June 8, 2022

An Authentic Approach to Raising VC Funding, with Hostfully CEO Margot Schmorak


Fresh off a major announcement that Hostfully successfully raised $4M in funding, Margot is part of only 2% of venture funded companies led by female founders. Margot credits her success to her ability to lead with transparency and authenticity that is rarely seen in the VC world. Mom of 3 beautiful children, she talks to us about how she balances a very busy work and home life and the challenges this has created along the way of building Hostfully into one of the most successful property management companies in the world.

CONTACT MARGOT SCHMORAK
margot@hostfully.com
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Hostfully

CONTACT ALEX & ANNIE
AlexandAnniePodcast.com
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Alex Husner - Linkedin
Annie Holcombe - Linkedin

Podcast Sponsored by Condo-World and Lexicon Travel

Transcript

Alex Husner: 

Welcome to Alex and Annie, the real women of vacation rentals. I'm Alex, and Annie, Annie. And we are joined today with the CEO and co founder of hopefully Margo shmorak. Margo, welcome. Welcome to the podcast. We're so excited to have you here today.

margot schmorak: 

Thank you so much. I'm really thrilled to be here.

Alex Husner: 

Awesome. So we actually, and when I say that I'm excited about everybody that comes on the show, and I really am. But we've been really excited to have you on the show for a couple of different reasons. We we first met Margo at the Vacation Rental Women's Summit. And got to see you on stage and you know, hadn't met you at that point, but just got to hear from you. And you gave so much great advice to the audience there about choosing a career path and being a woman in tech. And you know, working in the VC world, just a lot of different perspective, that was really interesting, we thought. And so when we reached out to you, we ended up we were able to reconnect in Chicago at the recent VRMA Spring forum. And the three of us had just the best little converse, I say, a little conversation because we were literally in the corner of the conference hall in a little circle, sitting Indian style, because we couldn't find any shares. And we just had such a great conversation. So we've just been looking forward to having you here. But But before we get started Mario, can you give our audience a little bit of history of who you are and what your involvement within the space has been?

margot schmorak: 

Yeah, thank you. So I'm really excited to be here too. It's a dream to be on your all female podcast. And I just I The feeling is mutual. So just a quick background about me, I grew up in Minnesota. I'm gonna start from the beginning, because I think we're gonna touch on some of these topics. But I'm used to being an outsider, I'm Jewish and Chinese half and half. And so I never quite fit into either of those communities, although I definitely claimed them as as an adult now. And I grew up there and went to Vassar College. And then after Vassar moved out to Colorado, and had a bunch of different jobs, but ended up applying to business school, and went to University of Michigan, and focused on strategy and marketing there and landed an internship at Apple, which was a much smaller company at the time, it was pre iPhone launch. And Apple had this amazing experience was there during the iPhone, on the day of iPhone launch, I helped to launch the iPhone developer program there. i At the time, I was also dating my now husband, and we were living here in Silicon Valley. And then got an it really big itch to leave apple and do something in a startup or something where I had more visibility into the rest of the business. I joined a company called cover Roo, and that pivoted a bunch of times. So I learned a lot about startups. And then I joined a company called service source where I really had no idea what I was doing when I joined but I figured I'll figure it out. And I had my first kid at that point. And I kind of wanted a job where I wasn't so responsible for everything I'm sure a lot of property managers can relate to just not being on the hook for every little thing, like you can in a small company. And so in that larger company, I had a lot of latitude actually to grow. And I started out as a senior manager and ended up getting promoted to director and senior director and then vice president and I was on, I was Chief of Staff to the head of Global Sales running a 250 unit. And then I was vice president of all marketing and strategy for the business. That company was going through a lot of transitions when I was there. So it gave me an opportunity to learn a ton about how a public company works. Not very big, but just different. And so after that I stopped working because I just wanted to find something that I could work on where I was really passionate about the output. And I was looking at education and traveled healthcare and met my co founder, David, who was an Airbnb super host. And he was iterating on this idea around guest experience in vacation rentals. And we started hopefully together. I thought it was a quick trip into a startup. But three years later, I was like, wow, we are still going and this is not fast. We need to keep going. In 2018 though, we had a big pivot where we we merged with RV rental, which is pretty management software. And and then the two companies really set us off on the trajectory that we're on today with boastfully where we're seeing rapid growth and, and a lot of, you know, we're solving a lot of mission critical problems for our customers. And now we have a big team we're about growing really fast and with staff members all around them around the world. We've got 40,000 properties that we're touching on a daily basis. We've got you know, just a lot of volume 2 million guests, traveler views on our guidebooks every month so it's just like a really decent sized business now and I feel so grateful to be here for this ride? And I'm the CEO and co founder of Hostfully I didn't mean mentioned that before. Yeah, that's super exciting. I, it's,

Annie Holcombe: 

