Storytelling for Startups

How to pitch investors, close customers, recruit talent, and woo partners.

Eliot Peper
Sep 16, 2014 · 7 min read

Storytelling is the defining skill of successful entrepreneurs. Some people think that technical brilliance, deep-seated passion, or unambiguous hustle are the most important founder traits. All of these certainly help. But the top 1% of founders distinguish themselves by their ability to weave a good tale.

There’s a very mundane reason for this. At the fuzzy front end of building a new company, most of what the CEO does on a daily basis is tell stories. Founders must lure investors to write them checks, convince friends and colleagues to join up, inspire their team to perform in the face of adversity, attract customers who have better things to do, and collaborate with partners whose goals may very well be divergent. That’s a prolific amount of storytelling even for an author like myself.

If storytelling is so important, why do most founders suck at it? Crappy stories hamstring otherwise stellar startups all the time. Companies flounder in the shallows. Missed opportunities pile up like debris after a hurricane. The good news is that improving your story might not take a lot of effort but could yield surprising results.

“The secret to good writing is having something to say. The secret to having something to say is to live an interesting life. What makes a story worth telling? If you feel like you can’t *not* tell it. If you *have* to share it with friends over drinks and they get excited (or laugh hard) and ask a ton of questions.”

Tim Ferriss, #1 NYT bestselling author and leading seed investor

Remember that high school teacher that made advanced algebra the most exciting item on the menu? Or the other teacher that somehow made World War II incredibly boring? Enthusiasm is contagious. Be yourself. Tell the truth. If you believe in what you’re doing then all you have to do is make yourself vulnerable and others will catch the bug. Let your passion peek through your professionalism.

“All our films suck at the beginning.”

Ed Catmull, President at Pixar and author of Creativity Inc.

Storytelling is a craft. Just like product development, you have to improve your story through practice, feedback, and iteration. What points does your audience engage with the most? Give them more of what they want. What moments light a spark in their eyes? Double down. When do they start to nod off? Cut! Pixar has axed multiple films late in their development because they simply weren’t up to snuff. You wouldn’t release a product that sucked. Bring that same level of quality control to the stories you share.

“Show, don’t tell.”

Writing adage

A demo is sexier than a description. A customer testimonial is more powerful than marketing material. Traction metrics are more convincing than projections. A solid lead investor is better than a group of “soft-circled” followers. Don’t fall into the trap of framing your startup vis a vis every reference point imaginable. Let your work speak for itself.

“Try to leave out the parts that readers tend to skip.”

Elmore Leonard, bestselling novelist and screenwriter

Drop the boring bits. Founders often spend a lot of time talking about their product. This makes perfect sense. They spend most of their time building that product and are deeply engaged with the technical details. The problem is that their audience usually doesn’t care that much about the product itself. They have other questions that need answering. What’s the overall market opportunity? Does the team have the right people to win? What’s the unfair advantage? If someone yawns during your pitch, skip to the next plot twist before you lose them forever.

While you’re at it, skip the acronyms and buzzwords too. They’re a crutch that can easily alienate your audience. If your story doesn’t make common sense, you’ve got bigger problems.

“Don’t make stuff because you want money. It will never make you enough money. Don’t make stuff because you want to get famous, because you will never feel famous enough. Make gifts for people. And work hard on making those gifts in the hope that those people will notice. Maybe they will notice how hard you worked and maybe they won’t. And if they don’t notice, I know it’s frustrating. But ultimately, that doesn’t change anything because your responsibility is not to the people you’re making the gift for, but to the gift itself.”

John Green, bestselling author of The Fault in Our Stars

Nothing is more transparent than someone overselling themselves. The only way to guarantee that you’ll sever the connection with your audience is by erecting a facade yourself. Don’t boast. Share what you are already accomplishing. Instead of saying “we’re in conversations with 17 new customers”, say “we closed 2 new customers this month.” Authenticity trumps bluster every time. Anyone you want to work with should know who you really are. Every product you release, every blog post you publish, every pitch you deliver, should be a gift.

“The fact of storytelling hints at a fundamental human unease, hints at human imperfection. Where there is perfection there is no story to tell.”

