Creating Your Perfect One Liner

The 3 Rs of creating the perfect one-liner

November 15, 2022
min read

Greetings, Chief Storytelling Officers.

Welcome to edition number 20 of the newsletter. It's wild to see 1,451 founders and storytellers reading this newsletter.

I want to say thank you for reading. I also want to say one more thing about the first 20 editions...

We're just getting started.

This one today will be all about the best way to build out your one liner. It's one of the trickiest parts for any speaker.

So if you're a founder, this will help you figure out how to build the perfect one liner for investors.

And if you're not a founder, today will help you create the perfect theme for any talk so you can make sure your message always lands.

Like Heath Ledger said as the Joker...


DEEP DIVE: One Line to Rule them All

You probably heard that tennis legend Serena Williams is calling it quits on her iconic career back in September. It was a truly monumental moment, because not only has she absolutely dominated the sport for nearly 25 years, but she’s paved the way for so many female and Black athletes to come.

To honor her accomplishments, Nike ran an ad about her after the US Open. The one minute short was spine-tingling and inspiring, but what grabbed me most was the ending tagline: “By changing nothing, she changed everything.”

That wordplay is so beautiful and perfect. It immediately grabbed my attention. I couldn’t get it out of my head for days after I saw the ad.

Ironically, the ad also coincided with a book I was reading at the time called Words That Work: It’s Not What You Say, It’s What People Hear by Dr. Frank Luntz. The book details how the tactical use of words and phrases can affect what we buy, who we vote for, and even what we believe in.

Think about it—one-liners shape our understanding of our past and present. . “Ask not what your country can do for you, ask what you can do for your country.” “The only thing we have to fear is fear itself.” “One small step for man, one giant leap for mankind.” They’re the phrases that stick with us. We don’t forget them.

When I was a trial lawyer, I obsessed over finding the perfect one-liner that could summarize a case and capture my audience.

One of the biggest one liners of my career came in a murder trial where I used a variation of a line in The West Wing when I was defended a client in a murder case where I believed he acted in self defense. As one of only two cases I ever tried on the defense side, this also ended up being the last trial of my career.

The line I used as my theme...

"Vengeance is not justice".

It worked. The jury connected to that line. They told me that line was repeated over and over in the deliberation room. And they ultimately voted not guilty on the murder charge to allow my client to go home a free man.

The magic of words is also the reason I landed on Performative Speaking as the name of my company.

Performative = performance art

Performativity = the ability for words to bring about change

Art + Change.

As a founder, this is EXACTLY what you’re trying to achieve. When you’re sharing your story with an investor, a recruit, or even your team, you want lines that are so powerful that people can’t forget them.

One liners can absolutely make or break a startup pitch. Unfortunately, the majority I hear are boring, confusing, and uninspired.

If you as a founder can’t quickly summarize what you do in a memorable way, it’s going to be a long and tough fundraise. There’s so much noise and so many companies that it’s hard to stand out.

So why don’t more founders have a stronger one-liner? The thing is, using our words to their fullest effect is hard and takes time. You have to REALLY think through how you’re going to come up with something so magical, so memorable, that it moves people in unimaginable ways. That they leave your pitch meeting unable to get you out of their head.

Here are three tips for crafting the perfect one-liner:


Even though it might seem like good one-liners are hand-delivered from the heavens, you might be surprised to find that most of them follow a structure or formula. This is because we humans are attracted to patterns we’re already familiar with. We know there’s a good chance the superhero is going to save the day, but it doesn’t stop us from seeing every Marvel movie, does it?

As such, I think a good place to start is doing some research on classic rhetorical devices and ways of writing.

One example is the Rule of Three, a pattern that for some reason is very mentally and emotionally satisfying. It dates back to the beginnings of oral history (think The Three Little Pigs and Goldilocks and the Three Bears), but is also very prevalent in modern rhetoric. What are the rights of all Americans? Life, Liberty, and the Pursuit of Happiness. What do you do when you’re on fire? Stop, Drop, and Roll. What sound do Rice Krispies make? Snap, Crackle, and Pop. The Rule of Three aids instant recall.

Another satisfying device is parallel structure, where phrases are balanced with repeated words or syllables. Great orators lean on this tool often—like Winston Churchill in 1945, when he proclaimed: “The inherent vice of capitalism is the unequal sharing of blessings; The inherent virtue of Socialism is the equal sharing of miseries.” Or Abraham Lincoln in his Gettysburg Address, when he said a government “of the people, by the people, for the people shall not perish from the earth.”

There are dozens of other devices and patterns—alliteration, onomatopoeia, repetition—many of which you probably learned in high school and wondered when they’d ever come in handy. That time is now. It’s a worthwhile investment to research and revisit these tools.


In 1972, a Jamaican named Clive Campbell was DJing his sister’s birthday party in the Bronx when he began looping the drum beat of a song and talking over it. Knowing he was onto something, he refined this “break beat” style of DJing over the next few years at parties. It caught on and spawned a massive grassroots musical revolution. Most historians attribute Campbell—better known as DJ Kool Herc—for inventing what we’ve come to known as hip hop.

