to be resilient, you need to communicate well, you need to have patience and empathy, you need to listen. The more you can do that, the more people are going to want to work with you, and then the more you can do yourself. So I am able to do all these crazy things, but it's mainly because I have an amazing team with me that are also enjoying what they're doing too.

Heather Bayer
So do you believe that these things are.... You were born like this, or have you learned all these skills along the way, basically asking, can anybody do this? Or do you have to be the extra special person that has all these qualities?

Margot Schmorak
No, man, I... So we were talking before the interview about how I was like a bit of a philanderer for a long time in my life. So I think it really took me  some time to hit my stride and just understand who I am and what I'm capable of. I was not very happy in my 20s. I did a lot of adventurous things, explored a lot of new things, but definitely not like a leader at all; I was just there.

Margot Schmorak
I think that there's a couple of things that are so important. First of all, is just mental health. So I say this with a lot of compassion. My family has many suicides. Unfortunately, my great grandmother committed suicide and it left indelible marks in generations. And so having the awareness of my own mental health, making sure that I'm taking care of myself, that's the most important thing you can do, which includes sleeping, exercising, and just mental health. If you're not doing well, you got to raise the flag and tell people about it. So I had a little bout of postpartum depression after my third kid. A lot of it had to do with sleep. I'd had enough life experience and gone to therapy that I was like, whoa, I'm not okay, I need to make a shift.

Margot Schmorak
So I think my advice to people is make sure that you take really good care of your own mental health and address those issues that are coming up for you on a recurring basis. If you are going to sleep or waking up in the morning worrying about things, or thinking about things that's not the most positive, that's the place to start. So does everyone want this life? No, and that's totally fine. But does everyone want to live a life where they feel whole, they feel satisfied and they feel appreciated and they feel seen? Those are things that actually managing your own mental health can help you with. So I think the work actually is pretty internal on that one.

Heather Bayer
Yeah. Let's talk tech for a moment. I see a lot of women in tech, but nowhere near enough I was talking to Amy Hinote the other day about the attendance at the DARM Conference, and she was saying it is 75-80% male.

Margot Schmorak
Attendees at DARM? I'm one of the very few female speakers, too. She's like, What can you do? And I was like, Well, I'm only one. It'd be nice if there were more women there.

Heather Bayer
We're going to come along in a second and talk about imposter syndrome, because I think it's all very tied in together for particularly those women upcoming in the industry who are trying to break into tech roles, but it is a very male-dominated space. So there's challenges, there's also opportunities. Can you just share a bit of your knowledge on that in terms of those women that you have working at Hostfully in those roles?

Margot Schmorak
Like interested in tech and getting started with....

Heather Bayer
Yeah.

Margot Schmorak
So first of all, maybe you're talking to the wrong person. My first trophy was a math tournament trophy. So I'm just very comfortable with numbers. It's my heritage. But I do think that there's the 'fake it until you make it', which you just said to me about your mother - and I hope that the listeners can hear that story - is totally true. You talk to women and men, and they just feel totally differently about their ability to figure it out when they get there. And I actually think the women we've hired at Hostfully are not... they don't suffer from any self-confidence issue. We've hired them because they already have that. So maybe it's even before the interview process. It's just about your own thoughts around what you can be doing for your career and yourself. But why is the attendance so poor at DARM for women? I don't know. I mean, we're doing the stuff that you need to know for vacation rentals, it's not calculus, it's basic math, and looking at patterns and understanding what your key metrics are and why they're important and then just tracking them over time. And that's the stuff that anybody can do. It doesn't matter.

Margot Schmorak
In fact, younger people could do it, older people could do it. People who don't speak English can do it, people who.... Whatever, it doesn't really matter. So I think there's just, I don't know, maybe there's just like fear or worry about that black and white version of success when it comes to data. I don't know.

Heather Bayer
Well, that's what I'm wondering. I'm sure there are many very competent people, but they have that fear. They have that self-doubt that creeps in, that says, This is a very male-dominated space in this industry. I feel that I am competent to do it, but how do I make that step in there and show that competence?

