Chris Shifflett (2:37)

Yeah, thanks for having us.

Jessica Hish (2:38)

Happy to be here. Yeah.

Aaron Walter (2:40)

Oh, so excited to have you on the show, both of you. So I met you both maybe at similar times back in the day in Brooklyn in Dumbo at Studio Mates, which our friend, our common friend, Tina Roth Eisenberg started. And I often described Studio Mates in that time period. Was this like 2010ish 2012? Maybe.

Jessica Hish (3:03)

Maybe even a little earlier? Yeah, maybe.

Chris Shifflett (3:05)

Yeah.

Aaron Walter (3:06)

Could have been earlier. Yeah, I described it to people as kind of like the late 1960s Yankees. It's like an embarrassment of talent. It was like, here, here's Jessica, here's Chris, here's Jason Santa Maria. And on and on and on. It was so many talented people in one place. What was it like there in that special time and special spot?

Jessica Hish (3:26)

Oh, it was super fun. Tina had the space with Chris and Cameron and a couple other folks before Jason and Jesse and all those folks moved in next door. So I used to have a studio at the Pencil Factory up in Greenpoint. And then when I bought an apartment in Bushwick, I was like, I don't need a studio anymore. I can work from home. I have this new apartment. And that lasted for like four months. And then I was super lonely and all of the spaces with all the illustrators in Greenpoint were full up. So then I had heard of Tina's spot because I knew Tina and a friend of mine that was in her space was like, hey, maybe you can do part time and share the desk with me there. So I moved in. Coming from a world of all illustration people and being the web tinkerer of that group into Tina's space and being like the only non full time web person in that space. But it was amazing. I feel like me and Chris and everybody really hit it off immediately. We brought some levity to the space and started having like beer Fridays on our own before it turned into like a rock band full thing. But yeah, it just started with me, Chris and Cameron every Friday at 4pm going down to the fancy corner store and trying out a different random beer together to have some camaraderie and stuff. And yeah, that's where the friendship really started.

Chris Shifflett (4:44)

And people talk about how sometimes the good old days are hard to notice when you're in them. But I think all of us really felt like that was a magic space and a magic time in terms of the web. I think that it was this period of experimentation. Things were fun. Even companies, you know, it was important for them to have open APIs so that you could tinker with their stuff or tinker with your data on their website. And people were just making things. And it felt like this era of possibility. It was also kind of like the golden age of Twitter. We were all connected again. Everyone had iPhones. It was just like things that now feel stale and less fun were new then. Yeah, it was just a really magical period of time. It's a great time to get to know people.

Jessica Hish (5:30)

Yeah, it felt like everything was a Friendly chat room. Twitter was a friendly chat room. Our studios were friendly chat rooms. Everything was just a really good hangout. And it's not like we weren't working and working really hard during that time, but it was just so good to be surrounded by motivated people, passionate about what they do. But also we're there to really appreciate the time spent together because we're all working on our own things. But the idea that we're all working on our own things collectively and are able to support each other and ask each other questions and stuff, that was really awesome.

Aaron Walter (6:04)

You know, we can't talk about that time period without talking about Brooklyn Beta, which was really a seminal conference. Not really a conference. It was a gathering of really talented folks and really interesting people. And it brought diverse skill sets and perspectives into a single place at the right scale where people could really connect and talk to each other. Chris, you co founded that and co ran that. Can you talk a little bit about the. It sounds like a big word, but like the legacy of Brooklyn Beta that it brought people together and people have stayed connected since then.

Chris Shifflett (6:40)

Yeah, I mean, that was such a fun time. In a way, Studio Mates felt like it was this core group of what became this broader community in Brooklyn Beta. So I met Cameron there at Studiomates, along with Jessica and other folks, and we decided we want to do a conference together for a few different reasons. I mean, conferences were fun back then too. That's another thing that it feels like we've lost a little bit. There are fewer and fewer of these kind of independent, really community oriented conferences. But one of the ones that really blew me away was Webstock. And I spoke there one year. I think Jessica had spoken there, Jason spoke there, like, so several of us have had this experience of just the hospitality there in New Zealand, the quality of the experience, it wasn't really like, you know, oh, what speakers did they have? As a speaker, you felt like a true vip, but they kind of treated everyone that way. And I thought, wow, if we could be half as good as Webstock, you know, we'd be really onto something great. After the first one, people really liked it and would say, like, really flattering things, you know, like, this is the best conference I've ever been to and things like that. And it always just made me think, well, how that's because you've not been to Webstock before. But yeah, it really felt like the studio mates, broader community, all having an excuse to come to Brooklyn, and we just poured our hearts into that. And the food was, you know, Restaurants that we loved, many of which had never catered before. We just talked them into it. Speakers spoke, because we just talked them into it. We didn't have a reputation to lean on the first year or two. It was just trying to convince people to come and speak and restaurants to make great food and all that fun stuff. And then as it got a little bit bigger, you know, it's hard to think that 300 people was the bigger version. But year two, it kind of was, because we only had maybe 100 people or so the first year. But we realized that it would be very difficult to make every single person feel as respected, I guess, and as when it was such a small, intimate event. So one of the ideas we had to change that, that ended up being a huge amount of work. But I think people really did appreciate it was Cameron and I just split the attendee list in half, and we each wrote every single bio of every person there. And Tina, I probably never even told her this, but to me, she kind of inspired that idea because when people would come to studio mates like visit, and we had visitors all the time, she would tend to introduce each of us to the guest. And she always talked us up in a way that you would never do. So if you were talking about yourself, you know, like, oh, this person's amazing, blah, blah, blah. And I thought, I just loved that so much. I want to give that to everyone. So basically, everyone's badge was a bio that we wrote that just heaped on the praise like a friend would, you know, and really talked you up. And people loved that so much. I saw people saying hey to each other, and they would each be holding each other's badge because they wanted to read the bio, even if you already knew the person.

