Good for saving the day in live performances, speeches, client presentations, and any situation where humanizing yourself will help you connect with your audience.
You were racking your brain for awesome stories you can use to captivate and disarm your audiences, and trying to figure out the best way to tell them. When you do, you’re going to make mistakes. It’s inevitable. But you can let those mistakes crush you or use them to make your pitch even more effective.
We’re afraid of making mistakes. It’s perfectly normal. But few people seem to appreciate how much power there is in embracing mistakes and using them to tickle someone’s funny bone or make a human connection. I’ll illustrate by telling you about one of the funniest things that’s ever happened to me.
When I was a kid in England I had an old piece of shit Mini, and I loved it. Then when I was living in the United States an all-new version of the Mini became available, and I was delighted. My then-wife Randi had a Beetle and didn’t like it. I said, “Why don’t we go look at Minis? They’re really cool. They suit your personality.” So we drove to Ferman BMW and the salesman said, “You want to go for a test drive?” Of course we did. Then he offered to drive, which was odd. He said, “I’ll drive out and you can drive back.” Okay.
We got in the Mini, with Randi in the back, and he said, “This has got some power. You should put seat belts on.” We did, and then this guy spun the wheels like he was auditioning for The Italian Job. He laid rubber taking off—we were still in the dealership lot, mind you—and he tore around a corner like Mario Andretti, and I’ve driven with Mario. It was terrifying.
Well, the parking lot was cambered, like the back of a whale, and he hit that slope going about eighty miles an hour. We caught air and Randi was screaming in the back for him to stop. Then we landed on the tarmac and immediately spun sideways, skidding through an adjacent parking lot. I was thinking, I’m going to die. I was a second from reaching over and punching this guy in the face when—you know those big lights in the middle of parking lots with high curbstones around them? We smacked into one, hard, bending the front wheel under the car horizontally. We had snapped the axle!
So we sat there, shaking, like you do, taking inventory. Are we safe? Are we alive? Randi was sobbing and I was furious. I screamed, “What the fuck are you doing?”
He said, “It’s not that bad, it’s not that bad.”
“Not that bad? This car is not even drivable and you’re an asshole.” I let Randi out of the back and we walked back to the dealership, shaken. All the while, I was waiting for Ashton Kutcher to come out and tell me I’d been punked. We got back to the dealership, walked in, and Aaron, the sales manager, took a look at us and said, “What happened?”
I was still seething. “Your guy ran into the curb. He almost killed us.”
Aaron said, “That’s not very good, is it?”
Really? That’s all you have to say? “Before I leave this dealership,” I said, “I want that guy to be not working here anymore. He shouldn’t be allowed to take people on test drives. He’s dangerous.” They called the manager and he said, “I wouldn’t be that worried about it.”
I glared at him. “We nearly died.”
His response was to pretend the whole thing was just some lark, some misunderstanding, and to try and offer me some piss-poor discount on a Mini. You know what? I might have actually bought the car—if they’d had the balls to own the mistake, fire the salesman, and use the situation to pitch me. If Aaron had laughed and said, “Sorry you almost died, but how about that power? Can you imagine a car that handles like that on a mountain road?” I would’ve respected the chutzpah and probably said, “Yeah, dude, it was fast.”
They would’ve had to knock a massive amount off the price of the car for, you know, almost killing us, but I would have bought the car. But they blew it. They could’ve had a story and a customer, but they wimped out and we walked. We went and bought a Range Rover instead.
They say it’s not the crime, it’s the cover-up. Right? Absolutely true, and yet it amazes me how many people screw up during a pitch, think no one will notice, and then pretend it didn’t happen. That does. Not. Work. Trust me, everyone saw what just happened, and it’s a moment of truth. Moments of truth are when you show who you are and reveal your character. If you’re a pitching superhero, you use mistakes to make yourself accessible, make people laugh, and break the force field a little more.
A few years ago, there was a host on a shopping network. Great gal. One day, she was live, selling these plates that were supposedly unbreakable. Yeah, you know where this is going, don’t you? She opened up her pitch and went on and on about these wonderful plates that you could drop and abuse and they would not break. And then she dropped one.
