When Your Side Gig Becomes Your Main Gig with Michael Sacca

How I Built It
How I Built It
When Your Side Gig Becomes Your Main Gig with Michael Sacca

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We close out Season 2 talking to Michael Sacca of Crew and Unsplash. Crew has since been acquired by Dribbble, but the story of how they got to where they are is great! We discuss startups, finding the right balance, and how a simple side project can be the thing that changes your main business.  It’s a great way to end Season 2, so  have a listen!

Show Notes


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Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks “How did you build that?” Today, my guest is Michael Sacca, is that right?

Michael Sacca: That is right!

Joe Casabona: Awesome, awesome.

Michael Sacca: Yeah, I’m excited to be here.

Joe Casabona: Yeah, thanks so much for joining me. I’m very excited to have you on the show. I’m especially excited ’cause most of my guests are in the WordPress world, but I am trying to branch out so I’m glad to have you on the show.

Michael Sacca: Thank you!

Joe Casabona: So you are the CEO and founder of Crew, is that right?

Michael Sacca: No, no, no, sorry, president. President of ‘Crew of Mikael Show’. Very similar name if you say it fast. He’s the founding CEO of Crew and he founded Crew and Unsplash.

Joe Casabona: Gotcha.

Michael Sacca: And so now because Crew and Unsplash are growing so fast, he is moved over to focus on that full time and I’ve stepped up to be the president of Crew.

Joe Casabona: Oh, fantastic. So today we’re gonna talk about Crew. So why don’t you tell us a little bit about who you are and what you’re doing or what Crew does?

Michael Sacca: Yeah, so Crew is a vetted network of designers and developers. And as projects come through we help to match them, we help to build trust in that freelance economy so whether you have a project or whether you’re a freelancer looking for work, we can help you. So it’s a marketplace for that kind of talent.

And then myself, I built an agency at San Diego for five years and that’s really where I learned about the freelance economy, learned about contracting freelancing, a lot of the problems that come up and just exist generally in the industry. And that’s really why I was so passionate about joining the Crew team, to help solve this problem. And yeah, so I also host Rocketship.fm which is a podcast for entrepreneurs and I’ve been doing that on the side for about three years. So we can talk a bit about you know, managing side projects to that one.

Joe Casabona: Yeah, yeah. That would be great. So the idea for Crew, so Crew existed before you joined, is that right?

Michael Sacca: I was the 14th employee

Joe Casabona: 14th employee OK. So can you tell us a little bit about the, you know what it’s like kind of joining a startup like this ’cause I think that would be a great perspective?

Michael Sacca: Absolutely. So yeah. So I was the 14th employee in a remote team and when I came on, I came on to do our partnerships in sales. And so even at 14 there’s not a whole lot of organization and process around. So most of the time there were four founders and when you get hired you’re basically picking off one of the jobs that they used to do in the 20th of their time, right? So it’s all in their head which is just its normal right? So, and you come in and you start to put your own process together and you start to learn from them, what worked. And so we had one referral partner, one big referral partner. And I came in to grow that so when you come in, it was great ’cause I got to kind of build my own job in a way, you know, so like it was partnerships, it was sales and it was up to me to decide what to work on that would have the biggest impact, right? So I did a mix of long-term and short-term partnerships as well as eventually just direct sales cause we found that worked really well. And then I started to hire people under me too to pick off those pieces that I had been doing. It’s just a constant cycle, right? So yeah 14, it was great. At 35 we grew too pretty quickly ’cause we raised our Series A and that’s a whole another beast, right? So as companies grow it’s really hard to stay on top of disseminating information, keeping everyone up to date, keeping everyone inspired about what you’re doing, you know, at four people in a room it’s pretty easy, you know, you’re all really passionate or even if you’re just one or two, right? You’re passionate, you work hard, you get it done. When you’re 35 you have to instill that same level of passion into each person that comes on board. You just have a lot less time to do it. So I think that’s a huge challenge for growing companies.

Joe Casabona: Yeah, absolutely. So the company more than doubled since you joined and you kind of it’s that’s really cool, you get to build your own job and then you hire employees. What kind of research did you do when kind of shaping, essentially shaping your job description, right? Like what went well into that?

