Oren Klaff – How To Pitch Anything

This week’s episode of London Real brings you the investment banker and pitch master Oren Klaff.

As I’m sure you know this is Oren’s second visit to the show, and his first time back since we created our brand new studio and launched London Real Academy.

Oren is a man brimming with energy, stories, humour, and insights on life, as well as being an absolute killer when it comes to the business pitch.

And let’s be clear here — when we talk of the Oren Klaff pitch we are not talking small-time fundraising, job interviews or your monthly visit to a bank manager.

Oren plays in the big league every day, dealing with tough people in tough industries and playing for big money.

This is one of those episodes that is, beginning to end, packed with tips, knowledge and practical advice on getting things done, and winning people over to your ideas.

We kick off the interview by talking about Oren’s style, his approach to what he does.

He tells me about how he was chased and courted by Tony Robbins!

It’s an incredible story, about how the world’s best motivational speaker refused to take no for an answer from Oren.

Oren talks a lot about ‘bringing the thunder’ and it sums up what his pitch style is all about.

Oren’s idea of a pitch is different from what maybe pops into your head at first.

He’s not interested in slides and slides of presentations, facts and figures and reams of data.

For Oren, a pitch is a primal experience, an extreme sport, a kind of psychedelic experience in itself.

The objective is to control the environment socially, to almost short-circuit your audience into listening to you.

And ultimately, it’s about making them know that without your service it’s bad news for their company.

Not just bad news. PAIN!

Oren works with the reptilian brain, fight or flight.

His pitches are slick, short and sharp and hit the audience or potential clients where it hurts.

You’re going to get genuine, applicable templates from this episode.

I get him to break down each moment of a typical pitch, each phase of the operation, from walking into the room, to closing.

Some of the things you’ll hear are going to be counter-intuitive. Some tips will strike you as outrageous.

All of them, if you decide to apply them in real life, will shift up your game.

We talk about the difference between selling and pitching, and the difference lies in outcome.

What makes having a top-notch pitch so important is that it is usually do or die.

You have to grab the investor or client in a flash, and there’s no second chance.

What I love about Oren is this balance he has between intensity and approachability.

He’s always ON, and leans into every discussion and invests the moment.

At the same time, though, he’s great at putting you at ease, and entertaining you.

In fact, he’s a master of this gentle swing back and forth between serious and witty, and it’s this manoeuvre that must make him an assassin in the boardroom.

It also happens to make him a joy to hang out with, and a charming and rewarding guest to interview.

Since we last spoke Oren has developed a love of comedy, and he uses the art of a comedian in a lot of his examples when explaining pitch techniques.

Especially look out for Oren’s top three mistakes newbies always make.

All I can say is that having that balance between being serious enough to win the trust of a client, but also being able to charm them and make them laugh – is CRUCIAL.

And this strange mix of qualities that Oren embodies, is what makes him such an interesting character.

He’s friendly, hilarious, and has this wide-eyed, enthusiastic energy. But he’s made of steel, too.

You can’t walk into big corporate boardrooms and pitch for fifty or a hundred million dollars without having serious metal.

Oren doesn’t just accept the laws of capitalism, he actually seems to LOVE them.

But he’s no hard-hearted investment banker.

With Oren Klaff you get a guy who loves to pull the trigger on high-stakes deals, but who also loves interacting with human beings.

My guess is that underneath the big money and the extreme rush of making huge deals on a daily basis, is a simple love of human psychology in action.

You should watch out for Oren’s hilarious story about his conference lunch with NFL player Emmitt Smith, and how he spent 45 minutes winning this guy over.

It’s a brilliant example of Oren’s crazy courage and persistence, but it also brings out how much he loves a challenge.

The higher the stakes, the more Oren wants to play.

Oren is super-confident in his work. He’s refined his method so much that it basically has a perfect hit rate.

But in his own way, Oren seems to enjoy vulnerability, and this adds to his skills in my view.

It’s not just about business, it’s about testing yourself, finding your weaknesses and growing.

This episode is going to fly by, and you’re probably going to need to watch it twice.

Oren talks about so much, gets really deep into the mechanics of the pitch.

But like I said, he’ll make you laugh and touch your heart and you won’t even know how he does it.

And if you are one those types that thinks business and ‘pitching’ is ‘not for you’, then Oren has a lot to say about that too.

We’re always pitching, because we all need to win support to get things done.

So I hope you are sitting comfortably, because this interview is a RIDE believe me.

Ladies and gentlemen, I give you Oren Klaff.

[6:52] What changed since our last interview.

[9:00] Talking at Tony Robbin’s stage.

[12:10] Why I like the big stages of 5000 people.

[13:45] When you have a message to give, it makes a difference.

