Your Story is Your Moat

A Conversation with Obama Speechwriter Terry Szuplat

Founders are outsourcing their voice to ChatGPT. Pitch decks all sound the same. Nobody knows what anyone actually believes anymore. And here’s the kicker: raising money is storytelling. You need to get investors and employees to believe in a future that doesn’t yet exist. In a world flooded with AI-generated everything, a human voice—a real one—cuts through louder than ever.

Which is why I sat down with Terry Szuplat, former Obama White House speechwriter and author of Say It Well, winner of Porchlight’s best marketing and communications book of 2024. Here’s our conversation, edited for clarity and ease of readability:

Tom: Pitching to raise money is basically an exercise in storytelling. How can highly technical founders—who’ve been rewarded in classrooms for having the answer, not worrying about storytelling—make this mindset shift?

Terry: So much of our lives, particularly in academia, we’re told: provide evidence, provide data. That’s the way to make your case. But there’s a limit to what stats and numbers can do.

There was a fascinating study at the University of Pennsylvania where participants were given real money to donate during a food crisis. One pitch was all about stats—how many people were impacted, how big the problem was. Another pitch told one story of one kid and the difference your donation can make. Which raised more money? Of course, the story.

But here’s what was fascinating: there was a third group where they combined the statistics with the story—which is what we used to do at the White House. The donations actually went down.

I reached out to the professor who conducted this study and asked what was going on. She said something so obvious we all forget: you can’t have a human connection with statistics. That’s not what moves people. The more you load something up with numbers, the more likely you are to lose your audience. Great leaders, great fundraisers are great storytellers. If you’re drawn to facts and tend to rely too much on data, well, let’s look at the data—stories are actually more powerful than data.

Tom: In the age of AI, all the competitors in one of our companies are saying all the same things with that ChatGPT-like twang. Beyond having a good story, how do we punch through and not sound like AI slop?

Terry: This has always been a problem. When people come to speechwriters like me, they often ask, “What should I say?” One of our initial responses is: say what only you can say.

AI is just exacerbating a problem that’s been around forever—everyone tends to sound like everybody else. Put yourself in the position of the audience. Imagine you’re the third or fourth speaker at a conference and everyone’s saying what you were already going to say. That’s a great sign you weren’t saying anything particularly unique.

You’ve got to stand out. What can you say that nobody else can say? That word “only” is key. I’ve worked with companies who say, “Here’s the problem, Terry. There isn’t anything we can say that anyone else can’t say.” That’s not a communications problem—that’s a mission problem. You haven’t found your niche, your competitive advantage.

I always encourage people to answer this simple sentence: “We are the only company that...” If you cannot answer that, you do not have a compelling pitch.

Tom: That requires getting personal, which is misery-making for most technical founders. You’re asking people to be vulnerable.

Terry: Why should they choose you? On some level there’s only so much you can say about the differentiating qualities of different products. But what is truly different is you and the story that you bring. We see this throughout history—great business leaders realize they’re not just selling a product, they’re selling a set of values and themselves.

If a potential investor or customer can go either way and they’re having trouble deciding, it’s going to be the founder, the CEO, their story, their passion that might tip the scale in your favor. I’ve talked to corporate speechwriters who say their CEO doesn’t want to get personal—they don’t want to be vulnerable. And I ask, “How are the speeches?” “Oh, they’re terrible. They’re boring. They sound like everybody else.”

We’re not telling people to divulge what you say to your therapist. But the whys of why you do this work—how did you come to it? So often founders are trying to solve problems they’ve already encountered in their own life. Tell that story. That’s a powerful story.

Tom: I remember being asked to speak to entrepreneurs at Stanford years ago, and they insisted I not talk about entrepreneurship—they wanted my personal story. I thought, “who cares?” But when I got up there and just went for it, it was astounding how much people needed to hear it. Afterwards people were high-fiving me, telling me how important it was.

Terry: That’s what a lot of people say—”I don’t really have anything to say about me, I’m just like everybody else.” That’s very humble, and that’s appealing. But what does it have to do with anything? It has to do with everything. You are a human being speaking to other human beings. Humans connect with each other as fellow human beings. That means stories, that means opening up, that means being vulnerable.

We’ve seen it over and over again—politicians who are too robotic, business leaders who are too sterile—their audiences can’t connect with them. You’re not being arrogant. You’re doing it because it’s one of the most powerful ways you connect with your audience.

Tom: You wrote about how Obama asked you to write two speeches about General Stanley McChrystal—one accepting his resignation after that Rolling Stone interview, the other keeping him on. How did seeing the words on the page help him decide?

Terry: I include that in the book as a powerful example of why we should write things down—it helps us see the strengths and weaknesses of our arguments. It’s easy to BS and brainstorm in a room, but once you have to put words down, make your argument, then see it, all of a sudden you see—and your team sees—that’s actually not a very compelling argument.

I remember being on the fence about that situation. But the moment I saw those two drafts and read them, I realized, “Oh, he has to go.” This is not good for civil-military relations, not good for civilian control of the military in the middle of a war. You can’t have a general speaking like this about the Commander in Chief. It just wasn’t tenable. But it was only when I saw that written down.

Writing doesn’t just send important signals to external audiences—it’s the marching orders for your team. A lot of President Obama’s speeches weren’t just speeches to the American people. They were speeches to the 2 million military and civilian employees of the federal government who needed to carry out those policies. They needed to know clearly what he believed and what direction he wanted them to go in.

Don’t wing it. We’ve seen over and over again in politics and business, when you wing it, you’re asking for trouble.

