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Building a Business Around the Life You Want to Live

Host Jon Penland, 

Entrepreneur Melissa Kwan wants to encourage people to think differently about their life. Melissa joins Reverse Engineered to discuss what elements and non-negotiables influenced her latest venture, eWebinar. Melissa and Jon also tackle the main goals of a CEO and how they evolve as your company grows.


58 minutes



Episode Summary

In this episode of Reverse Engineered, Jon Penland welcomes Melissa Kwan. Melissa has been an entrepreneur for over ten years and within that time has co-founded three companies. She’s currently the co-founder and CEO of eWebinar.

This episode centers on how Melissa designed eWebinar to fit the life she wanted to live by discovering her non-negotiables and focusing on her interests.

She also dives into the importance of founders being able to sell, her definition of it, and a recommended resource for those who may struggle with it.

If you want to hear more about Melissa’s entrepreneurial journey, tune in to the latest episode of the Reverse Engineered podcast.

Key Insights:

  • Design the life you want to live. According to Melissa, we have a significant amount of control over our lives. Every morning we have a new chance to start all over again. She says life design is all about understanding what our non-negotiables are. “I don’t take calls in the morning because that is my non-negotiable. I don’t work in the morning because I work late at night… So what does that mean? It means being honest to your customers about that.”
  • The idea of freedom leads to high motivation at work. Freedom plays a significant role in Melissa’s life, so she decided to create a company that gives others freedom. Her company’s culture is to give people control over their time, as long as they put customers first. “It’s everything for the customer. You can take a week off if you want. But if something is broken and it’s the customer, we need to fix it immediately. So there’s ownership and accountability to the customer, and that’s the culture.”
  • What are the main goals of a CEO? Having been a CEO for around ten years, Melissa shares her point of view of this position. According to her, your only job as a CEO is to make sure the company has money. Whether it’s through fundraising or investing your own money, as long as there’s revenue in your company, you’ve done your job. “You are the CEO, and you make sure there’s money in the bank to make payroll on the 15th or the 30th. There is nothing else that you have to do.”

Today’s Guest: Melissa Kwan, Co-Founder and CEO at eWebinar

Melissa has been a digital nomad for the past three years, living out of Airbnbs, sublets, and hotels. In the past 10 years, she’s founded three companies in industries such as real estate, manufacturing, hospitality, and technology.

Her current focus is eWebinar, a company helping clients turn any video into an interactive, automated webinar that can be set on a recurring schedule.

Episode Highlights

What Led Melissa to Become an Entrepreneur

“I think I was always creative, and I always thought about different ways to make money, but not for the sake of making money. It was always like, ‘Could I create something that somebody else will pay for?’. When I was in elementary school, for example, I would make these little origami cranes or turtles and see if I can get 25 cents. As a kid, you don’t think, ‘Oh, I’m trying to make a business.’ You’re just trying to make this thing and see if someone pays for it. 

I was always a very bad employee. I always jumped through different jobs, and I really hated authority. I had issues following instructions. I had a bunch of odd jobs before I started my first company. I didn’t think to myself, ‘I’m going to start a company.’ I just thought, ‘I really hate this job, and I want to create something of my own.'”

Freedom Means Different Things to Different People

“I think everybody defines freedom differently. Freedom, to me, is the ability to make your own choices at your own will. So where am I going to wake up in the morning? It’s choosing when and what you want to work on without someone telling you. And I haven’t achieved this yet, but it’s the freedom to travel and enjoy certain experiences without the limitations of maybe your finances. And that’s, actually, why I don’t have children.

I guess my idea of freedom is not to be trapped and not to be bound to someone else’s decision on where and what and who you can be.”

The Most Important Question to Ask Yourself When You’re Starting a Business

“If you don’t start with the right question of what kind of life do I want to live and find a business that fits that, you do the other thing. You start a business, and then you force a life that fits into your business.”

If I were to do anything again, I would start with the question of what is the life that I want to live and then find a business that fits that. Because whatever that business is, it’s going to be five to ten years.”

The Importance of Freedom in the Workplace

“What was interesting about what I’ve learned is the idea of freedom is more important than the execution of it. So everyone had the opportunity to work remotely, but they never did. But knowing that they could, prevented them from going to another company, like Amazon, Facebook, didn’t give them the same freedom. 

So we were able to compete as a tiny startup that wasn’t venture-backed with these massive companies because we gave the people the idea that they had control. And it wasn’t like a tactic. It was absolutely authentic and genuine. But what I learned was people need to know that they have control more than executing it.”

I’m Very Aware Of What I Don’t Know

”I’ve always been comfortable delegating. I’m very aware of what I don’t know and what I’m not good at. And I’m very comfortable delegating those tasks out. I almost never do anything I’m bad at. 

But I’m pretty good at a lot of the things I hate as well. I hate projections – I do them; I hate doing documenting – I do all that. I hate payroll, hiring, but I do all that. As a business owner, especially if you’re not venture-backed, you do have that choice to structure the business. But when it comes to getting business done, there are times, if the business is going to be a success, you have to engage in the tasks that need to happen, whether you like them or not.”

The Customers of Today Are Different

“Consumers are king nowadays. So you have to give them information when they want it, at the time they want it, but you still have to make sure they know that they’re heard.

That’s how picky we are nowadays. I challenge people to think about their own buying journey. If you are the customer, which you are because you’re the consumer of something else – when you want to buy a product, how do you want to be treated?”


[00:00:04] Jon Penland: Hi everyone, my name is Jon Penland, and this podcast is brought to you by Kinsta, a premium managed hosting provider. In today’s episode, we’re going to be chatting with Melissa Kwan, founder and CEO of eWebinar. Melissa, welcome to Reverse Engineered.

[00:00:19] Melissa Kwan: Thanks so much for having me, Jon.

[00:00:21] Jon Penland: We’re very pleased that you chose to be with us today. So to get us started, can you introduce yourself to our audience?

[00:00:28] Melissa Kwan: Yeah. My name is Melissa Kwan. I’m the co-founder and CEO of eWebinar. I’ve been in startups for a little over 10 years. This is my third company and a little fun fact about myself – I’ve been digital nomading for the past three years, living out of Airbnb, sublets, and hotels. And I’m currently joining you today from Hong Kong.

