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On this episode of the ‪@WhatWorked‬ podcast, Tyler Rachal and Mike Wu sit down with Melissa Kwan, Co-Founder and CEO at eWebinar. Are you interested in starting a business? Listen to this episode to learn how Melissa bootstrapped three startups.

We covered a ton of great topics:

• Building a lifestyle company that allows all employees to have a proper work-life balance
• How her hiring process keeps churn low
• Using podcast and personal branding for demand generation

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Transcript edited for clarity:

Tyler Rachal

Welcome back everybody to another great episode of What Worked. We are very excited to be joined by Melissa Kwan today. Melissa I feel like, you're obviously gonna get a chance to give us an introduction, but I think you're quickly becoming one of the most well-known bootstrappers on the internet. I don't know if you feel like that description, I don't know if that's an unwanted description. 

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Mike Wu

Yeah, how do you receive that?

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Tyler Rachal

But when I think of that, I think of you're synonymous with that.

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Melissa Kwan

I love that actually. That was the goal when I started.

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Tyler Rachal

Yeah, like this is all a long play vision that I had. Yeah, when I think of you, that's the first thing that comes to mind is you're sort of becoming one of the most prominent voices in  the bootstrapping community. But we're very excited to have Melissa on. She's the founder of eWebinar. She's done a ton of podcasts too. So we're fully expecting her to be a pro today. But Melissa, if you don't mind giving a quick introduction, maybe you're more than a bootstrapper and you want to share a little bit about yourself and I guess your journey so far.

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Melissa Kwan

Cool, well, thanks for that introduction. Yeah, I'm Melissa Kwan. I've been in startups for almost 15 years now on my third startup right now called eWebinar.I had two other startups in real estate tech for about 10 years, running eWebinar for five years now. And what eWebinar does is we turn videos into webinars, so you don't have to do them over and over again. So think of things like demos, onboarding, training sessions that you wish you didn't have to do over and over live. We turn a video into that. So you can do them 24 -7 for customers anywhere in the world. 

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I am a bootstrapper, but I am also an almost full -time digital nomad. So kind of cheating on that because we have a home base in Amsterdam, but we're rarely ever there. But in theory, that's where we unpack. And then I think now we probably spend like 11 months on the road.

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Tyler Rachal

I've got a question off the jump here. What is it about, you're probably the fifth or sixth person that I've talked to that has a home base in Amsterdam. What is it about Amsterdam that calls you? Love for cycling around town?

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Melissa Kwan

Well, it's definitely not the weather or the food, but they do throw incredible parties. And we actually, David and I left New York, I don't remember how many years, I guess, five, six years ago, to travel full time. We discovered Amsterdam because we kept going back for a specific party. So it was like a music community that would throw parties once a month called Gardens of Babylon. And we ended up just meeting more friends there that we felt like made it home more than anywhere else. We've both moved a lot since we were kids. 

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So after three years of nomading, we got sick of traveling and ended up getting a place in Amsterdam, but then the pandemic happened right after that. So ironically, we got a place to stop traveling, but then we ended up leaving for a year and a half. And after people could travel again, we, you know, we tried to spend more time there, but I think in the end we just like being on the road. Yeah, now we use that as a home base for the summer, but we mostly just go to fun places or warm places in the winter.

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Tyler Rachal

That's cool. I'm a music lover. What is Gardens of Babylon?

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Melissa Kwan

Yeah, it's more like house music. That's very prominent, I guess, in Europe. So it's more like deep house, melodic house, not techno. But now they actually have a lot of people that play instruments and sing and do live acts along with DJing. So I think that's kind of the new fad.

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Tyler Rachal

Yeah, definitely. I think Fred Again, I put him in that category. I feel like he's house plus the singing and a little bit of instrumentation too. That's super cool. And I guess one thing that I figured we jump right into, Mike and I are a big fan of what we call the more relatable stories about becoming an entrepreneur. And I think in listening to you on other podcasts and following your journey on the internet - we've never met before, by the way, formally, this is our first time meeting on this podcast, which is really cool. 

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But, I feel like you have one of those more relatable journeys. And what I mean by that is you're not, and I mean this as respectfully as possible, you're not a Sam Altman, you're not one of these kind of prodigy wunderkinds, scratching the algorithm on your dorm room window. Would you mind sharing a little bit more about your nine to five life and your first forays into entrepreneurship?

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Melissa Kwan

Yeah, I definitely think we are the majority. I think bootstrappers are the majority, but we just don't get the spotlight because it's not that interesting and it doesn't sell ads. Sam Altman, however, does. 

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Tyler Rachal

Sure.

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Melissa Kwan

Yeah, but even when I had nine to five jobs, the last one I had was at SAP like 14, 15 years ago, I was always dabbling with things on the side, but not super seriously. Like I would try things on the side with my friends, but didn't really know what that meant because my parents are not entrepreneurs. I just didn't really have an idea of what that meant to start your own business. But I was always fascinated with people who were from those families, especially as a teenager and in your early twenties, I'm always like, what are they doing? Right. 

