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Matt Cooper

Lessons and Skills Every Entrepreneur Must Have To Succeed – With the CEO of Skillshare

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Impacting Over 4 Million Students With Transformative Learning

With Matt Cooper, CEO of Skillshare

Courtesy of Levi Walton/Viceland

The only way I’m going to survive and the only way I’m going to be successful is if I learn how to get things done through other people. And that means I got to be a better manager, that means I got to be a better coach.

M
MATT COOPER

Matt Cooper is the CEO of Skillshare which has impacted over four million students with over 22,000 plus classes. They believe that learning is transformative – individually, socially, economically – and their mission is to connect life-long learners everywhere and build a more creative and prosperous world. 

In this podcast, Matt talks about his career change from investment banker to CEO of more than one startup company. With his background in finance, it was like a shift from pit mechanic to race car driver.

Before joining Skillshare, he was the CEO of Visually, an online marketplace for creative work that was acquired by ScribbleLive. Prior to Visually, he was the VP of Operations of a company now known as Upwork, the world’s largest marketplace for online work.

His expertise in company operations has given him much insight into building company culture, structuring a team that doesn’t leave the CEO isolated at the top, and how to create a SaaS company that stands out from other platforms.

He’s a father of four girls and spends most of his non-working hours driving them their various activities. When he does have a rare free moment, he enjoys surfing, fishing, running and anything outdoors.

Courtesy of CoFound Harlem

In this episode you’ll learn:

  • How Matt got into the startup world to avoid going back to a 90 hour work week at a job.
  • Advice for beginning a SaaS company.
  • How company culture is important for a rapidly growing company.
  • Skillshare’s advantage when competing with other platforms.
  • How royalty pool is another form of compensation for a teaching platform.
  • How to structure a team so the CEO doesn’t get lonely at the top.
  • A coaching-based methodology where you don’t need to know all the answers.
  • A community-based approach to teaching and the student connection.

Transcript

Dan Lok: Welcome to another episode of Dan Lok show. Today we are in actually New York City, and I’m with John Henry. Now John not only is an entrepreneur, but also a real estate investor as well as owns a venture capital company.

John Henry: That’s right.

Dan Lok: Now before we even talk about John’s story, I want to talk a little bit about this space.

John Henry: Let’s talk about it.

Dan Lok: Let’s talk about this space. Like what makes this space, co-working space, so special?

John Henry: First things first, thank you for having me on.

Dan Lok: Welcome man, welcome.

John Henry: Appreciate you. And look, what makes this space special is this is the proof right here. Like you’re on a one day trip, you came, you interviewed with Faiza, this content, that content lined up. We connected and it’s central in the city, a lotta energy here, there’s six floors.

Dan Lok: You can feel the entrepreneurial spirit.

John Henry: That’s right.

Dan Lok: The minute you walk in you can feel the hustling.

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Dan Lok: Welcome to another episode of Dan Lok show. Today we are in actually New York City, and I’m with John Henry. Now John not only is an entrepreneur, but also a real estate investor as well as owns a venture capital company.

John Henry: That’s right.

Dan Lok: Now before we even talk about John’s story, I want to talk a little bit about this space.

John Henry: Let’s talk about it.

Dan Lok: Let’s talk about this space. Like what makes this space, co-working space, so special?

John Henry: First things first, thank you for having me on.

Dan Lok: Welcome man, welcome.

John Henry: Appreciate you. And look, what makes this space special is this is the proof right here. Like you’re on a one day trip, you came, you interviewed with Faiza, this content, that content lined up. We connected and it’s central in the city, a lotta energy here, there’s six floors.

Dan Lok: You can feel the entrepreneurial spirit.

John Henry: That’s right.

Dan Lok: The minute you walk in you can feel the hustling.

John Henry: That’s right, and there’s a lot at WeWork’s, obviously, and this is … this, though, is billed as like the OG space, and there are a lot of veteran New York entrepreneurs here. There are several accelerators and several funds and stuff, and so yeah, I’m fortunate to be part of this community.
So we’re in Alley right now. Yeah, and that’s where we find ourselves.

Dan Lok: That’s awesome.

John Henry: Welcome to New York, man.

Dan Lok: Thank you, I love New York. The cold, it takes a couple of days to get used to. The minute I arrived, the airport, like wow! This is cold. I know New York, it’s cold. But this is cold!

John Henry: This is very cold.

Dan Lok: This is very cold. So John, take us back. How did you get into entrepreneurship?