I'm glad you brought up Apple because my husband is a self professed Apple like crazy like everything we own his apple, we have Apple stock, like the whole like we you know, he watches all the release dates and or videos and everything. And so I was curious, in that time that you spent there you said it was a good experience. What do you think you learn or took away from that that you've been able to use? I probably I guess in every step of the way, it seems like that they have a really good culture of cultivating entrepreneurship and being kind of on the cutting edge and really thinking outside the box. Do you think that that experience was was pivotal for you?

margot schmorak: 

Yeah, I do. So what Apple's really good at is pushing for innovation and like the very best. So at Apple, I would say like, that's where you kind of get that like neurotic, like, this thing has to be pixel perfect. And if it's not 100%, right, I can't live with it. That's that's the quality you get from Apple. I think that it does push for innovation and new thinking. And actually one of my projects was doing strategy presentations around the coupling of the iPhone software and hardware together and what impact that would have on the way mobile devices worked, which it really was revolutionary at the time. But I think Apple doesn't do a lot for entrepreneurship. what Apple does, is they your specific area. But you know, when your husband is like watching the product launches, that's what all the other employees Apple, that's when they find out about those products launching. So there's a yeah, there's a lot of secret. I mean, that's how Apple runs your business through trade secrets. And it works well for them. For me, actually, it was incredibly frustrating, because I like understanding how what I'm doing fits into the big picture. And at Apple that just wasn't part of the culture there. And I oftentimes got kind of my nose cut off, actually, because I was like, Well, can we work on this over here? Or what about that? Like, that's not your job, you focus on what you're doing? I mean, I had enough to do sort of, I actually I kind of didn't have enough to do I was playing scrabulous, like, six hours a day.

Alex Husner: 

Yeah, yeah, I was kind

margot schmorak: 

of bored. But I did, like the stuff I worked on was really high priority and important. But like the rest of time, I was just spinning my wheels. I mean, I literally had learned how to play the guitar that year, because I brought a guitar to the office. Oh, yeah.

Alex Husner: 

That's, that's really interesting. I mean, how have you taken what you learned there as far as from a leadership perspective, and applied that tastefully? Because I mean, I feel like that that would be very hard for me to be in an organization like that where you are, you can work really hard and your job can be really important. But if you can't connect it to the big picture of where that's going, I think that for me, that would be very difficult. But I mean, how have you taken what you've learned there and applied that to your team? And hopefully,

Unknown: 

yeah, so one of the things I think about a lot of at Hostfully, and this, this goes like during COVID, and during our current economic downturn, is that I believe, fundamentally, that if you give people more information, and it's clear, and they understand it, that they will make better decisions. And that like by sharing, and maybe oversharing, compared to most other leaders, I can actually do a better job of empowering my team. So I've actually like swung hard the other way, Alex, because I agree with you. Like, I think that the strongest if we are hiring very strong people that Hostfully, who are going to be thoughtful about the decisions they make, they have to have the right information. And if I'm not giving them the information, and the visibility and the transparency into what's going on, they're not going to make the right decisions. And actually, this is why I founded the company. So it at Service Source, Service Source has had a great culture. I love the people I worked with, but there were times when the senior management would have like something that they were pushing, but they didn't really share it with the broader organization. And it would be like a handful of people that would know what was going on. And I understand why they don't want to cause a lot of like, stress and anxiety and change, right? Because some Yeah, suited for that. But I remember looking around in a room and thinking, wow, like, so first of all, surface sores, there was a culture of like, if the CEO said to do it, do it. Yeah. And, and I remember saying like that CEO didn't have to do what he says to do. He hired us to think and actually make our own decisions about things. And they were like, Are you sure? And so I really tried to do that hopefully, and actually explicit about it. I'm like, I hired you to make the best judgment, given the information that you have. And it is our collective responsibility to make sure you have as much information as as, as we can give you. But it's also my responsibility as a CEO. So actually, like yesterday in the company, you know, there's like a lot of noise about capital markets, venture backed companies, what's going to happen? And I was like, Well, this is what I understand. I'm not an expert. This is what my going and assumption is, is my that process this, how it relates to his fleet. This is how it relates to your job and your tasks and what you're doing on a day to day basis. And if you if you have questions like, let's have that conversation, we did the same thing during COVID, of being like we were, I think I was May 21, which was like, right after all this shutdown, we completely change the plan. And we got on with everyone. And I cried in front of the whole team. And I said, like, I don't know what's going to happen, and I'm really freaked out. But this is what I do know. And this is how we're going to do it together. And I think it is, it's, it's funny, because almost like by being bold, more vulnerable, and more like showing, like, how anxious I was inspired a lot of confidence and trust in the team. And, and I think that's why we have just such a happy team, that it's just really devoted to the company in a lot of ways. So I don't you know, I'm not asking for loyalty or anything like that. But what I am asking for is like real thorough and deep engagement from everybody. But it's

Alex Husner: 

authentic interest, right? I mean, I don't think crying is a bad thing. And those situations, because I mean, you were showing up and being very authentic to yourself and how you felt, you know, and I'm sure your team really respected that too.