You know those moments when things go into slow motion? That was one of them. You could see the plate flipping end over end, her surprised face, the light glistening off the product. And then it hit the floor—and shattered into a million pieces. It was one of those perfect fuck-ups, like the perfect storm of home shopping. But, God love her, she laughed about it and said something like “Well, it’s a good thing these plates come with a money-back guarantee!” and kept on going. It was terrific.
We’re so terrified of mistakes that we like to pretend they don’t happen. When we do that we lose the chance to do things that can really earn warmth and love from an audience and even get them on our side: admit we’re human, solve problems, and prove that we are who we say we are when things are going well. That’s a lost opportunity, and I’m going to tell you how to take advantage of it instead.
It’s a reflex to back away from mistakes as fast you’d back away from a rattlesnake that you found on a hiking trail. But if you’re going to be a superpowered pitching pro, you actually need to do the opposite. Because when you’re trying to sell, persuade, or captivate anyone in any situation, you can be absolutely, 100 percent certain that three things will happen:
1. You will be nervous.
2. You will screw it up at least once, no matter how well prepared you are.
3. Somebody in the room will notice the first two, even if it’s just you.
When those things happen, you also have three choices:
1. If you’re the only one who noticed, keep going as though nothing has happened.
2. If your nerves or flub are so obvious that the other party can’t help but notice, pretend nothing happened and push on.
3. Acknowledge your slipup and use it to your advantage.
If you’ve ever done drama, your teacher or director probably told you, “If you make a mistake, keep going! The audience won’t know unless you stop and say, ‘Oh, shit!’” For the most part, that’s true, though I do wonder how thick a theatergoer would have to be not to pick up the mistake in “To be or not to be, that is the questlove.” But I digress. The point is, pitching isn’t theater. You might have an audience of one, up close and very personal. They’re likely to pick up on your mistakes, especially if this isn’t their first rodeo. A venture capital firm that’s watched thousands of entrepreneurs pass through with their pitch decks asking for money has probably seen every blunder a group of twenty-four-year-old Stanford grads can make—and all the ways they can try to cover them up, too.
So don’t try to fool your audience. Mistakes can be your best friends, so treat them that way. In other words…
Using this Pitch Power means reprogramming that part of your brain that screams, Shit! I forgot what I was going to say! Activate Distraction Mode! No. Stop. Don’t act cool, cover up, or anything else. As triathlete Chris “Macca” McCormack (who I mentioned earlier) says about that moment when he starts to suffer in a race, “Embrace the suck.” Own up to your mistake. Admit you’re nervous. Laugh about it. Get the other people laughing about it. Because guess what: we’ve all been there. We’ve all screwed up, dropped the meat in the dirt, and flubbed our lines. Love your mistakes and you’ll get them laughing with you, not at you.
When I talk with young people who are trying to learn how to pitch, one of the most common misconceptions is that being a great persuader or pitchman means not making mistakes: training the risk out of your presentation. But nothing could be further from the truth, for two reasons. First, you won’t learn Pitch Powers unless you’re willing to step onto the stage and risk looking like an idiot, like I did on the first day I pitched the car washer in the market in Devon. The only way you’ll learn is to step into the lion’s den, make mistakes, recover from them, and develop your tools. It’s that way with anything you do, really. If you don’t want to make mistakes, you’ll hide in your house eating Hot Pockets and watching Netflix and never come out. Don’t do that.
So if you accept mistakes as an integral part of pitching, then the obvious question is, “Okay, Sully, if I’m going to make mistakes, how do I make sure that I get as much out of them as possible?” Fair question. Here are six ways to do that:
1. Make ’em loud. They say, “Go big or go home,” and that includes your errors. Loud mistakes are the ones you make because you took a big, big risk with a potentially huge payoff. In finance, the bigger the potential return on your investment, the bigger the potential risk that you might lose it all, right? It’s the same in pitching. Sure, you can play it safe and ask out the plain-looking guy or gal who you know will say yes because they’re grateful for the attention, or you could risk getting shot down and ask out the supermodel over there. You might have to do the walk of shame—or you might just shock your mates and end up with the number of the hottest person at the club! Loud mistakes have the biggest possible payoff.
