Michael Karnjanaprakorn

“I will not lose, for even in defeat, there’s a valuable lesson learned, so it evens up for me.” – Jay-Z

Last year,  I wrote an article on “Five Entrepreneurial Lessons from 2009” which was a very pivotal year for me as an entrepreneur. My 2009 lessons revolved around focusing on focusing, working on the right thing, and taking time off.

There’s a natural progression that entrepreneurs make over time. For me, if 2009 was a year for exploration; 2010 was the year to make a commitment.

At the beginning of the year, I joined a startup called Hot Potato, which was eventually acquired by Facebook. After organizing four conferences, I stepped down from The Feast as the co-organizer. And I ended the year launching my own startup, Skillshare, which is a platform to learn anything, from anyone. It’s been a long journey (you can say a lifetime) so far but it’s also just the beginning. Hopefully, you’ll find some of these lessons below useful for your own entrepreneurial journey. Buckle up!

1. There’s no rush. Climb the ladder. In the corporate world, there’s a standard ladder to climb to get to the top. If you work in banking, you start off at the bottom as an analyst and work your way to the top by becoming a partner. In the world of entrepreneurship, there is a similar ladder to climb.

Entrepreneurs should start with small ideas and learn how to execute those ideas. Learn how to gain traction, learn from your mistakes, and learn how to make something out of nothing. And eventually the ideas you pursue get bigger and bigger.

Your bar gets higher. Your filter for what you work on gets higher. And this is something you can only develop over time by making your ideas happen.

2. Solve the right problem. As I climbed the idea-scale ladder, I spent a lot of time thinking about what would be the biggest possible problem I can solve – something truly disruptive and world-changing.

You can be the greatest idea person in the whole world, but if you’re solving the wrong problem, you’re still solving the wrong problem. Most startups don’t fail because they don’t have a great team, or stellar technology; they fail because they think they’re solving a problem people actually care about.

In September of 2010, I took a think week, which was an enlightening experience for me. It allowed me to make a clear decision on what I wanted to do next with personal and professional life. And most importantly, whether Skillshare was solving a huge problem with a disruptive solution. The power of time off is a very powerful thing to do for yourself.

3. Put a feather in your hat. At the beginning of 2010, I had breakfast with Zach Klein (College Humor, Vimeo, Boxee, Svpply) who convinced me to join Hot Potato to lead their product team. His selling point? I needed a feather in my hat.

At that point in my career, I spent all of my time forcing a good idea/pointless problem. I spent more time convincing people that it was a good idea than actually working on the idea, which is when I decided to scrap it completely to focus all of my time and energy on Hot Potato.

Hot Potato eventually got acquired by Facebook. I got a feather in my hat. And while walking down a random street in NYC, I came up with an idea to disrupt the education industry, which eventually turned into Skillshare. Everything fell into place when I decided to not force or rush my personal journey as an entrepreneur.

4. Finish your commitments. Over the years, I never realized the true time commitment of working on so many different ideas and projects. When we started The Feast Conference in 2008, I didn’t think it would actually expand to a global audience.

It was a good problem to have but that was the downfall of working on so many different ideas. Some of them actually took off and even though I wanted to move on to bigger and better things, I still had to ride them out to the end. In 2010, it took over 10 months to full transist out of The Feast, which sucked a lot of my time and energy away from Skillshare.

As you start thinking about all the ideas you are working on today, you should also think about how to exit out of them if they fail (easy), or transist out of them if they succeed (harder). Better yet, you should ask yourself if this is something you want to work on 5 years from today. If the answer is no, don’t even start.

5. Put your stake in the ground. The most important lesson I learned in 2010! When you’ve climbed the idea-ladder, figured out a big problem to solve, put a feather in your hat, and finished out your previous committments – it’s time to put your stake in the ground. Like they say in poker, it’s time to go all-in!

When that happens, buckle up and enjoy the ride. Because whether you succeed or fail – great things will happen.  Like Jay-Z says, “I will not lose, for even in defeat, there’s a valuable lesson learned, so it evens up for me.” Word.