How $4b Webflow Founder failed 3 times before getting it right - Vlad Magdalin

0:03I never wanted to start a company. The series of situations I was sort of put into, you know, the need to try to make income created this impression in me that nothing was like off the table. As I started going to college, as I started to have some work experience, I see this problem, this actual problem that exists in the world that I can see a much better way of solving and it absolutely should be solved. Welcome to Secret Leaders. Today, I'm joined by Vlad Magdalene, the co-founder and CEO of Webflow. With a recent valuation of over$4 billion, Webflow is pioneering the no-code movement, and it's no secret Vlad is leading the charge in this space.

0:44After leaving the USSR at the age of nine and immigrating to America, he realized there was strength in combining technical and creative disciplines. As such, Webflow was born. And after three failed attempts to get the company started, thankfully the fourth was a success, and we're able to hear his story today. So Vlad, welcome to Secret Leaders. Thank you, Dan. It's such a pleasure to be here. Dude, so I'm in so many places to start. Three failed attempts, USSR. I mean, let's, you know, excuse my basic bitch interest, but let's talk about USSR moving from there to the USA, assuming that's quite a formative experience.

1:25So talk to us a little bit about that. Yeah, it was absolutely a very formative experience. And we were just insanely lucky to even be able to get into this refugee program that even allowed us the opportunity to come to America. But I think that the biggest thing that that entire experience instilled in me was just the value of hard work because my family came here. You know, my parents had six kids. They were in their early 30s and, you know, starting a brand new life. They didn't speak the language, didn't know anything about, didn't have any degrees, didn't have any, you know, marketable skills.

2:04So it was a it was an adventure. Didn't feel like an adventure then, but in hindsight, an adventure in, you know, seeking new ways to make a living, try to figure out how, you know, seeing seeing my dad try to figure out how he can like get different forms of income without first speaking the language. you know he started to learn computers started to pull me in into more even as a kid into more projects to help him figure out how to you know try to take on new jobs or do like little side gigs and through that I learned design I learned this application called CorelDRAW where I would learn you know like vector illustration tools that then led to web design over time that led to different side jobs that taught me so many different skills.

2:57My parents would clean offices in the evenings and bring the entire family. We would kind of be cleaning these dental offices to make sure that our family had enough income to keep going, pay rent, et cetera. And I think through that experience, it was just part of it, I was just being a kid, but another part of it just seemed like this is just kind of what you had to do, what families had to do in order to survive and eventually thrive. And I think that just taught me that, you know, even when you don't have a specific skill, when you don't know what you're doing, just by taking that on and leaning in, even when you're kind of forced, there's so much that you can learn.

3:42And through that opens up more and more opportunities because you learn how to work, you learn how to do more and more things that gives you a bigger toolbox of, you know, what you can take into the next thing. But over, I think the biggest thing that it taught me actually is just the, how much luck plays into almost all success. Because had I, had my family not been able to get here, which kind of was a fluke in a lucky accident, my life would have been completely different so i can't claim a bunch of credit uh for you know the things that a lot of the things that i've done because so many of um so many of those things are a result of just being so incredibly lucky to be able just to be in this country and a big family right so you said six siblings six siblings five siblings so six kids total which is kind of a small family for uh for my where i grew up uh in russia okay terrifying thought my aunt has 13 children you know what i told someone a story yesterday about how i was watching a new jamie fox film called the burial and there's a story in that the main character in that has 13 kids i was like i've never heard of 13 what the hell and now you're here telling me it's yeah what the hell it's big i am i've got one daughter and I'm like it's quite a lot it's quite a lot that's so funny um okay so your small family of six um what like what about being uh one of six like do you feel like there's part of you know I guess you've just described luck and the question is if you're willing to share but you know how do your siblings uh equate as well the idea of luck because I'm assuming not every one of them has a four billion dollar company um not trying to make you turn on your siblings on audio podcasts but it's one of those things isn't it where it's like yeah there's luck but there's also how you seize the moment and actually even down to like where you are in the sibling pecking order and all of these things that like help you defy the odds against someone else right and so i guess i'm trying to get your perspective on how much is luck and how much of it is actually uniquely your attitude?

