Michael Sacca is a modern renaissance businessman who inspires tens of thousands of entrepreneurs each week on his podcast, Rocketship.fm. Sacca has climbed the ranks to become the President of a multi-million dollar business that supports companies and creators across 30 countries.

He’s leveraged his experience in a wide array of roles—like coder, podcaster, web design consultant, product developer, and sales lead—to grow his skill set as an entrepreneur, leading to several successful business ventures and eventually, a leadership role at someone else’s company.

He recently became the President of Crew, a business that matches freelance web designers and coders with companies in need of their services. His ambition, leadership skills and experience as a jack-of-all-trades wowed his superiors and fueled his rise through the ranks after starting there as a partnership manager.

Meanwhile, he continues to run Rocketship.fm and Brandisty, a web platform for storing and distributing brand assets.

Michael has a truly impressive toolbox of talents, but he’s very down-to-earth and honest about the sometimes haphazard nature of his career progression, which has occasionally been motivated simply by the need to make a buck.

In our interview, he opens up about his teenage years buying and selling Smashing Pumpkins concert tapes online, how he’s managed to change his mindset as he moved from role to role, the stresses and challenges of becoming a leader, and how nobody in business has all the answers all the time.

Michael is very active around the Internet, and there are lots of different ways you can continue to follow his story. For starters, you can tune into Rocketship.fm to get exclusive insights from his interviews with the brightest minds in tech and entrepreneurship.

You can also find him on Twitter @michaelsacca, follow his posts on everything that has to do with freelancing on the Crew blog, or read up on his latest adventures and musings over on Medium.

In this episode with Michael Sacca, you’ll learn:

  • How trading concert tapes online prepared him for entrepreneurship (6:08)
  • How to start a business as a web design consultant (8:30)
  • Why necessity can be a good motivator for your career (11:30)
  • Why you should quit your business if it’s making you miserable (13:10)
  • How to decide to end one business venture and embark on another (16:29)
  • How to transition from being your own boss to being someone else’s employee (19:41)
  • How Crew helps freelancers and project owners work with each other (22:28)
  • How to land a leadership position where you work (28:52)
  • The stresses that come with leadership roles (31:37)
  • How to lead and inspire a distributed team (35:07)
  • Why you don’t have to be perfect to be an entrepreneur (36:57)

Please enjoy this interview with Michael Sacca.

Links and Resources Mentioned in this Episode:

Companies and Organizations:




This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

DeveloperTown works with clients ranging from entrepreneurs to Fortune 100 companies who want to build and launch an app or digital product. They’re able to take the process they use with early stage companies to help big companies move like a startup.

So if you have an idea for a web or mobile app, or need help identifying the great ideas within your company, go to developertown.com/powderkeg.

If you like this episode, please subscribe and leave us a review on iTunes. You can also follow us on Soundcloud or Stitcher. We have an incredible lineup of interviews we’ll be releasing every Tuesday here on the Powderkeg Podcast.

Did you enjoy this conversation? Thank  Michael on Twitter!

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What stood out most to you about what Michael shares in this podcast?

For me, it’s how to lead and inspire a distributed team.

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Related Article: Growing a Remote-First Team


Episode Transcript

From VERGE headquarters in Indianapolis, I’m Matt Hunckler. With powderkeg igniting startups, and today, I talked with the president of a multimillion dollar tech business that supports companies and creators across 30 countries.

We’re a distributed team. And one of the biggest struggles that I have is leading from the inspirational side, a team that’s not in the same room with a distributed team. It’s hard to have those deeper planning sessions and then also kind of build rapport. Something that I really want to get better at is actually being able to inspire people through a video, which is a lot harder than I thought it would be.