margot schmorak: 

Yeah, they did. And I, you know, I remember at covering, we were going all through all these ups and downs. And at one point, this is not unusual in startups. So this is not the bad part. But if a company ran out of money, and they couldn't pay payroll, it happens, right? Yeah. And or I think we had to pick the they asked if we could take less for like three months or something like that. And I wasn't bothered that they asked me to take less, I was like, okay, you know, it's a startup like, that's what happens every once in a while. But what bothered me was that I didn't have the visibility to what was going on, I didn't understand, like, what was happening with fundraising, and I didn't understand that when the money came in, like, I should get paid more again. And like when that happened, you know, all that stuff, like, I was, like, I'm trustworthy, and I would have done, I would have done the right thing. And like, it would have been better for everybody. And I would have felt much more motivated to stay. So

Alex Husner: 

I want to know what's coming. And we saw that with a lot of companies during COVID, that they, instead of laying their teams off, they just, you know, cut back on salaries and bonuses and stuff like that, but also saw the other side of it that when sales started coming back in that was not given back to them. And I know from several friends that were in that situation, they're like, you know, what do you do? Because it's, it's not being communicated for a reason. I mean, that obviously, they they know that you remember that your pay has been dogged. And you're probably curious when it's going to come back. But yeah, I mean, not having that trust within an organization is definitely a setup for failure.

margot schmorak: 

Yeah. And I think navigating through downturns is hard. I'm not, you know, like that. That's a very difficult situation to be in. I think it's a missed opportunity, though, to say like, you know, we know that your pay is docked, and we're going to have to keep it docked for a few more months, even though sales are coming in. This is why Right, right, exactly. Like we had all our you know, this is why, just so that, because they're probably not going to leave, they're probably actually going to stick it out. But the place is going to be resentful. And and why not? Why not? When the employees trust by by explaining what's going on? It's just a missed opportunity, I think, in those situations. So, yeah. Anyway, so

Annie Holcombe: 

you know that, you know, you're coming up and you starting hopefully, one of the things we talked about at the woman's conference, when we first met and talked about subsequently is women going before VCs to try to get funding and that transparency. And I think that you know, what you're doing and for your staff is the the right thing to do. But I think that that, you know, how do you how do you use the transparency that you give to your team to try to foster a transparent conversation with VCs when you're trying to get funding? Because one of the comments that came out of the Women's Conference was that the questions that are asked to you are different than the ones that are asked to men. And it's not the same process, and that it's not very transparent as to how that process plays out. So what would you what can you enlighten us on on how that all works? And your thoughts of it?

margot schmorak: 

Sure. So most venture capitalists, not all, but most are white men. And they're looking, they're doing pattern matching. And it's really a gut feel thing. So they're looking for, like, patterns they're seeing with, you know, regards to the numbers, but also patterns with people. So they're looking for people who are curious, and, you know, and tenacious and smart and driven, and sometimes, like really focused on a financial win, for example. And my way of doing this is a little bit funny. So I'll just like put a few give you a few anecdotes of so. Okay, I'll start to finish that thought. When men meet me or another woman, or a person of color, or someone who's you know, gender queer, right? They're just they don't know what to do with us in some ways. They're just like, well, this person doesn't fit the archetype of what I'm used to. So I don't really know how to like evaluate them. So it's really subtle. I mean, we're talking about bias, right? We're talking about unconscious bias. Sometimes conscious bias, but let's put those people aside because they're, they're sort of like dying out there, which is good. And the reason why this happens is because the venture capitalists have investors themselves. And guess who those investors are all white men, right? So you basically just have this as the systemic bias men, because those are the people who are funding the process and have the power in the in the, in the hierarchy. Because you know, the VCs want to make their LPs happy. And they're all the same, because they trust each other. Because there's a bias actually, like a proven bias that says, like, if you look like somebody else, they're going to trust you more. That's just how it is. So the real way to fix this is actually to get more women, LPs. So that's why you have to have women who are very rich, like, you know, Mackenzie Bezos, and all these people at the top, they're actually just getting, but I'm to your questions. So like, how do you do? How do you navigate this? I mean, I definitely vacillate between being like, discouraged and sad and disappointed and angry. But there are a few things that I did in the fundraising cycle that I, I experimented with, and one of them was using the unconscious bias in my favor. So it's like if I meet somebody, and okay, so I don't know if the viewers can see. But behind me, there's a clean wall and there's a painting, it looks really nice, actually, in the room that I'm in professional. But when I was fundraising, that wall was like, a floor to ceiling bookcase filled with like, kids toys and games, and it looked like, I remember you telling you that it looks like super disorganized, and I, I thought like, should I change my background or like blur it out, like make it blue, hopefully, whatever. And I thought, You know what, know if that's the reason why they don't invest in me, or that's the bias that they're gonna like us to make this decision. They're not the right investor for me, and they're not the right investor for this company. So I waited until after the fundraising cycles over to make my room really nice. Because I kind of did it on purpose, because you know, what my looks my business looks great. And I pitch really well. And we have a lot of opportunity, and we will attract the right people. But I would rather screen the wrong people out faster. Because this is a numbers game with fundraising. It's like, and for me, it really was a numbers game. But I also can use like little things in my favor. So like, I'd rather get it fast. No, I would rather it attract the kind of investors who can see past some of those things and are not gonna emerge from that. And I'm, I have some amazing investors in this round, like one investor invested us exclusively on culture. That's what I believe in a lot of investors. And like you said, like, how do you get investors to see that I'm like, they don't see it. And honestly, a lot of them don't care. They don't care about how we treat our employees, they don't care about, they don't care about culture, they don't care about communication, internally, they just look at results. And some of the investors who invested don't care about any of that stuff, they just want the kind of results that we're gonna have them do. And I was able to get them in the round, which was really cool. So I'm like, I think I saw this really great thing today. And I posted on LinkedIn, actually, one of our investors, Arlen Hamilton, who's the first black, female, gay venture capitalist at a news with Mark Cuban. And because she, you know, from Shark Tank, and she made a Shi t shirt that said something like, make, like be the authentic use. So the people who are looking for you can find you, you know, I don't know if that's exactly what happened. But it's kind of that it's like, put yourself out there and don't try to be something else. Because if you're not yourself, you might not you might miss the people who are actually going to be your advocates and who are gonna ride with you on the rise.