5:56Yeah, that's a very interesting question. Well, first of all, I'm second in the pecking order. My older brother, you know, he's totally different. He ended up, I think I played the role as we were growing up in America of a little bit of like de facto older brother in the sense that my actual oldest brother was like so into reading books. He didn't, he was sort of like more, more isolated, but my parents were really strict in the sense that, you know, they needed to make sure that there was like relationships with our parents were like more transactional, right? Like in, in Russia, the reason you have so many, or at least where we grew up in like this super tiny village where everyone had their own farm, like it's sustenance farming, right?

6:46So you had kids in order to have more free labor, essentially. I mean, there's more mouths to feed, but you also get kind of the economies of scale. And our parents were in America were all around like, you know, they would just leave to try to go work, et cetera. And they would come back to expect like a clean house and, you know, homework to be done. And I sort of took on the role of the main kind of like leader slash enforcer because I didn't want to get get in trouble because we would all get in trouble. There's like corporal punishment was a normal thing in our culture where, you know, I took on this role of making sure that the house was in order.

7:26So that kind of gave me some some sort of natural leadership skills because a primarily because I didn't want to get in trouble and I didn't want my siblings to get in trouble. and and that I think that sort of differentiated me a little bit but funny story is one of my brothers is my co-founder so he uh this is my younger younger brother so a couple siblings removed um and we started this this fourth iteration together um and and that's because we worked so much together in like some of these projects that my dad took on and uh we just kind of had to whether it's for like businesses or like the local church or uh something that my dad needed help with it kind of like created this bond that we all sort of had this responsibility to work on this stuff together um but i think the the overall experience like i think they were all say we were so freaking lucky to um to to be given the the opportunity that we were maybe maybe it's a little bit different than like the younger the siblings get because i was nine years old when we left some of my siblings were like two or three so they don't they don't even remember what life was like compared to what we experienced in Russia.

8:39But, I mean, I would still think that most of them would attribute our journey to luck and some combination of being forced to work hard when push came to shove. But I think maybe uniquely had a little bit of a, because I was second oldest, had more of that responsibility to uh lead the family or lead the siblings when the parents were uh were not in the house got it okay um and you know also timing right like jokes aside but if you'd have gone to i'm sure uh people uh coming over to america from russia right now have a much harder time uh with that narrative and also much more difficult time just to be russian in somewhere like america i know that you're russian and ukrainian so you have like the both sides of the experience, but I actually would love to hear from you what your view is on that and having a foot in both realities as well.

9:40Oh, that's a deep topic. I mean, not just like the kind of the identity of coming from Russia, but for me, especially my full name is Vladimir, which is like Vladimir Putin, right? So like kind of dealing with that piece of kind of comparison to Vladimir Putin and sort of that sense of, you know, am I ashamed of that name? Is it something that brings a lot of kind of judgment or condemnation or maybe certain assumptions that people might make? But honestly, it wasn't that different when we first came in 1991 because that was like shortly after the Cold War. And the kind of collective psyche was that, you know, you see Russians as bad guys in movies.

10:31And there's kind of all of those jokes that came with like, okay, you know, the Russians are coming, there's like an invasion, etc. But I think the sum total was even though there were some of these jokes, some of these assumptions, some of these stereotypes, the vast, vast majority of people, once they, you know, got to see who you are as a person in this country gave us the benefit of the doubt. Like they, they came with, you know, acceptance and, and, you know, this positivity and grace that I think was very different from the stereotype. So the, the sum total of it was that, yes, we had some, you know, some some kids and sometimes even older folks sort of bullying or uh raising these you know stereotypes and questions uh that that made us feel like we didn't belong here we shouldn't be in this country etc but that was like one percent out of the the sum total of interactions we had with um everyone else who was like deeply accepting and and very um happy to see us like succeed and and you're in the west coast right exactly yeah so it may be different if i speak into you and Mississippi or something but yeah understood okay yeah so let's talk a little bit about then growing up as a Russian kid in America and I mean the land of ideas like the right place to be for building a company like what Webflow became so talk to me a little bit about getting into that journey.