Michael Sacca: It was a lot of market research and I think it’s the same that I did when I would build a startup or a business myself, right? At the agency, it was the same type of mentality where I’d go out and just talk to who our current customers are, what were we doing well, what could we be doing better, what are other areas that we could be satisfying that we’re not currently but maybe there, hiring someone else to do and maybe we can bring that relationship over to us. And then how do we build personas and how do we find more? So we had one agency that was sending us leads, there were five or 600 other agencies that look just like them, right? You know, and so could I go out and build those relationships. And what I tend to do is when I get stuck, when I don’t know what to do, I get out and talk to people. I either try to sell or I try to do market research and that generally gets me out of my funk of ’cause, you know, that’s what we’re doing, right? We build these online businesses, everything is automated but the truth is we’re solving problems for people and that’s where I find when I get stuck is when I get out and talk to people, I get inspired again. So…

Joe Casabona: That’s awesome. So aside from your responsibilities at Crew, there are two things I’d like to mention ‘cause I think a lot of the listeners are probably in a very similar position to me, I have a full-time job, I work on side projects. So there are two side projects I’d like to mention. The first is your podcast, ‘Rocketship.fm’, and then a side project that was part of Crew which was Unsplash. So maybe we could talk about first how do you balance your time with Rocketship.fm and what did Unsplash do for Crew?

Michael Sacca: Yeah, so for Rocketship, I’ve been doing it for about three years and we started it to learn because we didn’t know what the heck we were doing and we were trying to build the companies. And so we started just to talk to people because we could get on the phone. I think a lot of podcasters have a similar experience where you’re really seeking people out that can give you advice on what’s going on with you right now. But the joy is you get to share that with a lot of people and they’ll actually pick up your phone call, right? And so that’s why we started it and we were only going to do it for a couple of months but it kind of picked up. We found an audience and so we kept going, and now it’s been about three years I worked on that now about three to four hours a week. And I find time at night to do it. So I have two kids and a wife and so after the kids go to bed, you know after we have dinner and you know having spent time with my wife. 11:00 o’clock at night I’ll sometimes start doing that editing process. And so for me, that’s generally how it works a couple of nights a week but I love it. So you keep doing it and it does generate revenue which is always a nice genocide benefit, right? So yeah, but it’s tough. I mean finding the discipline. I think it’s all about finding consistency, especially with side projects, and not trying to do too much at once, right? ‘Cause, that’s when you get burned when you have too many of those 6:00 AM nights when you gotta get to work at nine and you’re losing focus at work, and then you’re burnt out for a couple of days. I think having realistic expectations of how fast you could move is really important and being very disciplined with finding a schedule and keeping to it. I find schedules are great for me like if I know that Monday and Wednesday I mix down my podcast, cool. like I don’t miss those days, and I don’t plan and I don’t make excuses.

Joe Casabona: Yeah, absolutely. And so before we went on Unsplash, there’s a lot of great advice in there especially because by the time this show comes out, I will be a new father, my wife is expecting in March.

Michael Sacca: Congratulations!

Joe Casabona: Thank you! So I think it’s very easy for freelancers, solo people, side project people to get distracted by all the shiny ideas that they have. I know I’m certainly guilty of it. So finding a schedule and really focusing is just great general advice if you are doing your own thing out there and it’s really great to hear. So Unsplash was a side project of Crew?

Michael Sacca: Yeah.

Joe Casabona: And I hear, I’ve read that it’s been instrumental in helping Crew succeed?

Michael Sacca: Yeah, it basically saved the company. So we needed to find more people who needed more projects and it was really early. So it’s still just the four founders, Mikael, Steph, Luke, and Angus and they knew that they were solving a problem with Crew but the growth wasn’t fast enough and they were in a local incubator here and so the expectation was that you do find a market and you’re able to prove. And Unsplash came out of the need to drive more traffic to Crew and the idea is Splash being Splashed images on a website, Crew being someone who builds websites. Can we build, can we give people these free images so that they don’t have to worry about paying for stock photography. And Mikael put up the landing page, we’d had like 10 photos that they had taken at a photo shoot recently or like the B sides of a photoshoot and a signup form. And they woke up and there’s like 10,000 people who downloaded it.

Joe Casabona: Wow!

