The SaaS Bootstrapper Podcast

TSB009: Growing business through creating great experiences, with Lee Rubenstein

Listen now:

Episode overview:

Today’s guest is the Co-founder of ArtSnacks, a subscription box for discovering your new favorite art supplies. He also also the creator of EatSleepDraw, an online art gallery where he posts 100% original content submitted by contributors across the globe, and is the largest user-submitted blog on Tumblr. Lee shares some amazing stories, including how met David Karp, Founder of Tumblr while working in a co-working space, and how his blog EatSleepDraw helped shape Tumblr.

Lee also talks about his thoughtful and passionate views on running ArtSnacks:

Lee also shares a 10% off coupon for your first ArtSnacks box!

Guest links:



@ArtSnacks on Twitter

@EatSleepDraw on Twitter

@LeeRubenstein on Twitter

Mentioned in this episode:

The interview:

Mac: Welcome to another episode of the SaaS Bootstrapper Podcast. Today’s guest is co-founder of ArtSnacks, a subscription box for discovering your new favorite art supplies. He’s also the creator of EatSleepDraw. EatSleepDraw is an online gallery where you post 100% original content submitted by contributors across the globe. It’s also the largest user-submitted blog on Tumblr which is pretty impressive. Lee Rubenstein, welcome to the show.

Lee: Hey, thanks for having me.

Mac: How are you?

Lee: I’m good, I’m good, I’m good. Thanks for that little setup, that was nice. You did your homework.

Mac: Yeah. Well, there’s a lot more I can say but I figure I’ll try to leave some of it for the conversation here, so. I see a lot of…I can’t really tell what it is but it looks like you have a lot of ArtSnacks behind you.

Lee: Oh, behind me right now?

Mac: Yeah.

Lee: Yeah, tons of sketch books, boxes that we’re working on, some art on the walls of some of my favorite artists. Yeah, I like to…if I find an artist, I like to buy their art and just…like, an original piece of art, so.

Mac: I like it, yeah.

Lee: And I’m just picky like that. I’m not really into prints. I’d rather own the actual thing, you know?

Mac: Well, I was wondering if I was gonna see mostly your art or other people’s art.

Lee: Oh, yeah. I mean, I do a lot of art kinda, like, internally for testing products and that sort of thing, but all the art on my walls are just artists that I admire or have befriended over the years, and yeah. Wanna support them, so I buy a piece.

Mac: So both of these projects…I actually don’t…you might have other projects as well or have done them in the past, but these two are both clearly art related. So where does this art…is this a passion of yours that you’ve always had or is this…

Lee: Oh, yeah. Oh, yeah. So art has been in our family and my grandfather was an artist, commercial artist. I don’t know how successful he was, but when he passed away, I inherited all of his art supplies. I knew as soon as I picked up a crayon that I wanted to get into art in some way and, as a kid, I took all art classes that I could, my parents are very supportive, and extracurricular art classes around town, like pre-college programs into visual art, and I just knew that I wanted to do something with art ever since I was young. So that’s kind of why it’s in my blood. Both my parents are not visual artists but they’re very creative and my sister as well is, I think, more creative than I am in some of her artistic ideas. But yeah, it’s in our family. I don’t know if art’s in our blood but definitely creativity is in our blood so that’s kinda where it comes from.

Mac: So is your career path all been somewhat following an art path or are these just newer?

Lee: Yeah. I don’t know. I mean, specifically with the two projects you mentioned, they started as projects, and I’m, like, all about having a side project and those two that you mentioned started as side projects. EatSleepDraw came first. I’m a type of guy that if I’m in a situation or an environment and…for example, in 2007 I was working in a shared office space in New York City. I was still in college and I was an intern for an animation studio, Frederator. I believe I was the first intern but he had the shared office space and he…and Frederator was the type of guy that would have all these creative people in his work space during the day. And one of the people that were working in there was David Carp, and this was before he started Tumblr, and I was on Blogger at the time and we became friends because I would go into the studio a couple days a week and he was working on some client work, developing websites for people, and on the side, he was building this thing called Tumblr and it was…I got in there really early. I believe I’m, like, user number seven of Tumblr. I was on Blogger at the time and this was back when Blogger was getting really big and I believe that they just transitioned over into Google, being a Google product.

