Raising Capital for the First Time

Andrew interviews Drew Wilson, Founder of Plasso. Hear about Drew's first experience raising funding and pitching to investors in Silicon Valley and his advice to entrepreneurs looking to raise funding.

Presented by
Andrew Verboncouer
Partner & CEO
Drew Wilson
Founder & CEO, Plasso

Andrew Verboncouer:  You're listening to the Seaworthy Podcast, Episode 10, Raising Capital for the First Time. Seaworthy is a podcast about building successful software. Today we're talking about going from bootstrapping products to the experience of raising a seed round with Drew Wilson of Plasso. 

I'm excited to have Drew Wilson on the show with me today. Drew is a designer, developer and maker shipping about 40 products into the wild. He's currently the founder and CEO of Plasso, a company building the future of e-commerce. Welcome to Seaworthy Drew - thanks for coming on the show today. How you doing?

Drew Wilson:   Hey, man, doing good. Thanks for having me.

Andrew Verboncouer:  Good. Yeah, absolutely. Thanks for coming. So you have a big history of shipping software, 40, about 40 products. We were talking about this just before the show here. And you always think it's around 20 - 37 that are in the wild that you've actually I guess, published? 

Drew Wilson:   Yeah, I've literally never counted. So that's why I don't know...

Andrew Verboncouer:  37, and then, you know, five or 10 that you're working on at any given time, I can imagine. Can you tell us a little bit more about your background and how you got started in design, development and business?

Drew Wilson:   Yes. So for design I back I think whenever Photoshop to was around is when I first started on Photoshop. And before that I was doing as a kid, I was like super an artist. I was doing like contact crayon, drawings, paintings, acrylics, that kind of stuff. And then my dad for his job. He's Photoshop when it's really early. And so I kind of got exposed to that early, he bought the very first digital camera ever made that was publicly available. So we got to take pictures with that. So that was super fun. And bringing those into Photoshop. He kind of showed us how you could do stuff. And I was before layers were introduced in Photoshop. So like, any edits you made were, like, permanent, there was no layers, which is he Yeah, so it's harder to work with. But I didn't really know like, what design was or anything at that time, I was just having fun with, you know, making things in Photoshop. So when I got a little older, and I did, I was exposed to what design was, it was pretty natural for me to hop into Photoshop and start making stuff. And that progressed into web stuff. Because in 1996, I made my first website for myself, just dig around with HTML. And I remember the first time I was exposed to, like, web design, and, like, understood what it was, was probably the Microsoft website in like, I guess it would have been like, '96, '97 around there. And I saw they had a sidebar and they had a header in between, like, where they meet, instead of being like square. It was like a rounded corner. How in the world that they do that?

Andrew Verboncouer:  Yea, what is this?

Drew Wilson:   Yea, I was like how, what is it so I inspected you know, this, like, the first time I like, seriously viewed source to see what was going on how they did that? Yeah, so then I kept making, you know, websites did print design, stuff like that. And then in 2002, I finally bit the bullet was like, fine, I'll teach myself how to code and never wanted to, I was like, I don't want to be like, staring at code thats so nerdy and boring. But I taught, I taught myself just because I didn't know anybody who, who was a developer, and I didn't have any money to pay anyone. And I had all these designs that I really wanted to, like, make interactive, you know, beyond just HTML. And so I, I started started learning it. And it was super fun. I mean, I absolutely love development now. So I've been been doing a lot of different kinds recently, moving from what I started with was just PHP into JavaScript, and, you know, development and also iOS and Mac development as well. 

Andrew Verboncouer:  So going back to what you said about rounded corners. I mean, back in the day, I think you had to do it with what, Gifs? 

Drew Wilson:   Yea, yea - you'd have to just put in an image and, you know, there wasn't any transparency in images back then. So you just, well, there was gifs, but they were like, they were really terrible. So they couldn't do shadows, right. Just like gifts are now like, if you try to transparency, it's no good. So you just usually just do that in Photoshop. You just set the background color, the image to be whatever it is going to be on the website and just use tables. And in that little corner there, you put a square image that looks rounded. 

Andrew Verboncouer:  Slight of hand. 

Drew Wilson:   Yes. 

Andrew Verboncouer:  Yeah. So um, thanks for that background on kind of how you got started. Obviously, that was what, 20 years ago now...1996? 

Drew Wilson:   Is that 20 years? Yea...

Andrew Verboncouer:  Yea, it's crazy. What do you like to do outside of work?

Drew Wilson:   Um, I I would say that I like to surf but that would be kind of lying. I mean I like to surf. But the last time I went was like a month and a half ago and I think this calendar year though, I've only gone out like three times but I do like to do that. It's just I don't really have any time for me. I mean got kids so that's what I like doing is if I'm not at work, I'm hanging out with my kids. So we go do a lot of stuff around here in Carlsbad. There's a lot of stuff to do. And being a dad of three little kids, six and four and two - It's a makes it difficult to, to have time to do anything else? You know, other than hanging out with them, so.

Andrew Verboncouer:  Right. Yeah. And speaking about the kids and your family and stuff. You guys recently traveled around the country for a year in an RV, was that - how was that experience? 

