Being an Entrepreneur Is a Dangerous Business

John Lewis
Nov 24, 2014 · 9 min read

How a 250cc motorcycle can help you get back on your entrepreneurial path.

I met a shaman once who told me that Westerners have lost the ability to be alert, awake, and observant with senses fully engaged and body relaxed. I considered this idea when I signed up for a three-day motorcycle trip with Wilderness Collective (WC), a nuts-to-bolts outfitter led by a young, tough and freewheeling Canadian guide named Steve Dubbeldam.

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In nature, it’s easier to quiet your cleverness.

WC promised us things that weren’t implicitly stated in the beautifully shot and well-edited promo videos on their website. It was clear from the site that we’d be well-fed and provided with all the creature comforts. It wasn’t as clear that we’d riding on loose gravel with a few treacherous river crossings and cliffs, and that we’d be led through fire roads we’d never be able to navigate on our own. On a personal note, I knew I was in way over my head as I had never ridden on dirt before and wasn’t sure what adjustments I would need to make until I was actually riding. If you’ve ever started a business, this sounds quite familiar.

You see, I had just spent the last five years of my life entrepreneuring in Beijing, China with a business of my own creation. I didn’t have a Steve Dubbeldam to lead the way to make sure I “got out”. I learned Mandarin “on the job” speaking to a patient, bilingual staff, and I definitely ate things for dinner that most Americans trim and toss. Riding dirt was comparable to learning a language with over 2,000 characters and trying to explain to demanding Chinese VC’s how I planned to spend 7.5 million rmb (over $1M USD): While I was in way over my head, it was all figure-outable. This feeling was exactly why I signed up for this trip, and is the hallmark of being an adaptable leader and engaged participant in the journey of life.

So this was more than thrill seeking, this was also about connection.

Connection to purpose.

Connection to self.

Connection to others.

Connection to nature.

And depending on what bike you decided to try, connected to a snappy, fun-to-ride Honda 250 (or 650). In my case, I rode both.

You take on a journey knowing damn well that you will meet obstacles unknown, and you will, with almost 100% certainty, find yourself in a situation where you will fall down and need to get back up.

The mythologist Joseph Campbell claimed this narrative in the form of the hero’s journey:

“A hero ventures forth from the world of common day into a region of supernatural wonder: fabulous forces are there encountered and a decisive victory is won: the hero comes back from this mysterious adventure with the power to bestow boons on his fellow man.”

Ahh, yes…of course.

The hero’s journey. The mysterious adventure.

What metaphor can we explore that connects entrepreneurs to the danger of the journey that leads to personal transformation?

Where is there danger and uncertainty countered with clarity of purpose?

No (De)Vices

As mentioned, WC and Steve have a strict no-electronics-on-the-trip policy. No cell phones. No cameras. The idea is that, without your (de)vices, you can be totally present with other riders (all men) and ultimately connect to your purpose as you rip through 100+ miles a day of John Muir’s perfectly preserved Sierra foothills en route to the Yosemite Valley. (Note to naturalists and John Muir fans: the “archetype of our oneness with earth” can be achieved with proper braking and increased throttle. More on that later.)

I tucked away our much loved (de)vices, and headed out to the unknown. (Fortunately, Steve and team documented the entire trip with still shots and video.)

Three hundred plus miles in three days of riding with new eight new fast friends and the WC staff (Steve, Yao, our videographer, and superstar Chris who somehow, in the middle of the Sierras, whipped-up cider braised pork shoulder, bison chili, and bacon-wrapped filet mignon, accompanied by handmade cocktails) I got clear on one thing real quick. Riding a motorcycle and running a business have a helluva lot in common, it really is all about the journey.

The Meaning of Life

Zen comes from truly seeing with eyes (and heart) that happiness, flow, ease, and the meaning of life can be achieved through the practice of being present.


Go back and read that sentence again.

I just handed you the meaning of life and it only took me three days to figure it out.

Realize, I have seen friends test the laws of gravity and the strength of human relationships to know this truth for themselves. In my case, I took a few turns too wide on this trip and applied too much brake and found myself face down in the Sierra dirt.

In 2003, I took a turn too wide on the Kancamagus Highway from rural Vermont through the white mountains of New Hampshire when “it” happened and my entire nervous system was set on fire. I misjudged a turn and found myself on the other side of that yellow line that separates motorcyclists from organ donors. Here in the Sierras, that feeling is no different except there isn’t much time to be present when throttle, poor judgement and gravity slam you face first into mother earth. That honor was shared by pretty much every guy on this trip, and certainly some more than others (no names here).

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The classroom where life lessons are taught.

Motorcycles and running a business both teach you life lessons and here are mine.

Lesson #1 — What’s behind you can be just as important as what’s in front of you.

