Analiza: Welcome to the Women of Color Rise Podcast. I'm Analiza Quiroz Wolf, proud Filipina American, mom of two, and former CEO of a nonprofit and Captain in the US Air Force. I'm on a mission to support having more diverse leaders at the table. We'll be talking with successful CEOs and C suite women leaders of color and learning about their leadership journeys. If you're a woman or woman of color, who wants a seat at the table, you're in the right place. Now let's get into today's show.

I'm excited to be with Melissa Kwan today. She's the co-founder and CEO of eWebinar. And what makes Melissa exciting are so many things, including that she's a startup successful three time queen, I'll call her, she's done this several times, including eWebinar. Her last company actually sold and was acquired back in 2019, was a real estate tech company. And in addition to being a startup queen, I'll call her, that she is also a nomad. And so she does throughout the world right now she's in Singapore. And she makes it work both in not just what she loves at work, but also with what she loves in her life. And so I'm really excited to bring Melissa in because she really believes in her values and lives it day by day. So excited to learn from you, Melissa, thanks so much for being here.

Melissa: Thanks so much for having me.

Analiza: So Melissa, I was introduced to you, because you've got this wonderful balance of both adventure, at work and at play. And so I want to go back to your roots. Because have you always been this way? Like did Melissa, young Melissa, have dreams of being a globetrotter and being also a startup queen? Like would you say that was the young listen dream?

Melissa: No, the young Melissa grew up in Hong Kong, so very conservative parents, so they just wanted a life for me that was better than their own. So they wanted me to be, you know, a professional of some sort, like, you know, an accountant, a doctor or lawyer that they could tell their friends about and be proud of, I just wanted to make a ton of money. And it wasn't like, I knew what money could buy, because we didn't grow up with a lot of money. Like my parents were middle class, it was that that's what I was told, right? Like, you need to have a lot of money. And these are all the things that you can have. And of course, growing up in Hong Kong, it's very, very materialistic culture. So I just always thought that I just wanted a lot of money without any concept of like, how I would get there.

And you know, after university, I worked, you know, small jobs here and there, but I never lasted very long. And throughout my life, I always tried to do like little side projects with my friends who, you know, were coming from entrepreneur families that I wasn't right. So I was always very jealous, envious of what they knew. But you know, as people know, unless you're focused on something, you're never actually going to succeed. So I dabbled in a lot of side projects, I can't even remember what they are.

And it wasn't until my last job, which was at SAP almost 13 years ago now, after I quit that, that I started my first company. So I don't think I grew up wanting to start my own company, because that was very discouraged where I came from, but I just always gravitated towards making my own decisions, freedom, enjoying smaller companies over larger companies calling my own shots being creative. So I think, you know, entrepreneurship, mostly found me versus, you know, the other way around.

Analiza: So tell me about this tension between your family. I'm Asian American, and when I think about entrepreneurial, just that idea that was not also like your parents, that was not the thing that they were saying, doctor, lawyer, you know, things like that. And I'm curious because you took this route. And while it wasn't, what was the path, like given to you as a kid, you went this path? And so how did you resolve the tension between this like family values, Asian values, and then also your pull toward entrepreneurship?

Melissa: I mean, it's super tough, right? For anyone who knows what we're talking about here, especially because when you're young adults, or when you're, you know, a teenager, you rely on your parents, right? Like you're living under their roof, right? Like, even though you've graduated, you're not making enough money to be on your own. So much like your boss. Like when your parents give you allowance, they get to tell you what to do. And so the tension, I think, never really resolved itself until I stopped relying on them but that actually took Many years. So my first company I ran for four years, my second company Spaceio, ran it for five years before it was acquired. So the first two companies combined was nine years.

I would say for seven, like a good seven, seven, a half of those years, like, they've had to bail me out multiple times. And there were two of those years where they just didn't even speak to me, because they just didn't understand why I wasn't taking my life seriously, it didn't want to occur to them, that the reason I was in that position was because I was taking my life seriously, because I was trying, because they don't have a concept of what it takes to start a company. My mom never worked. My dad worked in the same company for over 40 years before he retired. So when they allowed me I guess, to quit my job, and you know, gave me the blessing to start my first company thinking back, I think they just wanted to appease me, like they just wanted to, like, get me off their back.

And I think they just thought, Oh, this is like a phase, right? Like, it's just gonna last like maybe a year, maybe two years. I don't think in their wildest dreams, they would have thought like, this is how long it would take, like maxing out every credit card bill asking them to bail my credit card out multiple times, you know, asking them to, you know, for pretty big loans, like 20 to 40k loans, just so I can make payroll. I mean, that was really tough, right? And, but at the same time, like being daddy's girl, and you know, it was very hard for him to say no to me.

