Why Every Entrepreneur Must Learn to Ask the Right Questions

“Good decisions come from experience, and experience comes from bad decisions.”

This quote from an unknown author might be the most apt description of my life as an entrepreneur. Some decisions will change your life, but only if you ask the right questions.

In 2007 I was faced with one of those decisions — what to do with my life. I was finishing my master's degree in Management of Innovation and Business Development at Copenhagen Business School. The economy was bullish, industry was growing and graduates were in high demand. Like many of my peers, I got a steady influx of news about recruiting events and even a few interview requests too. At the same time, there was my study-mate, Gus.

Gus and I spent many nights enthusiastically discussing different startup ideas, which always lead me to the same perplexing question: “Should I get a job, or should I start a company?”

I sought advice from friends and family, but informing my decision became a public opinion poll that made my head spin. The problem was, depending on who I asked, I would get a different answer. When I talked to my mom the answer was (obviously): “Take the job, Kasper,” while some of my college friends would urge me to follow the startup dream.

One night I was sitting alone in my kitchen. A friend’s girlfriend had sublet me her apartment. She had for some inexplicable reason chosen to paint her kitchen walls a bright shade of pink. So, there I was, surrounded by this rosy hue and completely consumed by that nagging question: “What should I do with my life?”

Suddenly, it occurred to me that the only person I had not yet asked was myself. So I did. In that moment I realized that I had ignored all the job-related emails to spend my evenings scrutinizing my many startup ideas! I had to do it. And, I reasoned, with the job market the way it was, I could always find something to fall back on if my startup leap of faith turned out to be a disaster.

Ironically, my risk assessment turned out to be flawed, while the true argument — the motivation for doing it — has proved right ever since. The next morning I started my first company with Gus.

For me, the lesson was this; if you ask people for advice on big decisions, they will most likely tell you what they would do. That goes for launching companies, but is true for most of the advice I’ve gotten while scaling them as well. So while I truly support seeking counsel, I’m always cautious of the public opinion poll. I always have to remember to ask myself the question: “What would I do?” Quite often, the answer then is simple.

Two years later, I was again sitting in my kitchen. By then I had moved and the pink walls were gone. I was faced with another big decision to make: “Should I close my startup?” We had enjoyed great initial success and gotten seed investment, but ultimately we couldn’t make it work. Our business model was based on job advertising, and for those who remember (but would rather forget), it was much harder to sell job ads in the fall of 2008 compared to the spring of 2008, when we launched a well-received beta.

We had borrowed about $25,000 each to start the company, but our money was gone. Soon, our investors’ money would be gone too. We were faced with two options — borrow more money to pivot, or close up shop. The question I finally asked myself was this: “Is this idea important enough for you to invest more of your life in it?” This time I knew the answer was no.

The best decision I ever made was to start my first company; the second best was to close it down.

I was broke, but the wisdom I had gained was priceless. After closing down, I did actually manage to find that real job and receive my first real paycheck. Two months later these two guys, Jon Froda and Anders Pollas, started talking to me about joining the founding team of their new startup. I did again ask around for advice, and most reactions where in the ballpark of, “Interesting, but do you really think that idea can be done?”

I decided to do it. I wanted to go back into a basement to build another company, knowing full well that it could either be big (hence worth investing my life in) or it could be a massive disaster. I sent my bank guy this email:

“I need to borrow more money. I realize that I already owe, but, as you know, I am an optimist and believe the best defense is an attack.”

Luckily my bank guy trusted me, and for that I will be forever thankful.

The company was Podio. The mission was to change how people work. Two and a half years later, we had built an incredibly talented team comprised of 14 different nationalities in our offices in Copenhagen and San Francisco. We had changed how thousands and thousands of teams work together around the world, and we were acquired by Citrix.

Our lives and thereby our startups are based on the decisions we make, but more importantly, the questions we ask. So, what question did you ask yourself in your kitchen today?

Kasper Hulthin is a Danish serial entrepreneur. Most recently co-founded the work platform, Podio, which was acquired by Citrix in April 2012.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

Photo By: Ethan Lofton

About Kasper Hulthin

Kasper Hulthin is a danish serial entrepreneur. Most recently co-founded the work platform, Podio, which was acquired by Citrix in april 2012.

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