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Only stupid people start companies; or what I learned from trekking mountains

When I was younger, I started trekking mountains. A small essay on what trekking mountains has taught me about entrepreneurship


Duleepa Wijayawardhana

November 20, 2015

When I was younger, I started trekking mountains. One day my mum said to me “only stupid people climb mountains; you will die.”

I would consider myself lucky. I’ve created and continue to create companies and products. I’ve raised money, I’ve failed and fallen down more times than I can count and I continue. I’ve not had the luck of that elusive and amazing exit. Yet. But I would not be doing anything else with my life than to help take ideas to fruition that have a chance at changing the world. I think my mum might still consider me stupid and I’m okay with that. Which brings me back to climbing mountains…

1. Dreaming of cloudless summits

The Caucuses, Southern Russia

The excitement of planning your venture, whether it be scaling a mountain or scaling a problem is fun. The problems and issues are all ahead and the only thing that you see is a vision of you standing at the top, flag planted on the ground.

Something I heard at that panel was be careful who you tell how much of your idea. I cannot disagree more. In business, just like mountain climbing, success does not happen alone. You need to talk to people and network. In talking to people they will tell you, sometimes randomly, the very thing that will make you successful. Luck isn’t about getting a fantastic opportunity, luck is being introduced to the person who gives you that fantastic opportunity. I’m not saying go blab to everyone, but your execution is far more precious than your idea. Frankly few businesses, or treks, ever get beyond a dream.

2. A team for the ages

You should never climb alone. Without your teammates you are hardly likely to summit. Even those who climb Everest by themselves have a team at base camp. We lionize the great CEOs only to realize that without their talented network they would have had no chance in success.

Your job isn’t to build a product. Your job is to build the great team to visualize, support and build that great product or to take you up a mountain. On a mountain, alone, against the wilderness, you will surely find yourself in trouble. Trust those around you, make them great, and they will in turn make you great and your vision a reality. This is why you will see the same people starting companies together over and over again.

Climbing Mt. Elbrus, Russia

3. The exhilaration and the trepidation

When you first get to the trailhead and look up at what you are about to do there’s a sinking feeling at the pit of your stomach. And yet you look at your companions and you smile. This is the first test. This first night you will see if your equipment is all there. Did you train enough? Did you understand what you were getting into, did you get the right advice?

When your product hits your first customers were you right? Maybe you imagined the problem, maybe you didn’t execute on the solution. But it is exhilarating too. Looking up at the mountain, clouds still on the horizon, the wind picking up. You have actually achieved something that most people never get to. A product out in the wild, a climb up a deserted landscape to heights beyond our human imagination.

4. The grind in the middle

The difference between treks and a business venture is the length of the grind in the middle. With business the grind can take years. Every day you need to guide your venture, try to understand what you need. During this grind you will sometimes go to bed crying, wake up sore, put on a brave face and keep going. You will pivot, find new paths but you will continue.

And you will do it because you have built an amazing team who will sustain you, who will support you and who will carry you when you cannot go on, give you confidence when you have none and make you smile when you have nothing left in the tank. The strength of the team you have built and the vision you have laid down is what will make sure that when there is a storm, and food is low, when arguments flare and the end is no where in sight, the majority of the team will continue onwards towards the summit. Conversely when you have lost the team, look hard at your venture, lest you be left alone on a mountain, a zombie.

5. The search for the summit

Any trekker will tell you about false summits. There’s no worse feeling in the world than getting to the top of a rise and seeing another rise beyond. I can’t tell you how annoying it feels. I do know what it feels like to plant that flag, look at each of my teammates and celebrate that moment, that feeling that you have weathered everything nature and business threw at you and you still managed to win. And you did it together, with each other. Then it’s on to the next summit, the next adventure.

Yep we finally summited this thing

6. Telling is not the same as teaching. Listening is not the same as learning.

The last lesson, and ultimately, the most important one: Telling is not the same as teaching; listening is not the same as learning. Have you talked to someone coming down a mountain? They will invariably tell you how great it was. Similarly, in business, don’t always believe what people tell you. There are lots of talking heads. That includes me. Put me in a pub, give me a pint and a topic and my inner Newfoundlander will come out in spades. I can probably talk you through to my death… and then still keep going.

In reality, success comes from teaching and learning. Teach what you do to anyone and everyone. Your knowledge is not precious but sharing it is. Teaching means that you must also be willing to learn from the person or persons that you are teaching. It means, your way is not the highway, but you want to work with someone to achieve an end goal of a summit.

Similarly, listening is not the same as learning. Listen to those giving “advice” including this blog post, but discard probably 95% of what someone “tells” you and the remainder is probably the “teaching”. The story I tell people after I finish a climb is inherently missing all the bad stuff. Niall Brown and Michael Mannion who have both trekked and co-founded a company with me say I have a brain worm which eats all the bad stuff. We rewrite our own past and how things happened; take everything with a grain of salt.

Learning is putting something you heard into practice, analyzing success and failure, looking at the metrics and reacting accordingly to successfully pivot. Listening will get you out of the storm, learning will help you overcome a disaster. I’m still learning to learn.

So what’s the mountain climber’s mantra for business: Plan, Team, Work Hard, Team, Grind, Team, Execute, Team, Teach, Team, Learn, Team and Summit. Oh yeah, it’s okay to be “stupid.” Just always be learning.

The full team on the summit of Mt. Elbrus, 2006.

Unless otherwise noted, everything you see here (words, photos, drawings, ideas) belong to Duleepa Wijayawardhana.
Opinions expressed belong to Duleepa Wijayawardhana and never one of his current or former employers.

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