Entrepreneurs embrace embarrassment and pain – lessons from snowboarding

Just like my first time learning how to snowboard, entrepreneurs have to embrace embarrassment and pain to be successful

After being in Canada for 17 years, I finally went snowboarding for the first time 2 weeks ago. So here I am, a 27-year-old guy, on the bunny hills with little kids who are probably 7 or 8 year old passing me left, right and center. Not only that, about 80% of the time, I’m either on my ass or on my knees while those little kids perfectly carve the slopes. I feel like such a fool.There’s a part in me that says, “you’re too old for this. Just give up.” But, I push on, get up and try again.

Not only that, the next day after snowboarding, I felt like I was 50 years older than my age! My whole body was in pain: my wrists, elbows, neck, shoulder, knees, ankles and, especially, my ass! All the pain and embarrassment wasn’t all in vain. At the end, I finally got it.

Here’s what hit me after falling a gazillion times: The only way you can really learn something is if you’re willing to embrace embarrassment and pain. Why? To learn something, you have to put yourself beyond your comfort zone. You have push yourself to the point of failure. If you’re not pushing yourself to the point of failure, then you’ve probably already embraced your greatest enemy, status quo.

As I’ve mentioned before, if status quo is Goliath, entrepreneurs are the first ones who step up to take a swing at the enemy. Entrepreneurs always push themselves, their startup and their team to the point of failure. That’s why entrepreneurs embrace embarrassment and pain, especially those who are applying the lean startup techniques to their startup.

Embrace the embarrassment

One of the central principles of the lean startup method is to get your product into customers’ hands as quickly as possible. But one common worry with this concept is that this might lead companies to “release crap,” shipping too soon with a product of such low quality that you embarrass yourself and alienate potential customers. But, as Eric Ries points out in his blog, this thinking assumes so many things. What if customers actually like the “crap” product? Or what if we can’t get any of them to even try it? Or what if the features they demand you build are different from the ones you were planning to build? That’s why you build your minimum viable product  and get it to your customers’ hands as soon as it’s possible.

But, the minimum in minimum viable product does not mean that you should ship just anything at the earliest possible date. It means to ship as soon as it is possible to learn what you need to learn. It’s an opportunity to learn what attributes customers care about. Receive feedback from your customers that are both qualitative (what they like and don’t like) and quantitative (how many people use it and find it valuable). You can’t learn if you don’t ask. So, don’t be afraid to ask your customers and be embarrassed.

Embrace the pain

But building a minimum viable product is not enough. You also have to measure progress and learn from the results. Then you have to repeat the whole build-measure-learn cycle until you find a business model and product that’s profitable and scalable, which could take a few weeks or even a few years. If it sounds painful, it really is.

Some people think being an entrepreneur is really sexy… for those who have never done it. The reality is that it’s hard work, high pressure and exhausting emotionally & physically. It’s easy to lose your way. One moment you’re feeling like you’re on cloud nine; the next moment, everything is on fire, even your hard-earned cash. Every day you go home and face self doubt but you’ve got to come back in the morning strong. Your other co-founders, the team you’ve put together, are all looking at you for signs of weakness and self-doubt. You’ve got to accept customer losses as learning experiences and see how you can improve next time. You’ve got to hear all the doubters of your product, and there are A LOT of doubters out there. It’s far from sexy. It’s tough as hell.

Still want to be an entrepreneur? If you’re answer is yes, then you have to be willing to take punches everyday, fall down and then get up for round 2, 3, 4, whatever it takes. As Mark Suster (an entrepreneur turned VC) puts it, “resilience is one of the tell tale signs of an entrepreneur.”


The building of a startup and successful exit or IPO is equivalent to the mental and physical toughness of winning the gold medal at the snowboard superpipe at the Winter X games. It’s not easy. You have to be willing to be embarrassed and take pain, a lot of pain! You just have to stick to what you believe in. As Sir Winston Churchill once said, “Success is the ability to go from one failure to another with no loss of enthusiasm.

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Growth, analytics and inbound marketing professional. Computer science educated from University of Waterloo, full-stack developer turned growth hacker. Follow me at @RamliJohn. Ready to help you with your growth issues at http://bit.ly/help-me-ramlijohn

4 thoughts on “Entrepreneurs embrace embarrassment and pain – lessons from snowboarding

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