So I guess that tension was never fully resolved until the company was profitable. I wasn't asking them for money anymore. I was independent in New York, but they also just like really had to cut me off. Before, you know, I had to figure this out. And then eventually, I sold my company. And the first question my dad asked me was, so exactly how much money are you going to have in your account? It wasn't, congratulations. It wasn't like, good job. I know, you work really hard, like, the only measure of success for my parents was financial success. So I think that was very disheartening over the years, right, like my brother, and I always lived away from my parents.

So when my mom would come visit, the first thing she would say, after she got off the plane, is so when are you going to get a real job? And you don't need to hear that, right? Because you're already trying so hard, you're telling yourself that you're not doing a good enough job, because you're also not seeing the financial success. You're also the ones struggling, and then the person closest to you. Is validating that, I guess, right, validating the fact that you're not good enough. So there was just continuous tension here and there. But you know, obviously, that part's gone now. And luckily, I think as human beings, we have an incredible ability to forget pain.

Analiza: I mean, it's just like birth, right? Like, as a mom, myself, I'm like, Ah, let's have another one. I forget the most that told me because it is quite resilient of you to not only stomach having to build a company and Bootstrap. And this is something that you do write about, you talk about. And I'm curious, because there's something about being an entrepreneur, that's when I listen to you, when I'm listening to your different podcasts. It's part of your DNA. And I'm curious, what would you say those three things are that like, yes, yes, I'm resilient. But like, if you really are truly an entrepreneur, it means these things, like, for example, he had mentioned, you gotta be willing to get help, like, ask for help, you know, not have the money for payroll. And like, it's, I'd love to, like, get there. Because before, like, be strong, and like, what does that? Because it's so I love the specificity of that. Because then you just name for me, like three things that come to mind. If you really want to be an entrepreneur, just be ready that these are the three things that you're probably gonna have to get ready to face. So

Melissa: Yeah, I think my number one thing is, you have to be the person who's willing to keep going when giving up seems like it's the only option. Like everyone that I see that I know, who have achieved some sort of greatness, you know, have brought their company out, like, you know, from the dead. Are those people, like people that are willing to keep going when you're like, why are you still doing that? And then they make it right, like, I want to be very careful with that advice, because I also see a lot of people that don't make it. And I'm a believer that like saying no to things, opens you up to new opportunities. You can't just like hard work does not guarantee success. And of course, you have to know when to give up and be reasonable.

But if you want to be successful, against all odds, you have to be the one who just keeps going when everyone around us is like I would not see her as any lesser of an entrepreneur if she just gave up today because she tried really hard. Right? So I think that's number one.

Number two is I think you have to learn how to emotionally detach yourself from your company. And I'm still learning how to do that. Right? Like somebody writes in support and they're like, oh, this thing sucks. I'm like, you suck. Like they're like immediately calling your baby ugly and you're like, you know it hits a nerve right because you did this right, but you know, just sticking to the idea that you are trying to build something meaningful and scale that solution. And don't let other people get you down or get on your nerves, like people are gonna say no to you all the time. And if you take all of that very personally, you're gonna have really rough days, and the rough days are going to come from not seeing success from the things you're executing on.

So I think the one thing you can do for yourself is emotionally protect yourself, by understanding that you are not your product. What right when someone says no to you, they're not insulting you in any way or your intelligence, they're just saying this product is not for me right now. Or this product is not for me, I can't create value for my company by using your product.

And I think the last thing is, and as hard as this is, and I've had to learn this, also, the hard way is you need to have fun along the way. Like you need to have, like life work balance, this was something I did not have for my first two companies, because I was in survival mode, like for so long that I forgot to live. And I think a lot of people also forget that, like, as you're building your company, your life is happening at the same time, right? People are meeting their partners, getting married, going on dates, having children buying their homes, right, like, just don't be one of those people that say, Oh, when I become successful, sometime in the future, when I have all these things, then I'm gonna go and give myself permission to live my life. It's like people that are like, I'm only going to travel when I retire. Well, you don't know what the future looks like, right? And because this journey is so hard, if you don't allow yourself to have fun, and give yourself permission to live and build your company at the same time, I think everything just becomes that much harder. So I guess the number two and number three thing is just, you know, take care of yourself. And the first thing is like, just be relentless.

