In this Art of Charm podcast episode, Oren Klaff, an investor, venture capitalist, and author of Pitch Anything who has raised more than two billion dollars, explains how the croc brain filters every pitch, why neediness kills deals, and how frames like the prize frame and expert frame help you lead a presentation.
Listen on: YouTube | Apple Podcasts | Download the audio
Key Takeaways
- Information reaches a listener's neocortex only after it passes the croc brain, which asks a few primitive survival questions, and the midbrain, which asks where you sit in the social hierarchy.
- A spreadsheet, PDF, or demo provides certainty but does not create wanting, so a pitch should first make people want the deal and only then layer in the confirmatory details.
- Neediness kills deals because people instinctively pull back from someone who needs something from them, so the discipline is to behave as if you do not need the outcome while still working to close.
- In the prize frame, you treat your time, product, and expertise as the prize, and you treat money as a commodity, which also means screening buyers and investors because a bad one can be worse than none.
- Conflict and tension hold attention, so a pitch or a relationship needs something to resolve, and playful challenges such as framing someone's behavior as outside the norm can create that tension without being cruel.
- In a room full of people, you can organize the group by role: defer to the CEO, hold a direct high-stakes conversation with a peer, compliment the analysts, and gently reframe the lawyers.
- A strong pitch is a performance that answers the buyer's questions in the order they arise in the buyer's mind, and it ends with you leading the next step instead of handing all the power over by asking for questions.
- Doing your best, getting repetitions, and refusing to supplicate lets you accept losses, because you cannot get attached to the outcome of any single pitch.
Curious how people build this kind of presence in real conversations? See how the X Factor approach works.
Who is Oren Klaff?
Oren Klaff is an investor, venture capitalist, and author of Pitch Anything. According to the episode introduction, he has raised more than two billion dollars by understanding the prehistoric part of the brain he calls the croc brain. He works in the world of deals, and the episode shows how he applies the same ideas to sales pitches, raising money, getting a raise, and everyday social life. He described how a conversation with a cognitive psychologist changed his understanding of how information moves through the brain, and how a longtime business partner taught him much of what he knows about deal behavior. A new book, The User's Guide to Power, was described as coming out. He pointed listeners to the Pitch Anything website for more of his content.
Episode Chapters
- 04:02 How Information Moves Through the Brain
- 12:48 Neuro-Financing and Creating Wanting
- 22:40 Eradicating Neediness From Deals
- 28:45 The Prize Frame Explained
- 40:03 Using Conflict and Tension
- 53:54 Power, Expert, and Analyst Frames
- 67:58 Pitching as a Performance
- 71:07 Leading the Next Step
- 81:45 Getting the Meeting and Selling Smarter
- 90:36 Body Language, Reps, and Failure
How does the croc brain affect your pitch?
Around 04:02 in the episode
Oren explained that your message must get past the croc brain, which asks whether something is food, a mate, or a threat, and then past the midbrain, which cares about status, before the neocortex will engage with your ideas.
Oren described how his approach started with a cognitive psychologist. He thought he already understood psychology, but the psychologist told him he did not understand how the brain works. Oren said he stopped talking and started listening, and what he heard was a model of how information physically travels through the brain and gets broken up and reassembled along the way.
The first stop is the crocodile brain, near the brainstem. Oren said it cares about only a handful of things. When you open a pitch with ROI, IRR, and downside protection, that part of the listener's mind is just noticing something that moves and makes noise and asking whether it is something to eat, mate with, or kill. Your information has to get past that very primitive filter.
Next is the midbrain, which cares about social status. Oren said that if the listener believes you are beneath them in the dominance hierarchy, their focus narrows, their appreciation of you stays surface level, and they take risky behavior around you, such as checking their phone or taking calls. Only when they believe you are not beneath them does your information reach the neocortex, where your idea or project can actually be appreciated.
The hosts connected this to research on a mouse in a new environment, which has to explore the whole room until it feels safe before doing anything else. Oren tied that to the small talk that opens most meetings, such as skiing, vacations, or the big game, and described it as a way of seeking a safe space so the conversation can move forward.
What is neuro-financing and why do details come last?
Around 12:48 in the episode
Neuro-financing is Oren's way of describing the psychology under deal making: people want what they cannot have, chase what moves away, and value what they pay for. Details that create certainty come after desire.
Oren explained that most finance pitches fall into what he calls the analyst frame. There is a spreadsheet with assumptions, math, and projections. He said that talking about facts, details, and uncertainty tends to create fear, and that our brains were never designed for complex math.