Michael Sacca: Yeah like it got posted. I don’t know if it was product hunting back then. But it got posted somewhere and it caught traction and they didn’t stop like it wasn’t like 10,000 people that everyone forgot. 10 days later he put out another ten photos and people were now already sending in their photos that they wanted to be distributed on this. And Luke, who was one of the founders, I don’t believe he ever built anything on Crew, he immediately just took on Unsplash full time.

Joe Casabona: Gotcha.

Michael Sacca: And so we knew it had legs at that point. They knew it had legs at that point and we just nurtured it for the last three years. So he’s always had a team, a smaller team than Crew working on Unsplash full time because of that growth. And because he was driving cause it drove so much traffic, Crew naturally got traffic. And so it made it easier in our sales process too so we can go to agencies and say “Hey, you know Unsplash?” like “Yes, I’ve used Unsplash”. I’ve never to Crew but and so we could use it in that way. And then the traffic that it would drive to Crew it saved the business at that point in time.

Joe Casabona: Man…

Michael Sacca: which was awesome

Joe Casabona: Yeah, yeah. Well, you’re talking to an Unsplash user. I go to that well a lot. I’ve thought about submitting my own photos to it, but you know, I’ve got like that like impostor like I’m not a photographer but I like taking pictures and the pictures there, beautiful. I’ve been using it for years.

Michael Sacca: Thank you!

Joe Casabona: So that’s awesome. So man, then so there’s a couple of things. So, first of all, I always like to ask who you talked to for business advice? I think we touched on that a lot with your customers, so I would actually like to ask you like this kind of unscripted question about pushing the limits of free, right? Because I had Troy Dean from WP Elevation on the show and he’s kind of talked about that too. Unsplash is free royalty-free images that help grow.

Michael Sacca: Really extreme.

Joe Casabona: Yeah, what’s that? Yeah.

Michael Sacca: That’s pretty extreme.

Joe Casabona: Yeah, you just, you don’t see that anymore. I mean you go to, I stock photo and it’s like $1,000,000 is this photo which is like creepy weird photos, right? Like these are, these are great!

Michael Sacca: Oh my God!

Joe Casabona: Yeah, yeah. So this free resource helped build your business. How did you or how did Crew kind of, what did that funnel look like?

Michael Sacca: Yeah, so for Unsplash it was just, it was literally a link that said ‘built by’ and it’s the classic like build the plugin for WordPress. And then for the free version, you include your link always on their site and that drives traffic to you. And that’s really what worked for Unsplash so he was enough because there was a volume, there’s a volume of users that while not every user of Unsplash was a good fit for Crew, there was enough of a fraction of them that it worked. And they would come to Crew, they would start projects and then spend money with us and it was enough to fund keeping Unsplash going, right? It was worth it. And I mean we could talk a bit about the, I guess like the business model of free if you want, which is more like ’cause Unsplash is really more in that Instagram line, right?

Joe Casabona: Right.

Michael Sacca: And now we’ve broken off the companies in Unsplash needs to eventually bring in its own revenue. Because, and so that’s more in line with how do you monetize Instagram, right? And so how far can you push it and how do you fund that so that you could eventually get to that scale. And that’s really the goal there, right? But when you’re just talking free, we also do and we might be more interesting is we also have these tools, how much to make, just howmuchtomake.com and it’s how much to make an app, how much to make a website, and how much to make a logo and these are estimators. So there are mini tools that we’ve created that help people estimate how much their project would cost. And at the end of it the link is to hire someone on Crew. And so that was much more direct where like the effort to get those those up was pretty significant at the beginning but is a tool directly related to our market and to our customer. And then we gently push them into Crew if they do have the need and I think that someone that anyone can do in an industry because content is really, it’s saturated, it’s hard to get enough attention. So I think it’s interesting to think about what other value, and how do you provide value to your customers. Content’s one way but there’s a lot of different avenues depending on what you’re doing that you can get the customers attention, you build trust with them by providing them value that eventually you make the sale. It’s basically a way of automating the classic sales process which is add value add value add value. So…

Joe Casabona: Awesome. And yeah, and that’s I think that’s something that I certainly have trouble finding the balance of, right? because working in projects and you don’t wanna sell yourself short but you want to offer that value and you want to find something shareable. And I think you’ve done that with the kind of auxiliary free tools that you have for Crew, right? And at this point, I do want to get to the title question, which is how did you build it? So you are, it sounds like you’re more focused on like the sales aspect. But if we want to talk about tech or sales or whatever you’re most comfortable with.