That’s Michael Sokka, president of the Freelancer marketplace crew. He’s also the co host of rocket ship.fm, which is a podcast that inspires 10s of 1000s of entrepreneurs each week, that journey and the lessons learned along the way, coming up on powderkeg igniting startups, where each week, we share the untold stories of innovation, leadership and technology beyond Silicon Valley. I’m your host, Matt Hunckler. And I’m the founder and CEO of verge a network of local communities with global reach for tech entrepreneurs, investors and top talent outside of Silicon Valley. And you know, as my team and I have grown verge over the past seven years, we’ve had some really cool experiences. Looking back, we’ve hosted more than 1000 entrepreneurs on our stages at events around the world. And those founders have gone on to raise more than $500 in capital collectively. You know, they’re disrupting industries, creating wealth and changing the world. And most of these entrepreneurs, the cool thing is they’re leading from areas outside of Silicon Valley. They’re using their talents, their strategies, their local resources, to build tech driven businesses that matter. That’s why we started this podcast. Each guest has their own powderkeg, full of raw skills and talents that ignited their startups and fueled their growth. These are their stories, you can find me on Twitter and on Instagram at Hunckler. That’s at Hu NCKLE are, please let me know how verge powderkeg. And I can help you with your entrepreneurial journey. Because we’d love to help, I’d love to hear what’s going on with you, and maybe even promote through our network as well as we continue to grow this awesome community of listeners. This episode of Powder Keg is brought to you by developer town. Now in previous episodes, you’ve heard us talk about how developer town helps business leaders turn great ideas into product with traction. And of course, they have a ton of experience doing this themselves. But they also go out of their way to hear from outside perspectives. And recently, the marketing team at developer town traveled to Manhattan to meet with my good friend, Derek Mach. And he and I actually go way back, like all the way back to freshman year of college at Purdue, where we were living across the hall from each other in the dorms. Now, of course, Derek is a really smart guy, he has risen through the ranks. He’s now the senior innovation brand manager at Anheuser Busch InBev. And in this interview, Derek explains how innovation comes from both an emotional connection to the product that you’re innovating, as well as the right company culture to foster that innovation.

I knew that I had an opportunity to learn even more about emotion led brain building. I knew it was a culture that really aligned with me and I’ll talk I’m happy to talk about our corporate culture here. A culture of ownership a culture of meritocracy, a culture of never being truly satisfied or complacent. The category is one that’s easy to talk about, right? Alcohol has been bringing in beer in particular has been bringing people together for literally millennia, there’s some evidence that people started harvesting grain first for brewing, before even even even baking, things like bread, so foggy history, but super interesting nonetheless. So for me that was really motivating. And then finally getting on the campus at the time we were in, in St. Louis meeting the innovation team meeting the broader marketing team, meeting the folks brewing the beer, touring, literally going through the brewery touring the brewery, meeting some of our clients, they’ll seeing the history seeing the archives. For me, it’s it’s a place that is really storied has an amazing past but also has an incredible vision for the future and a mantra of continuing to dream ever bigger is the way I characterize it. And I love that charge, particularly working in innovation here, I get to help be a part of that.

So clearly, innovation can’t exist in a silo. It takes thoughtfulness and immersing yourself in the different areas of the business. This is what I love about developer town. They take this approach when working with enterprise clients understanding the business context as a necessary component of designing a web or mobile product. You can learn more about that process and developer town at developer town.com/powderkeg. Developer town, start something. Today we’re talking with Mr. Michael Sokka, who’s hanging out in Montreal, Quebec, just killing it at his tech company crew, and we’re going to talk all about his really incredible lessons that he’s learned climbing up through the ranks from sales guy all the We have to his current role as president. And while Michael may be headquartered in Quebec right now, we do not do this interview in French, thank goodness, my French is terrible about Michael has actually moved around quite a bit throughout his fascinating career starting and running companies all over the country, including Las Vegas, LA, San Diego, and now of course in Canada up in Quebec. So really interesting to hear how he’s navigated those big career moves, and how he’s taken advantage of some pretty cool career opportunities. We’re gonna get into talking about Michael’s hit podcast, rocket ship FM, which of course, you can just find online@rocketship.fm, with its 10s of 1000s, of weekly listeners, and you’re gonna learn some of his biggest insights from interviewing hundreds of entrepreneurs and technologists he’s had on as guests for his show. So we’re gonna totally nerd out, have some fun and just share a few startup stories like this sort of behind the music sort of vibe, where we’re going to kind of go back into Michael’s career, and work our way up to what he’s doing now at Crewe. So are you ready? Let’s set this thing off. Well, when did you actually first have your first inklings that you might be, in fact, a little bit entrepreneurial?

You I guess, at a young age, I always had various things going on, I started out like tape trading online. When I was like 12, which is kind of entrepreneurial we would be, it was in the early days of like geo cities, we would set up these pages of at that time, it was smashing pumpkins, live shows. And so I collected almost every single available bootleg tape. And this is just people going to the concert at the time with a tape recorder and literally recording. Sometimes you get lucky and you get like something off the soundboard. But I used to trade those and even sell them for people who didn’t have a collection. And I had hundreds and hundreds of tapes as a kid, and even started a little like business. I was buying equipment, so I could copy them faster. And that’s probably the first time I don’t think I really realized it. But it’s the first time i i I realized I liked organizing and kind of running and growing something. But I actually didn’t start any sort of entrepreneurial journey until I was about 26 or so.

