On today’s episode, we are live from VRMA in Las Vegas with Margot Lee Schmorak, the CEO and Co-founder of Hostfully. Margot was looking for her next role when broke into the industry in 2015. She met her Co-founder David Jacoby at their children’s preschool and went to work on entrepreneurial ideas in vacation rentals. As a leader, she prides herself on having an open and transparent culture at the company. Always be open to new ideas, ask for feedback, and see how everyone’s feeling daily. The last few years have been very heavy on us all and Margot discusses why she believes it’s so important to take time to manage your own mental health. This is something she is an advocate for not only at home but at her company as well. She discusses what it’s like to go full ninja mode and have that work-life balance. Listen to the end to hear about Hostfully’s new product launch and future plans. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Going Full Ninja Mode With Margot Lee Schmorak

In this episode, we have a special guest and we’re live from VRMA. How are you, Margot?

I’m good. How are you?

I am great. We’re so glad to have you here.

Thanks for having me.

We chatted about this. I can’t remember if it’s episode 77 or 78. It’s 1 of the 2 in Season 3. It’s been too long.

I get John’s shit all the time. We talk about the people going on the show and this is my partner in crime and everything, the DEI and the space and all-around badass. We talk about these things. We were like, “Margot hasn’t been on our show.” I was like, “Do you think she doesn’t like our show?” This is our speculation. I’ll say all that because I’m happy to say it with my worst voice. Thank you for coming over.

I wish you have some vocal warm-ups because we’re on day three of talking a lot.

There’s been a lot of talking. It’s been a busy show. Before we get into your story and how you came into this space, let’s do a show takeaway. We’ve both had an opportunity to present with you in separate presentations which are exciting. I appreciate the ask to be a part of that. That was great. What’s your biggest takeaway from the show in 2022? This is my fifth VRMA International. I skipped 1 because of COVID. What is your biggest takeaway?

For me, this is a big show in every way. There are more attendees. We’re in Las Vegas and the script is gigantic. It’s not human-sized. It was sold out for the first time. They stopped issuing new tickets. The vendor booths are bigger. The sessions are very well attended. I did a throw-it-together session with Mateo in the beginning. We had a lot of people there and a lot of engagement. I’m feeling its growth and a lot of interesting property managers and vendors. Everyone here is booming honestly.

I feel the same way. We’ve been doing this long time. I love to see new people coming in, seeing the exciting A products and projects they’re doing and the different tech that’s coming in. What’s also interesting is to see the tech that hasn’t made it. Look back at the last major show we were at. There’s a lot of new stuff coming into the space that isn’t here now. That’s the world we’re in because some things are going to stick, funded and should or shouldn’t have been funded. With you, it’s exciting to see the PMS side in who’s making the steps, climbing that ladder, putting out a new and interesting product and who has been well getting passed by.

The story of Hostfully is about to slow steps one in front of the other. In this industry, the market of COVID, travel and all these things that have happened over the past few years, there’s exploding fire bombs and we keep walking slowly. Everyone’s like, “Are you okay?” We’re like, “We’re good,” and keep walking. For Hostfully, the journey has been slow and steady. In 2022, we did expand the team a lot but in terms of our thought process of how we want to build the company, we’re doing the right thing next and try not to pay too much attention to what else is going on in the market. We’re trying to do what we think is the right thing. That might work and not work but I’m prepared to die trying.

You couldn’t go to a show and not miss yourself or your team. It’s wild-ass shirts and jackets. I saw some insane hats.

We’re shameless is what it is, in terms of a certain amount of age and love. If you love what you do and the people you work for, I’ll wear a sandwich board and a secret jacket. I’ll get up and tell a joke even though I’m not a comedian in front of an audience. You let it go because, at this point, it’s like trying. As long as it’s the right thing for our customers and their employees, I don’t care what it is, I’ll do whatever.

From a cultural standpoint, the buy-in is there. I want to get into your story as a leader in the space but when you look at the team, everyone is enthusiastic. When I talk to them, they love it. They believe in it and it exudes from them.

It’s also because no one at Hostfully who’s too cool for school. If you want to try something new, go for it. If you have this wacky idea, we want to hear it. If you’re not happy, we want to hear that too. A lot of the culture of Hostfully is being open, authentic and transparent and we are. I have to also say that is a very hard way to run a business.

