The SaaS Bootstrapper Podcast

TSB005: Why a serial bootstrapper decided to raise a seed round, with Drew Wilson

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Episode overview:

Drew Wilson is the Founder and CEO of Plasso. In this episode he talks about his process for bootstrapping a handful apps and products, and why he eventually decided to raise a seed round for his latest, after bootstrapping it to $10k-$20k/month by himself.

Previously, Drew created countless apps including Buffalo (blogging platform), Whiteboard, bulkDelete, KidCam, OffOf, Filtron, Lumo, and more. He talks about where he got the idea for these apps, how he bootstrapped them, and dissects his overnight success with Pictos, a set of icons he created for UI designers. Drew’s talks about his approach to finding success is to just keep trying, throwing things at the wall and see what sticks. He’s clearly been very productive, and successful. Yet another inspiring story from a serial bootsrapper.

Guest links:


Drew Wilson

@drewwilson on Twitter

Mentioned in this episode:










The interview:

Mac: Welcome to another episode of The SaaS Bootstrapper Podcast. Today’s guest is a prolific app developer. He has created a blogging platform called “Buffalo” as well as a handful maybe of more of a other iOs and Mac apps such as Whiteboard, Bulk Delete, KidCam, OFFOF, Filtron, I could keep going this list goes on. He also has created a set of icons for UI designers called Pictos and most recently he is the founder and CEO of Plasso. Drew Wilson welcome to the show.

Drew: Hey, thanks for having me.

Mac: It’s nice to have you here.

Drew: Yeah, yeah.

Mac: So, yeah as I mentioned I went to your website I knew about Plasso and I had never really looked into what… who was behind it and found your site and you just have this library of apps and things that you’ve built. It’s really inspiring and cool so let’s put Plasso aside for a second, kind of back up and because you seem to have built Plasso into sort of a it’s a bigger thing now with the team and we’ll get into that but how did you get into building all these smaller apps in the first place and what’s your background?

Drew: Yeah so I started making stuff on the web. I think the first website I made I was 13, that was 1996, hacked together like some HTML and made a little webpage for myself just kind of like where I started before. Even before that I was using Photoshop and just dinking around making designs you know stuff like that all those photos and I didn’t actually start coding like back end stuff until 2002 just out of need like I was like man, I really want to see my you know HTML sites or whatever, like be interactive and like be able to store data and so I didn’t know anybody so I just had to like teach myself so taught myself PHP and pretty soon after that I mean because I was trying to learn that on purpose so that way I could build some of my own stuff. I started making stuff that like other people could use. The first product that I sold like for sale because I have made some things that people could interact with before like some community kind of stuff but the first product that I made to sell was called Firerift and I spent like two years in the code cave, lost all my money and just to get this thing launched and it was a frontend CMS so everything was done in Javascript there was like a way to interact with the database using CSS, there’s a Javascript interface and there was a PHP interface and it was a little too futuristic for its time we built it adjacent temp loader back in 2007, in 2008 but it did not sell well and it was one of those things where you buy it and you would install it on your own server so it ended up being a lot of support needed because most people are paying $5 a month for these horrible servers you know and you don’t have any access to its stuff so trying to work around all that was you know horrible so I was like okay, I’m not going to do like distributed software ever again and pretty shortly after that I made Quixly which was… it was e-commerce, it was a way to sell your own digital goods and at the time it wasn’t anything out there was E-junkie and one that I can’t remember the name of so I was like it needs to be a good one so I made one, did not want to spend two years you know with an un-launched product so we got it out longer than I wanted but I think we got it out in eight months or something like that. And it didn’t do well either, the business model was not good but I used it to sell my own icons and I was kind of making it for that purpose too. I had these icons I was you know using for client work, I was like I’ll sell these things, I didn’t know what to price it at because the only icons that time were Glyphish and Hlvticons and Hlvticons was [49 for like 60-cent icons and Glyphish was free for a ton of icons so I was like I had no idea what to price it so I decided [9, put it up using Quixly and literally, not figurative literally, literally overnight it just exploded and so then I was able to fund all my other stuff after that just using a silly little icon revenue so.