Now, this is more of a paved road rule than dirt, but for any entrepreneur who has failed knows, your past does not predict your future but you carry it with you as part of your human experience.

In motorcycling I always check my mirrors because the stuff behind me, if ignored, will run me over. On the road, it might be a distracted motorist, a texter, or even a reader. (Sadly, I have actually seen people reading novels while driving in L.A. commuter traffic.)

Entrepreneurs build on the past to inform their future — but they never dwell on the failure. Entrepreneurs and motorcyclists both know about scar tissue and how it makes you tougher. (And let’s be honest, it also makes the story just that much better.)

Look in the mirrors, have an exit plan, and keep moving forward. At the same time, remember where you are from and know where you want to go.

Lesson #2 — Don’t target, fixate. On a motorcycle, your bike goes to where your eyes are looking.

If you stare at one thing too long, it can become too hard to focus on anything else. The spiritualists and self-help gurus will tell you that if you constantly think about one thing, it expands in your mind. Think you’re poor? Focus on your lack of abundance and it will continue to define your reality. In life, you might end up working too much or obsessing over a business relationship you want to control.

Look into the future, not at it.

Lesson #3 — When you ride, lead an examined life and be mindful of your surroundings.

Don’t think that little thing in the road isn’t important. Maybe it was an argument, a snarky comment you made, the copy you approved too quickly, or the loose end left undone. Nothing is little if left unexamined. On a bike, it can take the form of loose gravel or a flattened can that decides to become a moveable surface when you apply the brake.

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Throttle gets you out of trouble, (almost) every time.

Observe. Adjust. Focus. Throttle.

Next step, get off your bike, put the kickstand down, and help your bro push his bike out. Here’s lesson 3.5: If you get through a difficult period in your business, you are obligated to help someone else. Even if they don’t want help, and perhaps they won’t, but you should ask. You should feel an obligation to pull the next person through to where you are; to share your lessons.

Lesson #4 — It’s always about going your speed, not someone else’s.

Richard Branson explained in a TV interview that during difficult cash flow periods in his startup days with Virgin, he would investment-spend his way out of troubling financial times to show his competitors that he was still in the fight.

One of my fellow riders, Jesse, described how important it was for him to go his own pace on the trip as the “front” of the pack didn’t work for him.

Whether it’s an opportunity to go at your competition, or the chance to test limits and alter your approach — throttle makes the difference. Find that happy place between throttle and brake, between expanding and contracting, or being in the front or adjusting to a different position that works for you. Don’t compare yourself to others; find that sweet spot and own it in your business and in your life.

Lesson #5 — How you do one thing is how you do everything.

I tell my kids this story at least once a week. When I worked at Nike my boss always said that “God was in the details.” On a motorcycle it’s obvious within seconds if your preparation is rushed. On a solo ride, I didn’t pull my gloves over my jacket cuff and a bee flew up my sleeve at 75 mph on the PCH — and stung me on my arm. In business this means your code might be off and create bugs, or there’s a typo on your website which creates a lack of trust with your reader. Be obsessive.

Own the details and own your results.

Lesson #6 — Everything is relative.

This is my brother’s favorite expression, and he’s right.

Hell yeah motorcycles are dangerous…and so is starting a business. The danger is only relative to the danger of NOT doing the thing you need to do. If it’s in you it is in you and the pain of not having tried is not the movie you want to play back at the end of your life.

Back from the mysterious journey, I have my clarity of purpose and am happy to bestow these “boons” with my fellow man.

The energy associated with danger and uncertainty are most certainly your friend. This is not a speech about getting outside your comfort zone, this is more about channeling that crazy energy into your life’s purpose. Ultimately, the bike is nothing more than a tool to help you check in with yourself. It helps quell the cleverness and the business that distracts you and guides you back onto the ‘right’ spiritual (read: metaphorical) path. If you’re not sure what your path is, quiet the chatter in your head and identify a philosophy that resonates with the life you are meant to lead.

I have a few friends who have tattooed their life philosophy somewhere on their bodies. I am not a fan of tattoos generally speaking — but if I were, mine would be pretty simple.

“More throttle. Less brake.”

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Landon Ray (CEO of ONTRAPORT) and the author pause to enjoy the view of the Yosemite Valley.

(All photos courtesy of Wilderness Collective)

Modern Entrepreneur

The voices of small business owners, entrepreneurs, and…

John Lewis

Written by

Seeking the convergence between life and art…. Instagram: @johnnylewis

Modern Entrepreneur

The voices of small business owners, entrepreneurs, and business enthusiasts.

John Lewis

Written by

Seeking the convergence between life and art…. Instagram: @johnnylewis

Modern Entrepreneur

The voices of small business owners, entrepreneurs, and business enthusiasts.

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