10 Unconventional Lessons From Bootstrapping to $1M with Melissa Kwan, eWebinar

Leverage community led growth to skyrocket your business. Hey, Traction fam. It's your host, Lloyd Lobo. I've just released a book that I've been working on for some time. It's called from grassroots to greatness, Master 13 Game changing rules from some of the world's most iconic brands like Apple, Atlassian Crossfit, Harley Davidson, HubSpot, Red Bull and a lot more. So you can attract super fans of your own that will propel you to new heights. Your support would mean the world to me. Please grab your copy at from grassroots.

To greatness.com we spend so much time building our business because we want to be free. And then as our business grows, we keep working in the business and then we're not free. And then we forget that we started this to be free to begin with. So I want to make sure that I am and we are living the life that we intentionally wanted to build by doing what we do every day. Because there's this whole thing about, oh, I can do this thing later, I can do this thing when I hit 2 million, or I can do this thing when I sell my company. Well, you don't even know if you're going to be alive tomorrow, and that is the truth. So if you're not living now and spending time with people you have fun with and love now and going to see the places you want to see when you're young and can walk around and and can adventure, you're going to miss out on all this stuff.

I need some traction. You need some traction. Let's get some traction. Hey, what's up, innovators, entrepreneurs, visionaries and disruptors. This is your Traction podcast host, Lloyd Lobo. We're a community of over 100,000 people just like yourself on a mission to help you get the methods, the money and the madness to explode your business growth. Featuring stories and tactical advice straight from those who've done it before, like Shopify, Twilio, Asana, and many more. Hey, Traction fam. This is a special episode with one of my closest friends, an agony ant whose brutal honesty I rely on almost every day. Meet Melissa Kwan, the co founder and CEO of E. Webinar. Prior to E. Webinar, she's bootstrapped two other companies and had one exit, all while traveling the world like a nomad. Her story reflects her belief that work should never come at the cost of living one's life to the fullest. She has a knack for distilling her experiences into relatable anecdotes, which is what makes her a very inspiring speaker. So strap in for a no holds barred conversation. We're going to dive into some juicy, unfiltered insights and slay some unicorn porn as we challenge you about everything you knew about building, funding, and surviving in the tech world. Melissa, how you doing? Thank you for joining me.

I'm good. Thanks so much for having me. Lloyd.

It's funny to speak like this with you because we chat on WhatsApp 350 times a day. I think I have like four or five hundred chat messages with you, so this radio voice doesn't really work, but it's fine. We have a bunch of unconventional wisdoms in the startup world that we're going to slay on today's podcast episode with you. And you're unconventional in every sense, right from how you started the company to how you live your life to how you run the company and every other notion that is, this is how success looks like, this is how you should get to success. You've slayed that and you're killing it. So I want to get right into that. But first, give us your backstory. Immigrant family. How did you get into entrepreneurship?

I grew up in Calgary and then I went to the big city for university, which is Vancouver. That's going way back. But I'm not from a family of entrepreneurs. I think that's really important. And I'm from a family of super traditional Chinese family that just wanted me to marry rich and or be a profession that my parents could be proud of, quote unquote, like accountant, banker, doctor. And I didn't do any of that. But I did go to university and then became a receptionist immediately after that. Made my parents so mad because I wanted to be a real estate developer. So then I went to work as a receptionist at a real estate development firm. That was my first job. That's really going too far back. But I bootstrapped three companies. My first two companies were in real estate tech because my previous experience was really in the real estate business working for developers. But the last job that I left was actually at SAP, which was a huge company in Vancouver. It was like second to Oracle, and I wanted to work for a tech company and SAP was across the street from me, like in Yaletown. So I was like, oh, how great would it be if I could just wake up from bed and walk across the street to work? And that's actually how I picked the company. But I quit SAP and started my first company in real estate tech. Wanted it to be a product, but we were bootstrapped. So we said yes to everything and then very quickly became an agency. Also familiar story, but four years of chasing invoices and cold calling, I was like, yeah, screw this. I need a product that we sell to everyone. Instead of trying to beg people to pay me 20 grand, I probably need 20,000 people to pay me 10 bucks. So that first company transitioned into my second company, Spatio, which was open house check in app. And that was the one that was acquired in 2019. And that gave me the means to bootstrap this company, e Webinar with a lot less stress than I did before. So that's my backstory.

Why did you decide to do e Webinar over a hundred other things that you could have done.

A lot of people approach companies the wrong way. Lenny just came out with a podcast newsletter that was like, how to validate your idea. I interview like 300 people. And that was his podcast. And I'm reading this, like, how can you pick an idea based on the validity of whether it's going to make money in the market if you don't consider yourself at all? I had probably a hundred ideas, but 99 of them were not me. Even though they might make money in the market, I do not have the expertise to do that. So I think the first question anybody should ask themselves. And I Learned this after 10 years of working in real estate and not loving my job, is putting myself first and asking myself, okay, what are the things that make me happy? And find a product and career on top of that. So I actually, after Spatio was acquired, I made a list of 10 non negotiables I have to have in my next company. And I chose an idea based on that. I didn't choose the idea because I was like, oh, this is the one that's going to make the most cash. But coincidentally, e Webinar is something that's very close to my heart because my number one priority in life is freedom. Like, I do this for freedom. I do this to be not just financially free, but I do this so that I can spend more time with friends and family, so I can travel, so I can party. So what we're selling, an e Webinar is not webinars. We're selling time. We want to give people their time back. And that really aligned with my values. So just from having that list of 10 non negotiables that make me happy, I eliminated most of the ideas that I had. And that was actually how I picked it. But having said that, e Webinar is solving a problem that I personally lived with for five years in my previous startup. So I knew that problem of doing repetitive webinars intimately.

Well, a lot of what we do in life comes from a place of negotiables. So most people, and this is the western dream, the American dream, they can't afford to live the way they want to. Or other people's definition of success close to their work. Like if they work in the city, so they'll find a bigger house, they'll take a mortgage and they'll live a huge commute away and spend two, three hours a day commuting, picking, dropping kids and just running around. And a lot of even what you do as a founder in the business is negotiables, right? Especially your venture back. You're going to meet in the middle, let's negotiate, let's get this deal done a certain way. And I have these things I want and you have the other things that you agree on. And I feel like anytime we do things based on negotiables, we end up unhappy. We gotta start with non negotiables. When you start with non negotiables, you end up happier. I found this about myself as well. I lived in the Bay area of last 13 years and prior to that in New Jersey and before that Toronto. All our life we lived in the suburbs, commute everywhere. That was the way of life. Like commute two hours. And then the same way the business is all about negotiables, right? And you put the things you love or draw joy from on the back burner. And then after I exited boast, I ended up with mental health issues because I had put everything out. I put all my non negotiables on the back burner. And then the company became my identity and. And then one day I was no longer in the company and I felt this void. I ended up depressed when we moved to Dubai. Now my non negotiable is have to be walking to everything, have to be on the beach and I gotta be able to work out and socialize every single day. And I will not negotiate on those things with anyone. And I feel like a hundred x happier mentally. So kudos to you to start with that. What made you arrive at that thought process? Because a lot of immigrant kids were taught growing up everything is about you will work till you're 65 and then you will make this money and you'll retire. And by then, given the diets we are on, given the environment we're in, we're not functional anyway. But that is the thing that is imbibed in our brains. So kudos to you. How did you think of saying, hey, I am always going to start with non negotiables? If that means I don't make a lot more money, who cares? But I'm living every day happy.