Mac: Wow! okay so that brings up a lot of questions here so when you were doing all these things, were these side projects or were you all into this? Were you in school or was this after school? What was going on?

Drew: Yeah, so, being from the Pacific Northwest you might know this program in Washington State called Running Start where as long as you have a C average in high school you can do your last year’s of high school at the community college so I did that so when I graduated high school, I also graduated community college so I never went to school after that. So I wasn’t in school when I moved down to California right after that I was like hey I think I’m either going to like start my own business or design school. Design school’s like $67,000 a year, I was like I’ll start my own business. So for me I’ve been like full-time doing my own business kind of thing and so I was not in school and everything that I did, most of the things were like side projects that had client work that I was focusing on but when I did Firerift I was like I’m going to stop all client work and just focus on this and that’s when I said I lost all my money because I wasn’t doing any other work and I really didn’t have much savings so I was scraping by man. I sold off all my furniture, my house, I also had a side-business doing my wedding photography, I sold off all my camera gear. Yeah, it was not good. And then the payoff I was hoping to be huge but there was no payoff.

Mac: All right and you said we a few times, did you have a partner in some of these or…?

Drew: Yeah so with Firerift I was working with two people that I brought on, a buddy named Will Wilson and then Michael Zuna and Michael Zuna actually is the CTO of Plasso and he was a neighbor growing up so he’s like my older brother’s best friend so I’ve known him for like 20 years or more so we did that project together and then we did Plasso together so it’s like a big long gap really we didn’t do anything together but yeah.

Mac: Okay until also you… it sounds like your kind of edit core developer but you’ve mentioned potentially going to design school and I noticed a lot of your sites and apps look really good you must have I mean you have a good sense of design is that in creating icons, does that just kind of come sort of naturally to you would you say?

Drew: Yeah, yeah, I’d say it’s kind of actually the other way around like I started off like as a kid doing art, traditional art, cartogram paintings, charcoal, a lot of stuff and then I moved into using Photoshop and doing that same stuff in Photoshop and then I decided you know with the website stuff back in the ‘90’s it was always like, there was no like, there wasn’t really a concept of everything like works together, it’s just like text with like weird background patterns and like you put like a 3D floating logo here and something there. There wasn’t like a concept to like making everything flow together in like a one consistent user interface other than the actual system software so I remember seeing Microsoft’s website maybe it was like it must be ‘96 or something or maybe it’s ‘98, it was a little after I made my first site so sometime in ‘97 I don’t know I saw the website in the header, went to a sidebar and there was like this rounded corner here, I was like how in the world did they make a rounded corner like I like inspected the source and everythign for like the first time real seriously, trying to figure out how they made a rounded corner turns out, it’s you know, it’s two tables and they put an image there that had a you know, a built-in Photoshop of a rounded corner. I was like what? So I was like, that’s cool, you can make sides like look like there’s something and so I started up design like I said I didn’t get into back-end code until 2002 so I was always a designer like all the projects that I did and I learned, I taught myself, in the development so I could see my designs like and make them interactive but then I ended up. I always thought that I would hate development, i said there’s no way I’m going to be a developer so that’s like super boring and nerdy but then I ended up loving it so I ended up doing both.

Mac: That’s awesome. It’s exciting okay I’m still kind of trying to get all my, you brought up so many things that I had questions about so your first… your literal overnight success. Can you tell me a little bit more about that and like did you say that was a, it was icons?

Drew: Yup, those were my Pictos icons so I was definitely at like a low point in terms of like my career, financially and all that kind of stuff and it was fantastic to see things turn around literally overnight. I mean I woke up I’m like what there’s like people tweeting about it and then like oh this is so cool you should definitely go buy this and like telling people I’ve never even heard of a new or anything like that and I was like oh wow like people are actually buying this thing and i look at Quixly and I got a bunch of sales and like oh wow this is awesome I was like who knows you know just maybe that was like a couple of days but then it just kept going on and just kept getting more and more and like whoa what does this mean, is there a bank account I can hold this much money yeah, it wasn’t that much money but for me it was like the most money I like ever seen, I was like blown away and…

Mac: And so what contributed to that, to that overnight success?