This is where it helps to not mind looking a little like a fool. As you already know, I don’t. I’m willing to make an ass of myself to improve my odds in a situation. For example, about eighteen years ago there was a reality show called the Eco-Challenge, which was Mark Burnett’s first show before he did Survivor and The Apprentice. I’m a huge fan of Mark’s and I really wanted to be on Eco-Challenge—and I have been known to do crazy shit to meet people.
First, I watched all the episodes, and then sat down with my buddy in Tampa and I said, “I’m going to do the Eco-Challenge next year.” He started laughing at me, so I went on the website and filled out the application. It was funny: I had even assembled a team of four, but I hadn’t told the other people yet! Or it would’ve been funny if I’d gotten in, but I got an email back from a lady named Lisa Hennessy, who said that they didn’t have room for more teams but did have some individual spots left. If I wanted to do an individual application, she’d try and put me with a team.
I looked at the application for individuals and started sweating. You basically had to be superhuman: done an Ironman triathlon, swum across the English Channel, climbed a mountain, traversed a continent solo on a bike, or something like that. I didn’t have any of those credentials. So I put on my Persuader mask and thought, How am I going to make my application stand out?
I decided the only shot I had was to make it funny. After all, it was a TV show, which means it had to be entertaining. I had no problem being the class clown if it got me what I wanted. So I got a box and put my Boy Scout knot-tying certificates in there. I got pictures of me as a kid, my report card, and pictures of crazy things I did when I was ten or twelve years old. Then I filled the box up with “As Seen on TV” swag: Turbie Twists, a box of OxiClean, Sonic Scrubbers, every product I had ever sold on television. I put them all in a box that was so heavy I could barely lift it, and shipped it to the production offices.
It was a crazy long shot, but I knew there would be ten thousand envelopes in there and one massive box. It would stand out. The next month, I got a phone call from Lisa telling me they had chosen me for Eco-Challenge because mine was the funniest application they ever received. They had chosen me because I had made them laugh, not because of my credentials. Everyone in the office was wearing a Turbie Twist, this towel-like head wrap that looks like a turban. The whole thing cost me a hundred bucks, but I got on the show, met Mark Burnett, and made a ton of friends. If I hadn’t been willing to get creative, look stupid, and flop miserably, none of it would’ve happened.
2. Frontload your nervousness. People love when you can analyze your own nerves and cop to them, because we’ve all been there. There’s nothing wrong with going in and admitting to people that you’re jittery. I have been very honest in some pitching situations about how nervous I was, and that changes expectations in your favor. Instantly, you go from someone expected to deliver a flawless performance to someone working to overcome fear. Go as far as to say, “I am a nervous wreck right now, but I am going to do my best.” Already, you’ve won the crowd by being honest and vulnerable.
Being self-deprecating and owning your flaws is another way to do this. Comedians are great at it. If a comedian is an alcoholic, she’ll use it. If she got teased in school, she’ll bring it up in her act. Don’t pretend you’re perfect. Be flawed. If you have a strange speaking voice, get out in front of it by saying, “I know my voice is high pitched, but don’t worry, I supply all my own helium” or some such line. People will laugh with you if you can make fun of yourself. Don’t take yourself too seriously.
3. Plan your comebacks. Later, in the Training Montage section, I’m going to talk about the virtues of watching stand-up comedians to learn about mistakes. They’re brilliant at leveraging them. Hecklers are a common way that things can go awry in a comedy club, and good comics plan how to handle hecklers. Many years ago, when Steve Martin was a stand-up star, he had a terrific comeback when someone got rowdy at his shows. He would muse, “Yeah, I remember when I had my first beer…” The audience always howled at his soft mocking of the usually drunk heckler. That was a planned comeback, and you should have some idea of what you’ll say and do if you spill a glass of water, forget details from a story, or accidentally drop a “fuck” or “shit.” Leave yourself room to improvise, which you will get better at the more you pitch. But plan and rehearse some responses. If nothing else, they’ll be a relaxing security blanket.
