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How to create a fantastic work culture, with Matt Cooper and Chaya Weiner

You can’t over communicate — So many issues in a company are due to poor communication and a lack of alignment. We try really hard to keep everyone on the same page — weekly newsletters, weekly all-hands meetings, frequent internal blog posts, weekly metrics and operational meetings, Slack channels, etc. It takes a LOT of effort to keep everyone […]


You can’t over communicate — So many issues in a company are due to poor communication and a lack of alignment. We try really hard to keep everyone on the same page — weekly newsletters, weekly all-hands meetings, frequent internal blog posts, weekly metrics and operational meetings, Slack channels, etc. It takes a LOT of effort to keep everyone aligned, but it’s worth it.

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Matt Cooper is the CEO of Skillshare a company with a mission to connect life-long learners everywhere and build a more creative,prosperous, and generous world. Before joining Skillshare, Matt was the CEO of Visually, an online marketplace for creative work that was acquired by ScribbleLive in January 2016. Prior to Visually, he served as the VP of Operations, Enterprise and International for oDesk (now Upwork), the world’s largest marketplace for online work. Matt is a father of four amazing girls and spends most of his non-working hours driving them around in circles to their various activities. In his rare moments of free time, he enjoys surfing, fishing, running and anything outdoors.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I ended up in startups after working in banking, but when I think back I’ve always had an entrepreneurial bent. One of my first business ventures was building garbage racks on my neighbors’ fences. Back in Texas, before we had the big plastic garbage cans, we would just set our garbage bags in the back alley behind our house. Inevitably, dogs or raccoons would make the rounds, rip open the bags and spread the garbage all over the alley. I started building wooden racks on people’s fences to keep the garbage off the ground. Our family’s cocker spaniel, Tuggles, had a particular love of garbage. She turned out to be my best business development representative.

I continued to find myself as an entrepreneur starting multiple businesses. I went on to run a landscaping business in high school with my two best friends. After college while working in investment banking, I briefly had an event planning business. Before moving to California, I started a canoe rental business in southern Mississippi with my uncle (which failed spectacularly). In 2002 I quit my investment banking job to move out to California with my then girlfriend (now wife) and after 9 months of being an unemployed former telecom banker, I officially took the plunge into the Silicon Valley startup world and have been on that path ever since.

Can you share the most interesting story that happened to you since you began leading your company?

When I joined in late 2016, the company’s growth had plateaued so we started testing in paid marketing channels. Happily, we were seeing some success so in early 2017 we began to fundraise for our Series C. Michael (the founder) and I pitched 113 different venture capital firms, and received 0 term sheets. We were growing aggressively, but it was still early and none of these investors believed we could continue at this pace and do so efficiently.

After 6+ months of fundraising with no luck, I caught up with one of our existing investors, Albert Wenger from Union Square Ventures. I mentioned that from December to April our revenue had grown 30% and we were tracking ahead of our aggressive growth plans. He asked me to come in and pitch his partners again and give them the update. I spent almost two hours fielding rapid-fire questions from Albert, Fred Wilson and the rest of the USV partners. I was on my way home, completely exhausted, when Albert called to tell me they were going to use their opportunity fund to lead what ended up being a $20 million Series C. After talking to 113 firms, the investor who knew us the best and believed in our mission was going to lead the round.

It was a great day for Skillshare and it reinforced just how valuable it is to have a great set of investors around the table. We are really lucky to have investors like Albert and USV on our side. We beat our 2018 projections, by the way ;-).

Are you working on any exciting projects now? How do you think that will help people?

One of the reasons I joined Skillshare is the direct social and personal impact our product has. We often hear from members telling us how our teachers and classes have helped them find professional success and personal fulfillment. It’s a great feeling to know that pretty much everything we do to improve our product and user experience is helping people in a very tangible way.

That said, although there are a number of initiatives I’m really excited about, the one that comes to mind is our focus on the community aspects of our platform. Sure, you can take online classes from experts in their field, but we also know there’s incredible benefit in connecting with other students in the community. We’re building out more ways for members to connect, interact, get and give feedback on student projects, work together via Workshops and discuss topics of interest via discussion groups. Seeing the direct member-to-member interaction is a lot of fun.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

When I think about the times when I’ve been the most unhappy in a job, it usually boiled down to a lack of ownership, control or impact. My guess is that I’m not alone. I think it is really hard to feel good leaving the office every day if you don’t feel like your work matters, you don’t have the context of why you are asked to do some of the things you do, or you don’t feel like you are empowered to do the right thing and make a difference. Unfortunately, a lot of companies and managers don’t create a culture where ownership and impact are valued.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

If you have a team that is doing the bare minimum to get by or doesn’t really enjoy their work, it’s pretty obvious in the business results. When your employees are happy, enjoying the work that they do and have real purpose, you can see the results in the numbers. Our personal and professional lives are too closely linked for unhappiness not to bleed over which makes employee health and wellbeing critically important. It’s hard to be effective at work if your personal life is a mess, and it’s hard to go home and be a great parent, spouse or partner if you are miserable at work.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

1. Be transparent — This is something that is particularly important to me — we are very transparent about our goals, metrics, financials and challenges. With the whole team, we share our full financials every month, review our core business metrics every week, and we are crystal clear about what’s going well and where we need to improve. I teach an internal lunch and learn about how to read financial statements so that when we put the numbers on the board, everyone understands what they are looking at and what it means for the business. If everyone in the company knows how our business runs, understands where we get financial and operating leverage, and recognizes our biggest challenges and risks, then they are going to make much better decisions in their day-to-day roles.

