“Teaching is way harder than coding or building products.”

Michael Sacca | Co-Host at rocketship.fm & Partnerships at Crew

Interview by Thomas Peham

August 10, 2015

Photos by Michael Sacca

Make your startup a rocketship.

Michael is working at Crew - a marketplace for creatives by day, and hosting a tech & startup podcast by night.

Michael Sacca shares the challenges and lessons learned of remote teams and what he thinks about the web development trends.

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Thanks a lot for your time Michael. Can you tell us a bit about yourself?

Yeah, absolutely. I currently lead partnerships at Crew and I also co-host rocketship.fm with Matt Goldman and Joelle Steiniger. Rocketship is something we've been doing for going on a year and a half.

It doesn't take a lot of time out of our week, but we're able to provide a lot of value so we've just kept doing it. It's just been one of those projects that is ongoing for us, and is incredibly valuable because of the of the people we get to meet.

How do you balance those activities?

Balance is always a hard thing to achieve. For Rocketship, because we've been doing it for about a year and a half, we've been able to streamline a lot of the processes.

We have an audio engineer who helps us out with the mixdown process. For me it takes about two hours a week. We've streamlined the whole thing and so it doesn't take up a lot of time.

We focus on what's providing value for us, which is having conversations with people that we respect.

How does a typical day in the life of Michael Sacca look like?

I have two children. I have a 3-week-old and a 3-year-old. My day usually starts around 6:00. And then by 7:00 I can start answering some emails, so I do emails in the morning and then I try to get into a coworking spot by 9:00.

I work remote for Crew. Crew's based in Montreal and I work from Las Vegas. I try to get into a coworking spot around 9:00 and handle any writing and stuff in the morning, and then in the afternoon do any project or production work that's needed. I'm usually home by 6pm.

Can you share some insights on Crew, and what you guys are doing?

At Crew we are providing a marketplace for creative professionals to connect with high quality projects and for entrepreneurs and companies to find vetted and trusted creative talent. Our job is to make that process as easy as possible for this new economy of professionals and independent studios.

People come to us, we help budget and scope the project, and then we match those projects with professionals that meet the budget and the skills needed. What I'm doing is building partnerships with companies and agencies.

Can you share some insights on how you stay productive as a remote worker?

Remote work is tough because sometimes it can be a little lonely. You can’t have a quick conversation with colleagues in your office.

I try to process everything out, so I definitely have my day planned with the tasks that I want to get done and the things that I need to do.

I just try to stay focused on getting those done, and then it's really important to have those skype calls and those meetings with the team to stay on track.

Those usually give me a bit of a boost in energy and productivity. Sometimes when I'm feeling sluggish and not quite sure of what to focus on, I'll arrange a quick skype call with a teammate to touch base.

That usually helps to rejuvenate me.

There is something to being in the same room as people, which is incredibly important, and I think it's important for teams to get together as often as possible, even if they work remote. To get together and revive that energy that you have, because you're all working on the same goal, but sometimes you can focus when you're remote.

Are there any other tools which help you to stay focused?

Our stack is Trello and Slack. That's how we keep everything organized. We have countless Trello boards, and we have all of our projects, our goals, our notes in Trello.

We use Slack for all of our quick communication and Skype seems to be the one that we've stuck with for phone calls. We have used google hangouts, and we've use speak.io, which is an amazing product that integrates right with Slack, but Skype is just still our go to.

So, Crew is a complete remote company?

Yeah. We have a core office in Montreal, but most of the team works in a remote manner.

One of the really big things is when you have that office, is keeping everything in Slack. Those conversations that are had in the office aren't captured anywhere else.

One thing that we've really worked hard on is taking those conversations to Slack to keep everyone on the team updated, which has been really important.

If you feel out of the loop it can be demotivating. We've tried as hard as we can, even when people are in the same room, to talk on Slack. We can have our social conversations outside of course, but keep the business chat in there. That's really helped because that way everyone can be involved.

We have teammates in Toronto, Vancouver, I'm in Las Vegas, we have England and Finland I believe, so it's a very spread out group, but we make it work.

We have a lot of families and people that are happy coming to work in a remote manner and I think that's the most important part.

Has there been any great advice or wisdom you've ever received which you'd like to share with us?

The biggest thing that I've learned is communication.

I think poor communication kills everything whether there's a miscommunication avoiding hard conversations with teammates or co-founders.

When you're not on the same page and you're leaving things in a gray area, that's always been when things have gone wrong for me. This is when everything falls apart. I've had many projects fall apart with co-founders, where we weren't on the same page.

We were on the same page on 80% of things, but we weren't on the same page for 20%. We avoided those important conversations of who would lead or who was in charge of this or that, or what were our expectations for the project.

We just let those slip and we just built really fast. At a point it would start to disintegrate. It's impossible to grow if your head is unstable.

Communication is vital and it's so hard, it's an art form.

Getting everything out on the table before it becomes a big issue. Just like in a marriage or in a relationship, it applies directly to business and partnerships.