Jessica Hish (9:50)

I think one of the things that I've never said, Chris, in terms of Brooklyn Betas being so rare, is like, I've been to a ton of conferences and talked to a lot of conference organizers. And hosting a conference in a cool city is such a risk because so many people that attend conferences when they're actually in cool places just use it as a tourism. Excuse me. And I think that that really speaks to how awesome the event was and the community that you built around it. The programming, the side stuff that people were really there for, that they didn't just use it as an excuse to go around New York. A lot of the attendees were native New Yorkers, and they didn't use it as, I'll pop in for the talks that I want to go to. And then Otherwise be at my office, which happens for a lot of events that are held in New York or LA or any other place like that.

Chris Shifflett (10:37)

We prevented that a little bit by not telling anyone a schedule. And when we had a schedule, we rarely stuck to it. So you kind of had to just be there and be part of the experience. You didn't know what you were missing when you weren't around.

Eli Woolery (10:49)

So both of you spent a lot of your career, apart from these things like conferences, doing client work and you've both become very well known for the work you do. And now you're on a slightly different path and you're making basically a SaaS app. And having been in the startup world for a while and now Aaron and I are doing the show independently, I kind of get the draw for like doing your own thing and then also all the stress that comes along with it too. So it's kind of a double edged sword. But what drew you both to start this new venture?

Jessica Hish (11:18)

I'll kick us off because I was sitting in my office here in Oakland thinking about how it had been a really long time since I had an excuse to like tinker on the web or do any fun things. I had just been sort of seeing things bubble up over time with the death of Twitter and a lot of things of people being like, man, the Internet used to be fun and now it's just not fun. Everything is just people selling things to each other. No one's making stuff for the pure joy of it. Everything's about how do I become a unicorn, how do I get rich quick, how do I extract as much value from this thing as possible instead of just making stuff that's just purely about I want to make this. It brings me joy to make this. This is a thing I want for myself, therefore I'm making it. So I really called Chris out of the blue. I call people sometimes from my car cause I drive a lot. But Chris was not on my phone. A friend listen. But I was thinking to myself, I would love to build cool products for a more niche audience. Who do I know that has the same passion for this kind of stuff as me? Who loves community and wants to serve community, who would rather dive into building a good small business rather than trying to shoot for the moon with everything that they make and build? Because I live in the Bay Area, which is Moonshot Land usa, going through my friend group here, they would be like, oh, so you want to make a thing that's just a small business that makes a modest amount of money. They're like, I'm going to go do my AI thing and make a billion dollars. And so when I called Chris, we had this really amazing brainstorm where I had gone to him initially suggesting that we do a really quick, sprinty project. But we were talking about all the things that we wish we could build that were kind of related to that, which ended up really being the roadmap for studio works. And so as we were talking about it, I was just like, oh, we could do this. And Chris was like, we could do this. And at the end of the conversation, Chris was like, y. But I haven't done proper hands on web development since pre css, so we probably need a development team to help us with this. Let's put a pin in it and come back later.

Chris Shifflett (13:27)

When you're brainstorming like that with someone, it's fun because you're not really constrained by what you actually can do. You're only constrained by your imagination. And both of us had been running our own creative studios for a long time by this point. So we had a lot of the same pain points and a lot of the same kind of embarrassing stories. We had anecdotes about QuickBooks, sending a reminder to an invoice that was outstanding, but it wasn't really. It just hadn't been reconciled, Right? And you're copied on that reminder and you just feel immediately embarrassed, like they make you look bad to your clients and you feel guilty because you feel like you're just failing at business. And so we had all these ideas that were around helping people like us not only just run their businesses a little bit simpler, like tools that were just a lot simpler and more bespoke to us, but that also made you look good, made you look really professional. Cause that was very important to us. So I think Jessica had a couple of conferences to speak at, and I got to wireframing again. Wireframing is also easy. You know, you can just kind of go where your imagination takes you. And I kind of mapped out this whole project. And also while Jessica was away, Sean and Nick, who are on the team now, both reached out because they had both quit their job on the same day. And I remember specifically talking to Nick because I know that he's in a position to be able to take this kind of a risk. So I was like, please, whatever you do, invest in yourself for the next year. You know, don't just take another job. If I can convince you of anything, as a friend, do this. And I was like, now, I would love it if you would invest in yourself with something that I'm working on also. So let me try to convince you of that. And Sean and Nick both came to Boulder here at Roost, and we had kind of this mini summit where I walked through a lot of my business ideas. I was looking to do something new and I wanted to bring up StudioWorks as one of the ideas. But I wasn't trying to bias it. I was genuinely curious if they would want to work with me. Which of these kind of things to pursue seemed the most interesting because I know that they're also very seasoned. And as much as we might love fun Internet projects and kind of that era, we also have families to feed now and needed to pursue something that had the most chance of success. And, yeah, it was very fun to then call Jessica and say, like, I think they're in. StudioWorks is the thing that all four of us are most excited to work on. And Nick and Sean are, you know, the best of the best. I worked with Sean building out Samsung's global E commerce platform. So there's no amount of scale or sophistication that we couldn't handle with this small team of four. So it was like, hey, all those ideas we brainstormed, they're all possible. Let's go.

Aaron Walter (16:28)

For listeners, that's Nick Sloan and Sean Coates, who you're working with.

Jessica Hish (16:33)

Yeah. And I mean, Chris has started and been a part of lots of complex software businesses, but for me, as a lettering artist and author and primarily someone who works for themselves as a creative, people might feel like it seems a little out of nowhere to suddenly be making a startup, being the primary product designer of a startup. But the thing that really drew me to being so passionate about studioworks wasn't just the team, because obviously anyone will tell you that you don't invest in a product, you invest in the team and the people behind it because they're the ones that are actually going to make it successful. So I'm such a people believer. But it also, all of a sudden, as we started really talking through it and Chris was wireframing things, it became so clear that studioworks was the thing that took every single thing that I've done in my life and just distilled it into one thing. I love being a resource for people and helping with that. I've written and given courses on pricing work and how to make more money. I've made a big part of who I am and my business about helping other creatives get paid better, manage their time better, basically just live their lives better through the way that they structure their businesses so that they can have a more sustainable career. And it felt like studioworks was a way for me to take all that passion and a lot of the resources that I've already created and funnel them into a thing that could actually scale and be way more impactful than an individual course or something like that.

Aaron Walter (18:09)

Can you give us a quick synopsis of what StudioWorks does does for its customers? How does it solve problems for independent creative people?