[00:00:49] Jon Penland: Awesome. Okay. Three companies over 10 years, how much time has eWebinar been what you’ve been working on?

[00:00:58] Melissa Kwan: It’s been two years now. The product’s been live for the past eight months, but we’ve been working on that long before anyone’s ever seen the product.

[00:01:08] Jon Penland: So you launched eWebinar then entirely as a digital nomad, is that right?

[00:01:13] Melissa Kwan: Yes, that’s correct.

[00:01:16] Jon Penland: Okay. Wow. Okay. Fantastic. So for anyone who may not be familiar with eWebinar, give us a quick rundown of what eWebinar is.

[00:01:23] Melissa Kwan: Yeah. So eWebinar takes any video and turns it into an interactive, automated webinar that you can set on a recurring schedule. We save people from doing the same webinar over and over again, and we help you deliver the perfect webinar every time without you there.

[00:01:43] Jon Penland: Okay. So it sounds like this is going to be then obviously a product for marketers. Do you see other applications like online learning, or is this primarily a marketing focus tool, right now? 

[00:01:52] Melissa Kwan: Actually, that’s interesting you say that because over 90% of our customers use eWebinar in customer success. So I define customer success as anything post-sales. So it could be training, onboarding, upselling. And then close to 10% of our customers are in marketing and sales that use eWebinar to deliver a demo that can happen at any point of the day. But what makes it really makes us unique as a product is we take a video and we combine it with live chat and real-time interactions to deliver an engaging experience for attendees without you being there. So you get the whole idea of eWebinars built around freedom, right? So our mission is to help you get your time back.

[00:02:39] Jon Penland: Yeah, it’s interesting. As you were talking about eWebinar and as I was looking at it a little bit prior to this conversation I was putting on my operational hat going I could actually see a lot of value in this product for, cause as the operational guy, I deal with HR. And so we do a lot of onboarding and training and I was sitting here going – I can actually see some application for this product in that setting where you could deliver information and you could have the HR person there live answering questions, but the training could be automated a little bit. So I can see a lot of different applications.

[00:03:13] So eWebinar, as you alluded to, this isn’t your first foray into launching your own company? You mentioned you’ve launched three companies over the last 10 years, if I caught that correctly. So what led you down this path from the beginning, 10 years ago as you’re launching your first venture, what led you down that path of starting your own company?

[00:03:35] Melissa Kwan: So what’s interesting is I don’t think people decide one day that they’re gonna become an entrepreneur.  If you want to make money, there are many different ways to make money. In fact, if you want to make money, you should not be an entrepreneur. 

[00:03:58] The chances of you failing is actually much higher than you succeeding. And you would know that. Like having been an entrepreneur and also seeing other entrepreneurs trying to launch their business. So I think I was always entrepreneurial but not knowing that because I didn’t grow up in a family that like, my family didn’t start their own businesses.

[00:04:17] My mom was a housewife and my dad worked for the same company for 40 years. Their only hope for my brother and I were just like, we would be an investment banker or a doctor or an accountant. That’s something that gave us a regular paycheck, something they had to work really hard for. But I think I was always creative and I always thought about different ways to make money, but not for the sake of making money. It was always like, could I create something that somebody else will pay for? So when I was in elementary school, for example, I would make these little origami cranes or turtles and see if I could sell them for 25 cents.

[00:04:56] As a kid, you don’t think – “Oh, I’m trying to make a business.” You’re just trying to be like, “Okay, I’m making this thing, and will someone pay for it?” I was always a very bad employee. I always jumped through different jobs and I really hated authority and I had issues following instructions. I had a bunch of odd jobs before I started my first company. And it wasn’t like, I didn’t think to myself – I’m going to start a company. I just thought I really hate this job and I want to create something of my own. 

[00:05:31] It wasn’t certain, it actually, when I look at my parents and how conservative they are, I don’t actually know what led me down this path. It was something that made me think I want to create something, whatever that thing might be, and I wonder if somebody will pay for it.

[00:05:50] Jon Penland: Yeah. Yeah. That’s interesting. It’s funny, the idea that I feel like I’m hearing come through there, you have said a couple of different times something along the lines of, “Can I make something and have somebody pay for it? Can I do my own thing?” And there’s something as I was reading about your philosophy as you approached eWebinar, something that I’ve seen you write a couple of different times is this idea that freedom is my number one priority in life. And actually, I think you already mentioned that once early on when you were introducing yourself. So I wanted to unpack that a bit because I feel like what I’m hearing is that really, that was a driving factor from the beginning. You struggled as an employee because you didn’t take necessarily instruction particularly well, and then you launched your own ventures. So let’s unpack that a little bit. When you say that freedom is your number one priority, what does that look like to you?

[00:06:46] Melissa Kwan: So that’s a great question. And I don’t think a lot of people have asked me that and I think everybody defines freedom differently, right? Like freedom to me is the ability to make your own choices at your own will.  So where am I gonna wake up in the morning, when – it’s choosing when and what you want to work on without someone telling you. It’s the freedom, and I haven’t achieved this yet, but it’s the freedom to travel and enjoy certain experiences without the limitations of maybe your finances or, and that’s actually why I don’t have, I don’t have children.

[00:07:32] Jon Penland: Sure.

[00:07:33] Melissa Kwan: So the idea that like, so my like, I guess my idea of freedom is like to not be trapped, to not be bound to someone else’s decision on where and what and who you can be.

[00:07:45] Jon Penland: So that carries with it a couple of different, I feel like, factors. So there’s definitely a time component there in terms of wanting to have control over your own time. There’s certainly a finance component there in the sense that a certain degree of financial independence is necessary to enjoy freedom.

[00:08:10] As you look at your entrepreneurial journey, usually people do not necessarily associate time freedom with starting your own company, because that tends to be a very time-consuming thing. I am not one of the founders of Kinsta, I joined early on, but I’ve watched the founders of Kinsta, and time scarcity is something, especially early on, that they really struggled with.

[00:08:35] So I’m just curious as you had these different ventures that you started – how did time and the desire to have freedom factor in as you’re starting companies and trying to manage your time and not let it consume all of your time?

[00:08:49] Melissa Kwan: The reality is when you’re starting a business, it consumes all of your time. But it is you choosing the hours of time that it consumes, right? Starting a business means you work more, but at your own time, and that’s really important because when you work for another company, it’s nine to five, nine to six, ten to four, whatever it is.

