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Building an agency, launching software products, choosing a job, and maintaining creative outlets

Michael Sacca is the VP of Product at Dribbble and cohost of Rocketship.fm. He started his career 15 years ago as a Product Designer, eventually founding a cutting-edge product agency that built applications for Scholastic, GE, Nike, Siemens, Kobe Bryant and more. In this episode we talk about building an agency, launching software products, working a 9-5 job, creative outlets, and the role that Constraints play in all of our decisions.

Transcript and show notes can be found here



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Michael Sacca 0:00
But with an agency, it's really all on you to sell. Right? And so you never really know where your next client is coming from. We never knew if Scholastic was going to come back next year with a new app. So we put all of that time and effort into that relationship. And then sometimes they come back sometimes they don't.

Jay Clouse 0:16
Welcome to creative elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show.

Jay Clouse
Hello, Welcome. Welcome. Welcome to another episode of creative elements. I am forever grateful to today's guests. And since you're listening to the show, you owe him a little bit of gratitude to which I'll get to here in a second. Today I'm talking with Michael Sacca. Michael is the VP product at Dribbble. He started his career 15 years ago as a product designer. And he started a product agency that built applications for Scholastic, GE, Nike, Siemens, Kobe Bryant, and more. And then he created a software tool for brand Asset Management called Brandisty, which I used a lot and actually had no idea he was a part of until this very conversation. It was acquired in 2014, and is now owned by envision, and he was the president of Crew, a freelance design and development marketplace and former parent company of Unsplash, the popular stock photo website. As you can see, Michael has had quite the career for a product designer. And that wasn't even how I knew him. Michael has been running the show Rocket Ship since 2014. It's actually one of the first podcast that I ever listened to as a budding product manager myself back in the day, and it's one of the highest production quality shows that I've ever heard. Back in March of 2019, I was introduced to Michael over email. I was about a year into running my other podcast called Upside and was trying to learn from more experienced and successful podcasters. Michael and I chatted over the phone for about 30 minutes, we had a great conversation. And he talked quite a bit about how great of an experience he's had working with the Podglomerate. This very show is now on The Podglomerate network because Michael introduced me to Jeff, the CEO in April of 2019. And without The Podglomerate, Creative Elements may not even exist. So I'll say it again, I'm grateful to have met and know Michael. In this episode, we talked about Michael's own path, which covers a lot of different paths that a lot of us have probably considered at one point or another. We talked about building an agency and closing that agency down. We talked about building software products and the challenges that come with it. We talked about working a nine to five job with a team and why it can be a really great choice. We talked about creative outlets and balancing a side project with a nine to five job and ultimately the role that constraints play in all of our decisions. I'd love to hear your thoughts on this episode. As you listen, you can find me on Twitter or on Instagram @JayClouse. Go ahead, say hello, tell me that you're listening right now. Take a screenshot if you want. But now let's talk to Michael.

Michael Sacca 3:19
This is longer ago than I would care to admit. But yeah, I had graduated college I built a recording studio in in Massachusetts. It failed, right? Building a recording studio is quite hard, especially when you try and do it in your living room. But we were always ambitious. So I was kind of moving on from from that phase in my in my life, my early 20s. And I moved out to Los Angeles because I had a music business degree from college, which I think we were one of the only universities that offered a music business degree. So I went out to LA to get a job and I applied at all of the big record labels. I applied at any of the big agencies CAA and I got rejected from all of them because none of them had ever heard of a music business degree, they had all largely been either self taught or came up through a path of connections. And I didn't have any of those. So I ended up working at restaurants in Los Angeles. And my, my roommate at the time, who I met on Craigslist, would wake up around noon, he'd come home around four. And he had this job. He's making three times as much money as I was. And he has this job that they couldn't fire him because he was a he taught himself PHP. And he had built this little app that they ran practically their entire business on. And I realized that this was probably a much, much better path than the one that that I was on at the time. And so I started kind of piggybacking on his work, and I started learning basically from him. So I taught myself design, which was something that complemented his skill set. And then I started to learn how to code first on the front end and eventually, a bit on the back end. And so that was really kind of My motivation was to get out of doing what I was doing right working at the the restaurants in LA and I was just not happy right with where I was at. I finally decided to quit the restaurant I had, like a client lined up paying me $25 an hour. And I just started taking all the overflow work from from my friend Ethan, who I could. And and that really led me to this path in tech. And right so the first three years, it was a lot of long days teaching myself while actually taking on paid work.