And with that original business, even though you know, maybe you didn’t have employees, or any funding or anything like that, was it earning money for kind of, you know, some side pleasures that sort of drove you? Or was it more like, sort of like building the fort, building something, having something kind of bigger than yourself that was driving you when you’re starting that first business? Yeah, I

wish I could say I think it was more of an obsessive compulsion to own every single live Smashing Pumpkins tape. It was like a collector’s dream, that there were these it was it was more of the hunt to get everything rare that someone else didn’t have. And that was really I think, what what drove me it did make a little bit of money. But I basically just bought more tapes, and some equipment with it. But it was more of that collectors like compulsion, I think,

well, and I know you’re a vinyl fan now. I see you old habits die hard a little bit. Yes. That’s awesome. Well, we get we’ll have to riff on that later, because I’ve got a collection myself. But I would love to find out a little bit more about that company started when you were 26.

Yeah, yeah. So at 26 I quit working at a restaurant, I was in LA. And I just I quit the restaurant job to figure out how to code. So I wanted to learn how to code my roommate was doing it. He was really successful. He was working less hours than me making three times the money. And basically living a very leisurely lifestyle in Los Angeles. We were living in Santa Monica at the time. And I was like, I could do this, right. So I quit. And I gave myself a month to figure out how to design and start writing some front end, I had some experience from tape trading and building the websites then. But technology had changed a lot in those 10 years. And so I still had a lot to learn. So I started he started handing off clients that he didn’t want to deal with, to me. And that first month, I was able to pay my rent. I mean, I worked a ton. But I was able to figure out enough to where I was making like $15 An hour writing code. But I could pay my my $900 a month in rent, and we actually left Los Angeles moved to Las Vegas that month, so that we could our rent was a little bit my wife and I, our rent was lower in Las Vegas, and I could actually focus on learning this new skill and eventually building a business out of it.

And in those early days of that business, how did you eventually scale beyond yourself? What kinds of tools or resources Did he is? Yeah. So

I brought on a lot of partners that a lot of them didn’t work out. I really wanted to work with the team. That was my goal. And so I, you know, after about three years, we finally built it enough where I moved down to San Diego, and we started hiring employees. Some of the tools we used, a lot of them aren’t even around anymore, because they’re so long ago. Sure. But I used to love like, do.com when it was a task management, oh, yeah, it’s just really simple task management. I loved that. And we built a lot of the early kind of like infrastructure on small projects like that. But back then it was a lot of email. We didn’t have slack, there wasn’t anything like that. So it was a lot of email and a lot of Google Docs.

Wow. And you kind of took this concept that was sort of inspired by a friend, did you eventually grow that business bigger than your friends business? Or did you end up partnering with him in some way?

No. So we went different paths. He now works at IBM and Watson. So he’s done really well for himself. And then I’ve taken more of the entrepreneurial path. So as he just kept, like teaching himself how to code how to code and he became incredibly talented, but and then I went from design to front end development to business development and sales and now to present so we taking slightly different different paths there to get there.

Well, it’s a really interesting path. And I’d love to dig in on that, because you don’t always hear tape trader, to consultancy, you know, founder to sales, to back to President role. So can you can you talk me through that a little bit? How did you did you know how to navigate that, or were you kind of figuring it out one step at a time,

I think it was totally haphazard, and figuring out one step at a time like so it regionally to get clients, I needed to design and I needed to build websites that needed to happen to pay the bills, and then in correlation with that, because you’re only one person. And eventually, like, we were five people, I still needed to do the sales and the marketing of the agency, in order to get bigger and bigger clients. And eventually, we were working with scholastic and Nike, we did a project with Kobe Bryant and GE. And so we were working with larger clients. But to do that, I needed to know how to write the contracts and how to sell the contracts, and compete with other agencies for that work. And so that’s where I think a lot of those business development skills were but I still saw myself as a designer most of that time. And those business development skills were the essentials to do design. And at some point, it flipped. Like when I started working at Crewe, I was hired to do partnerships, but I still wanted to design things, but they just didn’t let me. So I wasn’t allowed to touch the code. I wasn’t allowed to put any designs together. I did write it all scoped docs in a in a Google Doc. And so that’s so then I, you know, I started refining my partnership and sales skills. And so it was a very natural evolution. And it was largely built out of necessity to make money.