[00:09:12] And when you’re off work, you’re off work. And for some people that’s freedom, right? The freedom to do more than what you are willing to, right? But for me, like, I want to spend all the hours I can on it, but only when I want to, not because I have to, and that is my definition of freedom. I wake up in the morning, I do a few hours, I take the entire afternoon off and then I start work again from six or seven PM until three or four in the morning. 

[00:09:45] So it doesn’t mean I work less. It means I work more, but I am more energized because I work at the hours that I feel most productive. So how is that not complete freedom? 

[00:10:00] Jon Penland: And I’m curious because, as somebody, again, in the operational side of a business, there’s a lot that is dictated to our company by our customers in terms of timing and availability. Have you made certain choices in how you structure and build your own businesses to try and pull back some of that control where we’re obviously, as you’ve described, you’re working early, you’re taking the afternoon off and then you’re working late into the evening. Are there structural choices you’ve made about this is how we’re going to design this business to allow me to operate it? And what do some of those choices look like?

[00:10:41] Melissa Kwan: So the word design is really interesting, right? So I’ve written about designing your life, where like I believe in life design, right? The idea that like, it is incredible, the amount of, control, it’s amazing. The amount of control you can have over your life if you decide today that I’m going to design the life that I want to live. So what does that mean? It means understanding your non-negotiables. Right? So I don’t take calls in the morning, that is my non-negotiable. I don’t wake up in the morning because I work late at night unless I really want to, but I try to avoid it.

[00:11:29] So what does that mean? It means being honest to your customers about that. If your customer says, okay, can you make it at 9:00 AM? No, I can’t. I don’t take calls in the morning. But it’s having the confidence to say that because at once you are, once you have conviction in your non-negotiables, you make choices accordingly.

[00:11:47] So you can have the conviction to tell your customer – I don’t do this so we can work out something that works for the both of us. It is actually amazing how much people will accommodate that and respect that. Because people just, they’re too yielding. They’re too accommodating.

[00:12:05] Jon Penland: Yeah. Yeah. And I’m curious, is this something that you knew early on, or is this something you, again, you’ve been doing this for 10 years, right? So I, it seems likely to me that when you first launched your first venture, maybe you didn’t have that rule and that’s one that you built in overtime. Or I guess, what I’m asking is are these things that you’ve learned over time and designed into eWebinar, but maybe didn’t have in place in some of your prior ventures? Are these kinds of learned, lessons learned along the way?

[00:12:36] Melissa Kwan: Yeah. I think I’ve, say, I’ve been doing this for 10 years and maybe a little over ten, but say I’ve been doing this for 10 years. I didn’t really come to know what would make me happy, what makes me truly happy, and what my non-negotiables are until maybe two years ago. Because as an entrepreneur, you’re tied up into making something work. You’re so enthralled into trying to pay other people’s bills, you don’t have time to think about what makes you happy.

[00:13:09] Jon Penland: Right. Yeah.

[00:13:12] Melissa Kwan: Being able to make those decisions is a luxury. And some people get there a lot faster. Like, I didn’t get there until a couple of years ago, but I think it’s an earned privilege. But it’s also like confidence is earned, because when you’re new you have no idea what you’re doing. So the customer says – I need you to do this. You do it. And then at the end of the day, you feel bad about it. You’re like – wait, that’s not what makes me happy. I’m doing it but I hate you for that. And it takes a lot of confidence and knowing that you can say no to be like – no, this is actually what makes me happy.

[00:13:49] Jon Penland: Yeah. Yeah. And something that I noticed as I was, again, doing some research prior to this call, is that I feel like you did… You talk about these ideas being earned, but I feel like when you launched eWebinar, you did pre-make a lot of these decisions. I was looking at some of the kind of foundational ideas and I know there were three ideas: create something I can be excited about every day, be able to share our successes with friends, build a fully remote team. It feels like as you went along, you learn these lessons and you were able to dictate those terms you designed eWebinar out of the gate in that way. Is that accurate? Were you intentionally designing eWebinar in a way that allowed this to work?

[00:14:34] Melissa Kwan: Yeah, so that, that is absolutely accurate. So in my previous company… So my first company, I ran it for three years, which kind of transitioned into my second company, which I ran for five years. So together, that was an eight-year journey, and this one I’ve been doing for two. I can honestly say that in those eight years I was miserable.

[00:15:00] Jon Penland: Okay. Yeah.

[00:15:01] Melissa Kwan: I was miserable because I didn’t ask myself the right question when I started. I think a lot of people think – oh, I’m going to start a company because I’m supposed to, or my peers are, or I think I have a really cool idea and I think it’s going to become something or I’m going to make a ton of money.

[00:15:19] But what is hugely underrated is people don’t ask themselves, what is the life that I want to live? It has absolutely nothing to do with your business. But understanding that that is important to you is a maturity thing, right? Because a lot of times, like you’re young, you’re in your twenties, you do what you think you’re supposed to, you pretend to know what, you pretend to know what you don’t and then eventually you figure it out.

[00:15:48] But in your twenties you don’t think – “What is the life that I want to live?” You’re still living your life. You’re still figuring out like, “Do I like red wine or white wine? Do I like to travel or not? Do I like this person or not? Do I like my friends?” I don’t even know.

[00:16:06] So until you can actually figure that out, you don’t know the life that you want to live. And the reason why I think it’s hugely underrated is because, your career is, especially as a founder, your career becomes such a big part of you that your life becomes your work. So if you don’t start with the right question of what kind of life do I want to live and find a business that fits that you do the other thing, which I’ve fallen into, which a lot of my peers have fallen into as well – you start a business and then you force a life that fits into your business.

[00:16:42] So I was just miserable because I built a business in real estate because that was my experience. I never really liked it, but it was my experience and I did it and then I thought – “Oh, maybe I’ll make some money.” And then I just kept doing it. But then I realize I’m too deep into it. I’m not making any money. And I hate industry.  Luckily, we kept going and we had, we had a good outcome, but I knew coming out of that, that if I were to do anything again, I would start with the question of what is the life that I want to live and then find a business that fits that because whatever that business is, it’s going to be five to ten years.