Annie Holcombe: 

So your two people will come if

margot schmorak: 

you wait, that's right. And maybe that's enough, you don't need raising money, I don't need every investor I just need a couple.

Alex Husner: 

Anyone if you're I love that you did that and that you were transparent and showing Yes, I am a mom and an active mom and you have three active children that you clearly care the world about. So I think that's important to show and and if they aren't for you then they'll move on and they'll find somebody else but it's to put on a guy's and try and make somebody happy thinking that you are one way that you're not you're just setting yourself up at the company up for failure in any capacity. You know, when you do that, so I think that's that was a smart move for sure. But I am curious. I mean, that's that's your your your life and how busy you are within your career. You do have three children. Talk about that a little bit. I mean, how do you balance that mom life and what is your support system look like? That allows you to do that?

margot schmorak: 

Yeah. First of all, I just want to say that I've totally like acted the part of like being Altarum you know, like polished and stuff and so like I you know, I really like I'm still struggling with this today like, who am I? And what do I, you know, what are the different environments? So, for anyone else who's on that journey, like, don't worry. But, no, it's my life today. Yeah, a lot of it is it is infrastructure, just like you said. So we have an au pair, we have an apartment that's attached to her house, she lives there. She does like the morning craziness with lunches and drop offs. And my kids school starts really early, which a lot of other parents dislike, but I love because then I get to do meetings like this. And to start my day at a good time. Yeah, and my husband and I are very involved in everything. He he's probably less a little bit less involved with like the day to day stuff with the kids. But he does the laundry for example, I like I think I've done like two loads of laundry in the last 10 years. Like he's like the regular things you like, like, like making sure like the garage door app is working. And like, Yeah, I'm a little more responsible for like the minutia of children, you know, which is very taxing. I know, other people understand this. And that's a lot for me. But there are opare is a full time person in our house. And she's amazing. And we've had Au Pairs ever since I had two kids. And that's the infrastructure. Yeah,

Alex Husner: 

I grew up with an au pair. And actually, my mom, she's, she had a brain aneurysm about six years ago, and she's in assisted living now. And, you know, growing up, our au pair lived with us until I was I think four and she was from Holland. And she ended up she moved to the States after that. And we've stayed, we've stayed in touch over the years, but really haven't reconnected until just recently, kind of with what my mom has gone through, and just saw her recently, they live in Raleigh, and her and her family came down to visit but I mean, she's kind of become like my second mom. So I mean, the the impact that those relationships have, at a young age are really important. So and it's worked out great, because I don't have my mom, but I do have her. So that was a good thing for me.

margot schmorak: 

Yeah, I think I think there's this thing when you first start thinking about having children about, like, if I bring somebody else in, like, will they replace me or my kids? Like, not? My mom, and that's, like, you know, that, like, there's been ample studies that have shown, like, none of that stuff happens. I mean, it's all just like, the quality of the time you're spending with your kids, you know, do you really tune in, listen to them. And, and, and I also have, from day one have just been like, more love is more love, like if my kids are getting more love from their teachers or from their other family members, or au pair, like it's just more love, like, they're not going to suffer for that. So why Why should I be holding it back? Yeah.