Drew Wilson:   Yeah, it was it was cool man. It was like totally on a whim. We had just moved from here in Southern California, up to Washington state where we were - my wife and I are both from and we quickly realized that you know what, it's not for us. So six months into our one year lease, we decided on a car trip like hey, let's just RV the country. So we just did it. We sold everything and got an RV and started RV'ing the country, which was super cool. We didn't have any intention of like seeing every state or anything like that. We're just going to circle the country. And we didn't know exactly how long we do it. We figured maybe like six months or something, but ended up being almost a full year and we ended up staying every stage in the lower 48, obviously. So it was it was amazing. It was such a fun trip. And yeah, we took our three kids with us. We had a big 41 foot fifth wheel that we hooked into the back of our huge F-350 and the RV had two bedrooms, two bathrooms. It was crazy.

Andrew Verboncouer:  Yea that sounds cool. So did you end up hitting every state? 

Drew Wilson:   Yeah, yeah, 

Andrew Verboncouer:  In the continental? 

Drew Wilson:   Yep, we stayed. And there's only two states that we stayed just one night in every other state we stayed longer. And that was Delaware and West Virginia. We only were able to stay one night. But the rest of them, we stayed longer. Which is cool. 

Andrew Verboncouer:  So you came to Wisconsin? Where did you guys end up staying?

Drew Wilson:   Um, we stayed on a super cool river. And I can't remember the name of the river because it was one of a bajillion that we stayed on. But it was a really cool place, that whole area there, you know, it's just like, there's so much open space. And so the campground, I guess that we stayed at was just massive open fields of grass, and we like the RV spots were like, right on the grass and everything. And it was cool. 

Andrew Verboncouer:  Yeah, that's cool. And so while you were doing this, you were working remotely. I remember seeing a picture of your iMac bolted down, so it didn't go anywhere.

Drew Wilson:   Yep, yep. Yeah, I lucked out, we got the fifth wheel. We got for a couple reasons. One, it's like one 10th of the price of an RV. Tww, it's safer. Because your kids are riding up in the truck with you not, you know, seat belted into one of the seats, because a seat belts in RV's aren't actually attached to anything they're screwed into the floor. So they're not, they're not real, they're just pretend. So that's another reason. And then also, it had an office in the main bedroom. And by office. I mean, it had a desk and by desk, I mean, have a little small piece of wood that have an area for your legs to go underneath. And it was literally as wide as my iMac. Like almost to the millimeter. So I just like squeeze it in there. And the leg space was a joke, you know, you could barely extend it but it was the only literally the ony RV that I could have bought that had that, and also a separate bedroom. So worked out. 

Andrew Verboncouer:  Yeah, that sounds pretty cool. Did you end up doing a lot of working from the road? I imagine driving around that now. 

Drew Wilson:   You know, I thought about, you know what, I'm gonna do this RV trip and get rid of all my other products. And just focus on Plasso. Yeah, like for some reason it didn't cross my mind that traveling itself is like, a full time job. And then traveling with kids is like, even more so, you know, because you're like, literally traveling, you're in the car driving all the time, especially if you're seeing every state in America. So there's literally no time for anything else. So yeah, I barely worked on the on the trip, which was not my intention. So it wasn't -  that aspect was not so great. Because at that point, I still needed to work in order to make money. So yeah, I nuked my bank account, basically.

Andrew Verboncouer:  For a year. And then, you know, maybe wonder how the dynamic is with your kids. You know, they expect you to spend a lot more time with them, you know, then you would at home? 

Drew Wilson:   Yea no, I mean, it was so great. Yeah, yeah. No, it's so great. Like, kids are so adaptable, like, whatever you do is normal to them. So they weren't like, like, Hey, when are we going to live in a house, you know, it was just normal for them to be in the RV. And, yeah, it was super cool. Like, I've always worked from home and always spent a lot of time with my kids and coming back from the RV trip. I mean, that was the case. I mean, we were up in Washington for a little while after. And then we moved to San Francisco for six months after that. And then even I moved back here for a few months, I was still working at my house until I got an office here. Separate for Plasso - so now I work out of the office which is really actually the first time I've ever not worked from home my entire life.

Andrew Verboncouer:  So for the kids it's a bit of an adjustment, but it's really not so bad. Because I'm decently close to my house. And, and some days I still you know, work from home with the kids and everything. It works out great. It's actually - I never wanted to you know, work away from home because I want to be around my kids but works out good for my wife that I'm not there because then she doesn't have to worry about the kids like knocking on my door or coming in, or that kind of thing.  Yeah, thats tough you know. I know quite a few people who work from home a lot and with kids, it makes you feel bad that Hey, Dad, can we go play? You know? 

Drew Wilson:   Yeah, yeah, you know, they get used to it after a while. Yeah, they get used to it. I mean, they might, if you started to work from home, like from being an office or something, they'll probably ask you that. But after like, probably a few weeks, they understand the concept of you're at work. That kind of thing. So, it's not that bad. Yeah.

Andrew Verboncouer:  So you've built almost 40 products, right? So which one, you mentioned Plasso kind of while you were on the road, but which ones have been your your favorite so far? To build? I mean, I know there's a lot. 