And so being an artist, Blogger was so intimidating with that big, white box and the blinking cursor, and David saw it as an opportunity to create something totally new and fresh and kinda make it into different digestible post types, right, if you wannna post a picture, post a picture, if you wanna post a chat, a link, just a video, it’s not as intimidating to get into blogging, and so I immediately gravitated towards that. I thought it was a stupid name at the time. You know, he was trying to be like Flickr, where he dropped the “E” at the end, and so it’s just funny because now they’re owned by the same company and they both…you know, Yahoo bought them recently, few years ago. So not seeing that, I thought it was a stupid name but I totally got what he was trying to achieve with his product. And so being in the unique position where I basically had the ear of the creator of this new thing, I was being selfish almost. I mean, all the things…like, cautiously selfish. It’s like, “Oh, well, this is great. I love posting during the day on Tumblr.” And I told David, I was like, “I’m not gonna sign up for Tumblr unless I get the username ‘’.” And he’s like, “Fine. I’ll give you Lee because it’s such a short name.” And so that was exciting for me so now that got me more involved and then I totally got it, it was great posting my art throughout the day, things I was working on, and I was like, “This is great. I wanna create a blog where it’s just about art.” And so me and my…Ben Roselee [SP] was also an intern there. We started posting our art and we were like, “We gotta think of a name for this place.” And so we called it EatSleepDraw, and so it was just the two of us posting our art throughout the day, at the end of the day, doodle sketches, whatever.

And then I went to David and I basically said, “Hey, Ben and I created this thing. Can we make it bigger? I wanna invite all my friends to post their art.” And he’s like, “Oh, you mean, like, multiple authors?” And I was like, “Yeah,” not thinking that maybe he had some sort of product roadmap down the line that he was gonna have, like, multiple authors on a blog. So he opened EatSleepDraw to have multiple authors, I got all my buddies on board, my friends from art school, and it got to the point where it was like 50 artists posting art at all these different times and I would have to go and…if I get an email from someone saying, “Hey, I love EatSleepDraw. I wanna post my art,” I would have to walk them through the steps to sign up for Tumblr, and create an account, and then invite them as an author.

So I went back to David and I was like, “This is way too complicated. I got projects I gotta work on. Can’t you just, like, build a thing to have people submit their art and if we like it, we’ll post it?” And he’s like, “Oh, you mean like user submissions?” And I was like, “Yeah, yeah, that’s exactly what I want.” So he enabled public user submissions on EatSleepDraw. That time, I believe we bought the .com because we were like, “Okay, this is gonna be a big thing. We have no idea where Tumblr’s going, but we wanna have this as a place for art where people can post their stuff.”

And for, like, the first six months, we were the only tumblelog on the Tumblr network that had public submissions enabled, and I would get even more emails saying, “Hey, how did you hack Tumblr,” and that sorta thing. And so it just kinda spawned out from there. Eventually, everyone got public submissions on their Tumblr, but I saw it as being in a unique position where I could basically be in the ear of someone creating a new product and kinda mold it and shape it in the way that would benefit not only me and wanting to see cool art that people are making, but also this Tumblr community that was starting to develop. And so, fast forward to now, we’ve been publishing art for, like, nine years on We’re still based on Tumblr as part of the Tumblr blogging network, and we have over…I think I checked this morning, like, 850,000 followers every day on our tumblelog, which is just totally mind-blowing, but more impressive for me is just the…not only the sheer quantity of art that is submitted on a weekly basis, I believe we get, like, close to 1,000 pieces of art submitted to every week, but just quality of the art, and people from all over the world, and all different skill levels that are taking…it’s such a huge thing to put yourself out there and blindly submit your thing that you created for someone to judge.