[00:17:27] I’m willing to commit to it, but I’m not willing to commit to it if it doesn’t give me a lifestyle that I love, which at that point was digital nomading, having a remote team, having a team accept and the fact that I am remote as well. But also, because freedom is just such an important thing to me, to create something that gives other people their freedom.

[00:17:52] The feeling that I have when I feel ultimate control is the feeling that I want to give someone else. And that’s what this business is about.

[00:18:03] Jon Penland: Yeah. Yeah. I have so many notes jotted down here of questions that I want to ask coming out of that answer. So I’m going to try to get to them. Something you touched on there at the end is that something that’s important to you is that what you’re doing today, give other people their freedom, give other people the opportunity to experience the same sort of freedom that you find so valuable in your own life.

[00:18:31] Can you speak to that a bit? What are some of the choices or some of the ways that you’ve approached setting up eWebinar, just practically speaking that have allowed other people to enjoy the same types of freedoms?

[00:18:42] Melissa Kwan: I think number one is our whole team is remote. So I’ve always been working remotely. In my previous company, our team is in Vancouver, but everyone has the opportunity to work remote. They just never really took that opportunity.

[00:18:54] What was interesting about what I’ve learned is the idea of freedom is more important than the execution of it. Everyone had the opportunity to work remotely, but they never did. But knowing that they could prevented them from going to another company like an Amazon, like a Facebook that didn’t give them the same freedom. So we were able to compete as a tiny startup, that wasn’t venture-backed, with these massive companies, because we gave the people the idea that they had control.  And it wasn’t a tactic. It was like, it was absolutely authentic and genuine. But what I learned was like – people need to know that they have control more than executing it.

[00:19:43] Jon Penland: Yeah. Yeah.

[00:19:44] Melissa Kwan: And this time around, our dev team is in Vietnam and Belarus. We have team members in Vancouver, New York, in Hong Kong as well.

[00:19:56] I don’t believe that talent is tied to geography, especially in this day and age where the world is flat, like my first company, its name is Flat World Applications. Especially with all the technology that we have today, talent is wherever you can find it. 

[00:20:14] And I truly believe that people are most productive when they get to choose where they wake up in the morning.

[00:20:23] And maybe that’s not the same thing for everybody, but I want to work with people that have the same philosophy and the same idea of how they want to live and I want to attract people that are like myself. So when you have that culture, other people kind of gravitate towards that. That’s one thing is like, everything is set up so that everyone’s a contractor or they’re full time, but they’re paid as a contractor but everyone can be anywhere they want. There is one caveat though, is as long as the customer comes first. 

[00:20:56] Jon Penland: Sure, sure. Absolutely. Yeah.

[00:20:57] Melissa Kwan: If you’re okay with that, then there are no after-hours, there are no weekends. And we don’t expect people to be on call for the weekend, but if there is something that needs to be delivered and if something is broken, it needs to be okay that you’re there to fix it for a couple of hours. 

[00:21:17] Jon Penland: Yeah. There needs to be an all-hands-on-deck mentality where folks aren’t necessarily watching their watch or watching the clock.

[00:21:26] Melissa Kwan: But then you end up designing an organization that is very customer-centric. It’s everything for the customer. You can take a week off if you want, but if something is broken and it’s the customer, we need to fix it immediately. So there’s ownership and accountability to the customer and that’s the culture.

[00:21:43] Jon Penland: Yeah. Yeah. It’s really so interesting to hear you talk because so much of what you are saying aligns so closely with the way Kinsta is set up. We, likewise are distributed team, we’re all over the place. We likewise have a flexible leave policy and folks can work from anywhere in the world that they want to.

[00:22:05] And as much as possible, we do have customer support teams and whatnot that we provide 24/7 coverage. We have to have folks online at certain times, but outside of that, we offer a good deal of flexibility around scheduling and whatnot. And so there’s just a lot of alignment between what you’re describing and then you even get into the concept of ownership.

[00:22:15] And that is something we harp on all the time. Within the company is the need to really own your function, own your job. We expect you to be the expert to really own what it is that you do. And for our customers to come first, being customer-centric is a core value for us as well. So a lot of what you’re saying resonates so closely with my own experience of working at Kinsta. And another idea that you expressed, the idea of freedom is more important. I can remember when I was working, this was prior to Kinsta, I reached a point that, there was a time when I was working for this particular company where financially doing something else was not viable. I needed that paycheck. And then I reached a couple of financial goals and suddenly I had some money in the bank and I didn’t have debt breathing down my neck.

[00:23:14] And I actually had the freedom. Like, I had the potential to go do something else. And at the same time, my job satisfaction rocketed because as soon as the sense of being trapped was gone, I felt like I was showing up by choice. And all of a sudden, my satisfaction with being there was so much higher. I really think there’s a lot of truth to that.

[00:23:35] That the idea of freedom, the sense that I’m not trapped is more important really than the specific fact that folks could work remotely.

[00:23:43] Melissa Kwan: Yeah. Yeah. And I think once you give, there’s also, like, a certain amount of trust that needs to go with that. 

[00:23:53] But when your team members know that you’re not breathing down their neck and micromanaging, like the moment they know that you trust that they have ownership over their task, I think people just deliver. You don’t have to worry about them. 

[00:24:09] We don’t have, this is probably unique because we have a small, very small company, but we never really had yearly reviews. People just did stuff and it was like a very lateral organization, but that’s what I prefer, right? I’m the founder of the company, but I’ve never enjoyed managing people. I’ve actually, I’ve actually hated managing people. So it’s better that people manage themselves.

[00:24:42] Jon Penland: Yeah. That’s, that actually leads me into one of the other questions that came up a moment ago in my mind, which is, you’ve talked a lot about setting up the company, such that it supports a lot of freedom in your lifestyle. I was curious if you’ve made the same types of choices in setting up the company, such that you have a degree of freedom in the tasks that you engage in. And you just mentioned management as being something that you don’t particularly love. Are there other things, other choices you’ve made, you’re on your third startup, are there things from the prior two that you said, I’ll start another company, but I’m not doing that.

[00:25:19] That is not something that I personally, it just doesn’t, I don’t enjoy doing that. It needs to be done, but it’s not something I’m going to be engaged in. I’m going to find somebody who that resonates with. So have you made those sorts of choices around the tasks you take on?