Michael Sacca: I mean if we talk about, we can talk about Unsplash and how we built it, right? The first version was literally a Tumblr blog and with like a Wufoo sign-up form. And Crew started much the same way, Crew was a Wufoo signup form for both sides. So if you had a project, you filled out a web form and if you wanted to work on projects you filled out a web form. 

And for Unsplash, the Tumblr blog just showed all of the images and that was enough to get off the ground and get traction to know that “OK this is an idea we should do without building a ton of infrastructure.” Then we built the infrastructure, we used Ruby on Rails to build the first basic site for Unsplash. But before that, it was all tools that Mikael, the founding CEO, that he could set up without having to do any technical work. Just some base level styling may be, and send out an email and it was all things that he was very comfortable with. And then if it didn’t work, he lost a couple hours you know, and so it wasn’t a big deal. We tried, these weren’t the only two things that we tried right but these were the two that stuck. What’s really tough is when you spend weeks or months trying to build this side project to your main business and then you put it out there and it just doesn’t catch on, you know. It wasn’t the right thing. So that’s what’s really it’s you have to be smart with your time, your resources, and even if you can build it doesn’t mean you should, right? Just find the simplest way to get the base version out there. And if that version solves the core problem, you probably got something sticky.

Joe Casabona: Yeah. So that’s also, that’s your minimum viable product. Essentially you used other tools which are great ’cause you didn’t, you know, I’ve been in the position where I sank hours into developing this plugin or some idea and I was like “This is gonna be great.” And then like when nobody came, right? ‘Cause I always take like a very Field of Dreams approach to it by building… Well nobody came. I got discouraged. But yeah, you know this way it’s it’s got a minimum viable product out using whatever tools are at your disposal and you could always iterate. 

Michael Sacca: Yeah. So yeah it could be just like a preview video for a plugin that’s not built, right? Like that will tell you whether people click on it if they want it and that’s how we use our time is when we’re working on, you know, if we have a full-time job, our time is limited. We don’t have a lot of time but we want to but we have a passion to work on something else to build something for ourselves. And but the worst thing to do is get burned out trying to do that.

Joe Casabona: Yeah, absolutely. Especially you know, there’s a lot of talk about work-life balance and there’s you know, there’s like strong opinions about working well, like trying different things but I mean you know, if I’m prioritizing my time, my wife works nights.

Michael Sacca: oh OK.

Joe Casabona: Yeah, she’s a night shift nurse and so when she’s home you know, I wanna spend time with her. And when my daughter is born you know, I’m gonna have to find a balance to whatever two labels you wanna put on those. So that’s I mean, we do have to spend our time wisely. So from minimum viable product to the Wufoo forms and Tumblr, how did the iteration process go? You said you built that on Ruby on Rails, what was scaling those products like especially ’cause it seems like you saw basically overnight success with Unsplash?

Michael Sacca: Yeah, Unsplash was I think, it’s fair to say hell to scale because no one working on it had scaled something like that. So all of a sudden we have people, we have large files being downloaded. I mean these images you can use on a billboard at times, right? So these are incredibly large images that they’re being downloaded millions of times a day. It was tough, it was really tough. Luke learned, I think it would be fair to say he’s learned a ton through the process of building it. And so the initial versions were built on Ruby and then we hired some developers you know, a couple months in to also help. And now eventually it’s now built on react. But I wish I could tell you more about like the nitty-gritty of what they ran into. I just know that working on a product at that size was an incredible learning process.

For Crew, we used CakePHP and built out kind of a fully custom system that could handle all the inbound projects. And that like we are now probably three years in and we have you know, it’s time to clean up that technical debt. And so I think a lot of engineers can relate when you’re trying to move fast. It’s tough to balance the business side and the engineering side where you really do need to clean this stuff up but you also can’t afford to lose a couple of months. So that’s kind of where we’re at now, it’s not the worst problem to have though. So yeah.