Jay Clouse 5:32
What year ish was this?

Michael Sacca 5:35
So let's see, this was 12, 15 years ago, probably more probably like 16 years ago.

Jay Clouse 5:42
Early 2000s.

Michael Sacca 5:42
Yeah. And so mobile was just starting to kind of pick up so I taught myself the front end, the back end, I had started picking up a pretty steady client base a couple years and I worked for Kobe Bryant that really helped to pick up momentum, at least People started to trust you more. Eventually, I got some big contracts with Scholastic and GE building mobile web apps. And so what we had done is I had found a partner, who I also met on Craigslist and the day, but I had found a partner and we decided to go all in on html5 mobile web apps. Sencha was the big framework at the time, which I don't know if it's around anymore. But, but it was a bit it was on the cusp. And so there was a lot of companies that were interested in it because you could launch the Android and iOS with one code base. That was our that was our pitch. There wasn't a lot of agencies doing this. And so we were able to land those big contracts with GE, who was very interested in this and and scholastic. And that kind of set the trajectory for building an agency. And so this is about five years in and we ended up renting a space in downtown San Diego. I moved with my wife to San Diego from Las Vegas where we were living, and we went in all in on this creative agency.

Jay Clouse 6:58
Something I want to stop and double click on here. You know, you taught yourself how to code, which is super difficult and a scarce skill set in early 2000s. And then that led to a contract with Kobe Bryant, Scholastic and GE. Well, if I'm listening to this, and I'm saying I want big name clients, sure I get that. Okay, let's, let's say you had this super differentiated approach and skill set that was a competitive advantage. How did you get the meeting in the first place?

Michael Sacca 7:26
Right, so they actually reached out to me so Kobe was just the contact of someone who was already working in the agency, they had actually won the Kobe contract, but they couldn't, they didn't want to do the front end code. And so they were an agency in Los Angeles, and they reached out to me to basically do the work, but I was able to put it on my portfolio. I made sure that in the contract, I could advertise that I had done the work with Kobe Bryant, and we ended up coding a good part of the site, KB24.com and so we were able to leverage that as trust. And then we did another small project with a local Mac store. And it didn't go anywhere, right? They never, we didn't actually get get paid for it. But we had built a scheduling prototype. And we were able to put that up on our portfolio. And so now we had two big names that we could say we've at least worked with. And so when we started doing this kind of html5 work, that's when scholastic, they actually called us to submit an RFP, because we were one of five agencies on the central site that were featured. And we had done some small projects with them, but nothing too big. But it was just kind of, I want to say luck, but it was strategic in the sense that we positioned ourselves as with a niche skill set that was highly valued and highly paid, right? Because if there's only so many agencies that can do this type of work at the time, you can charge a lot for it. And that was our goal, right? If we're going to do client work, let's charge as much as we can for it. Let's find the niche and we wrote that niche until it became saturated. And then we moved over into nodes. So that was always kind of a theme for the agency was to try to stay on the cutting edge so that we could charge a premium, even though we were very small.

Jay Clouse 9:12
That makes a lot of intuitive sense. But it takes a little bit of imagination to even get there. So is that something that someone counseled you to do? Or how did you come up with that as a strategy in the first place?

Michael Sacca 9:22
I think it was just, we saw, we got some initial eyeballs with it. So we built this app for Mac. And that was really just kind of scratching our own itch. We were working with a local manager there who wanted to build a scheduling app, and then pitch it up to corporate. So we're like, Alright, well, we got some free time. Let's do this. So we started scratching our own itch. And then we had another client who wanted a mobile app. And we were like, We don't write iOS. We don't write Java, right. We don't write. There's Objective C, I guess at the time. And so with that, we were trying to figure out how do we take on this client and say yes, but solve it in a way where we could use our skill set. And we we put that client up on our portfolio. You know, we went out to Dribbble, we went out to the various sites. And somehow we kept getting inbound leads for this type of work. So we knew we were onto something. So it was really more positive signals in the market led us down this this directive path.

