Michael Karnjanaprakorn

If you take the best team executing an idea in a huge market and put them in the wrong  startup culture, they’re destined to fail. Jack Dorsey talks about creating Square as “one startup with many startups inside” which is something I spend a lot of time thinking about for Skillshare. How can we create a culture that  allows entrepreneurial talent to thrive and succeed?

We love entrepreneurs. We love working with them. We love recruiting them. But, entrepreneurial folks thrive in a different culture from the norm. They love taking ownership, influencing major decisions, and having the freedom to swing for the fences. In a way, they’re running a startup within our startup. The challenge is balancing the big picture of what’s most important and giving individuals complete autonomy to excel. Below, I’ll share some of my thoughts around creating an entrepreneurial startup culture from my experience at Skillshare.

1. Hire Entrepreneurs, Not Employees. Entrepreneurial drive is the #1 trait we look for in recruiting and hiring. While most companies want to be known for having great engineers, product; or marketing folks; we want to be known for the entrepreneurs that emerge out of Skillshare (similar to the PayPal Mafia). We even created a role called “Founder Apprentice” to groom future entrepreneurs. And joke internally that the only time someone leaves Skillshare will be to start their own company.

Last year I read an article from Steve Newcomb about renting entrepreneurs, ”let me rent you for 6 months.  You’ll learn an insane amount about building a startup from me that will help you prepare to start up your first company.” At Skillshare, we believe that an entrepreneur working with us for 24 months will provide us more value than an employee working with us for 24 years.

2. Startups within Startups. At Skillshare, we have a flat organization and foster ownership in everything we do. Everyone on our team is tasked with exactly one priority, and everyone on our team has the same responsibility — creative problem solving.

The usual norms around productivity and organization (top-down deadlines, standing meetings, traditional product/project management) don’t mesh well with entrepreneurs. This weekend, I read a great article about the Github culture, “we do things differently at GitHub: we work out of chat rooms, we don’t enforce hours, and we have zero managers. People work on what they want to work on. Product development is driven by whoever wants to drive product.”

We’ve shifted our focus to results and Big Hairy Audacious Goals (BHAG), which has shifted our focus away from creating a rigid process. For example, we had a team retreat in October to talk about the company goals for the next 6 and 12 months, which everyone created together. From there, ad-hoc teams started forming around new ideas to hit our milestones. Now, we’re in the process of creating new teams around these new ideas and everyone on our team will be the CEO of Something, which allows us to get rid of “managers”.

3. Anti-Meetings. I’ve read a lot about the PayPal Mafia culture on cracking down on meetings. We follow a similar cultural principle to reinforce that action and making ideas happen are the most important tenets of our culture. Meetings are expensive (time-wise) and also interrupt creative flow, which is what leads to true innovation.

4. Feedback & Personal Development. However, there’s one meeting that is mandatory at Skillshare. Every Friday, Malcolm and I spend 20-30 mins in a one-on-one meeting with individuals on our team as a form of professional development. This allows them to tell us what they like/dislike about Skillshare and allows us to give them feedback on their performance.

We also spend the other half of the meeting coaching/mentoring them on anything from building a personal brand to fundraising for startups to calculated risks & decision making principles. This is extremely valuable because entrepreneurs are constantly looking to learn new skills.

5. Fun. We also have the usual cool perks: friday team lunches, stipends to attend Skillshare classes, TaskRabbit credits to run personal errands, new MacBook Air laptops, YogaWorks monthly discounts, bi-yearly team retreats, and game and/or bar nights. We also setup field trips with other startups like Kickstarter to check out new exhibits at MoMA, conduct cross-design feedback with Svpply, and invite our investors to stop by the office to have lunch with our team.

As we start thinking about creating an entrepreneurial startup culture, I always look to create small things that can make a huge impact and reinforce our culture. Up next, we’ll experiment with a company chatroom (yes, we don’t have one yet!) to reduce emails and meetings, writing a company manifesto to attract more like-minded entrepreneurial people, and setting up company metrics to objectively measure our results.

Is there anything you do at your startup to create an entrepreneurial startup culture? If so, I’d love to hear them in the comments section below!

Michael Karnjanaprakorn is one of the co-founders of Skillshare. We’re also looking for entrepreneurial folks to join our team.