And so we take that responsibility very seriously when we’re actually looking at people’s art. And so I have help on that now, it’s run by myself, but really the day-to-day operations of are handed off to Anthony, a friend who I went to college with. We both have art degrees, we know what to look for, and we’ve published over probably 60,000 pieces of art in 9 years and every day, every hour and a half, constantly it’s just this circle of constantly publishing art throughout the day, 24 hours a day, 365. So it’s really kinda gotten bigger than we ever thought it would be, and one of our subscribers or followers wrote about it and we’re like, “This is a marvelous fountain of art.” And we’ve always kinda felt very honored to be the stewards of this, you know, this place on the Internet where people can get inspired. You don’t have to submit your art, you can just look through and, you know, if you do wanna submit your art, you can post…you can submit your piece and link to whatever you want, if you wanna sell prints, or go to your blog, or portfolio, or whatever. And so, you know…and we actually made it a fact when we first turned on public submissions that we wanted to be able to accept art from people that are not members of Tumblr, so…and that’s been since day one. You don’t have to be a member of Tumblr [inaudible 00:10:20], or you can just go to and you can just submit your art, and if we like it, we post it.

Mac: Wow. That’s a…

Lee: Yeah, so it’s good. It’s this thing that’s been living for the last nine years. It’s kinda slowly growing and growing.

Mac: Well yeah and I love…it’s amazing that…it sounds like you definitely had an impact on the direction of Tumblr as well and I’m sure that was a lot of importance to him to have all that feedback from you that you’re actually using it and these are your needs, and it’s also really interesting that there was a time when a lotta these features were just boxed into your blog itself and then finally, at some point, must’ve realized that, “Oh, man. There’s a wider need for this,” and that’s really great.

Lee: Yeah, I think part of it also…there were a lot of bugs early on.

Mac: Sure.

Lee: There’s a lotta bugs with the posting mechanism, but once they figured that out, yeah, they rolled it out to everybody and now everyone can have that enabled on their tumblelog.

Mac: That’s really cool. So that’s a lot of followers for EatSleepDraw. So I have a question about your…the vetting process. Do you do much…it sounds like you approve all the…do you approve literally every post that goes up?

Lee: So the answer is yes, a human looks at every single piece of art that is submitted. There’s no algorithms or anything like that, but I can say it’s either myself or Anthony that is looking at the piece of art that’s submitted, and the great thing about Tumblr is that once you click “Approve” on a submitted post, it goes into this, like, queue, and so it just…you set frequency in terms of posts, so he looks at it maybe once a week, maybe every other week and queues up couple of hundred pieces of art, and then it just goes in line and sets it to autopilot and that’s it. Unless, you know, we have sponsored posts that we have to schedule in, but yeah that’s why it’s a marvelous fountain of art, you know…

Mac: That’s really cool.

Lee: …it’s on autopilot.

Mac: So yeah. So at some point, you realized that you could monetize this a bit and you started finding sponsors for the blog. So can you talk a little bit about that? The whole process of at what point did you realize that that might be a good option and what…how you went about finding sponsors, and how you figured out how to utilize those, and incorporate those, and charge them?

Lee: Yeah, I mean, I think the overall advertising industry online, it’s gearing towards what they like to call native advertising, but we like to call sponsored posts, and I think those are the same thing. So we started rolling out sponsored posts several years ago, and so even though we have 800,000 plus followers, the majority of those people that are viewing the content from EatSleepDraw are viewing them internally on the Tumblr dashboard, and a follower’s following not only our blog but other blogs that they follow on the Tumblr network. So we knew that regular pop-up ads and standard ad units weren’t gonna work to this audience because, really, the eyeballs are internally in the dashboard. So we knew that very early on.

So sponsored posts are basically the only way that we can sell eyeball audiences, you know what I mean? So that’s kinda where our strategic value was from day one. We also we’re approached a lot just…you can just see the amount of notes that we get and likes and comments that, like, people that…as Tumblr grew, brands started coming on and we would get contacted by all different types of brands and people that wanna advertise, and we’ve always been very, very protective of the audience because we’ve seen a lot of other sites that exploit it, right? They’ll sell anything, right? Where we really wanted to add value to the community that we built.

So one of our long-time sponsors is Squarespace. I have a feeling they, like, sponsor everything on the Internet: podcasts, blogs, everything, but they’ve been a great sponsor for us because we have a lot of young artists that follow our site and they’re on Tumblr and they want to develop a portfolio, take their work off of Tumblr, get, like, a Squarespace portfolio site, very easy for them to do. So they’ve been a really great partner of ours and adding value to our artist community, get their own website, get off Tumblr sorta thing.