Jessica Hish (18:19)

First thing, we ended up focusing on invoicing as our first thing that we do. So invoicing and payments. And part of that was based on my own experience and the experience of other creatives in that usually if you run your own business, you're doing everything very analog from the jump. And the first thing that you decide to grow up with is to suddenly start using a platform like QuickBooks or FreshBooks or something to start better tracking your money. But the problem with all of the platforms that are out there is that they are these really complex rich accounting and bookkeeping software. And for the most part, finding the thing in the product that you're actually using takes 20 clicks and steps. Their business model is built around you getting paid through them. So therefore, they collect money from you. There's only one experience that you can have with it, which is you send an invoice. And the only interaction that your client can have with that invoice is to pay via that platform. But as a creative, Chris and I both know that when you get paid by clients, you get paid every which way from Sunday. So you get paid on bill.com, you get paid through whatever bespoke system that they have. You get paid by check, you get paid by wire, you get paid by whatever. And on every other platform, there's not a way for your client to really interact with an invoice in that way, because there's no incentive for those companies to build that interaction. So, first and foremost, business wise, one of the big things was we're not trying to make money from your money. So we don't take any transaction fee from anything that gets paid through StudioWorks. We just use Stripe's bare bones financial infrastructure price, which FreshBooks builds on top of. Stripe has an invoicing platform that they charge on top of. So we are literally the cheapest way that you can receive an ACH transfer, which is huge because we don't take money from that and we don't rely on that as a part of our business structure. We can build really cool workflows for clients to actually make the online invoicing thing way more useful. So we have this mark as paid flow where a client can say, I'm paying through bill.com on X date, mark as paid, which then stops them from getting alerts about. You have an unpaid invoice and it gives the studio data about how things have happened. So that if you have to have a conversation with your client about not receiving a payment, you have stuff to talk to them about. So it just really makes all those conversations a lot easier. Right now, if you're using anything else and a client sends you a check, they don't have a way to tell you the checks in the mail other than just emailing you about it. But with us, if they don't say, I sent the check, you can say, hey, I assume this was paid. Can you mark it as paid? And that allows you to go in with good intent. And then if they actually go in and mark as paid, you have data. So if they said they sent the check three weeks ago and you haven't received it, you can write them and say, hey, it looks like you sent the check three weeks ago. It hasn't shown up. Can you talk to the accounting department about reissuing a check? So it just makes that interaction way better. One of our goals, which Chris already talked about a little bit, is just making you look super professional to your clients and just making everything about the business end of it feel like you have a team helping you with it. Even though it's just really good software.

Chris Shifflett (21:41)

Even that little interaction I think helps people feel like they're presenting themselves so much more professionally. Because, for example, I've seen a lot of people send invoices where they'll have a note and they list the five different ways to pay and all the information you might need to pay in any of these ways. Because they don't really know. And for us, we can provide the same information, but only as needed. So if a client is sending you a check, well, they might only know your name because a lot of our customers are independent creatives who maybe operate under a business, but it's just them. So if you get sent a check for just your name, that could be complicated for you. So if they choose check, we tell them like your official legal business name, the address where they need to send the check, and then they tell you the date that they sent it. So we create this micro little interaction to just make this much more seamless and kind of like a first class citizen in Terms of experience.

Jessica Hish (22:36)

This is the thing that separates studioworks from a lot of these other things is thinking about how important those small moments can be in the relationship with you and a client. One of the things that we built in that seems like, oh, of course, why doesn't everyone do that? Is in terms of reminders, we have a thing where the studio gets a heads up email before a reminder gets sent out to the client. So say you're in a hairy situation with the client because you didn't send things on time or whatever. You get the heads up before they get a reminder about the invoice because you might want to cancel that reminder and send it at a later date because you don't want to look bad, you want to make sure that everything works. Or maybe they paid and they didn't mark it as paid and you have to go and rectify that. It gives you a moment to do that. Looking for moments like that is something that we're doing all over the place in the product. And so we started with invoicing and payments and obviously that's really important in just the relationship with clients and also you keeping more of your money and us not taking any of the money. But Studio Works is and will be a lot more than that. We just launched a way to add clients and our goal with that product is to make it sort of like a light CRM. Like a CRM that would actually be useful to small studios. So things like reminding you, oh, well, you last worked with this person one year ago, you might want to reach out again, doing birthday reminders, figuring out ways to bring people to top of mind so that you can not only have a really, really good address book of everyone that you've worked with and track people, but also for us to create those little moments of bringing people up in your mind so that you can actually have better relationships with people. Because right now most CRMs are meant to mostly be about data.

Chris Shifflett (24:27)

It's like a sales pipeline.

Jessica Hish (24:29)

Yeah, it's like a sales pipeline and it feels very inhuman. And we want to make a very human CRM for the Studio Works folks because most of our people are independent people. And it's all about relationships. It's not about the relationship with the sales team at a larger company, it's about the individual relationship. So we're even talking about how do we link a contact's LinkedIn page so that you can get an alert when they move to a different company. I mean, yes, you can totally do that on LinkedIn, but people use LinkedIn in different ways. And LinkedIn is a social network ultimately. Sometimes you don't want to be on a social network all day and you just want to get done with the business that you want to get done with.

Eli Woolery (25:12)

I love all these features and I would have loved to have this 10 years ago when I was doing more client work. And I'm still going to probably move over from fresh Books because I don't love fresh Books and I want to support you guys and it sounds like an amazing venture. I want to talk more about where you planned ahead in the future as much as you can. But just backing up again a little bit. I'm curious for our audience sake. I think a lot of folks are thinking about how might I become an entrepreneur? Just given the challenges in the job market right now in tech, they might not have a choice. They might think, I have to figure this out, either do client work or build my own product. And now with all the capabilities that AI is giving us and the small team that you have able to create this product, I'm wondering if you could talk a little bit about having your background and skills as a designer, which certainly help in the obvious things like designing a landing page or designing your logo content, et cetera. But what are the non obvious things that we as designers might bring to a more entrepreneurial venture?