Jay Clouse 10:20
Inbound leads, if only we were all so lucky. But that's what happens when you build a name for yourself as a person or a team that solves a problem that other people can't. It also happens when you have some great portfolio pieces to point to. But this was an introduction to one of Michael's first constraints, there was a limit of how much Michael's small team could take on and there are a few ways you can deal with that constraint. You can raise your rates, you can say no, or you can staff up into a bigger agency, and Michael's team chose to staff up.

Michael Sacca 10:50
Yeah, we only staffed up to about 10. And so we stayed fairly small. And what we always wanted to do was build our own products. So we would do basically half client work where we charged as much as we possibly could, and then half personal projects. And and so that was our goal was to always be like Basecamp. They had that agency before, they would that that was our hero, right or Teehana+Lax at the time, where they were able to successfully launch initiative product initiatives that they owned themselves, but they were still, you know, able to fund that through the client work. And eventually, you know, Basecamp, set themselves free and was solely dedicated to Basecamp. So that was always our goal. That was the model that we were trying to achieve. So we did work with all of these large clients, we staffed up to the minimum that we had to so we only ever brought people on when we absolutely needed to, and we were doing too much work ourselves. And we always took that approach. So we were always selling but then we were always building and our goal was never to have a large agency.

Jay Clouse 11:50
Can you talk to me about what it means to hire in an agency setting?

Michael Sacca 11:55
Yeah, so the hiring is terrifying in an agency because you know with a patient product you can hire based on predictive revenue or projected revenue, right? You know, if you bring on a new head of marketing, then you can, you know, expect to grow your revenue by x percentage, but with an agency, it's really all on you to sell, right? And so you never really know where your next client is coming from. We never knew if scholastic was going to come back next year with a new app. So we put all of that time and effort into that relationship. And then sometimes they come back, sometimes they don't. And so we always had to be one step ahead, where we were building and then selling and that that was really why we never wanted to grow big because that pressure wasn't necessarily something that we were comfortable with, or we were really interested in building a business on top of. So yeah, hiring is terrifying. That's why agencies use a ton of contract work so you can scale up and scale down so scholastic doesn't come back for a second contract. Well, now, you know, you just let the contractors know that. We can't renew it, but it's it's much easier to do that than to let go of employees. Pay severance, you know and deal with more permanent situation. So that was the approach that we took was to hire the least number of people as possible. And it is a huge risk when you bring someone on to an agency, especially a small agency, where you don't yet really have that predictive deal flow. And you are still fighting for every deal that you get against bigger and bigger agencies with more talent. So we would bring on people that did skills that we felt like we could sell, but again, it's never a guarantee.

Jay Clouse 13:33
I think that's an important thing to know, for someone who may be interested in working for an agency, you know, because these agencies get a lot of people who would love to work there. But sometimes on the inside, they don't even know if they're going to be able to keep that commitment to the employee six months from now, 12 months from now.

Michael Sacca 13:50
It's absolutely true. Yeah.

Jay Clouse 14:08
When we come back, we'll talk about some of the products that Michael's agency created internally. Welcome back to creative elements is the early 2000s. And Michael Sacca's agency is up and running. They've hired a couple full timers, but they're mostly running with contractors. And the team is trying to spend half of its time creating their own products, the way agencies like Basecamp did before them. But did they get any products in the market?

Michael Sacca 14:18
Yeah, yeah yeah we did. I mean, we learned a lot actually, we built the first thing we built was an iOS game called bilingual child. And we ended up making a whole series about nine of these. And so this was a language learning game for kids. And again, it was a market opportunity that we saw there was a Montessori app that was printing money at the time. It was huge on Hacker News. And it was a very simple game that just taught kids how to trace letters. So we thought, what if we taught them language and so you know, we hired some some voice actors, we did like about 100 vocabulary words, it was very simple, it would say that in English, it would say it in Spanish. And then we did the the reverse. And so we launched those, that app still makes money today. It became one of the very popular apps in the app store. It was featured by Apple at one time. And so for about 10 years, it has been fairly consistent.