That's the biggest lie that we live with. Not just with Asian parents, but conventionally in social norms, right? Like you study, you pick a major, you get a job in that major, and then you work a lot to get a mortgage, and then you get married, you have kids, and then you up your mortgage, and then you up your mortgage again. That's what we were taught. Maybe culturally it's more that way because it's all about, like, the next generation and all those things. But I want to make sure that I address this point as living the way that I do now. And having that list of non negotiables was an earned privilege. People come to me and they're like, oh, of course you can bootstrap you webinar because you had a sale. It's like, well, it wasn't always like that. I had 10 years of not being like that. I also took agency work and consulting, and I also didn't know if I was going to miss payroll. And for two years, I only had a hundred bucks in my account and I was living in New York. So I would siphon money into my account after the 15th and the 30th, when I knew everyone else was paid to make sure I could cover my rent. And then I didn't want to put too much money in my account in case I didn't get another project before the month ended. That was how I lived for many years. So I want to say that, yes, having non negotiables is super important, but I'm 40. I just turned 40 and I started my first company out of SAP when I was 27. So all of this learning and experience was an earned privilege. And I do think that if you're in your 20s, maybe it's not an age thing, maybe it's where you are in your journey. You gotta pay your dues before you can earn that privilege of choosing the way you live. So I think how I came up with that thought process was through a process of elimination of doing so many things that I absolutely hated. Speaking of things that are unconventional to the way I live and how I build my businesses, I spent years going to conferences and networking events and sitting at booths so I could sell my software and meet people in real Life that coming here, I'm like, I am not going to do that again. So I need a product that can sell a hundred percent through the Internet. I do not spend time networking with anybody. I will not talk to anyone on the phone. And if someone's like, oh, my friend also lives in Amsterdam and they have a startup, will you meet them? The answer is no. I spend my time in real life, time with my friends. So it was all through a process of elimination, but I did pay my dues and I learned what I liked and what I didn't like to create that list. And I think that's what life is about. It's a process of elimination. But I still did them because I had to. And you had mentioned, well, now that I sold part of both or took some money off the table, I'm able to do X. And it sounds like that was like that for you too. Like, I know you paid your dues as well.

That is well said. Because you got to earn the rights in everything. So, like, even when you compare it to companies, you can't just go and build a second product and a third product and a fourth product. If you look at every company that's at 100 million in revenue, bootstrap or venture back in material, you can't build a second product if you've not earned the right to do that, your first product is not loved and whatnot. And the same thing in life. You can't just say, these are my non negotiables. You're going to end up very poor and on the street. So that is a good way of putting it. And I'm glad we dove into that because I don't want listeners, especially the young listeners, to think that, okay, they can start by just doing nothing and having non negotiables and make it. Because this is the problem in the current workforce that we face is a lot of kids coming out of school have non negotiables almost immediately.

I'm half joking when I say this, but have we not taken mental health too far? In my days when we were starting out, there was no mental health. Even seven years ago, when I was at my darkest place, living in New York, having no money, I just did what was required. I wasn't like, oh, I'm burning out. What's burnout, right? What's mental health? But I feel like now it's like this impacts my mental health. And I do think there's a big part of that. Like, I don't want to make light of that, but there Was a time when I just had to power through even when I didn't want to, even when everything sucked so bad. And my parents wouldn't talk to me for two years because I'd asked them to bail out my credit card so many times. I didn't have a credit card until my company was acquired. And then I had to put in like a security deposit to build up my credit again. That's how bad it was. But I think there's a fine line between, okay, I'm gonna power through and do this because I'm earning my right to more freedom or my non negotiables and living the way I want to, to, oh, I can't do this because it's impacting my wellbeing. I don't know what you think about that. And I feel like people give up really quickly right now. I don't know if it's just like the people I come in touch with and lightly mentor, but I feel like people give up too quickly almost nowadays with even the job hopping and stuff like that. I've personally experienced.

I keep seeing these YouTube shorts or Insta reels with this quote that tough people create easy times, easy times create weak people, and weak people create difficult times. And there's some truth to that because if I look at my grandparents, they just wanted to put food on the table. My grandparents lived in the slums of India, in a village, remote village in southern India. They just wanted to put food on the table. My parents were working as soon as they had any bearings. When they're 8, 9, 10, 11, they're working in the fields or my mom was in Mumbai in the slums. They were like just doing some work. Then my parents, for better prospects, moved to Kuwait. That was the time where people didn't have access to the West. They moved to Kuwait and better pay and some stability. And they wanted to have things and givers, just things. So education, house, television, all of that stuff. And then our generation came along and we wanted experiences. We had the stability of the food in the house and we care less about things and more about experience. But I feel like part of it has to be as a generation with kids. We have to be blamed a little bit because we coddle our kids too much. We want our kids to have everything and we give into every fancy of our kids. Now, I'm not saying beat your kids. I got beat up by my teachers. I'm not saying do that. That is extreme. But where does it stop? Is the thing when you keep creating a safe place and a safe place and a safe place. The world becomes so safe that you can't step into reality anymore. And that's what's happening today is the slightest difficulty and people don't want to be there. They quit jobs, they jump jobs. I'm not saying that being true for everyone, but pain is a precondition for growth. In the gym, if you don't keep increasing the weight or doing more reps, you're not going to get stronger, you're not going to get fitter. Same thing in the business. If you don't keep taking on new challenges and achieving new targets, your business is not going to grow. So if you keep looking for a safe place, I'm just afraid that it's going to hinder your growth. So there is that balance. I truly agree that we may have pushed mental health too far, but I have suffered mental health issues. I have been depressed. There's a line between what's real there and what is triggering. We seem to get be a society that's starting to get triggered by every little thing.

I totally see your point. There's a few things that are going through my head that are just like driving me insane. But adversity is required for learning. And I think a lot of people, they look at what I've achieved or what you've achieved and like, oh, I want that as well. I want to be a digital nomad. I talked about this at a recruiting session earlier this year and they were so inspired by having a fully remote team and how I was a digital nomad and how they want that as well. And we want those people because we have a fully remote team. But in order to learn as a junior, as in a remote team is actually quite hard because you don't learn by osmosis. So it takes a certain type of person that is self motivated. You have to be curious. You have to go and figure out your own problems and reach out to your team members and set up those conversations. And we looked at over 50 resumes. We were hiring for a junior dev. We wanted someone who was smart. We didn't care they had experience. We just wanted someone who was good at problem solving and had good attitude. And then we looked at 20 of them. We gave 20 of them like a coding test. And then David, my CTO interviewed like 10 of them, which took a significant amount of time. And then we hired someone who had no experience. His last experience was in retail. He was super smart, such a good attitude. He loved our company. He seemed to align with the Values. He was super excited about where we are and we brought him on board. We were all really excited. Three months later, out of nowhere, he quits. And then we realized that for two and a half of those months he was looking for a new job. And every week we had checked in with him to make sure that he was doing okay because we knew we were remote. And it was like, well, why are you quitting? Also like, this just came out of nowhere. I thought you were happy. Oh, I just wasn't sure if being a developer was really what I wanted and if I could really go to work solving problems every day. So I'm just gonna go and work for a bank that is literally the opposite of us. Co work for a bank as a product manager, not even like what he went to school for. And in that moment I'm like, well, you've told me how much do you aspire to living the life that we have but a few hard problems? And you're like, I don't know if this is right for me. You don't even stick with it for longer than 90 days. I mean, that just blows my mind. But this is actually one of the two instances that I've personally experienced in just in the last year. And I'd hate to say this, but this is usually with younger people.

That is the unfortunate reality of creating too much of a safe space is where does it end? I've always admired your brutal honesty in a world where we all sugar coating and fake nice teas. My kids don't even have a grading system. I understand, but where does it stop? If we want to create a safe place because we don't want them to feel overwhelmed or feel triggered, then when they get into the workforce and reality sinks in, it's a competition out there. Two businesses compete, employees compete for promotions or salespeople compete for commissions or bonuses, things like that. The world is a competition. Doesn't mean competition is bad. We've created this narrative that competition is a bad thing. But regardless, if there's no competition, people just remain status quo.

