Matt Cooper is in the business of enabling jacks-of-trades. In 2003, after leaving his investment banking job in New York and relocating to California, he landed at a startup that sold recruiting services to venture-backed companies in Silicon Valley. In 2008 he moved on to run operations at oDesk—the freelancing platform now known as Upwork—remaining there for five years before becoming the CEO of content creation platform Visual.ly. Cooper’s tenure at the company ended shortly after the platform was bought in early 2016, and he joined Skillshare as COO in November and became its CEO a year later.
During his career building and running freelance platforms, the gig economy exploded. Defined by the rise in popularity of short-term freelance work, or “gigs,” its growth enabled to professionals to eschew full-time roles for project-based work. The style of working became popular among designers, writers and engineers (and many other deliverable-based roles), and by the mid 2010s, companies—particularly ones with limited resources—were tapping into the scores of workers available to work on online platforms.
Cooper and Skillshare have been at the center of the gig economy, offering critical educational and skill development support to people looking to either hone their professional skills or break into the gig game altogether. The pandemic, which required companies across the globe to quickly get comfortable with remote work, may have helped further accelerate the trend by proving to those who had yet to embrace it that productivity can remain high no matter where employees are located—a truth that many gig economy participants have been familiar with for years.
As part of our Office Hours Q&A series on @AmericanExpressBusiness, we asked Cooper to share his insights on the future of self-learning and the gig economy as well as how he and the company were able to raise their Series D despite the lockdown.
SaaS and digital startups have opened up new disciplines through the tools they’ve created – in the modern era, the creatively inclined have been able to turn to Skillshare to learn professional skills from site and UX design to animation, illustration and editing. What self-learning professional disciplines do you think will emerge in the next five or ten years? What tools will people be turning to Skillshare to learn them?
Many of the creative skills that members have been coming to us for, like UX design and animation will still be popular and useful in the workforce in the next 5 to 10 years. Much of the foundational elements of these careers and skill sets will remain important. Increasingly we’re seeing more employers value creativity as a skill in the workplace. Creativity is among the top three skills workers will need.
Traditionally, business education has been delivered formally through universities or MBA programs. Do you think the rise of instant-access education and comfort with the digital-first approach of our new normal will evolve business education? Do you see it ‘democratizing’ it, especially for entrepreneurs and small business owners?
Yes, we are bullish on the idea that digital-first approaches to education can democratize access, and is increasingly practical for entrepreneurs and small-business owners. We now have over 30,000 classes for a $99 yearly subscription. If you are looking to add certain skills to your entrepreneur’s toolkit, you really can’t beat that deal.
Continued learning is an extremely positive activity—both personally and professionally. Learning is good for your brain, self-esteem, and emotional well-being. When we master something, it’s extremely rewarding. By taking the time to invest in personal or professional goals and dreams, you’re practicing self-care.
—Matt Cooper
Despite the lockdown, Skillshare was able to raise its Series D during the pandemic. Can you explain your approach to raising money during a period of extreme uncertainty? What were your conversations with investors like, and what did you find resonated most as you progressed through them?
Skillshare was cash-flow positive as we were out raising the round, so we were approaching the funding raise as an opportunity to accelerate our already-healthy growth. Our goal was to find an investment partner who supported our mission and vision and whose values and culture aligned with those of our existing board.
Raising a funding round during a pandemic was without a doubt challenging, but it was also a rewarding experience. To find the right partner, we met with a broad swath of venture capital firms - 65 in total to be precise. The pandemic and inability to meet with investors face-to-face actually enabled us to cast a much wider net than we could have pre-pandemic. It allowed us to introduce Skillshare to a significantly larger audience, drum up awareness and use those introductions to plant valuable seeds for the future.
Admittedly, I had some concerns about raising a significant round virtually, including whether we’d truly be able to get to know our investors through a screen. But in fact, Zoom made the experience more personal, not less. We skipped a lot of formalities that are more draining than productive. And it turns out you can learn a lot about someone based on what’s behind them in a video call in their home versus the sanitized environment of a big VC boardroom. Behind my desk, I have a wooden surfboard mounted on my wall which I built and shaped by hand (looks awesome, rides terrible) and it turned out to be a great icebreaker. Like me, every investor had a stamp of personality — photos, bikes, art, kids — in their home offices that helped us to build rapport right away.
It made the experience that much more human and deepened our connections in ways that wouldn’t have been possible pre-COVID. We really got to know our investors on a personal level, giving us a fuller idea of who we’d be adding to our board. We wanted someone who already fit the mold of the rest of our board: strategic, generous, and proactive.
In terms of what resonated most with our prospective investors was the overall health of our business and our pivot to focus on to be a market leader in creative learning. Additionally the fact that we have pockets of new member bases popping up in different corners of the world, without having spent marketing or advertising in those markets, was appealing to investors. International expansion is a key priority for us going forward and that struck a positive chord with investors.
As more and more people turn to Skillshare to learn, more and more will be needed to teach. What data do you use to determine what new ‘courses’ your team seeks to fill, and what’s the process for finding and vetting the right teachers? Do you find learners are willing to embrace teachers even if they lack certain certifications or credentials?
Our teachers are creatives, entrepreneurs, and professionals who are great at what they do and passionate about sharing their skills with others. Each has a unique background, perspective and teaching style and that in itself if appealing enough to our members. When you can see their work and hear the depth and breadth of their expertise, that’s the most important credential. Our most successful classes teach a creative skill with a real-world application. Specialized classes that teach a distinct skill tend to be the most popular.
Looking more closely at the data tied to content, we track value by campaign and by real metrics, like views over subscribers/followers, sign ups instead of clicks, and through the conversion to a paid account to look at actual revenue impact. We have data on 10,000+ campaigns that we leverage to dictate pricing and where we want to make long term investments - whether it be a specific skill / vertical or a teacher personality. We can also use this data to determine which types of videos have better chance of success (categories, video length, titles, thumbnails etc).
Lastly we also built relationships with thousands of creators and agencies that have given us a ‘first mover’ advantage. We often get a first look at a lot of new opportunities and personalities before others.
Finally, what role do you think learning plays in self-care? Why do you think many of us are constantly looking to be intellectually and creatively challenged, and how do you think that evolves in the future?
Continued learning is an extremely positive activity—both personally and professionally. Learning is good for your brain, self-esteem, and emotional well-being. When we master something, it’s extremely rewarding. By taking the time to invest in personal or professional goals and dreams, you’re practicing self-care.
Through the pandemic, we also heard anecdotally from members that they were feeling discourage or frustrated. Doing something creative was a way for them to lift their spirits and do something productive. Doing something creative that involves actually creating something – like baking, drawing, doing a puzzle, etc – is like revving the engine of your mind. You’re shaking off the cobwebs and getting your brain moving. Creative activities can also be a stress reducer.