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And I guess the last job that I quit was SAP and I just hated the corporate environment. And that was the largest company I ever worked for. Previous to that I had nine to fives, but with smaller companies where I could still kind of like call my own shots, be my own person, be creative. But when you're in a big corporation, all of that kind of goes away, right? Like you're not really measured by what you do, I guess. Like you're kind of measured by managing up and who your managers are and making them like you and getting a good list of accounts. And then you can make some money from that.

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So it was just a world that I didn't really understand and I really hated it. So I walked out of there thinking I was ready to start my first business. I think I was 27 and had no idea what I was going to do. I just wanted to start a business and I didn't even know that a tech business was called a startup. It was just not a big thing and I was in Vancouver at the time and there was no startup weekend or coworking spaces. It all kind of came up in the year that I had quit.

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And it was just like go to meetup.com and once a month, you would meet at a restaurant and then you would talk about your ideas, right? So that was when I quit my job. And then I realized that if you build a tech company, that's called a startup. So that was kind of the initial parts of my journey, but I didn't quit because I had an idea of a thing I wanted to build. I just didn't want to be working for someone else anymore. And I wanted to do something else on my own and I felt like I was ready. But in hindsight, I wasn't. I should have, I guess, done a bit more research. But sometimes, you need that naivety to be able to do something else and take that leap.

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Tyler Rachal

Couldn't agree more. I think that the whole being ready thing, that was on my mind a lot. And to be honest, meeting Mike and having a co-founder, that was the thing that allowed me to take the leap. But as I look back on it, it's wild when you actually become an entrepreneur, how much you learn every single year. And I always think back to when we started, we really knew nothing, when I think about what we know now. 

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On that note, do you ever think about, because as I understand, was your first business the agency where you were basically developing? 

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Melissa Kwan

Yes. 

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Tyler Rachal

Do you ever think back to that time and think what would you have done if you started a company with what's available today? So when you think about newer trends, no code, low code, right? You wouldn't need to be a developer to build things. Or potentially you do you be one of these people online selling courses or that sort of thing. Do you ever think what you would do differently if you were given what's available today?

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Melissa Kwan

Yeah, I mean, it depends what is available to me in that scenario, right? I mean, would I start the same company again? Probably not. I think I could say that about every company I've started. Would I start a eWebinar again? Probably not. Like I just wouldn't start another tech company again. Like, and I've said that many times, but I think when you have a dream of something, it's always better than actually executing that dream. I also don't believe that I could have taken a shortcut because my parents were not founders. I didn't really know what a tech company was. I didn't really understand what it entailed to hire developers to build something. Like I was so green that I thought there was only one language for code and there was one path to get to an outcome.

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Tyler Rachal

Sure.

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Melissa Kwan

Like if I wanted to build a website, I would get a website. But I didn't realize that there's different qualities of a website that you can get based on the developer that you hire. So all of that was like learned and I needed to go through that to learn what I know today. So if I didn't have an agency, I wouldn't know that I don't wanna build an agency. And if I didn't have that agency, I wouldn't have discovered really real estate tech and prop tech in that whole industry and started traveling to New York. And then I wouldn't have moved to New York and I wouldn't have met my life partner who is now my CTO. And then I wouldn't have eWebinar in the way that I have today. So of course, I would make a lot of decisions differently, but I still don't think that my journey could have been much different because I needed to go through all those things.

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Tyler Rachal

Yeah, absolutely. Mike and I have an agency, so I think this all resonates a ton and I think there's this myth with doing a startup where you're supposed to say, this is my life mission and I love this. And it's kind of funny because I think about people that are like, you know, back when we had the toilet paper shortages during the pandemic, right? 

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Melissa Kwan

Yeah, that was ridiculous.

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Tyler Rachal

That was ridiculous. And people were like, I'm building the greatest bidet ever created, right? And they're like, I'm just really passionate about toilets. And I'm like, you're not, you're just, know, like a Stanford kid that had some type of engineering background and you're able to put together this product fairly quickly, looks cool, and you marketed it well, but you don't have to love that. So I totally resonate. Mike, you look like you wanna ask a question.

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Mike Wu

Yeah, Melissa, one thing that I just want to say thank you for is how you've documented your journey and you share your learnings almost it seems like in real time, on how you're growing the business and just growing as a bootstrap founder/CEO as well. And we're talking about this theme as like learning from this business to the second business to eWebinar. You come from a sales background. You said 14 years ago, your last job was at SAP doing sales.

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You've talked about how you learned, you're learning more about go to market, sales and marketing, product, that sort of thing, operations. As a bootstrap founder, I'm asking for myself honestly, probably Tyler too, but I'm curious to know how you have thought about your personal development as a founder CEO over the years. If you've kind of gone the route of trying to be very well -rounded, wear many hats, or how you think about being T -shaped, I guess it would be called, and going really deep in certain areas. Do you have any reflections on that, what you've done, if you'd do anything differently around that, and how you're thinking about doing that going forward?

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Melissa Kwan

I mean, I don't think I ever had the luxury of choosing. I've always just worn many hats and then we always run really small teams. Like my goal is not to have the biggest company possible, right? My goal is to have the smallest company possible with the most capable people that are hopefully the highest paid. That's my goal. When I read about companies having like a hundred people, that's a bad thing for me. That's like my nightmare. 