It requires a little bit more in terms of emotional wells to draw from sometimes. I spend a lot of time thinking about my mental health and my employees’ mental health. That’s what translates to the customer experience because we don’t give anyone coaching on being enthusiastic. I never said that but I said, “This is what we’re trying to do. We had these creative ideas. We’re going to give it a shot. What do you think?” “We don’t like it.” “Let’s do something else.” We went through several ideas on the way to this conference that got scrapped. One was about the environment we were going to do an anti-swag, which is cool.

We were also looking at doing where people contribute to the environment. We felt it wouldn’t show enough at the conference. It would be a good gesture but it wouldn’t have the same impression. We were like, “We could buy these jackets.” It’s low-key and there’s not a big impact on those jackets. Those were two of the ideas but we had several different ideas about what we wanted to do.

To talk about the environmental thing in the sustainability in this space, my wife talks about all these conferences and stuff I go to and how wasteful they are. She’s watching documentaries on how this can be better. Shout-out to, not at this conference, but Book Direct Show that took the biggest step forward in doing a greener show. Everyone had their water balls. There were water-built stations. There were no plastics. The biggest thing I thought was huge. We have all these lanyards and badges. It’s such a waste because I’m sick of taking a moment. I throw them away.

You have a collection.

It’s the actual biggest impact of conferences, which is a problem and we have not figured out how to self assists with the flights. That is where we are killing the environment and it is a tough thing to do. You could buy carbon offsets but the effectiveness of those carbon offsets is questionable. We have a problem but it’s good that we say we have a problem. We need to acknowledge this. Do you need to fly someone in from Europe to come to this show? They can go take a shorter flight. That’s a big impact.

This is quick to wrap up my thought before I forget. One of the biggest impacts I thought that the Book Direct Show did on a much smaller scale is they had paper badges. It was cardboard but it was thinner cardboard and had a lanyard that you returned. They encouraged you and they’re using it next year for the next one. I’m like, “It’s so brilliant because mine end up in a hotel garbage can every time if I was Mateo and I have a collection.”

It’s all supply chain stuff, ordering it and shipping it. It’s a big issue. I would love for us to approve that. I heard this podcast though more about founder stories and stuff. Are we going to talk about that?

If John will let us and we want to get into it because your story is incredible. Even with where I met you and what I’ve witnessed from the time that we’ve been able to spend together and what I continue to see you do as a leader in this space as a mom and a wife. We have a good relationship and I love it.

We hang out and we have a friendship. It’s different.

This is my partner in crime for sure. Every time I go to San Francisco, I call her to try and meet for lunch and eat breakfast. This is what I love about this space in this industry. John, you and I have a similar relationship. I’ve never heard your full story. How did you get to this place and come to be the founder? I’ve seen the fight. We’ve talked about the fight. You’ve done so much. You’ve raised money. You are raising kids. You’re a wife and have a family. You love music. There’s so much that makes you you. How did you get here? Where did you come from that to get here?

There are lots of people who are doing a lot of this. They’re moms and dads. You are like a mega dad raising families, running companies and having a lot of interest. The reason why I’m here, CEO of Hostfully, has to do with the fact that I got lucky early in my career. I was a hippie living in Boulder. I was working in an architecture firm. I was making $28,000 a year and has loving life, dating a musician and having a super fun time there.

I started to apply for other jobs and I couldn’t get them. I was an office manager and a business manager at an architecture firm. People were like, “We don’t know what to think of her. She looks like another secretary,” which is fine. I get it. My dad’s like, “You need to go back to grad school. I was like, “For what?” He’s like, “Go back and get an MBA.” I didn’t know which school to go to. I interviewed doctors, lawyers and people who went to business school, interviewing ten of each. The business school people were by far the happiest.

They were like, “I have much flexibility, I can make all this money.” The doctors were miserable because they were all still in school. The lawyers were miserable because none of them were doing what they set out to do in the beginning. They wanted to fight for justice but they ended up at a law firm or doing legal clerk stuff and they weren’t happy. I was like, “Business school it is.” I went to business school and all my friends were like, “You’re selling out. Are you going to be top?” I was like, “I guess I am but I’m going to still be me.”

I took that comment to heart and my friend Mendel said that to me. I don’t want to lose that part of myself. I want to try to keep it. I went to business school. I was a total oddball at business school. I was the only one who had the background that I had. I interviewed and found a job at Apple, which was a lucky break in some ways. I worked hard and did a good job but I hated working there because Apple’s a weird company and I don’t know how many of your readers know but it’s super secretive.