Drew Wilson:   Yeah, um honestly I, I would say Plasso just because it was a display of skill. And by that I mean Plasso's doing well, not because of luck. Whereas like, for instance, my icons that I launched previously Pictose, they did really well in the literal sense of the term overnight success and totally changed the trajectory of my career. But that was right place at right time kind of thing. I did not know that, you know, icons for this underserved market. And there was literally nothing out there, I just happened to launch my icons, when literally nothing else was out there. Nowadays, like the the race to the bottom on pricing icons is since passed, and everything you can get the best icons for free. But when I launched them, that was absolutely not the case. You could not find any icons. And so I happen to be in the right place, right time. Whereas with this e commerce platform, this is actually my third attempt at doing e commerce. And each time a little different. And so this is more a conscious effort to make something work. So in that sense, it's a lot more fulfilling, because it's like something you made work, you know what I mean? 

Andrew Verboncouer:  Right - yea, it's cool. So why don't you tell us a little bit about Plasso, and what it is.  

Drew Wilson: Yea Plasso's an e commerce platform, the main thing that we're doing right now that really no one else is - we're enabling you to create a subscription or membership business without any development or technical knowledge needed. So what that means is, you can sign up on Plasso. And after a few clicks and or taps, you can have a subscription business up and running. So you could start charging people on a recurring basis, like every month or every year, two weeks, whatever you want it to be all of that having to do anything other than click a few buttons and SAS or recurring revenue is is a very smart business to get into. And so it works out really great for our customers, and great for us, because there's really no one else doing this right now. If you look at the big e commerce players, Squarespace, square, Shopify, big commerce, none them have any recurring payments. So by us doing it, we're coming into a completely unserved market, which is great for us, I mean, we do all the other e commerce stuff as well, but we're really pushing the subscription aspect to our business just because that's what we're doing different. 

Andrew Verboncouer: Right. So is that you know, is it like products like box services that are coming every month? Or is it more you mentioned SAS or is it a good mix of both?

Drew Wilson:   Its a mix it a lot of stuff, really, um, there are a lot of subscription boxes, like for instance, art snacks, one of our customers artsnacks.co, you can sign up with them via Plasso and they will send you a box of high quality art supplies every month, and you don't know you're getting until it arrives. So there's and there's some organic coffee companies doing the same thing using Plasso and a handful of other subscription box companies. There's also people who are using it to handle their membership payments for like gyms and co working spaces. Matter of fact, the CO working space below our offices brand new here to Carlsbad called common grounds. They're using Plasso to power all their payments, and they're expanding nationally. So Plasso will go with them as they expand, which is super cool. And then yeah, then the people doing it to some people saw advice on subscription. There's customers that have like a luxury taxi cab service, they use Plasso to handle their billing. There's a there's a getaway company, kind of like a like a curated Airbnb kind of thing for tiny houses. And they use Plasso to handle their billing, so by different companies doing cool stuff. And what's great about Plasso is we're - kind of like back in the day, when Shopify came about. They enabled like new business, because before in order to accept payments online, you had to submit or or put up a ton of upfront cash to have someone build this for you. And Shopify made it so that way, you could just try it out with no upfront cost. And no one's really done that for subscriptions yet. So that's what we're doing. You don't have to hire someone and pay someone to build out a system just to see if your idea works. You can just sign up with Plasso, and no upfront cost at all. Try it out and see if your business works. So we're enabling new businesses and people with ideas can now like realize those things really easily. 

Andrew Verboncouer:  For sure. Yeah, that mitigates a ton of the risk I mean, you know, using it as a merchant account, or Authorize.net back in the day, you're paying thousands of dollars just to get something going. Yep.  Yea that's cool. So you guys recently relaunched the whole platform, new design, lots of new features, and I noticed the different verticals in there. And how is the past - I think it's been one or two weeks since the new launch - How's that gone for you guys? 

Drew Wilson:   Yea, it's been a week today, I think, right? Or maybe a week - tomorrow will have been a week. Yeah, no, it's, it's been super great, super fantastic. Got a lot of new people signing up. The main thing that I'm most excited about is that before, up until now, I had left the original design that I launched with Plasso up. And so it didn't really describe what class so even did that, well, I was just a one pager. And now like the marketing site is like, really dialed in as far as like properly showing what we offer and the different verticals, and how each different product conserve different market. Second thing - so it's so much better for me to be able to tell people what Plasso does and show them what it does, just by pointing to the website. Whereas before, I never had that. So that's super cool. And there's a ton of work still to be done there. We'd spent a lot of time working on some videos, one of them's launched with the site. And we have a handful more that we're going to be rolling out every every month or so. And so there's a lot of lot of cool stuff working on on the marketing stuff. That is something that we never had before. So I'm super excited to get into that aspect. We're still doing a ton of stuff on the product side product development, but the marketing aspect of the business is something that wasn't there before. So yeah. 

Andrew Verboncouer:  Yea if I remember, you know, the landing page from before was from what space box? Was it? 

Drew Wilson: Well, it was different than space box. But yeah, pretty similar. Yeah.  