Jay Clouse 15:11

Michael Sacca 15:12
Generating just residual revenue. We haven't updated it in about eight years, but it's still out there. And then we ended up doing about nine of those. And then from there, we tried to do a huge language learning game with like a map. And this interactive gameplay. That didn't work out quite as well. We wasted about a year trying to bring that out. We never released it. It was called Lingual. We did a kickstarter for it even. And so that was tough. We never got it to a point we were happy with it and ended up kind of fizzling out. But from there, we built Brandisty which is a brand asset management system. And that was probably our most successful in terms of recognition. We had some big clients on it, and we kind of shut down the agency and went all in on that product. Towards the end, we lost around $150,000. In doing that, that was the cash that we had saved up from running the agency that we had in the bank. But it was a very purposeful decision. We had all kind of burnt out on the agency at that point. So we said we this is either gonna work or it's not. And we we decided just to put it all in on taking this thing to market. That's actually why I started the Rocket Ship podcast, because I realized that we had no idea what we were doing. We could build the product, the product functioned. But we not to market it. We didn't know how to actually take it and make it something that was standalone. We were able to get traction. We were able to at the time medium was just starting so I you know, I was able to market it through writing, which got a lot of attention, but it didn't get a lot of purchases because what wasn't targeted right. It was just kind of like the startup community. Startup community doesn't have any money. When you're looking at like brand asset management systems. They started around between 100 and 500,000 a year. And then we're coming in here with a $20 a month product that the the big people didn't trust because it's only $20 a month built by like, you know, the small agency they've never heard of. And then you've got like the established players with full sales teams and robust contracts and robust feature sets. And so there was a gap in the market where we could acquire free customers all day, but upgrading them even just to $20 a month was near impossible. And I was just trying to figure out what we were doing wrong because it seemed like we had interest but we couldn't turn kind of the revenue, the table on the revenue, and that was it was the big, unknown. And so that's, you know, we started Rocket Ship to start getting advice from people. In the end, it didn't work, but it was able to open up that opportunity to at least start to learn and I did eventually sell Brandisty to another brand asset management system that was then acquired by envision shortly after.

Jay Clouse 17:58
A lot of creative service, basic businesses try to follow the path that Michael is describing. At some point, they get frustrated with spending all of their time on other people's visions. Maybe a client doesn't actually use the work they spent so much time creating, and they start building their own projects. But a great part about freelancing or agency work is the variety of projects you can dip your toe into. So I've always wondered if those teams who start building their own products internally end up missing the variety that comes with client work?

Michael Sacca 18:26
No, it's actually a relief coming from the agency side, because after for a good five years, you're working on other people's vision, and you're running from one to the other. And I always wanted to do the follow up because I felt like we never learned enough. We would build on our assumptions, because there was no data at the beginning. And then I wanted to learn. Well, what do people really want and we never got to do that phase of any of these projects, right? We never got to do the follow on work. And so Brandisty allowed us to do that follow on work, to actually iterate to listen to the market to interview customers and start to build features based on what they were looking for. We couldn't do it fast enough, because we weren't big in a big enough team. But at the same time, that was the opportunity that I really want. And that's why I eventually moved on to Crew. Because I knew that I wanted to wake up every morning and actually build upon the same mission in the same product to improve that rather than trying to do so many different little things that didn't have a big impact. I fell in love with Crew as soon as they launched it. We had Mikael on the podcast. And Crew was a freelance marketplace. So we had clients coming in looking for work, we had freelancers coming in looking for to find projects, and we were the middleman we were matching them with it. So I knew that pain very personally from you know, from freelancing from them building an agency, I knew how scary it is to not know where your next project is coming from. And the whole premise was of crew was to solve that problem. We negotiated the budget so that by the time the project came to the freelancer They knew exactly what the project was, how big the budget was, what the scope was. And all they had to do was basically submit their portfolio, have a good conversation with the client hopefully landed, but the client was talking to three people at the most not. And so we did our best just to make the experience great for both sides of the mark of it. Still kind of sucks today trying to find a freelancer. But that was the big problem we're trying to solve is just a mission that that really resonated with me. I started something else after brand to see with a good friend who's an ex Google engineer. And so we had been kicking the tires on on this idea for about six months, we started building, but Mikael reached out and he just had such a great pitch. And he's like, I just want you to come on board and run the partnerships for me. And, you know, I had a conversation with my wife and it just it seemed to make sense, but it wasn't something that I applied for wasn't something I was necessarily looking for but when the opportunity was there and I knew I should probably take it.