It's funny you mentioned that, because my best friend's kids in Vancouver, their school no longer has homework and they no longer have exams. I forgot the word for the learning. But there's no exam, there's no grading, there's no homework. They just go to school and there's no curriculum. They just go and play and learn through like I don't know what it is, but I'm like, how do they take provincial exams? How do you get into A university or like, take your SATs. I don't know how the education system works right now, but if you wanted to transfer to another school and they do have a curriculum and exams, how do you adjust to that? I don't know what the world has turned into, but it's really weird. And you're right. If you come and work in the real world and you can't have anybody tell you you're not good enough, that you need to improve. Like, we have to sugarcoat everything. It's really hard not just to hire the right person, but also to nurture the right person because they cannot take criticism. This actually happened in our company where we hired someone who we were again, excited about just part time, like helping us with some marketing task. Marketing coordinator. She spends half her time in school and she wasn't performing. And it was just maybe two, three months after we realized, okay, we need to have a conversation. And her manager was like, okay, let's get on a call. And starts to lead into her a little bit about how she wasn't showing up for her calls, like scheduled calls. She said she wasn't checking in. And then she was like, I'm not in the mind space to have this conversation right now. I need to go like, are you serious? We're paying you. You don't show up, you don't deliver, you don't do what you say you will. And we're just leaning into you, like a little bit. And then you're not in the mind space to have this conversation. It's tough, right? But you don't know what you don't know. So I feel like it's tough to be in that generation, but also you want to be as an employer, as empathetic as possible. It's hard. Like, I don't know where that line is, where you're not being empathetic versus you just need to do what you need to do.

You definitely need to lead with empathy. But my urge to parents is don't try to molly coddle your kids and create so much of a safe place for them that when they go out there, it's difficult for them to adapt to the reality of the world, because the world is not this way. You go into business, you at the workplace need to communicate with other people who are at all levels, not just at where you are. And so you need to share the space with everyone. And if you're always getting offended or you're always triggered or you can't handle too much, I'll give you an Example, my wife's a physician. She's an ER physician and she's just back in the US doing shift work at Stanford. And they had a student come in for an internship. Physician's assistant student. And the student is now complaining all day of the first day of internship. Don't you guys have a life? Why would anyone do this? These long hours are inhumane, bro. You signed up to be in the medical space, you went to school to be a physician's assistant, you wanted to go into ER and you asked for a job and now you're going to sit and complain. And this is the problem, right? We coddle our kids too much and it's going to lead to bad things. It's going to lead to a generation that is too soft and can't handle the harsh realities of the world, at least on the West. So that leads me to one of the first misconceptions here is no employees, all contractors. I hate managing people. Tell me about that.

Yeah, that's a nice lead in. So that's definitely one of the more unconventional business mantras that I now live. I've always had a small team, but I was always and still am really, really bad at having these types of confrontational conversations because I try to be as empathetic as possible and I just know I'm not a good people manager. I love building companies and selling stuff and creating, but people is just not my strong suit. So coming into this company, I vowed to never hire employees again. But as a bootstrap company, that's also how it makes this company financially possible. We can't hire anywhere in the west because we can't compete with any funded startup or any company. How are you going to hire someone for like 25% of the cost? It's not that I want to not pay them, it's just I can't afford it. So being open to hiring someone anywhere in the world, in other words, outsourcing and not having a physical location, and I always had a remote team anyway, opens you up to talent anywhere in the world. So you can hire based on really talent and attitude and value alignment and then pay them market rate or higher in the country where they're at. I'd rather do that, and this is what we do now, than to try to convince someone that could get paid double next door to work for you only to have them leave. But I think financially that's the second priority. The first priority is I know that I'm not good at managing people, so everyone has to be a Contractor. I don't want to have this long notice period. I don't really want to deal with HR issues and employment issues and things like that. And I want to make sure that everybody we hire is excited about what we do or else they don't have to be here. I want to give them the freedom to leave. This is two way street. And I think a lot of people think, oh, if I hire contractors, they're not as dedicated. That is untrue. You can hire a contractor and have them be full time for you. You're just paying them as a contractor because they're not in your country. And they could have side projects if they want to. Every single person on our team, including our cto, my co founder, can have a side project if they want to. We encourage that for creativity. We but as long as it doesn't interfere with our customers and your everyday Eddie Webinar so I think you get to define what your contractor means in your company. And in many cases I find contractors to be even more dedicated because they can work on the thing that is just their expertise, not all the things you want them to work on because you own a hundred percent of their time, because they can do what they're great at for you and someone else, I actually think it's a win win. But I also think if you have a company, you should be very honest about what you're bad at and maybe not do those things. And in my case, I know I'm bad with emotions and managing people maybe because I'm brutally honest. It's like I'm unable to have that conversation and then I'm brutally honest. So then the contrast is like too big.

From all your experience hiring contractors and working with no employees because you hate managing people, what are some things like maybe two or three tips you have for people wanting to go that route? For contracting, you mean basically I don't want any employees. I want to work with people anywhere, work on my schedule. Nomad Remote what is the playbook here? Maybe the top four or five things to do to work remote, manage contractors, work with a bunch of generalists, top.

Learnings maybe if you're working with developers, it's going to be very, very difficult for you to hire someone directly. We always go through a development shop. We don't hire developers one on one direct. And the reason for that is because a lot of times developers don't work out in the beginning and then you have to swap them out and it becomes very painful. So if you work with a development shop they might have a hundred people and if someone doesn't align with your company, they can actually do the swapping out and there's a PM in the middle that helps with that conversation, which actually helps me with the people management. And you should always work with a shop that your friends have worked with and validate because there's so many out there, right? Every day on LinkedIn there's like 20 people that are like, hey, I can hire developers for you. My developers are the best. If everyone has the best developers, that would be amazing. But that's not true. So I think work with people and companies that your friends have worked with so that you save yourself months of pain of like trying new people. But I also think it's really important to be super honest and upfront about your company culture to make sure they fit in because it's a remote team. So for us it's things like we never micromanage. So you have to be self motivated. You have to be someone that really values being remote. So maybe you have a young family and you like the freedom. We don't care about the hours that you work as long as your deliverables are there. We don't have a holiday policy. But you, you have to be there for the customer. So just have like super clear expectations of what your time commitment and what your company culture is. Because it's super easy for someone to hear that and be like, yeah, I love that I am that person. Everyone loves that whole idea of freedom. But not everybody is made to be a self motivator. And it becomes clear very quickly once they join the team if they fit into that culture or not. But if you're not super honest and upfront about those things, then you can't bring it up later if they don't want to show up after 5 or it's a weekend so you can't reach them. But then there's a customer issue. So I think those are like the two main things is work with people your friends have validated and second, just be super honest about the remote nature of your team and what that means for their work environment and deliverables.

Starting a company with your partner. Conventional wisdom says it never works. A husband and wife or girlfriend boyfriend couples basically never works. What made you opt for this and what did you learn through the journey to make it work?

Yeah, that was an accident. When I was starting e webinar, if someone said, hey, you should start it with your life partner David, I'd be like, no way. Could never work with him. But actually I was so tired of having a co founder that I came into e webinar thinking I could do this alone. That was naivety on my part. I had two companies with the same co founder and we were best friends while we were building companies. But there were fundamental issues that we never resolved. And the thing that kept coming up was like he was a great engineer, but he was not a great cto. So he was a bottleneck for a lot of things. But he also didn't have experience working in other companies. I was his first work experience. So we just felt like that journey, our lives was over and that we had done some good work. So moving into a new company I thought, I don't want those same issues again, because for a non technical person to manage a technical team, it's not possible. So if you don't have a great CTO co founder who you trust, whose experience as a leader to manage a development team, you're going to have a really tough journey, which I did. So coming to this company, I thought I could just hire a dev shop to be my CTO co founder, cross unquote. And I can do what I do best, which is building the business. So I actually hired a dev shop, unfortunately, which my friend owned out of Canada, with the idea that after they build the first version that I would transition the team to Vietnam because it was going to be much cheaper. And David at that time he was a fractional CTO for other startups. He was going to be a silent advisor to see how the V1 product was delivered and then he would be the bridge from that team over to Vietnam. I think dev shops are really great at working on ready products, like building features of products, but not from like 0 to 1. And I didn't really know that to build a product from 0 to 1 really takes a lot of trial and error. And dev shops just don't operate that way. They operate on either hours or your project you're going to deliver. So they don't have time to do that.