Andrew Verboncouer: Cool. Yeah. Well, that's great to hear that everything's going well. And, and things are going good. So kind of stepping back to it. You mentioned that this is really the third try or the, you know, the third at bat for this e commerce platform. Can you talk a little bit about where you got the idea and kind of the progression from when you started it to now? 

Drew Wilson:   Yea so my first attempt, I guess I'll say was with a product called Quixly. And I built Quixly in 2009, and I think I launched it in 2010. Or maybe I want you to us, I can't remember. But that was quickly I was building has a way to suit my soul from what I just gone through with the product before that called fire left, which I spent two years in a code cave, working on this CMS front end, CMS, like, wrote one of the first Jason templaters, all this kind of crazy crap. And it's just way too futuristic. And no one knew what the crap what's going on with it. And so it did not sell. It was horrible failure. And I had like, wrapped my entire life up into this thing. And all my money and all my furniture I sold and everything. So it was not it was not so fun coming off of that. And then Southern Cal just got to build something quickly, and just get it out there. And so digital delivery was underserved and no one was really doing anything. There was a company called he junkie, which looks like it's from the 90s, and there wasn't really anything there. So like, sweet. Let's do that. I also build these icons. It'll be great to sell these icons with this. So I built a digital delivery platform called Quixly, which allowed you to sell your digital goods like files, and it was built on PayPal and Google Wallet. Because stripe didn't exist at the time. And the platform did alright. There's people that signed up, but it didn't really make any money. However, it enabled me to make a ton of money because I was selling my picture icons, which did super well, selling it through quickly. But quickly, the business model there never worked. Because it was built on the old school way of doing things like based on how much storage you're using, and file transfers, and all that kind of stuff. And that just doesn't work out. So that never really went anywhere as a platform. And then I ran that until like 2012, and I shut it down after I made sure I made space box. So this is my second attempt at e commerce and stripe it come out really I think they launched in 2010. But they didn't really come out in 2011 when they actually made it like publicly available to anyone. And I was on somehow I got on the early beta list. I can't remember why. Oh, yeah. Patrick had reached out to me about doing design for the company. And I said no.

Andrew Verboncouer:  No, I'm working on this Quixly thing. 

Drew Wilson:   Yeah. So he put me on their their beta list. So I got this tryout stripe, actually, for the - we were going to put it, build it into Quixly, we were thinking about it because I was still running that, but ended up just like letting us sit there for a while. And also, you know, stripe needs a human interface. It's rad API. But it needs like a human interface. So anyone can use it. So I was like, I'm going to build something just a quick like a quick little products that people can sign up attached or stripe account. And then like accept payments. And they'll have to build anything. And I asked my son like, hey what should daddy name his new app? And he was like space box, and I'm like sweet. So, he was two at the time. So he named it. So we launched space box, which was like a human interface, we strive to quickly and easily accept payments with your stripe account. And then that evolved and people liked it. And I started adding more and more features. And of course, since I had done Quixly, the whole digital delivery aspect was in there already. And spacebox was essentially what Plasso's pay me page or pay-me product is now, where you just you can go to us,  to be able to space box, your email address. And there's a little page and we just go there and pay you. And so that's still exists in Plasso today. But it's from way back then. But spacebox never really did that. Also, the business models did not work. I was like a freemium model. So you can sign up for free. And you could add up to two spaces and spaces were like product pages. So this is separate from like, your pay me page. This is like, if you have a product to sell, you get out of the two spaces for free. If you want to have more, you pay X amount of dollars per month. But that didn't really work. Because people would just go sign up to accounts, you know, to get by that if you see a lot of that I didn't really moderate too well. But I know there are people doing that. And then yeah, just the business model. General freemium just didn't really work for e commerce. Because most people aren't going to sell very much. And, if you're not taking anything from them, you're not gonna be making anything for most users. So I I just, I really liked the aspect of e commerce of payments I always have. And so I wanted to continue with space box. But I needed like a new business model, I needed to change that. So I changed it all and relaunched and re developed everything from scratch, and design the whole new interface, all that jazz and relaunched as Plasso. And that was in May of 2014. So I relaunched as Plasso, and then the business model, the new one was working and, and I started making money off the platform, which is fantastic. And right when it getting going was also the time that we had kind of uprooted moved to Washington and then we decided to do the RV trip which is - I thought was gonna be able to hunker down and, and like really work on Plasso. But that ended up not being the case. So when I got back, I decided to move to San Francisco and, raise money for Plasso so I could build a team around it, because it started getting to the point where it was doing really well. But as a consequence of that, there was a lot of not necessarily like customer support emails, I mean, there's a lot of that to answer. But more like customers need this, that, or the other feature to work better. And so all my time was being spent on like changing features or making things a slightly better or fixing bugs, that kind of stuff. And I didn't really have any time to spend on progressing the platform or do any marketing whatsoever, or any of the stuff you need to do in order to make a business a business. So I was like, you know, I need some help. And I can either try to grow this organically and just like bring on one person part time to help me out with stuff and hopefully, slowly slowly grow. Or I could just take advantage of the industry that we're in, go to San Francisco and raise some money and build a team and just, you know, go out and do this way faster. And I had done bootstrapping my entire career. So I know how that game is. And I think for this platform it - because of what what I was doing, and I guess the urgency of it, like I definitely needed to have a team helping me right away. Raising money was the best way to do that.