He boiled the neurology of finance down to three ideas: people want what they cannot have, people chase that which moves away from them, and people only value that which they pay for. He acknowledged that numbers, pro forma assumptions, and exit strategies must be communicated, but said they have to sit inside that context.
This leads to what he calls confirmatory diligence. Spreadsheets, PDFs, press clippings, PowerPoint decks, demos, user experiences, and rankings all provide certainty, but Oren said they are not compelling. In a deal he sets that material aside at first, asks what is compelling, and waits until the buyer says they are compelled or want it. Then the certainty-providing material tips them over the edge.
A host noted that, as the book says, packing the pitch itself with spreadsheets and pro forma tends to bog it down. Oren's summary was that you first have to create wanting and then provide the details that make that desire feel more certain.
Why does neediness kill deals?
Around 22:40 in the episode
Oren said neediness triggers a fear response, makes the other side dig in, and slows or kills deals, so you have to behave as though you do not need the outcome even when you really want it.
Oren credited a longtime business partner, Russ, with teaching him to eradicate neediness. He described a partner who would walk away from deals that did not meet his terms, even when Oren personally wanted the fee, and who communicated with short, blunt, funny messages. Oren said the partner never explained the reasoning, so he took notes and reverse engineered the pattern until his own attempts started working.
The lesson he drew was about the long game. By not acting needy and by controlling the frame, you convert far more transactions, and the ones you lose were either going to be lost anyway or would not have been good partnerships. Oren said you will lose some dates, some deals, and some customers, but the number you tip in your favor is what matters.
He also described integrity as something you do for yourself, comparing it to the integrity reps in Navy SEAL style workouts, where nobody can watch you the whole time. His version is never acting needy even when nobody would notice.
As a possible explanation, Oren speculated that in early human societies people owned very little, so anyone who came to you in need created fear because you had nothing to spare. He was open that this may or may not be scientific. In modern deals, he said, the moment someone says they need the transaction there is a surge of power on the other side. The tension of pitching is managing two forces at once: you cannot seem like you need it, but you do need to close.
What is the prize frame in a pitch?
Around 28:45 in the episode
The prize frame is the idea that one person in any relationship or deal is the prize and the other is the supplicant. Oren recommends framing yourself, your product, and your time as the prize and treating money as a commodity.
Oren said most of us are wired to see the investor or buyer as the prize, like a contestant performing for judges on a talent show. He argued that you need to break that frame. He also pushed back on win-win thinking in deal making, saying negotiation advice built for high-stakes standoffs does not fit ordinary deals where the other party does not have to work with you.
His way of organizing the prize frame is to remember that money is a commodity he can get anywhere. If all a buyer can offer is money, then what the buyer actually needs is a good product and a good partner. He described knowing his subject better than anyone, working harder, being fair and fun to work with, and finishing what he starts. From that position, the buyer has to show they are worthy of working with him.
He added an important caution for people starting out. A bad customer or a bad investor can be worse than none and can ruin your life, so you do have to test, interrogate, and screen them. That means commoditizing the buyer and recognizing that your time, product, and ability are the prize in the relationship.
The hosts connected this to social life. Whether you are meeting friends or pitching yourself to a potential partner, coming in needy and trying to get fun, validation, or attention from others places you lower on the dominance hierarchy, and people tend to steer clear.
How can conflict and tension make you more persuasive?
Around 40:03 in the episode
Oren explained that humans are drawn to conflict because it lets us learn how disputes get resolved, so a pitch or relationship with no tension gives people nothing to engage with. Playful challenge supplies that tension.
Oren called conflict one of his key topics. He said a commercial, a video, a movie, or a TV show needs conflict that can then be resolved, and the same is true in human interaction. When two people are fighting outside the office, everyone rushes to look. He suggested this is a kind of simulation engine, because in the distant past conflict was dangerous and watching how others resolved it taught you how to get out of it yourself.
From that he said the missing ingredient in many pitches is tension. They are sweet and idealistic, with a perfect product for a perfect market and no real competition. Any joke or story has a setup, a path to payoff, and a payoff, and the payoff is satisfaction from resolving tension. He gave a movie bar scene as an illustration, where a smooth, tension-free exchange does not match real life.
He described a tool he uses with busy, wealthy friends and contacts: playful one-upmanship. He calls and asks how their work is going by teasingly minimizing it, calling it cake decorating, and they respond with something back. The tension gets filled, they remember him, and the relationship stays alive. He also described the moral authority frame, where you frame someone's behavior as slightly outside the norm, such as showing up a few minutes late to a call, so the other person apologizes and a collegial, fun dynamic forms.