Depends on the kind of dev shop you go to. And it could be very expensive because there's some dev shops that work exclusively with startups and they just help you validate the idea, build this mvp. But it's a heavy process as one of the founders needs to have a lot of product management skills, otherwise they'll go on a wild goose chase.

And that was a problem. So the product wasn't working. David was like, oh, they're doing this wrong, they're doing this wrong. They're making the wrong decisions. And at that point I've been with David for like four years. I knew he could code, but I didn't really know how well he could code. So we got into a fight this one day and I'm like, you know what, why don't you help? Because I don't know what you're talking about. You're just screaming at them but you're not coding and this is my friend's company and that he says he's going to handle it but obviously things aren't working. So why don't you help code? So within a week of him helping as a volunteer, the product started working. Even though I don't code, I know good software from bad software. One works and one doesn't. So then we had a very serious conversation at that point about why am I paying this company hundreds of thousands. Like it wasn't a small amount. Try to get this V1 out. But it's not working and the time to delivery is getting dragged on. Whereas maybe we should end that relationship. You can be my CTO and co founder. We can work out whatever works for you. But just know that you're coming in a year later. So that was how it happened. It happened by accident. And he at that point didn't have a full time project to work on. He was kind of looking for his next thing. But as far as how do we make it work, it just makes me cringe when I hear about husband and wife or like partner teams that don't have things documented. You need to treat your partner like any co founder and go through your lawyers and have all your shareholders agreement, everything like your vesting schedules, like everything documented. If this doesn't work out, no one's going to look out for each other if this relationship doesn't work out. So that was number one is everything was documented. But I also had a very honest conversation with him about how much equity do you need to feel involved in the business.

So it wasn't 50 50. What is that equity split and how do you decide? Especially with partner couples. Right. Because depends on your relationship. Sometimes it is 50, 50 on the personal side. But how do you decide then who is the CEO in your case it was very clear because you brought him in for a specific skill set. But then how do you decide what the right equity split is and how do you have that conversation when the person is your partner?

Yeah. There's only one way is honesty. Right. And that's exactly what I did was because he was there for the last few years of my previous startup and he knew that one of the biggest gripes I had was I split my company with my CTO when I built the business and he built the product. Those two things are very different. I actually don't believe that two co founders can have equal contribution. You're like, you're the CTO. A lot of CTOs don't build the business, they built the product. And the difference between that is a CEO makes sure there's money in the bank. The CEO takes all the financial risk. Mostly the CEO goes and recruits, figures out product market fit, sells the product, goes to the events, markets the product and then hires the team to continuously do all those things and delegate. The CTO maybe hires a development team and builds the product. Do you see the difference? One is the product and one is the business. He's 12 years old than me and he worked in Microsoft for over 20 years. So he knows the difference between the two. And I don't believe businesses are democracies. I'm not going to split half the company with you. I'm going to do most of stuff like I am. That's why I basically laid it out for him is these are the things I'm going to do. These are the things that I expect you to do. You can correct me if I'm wrong, but how much equity would you need to feel involved and as if you're part of the business so that you feel like you're a true co founder, knowing that these are responsibilities. So he named a percentage, we agreed on it, and that was how he came up with the split. I know a lot of founders who split it down the middle and eventually will be like, well, I'm putting in more work than this other person. And then they start building this resentment.

Me and Alex split it down the middle. Maybe this is a conversation for another time, but effectively Alex was CEO, I was president. We had some unique skill sets that were complementary to each other in the sense Alex was making sure operationally the company's running and the company was profitable and had money in the bank. And I was responsible for blowing up, meeting customers, press, evangelizing, doing everything that was front facing, willing the business into existence. And he was responsible for everything back facing that was making sure the business doesn't go to the ground. So even sometimes you run into those situations, we're 5050 and well, this is a conversation for a completely different episode. But in a situation like that, I've started to feel that even the founder CEO title sometimes is at loggerheads with one another as you scale a company to 10 million like we did and now it's over 20. Because the job of a CEO is to stabilize the business once you're at scale, especially once you're at scale. And the job of the founder is to inject new risk into the business like new products, new markets, new technologies, new ICPs is what we see. It's like having a title like CTO and chief luddite is what Jason Freed from Basecamp said, but different, completely different set of problems at a different stage. Because with 0 to 1 and a few million, several million, it was a good jam. But then once you get beyond a certain point, it's like, I'm not the person to be the CEO because I don't care about stabilizing the business. Then Alex, he doesn't draw joy in being the face of the company or doing anything that's front facing. And those are some things you need to do is you need to sell, you need to evangelize the company, you need to talk to investors, you need to talk to media, you need to pull the insights and bring it to the product team. You need to be out there. Right? Those are skills you need. That's why I brought this up. So different perspectives at different stages. How would you handle a situation like that? We were 50, 50 effectively. It worked well. And then of course we sold 52% of both. And then over time it wasn't the right fit for a company at scale where you mentally operate. 50, 50.

I mean, if you were to start a company today and you were going to be a CEO, you know what you can deliver for a company. You know your skills, you've got a huge community, you've got founder community supporting you. You're the creative go to market growth guy. And someone comes to you and was like, lloyd, let's start a company. You're excited about it. And he says, or she says, let's split in the middle. What are you going to say?

I wouldn't do it.

How would you handle that conversation?

I think now we're wiser. I often say this because this is a key question when coming up with founding teams. This is the most probably important thing when you're starting a company that nobody does. Great companies are built on great alignment. If you don't have alignment going in, meaning one person doesn't appreciate the other person for their engineering skills and the other person thinks this person is always overselling or not the best salesperson when you're poor and there's no money, you're going to make it work. But as soon as you're starting to do well and more people join, there's going to be a misalignment and that will be quite visible as you argue. So I think one of the key things is finding alignment. For me now, non negotiables is what are my values. Writing that down, it's beyond who does what, what are my values that I care about. I care about community, I care about transparency, I care about the ability to work from anywhere, autonomy, I care about companionship. I want to build a community led business and that requires a different DNA. And I also care about not going in the office again now. So those are some non negotiable values I have. But then there are skill sets I bring to the table. Now, even if the person has complimentary skill sets, but they don't align on values, I will never go into business because for me impact is more important than making money. I have this fundamental belief that if you focus exclusively on money, you make short term decisions. If you focus exclusively on control, you destroy relationships. The only way to build something lasting and be happy is, is focus on the impact. And I'm not saying money is not important, money is important. But if you just nickel and dime every decision, then you're not thinking about the big picture. So for me those values are important. Sometimes your values end up being in violent opposition of each other. But regardless of how great or skilled you are, because like you said, you end up earning the rights to have some non negotiables. But you're absolutely right, assuming there's an alignment of core values. Ben, if somebody is willing a business into existence, meaning has investor relationships, has media relationships, has a community, regardless, like I don't know if I ever want the title CEO. I love the title founder. I'm a zero to one person if I ever did. Again, I don't know if I want the title CEO. Now this is how the world operates where even if you're doing all the front facing work and bringing investors and willing things into existence, if you don't have the title CEO, people will not take your word seriously. Let's say in a board meeting, even if you brought the investors there, even if you brought all the key customers, brought all the key partners, the media, you run the community. Basically you're the face and you've willed it. And the other person has the title CEO, but they're doing all the back end and the infra and their operations just as a function of that person having the CEO title, the board will listen to the person with the CEO title. And that is the reality because the title matters. And so what I would do is I would find somebody with technical capabilities as a CTO co founder and it's clear that the company is four or five parts and how to divide that. But at certain point of scale, I would never give up the CEO title knowing now what I didn't know before or I would fight for that title if I was going in a relationship where I'm not the idea person. But what I would do once I have that title is never give it up and bring a really good chief operating officer, maybe at 4 or 5 million in revenue so they can do all the back end the grunt work, the things that are stabilizing the business, bring on a chief operating officer. So I could do the injecting the risk in the business.