4. Breathe. When you mess up, don’t panic and rush to cover up your mistake. Stop. Slow down. Breathe. Take a pause. Find a moment. When you pause, the audience pauses with that pause. They will feel the gap. Even though it may feel like an uncomfortably long silence, you are allowing your audience to process what just happened: you’re nervous, you made an error, now you’re regaining your composure. Believe me, you will earn more respect from the people listening by taking a moment to gather yourself, which is what a professional would do, instead of rushing on like nothing happened.
5. Get them on your side. You’ve heard about that old trick for nervous public speakers where you’re supposed to imagine the audience members in their underwear. The idea is that we’re all human. You could just as easily imagine the audience spilling coffee or having a PowerPoint crash in mid-presentation, because there’s no one you can pitch who hasn’t made mistakes that seemed catastrophic at the time. But you know what’s funny? If you ask them about those same mistakes today, they’ll laugh. Misfortunes make the best stories!
So, when you trip over your tongue, say, “Well, I blew that punchline. Who hasn’t done that, right?” Odds are you’ll get smiles, maybe a few shared stories, and some priceless common ground.
6. Find a scapegoat. I don’t mean someone to blame for real, but a comic sense. If you’re pitching as a group or team—soliciting venture capital, to go back to my earlier example—designate one person as the clown or jester: the one who gets the blame in a tongue-in-cheek way when something goes wrong.
I did this all the time pitching in street markets and in home shows. Inevitably, some small piece of the Smart Mop or Amazing Washmatik would break at some point, because in doing fifty pitches a day we tortured those products. So I’d pull the mop out of my bucket and there’d be no mop, just a stick. Guess who knew? Nobody. I’d have a hundred people in front of me and without missing a beat I’d say, “Ladies and gentlemen, I’ll bet you think the mop I’m using is the only one that works, right? You’ve been to these fairs before and seen a lot of bogus products. Well, I’m going to prove that every one of these mops is as good as the next. Pick one and I’ll do my demo with it.” Then I would casually set the broken mop aside and keep going.
If a mistake was too obvious to miss, however, I always had a—well, in America they call him a prat; in England, he’s the schlepper. Anyway, I always had a whipping boy who couldn’t do anything right, was to blame for whatever went wrong, and who I used to scream at all the time. If I was selling a vegetable slicer, I could turn my back to my crowd and yell, “Where the heck is my tomato?” and the people would be howling. Try turning your back on your audience anywhere else and see how many of them leave.
It was a two-man comedy act, and the prat was my court jester. I announced us by saying things like “We’re the Symbolics! I’m Sim, and he’s Bollocks!” or “I’m Anthony the Magnificent, and this is my partner… John.” I was always riding his ass and the crowd loved it because he was useless. If something broke or I didn’t have a mop head or chamois, I would turn around and berate this poor bloke, then turn back to the crowd and say, “You just can’t get good help anymore!” They would be wetting their pants while he scrambled and fumbled to get me what I needed. It was perfect.
Remember, the people you’re persuading are just people. Make them laugh or touch their empathy and you’re one big step closer to getting what you want. Don’t fear mistakes; treat them as one more tool.
I know, I know. That’s hard to do. We’re programmed in our society to cover up our mistakes and fear failure more than death. But here’s a reality that makes it easier to embrace mistakes: most people are going to want you to succeed. I’ve already talked about what I call the “ace to the top of the deck” effect, which is where the person conducting auditions, interviewing job applicants, or getting hit on over and over at the bar is dying for someone to step up and be amazing so the whole thing can be over. But this isn’t that.
This is simpler. Most people are decent and they want to see everyone do well. That’s why audition reality shows like The Voice are incredibly popular: people are putting it all on the line, risking national humiliation, and we really, really want to see them do well. It’s human nature, written into the DNA. We’re altruistic. If you ask for help, people will try to help you. If you watch Shark Tank, you see a lot of people crash and burn and cry, but you want to see people succeed. So do the hosts. People you pitch will mostly be the same way. They know that you are powering through the same kind of crushing anxiety that they would be feeling if they were in your shoes. That’s nearly universal. You’ve got to be a sociopath to really want to watch somebody fail.