If you’re working on this or that product, you will never be able to speak about either product to each other. It’s frustrating as an entrepreneur because you can’t ask questions. I can’t be like, “John, what are you working on?” “Sorry, it’s confidential.” That’s how everything is at Apple. I didn’t like it. I was like, “I got to leave.”

After that, I went to this company called ServiceSource and this is where a bunch of things happened that all worked in my favor. I did a good job. I ended up getting promoted and I pitched myself to another leader in the company because I saw he was making more of an impact and he got promoted shortly after that.

I went from being a Senior Manager to being Vice President in three years in a public company and that is unusual. I also had a kit in the tech. I remember in the last promotion sitting with the CEO in his office and he’s like, “We want you to do this head of the marketing role.” I was thinking in my head, “There’s no way. This is stupid.” I had a baby. I’m breastfeeding. I’m barely sleeping. I’m tired. We got a no-pair for the first time. I was trying to figure out my life and how it all works. I remember thinking, “Don’t say anything, Margot. Don’t screw it up. Say yes and you’ll figure it out later,” which is like hospitality.

I didn’t know what I was going to do, honestly. I took the job and worked hard for nine months. I brought my newborn to a conference and had to run upstairs and pump all the time. It was brutal. The people love babies and everyone wanted to hold the baby. It was pre-COVID so everyone could hold the baby. It’s fine. I took that job. In this new phase, I’d run marketing at a public company with a $5 million budget and a huge team. I was in my mid-30s. I saw my career being CMO of outsourcing companies, which was what ServiceSource was. It was a managed services company but I don’t think that’s my thing.

That’s not going to make me happy in my life. How do I figure out something different? I was at the restaurant we went to for lunch, Brennan’s in New Orleans, with my husband. I was like, “I am not digging what I’m doing.” He’s like, “You should quit.” “Are you serious?” “You didn’t take enough time off with the baby as you wanted to. You’re tired. We’re doing okay financially. Why don’t you take a break?” I did and was off for 3 or 4 months. For me, it’s hard to not work. I like to work.

I was sleeping, watching Netflix, doing yoga, going for walks and meeting with people. I then was like, “I want to start working.” I met my cofounder, David. His kids went to state preschools like mine. He was iterating on this idea around Airbnb and providing better hospitality. We started there. David is an exceptional sales guy. I thought the idea was terrible when I met him. I was like, “I don’t get this. I don’t understand how you’re going to make money.” That product itself does make money but not a ton of money. I wasn’t route but this is a new industry for me. I don’t think it’s new anymore. Now I know more about it.

When did you meet David and decide to go ahead and start? Was it Hostfully at that time?

It was 2015. We had a placeholder name, which was Guidebk without the O’s, which is a terrible name. Look us up under the Articles of Incorporation Center. We had a placeholder name and went to the Airbnb open. We went to 2 of them, 1 in 2016 and 1 in 2017. 2016 was in Paris and 2017 was in Los Angeles. We started trying to figure this out like, “Could we do something?”

David has known this industry a lot more. He was guiding us on how to solve the needs of the customer. My strength comes from listening and being more of a product designer. How do we construct a solution that would be meaningful for this customer? How do we go to market? What’s that look like? The two of us have extremely complementary skills. I’m a big idea vision person. He’s the follow-up in person. I’m admittedly not good at that but you need both. We’ve been working together for a long time. We’re like brother and sister at this point. Our families know each other. We live less than 1 mile from each other too. It’s nice.

You realized that the trajectory that you were on wasn’t correct for you or your family. It wasn’t correct for where you were at that time in your life. You had the balls, for lack of a better term to say, “This isn’t for me. Let’s do something different.” You took the time as hard as that was. I could see that if I had, I wouldn’t be able to do it.

I have this adage, which is if someone is thinking about making a change, it means that the change will always be good. If a friend comes to you and says, “I’m thinking about doing this new thing, leaving my job or making a change in my interpersonal relations,” usually, they need to be pushed to make that change. Rarely do people look back and say, “I regret making the change.”

I can’t think of any maybe 1 or 2 instances of prior people I’ve had conversations or relationships with whom I have regretted a change that stays main.