Now that we've learned what it takes to lift a business, I actually recommend this to other people where you don't need to jump into a co founder split equity relationship. Today, the best way to figure out if you work well together is work with each other as the other person, as a contractor, pay them. You don't have to split equity if you're paying somebody. So let's try to work together, see if our values align and how well we even work together before we start signing contracts that we can't get out of. And then once you know you work well together, I want to be each other's co founders. And after working together, then you know how each other can contribute and where then you can have a much more informed conversation about what the split should be. But I think the whole myth of, oh, it's a co founder, I just split it down the middle. I honestly think that's bullshit. So that's kind of the conversation that I had. But luckily David was there in the last few years of my previous startup, so I really didn't have to explain this very much. But he also had an appreciation for what I had to do to lift that company from the dead and then eventually getting it acquired.

Because a lot of problems will come through. Right? Because the thing is, when you're poor, values are things that you don't focus on. It's like, I just need to bring food on the table. You're super focused on the one goal and so you don't think about values.

We're just surviving.

You're just surviving. Exactly. Like, who has that energy? Because especially us coming from immigrant backgrounds, we Know that when you're surviving, you can't have many options, you can't have negotiables, you're not thinking about values. But you know, in a founding relationship, I think that is the most important thing. And I say to people that don't read somebody's lips or what's written on the wall, observe the actions. So if a situation takes place and you're transparent and the other person doesn't like to share, then that's a red flag. If you're a people oriented person and you love to build a community led business and somebody else doesn't care much about people, then that's a flag. Because what will happen is it's fine in the beginning, but after your decision making is going to be very conflicted because say you want to announce something and it's always going to be why are you sharing that? People should be on a need to know basis. Or it's like, why are you giving this piece of information away? No, nobody needs to know that sort of thing. And so you got to think very deeply about values now. I love your lifestyle. After I left the day to day at post, I nomaded for eight, nine months. This wasn't intentional living at all. I worked and worked and worked and slogged and slogged and never cared about my family or anything for the longest time. And all I saw was work. And then of course we got into this conversation with the growth equity firm. They're going to buy a big chunk of the company. The due diligence process sucked the life of me. Covid was happening so we had to cancel the traction conference at the same time. So we took everything online and now rather than doing a virtual summit, we're doing two live webinars a week. So there's lots of stuff going on. And then the way the decision led up after the exit cashed out, I didn't spend any time with family. Said I'll take everyone to Bora Bora. That trip didn't happen because I got Covid almost died. We added 100 some odd people to the company tailspin. One thing led to another. I was at loggerheads with the new C suite, left the day to day operations of the company and I felt lost because I'm like, I sacrificed my whole life, my family and kids for this company and today the company doesn't need me. I'm no longer there. Prior to that, my daughter came and told me, dad, you never spent enough time with us, right? And I said, there's so Many people in the company. The company has grown from like 30, 40 to 130. We need to make sure we're doing right by them. And she says, why don't you work for somebody who thinks like that so I can have my dad back. Every time my wife went into labor, I was at a different offsite and had to fly back to see the birth of my kids. So when I was at loggerheads with the new C suite that came in and I recommended the board, they fired them. Obviously, their reaction was, dude, like, what's wrong with you? You've had a very stressful year, and now you're at loggerheads with these people who have not even been in the seats for two months, but you don't want them there. Why don't you take a paternity leave and we'll figure out the right role for you when you come back. Now, as a founder who helped will this thing into existence, build the community, everything. When you say take a paternity leave, it's like the writing's on the wall. So go home. I cry. I talk to my wife, and I deeply cry. And I said, I'm sorry for all the times I wasn't there for you. Today, the company doesn't meet me and I have nothing. I've lost everything. So I ended up very depressed because I didn't live intentionally and I came into some money. So I randomly called friends and say, show up here. I'm going to pay for the hotel, or I'll just fly you there. Come, let's party. Let's party. And this is how insane I became. I not only became overweight and drunk, like an addictive personality, because I just felt like I didn't enjoy my life last 15, 20 years. And my wife, being a physician, understood what I was going through. But I was at a conference in Romania after conference speaker retreat, and we're in the middle of nowhere, a few hours from Bucharest, maybe four or five hours. Two in the morning hits, and I get a call from some friends saying they're in Costa Rica now. Romania to Costa Rica, right? And I'm frantically calling an Uber, and there's no Uber coming for half an hour. Half an hour later, an Uber shows up, and the conference organizer and others who are hanging out in the pool at 2 in the morning, like, what are you doing? I'm like, hold on a second. I tell the Uber driver, can you give me five minutes? I've been trying to get an Uber for the longest time. I book my flight to Costa Rica. When the Uber shows up, I'm like, guys, I'm heading to Costa Rica. I have a few friends. I'll see you. And I get in the Uber, three hour trip to Bucharest, make the 6:30 or 7:00am flight, and I head to Costa Rica. That's how crazy I became, because I just felt when that incident happened that I hadn't enjoyed my life as an immigrant, moved to Canada and then the US it was like school and then work and then company after company startups. I only ever worked at startups after graduating, so I felt like I didn't enjoy my life and I needed to live like the snowman. And if I could go back in time and change, I would live very intentionally. Optimizing for fun and advocating that for yourself and the team. Walk us through that journey. Because today I can't keep track of where you are at any given time.

So I was still in my previous startup and David and I, we just had a rolly because we hate checking luggage. We realized we were paying an crazy amount of rent just for a room in a shared house, which I started at a co living space. And I was just putting the same amount in Airbnb to see where else we can be. And you could get these incredible apartments in Cape Town or Santiago or whatever. So we're like, why don't we just do that, Put a few boxes in storage and just live on the road out of this thing called Airbnb. And then that ended up being three years of our lives. And then we found Amsterdam along the way and built a community here. So we have a home in Amsterdam, but we actually travel nine months of the year. I never traveled as a kid. My dad hated traveling. So my first real trip was in my mid-20s when I went backpacking to Europe by myself for two and a half months and then really got to see the world. And I think that we spend so much time building our business because we want to be free. And then as our business grows, we keep working in the business and then we're not free. And then we forget that we started this to be free to begin with. So I want to make sure that I am, and we are living the life that we intentionally wanted to build by doing what we do every day. Because there's this whole thing about, oh, I can do this thing later, I can do this thing when I hit 2 million or I can do this thing when I sell my company. Well, you don't even know if you're gonna be alive tomorrow. And that is the truth. So if you're not living now and spending time with people you have fun with and love now, and going to see the places you wanna see when you're young and can walk around and can adventure, you're gonna miss out on all this stuff. Because we forget that when we're building our company, life happens in parallel. And as founders, we're very good at delayed gratification. While our friends are getting married, having kids, buying their first apartments, going on all these trips, you're like, it's not my time yet. I will do that later. And then you lie yourself enough that you feel like that's your normal. That is not normal. So I realized this when I left New York to travel full time is the world is so much bigger than work. That was the first time I realized that I don't have to work all the time. My life doesn't have to be optimizing for dollars, fame and fortune and success. None of that stuff actually matters because all of that stuff enables the things that are important, which is just life just experiencing. So that was really a fundamental shift that I had, I guess, in my mid to late 30s. And I want that for other people. I want to be an advocate for that. Because I was the founder who did nothing but work. Because I was in survival mode and then I wasn't in survival mode, right? So again, earn privilege. It wasn't until Spatio broke even that I even had the mind share to think, what do I want? And that's actually why we left New York to travel full time. Because the day we broke even, I thought to myself, okay, I spent 10 years paying other people's bills. If this is going to be hard, what's the one thing I can do for me that's going to make this more fun and traveling more and living on the road was something I always wanted to do. That was kind of the thought process. And now that my priorities, I feel like, are more straight. Of course work is important because everything I love is bought with cash, right? With money. So I don't want to ignore my desire for financial success. It's just money is no longer the thing I only love. I actually love living and spending time with friends and family and traveling way more. And I do what I do every day because I want more of that. And I want to make sure everybody on our team knows that these things are important. And that's why we don't care if people leave on a Friday or don't come to work on a Monday. As long as they tell us where they are. That's why we don't have vacation policies or we're very, very relaxed. Because we want to make sure that the way we live gets distilled to the people that are giving us their time. While we are paying them to be part of the team, I think it's more important that they're giving us their life. So this is a way that we give back to them.

