Oren Klaff

Bestselling author of Pitch Anything & Flip the Script. Investment banker, entrepreneur, master of persuasion. Teaching you to win deals & influence people.

[Oren Klaff @orenklaff]

Most people walk into investor meetings with their hands out.
Not me.
Here’s how I start the call:

“Just want to make sure we’re efficient with time, because we’re fully capitalized and don’t need any money.”

Yeah, it throws them off. Confuses the hell out of investors who were ready to say “no” before they even heard the pitch.
But here’s the game:
Ask for money, get an opinion.
Ask for an opinion, get the money.

It’s not about begging - it’s about positioning.
If you want capital chasing you, stop acting like you need it.

[Oren Klaff @orenklaff]

Most people spend their time blaming the Fed, the news, or “the economy” for why they’re not winning.

But that’s not how the real game is played. Winners don’t get distracted by noise, they hunt down the bottleneck that controls the outcome, and they take control.

Every deal, every market, every opportunity - there’s always a choke point. If you’re not the one owning it, you’re just waiting for someone else to make the call.

It’s not about having a genius IQ or catching the next Bitcoin wave. It’s about seeing the real lever that moves the money… and pulling it first.

Stop watching from the sidelines. Get to the table. Find the bottleneck. Control the game.

[Oren Klaff @orenklaff]

Everyone loves to talk about the “big money.” 

The wild inventions, the 200-mile-per-gallon carburetor, the robo-legs, the next Tesla hiding in a garage somewhere.
You see the headlines, you want in. Who doesn’t?

But here’s what you’re not hearing:
Those deals don’t need your $25K. Hell, they don’t even need your $250K.
The people who actually get in are managing $300 million funds.
They’re in Silicon Valley, not scrolling YouTube in Scottsdale. They have the relationships, the access, and the firepower.
Their entire job is to multiply money, and even they miss the big ones most of the time.

So when you’re sitting at home in Destin, Arizona, Newark - spamming your “expertise” on crypto, medtech, or whatever’s hot this week - just know:
You’re not even on the field. You’re in the parking lot, listening to the game on AM radio.

Why?
No access. No track record. No way in. And even if you did get a meeting, your check is too small for them to care.

Here's the truth.
Stop wasting your time chasing lottery tickets.
Start building real skills, real relationships, and a reputation people trust.
Because until you do, the game is being played way over your head and your money isn’t even in the room.

[Oren Klaff @orenklaff]

Stop fetishizing cold traffic.
Work your territory. Build real relationships. Nurture your leads.
That’s how you get deals that close.

Instagram will sell you the dream: “30 clicks to 30 million.”
Stop chasing shortcuts and start mastering the fundamentals.

Real dealmakers aren’t gambling - they’re building engines that run hot because they know their territory inside and out.

[Oren Klaff @orenklaff]

Luxury is not about what you own. It’s about where you get in.

Milan taught me something you don’t learn on the outside:
The power isn’t in the price tag. It’s in your access.

Most people are chasing the crowd, hoping to look important.
But the real moves are made behind closed doors, long before the crowd even shows up.

If you want to play at the top level, stop measuring yourself by what you flash - start measuring by the rooms you’re invited into.

Get inside the circle. That’s where the game really starts.

[Oren Klaff @orenklaff]

If you’re not at the table, you’re on the menu.

Everybody’s chasing the Silicon Valley unicorn or the next Bitcoin moonshot - good luck with that.

Here’s the real play: Make real money in the real economy - with dirt, machines, and deals you can actually see, touch, and control.

Forget waiting for your “Tom Brady moment.” You don’t need to be a unicorn. You need to show up, do the real work, and get paid like a pro.

Average day. Average speed. Average intelligence. Extraordinary results - if you stop playing the fantasy game and start playing the real one.

Watch or listen here: https://t.co/mxaYXIx7oU

[Oren Klaff @orenklaff]

Most people think they’re in control.

Here’s the truth...There’s a hidden bottleneck in every deal, every business, every shot at real money. And if you don’t frame the game...You’re just another piece getting moved around.

In this episode, I’m exposing the choke points the pros see (and everyone else ignores).
— Why does the bottleneck always control the outcome
— How to frame the game so you’re the one making the rules
— And the hard truth: You’re either running the table, or you’re getting run over.

If you’re ready to stop playing defense and actually win, this is your episode.

Watch now.
Or keep getting played.

Watch or listen here: https://t.co/mxaYXIx7oU

[Oren Klaff @orenklaff]

You want to scale? Get status.
No status? Nobody’s listening. Nobody’s following.
Status is the ticket & without it, you’re invisible.
If you don’t have it, go get it.
And if you don’t know how, follow someone who does.

In business, status isn’t optional. It’s the game.

[Oren Klaff @orenklaff]

Everybody’s out here hustling, chasing deals, cold-calling, begging for five minutes of attention.
Stop.