Interesting. So if you had a company that was supporting your five member team, you’re working with these big clients like Nike and Ge, why did you end up going and working for another business? Yeah,

so agency work is tough. Again, consulting is tough. And so I loved the creative aspect of it. But having to find the next project every month, or every couple months. It was really draining, and I wasn’t enjoying my life, like I was living in San Diego is beautiful, I could walk to work. But honestly, like, when I when I stepped back, I wasn’t enjoying my time, because I was doing things that I didn’t enjoy doing. And I spending more of my time on like the business development of an agency, which I really didn’t enjoy. What I really wanted to do was when we scratched our itch, but I wanted to live off of a product. So I wanted to have a product that I woke up every day and improved. That was my goal. And that’s why we built Brandis D, we built bilingual child, which is a language learning application for kids. And that was all in an effort to try to quote unquote, set ourselves free from the consulting, I reached a point where I just didn’t want to do it anymore. Where I just I dreaded walking into the office that we had built. And I realized at that point I needed to change. And so that’s that’s when I decided to walk away from

it. Was there a mentor or a support system that you kind of called on while you were making that decision?

Yeah, so I was doing the podcast, rocket ship. And I started that about eight months, you know, before I and we were building brand dusty, and, you know, we had this kind of startup dream there. And so I was building my network through the podcast because we were doing two or three interviews a week with people that we really admired a lot of people that were in San Francisco at the time that we looked up Up to. And so I had calls with Heaton Shah and some of the other people that really inspired me to take the leap. But also I realized how much I needed to learn. Like I would get on the phone with Heaton. And I would have three or four pages of notes in 10 minutes. And he’s just standing outside of his office is nothing to him. This is just like, like, second, he just knew it. And, and yet, I’m just scribbling down tons of notes. And I realized that there was so much for me to learn. And to do that I really needed to be dedicated to building something, and really kind of going deeper than you’re able to go as a consultant.

And talk to me about how you wound that down. How did you make that leap from running a consultancy and trying to start products on the side to transitioning over to, to a product is it as graceful as it sounds?

Never that great. But, but the the guys I was running the agency with, they continued on with the agency. And I went to Vegas and joined an incubator program in Vegas, and started a company with my friend who had recently left Google. And he was a developer there at at Google. And he was kind of in transition as well. And so we started a company. We worked on it for about six months, but we couldn’t quite get it to where we wanted it to go. We were happy kind of taking the next step.

Talk to me about that decision. Because it’s probably easy to say now, it probably wasn’t easy to say back then when you’re six months in of probably pulling late nights and weekends to make something work. How did you make that decision to close down before committing another 612 18 months

ago? Well, I mean, part of it was I kind of run out of personal runway. And part of it was I could see that we had another 12 months till we could go to market with what we wanted to do. And we weren’t making fast enough progress as a two person team. You know, it just us working together at that time just wasn’t quite. We weren’t working fast enough. And so while I wanted to continue doing it, when I looked at it, I felt a burden that I just I didn’t see a way out of and so it just it was a safe time to kind of call it quits. And he’s gone on. And he has his own startup, and they’re doing phenomenal. But I think for me at that time, maybe it was because I was still burnt out. But I really just wasn’t able to get kind of get over the hurdle and do what I needed to do for it. And I knew that and so it was just the right decision.

How was your relationship with your family at that time?

Probably better than ever since I left when I was at the agency, I was not happy. And so once we moved back to Vegas, when I left the agency, and we we, I really was able to spend more time with my kids and my wife. And so we were we were in a really good spot. And I also didn’t want to lose that, you know, I just had a second child who was just born. And I didn’t want to lose that time. And that’s just a personal decision, I think. But I knew that if I was going to do this and make it a success, that I probably would be giving up the same amount of time that I had given up for five years. And for me at that moment, it wasn’t the right thing.

Well, it’s pretty awesome that you were able to have that perspective and experience going into it. Just because I feel like so many founders, or at least first time product founders don’t have that experience, have already done something entrepreneurial, to know what it feels like when you are, you know, running at, you know, redlining at all times, you know, month after month after month, and how that can compound. And so it’s cool that you were able to almost design, it sounds like you almost designed the business and your role in it around the lifestyle you wanted to have.

Yeah, yeah. And I think knowing when, like, knowing when to either walk away, or knowing what you’re getting into is really important. Right? So like knowing that this is going to be a lot of time. And is this the right time in my life to do it. Not that it won’t be in five years, right. But But at that moment, it just wasn’t the right time. And at that point, I did have some mentors around me that I was able to bounce this off of as like a pretty good sounding board. And so I knew I knew I was making the right thing for my gut.