Analiza: Absolutely don't give up. And number two is, when things feel personal, it's not about you. And third is have fun. I love that. I want to come back to this idea of focus, because you've said it several times. And I feel like that's not easy, right? To really be successful. You got to focus and say no, and I'm curious, how did you always know that? Or did you learn that the hard way? Like, that's a hard thing. It's hard to focus when you put all the eggs in one basket, right? Like even think about diversification of investments, you got to put different eggs in different baskets in case that one basket goes south, you got a basket. But I get that concept. But emotionally, it's so damn hard. So I'm curious, how did you learn that lesson? And how did you put that into practice?

Melissa: So I had to learn that the hard way my first company started as a product company, but it turned into an agency because we suggest to everything, right? Like we had this like beautiful iPad brochure for real estate projects that people could download. We're like, Okay, this is the product. But when you're Bootstrap, and you need the money, you need the contracts. Everybody who sells who is like, Oh, what, but I need this one other thing, oh, but I need this one other thing. But I don't want the thing that the other person has, I want to be different and special. So because we needed the money, I said yes to a lot of things. And before you knew it, we were a custom apps company.

And anyone that's run an agency before knows that that's a super tough business, right? The moment you stop selling, your money stops coming, the bigger your projects, the bigger your team. And then you have to keep the big projects like coming in, right. And that's actually why I bridged my first company into my second one, which was my first like true product company, which was Spacio. Eventually, that was acquired in 2019.

But from that experience, I learned that you have to understand who you want to serve, and the product that you want to become, right. And you have to say no to everything that does not serve the core purpose of why you exist. So to give an example, you know, eWebinar is a webinar automation company, like what we do is we deliver the best attendee experience, right, we deliver the best webinar automation experience out there. And of course, our customers every single day. They're like, Oh, can you have email open rates, you know, the emails that you get when you have a reminder or follow up after the webinar? I'm like, well, we don't do that. So if you want better emails, you have to link this up to your CRM and let your CRM do that. Oh, well, I wish you could have that. So can you add it to the wish list? Well, I'm sure that you want us to be a CRM and marketing email. And you know, social media posts like posting tool like, I'm sure you want us to be all those things, but the core of what we do is to deliver an incredible video experience. So anything outside of that has to give, and yeah, like people cancel every day because we don't have one feature that they want. But the thing is, I know we have 100 other features that they're not even looking at.

So this is actually one thing that you can feel very personal about is oh, that customer left me because I said no to that customer. So that customer doesn't like me anymore. And then maybe you feel compelled to Oh, like, if I build this thing, I'm gonna win this one customer back, let me tell you something if you have 100 features, but they find the one that you don't have, it doesn't matter how many you build for them, they're never going to stay, they're gonna find another one and another one and another one. So I think also understanding that, just because a company doesn't hit 100% of their goals with your product does not mean that they're not getting value from your product, right? So that's something really important to remember. And, you know, saying no to things means saying yes to things that actually serve the core purpose of why you exist.

Analiza: Awesome. Tell me, Melissa, do you apply that idea? Outside of just the core business? Do you apply it to life, even as you live in so many different places? I'm just curious, because it's such a, it could be life mantra, right, like focus, focus, focus, and therefore get the life you want, especially the type of life you live. I'm curious.

Melissa: Yeah, I guess I'm way less disciplined in my everyday life, like in my lifestyle, and in my social life than I am at work, I have to at work, because we have systems, I have a team, we have to grow a company. And you know, there's a way to grow the company. But when it comes to like, just my life in general, like I just try to live every day as it comes, I try to have as much fun as possible. I try not to apply that much structure to it. Because that's like my vacation time. Like I'm working so many hours during the day, that when I'm not working, I just want to wing it.

But as you're saying that I mean, I think it brings up a good point is like I think one of the things that we should all be doing and maybe I should be doing more of is saying no to people that don't serve you. And I think we all have some of those, right? Whether it's like friends by association, or people in your life that kind of suck your energy. I'm not so good at saying no to those things today. But it's definitely like one of those things I've noticed and I want to work on

Analiza: Melissa your nomad lifestyle is, I mean, I don't know many people who have the lifestyle you do usually it's like, if I know someone who does a business and also lives abroad, permanently abroad, or long stints like three years, two years, or someone who takes trips, like I take long summers, and then I'll come back to the states and just share with our audience. What does it mean to be a nomad? What does your life look like? I mean, even this past year, like just give us a glimpse.