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So what I do now because I do have more people on my team now than I ever had at Spacio, is I try to hire people for things that I'm really just not good at. But I do recognize that every time we have made a mistake on hiring or investing in something, it's because I try to pay someone else to take away a pain that I don't understand.

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So for example, right, like we've hired so many different marketing agencies that didn't work out, but it also didn't work out because I didn't know how to interview for them. And therefore, hired people that were just not at our stage. Right? Like if a company says, we can do what you want us to do and I'm like, great, here's a retainer. Of course they're going to take it, right? They're never going to say, well, we've never taken a company from zero to one. And then we don't realize that until months later, and then we have to do that again and again and again. 

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So I think what I've learned now is like, I at least have to learn a bit of it and have some context. Either it's myself, my co-founder or our COO, which is basically the third co-founder. And then we go and take our knowledge to try to hire someone that can do that job. So I don't try to do everything, especially for the things that I just really, really hate doing. But it's really important to me that either myself or some other executive on the team has a basic understanding of it before we go out and try to hire for that role. 

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And when we do that, we've made a commitment to only hire senior people because of the nature of our company. The nature of our company is it's remote and everybody's spread across the world. And so you have to be of a certain place in your life to appreciate the benefit of that. And you also have to have a certain level of experience and seniority to be self-motivated, know exactly what to do. And we don't have to micromanage you.. The problem is because we're such a small team, the moment someone else has to micromanage you, you're taking away from them and you're not adding to them. And we just can't have that because we run such a tight ship.

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Mike Wu

There's a lot of clarity in what you're saying. You know exactly what you need. And obviously you've learned through experience and trial and error, but are there certain core principles or values that you've created for eWebinar? You're saying, hey, we're remote. That's one thing. But also, it sounds like you have some goals that you're trying to attain. Pay people high wages, I think you have certain revenue goals too, I don't know if there's a time horizon on that. But are there certain parameters that you've set that the company understands and then it helps you make decisions like this on who to hire, at what level do we hire and that sort of thing. Do you have those like written out? Do you follow an EOS or something like that that a lot of companies use?

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Melissa Kwan 

No, we're definitely way too small to have no systems. It's all in our heads. But, you know, we can only hire people in countries where we can afford. So we don't hire from North America mostly because we can't afford them, but also because it's just a different work culture, right? A lot of people in the US and Canada might always be looking for the next best opportunity. And for us as a bootstrap company, not only can we not afford to compete on wages and salaries and benefits, training costs is really high for someone like us. So when someone leaves, the pain is really felt. And that's the kind of conversation we have with people, no matter what country they're from. And I share past experiences where we did try to hire from North America and we've told people, if you leave, if you don't take us seriously, if you're looking for another opportunity or if you treat us as a stepping stone, we're gonna feel the pain. So if that's what you're looking for, do not take this opportunity. And people acknowledge that, but three months later, they're like, yeah, I'm just gonna go somewhere else. And then it turns out they've been looking for a job since month one and never shared that with us. And that's really painful. And so what that does to us as a company is we have to hire from countries we can afford, and then we have to pay them more than what they can get on the open market.

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And the thing is we want a lifestyle company and what that means for me is I want everybody involved to have a great lifestyle. So paying someone the least is not something that I optimize for. One of my favorite questions is to ask somebody, at the end of week if we want to hire them, then I asked them, what is a salary range that you know, you would consider high for your role?

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Like what is something that you can make that could give you a good life where you are within what you're able to contribute? And they'll give me a range. I ask that because I want to know if we can hit it. That's the reason for that. If not today, then what is the probation period? So that's more important for me that if people are giving us their time, we're giving them the life that they could get with us and not elsewhere. And that's how we breed loyalty, but also motivation. And like people feel really connected because they feel like we care about them. We're not just saying we care about you, right? Because it's such a small team, I know where everyone kind of sits, but that also means that if you don't deliver because everyone's so visible, then you're not really gonna last. But for us, we don't have a lot of churn in people because if the attitude just doesn't really fit the culture I'm talking about, it's really obvious within the first month or two.

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Tyler Rachal

Wow. This all resonates. Mike and I are both smiling and nodding vigorously. You know, I think with Hireframe, there's this notion that our value proposition is just, we're working with mostly North American companies and we're helping them typically save a lot on certain roles. But to your point, what I really find the value is for our customers is that now with how competitive things are, I don't care if you're a bootstrap company or if you've actually raised a lot of venture funding. Venture capital is not around every corner anymore. We're well past the zero interest rate period. Who knows if those days will return or what they'll look like when they do. 

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But companies are really being forced to allocate very, very specific budgets for certain roles. They just can't pay beyond that. And that's where I see, to your point, it's less about moving these jobs from places like North America or parts of Europe where it's more expensive in the labor market. It's more about, I just look at that simple equation. You are not going to be successful unless you're able to provide a competitive salary. Otherwise the person's just gonna eventually leave for a couple thousand bucks at another place. And so it's really about finding that because churn to your business and I think for many others is just so impactful. It really, really hurts you, especially when you have, I imagine at eWebinar for most of your hires, they're managing entire functions versus being part of like a larger team of everyone doing the same thing. Is that kind of fair?