Andrew Verboncouer:  Yea, I mean, it sounds like it, you know, with that, with the market and who your customers are, and they're not tech savvy, that you know, things can always be improved and streamlined. Just going back to you know, you pivoting from you know, Quixly, to space box, and now you're at Plasso is kind of the third life of this e commerce solution. Do you think the biggest changes in what you guys have done, the biggest pivots, have all been focused around that business model? Or were there any kind of key elements you think that helped, you know, take it to the next level with each iteration or each new launch? 

Drew Wilson:   Yea, so when I launched space box it was completely from scratch it didn't have any of Quixly's actual code base or anything, it was all just me 100% and I started adding features based on what I thought would be cool. And mainly what people are asking for, we just kind of different because most of my other products that I built, I built a tool or something for myself the way I wanted to be where a space box, I don't need a human interface for stripe, I'm a developer, I can make my own way. But I wanted other people to have a way to do it. So even though I myself would use spacebox and I did, I used it for Pictose, it wasn't something that I needed. So it's a little different in that sense, where I'm building something for that people with, with spacewalks.

Andrew Verboncouer:  Right.

Drew Wilson:   And when I relaunched Plasso, so it was 100% me again, just doing everything. So the few things that I could change that could add, like I said, we're all just based on like, what customers were wanting, I have grand visions for the platform, and things I wanted to add, but all those things would take were taking a long time because of all the support stuff I was doing. So yeah, so I mean, I guess as far as I can, how I was coming up with new features, and everything, a lot of it for space box and for Plasso was based on customer feedback. And, also, you know, things that I wanted to see in there personally, but...

Andrew Verboncouer:  Right, yeah, yeah. So just using customers to kind of guide where it goes, and, you know, simplifying some processes that might have been more difficult to them.  Well, and it's so much about the messaging, too, because, yeah, a lot of people are only going to, you know, they're not going to know anything about you, or your previous stuff. They're going to know this five minutes of what you're going to tell them. 

Drew Wilson:   Yea, and I never, I never even had like a complete - I knew I wanted to be like the place for people to go to services online. But I didn't really know what that meant. Until I went through the process of raising money. When I did that, it like crystal clarifies your like business model and your path, like to get to where you want to go, because you have to say it so many times with different people in different ways, and everyone wants to hear it a different way. And so you work through that, like for months, you know, every day, you're working through that for months. So you like, you really get to know, like, your different options, and different ways, different scenarios. So just by going through that, you know, exercise of raising money, it clarifies so much. And like, even if I wasn't gonna raise money in the future, I would like raise money, or at least try to just, like, get that clarity in vision. It's, it's so much different than like bootstrapping something. It's pretty cool. Yeah. And, every time you meet with someone, like if you're pitching or, or whatever, it really is a sales pitch that you're doing. And so it clarifies that marketing aspect as well. It's like, how can I, you know, super quickly get to the very point of what Plasso's doing and why it's special. Again, raising money like made that happen. Whereas 100% would have taken a long time without it. Because if you're just bootstrapping, you're just like, like, Okay, how can I easily, like most simply, message this, and you put it out there, and then then you have to like, wait for a customer to tell you, I don't understand what this is where you have to, like, send an email, blast all your customers to like, be like, Hey, does this make sense? Like, how you're going to do sales, you're not like going and doing direct sales, like when you're bootstrapping typically, but by raising money you are going and like, essentially doing direct sales to individual customers, if you will, and explain your business to them. So it helps clarify that. 

Andrew Verboncouer:  Yeah so you recently raised - what was it 1.2 million? 

Drew Wilson:   Yeah, just under.  

Andrew Verboncouer:  Is that a series A, I mean, was that considered series A? No, that's seed round.  So that was your seed round? 

Drew Wilson:   Yeah, pure, purely angels. There is no VC money in there. Which is, which is great, which is what I wanted to do. So super fortunate to be able to do that. So it was a, it was a very fun experience, in the sense that I knew going in, I have no idea what I'm doing. And I've never done this before. And it's kind of fun thinking about the fact that, okay, I'm copying myself, I know, raise money. And I know, I'm going to get discouraged and feel like, I'm not gonna be able to raise money. But I know like, at some point, I had no idea how long it would take to raise money. But at some point, all this will be done. And I will, like, have this whole new base of knowledge to pull from, right. And knowing, you know, that it's only going to be like, a few months at most, or something like that is kind of exciting to like, it's kind of thing that I kind of thought it was like sitting in the matrix chair where they just like, inject your your brain with all the information real quick. I was like, it's kind of exciting to know that that's what's going to happen. 

Andrew Verboncouer:  Yeah, it's a different world. I mean,  I can imagine coming from bootstrapping, you know, 37 products to, you know, raising for your, your first time even being a seasoned entrepreneur and, you know, changing business models and things like that, coming into this. 