Margot Schmorak
Yeah. Well, I do think it's helpful to have a couple of examples of other people, like when you went with the 'fake it until you make it' strategy. And sometimes, I don't do this anymore, but earlier in my career, I would actually think of what my husband would do. We were basically educated the same. He's got a computer science degree, we went to business school together. And I would be like, What would my husband do? What would you say in this moment? And I might actually just copy him, because I didn't have an example. But I think now there are more and more women involved. So even though there's 80% men, there are 20% women. So if you want to get into the field, go and hang out with the 20% women, watch them. What are they doing? Listen to Julie Brinkman, the CEO of Beyond. Listen to Amy Hinote. Go talk to them, build relationships with these people. And you can pretend to copy them sometimes, and that's okay. You don't need to be correct all the time. But I think you got to really go out and find those voices. And as a CEO of a software company, I've done that too.  I spend a lot of time listening and reading about other women who are leading companies to try and figure out what my style is. So it's not zero, but it's not enough.

Heather Bayer
I still do this. I still look at women who are CEOs of some of the biggest companies and study them and look at what are they doing, how do they carry themselves, what are they like in meetings. You can go online and you can study these women. I always remember... Years and years and years ago, I was training as a psychotherapist and I was learning about a woman called Virginia Satir, who did a lot of family therapy way back in probably the '50s, '60s, I guess. She was talking not so much about 'fake it until you make it', but about modeling, looking at what other families do and modeling behavior, where that behavior is working, then try that behavior yourself. It's a very simple concept, the whole concept of looking at somebody who's doing something great that you feel that you could emulate and then modeling that behavior. That's something from that training that I never lost. And it's all out there now. You can follow virtually anybody. Watch the TED Talks, I think, are one of the best things. Watch these people doing a TED Talk and emulate that.

Margot Schmorak
Yes, that and the resourcing question is also really important. I think that sometimes you can see the TED Talk and then you don't understand that there's a lot of people behind the scenes helping to support this whatever person process, image and just taking it all with a grain of salt. Because sometimes the media does a bad job at creating these fictitious CEOs who... always they're wearing clothes and their body's perfect and they somehow have children without looking fat. And how do you... That doesn't exist. So you have to take it also with a grain of salt. And remember that the media likes to build people up and take them down, which happens to a lot of female CEOs. So there's this you go up to the top of the mountain and then you fall off hard all the way down to the bottom. And one of the things that a lot of female CEOs that I hang out with talk about is the take down article, which inevitably comes after the media props up any CEO. There's always a take down article, which is way more harsh than would be written about any man.  So I think you just have to just take it all in with stride.

Heather Bayer
Yeah, what comes to mind with you saying that is something I saw on LinkedIn the other day, and it was about a woman, can't remember who it was, but leaving a company. And the headline wasn't, She leaves after 15 years of amazing accomplishments. It was a take down. It was a real take down, which took away all those years of accomplishments and just wiped it out in a moment.

Margot Schmorak
Yeah, exactly. And those articles are not written about men.  I don't know what's going on there, but I don't like it.

Heather Bayer
Hey, you're joining me on a panel of industry leaders at the Women's Summit to talk about imposter syndrome.

Margot Schmorak
Yes.

Heather Bayer
I wanted to ask, how has self doubt.... When I'm talking to you now, I'm thinking, Oh, my gosh, I'll be interested to see your stories, because I can't imagine you having self-doubt. But I think it impacts everybody. But how has it impacted you in your career? I think the most important thing is, what do you do to combat these feelings, because so many people have them?

Margot Schmorak
So this is where I think age and experience helps, because for a long time I felt like I don't know what I'm doing. And it's my first time and I'm new to this. And who am I to be the one raising this money, hiring this employee, building this product, building this company? And I still feel like that actually, even every day. Sometimes I'm like, really? I'm still the CEO. I'm doing this. We have a big team now. Really? And the people around are like, yeah, this is great. I'm like, Okay, well, they seem okay with it. But no, I think the imposter syndrome never goes away.

Margot Schmorak
It's actually a very healthy thing to have imposter syndrome, because you're always questioning how much better you could be and whether you're making the right choices. And that's really healthy. If we ever get into a headspace where we're not questioning those things, then we're delusional or narcissistic, egotistical, whatever. Those things, that's not helpful whenever you're trying to work with anybody else. So I think imposter syndrome is actually not a terrible thing. I think you balance imposter syndrome with this sense of being really present in the moment and maintaining a really healthy sense of focus and trusting that you will be making the right decision when it happens.

Margot Schmorak
So there's been many times in the course of Hostfully, where we've been thinking about something that's going to happen in the future. And I think, oh, my gosh, how am I ever going to navigate through that? Even like a financing round. I've never done that before. It's a lot of money, right? I've got to review legal documents of which I have no context. I have to talk to different investors and references and all these things, due diligence materials. I've never done any of that before. But I guess at some point in the last couple of years, actually, probably since I was like 42, 41, I've just been like, Well, I made it this far and it's gone pretty well. So I think I should just stop worrying about it so much and just try to take it every day at a time. And so I don't plan out very much ahead except for vacations, because you have to do that. But I'm always like, I'll meet the challenges when they arise and I will handle them like I've always handled them. And my life has gone pretty well so far. So I think it will go okay, even if I make some mistakes.