Drew: For that day I think I had a decent following on Twitter maybe I had like 2,000 or something like that, people following me so that was a pretty good amount they’re all designers pretty much, they’re all user interface designers or web developers or something like that so they can all make use of it and the main reason it was successful is because there was literally no competition and it was a product that made sense like it made your life easier, you wouldn’t have to design these icons. I didn’t stylize them in the sense of like they have like a unique theme to them. They were just like super generic looking so they could work with a lot of stuff and that wasn’t like a conscious decision. I just wanted generic looking stuff because I liked generic looking stuff but it turns out that worked but the main reason it worked I a hundred percent was lucky on timing. Now when I like… launched then Pictos 2 then 3, those did super well. and it was a big break and then there was Pictos Outlines and Pictos 4 and it started taking off and by the time I was there everybody was selling icons and because so many people started selling icons they were easy to make, I mean you sit down for like a month making icons and then you can watch the set and not have to work again because there was you know really easy to make there were tons of designers that were like oh I’m going to hop on this and a lot of them are using my software Quixly itself. I was able to see how the upkeep were doing and it quickly just became a race to the bottom where people are like all right let’s charge less, let’s charge less to get these sales up and people were offering like lifetime like improvements in these icons products, I was like what in the world like this is insane and so now I mean they’re all free.

Mac: Yeah.

Drew: Like you could get the best icons for free and that was absolutely not the case when I launched, there was Glyphish and Hlvticons and that was like it so it was a hundred percent timing, that’s the only reason I was successful I knew that and I knew that it would taper off and die and so I was like I got to make the most of this time while I have this money I just got to make as much stuff as I can and do what I’ve always wanted that kind of thing and that’s why I ended up making a lot of stuff.

Mac: That’s great so it doesn’t sound like it was like necessarily a big marketing push it was kind of right place, right time and you were in the community so you could reach people but I mean even 2,000 Twitter followers, that’s cool but you know the lifetime of a tweet…

Drew: Yup. It was a hundred percent timing and I had like Dribble had come out like a year before something like that so I was one of the first people on Dribble but there was other than that there was zero marketing, still to this day I’ve never marketed Pictos.

Mac: Yeah can you do you even know can you give us a sense of numbers on any of that over any sort of timeframe?

Drew: Yeah I was making like so another successful app of mine was Screeny which was screen recording for your Mac because back when I launched it when days of leopard there was no way to do it and then they added it in Quicktime with Line with Mac OS 10 Lion so that was doing really well. I spent about $90,000 building that because at that time I didn’t know how to make Mac apps very well so I hired someone else and so I spent about $90,000 making that and doing a couple of updates and I think that thing brought me like close to $100,000 like all said and done over time but monthly like at the height of when that was out and Pictos was out I think was making like $10,000 a month or something between those two and so it was like way more than enough to support me but I wasn’t like saving any of that money and nor did I want to I was just a hundred percent putting that back into paying other people to help me build different things, that kind of stuff so all that money went into you know making more stuff.

Mac: Okay so that, there’s other list the rest of these apps did you build most of these or is it a combination?

Drew: Yeah so like let’s see the iPhone KidCam and Bulk Delete I partnered up with my buddy Eric, @madclouds on Twitter, Eric Bye and we made those together, he’s local and he wanted to make some stuff, I’m like yeah I’ll make some stuff with you let’s do it so we did those two things and then Filtron I had paid developers to help me build the iOs app but then I ran out of money so I ended up taking over that and the mac app so then by the time we launched everything it was all me doing all the development and the design all that stuff and everything else. Back in the day, I did Roon with Sam Selfies so he and I wanted to do a blogging platform. He overheard me talking to a buddy about me wanting to build one so we teamed up together to do it and then that got acquired by ghosts and then I built my own the way I wanted to do it just all by myself so I built that all by myself, built Namebox by myself, Bulk Delete by myself — yes, it’s kind of a combo. I’d say like half of them I’ve done alone, half of them I’ve partnered.