That was the nature of Billy’s and my reality show, Pitchmen. These inexperienced entrepreneurs would come to us with products and pitch us on them, and of course they would be terrible at it. But we would see something in one of them that stood out, and we’d put them on the show and teach them how to pitch. They’d still be awful at it, and they would make mistakes and get better, but by the time we took them out to pitch product development or marketing companies, they would still be as green as month-old ground beef.
Didn’t matter. Why? Because we knew that even the hardened direct-response pros they’d be pitching would respect the hell of the fact that they were out there doing it at all. They would be forgiving of mistakes and awkwardness because they wanted them to be successful. Never forget that and it will help to win in some important situations:
• Meeting someone intimidating. I’ve done some stupid stuff to meet famous people, but the best advice is the simplest. Do it. Don’t psych yourself out. Case in point: my mum loves Mick Fleetwood of Fleetwood Mac, but he famously doesn’t take photos with fans. Challenge accepted. Fleetwood Mac were in concert in Tampa and I was with the tour manager, Bobby Hare, a good friend. My mum and I had backstage passes and we were leaving through the rear parking lot when I saw four Cadillac Escalades, which is what the band members ride in instead of a tour bus. I said, “Let’s wait here. The band’s going to come out any second. Let’s see what will happen.”
The next moment, I saw Mick Fleetwood walk out. Mum whispers, “Fuck me, it’s Mick Fleetwood.”
I said, “Let’s go and ask him for a picture,” but she got scared.
“No, no, I can’t, I can’t.” But I took her by the hand and pulled her along. I was going to pitch my way into a picture for her. Understand, this was like walking up to the president, with security guards on high alert; I didn’t want to get Tased. So I looked at Bobby, and then at Mick. Bobby gave Mick a little nod and wink to say, It’s okay, and I knew we were in.
I said, “Mum, just go and ask him. You’re seventy-two years old; he’s not going to be mean to you.” I pushed her forward and said, “Mr. Fleetwood, say hi to my mum.” She got the picture, looking like she’d died, gone to heaven, and won the lottery at the same time. Now she has a photo of her and Mick Fleetwood on her fridge.
• Following a dull speaker. If the person speaking before you at an event is a crashing bore, your audience might be begging for you to put them out of their misery. Instead, be their hero by making fun of yourself or talking about your own mistakes. You’ll change the atmosphere in the room and win their devotion.
• Most social situations. From dating to parties to nights out, social occasions are full of people trying to look effortlessly cool, flawless, and successful. If you’re the person who wears mismatched socks, mispronounces the name of the wine, or drips salsa on your shirt, so what? Make light of it. Make a joke out of it. Get into it. You’ll be the entertaining one everybody else wants to hang around with.
Like most stand-up comedians, Carole Montgomery knows the value of embracing a flub and turning a heckler’s comment into a side-splitting quip. She’s been doing stand-up since the mid-1980s, first in New York (where she now lives), later in Los Angeles, and for years as a headliner in Las Vegas at hotels like the Riviera and the Luxor. She talked to me about the times she’s dealt with unexpected reverses in her shows and turned them to her advantage.
“Twenty-five years ago, I was working the Pittsburgh Funny Bone when, in the middle of my act, all of a sudden the lights went out,” she says. “I mean, it was pitch black. The thing was, the club was in a mall and without electricity, nobody could leave. Well, I have a loud voice, so I told people to relax and they did. But I had to keep doing my act to keep them relaxed, and a lot of my stuff depended on my facial expressions, so they needed to be able to see my face. I had the emcee go into the balcony with a flashlight and shine it on me, and I did my whole act like that. I didn’t change my act a bit, and we got through it.
“Another time in Vegas,” Carole continues, “I was on stage doing my act and saw somebody in the second row grab their chest. I made a joke of it, because that’s what you did but this woman really had a heart attack. Then a minute later, the woman next to her had a heart attack. We had to stop the show and call the paramedics. What could I do? I said, ‘The owner will return your money, but when we get these people to the hospital, if you want to stay, I’ll do the show for you guys.’ It took maybe forty-five minutes to get them out of the room, and then I went back on stage and did my full show—and hardly anybody left!