When I think about your career, and sort of how you went from consultancy, to product company to then going in and jumping in as an employee. I imagine. It took some sort of changing your identity once again. It’s true to really take that on can you Talk to me about the internal self talk that was going on there and the mental preparation you had to do. Yeah. So

when I like so I kept up with McHale, the the CEO and founder of group, I had kept up with him since he started as for about two years, so I had started Brandis at around the same time that they had started booth. And I was just had a ton of respect for him. And he had reached out when I left the agency and said, hey, you know, I’ve got this partnership position, you know, let me know, if you’re interested, we talked about it a little bit. And then when I was shutting down, like the kind of interim startup, I reached back out to him again, but I knew that when I was going to take the position, I while I had been kind of the leader, up until that point, I knew I my role now was to support him, you know, make his life easier and saw and take off his plate, the things that that he needed, so that he could go out and raise money or work on the vision and do some of the bigger initiatives that a CEO needs to do. And the hardest thing at a startup is, is wearing so many hats, and the founding team wears a ton of hats, they do marketing, they do sales, they do everything. And so I knew my job stepping into that role was to make his life easier, right or, or give him back some of the time that he needed to continue to build so that we could reach the next level. And so I still had kind of a leadership role inside of the team, I definitely had to kind of take on the perspective that for the next couple years, I probably won’t be the leader, you know, and I’m gonna have I fall in line and do my best to make this company success. I already kind of loved the idea of crew and the mission. So it really wasn’t that hard. But there definitely was a very purposeful acknowledgement that I might not do everything my way.

Sure, that’s probably a good reminder to yourself, before you get yourself into any sticky situations in the new role, but the

thing is, people are growing like he had grown a business bigger than I had. So I had a ton to learn to write. And so when when we when we’re open to not doing everything our way, I think we’re also open to growth, so to and to learn from people that are doing it maybe slightly differently than we would, but learning what that looks like and what that feels like and what the results of that are. So I was excited.

Well talk to me about the business at that time. You know, well, first of all, maybe give us, obviously, our listeners heard an introduction, what crew is all about and what they do, but I’d love to hear it from you, Michael, because I’m sure that you have a different spin in your own flavor of it. But also maybe give us an idea of where the business was when you jumped in.

Yes, so we basically project match between freelancers and project owners for web, web and design projects. So we have a vetted network of designers and developers and we have people with ideas or projects or companies that need to hire that come in, and we help to match them up. And the real goal is to help solve some of the problems around the freelance community and make it easier for people who are freelancing, and to build trust with people who are hiring freelancers, because I come from being a freelancer. And I know a lot of the stress that that it’s like when you are a freelancer, you need to find constant work, you need to find good work that pays you enough. That takes up a lot of time. And when you’re hiring freelancers, you oftentimes they disappear. They’re they’re unreliable, or the word quality varies. And so that is why we exist is to help fill that gap. And so when I joined, we were 14 people. And we were a big like we were largely reliant on content marketing. So, McHale was able to write huge blog pieces that spread, and we get picked up and syndicated. And that’s where a lot of our inbound interest came from.

Now, I know that the company is headquartered in Montreal, Quebec. Does that mean that you relocated there, or did you work remotely?

I was remote. I just relocated about a month ago.

Okay, great. So you’re up in Montreal now? Yeah, that’s great. Well, we’ll dig in and a little bit on the tech community there. I’m not sure if you’ve had a chance to plug in yet. But we’d love to get kind of your perspective there. Totally. Yeah. But it sounds like you had kind of a cool opportunity there getting in so early. When there’s just 14 people, the company is still kind of growing and getting its traction with some of the content marketing had Unsplash already been launched at that point.

Yeah. So we had Unsplash was launched, Onslaught actually launched when it was still just the founders. And so Luke, Luke Chesser, who, who has led Unsplash for for the last two or three years, he he was one of two or three people that we had on at that time that were fully focused on Unsplash but he’s always been focused on Unsplash. Okay, and tell me about the problem that Unsplash is solving?

Yeah, so Unsplash is royalty and commercial, leave free licensed photos. And so it was designed to help with that splash page. So What image do you use on your splash page to get your website up quick, because crew was building landing pages, right? So that’s, that’s where it started. And now it’s it’s ballooned into, essentially stock free stock photo for all types of use cases. We’ve seen them on billboards, we see them all over the web. Most major companies have published something within Unsplash photo. And so that has become and we can talk about that. But that’s become its own its own beast, essentially. And it’s growing. It’s like the third fastest growing photo sharing company. I think today.