Mac: And overall how did they do and what type of marketing do you do for them, clearly now I think you’re focused on Plasso again but…

Drew: Yeah so what I really wanted to do is because I only had a limited amount of time, a limited amount of money was I wanted to find something that have like its own legs and would like do well on its own and the product like resonate enough because I had like an experience that once with Pictos where the product resonated enough that it did really well and it’s super motivating when you’re building something like that versus building something, where you like have to force it and you have to sell, sell, sell just to be able to make some money like that didn’t really appeal to me so I wanted to make something that had its own legs and so that’s kind of why I was doing a bunch of different stuff I’m like hey you know what maybe blogging seems to… let’s try blogging, turns out not really, maybe domains are huge and it still can be that one’s still kind of an if but in the way that I did it not really, with Quixly maybe digital delivery is huge, I found out no it’s not at all and the fact there’s another company that was really big with that called Gumroad and then they ended up burning through all their cash and having to go down to just one person again and it’s just because that industry at this moment is not, is not big, it’s not a lot of revenue, it’s not really too there, so I wanted to try a bunch of different things try Mac apps, iOs apps when Bulk Delete came out there was no way to Bulk Delete your photos but then Apple quickly added that to their Main Photos app so yeah just trying a bunch of different things to see like what would stick and turned out that Plasso was that thing so then I focused full-time on Plasso.

Mac: So marketing those was it similar still was it you know put it up in that in a lot of cases up in App Store and kind of hope to get noticed and then notice you know…

Drew: With Plasso, yeah with like most of my stuff trying to think of anything that I really spent a bunch of time marketing I honestly haven’t on anything actually.

Mac: So you pretty much build it put it up in the App Store, make a website and tell your friends? Then that’s…

Drew: Yup. That is what I do a lot like when a product came out I would launch it on product time to give people time to talk about it but I was always kind of had the mindset of like I don’t want to spend a bunch of money marketing this stuff, I’d rather if its not going to take off, I’d rather take that money that I was going to spend marketing it and putting it into something else that will kind of like work on its own and that isn’t necessarily like the best way to go about it, it is just the way I wanted to go about it I was very well aware that I could take all my money and put it all onto one thing but I didn’t want to do that because if it doesn’t work out I wouldn’t have any money to build something else afterwards.

Mac: Right.

Drew: So I decided to do a different approach was to build a bunch of things and for me personally it was fantastic because I got to grow a bunch as a developer, as a designer, as a business owner, I got to learn a bunch about different markets so that was the approach that I wanted to take.

Mac: Okay so where… now we’re getting up to Plasso where did that idea come from and how did that whole thing come about?

Drew: Yeah so it kind of started back in the days of Quixly which was my digital delivery service the business model there did not work because it was 2009 or ‘10 when I launched it and it was the days where like you would charge for how much storage someone uses so Quixly build it based on how much storage you’re using and I think one other metric and I can’t remember what that was but that obviously doesn’t work as a matter of fact when I was building Quixly it was kind of before AWS was big or anything like that and I’m trying to remember – I’m pretty sure they were around but I think they were pretty expensive so we were actually looking at different server farms here in the area, different co-locating spots for like basic put our own servers in there because storage was such an issue but those days are long gone.

So anyhow that business model didn’t work, the software was great though and I ran after like i think 2009 or ‘10 until 2012 when I launched Space Box and Space Box is an app that I let my son name, he was two at the time like what’s should daddy name the app he’s like Space Box, all right sweet so he named that thing and that was my attempt to like a human interface to Stripe so Stripe have just launched really two years before but they were working on stuff with YC and everything so they never really launched until the year prior or maybe even that year when they started getting popular and so I was like okay this is a cool API but let’s make like a way for anyone to interact with it so I built Space Box where you could create your own payment spaces, payments page and then somebody can just go there and like pay with their credit card and then I had the idea of like adding products into it but again the business model there wasn’t good and for that reason it was because I had a free plan so it’s kind of like freemium where you go in and use it for free and if you wanted to add more than two spaces, two payment pages then you have to upgrade and pay a monthly fee but that wasn’t the greatest because someone could just go and make two accounts you know or three accounts or whatever so there was a couple of issues with that and the way that business model worked aside from what I just mentioned and so I never really made much money from Space Box at all even though I used it to sell my icons and tickets to my conference stuff like that and then and so I think I ran that, yeah, I ran that in 2014 in like summer of 2014 I rebranded and I relaunched as Plasso and…