Tom: I’ve learned to write everything down, then distill it into five key things so I’m not reading from a script. But having perfect precision and clarity on what you want to say, with your thoughts organized in advance—I can’t agree more.

Terry: You mentioned not reciting a speech, and there’s a whole debate about this. People say you should never read a speech, never read a script. I think that’s too simplistic. You shouldn’t recite speeches—that’s the right way to say it.

Most people don’t have a photographic memory. When you try to memorize, you’re focusing on the wrong thing—the moment you miss one word or sentence, you’re completely thrown off. Presidents read speeches all the time. Great leaders read speeches. Some of the greatest speeches of all time were written down.

The question is not whether you read—it’s whether it’s authentic, whether it’s good. You can have a script and read it terribly with bad body language and bad delivery. So write it down. If you don’t write it down, how do you practice consistently? You’ve got to have something to work off of. The more you practice, the more you read it out loud, the better you’ll be when you actually deliver it.

Tom: Obama was one of the most talented communicators in an awful long time. What techniques did he use to make complex ideas simple, emotional, and memorable?

Terry: Don’t believe what you see online—all these posts saying there’s 12 or 14 key elements of a great presentation. I’ve been doing this for 30 years. No one ever told me what these 14 elements are. It’s actually not that complicated.

We’d often meet with the President in the Oval Office before a big speech. I wasn’t on his 2008 campaign—I joined a few months into his presidency. In early meetings, he’d give us guidance, walk through everything, then say something like, “Make sure it has a beginning, a middle, and an end.”

I’d nod like I knew what he was talking about, but I was thinking, “What does that mean? Of course you start speaking, keep speaking, stop speaking.”

What he was getting at—and remember, before he became a politician, he was a writer, an author with a deep appreciation for narrative arc—was that a great presentation, just like any great story, has a clear beginning, middle, and end. Going back to Aristotle over 2,000 years ago: you set up a problem, you solve the problem, you show what the future can be like with your problem fixed.

We wrote over 3,000 speeches for the President during those eight years. If you go back and look, just about every single one breaks down into this three-part framework: problem, solution, vision of the future.

You’re putting together an elevator pitch? Even if you only have seconds, hit those three points: What’s the clear problem you’re trying to solve? What’s your solution? How is their life, their world different, better because of it? That’s all you need to do.

Tom: Those White House Correspondents’ Dinners were awesome—Obama was joyful, fun, good with jokes. How important is humor, and when should you inject it?

Terry: People approach me and say, “I’m giving this speech, give me a joke. I need an opening joke.” That’s the wrong way to think about it. You don’t need a quote-unquote joke. You’re not a standup comedian. Humor is different than a joke. There are all sorts of ways you can bring lightness and levity without a setup and delivery.

The Correspondents’ Dinners almost mislead people. Obama had great comedic timing, but those were very unique situations where he was almost in the role of a standup comic. In those 3,000 other speeches, it was just a little piece of levity, a little lightness to get people smiling.

I teach speechwriting at American University, and I always tell my students: just say a little something to put the audience at ease. Not a joke—something about your own life, something about their experience, some shared connection.

The interesting thing is we do this all the time in conversations with colleagues, friends, and family. Most of us don’t speak without any humor or levity in regular life. We just have to bring that same authenticity to our presentations.

Lightning Round

Tom: What’s one myth about storytelling every founder in tech needs to forget?

Terry: “It’s not about me. They don’t want to hear about me.” They do. They really do. It’s not all about you, but they do want to hear something about you.

Tom: What’s the clearest sign a founder has botched his own messaging?

Terry: When they’re no longer talking about the things, ideas, and values that inspired them to start the company in the first place.

Tom: What’s one Obama speechwriting principle every CEO should adopt?

Terry: Know what you believe. I asked him once what makes a great public speaker. I thought he’d talk about narrative arc, storytelling. He said great leaders, great speakers are people who know who they are, know what they believe, and speak from a place of conviction.

Tom: When does being yourself actually hurt your pitch?

Terry: I’m a huge believer in vulnerability and honesty—that’s a credibility boost. But if markets and funders are looking to you for answers and you don’t have them, that’s a problem. We had a famous example in the Obama administration where the Treasury Secretary went out during the financial crisis, and the money line in the speech was “We’ll have more details next week.” The stock market tanked the moment he said that. If folks are looking for answers, that’s the moment for answers. That’s a leadership moment you can’t not deliver.

Tom: What excites you most about how AI and human communication can work together?

Terry: The speed with which it helps us do research and find those little nuggets that can bring a presentation alive—a story, an anecdote, a fact. Often it takes hours to dig through and find those things. If AI can help us find those little nuggets we can sprinkle through our presentations to make them beautiful, that excites me.

Tom: This conversation has been full of nuggets and actionable thinking for people struggling with these problems. The journey is probably never over, right?

Terry: Absolutely. President Obama was very candid about this—even as president, he was working to get better. Public speaking and communication is a skill. Like anything, you only get better the more you do it.

Tom: I remember in the book when Obama says, “Listen, you should have seen me way back when I really sucked.”

Terry: People forget—folks see someone like Barack Obama and say, “Oh, what a naturally gifted speaker,” which is basically telling yourself you can never be that. What you’re seeing when you see someone at the top of their game is years and decades of hard work to get there. They’ve put in the reps.

We may never sing like Taylor Swift or give a speech like Barack Obama, but we all can get better. That’s what I’ve tried to lay out in the book—ways all of us can improve.