Jessica Hish (26:06)

One of the biggest things is actually building for an audience that you really care about. I think that a lot of people now, especially with the AI landscape of just being like, how do I make the thing that is going to make all the money? They tend to just follow the success of other things. They feel for the wind in the air and they go, that thing seems to be successful. I bet I could make a better version of that thing. But if you don't care about what the product is or who the audience is and you don't want to like throw all of your passion behind that, it's really hard to make something successful. I've actually been joking with my husband. We have a lot of friends who are serial entrepreneurs and people will ask me to help with logo stuff. And sometimes I like to do things for equity and things like that. But I have kind of a rule where I'm just like, if you're already rich, I probably shouldn't do an equity trade because you don't need to make money from this thing that you're doing. It's really hard to do everything on your own. You know, now there's a lot of like, there's going to be so many One and two person AI driven companies, you need people. You can't do things on your own. Even with us having four people, we would benefit by having a couple extra people to help with customer service and marketing and sales and all that kind of jazz that you can't really let AI do because it's inhuman and people don't react well to it. But yeah, you have to really want that thing to be real and to happen and to have the worst case scenario for it to be a thing that you personally would love to have in the world. And don't work with people that are already rich because they don't need it to be successful.

Eli Woolery (27:42)

I've made that mistake before.

Jessica Hish (27:44)

Yeah, they can just kind of faff about and be like, this is a cool, fun project. Everybody has to have a lot of skin in the game. Financially, if someone does not need it to succeed, financially, it will not succeed. So you need to make sure that everyone on the team needs it to succeed.

Chris Shifflett (27:59)

Designers bring a lot of observation skills to problems that are through practice or their orientation or whatever that help identify weak points in a lot of experiences, particularly like for their clients or any experience that they care a lot about. So the embarrassment of the reminder going to your client that we spoke about or I've had illustrators tell me how line items don't really work for them on invoices because they'll put three times 500 or something. And an accounting department at a big company thinks that's a very high hourly rate for something and they flag it. And I think there are lots of these little details that other companies just would never really bother addressing. Not because they can't or because they're hard, but because they literally just don't notice. I think designers are really good at noticing things because anything that's not quite right really stands out like a sore thumb.

Aaron Walter (28:59)

Yeah, it is a burden being a designer and seeing all the flaws. We can't help it.

Jessica Hish (29:05)

Yeah. One thing is definitely keep your eyes open, look for problems that you want to solve. I think another thing is entrepreneur as a term feels loaded because it feels like it's more connected with growth and raising money and all kinds of stuff, versus just being a small business owner. One of our goals with studioworks is to show that you could make a sustainable small business and that it doesn't all have to follow the venture capital growth above all model. That's one thing that designers are not very knowledgeable about, is how that world works. Because what they do is they see these success stories of oh, now that I have AI, I can make my own company and I'll raise money and blah blah, blah, and I'll get rich. But basically anything within the venture capital fundraising world is not about let's make the best thing, it's about let's make the most money or let's have the most growth, just because there's an expectation for that to be what the investors get. They want a 50x return. And so I just know plenty of people who have set out to build a thing and then fundraised for that thing. And we're basically forced to pivot just because the thing that they were making was not 10xing fast enough. And then you end up in this world in which you're building a thing that you don't really care about because you're doing it because you need to make money. And you need to make money for other people, not even for yourself. That's the one red flag that I would raise to designers that are starting down this entrepreneurial path is first and foremost, start by trying to make a modest small business, whether that's making your own creative studio into a modest small business. Keep your overhead low, downsize as best you can so that you don't need a lot of capital to make it work, and then try to get that going. Because if you do need money eventually to grow, just because you need more staff than you can get to be a part of your founding team or whatever, it's way easier if you have something that has some momentum behind it. So definitely try to do it as light as possible from the jump.

Aaron Walter (31:14)

We'll return to the conversation after this quick break.

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Aaron Walter (32:25)

And now back to the show.

Aaron Walter (32:32)

You know, I can't help but see some of the spirit of your origin stories that we talked about earlier. The spirit of Studio Mates. The spirit, spirit of Brooklyn Beta, which was about community and sharing and creativity and connection. And Studio works out of the gate like the early versions of what you've built, which is quite wonderful. Education and resources and community, those things are baked into what you're making. What's the vision that you have for how this could not only help designers solve the day to day problems, but also allow them to realize their potential?

Jessica Hish (33:14)

We are just in this really wonderful rare position of having four people on our team that have these deep skill sets that are passionate about the thing. So community really is at the core of what we've built and how we don't take for granted the fact that we were all surrounded by talented, passionate people starting out. That's the thing that's really rare in building a company is being able to have everyone be as bought in. But in terms of actually supporting the community, what our goal is is like there's just four of us, we don't have any funding, we all have families and stuff that we have to support and things like that. But beyond that, our vision is to really make Studio Works into this generosity machine for the community. So we're doing that in ways that we can now by building educational stuff into the product. I'm building like a really wild resource library that's going to be just open and available to, but then we're hosting workshops and talks. We have a weekly designtrepreneur meetup that's a support group for folks. We do co working sessions and those are just all part of being a studioworks member. And so we really do want it to be this very wonderful close knit community where other people can find their people in that way. Because we do feel so lucky that we've been able to do that. And Chris, we talk a lot about the sort of pandemic pizza place where pizza places became everyone's backbone during the pandemic just because you were stuck at home and couldn't even necessarily go to the grocery store all the time or whatever. And the pizza place became this thing that you could really rely on to sustain you and be a backup. And we know that because of AI and all the disruptions that are happening, just because of the economy and all kinds of things, there's going to be a lot of people that are forced into freelance that maybe never had it as their dream. And we want to build A safe landing spot for them. They won't know how weird and not great. A lot of the other things that they could have used are because they're going to have this thing to start that was built just for them and to have all these things that can help guide them into that way so they don't have to make the mistakes that we all made early in our career. I think that's something that Chris and I and everyone on the team really has in common, is that we do not believe in the whole. Because I went through a hard thing, you have to go through a hard thing. We definitely stood on the shoulders of other people. Other people helped us in our path, and all we want to do is make something that can help other people on their path. I don't think that you have to put in your dues. Yes, of course, experience is very helpful in terms of learning and making mistakes is helpful, but I don't want to force people into making mistakes because I feel like it's part of the educational process. I want to help them not make those mistakes.