Mac: It was just , just you?

Drew: Yeah all this time. Space Box was a hundred percent just me and Plasso a hundred percent just me, and the Valio Con a hundred percent just me, supporting and all that stuff and then I launched that in 2014 and the business model was doing a lot better because I got rid of the free plan and I changed it so that way it’s essentially free, you could sign up you don’t pay any monthly fee and you only pay us when you make money because we charge a transaction fee so that works out really well for people to be able to try it out and if you’re doing successful, if they’re successful and their products are selling they could just upgrade to another plan pay a little monthly fee and reduce their transaction fee and then you can upgrade it even further to reduce the transaction fee further so that ends up working out really well for people who want to sell stuff which is obviously what Plasso enables you to do sell stuff so the business model’s working I was making a good amount of money from it and so I was like yeah it’s either going to be I’ll just try to grill this thing super slowly on my own or I go out and raise money and just try to you know do it really quickly and I had already built a bunch of stuff that worked with many different people before building things so I was like yeah I could totally handle this like you know the concept of like working with other people and like directing them and myself having done like all aspects of building software, I was like yeah I feel super comfortable like you know with who I can hire, I already has people in mind and raised money so I could build a team and then take us to the next level a lot faster than what I can do on my own.

Mac: So were you already at a place where you could have a sustainable living from Plasso even before you decide to raise money?

Drew: Yes. Yup. I was making enough money to pay for myself and some just a little bit, it wasn’t… it wasn’t like wildly, fantastically successful to the point where I’m like a millionaire or anything like that but it was enough that when I went to raise money even though it was February of 2016 when all those articles started coming about how the VC tides have changed and like money’s tightening up and all that kind of stuff. I was like oh perfect right when I’m going raise this stuff happens but because of the fact that I was making money is why I was able to raise money so it definitely helps out if you can actually go through the fire yourself, not just so you can raise money but so you can actually appreciate money.

Mac: All right so your decision to raise money was based it sounds like just on wanting to make it bigger faster…

Drew: Yes.

Mac: …as opposed to…

Drew: A hundred percent yeah. While I raised money because there’s like a bunch of stuff that I wanted to do to the platform, been working with e-commerce type things myself for years and I have like a pretty clear direction in my head what exactly I wanted to do where I want to take it but in order to get there just by myself will be very difficult. It actually got to the point where it would be impossible because the amount of you know support that I was doing for my customers fixing things, adding things, all that kind of stuff I had no time to progress the platform you know to where I want to see it I was purely just you know supporting customers and if it was like a… if it was like a small kind of you know app or like a little service that might be fine but what I want to do is take this to be huge I want it to be the place to start a business on the internet so in order to do that, yeah, I could go at it by myself and slowly you know build which I’ve done in the past always bootstrapped everything but this time I was like you know I don’t want to do that anymore. I want to take it to the next level.

Mac: And so I’m curious why Plasso is different and why that’s the one you decided to raise money for do you think it’s because of the level of success that you’re seeing with it or do you think it’s because of the timing in your life and you’re okay I’ve done all these other things before now I’m ready to just kind of make this the one.