Joe Casabona: That’s, yeah, yeah. Man, that’s great! Well, I’m excited to see like where that goes, how both websites evolved. So it was a slower build with Crew, is that right?

Michael Sacca: Yeah, it, I think because we didn’t have the necessity of scale than Unsplash has. It was, we were able to take our time a little bit and experiment a little more. Where in Unsplash you know, they kind of had to get it right or the site would just go down, yeah.

Joe Casabona: Yeah, absolutely. Yeah, OK. So we’ve talked about, we have about 10 or so minutes left.

Michael Sacca: Sure.

Joe Casabona: We’ve kind of talked about where the product was at and where it is now. But what are your plans for the future? And we can talk about Crew or Unsplash or both you know.

Michael Sacca: Let’s do both, yeah. So for Unsplash I think, I mean the goal is just to keep growing. No major changes except for the product, right? So still free photos, still focusing on high quality. I think one of the big things for 2017 is starting to even diversify some of the content that’s on there and finding creators who may be taking like photos of people or different sceneries and things that you know, traditionally have a lot of hikers and really beautiful imagery. And will continue to do that but what else can we do like where else can we expand to.

And then for Crew, we’re working on automating the matching process. And so for anything under $10,000 can we just find you that match and instantly kind of like an Uber situation, right? And then growing our network of freelancers. And so we’re really focused on SEO, we’re focused on SCM this year and really just kind of getting down to the nitty-gritty of selling better projects and focused on the growth.

Joe Casabona: Nice, so you want to grow freelancers. If there are freelancers listening, what do you recommend for them you know, like signing up for Crew, setting up marketing themselves being Crew?

Michael Sacca: Yeah. No, absolutely go to crew.co and you’ll find the link where you can start to fill out your profile and then we let all of our profiles usually within a week and we let you know, if you’re in, if you’re on the waitlist or what you would need to improve to kind of meet the standards. But we try to be really transparent with it so that you know what you need to do. And I know sometimes like people have waited on the waitlist for a long time ’cause we had 100,000 people have signed up for the waitlist up until this point. But we just rolled out some tools so we can get through it faster and really scale it. So yeah, so go to crew.co and signup and will hopefully get you on.

Joe Casabona: Yeah, definitely. And I think this is something, again that I’ve had a problem with. And so I suspect I’m not the only person. What are maybe some of the bigger issues that you see with, what’s the regular feedback that you give to freelancers to kind of improve their profiles? ‘Cause again marketing is something that’s so hard for me to do. So…

Michael Sacca: It is. It’s hard for the developers, they have a really hard time. I think the best thing is getting good networking and having personal recommendations. That’s how you build trust fast. For designers, I think dribble and those types of portfolio systems have really done a disservice to the industry of design. I think it’s important you have to have it, you have to have your dribble, you have to have your Behance but when a client is coming, the first thing that they’re always looking for is a project that’s near their project. So when you’re pursuing projects, literally if you haven’t done a medical website and you have a medical client, if your competitor someone who’s bidding on that project as well have done a medical website, more likely that they’re going to get it.

Joe Casabona: Yeah.

Michael Sacca: And so focus on people that are in line with what you’ve done, and start to reach out. But you’ll have the most success when you have experience in an industry. I think case studies are incredibly important so that we can actually see the thought process that goes through. And clients can see that it’s not just the design, it’s not just a website, and it’s not just the development that there was thought and reasoning behind why these decisions were made and how you felt about them. So I think case studies can be incredibly important to build trust. And I think the most important is when you’re talking to a client is to not focus on things like the budget, to not focus on, you know, the answers that you necessarily need but to focus on the problem and the solution that they have that you can provide for them and to build that trust and rapport before bringing the budget to them. And we used to call it ‘the no proposal’ proposal where you know we would just get on the phone, we would do a phone call or two and kind of feel them out, but we wouldn’t give them a rate until we fully understood the project. And that process, wasn’t just about fully understanding the process, it was about building their trust with them so that they were bringing us. They had invested so much time in getting us up to speed on the project that it would be almost a disservice not to hire us.

Joe Casabona: Yeah, absolutely. And I mean the more you understand about the project from the beginning the more accurately you can quote too.

Michael Sacca: Totally yes.