Aaron Walter (36:00)

Jessica, can you talk a little bit about the resources that are built in?

Jessica Hish (36:04)

Yeah, totally. So currently we have a network, a social network that is not meant to be like a you're there all the time social network, because we're all spread very thin already. It's meant to be sort of this asynchronous chat room that you could go in and have a pricing question and within a few hours to a day or two, someone comes in and answers it for you. Right now it's on Mighty, but we'll be migrating over to Circle, and within that community, I put a ton of resources for all kinds of vendors of things. Our members have been really good at sharing resources when they find them. So we have type designers and illustrators and web people and photographers that have all been sharing like, this is my favorite thing here. If you need to do this, go to here. And so people are actively working on building a resource library within our social network. But then also I'm working on a separate resource library which has all of the things that you casually end up having to look up as a designer or creative, like color conversions, paper sizes, screen dimensions, safe areas on social media, all the things that are hard to find, we're consolidating them into one place. And then the other thing that we're building as a part of that is an actual resource for your clients. So that when clients have questions about something or they don't understand what a file format is, you don't have to be the one educating them. You can send them to this page that shows them. Here's why we sent you a SVG instead of a jpeg. And also don't scale the JPEG in this way. Here's what RGB color space means and why it looks different on my screen versus your screen. Giving our studios that are on there the resources for their clients. Because everyone that I've talked to does this on their own already. They basically just have a bucket of PDFs that they send to clients to explain stuff to them. And wouldn't it be nice if there was a continually updated place that had all the things that you ever need to clarify with your clients?

Chris Shifflett (38:03)

So, Chris, I'm curious.

Eli Woolery (38:04)

I know we're bouncing back and forth between your product and then your sort of story as founders, but talk to us a little bit more about what someone might look for in either a partner or co founder. I know Aaron and I were lucky that we were able to work together for many years before we started off on this venture, and we share the same goals. We have great overlapping skills and complementary skills. So those are certainly things. But what, in your experience are some things to look out for?

Chris Shifflett (38:30)

I feel like I've been very fortunate to work with a lot of really good people in my career. Like really, really lucky. The things that I think work really well are when people are really good at what they do, but they haven't gotten to that point where they feel like they've made it so they're no longer willing to work hard, or they feel like maybe their opinion should carry more weight. Opinions need to be independent from the people who hold them. They need to win or lose on their own merits, and I feel like that happens if people are just trying to make a good thing and do some good work. If you really focus on the work as being this separate entity, it's not your identity and everyone's just shaping it and trying to make it as good as it can be. Those relationships tend to work really well. People take pushback better. You don't try to have your idea win unless you genuinely think it's the best idea. Maybe it's actually a really good sign. If no one really remembers whose idea certain things were, or everyone remembers it as their own idea, that's probably a good sign of a healthy culture. I've been really fortunate to work with a lot of people like that in my career, and a lot of it was just luck. Being at Studio Mates during that time, I got to meet a lot of really great people. And I think what Jessica was alluding to earlier, you know, with the community stuff that we're doing and things like that, it is a lot more than a product that we're building. And I think it's because even though, yes, we've both suffered in the sense that we've suffered bad tools and learning a lot of things the hard way, we've also both benefited from a lot of support from other people and know what that's like as well. You know, people that you can ask, hey, I've got this tricky client situation. You know, they paid for this, but now they want this other thing or what do you do for health insurance? Or like, you know, all these kind of questions that come up. And honestly, a lot of the mechanics of running a business feel really intimidating to people in ways that I think dissuade people from starting their own businesses. And it would make me feel really proud if studioworks could help change that and democratize the business side of running a creative business and make it feel a bit more accessible to more of these types of folks.

Jessica Hish (40:51)

Chris and I talked a lot early on when we were building Studio Works about how if we suddenly had 20,000 customers, it wouldn't necessarily be a good thing. Because what we love about our people is that everyone gets it. The people that have joined and have been with us from the start, they believe in the holistic vision of it. Yes, they're using the product and really loving it. But the thing that's really lovely about it growing in a more organic way is that everybody that's in is in. When people have to leave, if people have to cancel their subscriptions, they send these lovely apologetic emails of like, I'm so sorry, but I got a full time job. And we're like, congratulations. You know, so everybody that ends up in our universe, I feel like are people that really get it. And to go back to the studio mates time, I had this really silly Internet project at the time called the Internet sends me Cake. What I did was I made a Tumblr and people would send me cake in the mail or deliver it to me and I would judge their cake and then link people to their portfolio website because people were asking me all the time to help promote their businesses. And I was like, we need to make this into something fun and weird. So I'm like, I'm only going to judge you on your cake. And if your cake is inventive and good, then I will promote your portfolio. Because obviously if you care about cake. You care about your portfolio. And Tina and a bunch of the folks in the studio were just like, are you not afraid someone will poison you? You know, they were very concerned about strangers sending me food that I would then eat. And I was like, no, because anyone that is doing this, they get it. You attract the energy that you put out into the world. If you put out trust, if you put out generosity, if you put out the things that you want reflected back to you, that's what you get. And the thing that has been so cool about studio work so far is our community is so supportive. I now have a group chat with everybody that comes to our designtrepreneur thing. And we were all sending each other turkey picks on Thanksgiving and stuff. And these are people from all over the country that have never had an excuse to know each other in the past. If you build the thing that has the energy that you want, the people come to it that have that energy as well. I feel like the Internet has gotten so impersonal over time. We've been trained that there's not a way to actually have a human interaction with people anymore. Just because algorithms have really shifted how we behave online. There's not an intimate space that's not created in a way that becomes too insular. It's really hard to find that balance of making something that feels open and accessible and human, but that doesn't get immediately taken over by bad actors. And so we just want to show people that there's people on the Internet and that relationships and the people are the thing that are the most important thing. And so we're really building to help encourage people to foster those relationships, not just with their peers and with each other, but with their clients. That really, that's the way forward. Even with all these technological innovations, it's just all about the people and the people connections.