There’s a strong psychological bias that we have, which is around safety, security and no ability or whatever you’ve gone on. “Even the devil is better than the devil you don’t.” That’s a terrible saying because the thing that you’re going to is 99% of the time is better than why you’re at it. You can’t compare them. They’re not devil to devil. We have a bias against change as humans.

What Hostfully was when you first get started is constantly evolving. We alluded to tech that comes, fails and doesn’t make it. Where do you see Hostfully’s strong suit for your software provider? How do you keep making more strides and you’re grabbing an adequate market share? Tell me if you are. I see you scaling. I see your market share grab. It’s nice to see.

The thing that it comes down to, and I don’t do the best job at this but I’m getting better at it, is being focused and intentional about what you’re doing. With our product, we knew that we wanted to build a platform product. We wanted one that was as open API driven as it can be. This has been a big differentiator from companies that have not done well. A high degree of success is correlated with whether the platform is open.

Other companies are doing that with Hostfully, which is great. We were very intentional about that. We do that all over the company. I’m talking to four candidates who are amazing people. None of them are exactly perfect for the job that we want and I will not pull the trigger on hiring them or building the feature until I know exactly that that is what we want. Some people think about it as saying no all the time but I think about it as saying yes to the thing that you’re focused on.

It’s about the intentionality of making a change. When I decided that I wanted to be a founder of a company, I didn’t care about being a CEO. I did want to be a founder because I wanted to influence culture. That’s what I cared about. I want to be the one who influences culture and says, “You should take a vacation, paternity leave, maternity leave or a day off when your parents are having a hard time.”

We have a person who couldn’t come to this conference because her dad’s sick. “You should be home taking care of your family.” That is the culture of Hostfully. I am very focused on that. I don’t give it all. I’m very open. I love people, ideas and talking about things but on the things that I care about, I don’t give it all. I would encourage readers to find the things that they care about and don’t sacrifice. Life’s too short. We don’t have that much time here. Get done what you want to get done.

At the end of the day, we’re driven by work, founding products and projects and doing different things but it still comes down to what we do to make money. Ultimately, families and everything else is by far the most important. Also relationships. I fully and wholeheartedly believe that work is a huge part of my identity and not everyone does that. In my spare time, I like working. Not everyone drives and my wife is not that. That’s why we work well together. Find out what drives you and keep going in that direction.

I love being a mom. Being a mom is my favorite job and I will do as much as I can but I also know that I’m a better mom when I work. That’s a personal choice everybody needs to make. Knowing yourself and figuring out your center point is important.

That’s interesting because this goes into this question. What are your whys that have built your leadership style? I’ve heard so many different pieces in knowing you, the things that come together and make you rip. I want to know your why and how it comes off as deliberately intentional in the things that you do. I know it’s not always that way and lots of different things influence that. How did you get to this? It’s an outlier. I’ve seen you as a leader and I look up to admire you. There are a lot of leaders and people in the space. It’s not like I don’t like them but I don’t necessarily think that leadership spurs. It’s the action that they do. When you see it done right, it speaks for itself.

I truly believe that everybody is a leader. The people whom I work with and my friends, they’ll tell you that I’m the first to relinquish my leadership or control over the situation. I’m fine going along with the flow. Last time we were trying to figure out what to do and people are like, “I want to do this or that,” I’m like, “Honestly, I’m dumb for whatever. Let’s do this.” I don’t have a sense of one needing to be in control and that gives me an advantage.

The second thing is I do spend a lot of time thinking about how other people feel. I’m a classic who put myself in the other person’s shoes. Where are they coming from? How are they feeling? What would be important to them? When I’m thinking about how I interact with people, my team, even you and friends, I’ll be like, “Where are they coming from? How’s Mateo’s family?” “He’s in town for a difficult thing.” What’s that going to feel like? He’s coming to the city to meet me. I’m thinking about the other person generously. I don’t try to sell or lean into that.

There’s another thing that I learned early on. There were a couple of key moments and it’s so funny that they come up in these weird ways but we were at this conference with ServiceSource, the company I was with. There was a guy who was drawing caricatures and was like, “Let’s draw you at your best, John.” He would interview the other people on your team and be like “What’s John when he’s on fire? What’s John at his worst? What are the things that get in your way?”

For me, the drawing was Margot at my best ninja. He’s like “You’re so capable. People want to watch you and want you to lead.” The person at my worst was the scream. When you let your anxiety or worries get in the way, you can also devastate a project. It’s fine. It either goes up or down. The more you could stay in that calm, collected and cool energy, people want to listen to you and I took it to heart. Also, it’s great to have a drive. I’m a visual person. I want us all to do this.