What would you call the most important lessons learned when co-founding various companies?

For me a lot of the breakdown has always been communication. I've learned a lot about going to market, about building products and staying on track, doing user testing. We have done a ton of that, but the reason the project's always failed was communication.

That's probably the biggest lesson I've learned when running my own agency and co-founding several projects.

Has there been any "aha" moment in your life where technology really clicked for you?

We built this application, and we thought we have a great idea, but I never put out a product before. So we put some geo tracking in it so we could actually see on a map where it was being used.

We launched it and we were up in the iTunes store and all of a sudden the pins started dropping, and you realized that people in Africa, in Europe, in India, in China are now downloading your software, and using it.

You could actually see throughout the day as people were waking up, or maybe it was their afternoon and they were finding something new for their child. It was amazing that 10 years ago that wasn't even possible and now we were building software that was reaching people that we had never met throughout the world, that we never even marketed to. They just found us in that Apple store and it was absolutely incredible.

We realized you could actually build a real business here with just three people and go global.

It felt really inspiring, because you realize that you're touching people's lives all over the world. You've built this software, but it actually has an emotional effect on people everywhere. That was an "aha" moment, in how powerful these tools are.

You also worked as a professor at University. What was your motivation to start lecturing?

I taught CSS and HTML at a local university here in Las Vegas. I was in Las Vegas at the time, and when I was teaching it was before Tony Hsieh had moved Zappos downtown, and before the tech fund was in existence, and so there wasn't a lot going on.

I was running an agency and I was having trouble finding people to work with.

So for teaching, it was my way of giving back, helping the community grow, so that we could have more people who could work in this area.

Teaching is hard work though, that's way harder than coding or building products.

That's probably the hardest thing I've ever done.

Going back to your current job at Crew. Can you share some challenges being the intermediate between companies and creative people & remote workers?

It's good that we're all connected around one goal, so even digital nomads and agencies and clients, they all have the same goal in mind.

They all love building products, so we have that going for us.

It doesn't matter where you are on the globe, as long as you're dedicated to doing the work that you agreed to do, and doing a great job.

We've found some of the best people out there, so it's usually not an issue on that side. It's more about the regular business challenges, like getting in front of people, getting in front of agencies and just being able to share our story, and making them part of that story.

That's always a challenge with any business that you take to market, is just how do we get that visibility in people's incredibly busy days.

Creative directors and CEOs and presidents of agencies have an incredibly busy day. That's just the nature of their work. Getting that 15 minutes and convincing them that giving us that 15 minutes is worth it, is one of the biggest challenges that I have, but it's fun. Its a good challenge to take on.

And what’s your best trick to get that 15 minutes?

In crafting the right email. It's not just spending time sending a lot of emails, but it's spending time crafting the value to them and what they can get from us.

When we flip it to their perspective and what they get from us, it gets a much higher response.

People are much more open to hearing what we're doing. That's been a great lesson. Doing your research is another incredibly important thing.

Doing that research on LinkedIn and actually doing the discovery is incredibly important, and finding the right people to talk to. It's different for every product, but there's someone at the organization who's interested in what you're building, and finding them is incredibly important.

I come from being a designer, so this is all a new frontier in a way. It's exciting though. I like the change of pace.

As the co-host of rocketship.fm you interviewed some truly inspring people. What do you think will be the next major challenges coming in in web design or web development in the next years?

I think we'll see more of a fusion of software and hardware companies.

There's a lot of movement in biotech and food, and I think we'll see software integrated into those different sectors. I think in the last five years we've seen software stand alone. It'll continue to stand alone, but I think there'll be more opportunities for software engineers and designers to be integrated into these other product types. Probably in the ways we haven't thought about.

Right now we focus on SaaS apps. I think we move on to just different problems and I think that's incredibly exciting.

Is there any useful resource or any book or blog out there that you would recommend to others who want to get started as a web designer?

There's a ton of amazing resources out there, you just have to be hungry and want to learn, because the resources change every day. Back at the days, it read a lot on Smashing Magazine and Nettuts. Friends and colleagues have also been an incredible useful resource.

Is there any project or technology out there you would like to explore more at the moment?

There's so much out there right now, but there's also so much undone and incomplete that shouldn't be used in production. I'm looking forward to seeing some of the projects that have felt cowboy coded reach a solid foundation.

I think we could build much cooler stuff if we stop focusing on the tools that we’re using so much. And actually start building.

I think that's the really exciting part about technology, is when anyone with an idea can make it come to life rather than focusing on the underlying languages.

What advice would you give yourself as a 14-year-old?

Go to computer science school. I was into computers at 14 and I was taking them apart and building them, but for some reason I didn't see it as a career and I didn't see what was happening.

So I went to art school which was great, but I think if I had stuck in those key teenage years, I could've been more on the other side of technology, which I think is incredibly exciting.

I'm on the frontend now, but I could've gotten a better education in computer science. And I kind of wish I had done that at 14.

Thanks so much for your time Michael!

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