Summit, Or Die

Julian Aldridge
Illuminate
Published in
7 min readAug 2, 2024

Three Lesser Known Challengers Who Risked It All For A View From The Top

Masada at sunrise

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” — Mark Twain

Nearly two thousand years ago, during the first Roman-Jewish war, up to a thousand Jews committed mass suicide rather than submit to the amassed Roman forces who had laid siege to the mountain top citadel named Masada.

This was one of the legendary events of the time, and the last stand of the Jewish patriots who chose death rather than slavery. As such, it signified the start of the dispersion of Jews around the planet, and, for many, is a symbol of the eternal fight between oppression and liberty.

For my traveling companion and I though, Masada had slightly mor prosaic significance as we journeyed along the Dead Sea and into the Judean desert: destination Cairo.

For a week or so all we’d heard about was the jaw dropping sunrise that could only be seen from the top of Masada. According to anyone we’d spoken to, it was the ninth wonder of the world — an epic view from one of the most important Jewish sites in the Holy Land.

And so, my traveling companion and I made a promise to ourselves to stop en-route to Cairo, via the Sinai. This was the summer of 1982, and neither of us had any real idea of how we were going to get into Egypt, let alone to the big city with the pyramids, but that’s for another blog.

The bus had dropped us off at the base of the mountain on route 90 as dusk was approaching, the golden hour setting the eastern slopes on fire. It was spectacular, forbidding and rather daunting. However, we’d been told that the hike to the summit should take less than two hours, even with our backpacks.

We’d Made A Promise To Ourselves To Summit Masada. And Summit It We Would

There was only one problem. A very large sign in Hebrew and English informed all visitors that it was forbidden to climb Masada at night. Not forbidden in a ‘you really mustn’t eat you food that quickly’ kind of way, but more of a ‘should you chose to do this you risk death, dismemberment and eternal familial disgrace’, manner.

The sign was very clear: Israeli troops had a right to shoot on site anyone choosing to ascend the slopes at night. To back that up, a few huge spotlights constantly coursed over the mountain, just to make the target practice easier.

Decisions, decisions.

We could camp at the bottom and head up in the morning, but in so doing, we would never get to see the famed sunrise. Or, we could risk life and limb and head up.

What would you have done, aged 20?

In the life of every Challenger, there are inflection points. Times when a person or company has to decide — should I try for the summit? Should I wait? Or should I chart another course.

Here are three lesser known entrepreneurs who chose the riskier route — but who reaped the rewards of their bravery.

FUBU. Would you risk losing your house to grow your business? That was the choice that Daymond John, now a household name and a Shark on the infamous Shark Tank, took thirty years ago. At the time their street-cred brand was still in its infancy, but was about to explode, after childhood friend LL Cool J had worn a FUBU hat when filming a Gap commercial. Seriously.

Suddenly the Brooklyn based brand was an urban hit, and, after exhibiting at Las Vegas’ Magic fashion show in 1974, had $300,000 of orders.

The only problem? Actually making those orders.

Despite taking out a second mortgage to fund the business, they were still hopelessly unable to fulfill the demand. So, after 26 out of 27 banks had turned down their request for a loan, Daymond’s mother put an ad, using their last $5,00 of savings in the NY Times, looking for funding.

One last roll of the dice, and finally they had a manufacturer on board in the shape of Samsung Textiles.

Since then, Daymond has put his money where his heart is by investing in other startups, currently to the tune of over $9 million.

FedEx. Would you risk your entire business, and $100 million of investment, on a card game? No. I thought not. But that’s exactly what Frederick W. Smith, the founder of FedEx did. Founded in 1971 using his $4 million inheritance (worth about $28 million today) and a further $91 ($400) million in VC funds, the company got off to a flying start delivering packages, initially mostly in the US, overnight, by plane.

However, the OPEC oil crisis that his in 1977 doubled fuel prices, resulting in the still nascent firm losing a million dollars a month. By the end of the year, having failed to raise any additional capital, FedEx was on the verge of bankruptcy, with just $5,000 in their bank account.

Time for a big gamble.

So, Fred did what any (in)sane person would do and went to Vegas, betting the remaining cash on Blackjack, and coming back with just enough money to refuel the planes, and keep the company flying until new investors could be found.