12:08To be honest I never wanted to start a company like that wasn't a that wasn't something that was, you know, I saw various people in kind of the area where I grew up in Sacramento start businesses, but there were things like a dentist office or a, you know, a video, videographer making wedding videos or something like that. So that was never really an appealing path for me. I was just always assumed that I would go, you know, grow up, go to college, get a job, work a regular job, et cetera. But I think the series of situations I was sort of put into by my dad, by, you know, the need to try to make income created this, you know, impression in me that, you know, nothing was like off the table.

13:00Like if there was a problem that I had a inkling around being able to solve, like I could figure out a way to solve that problem. And it was only over, like, as I started going to college, as I started to have some work experience, that these ideas for what Webflow eventually ended up becoming started to manifest. And it was mostly around, it was still like the idea. It wasn't like, I want to go start a business. It's like, I see this problem, this actual problem that exists in the world that I can see a much better way of solving. And it absolutely should be solved. So that started the ball rolling around, like, how would I actually, you know, start to solve it?

13:43And that went all the way back to, you know, going to art school and then getting a job in a web design agency where some of these insights started to like the aha moments came around like, oh, there could be a way better way of creating for the web inside of this visual development software. Um, but I think it's a, um, trying to link that to kind of my, um, my journey as a, as a refugee or as an immigrant. Um, and, and the main thing I can, I can link that to is just the fact that I had to, I was put into so many different situations where I just had to figure it out that that journey gave me the confidence when I did want to go figure out, you know, how would actually build this thing that I was pretty confident that I would be able to figure it out, even though there's so many unknowns and so many people telling me like this isn't going to work or, you know, other people have tried and there must be a reason why it didn't work, etc.

14:46So talk to me a little bit about like inspirations. So, you know, you've talked, obviously you've got like the dentist surgeries, the videographers, you've got people who do business broadly around you but you're also obviously in a place famous around the world for enabling people to follow vision and yours is no linear path so talk to me a little bit about where the inspiration comes from to go and do something like this and is the vision so big the first time around that's a great question um I think there's so many different sources of inspiration. Like I can, you know, I can quote you a list of, of people who, you know, had followed like Steve Jobs and a bunch of Ted, Ted speakers who I would, you know, watch their, watch their speeches or talks and be really inspired around like, you know, these are folks who see a picture of a different world and go out and create it, right.

15:47And kind of run through walls to make that happen. I think the full, there's two big sources of inspiration that I think were the most critical for me. So one was Pixar. Seeing what Pixar was able to do, you know, it was a relatively small team at the time. Now it's like late nineties that they were able to take this new medium of 3D animation and build software around that to tell those stories and empower animators and these creatives to leverage this new medium, this very technical medium, and then bring these amazing magical stories to the big screen. When I looked at that team, when I looked at what Pixar was able to do like hit after hit um it was just like how you know i just wanted to learn how they were able to get uh such a creative and deeply technical endeavor um uh and you know like i said before like run through walls to make that happen to bring that magical um like those magical stories to uh to the screen where just watching them you could tell that they were pushing the boundaries of what was possible.

17:03Every new film was like, whoa, they're getting like hair to look perfect. Now they're getting water to look perfect. Now they're getting, like to me, it was both like a creative and technical achievement every time you would watch one of these movies. And the second big inspiration was this person named Brett Victor, who has a series of, I think he was like a researcher and then he worked at Apple for a while on like visual user interfaces. for like the iPad interface. But ultimately he has this website called worrydream.com where he had a bunch of talks. And one time I happened to see this video called inventing on principle, which is all around the combination of programming or writing code in like a text editor, and then seeing the output of that code in an actual like application or UI or like a visual expression of that, like, and bridging that gap to where you don't think of code as a separate thing, or this, like, end result as a separate thing, but, like, they're so deeply connected that when you change the code, the UI changes, or if you change the UI, the code behind the scenes changes.