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Melissa Kwan

Yeah, absolutely.

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Mike Wu

We're kind of on this topic of hiring folks in different countries, working for a remote company, but all working together. And there's different kind of threads here that are going through my head, cross-cultural communication, values, work styles, that sort of thing. And then Melissa, maybe come to wWebinar. I'm curious to know what, if someone joins eWebinar, what does that

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onboarding look like? What eWebinars do you guys have set up for them as they're coming through? We think a lot about onboarding. It's something we're kind of overhauling today to really make sure that our onboarding program is being worked on because that has a lot to do with the employee experience, their first experience with Hireframe. So I’m curious to know how you use eWebinar at eWebinar.

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Tyler Rachal

I was gonna say, it also sounds like you do a great job of expectation setting. So I'm curious about what you say to someone, hey congrats, here's your offer. Now here's what to expect, I'm curious what you say.

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Melissa Kwan

Yeah, I guess everything is just so informal. We're just like such a chill company. Like the thing is all of us hate calls. We have like one call a week between five people that are more of the execs of the company. And I don't think anybody enjoys that call. 

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Mike Wu

Can we do this over email?

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Melissa Kwan

Yeah, like we're just all in different time zones, people are kind of living on their own timelines all the time, right? And so for onboarding for eWebinar, think when it comes to product and learning the product, David, who's our CTO, he's got a couple of eWebinars where he just walks through the product. Like every single page, this is why things are there. Because it's really important, not just for anyone to understand like, here's how I diagnose this issue, but it's been three and a half years since the product's been live on the market. The company's been around for five years. It took us a year and a half to build the product. But it's really important for everybody on the team, no matter what function you're in, to understand why is a function there? How do people use it? How do they use it in their business to get success? Why did we move this over here? Why do we have this scheduling? Why is a button moved over here? When they have integration issues, what are they trying to do in their business? Not technologically, what are they trying to do? 

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So I have David just do like really deep walkthroughs of the product in this way, right? Kind of like injecting business sense into it. Because that's just not something he wants to do like multiple times. It's also not something I can do because he's really talking to the product people and developers. Like these are the majority of people that we hire.

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And if there is turnover, we hire developers to a dev shop. So while they are remote, the dev shop has an office locally. And if somebody doesn't work out, then they bring in someone else and we don't actually do the hiring, they do the first level interview. But we get to say yes or no, but at the end of the day, that's the only people who we have turnover on. So when they come in, they really just go over the product-based eWebinars to really understand why people use what we create. And I think that makes it easier for them to understand why they're building certain things and why they're spending time on certain things. 

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Outside of that, for customer success, we've got our guy who heads that, who just has notion docs of frequently asked questions, how to diagnose those, where you go. I'm actually not super sure if that's up to date. I think it should be. But we also try to make it as hands-off as possible, right? Every month we figure out, okay, what are people asking the most? And then what are the help articles that we can write to reduce that? Because everything that we do is to reduce work and lower burn, increase revenue. And one of the things that we can do to make people's time more efficient and effective is to make as many assets hands off as possible. So a lot of our time kind of goes towards that. And frankly, I don't manage anybody. I know that I'm not a good manager. So I know what's going on with product because David's my CTO and also my life partner, so I always know what's going on. And I think at this point, the product's kind of grown beyond my personal understanding. There's so many things in it that I'm not using anymore on a daily basis.

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And then Todd, who's my COO, he's like a jack-of-all-trades guy and he also manages all of our digital marketing, all of our content and he's like our PM. And so the people that we hire around marketing and content are actually under him because they were hired to take things off of his plate. So I really just work with our COO and our CTO. Luckily, it's kind of designed that way. So if there's any kind of onboarding, it actually goes through the two of them and I just make sure that people are happy they're being communicated to. I think David runs into this, because developers are just more introverted to begin with. I think he gets into this mode where he doesn't talk to anybody. But it's also important, I guess, for me to remind him, like, if we have new hires, if they report to him that it's like, maybe a nice thing to just reach out and make sure they're still there and make sure they know that they're being cared for. And as far as what happens when we give people an offer, it's super easy. David has a conversation with them that's more technical based. And then I have a conversation with them around expectations of working for a lifestyle business that is not a typical tech unicorn. So the things that we're talking about, right? Like you can enjoy the benefits of being remote, but you also have to show up with something breaks on the weekend.

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Tyler Rachal

Sure.

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Melissa Kwan

And we try to make sure that people have their holidays, they take their me days, that they're not working on the weekends. But if you are the only person who can fix it, and that doesn't really happen a lot, but if you are and you don't respond because it's the weekend, well then you can't have both. And that's the conversation that I have with. So I have to gauge like, and also the conversation they have with me is more around their own priorities, as a human being. So I ask them for example, what are the top three things that you care about in your life? So some people would be like, family, or spending more time with friends, or I want a remote job because now I'm spending two hours a day traveling to an office. So I kind of have an idea of how much do they value a role specifically with us? Because we can't give them the highest pay. So I have to know is there anything else we can offer them in exchange for pay? Right? So if Amazon comes knocking on their door, I gotta know that they're not just gonna leave without having a conversation with me. 