We’ve also partnered with other art supply brands that wanna promote new products, new colors, stuff like that. So we’re not gonna run an ad for Toyota. You know, it just doesn’t make sense for our audience. So we’re very, very conscious about the advertisers that we bring in, and we’ve always positioned them as sponsors because you’re sponsoring this community and our sponsorships are exclusive for the week, and the advertiser or sponsor feels like, you know, they’re getting their money’s worth and they’re also feeling good about sponsoring the community, and yeah, we just have a very strong voice and need to respect our followers’ time. So that’s kind of our positioning map [SP].

It’s not a huge business, if you wanna go about the business side of it. It’s not a huge business. It’s still a side project, side business that Anthony and I run. He has a full-time day job. He’s not…you know, it’s always been a side business and, you know, we care more about keeping the community up and going and providing sponsorships that will get people inspired, or get people looking more professional, or that sorta thing. So it’s really not a huge business, but if I could transition over to my day job which basically spawned out of this huge audience of 800,000 plus followers.

Mac: Well, yeah. So let’s talk about that. So at that point…well, let’s see, what was it? Maybe 2013 you started ArtSnacks, so.

Lee: Yeah, it was funny. It started with a phone call. It was a phone call from my sister. She called me up. It was around this time about…well actually, almost four years ago, around this time of year, on holiday time, and she called me up and she’s like, “Oh, what do you think about getting Birchbox for your wife? I wanna gift to your wife, Birchbox.” And I was like, “What is Birchbox?” I had no idea what it was and she explained to me, “You know, it’s like you get beauty samples, and product samples, and smells, and lotions. You know, samples sizes in the mail and it’s a surprise and you gift it to either yourself or someone else.” And I was like, “Oh, that’s a great idea. Her favorite store is Sephora. You know, she’s a girly girl and she would love that.” And then I was like, “Is there anything like that for me?” And my sister’s like, “You want lotions and smells?” I was like, “No, no, no, no. I don’t want that.” I was like, “I want, like, an art box. Is there an art box out there? I want…you know, I like pens, and markers, and inks, and brushes, and art supplies.”

Mac: Was this literally while you were on the phone in this conversation that you were…

Lee: Yes, this is the conversation. Yeah, yeah, absolutely.

Mac: That’s amazing.

Lee: So she was like, “Oh, wow. I don’t know, maybe.” And so, I was like, “Yes, get that for Lauren. She’ll love Birchbox. But let’s talk about me for a second. What are you getting me?” Again, going back to the whole selfish, like, “What…” I was like…the closest thing that we could find after doing some initial research was, like, a craft of the month, right? And I have much respect for the crafting industry, it’s just not what I was looking for. I was looking for something totally just very focused on art materials and art supplies. These craft of the month boxes were giving everyone directions and everyone would make the same thing, and while neat, not…kinda boring, right?

So we…you know, everyone’s making the same thing’s kinda boring to me. So what I was like, “Well, if there’s anything that…nothing out there that is exactly what I’m looking for, why don’t we make it? Why don’t we try to see if, like, this is…is there a reason why people…this thing doesn’t exist?” And she’s like, “Oh, okay.” And so about three months go by and, you know, we’re talking about this idea. She’s living in Boston, I’m in New York, and there was no art supply subscription boxes out there. And so we were like, you know, “What are we gonna call this thing? You know, how much are we gonna charge people? How many items in the box?” We had way more questions than answers, like how…who’s gonna ship this stuff? You know, how are we gonna manage members? Are we going to take people’s money, manage their accounts? Like, I’m not a developer, I’m, you know, a creative guy, marketing background, but we just didn’t know if people would even sign up for a thing like this, right? So we settled on, you know, what we wanted to call it, and what it was gonna look like, and some of the initial marketing things, and I was all stressed out about…okay, launching. You know, we don’t really have a budget for advertising and my sister, like, pulls me back and she’s like, “No, dummy. We’re just gonna make sure it works and then you’re gonna blog it on EatSleepDraw, and hopefully people will sign up.” And I was like, “You’re absolutely right. You know, I’m overthinking it.”