Heather Bayer
I think that is great for people to think about, is to say, I've made it to here. I must have done something right to get it here.

Margot Schmorak
Exactly.

Heather Bayer
If they haven't found out yet, then it's unlikely that I'm going to be found out now to not be competent or not have enough knowledge or thinking that they're just not qualified to be in that position. But if you've made it that far, it goes back to....

Margot Schmorak
You're qualified!

Heather Bayer
Yeah, it goes back to my mom and her getting a job as an office manager as her very first job when she was in her 30s, never worked in her life before. But she said, Well, I've managed my home and my husband's been away on deployment for months at a time, and I've worked with all the plumbers and the maintenance people who've come through the home and I've booked things. Yeah, I'm competent. I wish she was still around, actually, so I could ask her that question and say, Did you ever suffer self-doubt? But from the times I remember talking about her and she just simply said, If I trust myself that I can do it, then I can do it.  And if it doesn't work, then I'll go do something else.

Margot Schmorak
Exactly. Well, I would be curious to know how much she asked questions. First of all, it's good to have a tendency to want to know the root cause of something like, Okay, you need to distribute these files to these people this time. Why? I'm curious about the why culture in the company that she joined, whether there were people there who would help to answer those questions, or whether she was just a person that wanted to ask it herself and figure it out herself. But those are the... I think those things can make it easier or harder because if you go into a place where no one wants you to know why or no one wants to help you with answering those questions, then it's harder. So that's why I think I'm a little bit of an over-sharer, because I'm trying to open it up to say it's okay to ask why, it's okay to ask, quote-unquote, dumb questions. There really are no dumb questions. If you're asking a quote-unquote, dumb question, it means that the organization has not given you the training or support that you need. So yeah, I would be curious about that too with your mom, though.

Heather Bayer
I wish I'd worked for you. I would love to come to work for you, Margot. So for those women, and there are a lot listening to this show who don't have their own companies, they're working at companies, what advice do you offer them if they're aspiring to leadership positions, particularly perhaps in revenue management?

Margot Schmorak
So first of all, be the why person. Understand why the company exists, what's going to make that company successful, what is the urgent goal, and then what is the strategy, the long-term strategy? And line up your work with the company. I remember figuring this out early days, just do a good job. Do the job that you need to do to help the company. The second thing I would say is make sure that you're in an environment that is going to support you. And if there's anything 'wonky' about it, move on. That's terrible advice. But I did have that experience once where I was like, there's just something weird going on. Ended up being the head of my department was having an affair with somebody else, and there was just a lot of distraction. And so I was doing a good job, but there was just too much drama and stuff around me. And so it clouded what the whole department was doing. And I left and I'm really happy I left. Actually, something deep inside was like, This isn't good. I got to get out of here. So set your own boundaries about what you want to tolerate and do a really good job.  That's like baseline.

Margot Schmorak
And then the third thing is, once you've figured out the why and the purpose of the company, align yourself with the people that are also doing that. So find the... I've done a thing in another company where I basically found the person that was really pursuing the strategy and was making the most impact. And I said, I want to work for you. I want to transition out of the department I'm in and I want to move into your department. And it took time, took about six months, but I managed to do it, and that really helped to catapult my career. Those are some really practical things you can do. But yeah, I'm just.... honestly, I'm also an intense learner. I will fill up my brain with other things. So I have a lot going on that's quite stressful right now with just work and life, and it's a lot. So yesterday, a couple of days ago, I was like, I'm going to learn Spanish on Duolingo, because I need something that's just learning and keeping my mind busy, but not goal oriented. And I actually have done this in other times of my life at Hostfully, where I took an adult tumbling class, like a gymnastics tumbling class.

Margot Schmorak
I'm really bad and it's great. And it just fills my mind so that I'm not spinning out about the things that I can't control, because I think that's when stress happens when you're feeling imposter syndrome, you're feeling like you can't control something, it's feeling out of control. So if you're a data geek, which is probably what people are thinking about DARM and attending the conference, find other things to fill your mind. So you're not obsessing about stuff that you can't make an impact in. That's my tip.

Heather Bayer
I'm showing a book to Margot. Can you see it?

Margot Schmorak
Oh, yes! You're doing it?