Joe Casabona: That’s great. You know I’ve always told fellow freelancers to find a niche because when you do find a niche let’s say medical websites, you slowly gain domain knowledge of that industry. And then you can again, you can build better projects and understand the problems more. So that’s absolutely fantastic advice. So as we wind down our time here, I want to ask you my favorite question which is, do you have any trade secrets for us?

Michael Sacca: Trade secrets. So I told you ‘the no proposal’ proposal which is just the delay that the proposal process and builds their trust so that they are vested in you. I would say hmmm, help me out here. What kind of secret would you be looking for? I’m sure I’ve got something.

Joe Casabona: Yeah, well you know there’s, we have gotten a lot of great advice in this episode but one of my favorites, and the reason it’s my favorite is that it’s super open-ended. So well, so actually you know you said that you started businesses before you came to Crew, right?

Michael Sacca: Yeah.

Joe Casabona: So what maybe give us a gem from that experience you know like you’re starting a Business Today. What’s something that you wish you knew when you started your first business?

Michael Sacca: Sure. Doing the research. So I’ve started so many businesses in markets that were never going to go anywhere. Do jobs to be done right? One of the best frameworks for figuring out if you’re actually solving the problem. So if you look up Bob Moesta or Clay Christensen, they have so much material on how to do these customer interviews that are, that they basically are taking tactics from like FBI interrogation. And so it’s not about asking the customer will you purchase this? Is this a good idea? It’s about knowing the root cause for why they would even consider purchasing your product and there are some amazing case studies. And when you start to do that work it’s similar to sales because you’re learning why, but you can stop wasting your time trying things out and building in all ideas that are good when they are there in the very beginning, right? But when we bring them to market, they start to refine themselves. You can do that refinement before you ever start building. So I love the jobs to be done in the framework. Ryan Singer from base camp is also a huge believer in it and that he’s kind of a product guru if you will. And so I would say do more talking and research and a little bit less building at the very beginning cause when you can actually solve a problem, you get the results like on Splash where it seems like a random occurrence that it just blew up and kept growing but it solved, it hit a root, it hit a need in the industry and solving the problems would keep it that opportunity.

Joe Casabona: Yeah, that’s great. So I mean one of my favorite books I talk about it all the time on the show, ‘Start With Why’. It sounds like you’re starting with Y right? You’re not just going off and building a thing because you think it needs to be built. And I think the other takeaway here is that if you ask 10 people, “Do you think this is a good idea?” none of that won’t probably say yes because they don’t have to put any money towards it.

Michael Sacca: And then if you ask them would you pay for it, five out of ten would say yes. And then if you ask them for the money, everyone would probably walk away.

Joe Casabona: Right, exactly. So that’s great you mentioned a lot of great resources. They’ll all be in the show notes for anybody listening to. So Michael, thank you so much for joining me today.

Michael Sacca: Thank you! I appreciate the time too.

Joe Casabona: Yeah, absolutely. It was a great time. Thank you too to everybody out there listening.

Thanks to our sponsors and until next time get out there and build something.

And that’s a wrap on Season Two. I want to thank everybody out there for the great support that you’ve given me over the last few months. This podcast has bloomed into something that I didn’t think possible especially within the first few months. So once again, thank you so much to all the listeners out there, thank you to everybody who has sponsored the show over the first two seasons.

And the guests, thank you all for taking the time out of your busy schedules to come to talk to me about something that you built.

We’re going to take a couple of weeks hitis as the show’s gonna come back on June 13th and it’s going to be better than ever. There’s going to be some new audio, a couple of new segments, and lots more sponsors and information and things like that. 

I also want to get to know you better so I’m still recording Season Three and I wanna give you the things that you wanna listen to ask the listeners. So if you haven’t yet, please go over to buildpodcast.net/survey and take the survey there. It’ll only take you a few minutes and virtually every question there is optional so only answer what you are most comfortable with. Again that is buildodcast.net/survey. And one more ask, help people find this in apple podcasts, right? I think that’s what they renamed iTunes too. Help people find this in Apple podcasts by rating and reviewing it. It’s the best way to help people discover us. 

So again, thank you so much everybody out there for listening, for sponsoring, for being on the show. And until next season, get out there and build something.

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