Leverage community led growth to skyrocket your business. Hey, traction fam. It's your host, Lloyd Lobo. I've just released a book that I've been working on for some time. It's called From Grassroots to greatness. Master 13 Game changing rules from some of the world's most iconic brands like Apple, Atlassian Crossfit, Harley Davidson, HubSpot, Red Bull and a lot more. So you can attract super fans of your own that will propel you to new heights. Your support would mean the world to me. Please grab your copy at from grassroots to greatness.com well said. You know, all my life I chased success looking for happiness. And success was other people's definition, which is money, which is promotions, which is exits, whatever it is. And then when that came, I ended up depressed. And then I realized success is not money. If money doesn't buy you freedom, success is freedom. The ability to do what you want, where you want, with whom you want, when you want, on your time, in your prime, in your prime is key. Because the western dream, the American dream is what all my friends who live in the Bay Area, right, this is why I ejected out of there. They wake up few hours early so they can drop their kids, get food ready and commute. Long commute, Bay Area traffic, horrible. Any city. Then they stay late, pick up their kids running around traffic, et cetera. And in our immigrant cultures, we've been told that go to work an hour early, be the first person to get there and the last person to leave. Then you commute all of this stuff. Then you have your mortgage, you have car payments, you have all these things that you need to pay for kids, school and then sales tax, property tax, income tax, federal and state. You're already out more than 50% so you have just enough energy to have one nice dinner on the weekend. And, and Sundays, I kid you not, I used to dread Sundays. I had like Sunday PTSD because it was all these things I needed to do for the rest of the week to prepare, like Costco line and all of this. I had Sunday PTSD for the longest time. When in reality you can just figure out what would improve your companionship. So there was a study done on the blue zones, the five towns or whatever where people live functionally to a hundred. It's called blue zones. And they had nine common traits. And four or five of those nine common traits were social things, community related, companionship, people who you hang out with, how you live, walking. Now, if you live in the suburbs, you're not incentivized to walk. Where I lived in the Bay Area, Melissa, I kid you not. It was five miles to get to the main road. It was like 15 minute drive to get to the biggest grocery store. Yes, it was on a big golf course on the hill. It looked good, but it's not conducive to walking around. Whereas if you live in the city or somewhere where you're functionally walking, your health is already better as a function of just meeting people every day and seeing them on your walk. Your mind just expands. So this is something that I would do hands down, and I recommend people to start with, like, what is your personal definition of success? Think about what you want to do at 65. Because you know, at 65 you're not going to be able to do half those things and figure out, how do I do them today and build my work around that intentional life. So I love that. So bootstrapping then versus raising makes a lot of sense because if you want to live intentionally and you want to do some of the things you've mentioned, you can't raise venture capital because it's triple, triple, double, double, double. It sounds like the Tim Hortons.

Yeah, right. Like if I have institutional investors, like a boss, I wouldn't be able to do any of these things. They'd be like, you have to have an office, you need to hire people, employees work harder for you. I wouldn't be able to work four days a week or just bounce whenever I want to because I have to at least put on this dog and pony show to be like, there for my team. I wrote about this very recently. A lot of people think bootstrapping is a financial decision because, like, oh, you want to keep all your equity. That's not true. Like, I think for a lot of people, including myself, bootstrapping is a lifestyle choice, whereas raising money is a financial decision a lot of times without consideration of the lifestyle that comes with it.

I want you to pause for a second because you use the word lifestyle and I want to say this out loud, that the VC world and the Silicon Valley and the tech world will tell you A lot of the times that this is just a lifestyle business, don't listen to that. Having a good lifestyle is not a bad thing. They're saying it because if you live intentionally and build a business that you want to live and work for whatever that is. But if, say you want to build a business which is around your life, it's not VC fundable, it doesn't generate a return. And I'm not saying they're wrong. They take a lot of money from the market and LPs and institutions and they get that money based on the fact that they can make a return. So they have to push you to go triple, triple, double, double, double and IPO. But the reality is 99% of the startups that go on that journey, they fail. Like, I've only worked at venture backed startups, they all failed. And the only company that I worked for that did well and brought me to financial freedom was Bootstrap. So that just tells you what are the odds here, right? Of course you'll hit the lottery. You may get an Instagram or you may end up at a Google, but the odds are against you. So think about the life you want to live. Think about what your definition of success is before you go on this journey. Because when you go into a relationship with a VC or any conversation, you're automatically misaligned. They want to generate the highest return and over time they will push you for that. And you are not thinking that way. That seven or ten years I want to have the highest return. So what do I do? Most founders don't think that way. The best thing is look at the term sheet. The term sheet says in seven or 10 years they can ask you to sell the company. That's why Zoho CEO said no to a VC term sheet this big time. You know, let's go. Unnamed VC was like, you're going to say no because of a standard clause that says we can have you liquidate in seven or 10 years. He's like, I don't like this clause. I'm married to my company. And he refused it and he's bootstrapped to a billion.

Anything under a billion is a lifestyle company. I'll take it. And they diminish the value of that because it's good for their business. They make you feel like you're not ambitious enough. They make you feel like you need them and this is the way to success. And you go and beg them for money and now you're in the race and that's good for them. But it's not good for you. So exactly. That is like ask yourself the life you want to live. What is the life I want to live for the next 10 years? Do I want a life, do I want to socialize or do I want to succeed so bad that I'm willing to work and dream this 247 and either crash it or IPO this thing and maybe you'll sell somewhere in between. If that gets you excited, right. If that's what you really want to do, then you should go and do that. But I think unless that really gets you excited, that's probably not your best path. Nobody really believes you, right, when you say this to them. I preach this quite a bit, but nobody really believes you. I don't know if you have that experience.

I don't know because I think it's imbibed in us to think about what? Working, working, working. My parents still today, now, for the longest time they didn't know what I did for a living. Okay. And they kept saying, get a job, it's not nice. Your wife's paying the bills, yada, yada, yada. Startup after startup that I worked for that didn't work out. The salaries were so low. And then with trapping boast was a hardship. Never had the greatest money for the longest time. And then when we did the growth equity deal, it was all over the press and everything and they finally, they were happy because okay. Came in with some money. But now that the last two years I've been doing nothing, just launched a book, chilling. They asked me, they're like, you're so young, how can you not do anything? Why are you just dipping into the money you made to pay for your lifestyle?

Because I have a lot of it.

Yeah, they keep saying this so they don't understand because the generation before us cannot comprehend this. And it's been imbibed in us to work till you're 65 or else. There's no or else. Although a lot of people are coddled and everything else. This is where the new generation probably will live more intentionally because they genuinely care about experience and self care more than the generations preceding. But there has to be a balance. It's not like, hey, I'm going to live intentionally and do self care and do all of it. But just check out when it comes to work, there has to be a balance. Let's go unnamed, but in all your VC experiences or dealing with investors, what has been the worst experience you've had?