The hosts added two cautions. Written communication loses nuance, so playful teasing can need extra signals. And people learning the skill often swing too far, so calibration takes practice.
How do you handle the power frame in the boardroom?
Around 53:54 in the episode
Oren said you break the power frame with the expert frame: show expertise they need and keep moving forward without needing their approval. He also described organizing a room by role so each person is treated appropriately.
Oren described the power frame as the behavior of someone who barely responds to your presentation, grunts, or just wants information. It can come from an analyst or a CEO. He said this leaves two bad options: becoming the supplicant who keeps asking if they have questions, or fighting power frame against power frame over minutes on the calendar.
His alternative is the expert frame. When you have expertise someone needs and lacks, they have no power over you, and if you also continue discussing it without needing their attention or acceptance, you can overcome the power frame. He stressed naming these situations, such as the prize frame, the power frame, the expert frame, and the analyst frame, because you cannot deal with a scenario until you give it a name.
For a room with several people, he described organizing them into dominance hierarchy positions. Show deference to the CEO. Find a peer on their side and have a direct, high-stakes conversation. Be complimentary toward the analysts, who will try to poke holes, and tell them in advance that they are smarter on the numbers and will find errors. Gently reframe the lawyers with humor.
Oren explained the reason for building up the analysts: they make themselves look good by disproving your numbers, so agreeing in advance takes the energy out of that. He also told a story about walking into a publisher meeting and thanking the assistant, then asking when he could meet the person in charge, which created fun for the room. The hosts compared the tactic to complimenting a group of friends while teasing the person you are interested in.
How should you structure a pitch presentation?
Around 67:58 in the episode
Oren said a pitch is infotainment and a performance. Give buyers information in the order the questions come up in their minds, raise the obvious objections yourself, and manage the frames throughout.
Oren said that in a deal or business presentation your job is infotainment. Information alone could be mailed in a FedEx packet or attached to an email, but people come to meetings to learn, meet interesting people, hear novel ideas, and be entertained. He compared the preparation to a comedian whose off-the-cuff set is the result of long practice.
He explained that buyers want information in the order their questions arise, and that this order is the presentation, not whatever you most want to say. He outlined a sequence: the big idea, how things are changing, the problem, the solution, how it works, the key assumptions, the pro forma and downside protection, the team, and who else uses or believes in it. He said this can be done correctly in roughly 15 to 20 minutes.
He also described raising the obvious skepticism up front. If listeners are likely to wonder whether something is even legal, he says so and explains what the team did to answer it, rather than waiting for the question at the end. He said this is why he rarely gets questions in the middle of a presentation.
Oren also made the point that presentations improve every time you give them, and that treating the pitch as a performance is what makes it feel professional.
I haven't been asked a question in a middle of a presentation in ten years
What should you do at the end of a pitch?
Around 71:07 in the episode
Do not end by asking whether they have questions, because that hands all the power to the buyer. Oren described leading with a challenge or clear next steps so the other person responds to you.
The hosts framed the last stage as leadership, and Oren said it is where many pitches fail. After you have delivered the objective information, the subjective information, and the rapport, asking what they think or whether they have questions is the moment the buyer takes over. They say they are very interested, will talk it over with partners or a committee, and will get back to you. Then they disappear and you are chasing them.
The hosts offered a social parallel: after doing all the work to build interest, a person asks someone to hang out sometime and hands over the ball. They argued that you should make clear statements about what happens next, such as stating when you will send the contract or proposing a specific time to meet, because the other person has not yet done the work of facing rejection.
Oren described a more aggressive script of his own. He tells the buyer he likes them and sees a fit, but says that if they handed him a check right now he would hand it back because he does not know enough about them, how they behave when deals go sideways, or what they have done before. That challenge flips the roles.
He explained why it works: after a well-organized performance, the buyer has no equally polished presentation to give back, so they start fumbling. Because their social status has dropped slightly, they want it back, and you can help them tell their story so that they end up on a peer level and want to work with you.
How do you get a pitch meeting in the first place?
Around 81:45 in the episode
Oren said the way to get the meeting is context plus a sense that winter is coming, meaning something in the listener's world is changing and they should prepare. He also warned against feature and benefit selling.
When asked about the elevator pitch, Oren said it is a little weird and tied to older books. He said two things matter today: a message that winter is coming, borrowed from Game of Thrones, meaning something is changing dynamically in the listener's world and they must prepare, and context that shows you are not wasting their time.
He illustrated context with an example of someone who references his blog, mentions his book dropping and a specific moment in a past broadcast, and only then notes a problem with his website. By then he is not even aware that he is being sold to. He added that a stronger version states the change coming to the industry and what happens to those who are not ready.