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And there's been one case, very recently actually, where the guy, no matter how I position the question, he did not care about anything except for money. And he actually came as a fairly high recommendation from someone who's worked with him in the past. But then I just told him within 10 minutes, I can't even dive into this conversation because there is absolutely nothing I can offer you that's gonna make you happy. And I even asked him if somebody came in and offered you a high salary, would you leave? And he was like, yes. I'm like, well, then we have nothing to talk about. And that's okay, right? Like he knows his priorities.

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Tyler Rachal

Points for honesty but I totally get that I think there's this notion too during these conversations that it's like as the founder you're sitting on some budget that you haven't really made available to them it's like they could pay me more when in fact, I really appreciate your perspective on this because it's not just a function of could you do it it's like would that be a good situation for either party, right? You give someone more than you really can and then there'll be kind of unfair expectations on them as far as the value creation they could do for the business.

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Mike Wu

I wanted to ask one question about this topic, You seem to have your talent acquisition quite dialed in. And I think for any small business, especially bootstrapped, but even venture backed startups who don't have a brand yet, maybe it's a first time founder, it's hard to attract high quality talent and convince them to join your company aligned with your mission and your values. And so you mentioned comp is something that you can't offer the highest comp. So for the folks that you are trying to attract, what are those things that you can offer or that some of your team is drawn to at the eWebinar?

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Melissa Kwan

I think talent acquisition will always be tough for any company, regardless of your brand, unless you are, you know, a Facebook or Amazon, people really want those benefits and you pay a lot or you're a chatGPT and you're the new kid on the block, right? Like it's going to be a challenge for everybody. But what we can offer, all things being equal. First of all, I don't think salary can meet that far off. Like you can be a little bit off, but like not like 50%. So, which is why we need to look elsewhere. But what we can offer are, you know, things like agency, right? You manage your own time, there's no vacation policy. And we don't say that because we think, you're not gonna take any vacations if there's no vacation policy, right? I've seen that written up as well. But we encourage people to take your me days. If you want to take Friday off, just let people know that you're not there. Don't just disappear. But also, you can be remote. You can be anywhere. And we don't just say that. We show them that by living the life that we live. When we go to Burning Man and we have nine days off, or when we're traveling somewhere, we don't hide that from our team. 

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We try to lead by example. As long as within reason, no one's taken that out of context yet. But also things like we don't do calls, there's no meetings, you just deliver. There's stuff on a board. You pick them up, you do them. The customer always comes first, right? So if something breaks, it relates to a customer, you got to fix it. And you just perform and you basically give us your deliverables on time. You hold yourself accountable to the things that you're given and everything's good. But that's it. And it doesn't sound like a lot, but I don't think a lot of companies can offer that. We don't micromanage ever. If we micromanage, you're gone.

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Mike Wu

I think it's very rare. I think to create this culture and actually uphold it I think is more challenging than the traditional, hey, I need you to clock in at nine and I need your time card. I think that's easier to do than what you've created with this culture of accountability and agency.

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Melissa Kwan

Yeah, and when we hire from places like Turkey or the Philippines, their average salary is not very high. So we try to pay above that fairly quickly. And in some cases, double, triple, or even quadruple that. So if somebody shows up and they actually do what is expected of them, we very quickly increase their pay to show them hey, we appreciate you, but this is also money that I would be spending in North America if I were to hire for the same role. So in theory, we're like both getting a deal, but we don't have a thing where you have to be here for a year before you get a salary raise. Like, you know, the guy that we hired that finally took over customer support, like this was the role that we literally could not hire for, which meant that David, COO, and myself were sitting in support until last year. And as soon as he came in within the first month, we gave him a bump. Two months later, we gave him another bump. Three months later, we gave him another bump, right? Because the value we were getting from this guy was so high that we wanted to make sure that, you know, he's going to stay. And there's no way that he's going to get another role locally at least, you know, because he's, he's also quite junior. So I think like having that like they have job security but like we also have job security because if he leaves and it's a huge impact on us

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Tyler Rachal

Absolutely. I'm picturing you two having to answer support tickets while at Burning Man while there's some sort of like late night rave going on behind you and you're trying to help someone  work some feature. 

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Mike Wu

Recover their password.

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Tyler Rachal

Yeah, exactly. I think password resets are a thing of the past officially now. That'll save your Burning Man experience. But I am curious, you're very thoughtful. That comes across immediately. How do you think about structuring your day? And how does that align with what is top of mind and highest priority right now for you at running the show at eWebinar?

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Melissa Kwan

Yeah, I mean, I don't have a structure. There are things that I need to do. And I use Monday or our whole companies on Monday. It's kind of like a spreadsheet style to do list. There are things that I know I need to do. And I don't really have issues with self-discipline. It kind of just gets done. 

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But what I don't like is structure. So I'm a late owl, I get up at probably 11 or noon every day, but I don't get to bed until  two or three. I don't get so many hours in at a time, but when I'm around, I'll be doing stuff and if I want to go out for lunch with a friend or if I want to go out for dinner, then I will. The days where I have to work at night now are kind of gone. I don't really do that anymore, but I'm always there when somebody needs me. Like if I'm blocking someone, then that block needs to be removed. And I think David is also the same way. Obviously this is an earned privilege because we are kind of where we are today, but we put on a lot of front load work to get to where we are. But I think the key for me, because I'm not a structured person, is having no structure. And if I don't want to work on Friday at all, then I'm not going to do it.