Just institutional VCs. I haven't dealt with a lot of VCs. But some experience comes to mind because when I was running Spatio, I did try to raise money because I was so poor. But while I was raising money, I was also growing the business, so I was kind of running both in parallel. And then I started hitting part of market fit, selling more deals. And then eventually we broke even. So then I didn't need other people's money anymore. And that's how I know the difference between trying to raise money and actually trying to grow a company, which the latter is actually much easier. But I remember, like, when I went to pitch VCs, I was living in New York, 9 out of 10 of them would be like, maybe you should just work for one of my portfolio companies instead. And you're in a pitch. So it's very demeaning and really discouraging. Not only are they like, okay, well, this is a shitty business, but they're like, well, why don't you just stop what you're doing and just work for my portfolio company? Because you're a great salesperson. You come out of that feeling useless. Right. And worthless and dumb that you're spending all this time building something that they don't believe in because you want that validation. And maybe it wasn't their fault. Like, I don't think that that was, like, the intention to make me feel bad, because ultimately their priority is in the companies that they invested in. But it made me feel bad as a human being and as a founder.

That's a very condescending thing to say. Go work for one of my portfolio companies, which I see happening every so often, that conversation.

Yeah. And actually, I had one private investor in Spatio that really lifted us out of debt. He was just a rich guy and he was kind of an angel investor. He was the one person that actually gave us money. And it was really like a turning point. But he was so rich that he had a guy running his fund, like his bank account. And this guy was operating as his fund manager. But I'm not kidding you, he would call me every Friday. And this is from having zero investors to, like, now this one angel investor that I had to manage, he would call me every Friday after work and scream at me about how my accounting statements are not in order and what am I going to do to market this company and what's the future? Because he was getting pressure from this rich guy that had never invested in a startup before. So then he immediately wanted his money back. So while I didn't have real investors, that micro experience made Me realize that there is no free money. And I know that not everybody's like that, but that's my personal horror story is just like, okay, so you gave me 250k and I gave you the right to call me every Friday after hour and scream at me about my accounting statements, which I don't even really know how to read. As a founder, this is the one.

Thing I want to say. I have now lived in several cities across the world. Like you have, probably a lot less than you, but definitely like Kuwait, Dubai, then Toronto, Vancouver, Calgary, New Jersey, Philly, San Francisco. And I'll tell you one thing, early in my career, I did a lot of work with Startup Weekend. So I went from city to city, every small tier city that was out there in the States, some in Europe as well, to volunteer and do startup weekends. It was a great, great community. And what I found is that in these smaller cities that are not significant startup hubs, it's easier to come across people like that. And the one thing I'll tell you is just being in and around Silicon Valley's ecosystem, no matter what is said, people are not like that. You'll take money from investors and it's like they won't even check in with you. Sometimes it's like you gotta update them. It's on you. I'm in a number of investments with other angels that they even forgot. And so I think that depends on the values and the DNAs of the environment you grew up in.

Well, I took money from someone who's never, ever invested in a startup. That's a red flag. But I didn't know and I was so desperate. And when you're desperate in survival mode, you're not thinking again about values. You don't have time to ask your friends. Someone's like, okay, yeah, I'll save you. Not only was I personally in hundreds of thousands of dollars worth of debt, I hadn't paid my accountant and my lawyer for like three, four years up to that point. And these are people that keep my company running. So as soon as that check came in, I think close to a hundred grand of it went to just paying debt just to get our head above water. And then we were able to hire, you know, the first developer. So I wouldn't have changed anything for it. But I did learn that shareholders are important. Equity is like toothpaste. Once you get it out of the tube, you can't stuff it back in. Whether it's an institutional investor or friends and family or an angel investor, you need to Be super careful whether there is value alignment, whether they're experienced, it doesn't even matter if they're going to add value. It's are they going to take it away? Are they going to make your life worse by being in it? And that was my micro experience, but it also made me a lot cautious about who's on our cap table. And I think that was a really important lesson to learn.

You said it right. Equity is like toothpaste. I love that. So be wise in terms of who you bring on as a partner. And once you make that decision, just mentally clear ahead because you've done it and now you got to bear the cross of your decisions. Another unconventional thing you did was you started a company without talking to a single customer. Now there are some folks who advocate for that, like Keith Raboy, PayPal mafia, who's been built open door and now open store. And prior to that, LinkedIn Early Team, PayPal Early Team. And he says making a startup is like making a movie. You don't go and ask what movie should I make, what should the script be, what actor should I cast? You have a great vision and you execute on it. You build a team and you produce it and you market it and cut a trailer that interrupts people. There are some great startups Keith has done, but for the vast majority of the people, if they don't have experience, they don't have the resources and the funding or the know how to do that to make a movie, it takes a long time.

Yeah, but I mean I think Keith is like a top 1% of 1% when he does this. He is so confident about the Blue Ocean thing that he's putting out there that is going to create a before and after in the world. I'm not as ambitious or as experienced as Keith, not as bold as him, but I was able to do it because I didn't pick a brand new product. And I think that was something that I learned is in my first two companies within real estate. I created a Blue Ocean product and I thought, oh, that means more customers, no one's going to compete with me. But it's actually worse. Like the reason why it took me so long to find product market fit was because the education cycle to close the first customer was so long and then you repeat it for the second and the third. So coming to E Webinar, I actually have a friend who is a wizard at this. He is the absolute best second mover I've ever seen. He has built multimillion dollar businesses by being the second mover, because his whole philosophy is, someone's opened the market for you, so someone's done all the research, take their product, make it 10 times better. And actually that was a light bulb moment for me. I talked to him after I sold Spatio and I'm like, you're so right. So I promised myself I would never do a blue ocean opportunity again. Not only did I know the problem that we were solving intimately, well, with e webinar, there are products out there that I thought sucked and that I could make 10 times better. So I didn't need to talk to people to give me doubt. That was actually the primary reason why I didn't. Because if you ask someone for feedback, they love criticizing you. People love being in a peanut gallery. I don't want to give them the opportunity to beat me down when I felt so confident about the product I wanted to put out there. So I came at it from a different angle. I love what Keith said about why would you ask customers for feedback? You just put a product out there and you market it and you make them buy it. And actually that's what I'm really good at is crafting pitches to sell something that doesn't exist today or is like about to exist. But I encouraged founders to think about that. Do you really want to put out a brand new product or a product that exists and then you can make it 10 times better?

I have somewhere meet in the middle kind of view. Right. Because what we did with Boast also was a very crowded market. R and D tax credits, every big four was doing it. We just picked that market. We knew there was a pain point because it sucked and we just made it 10x better. We didn't pick a new market or a new product or create a new category, whether the function of it. R and D tax automation ended up becoming a category because it was just a service before. But new entrepreneurs who haven't earned the right, like you or Keith, it's important to talk to customers because if you don't talk to customers or just don't have this ability to communicate, then it's going to be very hard to will something into existence. Because everything is communication. Convincing media, investors getting feedback, later on, getting on podcasts, evangelizing VCs, whatever it is, the early employees to work on low pay, it's all communication.

Well, you need to have confidence that you can sell it. I did. But yeah, if you don't have the confidence that you could sell it, then you shouldn't do that. But I Remember watching, you know, Jack Ma, like the Alibaba founder?

Yeah, yeah, yeah.

I remember watching. There was like a documentary made on him, like years ago, like he was coming with Alibaba to compete with ebay in China. And he said something that I never forgot is I don't need to prove the market. Ebay already did that. I just need to prove how big it can be. And that's amazing. That is kind of in line with my friend who's like the best second mover is like, take something that's out there, cut down years of research, and just do something better.