That’s incredible. And I definitely want to dig in on that piece. Because I think it’s so fascinating how sort of an intrapreneurial endeavor that started within crew is now is now scaling up into something bigger than maybe even potentially bigger than crew.

I think it’s safe to say, Yeah,

that’s amazing. That’s amazing. So talk to me about how you how you kind of plugged into that. And what were you doing at the time when you join when it was just 12? People?

Yes. So when I first joined, I was brought on to lead our partnerships. And so we initially it was a lot of business development, really, we had a couple of kind of hypotheses about who we could partner with. So we’re talking a lot of agencies freelancers, seeing how we can get a referral program going. And we learned a ton the first year, and then the second year, it was more on the company placement side. So it was it was very outbound sales. So we’re talking to companies and large agencies who need to scale up and down and doing like, almost direct sales to them. So partnerships kind of became sales. And we saw some huge growth from there. And we really learn to work customer was by actually going out and talking to them, which wasn’t something that we had done much of before. We knew that if we put out great content, people would come. But we didn’t always know who they were, why they were coming, why they were basically using crew to source freelancers. And so those were some of the big lessons that we learned simply by just doing old school sales. And that’s what I did for the last year before stepping into a president’s role.

As you were doing the sales side of things. Were you doing it solo? Are you part of a team? Are you leading a team?

Yeah, so I started off solo. And so I was very much like, outside of a lot of what the company’s initiatives were. And so I would set my own goals and my own initiatives, essentially what I’d be focusing on, and I’ll try to bring as many of those lessons back from talking to people to the team. And then eventually, I was managing kind of my own my own initiatives, with people’s part time. So people would kind of dedicate part of their day to this sales initiative. And then we did grow a team, a small team of salespeople that worked under me. And so that was that was the most recent iteration was we had a dedicated team to sales because we were bringing in 40% of our revenue from this small sales team.

That’s incredible. Is this all self funded at that time? Or were you guys raising your seed series? Or even your series? I know you’ve, you’ve already raised your series A now but when did all of that take place?

Yeah. So when I was brought on, we were just closing the series A and I think we announced it like six months later. So at that point, we had raised the 14 14 million total that was that the last round was about 8 million.

Awesome. Well, it seems like a really cool ride, riding up through the sales ranks, and ultimately to the president position. I mean, the the story can’t have a better ending than that. Right? Except maybe, you know, if and when you haven’t have an exit, right? Talk to me about how you navigated that, when did the that opportunity even present itself? Did you go into the sales role, knowing that that path was going to be available?

No, no, I mean, you go into a startup, you don’t really know how the company is going to shape. And so for the longest time, like I eventually, I was leading a small sales team. But it was always unclear if we were going to go down a heavy sales path, or if we were going to go down a marketing path. And, and so it was never, we never had a clear path for where I could grow, I guess. Right. And that’s, that’s very typical in startups, because you’re really trying to figure out the business model. And then when you find something that works, you invest in it more. And we had just kind of figured out that sales could work, but we weren’t quite convinced that sales was the way to scale because then you’re just scaling more salespeople. And for a business like ours is doesn’t always make sense. So we were still kind of debating that. But what we did see was Unsplash was growing like crazy. And it needed its own dedicated leadership. And so the board made a decision that it made sense for McHale and Steph, who’s our COO, to focus 100% of their time on Unsplash. And then the question was, what do we do with crew? And so, about two days, this is about two months ago, but two days before the board meeting, they came in and asked if I would step up into it, like a General Manager, which became the President’s position. And two days later, I was in Montreal, pitching to the board, our 2017 plan. And for the last for the last two months, we’ve been doing a lot of that planning for 2017. What are we going to do? What is this company going to look like? But it was all it all happened really quick. And it was all it was all built out of the problem that Unsplash needed focus and, and crew needed to continue being crew. And so they felt that this was the best solution without leaving either company in limbo,

that had to have been a crazy moment when they first offered that position to you, or were you expecting it?

No, not at all. I wasn’t at all actually, we were preparing to move up to Montreal independent of that. And so I was actually more focused on kind of getting my partnership stuff rolling for q4, because I knew I was going to spend a lot of time on the road, moving my whole family up to Montreal, I was living in Vegas, so we’re literally moving across the continent there.

Talk to you about how you’re feeling at that time, when you got that offer, what what was going through your mind


good stress or bad stress.