[00:25:35] Melissa Kwan: I think I’ve always, I’ve always been comfortable delegating, so I’m not one of those founders. Like I’m very aware of what I don’t know and what I’m not good at. And I’m very comfortable delegating those tasks out. I almost never do anything I’m bad at. One of the things that I teach my little cousin and I think about this a lot. Like, he hated math, right?

[00:26:02] He was horrible at math. And he was like, I’m bad at it because I hate it. I’m 10 years older than him, so my aunt was always asking me to give him some mentorship. And I told him anybody can be good at what they love. 

[00:26:20] Jon Penland: Sure. 

[00:26:20] Melissa Kwan: In order to be great, you have to also be good at the things you don’t love. Because not everybody can do that.

[00:26:29] So I recognize that there are many tasks, especially in starting a company that, are just mundane and repetitive. It’s just administration and I don’t want to do them. I also recognize that I don’t have the luxury. So from that perspective, it’s I don’t have to do it, but if I want my business to be successful, then I do have to. The way that I structured my business is I never do anything that I’m bad at.

[00:27:02] Jon Penland: Okay.

[00:27:03] Melissa Kwan: But I’m pretty good at a lot of the things I hate as well. Right. Like I hate doing projections. I do them. I hate doing documenting. I do all that. Like I hate payroll and hiring, but I do all that.

[00:27:20] And I think that’s the one thing as a business owner, especially if you’re not venture-backed, like you just don’t have the choice. So are you going to see this through or not? 

[00:27:33] Jon Penland: So you do have that, that choice to structure the business, such that it works for your life, but when it comes to getting business done, there are times where in order to, if the business is going to be a success, you have to engage in the tasks that need to happen, whether you like them or not.

[00:27:49] Melissa Kwan: Because yeah, cause, what are you doing it for? 

[00:27:52] You’re doing it so that at some point in the future you can have financial freedom or the freedom to choose. You just can’t do it now. So if doing certain things that you don’t want today means it takes you closer to your ultimate goal, then those are just things that, those are just tasks that you have to do, to take you closer to what you ultimately want to achieve.

[00:28:15] Jon Penland: And that’s interesting, I feel like what I’m seeing is a bit of a differentiation between what might be more of an entrepreneurial or a founder mentality versus an employee mentality. And I say that as an employee. To be clear, I’m not disparaging. I’m an employee, I’m not a founder. But I feel like a lot of times, and I interact a lot with our HR function internally, folks get really oriented towards the responsibilities of a role and what am I going to be doing day to day. And it sounds like what you’re saying is that as a founder, as an entrepreneur, you really can’t be focused on that.

[00:28:53] Now, obviously you need to be productive and get those things done, but you don’t really have a job description. You don’t have that luxury of saying, what is it that I’m going to be focused on. Your job is to move the business from where it is today, to where you’re trying to get. And whatever that means is what it means.

[00:29:10] Melissa Kwan: A CEO’s goal, a CEO’s only job is to make sure there’s money in the bank. So is that through revenue, right? Is that through raising funds or is that through investing your own money? 

[00:29:21] So if my ultimate goal is to make sure that there’s money in the bank, so the company keeps going and people keep working for us, then I will do whatever it takes to make sure there’s money in the bank. So is that project management, because we think that this particular feature is going to make us revenue. So is it to see that through or is it like to make sure that we have projections so that we understand exactly where we are in the business today?

[00:29:49] I don’t know how to do a spreadsheet. Like somebody had to teach me that. But now that I know it, it’s just like something that we have to do. Is it like motivating people so that, they’re going to keep going, even though we’re not paying market salaries? But it all boils down to, you are the CEO and you make sure there’s money in the bank to make payroll on the 15th or 30th. There is nothing else that you have to do.

[00:30:13] Jon Penland: Yeah. That’s interesting. I see, again, a lot of parallels between what I see happening at Kinsta, where I see our CEO early on actually building out product. And then as time went on being really focused on customer service and then being really focused on infrastructure. And then today he’s a lot more focused on, long-term vision and strategy.

[00:30:35] And his focus has changed, as we were just having a conversation about it yesterday. And a lot of his focus right now is around communication, right? Just about making sure that everybody in the company understands what’s happening, what the priorities are, where we’re going. And so it, it’s interesting to see that, that same type of thing playing out at Kinsta, where the job of the CEO is to say what does the company need today? What does this company need today? And that is going to be a different answer as time goes on. So the last question that I had come up with as you were speaking a minute ago so looking back and then we’ll shift into a little bit of a different topic.

[00:31:17] It strikes me that you’re a digital nomad who has built a product. You’re a digital nomad who prioritizes freedom, who has built a product that is heavy on automation. Is there some alignment there, is this a situation where you’re going, I need this product for my own life.

[00:31:36] Is there some alignment there between your own priorities and the product you built?

[00:31:41] Melissa Kwan: It’s perfect alignment. So in my past company, I ran it for five years. It was a SAAS company. As a lot of listeners might know, SAAS companies make money based on adoption and engagement.

[00:31:56] Somebody signs up. If they know how to use your product, they will be sticky. If they don’t know how to use your product, they unsubscribe.

[00:32:05] And my last company was an enterprise SAAS software. So we’re constantly selling to bigger companies that make sure their team members, agents, employees use it. But if their team members don’t use it, you don’t get the renewal. 

[00:32:17] So making a sale is step one. Like, making the sale is day one to like the rest of your life with that company. And every company wants you to kick it off. Not a sales manager, not a customer support person, but as a startup, when they’ve taken a chance on you, they want you to kick it off. So I realized I was selling software into a company and then every single company wanted me to do the onboarding, wanted me to do the kickoff, wanted me to the training, which was fine, but as we got even a little bit more successful, I don’t mean like really successful. As we started to sign on our fifth and sixth customers, those kick-off webinars were unmanageable because everybody wanted you to kick off, but the biggest problem with webinars is someone needs to do them.

[00:33:14] Jon Penland: Sure. 

[00:33:15] Melissa Kwan: Right. You’re here doing a podcast, might as well be a webinar, but you’re interviewing. And that happens once. So when you have a thousand-person company and you do one kickoff, it’s not enough, because maybe a hundred people can make it.

[00:33:32] So a hundred people sign up, 50 people show up. And then they sign up for the replay, but there’s no engagement. I was constantly doing these kickoffs for different customers but I was only doing one. So the impact that I was having was very low and the biggest other problem was every single one of those kickoffs were exactly the same. 