Jay Clouse 20:58
What was it like going from running your own agency to running a product to now helping build someone else's vision even though you were bought into it. Was that strange or hard for you?

Michael Sacca 21:05
It felt like retirement, actually, in a way. Like I knew I was worked hard, but Mikael and Steph, now there was a leadership group that I wasn't necessarily part of. And so a lot of the big decisions, a lot of the stress of raising funds of hitting metrics, it wasn't as much my burden, right, I could focus in on partnerships and sales and hitting our numbers there. But it actually relieved a lot of the burden for that time of having to worry about everything, right. I had a bigger team, we were like, We were 16 people. When I joined, we grew to about 40. And so all of a sudden, we had a lot of people and a lot of hands to do all the work, which was something we never had at the agency I was I was taking sales calls and then running over and designing someone's app, you know, and context switching constantly at the agency just to stay alive. Here at Crew, I could, you know, send that over to design team. Ask the development team to build something. Ask Mckell What's our next big initiative? Right? None of that necessarily. So it was a blast. I, what they built it on splashes is incredible. But it was nice to be able to focus and I just had a son. And I really needed that some of that that pressure taken off at that time.

Jay Clouse 22:24
Michael worked at crew for just over two years before that company was acquired by his current employer Dribbble in 2017. While building out the core product for crew, the founding team started a side project called Unsplash, which provides beautiful free images and photos for people to use on the web. I bet you've already heard of Unsplash before, and if you haven't, I would guarantee you've seen some of their photos used across the internet. And so it wasn't long until the team at Crew faced their own capacity constraints.

Michael Sacca 22:54
At some point Unsplash took over importance. Unsplash just grew like a weed. It was a side project that crew that we had built just to get attention for Crew. It was again, it was just kind of by accident Mckell and, and Luke and Steph, they had put up 10 pictures on this shoddy blog and said here, have them for free and it blew up from there. And so then every week they were posting another 10 pictures. And then people started submitting pictures. And that's what became Unsplash and Unsplash had more traffic than Crew. And so they had kind of decided, you know, this is actually the big opportunity for us is and I don't think they got that wrong at all. And so they had asked me to find a home for Crew, essentially because they went and focused on unsplash. And so we went out and pitched various companies who were in the space and Dribbble just made the most sense. It was also something like I grew up on Dribbble. I remember getting my first Dribbble invite and so when I was talking to Zach again, Dribbble just had kind of a personal mission. For me, it was still trying, we're still trying to solve that freelance work problem, but just on a much bigger scale right We Dribbble does, you know 5.5 million visitors a month. And so this was just the scale, we didn't even have it at Crew. And so it was a natural fit, I think for the team.

Jay Clouse 24:12
After the break, we talked about how Michael balances a successful side project while maintaining his full time role. right after this. Welcome back. We had just followed Michael's career up to where he is today. He went from agency to software product with brand dusty to freelance marketplace with Crew and today he is the VP of product at Dribbble. Michael is obviously a wildly talented and experienced guy. He taught himself design he taught himself how to code. A lot of times we really glorify the entrepreneur. on this show, I mostly speak with creators who are all in on their own projects. So I wondered if a talented guy like Michael ever missed the days of being out on his own, if he ever feels tension with his own creative self, and if so how he deals with it.