Aaron Walter (44:04)

Speaking of just getting it, one thing that caught my attention is how StudioWorks is beautifully designed. It feels like a product that is designed by designers, people who do care about this. And you've gone to the trouble of partnering with type foundries to have a variety of fonts available for your customers, users to be able to design their identity to their clients and present themselves well. And that, ironically, is something that, with most products that are in this category, that's just not even considered. Can you talk a little bit about the design process of the product and how you think about things like this?

Jessica Hish (44:46)

The reason why other companies don't do it is they perceive anyone that touches their product as a potential customer. They take every opportunity to basically advertise themselves to the people that are interacting with their product. And they're not trying to advertise you as a customer to other potential customers. And we just take the opposite approach where we know that the clients that our people are interacting with are probably not potential customers. Even if they are, I don't think we're doing our company a disservice by highlighting our people behind it. So we just really wanted to make it feel like a white labeled, fancy pants, custom developed thing for each of the studios because it's something that's not accessible to them. If you think about larger design studios, they can hire a development agency to build a crazy custom backend for file management and all kinds of stuff, but independent creatives and really small studios just never have that ability. And it feels like you're just kind of scotch taping a bunch of different products together that are serving a purpose, but not creating this cohesive whole that makes you look more professional in the eyes of your clients. And one of the things that both Chris and I believe in is that design is very meaningful in the success of anything. If you've ever sold a house, you know that staging matters a lot. If you have a well designed house with good staging, you will get 10, 20% more than if you don't. Design is the same thing with even just the paperwork and stuff that we share with clients. If it looks professional, you can justify higher prices. If it looks professional and is streamlined, you can get paid faster because you look like a person who's on top of that kind of stuff. Anybody who looks like they might have a legal team is someone who's going to get paid faster. What we want is for our studios that use our software to look so professional that if they're chasing down a check from a client, even if it's for not that much money, that accounting studio firm looks at everything that's come their way and said, oh, these guys are the real deal. We should probably make that happen. And also look how easy they made it, you know. So with the overall design, Chris and I work really well together. The thing that makes the team so amazing is that we're all very polymathic. I am of course a designer, but I also can do HTML and CSS and PHP writing and all kinds of stuff, which allows me to communicate really clearly with Nick because he's doing all our front end stuff. And I can understand how to design for limitations and different modalities of building versus if you're a designer that doesn't have any experience with UI design or development, you might design something that's quite difficult to accomplish instead of focusing on the thing that is the most streamlined approach. And Chris is incredible at making a thing that is the most streamlined way of doing the thing. Anytime I design a thing, Chris looks at it and goes, what if we made it this and just take some things away? And I'm like, oh, that is better. You're right.

Aaron Walter (47:53)

I love those type of people.

Jessica Hish (47:55)

Yeah. But then whenever he does writing or things like that for the site, I'm like, we need to jazz this up a little bit. So he's really good at getting to the core of it and then I'm good at adding a little bit of warmth to it. And so we're able to really work together. We co work a lot. I'll be in Figma with him on Zoom and we're talking through how we want to do things. So we really do co design quite a bit. Because for me, the UI design and the experience design is not about skinning the product and making it look pretty. It's about how do we make this interaction so easy and seamless and straightforward that it's like you didn't even notice that you were doing work? How do we make that experience so quick and straightforward that you're in and out, you're doing your thing, and then you have to log into your QuickBooks after six months of using us, and you're like, oh, my God, how did I deal with this for years of my life? The hours lost. We wanted to be shocking about how easy and straightforward and delightful it is to do basic stuff.

Chris Shifflett (49:00)

Yeah. One of our core tenets is simplicity, which is easy to say and really hard to pull off, but it's because we see so many people, I think, ourselves included, who feel intimidated by a lot of the complex business tools out there. And it makes running a business feel complicated and even time consuming. We want creative people to spend most of their time doing the work that they want to be doing, not running their business. So we almost want to be provocative with how simple we make these tools. Like, wait, is that all I need to do? Is that all the bookkeeping I need to do? Don't I need some charts and graphs to think about things. We really scrutinize everything that we add so that we can make this product richer and richer over time without falling into the trap of so many other companies that just continue adding features and features and features until the thing feels overwhelming again. We are really trying hard to keep it simple and to make everything the bare essentials of what you need to run a business so that you can spend most of your time running your business. Some people question how diligently we pursue this goal and how we care about things like design and why it should really matter. And an analogy I used with a friend of mine recently was that back when TSA PreCheck was first coming out, I eagerly signed up, and for a while, lines at the airport were much shorter, and that was great. And then I remember recommending it to someone who said, well, the TSA PreCheck lines are just as long as the regular lines. Why would I get it? And to me, that was an absurd question, because I was like, well, you get to go through security with your dignity. It's not the shorter line that's a side benefit, you know, And I think for Studio Works, the lower fees or something like that, that's kind of like our example of the shorter lines. We're really trying to give designers their dignity. We don't want you to feel embarrassed that you're not businessy enough because you feel overwhelmed by your tools. We want you to love your tools, to send an invoice and feel proud of how you're presenting yourself. And so we've gone through great pains not only to make it simple, but to make it beautiful. To make the whole client experience is very your brand forward. It's not us trying to, you know, impress our brand upon your clients, and we think those things matter.

Jessica Hish (51:22)

A secret mission that we have is also convincing people they don't need to use bookkeeping software, because we have a lot of customers that are like, I really love what you're doing. But my accountant uses QuickBooks. And to me, there's a lot of software, not just bookkeeping software, but a lot of software that's solving a problem that's not a real problem. And I have a lot of expenses. I have technically four businesses because I have two brick and mortar shops. I've got Studio Works. I've got my own business. I sell books. I do all kinds of things, and I do my bookkeeping once a year. It takes me four hours. I just export my CSVs. My accountant also uses QuickBooks. I can send him CSVs or I can export my CSVs as QuickBooks format. And I used to use Mint, and I used to do all those things that auto import your expenses, and it's hours per week correcting the auto import. This is my Roman Empire. Now is, how do I Convince people that actually some of these tools, while you feel more professional, because you're paying 60 bucks a month for this thing that's attached to your bank account, it's actually making you do more work. A big thing for Studio Works is, you know, the simplicity on purpose, but also really explaining to people the most straightforward way to do the things that they need to do for their business and what things matter and what things don't. The bookkeeping hill is a hill that I'm on right now, just because we had debated on whether we were going to build a complex bookkeeping product as a part of Studio Works, but ultimately we would just be making more work for people like all these other things do. So we're focusing on the things that other things don't do well. Like if you're just a person that loves to do two to three hours of bookkeeping a week, and that's organizing your sock drawer and you enjoy that, I'm not going to take that away from you. You do that.