2. Focus on impact — So many companies make the mistake of rewarding activity over impact. At Skillshare, we don’t care how busy you are or how many hours you are working — we care about the impact you’re driving for the business. We can work 24/7, but if the important financial numbers aren’t moving then we’re not focused on the right things. When we miss our numbers, we take a hard look at why and where we can improve. And when we hit our numbers, we celebrate and recognize the impact.

3. Keep the boat steady — At my first startup, the CEO was a collegiate rower and signed up the entire executive team for a combination rowing and leadership workshop. We did an exercise where there were 4 of us in the boat rowing — our CEO who was a great rower, me (who was good enough), and then two people who were really, really bad at rowing. We couldn’t get our timing right and we were all over the place. At one point the facilitator told our CEO and me to stop rowing and just hold the boat steady, and let the other two people row. The boat actually went faster without us rowing. The management lesson was pretty obvious. There’s a natural desire for capable managers to grab an oar and start rowing like mad, but it’s often counter productive. Oftentimes the best thing you can do is just keep the boat steady and let everyone else pull.

4. Avoid “adding too much value” — I read a post years ago by Marshall Goldsmith about “adding too much value.” He points out that capable managers have a tendency to want to make things better and prove that they can add value. When an employee comes to them with a proposal or idea, the urge is to say “yes, but what if we…” and start to ‘improve’ it. As soon as you do that, the idea starts to become your idea rather than their idea. Even if you are truly improving it, you are also demotivating the employee. The company will likely get a better result if the employees execute on an idea that they are 100% behind, rather than your slightly better idea that they now have no ownership of. Just like keeping the boat steady, sometimes you just need to say, “Great idea, I look forward to seeing the results!”

5. You can’t over communicate — So many issues in a company are due to poor communication and a lack of alignment. We try really hard to keep everyone on the same page — weekly newsletters, weekly all-hands meetings, frequent internal blog posts, weekly metrics and operational meetings, Slack channels, etc. It takes a LOT of effort to keep everyone aligned, but it’s worth it.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

Work is changing pretty dramatically. My dad worked for one company for 20 years, I’ve worked for 5 companies over 20 years, and now people are working for 5 companies within a single year. Teams are distributed, they are global, and ‘work’ is no longer a place. There’s a blending of personal and professional time that makes it hard to distinguish between the two — I work from home on Tuesdays and get to take my daughter to volleyball at 4pm. But you’ll also find me answering emails at soccer games and working on projects over the weekend. I think employers are coming around to the idea of a more flexible working schedule and more employee control over how and when they work, but we still have a ways to go.

How would you describe your leadership or management style? Can you give us a few examples?

I tend to get high marks for being very approachable and direct. I truly believe there is no job that is beneath me and I don’t take myself too seriously. Lastly, as I’ve mentioned a few times in this interview is my emphasis on transparency. These are things I always appreciated in the people I worked for, and I’m very aware of it now that I’m managing others.

Every now and then someone will ask when Skillshare is going to hire someone in IT, and I proudly tell them that we already have someone — me. I installed all of the A/V equipment in the office, so when something breaks I’m usually the one under the table fixing it. When we had a mouse on the loose in the office, one of the engineers and I trapped it behind a cabinet and dispatched it. We had a VP of Engineering candidate in for interviews, and he was pretty impressed. If it needs to get done and it will move things forward, I’m in. I take a lot of pleasure in doing the little things to ‘steady the boat’ for everyone else.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There’s a long list — I’ve had the good fortune of working with and for some great people over the years. My first manager at JPMorgan was Kevin Kelty and I don’t think I could have had a better boss. He worked me relentlessly but really invested in my professional development and truly appreciated how hard I worked. That was a rarity in banking. One of my colleagues at my first startup, Jack Phillips, was an amazing people manager and I learned a lot of the management mechanics from watching how he led his teams. The oDesk CEO, Gary Swart, gave me a lot of opportunity and I learned a ton from him and our amazing management team — Odysseas Tsatalos, Jaleh Bisharat, Greg Stanger, Stephane Kasriel. I’ve been really lucky to work with some really impressive people over the years, and these are just a few of them.

However, if I had to pick one person, it would be my dad. He started his career in the Air Force, and then spent 20+ years in sales and account management with HP. He’s now an executive coach. As I’ve taken on more management responsibilities over the years, I can’t really convey how valuable it’s been to be able to pick up the phone and get both parental support and an executive coaching session in the same call. He knows me better than anyone and he’s great at knowing when to just listen, when to be supportive, and when to tell me I’m being an idiot (in a very loving way).

How have you used your success to bring goodness to the world?

I’ve been lucky to work for two companies that have a very clear social impact. At oDesk (now Upwork), I ran operations, enterprise and international. On the international trips, I would have people coming up to me with tears in their eyes telling me about how their ability to earn a living working for US companies from places like Bangladesh fundamentally changed their lives and opened up countless opportunities for their children. Similarly at Skillshare, we hear stories every day from teachers and students who have been able to completely change their personal and professional lives because of the classes they teach or the skills they’ve learned. It’s a really rare thing to be part of two great businesses that have such a positive social impact.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“You can solve any problem if you can break it down into small enough pieces.” There are so many challenges, problems and opportunities that are just really hard to get your head around when you first look at it. Whether it’s running a marathon or putting a man on the moon, you start by breaking it down into little steps that you can handle and then you start grinding away. Some problems are only solved over generations, but ultimately you keep grinding until you get it done. I happen to really like the grind.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’ve been thinking for a while about the idea of creating a national education endowment fund. The top colleges have billions of dollars in endowments from their alumni — why don’t we have a massive national endowment fund that benefits public K-12 education?

Thank you for these fantastic insights. We wish you continued success!

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