Oren also criticized feature and benefit selling. A feature is objective and a benefit is subjective, so alternating them tries to make the listener believe something that is not a fact, which feels like being sold. He suggested telling the buyer plainly what the product is, then why it is good for them, rolling it into a value proposition, and asking for the decision.
He argued old sales methods came from a time when salespeople held information buyers could not easily check. Today buyers fact-check online and may know more than you do, so expectations for concise, accurate information are higher. The conversation also touched on the Al Pacino soundboard from the film Glengarry Glen Ross as a way to build responses without supplicating, and on coffee shops being poor places for meetings or dates because of interruptions and distractions.
How do you handle failure and body language when pitching?
Around 90:36 in the episode
Oren said repetitions turn conscious variables into habits so you can focus on what matters, and that you handle failure by preparing, doing your best, and keeping your integrity instead of begging or becoming attached to the outcome.
On body language, Oren said he is not especially aware of his own, though audiences react well to it. He credited a voice coach, Roger Love, with helping him stop using symmetrical, parallel hand movements, saying asymmetrical movement reads as natural and powerful, while matched movements can look like a politician or a preacher. Both he and the hosts said video feedback and reps reveal habits you do not notice.
He used a motorcycle track analogy for reading other people. On your first time on a racetrack every small variable seems like a disaster, but with repetition you park each one in the subconscious and focus only on the big variables. Only then can you observe the other person. Oren said his business, where each pitch is different, limits how far he gets with that. The hosts added that reading arm positions alone can mislead and that science does not back mind reading from posture.
He compared a good presentation to a rock band that plays the same strong set in every city instead of reacting to where it is. Review comes after the performance, not during it.
On handling failure, Oren said the answer is knowing you prepared, thought about what was best for the other person, brought your best material, and tried to help authentically. If that does not work, you did your best and you do not change your values, beg, or supplicate. He mentioned that stoic ideas helped him through down times. He also shared a personal note about integrating the different versions of himself, because people pick up on inconsistency, and he said that is why being reactive with different archetypes can come across as inauthentic.
Want to see what it looks like to walk into any room and own it? Find out how X Factor works.
Frequently Asked Questions
Who is Oren Klaff?
Oren Klaff is an investor, venture capitalist, and the author of Pitch Anything. The episode introduction says he has raised more than two billion dollars by understanding the prehistoric part of the brain he calls the croc brain, and a new book, The User's Guide to Power, was described as coming out.
What did Oren Klaff say about the art of the pitch on The Art of Charm podcast?
Oren said a pitch must get past the croc brain and the midbrain before it reaches the neocortex. He discussed creating wanting before details, eradicating neediness, using the prize and expert frames, adding tension, structuring a presentation as a performance, and leading the next step instead of asking for questions.
What is the croc brain according to Oren Klaff?
In the episode, Oren described the croc brain as the primitive part of the brain near the brainstem that cares about a few survival questions, such as whether something is food, a mate, or a threat. Information must get past it, then past the status-focused midbrain, before the neocortex engages.
What is the prize frame?
The prize frame is the idea that in any deal or relationship, one person is the prize and the other is the supplicant. Oren recommends seeing your product, expertise, and time as the prize and money as a commodity, while screening buyers or investors because a bad one can be worse than none.
What is confirmatory diligence?
Oren used the term for material such as spreadsheets, PDFs, press clippings, demos, and rankings that provide certainty but are not compelling. He said a pitch should first create wanting, and only after the buyer is compelled should this material be layered in to tip them over the edge.
Why does Oren Klaff say neediness kills deals?
Oren said neediness creates a fear response and gives the other side a surge of power, so they dig in and slow things down. He described learning from a business partner to behave as if he did not need the outcome, which converts more deals even though some are lost.
What should you do at the end of a pitch?
Oren said asking whether the buyer has questions hands them control, and they often say they will get back to you and then disappear. He described leading instead, with clear next steps or a challenge that says you do not yet know enough about them to commit.
Where can I learn more about Oren Klaff's work?
Oren pointed listeners to the Pitch Anything website, where he said putting your name in unlocks a cascade of content. He also mentioned being on Instagram and Twitter. The episode also covered his book Pitch Anything and a new book, The User's Guide to Power, described as coming out.
More Episodes Like This
- Oren Klaff | How to Pitch Anything (Episode 347)
- Art of Charm Toolbox | Perfecting Your Elevator Pitch (Episode 550)
- Chris Voss | Never Split the Difference (Episode 534)
- Robert Cialdini | Pre-suasion (Episode 543)
- Steve Sims on Networking and Making Things Happen | Episode 682