Melissa: Yeah, I mean, I think it's way easier to do when you don't have children. So I don't have kids. So I mean, that's by design by choice. My startup is my kid. And my partner, David, who's actually my co-founder to eWebinar, he has two kids, but they're like young adults, like older teenagers that live with their mom in Paris. So four years ago, we left New York to travel full time, like we were paying astronomical rent in New York, and also traveling.

So one day, I'm like, well, for 3500 a month that we're paying for this room in New York, what can that get us somewhere else? Right, because I've always worked remote before it was cool. Like I worked remote like 12 years ago, because we couldn't afford an office like everyone's remote. But you know, I was looking at Airbnb, like looking at, you know, Chile, Argentina, Vietnam, like what we could get. And I'm like, look at these amazing places that we could get for like half the price. And at that time, like these, like New Age storage units had come up, you know, like box and all those things where you would like, put your stuff in two boxes and call back with an app. So just the idea of being able to store a few boxes in New York, come back and repack when we want to. And mostly travel the world became really easy. So we just left New York to give it a try. And then we ended up doing it for three years.

So we just did it, like on a hand carry even. It was like we hate checking in luggage. And honestly, I think about it now. And it's like, probably some of the best days of my life. We ended up finding Amsterdam, like Amsterdam is, you know, one of the best cities in the world, like super high center of living people just want to have fun, like clean water, clean air, it's fairly affordable if you don't make money locally.

So we actually in 2019, when I sold my company, we ended up buying an apartment in Amsterdam to be our home base. Because after three years of traveling and living in someone else's space, you kind of miss having your own space. Like and the thing is David and I have never had our own space, right. We met like in a shared house in New York.

And so ironically, after six months of renovating our apartment and never really living in it in Amsterdam, COVID happen. And like in March of 2020 we had a plane ticket. I think it was like March 18 or something like the day that the lockdowns were announced like that was the last day you could fly. We had a ticket to visit our friends in Hawaii. And David was like, oh, let's just go because we get stuck. We'll just get stuck in Hawaii. We ended up getting stuck in Hawaii for four months, and then we had to leave the US so then we went to Vancouver for three months and then we were stuck in hell Congress of a month. So the ironic thing is, we were so sick of traveling that we found an apartment to be in Amsterdam. However, because of COVID, we didn't go back for a year and a half.

So, yeah, and then, you know, in the past year, I think traveling has gotten much less affordable than it used to be. So even though you know, we do travel, we travel very differently. So before it was like, let's go to my Mondo, choose a cheap flight, find an Airbnb and see what we can do and then see what the next destination is next week. But now it's like, Okay, where can we go that maybe we have, you know, a friend's place we can sublet, or a friend spice we could say at, and how long can we stay there. And you know, so we have to be a lot more mindful, because the world has just gotten way too expensive.

Analiza: Melissa, one of the things that you have mentioned besides being a nomad, startup queen, is that you also have tips on running a company on autopilot. And I know that you run a product company and for our audience, there's different types of companies that they lead. I'm curious, what of that running a company on autopilot? Can you share with the audience? Maybe not including that your partner is your co founder, but any other you know, kind of tips about how to do that, that we might be able to take and learn from you?

Melissa: Yeah, I mean, I think a nice little backstory is why I'm even building eWebinar in the first place. Right. So in my previous company, we were already nomading. And my previous company, I was also Bootstrap. So I was everything except for code. So anyone that's sold, you know, especially business software before knows that when you sign a contract, that's the first day with your customer, that's the first day of the rest of your life with that customer, you need to onboard them, train them, there's feature updates, feature releases, they have a huge team, lots of employees, you have to train them. And you do that through webinars, right. But when you do a live webinar, nobody comes to the webinar, because they have better things to do.

So I was the person because I was everything except for code, doing all those on boardings, and demos and trainings. But all those were exactly the same. So I would be 4am in Kyoto, going to the hotel lobby, and doing a webinar that I did three hours ago, I felt like I spent a decade earning this freedom. But now my whole schedule was tied to my customers demos, which didn't make any sense. So I had always envisioned this product that would do my job for me. Well, I could just go and have fun, right? I want to stay out, I don't want to get up at 4am. Like I don't want to do the same thing over and over.

So that was actually the first idea of eWebinar. And I thought one day if I'm not doing this anymore, like this is the problem that I'm going to solve because it was hindering the way that I wanted to live my life so much that I know other people were also living that pain. So I think a lot of people think that if I work harder, if I work more, if I'm more productive, then I can be more successful. I'm a huge advocate for working less, and finding more creative ways to work, right? When it comes to doing things on autopilot, right? Do you have to have every communication in real time? No, right? In fact, having asynchronous communication, whether it's text or voice notes, or video is something that we already do in our everyday life with our friends and family, on text on WeChat. Why can't we apply that to business? Right? Why don't we be more efficient, like especially nowadays, we're all on our own timeline.