And so we launched for, like, a first box preorder February 1st, 2013, and did a preorder for a month, and then we were off to the races. We’ve shipped every month since February 2013, and it’s just grown. For the first two years, my sister and I both had full-time day jobs and it was sustainable. It’s been profitable since day one and we kinda launched this thing where it’s a very unique curated experience and it turned into ArtSnacks, which is what it is today, four or five items, thoughtful considered curation, the products are going to work well together right out of the box. You’re gonna get a little info card of what is featured this month, what it works well with, tips and tricks, links to videos online to how to use them. We’re gonna send you a piece of candy, because it wouldn’t be ArtSnacks without a piece of candy, and that’s deliberate. We don’t really advertise that we send candy, it just kinda shows up every month. Different candy, different art supplies every month, and then a sticker, some kind of button with our logo on it, wrapped up little burrito with a cute bow and that’s it. It’s like a little art snack. It’s a little kick in the beginning of every month for you to, like, try new materials. Our customers don’t know what they’re getting ahead of time and we are very, very focused on doing, like, exclusive first look products. We moved to a place where, you know, we’re really, really focused on product, and where the industry is going, and where we wanna with what we’ve created, and we’re just really, really excited about art supplies.

We’ve always been excited about art supplies. Ever since my grandfather…I inherited his art materials, you know? I still have his art box behind me, so I’ve always been artistic and very into materials themselves, as well as techniques and how to use them, and so unlike the craft of the month where when we did research, everyone’s making the same craft, everyone gets directions. With ArtSnacks, there are no directions. Everyone’s getting the same art supplies. People will get different colors, right, but then we have this social layer that we’ve kinda built on top of our subscription box where you get your supplies for December, you’re gonna get same supplies maybe slightly different colors. Everyone’s gonna…that gets the box is gonna make their ArtSnacks challenge as we like to call it. They’re gonna create an original piece of art using only the items that we send them for that month, and then they’re gonna share it on their social media site of choice, “#artsnackschallenge”, and you get to see what everyone is making that’s different with the same supply. So that’s really exciting. So that’s kind of, like, ties up our whole service in a little bow and also kinda helps with the word of mouth marketing of our service.

Mac: I love that. That’s a really good idea. I’m gonna have to go look. Seems like…I was starting to wonder if you’re ever gonna say that you were having them then push pack into EatSleepDraw or…

Lee: Well, I mean, it’s gonna happen. It’s definitely a different…in terms of a business, it’s definitely a separate business, right, different paperwork, different bank accounts, stuff like that. We really see it as a sister company, right, that operates in the same universe, but if people submit their artwork from some of the challenges they do on ArtSnacks to EatSleepDraw, we’re fine with that. And I think the whole thing is we have this great community that…what do you do with 800,000 plus artists? You sell them art supplies, of course. So it was just. like, sitting right in front of us and we kinda just…if it’s gonna work, we’re gonna continue to do it. So that’s kinda how it sits in terms of two businesses that coexist next to each other, right?

Mac: Sure. But yeah, you were really fortunate to have had that enormous built in audience from day one to…I mean, that’s…you’re not gonna get any better direct marketing than that for that price.

Lee: Super targeted, super focused.

Mac: So I assume you went and blogged about it on the Tumblr blog, and right away, were you getting signups? I assume.

Lee: Yeah, it’s grown exponentially month over month. I’m not gonna share too many numbers, but I think in terms of subscription-based businesses, churn is a really important metric that I’m sure your audience will know about. You know, we have a very low churn rate. We retain customers for a long period of times, and focusing on product…you know, on a software product is different than, I would say, focusing on, like, actual physical products, right, because you wanna keep people engaged and I don’t think we’ve ever repeated a product in, like, almost four years of sending out art supplies. We’ve done different colors and print variations like on paint brushes, you get different bristles, different materials, that sort of thing. But yeah, keeping those customers engaged is really important.

Mac: So you had mentioned when you were first starting off that there were all these questions unanswered. You didn’t know, “How do we charge for this? How do we do all of it?” What would you say were the biggest challenges, really, just starting off? I mean, it seems like…yeah, go ahead.