Two years later, and FedEx was in the black. All thanks to Blackjack. Now that’s a gamble that paid off, handsomely.

5-Hour Energy. Sometimes it’s not the gambles you take during the development of a business that really pay off, it’s the gambles you take setting yourself up for success years before you open shop. Such is the case with Manoj Bhargava, an Indian entrepreneur who may, or may not, be the richest man from the subcontinent residing in the USA.

Challengers know that it takes a very special mindset the challenge the incumbents, and win. For Manoj, cultivating that mental clarity and fortitude took a decade or more, courtesy of various ashrams, called Hansloks, in India. Essentially dedicated to spiritual growth and enlightenment, these ashrams focus on the stilling of the mind through intense meditation.

Equivalent, perhaps, to the years of training that mountaineers do prior to a major summit, Manoj’s focus on his mental acuity paid off when, after driving taxis in New York, he returned to India to focus on his family’s plastics business, before marrying and moving to that entrepreneurial mecca called Detroit. It was there that he founded 5-Hour Energy, a business now worth billions.

The moral of the story? The only risk is not taking a risk. And that applies to budding entrepreneurs as much as established executives looking to turn around their businesses, or chart a new course towards greener, richer pastures.

The Only Risk Is Taking No Risk

Although I was blissfully unaware of this gem of management theory forty two years ago, I had already subscribed to that mantra when traveling.

For better, or worse.

Gazing up at the peak some 1,424 feet (434 meters) above us, we decided to wait. Until it got truly dark, at least. Less chance of being spotted (and shot), we reasoned. Ninety minutes later, with the temperature still in the nineties, we set off, carefully picking our way along the rocky trail.

Immediately things went from problematic to potentially disastrous, as one of my not-exactly-built-for-extreme-hiking flip flops broke. Irreparably. Barefoot it was to be.

Clearly I wouldn’t be writing this blog if we didn’t make it, but it was no picnic. I’m not sure if the Israeli soldiers would really have shot to kill, but, fortunately, we didn’t test their decision making powers, as we scrambled up the steep, stone-strewn path, hiding behind boulders whenever the searchlight came close.

When we finally reached the top, we found another hundred or so Lonely Planet-ers sharing the small, relatively flat plateau. Some reading by flashlight, others huddled around a small fire quietly sharing travel stories, and a few already sound asleep.

A few hours later, and we got to witnessed the most ferocious fireball as it peaked over the Jordanian mountains, illuminating the Dead Sea below. All to the backdrop of chanting and singing. I’m not vaguely religious, but this was a truly spiritual moment, steeped in history, suffering, belief, and pathos.

Never Judge Yesterday’s Decisions Based On Today’s Facts

Looking back now, I’d never advise anyone to make the choice we did. But I’m pretty sure that many entrepreneurs would say the same thing about some of their bigger gambles. What seemed entirely logical at the time, in retrospect often looks insanely irresponsible.

But that’s the point. When would be moguls make those decisions, it’s based on the information and risk-reward equation of the time. A decade later, all the components of the equation will have changed — as they should.

Entrepreneurs should never judge yesterday’s decisions based on today’s facts. That’s like judging Olympians of 1962 against today’s times and distances, or the diet of our grandparents against today’s nutritional standards. It makes no sense. Different eras call for different criteria, different metrics, and different decisions. Period.

Today, you can catch a cable car up to the top in just a few minutes. There are even sunrise tours that depart from various Israeli destinations, all of which can be accomplished without fear of ripped feet, dehydration, or death by sniper fire.

But, what’s the fun in that?

………..

Julian founded his agency, Enact, to help brands of all sizes discover, define, articulate, and amplify their Challenger Story. Illuminate is published weekly, and his new book Illuminate: A Challenger’s Handbook, Volume 2 is now available on Amazon. He can be reached at Julian@EnactAgency.com

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Illuminate
Illuminate

Published in Illuminate

Stories from the Frontline of Challenger Brand Strategy

Julian Aldridge
Julian Aldridge

Written by Julian Aldridge

Julian is a passionate advocate of the power of thinking and acting like a Challenger. He founded EnactAgency in 2010 to help brands enact their Challenger DNA