Alex Husner: 

One thing we talked about when we were all sitting in that little semi circle was I mean, confidence and how to create that. And you mentioned growing up in high school feeling like you didn't, you know, physically look like the kids you that you went to school with and the impact that that had on you. And I'm just curious when, as you continue to grow in your academic career and in your early business career, like what was it that gave you the confidence to now be this incredible leader of the company? Like how did you how did you build that confidence?

margot schmorak: 

Well, I didn't feel that confident until like, I can't. I've always been I love always love solving problems and fixing things and making things better. But it wasn't until in the middle of my career at service source when I had this moment of realization and I won't be interesting for everyone to consider this for yourself. So we had this caricature artists come to a company event and draw us at our best and at our worst and and I asked Oh, and they said like ask the people around you like what it is. And there's this guy Jeff Bailey who was a friend at the time I haven't talked to him for a while but he's good guy. And he's and he said yeah, he went up to the character I just need like whispered in his ear and and I and then the character is through it. And on one side was me as like a ninja like super capable I got you know, I can do everything. And then the other side of me was like Margo as The Scream like the you know what I'm talking about, right? Yeah. And I was like, what is that? And he said, When you are comfortable and being yourself like you are so incredibly capable, but when you're overwhelmed it's like stresses everybody out all around you and you don't add a lot and it was this awakening for me because I thought like all I have to do then to be my best is just not be overwhelmed to actually like yeah, pretty simple but effective. Cool. Yeah. And it was just like if I can and I'm an upset I'm a highest highs and low lows person like that's how I am my husband and I were joking about it the other day, but if I It says I don't need to get rid of my high highs and low lows. But like, in, in hearing how he was talking about it, I was like, I can be a really good leader if I just like, remain calm and then just do what I already do. I don't actually have to change any part of myself, I just yeah, just just calm down a little bit. And so I think like, that was really a big confidence boost for me, I needed the external like view to understand that, and I'm grateful to have gotten that. And now it's like, yeah, I just feel like the more I lean into, like, who I really am, and being a positive person and, and staying calm, and like maintaining my mental health sleeping, like, yeah, I can do really great things. It just like I have to take care of myself first. So that's the most important thing. Yeah.

Annie Holcombe: 

So um, the the confidence building, one of the things that I love about you, and I think that you just, you talked about it, every time we've chatted, is about you wanting to elevate other women, regardless of the industry that are they're in, but other women that are trying to be CEOs and venture back CEOs. And you were talking to us off camera about a group that you put together recently that it was just women from all over? Can you tell us a little bit about that? And kind of what your what your goal was for that? And if this is an ongoing project for you?

margot schmorak: 

Yeah, so um, well, first of all, I think I just naturally I really see value in everybody, it doesn't matter like how smart you are, or where you came from, or whether we speak the same language, like I'm like, I believe that each human is the same amount of value. So I think that actually is like a big deal. And I think that's really important. In my like, philosophy about life. It just, I feel like life is short, and we just don't know what's gonna happen. So we have to, like, we have to treat each other with that level of respect. Otherwise, we're just not gonna get anywhere. So that's like an important premise. But yeah, with this group, this moms group that it's a moms group. That's the funny part. So there were a few women who connected in part of one of our, our one of our investors, they have these like Slack groups that we're in, and we were connecting in there about maternity leave. And another woman who actually her her co founder was going on maternity leave was like, I need to know how to support this, Mike, my co founder, I have a lot of questions. And so we got into it, there were like two or three of us. And we were having conversations about like this, how you what you can do, this is what she should plan for, this is what you should plan for here. I wrote a blog post about it, like let me help you out, you know, normal like mentorship, co mentorship kind of stuff. And then we realized that there, there were more women that wanted to hear this conversation. And so she started this group called VC back moms. And it's a self organized group of women who have raised venture capital for their startups. So you don't need to be CEO, you can be co founder. And the venture backed is a kind of a a, like, it sort of like, is an indicator of how serious you are. Because like when you take in other people's money, there's definitely like, a higher level of responsibility for that. Oftentimes, you know, millions, we're talking like millions of dollars, I think everyone in the in the group has probably raised at least over a million dollars for their, their company. And in the beginning, the joke was like, Oh, great, it'd be all 12 of us, and we can like have a chat together. But then it was like 12, and then it was 65. And now it's like 110. And, and yesterday on LinkedIn, somebody tagged me again, there was another woman who's like, I'm out pitching pregnant. And this is crazy. And you know, I'm trying to figure out how to think about like, maternity leave and run a company on having kids like, I feel like no one's out there. And my friend was like, Margo has a group. And so like now, it's like, we're able to assemble this group. And then last weekend, this magical thing happened, which was, I was like, let's have a retreat and get everyone together. So we invited I invited seven. One person I knew very well, but the other I invited six strangers or seven strangers.