Drew Wilson:   Totally, yeah.  Yeah, it's definitely different. But it's different, in a good way it makes you because the VC world or in the investment world in general, they're not like they're not the product world, not like the entrepreneur world, they're like, the business dude world, right? It's completely different, what they are concerned with, versus what like a CEO is concerned with, or like a right, so they're more like the CFO, I guess they're like, more concerned with like, the financials. And like, all that stuff. So when you actually go to raise money, if you're like me, and you're not like a CFO, it forces you to think that way. And it's a it's good, though, like thinking that way is like, so incredibly necessary - way more than I ever thought it was. And having that skill set is incredibly necessary to like, have a successful business. Of course, there's always the, the getting lucky thing where you can have successful business not because what you did, but just because you're right place the right time. But that's not the case usually. So having that knowledge and that experience coming, you know, coming from like the numbers side and everything is super valuable.

Andrew Verboncouer:  Seaworthy is brought to you by Headway. A product focus team for higher, Headway helps companies validate ideas, build out products and grow through experimentation and technical execution. If you have an idea that you're looking to gain traction on, or a current product you're building that needs expertise with product design or development, check us out at @headway.io and let's make waves.  You said you it was just you, you know, solo managing this - you're customer service, you had all of these other things to do, you wanted to get to certain features customers are asking to, but had to play like this balancing act and knew you wanted to scale this beyond you. Is that the first time you've had people involved that weren't partners. You mean with Plasso?  Yea, with Plasso.

Drew Wilson:   Yeah, that's the very first time. Yep. So up until then, up until I started raising money, like, every line of code, every pixel, every support emails, just me throughout the whole history. But once I raised money, the intention was to, you know, hire a team and change all that. And so that is what happened. Fortunately, I was able to raise money, and I was able to hire a super killer team that I'm super fortunate to have, and we're pushing things really fast now. So it's super great. Yeah.

Andrew Verboncouer:  You mentioned it was from a lot of lot of angels. How did you go around, go about making those connections? Introductions? I'm assuming your name had a little bit of reputation in some circles. I mean, most, you know, certainly a lot of people I talked to you, even from this area are familiar with you, and your work.

Drew Wilson:   Yeah, it's unfortunately, that does not translate in any way to the world of investors. So I'm a complete unknown in their mind. And I knew that going in. I knew that going in, because I know that I do not know any investors. But what I did, my buddy Alex Maccaw, he's super cool. He runs Clearbit, he had just raised money, right around the same time, I was thinking about it. So he was kind of telling me, he's gone through it, all the things he's doing. And he's super smart guy, and he was good enough to get me interested his investors, and he, when he raised a seed round, he raised from SV angel, first round, and a bunch of other bigger companies. So when I moved to San Francisco, and I was going to raise money, I was like, Hey, can you hook me up? He's like, Yeah, sure. And so that was, that was it, I had asked other people who, you know, worked with VCs or whatever, but no one else panned out, which is what I find a lot of people say, they know investors, but they don't actually know him enough to like, if they say, meet with this guy, then meet with them. Usually, that only comes when either their actual friends with them, or they are an entrepreneur that you know, has been invested in by them. And that was the case of Alex. So he hooked me up with those investors. So when I was gonna raise money, I didn't know at all what I was doing. And for some reason, I didn't even think to, like, make a real pitch, you know, I can now you see on Shark Tank, I thought the seed round just gonna be a casual conversation. And that was the case for for one of the investors that's all they wanted, they didn't want anything else. But everyone else wanted, you know, the real pitch and I did not have that it starts. So my very first meeting with an investor like a VC, was SV Angel. And then like a week later, was first round. So like the two biggest and I go in there, not knowing anything, but fortunately, I had had some practice. The day before I met with SV Angel I met with, like a decently high profile angel investor at his mansion. And he tore me apart for an hour and a half, it was the most awkward, horrible conversation, lots of long pauses by me, just staring at him having no idea what to say, feeling terrible. So after that, I realize, okay, things have got to change I need, I need real pitch. And it's funny, cuz I didn't even know I needed one going in. It's not like I was avoiding just, I didn't realize it needed work. And so I got one together, I met with SV Angel, and it. But still, I didn't understand a lot of the basics about how not necessarily how to pitch but just like the terminology behind investing, there's a lot of stuff that goes into they want to see that they expect you to know also, I didn't have all my numbers dialed in. I mean, I had numbers like basic ones, but there was like a lot of detailed numbers they wanted, and I was like, no one's going to want that for C round. That's what some advice I was getting, as well as sending out Yeah, you can eat all that stuff for seed round. But it was February 2016, when all those articles started coming out about saying like fundraise -  funding is like, totally changed, like, no one's putting money anywhere, that kind of thing. So that's when I started was in February when all those articles started coming out. And so people were wanting to see a lot of metrics, especially since I was already making money. And it wasn't just an idea. They needed a everything from me. If I was just an idea, then obviously, I've nothing to show and everything's just BS. But so yeah, I met with SV Angel and first round, and from there, they introduced me to some other investors. And then also there was a few people that I knew that I was able to race a little bit of money from, and then someone to come along, who's cool guy he had, he ran an ad platform that he sold for a lot of money. He had wanted me to be a designer for him years and years ago, he'd asked a few times I said, No, and, and I hit him up. I was like, Hey, I know you're in the valley. I know you're like, into angel investing. Like, would you want to hear about what I'm doing? He said, yeah. So he hooked me up big time. He put me on his, his Angel's syndicate after our phone call. And so all the people that follow him on Angels can invest into a syndicate, and then it just ends up being like, one one person on my cap table. So his company goes on there. So I raised some money through him. And that was other than the small stuff I was able to get on my own. His was like, the first large amount of money I got, it was about, like, all 300,000, and then, and then I pitched a time and everyone gave me a note for the same reason, which was, what if one of the big players does this? I'm like, well they haven't for like, a decade or more. So I mean, it's, of course, whatever, you know, but everyone who said yes, and yes, for the same reason, which was, oh, wow, no one's doing this. This is a great opportunity.  And so it was probably so from when I first started raising until I close my round, it was five months. And so it was crickets for me in between, like, month after like the first month up. And, you know, for four months, it was crickets. And it was it was difficult as I was not trying to raise money. And we had tons of meetings, lots of things always happen. But nothing fully panned out until I sent out an investor update. And one of my previous investors who had never actually met because they were in the angel syndicate. You don't get to see who those people are. Really, they're like, oh, wow, this amazing update, like we want to give you more money. Do you want to take another 500,000? Like, yes. So And oh, by the way, we'll get our our buddies to put in another 300 or more. And so from that initial investor update email to them emailing back for the first time, me never hearing from them to them actually putting money my account was less than 24 hours. So it was like angels...

