As a full-time graduate student and full-time editor, I’ve done a lot of public speaking in recent times. Sadly, I don’t recall practicing before any of these moments. Sure, I took notes for reference but actually saying words out loud? Nope. I know I’m not the only one who walks into a meeting or presentation thinking they’ve got it handled only to realize they’ve forgotten to share important info or wish they’d put their checklist in a different order. Practicing is a necessity and an art well worth learning, whether you’re pitching a business idea, teaching an online course, or recording video content for your website (among many other scenarios you’ll want a dress rehearsal for).
In his book Backable: The Surprising Truth Behind What Makes People Take a Chance on You, Suneel Gupta, with Carlye Adler, reminds us that knowing how to persuade others matters just as much talent, connection and ideas. Getting into the room is one thing. Getting everyone in that room on your side is what really seals the deal and practicing is the essential skill that could make or break these encounters.
Before clicking into your next Zoom presentation or walking into a pitch meeting, read on for game-changing advice from Gupta and Adler on becoming a better public speaker, including why the number “21” is so important.
Describe the mindset that typically tricks us into thinking practice isn’t necessary.
It’s not that we think we don’t have to be prepared as much as we are preparing the wrong way. We prepare wrong. Before I learned this, I made this mistake…many times. In one, a particularly high stakes interview with Jack Dorsey—you can read all the embarrassing details in the book—I did my research, wrote down notes, and prepped questions—I did all the things we do to prepare for an interview. But I missed something key: I didn’t practice.
Oren Jacob, the former CTO of Pixar and someone who was been thrown into the Backable epicenter of the universe, showed me how short-sighted I’d been to skip that step. “When you were studying for a test in law school, would you take practice tests, right? So, for a law school exam, you would spend hours practicing, but for a meeting that could have changed your career, you didn’t practice at all?”
He wasn’t trying to make me feel bad, but it was a wake-up call. Not just because of the Jack Dorsey meeting but because of every meaningful interaction in my career until that point. All the presentations, interviews, coffees. I couldn’t think of a time when I actually practiced before the meeting.
Having now coached founders and creators, I’ve seen firsthand how exceedingly rare it is for someone to practice before their pitch. We’ll spend hours researching, outlining, pulling together slides—but very little time practicing what we’re going to share. The feeling seems to be that if we have the right content and we know it well enough, then there’s no need for practice.
But I’ve found that backable people tend to practice their pitch extensively before walking into the room. They practice with friends, family, and colleagues. They’re rehearsing on jogs with running partners, in the break room, and during happy hour. They prepare themselves for high-stakes pitches through lots of low-stakes practice sessions—what I now call exhibition matches.
What is the “rule of 21?”
My friend Josh Linkner is an award-winning jazz musician and keynote speaker, and he actually just published a book too. Linkner told me that great musicians and speakers are able to pull off legendary performances not from believing that everything will go right—but from being confident enough for everything to go wrong.
He said something I found kind of shocking: “When I play jazz, I go into a gig with a lot of confidence. But confidence isn’t what you think. It’s not that I’m going to play it perfectly. It’s knowing that I’m for sure going to screw something up. But because I’ve practiced so much, I have confidence that I can recover. Knowing that makes me feel bulletproof onstage.”
I wanted to feel bulletproof onstage so as I was preparing to give a speech to more than seven hundred fund managers in California, I asked him how many reps I needed to play. His answer made my face fall: “Twenty-one practice rounds.” Up to that point, I couldn’t remember practicing anything twenty-one times. And yet, when I later shared the Rule of 21 with highly backable people, no one batted an eye.
So, I got started. I did my first exhibition matches with my wife and kids until they got tired of hearing my speech. Then I went to friends. Calling someone I hadn’t spoken to in a while and asking, “Would you mind if I gave you a practice run of my speech over Zoom?” felt awkward. But very few people declined and I found myself not only reconnecting with friends but also inching closer to my target of twenty-one.
Around my tenth practice round, I felt something new. I knew the material so well that I no longer needed to focus on it. Instead, I could use that attention span to survey my audience. I could observe how each message was landing and make adjustments along the way. In earlier practice rounds, if someone seemed confused, I’d simply move on to the next point. Now I found myself being able to adjust on the fly—I would slow down and re-emphasize for clarity. If they seemed excited, I’d dial up my energy even more. If they laughed, I’d smile with them. My talk was starting to feel more like a dance than a pitch.
Why 21 times as opposed to 5 or 50 times? Is there a science behind it?
Such a great question and I’m laughing because we had this debate when we wrote the book. Will 21 times be overwhelming for people? Could you get the same effect in 10? What happens when you do more than 21? I couldn’t find the real science behind this. In fact, the rule that mostly pops up had to do with a “21-foot rule” in policing. But what it’s come down to is this, although practicing 21 seemed excessive to me on the surface, it is what worked in practice.