Alex Husner: 

That's incredible.

margot schmorak: 

And we spent the weekend we slept over in like, wow, people were in like bunk beds together, or like sleeping on the floor. I mean, it was not like luxury accommodations, it was just like, Let's hang out and have like 24 hours, people went from LA and took like, 6am flights back, like, it was really amazing. And it was just, there's so much pent up demand for finding these micro communities. And I, I hope that this story kind of inspires other people to find their own micro community, because there's a lot, you know, you can be on LinkedIn, you can be on Facebook and these big groups and feel kind of lost, but there's probably a handful of people that are really struggling through exactly what you are and like join up like, it's our as a Yeah, I

Alex Husner: 

know, in my career that's been super helpful and important for me, just in our local market here. I mean, just keeping in touch with and having my little group of friends that are kind of do the same thing for their companies, you know, and we compare notes and it's just it's so good to have that support system that it's not it's not within your company, but they're doing something similar but it's also not your close friend group, but it's not your family. I mean, it's that's just your kind of your key group. You look to when you have questions that you want to make sure you're going in the right direction. But yeah, really, really cool. And that's, I love that they all came and stayed at your house. What a way to welcome them with open arms. I think that's great.

margot schmorak: 

Yeah, yeah, that was really fun. It was great. It was kind of magical. It was it was it was unlike anything I've ever been to before. Because yeah, like you said, like, these people are not close friends. But people were very, like, willing to have pretty intimate conversations with each other. Not not like over overly, but just real talk, you know, about the struggles of being of any? Yeah, yeah. You know?

Annie Holcombe: 

So was that something that you just felt like, hey, I need this for me. So I'm just going to put it out there to see who like gravitates towards it? Or is it just something that it was kind of an organic conversation that was going on, and you just decided to take the lead on it?

margot schmorak: 

I didn't, I didn't really take the lead on it. What I did, what I do feel, though, is that I feel like we are all pioneers. Like if you are part of a marginalized population, you are a pioneer, by definition, like, Yeah, and so the best thing you can do is like, leave a trail, you know, for the next person. Because it just makes it a little bit easier for them like 5% easier, right? Like, you're not going to just like leave your little, your little gold dust trail, and they can they can follow you. So I started doing this when I was at service source, and I had my first kid and I was pumping and there was like, no pumping room. And this was like before, you know, mothers rooms were everywhere. And I was like, This is bullshit, like women should not pumping in office rooms or expect to do it in the bathroom, God forbid, right? So so in that role, or can we get credit pumping up, they're like, We don't have any budget. And I was like, This is so stupid. Like, I can't, I can't believe I cannot believe we're having this conversation. I was like, Screw it. I'm just gonna take budget. Now at that point, I was head of marketing. And I was like, I'm just taking my budget, and they were like, That's not allowed. And I was like, I don't care, someone can come. And if I got it, I was like, here's five, we're gonna spend it on this painting and putting a fridge and a sink in this mother's room. And it's like, be like, that's what we're gonna do, you know. And with this group who it was like, we Oh, same thing with maternity leave. People were like, No one goes on maternity leave while they're running a startup. You don't tell your investors, you know, don't tell your investors, you're pregnant. And I was like, well, that's so stupid like this is we have to live in a world where women can do this. At the same time. This is crazy. I wrote this blog post, actually, I wrote up, I was in a group. It was like a private social network group. It's now called Alpha. At the time, I had another name. And I wrote this long thing in there. And people were like, well, this is amazing. And I had all these likes. And then I was like, You know what? Why is it the private social group? I'm gonna put it in public. Yeah, like, exactly. Yeah. And so that that post, like, it is crazy. As was written four years ago, people are still sharing it all the time. And, yeah, it just looks like what here's my plan. I mean, I don't have all the answers. But I was like, here's an example. I've had women reach out to me. And they were like, that's the first time I've heard of a CEO talking about this. Who has not merit Marissa Mayer from? From Oh, my gosh, no. And they were like, thank you for doing that. Because I'm trying to figure this out. So that's like, what I'm good at is like just sort of packaging up my story. And being like, this is what I did. I don't know if it was right or wrong, but hopefully it helps you. Yeah. And then. And then Amelia, who's the real leader of the VC back to mom's group is the people person, she's like, the community builder. She just like brings people in and, and follows up and like, and it's just brainstorming about that her her app is actually a community as well. So it makes sense for her. But she's really the one who started this group. And then I was like, Well, we I can do a retreat. Like I'm happy to not be the lead. I love not being I love it when other people tell me what

Alex Husner: 

to do. Exactly. Every once in a while. Yeah. I think I mean, you're you're the point that are the takeaway I'm getting from that is that I mean, if you're thinking something, somebody else is probably thinking the same thing. Right? So in that case, you know, don't put it in the private group put it out there because somebody else probably doesn't have the confidence to put it out there in the first place. But seeing you do that inspires them to want to continue that conversation and open up something that needs to be talked about.

margot schmorak: 

Yeah, exactly. And you know, that like mama bear thing that comes with women, sometimes after they have a kid and they kind of don't care anymore about other what other people think of them. It's like leverage that. Yeah, exactly. Like