Lee: Starting off…I mean, starting off was, “It’s gonna work.” And after doing research on the subscription box, it was almost like a trend early in, like, 2013, maybe 2012, 2013 where you’re seeing all these beauty boxes pop up and some get really popular, and some kinda fall away, and that sorta thing. So there are, like…the business model is not…we basically stole our business model, right, from Birchbox and did as much research as we could in terms of, like, what challenges we’re gonna face if we scale up, you know, if people start signing up, but shipping is really hard. Shipping is really hard if you’ve never done it before. I’m not talking about shipping software, I’m talking about literally schlepping to the post office hundreds of boxes…

Mac: Hundreds of…

Lee: …without a vehicle in New York City, trying to, like, navigate through the streets when it’s raining. You know, those are just, like, everyday, like, basic operational challenges. Launching and taking people’s money is the easy part if you figure that out, there’s tons of software available, but shipping is really, really hard, and shipping on time, and being consistent is really important. And so we learned very quickly that that was probably more important than some of the items that we were shipping early on.

Mac: So just a logistical question that that brings up. Do you send all the subscribers the products at the same time or is it based off of when they signed up? Like, do they all get it the first of the month or if I sign up on the 15th, do I get it more in the middle of the month?

Lee: Yeah, great question. So we will ship them all at the same time. Because we don’t…we’re very customer-focused, right, so we ship all of our boxes out at the same time, and we’ve gotten to a point now with software and other things, where we know to the day that 89% of our customers are gonna get their box on that day. So we can plan around that. We can plan marketing around that, we can plan emails around that. And so I don’t know what other subscription boxes do because I only know the one that we run, but yeah, going into it…let me back up a little bit. There’s no way that ArtSnacks would be successful without a few people behind the scenes and some people sitting in copilot. One of them is my sister. She’s my younger sister. I’m older about five and a half years, and she comes from a totally different design experience. She used to work at this website maybe you know, maybe you don’t, maybe your wife knows it, They do, like, flash sales and deals and stuff like that. So she’s coming from that world, that design, fashion, online world. And so we basically…when we started creating this ArtSnack brand, you know, what do we wanna make people feel when they subscribe to our service? What is our website going to look like? And we’re really positioning ArtSnacks as a way to discover new materials. And so that’s really been her focus, very brand-focused, very product-focused. Photography is extremely important, especially in this type of business. We’re in the art business, it’s a visual medium, it’s gotta look good, right? Instagram’s gotta look good, email’s gotta look good, and that sorta thing.

So her task was to make us look good, right, and having that…you know, she’s a co-founder, and really, we’ve been…she’s focused on that and I’m focused more on operations and logistics, and some of the business end of it, and some marketing aspects of it. But yeah, finding someone, like, if you’re starting something, finding someone that complements you in your skill set is so important. It just so happens to be that she’s my younger sister, right? It just worked out that way. And so we’ve always considered ourselves, like, a small business, you know? It’s a family business, obviously, because she’s my sister, but it’s also a small business. We’ve never considered ourselves a startup mainly because if you don’t consider yourself a startup, then you’re a small business.

Mac: Right. Well, and we can argue terminology and what even a startup means, but profitable from day one with just…being able to just blast out to that audience and know that…I mean, this is…like, go from day one with no overhead and that’s all. That’s pretty, pretty great.

Lee: It’s one of the magic special sauces of subscription, you know? Recurring revenue is amazing.

Mac: It is. So do you guys have any other help now or is it still just the two of you?

Lee: We literally last month hired our first employee.

Mac: Okay. And what’s their task?

Lee: And she…her name is Madison. She is in charge of email customer service. We pride ourselves on our customer service. We subscribe to the Zappos philosophy. I don’t know if you’re familiar with his book, “Delivering Happiness”. We subscribe to his philosophy. Everyone should be in the trenches doing customer service when appropriate. And the difference between us is that we care. We care about our customers, we care about the product we’re sending people, and Madison, who we recently hired, she’s great because she used to be a customer of ours. So she…hiring a customer did not work on the other side of the coin and be part of our team and help us grow. It’s, like, great. It’s amazing. She’s already familiar with what we’re doing and how we operate as a customer. So, yeah. So it’s just the three of us and then we have a fulfillment partner who’s been great, and yeah.

Mac: Does that mean you’re not…

Lee: Like I said, small business.

Mac: Yeah, so you have a fulfillment partner. Does that mean you’re not actually packing and shipping the boxes anymore?