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Tyler Rachal

Yeah, it goes back to your intentional decisions around lifestyle and not taking on venture funding, bootstrapping and getting to this point. I am curious because as I think about your background, right? You started off agency and eventually got yourself into becoming a product founder. If I'll play a little hypothetical here, let's say Melissa the product founder is at a cocktail party with Melissa the agency owner. I'm just kind of curious what you feel like an agency owner would benefit from learning from someone who's a product founder and vice versa. Just curious what your answer is, because there's some things that I feel like you've picked up from both experiences that I think are highly valuable at the other.

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Melissa Kwan

Yeah, I mean, I think every agency owner wants to be a product company, is that not a universal truth? Yeah, I mean, I think agencies are hard, right? Like it's, you know, you're always chasing a new deal, chasing the invoice. Nobody wants to pay you, right? It's never net 30 days. It's like net 300. And that's why I personally got out of it. I really don't know a lot of companies like friends of mine that have successfully transitioned from an agency to a product. Everybody's tried, but I know one company that was able to successfully do that. And then the CEO also removing himself from the agency and that took like years. 

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So I mean, if I knew back then what I know today, I think I would have experimented more of my own products on the side. And I would have tried to make mini products out of the stuff that I was building for other people and see what I was like what I could productize and then see if I could spring up like like micro SaaS companies kind of on the side to be able to float myself and my co-founder while we like wean off the agency, which is which is I think what a lot of companies try to do. But ultimately, it's just super hard to build a product company if you're not a hundred percent into it. Cause it's not just the product, right? The product is like one tiny piece of a whole business. And at the end of day, it's also mind share. Like if you're running people, you got to run the agency, you got to build stuff, you got to close deals, you got to chase invoices. Like you really don't have the mind share and the energy to put into a brand new business. So while I know that I should have done more of that. I'm not sure if that would have been possible because what I did in the end was I took the revenue in my previous business, I took a loan against it and that was my startup capital for my second company. And that was how I was able to not take contracts for the amount of time that I was building the new product.

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Tyler Rachal

You're able to give it its proper focus. Do you feel like there's anything though that you took from your agency background into now being a product founder? Things that as you have peers that say have only been product founders, maybe things that you personally don't have any struggles with, but they struggle mightily with. I'm just curious what your take is on that.

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Melissa Kwan

Yeah, I guess there's not really, the two businesses are just so different, but what I was able to take from my agency business, because we were building applications on the iPad for real estate developers. I was able to use that to get into real estate conferences, getting to know like the property tech startup founders, and then understanding what it meant to build a product within, you know, within the industry.

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So I didn't really learn how to run a company better or how to build a product better, but I think a lot of agency owners, and I could be wrong on this, are quite isolated. There's startup events that a lot of startup founders go to, but you very rarely run into agency founders. They kind of see themselves as a different business. And what I think my greatest benefit that I got from my agency was I just went to all the startup events, also particularly in that industry. And I was able to build a product in that industry and sell through a lot of my friends because of that experience.

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Tyler Rachal

Yeah, agencies are a lonely existence. You're absolutely right. It's actually something that I've made a goal for this year, I have now been reaching out to every agency owner that I see, even regardless of sometimes they're direct competitors, just because I find that every conversation I have, it's, it's, it's enlightening. There's something that they figured out and they're just not really sharing it with anyone. Because I think to your point, there's not these kind of built in communities that are easy to access. You as the agency person too, I don't know if this was your experience, but it's when you, when you walk in the room and you're the agency person, you kind of stick out. Everyone's kind of like, are you trying to sell me on something? Cause usually you are right. 

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Melissa Kwan

Of course, always.

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Tyler Rachal

And so I remember I would be in many awkward, you know, like founders dinner type events and everyone's like, I'm disrupting, you know, healthcare. And I'm like, I'm here to sell you something. So totally get that. But I do find that, that when you do actually talk with agency owners, it's hugely valuable. And it's a shame that more of us don't kind of get out there. I also think too, that there's this element of agency life where there's always a fire. And I think so often you just, you feel like if you don't constantly make yourself available to put out those fires, then your business is going to go under. So I think there's that part too. Mike, it seemed like you wanted to ask a question.

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Mike Wu 

Yeah, correct me if I'm wrong or reframe this, but we talked about your agency life, your tech product life, are you also building a media empire? It kind of seems that way with the podcast and then with your founder next door, you write a ton on LinkedIn and maybe that's so there's some crossover with your newsletter, but what's your what's your strategy around or you know your plan with the media, the content stuff that you're doing? Do you consider that different, is that the third leg of the stool here?

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Melissa Kwan

I mean, that is all kind of demand generation for  eWebinar, right? I gotta be super scrappy. Like we don't spend any money on marketing. I think we spend like less than a thousand bucks a month, just on retargeting, just trying to own the audience we already know, or that already know about us. We don't do anything on top of that. So there is no other way outside of building a brand for myself, writing on LinkedIn, doing newsletters, writing content, also SEO. I don't write the SEO content, someone else does, but that's just kind of another channel. There is no other way to get people to know about us.