[00:33:52] Jon Penland: Yeah. 

[00:33:52] Melissa Kwan: I was like, okay, I’m traveling. So I basically created a life where I can travel and enjoy it. And we were in Chile, we were in Vietnam, all these really cool places. And I was supposed to be winning at life, but my entire schedule was dictated by my customer’s demos.

[00:34:18] How crazy is that? Like, you’re traveling around the world. You’ve earned this, but, I was like 4:00 AM in Kyoto doing a demo because that’s what was required to make, to make sure that my company, like my customer feels loved and my company keeps going. So years ago I was already like, I wish there could be a solution that can take a video and deliver it like a real-time webinar, but it must have a component, like a live chat component, that makes the customer feel like they’re being heard. And there were automated webinar companies out there, but they were poorly built. If I had to compare, it would be like a Wix to like a GeoCities. Do you remember GeoCities, like just super scrappy? And there was, but it was either that, or a YouTube video. Nobody wants to watch a YouTube video.

[00:35:17] Jon Penland: Absolutely. 

[00:35:17] Melissa Kwan: A webinar is to put on your calendar. There’s two-way engagement, there’s conversation. In a YouTube video, you can send it out, but do you know if they watched it?

[00:35:26] Can you follow up? Like it’s a push versus pull, right? So I envision a product that would allow me to train and onboard and sell to my customers and my prospects without being there, but it does not lose the two-way engagement, which is so important nowadays.  

[00:35:47] And so like the freedom that I didn’t have and the product that I had envisioned that would give me that freedom is the product that we have today.

[00:36:00] Jon Penland: Yeah. Which kind of leads me to the next question. Do you guys use your own product then for onboarding your own new customers? Is that the way that works?

[00:36:11] Melissa Kwan: Yeah. So anytime someone wants a demo from me, I don’t give a live demo. So it’s, here’s a demo. You can join your own time. We run it 10 times a week. I’m moderating it. And what’s ironic is for the first two months that we had to get the business going, I was doing at least 25 live one-on-one demos because that’s what was required. But I did it for two months until we got our initial set of customers going. We had some use cases going, and then now what’s interesting is, I will still do a live demo for a friend or like a friend of a friend. 

[00:36:52] But, a hundred percent of the time if I say, I am happy to do a live demo for you, or here’s a 15-minute demo that you can join on your own time, and I will be a resource to you if you have questions afterwards. A hundred percent of the time, they don’t want a time on my calendar. So if you think about how consumer behaviors have shifted.

[00:37:17] Jon Penland: Yeah. 

[00:37:17] Melissa Kwan: If somebody says, Jon, I want to learn more about your company and you say great, schedule a time with me. They’re going to bounce. Really? Like you don’t gate your content. Like consumers are so savvy nowadays. They want to do their own research and they don’t want to talk to a salesperson until they’re ready.

[00:37:35] Jon Penland: Yep.

[00:37:36] Melissa Kwan: What we do is we make that content available all the time and you can step in when you want to.

[00:37:45] Jon Penland: Sure. Yeah. It feels like the classic distinction between calling and texting, right? Where it’s don’t call me, text me…

[00:37:54] Melissa Kwan: Yeah, know. When someone calls I’m like, is something wrong?

[00:37:58] Jon Penland: Right, exactly. So it, and it feels like the same sort of shift where folks are more comfortable when they can engage with content on their own schedule and in a way where they don’t necessarily feel pressured in the moment to have to respond. It reduces the pressure factor for the recipient, for the viewer.

[00:38:19] Melissa Kwan: Anybody nowadays knows that if I talk to a salesperson, I’m never getting rid of them. That’s what they’re thinking and I know that because I’m a salesperson. 

[00:38:28] But consumers are king nowadays, right? You have to give them information when they want it, at the time they want it, but you still have to make sure they know that they’re heard. That’s how picky we are nowadays. I challenge people to think about their own buying journey. If you were the customer which you are, you’re the consumer of something else, when you want to buy a product, how do you want to be treated? 

[00:39:05] But from the other side, like if I’m a salesperson and I don’t have to talk to someone and only make the sale, when they’re ready, like awesome.

[00:39:12] Jon Penland: Yeah. That’s fantastic. Yeah. It’s interesting that you highlight the need that you give them the content at the time that they want to consume it, but you still make yourself available as a resource. That’s really powerful. That’s a really powerful insight. So I want to shift gears here a little bit and ask a couple of questions that veer more into the personal freedom that you’ve talked about a little bit, because as you’ve mentioned, you are a digital nomad and I’m curious, how has the pandemic affected your travel and your lifestyle over the last year or so?

[00:39:47] Melissa Kwan: So ironically, we got a place. So we traveled for two and a half years, my partner and I… Fell in love with Amsterdam. It’s one of the most amazing cities in the world. I’ve recently lived in New York, left three years ago. And we got a place in Amsterdam because we were so sick of traveling.

[00:40:07] Cause we’re like, okay, it’s been two and a half years. Like we need a home base and we hate checking in luggage. So we only have a hand, like a handheld on the premise that anything you want, you can buy, but we’re fairly simple. Like we don’t care a ton about fashion.

[00:40:26] If I could wear the same thing every day, I would, but it was more about the experience of being somewhere else.  And we’re finally sick of it and we got a place in Amsterdam, but about a year ago and because of COVID we haven’t been back for one year. So we got a place to stop traveling, but because of COVID, we escaped.

[00:40:46] So we actually, what was so crazy, it was like we, at the beginning of the pandemic, we had a trip that was planned to see some friends in Hawaii, who we had met at Burning Man. And I think it was like March 13th or something was, it was or date like was what was when we’re flying.

[00:41:08] But I don’t know if you remember that, but March 14th was like when the whole world had shut down.

[00:41:15] So when we were going to the airport, my friend had texted me and said –  “Hey, all this stuff is being announced. I don’t know if you still want to come. It’s okay, we won’t be offended if you don’t want to come.” And I didn’t actually, I mean, myself and the rest of the world was just underestimating. 

[00:41:33] Like I thought it was like, yeah, a couple of weeks. Yeah. It was like, yeah, a couple weeks. Okay. We’ll just go there, we’ll be stuck for a couple of weeks. So we landed in Hawaii on a Big Island and the whole world had shut down. Then we ended up being in Hawaii for four months. And then we went to Vancouver. We spent the summer in Vancouver, where I’m from, for four months. We went back to Amsterdam for two weeks cause my partner hadn’t seen his kids for – he hadn’t seen his kids for nine months at that point. So he was like, I need to be dad.

