Creating an Entrepreneurial Startup Culture

by mikekarnj on October 3, 2011

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.

Joining the Collaborative Family

by mikekarnj on May 23, 2011


I’m excited to announce that I’ve joined Collaborative Fund as a Venture Advisor. Collaborative supports creative entrepreneurs who want to change the world and make it a better place.  In other words, they look to invest in for-profit/for-good startups with a focus on Collaborative Consumption. Some of their portfolio companies include Kickstarter, Taskrabbit, BankSimple, and Skillshare.

I’ll still be spending the majority of my time building and growing Skillshare but will be working alongside Jessica Jackley (Kiva/Profounder) as an Advisor with my primary focus on New York City. My time will be split between advising portfolio companies on product and investing in my peers & colleagues that are creating amazing things to make the world a better place.

I’m excited to work with Craig Shapiro (former President of GOOD) who is someone that I admire greatly, and to formally work with Rachel Botsman who has been a personal mentor for years.  And even more excited to support and grow other companies creating world-shaking change.  I’ve always believed in the power of entrepreneurship & creativity to create real lasting positive change and feel truly blessed to help other remarkable entrepreneurs do the same!

Collaborative is currently also looking for an “apprentice” so please apply if interested.

Stop Building Apps and Start Disrupting Industries

by mikekarnj on May 15, 2011

You either build something that makes the world a better place or you don’t. There are complete industries built on creating arbitrary value for the world (investment banking). And there are complete industries built around innovation and creating value for the world (technology).

If you’re an entrepreneur where your success is built around the value you create for the world (e.g. Apple) , you have an opportunity to disrupt entire industries. The world doesn’t need another “Groupon for X”; we need more companies disrupting archaic institutions like healthcare, education, insurance, government, and banking. We need more companies like Uber that receive cease & desist letters from their city to shut down. And more companies like ProFounder, Votizen, BankSimple, and Massive Health that utilize the power of the web to democratize entire industries.

So, the next time you think about starting or joining a company, think about your individual impact on the world. You have a real opportunity to make it better.

Join Forces like Voltron

by mikekarnj on March 24, 2011

“If everyone is moving forward together, then success takes care of itself.” – Henry Ford

It is argued that one of the best teams in the history of the NBA were the 1995-1996 Chicago Bulls. They had a great trio with Michael Jordan, Scottie Pippen and Dennis Rodman with a stellar supporting bench. They set the record for most wins in the regular season (72-10), ended the season winning 87 of 100 games (including the playoffs), and ended up winning three championships in a row during their reign.

I believe that if age wasn’t an issue, the players on the 95-96 Chicago Bulls team would still be winning championships today. And the players on their bench would be leading other teams to championships. Maybe additional three-peats? But they couldn’t do it without each other.

If you think of the startup world, the same holds true for great entrepreneurs and companies. If you look at the Paypal Mafia, Facebook Mafia, and Google Mafia; they’ve produced a list of great startups from their alumni including Youtube, Linkedin, Kiva, Yelp, Quora, Asana, etc. It’s almost mind-blowing what they’ve accomplished. The best part? Unlike the NBA, getting experience over time is a huge bonus and advantage for success.

“You never think it could happen to you. But seeing Peter and Max and the guys come up with ideas and seeing how to make things work gave me a lot of insight. You may not have a business degree, but you see how to put the process into effect. The experience helped me realize the payoff of being involved in a startup.”
– Chad Hurley, Youtube Co-Founder, Paypal Designer

Chad Hurley came into Paypal as a designer and left co-founding Youtube. So, what is the secret behind all of their success? I believe it comes down to two factors: 1) great teams and 2) great cultures that nurture entrepreneurs.

The world needs more great companies cultivating successful entrepreneurs. Not more startups.

Why buy silver, when you can rent gold? At Virgance, Steve Newcomb loves “renting” entrepreneurs. “I can’t tell you how many people I interviewed at Powerset who told me they really didn’t want to join because they wanted to startup their own company.  Whenever anyone told me that, I would go in for the kill and not let them leave until they agreed to join.  My pitch to them was simple.  “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.  You’ll have the pedigree of Powerset standing behind you; and you’ll have some cash in your pocket.”