Most companies have been second movers. There was products before Airbnb. There were products before Zoom. So assuming that they created categories is a hard one. HubSpot created a category with marketing automation, but in most cases, people. For most products categories existed even before Airbnb. There was VRBO and other things. They just made it better. As we close out, I know you gotta run. I want to dive into the future of go to market. Brands centered around the company versus brands centered around the founders, the people. You are banned on LinkedIn. Then something happened and you've become a viral sensation. I'd like to say you're the fastest growing LinkedIn influencer of all time.

That's a big statement. I'm not sure if I can live up to that.

And then you're a podcasting superstar. You're on hundreds of podcasts and today, where media is bought, you've earned it. You've earned the right not only to live on your own time, in your prime and live intentionally, but you're also earning a lot of media. You were banned on LinkedIn and then you became a viral sensation. Break that down for us. How did that happen? And the future of go to market centered around people versus centered around products.

I just showed up every day. That's the net of what I did. Like, I realized I was running out of tricks to sell my products. I didn't know how to sell it through inbound. I'm a sales led founder. I'm from a sales led background.

That sales led experience is what gave you the confidence. I was an engineer and the first job I took because I asked a founder like yourself what's the best skill? And they said sales. And I learned to sell and nobody would give me a job as a software engineer. So I begged my way into cold calling because they were like, awkward engineer, he can't be an ae. And you learn to pivot on the fly and polish your messaging. So we went Back to this confidence. Like I was confident and you brought up Alibaba, but we ignored a good part of your journey where you were a sales.

Yeah, I'm a salesperson.

The confidence comes from that.

Yeah. So I was running out of tricks because nobody picks up a phone for a hundred dollar product. And I saw that all these people were writing on LinkedIn. And then it became more than a resume site. I hadn't logged in for years before that. So you actually told me about Justin Welsh. I started following his content. He had a course on how to write on LinkedIn. I took that, took two weeks to kind of go through all the videos and the exercises and I just started posting on LinkedIn and four to six times a week, every week since mid June of last year. So it's been 14 months. And I just try different templates and things that work for me. And I would consider myself a writer, but not publicly. I write a lot to myself. I've written a few articles before, but takes a lot out of me for me to write, but I enjoy it. So Justin basically says, like, pick an expertise that you can write about that attracts the audience you care about. And since I bootstrap three companies, naturally I'm going to write about my experiences. It's all these stories that I'm talking about with you. I just wrote about a mini story every week, a few mini stories here and there. And a couple months ago I wrote this thing just pounded out in 10 minutes about shocking surprises on our way to a million. Somehow that went viral and then I just copied the format on a new thing. And I've been doing that week over week now. There's no magic bullet. It's not like I try to hack the system or I try to write for reality. Actually, like LinkedIn does not not want you to write for virality. They want the right content going to the right audience. And viral content is an indication to them that you're trying to trick the algorithm, if that makes sense. So you really have to write authentic content. So I want to say that I write from my heart and I don't write from my brain. So every week when I write a piece of long form content, I get a feel for what inspires me that week. And that is the thing I write about. But it's just unconditional consistency, my friend. It's just showing up all the time. Even when I don't want to, I show up.

I've had the good fortune of working with Jason Lemkin as a mentor, as a friend as a guide for a very long time. And the one thing I observed, and he says this a lot, is consistency is the magic ingredient that turns small actions into big achievements. And he was posting on Quora, writing two, three posts a day every day, and he actually seeded it with questions. And he blew up on Quora and he eventually hosted a meetup and a lot of people showed up and that transformed into Saster. But he still writes today. There are some posts, maybe somebody else writes, but I know when it's him written posts, he writes at least one piece of content every single day. And that consistency, the compound interest on that is really, really key. But the other thing you said was, I'm a founder. I was just writing my learnings. So you had probably an ideal customer profile in mind. You were writing for a specific audience. You're not just writing for everybody. You're writing for a specific audience. And you are adding value and you're doing it consistently. And now you have this audience forming and that audience is now interacting with you. And I can see if Melissa does a meetup in some key cities where your audience is, people will congregate and that'll turn into a community. So I love this. What is your take on brands centered around founders and brands centered around the company or the product? Because I'm seeing that shift with a lot of folks with Andrew Gazdecki, with you, and a lot of influencers out there that are just imbibing their brand, like Sam Jacobs with Pavilion. I know more about Sam Jacobs than I know about Pavilion. And as a function of Sam Jacobs, I am checking out Pavilion.

I think nowadays it's not just tech companies. We care about the people behind the product. If I'm buying this shirt, where did it come from? Who's the founder? Who made it? What material is it? Is it sustainable? Does it save whales? I feel like there's a fundamental shift from consumer goods a few years ago till now. When people invest in a company in a product, they want to know who's behind it and are they legitimate. Can I trust this person? It's all about trust. Do I want to invest in this person? Do I feel close to this person? It's really weird because I feel like a lot of relationships have moved online and there are so many people who I consider friends in my peer group, in my communities that I will never meet in real life. That's kind of cool, but it's new. So I think when you put yourself out there, like publicly and center the message around you, people feel connected to you, as if you're their friend. And people want to buy from their friends, they want to support their friends. And I get that feeling as well. We recently chose to sign up for User Pilot. There are probably 10 other companies that we can sign up for. But I've interacted with her head of marketing, Emelia. I feel like she's my friend and I feel like if this product fails that she has my back. And that's how I made that decision. Of course it has to be a good product as well. But that's how I feel about how people make decisions today is they no longer care just about how good the product is. They also care about the humans behind it. And any executive, any founder who is not putting themselves out there building their own brand, letting their customers know that they're here for them is I think missing out on the future of marketing is personal. So I would encourage anybody listening to this is to start doing that because it just makes you real people feel like that about you as well. And I also have seen what creators like you, like Justin, have been able to do with such a big audience and community. You literally can put anything out there right now and you can't fail because you have people that support you. And I want to be in that position. I might not be running e webinar for the rest of my life, but if I ever choose to do something again, I love for there to be a built in audience that I can either consult with or put a product out to. Maybe I can be a solopreneur, but I feel like a lot of this is like seeding my future.

And it's a great way to wrap up is it's neither the destination nor the journey, but the companions that matter the most. And I put out the book today, the pre release for the book From Grassroots to Greatness, which is all about community. And I found one very common theme across every obscure idea that turned into an iconic brand or a religion. From Christ to CrossFit, somebody buys your product or listens to you, have an audience, you bring them together, it becomes a community. That community comes together to create impact. It becomes a movement. And then through rituals and undying beliefs in its purpose, it turns into a cult or a religion. So thank you so much. Any last piece of unconventional advice that founders ignore but shouldn't.

This is something that we touched on earlier. This conversation is like don't pick a company or a product because there's market potential. Right? I think every advisor or whatever startup book you read teaches you how to validate an idea with customers and approach it from a very professional business like revenue angle. I don't think that's the right thing to do. I think the first question you should ask yourself is what makes me happy, how do I want to live and what can't I live without? Once you have those things in front of you, I think you'll realize that 95% of the products that are out there don't fit your own idea of personal lifestyle success.

This has been fantastic. I look forward to doing many more of these. Melissa I know it chewed a lot of your time so have a great one. Love and Peace.

Thanks so much.

Lord, I need some Traction. Leverage community led growth to skyrocket your business. Hey Traction fam, It's your host, Lloyd Lobo. I've just released a book that I've been working on for some time. It's called from grassroots to greatness, Master 13 Game changing rules from some of the world's most iconic brands like Apple, Atlas, Atlassian, CrossFit, Harley Davidson, HubSpot, Red Bull, and a lot more so you can attract super fans of your own that will propel you to new heights. Your support would mean the world to me. Please grab your copy at from grassroots to greatness.com thank you for listening and we hope you enjoyed this week's episode of the Traction podcast. If you enjoyed the show, please leave us a five star review.

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