Heather Bayer
I'm 173 days into Duolingo Spanish.

Margot Schmorak
Oh, my gosh.

Heather Bayer
I'm 173 days ahead of you.

Margot Schmorak
Yeah, exactly. I just started a couple... I was in Mexico. You should do it and come next year at the conference. We'll do a talk in Spanish together.

Heather Bayer
Oh, that..... a whole year. We can do this. Now that's accountability.

Margot Schmorak
I know.  I want to try to do a little bit of it in Spanish. I mean, my Spanish is okay, I understand some, but speaking is really poor, so I just need to work out it.

Heather Bayer
Well, people who are saying to me, Why...

Margot Schmorak
It's just fun. Yeah.  Why Spanish? Are they asking you?

Heather Bayer
Well, they're asking me, Why? You're a Canadian, why aren't you learning French? Because I have no desire to go to Quebec. But I do want to buy a house in Costa Rica at some point.

Margot Schmorak
There you go.

Heather Bayer
I'm turning around to check that my husband's not listening to that. But I thought that learning Spanish.... yes. So yes, but I'm very much along that same wavelength of just keeping that learning going, whether it's a language or whether it's new yoga moves or something. I have this thing about I want really... I loved pottery at school. I'd love to really learn how to throw a pot and sit and do that whole thing with wet clay. But yes, if you've got a passion out there or something you're interested in, it is really super helpful to go out and do something different that's outside of everything else that you do, right?

Margot Schmorak
Yes. And do it in a non-goal oriented way too. In a way where you're just like, I'll just try this a little bit. Sometimes it can develop into something and sometimes it doesn't need to, and that's okay. I was also doing a flying trapeze class for a while, and I met this other guy in the class and he's like, So what move are you working on? And I was like, Honestly, I'm just having fun with it. I have enough goals in my daily life. I don't need to add more goals. And then we were chatting and it turned out he was a co-founder of his company. And he's like, I totally get it. It's the same thing. He's like, I need to take the goals out of this because it's not healthy. I was like, Yeah, just be chill about it a little bit. It's okay.

Heather Bayer
Margot, you are really inspiring, but I want to know who inspires you, and why?

Margot Schmorak
Who inspires me? Children inspire me a lot. I love my own children, but just children in general. I find so much inspiration from watching children navigate this world that they're just seeing for the first time and finding ways to brilliantly cope with whatever challenges are happening. I don't think I could ever be a teacher, but I really love being around kids. So that's very inspiring for me.

Margot Schmorak
I'm inspired by all the women's rights people of all time, whether it's Jane Addams, finding ways to serve the poor to Rosa Parks and women throughout history who've done amazing things to change the way people think about women. Yeah, I'm not a big book person, like business book person. I read a lot of fiction and biology books. I don't really obsess over current business leaders or follow people like that as much. I get more of an inner life, I think, around that. But yeah, I'm really inspired by artists and children.

Heather Bayer
I love that, being inspired by children. I must look at my granddaughters in a different way.

Margot Schmorak
Yeah. Oh, my gosh. Well, if your granddaughter is 12, I have a 12-year-old too. It's like a dog eat dog world in middle school. I watch the kids and I'm like, wow, if you are able to make it through this, you're going to be able to do anything. I think it's really intense for them. And maybe, I have a memory like an elephant, I remember so much of my own childhood. So I have this flashing back and forth thing that happens when I'm around kids and it's healthy. So yeah.

Heather Bayer
It's been an absolute pleasure having you with me. I want you to just tell us a little bit about Hostfully before you depart, because I think that's really important. I'm sure most people have heard of Hostfully, but they'd like to hear just a little bit more about what the company is doing and where it's heading.

Margot Schmorak
Yeah. So Hostfully is a property management software company. We have two products. We have our property management platform, which is like what you would probably think of as a traditional PMS. It includes a way to get reservations across all the different booking platforms. We are a preferred partner of Airbnb, Booking.com, and Vrbo. And we also offer beautiful direct bookings website. And then you can also hook up with a channel manager to reach more platforms. We also have a centralized calendar where you can see all of your reservations in one place. We have a great dashboard and pipeline. I was just on a call. We're making some really big revisions to that over the next couple of quarters. And we have a unified inbox where you can see all your guest messages. You can have automated responses to make it just easier for you to get through the day-to-day and be able to respond to guests either in an automated way or in a personalized way, depending on what the needs are of that guest. And then we also help to process payments using Stripe or PayPal.

