In The Deep Dive, The Origin Story Comes To Life

We love to project our dreams on to successful entrepreneurs. Look how successful they are! Oh, the private jet! Oh the big stage. The IPO. Boy they’ve got it made.

But while we focus on the heights in a transformative story, whether told in a TED Talk, a dinner table conversation, or the recent top of the charts biography, it’s the depths that are hard to tell.

But it’s where all the power of transformation can be found.

I had a moment in my own entrepreneurial journey that showed me this. We had two small kids, a vision of helping the world tell better stories, and the waning idea that tomorrow things were going to be better. At the plum bottom of this adventure, I’d go out and check my mail three times a day. As if practicing some strange entrepreneurial asana, I would reach into the mailbox, searching left, right, then closing it – and then glancing in one more time. Isn’t the check here yet?

But it wasn’t – so often it wasn’t. The river had run dry.

One day, a friend came over to visit with my wife Ahri. Our house was so often a center of activity. We hosted people all the time, for dinners, holidays, events. So the friend walked in with her cup of coffee, said hello in her thick New York accent, and walked towards the kitchen. “This coffee is way too strong. Do you have any milk?”

She went to the fridge, opened it, and froze. She looked up at Ahri, confused.

Why? Well, because the fridge was empty. Empty, as in a bottle of ketchup with too little ketchup to even merit it being there. Ahri’s friend slowly closed the fridge…and never spoke of it again.

The check came in that afternoon. The fridge soon had food again, and the pod of kids that were constantly running around our house had no interruption of muffins and milk. And somehow, with toothpicks, chewing gum, and a lot of love, we kept it together, day by day. Largely a credit to Ahri’s ability to find magic in tiny things, the kids never knew our lives were anything but abundant. The business grew bit by bit. And finally, months and months and months later, I finished my book. The calls somehow grew exponentially. The waters began to flow again.

It seems like a moment that stands on it’s own, packed far behind us. But it is to us tied to so many other moments of trial at the bottom of our journey. If you’ve ever tried to create something, leveraged yourself well beyond your means to bring a vision to life, you know what I’m talking about. There are some stories that just feel a lot better to tell in retrospect.

But part of what helped me navigate these empty fridge days was that I became fascinated with what the mythologist Joseph Campbell called the Belly of the Whale. I started exploring more and more how innovators and creators get through the darkest hour – the Innermost Cave. At one point I even did a whole storytelling event about founders diving in deep, called The Turnaround.

The Innermost Cave is a critical ingredient in your transformation recipe. There’s no forcing your way through if you’re talking about a big change or life-guiding insight. There’s no punching through the wall, or skipping the hard part. And it’s not simply about being calm, either. There’s something much deeper, more nuanced in emerging through the darkest hour.

This pivot is beautifully identified over and over again in the podcast, “How I Built This,” by Guy Raz. In it, nearly every single entrepreneurial journey comes with an Innermost Cave, where you don’t know how things are going to turn out. Sometimes it’s remembering something important from long ago. Sometimes it’s patience and enduring the hardship until something shifts. Sometimes it’s just pure luck…and so often, luck does favor the prepared.

It’s funny, you know these entrepreneurs are successful innovators, otherwise they wouldn’t be featured in such a podcast. They’ve come through the trials to the (at least in our minds) flower-laden meadow of success. But you don’t know how! And while it’s the why that sends you on the journey, when it comes to getting out of the Innermost Cave, it’s from the understanding how that we can all glean some insight – and some energy.

In each “How I Built This” interview, Guy takes the listener on a journey through the life of entrepreneurs and innovators like Jake Burton of Burton Snowboards, John Mackay of Whole Foods, Sarah Blakely of Spanx, and Maureen and Tony Wheeler of Lonely Planet. And in each story, the power is in the innermost cave to the Until Finally moment, where the light bulb goes off.

And the power, in my studies, lives right between those two: The Innermost Cave and the Until Finally moment. Here are just a few examples from HIBT stories:

Jake Burton Carpenter, of Burton Snowboards, is a legend in the snowboard industry, inspiring visions of fresh powder and epic times. But the first time he went out to sell his new product, things were very different: “I was like Willy Loman. I was a traveling salesman. I would load up my car, a Volvo wagon…and I remember once going out with 38 snowboards and I drove out across New York state visiting dealers…coming back with 40. Because one guy gave me two back.”

