6 min read.

The CEO of my first startup was a competitive rower in college. One of his teammates, who went on to compete in the Olympics, started a management training course that integrated classroom discussions with lessons on the water, rowing with a team. Our executive team attended one of his sessions. There are three lessons I took away from it that have stuck with me and feel especially important given the tough year we’ve had and the uncertainty that all companies continue to face during the pandemic.

Lesson 1: Set the right pace

In one of the first exercises, the facilitator put us all…


Today we announced that Skillshare has raised a $66 million Series D funding round, led by OMERS Growth Equity. The last few months have been pivotal for the company, and like everything else in 2020, the path to funding was full of surprises. I wanted to share a few lessons learned from the process.

The value of focus

This isn’t necessarily a new lesson, but it was a valuable one to reinforce nonetheless. When I joined three years ago, Skillshare had pivoted away from its in-person teaching model several years earlier. We were using our open platform to teach as…


Like many business leaders, we’ve watched the COVID-19 updates closely and, after reading calls early this week for NYC companies to work from home, we decided to initiate a work from home policy for all Skillshare employees through March 27. We want to do our part to reduce the spread of the virus and keep our teams, families, and communities safe.

Though Skillshare isn’t a fully remote team, we do have some practice working from home. Twenty-five percent of our workforce is already distributed across the world, and every Tuesday our NYC staff works from home. …


At Skillshare, we’ve always wanted to be a community that embraces and supports what people care about most. Over the past decade, we built an entire pedagogy and product around the idea that learning isn’t about doing a specific thing a specific way but about learning how to think, practice, and adapt a process to your unique real-world dreams and goals. It’s always been, and will always be, a community for empowerment.

One of the things that started to emerge a few years ago, however, was that there are a lot of places on the internet sharing knowledge. …


The Skillshare team in a recent design sprint

I have the opportunity to meet with other CEOs on a pretty frequent basis. I’m part of a CEO group in NYC that meets monthly for breakfast, attend a few other networking groups that meet several times a year, and each of our investors has an annual portfolio company meeting. A consistent topic of discussion and sharing of best practices is the cadence of how we run the business — annual/quarterly/monthly routines, planning, communications, check-ins, goal setting, etc.

The focus of this post is how we run Skillshare today. I want to emphasize today, as we regularly tweak and update…


Many companies are looking for ways to level the playing field in the workforce but often struggle with what policies or organizational changes to make. Bpeace recently recognized Skillshare as an employer who has made progress in this area. We still have a lot of work to do, but I thought I’d share 7 changes we’ve made to level the playing field at Skillshare and provide a better work experience for all our employees.

1. Flexible Working Model

We’re flexible about our employees working from home. Our philosophy is ‘do what you need to do and be an adult, and…


A guide for how many options a startup should grant, and how potential and current employees can evaluate their option value.

One of Skillshare’s core company values is transparency. We share as much information as we can with our team: metrics, financials, long-term vision, challenges. I’m a firm believer that the worst thing you can do is hide information from your team. This doesn’t mean you share everything — our employee reviews don’t get posted on the refrigerator, and there are situations where you can reach information overload. But whether in business or life, when you find yourself hesitant to…


Skillshare Headquarters in NYC

Occasionally I read a tweet or post about how hard it is to be a startup CEO, and how it can be very lonely at the top. I have a pretty visceral reaction to that because first, you are a CEO; nobody feels sorry for you. And second, if you’re doing your job well, it should never be lonely. Here’s how to make sure you’re surrounded by people who can help you make tough business decisions.

Hire The Right Executives

I learned early on the value of a strong executive team. At a company I used to work for, our…


The popular media narrative around the gig economy is that it’s just full-time work, minus the benefits and stability. Unfortunately, that is a narrow characterization as a result of viewing freelancing through the traditional lens of full-time employment with a single company.

While some people see risk and instability, many of the 35% of Americans who are freelancing see the freedom, opportunity, and an improved lifestyle that comes with being an entrepreneur and business owner. …


Image via: Pexels

Buzzwords like “digital nomad,” or “remote worker,” are indicative of something bigger. Currently, freelancers are estimated to account for 34% of the workforce. By 2020, that number is set to reach 43%. Freelancing and gig economy work is often painted as the job of last resort, but people are voting with their feet: freelancing is growing rapidly while 6.6 million traditional jobs remain unfilled, an all-time high.

Employers looking to hire full-time employees are no longer competing with other full-time offers but with the flexibility, freedom, and accountability offered by freelancing and gig economy work . …

Matt Cooper

CEO of Skillshare

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