Most companies raise capital to accelerate their growth and success faster than bootstrapping it. As an entrepreneur, if you think about your personal equity, you’ll reach success much faster by joining great teams and getting a feather in your hat. You’ll learn about entrepreneurship in the process and learn more about being a successful entrepreneur. You’ll also minimize your risk of failing at your next company, which is what it’s all about right?

Carter Cleveland at has a founder internship. We call ours a founder apprenticeship. But the idea is the same: we’re nurturing future entrepreneurs, and more startups need to be doing the same.

On the other side of the coin, we need more entrepreneurs working together. $41M pre-launch doesn’t happen without a great team. Look at Lebron, Wade and Bosh. I’m sure they’ll 4-peat in their lifetime which is something that could have never happened without them joining forces like voltron.

So, if you’re an entrepreneur with the itch to start your own company, you should really consider joining  a great team, which will allow all of you to achieve greatness. Like Jim Rohn says, “you are the average of the 5 people you spend the most time with.”

Why We’re Building Skillshare

by mikekarnj on February 24, 2011

“Learning is not a product of schooling but the lifelong attempt to acquire it.” – Albert Einstein

Skillshare is a community marketplace to learn anything from anyone. Our mission is to flip the traditional notion of education on its head and democratize learning. We’re building Skillshare because we believe the world needs a learning revolution. Piquing your curiosity, finding new passions, and learning new things should be a lifelong process.

As our team started to think about what the educational landscape of the future could look like, we got excited by the range of possibilities. What could complement traditional institutions? How could we use the power of the web to spread ideas, skills, and knowledge? Where and when should learning happen?

This exploration led us to think about the difference between learning and schooling. While learning traditionally happens within the four walls of a classroom, why couldn’t learning exist outside of school? We all know that NYU is a great university, but what about New York City? Everyone that lives here has something valuable, interesting, and unique to share with others. We just need a platform to unlock this knowledge, and thus, Skillshare was born.

We believe that the world’s most abundance resources are knowledge and skills. Unfortunately, this isn’t being easily shared between people but if we can build a platform to facilitate and share this excess resource, we can unlock what we believe matters the most in the world: happiness, purpose, and fulfillment.

So, in short, here’s the vision behind why we’re building Skillshare:

1. Learning should be a lifelong process. The community of peers centered around learning is something magical that happens during college, but why does that have to stop? Going to class, interacting with teachers, making new friends – these are all amazing benefits of college. Why can’t we continue this magic after college? The answer is really simple. We shouldn’t. We believe that learning should happen in communities around shared interests. We have the opportunity to turn the city of New York into one of the world’s great universities.

2. New skills are being introduced everyday. While it’s great to learn multi-variable calculus or the economics of china during school, what about the other 99% of skills that will never see the light of day? By the time a college starts teaching “Mastery in Online Community Management”, it will become so outdated and irrelevant. Traditional education will never catch up to the skills needed in the market today. We are creating Skillshare to facilitate peer-to-peer learning when it matters the most – right now. A company like Foursquare can create their own school to teach courses on “LBS development for mobile devices” and recruit directly from the best of the best. Revolutionary.

3. Learning should be fun and interesting. Lastly, learning for the sake of learning should just, well, be fun! I mean, who doesn’t want to learn “how to travel around the world before you’re 65″, “propose to your girlfriend”, or “bake the crackpies from the Momofuku Bakery”? A recent article from the NYT titled, “Consumers Find Ways to Spend Less and Find Happiness” found that “a $20,000 increase in spending on leisure (such as classes) was equivalent to the happiness boost one gets from marriage.” Our goal is to increase the gross happiness index around the world by staying passionate and having fun.

Everyone has something valuable to share and teach. Nothing will ever replace the magic that happens when passionate people get together to learn from each other. We don’t learn from books. We learn from the people that wrote them.

Henry Ford said it best when he said that “anyone who stops learning is old, whether at twenty or eighty.” We hope to change this and deliver a learning revolution to the world.

If the idea of disrupting education and learning excites you,  join our team. This article is also cross-posted on Skillshare.