Aaron Walter (53:11)

That's a special type of person.

Jessica Hish (53:12)

It's a special type of person. But where we're going to take Studio Works, which has always been on our roadmap, is dealing with the onboarding side of working with a client. So sending proposals and scope of works that then can automatically feed into an MSA that can then automatically feed into your invoicing. So then it just becomes one streamlined pipeline of moving things forward. And so that's really where we're at. The way that a lot of other platforms handle proposals is that they treat it more like a sales pitch. So it's meant to be basically like a fancy PDF on the Internet that is like, here are our skills, here's why you should hire us. Whereas the way that we're approaching proposals is more like how independent businesses do it, which is to send a scope of work that becomes a light contract. We want to make it flexible to how different people do business, but ultimately, most people that are working for smaller clients can get by with a proposal and an invoice. And so we want to make sure that we can scale to how everybody does business. But we want to really make it so that it's super straightforward. You can request edits and cosign and all kinds of things online so that you don't need to download a PDF, open it in preview, sign it with, whatever, you know, how do we make the thing so that you're not having to jankily put together all of the things that you do to get a project started?

Aaron Walter (54:31)

What do each of you like about being independent?

Jessica Hish (54:35)

I love the flexibility to work on things that I'm passionate about when I'm passionate about them. That's a big thing for me, which has been a bit of a pain point with the team sometimes where I'm like, okay, well, this week studio works is happening for me from 8pm until 2am because I'm doing this other thing during the day. My day job can flip into a night job. And I love that because if I'm suddenly really passion about a thing that's best done during the day because I have access to the resources that I need to during the day versus when I can be in like a solo hole at nighttime, I have the ability to do that. So I love that. And also the flexibility to be able to have my business map to my family rather than having my family map to my business. On Mondays, I pick my son up at 2:20 and he does drum lessons before I do drum lessons. And every Monday he starts his day off going, Monday's my favorite day of the week. And I'm like, me too, man, me too.

Chris Shifflett (55:33)

That's great.

Jessica Hish (55:34)

If I wasn't working for myself, that's not something I'd be able to do. Even with the whole work from home flexibility that a lot of people have now, you're still on the hook for zooms and meetings and all kinds of stuff throughout the day. And I think when you can manage your own time and your own life, you get to actually build the life that you want, not just build the career that you want.

Chris Shifflett (55:55)

My answer would echo a lot of what Jessica said, especially about trying to shape your work to your family, not the other way around. I think that's pretty important. But there's also like this emotional part of it that's the feeling of freedom. I don't know why, but that's always felt really important to me. And I'm happiest when I feel free. I can even think of analogies that also kind of reinforce this about myself. So, for example, when I lived in New York, I biked everywhere to get around. Not all the time. I would hop on the subway sometimes, but whenever. Citi Bike was first launched, you know, this bike share program in New York, I started using it and a lot of people didn't really understand that because, like, I had my own bike and it was better. But what I really loved about Citi Bike was hopping on a bike, going somewhere, docking it. You wash your hands of that whole situation, you're free again. Let's see where the day takes me. You might go back to that same station to go home later, but you might not. You're not really tied to that. And the other thing that I do a lot is I love to go backpacking. So it's just like camping, but you have everything you need on your back. And there's something about being deep in the wilderness. I always have a plan. There's somewhere that I'm going that I plan to like camp over by this lake or something. But that mountain to the east, you could just, just go there. Instead you feel this complete freedom that you have everything you need right there with you. The entrepreneurial spirit to me is kind of that. It's people that are seeking that kind of freedom. It shapes a lot of your life if you can get there, how you're able to live your life and the sort of life you're able to design for you and your family.

Jessica Hish (57:32)

I think a thing that's important to remember though is that the entrepreneurial spirit is not natural to most people. It is a thing that you get thrust into or that you have to embrace just because of the nature of the things that you want to do, because there is not a sustainable full time thing for the thing that you are passionate about. And I think a lot of us that start off as independent creatives or entrepreneurs at first were operating out of a place of fear in terms of diversifying yourself. Yes, it's easier to get clients if you have a specialty, but you also have to have your finger in a lot of pies just because that thing doesn't always work out at this time. So you end up kind of splinting yourself into a lot of different places just because you're trying to survive and you're trying to make sure that you have something going on if this other thing doesn't work out. So it starts out of this survival mechanism and a little bit out of a fear based thing. But eventually, once you can kind of prove to yourself that things will work out because you just keep going and you care and you're passionate about it. There's this ceramic dish. I need to track down the artist of it, but it keeps popping up in my feed and it says, I will succeed because I am insane. And I love it so much because there's this thing of just kind of at some point you just believe that it's all gonna work out because you're like, no matter what, I'll have something to do. I've got my backup plan. I've done This a million times. I have doomsday preppered my career 400 million times. And then instead of operating out of a place of fear, you can just operate out of a place of curiosity and passion. And when that switches over, it's incredible. It's just an incredible thing where you know that something financially will be okay. Worst case scenario, I'm barista, you know, like. Like, whatever. Like, I'll figure it out. It doesn't matter.

Aaron Walter (59:34)

And no shame in that. That's a great game.

Jessica Hish (59:36)

No shame. I'm a big believer in you keep your day job to sustain whatever it is that you want to do. I gave this talk once that was called I am Batman and you'd can be too. And it was this idea that Batman only exists because of Bruce Wayne. Batman's cool and doing all kinds of cool stuff, but he is incapable of doing that stuff without the financial benefactor of Bruce Wayne. So you figure out what your Bruce Wayne is. Whatever it is, if it's a day job or some version of a thing, that's not creativity at all. That's your Bruce Wayne so that you can be Batman. And if Batman can take up more of your life, amazing. But that only happens when Bruce Wayne is really killing it. It rules when Bruce Wayne becomes something that is a little sustainable and like, it's not a grind because it just gives you more space to be curious and try things and pursue those passions. And if it happens at a time in your life where normally we start getting locked down and stone brick mindset instead of growth mindset, all the better because you can actually keep that vitality mentally and creatively going instead of getting into that really static place that a lot of us get into in our 40s and 50s and stuff.