Michael Sacca 25:00
Yeah, so that's a good question. I mean, I still do Rocket Ship, right. And so I always need something, I need a project that I own, and that I have that creative outlet. And whether that's design or audio, I definitely need to be creating something. But at the same time when you're working on something that is kind of core to your experience, like Dribbble, and you know how big of an impact it can have and how big of a breach it has. It's hard to not want to do that as well. Right? So I am definitely all in on on the mission at Dribbble. And I don't have kind of a creative longing to go out on my own at this point. But I do like to have a side project really just to stay fresh, right? It really just to be able to flex some of the skills I don't get to do at work every day. And that's what Rocket Ship has always scratched that itch for me before Rocket Ship. It was it was small apps that I would build. I built benchwarmer, which was one of the first chrome plugins for for Dribbble. But yeah, so I need a creative outlet. But I don't need it to be my main thing.

Jay Clouse 26:02
Rocket Ship. You said you started this while you're at Brandisty. And it was a means for you to meet people to learn what you didn't know about building the product that you're building. Can you talk more about the inception of that when it was because I think is still pretty early on and even podcasting, and what you thought the potential of that show was?

Michael Sacca 26:22
Yeah, so this is about seven years ago, I guess. 2014, already six years ago, we we did was we started it to write a book because we were very hard on ourselves. And we thought that we should write a book on how to launch a product. And through writing that book and launching a product, we'll learn how to launch a product, which is a terrible idea. And so we we started interviewing people, we were all about bootstrapping. So we were very anti-funding. We were in San Diego which had no funding and so we kind of had to be a bootstrapped. With this bootstrap mentality. I'd met Matt Goldman and Joelle now, Goldman And we just wanted to do something together. They were great people were just looking for a project to do. And we thought, well, let's write this book. How do we write a book? Well, let's interview people. So we started recording the interviews. And as we were releasing them, the interviews, were getting a ton of attention, because there was just a gap again, in content for bootstrappers at that time, so there was this whole bootstrappers movement. Micro comp was just starting. Heaton Shah was was kind of the celebrity entrepreneur at that time. But there wasn't a lot of content on how to do it well, and what people were experiencing, and it was still seen as you have to raise funding, and we were in this real funding time in the market. And so everything was startups funding go big, and you know, fail fast. And then there was this bootstrapper small community emerging that I guess wasn't as small as we thought because that the interview started picking up steam, we were getting 100, 200, 300 listings, which was more than we ever anticipated. And then we had people reach out like envision to sponsor the show. And so that we had sponsors from like episode two and on. And so again, we just got these positive signals that All right, well maybe we're onto something weren't huge signals but but we felt like we were onto something. So we never actually wrote the book. And we just kept going with the podcast. We were releasing three episodes a week at the time.

Jay Clouse 28:18

Michael Sacca 28:19
And for the first three years, it was all just straight interviews with entrepreneurs. And we would record them, you know, right in our office there in San Diego.

Jay Clouse 28:28
Crazy. And at the same time, what was Rocket Ship? Like when you made the move to go to Crew? Where were things then?

Michael Sacca 28:34
Yeah, so it was fairly well established. At that point. We never went an episode without sponsorship. So it was it was already a small business at that time. And so when I went to Crew, they saw it as an advantage. It was a way to get visibility out there. You know, I would talk about crew on the podcast, so they didn't mind and they were they were all about side projects. Anyway. So when I went to crew, I talked to Mikael. He had no problem with continuing it. And so it was something that once I had a full time job, I really had to be cognizant of the amount of time I was spending. So that's when we really started to optimize the format and and try to find a format that work that we could do in a couple hours a week. And that was always the goal to create the highest quality show we could with the least amount of time.

Jay Clouse 29:19
Did you ever think about at this time building Rocketship up to a sustaining business for you and the team as opposed to having a job?