Lee: Not anymore, no. We’ve been working with them for about two years. They’ve been great and there’s no way we would’ve been able to scale, you know, long-term without having a fulfillment partner.

Mac: Sure. Well, this has been really, really inspiring. Touched on a lot of really great things. And when I asked you for a little information before the show, you just threw out some very genuine, honest feedback, or, I guess, advice, or just…and you did also just touch on it, but, like, your philosophy and you mentioned it’s about how you make people feel, and you mentioned to me, “Give people more than they expect,” which maybe is also what that piece of candy is in the box, but.

Lee: Absolutely, yep, yep.

Mac: But you mentioned a few other things to me too that I’d like you to touch on if you could. You said surround yourself with people who make you better and create something that you want, and these are all…it just shows to me that you truly do care about what…you love what you’re doing and you also very much care about it in your customers, and I think that that’s often the case. I don’t think it’s the case as much as I’d like to see it is. So if you could touch on some of those in your sort of approach to the whole…your whole business here.

Lee: Yeah, you want me to go down the list here that we have?

Mac: Yeah, sure.

Lee: Okay, yeah. It’s not what you make, it’s how you make people feel. I think people…at least when they’re starting a new thing whether it’s a project, or a business, or whatever, they get caught up in the mechanics and the actual, like, functioning of the thing and can sometimes not put theirselves in the customer seat and how they’re gonna make them feel when they actually click the button and after the click the button, right, to sign up, because it’s just really important. If you don’t have any contact with a customer once a month when they receive a box in the mail what can you build around that to make them feel special, to make them feel like they’re getting their money’s worth, to make them feel like they’re part of a community, right? So that’s where I’m going with, “It’s not what you make, it’s how you make people feel.” And then you touched on give people more than what they expect, piece of candy, you’re absolutely right. That’s why we do it. We don’t advertise that piece of candy, it just shows up every month, more than they expect, and part of the experience that we’re focusing on is, you know, you get so excited, your ArtSnacks box is in the mail, you grab it, you open it, you rip it open, and it comes with candy, and you start chomping on the candy and testing out your art supplies. Like, that’s what we want.

Mac: It’s a good experience.

Lee: That’s the experience that we want. Yeah, yeah. You’re chomping on your candy, you got a little sugar rush going, and you’re just super pumped because you got this amazing Japanese brush marker that you can’t even get in the United States, and you own it, right? That’s what we want. That’s the experience that we want for our customers. So giving people more than they expect.

One thing we didn’t mention, for an idea to work, it has to be obviously good. Kind of a, you know, floaty piece of advice, but if you break it down, for an idea to work, you know, why is Birchbox so successful or has been so successful is you just break it down to the thing, they’re sending makeup samples in the mail, and kind of our hypothesis for ArtSnacks back when we started thinking about, you know, is this even a good idea, is… “Well, if they’re sending makeup supplies in the mail, aren’t…makeup…isn’t makeup just art supplies for your face? Why don’t we just send art supplies?” You know, like, it’s, like, it’s gotta be obvious. Like, that’s what makeup is and cosmetics is, it’s art supplies for your face.

Mac: It’s too funny.

Lee: “So let’s just send art supplies and it’ll work, I’m sure.” And having a built-up…built-in audience is just icing on the cake, but, like, breaking down ideas into, like, what they actually are, you know, before executing is really important. So it’s gotta be obviously good. Surround yourself with people who make you better. My wife is amazing, my in-laws are amazing, my parents, my sister is amazing. Surrounding people… You have a crazy idea to send art supplies in the mail, you know, kinda crazy if you’ve never done it before, so.

Mac: Yes, sir.

Lee: You know, surrounding yourself with people who make you better and also complementary skills and that sorta thing. But being in a one bedroom apartment in New York City with hundreds of boxes around you when you launched several months ago and tapping your wife to, “Hey, could you open the door,” or “come with me at six in the morning to the post office so that we can, you know, ship out on time?” There’s a reason why I married her, because…

Mac: Right, you’ve got some good support.