Drew: Yup so for me like when I did Firerift my first piece of software I raised money, I raised $20,000 from a buddy who wanted to invest in it. It’s a horrible mistake because I eventually paid him back by other means but $20,000 is such an insanely small amount of money. I mean I never saw a dime of it nor did I want to I just used it to pay people to help me but it goes nowhere so small right and I wish I would’ve known that back then and then I did a thing called Dialoggs which was essentially slack except like public so anyone could make these rooms. When I was in 2012 I actually interviewed at YC for that but they didn’t accept us for that and then also someone afterwards gave me $20,000 so I’m not going to make the same mistake again thinking if I just get $20,000 I could pay my developer this much time it will get to a point where it’s successful but no so through those two things I learned like I do not ever want to raise money for something that I could build myself, to see how well it will do if we’re talking about that small amount of money and so anything I did like after that I was like yeah this is not something I want to raise money for because from my experience working in like other kinds of apps I know how often things fail and how often things are unsuccessful and I don’t want to put someone else’s money in that risk when I kind of know in myself there’s like a super small chance it’s going to work out, I’d rather just learn the lesson myself and go through the fire myself because if it works out when you come out of the other side like you’re in a way better position to raise money and with way better terms all that kind of stuff and I was totally fine with doing that this way for… so when I got Plasso and I’m like thinking about Plasso might take, this thing could be really big because of the market that it’s in because the need that’s you know this could be going much bigger than like you know a photo editing app or something like that right it’s a way bigger market so there’s that and then there’s also the fact that it’s already doing well by itself right that’s showing me that its got traction all by itself just offering from its feature set so that was like another thing and then it had gotten to the point for me personally where I really wanted to raise money and to try that out because I’ve done it for so long by myself and I already do appreciate money when it comes in and frugal in that kind of sense that I feel comfortable raising money and I feel comfortable specifically raising money for Plasso because of the fact that it’s already making money so the risk is a lot less for anyone who decides to give me money that kind of thing so.

Mac: Yeah so what was the process like going out and raising money did you … were they like connections that you had or did you… is this all new territory for you?

Drew: It was a hundred percent new territory for me. In the past like I said it was probably had given me some a little bit of money, each time $20,000, to the dime but in this case it was going to be something different if I wanted to raise money, I wanted to raise around $1,000,000 and that’s going to be obviously, in a whole other scale than what I had done before and I felt out the area in San Diego and unfortunately San Diego doesn’t really have a very active like an angel or even a VC environment so not only that the terms here are kind of like shark-tanky where they want to offer nothing you know.

Mac: Yeah.

Drew: I mean it’s more like… it’s more realistic and it’s more like what the rest of the world is doing but I think just the move to San Francisco and have it’d be totally different why you wouldn’t do that right so I got an ardeen[SP] in the country friar with my family and we stopped off in San Francisco and I stayed there for six months straight and so going up there I didn’t know any angels or VC’s at all, not a single one but I did have a buddy who had just recently raised money and a couple other pals who knew some angels but really those didn’t like pan out, other people say yeah I worked with angels, I know angels but it doesn’t really mean anything unless they raise money from it right so my buddy had raised money from SV Angel for first round a bunch of other big companies and such, he got me meetings with them so my very first meeting with a VC was at SV Angel and my second one was the first round so two biggest ones in the valley. But before that I did have meeting with one of his angel investors, it was horrible I mean it was great but it was horrible because I for some reason I don’t know why I didn’t like put a whole pitch together for something I was just thinking oh it was just a seed and we don’t need all that stuff, I don’t know why I was thinking that and so I met with this angel and he just tore me apart for an hour and a half in his mansion. Yeah, it was no fun a lot of awkward silences, me just like looking at the having no idea what to say next, it was horrible.

Mac: Did you just go in and you were just winging it you really didn’t have a…

Drew: Yeah so then I went and made a whole pitch and everything a couple of days later I met with SV Angel and still there was a lot of things about the industry itself and the way that VC works and the way that funding works I just didn’t get so I swung and missed a bunch in the beginning but then you know I got better I learned it all and I knew you know I knew like you know this was something I had no idea about I’m going to fail hard but I can enjoy that because then I could learn quickly. So I ended up after five months raising (.2 million just under which at that point I was like yeah, this is good enough for me let’s be done so I could get back to building so it’s not like an easy thing I mean I didn’t expect it to be easy but it’s definitely not an easy thing to go and raise money so I thought it was super cool that I was able to do it and the best part about it is that I was able to build like you know a team that I wanted and still stay here in Carlsbad so it was pretty fantastic the way it worked out so.