Ben Okri, acclaimed Nigerian poet and novelist

Founders tend to focus their story on the solution their startup posits and the utopian vision they will realize if successful. But that’s boring. What if Star Wars started after the Rebels had defeated the Empire? Or if the Hunger Games began once Katniss Everdeen had overthrown the Capitol? Or if Harry Potter had already ousted Lord Voldemort before the first book began?

Good stories focus on the act of overcoming incredible obstacles. The hurdles are the interesting part, not the medal ceremony. Think about the last time you watched the Olympics.

What does this mean for founders? Focus on why the world is broken, not how you’re going to fix it. Articulate all the angles of the problem you’re attacking. How does it impact people emotionally, financially? How does it make their lives miserable? Why is it so hard to deal with? The better you illustrate their pain, the more the tension builds. Your solution is the punch line, don’t steal its thunder.

“Empathy is about standing in someone else’s shoes, feeling with his or her heart, seeing with his or her eyes. Not only is empathy hard to outsource and automate, but it makes the world a better place.”

Daniel H. Pink, #1 NYT bestselling author of Drive

Know your audience. Why are they taking this meeting with you? What drives them? Who inspires them? What would delight them? Customers, talent, press, team, and partners all care about different things. Reflect on what their goals and priorities are. Figure out what the perfect gift would be for them. Make their days.

Many early stage founders devote a lot of mindshare to pitching investors, so let’s take them as an example. What motivates early stage investor decision-making? Most people think it’s projected returns, differentiated technology, or a particularly clever idea. Nope.

What actually drives investors to write checks? Fear of missing out. Early stage investors spend all day listening to pitches by entrepreneurs. But how do you pick the needle from the haystack? How do you know you’re not passing on the next Google/Facebook/Twitter? That question loiters in the psychological shadows of every coffee meeting. A seed investor’s worst nightmare is missing out on the hottest deals, especially because such a minuscule percentage of deals return almost all the profits.

Entrepreneurs can play on those precise heartstrings. How can you make an investor feel like they’re about to miss the boat? Demonstrate all the progress you’ve made and how the train is leaving the station already. Share how much competition you’ve built around the deal, how many other respected investors want in. Illustrate how you will be wildly successful even without their check. The easiest way to raise money is to not need it.

What themes should you touch on? Investors measure the success of their portfolios based on Internal Rate of Return or IRR. But IRR also fills in for the traits they look for in startups: Inevitable, Relentless, Resourceful. Founders with these qualities can’t help but find success, even if it’s unplanned. When you’re pitching investors, make sure your story highlights examples of how your startup lives out those themes.

“If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.”

Antoine de Saint-Exupéry, pioneering aviator and author of The Little Prince

Stories are human things. They help us make sense of complex problems. They orient us in the never-ending whirlpool of personal experience. They allow us to communicate and form our own identities. They bring us to tears and inspire us to transcendent action.

Entrepreneurs must master storytelling to find success. Good companies are people-driven just as good books are character-driven. And there’s this weird thing about people, they’re story-driven.

Need help crafting your story? I work with entrepreneurs, executives, and investors to articulate, refine, and share the stories that define them.

Eliot Peper is the author of Cumulus, Neon Fever Dream, and The Uncommon Series. He’s helped build technology businesses, survived dengue fever, translated Virgil’s Aeneid from the original Latin, worked as an entrepreneur-in-residence at a venture capital firm, and explored the ancient Himalayan kingdom of Mustang. His writing has appeared in Popular Science, Businessweek, TechCrunch, io9, VentureBeat, Entrepreneur, Forbes, Xconomy, and Ars Technica, and he has been a speaker at places like Google, Qualcomm, and Future in Review.

Startup Lessons Learned

Lessons learned the hard way — submissions tweet…

Eliot Peper

Written by

Novelist: Veil, Breach, Borderless, Bandwidth, Cumulus, Neon Fever Dream, True Blue, and the Uncommon Series (

Startup Lessons Learned

Lessons learned the hard way — submissions tweet @michaelsacca

Eliot Peper

Written by

Novelist: Veil, Breach, Borderless, Bandwidth, Cumulus, Neon Fever Dream, True Blue, and the Uncommon Series (

Startup Lessons Learned

Lessons learned the hard way — submissions tweet @michaelsacca

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store