Lee: …she put up with me, that’s sorta thing. So you gotta get support system around you, it’s important. And then create something that you want, you know? ArtSnacks, sending, you know, art supply monthly subscription box, people may have had ideas before we launched but we were the first. I believe we were the first. I’m gonna call it on your show that we were the first art supply subscription box, and we wanted it to exist and so we willed it and worked to make it be. You know what I mean? And so we really wanted it to exist so we created something that we wanted to exist and that’s what it is.

Mac: Do you send yourself a box every month? Do you actually…

Lee: I do. I send myself multiple boxes actually.

Mac: That’s great. Lee, well, it’s been…that’s all really great, again, and very inspiring, good stuff to hear. And I have one final question before we close down here, but you mentioned a little earlier how…that this was a bit of a crazy idea to send art in an art subscription box, art supplies subscription box, but you’ve also then mentioned it has to be an obviously good idea. So I’m trying to gauge how confident you were. So now, looking back, and I hear that idea and I’m like, “Yeah, of course that’s gonna work. People…all kinds of people love art and love art supplies. Why wouldn’t they like this? Who wouldn’t wanna just get a box of art supplies at the door?” But when you were actually having this idea and considering actually implementing it and making it happen with your sister, what was your confidence level, do you think, at the time of…that it would go?

Lee: Well, yeah. I mean, this wasn’t the first side project, I could tell you that. There were a lot other side projects. Having a very focused audience of artists on EatSleepDraw, it’s like, “Okay. Well, let’s do a magazine. Let’s do EatSleepDraw Magazine and then let’s sell prints of people’s artwork.” Like, this is not the first idea. So I will frame the conversation there that this just so happened to stick, right? And confidence, all of those projects that I mentioned previously, the magazine, selling people’s prints online, when I have a side project, if it doesn’t work within, say, three, four months, I shut it down. I shut it down and I move onto the next idea because it could be anything. It could be timing, could be audience, could be execution. It could be anything. So I’m the type of guy that if I have an idea, I’ll kinda sit on it for a little bit. I’ll do research on the side until something sticks and then I just go in that direction, really.

So confidence level. I was confident I was gonna launch it. Was I confident in would people sign up? No, I had no idea how many people would sign up, if it worked like my sister said, and if it was a good idea, and if people were willing to risk…there’s so many factors that could go wrong: product not showing up, price point being wrong when launching, so, like, everything had to be considered before launching this particular side project. It just so happens that it kinda spawned into a full-time job after two years of doing it on the side.

Mac: That’s really great. Lee, well, super exciting, so.

Lee: Are we outta time? Don’t tell me we’re outta time.

Mac: Do you have more? Let’s go.

Lee: I don’t know. What else do you wanna talk about?

Mac: Well, I could keep going, but you’ve just covered so much really useful stuff that I think listeners have a lot to think about. So if you have anything else you’d like to bring up.

Lee: No, I’d love to give a coupon code to your listeners if that’s okay.

Mac: Let’s do it, yeah.

Lee: So let’s do coupon code…I’m literally making this up on the spot, and after I read it off the call, I’m gonna put it in. So let’s do “SAASMAC”. Let’s do that.

Mac: Sounds good.

Lee: S-A-A-S-M-A-C. We’ll do that.

Mac: And where should they go to utilize that?

Lee: Yeah, so go to and using coupon code “SAASMAC” will get them 10% off their first month of ArtSnacks.

Mac: That’s great. That’s really generous of you. So as we record this, it’s nearing the holidays. Do you get an uptake in subscriptions at this time?

Lee: Yeah, fourth quarter is huge for us. Gifting, people buying yearly subscriptions for themselves to, like, challenge themselves in the new year. We’ve really expanded our business. We do these collection boxes, big boxes, one-off collections usually around a certain theme. We have an online shop now where people can buy previous boxes that we featured. Yeah, we’re pretty busy. That’s why we hired our first employee.

Mac: That’s great. Well congratulations, Lee. Is there anywhere else people should find you? I think we’ve mentioned the domains. I just wanna…

Lee: Yeah, EatSleep…,, if you wanna look at cool art. Follow me on Twitter @leerubenstein, one word, or go to Use “SAASMAC”, get 10% off.

Mac: Sounds good, Lee. Well thanks again.

Lee: Thanks, Mac.

Mac: Been great talking to you.

Lee: My pleasure, thanks.

Mac: Take care.