Mac: And so when was that? When did you come back to Carlsbad?

Drew: Yeah so I came back in June of this year.

Mac: Oh wow! Okay.

Drew: Yeah that was when I also finished off the round.

Mac: And so you just… you said eight people now?

Drew: Yup, yeah.

Mac: You have a team of eight? And so you just put that team together? You pretty much already knew who was going to be it sounds like.

Drew: Yup, yeah.

Mac: A chunk of it.

Drew: I mean there’s still a bunch of people that I’d love to hire but just like I said from knowing people over the years , from working with other people, there’s a lot of people that I want to work with so hopefully in the future it’ll happen.

Mac: So can you tell me at the time of I worked with a lot of start-ups and I see the difficulties in raising money at various points and I’m curious what you’re feeling maybe what was your you know your MRR at the time of raising money or what would you say is a good amount to be bringing in on your own if you want to go out and raise some money?

Drew: Yeah I think like most people or maybe it’s just what I read. It seems like a lot of people think that you got to kind of have some kind of revenue if you’re going to be doing like a B to B kind of business if you’re going to raise money because that’s kind of what we do. If you’re doing like a consumer kind of business you probably don’t need to have any money that you’re making you just need to have people download your app or using your service or whatever it is from my experience people who are raising money in that aren’t making money and even after they raise money they’re not making money I mean like even some of the biggest companies right now are not making money Twitter so you don’t really need to have any money through dealing that kind of an app or a project but if you are going to do B and B you probably are going to need to make some money and I will probably say you need to make around $10,000 to $20,000 a month. If you’re making that kind of money you should have no problem getting a seed round and by no problem I mean there’s going to be someone who wants to give you that money. It might take you five months like it did me because that’s kind of the range I was in, making between 10 and 20 and when I went out to raise money so I know that if I wasn’t making that kind of money like I would not have raised any money at all so from my limited experience raising money in the big leagues once I would suggest that if you’re going to do B to B you should make like between 10 or 20, closer to 20 obviously is better but yeah after that I mean after you get someone believing in you and you get somebody you should be able to go bring that MRR up and then as long as you’re growing at a good rate you can have your existing investors give you follow-arm or if you’re doing pretty well you should be able to get a Series A because you are making money especially if you’re profitable, if you hire slim enough and you’re able to get profitable you can or cannot raise money because you go it alone you know and build it that way so.

Mac: So has it been overall a good experience for you?

Drew: Yeah it’s been super great, it’s been… it’s wild like right after I launched Pictos I moved to right where I am right here not the specific unit but in this area right here and so I think like a month after I launched Pictos I moved here because Pictos started doing so well and I was like yeah one day I’m going to have my own business here and employees here all that kind of stuff and it happened to be that I ended up back here with an office with my own employees and everything so it’s definitely like living the dream I mean it’s by no … just because I raised money and I brought on a bunch of people so you go from profitable to not profitable you need to work your way back up so until I get to that point it’s always going to be like oh gosh I’m not profitable anymore so there’s always that feeling but that’s a good feeling since you’re the driver right but once I get there I think I’ll have a better time like, be like yey, yey I finally made it that kind of thing you know so.

Mac: So what’s next, what’s on the books for Plasso? What are you guys up to now and where do you see yourself?

Drew: Yeah, yeah so we got since I raised money, we’ve been spending a lot of time like behind the scenes doing a bunch of stuff and we just launched yesterday it went really well, just relaunched yesterday I’ll say.

Mac: The product hunt.

