Introduction

I was tired, frustrated, and confused about what to do next. Two years after I finished my MBA at the University of Texas at Austin, I began my first start-up, a tech company with my best friend. We were months into the launch and were readying to approach angel investors for our first outside investment.

We had been working on our business plan and pitch deck for months and had been told by peers and informal advisors that there were still umpteen things wrong even after all the updates and changes we’d made. She and I felt completely lost. It was late afternoon on a Monday when I remembered a monthly meeting that night at the Austin Software Council where they would be bringing in a speaker to talk all things start-up. We were still chipping away at our deck, and I had originally planned to skip the talk because we had too much to do. There was no time to listen to someone yammer on about their start-up when ours needed so much work.

However, completely drained by the current challenge, I decided to get out of my apartment and step away from my computer to take a break from the grind. I arrived late to the meeting and had no clue who the speaker was, but the two-hundred-seat auditorium was packed. I assumed the guy was important but didn’t recognize him as he stood at the podium.

He carried a duffle bag to the podium and began by stating that he’d like to tell his story using a set of T-shirts he had in the duffle bag. He reached over and pulled out a T-shirt with a company logo on it. He held it up for everyone to see and said, “This was my first company.”

I had never heard the company name or seen the logo before. “This was a cool idea,” he said, “but we never could get the technology to work.” He put that shirt down, reached into the duffle bag, and pulled out another shirt. Again, unrecognizable. “Now, this company was a cool idea,” he began. “We got it to work, but we couldn’t turn it into a product that anybody cared about, so that company failed as well.” He put that shirt down and pulled out another. “This was our third company. It was a great idea and great technology. We turned it into a product that worked, but nobody would buy it. It was a terribly frustrating situation.” He shook his head, put that shirt down, and pulled out yet another. “This company was a great idea, great technology, and a great product. We started selling, but a key partner didn’t want the product to continue, so we ended up shutting it down.”

He put that T-shirt back in the bag, and at this point, I remember thinking, This man has failed multiple times, and he’s confidently sharing his failures; he has to be someone special. He went on to share another failure. From what I recall, this was another great idea, great company, great team, incredible technology, product, and market opportunity, but it was just the wrong timing. They lost millions of their investors’ money. At this point, I was thinking, Who is this guy?

Finally, he held up his last T-shirt but kept the name on it hidden. Then he said, “This was a great company. Great idea, great technology, great market opportunity, great founding team. And the people that had just lost the money in our previous company? They funded us.”

He turned the shirt around, and in big letters on the front, it said AOL.

AOL, or America Online Inc., was one of the most successful and recognized web brands in the 1990s and an early pioneer of the internet. The man on the stage that night was Marc Seriff, one of the original founders.

That night, I went home with a new sense of optimism and vigor to complete the deck and business plan. The work paid off. Within a few weeks, we closed our first $100,000 seed investment. The company I founded would go on to have its own ups and downs, but what remained from that experience that night was Marc Seriff’s story and the inspiration it gave me.

When I spoke to Marc recently, I told him how he’d inspired me. He was humbly honored. Though I may not have remembered the exact dialogue or all the exact details of his story, the spirit of what Marc said and the message of perseverance and determination were the same. All these years later, I can still picture Marc on stage with his duffle bag and T-shirts. I remember exactly what I felt, what I saw, and how it motivated me. I didn’t know it at the time, but that talk planted the entrepreneurial storytelling seed in me, and I would soon come to learn how powerful story can be.

The Entrepreneur’s Journey

Entrepreneurship is one of the most rewarding and fulfilling endeavors you can undertake. Few things give you the kind of personal pride and internal reverence that comes with being called a founder, where every decision starts with you—from the company name to the culture to the product you want to build or service you provide.

At the same time, few things are more all-consuming than launching a company. You are often operating on an island, responsible for everything with no one to turn to. You alone are the champion of your idea. No one has ever heard of your business or knows who you are or what your product does. You work with few resources on a limited runway, constantly punching above your weight class.

To compete as a start-up, you need something that levels the playing field. You need something that allows you to compete no matter the time, place, setting, or resources. You need an instrument of persuasion and influence that gives you an advantage over market gorillas one hundred times your size.

That instrument is your story.

Twenty years after hearing Marc Seriff’s story, the lesson remains the same: a great story changes everything. A compelling story has the power to catalyze movements, disrupt industries, and topple giants. It can help build empires, create legends, and rewrite history. Almost every successful entrepreneur started his or her company with a story. And every founder can create a great story—regardless of industry, age, or resources. The more you invest in story, the more it will help you accomplish your goals. In fact, there is a direct correlation between success and the entrepreneur’s ability to create and tell their founding story.

Blake Mycoskie, the founder of TOMS, knows this well. One day, Blake was in an airport and saw a woman wearing a pair of the shoes he’d designed and manufactured. Without identifying himself, he told her, “I really like your shoes.” The woman turned to him and said, “Oh, these shoes are amazing. The company that sells these shoes is incredible. For every pair that gets bought, a child in need in another country gets an equal pair of shoes. It’s truly amazing.”

He kind of smiled to himself and said, “That’s great,” and started walking away.

The woman reached over his shoulder, grabbed him, and said, louder and with more emotion, “No, you don’t understand; for every pair of shoes that a person buys, a child in need, a person in need, gets a free pair of shoes. That’s unbelievable.”

She was so passionate about the idea that Blake realized something exceptionally powerful that day. The very product, the very thing that he was selling, was a story; and because of that story, his customers had become his evangelists. Once an audience understands an idea like Blake Mycoskie’s—that for every pair of shoes that you buy, someone else in another country who has no money is going to get a pair of shoes—they will forever be tied to that association.

That’s the real power of the story—to create an immeasurable connection between you and your audience. Connection is the magic that makes stories work, more so than any fact or figure you could ever share. Story is one of those rare tools that simultaneously connects us yet allows us to distinguish ourselves by bringing to light our uniqueness.

Discovering the Power of Story

As an entrepreneur who’s spent the last fifteen years filming entrepreneurs like Blake Mycoskie for a living, I know firsthand how powerful story is. My production company is responsible for capturing and sharing the stories of entrepreneurs worldwide. I’ve produced videos for TV networks, magazines, and corporations as well as for the founders themselves. I’ve even created and produced a series for CNBC called American Made. I have the good fortune to be around the best of the best, having filmed more than five hundred of the top entrepreneurs in the world, including the founders of Starbucks, Whole Foods, LinkedIn, Paul Mitchell, Dropbox, Zappos, and The Knot.

But before I delved into producing videos, I was a founder looking for ways to bring my ideas to life and figuring out how to get the resources I needed to build companies around them. I’ve been told no by dozens of media outlets, hundreds of investors, and thousands of prospects. I’ve started eight companies and organizations, crashed and burned miserably a few times, and had some good fortune in others. My path has been...