I remember that by my fifteenth exhibition match, I felt unflappable. My three-year-old daughter could kick open the door in the middle of a practice session and drag me to the kitchen to pour her a glass of milk, and I could still pick up where I left off without losing any momentum. Backers will rarely sit quietly through an entire pitch unless they’re bored. They cut in with questions, ask you to go back, ask you to jump ahead. None of this is bad, because it means your backer is actually engaged.
And if you can glide through the choppiness—jumping from point 3 to point 9 and then transitioning smoothly back to 4—those are the moments when your confidence shines through. So, I kept going, I kept practicing and by the time I had practiced twenty-one times and was almost hoping for a mishap so that I could flex my newly built recovery muscles. 21 times is what it took for me to feel certain that whatever happened, I could navigate it—21 times is what it took to feel bulletproof.
Is it best to practice alone or with others?
With others. It is the insights we gain from others that will help take us to the next level. When I was struggling to get investors interested in my startup Rise, I was introduced to Leah Solivan, the founder and then CEO of TaskRabbit, one of the hotter online marketplaces at the time. We met at her go-to breakfast spot and I pitched her as if she were an investor. When I finished, we went through her list of notes—my presentation was too long; it was bloated with facts and figures; it was missing a concise, memorable story. Solivan poked holes but then helped me rebuild a new outline from scratch. That revamped pitch was the one that went on to be backable.
In the book, I talk about a story with Barack Obama. I know it’s hard to believe now, but back when Barack Obama ran for Congress he was defeated by a two-to-one margin. Believe it or not, Barack Obama was seen as boring. Reporters described him as “stilted” and “professorial.”. Ted McClelland, a journalist who covered Obama during his congressional loss, said that his speeches were so dry they “sucked the life out of the room.”
That’s not the Barack Obama we know, and it all changed thanks in part to a new ally—the Reverend Jesse Jackson. While Obama knew how to educate an audience, the reverend knew how to move an audience. If he was going to reach the highest levels of office, Obama needed both. So, Jackson helped Obama become a frequent speaker for his coalition, the Rainbow PUSH. It was there that Obama played many exhibition matches, honing a style that would ultimately become the foundation for his 2004 keynote—the speech that changed everything for him—and everyone else.
Finally, something I learned is that it’s not just practicing with one person, but with a set of people—what I call your Backable Circle. Surround yourself with a small group of trusted people who bring different perspectives and play different roles to get you ready for a backer. These different roles are the 4 Cs—your Collaborator, Coach, Cheerleader, and Critic, or what I call your “Cheddar.” I explain why I named this person Cheddar in the book, and that’s a fun story that stems from Eminem and my Detroit roots, here I’ll just get to the point and say this is a person who will deliberately poke holes in your ideas, sometimes in a way that is deeply annoying. But this is one of the most important roles because, in the end, Cheddar is the one who’s going to help you get ahead of a backer’s objections.
What is the best setting for practice?
If you can, practice at the same time as your pitch. Schedule the meeting in advance and then practice at that exact same time. Great test takers do this—they take practice tests at the same time they expect to take the real one. It gets your mind trained to be in the right place at the right time.
These practice rounds should take place in public but in a low-stakes situation. For backable people, no venue is too small for an exhibition match. The only requirement is the ability to practice in front of someone other than yourself. Simply having a real human staring at you is enough to put you into real practice mode. I’ve now played plenty of exhibition matches in front of my eight-year-old daughter.
The key is to treat each one of these exhibition matches as if you were in front of a real backer. I used to make the mistake of giving a director’s commentary during my exhibition matches. I’d say things like, “First I’m going to talk about the size of the digital therapeutics market; then I’ll discuss how we’re different from the competitors.” But that’s not a real exhibition match.
When a friend asks what you’re working on, instead of giving them the thirty-second summary, ask, “Do you have fifteen minutes for me to practice my pitch?” I’ve found that not only deepens my practice but deepens my relationships.
Are there any practicing hacks that can be applied to non-verbal work, like say, an important email or social media interaction?
Read what you’re about to send out loud. One thing I learned is that our ears are excellent editors. When I was reading Backable out loud for the audio version I caught lots of mistakes in the print version. Plus, it gives you a better sense of what it might really sound like in the reader’s head.
How can we check in with ourselves physically before a meeting?
Before a big meeting, I literally imagine myself pressing a giant “reset” button. It’s literally a wipe of everything that’s happened that day so that I can be tuned into what’s happening next. It takes practice, and your reset button becomes more effective over time.
I also do something that I learned from Maureen Taylor, a communications guru who coaches some of the biggest names in Silicon Valley. I was trying to get companies to partner with Rise and getting a lot of passes. I went to Taylor for help and she did something that surprised me. She quoted Charlie Parker: “You’ve got to learn your instrument. Then you practice, practice, practice. And then, when you finally get up there on the bandstand, forget all that and just wail.”
Riffing off of Parker, Taylor shared two words that have become my mantra: “Forget yourself.” I now take those two words with me everywhere—to meetings, to presentations, even to dinners with friends. Those two words helped Rise land successful partnerships and our next rounds of funding and unleashed more magic than I ever could have anticipated.
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