Michael Sacca 29:28
Yeah, we did. I just didn't want to do it. It was the influencer, that that was kind of the model. It maybe still is, but it was the influencer model. And I never felt comfortable in that position. We had it especially in the beginning. In the podcast, we barely had a personality we always wanted the guest to be the personality. It wasn't until later on that took more of the reins in the show. But I also I just never felt comfortable with that giving advice. Once you're working. The advice isn't as clean as you see on Instagram, and I felt like that was the path to success in that area was to become some sort of influencer expert. And that wasn't something we ever really wanted to do. And so we we always kept it as a fun side project, something that we enjoy the creative outlet, rather than trying to force it into something that we weren't passionate about doing.

Jay Clouse 30:22
How do you think about managing the full time job and the side projects that now generates real revenue? I was listening to another interview you did this morning and back in 2018, you said that rocket ship was doing close to $10,000 a month pretty reliably. So if someone else builds up to that position, which would be an awesome position to be in. How do you think about holding on to both things versus going back to the brand is the attempt of doubling down?

Michael Sacca 30:47

Jay Clouse 30:48
And and any other advice you'd give for someone in that position?

Michael Sacca 30:51
Yeah, I think you have to look at everything for what it is I like like we were talking about before we could have tried to make Rocket Ship something that it wasn't but we want it to be true to what we had built and true to ourselves and what we wanted to create. And so yeah, Rocket Ship will never be the only thing that I do. And, you know, to balance the time, we've tried to optimize it to the point where it takes us maybe two hours a week to put out the show. But our goal is to be you know, the quality of NPR. I don't think we're there. But that's the goal, right? But can we do that with two hours a week of our time. And so that's the challenge with Rocket Ship. And I think if we had all the time in the world, I don't know how much better the show would be almost those constraints kind of make it what it is. And it forces us to be creative with our time, be creative with our process and hone all of that in I think you just you have to be true to what you what you want to do. We probably could have made Rocket Ship something that we did full time. I just when I saw the result of what that would have been. It wasn't the life that that I really wanted. I wanted more creative freedom. And so while it sounds like you would I, I kind of knew what the market needed. And it wouldn't have given me that freedom that we do enjoy today where we can just kind of put out whatever we want. Sometimes people hate it, honestly. But if they let us know, but I don't really care, I guess at the end of the day is like, this is our interpretation of what's happening in the world. And this is our space to express it. And it doesn't have to be anything else. Because I don't have to worry about is my income going to go away? Can I feed my family, this it's just a creative outlet.

Jay Clouse 32:30
You probably talk to people that are pretty early in their career all the time. If someone comes to you and says, hey, I've been doing a little bit of freelancing, and I'm thinking about scaling this up, but it's really hard. I struggle with it. How do you tease out or recommend they think about their path in terms of should I keep building my own thing, maybe scale up to an agency? Or should I join a team somewhere and be a really great player within a really great team with higher impact?

Michael Sacca 32:57
It's a great question and I think it depends on trajectory. So like, much like we talked about, in the early days, we had a trajectory, right? We had Kobe Bryant, and then Scholastic and then GE coming to us. So we had we had these signals from the market that things were working. And even when things were hard, we knew that we were doing something that these large companies respected and needed. And we always were modifying our pitch to get there, but we had a trajectory if we didn't have that trajectory, I don't think it would have been possible. And so it's also Are you good at sales? And like when things get hard. Can you hit the road and and drum up business and do you want to a lot of people don't and and so I think there's always a couple factors. If you have natural inbound, and you have to get to the point where it's painful, and you have too much work, you're turning away too much work and then you're going to hire someone to take on some of the the overflow. I think it's a natural progression into an agency but that has everything to do with trajectory. If you want to do something, but you don't have people knocking down your door to do it, it might not be the right time, right? Or you just got to get ready for, you know, to knock on doors and do the sales. And if you don't want to do that joining a larger company is one way to get that trajectory. Right. So a lot of people join agencies and they get Nike and they get Adidas and they get you know, all these great brands under their belt, and then they go out on their own right? And they leverage that agency's name. So now, you came from AKQA or fantasy, right? So that's on your resume, people trust you. And you worked with Nike, and you know, Google one now that's on your resume. And you could look at people like Hally from Ueno, who came from medium, and then Google, and then freelancing with those same companies. And he was able to leverage that portfolio into building one of the best agencies out there today, but there's no way he would have just built Ueno without working in Silicon Valley for 5 to 10 years. And so I think it's all about building that momentum and the trajectory and it really depends where you are on that cycle. And if it feels too hard, you might just not have the momentum to do it because it's not easy.