Drew: Yeah, yeah it went really good, got a lot of people checking it out and this is really the first we have like publicly launched anything since I raised money what I wanted to do is take some time to like redo the text stack because it was like the Drew Wilson framework and that’s not… super fast and easy for me to work with but not necessarily the team so we kind of like re-worked some of the way the back end works and I really wanted to continue with like the shift that, shift often thing and so we built in some guardrails to it and to anyone could kind of of mess with products and actual system… the product code like the back end code but never actually touch or ruin the system so we built it that way so that way everyone who works here can kind of mess with code because I hired designers who are also developers so all of us you know touch code and so took some time to do that also took some time to build in a few systems for our future products that we’re going to release. And even built some of those future products already and they’re kind of waiting in the wings and what I wanted to do was come out with a relaunch like we did then we’ll have a new launch coming out in a few weeks after that we have another launch so we’ve got like a few things where we launch like the next four to six months and we kind of spend a lot of time on the… while we’re staying quiet building that stuff so that way we could it’s kind of my marketing plan is to always be launching something new, something cool which will you know get people to talk about it all that kind of stuff.

Mac: So these are entirely new products here you’re referring to now?

Drew: So these are new products inside of Plasso so.

Mac: Inside of Plasso okay.

Drew: Yeah, yeah so we have like a membership product which allows you to do subscription billing super easily and the whole pitch with Plaso 2 is there’s no coding or development required, you don’t touch code you just click, click, click and you’re done so we have the membership product, we have the storefront product which is more one of sales, sell yourself digital goods, we have the invoice product and the payment product which is what Space Box originally started with where you just go to and people can just go there and pay you at any time and then we have a handful of new stuff that we’ll be launching pretty soon. So those are what I mean by products.

Mac: Is your son bummed it’s not called Space Box anymore?

Drew: He doesn’t mind, that’s kind of funny because I really wanted like when I was rebranding Space Box I wanted a dictionary name and so I came up with the idea of Plasso, I’m like sweet. There happens to be available so I bought it and I did trademark searches for anyone you know with Plasso with a K and a C or other strange callings nothing right, nothing in the tech world, like, sweet I’m going to be Plasso, bought the domain, did the branding like you see there except it ended in IC and was ready to rock and roll I’d like posted something on Twitter about Plasso and a week later I got an envelope in the mail from some company it was a cease and desist I was like what is this? Like they saw that one random tweet and it was a company called Plastiq ending with a Q and I’d never thought when I did the trademark search I never thought that anything with a Q and it doesn’t do like searches like that so I was like great and they happened to be like in the price payments or something and they wanted the domain they wanted all the logos I’m like no, no, no, no so I hit up the CEO and I was like hey sorry man our lawyers are just crazy sorry I know all that stuff but you can’t use the name I was like okay fine so I still have the domain name but I was like okay I like what I did with the branding but I got to somehow like somehow keep that but change the name and I was like I don’t want to deal with domain traps, I got to find domains like all of them are available and so I just ended plas and a bunch of different things and I found that SSO was something that was available so Plasso’s available I was like I’m going with that the .com was available, everything was available. I’m sorry the .com was expiring in like a month, I was like perfect I’m not going to tell anybody anything, I back-ordered on a bunch of different services for the .com and when it came to expire because it was already expired, it was coming back to market like it was like…

Mac: Okay and there was nothing actually out there?

Drew: Yeah it was like coming back to market, the person already let it go, it’s already past their renewal time, everything it was like perfect but somehow someone else like snaked it out, out from under me and someone else got the but I got literally everything else so I launched as, we were .co for a long time until I saved up enough money to buy the .com from the person and then just yesterday we relaunched as

Mac: Oh man, that’s amazing…. I like it, I like it well Drew this has really been awesome, very inspiring. Good luck with the new launch and I’m excited to see where you take Plasso. Can you tell listeners where they can find you?

Drew: Yeah you can find me on Twitter @drewwilson. You can go to or, if it’s easier. I don’t know why domains are one of my hobbies for some reason but I’m sure everybody else does too but yeah find me on Twitter, you can find Plasso @paywithplasso. Someone has Plasso and they don’t use it you know one of those typical things but we’re at paywithplasso so.

Mac: That’s great. Well thanks again, it’s been great and good luck with everything Drew.

Drew: All right, thank you.

Mac: Thank you, take care.