Andrew Verboncouer:  Are you selling this investor update? It was Angeles quickest transaction ever.  Oh, that's awesome. 

Drew Wilson:   Which was cool to hear from them. And then so then their buddies putting some money. So at that point, I was like all right, I'm done. And ended up raising like I said just under 1.2 million. 

Andrew Verboncouer:  Was that your goal? Or? 

Drew Wilson:   Yeah, roundabouts. My goal was like 1.5. So it was close enough. You said. 

Andrew Verboncouer:  You said I'm good. Let's get back to work. 

Drew Wilson:   Let's get back to work. Yep. So yeah. So then, then I was able to bring on some more people on the team. Because with that initial 300 I brought on a few people right away. And then I brought on some more people. And yeah, and the rest is history. 

Andrew Verboncouer:  Yeah, it's cool. The fastest turnaround Angeles history put that in....yeah I mean, it sounds like, you know, kind of thrown into the lions den here. You had to iterate pretty quickly on on your pitch, and you know where you're going. 

Drew Wilson:   Yeah, tons of innovation, like in Lyft rides to the city back from my house, I'd be like, on my computer, like, changing slides all the time. 

Andrew Verboncouer:  So what advice would you give to people, entrepreneurs, makers, whatever, looking to raise for the first time? 

Drew Wilson:   I would definitely suggest just because of my background as like a bootstrapper, I would definitely suggest that if you're going to raise money, that you test the business yourself first, and you build it yourself, and you try it out yourself. And you see if it works. For me, it's like a big deal to take someone else's money, I don't feel like I'm raising from investors, I feel like I'm taking someone else's money. And, and it's typically not the case. Whereas people expect to be given money. And if I'm not giving money, I'm not going to try this idea, right. Where I think if you take on a lot of the risk yourself, it'll teach you so much, and make you such a better CEO, or whatever you end up being after you raise money. It'll make you so much better at knowing how to run a company, and how to make sure that you have enough money, all that kind of stuff. If you do it all yourself first, yeah, if your life is on the line, you're going to act differently. And if you can do that enough, before you go raise money, you'll be a lot better at managing the money that you raise. So I would suggest that if you're going to go raise money, that you build it all yourself first, try to make some money first. If you're making money, it's a lot easier to raise money. If I was not making money, there's no way that I would have gotten investment in Plasso. And because I was making money, I was I was able to do that. So I would suggest, I suggest you try and get it to like 10 to 20,000 per month before you go raise money. 

Andrew Verboncouer:  Yea, one that's going to give you a way better terms too. 

Drew Wilson:   Oh, yeah. 

Andrew Verboncouer:  You got to earn it. But it'll give you a better term.  So you mentioned adding, you know, new people to the team. How big is your team now?  There are eight of us. Yeah, remote team. Some of us are located in San Diego, but some of them are in London, three of them up in the Pacific Northwest. One just moved from San Diego to Boulder. Yeah. Sounds like a good a good displacement. So what is London from California? Is that eight hours? 

Drew Wilson:   Yeah, it's like eight or nine hours. It's pretty crazy. 

Andrew Verboncouer:  How does it - How does that work out with the team?

Drew Wilson:   Yea, so we have like, a weekly meeting that we do on Mondays. And we do that at 10am, which has been like, 6pm London Standard Time. So it works out okay for them.