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Mike Wu

Yeah, and so you're thinking very top of funnel, just like, hey, we need more eyeballs on Melissa, on me, and then the next click will be the one on eWebinar.

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Melissa Kwan

Yeah, I think nowadays, consumer products have already done this for many years, right? Before we'd buy a product and be like, what's the brand name? But now we're like, well, what's the story? Who's behind it? What are the founders? Is it sustainable? We could go and read about it. We don't just go and buy the latest Louis Vuitton anymore. I mean, some people do, but most people are like, what's the story? And then people are sold on the story.

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And I think I'm only starting to see that, I guess, in the past couple of years with technology, right? Who are the founders? Do I know them? Is there credibility? And I certainly don't think that people are signing up because they're seeing me on LinkedIn, but I think they learn about the company because I'm on there and because I'm on there, it makes it more human. I think it makes it seem like, you know, they have a direct channel to me if something goes wrong. It's the closest to like making a friend, I guess. Right? Like reading someone's content, being able to engage them on DMs or on comments is like the next wave of making a friend. Like there's people that I know I'm never going to meet in real life, but I still feel like they're my friend because I met them on social media. Now we're in a chat group, you know, like, so I think it's an interesting shift. 

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Mike Wu

Yeah. Now we're on a podcast.

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Melissa Kwan

For me, it is top of funnel, but it is also a branding exercise for when someone finds out about eWebinar, maybe they'll do some research and then maybe they'll realize that we're a real company and not second guess that. And then maybe they'll try us out instead of a competitor.

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Mike Wu

Yeah, you've built a large audience and you're building it. I don't know if you plan on running eWebinar forever, but I imagine, do you ever think about how this audience could help with the next business and the business after that? Is that the way you're thinking about your content and the audience you're building?

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Melissa Kwan

Well, hopefully I'll never have to start another business. Not because I'm running this forever. Hopefully I sell this for some retirement level cash and I never have to do this again. But you know, what's interesting is like I follow the Codie Sanchez, Alex Hormozis of the world, just to see their content, what they're doing, how they write their descriptions, titles. And what I know for a fact is if you have an audience, you can't fail. An engaged audience, right? And so I don't know what the next step is, but my biggest regret is to sit there and have done nothing for the two years that I was waiting for eWebinar to get built. And I had freshly sold my company. So had I known back then what I know today, I would have just gone on like every acquisition podcast. I would have tried to get onto media. I would have started writing content about selling a company. Like I just didn't know any of that stuff. So I feel like I wasted that time and I only started building an audience when I realized that's what people like me are doing. Only when I ran out of leads to call, about nine months after eWebinar was launched, right?

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So I don't know where this is all gonna take me, but maybe, right? Like maybe this audience will help me do the next thing. But also something I don't think a lot of people realize is like when you're writing, in creating things, you're kind of getting your brain into a different mode. So you start to become also more creative in your business. And I think you're also learning a lot. Like when people engage with my comments, we start chatting, like we start having a side conversation, like, and I now have what I, what I feel like is a pretty good support group of founders where like, if I put a question out there, it gets answered pretty immediately.

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And so these are all the byproducts of writing that nobody really talks about. So it's getting more creative. It's restarting your brain. It's becoming a better entrepreneur, a better manager, but also having a better support group. And all of that comes from putting your name out there and then other people kind of come to you and then, you start to brainstorm other things. So I think that that part of it is more important than building the biggest audience ever that can help me make more money in the future. Hopefully that also comes.

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Tyler Rachal

A lot of times I'll talk to other founders, you have your kind of expertise as a founder, things that you've done in your past that other founders could benefit from. And for me, that's outbound. I've done a lot of sales, but specifically sales like enterprise sales where you're not selling a ton of deals, you're doing, call it 10 to 12 deals a year, but they're large deals. And it involves a lot of like a very high level of prospecting and relationship building and all that sort of stuff and I give any founder that will listen to this advice that needs to get into that I give them the same tip I say pick a timeline, ideally 90 days, take 90 days and write five cold emails a day to whoever you deem to be your core customer and it has to be completely try not to do the copy and paste templatize thing, try to really force yourself to write five different emails. 

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The unexpected benefit that you get from that is it is forcing your brain to think creatively about your business. You question every word because that is all you have to capture someone's attention. So every single word has major meaning and potential. And it's just this incredible thing that I find you realize those values and benefits in other parts of your marketing where you start to describe your business better on the website because you  put yourself through those mental hurdles, if you will, which it sounds like you're doing that, but you're, you're doing it publicly, is that fair to say?

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Melissa Kwan

Yeah and I think because we're remote and I don't have people around me, it's hard to get inspiration. So when people interact with a post or my writing, my articles or they just send me a message, it makes me think about other things that I could either write about or execute. You know, so I think that's also kind of a byproduct that I have is ideas come when I interact with other people, smart people. That just doesn't happen when I don't do those things.