Stand up, get in front of a group, even if it’s five people.
When you’re the one at the front of the room, you’re not “networking” you’re the main event.

People chase you.

No more desperate DMs. No more pitching in the dark.

Control the frame, control the room.

[Oren Klaff @orenklaff]

Rolex or Richard Mille. Which One Are You Actually Building?

Everybody wants to flex like Richard Mille - new face, new hype, chasing this season’s dopamine.
But let’s be real, most of those guys wind up with yesterday’s news on their wrist and nothing in the vault.

 I like Rolex thinking.
Minimal changes. Quiet confidence.
Five years from now is still valuable.
No need to scream about it.

Here’s the question for your business, your brand, your deals:
Are you playing the long game - compounding value, getting more solid with time?
Or are you chasing pop culture, jumping trend to trend, hoping for the next sugar high?

Watch the market.
Everyone says they want to build a Rolex, but most can’t resist the Mille.

Stay boring, stay rich.
Or go hype, go broke.
Choose wisely.

[Oren Klaff @orenklaff]

Most people see a polished slab and think it just shows up that way.

Here’s the truth...Nothing worth building gets handed to you. There’s sweat, arguments, wrong turns, and the occasional miracle buried in every project.

We took all the hits, made the tough calls, and built something you can actually put your name on.

This isn’t theory. It’s execution. It’s showing up when things get ugly, sorting through problems, and turning raw material into something you want to show off.

If you want pretty pictures, open Pinterest.

If you want something that lasts, call us.

[Oren Klaff @orenklaff]

Everybody wants to look like they’re winning.
Few actually are.

Here’s the reality.
It’s not the guy flexing their Rolex at the party who gets the deal. It’s the one you never saw coming, because he was already in the room where it happened.

Stop dressing for attention.
Start moving for access.

If you’re tired of chasing the outer ring, time for a switch up.

[Oren Klaff @orenklaff]

When I send an LOI, it’s not just a handshake and a smile. It’s got meat, potatoes, and the whole damn steakhouse.

My LOIs are so dialed-in, you could almost swap the letterhead and call it a definitive agreement.

If you’re giving or getting an LOI and it’s missing details -  You’re not dealmaking. You’re just playing dress-up.

Real dealmakers put the terms on the table up front.
Anything less is just smoke.

[Oren Klaff @orenklaff]

Every new deal is on the same desperate hunt: Money.
Doesn’t matter how good it is.

The real skill is getting out of Dumpsville and into the room where the money actually moves.

If you’re tired of hearing “no,” you’re finally ready to play the real game.

[Oren Klaff @orenklaff]

Stepping inside the circle in Milan.

In Episode 47 of The Game of Money, I break down what most people get wrong about luxury and why dealmakers don’t play on the outside.

Forget the hype. Real access, real power, real deals.

Want to know how Milan’s elite actually move?

Hit the link. Get inside the circle. https://t.co/mxaYXIx7oU

[Oren Klaff @orenklaff]

You want to know real leverage? Try this.

[Oren Klaff @orenklaff]

Here’s the game: Be ALL IN. Without being desperate. Show up like you need nothing, but deliver like you need everything.

If you can do that, you hold the cards.

99% of deals are lost because you’re either too available… or too unavailable. Find the tension. Stay in the pocket. That’s how you win.

[Oren Klaff @orenklaff]

Everyone wants the million-dollar check.
But here’s what they don’t tell you: If you’ve never closed $150k, why are you out here chasing $3 million?

Shrink your ambition to what you can actually deliver. Get one high-confidence investor. Treat them like royalty. Stack wins.
Big deals don’t go to “big dreamers” they go to repeat performers.

Don’t “vision-board” your way to $1M. Close $100k first. Build a track record, not a fantasy.

[Oren Klaff @orenklaff]

In Milan. Shooting the podcast at a design studio where everything’s intentional.

That’s how your pitch should feel.

Most people walk into a room and start talking.
They haven’t thought about the frame, the environment, the pacing - none of it.

But in high-stakes deals, how you set the room matters just as much as what you say in it.

If your pitch feels like it was thrown together in a Starbucks, that’s how they’ll treat your deal.

[Oren Klaff @orenklaff]

How do you know when to walk away?

Here’s the play:
You don’t wait until you’re desperate. You set your terms before you even sit down.
Know what a win looks like, before the cards are dealt, before the emotions kick in, before the room gets noisy.

Amateurs chase losses and cling to hope. Pros have an exit plan.
They spot the signs:

The odds start tilting against you

The conversation shifts from strategy to luck

You’ve hit your target and the upside is shrinking

I never leave it to chance. I leave when the math, and my gut, tell me the next hand isn’t worth playing.

It’s not ego. It’s discipline.

Anyone can play a hand. The real game is knowing when to cash out and move to the next opportunity.