I mean, it was really exciting, obviously, right? Like I was incredible. I had I had followed this company from its infancy when they were just four founders joined it when they were 14, and now had the opportunity to lead kind of the next version of it. So I mean, that part of me was incredibly excited. And then there was the other part of me, which is like, Alright, now I actually have to lead this company, which I have a ton of respect for. And then there are those planning and you know, the the board meetings and everything else that you have to do that comes with leadership. And you move out of your what you’ve done really well at, you know, we were bringing in 40% of our sales from direct sales. And now, we don’t have anyone to fill that role. And I have to step into a new position. So figuring some of those things out can be I don’t know, a little worrisome. But you get through it. Right. And so that was my initial, my initial reaction was, how are we going to keep doing what we’re doing when I have a different focus?

So you kind of went into problem solving mode, and tried to stay pragmatic through that whole experience?

Yeah, while driving across the country in a Penske, which was a

bold move.

Probably not my best decision in life. But um, yeah, that was, that was it.

That’s incredible. So talk to me a little bit more about that transition, because I imagine you’re not only having to deal with handing off things from the sales side, and recruiting someone in, but you’re also needing to learn, you know, a little bit of the leadership side, obviously, you’ve been shadowing or, you know, paying attention to how these co founders were running the business previously. But what needed to shift with you again, you know, we’re talking here again, yet another identity change for you. Yeah. Talk to me about what helped make that shift in that transition, that clearly, you’re probably still making, considering the news was just announced, you know, less than a week ago.

So yeah, so I think what made it real was sitting down with the board and starting to have a real discussion around where we could go as a company, and actually having holes poked in some of the assumptions that I already had. And some of the initial ideas that I had for where we needed to go. And so I think that really made it real. And having that sounding board is is really crucial. With crew, we already had a lot of that infrastructure set up. But so we have people who have been with the business and invested in the business for the last couple of years. And so they know us really well. But what sitting down with them made it real. For me, personally, you know, we’re a distributed team. And one of the biggest struggles that I have is leading from the inspirational side, a team that’s not in the same room. I’ve always led teams that sat down together, and I always found it easy to have those discussions. But with a distributed team, it’s hard to have those deeper planning sessions and then also kind of build rapport with each other. So that’s something I’m still figuring out but something that I really want to get better at is actually being able to To inspire people through a video, you know, a video chat, which is a lot harder than I thought it would be?

Absolutely. What are some of the things that the co founders did to run that distributed team effectively.

So they, they gave a lot of, I guess, autonomy to everybody, which I think is good. And then they allowed, they set up team leads that then handled a lot of the day to day. And so they set up some great infrastructure, we use Trello. With the new move, we switched over to Basecamp. But a lot of good processes and Trello for communication and using Slack only for very specific types of messages. And they’ve always been very keen on people’s time and distraction. And so using Trello, or Basecamp, to make, I guess, requests, knots feel so urgent, is really the important part. So people can do that focused work. And they’ve done a great job at that, because people are in all different times of their day, when they get in some people get in the morning, and they want to get all those tasks in. But maybe someone that they’re talking to is at the end of the day, and is trying to do the focus work so they can wrap up. So being very cognizant of that is something that is a message that they continually reiterated and really tried to master, I think we’re at a pretty good point now where people can collaborate well, you know, McHale is a phenomenal leader, and trying to step into that role, where he can really inspire and bring that kind of inspiration out of people. And I think, kind of filling that role has been the hardest part, when you step in, you have someone who people, everyone works at the company because of him. And you know, he’s not in our day to day now. And I have to be that and so that that is something that I’ve really been trying to work on.

I imagine all of your interviews that you’ve done with rocket ship FM over the years, have been immensely helpful with some of the roles you’ve taken on? What are some of the lessons that you’ve learned in those conversations that you’re looking forward to implementing in this new role as president?

That’s a good I mean, the biggest thing I’ve learned from from interviewing so many people is that no one really knows what they’re doing in this role, which I think is it kind of gives me some, I guess, resolve, in that a lot of us are still figuring this stuff out. And that. And that’s been not everyone who we see who we read has all the answers, and they’re still struggling with things in their own businesses, they still have problems inside of their own business that they don’t necessarily know how to solve, but they’re trying to. And that kind of sounds like a cop out. But that has been probably the most reassuring thing is that it’s okay to not be perfect. And that I can I can make mistakes, as long as I’m trying to better them. And being able to kind of take a step back and acknowledge those mistakes, and work on those specific skills, but you don’t have to have every skill all the time. And I think we kind of missed that we try to be perfect in every way. But it’s okay to be good at what we’re good at and lack in some of the things that we’re not as good at.