18:16And when I saw this video, you know, I was working a full-time job at Intuit, and I already had a lot of the ideas behind Webflow. I already tried to start it multiple times. It was not as grand and as big of a vision as it ended up becoming or as it became after that, after I watched that video. But seeing that, seeing that talk, it's like a 45 minute conference talk that he did, you know, many, many years ago, like 15 years ago or something like that. It had this combination of all of those concepts of visual manipulation and visual development. Plus he asked this core question, like, why do you do the work that you do?

18:57Why is it meaningful? What purpose does it bring to the world? What purpose and fulfillment does it bring to you as a person? And the fact that these two things were connected, like something that, you know, was all around like this visual and computing realm, which I already was, you know, deeply inspired by the folks at Pixar and everything that they were doing, and bringing it together there was like this actual development programming kind of animation route, like bringing these two worlds together. Literally the next morning I called my boss and said, I'm going to be leaving my job and working on this thing full time because that video is just so, that conference talk so perfectly combined these two concepts that after that, I was like, this needs to become a reality.

19:46Like I need to make Webflow a real thing that actually, you know, benefits humans in the way that I imagine, like makes the new medium of the web, similar to how 3D was democratized, bringing the power of this new medium to more and more people. And that the combination of those things made me believe that that was possible. and that again got the ball rolling um it's sometimes like that initial inspiration is like the main thing that you need that sustains you for many many years even after you see a lot of setbacks and that's what it was for me it was like um i kept going back to that video to to the inspiration behind inventing on principle um that kept kept uh this underlying belief that this is not only possible, but it's inevitable.

20:45That got me through a lot of like the darker moments, especially in the early years, where it just wasn't a sure thing that this was going to work out. One of my favorite quotes is when the student is ready, the teacher appears. I think what I love about that quote so much is how applicable it can be to various stages in your life where you can come across the exact same video nothing changes you are just not in a place where it matters in your life and then another time you'll come across the same thing and it will totally change your life and nothing has changed except for where you are on that journey and how you interpret it and uh what's really important as well about that that saying is I think people put a great emphasis on needing mentorship.

21:35You know, can I speak to you for some mentorship? Can you be my coach? Can you X, Y, and Z? We live in a world where most things are recorded and the purpose of a podcast like this and YouTube and other things is mentorship is free all over the internet and so is inspiration to hit you at the right time. And what you've just discussed is amazing because it is literally the right teacher with the right message for the right student at the right time you know literally on a video um you didn't need to meet this person it just hit you at the right time and changed your life and created a massive organization and a you know rocket ship in the no code space i find all of that fascinating speaking about another teacher what was your favorite pixar film what can we say is your other favorite teacher there uh it's tough to pick um uh i think it used to be toy story 2 um now it's um uh if if you uh if you have to pull it out of me um it's shoot i totally i'm like totally blanking that always happens to people when you ask a question they're like this is my favorite and shit what's the no what's the one about feelings oh right inside out inside out why why did i blank on that it's it's my favorite movie so like that in san francisco yeah it's uh exactly um i'm embarrassed that i forgot the name but that that is absolutely my favorite so far i'm not sure we can edit that out my friend it shows that you're you're human after all yeah yeah um right okay so um though you did a tweet a while ago this is how i came in contact with you because obviously it went viral and it was all about um you know the multiple times that you tried to start webflow and the multiple times you failed and basically keep going you know it's kind of the lesson there talk to us a little bit about the the failing three times you know and what was your original vision for webflow because you sort of alluded to it and how did a vision evolve from failure into the vision for where you want to take it today?

23:47I think that kind of goes back to what you said about the right teacher at the right time or something like that. The initial iteration of Webflow was all the way back in 2005. And that came out of some of the inspiration from Pixar. But also, it didn't quite hit this. I didn't imagine it to be as like visual as it ended up being. The first iteration was very much like a configuration driven, you know, all software back then was, it was more, it was like less delightful, less intuitive. It was more like forms driven where you would have, you know, here's like a page where you like configure something.