Alex Husner: 

keep that going. When we were at the Women's Summit, the presentation that you did, I think it was based on like career changes, but I mean, you had you had this matrix of how you help people or advise people to have a make a decision if they're Gonna make a career change. And I think that doesn't necessarily have to just be career oriented, but just life change. And I think that's really an interesting topic for our audience. So can you talk a little bit about that criteria? And what you included in that speech in that talk?

margot schmorak: 

Yeah. Well, honestly, I don't remember all the criteria off the top of my

Alex Husner: 

head, or maybe just advice around that topics? I remember it was it was really good.

margot schmorak: 

Yeah, no, I think I can come up with it. So basically, I've made a bunch of different choices, career choices in my life, I went from making, you know, under $30,000, and working in an architecture firm, and to going Business School and then coming out and making six figures and, and so like, I, I've been to these, like big shifts in my life. And I'm really grateful for them, because I think it's helped me see why the navigation is so important. Whereas like, if you were in a job where like, things were more linear, I think it's like, not as important to have these frameworks. So they've been really important. When you look at any job, you look at people, you look at compensation, you look at, like, the actual job. And there's some other aspects of it too, like, oh, growth for me. And then there was also meaning. And I think when the in the talk that I gave, I said, like, for several years, I was looking at everything, but meaning because I didn't think that I deserved to have a job that had meaning. I didn't say that at the top, but that's the truth. Yeah. And and now I'm like, you can have meaning in whatever job you want. You just like maybe it's not like starting a nonprofit, or, you know, like doing something that's kind of arc typically meaningful, maybe it's like just creating a company. Good, and they can support their families, and they can live lives that are balanced. Or maybe it's like, for me the meaning and hopefully, is being a visible female leader, I hope that it's really easy for the next woman to do this. And I hope she does better than me. So, like, that is, that's meaning, you know, like, that's that you don't have to, you don't have to forego, like certain parts of your job for others. And I think for anyone in the travel industry, um, you're creating meaning for your travelers, meaningful experience, like you're, you're opening them to a new place and helping them understand a new, a new culture of the place they're visiting, even if, if I'm going from here to Savannah, Georgia, like, just because we're both in the United States, it doesn't matter. Like I still can learn a lot about what the experience of people are there and how my life is different and like what different, you know, amazing things they have in their culture that I've never seen before. And I think that for anyone in the travel industry, you're contributing to all that. So that's, that's, that's all. That's actually why I started with Hostfully too. Yeah,

Alex Husner: 

yeah. Annie that reminds me of the quote that we love from Heather Monahans book about leaving footprints in the sand.

Annie Holcombe: 

Yeah, yeah. Just read about that about you. You know, you're you're blazing a trail and in some respects, but it's like, what's gonna matter when you're gone? What what is that trail that you left behind? What are those footprints that are left for other people to follow in? And it's kind of goes to a question that I had everything that you just said is, what can I think we as an industry, vacation rentals as an industry, but just in general, how can we begin to plant the seeds of developing future leaders in women that are coming up now like coming out of college, and, you know, give them the tools and the guidance and help them be the best that they can be?

margot schmorak: 

Well, I think that women who are experienced in this industry can reach down and like, open the door for mentorship. One of the things that I do, and honestly, anyone who's listening to this podcast can use this, but I have, I'll basically meet with anyone, if anyone wants, like, time with me, I have a half hour Calendly thing that I send out, it's just like you want some time, I'll give you 30 minutes, no problem, like I just give give people time. And I think that everyone can do that for each other. And and then for women that are trying to grow, like you have to take the initiative to reach out and, and and take that time, you know, don't be afraid to ask and sorry. Don't be afraid to ask and, and maybe you'll get turned down a few times. But the benefit of having those interactions will really help you. And so I think like it's just like that bridge of kind of reaching back. I don't know the footprints in the sand thing specifically, but I think I get the gist of it. So that's one thing I think that women can do for each other. I think the other thing is like, talk about how it's hard. You don't have to be, you know, lying to yourself or others about how challenging it might be. I think in a lot of ways, trying to bust through like the different hierarchies of management in smaller communities within smaller companies is a lot harder than it is where I am right now. And you will find people who don't believe that you can do it and there They they're not they're not right. I mean, like, you have to just kind of listen to your own inner voice that says like, I know this business, and I know what to do. And I have an idea and it's good and you find out, find the other people are going to support you, when someone says, No, just take it and move on and find the group that's going to be supportive. So I actually think that if like, there are a lot of really amazing women that are running great businesses in our industry, like amazing, and so they are, first of all, go talk to them. But secondly, like, I also acknowledged that a lot of sexism and and challenge for women is in these like little communities. And I think it's actually a harder fought battle than is from my perspective here in San Francisco. So you don't need to be like, Oh, I know going in, it's going to be challenging, but it's just like, resource yourself with the other women that have been through it before. There are lots out there, and they will help you, including me, and including you, right, like you. You're all we're doing together. Yeah,

Alex Husner: 