[00:42:03] And as soon as we got there, we play dad, and after that I was like, okay, so it’s not yet winter, COVID is everywhere. And the thing is – we’re starting a business, so I don’t want to take a risk. So my life partner is also our CTO. My co-founder. So I was like, okay, we are in the beginning of our business. If either of us get sick, if we’re out five days, the business goes down. And if we’re out for a few weeks or in the worst case scenario, if one of us are out forever, there’s no business. And all of our investors are our friends.

[00:42:45] We’re not playing with random people’s money. Like we’re responsible for our friends’ money. So we spent a couple of weeks in Amsterdam and it was nice to be home after so long, but I was like, okay, let’s make the sensible decision. Let’s leave Europe cause it’s going to meltdown when winter comes and let’s go to a place with very little virus.

[00:43:09] And my family’s from Hong Kong originally, so we were able to come here. So we’ve been here for a few months now. The original question is how has COVID affected our travel? Previous to COVID we were traveling once every week or two weeks. But because of COVID, we are now in places for extended periods of time.

[00:43:33] So we are in every place for three or four months, because with the quarantine it doesn’t make sense. 

[00:43:40] Jon Penland: It doesn’t make any sense to land somewhere and stay in quarantine for two weeks and then pack up and go somewhere else to quarantine for two more weeks.

[00:40:06] Melissa Kwan: But then you get to know cities that you’re in a different way.

[00:43:51] Jon Penland: Yeah. And I imagine it’s, it’s, you’re also getting to know them in a different way than you would in non-pandemic times because the cities themselves are quite different right now. 

[00:44:05] Melissa Kwan: We were in Hawaii where there were no tourists. So our friends, our local friends were saying they’ve never seen the beaches completely empty.  

[00:44:14] It was like, you couldn’t be on a beach. Like you could go swim, but you couldn’t linger. Every single beach was empty. Could you imagine a city that thrives on tourism has no tourists? We were able to see it in a different way.

[00:44:32] Jon Penland: Yeah, absolutely. Yeah. And I’m curious, staying on the digital nomad front, do you find being a digital nomad to be a hindrance to your work or to be actually an advantage in the work that you do?

[00:44:43] Melissa Kwan: I don’t think it’s one or the other. I think for me, I think it goes back to what kind of life do you want to live. If this is the life that makes you happy, if this is how you are most productive, if you thrive in this way, then, it’s an advantage. But if you need structure… Like my previous co-founder to my other business, he doesn’t really like traveling.

[00:45:09] He likes 9-to-5, he likes having a team in the office. He wouldn’t thrive in this way. So I don’t think being a digital nomad allows me to start this business. I think I would’ve done it anyway, but I am at my happiest when I am in this state. And in that way, I’m able to contribute to my business in a way that I wouldn’t otherwise.

[00:46:42] Jon Penland: That’s really what jumps out to me is that as I hear you talking about, how much the way that you live means to you, I feel like what I see is that inspiring you to create work experiences for other people in a specific kind of way. And so you enable other people to have freedom and to have ownership over their roles and to have to enjoy some of those own freedoms themselves without necessarily having to go out and create their own company. And I think that, again, speaking from the perspective of a company that has a similar approach, I think that bears huge fruit in the success of your own business. 

[00:46:16] Melissa Kwan: I also want to encourage people to think differently about their life. How many times do you hear someone say –  Oh, I wish I could do X when I was young or I wish I could be more like you. The only thing that’s stopping you and, providing you don’t have kids or any dependence, right?

[00:46:40] Like the only thing that’s stopping you in living that life is the decision that you have to make. I knew a lot of people in their forties, they have young kids or in their thirties, they have young kids and I’m like, Oh, I wish in my twenties, like I would have done this.

[00:6:53] Right now travel is so affordable. It’s never been more accessible. It’s never been more affordable. And then with Airbnb and communities you can sublet from, it’s never been easier to go to a place, sublet something for a month, tap into a community. And the thing about change that I love the most is you can change again if it doesn’t work. It is so much easier to go back to what you know, than to move forward to what you don’t. 

[00:47:27] If you want to go somewhere, just go. If you think I wish I can do this, just go do it because you can correct that decision if you don’t like it. So I want to through this particular lifestyle, encourage people to think, yes, you can do it.

[00:47:48] There is actually nothing that is tying you back from not doing it. There’s no reason why you have to be home at a certain time or whatever it might be like. You just have to make that decision to let it go. And I think we have manufactured tie to like physical things.

[00:48:10] We’re tied to our home, tied to our bed, we’re tied to stuff. But all of this stuff you realize, if you’re willing to give that up there is nothing that’s more liberating.

[00:48:23] Because your stuff ultimately controls you. Isn’t that so ironic, that you want to control your things and then ultimately your things control you because you feel like you have to be there for it.

[00:48:37] Jon Penland: Right. Yep. You’re absolutely right. A few years ago, my wife and I and our family, we actually spent a couple of years doing the digital nomad thing here in the United States in an RV. So we spent three years and we hit like 26 different states over the course of three years. And we’ve intentionally chosen to settle back down, yeah, where we’re at today, specifically so that the kids could get involved in things like recreation, sports, and those types of things that really need to be tied to a specific location. And it’s been interesting having been controlled by things in the past and going through that phase where we really had to disentangle so that we could go on the road for three years and now coming back and as we’re making those decisions, again, we’re so much more critical about those decisions.

[00:49:26] Like I’m looking at a vehicle now and I’m going, I’m not buying that vehicle if I can’t sell it. I’m not buying that house if I can’t sell it. If I’m gonna make a commitment, I’m going to make a commitment that can be unmade at some point, because I have enjoyed that freedom.

[00:49:44] And if I want that freedom again, I want to know it’s not that far away, that the option is still there if I decided I wanted to go that direction. 

[00:49:50] Melissa Kwan: Yeah. The thing about stuff is… So, I lived in this apartment for 10 years in Vancouver. When I moved to New York, I had to boil everything down to a single room. So in my last two hours before I headed to the airport, I sold my car, I posted on Facebook whatever I can sell, come and pick it up. And maybe a month after I moved to New York and maybe less than that, I don’t even remember what I gave away.