“Nobody wanted any part of it. I had a few days that it was tough getting out of bed, just motivating myself….I had to let go of my two relatives and my friend very quickly.”

The Innermost Cave was deep, and he didn’t know how to get out. But the next year they did 350 boards. And he kept at it. He was doing all the assembly of the boards, and all of the selling, on the road, visiting ski shops and resorts. And two long years after his first sales journey, things changed. The key in emerging? “Exposure. Getting out there, word of mouth, advertising.” Persistence. Faith. Believing that the Until Finally moment would come. And it did: “I remember one day in that second winter of selling, and packing up that 700th board. And I remember thinking. Wow. That’s over doubling.”

He knew he was on the way.

Sarah Blakely of Spanx is synonymous with an iconic powerhouse founder. But not too long ago, she was selling fax machines, struggling to get her idea off the ground late at night. But no one would take her call (or fax). She knew that she had to get a big fish, and so she went after Neiman Marcus, calling for days on end, trying to get the buyer. And finally she did.

“Hi, I’m Sara Blakely and I invented a product that is going to change the way your customers wear clothes. And if you give me a few minutes of your time I’ll fly to Dallas and show you.” To her surprise, the buyer, Diane, said, “Well, if you’re going to fly here I’ll give you ten minutes.”

So Sara headed to Dallas with her few essentials. “I have a ziplock bag from my kitchen with a prototype in it, a color copy of the packaging that I had created on my friend’s computer, and my lucky red backpack from college that all of my friends begged me not to bring.” And the meeting wasn’t going well. Sarah was losing her.

Until finally, Sara stepped out on a limb. “I said, ‘You know, Diane, will you just come with me to the bathroom?”

“Excuse me?”

“I want to show you my own product, before and after,” said Sara.

So they did. Sara showed her pants without Spanx, walked in to the stall and put on the Spanx, and walked back out to show Diane the difference. “She looked at me and said, ‘Wow I get it. It’s brilliant.'”

Diane placed an order for seven stores. And the game was on.

John Mackey started Whole Foods as a small natural foods store in Austin, Texas. One year later, during the flood of the century, his store was several feet deep in water.

“The sheer weight of the water broke through the glass,” he said.

Cars were floating down the street, and with it his dreams. The store was being looted. He went in with a paper bag and went to the safe and got all of the cash out.

“We had to rebuild the store, and we just didn’t have the money.”

“By all rights, Whole Foods should have died in that flood.”

Until finally, “There was a benefit held for the store, and the team members worked for free. Our bank loaned us money, on my signature, which was worthless. And the investors decided to kick in more cash. So we were able to move in 30 days later. That just pulled everybody together. We really united around that near-death experience.”

And so it continued. The power from the depths.

Tony and Maureen Wheeler of Lonely Planet have served as a lighthouse to backpackers all around the world. But they had their share of ’empty fridge’ moments. In the early 70s, they had traveled across Asia from England, arriving in Australia with only a camera and 27 cents.

They sold the camera, and got day jobs. But so many people had been asking for their stories and information about their trip, they decided to make a book of it, called Across Asia on the Cheap which was compiled in 96 pages. They kept in boxes in their apartment, and sold it book store to book store.

Until finally, they found a woman who said: “My flatmate is a journalist and she wants to interview you and your partner on television.”

Any traveler who has wondered how to find a good banana pancake in Benares or a good place to learn to salsa dance in Havana can look at what the Wheelers created with admiration – and even some envy.

But as in the depth of any transformative moment, while the story may now be history, the power, in fact, comes from the mystery. Not every story in your collection will have this depth, but there will be a few.

And, if they are well shaped, those few innermost cave stories will not only guide your audiences in their journeys, they will guide you.


Jay Golden is founder of Retellable, a storytelling coaching and training company focused on leadership development and public speaking. His book, Retellable: How Your Essential Stories Unlock Power and Purpose, is available on Amazon and Audible.

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