Margot Schmorak
And then we also have a digital guidebook platform, and that's actually the original heritage of the company that helps.... it's a mobile responsive website that helps you give your guests property information and local recommendations. Our vision for Hostfully is we want to be the most powerful platform and most easy to use platform for short-term property managers everywhere. Right now, our strengths lie in this platform nature of our product. So Hostfully is one of just a handful of companies that you can use to connect to almost any other software company in the industry, whether it's dynamic pricing or insurance.

Margot Schmorak
And I love actually just getting back to where your heart is with the company.  One of the big missions that I also wanted with Hostfully was to have a product where it almost.... people can touch and feel it, and also they can integrate it into their daily life for it to make an impact. And we're doing that for our customers, which is really, really wonderful. But I love that our customers can flexibly choose what options they want, so they're not locked into one way of doing their direct bookings, one way of doing their payment processing. They can choose from a variety of different ways to service their business and their unique needs.

Margot Schmorak
And that's the power of this industry is that our customers, property managers, are in region, and they are closely connected with their customers, their cleaning staff, their owners. And the needs of those businesses are all different because the regions are all different. Whether your inventory is all spread out in different geographies or whether it's in one building, those businesses have totally different needs, whether it's on a beach town or a mountain town, those different needs. So I love that Hostfully is a platform product so that we can adjust the makeup of your tech stack to suit those different businesses. That's something I'm really excited about. And we're in a unique position to be a leader on that. And we're just really excited to keep going.

Heather Bayer
Well, if I look back to the amount of times I've interviewed David over the years, you've been around in this space for so long and such an established company, and I really wish you well for the future. And of course, as we say, if you're in this business at all and you want to be successful, you've got to have the two. You've got to have a property management system, you've got to have a digital guidebook. Absolutely. That digital guidebook is 100% necessary for every single operator these days, so I'm glad you've got that.

Heather Bayer
Margot, it's been a real pleasure. Can't wait to meet up with you in a few days at the Vacation Rental Women's Summit to talk about imposter syndrome on the panel and all sorts of other things. I just want to thank you so much for joining me. Been a long time coming. It's been absolutely worthwhile, worth the wait. Thank you.

Margot Schmorak
Thank you.

Heather Bayer
Thank you so much, Margot, for joining me and for talking about things that are not as specifically vacation rental related as we normally discuss on this show. It was really, really interesting. I love this culture at Hostfully. If you're out there thinking of a job, maybe this is a place to be aiming for. It sounds a great place to work in, and Margot sounds like she's a great person to work for. I'll leave that one with you.

Heather Bayer
I will put all the details of Hostfully on the Show Notes and also the information on the Vacation Rental Women's Summit, which I know is only a few days away, but there's still room available if you're just deciding that, Hey, I need to have somewhere to go next Sunday, Monday, Tuesday. This is going to be a fabulous event and I think I will bite the bullet, buy my air tickets and book a hotel room and go. Then, of course, there is the DARM Conference on Wednesday and Thursday as well.

Heather Bayer
If you're listening to this after the Vacation Rental Women's Summit has taken place and you want to go to the VRWS website within about 3-4 weeks of the event, the recordings of the majority of the sessions will be uploaded.  You can purchase those and then at your leisure, go through all the sessions, which are just super, super interesting. You can go check them out at Vacation Rental Women's Summit the website, and you can see the schedule of events. So even if you can't go, you can check out what you might be able to catch up on at a later date.

Heather Bayer
Just a reminder to listen to The Tipping Point, our Monday episode. It's a short episode, around 7-10 minutes. It's just focused on a single topic and gives some actionable information. You can listen to it, you can follow that topic, and go away with some things that you can do the moment you've stopped listening. I encourage you to go over to vacationrentalformula.com, go to podcasts [Resources> Vacation Rental Success Podcast], and have a look at some of the most recent episodes we've done. They are really interesting. We are bringing on guests as well to talk about their superpowers and ask them to share some of their best knowledge with you.

Heather Bayer
That's it for another week. Always so enjoyable to be with you and to bring you more interviews and episodes that are going to make your day. Please leave us a review if you have enjoyed this. I'm just like you, wanting your five star reviews for your property. I want exactly the same for the podcast. So if you have some time and you can go to your platform of choice that you listen to your podcast on and leave us a really good review, I would really love that. I thank you so much and it helps me to appreciate how many people actually listen to the show. So have a great day and I will see you again next week.

Heather Bayer
It's been a pleasure as ever being with you. If there's anything you'd like to comment on, then join the conversation on the Show Notes for the episode at vacationrentalformula.com. We'd love to hear from you and I look forward to being with you again next week.