24:34And that's kind of what the first version was that first original vision. I wouldn't even call it a vision. The vision was more around like how can I, as I'm getting more and more clients that I'm building websites for, how can I create something that speeds that up for me? And I was a developer. I wasn't as much of a designer. So I was like solving that problem for myself. It was, you could say that it was no code or like less code or low code, but it was more around like, okay, how do I create frameworks for myself as a programmer to save some of the repetitive tasks and make creating these dynamic web applications easier as I get more and more clients.

25:16Over time, and at the time, the web was entering this web 2.0 era where we kind of had these dark ages after the dot-com crash where there was a lot of skepticism around, well, is the web going to be a viable medium for you know, delivering applications or is it even going to be like a huge medium for just overall distribution of content, etc. I mean, obviously the answer is yes, but the question was around how quickly and how much. And that that first iteration, I tried to start as a business and like wrote, you know, the vast majority of what I believe to be like the code base that, you know, could bring it to market.

25:59and there was like a series of technical and like this framework that I had based everything on was by this company in Bulgaria that went out of business and then I didn't have you know the source code to their sort of like this core library that I was basing everything around and I just felt like the whole thing self-destructed like it's just the technology that I was built on, I just couldn't, I had to do like a full rewrite and it couldn't sustain itself. So that felt like a failure because I'm like, all right, now I, you know, I kind of have to start from scratch. And it coincided with a lot of like life events that I was just graduating.

26:39I fell in love and was engaged to be married and, you know, kind of had to get a real job. So I felt pretty discouraged that, hey, here's this thing that I poured like more than a year into and wrote my senior project around and almost got to working. And then, you know, by no fault of my own, this company went out of business and I can't like recover anything here. And I felt like I didn't have enough time because I had to go get a job and start to make a living and, you know, kind of provide for my future wife, et cetera. And then the second time around was a couple years later where I still had this itch and I started rebuilding it sort of like nights and weekends while I had this job at Intuit.

27:21And I kind of, you know, gave it a shot, then spent a bunch of time trying to build the product. But again, I took it into so many different sort of versions, depending on like which client that I got. You know, the requirements changed a ton. So I was like kind of all over the place and didn't quite know what I was building. and that petered out over time. And then about a year later, I got re-inspired again. I was like, okay, I need to, I need to, this was sort of 2007, 2008 when YC was becoming a thing, more and more of, you know, convertible notes started to become a thing. You start to see more and more startups being funded in this like early seed stage.

28:04And that's when like the, like got re-inspired again and actually found a couple of co-founders that were working with me at Intuit, where we sort of started spending nights and weekends on it together, started to put together like a business plan, got some funding, got incorporated, and started, you know, building pitch decks, started, you know, coding the product. And again, a lot of unfortunate series, both fortunate and unfortunate series of events happened where we just ran out of money, ran out of, you know, one of the co-founders decided it wasn't for him because we're not showing any traction.

28:43We're not able to find any investors to talk to. And then we had this trademark situation where we applied for a trademark and it got both denied and already had the domain Webflow.com, which I took out a bunch of credit card loans to pay for, but couldn't get the actual trademark to use the name as our official doing business as type of name. and that combination of all of those things running out of money, running out of, you know, starting to lose some of this kind of momentum with co-founders and the technology at the time, like in 2007, wasn't quite, browsers weren't sophisticated enough to enable building something like truly visual inside the browser.

29:29So it was still like this sort of like configuration driven approach, combined with almost like a Squarespace-y like, you know, very simple site builder and like UI builder. And again, because of all those like factors, it ended up petering out again, where I was like, ah, this just is, all the signs are pointing to this isn't going to work. And at the same time, multiple other startups in the space, like Weebly were really taking off and getting, they got like a large, I remember Weebly getting almost like a, I think a$25 million round from Sequoia, which is unheard of. And, and part of my mindset at the time was like, okay, well, somebody else is going to like run away with this and, you know, solve this problem.