Andrew Verboncouer:  Gotcha. Yeah.  So you guys are mainly meeting once a week, other than -  like, as a team, I guess?  Yea we will meet as a team once a week. And then we're on Slack, like, all day as well, talking to each other doing, you know, meetings back and forth, you know, with individuals, whatnot, if we need to, like on demand kind of stuff. But the only like, scheduled meeting that we have is on Mondays. Gotcha. So, do you guys do any, like agile Scrum con-bond type of flow to prioritize what you guys are doing that week? Or that sprint? Or is it more...What's the kind of makeup there to manage, like, what you guys are doing? And prepare?

Drew Wilson:   Yeah, yeah, so we have, we don't do anything like that at all. We just, I mean, things are going to be changing here. Pretty soon, we were using GitHub issues to handle stuff. But there's so much stuff to work on. And so many things popping up all the time. It doesn't make sense for us to have any like, like, set in stone scheduled, like, get this done first kind of thing right now. I've always been reactive. Like when I'm like, building products, and like, making sure I'm like putting out the hottest fires, you know, so that still is the case. 

Andrew Verboncouer:  Well Yea that's, part of being agile, for sure, is being able to re prioritize, you know, this over that.

Drew Wilson:   Yep, exactly. So basically, what we do is, all of us are super familiar with, like, the different products, we're building what, what needs to happen in order to get there. And so we're all kind of like working on those things. And, and typically, people work on things on their own. So in the sense of, like, Hey, we need to build this system. So just go do that system. And that person will just go to that system all by my lonesome. And then when that's done, it's done. So there's like the designers that I hired both our developers as well. So pretty much everyone on the team is a developer. And so we all will go to our own things and then merge those things into the master mansion, and yay we're done. So we get actually a lot of different things done at one time, even for being a small team, which is fantastic. And so we spent actually, a lot of time before we did our relaunch last week, since raising money, we spent a lot of time working on the infrastructure side of things so that way we can launch often and early that kind of thing to get that all out of the way before we started taking on a new influx of customers and really pushing the platform and from a marketing perspective so that way we don't have to take a stand back from like product or bug development and work on infrastructure - we tried to get that all done up front. 

Andrew Verboncouer:  Right yeah, with the launch did you guys get a lot of new customers signing up? I mean I think you guys did pretty well on product hunt if I remember? 

Drew Wilson:   Yeah, did did super great there. Yep. What's great about Plasso, it's been 100% word of mouth and still is. I mean, we've never actually paid for any advertising or anything like that yet. Like I said, never didn't even a drip of marketing didn't even have an email list for heaven's sake until we relaunched so -  none of that stuff. And it's just all grown word of mouth. And so with the relaunch of got a bunch of new customers, we have an email list now, which, surprisingly a ton of people signed up to. And yeah, so going forward, a lot of that stuff's going to change. And hopefully, we'll be able to grow the user signups even more. But yeah, they've like, probably by the end of this month, it'll have gone up by like, five times. That's really good. 

Andrew Verboncouer:  Yeah, yeah, that's awesome. Are there any tools that you guys use that you couldn't live without?

Drew Wilson:   Probably Slack. Like, that's a tool that we use. I mean, it's a close tie between slack and GitHub. I mean, I would say that we could run - if we didn't have GitHub, we couldn't run if we didn't have slack. We could maybe do it through GitHub, but right. Yeah, those two are the keystones for sure. And I recently visited GitHub and found out that I actually signed up like the month they launched. So I didn't realize how OG I was. 

Andrew Verboncouer:  Yeah, you start - what year did they launch? 

Drew Wilson:   I'd have to look, I think I want to say...actually, let me just look before I lie to you. I think it was 2007, yeah. 2007 - No, 2008. Yea. 

Andrew Verboncouer:  8 years ago. Yeah, that's cool. That really changed the landscape of development I would say. 

Drew Wilson:   Yes, it did.

Andrew Verboncouer:  Cool. Yeah, I mean, I appreciate all the insights and everything there's also a book that Drew was part of it you're fortunate enough to have a copy I'm looking on Amazon right now and it's $200 a piece. 

Drew Wilson:   That's kind of crazy

Andrew Verboncouer:  $295 for one - I have one in the office here, I'm you know thinking about trading it in but...

Drew Wilson:   You should do it dude, go buy yourself an iPod or something instead.

Andrew Verboncouer:  Yeah. Where can people find you Drew and follow along with you and Plasso? 

Drew Wilson:   Yeah. You can find me on Twitter @drewwilson. You can find Plasso on twitter @paywithplasso. We're also on instagram, youtube and facebook so you can see us there. But you can go to the website plasso.com, p-l-a-s-s-o. You can also go to my site drewwilson.com. That is where you can find us.

Andrew Verboncouer:  Perfect. Well, thanks again for coming on. 

Drew Wilson:   Yeah, man. Thanks for having me. 

Andrew Verboncouer:  Yea, it was a good time. 

Drew Wilson:   Super good to chat with you.

Andrew Verboncouer:  Likewise. All right, take care.

Drew Wilson:   Later.

Andrew Verboncouer:  Thanks for listening to Seaworthy. Connect with us and ask questions on Twitter @seaworthyfm. Make sure you subscribe, and if you enjoyed it, leave a review on iTunes. Sail forth and make waves! 

show notes
  • Raising Funding
  • Pitching to Investors in Silicon Valley
  • Advice to Entrepreneurs