Jay Clouse 35:06
Being on Dribbble. And previously at Crew, you've seen a ton of different people's portfolios and approach and you've hired at an agency you've been inside of an agency, how can somebody stand out if they want to get considered for one of these fairly scarce agency positions.

Michael Sacca 35:22
So I think that you either have to be in the top 1% of your skill, or you have to be good at selling. Because there's two things that really work, you either have to be exceptional, and your skill has to be so good that the agency can sell your work, right, and they know that you are going to level them up. Or you have to be really good at communicating and selling yourself, selling your work. Because that's the other skill of a designer isn't just doing the work, but it's communicating the why behind your work. It's selling, you know, it's the Mad Men kind of style, but it's selling yourself, your work your ideas. Those are two incredibly valuable skills. But if you're not good at either one, it's gonna be really tough.

Jay Clouse 36:01
You use the word constraints just a moment ago. And we talked about earlier how big you were into bootstrapping these companies that you're doing, which has its own very real financial constraint, or constraints, something that you think a lot about, and have, they played a bigger role than maybe we even talked about here.

Michael Sacca 36:17
I think constraints are the most beautiful thing because I can get wrapped up in perfectionism. I think we all can, especially as creatives, right? But when you start to just put constraints on either your time or your resources, that's when real creativity shines. I think the greatest art is built out of extreme constraints, right through life through experiences. But yeah, so I even at work, right, we always put constraints on our projects so that we can ship in time. And when I came to Dribbble, we didn't put constraints in place we built until we felt like it was ready. But the quality of the product wasn't where we wanted it to be ever. Right and and once we start putting constraints and time limits, the whole team gets a lot more creative. Right. And now it's like, what can we ship in six weeks, right? Rather than what can we ship in six months. And same with with Rocket Ship, I feel like the show is so much better than it was when we started. But a lot of that came through having to script the show, because that was the only way that we could work with an editor and get it at the quality that we wanted, having to actually put ourselves more in the show so that we weren't so reliant on the quality of the guest. And then getting a bit more creative on what story we were telling, so that we had our own opinions inside of the show. So the people listening, we're listening for us. And not just because we had a big name, we wanted people to come back each week for us. And that was how we could build a sustainable show. And so those were all the constraints that we had to put in place and then work around. And I think working without constraints is one of it creates some of the laziest product art in in writing, and you see it it's the second album problem, right? There's no constraints.

Jay Clouse 38:03
Hearing Michael's story we can learn a lot from the different paths that he's taken. It's natural for us to have the constant feeling that the grass is greener on some other side of the fence. But Michael's been on just about every side of the fence. And with every yard comes its own benefits and challenges. You may be aspiring to build your own agency. If you are, how do you feel about sales? How do you feel about the stress of providing enough income to support a team? You may be aspiring to build a software company like Brandisty or Basecamp. How do you feel about marketing or figuring out pricing? Nothing is without its own challenges. So starting from where you feel the most interest is a great idea, because it's your interest and curiosity that will push you through the unavoidable challenges that await you. And look, there's nothing wrong with maintaining a regular job. This show talks with a lot of creators who are building their own path, but I know that's not for everyone. So I hope this interview has shown you that as possible. To maintain a successful and even profitable creative outlet, while still working a regular nine to five job. If you want to learn more about rocket ship, visit rocketship.fm or search for Rocket Ship in this podcast player. You can find Michael on twitter @MichaelSacca and links to all of this will be in the show notes. Thanks to Michael for being on the show. Thank you to Emily Klaus for making the artwork for this episode. Thanks to Brian Skeel for mixing the show and also creating our theme music. If you like this episode, please tweet me @JayClouse and let me know if you really want to say thank you. Please leave a review on Apple podcasts. Thanks for listening. I'll talk to you next week.