30:15So I felt pretty discouraged. And it was also around the time that my wife and I started talking about having kids, I moved back to Sacramento to be closer to family. And all these factors kind of came together to, and like it slowly died again. And it wasn't until many years later when I saw this inventing on principle video. And by that time I was already, you know, in Sacramento had two kids, felt like I couldn't take any risks. And, you know, we didn't have much in terms of savings. and it was only after watching that video that everything just like rushed back in or like okay this is a the fact that the this this vision or this idea morphed into hey and and the technology at the time in 2012 this like last iteration browsers is caught up and like responsive web design became a thing where you could you could build so much more in the browser with new browser APIs like Chrome and Safari and Firefox had gotten so advanced at that point through the creation, you know, applications like Google Maps started to push the boundaries of like what you could do in the browser.

31:26And, you know, combined with this inventing on principle video, like that reformed everything and like re-energized me, even to the degree where I was like, man, I know this like failed three times in the past, but things are so fundamentally different now that, you know, over the last five years, this, what I thought Weebly was going to turn into like this multi-billion dollar company that just takes over how, um, how people create for the web, especially like professional things for the web, um, that didn't really manifest. Um, you know, there's more and more demand for responsive design and doing things visually, um, that it was enough of a, um, kind of groundswell of great signals, uh, that made me forget about all the failures, I was like, all right, this is definitely worth another shot.

32:16Enough so that, you know, like picked up our family and moved to the Bay Area kind of sight unseen. Found the first like condo we could like live in and just went heads down to work on it as much as I could. Yeah. So one of the things that often becomes a common theme in entrepreneurial stories of great success is actually there's a time and place for risk. and for a lot of people it's not the place that you've just discussed you know you know by the time you've got two kids and the wife and a really well-paying job and things are good it's very hard like very very hard to have the balls to decide to throw that all away to take the risk and obviously even harder to try and convince everyone else you're not crazy so a can you tell us a little bit about how you and your wife handled that conversation at the time?

33:09Did she think you were mental? And secondly, for other people who are in a situation like you've led and are like, God, I really want to do this thing, but is now the right time? What would you say to them? It was a lot of conversations that led to, it wasn't just the initial conversation where, you know, I had to convince my wife that this was like a good idea to kind of drop everything and risk such a, I wouldn't say like my job was like super high paying, but it was stable. And it was, it was something where we could, we could know that our, you know, kids were safe, we had health insurance, etc.

33:56I think the thing that brought her over the edge initially was the fact that that I was able to convince myself and her that three months in, we would somehow get we would get funding to replace my or replace close to my previous income, which in hindsight ended up being like way wishful thinking that that didn't happen until a couple of years later in reality. But initially, when, you know, put together this plan around like, well, we could sell all of the Intuit stock that we had, which is like very minimal. Like, I think it was selling all of it netted something like$15 ,000, which I know sounds like a privileged thing to say that that's minimal.

34:42But for us, it was like, okay, maybe that's three months of runway that gets us to, if we do a Kickstarter and create like this video that gets people to realize that they want what we're building, then that will create an influx of cash and we'll be off to the races. So that was the initial conversation. We're just like both inspired and motivated that like, hey, this is, you know, this is a kind of feels like my life's work. I've been, I tried to do it three different times. Like something is like the universe is telling me that this needs to happen again. So it's just definitely on board. But three months go by, right?

35:20Like we move here and then all sorts of, you know, we actually like start, start the company, my brother joins. but then that money runs out right then you start to like borrow against credit cards then you know my my one of my daughters unfortunately had this big medical event and we only had catastrophic health insurance which you know has like massive deductibles and through a lot of like unfortunate events we end up being like way in debt right and and then the conversations get a lot harder around like when do you stop when do you consider going back to um you know we're already having conversations around going back to my old job and uh moonlighting like continuing to work on webflow um nights and weekends etc but i think there was always like this um kind of there's something next like some hope that was hey if this if this happens if we get into yc or if we launch something and people resonate with it um like it makes sense to keep going in some way.

36:22And we got very close to the edge where we almost gave up and went back to my old job. But it was always like on this. And we pushed our, you know, family budget way beyond what it should have gone. So there's a lot of like survivorship bias in what I can say here around like the decisions I made were probably completely foolish financially, right? And I would probably if I had a close friend going through the same thing, I would probably not recommend, recommend them to keep like pulling money out from like credit cards or like these balance transfer offers because, you know, to keep the company afloat, right?