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Tyler Rachal

Totally. I have a question. This is a personal question for you. I'm curious. You use the word digital nomad. In just listening and preparing for this podcast and doing a lot of research on you, what would you say your community is? If you were to walk into a room of people, where do you feel like you belong and where do you feel like maybe you don't belong? In the nicest way, I guess.

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Mike Wu

Yeah, let's all take five minutes and label ourselves.

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Melissa Kwan

Yeah, that's interesting. Yeah, I don't have any friends in startups. So my social circle in my life, actually very few people really talk about what they do. There was a time in my life where like all I had were startup friends, but it was just a function of where I lived. I spent three years in New York. I wanted to build my business. I wanted to know people in the industry. And then all we talked about was business, and it was just so tiring. Like it got really tiring. So when David and I left New York to travel, the thing that compelled us to Amsterdam was like work is not a thing in Europe. Like people don't talk about their work everywhere they go. Like what do you do? is not a thing, right? And that was amazing to me because coming from New York, like that's all people cared about. It was like, what do you do? You know, it's a city of opportunity, not so much friendships.

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And so I think just by nature of that, a lot of our friends are people that we like that love what we do. So we do a lot of partying actually. So we go to a lot of festivals, we go to a lot of house music events, a lot of retreats that are kind of around that. So my social circle are just people that like to party. And sometimes, they also have businesses on the side, and, like me, they don't talk about it. So I actually don't know what a lot of my friends do. And I'm sure a lot of my friends don't know what I do, but it's like a very non-American, non-Canadian thing.

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Mike Wu

That's so cool.

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Tyler Rachal

Very non-American. My wife and I, whenever we go to, for example, a wedding, one of the things that we use as a gauge as to if we had a good time or not is we'll talk about if we didn't talk about what we did. You know, that's one of the most refreshing things. We'll be like, and it's like a, it's a byproduct of having really just interesting people that have a lot more to say and sort of talk about outside of just sizing you up for what you do. Now I will say there's that part of that, but I will say hand up. You mentioned New York, I'm from Philadelphia originally, and I am totally like East Coaster, startup founder. I will ask you within five seconds, I'm like, what do you do? Who do you do it for? I'm retraining myself later on in life that that's not so important, but it's honestly what I've done for most of my career.

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Melissa Kwan

Well, I mean, it's so natural though, in this part of the world.

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Mike Wu

It's so normal in the States.

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Melissa Kwan

Like it's just a thing and it's an easy opener, right? But I feel like the people that you want to know, the people that actually help you in your business, they don't wanna talk about that stuff. So the best way is to get to know them socially first. And actually like I like being surprised with what my friends do nowadays, but I will say that within my social circle, a lot of people have some sort of freedom in their time. So maybe they don't have their own business per se, like in the way that we understand, but you know, maybe they're a writer for someone or a photographer or you know, a meditation teacher or a yoga teacher, like something that gives them freedom because otherwise you can't show up for the things that we love. So I think that's probably like a common thread.

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Tyler Rachal

I know we're coming up on time, I wanna be respectful of your time, Melissa. And I'll also say on a personal note, as much as I have enjoyed this conversation, I will candidly share with you that I am so not a partier. I don't know if we could ever be like friends, friends. I think we could be friends like this, but you wouldn't catch me at Burning Man. I'm such a tired person. I would be just sleeping in the camper for most of the weekend. But yeah, I do wanna kind of be respectful of your time and Mike, I don't know if you had any closing thoughts or remaining questions for Melissa.

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Mike Wu

No, I would just ask Melissa if there's anything else that you'd like to mention. And we usually just wrap up asking our guests to plug anything that they like to plug or share how you'd like people to reach out. As you mentioned, you like when people engage.

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Tyler Rachal

Yeah, consider us your top of funnel here, so please.

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Melissa Kwan

Yeah, if you want to connect with me, the best way is through LinkedIn. Melissa Kwan. And if you're curious about eWebinar, how it can help you or your business, just ewebinar.com, and then on my LinkedIn profile, there's ways to sign up for my newsletter and different platforms I'm on. But if nothing else, you know, would love to connect with you and any questions, can just DM me on LinkedIn.

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Tyler Rachal

Or if you see Melissa at Burning Man, you just go up and just in the most friendly, non-aggressive way, just hello, nice to meet you. Let's talk about all things not work, I guess. 

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Melissa Kwan

Yeah. Don't ask me what I do.

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No, no, none of that. Ask you, you know, where are you gonna be? Where's the rave tonight? Well, thank you so much for your time. We really enjoyed it. It's really impressive what you've built. And honestly, just refreshing, Mike and I, when we started working together. We did all these exercises to make sure that we were the right partners for each other, almost like you would do in any other relationship. And we both found that we really connected in this kind of contrarian point of view where we were both like, we want nothing to do with thousands of employees or whatever. 

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Melissa Kwan

Yeah, sounds like a nightmare.

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Tyler Rachal

I mean, don't get me wrong. Billions of dollars would be nice, but it sounds like a miserable existence, honestly. So we appreciate the conversation, Melissa, and we wish you the best of luck. And we'll hopefully send more people to eWebinar very soon.

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Melissa Kwan

Thanks so much.

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Tyler Rachal

Thank you.

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Mike Wu

Thanks, Melissa.

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