“You have to roll with the punches,” she concludes. “I worked Vegas for ten years, and you learn how to be a crowd comic, the one warming up the audience. You go out and talk to people; you don’t know what they’re going to say and you don’t even know if they speak English. But once you know you can make them laugh, the rest is easy.”
All this good advice aside, there are a few situations where mistakes will really undermine you. Anytime you’re coming into a situation where the audience perceives you as an expert—something legal, medical, financial, technical—mistakes will just damage your credibility. It’s also bad when you make a mistake at what you’re there to convince your listeners you’re good at. For instance, if you’re pitching a client on your firm’s graphic design services, don’t come to a meeting with sample company logos where the company name is misspelled.
Finally, mistakes are most damaging when you’re doing something where near-flawless preparation is part of what you’re expected to deliver. If you audition for a play, you’re expected to know the audition scene or song backwards and forwards. A mistake won’t be taken as a charming sign that you’re human, but as a warning sign that you’re not capable of preparing like a professional.
Know the small number of situations where mistakes will ruin you and when faced with them, prepare and rehearse until you’re sick of the routine, then do it again.
There are two sides to training to hone this Pitch Power: seeing how other people handle mistakes and getting comfortable leveraging your own. For the first one, there are two can’t-miss venues. First, go anywhere you can find pitchmen on microphones pitching products: Costco, a weekend home show, a flea market, or a county fair. Stop and watch, even if you don’t buy (though that drives us crazy). See how the pitchman deals with dropping stuff, messes, or rude audience members. Remember that 90 percent of his responses are planned and honed over time until they look seamless. If you’re really brave, take him aside after his shift and ask him how he handles mistakes.
Second, watch tons of live stand-up and improv comedy. Go to clubs and “comedy sports” events and see how comics turn heckling, bad improv lines, and things like equipment failures into comedy gold. You’ll see that it’s mostly about acknowledging that the blunder happened, adopting a kind of eye-rolling “doesn’t this happen to everyone” attitude, and cracking wise.
What about getting comfortable with your own mistakes? For that, you have to learn by doing and take some risks, and the perfect way to do it is to try your own hand at comedy. Take a stand-up class, tell a few jokes at an open-mic night, or take an improv class. Improv is especially useful, not only because it forces you to think on your feet, but because it’s unpredictable.
My other suggestion is a repeat from the chapter on breaching the force field: try giving something away or pitching to the public in another situation where you have little or no control, like running a lemonade stand with your kids or offering car washes for charity. Try that sort of thing for hours and you’ll run the gamut of mistakes and embarrassments: rude customers, equipment breakdowns, lost supplies, spills, forgotten patter, even bad weather. You’ll be forced to think fast, keep your cool, maintain a smile, and turn that sow’s ear into a silk purse by making people laugh.
SCENARIOS FOR USING THE “LOVE YOUR MISTAKES” PITCH POWER
Q: You’re pitching and you forget a story or fact. You admit it, laugh at yourself, and look up to see nobody laughing with you. Do you comment on the lack of humor in the room or get serious and keep going?
A: Let it go and get on with it. One thing you can’t do is MAKE people have a sense of humor. Some don’t.
Q: You’re pitching and trip up, but you make it work for you by making fun of yourself. Great, except that now, someone in your audience decides to seize the floor by going on about how he made this ridiculous mistake this one time. Shut him down to get back control of the situation, or let him go and play off what he says?
A: Unless you’re on a tight schedule, work with your audience. Be transparent about not letting the other person drone on (“Hey, Joe, that’s hilarious but I’ve got to bore the pants off of three other companies before noon”) but be ready to jump in and use his/her story as an example of why mistakes aren’t fatal or something like that.
Q: You’ve said or done something tasteless and your audience looks appalled. Can this pitch be saved, or is it bound for the lava pit?
A: Depends on the audience. I like the line from Amadeus, after Mozart swears in front of the emperor: “I’m a vulgar man. But I assure you my music is not.” Own it, apologize, wink at the ones who secretly liked it, and pivot.