[00:50:20] That’s how little this stuff I held meant to me. I kept memorabilia and things like that packed in the box and shipped it to my mom’s house. The furniture that you spent too much money on, you don’t even remember, so why does it matter?

[00:50:35] Jon Penland: Yeah. Yeah. That’s so funny you say that, when we went on the road, we kept one like eight by four storage unit of stuff. And after we had been on the road for a year, we were like, we don’t even know what’s in that unit. Like we haven’t touched this stuff in a year. It’s just in a storage unit in Texas. I have no idea what’s even in that storage unit. Absolutely.

[00:50:52] Melissa Kwan: And you’re paying more to keep that storage unit than what’s inside. 

[00:50:56] Jon Penland: Exactly. Yeah. Like we probably had a thousand dollars worth of stuff in there and we’re paying a hundred dollars a month to keep it. Absolutely. Yeah. All right. I’m gonna move us forward to a conclusion here and I’ve got three questions to wrap us up and take us away.

[00:51:13] So the first is what advice would you give to a would-be entrepreneur, somebody starting out, looking at launching their first company. What’s some advice you would give that budding entrepreneur.

[00:51:25] Melissa Kwan: And that’s something that I had mentioned before is I would start with asking yourself, what is that life you want to live? And it could be simple things, right? Like people think it’s complicated, but it’s not, is it I want to live in Thailand? Then ultimately, do it now. 

[00:51:45] Figure out how to do that now and then figure out a business that fits that. Or, I want to serve a certain market or I want to leverage my past experience. Don’t do something because someone comes to you and says, Jon, I have a great idea.

[00:51:59] And you think you’re the person to do it. Yeah. Given enough time, anyone can make anything successful. And every choice that is in front of you is a choice that you can make. But one of those choices is going to help you get out of bed easier in the morning.

[00:52:15] So make the choice that makes you happiest, but you can’t make that decision unless you know exactly what life you want to lead. So I would say, start with that and then figure out what your non-negotiables are and then figure out the business that fits that.

[00:52:33] Jon Penland: Hmm. Okay. So start with your non-negotiables, start with the life you want to live, and then work on the idea from there. Nice. Okay.

[00:52:42] Melissa Kwan: Because if you don’t have that, any idea goes. Everything works. Everything’s awesome.

[00:52:48] Jon Penland: And I, I think the risk there is that you, you do something and then you get two years down the road and realize you hate it. Like you get two years down the road and worst-case scenario, maybe you’re successful and you really hate what you’re doing. You really…

[00:52:55] Melissa Kwan: But businesses can, right? Businesses are not a constant, but like where you ultimately want to get in your life, that doesn’t really change. And if you don’t make choices that fit that, fit those life choices, then you’re constantly going to think about, what else can you do to go back to it? And before you know it like you’re too deep into that business, you can’t let it go.

[00:53:29] Jon Penland: Yep. All right. Moving on to our second wrap-up question here. What is a go-to resource – and resource could be a newsletter, a conference, a blog, a community, a person, whatever – what’s a go-to resource for you for business or entrepreneurship wisdom.

[00:53:45] Melissa Kwan: There are, outside of having, I think it’s really important to have mentors, like people that you look up to and people you can go to, who may or may not be very close to you, but people that connect with where you are today and those people change over time. But outside of that, there are two books that I love.

[00:54:05] One is The Alchemist by Paulo Coelho. It’s a story, it’s a nice story. It’s like the ultimate journey of a boy that like left his home to chase his dream. But it’s very well-written, it’s a really easy read. You can probably finish it in a couple of days. But I realized that every time I read that book at different points in my life, different things appeal to me and it’s a nice getaway cause I read a lot of business stuff. It’s a nice break. It’s a really nice story. And there’s a lot of good nuggets in there. 

[00:54:47] But the other one is a book called The Presentation Secrets of Steve Jobs. He did not write it, Carmine Gallo did. And it’s a guy that just studied, like the way that he presents. I’ve been in sales all my life. I think that one of the skills that is always missing from founders is the ability to sell. And when you have the ability to sell, and the ability to sell is not like I’m selling you this car, I’m selling you this pen, right?

[00:55:27] The ability to sell to me means understanding where revenue comes from. Why is someone going to pay for X? If you don’t understand how to generate and how to create value, you cannot make the right product decisions. You can build an incredible product that generates no monetary value for somebody. So The Presentation Secrets of Steve Jobs helps you craft a presentation and guide someone to your desired outcome, but it’s all about value creation.

[00:55:53] Jon Penland: Absolutely. Yeah. It’s interesting to hear you talk about the need to sell as a CEO. The thing that occurs to me, and I’m not sure if this is necessarily directly relevant to that book, is that as a CEO at a startup, you’re going to be selling, but at any size company, you’re going to be selling ideas internally. Even if you’re not selling to customers, you’re going to be selling, you’ve got to get people on board with what it is that you’re trying to accomplish.

[00:56:20] Melissa Kwan: But the CEO comes up with a messaging for every product. Customer success is sales, support is sales, product management – they’re all sales. But you need to understand where the money comes from before you can craft that message.

[00:56:40] Jon Penland: Yeah. Yeah. I would even go so far as to say that in a sense, management is sales, in a sense, getting your own team on board with what it is you’re trying to accomplish is a form of sales. Yeah. All right. Last question. Where should our listeners go to learn more about you or about eWebinar? 

[00:56:54] Melissa Kwan: Definitely come to It’s spelt exactly how it sounds.   Lots of information on there if you’re curious about how we can automate your business. If you are doing repetitive webinars or if a team member is, and you hate doing that, we might be able to help you. So any onboarding training, marketing demos… And if you want to connect with me through LinkedIn it’s just Melissa Kwan. 

[00:57:30] Jon Penland: Okay. Awesome. So check out Melissa on LinkedIn and check out Thank you so much for joining me today, Melissa. It’s been an honor, a privilege to speak with you today on Reverse Engineered. And thank you to all of our listeners. That is it for today’s podcast. You can access the episode, show notes at That is K I N S T If you enjoyed this episode, don’t forget to subscribe to Reverse Engineered and leave us a review on Apple podcasts or the platform  you’re listening on right now and see you next time.

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