That’s really good advice for any entrepreneur. And for me. I really enjoyed Michael falling your entrepreneurial journey, you know, on medium and through rocketship FM, and I’m sure you’ll continue to do that. Maybe even more now that you’re in the president role, and needed to do a little more of that vision casting. Where can people find you? Obviously, rocket ship.fm is a good good place for the podcast.

Yeah, you can you can hear me at rocket ship. FM I’ll be be blogging@cru.co and on medium at Michael Sokka. Follow me on Twitter at Michael Sokka. And if you have anything specifically you want to talk about, shoot me an email michael.sokka@gmail.com

Well, you have so much experience playing so many different roles in so many different kinds of businesses at various stages. I hope a lot of our listeners take you up on that. You know, before we close, I always like to learn a little bit about where our guests are calling in from and I would love to learn a little bit more about the tech and entrepreneurial scene in Montreal.

Yeah, yeah, absolutely. So I’ve been in San Diego I’ve been in Vegas when the the kind of downtown scene was rising and falling. And then in Montreal, it’s it’s an interesting tech scene because we have we do have some very stable companies and Frank and oak and Shopify that are nationally recognized. And so there’s a lot of momentum behind the startup scene. And we’re also very close to New York. So a lot of the the The investment while there isn’t a ton of of investment necessarily at the larger stage of that series A in Montreal, it’s accessible. It’s right over, it’s an hour flight into New York. And so you see a lot of us investments in, in these Canadian companies, at least, it seems I’ve only been here a month. But it seems like there’s a lot of cross border involvement, especially with the the Canadian dollar being a little bit low right now. And so, US US investors can their money goes a little bit farther when you invest in Canada, the Canadian government also gives like, they match up to 250,000 of your initial raise. And they have the BDC, which is a basically a venture arm of the government, which helps to work with a lot of these local companies, and give some infrastructure to the community, which is something you don’t necessarily see in cities outside of San Francisco, in the States. So I think it’s pretty exciting. Right now there’s, there’s a lot of talent and the fact that we have companies that are succeeding, and hopefully those founders will exit and come back and invest in Montreal, again, it seems very hopeful and a little bit more hopeful than some of the other cities I’ve been in.

That’s actually really, really good to hear. I knew of, you know, a few of those companies that you mentioned, obviously, we’ll be paying attention to how that tech and startup community continue to evolve. I’m excited for that. But I’m even more excited for you, Michael, as you’re stepping into this new role in the huge opportunity, you have a crew, I’m sure a lot of our listeners will be following your journey, as well. Thank you so much for taking time to be on the show.

Thank you, I really appreciate it. Of course, man.

Hey, it’s your host, Matt Hunckler. Here again, that’s it for our hangout with Michael Sokka on powderkeg. But the party does not have to stop there. Please make sure you follow Michael on Twitter. He’s just at Michael Sokka. And that’s Michael S a cc a hit him up on Twitter, let them know what you learn. Just say thanks for being on the show. You of course can learn about his company crew@cru.co, as well as on his podcast, rocket ship FM at rocket ship.fm. You can get the full show notes, the transcript, everything else you need, like links and resources on our website powderkeg.co. You can also find some of our other guests that have been on the show, I think you’re gonna dig some of the conversations if you like this one, you’re gonna love some of the other ones that we’ve got there for you. I just wanted to remind you real quick that powderkeg is presented by verge which is a network of local communities with global reach for tech entrepreneurs, investors, and top talent growing companies beyond Silicon Valley, we have a ton of free resources for starting and growing your business at Virge hq.com. We also host several events every month around the country. So check us out and see where we’re at, I would love to link up with you in person, learn a little bit more about what you’re working on and how we can help. So again, that’s verge hq.com. And of course, you can always find me on Twitter and Instagram at Hunckler. That’s at hunc K L E R, I appreciate all of your feedback, all the conversation and dialogue there. Thank you so much for continuing to give great feedback, great ideas for future shows. And of course, let me know how I can help. I want to help you. I want to help your business. And I want to help make this podcast better and better. So that again, we’re helping more and more people. The more interviews we do, the more episodes we have. So thanks to everyone who has done that. And of course, thank you, thank you. Thank you to everyone who has left us a review this past week and subscribed on iTunes. You can leave us your honest review by using this link powder keg.co/itunes Please give us a subscribe while you’re at it. And we’ll be forever indebted to you. Because it’s your reviews. It’s your subscriptions and your feedback that helps us get better and reach more people to build bigger and better businesses that really matter. Thank you so much for tuning in.