Eli Woolery (60:51)

I love the Batman, Bruce Wayne metaphor, Chris. I also like what you said about bikes. And I try to go and I'm in a different city. Grab a bike. The cities that have bike shares. Word of caution, though. Aaron and I, a number of years ago were in Sydney and we decided to grab some bikes and ride around and didn't realize how draconian their helmet laws are. We got pulled over by the cops and we had to return the bikes because you're not allowed.

Aaron Walter (61:12)

We almost got arrested.

Chris Shifflett (61:13)

Yeah, that's right.

Aaron Walter (61:14)

We had been on the ground for maybe an hour. Yeah. In Sydney. And almost got arrested.

Chris Shifflett (61:19)

Yeah. Wow. Yeah, I actually have heard that about. I think it's the US and Australia are the most pro helmet cultures. Yeah. And both have, of course, the highest incidence.

Eli Woolery (61:30)

Right, right. Well, let's ask our rap question here, which we often ask of our guests. And before we started recording, we were talking about the Stranger Things shirt that I'm wearing, which is kind of inspiring me. It's a collab between Stranger Things and Santa Cruz Skate and Surf. And last time we were chatting, we talked about Antiques Roadshow, which is a great show. What for both of you is just inspiring you in your off time.

Chris Shifflett (61:54)

Right now, I'm inspired by everyone that's pursuing something that they really want to, even though it's hard. I think that's especially true these days because a lot of things are hard with AI, uncertainty, economic weirdness, global political instability, all the things. There's injustice everywhere you look. And it feels like it's either way more prevalent these days or it's way more in your face. So it can be really hard to kind of pursue something for joy or to try to contribute something positive to the world. But I think those who are. It's really important. It reminds me a little bit of the Fred Rogers quote where his mom told him, in times of strife or great tragedy, look for the helpers. People interpret that in lots of different ways. My way of interpreting it was just that she was trying to give him something to focus on that is positive when a lot of things aren't. So if you're one of those people out there doing something positive, no matter how small, you're inspiring a bunch of us, and it really does matter. So thank you.

Jessica Hish (62:58)

I'll piggyback on that just in that with doing a lot of public speaking and things like that. I've talked during some very stressy times for people to students that are graduating into a very unknown workforce and all that kind of thing, and also lived through a few of these iterations of there being a lot of upheaval and a lot of bad stuff going on and people being like, I don't know how to be a person in the world during this, I feel like I should quit everything and just be a volunteer or do whatever. And the thing that I have told folks, which I really believe in and really echoes what you said, Chris, is that. But there are certainly people that are born to change the world. They want to be on the ground, they want to be a nurse, they want to be doing the hard stuff in person, and they are passionate about that. But artists and creatives, their job is to remind those people why the world is worth saving. We need to create joy and beauty. Because if all you can focus on is the negative and the bad Stuff that's going on, you burn out really fast in those roles. That's really one of the main functions of art, is just to show what humans are capable of and the beauty in the world so that when you go through the hard times, you can be like, this is worth doing because this is worth saving. But the thing that's lighting me up right now is doing stained glass, you know.

Aaron Walter (64:25)

Nice.

Jessica Hish (64:27)

I have felt very alive in the last couple of years, pursuing a bunch of different mediums and interests that in a former life, I felt I was too intimidated to do or that it didn't contribute directly to my financial success or my life as a designer. And it feels incredible to want to make things just because you like to do it, even if it goes nowhere. There's stained glass things that I'm baking just for my house that I will never share a picture of on the Internet. That feels incredible. Coming out of this space of social media where everything you make and every moment that you have should be shared and maximized and monetized, just to be able to, like, find a way to create without the eye of Sauron on you is really nice.

Aaron Walter (65:16)

That's wonderful. Well, Jessica and Chris, thank you so much for what you're doing with StudioWorks. Where can people learn more about it and sign up and start operating their business more effectively?

Chris Shifflett (65:28)

Yeah, well, we actually set up a special page just for your listeners. If you sign up before the end of the year, you're going to get basically a lifetime discount, which is the same thing that we offered the people who we call founding members, those lovely souls who signed up before we even had a product. And that is at join StudioWorks app. App DesignBetter. So it'll be $29 a month for you for as long as you're a customer. And again, that's if you sign up before the end of the year. We think this is a special time where maybe you're open to trying something new. Start the new year fresh, and we'd love to show you a simpler, more beautiful way of running your business.

Jessica Hish (66:10)

Yeah, and our current subscription cost is $39 a month. And our goal, you know, we've talked a lot about the goals of the business over time, is that we not only don't want to raise our prices even as the product gets richer and richer and richer, but if there's a world in which we can sustain ourselves, we'll talk about lowering the prices for everyone, including folks that have these sort of deals. So what we want to do is just figure out how to get this thing really rocking and rolling so that we can make it even more accessible to folks. And there's no seats, there's no gotchas.

Chris Shifflett (66:45)

Yeah. There's one plan. Everything that we have. No feature gatekeeping. And we try to make everyone look as pro as everyone else.

Aaron Walter (66:53)

I love that. Well, Chris and Jessica, thank you so much for joining us on Design Better.

Chris Shifflett (66:57)

Yeah, thanks so much for having us.

Jessica Hish (66:59)

Yeah, thanks so much. This was great.

Aaron Walter (67:05)

This episode was produced by Eli Woolery and me, Aaron Walter. Walter, with engineering and production support from Brian Paik of Pacific Audio. If you found this episode useful, we hope that you'll leave us a review on Apple Podcasts, Spotify or wherever you listen to finer shows. Or simply drop a link to the show in your team's Slack channel. DesignBetterPodcast.com It'll really help others discover the show. Until next time.

Jessica Hish (67:35)

Sam.