I love that I love but

Annie Holcombe: 

I will thank you, you did give me some time recently, we had a great chat. And just really it was it was great for me, because it was just exactly what I needed at the time. And I think what you just said is important, because when I was coming up, I'm in my early 50s now and I was coming up in my 20s I didn't have any strong women leaders. And then it was probably when I got to Expedia, when there was a lot of women that were already kind of at a higher you know, C suite level leadership. But some one of the ladies kept saying to me, just fake it till you make it, fake it till you make it. And while I understand the premise of that, I feel like that's dishonest. It's it's not it's not genuinely what we need to look at is because faking it is not helping us, we need to be authentic, and be honest, and recognize our shortcomings and things that scare us and the things that are fearful and talk about them. So while you do want to like get step out there ahead of you know, before you have that experience. And before maybe you have that skill set to be truly successful. You also don't want to fake who you are as a person for such a long time that you lose, lose sight of that. So I think women are have been given mixed signals along the way. And so we have some work to do to kind of clarify that. But I think what you're doing and just in, in helping women within your space, and your level is tremendous. And again, I appreciate you taking time to talk with me. And then obviously to be on our show. It's it's wonderful.

margot schmorak: 

Yeah. And also, I don't think people ever feel like they've made it. And that.

Alex Husner: 

But you look back on, you know, five years actually, this is a good segue into one of our questions that we wanted to ask you, but you look back on five years, 10 years, and it's like, oh, my gosh, I have come so far. But you do I think that's all of us being driven ambitious people, you still feel like, I'm not there yet. I'm not there yet that you've you are there. I mean, it is the journey. But so that's one of our questions that we had for you that we always ask a couple extra questions at the end. And that one is what what what advice would you give yourself five years ago?

margot schmorak: 

Just to trust the path that you're on and to like, hang on, I'm just, you can edit this out. I'm just going to ask the person into my house if

Alex Husner: 

it's okay, no worries. And just start that part again. Are you ready?

margot schmorak: 

Sorry, no worries. So, okay, I'll start as if you just asked me the question. Perfect. Yep. So five years ago, I think I would have just told myself to just trust the path and just like, just trust the path that I'm on. And that I have the resources to do what I need to do. COVID was really difficult on me as like it was on everyone. And we all went through our huge challenges. And I actually think as a society, we don't really fully appreciate, like, how challenging that time was for everybody in so many ways, right? Like, just day to day life. Having small children was hard. I mean, navigating through different difficult political climates, no matter where you stand was really hard, right? Like thinking about your life and whether you might die was also hard. And I think I actually feel pretty proud of how I navigated through. But I wish I would have had that like now I have like a really deep trust in the fact that I know what to do when things get very tough. And I think at that time, I didn't really know that about myself. And so I actually don't have any like enlightening words for my five years ago itself. It's just like, stay the course and you're gonna be okay kind of thing. Yeah, you're gonna be good. Yeah.

Alex Husner: 

You won't miss what wasn't meant for you, right?

margot schmorak: 

Yeah. Don't you'll know the way you know, like when you get where when you get to an impasse like you'll know what to do. So don't don't worry about not knowing. Yeah,

Alex Husner: 

great advice.

Annie Holcombe: 

Well, I think we're kind of at time and we could talk to you, as we tell all our guests, we could talk forever. I think we need to do like a two part series on on everybody. But more of you are an incredible leader and very gracious with your time. And we appreciate you very much. And so thank you for coming on the show. And if anybody wants to get in touch with you, what is the best way for them to reach out to you?

margot schmorak: 

You can email me Margo at hostfully.com A R G O T at host flea.com. You can also contact me on Twitter, I'm pretty good over email, I use a good email filter. So it comes from a real person, I'll see your email. But those are good ways. Please do not contact me on LinkedIn. My LinkedIn is a load of crap and I get random inbound from like I occasionally will catch people like Annie because I was like I know who and but but like, yeah, email or Twitter is the best way to get in touch.

Alex Husner: 

Awesome. And we will include your contact information in our show notes for anybody if you want to just easily be able to get to Margo but thank you again for being on the show with us. If anybody wants to contact Annie and I you can go to Alex and Annie podcast.com And if you're enjoying listening to the show, please leave us a review on Apple or whatever podcast app that you choose. And until next time, thank you for tuning in and we will see you soon

Margot Lee Schmorak Profile Photo

Margot Lee Schmorak

CEO and Co-Founder Hostfully

Margot Schmorak is CEO and co-founder of Hostfully, a software platform for short-term and vacation rental managers founded in 2016. Margot was formerly at Apple where she launched the iPhone Developer Program in 2008, and she served as head of marketing for a $250 million business unit at ServiceSource. Margot is also a mom of three young kids and married to Ari Schmorak. She sings in an a cappella group, writes songs, and volunteers for DEI initiatives in the vacation rental industry and in her kids’ schools. She also loves mentoring other founders—especially women and people of color.