I’m in. There you go. Have a character.

We did that and took it to heart. I thought, “If I can be calm and make the best decisions that I can, I could be in that ninja mode all the time.” If I’m in the ninja mode only 30% of the time, what if I was in it 60% or 90% of the time? My life would be effing amazing. I’d be happy and I’d feel good. A lot of it is managing my mental health. We all feel anxious when we’re about to present, make a difficult decision or make hard trade-offs. It’s anxiety-producing. What I do is find what it is that will make me feel good, whether it’s sleeping more, which is a big one for me, going for a run or listening to music. Singing for me is a big cathartic thing that feels good. I spend a lot of time managing my mental health. The leadership style is a byproduct of mental health.

A lot can be learned from this. I love that you said every one of us is a leader. If people would think of themselves as leaders more, as opposed to just part of something or they’re a cog, lead and take stuff to heart, overall, we’ll see leaps and bounds in this industry or anything in general. How you lead and what you bring to this industry are refreshing. We appreciate this a lot. This is great.

Imagine if we all could be operating at our highest potential, how much better our lives would be together. That’s where I’m coming from. I am not a growth person. I’m more of an efficient person at heart. There are many smart people here. We don’t state the problem that we have, even with the environment. Say it out loud. You’re smart. I’m smart. We all have great ideas. If we’re able to operate at a higher level and share those ideas and feel competent, then we’re going to have a better working environment, whether it’s inside the company or outside the company with their customers. Life is too short not to live a joyful life like that.

Before we get out of here, I want to make sure that we know what’s new for Hostfully and you. We’ve come to the end of conference season for us. Most of us aren’t going to be traveling for a while but there are lots of follow up. Q4 is very busy. All of us are working our asses off to make sure that we get to where we need to be by the end of 2022. What’s new for Hostfully? What’s on the horizon?

It’s a little early but we’re launching our mobile app. It is live on Google Store.

Congratulations.

It’s in the app store review but it’ll get through it. We had one minor hiccup and I’ll make the adjustments. The tagline is, “Hostfully makes you happy,” which I love. Shout-out to Brad on our team. The mobile app is powerful. It lets you manage all of your stuff on the go. Hostfully is awesome. It has powerful distribution and central calendar functionality on it. That’s a big thing for Hostfully and it’s so beautiful. I’m excited.

I can’t wait to demo it because me coming from the PMS world before I came over to Hopper, it’s what most software sucks at. For most of our property management software, their mobile app is horrible. I try to put myself in the shoes of a property manager trying to go ahead and get this stuff done but I can’t. I’m excited. Can I get a demo soon?

Absolutely. It’s been a private beta with few customers and universally, they’ve been happy with it. We slowed down the release because it wasn’t working great for the larger sale property managers. We made a bunch of improvements and that works well. That is huge. It’s a fun new shiny object for us, honestly. We have leaned into our partner status with Airbnb, Booking.com, at VRBO because that’s one of the reasons why companies come to us.

They want good distribution capabilities. We’re working closely with all those companies to facilitate the best interaction that the property manager can have, whether it’s adding all the amenities, approving research results and having different channels, call it different things but how fast we are at responding to the data calls in there.

We are killing all three. We’re in the time of year when everyone’s hustling to get the rest of the year done. We’ve already done that with the chant with those partners. We’re in the bonus period, which has been fun. We’ve been seeing our comparative data against other PMS companies and they like to blind all the data but we could see that our growth is outpacing, almost everybody else in the industry. It’s cool and fun.

For property managers in this space, it’s hard to learn as a property manager how poor that is until shit breaks. That’s the big thing for us. We also have expanded our team a lot. We grew from 30 to around 80 people. We’ve got a big team. They’re so enthusiastic and passionate about working together. It’s been amazing.

They look good in peacock scholars and students. They speak fifteen languages. It’s insane. Margot, thank you so much for joining us. This has been a real treat. We squeezed it in. We made it happen. We appreciate you joining us. Thank you so much. You have to come back.

I know. I’ll do it again and I’m glad you were able to do this in person way more. Thanks.

Important Links

• Hostfully
• Book Direct Show
• Booking.com
• VRBO
• Megaphone.fm/AdChoices