And so your webinars just kind of a product of that, right? It does your job for you, we turn any video into an automated demo, onboarding, or, you know, training session training webinar. So you can run 100 of them every single month, and never actually have to be there to run it. And a lot of people think, oh, I can automate my workflows and my processes so I can be more productive elsewhere. Like, I don't think that's true, I think you should automate as much as you can. So you can go and live your life. Because that's what it's about.

Analiza: I mean, Melissa, that idea of automating beyond business is so key automate even your outfits, right just to have the your basic outfit picked out and throw things on breakfasts, your team rituals, like as much as we can pull out of the thinking so that you can have one more fun, but then to leave the work time for creative thinking, collaborating, problem solving, the better.

Melissa: I mean, I think there's a lot of like hustle culture that's out there that just needs to die, right? Like there's all this like, you need to work more, be more efficient work longer hours, if you leave work on New Year's Eve, and you're lazy, or you've been out of office, and that's bad. Like I just read that on LinkedIn today. I'm just like, this is insane, that we are supposed to be machines for other people. Right? Like, we don't even want to be machines for ourselves, right? Like if working all the time is what you want and what makes you happy then you should absolutely do that. But don't for a second thing that just because you work more means that you're going to get more at the end, right? A lot of times it means you're gonna get less and it goes back to my original point about like Don't forget to live your life and have fun, right? Because there are so few things in life and work that you can't wait for tomorrow to do. Right. And if you remove those artificial deadlines, right, then you also open up the possibility that you can spend more time with friends and family and with yourself.

Analiza: Love it. Melissa with that. Let's go to lightning round ready?

Melissa: Yep, absolutely.

Analiza: Chocolate or vanilla.

Melissa: Vanilla

Analiza: Cooking or take out.

Melissa: Take out.

Analiza: Climb a mountain or jump from a plane.

Melissa: Wow. Okay, that one's hard. I don't like climbing mountains and I do a fear of heights. But I have never jumped from a plane. So I think I'll jump from a plane.

Analiza: Have you ever worn socks with sandals?

Melissa: No, I think that's illegal.

Analiza: Oh, karaoke skills rated from 1 to 10 - 10 being Mariah Carey?

Melissa: Like negative one. I hate karaoke is like I just find it like so loud and like, offensive. So definitely like negative one.

Analiza: What's a recent look you read?

Melissa: I am right now reading Product like Growth. Because that's what I'm trying to learn right now.

Analiza: You're so studious. What's your favorite way to practice self care?

Melissa: Netflix and chill.

Analiza: What's a good professional development you've done?

Melissa: Professional Development? Wow, that's interesting. Like courses I've taken you mean? Sure, of course. Yeah. Like I think the most impactful thing I've done is take Justin Walsh's course on writing LinkedIn content.

Analiza: What's your definition of a Boss Mama?

Melissa: A Boss Mama? I'm like I've never heard that term before. I think it's just like any other boss. I think it's someone who leads by example.

Analiza: What advice would you give your younger self?

Melissa Kwan 26:45 Put all of your money in Bitcoin.

Analiza: Where can we find you like LinkedIn? E-webinar?

Melissa: Absolutely. If you want to connect with me, LinkedIn is best place. So my last name is spelled Kwan k w a n first name, Melissa. And if you're curious about your webinar, and what it can do for you and your business, it's ewebinar.com. Exactly as it sounds

Analiza: Perfect. And last question, final ask recommendation or any parting thoughts to share

Melissa: Any parting thoughts to share? I would say that if you have the opportunity to work remote, even if it's for a month, take it. Like don't think that you have to do it for a year or six months, like just leave, especially if you don't have any dependents. And because I think like working remote and seeing the world makes you a better leader. It makes you more creative, and it also brings new opportunities that you wouldn't otherwise know about today.

Analiza: Amazing. Thank you so much, Melissa, for your stories. I love it so much. Appreciate you.

Melissa: Thanks so much for having me.

Analiza: Thank you so much for carving out time today to hear today's podcast. Three things before you go. First, if you found it helpful, please leave a five star review. Second, please share with someone else you can share the link and posts on Facebook and say check it out. Lastly, I want to thank you for being a listener and you can go to get a free self care bonus called juice your joy at analizawolf.com/freebonus. Thank you so much.