[14:50] $100,000 engagement. Transforming people’s perspective of what is possible with their perspective.

[15:30] How I start all my speeches.

[17:25] Asking for $50m is something at the edge of the human experience. People want what they can’t have. People chase that which runs away from them. People only value that which they pay for.

[17:55] The buyer is programmed to say maybe or no. Hijacking the investor’s process and making it our process.

[18:30] Be yourself – horrible advice.

[20:56] Information has no convincing power in today’s world.

[21:10] When going into a pitch, you give people ideas. Make yourself the centre of the world for information they need to get ahead in their business.

[22:20] Pitching vs Selling

[27:34] Status and social proof.

[29:00] How to start a pitch?

[31:00] 2 kinds of pitching. Pitching to raise money. When to talk first.

[34:50] Important to run the pitch professionally. Take charge. Only speak for as long as you are compelling.

[36:38] Bring the size of your presentation down so that people are riveted at the edge of their seats.

[37:35] Have to provide insights. Oh yeah, that makes sense. Video you. Take picture of your slide. I did not think of the world in that way. But now you explained it in that way, I understand why something has been going wrong and something has been going right.

[38:21] The Greatest American Hero. Helping people to understand some of the randomness in life.

[40:10] Not just new information but information that they feel is usable and simple and accessible.

[40:20] What do you say to people who think I don’t pitch. You need resources to do things. You need people to agree with your perspective. Vacation pitch. Why go to Hawaii now.

[43:10] Pitching is American. The things that tantalises the brain receptors work everywhere.

[44:45] Offer somebody something, and then tell them they can’t have it. They will really want it.

[46:30] NPR. Receptors in the brain.

[47:40] I need simple things that work.

[49:20] Easy to do. Simple to measure and manage. High value response.

[52:10] If you write me a cheque… Given them the opportunity. Don’t give away free opportunity.

[54:17] Pitching and pickup. Peacocking. Negs

[59:00] Oren 10 years ago.

[1:00:00] Internal talk gets externalised. Little Oren needs to go take a seat. Big Oren is up.

[1:01:44] 3 biggest mistakes when going into a pitch.

[1:03:50] Make the pitch a practised presentation. Make the pitch sound fresh. How long to practice a pitch.

[1:04:21] With a slide deck, and a clicker, you should be able to click without looking. At slide 6. And then this happens. $8Billion dollar fades away if you don’t do this right. Never lost eye contact.

[1:04:45] Confidence monitor. Losing energy and rapport and transactional equity when looking back to the slides.

[1:05:38] No pencil. No paper. No pen. No briefcase. Going down to the mat. Billionaire, zero-inaire.

[1:06:31] Billion dollar bridges gets sold in 20 minutes. The less stuff you taking, the better your presentation.

[1:07:34] If I’m pitching you, I guarantee you buying something you don’t necessary want to own. Edutainment.

[1:07:55] Intensity. Have to get the humour and humility up to continue to amp up the intensity.

[1:09:20] Comedy. Sample presentation on a mop. Lindsay Lohan’s mini bar tab.

[1:09:45] We could be King. Philadelphia high school football team.

[1:10:24] Hunger and humble. Hunger and humility.

[1:10:55] You are controlling the social environment, but you have to make them happy to want to be there.

[1:11:24] I can’t pitch a tent.

[1:11:47] Take out the neediness. Take out the thank you. Take out time. Less is more. Stop displaying weak behaviours.

[1:12:15] Let the big boy come out.

[1:13:20] Begging.

[1:13:40] Present a “new” problem. Most people present a solution. Why the obvious choice will lead to problems. Introduce new information. Make the logical choice will lead to problems.

[1:16:49] Pitches that didn’t go well.

[1:18:03] Speaking to the Houston Texas Utility Association. Meeting Emmitt Smith. OMG are you Randall Cunningham?

[1:21:30] Talking to 3 old ladies.

[1:25:00] Red flags. Series A in Silicon Valley. Not familiar with the territory. Not understanding how buyers buy.

[1:27:40] None of what I see and half of what I hear. Understand the buyer’s process.

[1:28:26] Not going to break a buyer’s process.

[1:29:55] How venture capital firm works.

[1:30:31] Andreessen Horowitz. We are in a bull market in tech. They have so much deal flow.

[1:32:21] They get the best supplies. They get the premium deals. They get the first looks.

[1:34:02] Success secret.

[1:34:33] What does your family think of you, pitch anything?

[1:36:00] Advice to the 18 year old Oren.

[1:41:37] Best advice ever received.

[1:46:12] Advice for the 20 year old out there.

[1:48:20] What resources do you have for people.

[1:52:10] This is my art form and I care that people do this well.

Skip to toolbar