Herc didn’t write or record the music he rapped over, but he did adapt it in a whole new way. And that’s another avenue for you to travel down in search of your one-liner.

Great speakers, storytellers, and communicators borrow, remix, and use previous material as inspiration. They take from other worlds, time periods, and sectors. If you think about it, in MLK’s final speech in 1968, he borrowed heavily from The Bible. His line about being to the mountaintop is drawn from Moses and the journey to the Promised Land.

I’m not talking about ripping people off, like many accused Melania Trump of doing to Michele Obama in 2016. I mean repurposing common and culturally recognized concepts with your own twist.

In his book, Steal Like An Artist, author Austin Kleon says that nothing is original, so you should embrace influence, school yourself through the work of others, remix and reimagine your own path. Inevitably, you’ll fail to imitate the work perfectly, and that’s when the magic of blazing your own trail occurs.

Look at the greats. Deconstruct what they say and how they say it. Pull it apart and piece it back together in a way that’s wholly original.

After all, it was Pablo Picasso who famously said: “Good artists copy, great artists steal.”


I hate to break it to you, but when you’re trying to come up with that perfect one-liner—that tight, concise, memorable line that you’re going to use to define what you’re building—you’re going to get frustrated. That’s normal. If it was easy, everyone would have a perfect line, and then the words wouldn’t have the same effect. Instead, it’s going to take time, effort, energy, and a lot of failed attempts.

There’s a classic quote that exemplifies just this: “If I had more time, I would’ve written a shorter letter.” It’s often attributed to Mark Twain, but research suggests many have said similar things over the years, including Benjamin Franklin, Henry David Thoreau, and Woodrow Wilson.

All of these greats understood that boiling thoughts down to the perfect words takes time and effort. That’s where revision comes into play.

My good friend Justin Mikolay was a speechwriter for General David Petraeus, Jim Matthis, and Leon Panetta, and he’s always told me there are three secrets to getting a speech right: rewrite, rewrite, rewrite (side note: notice the Rule of Three and repetition in action here?). He said he’d often go through 10 or 15 revisions of a speech before he finally got it right.

I found the same to be true when I was a lawyer going into trials on a regular basis. I was forever trying to get the theme right, finding that one line that was the perfect summary of what the case was about. Many times, I wouldn’t get it right until I walked into court, because I was testing and re-testing and figuring it out.

There’s nothing wrong with tinkering. In fact, it’s how most wordsmiths find the right way to say something. Bestselling author David Sedaris is well known for his humorous essays and never-ending speaking schedules. Sedaris holds an average of 150 speaking events a year, but he rarely reads previously published material. Instead, he reads early drafts of unpublished stories, using each audience as guinea pigs.

“I write something over probably 12-18 times,” Sedaris said in his MasterClass. “I’ll read it in front of an audience and I’ll make notes, and I’ll rewrite it. Read it, rewrite it, read it, rewrite it. Because writing IS rewriting.”

I fully believe that the perfect one-liner is within every founder, but it’s not going to be easy. So few people are willing to put in the time, the effort, the energy to do it. But when you do, you rise above.

This is why there are certain speakers and storytellers and founders that people gravitate towards time and time again. If you ask, “Who’s the best speaker?” or “Who’s your favorite storyteller?” You’re going to hear the same names come up because they’ve monopolized attention and dominated the conversation around speaking and storytelling.

You’re not alone. You can do this. It’s worth it. If you get it right, you’re going to have a moment like Nike did in September, when they left me and so many others speechless about Serena Williams’s impact on the world.

RESOURCES for Founders and Storytellers

Want to research how the great orators became great? Start now with Winston Churchill. The Splendid and the Vile by Erik Larson is a book about Churchill at the outset of World War 2, and it provides interesting insights into his speechwriting practices. Or, if history isn’t your thing, you can read this great summary of Churchill’s 14 best writing tactics by Matt Tillotson on LinkedIn.

Last year, OpenAI announced a startup fund that would distribute to early-stage AI startups. AI is crazy hot right now and OpenAI announced it led a $23.5 million investment in Mem, a work-focused app that taps AI to automatically organize notes. A cool project with a lot of great backing. It's an exciting time inside of this space. Read the article about the announcement here.

Managing Partner of Antler US, Tyler Norwood, recently released an amazing episode with Tyler Tringas of Calm Fund. They talked about what VC does well and went into other models for founders that may want to take a different approach. I loved it because most founders chase venture capital when it's not the right path for them. This episode gives alternatives and dives deep into what it really means to be a venture backable founder.


Over the past 20 weeks I've loved reading all the stories of how readers like you have used these lessons to successfully fundraise, hire amazing people to your teams, and even give wedding toasts using these lessons.

I love hearing from all of you. Keep the wins coming. I read every single email.

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See you next week.

At Performative Speaking we work with founders that want to be world-class storytellers and fundraisers. We believe the biggest change makers will be the best storytellers and that's who we bring on as clients. It's not cheap, but you can always apply to talk to our team who will send it my way if it might be a fit by filling out this form.

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